# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_698_573_mecaach+h2f3-
_database_code_depnum_ccdc_archive 'CCDC 2263384'
loop_
_audit_author_name
_audit_author_address
'Evelin Gruden'
;Jozef Stefan Institute
Slovenia
;
_audit_update_record             
;
2023-05-16 deposited with the CCDC.	2023-06-20 downloaded from the CCDC.
;
_audit_creation_date             2022-03-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_SHELXL_version_number           2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H32 N, F3 H2'
_chemical_formula_sum            'C20 H34 F3 N'
_chemical_formula_weight         345.48
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H32 N F3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.8109(4)
_cell_length_b                   9.4778(3)
_cell_length_c                   20.4419(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.161(4)
_cell_angle_gamma                90
_cell_volume                     2039.53(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4945
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      71.7950
_cell_measurement_theta_min      4.2480
_shelx_estimated_absorpt_T_max   0.877
_shelx_estimated_absorpt_T_min   0.744
_exptl_absorpt_coefficient_mu    0.684
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.125
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 13 0.1046
0 0 -13 0.0965
0 5 -6 0.1677
0 -5 8 0.1852
7 0 -3 0.0958
-7 0 4 0.0972
5 4 2 0.1707
-7 1 5 0.0906
-5 -4 -2 0.1197
4 -4 -8 0.1568
5 0 -11 0.1042
3 5 2 0.1972
5 4 -5 0.1610
-6 -2 9 0.1206
-4 1 -9 0.0906
4 -1 10 0.1176

_exptl_crystal_size_max          0.459
_exptl_crystal_size_mid          0.222
_exptl_crystal_size_min          0.197
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0051 -0.9973 12.9998 -0.1167 0.9255 0.4106
-0.0053 -0.0024 -12.9999 0.0916 -0.8399 -0.5465
-0.0013 4.9978 -5.9996 0.1677 -0.8156 0.4272
0.0021 -4.9974 7.9996 -0.1818 0.9448 -0.3431
7.0001 -0.0000 -3.0070 -0.9812 -0.1591 0.0820
-6.9997 0.0002 4.0070 0.9741 0.2237 -0.0400
5.0027 3.9999 1.9952 -0.6297 -0.1883 0.7763
-6.9990 1.0002 5.0070 0.9921 0.2027 0.1379
-5.0027 -3.9999 -1.9952 0.6297 0.1883 -0.7763
3.9966 -4.0003 -8.0042 -0.6167 -0.1547 -0.7609
4.9964 -0.0017 -11.0049 -0.6384 -0.6859 -0.3138
3.0025 4.9995 1.9973 -0.3182 -0.2838 0.8527
4.9998 3.9986 -5.0047 -0.5803 -0.6406 0.4820
-5.9979 -1.9983 9.0058 0.7455 0.7229 -0.0718
-4.0042 0.9978 -8.9959 0.6613 -0.6869 -0.3614
4.0046 -0.9976 9.9959 -0.6683 0.7515 0.4034

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16584
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        70.000
_diffrn_reflns_theta_max         72.274
_diffrn_reflns_theta_min         4.281
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6426
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -73.00  35.00   1.00    2.46    --  -41.11  77.00 -20.00  108
  2  ω    -21.00  50.00   1.00    2.46    --   41.11 -77.00-146.00   71
  3  ω     51.00  82.00   1.00    9.84    --  103.58 -77.00-146.00   31
  4  ω    110.00 178.00   1.00    9.84    --  103.58  77.00 -20.00   68
  5  ω    -73.00  28.00   1.00    2.46    --  -41.11  77.00 120.00  101
  6  ω     38.00 112.00   1.00    2.46    --   41.11  57.00  90.00   74
  7  ω     20.00  63.00   1.00    2.46    --   41.11  57.00  60.00   43
  8  ω     57.00 109.00   1.00    2.46    --   41.11  57.00   0.00   52
  9  ω    103.00 178.00   1.00    9.84    --  103.58  77.00  60.00   75
 10  ω     26.00 116.00   1.00    9.84    --  103.58 -80.00 165.57   90
 11  ω     99.00 176.00   1.00    9.84    --  103.58  45.00  30.00   77
 12  ω     76.00 103.00   1.00    9.84    --  103.58 -79.00 131.21   27
 13  ω     64.00 115.00   1.00    9.84    --  103.58 -80.00-106.30   51
 14  ω     35.00  60.00   1.00    9.84    --  103.58 -80.00-106.30   25
 15  ω     86.00 173.00   1.00    9.84    --  103.58  45.00 120.00   87
 16  ω     76.00 103.00   1.00    9.84    --  103.58 -80.00  91.02   27
 17  ω     30.00  55.00   1.00    9.84    --  103.58 -79.00 -32.50   25
 18  ω     88.00 124.00   1.00    9.84    --  103.58 -79.00 -32.50   36
 19  ω     32.00  67.00   1.00    9.84    --  103.58 -45.00  30.00   35
 20  ω    104.00 150.00   1.00    9.84    --  103.58  77.00 150.00   46
 21  ω     81.00 108.00   1.00    9.84    --  103.58 -45.00  30.00   27
 22  ω     58.00  85.00   1.00    9.84    --  103.58 -79.00  47.66   27
 23  ω    118.00 168.00   1.00    9.84    --  103.58  45.00 -60.00   50
 24  ω     27.00 124.00   1.00    9.84    --  103.58 -80.00   5.22   97
 25  ω     41.00  66.00   1.00    9.84    --  103.58 -45.00   0.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1431681000
_diffrn_orient_matrix_UB_12      0.0251236000
_diffrn_orient_matrix_UB_13      -0.0069948000
_diffrn_orient_matrix_UB_21      0.0050320000
_diffrn_orient_matrix_UB_22      -0.0856080000
_diffrn_orient_matrix_UB_23      0.0646251000
_diffrn_orient_matrix_UB_31      0.0297611000
_diffrn_orient_matrix_UB_32      0.1359131000
_diffrn_orient_matrix_UB_33      0.0420024000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3211
_reflns_number_total             3973
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3973
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0498
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0650P)²+0.6968P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1391
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Uiso: H2B(0.05135)
3.a Ternary CH refined with riding coordinates:
 C16(H16), C19(H19)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C12(H12), C13(H13), C14(H14)
3.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C17(H17A,
 H17B,H17C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C21(H21B,H21A,H21C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.53038(12) 0.19539(13) 0.34687(6) 0.0268(3) Uani 1 1 d . . . . .
C2 C 0.51463(14) 0.28118(17) 0.29761(7) 0.0301(3) Uani 1 1 d . . . . .
H2 H 0.498733 0.378911 0.301963 0.036 Uiso 1 1 calc R U . . .
C3 C 0.52329(16) 0.21508(18) 0.23255(7) 0.0332(4) Uani 1 1 d . . . . .
C4 C 0.57555(17) 0.06739(18) 0.25575(8) 0.0367(4) Uani 1 1 d . . . . .
H4A H 0.667642 0.062728 0.257277 0.044 Uiso 1 1 calc R U . . .
H4B H 0.531776 -0.005525 0.224129 0.044 Uiso 1 1 calc R U . . .
C5 C 0.55155(16) 0.04191(17) 0.32664(8) 0.0318(3) Uani 1 1 d . . . . .
C6 C 0.61403(19) 0.3008(2) 0.20015(9) 0.0457(4) Uani 1 1 d . . . . .
H6A H 0.577868 0.394494 0.187869 0.069 Uiso 1 1 calc R U . . .
H6B H 0.625961 0.251962 0.159774 0.069 Uiso 1 1 calc R U . . .
H6C H 0.696179 0.310527 0.232135 0.069 Uiso 1 1 calc R U . . .
C7 C 0.39054(19) 0.2143(2) 0.18545(9) 0.0477(5) Uani 1 1 d . . . . .
H7A H 0.332242 0.160130 0.206097 0.072 Uiso 1 1 calc R U . . .
H7B H 0.395050 0.170902 0.142543 0.072 Uiso 1 1 calc R U . . .
H7C H 0.359608 0.311446 0.177640 0.072 Uiso 1 1 calc R U . . .
C8 C 0.66508(18) -0.0218(2) 0.37544(9) 0.0407(4) Uani 1 1 d . . . . .
H8A H 0.741964 0.030936 0.373173 0.061 Uiso 1 1 calc R U . . .
H8B H 0.674976 -0.120597 0.363448 0.061 Uiso 1 1 calc R U . . .
H8C H 0.651520 -0.016815 0.421184 0.061 Uiso 1 1 calc R U . . .
C9 C 0.43323(18) -0.04533(18) 0.32592(9) 0.0406(4) Uani 1 1 d . . . . .
H9A H 0.417655 -0.048588 0.371285 0.061 Uiso 1 1 calc R U . . .
H9B H 0.445623 -0.141387 0.310855 0.061 Uiso 1 1 calc R U . . .
H9C H 0.360134 -0.002252 0.295150 0.061 Uiso 1 1 calc R U . . .
C10 C 0.53133(14) 0.24139(16) 0.41527(7) 0.0275(3) Uani 1 1 d . . . . .
C11 C 0.41747(15) 0.24126(16) 0.43713(7) 0.0296(3) Uani 1 1 d . . . . .
C12 C 0.42438(16) 0.28514(18) 0.50316(8) 0.0342(4) Uani 1 1 d . . . . .
H12 H 0.349417 0.285438 0.520004 0.041 Uiso 1 1 calc R U . . .
C13 C 0.53768(17) 0.32806(18) 0.54448(8) 0.0369(4) Uani 1 1 d . . . . .
H13 H 0.540397 0.355281 0.589513 0.044 Uiso 1 1 calc R U . . .
C14 C 0.64718(16) 0.33139(18) 0.52029(8) 0.0357(4) Uani 1 1 d . . . . .
H14 H 0.724119 0.363343 0.548795 0.043 Uiso 1 1 calc R U . . .
C15 C 0.64710(15) 0.28887(17) 0.45495(8) 0.0308(3) Uani 1 1 d . . . . .
C16 C 0.28812(15) 0.20767(18) 0.39198(8) 0.0334(4) Uani 1 1 d . . . . .
H16 H 0.302274 0.169554 0.348653 0.040 Uiso 1 1 calc R U . . .
C17 C 0.21559(17) 0.0962(2) 0.42252(10) 0.0435(4) Uani 1 1 d . . . . .
H17A H 0.268357 0.011598 0.433577 0.065 Uiso 1 1 calc R U . . .
H17B H 0.136873 0.071785 0.390076 0.065 Uiso 1 1 calc R U . . .
H17C H 0.195108 0.133780 0.463446 0.065 Uiso 1 1 calc R U . . .
C18 C 0.20859(17) 0.3428(2) 0.37628(10) 0.0433(4) Uani 1 1 d . . . . .
H18A H 0.194467 0.383040 0.418137 0.065 Uiso 1 1 calc R U . . .
H18B H 0.126600 0.320331 0.346231 0.065 Uiso 1 1 calc R U . . .
H18C H 0.253933 0.411288 0.354449 0.065 Uiso 1 1 calc R U . . .
C19 C 0.76776(16) 0.3048(2) 0.42874(8) 0.0369(4) Uani 1 1 d . . . . .
H19 H 0.753855 0.254418 0.384689 0.044 Uiso 1 1 calc R U . . .
C20 C 0.79267(19) 0.4601(2) 0.41610(10) 0.0490(5) Uani 1 1 d . . . . .
H20A H 0.718914 0.499835 0.384499 0.074 Uiso 1 1 calc R U . . .
H20B H 0.867825 0.467865 0.397088 0.074 Uiso 1 1 calc R U . . .
H20C H 0.807235 0.512106 0.458599 0.074 Uiso 1 1 calc R U . . .
C21 C 0.88389(17) 0.2385(3) 0.47585(10) 0.0525(5) Uani 1 1 d . . . . .
H21B H 0.956359 0.241124 0.454506 0.079 Uiso 1 1 calc R U . . .
H21A H 0.864959 0.140298 0.485070 0.079 Uiso 1 1 calc R U . . .
H21C H 0.904617 0.291497 0.518085 0.079 Uiso 1 1 calc R U . . .
F1 F 0.35431(15) 0.56385(16) 0.26863(9) 0.0757(4) Uani 1 1 d . . . . .
H2B H 0.442(2) 0.601(2) 0.2673(11) 0.051 Uiso 1 1 d . U . . .
F2 F 0.55941(13) 0.63517(16) 0.29007(7) 0.0655(4) Uani 1 1 d . . . . .
H2A H 0.570(3) 0.675(4) 0.2290(18) 0.101(11) Uiso 1 1 d . . . . .
F3 F 0.60850(14) 0.6990(2) 0.18938(8) 0.0823(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.275(2) . ?
N1 C5 1.543(2) . ?
N1 C10 1.4626(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.492(2) . ?
C3 C4 1.543(2) . ?
C3 C6 1.535(2) . ?
C3 C7 1.535(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.548(2) . ?
C5 C8 1.519(2) . ?
C5 C9 1.520(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.402(2) . ?
C10 C15 1.402(2) . ?
C11 C12 1.398(2) . ?
C11 C16 1.523(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.383(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.395(2) . ?
C15 C19 1.526(2) . ?
C16 H16 1.0000 . ?
C16 C17 1.531(2) . ?
C16 C18 1.535(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19 1.0000 . ?
C19 C20 1.529(3) . ?
C19 C21 1.532(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21C 0.9800 . ?
F1 H2B 1.02(2) . ?
F2 H2B 1.29(2) . ?
F2 H2A 1.33(4) . ?
F3 H2A 1.01(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C5 113.00(12) . . ?
C2 N1 C10 122.38(13) . . ?
C10 N1 C5 124.60(12) . . ?
N1 C2 H2 122.8 . . ?
N1 C2 C3 114.32(14) . . ?
C3 C2 H2 122.8 . . ?
C2 C3 C4 101.52(12) . . ?
C2 C3 C6 109.77(14) . . ?
C2 C3 C7 108.76(15) . . ?
C6 C3 C4 112.79(15) . . ?
C6 C3 C7 109.26(14) . . ?
C7 C3 C4 114.40(15) . . ?
C3 C4 H4A 110.2 . . ?
C3 C4 H4B 110.2 . . ?
C3 C4 C5 107.55(13) . . ?
H4A C4 H4B 108.5 . . ?
C5 C4 H4A 110.2 . . ?
C5 C4 H4B 110.2 . . ?
N1 C5 C4 99.81(12) . . ?
C8 C5 N1 110.21(13) . . ?
C8 C5 C4 113.21(14) . . ?
C8 C5 C9 110.02(14) . . ?
C9 C5 N1 109.84(13) . . ?
C9 C5 C4 113.31(14) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 N1 119.27(13) . . ?
C15 C10 N1 117.38(13) . . ?
C15 C10 C11 123.30(14) . . ?
C10 C11 C16 123.96(14) . . ?
C12 C11 C10 116.72(14) . . ?
C12 C11 C16 119.14(14) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 C11 121.54(15) . . ?
C13 C12 H12 119.2 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.00(15) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 119.3 . . ?
C13 C14 C15 121.45(15) . . ?
C15 C14 H14 119.3 . . ?
C10 C15 C19 123.41(14) . . ?
C14 C15 C10 116.91(15) . . ?
C14 C15 C19 119.55(15) . . ?
C11 C16 H16 107.9 . . ?
C11 C16 C17 112.45(14) . . ?
C11 C16 C18 110.21(14) . . ?
C17 C16 H16 107.9 . . ?
C17 C16 C18 110.28(15) . . ?
C18 C16 H16 107.9 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C19 H19 107.7 . . ?
C15 C19 C20 110.62(15) . . ?
C15 C19 C21 112.48(14) . . ?
C20 C19 H19 107.7 . . ?
C20 C19 C21 110.53(16) . . ?
C21 C19 H19 107.7 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21B C21 H21A 109.5 . . ?
H21B C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H2B F2 H2A 91.3(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 -10.79(18) . . . . ?
N1 C2 C3 C6 -130.34(16) . . . . ?
N1 C2 C3 C7 110.17(16) . . . . ?
N1 C10 C11 C12 179.46(14) . . . . ?
N1 C10 C11 C16 -5.5(2) . . . . ?
N1 C10 C15 C14 -179.48(14) . . . . ?
N1 C10 C15 C19 4.7(2) . . . . ?
C2 N1 C5 C4 12.81(17) . . . . ?
C2 N1 C5 C8 132.13(15) . . . . ?
C2 N1 C5 C9 -106.48(15) . . . . ?
C2 N1 C10 C11 91.66(18) . . . . ?
C2 N1 C10 C15 -85.95(18) . . . . ?
C2 C3 C4 C5 18.32(16) . . . . ?
C3 C4 C5 N1 -18.66(16) . . . . ?
C3 C4 C5 C8 -135.77(15) . . . . ?
C3 C4 C5 C9 98.05(16) . . . . ?
C5 N1 C2 C3 -1.41(19) . . . . ?
C5 N1 C10 C11 -90.11(18) . . . . ?
C5 N1 C10 C15 92.29(18) . . . . ?
C6 C3 C4 C5 135.72(15) . . . . ?
C7 C3 C4 C5 -98.59(17) . . . . ?
C10 N1 C2 C3 177.02(13) . . . . ?
C10 N1 C5 C4 -165.57(13) . . . . ?
C10 N1 C5 C8 -46.25(19) . . . . ?
C10 N1 C5 C9 75.14(18) . . . . ?
C10 C11 C12 C13 0.8(2) . . . . ?
C10 C11 C16 C17 129.30(17) . . . . ?
C10 C11 C16 C18 -107.21(18) . . . . ?
C10 C15 C19 C20 103.76(18) . . . . ?
C10 C15 C19 C21 -132.11(18) . . . . ?
C11 C10 C15 C14 3.0(2) . . . . ?
C11 C10 C15 C19 -172.85(15) . . . . ?
C11 C12 C13 C14 1.5(3) . . . . ?
C12 C11 C16 C17 -55.7(2) . . . . ?
C12 C11 C16 C18 67.76(19) . . . . ?
C12 C13 C14 C15 -1.6(3) . . . . ?
C13 C14 C15 C10 -0.6(2) . . . . ?
C13 C14 C15 C19 175.42(16) . . . . ?
C14 C15 C19 C20 -72.00(19) . . . . ?
C14 C15 C19 C21 52.1(2) . . . . ?
C15 C10 C11 C12 -3.1(2) . . . . ?
C15 C10 C11 C16 172.00(15) . . . . ?
C16 C11 C12 C13 -174.58(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.227
_oxdiff_exptl_absorpt_empirical_full_min 0.840
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_910_605_mecaach+h2f3-_csf_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 2263386'
loop_
_audit_author_name
_audit_author_address
'Evelin Gruden'
;Jozef Stefan Institute
Slovenia
;
_audit_update_record             
;
2023-05-16 deposited with the CCDC.	2023-06-20 downloaded from the CCDC.
;
_audit_creation_date             2023-04-11
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H32 F N'
_chemical_formula_sum            'C20 H32 F N'
_chemical_formula_weight         305.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H30 N F'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.33810(10)
_cell_length_b                   12.42200(10)
_cell_length_c                   12.3701(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.4960(10)
_cell_angle_gamma                90
_cell_volume                     1817.85(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    22440
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.3070
_cell_measurement_theta_min      3.5370
_shelx_estimated_absorpt_T_max   0.886
_shelx_estimated_absorpt_T_min   0.836
_exptl_absorpt_coefficient_mu    0.548
_exptl_absorpt_correction_T_max  0.902
_exptl_absorpt_correction_T_min  0.858
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.88a (Rigaku Oxford Diffraction, 2023)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.116
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-7 -1 -1 0.1118
3 4 6 0.1507
8 -2 -2 0.1176
6 -3 -5 0.1672
7 0 1 0.1080
2 5 -6 0.1573
-2 -6 5 0.1553
1 -8 -2 0.1917
2 -6 -6 0.1518
-3 5 6 0.1467
-7 0 -1 0.1062
5 -6 -1 0.1664
7 3 -4 0.1406
-7 -4 3 0.1601
0 6 5 0.1528
-3 -6 -3 0.1860
-3 5 -5 0.1632
-1 8 1 0.1996

_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.307
_exptl_crystal_size_min          0.226
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-7.2032 -0.5993 -1.2658 0.7588 0.6490 -0.0555
2.6801 3.5382 5.6581 -0.4947 -0.4242 0.7585
7.8520 -1.5810 -2.1159 -0.6840 -0.5843 -0.4368
6.4029 -3.4346 -5.0822 -0.4203 -0.3582 -0.8337
7.4390 0.2465 0.7246 -0.7598 -0.6497 -0.0256
2.0995 5.3772 -5.9687 0.6266 -0.7325 -0.2661
-1.6047 -6.4474 4.8157 -0.6483 0.7580 0.0722
1.2787 -7.6533 -2.4491 -0.4099 0.4803 -0.7754
2.4960 -5.5398 -5.7633 -0.1224 0.1414 -0.9824
-2.6201 5.1289 6.1257 0.0787 -0.0902 0.9928
-7.2035 0.3855 -1.2942 0.8237 0.5669 0.0076
5.2983 -6.0436 -1.3493 -0.7844 0.0194 -0.6200
6.9700 3.2103 -4.2146 -0.1232 -0.9423 -0.3114
-6.7409 -4.1612 3.1375 0.1286 0.9822 0.1371
-0.3235 5.7732 5.4573 -0.0470 -0.3536 0.9342
-2.7670 -6.4757 -2.9481 0.0952 0.7231 -0.6842
-2.8592 4.7507 -4.7681 0.9664 -0.2313 -0.1125
-0.6535 8.0111 0.7829 0.5084 -0.5934 0.6240

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0083
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4451
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        70.000
_diffrn_reflns_theta_max         76.382
_diffrn_reflns_theta_min         3.736
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6426
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -6.00  24.00   1.00    3.12    --  -40.98  77.00   0.00   30
  2  ω    -64.00  30.00   1.00    3.12    --  -40.98  57.00-120.00   94
  3  ω    -74.00 -44.00   1.00    3.12    --  -40.98  77.00   0.00   30
  4  ω   -109.00 -18.00   1.00    3.12    --  -40.98 -57.00  90.00   91
  5  ω    -20.00  74.00   1.00    3.12    --   40.98 -77.00 -30.00   94
  6  ω     79.00 165.00   1.00   12.46    --  103.58  45.00   0.00   86
  7  ω     32.00  95.00   1.00   12.46    --  103.58 -45.00-180.00   63
  8  ω     92.00 119.00   1.00   12.46    --  103.58 -80.00 -89.12   27
  9  ω    106.00 177.00   1.00   12.46    --  103.58  77.00-150.00   71
 10  ω    102.00 130.00   1.00   12.46    --  103.58 -80.00 -47.70   28
 11  ω     90.00 173.00   1.00   12.46    --  103.58  45.00 -60.00   83
 12  ω    104.00 163.00   1.00   12.46    --  103.58  77.00-120.00   59
 13  ω     91.00 117.00   1.00   12.46    --  103.58  61.00-180.00   26
 14  ω    140.00 176.00   1.00   12.46    --  103.58  61.00-180.00   36
 15  ω     31.00 125.00   1.00   12.46    --  103.58 -80.00  12.23   94
 16  ω     76.00 101.00   1.00   12.46    --  103.58 -77.00  90.00   25
 17  ω     33.00  84.00   1.00   12.46    --  103.58 -80.00 -47.70   51
 18  ω     80.00 107.00   1.00   12.46    --  103.58 -80.00-124.76   27
 19  ω     78.00 103.00   1.00   12.46    --  103.58 -77.00  60.00   25
 20  ω     30.00  94.00   1.00   12.46    --  103.58 -77.00 120.00   64
 21  ω     27.00 117.00   1.00   12.46    --  103.58 -80.00 173.00   90
 22  ω     43.00  86.00   1.00   12.46    --  112.00 -56.00-168.00   43
 23  ω    -92.00 -14.00   1.00    3.12    --  -41.23 -57.00 -30.00   78
 24  ω    -74.00 -13.00   1.00    3.12    --  -41.23 -57.00 150.00   61
 25  ω   -114.00 -79.00   1.00    3.12    --  -41.23 -57.00 150.00   35
 26  ω   -113.00 -14.00   1.00    3.12    --  -41.23 -57.00 -90.00   99
 27  ω     10.00  40.00   1.00    3.12    --   41.23  76.00 -75.45   30
 28  ω     13.00  40.00   1.00    3.12    --   41.23  79.00 -30.13   27
 29  ω      8.00  40.00   1.00    3.12    --   41.23  80.00  67.44   32
 30  ω      9.00  41.00   1.00    3.12    --   41.23  80.00-127.42   32
 31  ω    -12.00  63.00   1.00    3.12    --   41.23 -77.00 120.00   75
 32  ω      9.00  41.00   1.00    3.12    --   41.23  77.00 114.90   32
 33  ω    -31.00  31.00   1.00    3.12    --   41.23 -57.00  30.00   62
 34  ω     83.00 108.00   1.00   12.46    --  112.00  61.00-150.00   25
 35  ω     86.00 114.00   1.00   12.46    --  112.00  45.00  30.00   28
 36  ω    141.00 174.00   1.00   12.46    --  112.00  61.00-150.00   33
 37  ω     86.00 134.00   1.00   12.46    --  112.00  45.00  90.00   48
 38  ω    140.00 178.00   1.00   12.46    --  112.00  56.00 -26.00   38
 39  ω     83.00 174.00   1.00   12.46    --  112.00  61.00 -90.00   91
 40  ω     86.00 144.00   1.00   12.46    --  112.00  45.00-120.00   58
 41  ω     35.00  74.00   1.00   12.46    --  112.00 -80.00  -3.09   39
 42  ω    133.00 166.00   1.00   12.46    --  112.00  45.00 -30.00   33
 43  ω    116.00 178.00   1.00   12.46    --  112.00  61.00 -60.00   62
 44  ω     84.00 126.00   1.00   12.46    --  112.00  56.00 -26.00   42
 45  ω     83.00 108.00   1.00   12.46    --  112.00  61.00 -60.00   25
 46  ω     39.00 118.00   1.00   12.46    --  112.00 -80.00 143.87   79
 47  ω     83.00 172.00   1.00   12.46    --  112.00  61.00 120.00   89
 48  ω     83.00 108.00   1.00   12.46    --  112.00  61.00  30.00   25
 49  ω    120.00 177.00   1.00   12.46    --  112.00  61.00  30.00   57
 50  ω     83.00 133.00   1.00   12.46    --  112.00  61.00-180.00   50
 51  ω    140.00 170.00   1.00   12.46    --  112.00  61.00-180.00   30
 52  ω     83.00 109.00   1.00   12.46    --  112.00  61.00  60.00   26
 53  ω     86.00 111.00   1.00   12.46    --  112.00  45.00 -30.00   25
 54  ω    121.00 147.00   1.00   12.46    --  112.00  45.00-180.00   26
 55  ω    120.00 178.00   1.00   12.46    --  112.00  61.00   0.00   58
 56  ω     86.00 158.00   1.00   12.46    --  112.00  45.00-150.00   72
 57  ω     35.00 130.00   1.00   12.46    --  112.00 -78.00 -40.78   95
 58  ω     83.00 109.00   1.00   12.46    --  112.00  61.00   0.00   26
 59  ω     89.00 142.00   1.00   12.46    --  112.00  45.00 -90.00   53
 60  ω     39.00  82.00   1.00   12.46    --  112.00 -77.00-180.00   43
 61  ω     98.00 143.00   1.00   12.46    --  112.00 -77.00-180.00   45
 62  ω     41.00 129.00   1.00   12.46    --  112.00 -45.00   0.00   88
 63  ω     94.00 122.00   1.00   12.46    --  112.00 -56.00-168.00   28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0962935000
_diffrn_orient_matrix_UB_12      0.0635811000
_diffrn_orient_matrix_UB_13      -0.0815797000
_diffrn_orient_matrix_UB_21      -0.0863163000
_diffrn_orient_matrix_UB_22      -0.0828442000
_diffrn_orient_matrix_UB_23      0.0177205000
_diffrn_orient_matrix_UB_31      -0.0153452000
_diffrn_orient_matrix_UB_32      0.0669221000
_diffrn_orient_matrix_UB_33      0.0994782000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4089
_reflns_number_total             4451
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         4451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0777P)²+0.2618P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1182
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.7790(15)
 0.2210(15)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C2(H2), C16(H16), C19(H19)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
3.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14)
3.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C17(H17A,
 H17B,H17C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.43763(6) 0.39845(6) 0.38609(7) 0.0343(2) Uani 1 1 d . . . . .
N1 N 0.27111(7) 0.39555(7) 0.44181(8) 0.0185(2) Uani 1 1 d . . . . .
C2 C 0.38746(9) 0.37625(9) 0.47652(9) 0.0217(2) Uani 1 1 d . . . . .
H2 H 0.424404 0.421053 0.544105 0.026 Uiso 1 1 calc R U . . .
C3 C 0.40242(10) 0.25592(9) 0.50622(10) 0.0252(3) Uani 1 1 d . . . . .
C4 C 0.29185(10) 0.20892(9) 0.42941(10) 0.0256(2) Uani 1 1 d . . . . .
H4A H 0.269485 0.144229 0.464632 0.031 Uiso 1 1 calc R U . . .
H4B H 0.302105 0.188043 0.355704 0.031 Uiso 1 1 calc R U . . .
C5 C 0.20014(9) 0.29663(8) 0.41307(9) 0.0202(2) Uani 1 1 d . . . . .
C6 C 0.50691(11) 0.20676(12) 0.48211(13) 0.0359(3) Uani 1 1 d . . . . .
H6A H 0.501495 0.215512 0.402011 0.054 Uiso 1 1 calc R U . . .
H6B H 0.511230 0.129977 0.501061 0.054 Uiso 1 1 calc R U . . .
H6C H 0.574919 0.243303 0.527816 0.054 Uiso 1 1 calc R U . . .
C7 C 0.41205(11) 0.23988(11) 0.63176(10) 0.0310(3) Uani 1 1 d . . . . .
H7A H 0.484232 0.269182 0.677594 0.047 Uiso 1 1 calc R U . . .
H7B H 0.408355 0.162868 0.647539 0.047 Uiso 1 1 calc R U . . .
H7C H 0.349697 0.277357 0.650211 0.047 Uiso 1 1 calc R U . . .
C8 C 0.12286(10) 0.29639(10) 0.29206(10) 0.0263(3) Uani 1 1 d . . . . .
H8A H 0.070982 0.357777 0.281272 0.039 Uiso 1 1 calc R U . . .
H8B H 0.079296 0.229312 0.278003 0.039 Uiso 1 1 calc R U . . .
H8C H 0.168781 0.301942 0.239365 0.039 Uiso 1 1 calc R U . . .
C9 C 0.12403(10) 0.28305(10) 0.49079(11) 0.0275(3) Uani 1 1 d . . . . .
H9A H 0.170988 0.275432 0.568909 0.041 Uiso 1 1 calc R U . . .
H9B H 0.077123 0.218625 0.468675 0.041 Uiso 1 1 calc R U . . .
H9C H 0.075307 0.346411 0.484510 0.041 Uiso 1 1 calc R U . . .
C10 C 0.22829(8) 0.50375(8) 0.43135(9) 0.0186(2) Uani 1 1 d . . . . .
C11 C 0.21006(9) 0.55565(9) 0.52663(9) 0.0208(2) Uani 1 1 d . . . . .
C12 C 0.17086(10) 0.66163(10) 0.51595(10) 0.0258(2) Uani 1 1 d . . . . .
H12 H 0.158278 0.696598 0.579619 0.031 Uiso 1 1 calc R U . . .
C13 C 0.14991(11) 0.71697(10) 0.41542(11) 0.0297(3) Uani 1 1 d . . . . .
H13 H 0.122330 0.788763 0.409682 0.036 Uiso 1 1 calc R U . . .
C14 C 0.16958(10) 0.66652(10) 0.32308(10) 0.0271(3) Uani 1 1 d . . . . .
H14 H 0.155686 0.704853 0.254029 0.033 Uiso 1 1 calc R U . . .
C15 C 0.20926(9) 0.56094(9) 0.32855(9) 0.0217(2) Uani 1 1 d . . . . .
C16 C 0.23597(9) 0.50291(9) 0.64235(9) 0.0222(2) Uani 1 1 d . . . . .
H16 H 0.256065 0.425938 0.634201 0.027 Uiso 1 1 calc R U . . .
C17 C 0.13373(11) 0.50495(10) 0.68974(11) 0.0295(3) Uani 1 1 d . . . . .
H17A H 0.115232 0.579676 0.702744 0.044 Uiso 1 1 calc R U . . .
H17B H 0.151872 0.465230 0.761089 0.044 Uiso 1 1 calc R U . . .
H17C H 0.068796 0.471256 0.635639 0.044 Uiso 1 1 calc R U . . .
C18 C 0.33791(10) 0.55729(11) 0.72509(10) 0.0312(3) Uani 1 1 d . . . . .
H18A H 0.402186 0.556846 0.693313 0.047 Uiso 1 1 calc R U . . .
H18B H 0.358074 0.517986 0.796727 0.047 Uiso 1 1 calc R U . . .
H18C H 0.318580 0.631772 0.738063 0.047 Uiso 1 1 calc R U . . .
C19 C 0.23454(10) 0.51565(9) 0.22373(9) 0.0240(2) Uani 1 1 d . . . . .
H19 H 0.257438 0.438644 0.238891 0.029 Uiso 1 1 calc R U . . .
C20 C 0.33289(11) 0.57602(11) 0.19853(12) 0.0335(3) Uani 1 1 d . . . . .
H20A H 0.312514 0.651960 0.183717 0.050 Uiso 1 1 calc R U . . .
H20B H 0.348959 0.544242 0.132221 0.050 Uiso 1 1 calc R U . . .
H20C H 0.400102 0.570487 0.263539 0.050 Uiso 1 1 calc R U . . .
C21 C 0.12992(12) 0.51913(11) 0.12049(11) 0.0330(3) Uani 1 1 d . . . . .
H21A H 0.109173 0.594223 0.100581 0.049 Uiso 1 1 calc R U . . .
H21B H 0.066853 0.482304 0.138272 0.049 Uiso 1 1 calc R U . . .
H21C H 0.147035 0.483093 0.056788 0.049 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.4505(13) . ?
N1 C2 1.3974(13) . ?
N1 C5 1.4921(13) . ?
N1 C10 1.4365(13) . ?
C2 H2 1.0000 . ?
C2 C3 1.5377(15) . ?
C3 C4 1.5390(16) . ?
C3 C6 1.5304(16) . ?
C3 C7 1.5365(17) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5422(15) . ?
C5 C8 1.5295(15) . ?
C5 C9 1.5320(15) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.4164(15) . ?
C10 C15 1.4167(15) . ?
C11 C12 1.3957(16) . ?
C11 C16 1.5233(15) . ?
C12 H12 0.9500 . ?
C12 C13 1.3796(18) . ?
C13 H13 0.9500 . ?
C13 C14 1.3834(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.3948(16) . ?
C15 C19 1.5247(15) . ?
C16 H16 1.0000 . ?
C16 C17 1.5348(16) . ?
C16 C18 1.5345(16) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19 1.0000 . ?
C19 C20 1.5319(17) . ?
C19 C21 1.5372(16) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C5 114.46(8) . . ?
C2 N1 C10 120.51(8) . . ?
C10 N1 C5 124.97(8) . . ?
F1 C2 H2 110.2 . . ?
F1 C2 C3 108.69(9) . . ?
N1 C2 F1 110.89(9) . . ?
N1 C2 H2 110.2 . . ?
N1 C2 C3 106.46(9) . . ?
C3 C2 H2 110.2 . . ?
C2 C3 C4 101.30(9) . . ?
C6 C3 C2 113.08(10) . . ?
C6 C3 C4 112.11(10) . . ?
C6 C3 C7 108.52(10) . . ?
C7 C3 C2 109.70(10) . . ?
C7 C3 C4 112.04(10) . . ?
C3 C4 H4A 110.2 . . ?
C3 C4 H4B 110.2 . . ?
C3 C4 C5 107.56(9) . . ?
H4A C4 H4B 108.5 . . ?
C5 C4 H4A 110.2 . . ?
C5 C4 H4B 110.2 . . ?
N1 C5 C4 101.04(8) . . ?
N1 C5 C8 113.28(9) . . ?
N1 C5 C9 111.34(9) . . ?
C8 C5 C4 110.93(9) . . ?
C8 C5 C9 106.92(9) . . ?
C9 C5 C4 113.43(9) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 N1 119.48(10) . . ?
C11 C10 C15 119.58(10) . . ?
C15 C10 N1 120.87(10) . . ?
C10 C11 C16 123.07(10) . . ?
C12 C11 C10 118.89(10) . . ?
C12 C11 C16 117.99(10) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 C11 121.77(11) . . ?
C13 C12 H12 119.1 . . ?
C12 C13 H13 120.4 . . ?
C12 C13 C14 119.12(11) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 119.1 . . ?
C13 C14 C15 121.82(11) . . ?
C15 C14 H14 119.1 . . ?
C10 C15 C19 123.82(10) . . ?
C14 C15 C10 118.78(10) . . ?
C14 C15 C19 117.35(10) . . ?
C11 C16 H16 108.0 . . ?
C11 C16 C17 112.07(9) . . ?
C11 C16 C18 110.55(9) . . ?
C17 C16 H16 108.0 . . ?
C18 C16 H16 108.0 . . ?
C18 C16 C17 110.17(10) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C19 H19 108.0 . . ?
C15 C19 C20 110.95(10) . . ?
C15 C19 C21 111.71(10) . . ?
C20 C19 H19 108.0 . . ?
C20 C19 C21 110.12(10) . . ?
C21 C19 H19 108.0 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.229
_oxdiff_exptl_absorpt_empirical_full_min 0.878
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.7790(15) 21890 13047 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.2210(15) 0 13047 nmt -0.9996 -0.0004 -0.5672 0.0001 -1.0005 0.0006 -0.0014
0.0005 0.9991

_twin_special_details            
;
Component 2 rotated by 179.9965° 
around [-0.27 -0.00 0.96] (reciprocal) or [-0.00 0.00 1.00] (direct)
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_mecaach+h3f4-
_database_code_depnum_ccdc_archive 'CCDC 2263388'
loop_
_audit_author_name
_audit_author_address
'Evelin Gruden'
;Jozef Stefan Institute
Slovenia
;
_audit_update_record             
;
2023-05-16 deposited with the CCDC.	2023-06-20 downloaded from the CCDC.
;
_audit_creation_date             2022-03-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_SHELXL_version_number           2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H32 N, F2 H, 2(F H)'
_chemical_formula_sum            'C20 H35 F4 N'
_chemical_formula_weight         365.49
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H35 N F4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.4339(3)
_cell_length_b                   14.8964(5)
_cell_length_c                   14.3883(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.056(3)
_cell_angle_gamma                90
_cell_volume                     2201.98(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5776
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      71.8690
_cell_measurement_theta_min      2.9320
_shelx_estimated_absorpt_T_max   0.829
_shelx_estimated_absorpt_T_min   0.666
_exptl_absorpt_coefficient_mu    0.724
_exptl_absorpt_correction_T_max  0.858
_exptl_absorpt_correction_T_min  0.726
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.102
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -1 2 0.1988
1 1 -2 0.2027
2 0 1 0.1460
-2 0 -1 0.1226
2 1 0 0.1592
-2 -1 0 0.1411
-1 0 -1 0.1528
-2 -2 -1 0.1842
2 2 1 0.2030
-1 -2 2 0.2335
-1 -2 -1 0.2357
1 2 1 0.2523
0 -1 2 0.2085
0 1 -2 0.2103
0 -1 0 0.2721
0 -1 -1 0.2754
0 1 1 0.2585
0 1 0 0.2744
2 -1 -1 0.1981
-1 0 2 0.2038
-2 1 1 0.1837
-1 1 -1 0.1886
2 0 -1 0.1545
-2 0 1 0.1308
0 0 1 0.2107
0 0 -1 0.2301

_exptl_crystal_size_max          0.612
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.269
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0000 -1.0000 2.0000 -0.0719 -0.1440 0.2077
1.0000 1.0000 -2.0000 0.0719 0.1440 -0.2077
2.0000 -0.0000 1.0000 0.1412 0.2566 0.1654
-2.0000 0.0000 -1.0000 -0.1412 -0.2566 -0.1654
2.0000 1.0000 0.0000 0.0969 0.3007 0.0289
-2.0000 -1.0000 -0.0000 -0.0969 -0.3007 -0.0289
-1.0000 0.0000 -1.0000 -0.0554 -0.1378 -0.1340
-2.0000 -2.0000 -1.0000 0.0084 -0.3825 -0.0978
2.0000 2.0000 1.0000 -0.0084 0.3825 0.0978
-1.0000 -2.0000 2.0000 0.0029 -0.2069 0.2415
-1.0000 -2.0000 -1.0000 0.0942 -0.2637 -0.0665
1.0000 2.0000 1.0000 -0.0942 0.2637 0.0665
0.0000 -1.0000 2.0000 0.0139 -0.0251 0.2391
-0.0000 1.0000 -2.0000 -0.0139 0.0251 -0.2391
0.0000 -1.0000 0.0000 0.0748 -0.0630 0.0338
0.0000 -1.0000 -1.0000 0.1052 -0.0819 -0.0689
-0.0000 1.0000 1.0000 -0.1052 0.0819 0.0689
-0.0000 1.0000 -0.0000 -0.0748 0.0630 -0.0338
2.0000 -1.0000 -1.0000 0.2769 0.1559 -0.0062
-1.0000 0.0000 2.0000 -0.1467 -0.0810 0.1740
-2.0000 1.0000 1.0000 -0.2769 -0.1559 0.0062
-1.0000 1.0000 -1.0000 -0.1302 -0.0748 -0.1678
2.0000 0.0000 -1.0000 0.2021 0.2188 -0.0400
-2.0000 -0.0000 1.0000 -0.2021 -0.2188 0.0400
-0.0000 -0.0000 1.0000 -0.0304 0.0189 0.1027
0.0000 0.0000 -1.0000 0.0304 -0.0189 -0.1027

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16124
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        70.000
_diffrn_reflns_theta_max         72.330
_diffrn_reflns_theta_min         4.303
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6426
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -70.00  35.00   1.00    2.13    --  -40.98  77.00 -30.00  105
  2  ω   -109.00 -17.00   1.00    2.13    --  -40.98 -57.00  90.00   92
  3  ω    -65.00  29.00   1.00    2.13    --  -40.98  57.00-120.00   94
  4  ω     27.00  71.00   1.00    2.13    --   40.98 -77.00   0.00   44
  5  ω     -7.00  20.00   1.00    2.13    --   40.98 -77.00   0.00   27
  6  ω     36.00 117.00   1.00    8.53    --  103.58 -45.00-180.00   81
  7  ω     26.00 109.00   1.00    8.53    --  103.58 -80.00  31.77   83
  8  ω     73.00 107.00   1.00    8.53    --  103.58 -78.00-112.15   34
  9  ω     81.00 176.00   1.00    8.53    --  103.58  45.00-150.00   95
 10  ω     29.00 106.00   1.00    8.53    --  103.58 -80.00  87.85   77
 11  ω    115.00 178.00   1.00    8.53    --  103.58  77.00  90.00   63
 12  ω    135.00 171.00   1.00    8.53    --  103.58  77.00-180.00   36
 13  ω    103.00 161.00   1.00    8.53    --  103.58  77.00-120.00   58
 14  ω     75.00 100.00   1.00    8.53    --  103.58  61.00   0.00   25
 15  ω     78.00 177.00   1.00    8.53    --  103.58  45.00 150.00   99
 16  ω     67.00  92.00   1.00    8.53    --  103.58 -79.00 -77.52   25
 17  ω     45.00 108.00   1.00    8.53    --  103.58 -80.00 -35.09   63
 18  ω     73.00 100.00   1.00    8.53    --  103.58 -77.00-150.00   27
 19  ω     31.00 107.00   1.00    8.53    --  103.58 -80.00 160.69   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0858473000
_diffrn_orient_matrix_UB_12      -0.0748025000
_diffrn_orient_matrix_UB_13      -0.0304468000
_diffrn_orient_matrix_UB_21      0.1188645000
_diffrn_orient_matrix_UB_22      0.0629503000
_diffrn_orient_matrix_UB_23      0.0189192000
_diffrn_orient_matrix_UB_31      0.0313532000
_diffrn_orient_matrix_UB_32      -0.0337747000
_diffrn_orient_matrix_UB_33      0.1026639000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3212
_reflns_number_total             4295
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         4295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0502
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0715P)²+0.4220P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1475
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All F(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16), C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C12(H12), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C17(H17A,
 H17B,H17C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.71540(12) 0.48153(8) 0.80493(9) 0.0369(3) Uani 1 1 d . . . . .
C2 C 0.61375(14) 0.45141(10) 0.75223(11) 0.0379(3) Uani 1 1 d . . . . .
H2 H 0.611522 0.394499 0.722193 0.045 Uiso 1 1 calc R U . . .
C3 C 0.49875(17) 0.51195(12) 0.74117(15) 0.0509(4) Uani 1 1 d . . . . .
C4 C 0.55801(19) 0.59735(13) 0.79286(17) 0.0624(5) Uani 1 1 d . . . . .
H4A H 0.565823 0.645308 0.746546 0.075 Uiso 1 1 calc R U . . .
H4B H 0.501168 0.619341 0.836351 0.075 Uiso 1 1 calc R U . . .
C5 C 0.69337(17) 0.57340(11) 0.84874(13) 0.0482(4) Uani 1 1 d . . . . .
C6 C 0.4486(2) 0.52788(15) 0.63615(19) 0.0779(7) Uani 1 1 d . . . . .
H6A H 0.519411 0.551203 0.606365 0.117 Uiso 1 1 calc R U . . .
H6B H 0.377260 0.571510 0.628701 0.117 Uiso 1 1 calc R U . . .
H6C H 0.417060 0.471144 0.606061 0.117 Uiso 1 1 calc R U . . .
C7 C 0.3929(2) 0.46716(17) 0.7870(2) 0.0796(7) Uani 1 1 d . . . . .
H7A H 0.317803 0.507423 0.782578 0.119 Uiso 1 1 calc R U . . .
H7B H 0.427423 0.454643 0.853540 0.119 Uiso 1 1 calc R U . . .
H7C H 0.365896 0.410818 0.754195 0.119 Uiso 1 1 calc R U . . .
C8 C 0.7974(2) 0.63874(13) 0.83390(18) 0.0657(6) Uani 1 1 d . . . . .
H8A H 0.883070 0.613789 0.860012 0.099 Uiso 1 1 calc R U . . .
H8B H 0.784994 0.695373 0.865827 0.099 Uiso 1 1 calc R U . . .
H8C H 0.792184 0.649717 0.766188 0.099 Uiso 1 1 calc R U . . .
C9 C 0.6931(3) 0.56050(16) 0.95361(16) 0.0759(7) Uani 1 1 d . . . . .
H9A H 0.626726 0.516205 0.962172 0.114 Uiso 1 1 calc R U . . .
H9B H 0.673686 0.617811 0.981565 0.114 Uiso 1 1 calc R U . . .
H9C H 0.778832 0.539167 0.984635 0.114 Uiso 1 1 calc R U . . .
C10 C 0.83944(14) 0.43333(10) 0.82022(11) 0.0361(3) Uani 1 1 d . . . . .
C11 C 0.92309(15) 0.44857(11) 0.75561(11) 0.0401(3) Uani 1 1 d . . . . .
C12 C 1.04098(16) 0.40152(12) 0.77052(13) 0.0481(4) Uani 1 1 d . . . . .
H12 H 1.100379 0.409800 0.728166 0.058 Uiso 1 1 calc R U . . .
C13 C 1.07244(16) 0.34340(13) 0.84552(14) 0.0508(4) Uani 1 1 d . . . . .
H13 H 1.154387 0.313860 0.855713 0.061 Uiso 1 1 calc R U . . .
C14 C 0.98565(17) 0.32784(12) 0.90594(13) 0.0472(4) Uani 1 1 d . . . . .
H14 H 1.008170 0.286767 0.956678 0.057 Uiso 1 1 calc R U . . .
C15 C 0.86555(15) 0.37126(10) 0.89390(11) 0.0394(3) Uani 1 1 d . . . . .
C16 C 0.88753(17) 0.50597(12) 0.66728(12) 0.0464(4) Uani 1 1 d . . . . .
H16 H 0.808709 0.542052 0.673656 0.056 Uiso 1 1 calc R U . . .
C17 C 0.9967(2) 0.57135(15) 0.65443(16) 0.0640(5) Uani 1 1 d . . . . .
H17A H 1.019554 0.608260 0.711283 0.096 Uiso 1 1 calc R U . . .
H17B H 0.966950 0.610190 0.599951 0.096 Uiso 1 1 calc R U . . .
H17C H 1.073245 0.537362 0.643830 0.096 Uiso 1 1 calc R U . . .
C18 C 0.8525(2) 0.44501(15) 0.58085(13) 0.0587(5) Uani 1 1 d . . . . .
H18A H 0.928375 0.408729 0.573361 0.088 Uiso 1 1 calc R U . . .
H18B H 0.826139 0.481922 0.524361 0.088 Uiso 1 1 calc R U . . .
H18C H 0.780540 0.405381 0.589519 0.088 Uiso 1 1 calc R U . . .
C19 C 0.76579(16) 0.34176(12) 0.95316(12) 0.0463(4) Uani 1 1 d . . . . .
H19 H 0.690556 0.384258 0.940670 0.056 Uiso 1 1 calc R U . . .
C20 C 0.8189(2) 0.34276(16) 1.05930(14) 0.0619(5) Uani 1 1 d . . . . .
H20A H 0.890784 0.299833 1.073597 0.093 Uiso 1 1 calc R U . . .
H20B H 0.749463 0.325948 1.093883 0.093 Uiso 1 1 calc R U . . .
H20C H 0.850314 0.403133 1.078373 0.093 Uiso 1 1 calc R U . . .
C21 C 0.71608(19) 0.24790(13) 0.92058(14) 0.0562(5) Uani 1 1 d . . . . .
H21A H 0.676966 0.249888 0.853541 0.084 Uiso 1 1 calc R U . . .
H21B H 0.650604 0.228484 0.957560 0.084 Uiso 1 1 calc R U . . .
H21C H 0.788945 0.205447 0.929857 0.084 Uiso 1 1 calc R U . . .
F1 F 0.56416(15) 0.28426(8) 0.63040(10) 0.0750(4) Uani 1 1 d . . . . .
F2 F 0.37080(17) 0.30405(14) 0.52184(17) 0.1100(6) Uani 1 1 d . . . . .
F3 F 0.37501(19) 0.24659(18) 0.37059(13) 0.1262(8) Uani 1 1 d . . . . .
F4 F 0.17538(17) 0.35393(11) 0.56923(12) 0.0918(5) Uani 1 1 d . . . . .
H2A H 0.364(4) 0.295(3) 0.445(3) 0.138 Uiso 1 1 d . U . . .
H4 H 0.243(4) 0.332(3) 0.543(3) 0.138 Uiso 1 1 d . U . . .
H1 H 0.484(4) 0.294(3) 0.590(3) 0.138 Uiso 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.273(2) . ?
N1 C5 1.541(2) . ?
N1 C10 1.4628(19) . ?
C2 H2 0.9500 . ?
C2 C3 1.487(2) . ?
C3 C4 1.547(3) . ?
C3 C6 1.529(3) . ?
C3 C7 1.534(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.540(3) . ?
C5 C8 1.501(3) . ?
C5 C9 1.522(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.400(2) . ?
C10 C15 1.397(2) . ?
C11 C12 1.399(2) . ?
C11 C16 1.523(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.378(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.380(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.394(2) . ?
C15 C19 1.521(2) . ?
C16 H16 1.0000 . ?
C16 C17 1.534(3) . ?
C16 C18 1.532(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19 1.0000 . ?
C19 C20 1.531(3) . ?
C19 C21 1.536(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
F1 H1 0.94(4) . ?
F2 H2A 1.10(5) . ?
F2 H1 1.41(4) . ?
F3 H2A 1.32(5) . ?
F4 H4 0.92(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C5 112.86(13) . . ?
C2 N1 C10 122.68(13) . . ?
C10 N1 C5 124.46(12) . . ?
N1 C2 H2 122.5 . . ?
N1 C2 C3 115.01(14) . . ?
C3 C2 H2 122.5 . . ?
C2 C3 C4 101.54(14) . . ?
C2 C3 C6 109.29(17) . . ?
C2 C3 C7 108.55(16) . . ?
C6 C3 C4 112.74(17) . . ?
C6 C3 C7 110.16(19) . . ?
C7 C3 C4 114.09(19) . . ?
C3 C4 H4A 110.0 . . ?
C3 C4 H4B 110.0 . . ?
H4A C4 H4B 108.4 . . ?
C5 C4 C3 108.27(14) . . ?
C5 C4 H4A 110.0 . . ?
C5 C4 H4B 110.0 . . ?
C4 C5 N1 100.43(13) . . ?
C8 C5 N1 110.77(14) . . ?
C8 C5 C4 113.31(17) . . ?
C8 C5 C9 110.45(18) . . ?
C9 C5 N1 108.65(15) . . ?
C9 C5 C4 112.75(18) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 N1 117.27(13) . . ?
C15 C10 N1 119.28(13) . . ?
C15 C10 C11 123.33(14) . . ?
C10 C11 C16 123.76(14) . . ?
C12 C11 C10 116.75(15) . . ?
C12 C11 C16 119.25(15) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.17(16) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.41(16) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 119.4 . . ?
C13 C14 C15 121.22(16) . . ?
C15 C14 H14 119.4 . . ?
C10 C15 C19 123.69(14) . . ?
C14 C15 C10 116.96(15) . . ?
C14 C15 C19 118.98(15) . . ?
C11 C16 H16 108.0 . . ?
C11 C16 C17 112.29(15) . . ?
C11 C16 C18 109.48(15) . . ?
C17 C16 H16 108.0 . . ?
C18 C16 H16 108.0 . . ?
C18 C16 C17 110.82(16) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C19 H19 108.0 . . ?
C15 C19 C20 113.12(14) . . ?
C15 C19 C21 108.65(15) . . ?
C20 C19 H19 108.0 . . ?
C20 C19 C21 110.94(16) . . ?
C21 C19 H19 108.0 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
H2A F2 H1 126(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 6.5(2) . . . . ?
N1 C2 C3 C6 125.78(17) . . . . ?
N1 C2 C3 C7 -114.04(19) . . . . ?
N1 C10 C11 C12 -179.48(13) . . . . ?
N1 C10 C11 C16 -5.0(2) . . . . ?
N1 C10 C15 C14 -179.40(14) . . . . ?
N1 C10 C15 C19 7.6(2) . . . . ?
C2 N1 C5 C4 -10.0(2) . . . . ?
C2 N1 C5 C8 -130.04(17) . . . . ?
C2 N1 C5 C9 108.47(18) . . . . ?
C2 N1 C10 C11 87.34(18) . . . . ?
C2 N1 C10 C15 -88.95(19) . . . . ?
C2 C3 C4 C5 -12.5(2) . . . . ?
C3 C4 C5 N1 13.5(2) . . . . ?
C3 C4 C5 C8 131.61(18) . . . . ?
C3 C4 C5 C9 -102.0(2) . . . . ?
C5 N1 C2 C3 2.3(2) . . . . ?
C5 N1 C10 C11 -91.81(18) . . . . ?
C5 N1 C10 C15 91.91(18) . . . . ?
C6 C3 C4 C5 -129.3(2) . . . . ?
C7 C3 C4 C5 104.0(2) . . . . ?
C10 N1 C2 C3 -176.89(14) . . . . ?
C10 N1 C5 C4 169.19(15) . . . . ?
C10 N1 C5 C8 49.2(2) . . . . ?
C10 N1 C5 C9 -72.3(2) . . . . ?
C10 C11 C12 C13 -0.2(2) . . . . ?
C10 C11 C16 C17 133.97(18) . . . . ?
C10 C11 C16 C18 -102.49(18) . . . . ?
C10 C15 C19 C20 -132.94(17) . . . . ?
C10 C15 C19 C21 103.41(18) . . . . ?
C11 C10 C15 C14 4.6(2) . . . . ?
C11 C10 C15 C19 -168.43(15) . . . . ?
C11 C12 C13 C14 2.4(3) . . . . ?
C12 C11 C16 C17 -51.7(2) . . . . ?
C12 C11 C16 C18 71.82(19) . . . . ?
C12 C13 C14 C15 -1.1(3) . . . . ?
C13 C14 C15 C10 -2.2(2) . . . . ?
C13 C14 C15 C19 171.09(16) . . . . ?
C14 C15 C19 C20 54.2(2) . . . . ?
C14 C15 C19 C21 -69.44(19) . . . . ?
C15 C10 C11 C12 -3.4(2) . . . . ?
C15 C10 C11 C16 171.08(14) . . . . ?
C16 C11 C12 C13 -174.90(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.222
_oxdiff_exptl_absorpt_empirical_full_min 0.813
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_773
_database_code_depnum_ccdc_archive 'CCDC 2263385'
loop_
_audit_author_name
_audit_author_address
'Evelin Gruden'
;Jozef Stefan Institute
Slovenia
;
_audit_update_record             
;
2023-05-16 deposited with the CCDC.	2023-06-20 downloaded from the CCDC.
;
_audit_creation_date             2023-04-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(F H), 2(F3 H2), 2(C20 H32 N)'
_chemical_formula_sum            'C40 H71 F9 N2'
_chemical_formula_weight         750.98
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.90751(18)
_cell_length_b                   31.7144(5)
_cell_length_c                   12.95482(18)
_cell_angle_alpha                90
_cell_angle_beta                 90.3955(14)
_cell_angle_gamma                90
_cell_volume                     4481.30(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11730
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.1580
_cell_measurement_theta_min      3.6290
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.756
_exptl_absorpt_correction_T_max  0.917
_exptl_absorpt_correction_T_min  0.872
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull light colourless'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.113
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1624
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 2 -7 0.1239
5 14 -1 0.1323
3 16 3 0.1501
-4 -3 6 0.0899
-5 -14 1 0.0838
3 -18 1 0.1284
3 -2 8 0.1401
-3 19 0 0.1233
-1 -6 -8 0.1745
-3 10 -6 0.1509
-2 -17 4 0.1136
1 20 -1 0.1164
2 15 -6 0.1411
5 -2 -6 0.1249
6 8 -1 0.1344
7 -5 0 0.1247
6 4 5 0.1609
-7 6 0 0.1423
-1 20 -2 0.1106

_exptl_crystal_size_max          0.344
_exptl_crystal_size_mid          0.288
_exptl_crystal_size_min          0.216
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            38097
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        70.000
_diffrn_reflns_theta_max         72.376
_diffrn_reflns_theta_min         2.787
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean 10.6426
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00   3.00   1.00   15.37    --  -41.11  47.00  61.00   63
  2  ω   -111.00 -33.00   1.00   15.37    --  -41.11 -73.00 101.00   78
  3  ω     68.00  94.00   1.00   61.47    --  103.58 -73.00 101.00   26
  4  ω    117.00 175.00   1.00   61.47    --  103.58  47.00  61.00   58
  5  ω     99.00 125.00   1.00   61.47    --  103.58 -73.00 101.00   26
  6  ω     72.00 117.00   1.00   61.47    --  103.58  73.00-129.00   45
  7  ω     54.00 130.00   1.00   61.47    --  103.58 -47.00 -87.00   76
  8  ω    -53.00 -27.00   1.00   15.37    --  -41.11  73.00-129.00   26
  9  ω    -21.00  22.00   1.00   15.37    --   41.11 -77.00-180.00   43
 10  ω    103.00 177.00   1.00   61.47    --  103.58  77.00 -90.00   74
 11  ω    105.00 131.00   1.00   61.47    --  103.58  77.00 -30.00   26
 12  ω    106.00 178.00   1.00   61.47    --  103.58  77.00 -60.00   72
 13  ω     39.00  98.00   1.00   15.37    --   41.23-133.00-137.00   59
 14  ω     61.00  87.00   1.00   61.47    --  103.58 178.00  60.00   26
 15  ω    107.00 133.00   1.00   61.47    --  103.58 178.00  60.00   26
 16  ω     41.00 101.00   1.00   61.47    --  103.58-111.00  90.00   60
 17  ω    -76.00 -51.00   1.00   15.37    --  -41.23 133.00 -69.00   25
 18  ω   -102.00 -24.00   1.00   15.37    --  -41.23 -38.00-150.00   78
 19  ω    -84.00 -27.00   1.00   15.37    --  -41.23 -38.00 -90.00   57
 20  ω    139.00 165.00   1.00   61.47    --  103.58  77.00   0.00   26
 21  ω     68.00 104.00   1.00   61.47    --  103.58-111.00  30.00   36
 22  ω     78.00 131.00   1.00   61.47    --  103.58  45.00  90.00   53
 23  ω    148.00 174.00   1.00   61.47    --  103.58  45.00  90.00   26
 24  ω     57.00 109.00   1.00   61.47    --  103.58-111.00-150.00   52
 25  ω     27.00  75.00   1.00   61.47    --  103.58 -94.00 120.00   48
 26  ω     78.00 109.00   1.00   61.47    --  103.58-111.00 -60.00   31
 27  ω     99.00 175.00   1.00   61.47    --  103.58  61.00-180.00   76
 28  ω     73.00 123.00   1.00   61.47    --  103.58 -61.00-180.00   50
 29  ω     84.00 109.00   1.00   61.47    --  103.58-111.00  90.00   25
 30  ω     31.00  57.00   1.00   61.47    --  103.58 -61.00 -60.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6680
_reflns_number_total             8757
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     518
_refine_ls_number_reflns         8757
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0607
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0885P)²+1.6771P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1666
_refine_ls_wR_factor_ref         0.1811
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.9812(5)
 0.0188(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H7A,H7B,H7C} of C7, All C(H,H) groups
 At 1.5 times of:
  {H21A,H21B,H21C} of C21, {H27A,H27B,H27C} of C27, {H29A,H29B,H29C} of C29,
  {H17A,H17B,H17C} of C17, {H26A,H26B,H26C} of C26, {H28A,H28B,H28C} of C28,
  {H18A,H18B,H18C} of C18, {H20A,H20B,H20C} of C20, {H37A,H37B,H37C} of C37,
  {H38A,H38B,H38C} of C38, {H41A,H41B,H41C} of C41, {H40A,H40B,H40C} of C40,
  {H8A,H8B,H8C} of C8, {H6A,H6B,H6C} of C6, {H9A,H9B,H9C} of C9
3. Others
 Sof(F1B)=Sof(F2B)=1-FVAR(1)
 Sof(F1A)=Sof(F2A)=FVAR(1)
 Fixed X: H23(0.71897) H1A(0.78908)
 Fixed Y: H23(0.53831) H1A(0.27568)
 Fixed Z: H23(0.91218) H1A(0.20184)
4.a Ternary CH refined with riding coordinates:
 C16(H16), C19(H19), C36(H36), C39(H39)
4.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C24(H24A,H24B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C12(H12), C13(H13), C14(H14), C22(H22), C32(H32), C33(H33), C34(H34)
4.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C17(H17A,
 H17B,H17C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C),
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,
 H29C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C40(H40A,H40B,H40C), C41(H41A,
 H41B,H41C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F4 F 0.8203(2) 0.24650(8) 0.42727(16) 0.1061(7) Uani 1 1 d . . . . .
H4 H 0.751(6) 0.2637(17) 0.405(4) 0.16(2) Uiso 1 1 d . . . . .
F22 F 0.7897(3) 0.61860(7) 0.83040(19) 0.1171(8) Uani 1 1 d . . . . .
H22A H 0.769(6) 0.594(2) 0.874(5) 0.18(2) Uiso 1 1 d . . . . .
F23 F 0.75206(19) 0.57225(6) 0.96044(14) 0.0849(5) Uani 1 1 d . . . . .
H23 H 0.718970 0.538310 0.912180 0.21(3) Uiso 1 1 d . . . . .
F25 F 0.6785(2) 0.50602(6) 0.89957(16) 0.1018(7) Uani 1 1 d . . . . .
F24 F 0.85227(18) 0.56668(6) 0.12611(14) 0.0814(5) Uani 1 1 d . . . . .
H24 H 0.820(4) 0.5701(13) 0.069(3) 0.105(14) Uiso 1 1 d . . . . .
F1A F 0.8261(13) 0.2802(4) 0.1373(9) 0.097(3) Uani 0.39(3) 1 d . . P A 1
H1A H 0.789080 0.275680 0.201840 0.16(2) Uiso 1 1 d . . . . .
F1B F 0.8043(11) 0.2576(10) 0.1356(6) 0.149(6) Uani 0.61(3) 1 d . . P A 2
F2A F 0.7509(8) 0.2938(4) 0.2963(8) 0.080(4) Uani 0.39(3) 1 d . . P A 1
H2A H 0.654(5) 0.3072(15) 0.279(3) 0.114(13) Uiso 1 1 d . . . . .
F2B F 0.726(2) 0.2780(8) 0.2892(8) 0.176(5) Uani 0.61(3) 1 d . . P A 2
F3 F 0.5612(3) 0.32250(12) 0.2794(2) 0.1559(12) Uani 1 1 d . . . . .
F21 F 0.90796(18) 0.59895(6) 0.68085(15) 0.0811(5) Uani 1 1 d . . . . .
H21 H 0.850(6) 0.6043(19) 0.722(5) 0.17(2) Uiso 1 1 d . . . . .
N1 N 0.71144(16) 0.27974(5) 0.84779(13) 0.0448(4) Uani 1 1 d . . . . .
C2 C 0.7126(2) 0.25520(7) 0.92554(18) 0.0508(5) Uani 1 1 d . . . . .
H2 H 0.729164 0.264773 0.993704 0.061 Uiso 1 1 calc R U . . .
C3 C 0.6858(2) 0.21034(8) 0.9009(2) 0.0640(7) Uani 1 1 d . . . . .
C4 C 0.6451(4) 0.21289(9) 0.7880(3) 0.0835(9) Uani 1 1 d . . . . .
H4A H 0.554970 0.209698 0.782521 0.100 Uiso 1 1 calc R U . . .
H4B H 0.683970 0.190071 0.747608 0.100 Uiso 1 1 calc R U . . .
C5 C 0.6842(3) 0.25605(7) 0.74609(19) 0.0602(6) Uani 1 1 d . . . . .
C6 C 0.5848(3) 0.19390(11) 0.9714(3) 0.0953(11) Uani 1 1 d . . . . .
H6A H 0.511576 0.211561 0.963514 0.143 Uiso 1 1 calc R U . . .
H6B H 0.613153 0.194817 1.043262 0.143 Uiso 1 1 calc R U . . .
H6C H 0.564773 0.164761 0.952498 0.143 Uiso 1 1 calc R U . . .
C7 C 0.8022(3) 0.18426(10) 0.9184(3) 0.0907(10) Uani 1 1 d . . . . .
H7A H 0.868251 0.195396 0.875289 0.109 Uiso 1 1 calc R U . . .
H7B H 0.786315 0.154800 0.899799 0.109 Uiso 1 1 calc R U . . .
H7C H 0.826664 0.185892 0.991206 0.109 Uiso 1 1 calc R U . . .
C8 C 0.7997(4) 0.25520(10) 0.6815(2) 0.0817(9) Uani 1 1 d . . . . .
H8A H 0.864075 0.239687 0.718582 0.122 Uiso 1 1 calc R U . . .
H8B H 0.827310 0.284133 0.668741 0.122 Uiso 1 1 calc R U . . .
H8C H 0.782466 0.241233 0.615518 0.122 Uiso 1 1 calc R U . . .
C9 C 0.5807(4) 0.27783(10) 0.6875(3) 0.0871(10) Uani 1 1 d . . . . .
H9A H 0.604372 0.306978 0.672271 0.131 Uiso 1 1 calc R U . . .
H9B H 0.506513 0.277777 0.729681 0.131 Uiso 1 1 calc R U . . .
H9C H 0.564684 0.262772 0.622725 0.131 Uiso 1 1 calc R U . . .
C10 C 0.73403(19) 0.32489(6) 0.85345(14) 0.0412(4) Uani 1 1 d . . . . .
C11 C 0.6333(2) 0.35161(7) 0.86776(15) 0.0459(5) Uani 1 1 d . . . . .
C12 C 0.6570(2) 0.39468(7) 0.86557(16) 0.0530(5) Uani 1 1 d . . . . .
H12 H 0.590975 0.413912 0.873682 0.064 Uiso 1 1 calc R U . . .
C13 C 0.7736(2) 0.41016(7) 0.85196(16) 0.0550(6) Uani 1 1 d . . . . .
H13 H 0.786638 0.439708 0.847177 0.066 Uiso 1 1 calc R U . . .
C14 C 0.8711(2) 0.38303(7) 0.84528(16) 0.0520(5) Uani 1 1 d . . . . .
H14 H 0.951584 0.394203 0.839377 0.062 Uiso 1 1 calc R U . . .
C15 C 0.85492(19) 0.33948(7) 0.84694(15) 0.0452(5) Uani 1 1 d . . . . .
C16 C 0.5071(2) 0.33587(8) 0.8954(2) 0.0599(6) Uani 1 1 d . . . . .
H16 H 0.504613 0.304901 0.880979 0.072 Uiso 1 1 calc R U . . .
C17 C 0.4057(3) 0.35664(12) 0.8316(3) 0.0878(10) Uani 1 1 d . . . . .
H17A H 0.420888 0.351895 0.758075 0.132 Uiso 1 1 calc R U . . .
H17B H 0.404652 0.386999 0.845663 0.132 Uiso 1 1 calc R U . . .
H17C H 0.326421 0.344359 0.850228 0.132 Uiso 1 1 calc R U . . .
C18 C 0.4848(3) 0.34214(12) 1.0120(2) 0.0826(9) Uani 1 1 d . . . . .
H18A H 0.486199 0.372317 1.028256 0.124 Uiso 1 1 calc R U . . .
H18B H 0.549274 0.327727 1.051519 0.124 Uiso 1 1 calc R U . . .
H18C H 0.404773 0.330352 1.030255 0.124 Uiso 1 1 calc R U . . .
C19 C 0.9663(2) 0.31077(9) 0.85187(19) 0.0570(6) Uani 1 1 d . . . . .
H19 H 0.938270 0.280998 0.842284 0.068 Uiso 1 1 calc R U . . .
C20 C 1.0586(3) 0.32118(13) 0.7670(3) 0.0861(9) Uani 1 1 d . . . . .
H20A H 1.124718 0.300266 0.767778 0.129 Uiso 1 1 calc R U . . .
H20B H 1.092995 0.349307 0.779146 0.129 Uiso 1 1 calc R U . . .
H20C H 1.017065 0.320643 0.699651 0.129 Uiso 1 1 calc R U . . .
C21 C 1.0293(3) 0.31443(11) 0.9583(2) 0.0757(8) Uani 1 1 d . . . . .
H21A H 0.971052 0.306619 1.012363 0.114 Uiso 1 1 calc R U . . .
H21B H 1.056628 0.343534 0.969248 0.114 Uiso 1 1 calc R U . . .
H21C H 1.100149 0.295465 0.961148 0.114 Uiso 1 1 calc R U . . .
N21 N 0.25873(14) 0.54122(5) 0.68704(11) 0.0367(3) Uani 1 1 d . . . . .
C22 C 0.16429(18) 0.55745(6) 0.72802(14) 0.0402(4) Uani 1 1 d . . . . .
H22 H 0.091145 0.562887 0.690072 0.048 Uiso 1 1 calc R U . . .
C23 C 0.1769(2) 0.56729(7) 0.83988(15) 0.0488(5) Uani 1 1 d . . . . .
C24 C 0.3034(3) 0.54867(11) 0.86527(18) 0.0733(8) Uani 1 1 d . . . . .
H24A H 0.294244 0.523561 0.909955 0.088 Uiso 1 1 calc R U . . .
H24B H 0.353791 0.569740 0.902700 0.088 Uiso 1 1 calc R U . . .
C25 C 0.36656(19) 0.53624(7) 0.76375(15) 0.0450(5) Uani 1 1 d . . . . .
C26 C 0.0749(3) 0.54511(10) 0.89925(18) 0.0688(7) Uani 1 1 d . . . . .
H26A H -0.004727 0.556596 0.877869 0.103 Uiso 1 1 calc R U . . .
H26B H 0.086807 0.549696 0.973457 0.103 Uiso 1 1 calc R U . . .
H26C H 0.077215 0.514814 0.884504 0.103 Uiso 1 1 calc R U . . .
C27 C 0.1689(3) 0.61502(8) 0.85423(19) 0.0701(7) Uani 1 1 d . . . . .
H27A H 0.231724 0.628785 0.812302 0.105 Uiso 1 1 calc R U . . .
H27B H 0.182266 0.622015 0.927129 0.105 Uiso 1 1 calc R U . . .
H27C H 0.087586 0.624879 0.832471 0.105 Uiso 1 1 calc R U . . .
C28 C 0.4113(2) 0.49114(8) 0.7655(2) 0.0566(6) Uani 1 1 d . . . . .
H28A H 0.345586 0.472676 0.789971 0.085 Uiso 1 1 calc R U . . .
H28B H 0.482275 0.488837 0.811984 0.085 Uiso 1 1 calc R U . . .
H28C H 0.435108 0.482657 0.695718 0.085 Uiso 1 1 calc R U . . .
C29 C 0.4695(2) 0.56545(8) 0.7324(2) 0.0567(6) Uani 1 1 d . . . . .
H29A H 0.496362 0.558293 0.662559 0.085 Uiso 1 1 calc R U . . .
H29B H 0.538369 0.562300 0.780756 0.085 Uiso 1 1 calc R U . . .
H29C H 0.440319 0.594673 0.733662 0.085 Uiso 1 1 calc R U . . .
C30 C 0.26459(16) 0.52950(6) 0.57798(13) 0.0359(4) Uani 1 1 d . . . . .
C31 C 0.29840(17) 0.56040(7) 0.50635(14) 0.0406(4) Uani 1 1 d . . . . .
C32 C 0.30715(19) 0.54753(8) 0.40372(16) 0.0487(5) Uani 1 1 d . . . . .
H32 H 0.330662 0.567453 0.352812 0.058 Uiso 1 1 calc R U . . .
C33 C 0.2827(2) 0.50693(8) 0.37457(15) 0.0533(5) Uani 1 1 d . . . . .
H33 H 0.292397 0.498795 0.304527 0.064 Uiso 1 1 calc R U . . .
C34 C 0.2440(2) 0.47765(7) 0.44637(16) 0.0500(5) Uani 1 1 d . . . . .
H34 H 0.224822 0.449823 0.424500 0.060 Uiso 1 1 calc R U . . .
C35 C 0.23271(18) 0.48826(6) 0.55048(15) 0.0413(4) Uani 1 1 d . . . . .
C36 C 0.3144(2) 0.60663(7) 0.53218(16) 0.0485(5) Uani 1 1 d . . . . .
H36 H 0.314990 0.609509 0.609049 0.058 Uiso 1 1 calc R U . . .
C37 C 0.4350(3) 0.62442(10) 0.4916(2) 0.0710(7) Uani 1 1 d . . . . .
H37A H 0.503582 0.607829 0.519196 0.107 Uiso 1 1 calc R U . . .
H37B H 0.443674 0.653842 0.513626 0.107 Uiso 1 1 calc R U . . .
H37C H 0.435093 0.623005 0.416062 0.107 Uiso 1 1 calc R U . . .
C38 C 0.2051(3) 0.63191(8) 0.4898(2) 0.0618(6) Uani 1 1 d . . . . .
H38A H 0.200968 0.628760 0.414568 0.093 Uiso 1 1 calc R U . . .
H38B H 0.215562 0.661761 0.507295 0.093 Uiso 1 1 calc R U . . .
H38C H 0.129168 0.621353 0.520344 0.093 Uiso 1 1 calc R U . . .
C39 C 0.1768(2) 0.45681(7) 0.62458(16) 0.0476(5) Uani 1 1 d . . . . .
H39 H 0.188758 0.467765 0.696326 0.057 Uiso 1 1 calc R U . . .
C40 C 0.2388(3) 0.41368(8) 0.6178(2) 0.0732(8) Uani 1 1 d . . . . .
H40A H 0.222398 0.401248 0.549828 0.110 Uiso 1 1 calc R U . . .
H40B H 0.206378 0.395149 0.671617 0.110 Uiso 1 1 calc R U . . .
H40C H 0.327489 0.416987 0.627552 0.110 Uiso 1 1 calc R U . . .
C41 C 0.0390(3) 0.45336(11) 0.6039(2) 0.0795(9) Uani 1 1 d . . . . .
H41A H 0.000886 0.481106 0.612428 0.119 Uiso 1 1 calc R U . . .
H41B H 0.002773 0.433402 0.652686 0.119 Uiso 1 1 calc R U . . .
H41C H 0.025068 0.443353 0.533172 0.119 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F4 H4 0.97(6) . ?
F22 H22A 0.99(7) . ?
F23 H22A 1.33(7) . ?
F23 H23 1.290 . ?
F25 H23 1.130 . ?
F24 H24 0.82(4) . ?
F1A H1A 0.942(12) . ?
F1B H1A 1.047(18) . ?
F2A H1A 1.417(12) . ?
F2A H2A 1.16(6) . ?
F2B H1A 1.329(12) . ?
F2B H2A 1.22(5) . ?
F3 H2A 1.12(6) . ?
F21 H21 0.84(6) . ?
N1 C2 1.273(3) . ?
N1 C5 1.544(3) . ?
N1 C10 1.455(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.487(4) . ?
C3 C4 1.528(4) . ?
C3 C6 1.527(4) . ?
C3 C7 1.531(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.534(4) . ?
C5 C8 1.518(4) . ?
C5 C9 1.521(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.401(3) . ?
C10 C15 1.401(3) . ?
C11 C12 1.391(3) . ?
C11 C16 1.510(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.376(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.371(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.393(3) . ?
C15 C19 1.520(3) . ?
C16 H16 1.0000 . ?
C16 C17 1.525(4) . ?
C16 C18 1.545(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19 1.0000 . ?
C19 C20 1.532(3) . ?
C19 C21 1.541(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
N21 C22 1.271(2) . ?
N21 C25 1.543(2) . ?
N21 C30 1.463(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.488(3) . ?
C23 C24 1.535(4) . ?
C23 C26 1.528(3) . ?
C23 C27 1.528(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.540(3) . ?
C25 C28 1.511(3) . ?
C25 C29 1.513(3) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 C31 1.401(3) . ?
C30 C35 1.399(3) . ?
C31 C32 1.395(3) . ?
C31 C36 1.514(3) . ?
C32 H32 0.9500 . ?
C32 C33 1.367(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.382(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.396(3) . ?
C35 C39 1.515(3) . ?
C36 H36 1.0000 . ?
C36 C37 1.528(3) . ?
C36 C38 1.535(3) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39 1.0000 . ?
C39 C40 1.529(4) . ?
C39 C41 1.529(4) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H22A F23 H23 94.0 . . ?
H1A F2A H2A 105(2) . . ?
H1A F2B H2A 107(2) . . ?
C2 N1 C5 112.25(19) . . ?
C2 N1 C10 124.14(19) . . ?
C10 N1 C5 123.61(16) . . ?
N1 C2 H2 122.8 . . ?
N1 C2 C3 114.5(2) . . ?
C3 C2 H2 122.8 . . ?
C2 C3 C4 102.13(19) . . ?
C2 C3 C6 109.9(2) . . ?
C2 C3 C7 108.9(2) . . ?
C4 C3 C7 113.9(3) . . ?
C6 C3 C4 112.6(3) . . ?
C6 C3 C7 109.2(2) . . ?
C3 C4 H4A 110.1 . . ?
C3 C4 H4B 110.1 . . ?
C3 C4 C5 107.8(2) . . ?
H4A C4 H4B 108.5 . . ?
C5 C4 H4A 110.1 . . ?
C5 C4 H4B 110.1 . . ?
C4 C5 N1 100.7(2) . . ?
C8 C5 N1 108.9(2) . . ?
C8 C5 C4 114.4(3) . . ?
C8 C5 C9 110.4(3) . . ?
C9 C5 N1 110.0(2) . . ?
C9 C5 C4 112.0(3) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 N1 118.01(18) . . ?
C15 C10 N1 118.78(18) . . ?
C15 C10 C11 123.19(19) . . ?
C10 C11 C16 123.3(2) . . ?
C12 C11 C10 116.5(2) . . ?
C12 C11 C16 120.0(2) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 C11 121.6(2) . . ?
C13 C12 H12 119.2 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.2(2) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.2 . . ?
C13 C14 C15 121.5(2) . . ?
C15 C14 H14 119.2 . . ?
C10 C15 C19 123.5(2) . . ?
C14 C15 C10 116.6(2) . . ?
C14 C15 C19 119.6(2) . . ?
C11 C16 H16 107.7 . . ?
C11 C16 C17 112.8(2) . . ?
C11 C16 C18 109.8(2) . . ?
C17 C16 H16 107.7 . . ?
C17 C16 C18 110.8(3) . . ?
C18 C16 H16 107.7 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C19 H19 108.4 . . ?
C15 C19 C20 111.7(2) . . ?
C15 C19 C21 110.1(2) . . ?
C20 C19 H19 108.4 . . ?
C20 C19 C21 109.6(2) . . ?
C21 C19 H19 108.4 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C22 N21 C25 112.89(15) . . ?
C22 N21 C30 123.18(16) . . ?
C30 N21 C25 123.92(15) . . ?
N21 C22 H22 122.5 . . ?
N21 C22 C23 114.97(18) . . ?
C23 C22 H22 122.5 . . ?
C22 C23 C24 101.82(17) . . ?
C22 C23 C26 109.33(19) . . ?
C22 C23 C27 108.75(18) . . ?
C26 C23 C24 111.8(2) . . ?
C27 C23 C24 114.0(2) . . ?
C27 C23 C26 110.6(2) . . ?
C23 C24 H24A 109.9 . . ?
C23 C24 H24B 109.9 . . ?
C23 C24 C25 108.81(18) . . ?
H24A C24 H24B 108.3 . . ?
C25 C24 H24A 109.9 . . ?
C25 C24 H24B 109.9 . . ?
C24 C25 N21 100.38(16) . . ?
C28 C25 N21 110.57(17) . . ?
C28 C25 C24 112.1(2) . . ?
C28 C25 C29 110.08(19) . . ?
C29 C25 N21 109.16(16) . . ?
C29 C25 C24 114.2(2) . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C23 C27 H27A 109.5 . . ?
C23 C27 H27B 109.5 . . ?
C23 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C25 C29 H29A 109.5 . . ?
C25 C29 H29B 109.5 . . ?
C25 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 N21 118.39(17) . . ?
C35 C30 N21 118.12(16) . . ?
C35 C30 C31 123.47(17) . . ?
C30 C31 C36 124.17(17) . . ?
C32 C31 C30 116.54(19) . . ?
C32 C31 C36 119.06(18) . . ?
C31 C32 H32 119.2 . . ?
C33 C32 C31 121.6(2) . . ?
C33 C32 H32 119.2 . . ?
C32 C33 H33 119.8 . . ?
C32 C33 C34 120.43(19) . . ?
C34 C33 H33 119.8 . . ?
C33 C34 H34 119.4 . . ?
C33 C34 C35 121.2(2) . . ?
C35 C34 H34 119.4 . . ?
C30 C35 C39 123.68(17) . . ?
C34 C35 C30 116.60(19) . . ?
C34 C35 C39 119.47(19) . . ?
C31 C36 H36 108.0 . . ?
C31 C36 C37 112.3(2) . . ?
C31 C36 C38 109.82(18) . . ?
C37 C36 H36 108.0 . . ?
C37 C36 C38 110.6(2) . . ?
C38 C36 H36 108.0 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C35 C39 H39 108.0 . . ?
C35 C39 C40 111.9(2) . . ?
C35 C39 C41 109.58(18) . . ?
C40 C39 H39 108.0 . . ?
C40 C39 C41 111.1(2) . . ?
C41 C39 H39 108.0 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C39 C41 H41A 109.5 . . ?
C39 C41 H41B 109.5 . . ?
C39 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 -9.2(3) . . . . ?
N1 C2 C3 C6 -128.9(3) . . . . ?
N1 C2 C3 C7 111.6(3) . . . . ?
N1 C10 C11 C12 -175.63(17) . . . . ?
N1 C10 C11 C16 10.7(3) . . . . ?
N1 C10 C15 C14 175.53(17) . . . . ?
N1 C10 C15 C19 -10.4(3) . . . . ?
C2 N1 C5 C4 10.6(3) . . . . ?
C2 N1 C5 C8 -110.0(2) . . . . ?
C2 N1 C5 C9 128.9(2) . . . . ?
C2 N1 C10 C11 -90.4(2) . . . . ?
C2 N1 C10 C15 88.1(2) . . . . ?
C2 C3 C4 C5 15.4(3) . . . . ?
C3 C4 C5 N1 -15.6(3) . . . . ?
C3 C4 C5 C8 100.9(3) . . . . ?
C3 C4 C5 C9 -132.5(3) . . . . ?
C5 N1 C2 C3 -1.0(3) . . . . ?
C5 N1 C10 C11 90.1(2) . . . . ?
C5 N1 C10 C15 -91.5(2) . . . . ?
C6 C3 C4 C5 133.2(3) . . . . ?
C7 C3 C4 C5 -101.8(3) . . . . ?
C10 N1 C2 C3 179.45(19) . . . . ?
C10 N1 C5 C4 -169.8(2) . . . . ?
C10 N1 C5 C8 69.6(3) . . . . ?
C10 N1 C5 C9 -51.5(3) . . . . ?
C10 C11 C12 C13 -1.2(3) . . . . ?
C10 C11 C16 C17 -134.8(3) . . . . ?
C10 C11 C16 C18 101.0(3) . . . . ?
C10 C15 C19 C20 133.6(2) . . . . ?
C10 C15 C19 C21 -104.4(3) . . . . ?
C11 C10 C15 C14 -6.1(3) . . . . ?
C11 C10 C15 C19 167.97(19) . . . . ?
C11 C12 C13 C14 -3.3(3) . . . . ?
C12 C11 C16 C17 51.7(3) . . . . ?
C12 C11 C16 C18 -72.5(3) . . . . ?
C12 C13 C14 C15 3.2(3) . . . . ?
C13 C14 C15 C10 1.4(3) . . . . ?
C13 C14 C15 C19 -172.9(2) . . . . ?
C14 C15 C19 C20 -52.5(3) . . . . ?
C14 C15 C19 C21 69.5(3) . . . . ?
C15 C10 C11 C12 6.0(3) . . . . ?
C15 C10 C11 C16 -167.7(2) . . . . ?
C16 C11 C12 C13 172.8(2) . . . . ?
N21 C22 C23 C24 -5.6(3) . . . . ?
N21 C22 C23 C26 -124.0(2) . . . . ?
N21 C22 C23 C27 115.0(2) . . . . ?
N21 C30 C31 C32 177.76(17) . . . . ?
N21 C30 C31 C36 -7.9(3) . . . . ?
N21 C30 C35 C34 -177.51(17) . . . . ?
N21 C30 C35 C39 8.3(3) . . . . ?
C22 N21 C25 C24 7.2(2) . . . . ?
C22 N21 C25 C28 125.7(2) . . . . ?
C22 N21 C25 C29 -113.1(2) . . . . ?
C22 N21 C30 C31 86.2(2) . . . . ?
C22 N21 C30 C35 -92.0(2) . . . . ?
C22 C23 C24 C25 9.9(3) . . . . ?
C23 C24 C25 N21 -10.3(3) . . . . ?
C23 C24 C25 C28 -127.7(2) . . . . ?
C23 C24 C25 C29 106.3(3) . . . . ?
C25 N21 C22 C23 -1.1(2) . . . . ?
C25 N21 C30 C31 -92.4(2) . . . . ?
C25 N21 C30 C35 89.4(2) . . . . ?
C26 C23 C24 C25 126.6(2) . . . . ?
C27 C23 C24 C25 -107.0(2) . . . . ?
C30 N21 C22 C23 -179.75(17) . . . . ?
C30 N21 C25 C24 -174.1(2) . . . . ?
C30 N21 C25 C28 -55.7(2) . . . . ?
C30 N21 C25 C29 65.6(2) . . . . ?
C30 C31 C32 C33 0.6(3) . . . . ?
C30 C31 C36 C37 131.2(2) . . . . ?
C30 C31 C36 C38 -105.3(2) . . . . ?
C30 C35 C39 C40 -133.9(2) . . . . ?
C30 C35 C39 C41 102.4(3) . . . . ?
C31 C30 C35 C34 4.4(3) . . . . ?
C31 C30 C35 C39 -169.84(18) . . . . ?
C31 C32 C33 C34 2.3(3) . . . . ?
C32 C31 C36 C37 -54.6(3) . . . . ?
C32 C31 C36 C38 69.0(2) . . . . ?
C32 C33 C34 C35 -2.1(3) . . . . ?
C33 C34 C35 C30 -1.2(3) . . . . ?
C33 C34 C35 C39 173.3(2) . . . . ?
C34 C35 C39 C40 52.1(3) . . . . ?
C34 C35 C39 C41 -71.6(3) . . . . ?
C35 C30 C31 C32 -4.1(3) . . . . ?
C35 C30 C31 C36 170.26(18) . . . . ?
C36 C31 C32 C33 -174.0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9812(5)
2 0.0188(5)

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: HF'
_chemical_properties_physical    Moisture-sensitive,Heat-sensitive
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_1438_caachf_tbuoh_mecn_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 2263387'
loop_
_audit_author_name
_audit_author_address
'Evelin Gruden'
;Jozef Stefan Institute
Slovenia
;
_audit_update_record             
;
2023-05-16 deposited with the CCDC.	2023-06-20 downloaded from the CCDC.
;
_audit_creation_date             2023-04-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C20 H32 F N), C20 H32 N, F2 H'
_chemical_formula_sum            'C60 H97 F4 N3'
_chemical_formula_weight         936.40
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3894(3)
_cell_length_b                   17.6755(7)
_cell_length_c                   17.8951(7)
_cell_angle_alpha                96.869(3)
_cell_angle_beta                 96.961(3)
_cell_angle_gamma                93.453(3)
_cell_volume                     2918.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7046
_cell_measurement_temperature    150.01(11)
_cell_measurement_theta_max      72.0660
_cell_measurement_theta_min      3.3470
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.546
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.066
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1028
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 8 7 0.0932
6 -2 -3 0.1314
6 0 -1 0.1327
-6 4 4 0.1426
0 9 -8 0.0686
0 -8 9 0.0434
-1 -11 2 0.0727
1 -11 -1 0.0802
0 -2 2 0.0619
0 2 -2 0.0891
1 -2 2 0.1131
1 -1 1 0.1304
2 -3 1 0.1242

_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.266
_exptl_crystal_size_min          0.121
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11761
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        70.000
_diffrn_reflns_theta_max         72.552
_diffrn_reflns_theta_min         3.324
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean 10.6426
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00  32.00   1.00   30.61    --  -40.98  58.00 -65.00   51
  2  ω   -112.00 -15.00   1.00   30.61    --  -40.98 -58.00 153.00   97
  3  ω     19.00  64.00   1.00   30.61    --   40.98  58.00 -65.00   45
  4  ω     -5.00  20.00   1.00   30.61    --   40.98 -58.00 153.00   25
  5  ω     76.00 174.00   1.00  122.43    --  103.58  58.00 -65.00   98
  6  ω     30.00  57.00   1.00  122.43    --  103.58 -58.00 153.00   27
  7  ω    -73.00  34.00   1.00   30.61    --  -40.98  77.00  30.00  107
  8  ω    -19.00  67.00   1.00   30.61    --   40.98 -77.00-120.00   86
  9  ω    -10.00  72.00   1.00   30.61    --   40.98 -77.00-180.00   82
 10  ω     44.00  74.00   1.00   30.61    --   40.98 -77.00  30.00   30
 11  ω     95.00 121.00   1.00  122.43    --  103.58  61.00 120.00   26
 12  ω     28.00 110.00   1.00  122.43    --  103.58 -80.00  70.42   82
 13  ω     33.00  60.00   1.00  122.43    --  103.58 -79.00 -60.58   27
 14  ω     77.00 105.00   1.00  122.43    --  103.58 -79.00-164.31   28
 15  ω    103.00 175.00   1.00  122.43    --  103.58  77.00   0.00   72
 16  ω    111.00 163.00   1.00  122.43    --  103.58  77.00  30.00   52
 17  ω     27.00  60.00   1.00  122.43    --  103.58 -79.00-164.31   33
 18  ω    131.00 161.00   1.00  122.43    --  103.58  61.00 120.00   30
 19  ω     89.00 122.00   1.00  122.43    --  103.58 -80.00  34.51   33
 20  ω     68.00 108.00   1.00  122.43    --  103.58 -80.00-101.19   40
 21  ω     36.00 136.00   1.00  122.43    --  103.58 -80.00 152.42  100
 22  ω    106.00 142.00   1.00  122.43    --  103.58  77.00 150.00   36
 23  ω     79.00 136.00   1.00  122.43    --  103.58 -79.00 -60.58   57
 24  ω    105.00 178.00   1.00  122.43    --  103.58  77.00-120.00   73
 25  ω     75.00 102.00   1.00  122.43    --  103.58 -80.00  21.66   27
 26  ω    122.00 149.00   1.00  122.43    --  103.58  77.00-150.00   27
 27  ω     31.00 122.00   1.00  122.43    --  103.58 -45.00 -60.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8607
_reflns_number_total             11761
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     702
_refine_ls_number_reflns         11761
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0566
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0982P)²+0.0761P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1491
_refine_ls_wR_factor_ref         0.1600
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.7935(10)
 0.2065(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All F(H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C47B) = Uanis(C47A)
Uanis(C44B) = Uanis(C44A)
4. Others
 Sof(F21B)=Sof(H22A)=1-FVAR(1)
 Sof(F21A)=Sof(H22)=FVAR(1)
 Sof(F41B)=Sof(H42A)=1-FVAR(2)
 Sof(F41A)=Sof(H42)=FVAR(2)
 Sof(C26B)=Sof(H26D)=Sof(H26E)=Sof(H26F)=Sof(C27B)=Sof(H27D)=Sof(H27E)=
 Sof(H27F)=1-FVAR(3)
 Sof(C26A)=Sof(H26A)=Sof(H26B)=Sof(H26C)=Sof(C27A)=Sof(H27A)=Sof(H27B)=
 Sof(H27C)=FVAR(3)
 Sof(C24B)=Sof(H24C)=Sof(H24D)=1-FVAR(4)
 Sof(C24A)=Sof(H24A)=Sof(H24B)=FVAR(4)
 Sof(C46B)=Sof(H46D)=Sof(H46E)=Sof(H46F)=Sof(C47B)=Sof(H47D)=Sof(H47E)=
 Sof(H47F)=1-FVAR(5)
 Sof(C46A)=Sof(H46A)=Sof(H46B)=Sof(H46C)=Sof(C47A)=Sof(H47A)=Sof(H47B)=
 Sof(H47C)=FVAR(5)
 Sof(C44B)=Sof(H44C)=Sof(H44D)=1-FVAR(6)
 Sof(C44A)=Sof(H44A)=Sof(H44B)=FVAR(6)
5.a Ternary CH refined with riding coordinates:
 C22(H22), C22(H22A), C36(H36), C39(H39), C42(H42), C42(H42A), C56(H56),
 C59(H59), C16(H16), C19(H19)
5.b Secondary CH2 refined with riding coordinates:
 C24A(H24A,H24B), C24B(H24C,H24D), C44A(H44A,H44B), C44B(H44C,H44D), C4(H4A,H4B)
5.c Aromatic/amide H refined with riding coordinates:
 C32(H32), C33(H33), C34(H34), C52(H52), C53(H53), C54(H54), C2(H2), C12(H12),
 C13(H13), C14(H14)
5.d Idealised Me refined as rotating group:
 C26A(H26A,H26B,H26C), C26B(H26D,H26E,H26F), C27A(H27A,H27B,H27C), C27B(H27D,
 H27E,H27F), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C37(H37A,H37B,H37C),
 C38(H38A,H38B,H38C), C40(H40A,H40B,H40C), C41(H41A,H41B,H41C), C46A(H46A,H46B,
 H46C), C46B(H46D,H46E,H46F), C47A(H47A,H47B,H47C), C47B(H47D,H47E,H47F),
 C48(H48A,H48B,H48C), C49(H49A,H49B,H49C), C57(H57A,H57B,H57C), C58(H58A,H58B,
 H58C), C60(H60A,H60B,H60C), C61(H61A,H61B,H61C), C6(H6A,H6B,H6C), C7(H7A,H7B,
 H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F21A F 0.5184(3) 0.31958(14) 0.76718(17) 0.0758(10) Uani 0.674(5) 1 d . . P A 1
F21B F 0.6839(9) 0.3047(4) 0.7277(4) 0.108(3) Uani 0.326(5) 1 d . . P A 2
N21 N 0.59257(19) 0.19451(10) 0.77430(11) 0.0403(4) Uani 1 1 d . . . . .
C22 C 0.6278(3) 0.27454(14) 0.78318(15) 0.0524(6) Uani 1 1 d . . . . .
H22 H 0.696978 0.283056 0.746177 0.063 Uiso 0.674(5) 1 calc R U P A 1
H22A H 0.534569 0.298380 0.787053 0.063 Uiso 0.326(5) 1 calc R U P A 2
C23 C 0.7149(3) 0.29368(14) 0.86223(16) 0.0560(6) Uani 1 1 d . . . . .
C24A C 0.7807(7) 0.2189(2) 0.8756(3) 0.0477(17) Uani 0.618(15) 1 d . . P B 1
H24A H 0.794570 0.213866 0.930448 0.057 Uiso 0.618(15) 1 calc R U P B 1
H24B H 0.875198 0.217096 0.856429 0.057 Uiso 0.618(15) 1 calc R U P B 1
C24B C 0.7083(14) 0.2215(5) 0.8987(5) 0.056(3) Uani 0.382(15) 1 d . . P B 2
H24C H 0.632385 0.222289 0.932585 0.067 Uiso 0.382(15) 1 calc R U P B 2
H24D H 0.801643 0.215828 0.929006 0.067 Uiso 0.382(15) 1 calc R U P B 2
C25 C 0.6728(3) 0.15356(14) 0.83151(15) 0.0523(6) Uani 1 1 d . . . . .
C26A C 0.8269(7) 0.3615(3) 0.8698(4) 0.099(3) Uani 0.662(8) 1 d . . P B 1
H26A H 0.907818 0.346437 0.842910 0.148 Uiso 0.662(8) 1 calc R U P B 1
H26B H 0.861681 0.377467 0.923537 0.148 Uiso 0.662(8) 1 calc R U P B 1
H26C H 0.783122 0.404027 0.847629 0.148 Uiso 0.662(8) 1 calc R U P B 1
C26B C 0.8701(10) 0.3084(7) 0.8363(6) 0.078(4) Uani 0.338(8) 1 d . . P B 2
H26D H 0.889572 0.264589 0.801019 0.117 Uiso 0.338(8) 1 calc R U P B 2
H26E H 0.943435 0.314957 0.880970 0.117 Uiso 0.338(8) 1 calc R U P B 2
H26F H 0.872451 0.354640 0.811156 0.117 Uiso 0.338(8) 1 calc R U P B 2
C27A C 0.6040(7) 0.3121(4) 0.9184(3) 0.087(2) Uani 0.662(8) 1 d . . P B 1
H27A H 0.575439 0.364247 0.915539 0.130 Uiso 0.662(8) 1 calc R U P B 1
H27B H 0.647603 0.307931 0.970222 0.130 Uiso 0.662(8) 1 calc R U P B 1
H27C H 0.518990 0.275890 0.904943 0.130 Uiso 0.662(8) 1 calc R U P B 1
C27B C 0.6870(11) 0.3657(6) 0.9102(6) 0.069(3) Uani 0.338(8) 1 d . . P B 2
H27D H 0.704905 0.409669 0.883230 0.104 Uiso 0.338(8) 1 calc R U P B 2
H27E H 0.751265 0.371499 0.958326 0.104 Uiso 0.338(8) 1 calc R U P B 2
H27F H 0.586781 0.362772 0.920444 0.104 Uiso 0.338(8) 1 calc R U P B 2
C28 C 0.5730(4) 0.1069(2) 0.8718(2) 0.0831(10) Uani 1 1 d . . . . .
H28A H 0.511340 0.140774 0.898365 0.125 Uiso 1 1 calc R U . . .
H28B H 0.630070 0.080274 0.908642 0.125 Uiso 1 1 calc R U . . .
H28C H 0.513018 0.069282 0.834598 0.125 Uiso 1 1 calc R U . . .
C29 C 0.7739(4) 0.0977(2) 0.7983(2) 0.0846(10) Uani 1 1 d . . . . .
H29A H 0.717596 0.057541 0.762367 0.127 Uiso 1 1 calc R U . . .
H29B H 0.826915 0.074677 0.839302 0.127 Uiso 1 1 calc R U . . .
H29C H 0.842092 0.125214 0.771817 0.127 Uiso 1 1 calc R U . . .
C30 C 0.5097(2) 0.15595(12) 0.70633(12) 0.0383(5) Uani 1 1 d . . . . .
C31 C 0.5726(3) 0.13827(13) 0.63950(14) 0.0456(5) Uani 1 1 d . . . . .
C32 C 0.4883(3) 0.09946(16) 0.57526(15) 0.0563(6) Uani 1 1 d . . . . .
H32 H 0.531177 0.086703 0.530428 0.068 Uiso 1 1 calc R U . . .
C33 C 0.3445(3) 0.07921(16) 0.57526(16) 0.0582(7) Uani 1 1 d . . . . .
H33 H 0.289203 0.052252 0.531088 0.070 Uiso 1 1 calc R U . . .
C34 C 0.2814(3) 0.09839(14) 0.64001(15) 0.0503(6) Uani 1 1 d . . . . .
H34 H 0.181871 0.084756 0.639828 0.060 Uiso 1 1 calc R U . . .
C35 C 0.3608(2) 0.13738(12) 0.70563(13) 0.0414(5) Uani 1 1 d . . . . .
C36 C 0.7275(3) 0.16415(16) 0.63296(17) 0.0561(6) Uani 1 1 d . . . . .
H36 H 0.776223 0.184487 0.684913 0.067 Uiso 1 1 calc R U . . .
C37 C 0.7280(4) 0.2291(2) 0.5838(2) 0.0935(12) Uani 1 1 d . . . . .
H37A H 0.678294 0.210710 0.532926 0.140 Uiso 1 1 calc R U . . .
H37B H 0.827559 0.246820 0.580111 0.140 Uiso 1 1 calc R U . . .
H37C H 0.678563 0.271464 0.606822 0.140 Uiso 1 1 calc R U . . .
C38 C 0.8114(3) 0.0981(2) 0.6009(2) 0.0839(10) Uani 1 1 d . . . . .
H38A H 0.810725 0.057563 0.633768 0.126 Uiso 1 1 calc R U . . .
H38B H 0.910969 0.117005 0.598839 0.126 Uiso 1 1 calc R U . . .
H38C H 0.765956 0.077668 0.549658 0.126 Uiso 1 1 calc R U . . .
C39 C 0.2808(3) 0.16292(13) 0.77208(14) 0.0461(5) Uani 1 1 d . . . . .
H39 H 0.353293 0.186119 0.815615 0.055 Uiso 1 1 calc R U . . .
C40 C 0.1805(3) 0.22414(15) 0.75103(17) 0.0586(7) Uani 1 1 d . . . . .
H40A H 0.235755 0.266013 0.733717 0.088 Uiso 1 1 calc R U . . .
H40B H 0.136277 0.243858 0.795569 0.088 Uiso 1 1 calc R U . . .
H40C H 0.105131 0.201829 0.710284 0.088 Uiso 1 1 calc R U . . .
C41 C 0.1954(3) 0.09653(16) 0.79792(18) 0.0634(7) Uani 1 1 d . . . . .
H41A H 0.123183 0.073065 0.756105 0.095 Uiso 1 1 calc R U . . .
H41B H 0.147268 0.115639 0.841256 0.095 Uiso 1 1 calc R U . . .
H41C H 0.260999 0.058356 0.812934 0.095 Uiso 1 1 calc R U . . .
F41A F 0.8107(3) 0.70071(15) 0.80719(16) 0.0617(10) Uani 0.566(5) 1 d . . P C 1
F41B F 0.6247(5) 0.6926(2) 0.8365(3) 0.0926(18) Uani 0.434(5) 1 d . . P C 2
N41 N 0.73116(18) 0.81676(10) 0.86424(10) 0.0386(4) Uani 1 1 d . . . . .
C42 C 0.7398(3) 0.73663(13) 0.86222(14) 0.0448(5) Uani 1 1 d . . . . .
H42 H 0.639386 0.712326 0.855446 0.054 Uiso 0.566(5) 1 calc R U P C 1
H42A H 0.812111 0.722695 0.827197 0.054 Uiso 0.434(5) 1 calc R U P C 2
C43 C 0.8107(3) 0.72594(16) 0.94228(16) 0.0626(7) Uani 1 1 d . . . . .
C44A C 0.9018(5) 0.80181(19) 0.9670(2) 0.0558(10) Uani 0.835(8) 1 d . . P D 1
H44A H 0.911546 0.814659 1.022848 0.067 Uiso 0.835(8) 1 calc R U P D 1
H44B H 0.999111 0.797963 0.951590 0.067 Uiso 0.835(8) 1 calc R U P D 1
C44B C 0.831(2) 0.7966(10) 0.9847(11) 0.0558(10) Uani 0.165(8) 1 d . . P D 2
H44C H 0.925537 0.801555 1.016822 0.067 Uiso 0.165(8) 1 calc R U P D 2
H44D H 0.755232 0.802569 1.018429 0.067 Uiso 0.165(8) 1 calc R U P D 2
C45 C 0.8250(3) 0.86323(14) 0.92837(14) 0.0483(6) Uani 1 1 d . . . . .
C46A C 0.8954(7) 0.6570(3) 0.9459(3) 0.098(2) Uani 0.846(6) 1 d . . P D 1
H46A H 0.931799 0.653087 0.998870 0.146 Uiso 0.846(6) 1 calc R U P D 1
H46B H 0.976427 0.661629 0.916598 0.146 Uiso 0.846(6) 1 calc R U P D 1
H46C H 0.833190 0.611022 0.924548 0.146 Uiso 0.846(6) 1 calc R U P D 1
C46B C 0.9782(18) 0.6991(17) 0.9108(12) 0.074(8) Uani 0.154(6) 1 d . . P D 2
H46D H 0.966464 0.645922 0.886648 0.111 Uiso 0.154(6) 1 calc R U P D 2
H46E H 1.053503 0.704253 0.954424 0.111 Uiso 0.154(6) 1 calc R U P D 2
H46F H 1.005470 0.732497 0.874087 0.111 Uiso 0.154(6) 1 calc R U P D 2
C47A C 0.6879(5) 0.7176(2) 0.9938(2) 0.0776(12) Uani 0.846(6) 1 d . . P D 1
H47A H 0.622672 0.758305 0.987537 0.116 Uiso 0.846(6) 1 calc R U P D 1
H47B H 0.730391 0.721580 1.047027 0.116 Uiso 0.846(6) 1 calc R U P D 1
H47C H 0.634025 0.667777 0.978900 0.116 Uiso 0.846(6) 1 calc R U P D 1
C47B C 0.768(3) 0.6556(13) 0.9681(12) 0.0776(12) Uani 0.154(6) 1 d . . P D 2
H47D H 0.666266 0.655514 0.976313 0.116 Uiso 0.154(6) 1 calc R U P D 2
H47E H 0.827055 0.650304 1.015815 0.116 Uiso 0.154(6) 1 calc R U P D 2
H47F H 0.779812 0.612832 0.929779 0.116 Uiso 0.154(6) 1 calc R U P D 2
C48 C 0.9414(3) 0.91498(19) 0.9031(2) 0.0756(9) Uani 1 1 d . . . . .
H48A H 1.000989 0.883870 0.872147 0.113 Uiso 1 1 calc R U . . .
H48B H 1.001850 0.942265 0.947816 0.113 Uiso 1 1 calc R U . . .
H48C H 0.896121 0.951979 0.872995 0.113 Uiso 1 1 calc R U . . .
C49 C 0.7379(3) 0.91478(16) 0.97770(16) 0.0571(7) Uani 1 1 d . . . . .
H49A H 0.689601 0.950353 0.946939 0.086 Uiso 1 1 calc R U . . .
H49B H 0.802606 0.943700 1.019917 0.086 Uiso 1 1 calc R U . . .
H49C H 0.665703 0.883241 0.997786 0.086 Uiso 1 1 calc R U . . .
C50 C 0.6534(2) 0.84927(11) 0.80352(12) 0.0348(4) Uani 1 1 d . . . . .
C51 C 0.7164(2) 0.86372(11) 0.73874(13) 0.0384(5) Uani 1 1 d . . . . .
C52 C 0.6380(2) 0.89821(13) 0.68228(14) 0.0440(5) Uani 1 1 d . . . . .
H52 H 0.681133 0.908383 0.638813 0.053 Uiso 1 1 calc R U . . .
C53 C 0.4991(2) 0.91786(13) 0.68828(14) 0.0451(5) Uani 1 1 d . . . . .
H53 H 0.448228 0.942633 0.650160 0.054 Uiso 1 1 calc R U . . .
C54 C 0.4357(2) 0.90104(12) 0.75010(13) 0.0408(5) Uani 1 1 d . . . . .
H54 H 0.339617 0.913575 0.753670 0.049 Uiso 1 1 calc R U . . .
C55 C 0.5083(2) 0.86605(11) 0.80796(12) 0.0360(4) Uani 1 1 d . . . . .
C56 C 0.8655(2) 0.84011(13) 0.72433(15) 0.0457(5) Uani 1 1 d . . . . .
H56 H 0.911416 0.820637 0.770969 0.055 Uiso 1 1 calc R U . . .
C57 C 0.8521(3) 0.77551(16) 0.65880(16) 0.0577(7) Uani 1 1 d . . . . .
H57A H 0.797300 0.731092 0.671893 0.087 Uiso 1 1 calc R U . . .
H57B H 0.948244 0.761475 0.649239 0.087 Uiso 1 1 calc R U . . .
H57C H 0.802043 0.792414 0.613124 0.087 Uiso 1 1 calc R U . . .
C58 C 0.9636(3) 0.90688(17) 0.7078(2) 0.0669(8) Uani 1 1 d . . . . .
H58A H 0.925134 0.923837 0.659684 0.100 Uiso 1 1 calc R U . . .
H58B H 1.060517 0.890281 0.704217 0.100 Uiso 1 1 calc R U . . .
H58C H 0.967814 0.949250 0.748864 0.100 Uiso 1 1 calc R U . . .
C59 C 0.4262(2) 0.84322(13) 0.87099(13) 0.0419(5) Uani 1 1 d . . . . .
H59 H 0.496150 0.824277 0.909926 0.050 Uiso 1 1 calc R U . . .
C60 C 0.3120(3) 0.77813(15) 0.84008(16) 0.0536(6) Uani 1 1 d . . . . .
H60A H 0.239691 0.796092 0.803422 0.080 Uiso 1 1 calc R U . . .
H60B H 0.265591 0.761185 0.882024 0.080 Uiso 1 1 calc R U . . .
H60C H 0.357564 0.735354 0.814984 0.080 Uiso 1 1 calc R U . . .
C61 C 0.3560(3) 0.91085(15) 0.91033(15) 0.0526(6) Uani 1 1 d . . . . .
H61A H 0.430346 0.951685 0.931371 0.079 Uiso 1 1 calc R U . . .
H61B H 0.306876 0.893885 0.951365 0.079 Uiso 1 1 calc R U . . .
H61C H 0.286125 0.930069 0.873305 0.079 Uiso 1 1 calc R U . . .
N1 N 0.22827(17) 0.50701(10) 0.68831(9) 0.0347(4) Uani 1 1 d . . . . .
C2 C 0.3219(2) 0.49573(11) 0.74290(12) 0.0363(4) Uani 1 1 d . . . . .
H2 H 0.417539 0.484626 0.736004 0.044 Uiso 1 1 calc R U . . .
C3 C 0.2690(2) 0.50139(13) 0.81819(12) 0.0424(5) Uani 1 1 d . . . . .
C4 C 0.1219(3) 0.53455(15) 0.80004(14) 0.0516(6) Uani 1 1 d . . . . .
H4A H 0.048597 0.509679 0.826365 0.062 Uiso 1 1 calc R U . . .
H4B H 0.129380 0.590171 0.817223 0.062 Uiso 1 1 calc R U . . .
C5 C 0.0790(2) 0.51921(13) 0.71369(13) 0.0432(5) Uani 1 1 d . . . . .
C6 C 0.2574(3) 0.42282(16) 0.84509(17) 0.0612(7) Uani 1 1 d . . . . .
H6A H 0.184300 0.389485 0.810639 0.092 Uiso 1 1 calc R U . . .
H6B H 0.229960 0.427957 0.896475 0.092 Uiso 1 1 calc R U . . .
H6C H 0.350538 0.400546 0.845451 0.092 Uiso 1 1 calc R U . . .
C7 C 0.3753(3) 0.55559(18) 0.87593(16) 0.0671(8) Uani 1 1 d . . . . .
H7A H 0.467808 0.532905 0.883361 0.101 Uiso 1 1 calc R U . . .
H7B H 0.336394 0.563518 0.924447 0.101 Uiso 1 1 calc R U . . .
H7C H 0.389072 0.604774 0.856668 0.101 Uiso 1 1 calc R U . . .
C8 C 0.0126(3) 0.58685(15) 0.68177(16) 0.0539(6) Uani 1 1 d . . . . .
H8A H 0.073025 0.633767 0.701656 0.081 Uiso 1 1 calc R U . . .
H8B H -0.083833 0.591268 0.696800 0.081 Uiso 1 1 calc R U . . .
H8C H 0.005735 0.579106 0.626261 0.081 Uiso 1 1 calc R U . . .
C9 C -0.0185(2) 0.44704(15) 0.68537(15) 0.0508(6) Uani 1 1 d . . . . .
H9A H -0.111584 0.451902 0.704286 0.076 Uiso 1 1 calc R U . . .
H9B H 0.026331 0.402961 0.703830 0.076 Uiso 1 1 calc R U . . .
H9C H -0.032890 0.439757 0.629742 0.076 Uiso 1 1 calc R U . . .
C10 C 0.25873(19) 0.50760(12) 0.61005(11) 0.0338(4) Uani 1 1 d . . . . .
C11 C 0.2499(2) 0.43840(12) 0.56212(12) 0.0367(5) Uani 1 1 d . . . . .
C12 C 0.2751(2) 0.44358(14) 0.48685(12) 0.0410(5) Uani 1 1 d . . . . .
H12 H 0.268085 0.398212 0.451875 0.049 Uiso 1 1 calc R U . . .
C13 C 0.3095(2) 0.51213(14) 0.46271(13) 0.0450(5) Uani 1 1 d . . . . .
H13 H 0.324289 0.513893 0.411336 0.054 Uiso 1 1 calc R U . . .
C14 C 0.3228(2) 0.57890(14) 0.51275(13) 0.0424(5) Uani 1 1 d . . . . .
H14 H 0.348299 0.626063 0.495523 0.051 Uiso 1 1 calc R U . . .
C15 C 0.2994(2) 0.57798(12) 0.58830(12) 0.0372(5) Uani 1 1 d . . . . .
C16 C 0.2285(2) 0.36033(12) 0.58717(13) 0.0428(5) Uani 1 1 d . . . . .
H16 H 0.209674 0.367523 0.641289 0.051 Uiso 1 1 calc R U . . .
C17 C 0.3663(3) 0.31819(14) 0.58326(16) 0.0529(6) Uani 1 1 d . . . . .
H17A H 0.384144 0.308125 0.530290 0.079 Uiso 1 1 calc R U . . .
H17B H 0.354757 0.269681 0.604064 0.079 Uiso 1 1 calc R U . . .
H17C H 0.447775 0.349884 0.612944 0.079 Uiso 1 1 calc R U . . .
C18 C 0.0997(3) 0.31192(16) 0.54007(18) 0.0633(7) Uani 1 1 d . . . . .
H18A H 0.012006 0.338687 0.544253 0.095 Uiso 1 1 calc R U . . .
H18B H 0.088706 0.262465 0.559151 0.095 Uiso 1 1 calc R U . . .
H18C H 0.116149 0.303734 0.486758 0.095 Uiso 1 1 calc R U . . .
C19 C 0.3334(2) 0.65129(13) 0.64345(13) 0.0417(5) Uani 1 1 d . . . . .
H19 H 0.297273 0.642357 0.692219 0.050 Uiso 1 1 calc R U . . .
C20 C 0.2618(4) 0.71966(15) 0.61535(16) 0.0626(7) Uani 1 1 d . . . . .
H20A H 0.305784 0.734305 0.571722 0.094 Uiso 1 1 calc R U . . .
H20B H 0.274846 0.762672 0.656148 0.094 Uiso 1 1 calc R U . . .
H20C H 0.158824 0.705936 0.600112 0.094 Uiso 1 1 calc R U . . .
C21 C 0.4965(3) 0.66876(18) 0.65976(18) 0.0670(8) Uani 1 1 d . . . . .
H21A H 0.541156 0.624484 0.677865 0.100 Uiso 1 1 calc R U . . .
H21B H 0.518751 0.713196 0.698717 0.100 Uiso 1 1 calc R U . . .
H21C H 0.534139 0.679801 0.613162 0.100 Uiso 1 1 calc R U . . .
F1 F 0.61334(15) 0.44753(9) 0.71678(10) 0.0626(4) Uani 1 1 d . . . . .
H1 H 0.667(4) 0.502(2) 0.758(2) 0.094 Uiso 1 1 d . U . . .
F2 F 0.7294(2) 0.55188(12) 0.78556(14) 0.0999(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F21A C22 1.361(3) . ?
F21B C22 1.329(8) . ?
N21 C22 1.419(3) . ?
N21 C25 1.482(3) . ?
N21 C30 1.434(3) . ?
C22 H22 1.0000 . ?
C22 H22A 1.0000 . ?
C22 C23 1.535(4) . ?
C23 C24A 1.524(5) . ?
C23 C24B 1.502(9) . ?
C23 C26A 1.528(6) . ?
C23 C26B 1.597(10) . ?
C23 C27A 1.556(6) . ?
C23 C27B 1.503(10) . ?
C24A H24A 0.9900 . ?
C24A H24B 0.9900 . ?
C24A C25 1.559(5) . ?
C24B H24C 0.9900 . ?
C24B H24D 0.9900 . ?
C24B C25 1.584(8) . ?
C25 C28 1.515(4) . ?
C25 C29 1.529(4) . ?
C26A H26A 0.9800 . ?
C26A H26B 0.9800 . ?
C26A H26C 0.9800 . ?
C26B H26D 0.9800 . ?
C26B H26E 0.9800 . ?
C26B H26F 0.9800 . ?
C27A H27A 0.9800 . ?
C27A H27B 0.9800 . ?
C27A H27C 0.9800 . ?
C27B H27D 0.9800 . ?
C27B H27E 0.9800 . ?
C27B H27F 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 C31 1.407(3) . ?
C30 C35 1.415(3) . ?
C31 C32 1.394(3) . ?
C31 C36 1.521(3) . ?
C32 H32 0.9500 . ?
C32 C33 1.375(4) . ?
C33 H33 0.9500 . ?
C33 C34 1.381(4) . ?
C34 H34 0.9500 . ?
C34 C35 1.394(3) . ?
C35 C39 1.521(3) . ?
C36 H36 1.0000 . ?
C36 C37 1.528(5) . ?
C36 C38 1.541(4) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39 1.0000 . ?
C39 C40 1.528(4) . ?
C39 C41 1.530(4) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
F41A C42 1.369(4) . ?
F41B C42 1.295(5) . ?
N41 C42 1.420(3) . ?
N41 C45 1.487(3) . ?
N41 C50 1.432(3) . ?
C42 H42 1.0000 . ?
C42 H42A 1.0000 . ?
C42 C43 1.543(3) . ?
C43 C44A 1.534(5) . ?
C43 C44B 1.372(17) . ?
C43 C46A 1.499(5) . ?
C43 C46B 1.804(17) . ?
C43 C47A 1.572(6) . ?
C43 C47B 1.43(2) . ?
C44A H44A 0.9900 . ?
C44A H44B 0.9900 . ?
C44A C45 1.526(4) . ?
C44B H44C 0.9900 . ?
C44B H44D 0.9900 . ?
C44B C45 1.64(2) . ?
C45 C48 1.529(4) . ?
C45 C49 1.533(3) . ?
C46A H46A 0.9800 . ?
C46A H46B 0.9800 . ?
C46A H46C 0.9800 . ?
C46B H46D 0.9800 . ?
C46B H46E 0.9800 . ?
C46B H46F 0.9800 . ?
C47A H47A 0.9800 . ?
C47A H47B 0.9800 . ?
C47A H47C 0.9800 . ?
C47B H47D 0.9800 . ?
C47B H47E 0.9800 . ?
C47B H47F 0.9800 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C50 C51 1.406(3) . ?
C50 C55 1.421(3) . ?
C51 C52 1.398(3) . ?
C51 C56 1.528(3) . ?
C52 H52 0.9500 . ?
C52 C53 1.383(3) . ?
C53 H53 0.9500 . ?
C53 C54 1.372(3) . ?
C54 H54 0.9500 . ?
C54 C55 1.397(3) . ?
C55 C59 1.520(3) . ?
C56 H56 1.0000 . ?
C56 C57 1.524(4) . ?
C56 C58 1.532(4) . ?
C57 H57A 0.9800 . ?
C57 H57B 0.9800 . ?
C57 H57C 0.9800 . ?
C58 H58A 0.9800 . ?
C58 H58B 0.9800 . ?
C58 H58C 0.9800 . ?
C59 H59 1.0000 . ?
C59 C60 1.528(3) . ?
C59 C61 1.538(3) . ?
C60 H60A 0.9800 . ?
C60 H60B 0.9800 . ?
C60 H60C 0.9800 . ?
C61 H61A 0.9800 . ?
C61 H61B 0.9800 . ?
C61 H61C 0.9800 . ?
N1 C2 1.275(3) . ?
N1 C5 1.545(3) . ?
N1 C10 1.464(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.486(3) . ?
C3 C4 1.546(3) . ?
C3 C6 1.525(4) . ?
C3 C7 1.542(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.536(3) . ?
C5 C8 1.520(3) . ?
C5 C9 1.521(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.399(3) . ?
C10 C15 1.393(3) . ?
C11 C12 1.408(3) . ?
C11 C16 1.511(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.368(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.383(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.398(3) . ?
C15 C19 1.524(3) . ?
C16 H16 1.0000 . ?
C16 C17 1.536(3) . ?
C16 C18 1.537(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19 1.0000 . ?
C19 C20 1.525(4) . ?
C19 C21 1.529(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
F1 H1 1.18(4) . ?
F2 H1 1.06(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C22 N21 C25 114.66(18) . . ?
C22 N21 C30 121.14(19) . . ?
C30 N21 C25 122.92(17) . . ?
F21A C22 N21 117.0(2) . . ?
F21A C22 H22 105.8 . . ?
F21A C22 C23 115.9(2) . . ?
F21B C22 N21 118.6(4) . . ?
F21B C22 H22A 105.5 . . ?
F21B C22 C23 115.3(4) . . ?
N21 C22 H22 105.8 . . ?
N21 C22 H22A 105.5 . . ?
N21 C22 C23 105.4(2) . . ?
C23 C22 H22 105.8 . . ?
C23 C22 H22A 105.5 . . ?
C22 C23 C26B 98.3(4) . . ?
C22 C23 C27A 106.3(3) . . ?
C24A C23 C22 103.2(2) . . ?
C24A C23 C26A 113.2(4) . . ?
C24A C23 C27A 110.4(4) . . ?
C24B C23 C22 106.1(3) . . ?
C24B C23 C26B 110.0(8) . . ?
C26A C23 C22 114.5(3) . . ?
C26A C23 C27A 109.0(4) . . ?
C27B C23 C22 118.0(4) . . ?
C27B C23 C24B 116.4(6) . . ?
C27B C23 C26B 106.4(6) . . ?
C23 C24A H24A 110.4 . . ?
C23 C24A H24B 110.4 . . ?
C23 C24A C25 106.4(3) . . ?
H24A C24A H24B 108.6 . . ?
C25 C24A H24A 110.4 . . ?
C25 C24A H24B 110.4 . . ?
C23 C24B H24C 110.5 . . ?
C23 C24B H24D 110.5 . . ?
C23 C24B C25 106.2(5) . . ?
H24C C24B H24D 108.7 . . ?
C25 C24B H24C 110.5 . . ?
C25 C24B H24D 110.5 . . ?
N21 C25 C24A 101.4(2) . . ?
N21 C25 C24B 99.3(4) . . ?
N21 C25 C28 112.0(2) . . ?
N21 C25 C29 113.7(2) . . ?
C28 C25 C24A 121.7(4) . . ?
C28 C25 C24B 95.5(5) . . ?
C28 C25 C29 106.0(3) . . ?
C29 C25 C24A 102.0(4) . . ?
C29 C25 C24B 128.9(5) . . ?
C23 C26A H26A 109.5 . . ?
C23 C26A H26B 109.5 . . ?
C23 C26A H26C 109.5 . . ?
H26A C26A H26B 109.5 . . ?
H26A C26A H26C 109.5 . . ?
H26B C26A H26C 109.5 . . ?
C23 C26B H26D 109.5 . . ?
C23 C26B H26E 109.5 . . ?
C23 C26B H26F 109.5 . . ?
H26D C26B H26E 109.5 . . ?
H26D C26B H26F 109.5 . . ?
H26E C26B H26F 109.5 . . ?
C23 C27A H27A 109.5 . . ?
C23 C27A H27B 109.5 . . ?
C23 C27A H27C 109.5 . . ?
H27A C27A H27B 109.5 . . ?
H27A C27A H27C 109.5 . . ?
H27B C27A H27C 109.5 . . ?
C23 C27B H27D 109.5 . . ?
C23 C27B H27E 109.5 . . ?
C23 C27B H27F 109.5 . . ?
H27D C27B H27E 109.5 . . ?
H27D C27B H27F 109.5 . . ?
H27E C27B H27F 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C25 C29 H29A 109.5 . . ?
C25 C29 H29B 109.5 . . ?
C25 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 N21 121.33(19) . . ?
C31 C30 C35 119.2(2) . . ?
C35 C30 N21 119.44(19) . . ?
C30 C31 C36 122.4(2) . . ?
C32 C31 C30 119.2(2) . . ?
C32 C31 C36 118.3(2) . . ?
C31 C32 H32 119.2 . . ?
C33 C32 C31 121.6(2) . . ?
C33 C32 H32 119.2 . . ?
C32 C33 H33 120.3 . . ?
C32 C33 C34 119.4(2) . . ?
C34 C33 H33 120.3 . . ?
C33 C34 H34 119.4 . . ?
C33 C34 C35 121.2(2) . . ?
C35 C34 H34 119.4 . . ?
C30 C35 C39 122.6(2) . . ?
C34 C35 C30 119.3(2) . . ?
C34 C35 C39 118.0(2) . . ?
C31 C36 H36 108.2 . . ?
C31 C36 C37 108.9(2) . . ?
C31 C36 C38 112.3(2) . . ?
C37 C36 H36 108.2 . . ?
C37 C36 C38 111.1(3) . . ?
C38 C36 H36 108.2 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C35 C39 H39 108.1 . . ?
C35 C39 C40 109.9(2) . . ?
C35 C39 C41 112.5(2) . . ?
C40 C39 H39 108.1 . . ?
C40 C39 C41 110.0(2) . . ?
C41 C39 H39 108.1 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C39 C41 H41A 109.5 . . ?
C39 C41 H41B 109.5 . . ?
C39 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C42 N41 C45 114.39(18) . . ?
C42 N41 C50 121.85(17) . . ?
C50 N41 C45 123.23(17) . . ?
F41A C42 N41 117.3(2) . . ?
F41A C42 H42 107.7 . . ?
F41A C42 C43 111.2(2) . . ?
F41B C42 N41 117.9(3) . . ?
F41B C42 H42A 105.9 . . ?
F41B C42 C43 115.7(3) . . ?
N41 C42 H42 107.7 . . ?
N41 C42 H42A 105.9 . . ?
N41 C42 C43 104.76(18) . . ?
C43 C42 H42 107.7 . . ?
C43 C42 H42A 105.9 . . ?
C42 C43 C46B 94.2(7) . . ?
C42 C43 C47A 107.9(2) . . ?
C44A C43 C42 102.2(2) . . ?
C44A C43 C47A 110.6(3) . . ?
C44B C43 C42 107.6(8) . . ?
C44B C43 C46B 109.8(14) . . ?
C44B C43 C47B 126.4(14) . . ?
C46A C43 C42 115.0(3) . . ?
C46A C43 C44A 113.7(3) . . ?
C46A C43 C47A 107.3(4) . . ?
C47B C43 C42 114.9(9) . . ?
C47B C43 C46B 98.4(16) . . ?
C43 C44A H44A 110.2 . . ?
C43 C44A H44B 110.2 . . ?
H44A C44A H44B 108.5 . . ?
C45 C44A C43 107.4(2) . . ?
C45 C44A H44A 110.2 . . ?
C45 C44A H44B 110.2 . . ?
C43 C44B H44C 109.7 . . ?
C43 C44B H44D 109.7 . . ?
C43 C44B C45 109.7(12) . . ?
H44C C44B H44D 108.2 . . ?
C45 C44B H44C 109.7 . . ?
C45 C44B H44D 109.7 . . ?
N41 C45 C44A 101.84(19) . . ?
N41 C45 C44B 95.8(6) . . ?
N41 C45 C48 113.5(2) . . ?
N41 C45 C49 111.66(19) . . ?
C44A C45 C48 106.7(3) . . ?
C44A C45 C49 116.2(3) . . ?
C48 C45 C44B 132.8(8) . . ?
C48 C45 C49 107.0(2) . . ?
C49 C45 C44B 94.2(8) . . ?
C43 C46A H46A 109.5 . . ?
C43 C46A H46B 109.5 . . ?
C43 C46A H46C 109.5 . . ?
H46A C46A H46B 109.5 . . ?
H46A C46A H46C 109.5 . . ?
H46B C46A H46C 109.5 . . ?
C43 C46B H46D 109.5 . . ?
C43 C46B H46E 109.5 . . ?
C43 C46B H46F 109.5 . . ?
H46D C46B H46E 109.5 . . ?
H46D C46B H46F 109.5 . . ?
H46E C46B H46F 109.5 . . ?
C43 C47A H47A 109.5 . . ?
C43 C47A H47B 109.5 . . ?
C43 C47A H47C 109.5 . . ?
H47A C47A H47B 109.5 . . ?
H47A C47A H47C 109.5 . . ?
H47B C47A H47C 109.5 . . ?
C43 C47B H47D 109.5 . . ?
C43 C47B H47E 109.5 . . ?
C43 C47B H47F 109.5 . . ?
H47D C47B H47E 109.5 . . ?
H47D C47B H47F 109.5 . . ?
H47E C47B H47F 109.5 . . ?
C45 C48 H48A 109.5 . . ?
C45 C48 H48B 109.5 . . ?
C45 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C45 C49 H49A 109.5 . . ?
C45 C49 H49B 109.5 . . ?
C45 C49 H49C 109.5 . . ?
H49A C49 H49B 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C51 C50 N41 121.56(18) . . ?
C51 C50 C55 119.03(19) . . ?
C55 C50 N41 119.41(19) . . ?
C50 C51 C56 123.3(2) . . ?
C52 C51 C50 119.4(2) . . ?
C52 C51 C56 117.2(2) . . ?
C51 C52 H52 119.3 . . ?
C53 C52 C51 121.5(2) . . ?
C53 C52 H52 119.3 . . ?
C52 C53 H53 120.5 . . ?
C54 C53 C52 119.0(2) . . ?
C54 C53 H53 120.5 . . ?
C53 C54 H54 119.0 . . ?
C53 C54 C55 122.0(2) . . ?
C55 C54 H54 119.0 . . ?
C50 C55 C59 122.41(19) . . ?
C54 C55 C50 118.9(2) . . ?
C54 C55 C59 118.61(19) . . ?
C51 C56 H56 108.1 . . ?
C51 C56 C58 112.5(2) . . ?
C57 C56 C51 110.01(19) . . ?
C57 C56 H56 108.1 . . ?
C57 C56 C58 109.9(2) . . ?
C58 C56 H56 108.1 . . ?
C56 C57 H57A 109.5 . . ?
C56 C57 H57B 109.5 . . ?
C56 C57 H57C 109.5 . . ?
H57A C57 H57B 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
C56 C58 H58A 109.5 . . ?
C56 C58 H58B 109.5 . . ?
C56 C58 H58C 109.5 . . ?
H58A C58 H58B 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C55 C59 H59 108.0 . . ?
C55 C59 C60 110.43(19) . . ?
C55 C59 C61 112.3(2) . . ?
C60 C59 H59 108.0 . . ?
C60 C59 C61 109.99(19) . . ?
C61 C59 H59 108.0 . . ?
C59 C60 H60A 109.5 . . ?
C59 C60 H60B 109.5 . . ?
C59 C60 H60C 109.5 . . ?
H60A C60 H60B 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
C59 C61 H61A 109.5 . . ?
C59 C61 H61B 109.5 . . ?
C59 C61 H61C 109.5 . . ?
H61A C61 H61B 109.5 . . ?
H61A C61 H61C 109.5 . . ?
H61B C61 H61C 109.5 . . ?
C2 N1 C5 112.59(17) . . ?
C2 N1 C10 123.67(17) . . ?
C10 N1 C5 123.74(16) . . ?
N1 C2 H2 122.8 . . ?
N1 C2 C3 114.44(19) . . ?
C3 C2 H2 122.8 . . ?
C2 C3 C4 101.26(18) . . ?
C2 C3 C6 110.33(19) . . ?
C2 C3 C7 109.0(2) . . ?
C6 C3 C4 113.6(2) . . ?
C6 C3 C7 109.4(2) . . ?
C7 C3 C4 113.0(2) . . ?
C3 C4 H4A 110.2 . . ?
C3 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
C5 C4 C3 107.50(18) . . ?
C5 C4 H4A 110.2 . . ?
C5 C4 H4B 110.2 . . ?
C4 C5 N1 99.68(17) . . ?
C8 C5 N1 111.70(18) . . ?
C8 C5 C4 112.3(2) . . ?
C8 C5 C9 109.3(2) . . ?
C9 C5 N1 108.05(17) . . ?
C9 C5 C4 115.4(2) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 N1 119.15(18) . . ?
C15 C10 N1 117.22(18) . . ?
C15 C10 C11 123.61(18) . . ?
C10 C11 C12 116.0(2) . . ?
C10 C11 C16 124.78(19) . . ?
C12 C11 C16 118.95(19) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 C11 121.8(2) . . ?
C13 C12 H12 119.1 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.3(2) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.5 . . ?
C13 C14 C15 121.0(2) . . ?
C15 C14 H14 119.5 . . ?
C10 C15 C14 117.15(19) . . ?
C10 C15 C19 123.74(19) . . ?
C14 C15 C19 118.8(2) . . ?
C11 C16 H16 108.0 . . ?
C11 C16 C17 109.95(18) . . ?
C11 C16 C18 112.5(2) . . ?
C17 C16 H16 108.0 . . ?
C17 C16 C18 110.2(2) . . ?
C18 C16 H16 108.0 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C19 H19 107.9 . . ?
C15 C19 C20 113.3(2) . . ?
C15 C19 C21 109.44(19) . . ?
C20 C19 H19 107.9 . . ?
C20 C19 C21 110.3(2) . . ?
C21 C19 H19 107.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F21A C22 C23 C24A 157.4(4) . . . . ?
F21A C22 C23 C26A -79.2(4) . . . . ?
F21A C22 C23 C27A 41.2(4) . . . . ?
F21B C22 C23 C24B -139.7(7) . . . . ?
F21B C22 C23 C26B -26.0(7) . . . . ?
F21B C22 C23 C27B 87.6(7) . . . . ?
N21 C22 C23 C24A 26.2(4) . . . . ?
N21 C22 C23 C24B -7.0(6) . . . . ?
N21 C22 C23 C26A 149.6(4) . . . . ?
N21 C22 C23 C26B 106.8(5) . . . . ?
N21 C22 C23 C27A -90.0(4) . . . . ?
N21 C22 C23 C27B -139.6(5) . . . . ?
N21 C30 C31 C32 178.8(2) . . . . ?
N21 C30 C31 C36 -5.0(3) . . . . ?
N21 C30 C35 C34 -178.6(2) . . . . ?
N21 C30 C35 C39 5.7(3) . . . . ?
C22 N21 C25 C24A -5.8(4) . . . . ?
C22 N21 C25 C24B 25.5(6) . . . . ?
C22 N21 C25 C28 125.4(3) . . . . ?
C22 N21 C25 C29 -114.5(3) . . . . ?
C22 N21 C30 C31 78.1(3) . . . . ?
C22 N21 C30 C35 -99.9(3) . . . . ?
C22 C23 C24A C25 -30.1(5) . . . . ?
C22 C23 C24B C25 22.3(9) . . . . ?
C23 C24A C25 N21 22.4(5) . . . . ?
C23 C24A C25 C28 -102.5(4) . . . . ?
C23 C24A C25 C29 140.0(4) . . . . ?
C23 C24B C25 N21 -28.0(8) . . . . ?
C23 C24B C25 C28 -141.5(7) . . . . ?
C23 C24B C25 C29 102.9(7) . . . . ?
C25 N21 C22 F21A -143.4(3) . . . . ?
C25 N21 C22 F21B 118.1(5) . . . . ?
C25 N21 C22 C23 -12.9(3) . . . . ?
C25 N21 C30 C31 -88.2(3) . . . . ?
C25 N21 C30 C35 93.8(3) . . . . ?
C26A C23 C24A C25 -154.5(5) . . . . ?
C26B C23 C24B C25 -83.1(8) . . . . ?
C27A C23 C24A C25 83.0(5) . . . . ?
C27B C23 C24B C25 155.9(6) . . . . ?
C30 N21 C22 F21A 49.2(4) . . . . ?
C30 N21 C22 F21B -49.4(5) . . . . ?
C30 N21 C22 C23 179.7(2) . . . . ?
C30 N21 C25 C24A 161.3(4) . . . . ?
C30 N21 C25 C24B -167.3(5) . . . . ?
C30 N21 C25 C28 -67.5(3) . . . . ?
C30 N21 C25 C29 52.7(3) . . . . ?
C30 C31 C32 C33 1.1(4) . . . . ?
C30 C31 C36 C37 -106.1(3) . . . . ?
C30 C31 C36 C38 130.5(3) . . . . ?
C30 C35 C39 C40 109.2(2) . . . . ?
C30 C35 C39 C41 -127.8(2) . . . . ?
C31 C30 C35 C34 3.4(3) . . . . ?
C31 C30 C35 C39 -172.4(2) . . . . ?
C31 C32 C33 C34 0.7(4) . . . . ?
C32 C31 C36 C37 70.1(3) . . . . ?
C32 C31 C36 C38 -53.3(3) . . . . ?
C32 C33 C34 C35 -0.5(4) . . . . ?
C33 C34 C35 C30 -1.5(4) . . . . ?
C33 C34 C35 C39 174.4(2) . . . . ?
C34 C35 C39 C40 -66.6(3) . . . . ?
C34 C35 C39 C41 56.4(3) . . . . ?
C35 C30 C31 C32 -3.2(3) . . . . ?
C35 C30 C31 C36 173.0(2) . . . . ?
C36 C31 C32 C33 -175.2(3) . . . . ?
F41A C42 C43 C44A 99.6(3) . . . . ?
F41A C42 C43 C46A -24.1(5) . . . . ?
F41A C42 C43 C47A -143.7(3) . . . . ?
F41B C42 C43 C44B -128.7(12) . . . . ?
F41B C42 C43 C46B 119.0(10) . . . . ?
F41B C42 C43 C47B 17.7(14) . . . . ?
N41 C42 C43 C44A -28.0(3) . . . . ?
N41 C42 C43 C44B 2.8(12) . . . . ?
N41 C42 C43 C46A -151.8(4) . . . . ?
N41 C42 C43 C46B -109.5(10) . . . . ?
N41 C42 C43 C47A 88.6(3) . . . . ?
N41 C42 C43 C47B 149.3(13) . . . . ?
N41 C50 C51 C52 -177.58(18) . . . . ?
N41 C50 C51 C56 5.5(3) . . . . ?
N41 C50 C55 C54 177.04(18) . . . . ?
N41 C50 C55 C59 -6.6(3) . . . . ?
C42 N41 C45 C44A 2.1(3) . . . . ?
C42 N41 C45 C44B -25.7(9) . . . . ?
C42 N41 C45 C48 116.4(3) . . . . ?
C42 N41 C45 C49 -122.5(2) . . . . ?
C42 N41 C50 C51 -84.1(3) . . . . ?
C42 N41 C50 C55 94.6(2) . . . . ?
C42 C43 C44A C45 30.3(3) . . . . ?
C42 C43 C44B C45 -19.1(16) . . . . ?
C43 C44A C45 N41 -20.5(3) . . . . ?
C43 C44A C45 C48 -139.8(3) . . . . ?
C43 C44A C45 C49 101.0(3) . . . . ?
C43 C44B C45 N41 26.8(15) . . . . ?
C43 C44B C45 C48 -103.1(13) . . . . ?
C43 C44B C45 C49 139.1(13) . . . . ?
C45 N41 C42 F41A -107.1(3) . . . . ?
C45 N41 C42 F41B 147.1(4) . . . . ?
C45 N41 C42 C43 16.8(3) . . . . ?
C45 N41 C50 C51 87.0(3) . . . . ?
C45 N41 C50 C55 -94.2(2) . . . . ?
C46A C43 C44A C45 154.8(3) . . . . ?
C46B C43 C44B C45 82.2(15) . . . . ?
C47A C43 C44A C45 -84.4(3) . . . . ?
C47B C43 C44B C45 -160.6(16) . . . . ?
C50 N41 C42 F41A 64.8(3) . . . . ?
C50 N41 C42 F41B -41.0(4) . . . . ?
C50 N41 C42 C43 -171.3(2) . . . . ?
C50 N41 C45 C44A -169.7(3) . . . . ?
C50 N41 C45 C44B 162.6(9) . . . . ?
C50 N41 C45 C48 -55.3(3) . . . . ?
C50 N41 C45 C49 65.7(3) . . . . ?
C50 C51 C52 C53 -0.6(3) . . . . ?
C50 C51 C56 C57 110.1(2) . . . . ?
C50 C51 C56 C58 -127.1(2) . . . . ?
C50 C55 C59 C60 -108.4(2) . . . . ?
C50 C55 C59 C61 128.4(2) . . . . ?
C51 C50 C55 C54 -4.2(3) . . . . ?
C51 C50 C55 C59 172.22(18) . . . . ?
C51 C52 C53 C54 -1.9(3) . . . . ?
C52 C51 C56 C57 -67.0(3) . . . . ?
C52 C51 C56 C58 55.9(3) . . . . ?
C52 C53 C54 C55 1.3(3) . . . . ?
C53 C54 C55 C50 1.7(3) . . . . ?
C53 C54 C55 C59 -174.8(2) . . . . ?
C54 C55 C59 C60 67.9(3) . . . . ?
C54 C55 C59 C61 -55.2(3) . . . . ?
C55 C50 C51 C52 3.6(3) . . . . ?
C55 C50 C51 C56 -173.31(18) . . . . ?
C56 C51 C52 C53 176.5(2) . . . . ?
N1 C2 C3 C4 -10.1(2) . . . . ?
N1 C2 C3 C6 110.4(2) . . . . ?
N1 C2 C3 C7 -129.5(2) . . . . ?
N1 C10 C11 C12 177.63(17) . . . . ?
N1 C10 C11 C16 -7.9(3) . . . . ?
N1 C10 C15 C14 -177.50(18) . . . . ?
N1 C10 C15 C19 8.7(3) . . . . ?
C2 N1 C5 C4 15.3(2) . . . . ?
C2 N1 C5 C8 134.2(2) . . . . ?
C2 N1 C5 C9 -105.6(2) . . . . ?
C2 N1 C10 C11 85.5(2) . . . . ?
C2 N1 C10 C15 -92.7(2) . . . . ?
C2 C3 C4 C5 19.4(2) . . . . ?
C3 C4 C5 N1 -20.7(2) . . . . ?
C3 C4 C5 C8 -139.1(2) . . . . ?
C3 C4 C5 C9 94.8(2) . . . . ?
C5 N1 C2 C3 -3.4(3) . . . . ?
C5 N1 C10 C11 -93.9(2) . . . . ?
C5 N1 C10 C15 87.9(2) . . . . ?
C6 C3 C4 C5 -98.9(2) . . . . ?
C7 C3 C4 C5 135.9(2) . . . . ?
C10 N1 C2 C3 177.14(18) . . . . ?
C10 N1 C5 C4 -165.24(19) . . . . ?
C10 N1 C5 C8 -46.4(3) . . . . ?
C10 N1 C5 C9 73.8(2) . . . . ?
C10 C11 C12 C13 1.5(3) . . . . ?
C10 C11 C16 C17 -110.6(2) . . . . ?
C10 C11 C16 C18 126.1(2) . . . . ?
C10 C15 C19 C20 -133.7(2) . . . . ?
C10 C15 C19 C21 102.8(3) . . . . ?
C11 C10 C15 C14 4.4(3) . . . . ?
C11 C10 C15 C19 -169.38(19) . . . . ?
C11 C12 C13 C14 1.1(3) . . . . ?
C12 C11 C16 C17 63.7(3) . . . . ?
C12 C11 C16 C18 -59.5(3) . . . . ?
C12 C13 C14 C15 -1.0(3) . . . . ?
C13 C14 C15 C10 -1.6(3) . . . . ?
C13 C14 C15 C19 172.50(19) . . . . ?
C14 C15 C19 C20 52.6(3) . . . . ?
C14 C15 C19 C21 -70.9(3) . . . . ?
C15 C10 C11 C12 -4.3(3) . . . . ?
C15 C10 C11 C16 170.17(19) . . . . ?
C16 C11 C12 C13 -173.37(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.7935(10)
2 0.2065(10)

_twin_special_details            
;
Component 2 rotated by 179.8280° 
around [0.00 1.00 0.00] (reciprocal) or [0.14 0.98 0.13] (direct)
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile and t-BuOH'
_chemical_properties_physical    Moisture-sensitive