# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_pyxk_br_2
_database_code_depnum_ccdc_archive 'CCDC 2341089'
loop_
_audit_author_name
_audit_author_address
'Petr Buikin'
;N S Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-05-15 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_audit_creation_date             2024-02-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Br), 0.5(C4 H12 O2), C18 H18 N2'
_chemical_formula_sum            'C20 H24 Br2 N2 O'
_chemical_formula_weight         468.23
_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 0.0033 0.0016 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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      orthorhombic
_space_group_IT_number           57
_space_group_name_H-M_alt        'P b c m'
_space_group_name_Hall           '-P 2c 2b'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y-1/2, z'

_cell_length_a                   12.7794(18)
_cell_length_b                   8.1003(12)
_cell_length_c                   19.956(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2065.8(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1905
_cell_measurement_temperature    140
_cell_measurement_theta_max      25.803
_cell_measurement_theta_min      2.590
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.440
_exptl_absorpt_coefficient_mu    3.934
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5009
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0850 before and 0.0416 after correction.
The Ratio of minimum to maximum transmission is 0.6714.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0673
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8538
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.088
_diffrn_reflns_theta_min         2.041
_diffrn_ambient_temperature      140
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2108
_reflns_number_total             2992
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         2992
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0312P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0846
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Sof: H10A(0.25) H10B(0.5) H10C(0.5) H11A(0.5) H11B(0.5)
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C11(H11A,H11B)
2.b Me refined with riding coordinates:
 C10(H10A,H10B,H10C)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9)
;
_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
Br1 Br 0.56683(3) 0.80377(5) 0.750000 0.02415(12) Uani 1 2 d S T P . .
Br2 Br 0.87603(3) 0.750000 0.500000 0.02721(12) Uani 1 2 d S T P . .
O1 O 0.7676(2) 0.5550(4) 0.750000 0.0351(8) Uani 1 2 d S T P . .
H1A H 0.727(4) 0.621(6) 0.750000 0.048(17) Uiso 1 2 d S . P . .
N1 N 0.71742(15) 0.3731(3) 0.61492(9) 0.0184(5) Uani 1 1 d . . . . .
C1 C 0.81021(19) 0.3605(3) 0.58364(13) 0.0230(6) Uani 1 1 d . . . . .
H1 H 0.835783 0.450123 0.557689 0.028 Uiso 1 1 calc R U . . .
C2 C 0.8681(2) 0.2185(4) 0.58904(14) 0.0296(7) Uani 1 1 d . . . . .
H2 H 0.933921 0.209989 0.567153 0.035 Uiso 1 1 calc R U . . .
C3 C 0.8304(2) 0.0879(4) 0.62647(13) 0.0287(6) Uani 1 1 d . . . . .
H3 H 0.868872 -0.012120 0.629703 0.034 Uiso 1 1 calc R U . . .
C4 C 0.7362(2) 0.1052(3) 0.65890(13) 0.0297(7) Uani 1 1 d . . . . .
H4 H 0.709723 0.017471 0.685576 0.036 Uiso 1 1 calc R U . . .
C5 C 0.6808(2) 0.2480(4) 0.65282(13) 0.0268(6) Uani 1 1 d . . . . .
H5 H 0.615878 0.259578 0.675480 0.032 Uiso 1 1 calc R U . . .
C6 C 0.6538(2) 0.5270(3) 0.60680(14) 0.0290(7) Uani 1 1 d . . . . .
H6A H 0.700984 0.620802 0.596808 0.035 Uiso 1 1 calc R U . . .
H6B H 0.617149 0.551384 0.649364 0.035 Uiso 1 1 calc R U . . .
C7 C 0.5742(2) 0.5103(3) 0.55110(12) 0.0197(6) Uani 1 1 d . . . . .
C8 C 0.4725(2) 0.4635(3) 0.56532(13) 0.0243(6) Uani 1 1 d . . . . .
H8 H 0.453197 0.438122 0.610126 0.029 Uiso 1 1 calc R U . . .
C9 C 0.3988(2) 0.4534(3) 0.51490(13) 0.0246(6) Uani 1 1 d . . . . .
H9 H 0.329165 0.421521 0.525299 0.029 Uiso 1 1 calc R U . . .
C10 C 0.9510(4) 0.5457(8) 0.750000 0.0753(19) Uani 1 2 d S T P . .
H10A H 1.013275 0.616338 0.750000 0.113 Uiso 0.5 1 calc R U P A -1
H10B H 0.951351 0.475876 0.790096 0.113 Uiso 0.5 1 calc R U P A -1
H10C H 0.951350 0.475876 0.709904 0.113 Uiso 0.5 1 calc R U P A -1
C11 C 0.8586(4) 0.6472(7) 0.750000 0.073(2) Uani 1 2 d S T P . .
H11A H 0.859386 0.719134 0.790095 0.087 Uiso 0.5 1 calc R U P . .
H11B H 0.859386 0.719133 0.709905 0.087 Uiso 0.5 1 calc R U P . .


_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
O1 H1A 0.75(4) . ?
O1 C11 1.381(5) . ?
N1 C1 1.344(3) . ?
N1 C5 1.348(3) . ?
N1 C6 1.497(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.372(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.373(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.362(4) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.513(3) . ?
C7 C8 1.384(4) . ?
C7 C9 1.393(3) 5_666 ?
C8 H8 0.9500 . ?
C8 C9 1.380(4) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10 C11 1.439(7) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?

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
C11 O1 H1A 101(4) . . ?
C1 N1 C5 120.6(2) . . ?
C1 N1 C6 119.5(2) . . ?
C5 N1 C6 119.9(2) . . ?
N1 C1 H1 119.9 . . ?
N1 C1 C2 120.2(2) . . ?
C2 C1 H1 119.9 . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.7(3) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 120.6 . . ?
C4 C3 C2 118.9(3) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
N1 C5 C4 120.6(2) . . ?
N1 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
N1 C6 H6A 109.3 . . ?
N1 C6 H6B 109.3 . . ?
N1 C6 C7 111.7(2) . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C8 C7 C6 120.4(2) . . ?
C8 C7 C9 119.0(2) . 5_666 ?
C9 C7 C6 120.6(2) 5_666 . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.5(2) . . ?
C9 C8 H8 119.8 . . ?
C7 C9 H9 119.7 5_666 . ?
C8 C9 C7 120.6(2) . 5_666 ?
C8 C9 H9 119.7 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C11 C10 H10C 109.5 . . ?
O1 C11 C10 112.5(5) . . ?
O1 C11 H11A 109.1 . . ?
O1 C11 H11B 109.1 . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?

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 C1 C2 C3 0.4(4) . . . . ?
N1 C6 C7 C8 95.2(3) . . . . ?
N1 C6 C7 C9 -86.8(3) . . . 5_666 ?
C1 N1 C5 C4 -1.4(4) . . . . ?
C1 N1 C6 C7 94.5(3) . . . . ?
C1 C2 C3 C4 -1.6(4) . . . . ?
C2 C3 C4 C5 1.3(4) . . . . ?
C3 C4 C5 N1 0.2(4) . . . . ?
C5 N1 C1 C2 1.1(4) . . . . ?
C5 N1 C6 C7 -84.8(3) . . . . ?
C6 N1 C1 C2 -178.2(2) . . . . ?
C6 N1 C5 C4 177.8(2) . . . . ?
C6 C7 C8 C9 177.9(2) . . . . ?
C7 C8 C9 C7 0.2(5) . . . 5_666 ?
C9 C7 C8 C9 -0.2(5) 5_666 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2341090'
loop_
_audit_author_name
_audit_author_address
'Petr Buikin'
;N S Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-04-20 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;

_audit_creation_date             2022-03-07T20:35:50-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C18 H18 N2, 2(I)'
_chemical_formula_sum            'C18 H18 I2 N2'
_chemical_formula_weight         516.14

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.8222(5)
_cell_length_b                   11.0457(8)
_cell_length_c                   12.1817(9)
_cell_angle_alpha                90
_cell_angle_beta                 94.692(2)
_cell_angle_gamma                90
_cell_volume                     914.89(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9949
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      31.53

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.874
_exptl_crystal_F_000             492
_exptl_special_details           
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 0.71075    6.826   11.059   12.189   90.015   94.731   90.018
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.436
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_correction_T_min  0.048
_exptl_absorpt_correction_T_max  0.1015
_shelx_estimated_absorpt_T_min   0.34
_shelx_estimated_absorpt_T_max   0.771

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS D8 VENTURE PHOTON III C14 IuS 3.0'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_number            14879
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.493
_diffrn_reflns_theta_max         31.529
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_Friedel_coverage         0
_reflns_number_total             3033
_reflns_number_gt                2822
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0200P)²+1.6000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3033
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0699
_refine_ls_wR_factor_gt          0.0689
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.163
_refine_diff_density_min         -0.807
_refine_diff_density_rms         0.112

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
I1 I 1.02209(2) 0.76794(2) 0.18397(2) 0.02705(6) Uani 1 1 d . . . . .
N1 N 0.4937(3) 0.52016(19) 0.30921(16) 0.0216(4) Uani 1 1 d . . . . .
C1 C 0.3385(4) 0.5510(2) 0.3649(2) 0.0257(5) Uani 1 1 d . . . . .
H1A H 0.21415 0.514285 0.346774 0.031 Uiso 1 1 calc R U . . .
C2 C 0.3598(4) 0.6360(2) 0.4483(2) 0.0297(5) Uani 1 1 d . . . . .
H2A H 0.250636 0.658103 0.48765 0.036 Uiso 1 1 calc R U . . .
C3 C 0.5425(5) 0.6885(2) 0.4739(2) 0.0302(5) Uani 1 1 d . . . . .
H3A H 0.560528 0.744657 0.532921 0.036 Uiso 1 1 calc R U . . .
C4 C 0.6985(4) 0.6588(3) 0.4131(2) 0.0299(5) Uani 1 1 d . . . . .
H4A H 0.822954 0.696463 0.42818 0.036 Uiso 1 1 calc R U . . .
C5 C 0.6705(4) 0.5739(2) 0.3306(2) 0.0264(5) Uani 1 1 d . . . . .
H5A H 0.776565 0.55288 0.288392 0.032 Uiso 1 1 calc R U . . .
C6 C 0.4718(4) 0.4208(2) 0.22581(19) 0.0240(4) Uani 1 1 d . . . . .
H6A H 0.342343 0.381447 0.230215 0.029 Uiso 1 1 calc R U . . .
H6B H 0.574755 0.359128 0.243739 0.029 Uiso 1 1 calc R U . . .
C7 C 0.4877(4) 0.4651(2) 0.10970(19) 0.0215(4) Uani 1 1 d . . . . .
C8 C 0.6672(4) 0.4610(2) 0.0625(2) 0.0240(4) Uani 1 1 d . . . . .
H8A H 0.781884 0.43437 0.10522 0.029 Uiso 1 1 calc R U . . .
C9 C 0.6796(4) 0.4957(2) -0.0467(2) 0.0233(4) Uani 1 1 d . . . . .
H9A H 0.802412 0.492587 -0.078187 0.028 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C1 1.347(3) . ?
N1 C5 1.350(3) . ?
N1 C6 1.495(3) . ?
C1 C2 1.382(4) . ?
C1 H1A 0.95 . ?
C2 C3 1.387(4) . ?
C2 H2A 0.95 . ?
C3 C4 1.384(4) . ?
C3 H3A 0.95 . ?
C4 C5 1.377(4) . ?
C4 H4A 0.95 . ?
C5 H5A 0.95 . ?
C6 C7 1.509(3) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C7 C9 1.391(3) 3_665 ?
C7 C8 1.395(3) . ?
C8 C9 1.394(3) . ?
C8 H8A 0.95 . ?
C9 H9A 0.95 . ?

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
C1 N1 C5 121.2(2) . . ?
C1 N1 C6 119.3(2) . . ?
C5 N1 C6 119.5(2) . . ?
N1 C1 C2 120.1(2) . . ?
N1 C1 H1A 119.9 . . ?
C2 C1 H1A 119.9 . . ?
C1 C2 C3 119.2(3) . . ?
C1 C2 H2A 120.4 . . ?
C3 C2 H2A 120.4 . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C5 C4 C3 119.0(3) . . ?
C5 C4 H4A 120.5 . . ?
C3 C4 H4A 120.5 . . ?
N1 C5 C4 120.6(2) . . ?
N1 C5 H5A 119.7 . . ?
C4 C5 H5A 119.7 . . ?
N1 C6 C7 112.87(19) . . ?
N1 C6 H6A 109 . . ?
C7 C6 H6A 109 . . ?
N1 C6 H6B 109 . . ?
C7 C6 H6B 109 . . ?
H6A C6 H6B 107.8 . . ?
C9 C7 C8 119.4(2) 3_665 . ?
C9 C7 C6 120.0(2) 3_665 . ?
C8 C7 C6 120.5(2) . . ?
C9 C8 C7 120.5(2) . . ?
C9 C8 H8A 119.7 . . ?
C7 C8 H8A 119.7 . . ?
C7 C9 C8 120.1(2) 3_665 . ?
C7 C9 H9A 120 3_665 . ?
C8 C9 H9A 120 . . ?

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2341092'
loop_
_audit_author_name
_audit_author_address
'Petr Buikin'
;N S Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-04-20 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_audit_creation_date             2024-04-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
_chemical_formula_moiety         '2(C18 H18 N2), Bi I6, 3(C2 H6 O S), I'
_chemical_formula_sum            'C42 H54 Bi I7 N4 O3 S3'
_chemical_formula_weight         1856.35
#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#
#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
# END of CIF
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z'
5 '-x, -y, -z'
6 'x, -y, z'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z'

_symmetry_Int_Tables_number      12
_cell_length_a                   16.9076(7)
_cell_length_b                   15.1942(7)
_cell_length_c                   13.5491(6)
_cell_angle_alpha                90
_cell_angle_beta                 125.4550(10)
_cell_angle_gamma                90
_cell_volume                     2835.3(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9992
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.97
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   0.765
_shelx_estimated_absorpt_T_min   0.484
#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    7.068
_exptl_absorpt_correction_T_max  0.182
_exptl_absorpt_correction_T_min  0.032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.174
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1720
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 0.71065   17.348   14.716   13.824   90.004  121.680   90.007
;
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25970
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.179
_diffrn_reflns_theta_min         2.055
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker AXS D8 VENTURE PHOTON III C14 IuS 3.0'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_reflns_Friedel_coverage         0
_reflns_number_gt                4934
_reflns_number_total             5397
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-2018 (Sheldrick, 2015)'
_refine_diff_density_max         0.794
_refine_diff_density_min         -1.469
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         5397
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0215
_refine_ls_restrained_S_all      0.985
_refine_ls_shift/su_max          0.01
_refine_ls_shift/su_mean         0
#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0200P)²+8.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0466
_refine_ls_wR_factor_ref         0.0484
_olex2_refinement_description    
;
1. Restrained distances
 S101-O101
 1.54 with sigma of 0.01
 S101-C101 = S101-C102
 1.78 with sigma of 0.01
 O101-C101 = O101-C102
 2.6 with sigma of 0.02
 C101-C102
 2.8 with sigma of 0.02
 S201-O201
 1.54 with sigma of 0.01
 S201-C201 = S201-C202
 1.78 with sigma of 0.01
 O201-C201 = O201-C202
 2.6 with sigma of 0.02
 C201-C202
 2.8 with sigma of 0.02
 S211-O211
 1.54 with sigma of 0.01
 S211-C211 = S211-C212
 1.78 with sigma of 0.01
 O211-C211 = O211-C212
 2.6 with sigma of 0.02
 C211-C212
 2.8 with sigma of 0.02
2. Others
 Uiso(S201)=Uiso(O201)=Uiso(C201)=Uiso(C202)=Uiso(S211)=Uiso(O211)=Uiso(C211)=
 Uiso(C212)=FVAR(1)
 Fixed Sof: S101(0.5) O101(0.5) C101(0.5) H10A(0.5) H10B(0.5) H10C(0.5)
 C102(0.5) H10D(0.5) H10E(0.5) H10F(0.5) S201(0.228) O201(0.228) C201(0.228)
 H20A(0.228) H20B(0.228) H20C(0.228) C202(0.228) H20D(0.228) H20E(0.228)
 H20F(0.228) S211(0.022) O211(0.022) C211(0.022) H21A(0.022) H21B(0.022)
 H21C(0.022) C212(0.022) H21D(0.022) H21E(0.022) H21F(0.022)
3.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
3.b Me refined with riding coordinates:
 C101(H10A,H10B,H10C), C102(H10D,H10E,H10F), C201(H20A,H20B,H20C), C202(H20D,
 H20E,H20F), C211(H21A,H21B,H21C), C212(H21D,H21E,H21F)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2A), C3(H3A), C4(H4A), C5(H5A), C8(H8A), C9(H9A)
;
#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#
_atom_sites_solution_hydrogens   geom
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
Bi1 Bi 0.5 0.5 1 0.01781(4) Uani 1 4 d S T P . .
I1 I 0.5 0.70455(2) 1 0.02832(5) Uani 1 2 d S T P . .
I2 I 0.44224(2) 0.5 0.74090(2) 0.03013(5) Uani 1 2 d S T P . .
I3 I 0.71342(2) 0.5 1.08331(2) 0.02276(4) Uani 1 2 d S T P . .
I4 I 0.5 0 0.5 0.02339(6) Uani 1 4 d S T P . .
N1 N 0.29487(14) 0.21663(13) 0.26152(17) 0.0231(4) Uani 1 1 d . . . . .
C1 C 0.36709(17) 0.18701(19) 0.2560(2) 0.0309(5) Uani 1 1 d . . . . .
H1A H 0.397499 0.132392 0.292479 0.037 Uiso 1 1 calc R U . . .
C2 C 0.39726(19) 0.2357(2) 0.1974(3) 0.0394(7) Uani 1 1 d . . . . .
H2A H 0.448052 0.214469 0.19314 0.047 Uiso 1 1 calc R U . . .
C3 C 0.3538(2) 0.3148(2) 0.1454(2) 0.0377(6) Uani 1 1 d . . . . .
H3A H 0.374566 0.348846 0.105554 0.045 Uiso 1 1 calc R U . . .
C4 C 0.2792(2) 0.34465(18) 0.1514(2) 0.0343(6) Uani 1 1 d . . . . .
H4A H 0.248274 0.399259 0.115737 0.041 Uiso 1 1 calc R U . . .
C5 C 0.25078(19) 0.29405(16) 0.2098(2) 0.0282(5) Uani 1 1 d . . . . .
H5A H 0.199402 0.3138 0.213814 0.034 Uiso 1 1 calc R U . . .
C6 C 0.25808(17) 0.16031(15) 0.3168(2) 0.0238(4) Uani 1 1 d . . . . .
H6A H 0.300728 0.108206 0.354503 0.029 Uiso 1 1 calc R U . . .
H6B H 0.192135 0.139158 0.252274 0.029 Uiso 1 1 calc R U . . .
C7 C 0.25432(16) 0.20841(14) 0.4112(2) 0.0212(4) Uani 1 1 d . . . . .
C8 C 0.33834(19) 0.2337(2) 0.5203(3) 0.0410(7) Uani 1 1 d . . . . .
H8A H 0.399666 0.222686 0.535043 0.049 Uiso 1 1 calc R U . . .
C9 C 0.33394(18) 0.2749(2) 0.6078(2) 0.0380(6) Uani 1 1 d . . . . .
H9A H 0.392327 0.292029 0.682104 0.046 Uiso 1 1 calc R U . . .
S101 S 0.09773(11) 0.46643(10) 0.22381(15) 0.0396(3) Uani 0.5 1 d D . P A -1
O101 O 0.1521(2) 0.5139(3) 0.1711(3) 0.0397(10) Uiso 0.5 1 d D . P A -1
C101 C 0.1638(4) 0.5162(5) 0.3721(5) 0.0501(17) Uiso 0.5 1 d D . P A -1
H10A H 0.138847 0.493612 0.416947 0.075 Uiso 0.5 1 calc R U P A -1
H10B H 0.232855 0.501684 0.416162 0.075 Uiso 0.5 1 calc R U P A -1
H10C H 0.155464 0.580179 0.363847 0.075 Uiso 0.5 1 calc R U P A -1
C102 C -0.0062(5) 0.5366(5) 0.1503(6) 0.0553(17) Uiso 0.5 1 d D . P A -1
H10D H -0.050158 0.518021 0.171483 0.083 Uiso 0.5 1 calc R U P A -1
H10E H 0.014391 0.597445 0.176821 0.083 Uiso 0.5 1 calc R U P A -1
H10F H -0.039959 0.532781 0.062378 0.083 Uiso 0.5 1 calc R U P A -1
S201 S 0.4826(3) 0.4164(2) 0.5224(3) 0.0421(6) Uiso 0.228 1 d D U P B -1
O201 O 0.4882(7) 0.3374(5) 0.4613(7) 0.0421(6) Uiso 0.228 1 d D U P B -1
C201 C 0.4041(10) 0.4956(12) 0.4115(14) 0.0421(6) Uiso 0.228 1 d D U P B -1
H20A H 0.400337 0.547546 0.451501 0.063 Uiso 0.228 1 calc R U P B -1
H20B H 0.429422 0.512811 0.36504 0.063 Uiso 0.228 1 calc R U P B -1
H20C H 0.339129 0.4702 0.356633 0.063 Uiso 0.228 1 calc R U P B -1
C202 C 0.5939(10) 0.4744(10) 0.5836(18) 0.0421(6) Uiso 0.228 1 d D U P B -1
H20D H 0.59481 0.527488 0.625281 0.063 Uiso 0.228 1 calc R U P B -1
H20E H 0.648634 0.436444 0.641144 0.063 Uiso 0.228 1 calc R U P B -1
H20F H 0.599206 0.491037 0.517739 0.063 Uiso 0.228 1 calc R U P B -1
S211 S 0.502(3) 0.4854(16) 0.492(4) 0.0421(6) Uiso 0.022 1 d D U P C -2
O211 O 0.484(7) 0.390(2) 0.445(7) 0.0421(6) Uiso 0.022 1 d D U P C -2
C211 C 0.383(5) 0.526(7) 0.427(8) 0.0421(6) Uiso 0.022 1 d D U P C -2
H21A H 0.386485 0.586951 0.451796 0.063 Uiso 0.022 1 calc R U P C -2
H21B H 0.345086 0.52221 0.338708 0.063 Uiso 0.022 1 calc R U P C -2
H21C H 0.351864 0.489804 0.455787 0.063 Uiso 0.022 1 calc R U P C -2
C212 C 0.552(7) 0.471(6) 0.648(4) 0.0421(6) Uiso 0.022 1 d D U P C -2
H21D H 0.566166 0.528952 0.686882 0.063 Uiso 0.022 1 calc R U P C -2
H21E H 0.504397 0.440495 0.655152 0.063 Uiso 0.022 1 calc R U P C -2
H21F H 0.61142 0.436456 0.686842 0.063 Uiso 0.022 1 calc R U P C -2


#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#
_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
Bi1 I1 3.1080(3) . ?
Bi1 I1 3.1080(3) 5_667 ?
Bi1 I2 3.0497(3) . ?
Bi1 I2 3.0496(3) 5_667 ?
Bi1 I3 3.0935(2) . ?
Bi1 I3 3.0935(2) 5_667 ?
N1 C1 1.344(3) . ?
N1 C5 1.351(3) . ?
N1 C6 1.490(3) . ?
C1 H1A 0.95 . ?
C1 C2 1.381(3) . ?
C2 H2A 0.95 . ?
C2 C3 1.371(4) . ?
C3 H3A 0.95 . ?
C3 C4 1.385(4) . ?
C4 H4A 0.95 . ?
C4 C5 1.375(3) . ?
C5 H5A 0.95 . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C6 C7 1.506(3) . ?
C7 C8 1.383(3) . ?
C7 C9 1.382(3) 7_556 ?
C8 H8A 0.95 . ?
C8 C9 1.381(4) . ?
C9 H9A 0.95 . ?
S101 O101 1.623(4) . ?
S101 C101 1.803(5) . ?
S101 C102 1.785(6) . ?
C101 H10A 0.98 . ?
C101 H10B 0.98 . ?
C101 H10C 0.98 . ?
C102 H10D 0.98 . ?
C102 H10E 0.98 . ?
C102 H10F 0.98 . ?
S201 O201 1.493(7) . ?
S201 C201 1.776(9) . ?
S201 C202 1.787(9) . ?
C201 H20A 0.98 . ?
C201 H20B 0.98 . ?
C201 H20C 0.98 . ?
C202 H20D 0.98 . ?
C202 H20E 0.98 . ?
C202 H20F 0.98 . ?
S211 O211 1.543(10) . ?
S211 C211 1.779(10) . ?
S211 C212 1.780(10) . ?
C211 H21A 0.98 . ?
C211 H21B 0.98 . ?
C211 H21C 0.98 . ?
C212 H21D 0.98 . ?
C212 H21E 0.98 . ?
C212 H21F 0.98 . ?

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
I1 Bi1 I1 180 . 5_667 ?
I2 Bi1 I1 90 5_667 . ?
I2 Bi1 I1 90 . . ?
I2 Bi1 I1 90 . 5_667 ?
I2 Bi1 I1 90 5_667 5_667 ?
I2 Bi1 I2 180 5_667 . ?
I2 Bi1 I3 93.045(6) 5_667 . ?
I2 Bi1 I3 86.954(6) 5_667 5_667 ?
I2 Bi1 I3 93.046(6) . 5_667 ?
I2 Bi1 I3 86.955(6) . . ?
I3 Bi1 I1 90 . . ?
I3 Bi1 I1 90 . 5_667 ?
I3 Bi1 I1 90 5_667 . ?
I3 Bi1 I1 90 5_667 5_667 ?
I3 Bi1 I3 180 . 5_667 ?
C1 N1 C5 120.6(2) . . ?
C1 N1 C6 119.6(2) . . ?
C5 N1 C6 119.7(2) . . ?
N1 C1 H1A 119.9 . . ?
N1 C1 C2 120.2(3) . . ?
C2 C1 H1A 119.9 . . ?
C1 C2 H2A 120.1 . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2A 120.1 . . ?
C2 C3 H3A 120.3 . . ?
C2 C3 C4 119.4(2) . . ?
C4 C3 H3A 120.3 . . ?
C3 C4 H4A 120.5 . . ?
C5 C4 C3 119.0(3) . . ?
C5 C4 H4A 120.5 . . ?
N1 C5 C4 120.9(3) . . ?
N1 C5 H5A 119.6 . . ?
C4 C5 H5A 119.6 . . ?
N1 C6 H6A 109.1 . . ?
N1 C6 H6B 109.1 . . ?
N1 C6 C7 112.58(18) . . ?
H6A C6 H6B 107.8 . . ?
C7 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
C8 C7 C6 121.2(2) . . ?
C9 C7 C6 120.2(2) 7_556 . ?
C9 C7 C8 118.5(2) 7_556 . ?
C7 C8 H8A 119.7 . . ?
C9 C8 C7 120.6(2) . . ?
C9 C8 H8A 119.7 . . ?
C7 C9 H9A 119.6 7_556 . ?
C8 C9 C7 120.9(2) . 7_556 ?
C8 C9 H9A 119.6 . . ?
O101 S101 C101 99.3(3) . . ?
O101 S101 C102 96.6(3) . . ?
C102 S101 C101 98.3(3) . . ?
S101 C101 H10A 109.5 . . ?
S101 C101 H10B 109.5 . . ?
S101 C101 H10C 109.5 . . ?
H10A C101 H10B 109.5 . . ?
H10A C101 H10C 109.5 . . ?
H10B C101 H10C 109.5 . . ?
S101 C102 H10D 109.5 . . ?
S101 C102 H10E 109.5 . . ?
S101 C102 H10F 109.5 . . ?
H10D C102 H10E 109.5 . . ?
H10D C102 H10F 109.5 . . ?
H10E C102 H10F 109.5 . . ?
O201 S201 C201 109.4(7) . . ?
O201 S201 C202 105.4(7) . . ?
C201 S201 C202 97.3(6) . . ?
S201 C201 H20A 109.5 . . ?
S201 C201 H20B 109.5 . . ?
S201 C201 H20C 109.5 . . ?
H20A C201 H20B 109.5 . . ?
H20A C201 H20C 109.5 . . ?
H20B C201 H20C 109.5 . . ?
S201 C202 H20D 109.5 . . ?
S201 C202 H20E 109.5 . . ?
S201 C202 H20F 109.5 . . ?
H20D C202 H20E 109.5 . . ?
H20D C202 H20F 109.5 . . ?
H20E C202 H20F 109.5 . . ?
O211 S211 C211 102.8(13) . . ?
O211 S211 C212 102.6(13) . . ?
C211 S211 C212 103.9(12) . . ?
S211 C211 H21A 109.5 . . ?
S211 C211 H21B 109.5 . . ?
S211 C211 H21C 109.4 . . ?
H21A C211 H21B 109.5 . . ?
H21A C211 H21C 109.5 . . ?
H21B C211 H21C 109.5 . . ?
S211 C212 H21D 109.5 . . ?
S211 C212 H21E 109.5 . . ?
S211 C212 H21F 109.5 . . ?
H21D C212 H21E 109.5 . . ?
H21D C212 H21F 109.5 . . ?
H21E C212 H21F 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2341091'
loop_
_audit_author_name
_audit_author_address
'Petr Buikin'
;N S Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-04-20 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_audit_creation_date             2024-04-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
_chemical_formula_moiety         '2(C18 H18 N2), Bi Br6, 3(C2 H6 O S), Br'
_chemical_formula_sum            'C42 H54 Bi Br7 N4 O3 S3'
_chemical_formula_weight         1527.42
#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#
#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
# END of CIF
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z'
5 '-x, -y, -z'
6 'x, -y, z'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z'

_symmetry_Int_Tables_number      12
_cell_length_a                   16.5194(9)
_cell_length_b                   14.5925(9)
_cell_length_c                   13.2748(7)
_cell_angle_alpha                90
_cell_angle_beta                 125.2900(10)
_cell_angle_gamma                90
_cell_volume                     2612.0(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9992
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.97
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   0.224
_shelx_estimated_absorpt_T_min   0.176
#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    8.889
_exptl_absorpt_correction_T_max  0.182
_exptl_absorpt_correction_T_min  0.032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.942
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1468
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_exptl_special_details           
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 0.71065   17.348   14.716   13.824   90.004  121.680   90.007
;
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22807
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.543
_diffrn_reflns_theta_min         2.056
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker AXS D8 VENTURE PHOTON III C14 IuS 3.0'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_reflns_Friedel_coverage         0
_reflns_number_gt                4043
_reflns_number_total             4494
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-2018 (Sheldrick, 2015)'
_refine_diff_density_max         1.392
_refine_diff_density_min         -1.65
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         4494
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0259
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0200P)²+8.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0579
_refine_ls_wR_factor_ref         0.0601
_olex2_refinement_description    
;
1. Restrained distances
 S101-O101
 1.54 with sigma of 0.01
 S101-C101 = S101-C102
 1.78 with sigma of 0.01
 O101-C101 = O101-C102
 2.6 with sigma of 0.02
 C101-C102
 2.8 with sigma of 0.02
 S201-O201
 1.54 with sigma of 0.01
 S201-C201 = S201-C202
 1.78 with sigma of 0.01
 O201-C201 = O201-C202
 2.6 with sigma of 0.02
 C201-C202
 2.8 with sigma of 0.02
 S211-O211
 1.54 with sigma of 0.01
 S211-C211 = S211-C212
 1.78 with sigma of 0.01
 O211-C211 = O211-C212
 2.6 with sigma of 0.02
 C211-C212
 2.8 with sigma of 0.02
2. Others
 Uiso(S201)=Uiso(O201)=Uiso(C201)=Uiso(C202)=Uiso(S211)=Uiso(O211)=Uiso(C211)=
 Uiso(C212)=FVAR(1)
 Fixed Sof: S101(0.5) O101(0.5) C101(0.5) H10A(0.5) H10B(0.5) H10C(0.5)
 C102(0.5) H10D(0.5) H10E(0.5) H10F(0.5) S201(0.2) O201(0.2) C201(0.2)
 H20A(0.2) H20B(0.2) H20C(0.2) C202(0.2) H20D(0.2) H20E(0.2) H20F(0.2)
 S211(0.05) O211(0.05) C211(0.05) H21A(0.05) H21B(0.05) H21C(0.05) C212(0.05)
 H21D(0.05) H21E(0.05) H21F(0.05)
3.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
3.b Me refined with riding coordinates:
 C101(H10A,H10B,H10C), C102(H10D,H10E,H10F), C201(H20A,H20B,H20C), C202(H20D,
 H20E,H20F), C211(H21A,H21B,H21C), C212(H21D,H21E,H21F)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2A), C3(H3A), C4(H4A), C5(H5A), C8(H8A), C9(H9A)
;
#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#
_atom_sites_solution_hydrogens   geom
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
Bi1 Bi 0.5 0.5 1 0.01998(5) Uani 1 4 d S T P . .
Br1 Br 0.5 0.69772(3) 1 0.03309(9) Uani 1 2 d S T P . .
Br2 Br 0.44930(3) 0.5 0.75686(3) 0.03480(9) Uani 1 2 d S T P . .
Br3 Br 0.70402(3) 0.5 1.08093(3) 0.02646(8) Uani 1 2 d S T P . .
Br4 Br 0.5 0 0.5 0.02556(10) Uani 1 4 d S T P . .
N1 N 0.29360(16) 0.21135(16) 0.2556(2) 0.0275(4) Uani 1 1 d . . . . .
C1 C 0.3709(2) 0.1829(3) 0.2558(3) 0.0433(8) Uani 1 1 d . . . . .
H1A H 0.404364 0.127708 0.296758 0.052 Uiso 1 1 calc R U . . .
C2 C 0.4016(2) 0.2342(3) 0.1964(4) 0.0596(12) Uani 1 1 d . . . . .
H2A H 0.455973 0.213844 0.195771 0.072 Uiso 1 1 calc R U . . .
C3 C 0.3540(2) 0.3144(3) 0.1381(3) 0.0506(10) Uani 1 1 d . . . . .
H3A H 0.375555 0.350278 0.098042 0.061 Uiso 1 1 calc R U . . .
C4 C 0.2748(2) 0.3421(2) 0.1387(3) 0.0386(7) Uani 1 1 d . . . . .
H4A H 0.240828 0.39729 0.098604 0.046 Uiso 1 1 calc R U . . .
C5 C 0.2449(2) 0.2893(2) 0.1978(3) 0.0313(6) Uani 1 1 d . . . . .
H5A H 0.189778 0.307936 0.197822 0.038 Uiso 1 1 calc R U . . .
C6 C 0.2576(2) 0.15326(19) 0.3144(3) 0.0282(5) Uani 1 1 d . . . . .
H6A H 0.302011 0.099651 0.353722 0.034 Uiso 1 1 calc R U . . .
H6B H 0.190403 0.130231 0.249892 0.034 Uiso 1 1 calc R U . . .
C7 C 0.25408(19) 0.20501(17) 0.4101(2) 0.0253(5) Uani 1 1 d . . . . .
C8 C 0.3380(2) 0.2412(3) 0.5134(4) 0.0535(10) Uani 1 1 d . . . . .
H8A H 0.399684 0.235578 0.523668 0.064 Uiso 1 1 calc R U . . .
C9 C 0.3345(2) 0.2857(3) 0.6029(3) 0.0459(8) Uani 1 1 d . . . . .
H9A H 0.393594 0.310044 0.673777 0.055 Uiso 1 1 calc R U . . .
S101 S 0.09328(12) 0.46564(11) 0.22400(16) 0.0391(3) Uani 0.5 1 d D . P A -1
O101 O 0.1496(3) 0.5148(3) 0.1709(3) 0.0381(10) Uiso 0.5 1 d D . P A -1
C101 C 0.1578(5) 0.5193(5) 0.3730(5) 0.0489(18) Uiso 0.5 1 d D . P A -1
H10A H 0.131646 0.496249 0.418209 0.073 Uiso 0.5 1 calc R U P A -1
H10B H 0.22872 0.505213 0.419341 0.073 Uiso 0.5 1 calc R U P A -1
H10C H 0.148276 0.585839 0.362717 0.073 Uiso 0.5 1 calc R U P A -1
C102 C -0.0162(5) 0.5351(5) 0.1426(7) 0.0510(17) Uiso 0.5 1 d D . P A -1
H10D H -0.061602 0.515233 0.163233 0.077 Uiso 0.5 1 calc R U P A -1
H10E H 0.001955 0.599372 0.166371 0.077 Uiso 0.5 1 calc R U P A -1
H10F H -0.048752 0.528636 0.053534 0.077 Uiso 0.5 1 calc R U P A -1
S201 S 0.4812(3) 0.4401(3) 0.5186(4) 0.0330(7) Uiso 0.2 1 d D U P B -1
O201 O 0.4807(7) 0.3571(6) 0.4501(9) 0.0330(7) Uiso 0.2 1 d D U P B -1
C201 C 0.4052(12) 0.5209(8) 0.3966(11) 0.0330(7) Uiso 0.2 1 d D U P B -1
H20A H 0.400759 0.578085 0.431841 0.05 Uiso 0.2 1 calc R U P B -1
H20B H 0.434902 0.533371 0.351914 0.05 Uiso 0.2 1 calc R U P B -1
H20C H 0.338647 0.495314 0.339496 0.05 Uiso 0.2 1 calc R U P B -1
C202 C 0.5996(8) 0.4900(12) 0.5799(14) 0.0330(7) Uiso 0.2 1 d D U P B -1
H20D H 0.607493 0.545228 0.626819 0.05 Uiso 0.2 1 calc R U P B -1
H20E H 0.651787 0.445878 0.634542 0.05 Uiso 0.2 1 calc R U P B -1
H20F H 0.604756 0.506294 0.512184 0.05 Uiso 0.2 1 calc R U P B -1
S211 S 0.5400(13) 0.4546(11) 0.5008(16) 0.0330(7) Uiso 0.05 1 d D U P C -2
O211 O 0.511(3) 0.3528(13) 0.488(4) 0.0330(7) Uiso 0.05 1 d D U P C -2
C211 C 0.423(2) 0.511(3) 0.425(4) 0.0330(7) Uiso 0.05 1 d D U P C -2
H21A H 0.433602 0.57772 0.427893 0.05 Uiso 0.05 1 calc R U P C -2
H21B H 0.380971 0.491287 0.338597 0.05 Uiso 0.05 1 calc R U P C -2
H21C H 0.391609 0.496235 0.466191 0.05 Uiso 0.05 1 calc R U P C -2
C212 C 0.597(3) 0.476(3) 0.6599(19) 0.0330(7) Uiso 0.05 1 d D U P C -2
H21D H 0.618352 0.54025 0.678421 0.05 Uiso 0.05 1 calc R U P C -2
H21E H 0.549298 0.464114 0.679855 0.05 Uiso 0.05 1 calc R U P C -2
H21F H 0.654612 0.435921 0.709415 0.05 Uiso 0.05 1 calc R U P C -2


#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#
_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
Bi1 Br1 2.8853(4) . ?
Bi1 Br1 2.8853(4) 5_667 ?
Bi1 Br2 2.8277(4) . ?
Bi1 Br2 2.8277(4) 5_667 ?
Bi1 Br3 2.8860(4) 5_667 ?
Bi1 Br3 2.8861(4) . ?
N1 C1 1.341(4) . ?
N1 C5 1.348(4) . ?
N1 C6 1.489(3) . ?
C1 H1A 0.95 . ?
C1 C2 1.379(4) . ?
C2 H2A 0.95 . ?
C2 C3 1.373(5) . ?
C3 H3A 0.95 . ?
C3 C4 1.374(5) . ?
C4 H4A 0.95 . ?
C4 C5 1.379(4) . ?
C5 H5A 0.95 . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C6 C7 1.508(4) . ?
C7 C8 1.373(4) . ?
C7 C9 1.378(4) 7_556 ?
C8 H8A 0.95 . ?
C8 C9 1.384(4) . ?
C9 H9A 0.95 . ?
S101 O101 1.622(4) . ?
S101 C101 1.796(5) . ?
S101 C102 1.791(6) . ?
C101 H10A 0.98 . ?
C101 H10B 0.98 . ?
C101 H10C 0.98 . ?
C102 H10D 0.98 . ?
C102 H10E 0.98 . ?
C102 H10F 0.98 . ?
S201 O201 1.511(7) . ?
S201 C201 1.800(8) . ?
S201 C202 1.784(8) . ?
C201 H20A 0.98 . ?
C201 H20B 0.98 . ?
C201 H20C 0.98 . ?
C202 H20D 0.98 . ?
C202 H20E 0.98 . ?
C202 H20F 0.98 . ?
S211 O211 1.539(10) . ?
S211 C211 1.779(10) . ?
S211 C212 1.775(10) . ?
C211 H21A 0.98 . ?
C211 H21B 0.98 . ?
C211 H21C 0.98 . ?
C212 H21D 0.98 . ?
C212 H21E 0.98 . ?
C212 H21F 0.98 . ?

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
Br1 Bi1 Br1 180 5_667 . ?
Br1 Bi1 Br3 90 . 5_667 ?
Br1 Bi1 Br3 90 5_667 5_667 ?
Br1 Bi1 Br3 90 5_667 . ?
Br1 Bi1 Br3 90 . . ?
Br2 Bi1 Br1 90 . . ?
Br2 Bi1 Br1 90 5_667 5_667 ?
Br2 Bi1 Br1 90 . 5_667 ?
Br2 Bi1 Br1 90 5_667 . ?
Br2 Bi1 Br2 180 5_667 . ?
Br2 Bi1 Br3 93.612(10) 5_667 . ?
Br2 Bi1 Br3 93.611(10) . 5_667 ?
Br2 Bi1 Br3 86.389(10) 5_667 5_667 ?
Br2 Bi1 Br3 86.388(11) . . ?
Br3 Bi1 Br3 180 5_667 . ?
C1 N1 C5 121.2(2) . . ?
C1 N1 C6 119.4(2) . . ?
C5 N1 C6 119.4(2) . . ?
N1 C1 H1A 120.2 . . ?
N1 C1 C2 119.7(3) . . ?
C2 C1 H1A 120.2 . . ?
C1 C2 H2A 119.9 . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2A 119.9 . . ?
C2 C3 H3A 120.5 . . ?
C2 C3 C4 119.0(3) . . ?
C4 C3 H3A 120.5 . . ?
C3 C4 H4A 120.2 . . ?
C3 C4 C5 119.7(3) . . ?
C5 C4 H4A 120.2 . . ?
N1 C5 C4 120.2(3) . . ?
N1 C5 H5A 119.9 . . ?
C4 C5 H5A 119.9 . . ?
N1 C6 H6A 109.2 . . ?
N1 C6 H6B 109.2 . . ?
N1 C6 C7 112.2(2) . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C8 C7 C6 121.7(3) . . ?
C8 C7 C9 118.3(3) . 7_556 ?
C9 C7 C6 119.9(2) 7_556 . ?
C7 C8 H8A 119.4 . . ?
C7 C8 C9 121.3(3) . . ?
C9 C8 H8A 119.4 . . ?
C7 C9 C8 120.4(3) 7_556 . ?
C7 C9 H9A 119.8 7_556 . ?
C8 C9 H9A 119.8 . . ?
O101 S101 C101 99.3(3) . . ?
O101 S101 C102 96.9(3) . . ?
C102 S101 C101 99.7(3) . . ?
S101 C101 H10A 109.5 . . ?
S101 C101 H10B 109.5 . . ?
S101 C101 H10C 109.5 . . ?
H10A C101 H10B 109.5 . . ?
H10A C101 H10C 109.5 . . ?
H10B C101 H10C 109.5 . . ?
S101 C102 H10D 109.5 . . ?
S101 C102 H10E 109.5 . . ?
S101 C102 H10F 109.5 . . ?
H10D C102 H10E 109.5 . . ?
H10D C102 H10F 109.5 . . ?
H10E C102 H10F 109.5 . . ?
O201 S201 C201 103.0(6) . . ?
O201 S201 C202 103.0(7) . . ?
C202 S201 C201 98.9(6) . . ?
S201 C201 H20A 109.5 . . ?
S201 C201 H20B 109.5 . . ?
S201 C201 H20C 109.5 . . ?
H20A C201 H20B 109.5 . . ?
H20A C201 H20C 109.5 . . ?
H20B C201 H20C 109.5 . . ?
S201 C202 H20D 109.5 . . ?
S201 C202 H20E 109.5 . . ?
S201 C202 H20F 109.5 . . ?
H20D C202 H20E 109.5 . . ?
H20D C202 H20F 109.5 . . ?
H20E C202 H20F 109.5 . . ?
O211 S211 C211 102.9(12) . . ?
O211 S211 C212 102.8(12) . . ?
C212 S211 C211 104.4(11) . . ?
S211 C211 H21A 109.5 . . ?
S211 C211 H21B 109.5 . . ?
S211 C211 H21C 109.5 . . ?
H21A C211 H21B 109.5 . . ?
H21A C211 H21C 109.5 . . ?
H21B C211 H21C 109.5 . . ?
S211 C212 H21D 109.5 . . ?
S211 C212 H21E 109.5 . . ?
S211 C212 H21F 109.5 . . ?
H21D C212 H21E 109.5 . . ?
H21D C212 H21F 109.5 . . ?
H21E C212 H21F 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2341096'
loop_
_audit_author_name
_audit_author_address
'Petr Buikin'
;N S Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-04-20 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_audit_creation_date             2024-04-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
_chemical_formula_moiety         '1.5(C18 H18 N2), Bi2 I9, C3 H7 N O'
_chemical_formula_sum            'C30 H34 Bi2 I9 N4 O'
_chemical_formula_weight         2026.67
#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#
#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
# END of CIF
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_symmetry_Int_Tables_number      2
_cell_length_a                   10.4022(5)
_cell_length_b                   12.5641(7)
_cell_length_c                   19.9063(10)
_cell_angle_alpha                94.466(2)
_cell_angle_beta                 103.2530(10)
_cell_angle_gamma                112.5700(10)
_cell_volume                     2298.2(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9992
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.97
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   0.29
_shelx_estimated_absorpt_T_min   0.17
#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    13.719
_exptl_absorpt_correction_T_max  0.182
_exptl_absorpt_correction_T_min  0.032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.929
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1786
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 0.71065   17.348   14.716   13.824   90.004  121.680   90.007
;
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            53186
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.595
_diffrn_reflns_theta_min         2.192
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker AXS D8 VENTURE PHOTON III C14 IuS 3.0'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_reflns_Friedel_coverage         0
_reflns_number_gt                14053
_reflns_number_total             15231
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-2018 (Sheldrick, 2015)'
_refine_diff_density_max         2.22
_refine_diff_density_min         -1.858
_refine_diff_density_rms         0.197
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         15231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0258
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0100P)²+4.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0576
_refine_ls_wR_factor_ref         0.0588
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C13(H13A,H13B), C24(H24A,H24B)
1.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2A), C3(H3A), C4(H4A), C5(H5A), C8(H8A), C9(H9A), C11(H11A),
 C12(H12A), C14(H14A), C15(H15A), C16(H16A), C17(H17A), C18(H18A), C19(H19A),
 C20(H20A), C21(H21A), C22(H22A), C23(H23A), C26(H26A), C27(H27A), C101(H10G)
1.c Idealised Me refined as rotating group:
 C102(H10A,H10B,H10C), C103(H10D,H10E,H10F)
;
#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#
_atom_sites_solution_hydrogens   geom
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
Bi2 Bi 0.17062(2) -0.15819(2) 0.32290(2) 0.01823(3) Uani 1 1 d . . . . .
Bi1 Bi 0.29079(2) 0.11953(2) 0.21336(2) 0.01713(3) Uani 1 1 d . . . . .
I1 I 0.34367(3) 0.11822(2) 0.37647(2) 0.02270(5) Uani 1 1 d . . . . .
I2 I -0.02713(3) -0.09347(2) 0.19324(2) 0.02176(5) Uani 1 1 d . . . . .
I3 I 0.37064(3) -0.09619(2) 0.20426(2) 0.02147(5) Uani 1 1 d . . . . .
I4 I 0.59687(3) 0.29000(2) 0.24485(2) 0.02477(5) Uani 1 1 d . . . . .
I5 I 0.17291(3) 0.30287(2) 0.22581(2) 0.02089(5) Uani 1 1 d . . . . .
I6 I 0.22243(3) 0.10521(2) 0.05896(2) 0.02029(5) Uani 1 1 d . . . . .
I7 I 0.38476(3) -0.19692(2) 0.43174(2) 0.02049(5) Uani 1 1 d . . . . .
I8 I 0.01433(3) -0.41474(2) 0.26532(2) 0.02470(5) Uani 1 1 d . . . . .
I9 I -0.00900(3) -0.16073(3) 0.41449(2) 0.03058(6) Uani 1 1 d . . . . .
N1 N 1.1243(3) 0.7901(3) 0.63337(16) 0.0198(6) Uani 1 1 d . . . . .
N2 N 0.5228(3) 0.5573(3) 0.33705(16) 0.0200(6) Uani 1 1 d . . . . .
N3 N 0.1716(3) 0.8053(3) -0.02668(16) 0.0191(6) Uani 1 1 d . . . . .
C1 C 1.1260(5) 0.8739(4) 0.6805(2) 0.0285(8) Uani 1 1 d . . . . .
H1A H 1.067534 0.852586 0.711705 0.034 Uiso 1 1 calc R U . . .
C2 C 1.2113(5) 0.9893(4) 0.6836(2) 0.0319(9) Uani 1 1 d . . . . .
H2A H 1.210937 1.048324 0.716389 0.038 Uiso 1 1 calc R U . . .
C3 C 1.2981(4) 1.0197(4) 0.6389(2) 0.0269(8) Uani 1 1 d . . . . .
H3A H 1.359068 1.099535 0.641151 0.032 Uiso 1 1 calc R U . . .
C4 C 1.2953(4) 0.9327(4) 0.5909(2) 0.0258(8) Uani 1 1 d . . . . .
H4A H 1.354268 0.952066 0.559815 0.031 Uiso 1 1 calc R U . . .
C5 C 1.2062(4) 0.8181(4) 0.5887(2) 0.0242(7) Uani 1 1 d . . . . .
H5A H 1.202375 0.757878 0.555311 0.029 Uiso 1 1 calc R U . . .
C6 C 1.0300(4) 0.6651(3) 0.6294(2) 0.0243(7) Uani 1 1 d . . . . .
H6A H 1.000832 0.655846 0.673296 0.029 Uiso 1 1 calc R U . . .
H6B H 1.085688 0.617468 0.625403 0.029 Uiso 1 1 calc R U . . .
C7 C 0.8946(4) 0.6195(3) 0.56722(19) 0.0208(7) Uani 1 1 d . . . . .
C8 C 0.8206(4) 0.6898(4) 0.5479(2) 0.0232(7) Uani 1 1 d . . . . .
H8A H 0.855813 0.767397 0.573176 0.028 Uiso 1 1 calc R U . . .
C9 C 0.6959(4) 0.6461(4) 0.4921(2) 0.0236(7) Uani 1 1 d . . . . .
H9A H 0.645628 0.693948 0.479554 0.028 Uiso 1 1 calc R U . . .
C10 C 0.6433(4) 0.5329(3) 0.4540(2) 0.0230(7) Uani 1 1 d . . . . .
C11 C 0.7172(5) 0.4632(4) 0.4737(2) 0.0287(8) Uani 1 1 d . . . . .
H11A H 0.682461 0.385701 0.448322 0.034 Uiso 1 1 calc R U . . .
C12 C 0.8420(5) 0.5065(4) 0.5306(2) 0.0270(8) Uani 1 1 d . . . . .
H12A H 0.890908 0.458086 0.544076 0.032 Uiso 1 1 calc R U . . .
C13 C 0.5090(5) 0.4851(4) 0.3929(2) 0.0284(8) Uani 1 1 d . . . . .
H13A H 0.489413 0.403947 0.372948 0.034 Uiso 1 1 calc R U . . .
H13B H 0.425463 0.482319 0.409724 0.034 Uiso 1 1 calc R U . . .
C14 C 0.6421(4) 0.5895(3) 0.3140(2) 0.0238(7) Uani 1 1 d . . . . .
H14A H 0.717702 0.567056 0.334153 0.029 Uiso 1 1 calc R U . . .
C15 C 0.6550(4) 0.6543(4) 0.2618(2) 0.0250(8) Uani 1 1 d . . . . .
H15A H 0.739888 0.678345 0.246179 0.03 Uiso 1 1 calc R U . . .
C16 C 0.5420(5) 0.6846(4) 0.2318(2) 0.0293(8) Uani 1 1 d . . . . .
H16A H 0.548856 0.729675 0.195599 0.035 Uiso 1 1 calc R U . . .
C17 C 0.4205(5) 0.6484(4) 0.2554(2) 0.0287(8) Uani 1 1 d . . . . .
H17A H 0.342264 0.667688 0.234895 0.034 Uiso 1 1 calc R U . . .
C18 C 0.4114(4) 0.5845(3) 0.3084(2) 0.0240(7) Uani 1 1 d . . . . .
H18A H 0.32747 0.559745 0.324713 0.029 Uiso 1 1 calc R U . . .
C19 C 0.1515(4) 0.8708(3) -0.07485(19) 0.0227(7) Uani 1 1 d . . . . .
H19A H 0.063452 0.880578 -0.087245 0.027 Uiso 1 1 calc R U . . .
C20 C 0.2590(5) 0.9238(4) -0.1063(2) 0.0270(8) Uani 1 1 d . . . . .
H20A H 0.245224 0.969904 -0.140571 0.032 Uiso 1 1 calc R U . . .
C21 C 0.3875(5) 0.9095(4) -0.0876(2) 0.0298(9) Uani 1 1 d . . . . .
H21A H 0.461758 0.94434 -0.109498 0.036 Uiso 1 1 calc R U . . .
C22 C 0.4061(4) 0.8436(4) -0.0364(2) 0.0284(8) Uani 1 1 d . . . . .
H22A H 0.494139 0.834137 -0.022287 0.034 Uiso 1 1 calc R U . . .
C23 C 0.2968(4) 0.7921(4) -0.0063(2) 0.0244(7) Uani 1 1 d . . . . .
H23A H 0.309182 0.74723 0.02896 0.029 Uiso 1 1 calc R U . . .
C24 C 0.0554(4) 0.7468(3) 0.0068(2) 0.0254(8) Uani 1 1 d . . . . .
H24A H -0.034297 0.754173 -0.017574 0.031 Uiso 1 1 calc R U . . .
H24B H 0.085542 0.785841 0.056426 0.031 Uiso 1 1 calc R U . . .
C25 C 0.0252(4) 0.6189(3) 0.0035(2) 0.0207(7) Uani 1 1 d . . . . .
C26 C -0.0263(4) 0.5432(4) -0.0612(2) 0.0249(8) Uani 1 1 d . . . . .
H26A H -0.044313 0.572353 -0.103423 0.03 Uiso 1 1 calc R U . . .
C27 C -0.0516(4) 0.4253(4) -0.0645(2) 0.0259(8) Uani 1 1 d . . . . .
H27A H -0.087256 0.374819 -0.108873 0.031 Uiso 1 1 calc R U . . .
O101 O 0.5033(4) 0.6983(4) 0.06842(19) 0.0469(9) Uani 1 1 d . . . . .
N101 N 0.5738(4) 0.5493(4) 0.0872(2) 0.0337(8) Uani 1 1 d . . . . .
C101 C 0.5956(5) 0.6568(4) 0.0748(2) 0.0350(10) Uani 1 1 d . . . . .
H10G H 0.688279 0.705224 0.07047 0.042 Uiso 1 1 calc R U . . .
C102 C 0.6838(6) 0.5044(6) 0.0922(3) 0.0492(14) Uani 1 1 d . . . . .
H10A H 0.768373 0.561801 0.081692 0.074 Uiso 1 1 calc R U . . .
H10B H 0.644813 0.430753 0.058558 0.074 Uiso 1 1 calc R U . . .
H10C H 0.712659 0.490088 0.139921 0.074 Uiso 1 1 calc R U . . .
C103 C 0.4318(6) 0.4685(5) 0.0946(3) 0.0436(12) Uani 1 1 d . . . . .
H10D H 0.36322 0.505233 0.085532 0.065 Uiso 1 1 calc R U . . .
H10E H 0.444528 0.451879 0.142412 0.065 Uiso 1 1 calc R U . . .
H10F H 0.393838 0.395116 0.060852 0.065 Uiso 1 1 calc R U . . .


#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#
_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
Bi2 I1 3.1911(3) . ?
Bi2 I2 3.2758(3) . ?
Bi2 I7 2.9455(3) . ?
Bi2 I8 2.9823(3) . ?
Bi2 I9 2.8882(3) . ?
Bi1 I1 3.1687(3) . ?
Bi1 I2 3.2697(3) . ?
Bi1 I3 3.1287(3) . ?
Bi1 I4 2.9595(3) . ?
Bi1 I5 3.0149(3) . ?
Bi1 I6 2.9663(3) . ?
N1 C1 1.346(5) . ?
N1 C5 1.344(5) . ?
N1 C6 1.482(5) . ?
N2 C13 1.487(5) . ?
N2 C14 1.349(5) . ?
N2 C18 1.348(5) . ?
N3 C19 1.343(5) . ?
N3 C23 1.351(5) . ?
N3 C24 1.486(5) . ?
C1 H1A 0.95 . ?
C1 C2 1.366(6) . ?
C2 H2A 0.95 . ?
C2 C3 1.383(6) . ?
C3 H3A 0.95 . ?
C3 C4 1.381(6) . ?
C4 H4A 0.95 . ?
C4 C5 1.372(6) . ?
C5 H5A 0.95 . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C6 C7 1.521(5) . ?
C7 C8 1.400(5) . ?
C7 C12 1.380(5) . ?
C8 H8A 0.95 . ?
C8 C9 1.384(5) . ?
C9 H9A 0.95 . ?
C9 C10 1.394(6) . ?
C10 C11 1.395(6) . ?
C10 C13 1.501(5) . ?
C11 H11A 0.95 . ?
C11 C12 1.397(6) . ?
C12 H12A 0.95 . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 H14A 0.95 . ?
C14 C15 1.369(5) . ?
C15 H15A 0.95 . ?
C15 C16 1.392(5) . ?
C16 H16A 0.95 . ?
C16 C17 1.374(6) . ?
C17 H17A 0.95 . ?
C17 C18 1.373(6) . ?
C18 H18A 0.95 . ?
C19 H19A 0.95 . ?
C19 C20 1.378(6) . ?
C20 H20A 0.95 . ?
C20 C21 1.387(6) . ?
C21 H21A 0.95 . ?
C21 C22 1.388(6) . ?
C22 H22A 0.95 . ?
C22 C23 1.370(6) . ?
C23 H23A 0.95 . ?
C24 H24A 0.99 . ?
C24 H24B 0.99 . ?
C24 C25 1.507(5) . ?
C25 C26 1.397(5) . ?
C25 C27 1.389(5) 2_565 ?
C26 H26A 0.95 . ?
C26 C27 1.395(6) . ?
C27 H27A 0.95 . ?
O101 C101 1.244(6) . ?
N101 C101 1.334(6) . ?
N101 C102 1.445(6) . ?
N101 C103 1.486(6) . ?
C101 H10G 0.95 . ?
C102 H10A 0.98 . ?
C102 H10B 0.98 . ?
C102 H10C 0.98 . ?
C103 H10D 0.98 . ?
C103 H10E 0.98 . ?
C103 H10F 0.98 . ?

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
I1 Bi2 I2 85.899(8) . . ?
I7 Bi2 I1 89.919(8) . . ?
I7 Bi2 I2 171.556(8) . . ?
I7 Bi2 I8 91.248(8) . . ?
I8 Bi2 I1 176.698(8) . . ?
I8 Bi2 I2 92.543(8) . . ?
I9 Bi2 I1 88.776(9) . . ?
I9 Bi2 I2 94.230(9) . . ?
I9 Bi2 I7 93.010(9) . . ?
I9 Bi2 I8 94.246(9) . . ?
I1 Bi1 I2 86.367(7) . . ?
I3 Bi1 I1 86.647(7) . . ?
I3 Bi1 I2 79.819(8) . . ?
I4 Bi1 I1 87.986(8) . . ?
I4 Bi1 I2 171.032(8) . . ?
I4 Bi1 I3 92.908(9) . . ?
I4 Bi1 I5 95.016(9) . . ?
I4 Bi1 I6 95.915(8) . . ?
I5 Bi1 I1 90.615(7) . . ?
I5 Bi1 I2 92.008(8) . . ?
I5 Bi1 I3 171.521(8) . . ?
I6 Bi1 I1 175.935(8) . . ?
I6 Bi1 I2 89.621(7) . . ?
I6 Bi1 I3 92.001(8) . . ?
I6 Bi1 I5 90.182(7) . . ?
Bi1 I1 Bi2 82.484(7) . . ?
Bi1 I2 Bi2 79.664(7) . . ?
C1 N1 C6 120.3(3) . . ?
C5 N1 C1 120.8(3) . . ?
C5 N1 C6 118.9(3) . . ?
C14 N2 C13 119.9(3) . . ?
C18 N2 C13 118.5(3) . . ?
C18 N2 C14 121.5(3) . . ?
C19 N3 C23 121.8(3) . . ?
C19 N3 C24 120.1(3) . . ?
C23 N3 C24 118.1(3) . . ?
N1 C1 H1A 119.8 . . ?
N1 C1 C2 120.4(4) . . ?
C2 C1 H1A 119.8 . . ?
C1 C2 H2A 120.2 . . ?
C1 C2 C3 119.6(4) . . ?
C3 C2 H2A 120.2 . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 C2 119.3(4) . . ?
C4 C3 H3A 120.3 . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 C3 119.2(4) . . ?
C5 C4 H4A 120.4 . . ?
N1 C5 C4 120.6(4) . . ?
N1 C5 H5A 119.7 . . ?
C4 C5 H5A 119.7 . . ?
N1 C6 H6A 109.1 . . ?
N1 C6 H6B 109.1 . . ?
N1 C6 C7 112.3(3) . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
C8 C7 C6 120.7(4) . . ?
C12 C7 C6 119.7(3) . . ?
C12 C7 C8 119.6(4) . . ?
C7 C8 H8A 120 . . ?
C9 C8 C7 120.0(4) . . ?
C9 C8 H8A 120 . . ?
C8 C9 H9A 119.6 . . ?
C8 C9 C10 120.9(4) . . ?
C10 C9 H9A 119.6 . . ?
C9 C10 C11 118.8(4) . . ?
C9 C10 C13 121.3(4) . . ?
C11 C10 C13 119.9(4) . . ?
C10 C11 H11A 119.8 . . ?
C10 C11 C12 120.4(4) . . ?
C12 C11 H11A 119.8 . . ?
C7 C12 C11 120.3(4) . . ?
C7 C12 H12A 119.8 . . ?
C11 C12 H12A 119.8 . . ?
N2 C13 C10 112.2(3) . . ?
N2 C13 H13A 109.2 . . ?
N2 C13 H13B 109.2 . . ?
C10 C13 H13A 109.2 . . ?
C10 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
N2 C14 H14A 119.8 . . ?
N2 C14 C15 120.5(4) . . ?
C15 C14 H14A 119.8 . . ?
C14 C15 H15A 120.5 . . ?
C14 C15 C16 119.1(4) . . ?
C16 C15 H15A 120.5 . . ?
C15 C16 H16A 120.4 . . ?
C17 C16 C15 119.1(4) . . ?
C17 C16 H16A 120.4 . . ?
C16 C17 H17A 119.8 . . ?
C18 C17 C16 120.4(4) . . ?
C18 C17 H17A 119.8 . . ?
N2 C18 C17 119.4(4) . . ?
N2 C18 H18A 120.3 . . ?
C17 C18 H18A 120.3 . . ?
N3 C19 H19A 120.1 . . ?
N3 C19 C20 119.8(4) . . ?
C20 C19 H19A 120.1 . . ?
C19 C20 H20A 120.2 . . ?
C19 C20 C21 119.7(4) . . ?
C21 C20 H20A 120.2 . . ?
C20 C21 H21A 120.5 . . ?
C20 C21 C22 119.0(4) . . ?
C22 C21 H21A 120.5 . . ?
C21 C22 H22A 120.1 . . ?
C23 C22 C21 119.7(4) . . ?
C23 C22 H22A 120.1 . . ?
N3 C23 C22 120.0(4) . . ?
N3 C23 H23A 120 . . ?
C22 C23 H23A 120 . . ?
N3 C24 H24A 109.5 . . ?
N3 C24 H24B 109.5 . . ?
N3 C24 C25 110.7(3) . . ?
H24A C24 H24B 108.1 . . ?
C25 C24 H24A 109.5 . . ?
C25 C24 H24B 109.5 . . ?
C26 C25 C24 120.5(3) . . ?
C27 C25 C24 120.7(4) 2_565 . ?
C27 C25 C26 118.8(4) 2_565 . ?
C25 C26 H26A 119.7 . . ?
C27 C26 C25 120.6(4) . . ?
C27 C26 H26A 119.7 . . ?
C25 C27 C26 120.6(4) 2_565 . ?
C25 C27 H27A 119.7 2_565 . ?
C26 C27 H27A 119.7 . . ?
C101 N101 C102 122.4(5) . . ?
C101 N101 C103 120.8(4) . . ?
C102 N101 C103 116.8(4) . . ?
O101 C101 N101 124.7(5) . . ?
O101 C101 H10G 117.6 . . ?
N101 C101 H10G 117.6 . . ?
N101 C102 H10A 109.5 . . ?
N101 C102 H10B 109.5 . . ?
N101 C102 H10C 109.5 . . ?
H10A C102 H10B 109.5 . . ?
H10A C102 H10C 109.5 . . ?
H10B C102 H10C 109.5 . . ?
N101 C103 H10D 109.5 . . ?
N101 C103 H10E 109.5 . . ?
N101 C103 H10F 109.5 . . ?
H10D C103 H10E 109.5 . . ?
H10D C103 H10F 109.5 . . ?
H10E C103 H10F 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_pyxk_bibr_1_4_dmso_new
_database_code_depnum_ccdc_archive 'CCDC 2341094'
loop_
_audit_author_name
_audit_author_address
'Petr Buikin'
;N S Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-05-15 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_audit_creation_date             2024-03-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 H6 Bi Br4 O S, C9 H9 N'
_chemical_formula_sum            'C11 H15 Bi Br4 N O S'
_chemical_formula_weight         737.92
_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 0.0033 0.0016 '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'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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                   11.442(3)
_cell_length_b                   13.461(3)
_cell_length_c                   12.460(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.555(7)
_cell_angle_gamma                90
_cell_volume                     1829.8(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5870
_cell_measurement_temperature    140
_cell_measurement_theta_max      27.768
_cell_measurement_theta_min      2.288
_shelx_estimated_absorpt_T_max   0.459
_shelx_estimated_absorpt_T_min   0.215
_exptl_absorpt_coefficient_mu    18.476
_exptl_absorpt_correction_T_max  0.0511
_exptl_absorpt_correction_T_min  0.0097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1692 before and 0.0587 after correction.
The Ratio of minimum to maximum transmission is 0.1898.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.679
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1340
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18230
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.015
_diffrn_reflns_theta_min         2.120
_diffrn_ambient_temperature      140
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3122
_reflns_number_total             3599
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         2.216
_refine_diff_density_min         -0.896
_refine_diff_density_rms         0.180
_refine_ls_extinction_coef       0.00274(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3599
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0323
_refine_ls_restrained_S_all      1.034
_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)+2.7346P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0785
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
1.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9)
1.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_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
Bi1 Bi 0.38616(2) 0.55578(2) 0.59907(2) 0.02595(11) Uani 1 1 d . . . . .
Br2 Br 0.59747(6) 0.64152(5) 0.73943(6) 0.03456(18) Uani 1 1 d . . . . .
Br4 Br 0.24957(6) 0.72188(5) 0.58934(6) 0.03866(19) Uani 1 1 d . . . . .
S1 S 0.14047(15) 0.48627(12) 0.34973(14) 0.0307(4) Uani 1 1 d . . . . .
O1 O 0.2088(4) 0.4632(3) 0.4724(4) 0.0342(11) Uani 1 1 d . . . . .
C10 C 0.0533(8) 0.3786(6) 0.2950(7) 0.054(2) Uani 1 1 d . . . . .
H10A H 0.107641 0.326978 0.281433 0.081 Uiso 1 1 calc R U . . .
H10B H -0.009127 0.395113 0.224070 0.081 Uiso 1 1 calc R U . . .
H10C H 0.013401 0.354181 0.349268 0.081 Uiso 1 1 calc R U . . .
C11 C 0.0195(8) 0.5663(6) 0.3531(8) 0.060(3) Uani 1 1 d . . . . .
H11A H -0.035723 0.531739 0.387220 0.089 Uiso 1 1 calc R U . . .
H11B H -0.025919 0.586300 0.276149 0.089 Uiso 1 1 calc R U . . .
H11C H 0.053100 0.625440 0.397641 0.089 Uiso 1 1 calc R U . . .
N007 N 0.2174(5) 0.1492(4) 0.4393(4) 0.0264(11) Uani 1 1 d . . . . .
C1 C 0.1048(6) 0.1144(5) 0.4279(6) 0.0307(15) Uani 1 1 d . . . . .
H1 H 0.067674 0.069200 0.368972 0.037 Uiso 1 1 calc R U . . .
C2 C 0.0425(6) 0.1439(5) 0.5012(6) 0.0341(16) Uani 1 1 d . . . . .
H2 H -0.037171 0.118946 0.494010 0.041 Uiso 1 1 calc R U . . .
C3 C 0.0979(8) 0.2105(5) 0.5854(7) 0.046(2) Uani 1 1 d . . . . .
H3 H 0.056917 0.230071 0.637983 0.055 Uiso 1 1 calc R U . . .
C4 C 0.2125(8) 0.2491(5) 0.5941(6) 0.0424(18) Uani 1 1 d . . . . .
H4 H 0.249678 0.296401 0.650776 0.051 Uiso 1 1 calc R U . . .
C5 C 0.2715(7) 0.2176(5) 0.5190(6) 0.0366(16) Uani 1 1 d . . . . .
H5 H 0.349813 0.243565 0.522877 0.044 Uiso 1 1 calc R U . . .
C6 C 0.2882(6) 0.1111(5) 0.3657(5) 0.0312(15) Uani 1 1 d . . . . .
H6A H 0.315451 0.167413 0.327976 0.037 Uiso 1 1 calc R U . . .
H6B H 0.235400 0.067498 0.306832 0.037 Uiso 1 1 calc R U . . .
C7 C 0.3981(6) 0.0536(4) 0.4348(5) 0.0266(14) Uani 1 1 d . . . . .
C8 C 0.5149(6) 0.0925(5) 0.4595(5) 0.0290(14) Uani 1 1 d . . . . .
H8 H 0.526101 0.156301 0.431605 0.035 Uiso 1 1 calc R U . . .
C9 C 0.3845(6) -0.0406(5) 0.4763(6) 0.0329(16) Uani 1 1 d . . . . .
H9 H 0.305207 -0.069171 0.460027 0.039 Uiso 1 1 calc R U . . .
Br3A Br 0.31064(6) 0.48078(5) 0.77046(6) 0.03591(18) Uani 1 1 d . . . A 1
Br1A Br 0.45485(6) 0.62927(5) 0.39690(6) 0.03089(17) 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
Bi1 Br2 2.7724(9) . ?
Bi1 Br4 2.7096(8) . ?
Bi1 O1 2.496(5) . ?
Bi1 Br3A 2.7276(9) . ?
Bi1 Br1A 3.0227(9) . ?
Bi1 Br1A 3.0761(9) 3_666 ?
S1 O1 1.524(5) . ?
S1 C10 1.775(8) . ?
S1 C11 1.764(8) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
N007 C1 1.338(8) . ?
N007 C5 1.359(8) . ?
N007 C6 1.486(8) . ?
C1 H1 0.9500 . ?
C1 C2 1.376(9) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(10) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(11) . ?
C4 H4 0.9500 . ?
C4 C5 1.376(10) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.506(8) . ?
C7 C8 1.380(9) . ?
C7 C9 1.395(8) . ?
C8 H8 0.9500 . ?
C8 C9 1.378(9) 3_656 ?
C9 H9 0.9500 . ?

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
Br2 Bi1 Br1A 85.86(3) . 3_666 ?
Br2 Bi1 Br1A 89.60(3) . . ?
Br4 Bi1 Br2 93.80(3) . . ?
Br4 Bi1 Br3A 91.48(3) . . ?
Br4 Bi1 Br1A 177.77(2) . 3_666 ?
Br4 Bi1 Br1A 89.09(2) . . ?
O1 Bi1 Br2 174.15(11) . . ?
O1 Bi1 Br4 92.04(11) . . ?
O1 Bi1 Br3A 85.47(11) . . ?
O1 Bi1 Br1A 88.29(11) . 3_666 ?
O1 Bi1 Br1A 90.15(11) . . ?
Br3A Bi1 Br2 94.71(3) . . ?
Br3A Bi1 Br1A 175.60(2) . . ?
Br3A Bi1 Br1A 90.74(2) . 3_666 ?
Br1A Bi1 Br1A 88.71(2) . 3_666 ?
O1 S1 C10 106.1(3) . . ?
O1 S1 C11 105.6(4) . . ?
C11 S1 C10 98.9(4) . . ?
S1 O1 Bi1 127.3(2) . . ?
S1 C10 H10A 109.5 . . ?
S1 C10 H10B 109.5 . . ?
S1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
S1 C11 H11A 109.5 . . ?
S1 C11 H11B 109.5 . . ?
S1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 N007 C5 121.7(6) . . ?
C1 N007 C6 120.1(5) . . ?
C5 N007 C6 118.2(5) . . ?
N007 C1 H1 119.8 . . ?
N007 C1 C2 120.3(6) . . ?
C2 C1 H1 119.8 . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.8(6) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.7(7) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.6(7) . . ?
C5 C4 H4 120.7 . . ?
N007 C5 C4 119.9(6) . . ?
N007 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
N007 C6 H6A 109.7 . . ?
N007 C6 H6B 109.7 . . ?
N007 C6 C7 109.9(5) . . ?
H6A C6 H6B 108.2 . . ?
C7 C6 H6A 109.7 . . ?
C7 C6 H6B 109.7 . . ?
C8 C7 C6 121.2(6) . . ?
C8 C7 C9 118.0(6) . . ?
C9 C7 C6 120.8(6) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.3(6) 3_656 . ?
C9 C8 H8 119.3 3_656 . ?
C7 C9 H9 119.7 . . ?
C8 C9 C7 120.6(6) 3_656 . ?
C8 C9 H9 119.7 3_656 . ?
Bi1 Br1A Bi1 91.29(2) . 3_666 ?

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
C10 S1 O1 Bi1 164.8(4) . . . . ?
C11 S1 O1 Bi1 -90.8(4) . . . . ?
N007 C1 C2 C3 0.7(10) . . . . ?
N007 C6 C7 C8 -106.4(7) . . . . ?
N007 C6 C7 C9 73.4(8) . . . . ?
C1 N007 C5 C4 3.2(10) . . . . ?
C1 N007 C6 C7 -113.3(6) . . . . ?
C1 C2 C3 C4 1.8(10) . . . . ?
C2 C3 C4 C5 -1.8(11) . . . . ?
C3 C4 C5 N007 -0.7(10) . . . . ?
C5 N007 C1 C2 -3.2(9) . . . . ?
C5 N007 C6 C7 65.1(7) . . . . ?
C6 N007 C1 C2 175.2(6) . . . . ?
C6 N007 C5 C4 -175.2(6) . . . . ?
C6 C7 C8 C9 179.3(6) . . . 3_656 ?
C6 C7 C9 C8 -179.3(6) . . . 3_656 ?
C8 C7 C9 C8 0.4(11) . . . 3_656 ?
C9 C7 C8 C9 -0.5(11) . . . 3_656 ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_pyxk_bii_dmso_1_4
_database_code_depnum_ccdc_archive 'CCDC 2341095'
loop_
_audit_author_name
_audit_author_address
'Petr Buikin'
;N S Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-05-15 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_audit_creation_date             2024-02-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 H6 Bi I4 O S, C9 H9 N'
_chemical_formula_sum            'C11 H15 Bi I4 N O S'
_chemical_formula_weight         925.88
_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 0.0033 0.0016 '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'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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                   11.7459(14)
_cell_length_b                   14.2042(19)
_cell_length_c                   12.5884(15)
_cell_angle_alpha                90
_cell_angle_beta                 106.018(4)
_cell_angle_gamma                90
_cell_volume                     2018.7(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5307
_cell_measurement_temperature    140
_cell_measurement_theta_max      25.845
_cell_measurement_theta_min      2.304
_shelx_estimated_absorpt_T_max   0.865
_shelx_estimated_absorpt_T_min   0.381
_exptl_absorpt_coefficient_mu    14.948
_exptl_absorpt_correction_T_max  0.0955
_exptl_absorpt_correction_T_min  0.0304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1596 before and 0.0625 after correction.
The Ratio of minimum to maximum transmission is 0.3873.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    3.046
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1628
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_unetI/netI     0.0581
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20088
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.017
_diffrn_reflns_theta_min         2.100
_diffrn_ambient_temperature      140
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3347
_reflns_number_total             3976
_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       'SAINT V8.30A (22 Oct 2012)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.30A (22 Oct 2012)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.019
_refine_diff_density_min         -1.473
_refine_diff_density_rms         0.221
_refine_ls_extinction_coef       0.00117(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3976
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0303
_refine_ls_restrained_S_all      1.026
_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)+(0.0159P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0680
_refine_ls_wR_factor_ref         0.0714
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
1.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9)
1.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_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
Bi1 Bi 0.38530(2) 0.44209(2) 0.60545(2) 0.02145(9) Uani 1 1 d . . . . .
I1 I 0.45214(4) 0.36736(3) 0.38956(4) 0.02437(12) Uani 1 1 d . . . . .
I2 I 0.24363(4) 0.27273(3) 0.59726(4) 0.03083(14) Uani 1 1 d . . . . .
I3 I 0.60242(4) 0.35045(3) 0.74904(4) 0.02735(13) Uani 1 1 d . . . . .
I4 I 0.30214(4) 0.52191(3) 0.78707(4) 0.02760(13) Uani 1 1 d . . . . .
S1 S 0.14964(17) 0.51223(13) 0.35983(15) 0.0279(4) Uani 1 1 d . . . . .
O1 O 0.2095(4) 0.5291(3) 0.4809(4) 0.0306(12) Uani 1 1 d . . . . .
C10 C 0.0326(8) 0.4339(5) 0.3573(7) 0.044(2) Uani 1 1 d . . . . .
H10A H 0.063376 0.379067 0.403553 0.066 Uiso 1 1 calc R U . . .
H10B H -0.003695 0.413298 0.281159 0.066 Uiso 1 1 calc R U . . .
H10C H -0.026911 0.465790 0.385724 0.066 Uiso 1 1 calc R U . . .
C11 C 0.0651(8) 0.6146(6) 0.3115(7) 0.045(2) Uani 1 1 d . . . . .
H11A H 0.015323 0.629244 0.360249 0.068 Uiso 1 1 calc R U . . .
H11B H 0.014746 0.603674 0.236291 0.068 Uiso 1 1 calc R U . . .
H11C H 0.118450 0.667582 0.311067 0.068 Uiso 1 1 calc R U . . .
N1 N 0.2260(5) 0.8567(4) 0.4385(4) 0.0215(13) Uani 1 1 d . . . . .
C1 C 0.1170(7) 0.8870(6) 0.4345(6) 0.0311(17) Uani 1 1 d . . . . .
H1 H 0.081154 0.936149 0.385426 0.037 Uiso 1 1 calc R U . . .
C2 C 0.0576(6) 0.8457(5) 0.5024(6) 0.0310(18) Uani 1 1 d . . . . .
H2 H -0.020492 0.865423 0.499346 0.037 Uiso 1 1 calc R U . . .
C3 C 0.1108(8) 0.7762(5) 0.5745(6) 0.035(2) Uani 1 1 d . . . . .
H3 H 0.070002 0.748046 0.621814 0.042 Uiso 1 1 calc R U . . .
C4 C 0.2241(7) 0.7474(5) 0.5781(6) 0.0352(19) Uani 1 1 d . . . . .
H4 H 0.263144 0.700611 0.629275 0.042 Uiso 1 1 calc R U . . .
C5 C 0.2784(7) 0.7871(5) 0.5072(6) 0.0323(18) Uani 1 1 d . . . . .
H5 H 0.354593 0.765463 0.506001 0.039 Uiso 1 1 calc R U . . .
C6 C 0.2924(6) 0.9028(5) 0.3676(6) 0.0259(16) Uani 1 1 d . . . . .
H6A H 0.240098 0.948488 0.317634 0.031 Uiso 1 1 calc R U . . .
H6B H 0.316825 0.854666 0.321367 0.031 Uiso 1 1 calc R U . . .
C7 C 0.3997(6) 0.9527(5) 0.4363(5) 0.0203(15) Uani 1 1 d . . . . .
C8 C 0.5126(6) 0.9133(5) 0.4541(6) 0.0249(16) Uani 1 1 d . . . . .
H8 H 0.521837 0.854475 0.421647 0.030 Uiso 1 1 calc R U . . .
C9 C 0.3887(6) 1.0399(5) 0.4807(6) 0.0257(16) Uani 1 1 d . . . . .
H9 H 0.312782 1.068362 0.466612 0.031 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
Bi1 I1 3.3029(6) 3_666 ?
Bi1 I1 3.2103(6) . ?
Bi1 I2 2.9107(6) . ?
Bi1 I3 2.9868(6) . ?
Bi1 I4 2.9495(6) . ?
Bi1 O1 2.543(5) . ?
S1 O1 1.512(5) . ?
S1 C10 1.762(8) . ?
S1 C11 1.772(8) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
N1 C1 1.339(9) . ?
N1 C5 1.346(9) . ?
N1 C6 1.490(8) . ?
C1 H1 0.9500 . ?
C1 C2 1.375(10) . ?
C2 H2 0.9500 . ?
C2 C3 1.369(11) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(10) . ?
C4 H4 0.9500 . ?
C4 C5 1.355(10) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.496(9) . ?
C7 C8 1.399(9) . ?
C7 C9 1.380(9) . ?
C8 H8 0.9500 . ?
C8 C9 1.390(10) 3_676 ?
C9 H9 0.9500 . ?

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
I1 Bi1 I1 90.684(14) . 3_666 ?
I2 Bi1 I1 88.151(16) . . ?
I2 Bi1 I1 178.833(15) . 3_666 ?
I2 Bi1 I3 92.613(18) . . ?
I2 Bi1 I4 92.106(17) . . ?
I3 Bi1 I1 90.047(16) . . ?
I3 Bi1 I1 87.308(16) . 3_666 ?
I4 Bi1 I1 173.701(16) . . ?
I4 Bi1 I1 89.060(15) . 3_666 ?
I4 Bi1 I3 96.227(17) . . ?
O1 Bi1 I1 88.86(11) . 3_666 ?
O1 Bi1 I1 89.19(11) . . ?
O1 Bi1 I2 91.20(11) . . ?
O1 Bi1 I3 176.09(11) . . ?
O1 Bi1 I4 84.51(11) . . ?
Bi1 I1 Bi1 89.318(14) . 3_666 ?
O1 S1 C10 105.2(4) . . ?
O1 S1 C11 106.1(3) . . ?
C10 S1 C11 98.7(4) . . ?
S1 O1 Bi1 128.1(3) . . ?
S1 C10 H10A 109.5 . . ?
S1 C10 H10B 109.5 . . ?
S1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
S1 C11 H11A 109.5 . . ?
S1 C11 H11B 109.5 . . ?
S1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 N1 C5 121.6(6) . . ?
C1 N1 C6 119.3(6) . . ?
C5 N1 C6 119.1(6) . . ?
N1 C1 H1 120.6 . . ?
N1 C1 C2 118.9(7) . . ?
C2 C1 H1 120.6 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(7) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.7(7) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.6(7) . . ?
C5 C4 H4 120.7 . . ?
N1 C5 C4 120.9(7) . . ?
N1 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
N1 C6 H6A 109.4 . . ?
N1 C6 H6B 109.4 . . ?
N1 C6 C7 111.0(5) . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C8 C7 C6 120.9(6) . . ?
C9 C7 C6 120.1(6) . . ?
C9 C7 C8 119.0(6) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.2(6) 3_676 . ?
C9 C8 H8 119.9 3_676 . ?
C7 C9 C8 120.8(6) . 3_676 ?
C7 C9 H9 119.6 . . ?
C8 C9 H9 119.6 3_676 . ?

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
C10 S1 O1 Bi1 93.0(4) . . . . ?
C11 S1 O1 Bi1 -163.0(4) . . . . ?
N1 C1 C2 C3 1.4(11) . . . . ?
N1 C6 C7 C8 102.5(7) . . . . ?
N1 C6 C7 C9 -79.2(8) . . . . ?
C1 N1 C5 C4 -2.6(11) . . . . ?
C1 N1 C6 C7 114.6(7) . . . . ?
C1 C2 C3 C4 -0.4(11) . . . . ?
C2 C3 C4 C5 -1.9(12) . . . . ?
C3 C4 C5 N1 3.4(12) . . . . ?
C5 N1 C1 C2 0.1(11) . . . . ?
C5 N1 C6 C7 -63.8(8) . . . . ?
C6 N1 C1 C2 -178.3(6) . . . . ?
C6 N1 C5 C4 175.8(7) . . . . ?
C6 C7 C8 C9 -179.2(6) . . . 3_676 ?
C6 C7 C9 C8 179.2(6) . . . 3_676 ?
C8 C7 C9 C8 -2.5(11) . . . 3_676 ?
C9 C7 C8 C9 2.4(11) . . . 3_676 ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_pyxk_bibr_4_1_dmso_0m
_database_code_depnum_ccdc_archive 'CCDC 2341099'
loop_
_audit_author_name
_audit_author_address
'Petr Buikin'
;N S Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-05-15 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_audit_creation_date             2024-03-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'Bi0.5 Br2.14 Cl0.86, Bi0.5 Br1.97 Cl1.03, 2(C9 H9 N), C9 H10 N'
_chemical_formula_sum            'C27 H28 Bi Br4.11 Cl1.89 N3'
_chemical_formula_weight         998.93
_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 0.0033 0.0016 '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'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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                   9.4546(10)
_cell_length_b                   13.2860(12)
_cell_length_c                   13.9063(11)
_cell_angle_alpha                81.087(3)
_cell_angle_beta                 76.125(4)
_cell_angle_gamma                69.233(4)
_cell_volume                     1581.0(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1780
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.681
_cell_measurement_theta_min      2.321
_shelx_estimated_absorpt_T_max   0.290
_shelx_estimated_absorpt_T_min   0.218
_exptl_absorpt_coefficient_mu    10.951
_exptl_absorpt_correction_T_max  0.2657
_exptl_absorpt_correction_T_min  0.1630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0906 before and 0.0451 after correction. The Ratio of minimum to maximum transmission is 0.6461. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.098
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             940
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0816
_diffrn_reflns_av_unetI/netI     0.0653
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            62971
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.597
_diffrn_reflns_theta_min         1.644
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7008
_reflns_number_total             9451
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         1.559
_refine_diff_density_min         -0.997
_refine_diff_density_rms         0.209
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         9451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.040
_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)+(0.0076P)²+3.8193P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0546
_refine_ls_wR_factor_ref         0.0633
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
Uanis(Cl0A) = Uanis(Br07)
Uanis(Br08) = Uanis(Cl1A)
Uanis(Cl2A) = Uanis(Br06)
Uanis(Cl3A) = Uanis(Br03)
Uanis(Cl4A) = Uanis(Br04)
Uanis(Cl) = Uanis(Br05)
2. Others
 Sof(Cl0A)=1-FVAR(1)
 Sof(Br07)=FVAR(1)
 Sof(Cl1A)=1-FVAR(2)
 Sof(Br08)=FVAR(2)
 Sof(Cl2A)=1-FVAR(3)
 Sof(Br06)=FVAR(3)
 Sof(Cl3A)=1-FVAR(4)
 Sof(Br03)=FVAR(4)
 Sof(Cl4A)=1-FVAR(5)
 Sof(Br04)=FVAR(5)
 Sof(Cl)=1-FVAR(6)
 Sof(Br05)=FVAR(6)
3.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C1BA(H1BA,H1BB), C9AA(H9AA,H9AB)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
 C18(H18), C3AA(H3AA), C8AA(H8AA), C4(H4), C2AA(H2AA), C4AA(H4AA), C0BA(H0BA),
 C7AA(H7AA), C6AA(H6AA), C1AA(H1AA), C5AA(H5AA), C0AA(H0AA)
;
_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
Bi01 Bi 1.000000 0.000000 0.500000 0.01536(6) Uani 1 2 d S T P . .
Bi02 Bi -0.500000 0.500000 1.000000 0.01720(6) Uani 1 2 d S T P . .
Br03 Br 0.9588(4) 0.1753(2) 0.34659(19) 0.0187(3) Uani 0.817(3) 1 d . . . A 1
Br04 Br -0.7500(5) 0.6325(3) 0.9105(4) 0.0224(4) Uani 0.744(4) 1 d . . . B 1
Br05 Br -0.33927(11) 0.65331(11) 0.93932(10) 0.0224(2) Uani 0.860(4) 1 d . . .
B 1
Br06 Br 1.0965(4) 0.1170(3) 0.6114(4) 0.0212(4) Uani 0.755(4) 1 d . . . A 1
Br07 Br 0.6922(11) 0.0806(9) 0.6033(7) 0.0238(7) Uani 0.573(4) 1 d . . . A 1
Br08 Br -0.353(2) 0.3933(15) 0.8199(12) 0.0190(13) Uani 0.362(3) 1 d . . . B 1
N1 N 0.3089(4) 0.3036(3) 0.3353(3) 0.0174(8) Uani 1 1 d . . . . .
C3 C -0.0461(5) 0.4220(4) 0.4735(4) 0.0226(10) Uani 1 1 d . . . . .
H3 H -0.078193 0.368492 0.455633 0.027 Uiso 1 1 calc R . . . .
N5 N 0.3023(4) 0.3562(3) 0.7197(3) 0.0212(8) Uani 1 1 d . . . . .
C7 C 0.0777(5) 0.4476(4) 0.4138(3) 0.0189(9) Uani 1 1 d . . . . .
C8 C 0.1178(6) 0.4268(4) 0.8610(4) 0.0313(12) Uani 1 1 d . . . . .
H8 H 0.088269 0.467082 0.917596 0.038 Uiso 1 1 calc R . . . .
C9 C 0.2600(6) 0.4111(4) 0.8005(4) 0.0278(11) Uani 1 1 d . . . . .
H9 H 0.329963 0.439749 0.816256 0.033 Uiso 1 1 calc R . . . .
C10 C 0.4601(5) 0.3361(4) 0.6582(4) 0.0261(11) Uani 1 1 d . . . . .
H10A H 0.492113 0.266766 0.627817 0.031 Uiso 1 1 calc R . . . .
H10B H 0.532218 0.328343 0.702191 0.031 Uiso 1 1 calc R . . . .
C11 C 0.1610(5) 0.3911(4) 0.3202(3) 0.0202(10) Uani 1 1 d . . . . .
H11A H 0.093502 0.359222 0.300062 0.024 Uiso 1 1 calc R . . . .
H11B H 0.184292 0.444323 0.266101 0.024 Uiso 1 1 calc R . . . .
C12 C 0.4459(5) 0.3143(4) 0.2897(3) 0.0202(10) Uani 1 1 d . . . . .
H12 H 0.449575 0.377809 0.248544 0.024 Uiso 1 1 calc R . . . .
C13 C -0.1240(5) 0.4742(4) 0.5596(3) 0.0231(10) Uani 1 1 d . . . . .
H13 H -0.209292 0.456311 0.600390 0.028 Uiso 1 1 calc R . . . .
C14 C 0.5744(5) 0.3916(4) 0.4881(4) 0.0264(11) Uani 1 1 d . . . . .
H14 H 0.626632 0.317007 0.479302 0.032 Uiso 1 1 calc R . . . .
C15 C 0.4010(5) 0.5331(4) 0.5880(4) 0.0253(11) Uani 1 1 d . . . . .
H15 H 0.332900 0.556615 0.648625 0.030 Uiso 1 1 calc R . . . .
C16 C 0.2050(6) 0.3147(4) 0.6961(4) 0.0266(11) Uani 1 1 d . . . . .
H16 H 0.235627 0.275962 0.638369 0.032 Uiso 1 1 calc R . . . .
C18 C 0.0176(6) 0.3835(4) 0.8387(4) 0.0288(11) Uani 1 1 d . . . . .
H18 H -0.080601 0.391945 0.880731 0.035 Uiso 1 1 calc R . . . .
C20 C 0.4746(5) 0.4227(4) 0.5774(3) 0.0208(10) Uani 1 1 d . . . . .
C3AA C 0.5739(6) 0.1426(4) 0.3641(4) 0.0261(11) Uani 1 1 d . . . . .
H3AA H 0.666300 0.086626 0.374357 0.031 Uiso 1 1 calc R . . . .
N2 N 0.6903(5) 0.0530(3) 0.8525(3) 0.0232(9) Uani 1 1 d . . . . .
C8AA C 0.6804(6) -0.0407(4) 0.8347(4) 0.0285(11) Uani 1 1 d . . . . .
H8AA H 0.771659 -0.097989 0.811751 0.034 Uiso 1 1 calc R . . . .
C4 C 0.5633(6) 0.1340(4) 0.8865(3) 0.0256(11) Uani 1 1 d . . . . .
H4 H 0.572728 0.199030 0.899997 0.031 Uiso 1 1 calc R . . . .
C2AA C 0.4326(6) 0.1333(4) 0.4108(4) 0.0326(12) Uani 1 1 d . . . . .
H2AA H 0.426480 0.071053 0.453263 0.039 Uiso 1 1 calc R . . . .
C6 C 0.9248(5) 0.0322(4) 0.9193(3) 0.0225(10) Uani 1 1 d . . . . .
C4AA C 0.5809(6) 0.2331(4) 0.3026(3) 0.0252(11) Uani 1 1 d . . . . .
H4AA H 0.677890 0.239635 0.269376 0.030 Uiso 1 1 calc R . . . .
C0BA C 1.0242(6) -0.0726(4) 0.9317(4) 0.0297(12) Uani 1 1 d . . . . .
H0BA H 1.041951 -0.123129 0.885054 0.036 Uiso 1 1 calc R . . . .
C7AA C 0.4198(6) 0.1243(4) 0.9019(4) 0.0297(12) Uani 1 1 d . . . . .
H7AA H 0.329931 0.182092 0.925724 0.036 Uiso 1 1 calc R . . . .
C1BA C 0.9020(6) 0.1039(4) 0.9879(4) 0.0313(12) Uani 1 1 d . . . . .
H1BA H 0.789628 0.131421 1.015267 0.038 Uiso 1 1 calc R . . . .
H1BB H 0.930617 0.166082 0.950891 0.038 Uiso 1 1 calc R . . . .
C6AA C 0.4081(6) 0.0296(4) 0.8825(4) 0.0284(11) Uani 1 1 d . . . . .
H6AA H 0.309419 0.022016 0.891993 0.034 Uiso 1 1 calc R . . . .
C1AA C 0.3010(6) 0.2152(4) 0.3949(4) 0.0282(11) Uani 1 1 d . . . . .
H1AA H 0.203008 0.209326 0.426414 0.034 Uiso 1 1 calc R . . . .
C5AA C 0.5384(6) -0.0538(4) 0.8495(4) 0.0303(12) Uani 1 1 d . . . . .
H5AA H 0.530886 -0.119895 0.837083 0.036 Uiso 1 1 calc R . . . .
C9AA C 0.8458(6) 0.0674(4) 0.8312(4) 0.0294(12) Uani 1 1 d . . . . .
H9AA H 0.833188 0.144449 0.811176 0.035 Uiso 1 1 calc R . . . .
H9AB H 0.912530 0.025101 0.774627 0.035 Uiso 1 1 calc R . . . .
C0AA C 0.0620(6) 0.3282(4) 0.7552(4) 0.0288(11) Uani 1 1 d . . . . .
H0AA H -0.006532 0.299203 0.738272 0.035 Uiso 1 1 calc R . . . .
Cl0A Cl 0.704(4) 0.083(3) 0.596(2) 0.0238(7) Uani 0.427(4) 1 d . . . A 2
Cl1A Cl -0.349(3) 0.397(2) 0.8311(17) 0.0190(13) Uani 0.638(3) 1 d . . . B 2
Cl2A Cl 1.079(4) 0.127(3) 0.609(3) 0.0212(4) Uani 0.245(4) 1 d . . . A 2
Cl3A Cl 0.958(5) 0.163(3) 0.357(2) 0.0187(3) Uani 0.183(3) 1 d . . . A 2
Cl4A Cl -0.738(4) 0.622(3) 0.904(3) 0.0224(4) Uani 0.256(4) 1 d . . . B 2
Cl Cl -0.371(2) 0.650(2) 0.9391(19) 0.0224(2) Uani 0.140(4) 1 d . . . B 2


_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
Bi01 Br03 2.8885(18) . ?
Bi01 Br03 2.8885(18) 2_756 ?
Bi01 Br06 2.842(5) 2_756 ?
Bi01 Br06 2.843(5) . ?
Bi01 Br07 2.818(9) 2_756 ?
Bi01 Br07 2.818(9) . ?
Bi01 Cl0A 2.70(3) . ?
Bi01 Cl0A 2.70(3) 2_756 ?
Bi01 Cl2A 2.81(4) . ?
Bi01 Cl2A 2.81(4) 2_756 ?
Bi01 Cl3A 2.69(3) 2_756 ?
Bi01 Cl3A 2.69(3) . ?
Bi02 Br04 2.832(5) . ?
Bi02 Br04 2.832(5) 2_467 ?
Bi02 Br05 2.8666(10) 2_467 ?
Bi02 Br05 2.8666(10) . ?
Bi02 Br08 2.871(16) 2_467 ?
Bi02 Br08 2.871(16) . ?
Bi02 Cl1A 2.73(2) . ?
Bi02 Cl1A 2.73(2) 2_467 ?
Bi02 Cl4A 2.76(4) 2_467 ?
Bi02 Cl4A 2.76(4) . ?
Bi02 Cl 2.62(2) 2_467 ?
Bi02 Cl 2.62(2) . ?
N1 C11 1.504(5) . ?
N1 C12 1.345(5) . ?
N1 C1AA 1.343(6) . ?
C3 C7 1.380(6) . ?
C3 C13 1.389(6) . ?
N5 C9 1.337(6) . ?
N5 C10 1.484(6) . ?
N5 C16 1.350(6) . ?
C7 C11 1.507(6) . ?
C7 C13 1.389(6) 2_566 ?
C8 C9 1.369(7) . ?
C8 C18 1.380(7) . ?
C10 C20 1.498(7) . ?
C12 C4AA 1.378(6) . ?
C14 C15 1.376(7) 2_666 ?
C14 C20 1.387(6) . ?
C15 C20 1.397(6) . ?
C16 C0AA 1.369(7) . ?
C18 C0AA 1.371(7) . ?
C3AA C2AA 1.377(7) . ?
C3AA C4AA 1.376(7) . ?
N2 C8AA 1.345(6) . ?
N2 C4 1.339(6) . ?
N2 C9AA 1.502(6) . ?
C8AA C5AA 1.378(7) . ?
C4 C7AA 1.371(7) . ?
C2AA C1AA 1.370(7) . ?
C6 C0BA 1.388(7) . ?
C6 C1BA 1.379(7) . ?
C6 C9AA 1.514(7) . ?
C0BA C1BA 1.390(7) 2_757 ?
C7AA C6AA 1.373(7) . ?
C6AA C5AA 1.369(7) . ?

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
Br03 Bi01 Br03 180.0 . 2_756 ?
Br06 Bi01 Br03 89.52(11) 2_756 . ?
Br06 Bi01 Br03 90.48(11) 2_756 2_756 ?
Br06 Bi01 Br03 89.52(11) . 2_756 ?
Br06 Bi01 Br03 90.48(11) . . ?
Br06 Bi01 Br06 180.0 2_756 . ?
Br07 Bi01 Br03 93.3(2) . . ?
Br07 Bi01 Br03 86.7(2) 2_756 . ?
Br07 Bi01 Br03 93.3(2) 2_756 2_756 ?
Br07 Bi01 Br03 86.7(2) . 2_756 ?
Br07 Bi01 Br06 91.3(3) 2_756 2_756 ?
Br07 Bi01 Br06 88.7(3) 2_756 . ?
Br07 Bi01 Br06 88.7(3) . 2_756 ?
Br07 Bi01 Br06 91.3(3) . . ?
Br07 Bi01 Br07 180.0 2_756 . ?
Cl0A Bi01 Cl2A 91.6(11) 2_756 . ?
Cl0A Bi01 Cl2A 88.4(11) . . ?
Cl2A Bi01 Cl2A 180.0 2_756 . ?
Cl3A Bi01 Cl0A 91.1(11) . . ?
Cl3A Bi01 Cl0A 88.9(11) 2_756 . ?
Cl3A Bi01 Cl2A 88.7(12) . . ?
Cl3A Bi01 Cl2A 91.3(12) 2_756 . ?
Cl3A Bi01 Cl3A 180.0 2_756 . ?
Br04 Bi02 Br04 180.00(16) . 2_467 ?
Br04 Bi02 Br05 87.80(11) . 2_467 ?
Br04 Bi02 Br05 92.20(11) 2_467 2_467 ?
Br04 Bi02 Br05 92.20(11) . . ?
Br04 Bi02 Br05 87.80(11) 2_467 . ?
Br04 Bi02 Br08 89.9(4) . 2_467 ?
Br04 Bi02 Br08 90.1(4) 2_467 2_467 ?
Br04 Bi02 Br08 90.1(4) . . ?
Br04 Bi02 Br08 89.9(4) 2_467 . ?
Br05 Bi02 Br05 180.0 . 2_467 ?
Br05 Bi02 Br08 88.5(4) . 2_467 ?
Br05 Bi02 Br08 91.5(4) . . ?
Br05 Bi02 Br08 88.5(4) 2_467 . ?
Br05 Bi02 Br08 91.5(4) 2_467 2_467 ?
Br08 Bi02 Br08 180.0(4) 2_467 . ?
Cl1A Bi02 Cl1A 180.0 2_467 . ?
Cl1A Bi02 Cl4A 90.8(8) 2_467 . ?
Cl1A Bi02 Cl4A 89.2(8) . . ?
Cl4A Bi02 Cl4A 180.0(11) 2_467 . ?
Cl Bi02 Cl1A 90.9(8) . . ?
Cl Bi02 Cl1A 89.1(8) 2_467 . ?
Cl Bi02 Cl4A 91.2(10) 2_467 . ?
Cl Bi02 Cl4A 88.8(10) . . ?
Cl Bi02 Cl 180.0 2_467 . ?
C12 N1 C11 120.3(4) . . ?
C1AA N1 C11 118.7(4) . . ?
C1AA N1 C12 121.0(4) . . ?
C7 C3 C13 120.2(4) . . ?
C9 N5 C10 119.9(4) . . ?
C9 N5 C16 120.4(4) . . ?
C16 N5 C10 119.6(4) . . ?
C3 C7 C11 119.9(4) . . ?
C3 C7 C13 119.6(4) . 2_566 ?
C13 C7 C11 120.5(4) 2_566 . ?
C9 C8 C18 119.2(5) . . ?
N5 C9 C8 121.1(5) . . ?
N5 C10 C20 114.3(4) . . ?
N1 C11 C7 111.1(4) . . ?
N1 C12 C4AA 120.0(4) . . ?
C3 C13 C7 120.2(4) . 2_566 ?
C15 C14 C20 121.1(4) 2_666 . ?
C14 C15 C20 121.1(4) 2_666 . ?
N5 C16 C0AA 120.0(4) . . ?
C0AA C18 C8 119.0(5) . . ?
C14 C20 C10 117.8(4) . . ?
C14 C20 C15 117.8(4) . . ?
C15 C20 C10 124.3(4) . . ?
C4AA C3AA C2AA 119.8(5) . . ?
C8AA N2 C9AA 119.3(4) . . ?
C4 N2 C8AA 120.8(4) . . ?
C4 N2 C9AA 119.9(4) . . ?
N2 C8AA C5AA 120.2(5) . . ?
N2 C4 C7AA 120.8(4) . . ?
C1AA C2AA C3AA 119.0(5) . . ?
C0BA C6 C9AA 120.6(4) . . ?
C1BA C6 C0BA 118.6(4) . . ?
C1BA C6 C9AA 120.8(5) . . ?
C3AA C4AA C12 119.4(4) . . ?
C6 C0BA C1BA 120.3(5) . 2_757 ?
C4 C7AA C6AA 118.9(5) . . ?
C6 C1BA C0BA 121.1(5) . 2_757 ?
C5AA C6AA C7AA 120.2(5) . . ?
N1 C1AA C2AA 120.8(5) . . ?
C6AA C5AA C8AA 119.1(5) . . ?
N2 C9AA C6 113.0(4) . . ?
C16 C0AA C18 120.2(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2341097'
loop_
_audit_author_name
_audit_author_address
'Petr Buikin'
;N S Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-05-15 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_audit_creation_date             2024-05-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi I6, 1.5(C18 H18 N2), C3 H7 N O'
_chemical_formula_sum            'C30 H34 Bi I6 N4 O'
_chemical_formula_weight         1436.99
_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 0.0033 0.0016 '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'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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                   11.0547(5)
_cell_length_b                   13.7612(6)
_cell_length_c                   13.8907(6)
_cell_angle_alpha                74.6500(10)
_cell_angle_beta                 87.7940(10)
_cell_angle_gamma                72.9350(10)
_cell_volume                     1946.28(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9992
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.97
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   0.523
_shelx_estimated_absorpt_T_min   0.234
_exptl_absorpt_coefficient_mu    9.316
_exptl_absorpt_correction_T_max  0.182
_exptl_absorpt_correction_T_min  0.032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.452
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1302
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 0.71065   17.348   14.716   13.824   90.004  121.680   90.007
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            46406
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.556
_diffrn_reflns_theta_min         2.116
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker AXS D8 VENTURE PHOTON III C14 IuS 3.0'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                12041
_reflns_number_total             12915
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-2018 (Sheldrick, 2015)'
_refine_diff_density_max         1.457
_refine_diff_density_min         -1.389
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       0.00048(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         12915
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0203
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0022P)²+2.1242P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0410
_refine_ls_wR_factor_ref         0.0417
_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. Uiso/Uaniso restraints and constraints
Uanis(N101) = Uanis(N111)
Uanis(C113) = Uanis(C101)
Uanis(O101) = Uanis(O111)
Uanis(C111) = Uanis(C103)
Uanis(C102) = Uanis(C112)
3. Others
 Sof(O111)=Sof(N111)=Sof(C111)=Sof(H111)=Sof(C112)=Sof(H11A)=Sof(H11B)=
 Sof(H11C)=Sof(C113)=Sof(H11D)=Sof(H11E)=Sof(H11F)=1-FVAR(1)
 Sof(O101)=Sof(N101)=Sof(C101)=Sof(H101)=Sof(C102)=Sof(H10A)=Sof(H10B)=
 Sof(H10C)=Sof(C103)=Sof(H10D)=Sof(H10E)=Sof(H10F)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C13(H13A,H13B), C24(H24A,H24B)
4.b Me refined with riding coordinates:
 C102(H10A,H10B,H10C), C103(H10D,H10E,H10F), C112(H11A,H11B,H11C), C113(H11D,
 H11E,H11F)
4.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21),
  C22(H22), C23(H23), C26(H26), C27(H27), C101(H101), C111(H111)
;
_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
Bi1 Bi 0.22415(2) 0.75634(2) 0.23853(2) 0.01655(2) Uani 1 1 d . . . . .
I1 I 0.44325(2) 0.68487(2) 0.11040(2) 0.02039(3) Uani 1 1 d . . . . .
I2 I 0.15835(2) 0.97646(2) 0.10854(2) 0.02171(3) Uani 1 1 d . . . . .
I3 I 0.00192(2) 0.82553(2) 0.38229(2) 0.02130(3) Uani 1 1 d . . . . .
I4 I 0.30322(2) 0.51821(2) 0.36873(2) 0.02164(3) Uani 1 1 d . . . . .
I5 I 0.39094(2) 0.82147(2) 0.36314(2) 0.02152(3) Uani 1 1 d . . . . .
I6 I 0.04563(2) 0.70216(2) 0.10495(2) 0.02758(4) Uani 1 1 d . . . . .
N1 N 0.71519(19) 0.04665(16) 0.13657(15) 0.0182(4) Uani 1 1 d . . . . .
N2 N 0.73588(19) 0.46035(15) 0.38486(14) 0.0183(4) Uani 1 1 d . . . . .
N3 N 0.2154(2) 0.2155(2) 0.3736(2) 0.0378(6) Uani 1 1 d . . . . .
C1 C 0.5885(2) 0.0829(2) 0.13767(19) 0.0228(5) Uani 1 1 d . . . . .
H1 H 0.549171 0.154413 0.137139 0.027 Uiso 1 1 calc R U . . .
C2 C 0.5152(3) 0.0171(2) 0.1396(2) 0.0271(5) Uani 1 1 d . . . . .
H2 H 0.425654 0.042462 0.141640 0.033 Uiso 1 1 calc R U . . .
C3 C 0.5733(3) -0.0867(2) 0.1385(2) 0.0292(6) Uani 1 1 d . . . . .
H3 H 0.524255 -0.132974 0.138577 0.035 Uiso 1 1 calc R U . . .
C4 C 0.7045(3) -0.1216(2) 0.1372(2) 0.0276(5) Uani 1 1 d . . . . .
H4 H 0.746019 -0.192510 0.136602 0.033 Uiso 1 1 calc R U . . .
C5 C 0.7746(3) -0.05352(19) 0.13666(18) 0.0231(5) Uani 1 1 d . . . . .
H5 H 0.864382 -0.077386 0.136378 0.028 Uiso 1 1 calc R U . . .
C6 C 0.7909(2) 0.1220(2) 0.12602(19) 0.0227(5) Uani 1 1 d . . . . .
H6A H 0.775966 0.170085 0.057734 0.027 Uiso 1 1 calc R U . . .
H6B H 0.882039 0.082286 0.134819 0.027 Uiso 1 1 calc R U . . .
C7 C 0.7577(2) 0.18641(19) 0.20105(18) 0.0198(4) Uani 1 1 d . . . . .
C8 C 0.6927(2) 0.2930(2) 0.17084(19) 0.0232(5) Uani 1 1 d . . . . .
H8 H 0.666378 0.325270 0.102619 0.028 Uiso 1 1 calc R U . . .
C9 C 0.6658(3) 0.3529(2) 0.23947(19) 0.0241(5) Uani 1 1 d . . . . .
H9 H 0.619978 0.425598 0.218231 0.029 Uiso 1 1 calc R U . . .
C10 C 0.7057(2) 0.30681(18) 0.33922(17) 0.0190(4) Uani 1 1 d . . . . .
C11 C 0.7702(2) 0.19970(19) 0.37005(18) 0.0220(5) Uani 1 1 d . . . . .
H11 H 0.797112 0.167453 0.438171 0.026 Uiso 1 1 calc R U . . .
C12 C 0.7953(2) 0.13984(19) 0.30108(19) 0.0221(5) Uani 1 1 d . . . . .
H12 H 0.838528 0.066588 0.322548 0.027 Uiso 1 1 calc R U . . .
C13 C 0.6791(3) 0.3716(2) 0.41361(19) 0.0232(5) Uani 1 1 d . . . . .
H13A H 0.586338 0.400179 0.417970 0.028 Uiso 1 1 calc R U . . .
H13B H 0.714015 0.326060 0.480375 0.028 Uiso 1 1 calc R U . . .
C14 C 0.6616(2) 0.5593(2) 0.34965(19) 0.0231(5) Uani 1 1 d . . . . .
H14 H 0.572618 0.572826 0.342411 0.028 Uiso 1 1 calc R U . . .
C15 C 0.7136(3) 0.6418(2) 0.3239(2) 0.0285(6) Uani 1 1 d . . . . .
H15 H 0.660786 0.711928 0.298291 0.034 Uiso 1 1 calc R U . . .
C16 C 0.8424(3) 0.6221(2) 0.3353(2) 0.0297(6) Uani 1 1 d . . . . .
H16 H 0.879384 0.678183 0.316601 0.036 Uiso 1 1 calc R U . . .
C17 C 0.9178(3) 0.5189(2) 0.3747(2) 0.0282(5) Uani 1 1 d . . . . .
H17 H 1.006645 0.503904 0.384421 0.034 Uiso 1 1 calc R U . . .
C18 C 0.8617(2) 0.4390(2) 0.3993(2) 0.0249(5) Uani 1 1 d . . . . .
H18 H 0.912167 0.368363 0.426635 0.030 Uiso 1 1 calc R U . . .
C19 C 0.1620(3) 0.3126(3) 0.3141(3) 0.0412(8) Uani 1 1 d . . . . .
H19 H 0.186254 0.370550 0.322858 0.049 Uiso 1 1 calc R U . . .
C20 C 0.0727(3) 0.3290(3) 0.2405(3) 0.0482(9) Uani 1 1 d . . . . .
H20 H 0.033671 0.397781 0.199371 0.058 Uiso 1 1 calc R U . . .
C21 C 0.0411(3) 0.2423(4) 0.2280(3) 0.0530(11) Uani 1 1 d . . . . .
H21 H -0.018983 0.251261 0.176819 0.064 Uiso 1 1 calc R U . . .
C22 C 0.0966(3) 0.1436(4) 0.2896(3) 0.0556(11) Uani 1 1 d . . . . .
H22 H 0.074572 0.084494 0.281352 0.067 Uiso 1 1 calc R U . . .
C23 C 0.1842(3) 0.1305(3) 0.3633(3) 0.0473(9) Uani 1 1 d . . . . .
H23 H 0.222316 0.062590 0.406438 0.057 Uiso 1 1 calc R U . . .
C24 C 0.3073(3) 0.2026(3) 0.4558(3) 0.0392(7) Uani 1 1 d . . . . .
H24A H 0.260412 0.210250 0.516879 0.047 Uiso 1 1 calc R U . . .
H24B H 0.348761 0.259202 0.436399 0.047 Uiso 1 1 calc R U . . .
C25 C 0.4074(3) 0.0971(3) 0.4788(3) 0.0360(7) Uani 1 1 d . . . . .
C26 C 0.4057(3) 0.0215(3) 0.5663(3) 0.0419(8) Uani 1 1 d . . . . .
H26 H 0.341199 0.036084 0.612056 0.050 Uiso 1 1 calc R U . . .
C27 C 0.4975(3) -0.0758(3) 0.5881(3) 0.0406(8) Uani 1 1 d . . . . .
H27 H 0.495552 -0.127717 0.648360 0.049 Uiso 1 1 calc R U . . .
O101 O 0.3474(3) 0.2354(3) 0.1571(3) 0.0397(7) Uani 0.612(3) 1 d . . P A 1
N101 N 0.2719(9) 0.3966(4) 0.0451(7) 0.0299(13) Uani 0.612(3) 1 d . . P A 1
C101 C 0.2828(6) 0.2919(6) 0.0822(5) 0.0349(11) Uani 0.612(3) 1 d . . P A 1
H101 H 0.237732 0.261183 0.047902 0.042 Uiso 0.612(3) 1 calc R U P A 1
C102 C 0.1945(5) 0.4545(4) -0.0458(4) 0.0416(10) Uani 0.612(3) 1 d . . P A 1
H10A H 0.195322 0.528138 -0.063511 0.062 Uiso 0.612(3) 1 calc R U P A 1
H10B H 0.228722 0.422794 -0.100241 0.062 Uiso 0.612(3) 1 calc R U P A 1
H10C H 0.107366 0.451629 -0.035067 0.062 Uiso 0.612(3) 1 calc R U P A 1
C103 C 0.3415(4) 0.4479(4) 0.0857(4) 0.0328(9) Uani 0.612(3) 1 d . . P A 1
H10D H 0.319550 0.522366 0.048245 0.049 Uiso 0.612(3) 1 calc R U P A 1
H10E H 0.321322 0.442631 0.155886 0.049 Uiso 0.612(3) 1 calc R U P A 1
H10F H 0.432264 0.414627 0.081338 0.049 Uiso 0.612(3) 1 calc R U P A 1
O111 O 0.3986(5) 0.2710(4) 0.2153(5) 0.0397(7) Uani 0.388(3) 1 d . . P A 2
N111 N 0.2845(16) 0.3670(8) 0.0676(12) 0.0299(13) Uani 0.388(3) 1 d . . P A 2
C111 C 0.3596(7) 0.3558(6) 0.1545(6) 0.0328(9) Uani 0.388(3) 1 d . . P A 2
H111 H 0.378841 0.415461 0.164356 0.039 Uiso 0.388(3) 1 calc R U P A 2
C112 C 0.2507(9) 0.4710(7) 0.0013(7) 0.0416(10) Uani 0.388(3) 1 d . . P A 2
H11A H 0.276279 0.518508 0.032332 0.062 Uiso 0.388(3) 1 calc R U P A 2
H11B H 0.293820 0.469455 -0.061486 0.062 Uiso 0.388(3) 1 calc R U P A 2
H11C H 0.158838 0.496193 -0.012305 0.062 Uiso 0.388(3) 1 calc R U P A 2
C113 C 0.2625(10) 0.2844(10) 0.0472(8) 0.0349(11) Uani 0.388(3) 1 d . . P A 2
H11D H 0.293792 0.221960 0.103556 0.052 Uiso 0.388(3) 1 calc R U P A 2
H11E H 0.171185 0.298556 0.036172 0.052 Uiso 0.388(3) 1 calc R U P A 2
H11F H 0.306167 0.271819 -0.013009 0.052 Uiso 0.388(3) 1 calc R U P A 2


_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
Bi1 I1 3.0328(2) . ?
Bi1 I2 2.9795(2) . ?
Bi1 I3 3.1915(2) . ?
Bi1 I4 3.1743(2) . ?
Bi1 I5 3.03903(19) . ?
Bi1 I6 3.1259(2) . ?
N1 C1 1.343(3) . ?
N1 C5 1.341(3) . ?
N1 C6 1.489(3) . ?
N2 C13 1.489(3) . ?
N2 C14 1.338(3) . ?
N2 C18 1.346(3) . ?
N3 C19 1.344(5) . ?
N3 C23 1.355(4) . ?
N3 C24 1.498(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.376(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.379(4) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.508(3) . ?
C7 C8 1.386(3) . ?
C7 C12 1.390(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.388(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.391(3) . ?
C10 C11 1.392(3) . ?
C10 C13 1.504(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.392(3) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14 0.9500 . ?
C14 C15 1.377(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.376(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.392(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.376(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C19 C20 1.376(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.392(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.374(6) . ?
C22 H22 0.9500 . ?
C22 C23 1.375(5) . ?
C23 H23 0.9500 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.508(5) . ?
C25 C26 1.378(5) . ?
C25 C27 1.394(4) 2_656 ?
C26 H26 0.9500 . ?
C26 C27 1.387(5) . ?
C27 H27 0.9500 . ?
O101 C101 1.225(8) . ?
N101 C101 1.366(8) . ?
N101 C102 1.453(10) . ?
N101 C103 1.405(11) . ?
C101 H101 0.9500 . ?
C102 H10A 0.9800 . ?
C102 H10B 0.9800 . ?
C102 H10C 0.9800 . ?
C103 H10D 0.9800 . ?
C103 H10E 0.9800 . ?
C103 H10F 0.9800 . ?
O111 C111 1.213(10) . ?
N111 C111 1.44(2) . ?
N111 C112 1.432(11) . ?
N111 C113 1.330(18) . ?
C111 H111 0.9500 . ?
C112 H11A 0.9800 . ?
C112 H11B 0.9800 . ?
C112 H11C 0.9800 . ?
C113 H11D 0.9800 . ?
C113 H11E 0.9800 . ?
C113 H11F 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
I1 Bi1 I3 177.354(5) . . ?
I1 Bi1 I4 85.702(5) . . ?
I1 Bi1 I5 91.424(6) . . ?
I1 Bi1 I6 89.446(6) . . ?
I2 Bi1 I1 91.521(5) . . ?
I2 Bi1 I3 90.366(5) . . ?
I2 Bi1 I4 177.156(5) . . ?
I2 Bi1 I5 86.966(6) . . ?
I2 Bi1 I6 90.063(6) . . ?
I4 Bi1 I3 92.430(5) . . ?
I5 Bi1 I3 86.824(6) . . ?
I5 Bi1 I4 93.708(6) . . ?
I5 Bi1 I6 176.925(6) . . ?
I6 Bi1 I3 92.407(6) . . ?
I6 Bi1 I4 89.298(6) . . ?
C1 N1 C6 118.9(2) . . ?
C5 N1 C1 121.8(2) . . ?
C5 N1 C6 119.0(2) . . ?
C14 N2 C13 120.1(2) . . ?
C14 N2 C18 121.3(2) . . ?
C18 N2 C13 118.6(2) . . ?
C19 N3 C23 121.6(3) . . ?
C19 N3 C24 118.7(3) . . ?
C23 N3 C24 119.7(3) . . ?
N1 C1 H1 119.8 . . ?
N1 C1 C2 120.4(2) . . ?
C2 C1 H1 119.8 . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.4(3) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.8(2) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
N1 C5 C4 119.6(2) . . ?
N1 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
N1 C6 H6A 109.1 . . ?
N1 C6 H6B 109.1 . . ?
N1 C6 C7 112.31(19) . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
C8 C7 C6 120.6(2) . . ?
C8 C7 C12 119.3(2) . . ?
C12 C7 C6 120.1(2) . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.5(2) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.2(2) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C11 119.5(2) . . ?
C9 C10 C13 120.5(2) . . ?
C11 C10 C13 120.0(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0(2) . . ?
C12 C11 H11 120.0 . . ?
C7 C12 C11 120.5(2) . . ?
C7 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
N2 C13 C10 111.47(19) . . ?
N2 C13 H13A 109.3 . . ?
N2 C13 H13B 109.3 . . ?
C10 C13 H13A 109.3 . . ?
C10 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
N2 C14 H14 119.9 . . ?
N2 C14 C15 120.3(2) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.7(3) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 120.4 . . ?
C15 C16 C17 119.2(2) . . ?
C17 C16 H16 120.4 . . ?
C16 C17 H17 120.5 . . ?
C18 C17 C16 119.1(2) . . ?
C18 C17 H17 120.5 . . ?
N2 C18 C17 120.4(2) . . ?
N2 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
N3 C19 H19 119.6 . . ?
N3 C19 C20 120.8(3) . . ?
C20 C19 H19 119.6 . . ?
C19 C20 H20 120.8 . . ?
C19 C20 C21 118.4(4) . . ?
C21 C20 H20 120.8 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 120.0(4) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.0(3) . . ?
C23 C22 H22 120.0 . . ?
N3 C23 C22 119.3(4) . . ?
N3 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
N3 C24 H24A 109.1 . . ?
N3 C24 H24B 109.1 . . ?
N3 C24 C25 112.5(2) . . ?
H24A C24 H24B 107.8 . . ?
C25 C24 H24A 109.1 . . ?
C25 C24 H24B 109.1 . . ?
C26 C25 C24 120.2(3) . . ?
C26 C25 C27 119.7(3) . 2_656 ?
C27 C25 C24 120.1(3) 2_656 . ?
C25 C26 H26 119.7 . . ?
C25 C26 C27 120.6(3) . . ?
C27 C26 H26 119.7 . . ?
C25 C27 H27 120.1 2_656 . ?
C26 C27 C25 119.7(3) . 2_656 ?
C26 C27 H27 120.1 . . ?
C101 N101 C102 118.4(8) . . ?
C101 N101 C103 122.7(7) . . ?
C103 N101 C102 118.6(4) . . ?
O101 C101 N101 123.7(7) . . ?
O101 C101 H101 118.1 . . ?
N101 C101 H101 118.1 . . ?
N101 C102 H10A 109.5 . . ?
N101 C102 H10B 109.5 . . ?
N101 C102 H10C 109.5 . . ?
H10A C102 H10B 109.5 . . ?
H10A C102 H10C 109.5 . . ?
H10B C102 H10C 109.5 . . ?
N101 C103 H10D 109.5 . . ?
N101 C103 H10E 109.5 . . ?
N101 C103 H10F 109.5 . . ?
H10D C103 H10E 109.5 . . ?
H10D C103 H10F 109.5 . . ?
H10E C103 H10F 109.5 . . ?
C112 N111 C111 113.7(12) . . ?
C113 N111 C111 121.7(9) . . ?
C113 N111 C112 124.2(15) . . ?
O111 C111 N111 120.7(8) . . ?
O111 C111 H111 119.6 . . ?
N111 C111 H111 119.6 . . ?
N111 C112 H11A 109.5 . . ?
N111 C112 H11B 109.5 . . ?
N111 C112 H11C 109.5 . . ?
H11A C112 H11B 109.5 . . ?
H11A C112 H11C 109.5 . . ?
H11B C112 H11C 109.5 . . ?
N111 C113 H11D 109.5 . . ?
N111 C113 H11E 109.5 . . ?
N111 C113 H11F 109.5 . . ?
H11D C113 H11E 109.5 . . ?
H11D C113 H11F 109.5 . . ?
H11E C113 H11F 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 C1 C2 C3 -1.2(4) . . . . ?
N1 C6 C7 C8 -109.3(3) . . . . ?
N1 C6 C7 C12 72.6(3) . . . . ?
N2 C14 C15 C16 -0.6(4) . . . . ?
N3 C19 C20 C21 -1.3(5) . . . . ?
N3 C24 C25 C26 -108.5(3) . . . . ?
N3 C24 C25 C27 71.9(4) . . . 2_656 ?
C1 N1 C5 C4 0.5(4) . . . . ?
C1 N1 C6 C7 51.9(3) . . . . ?
C1 C2 C3 C4 1.1(4) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 N1 -0.6(4) . . . . ?
C5 N1 C1 C2 0.4(4) . . . . ?
C5 N1 C6 C7 -133.3(2) . . . . ?
C6 N1 C1 C2 175.0(2) . . . . ?
C6 N1 C5 C4 -174.1(2) . . . . ?
C6 C7 C8 C9 -177.9(2) . . . . ?
C6 C7 C12 C11 177.0(2) . . . . ?
C7 C8 C9 C10 1.0(4) . . . . ?
C8 C7 C12 C11 -1.2(4) . . . . ?
C8 C9 C10 C11 -1.5(4) . . . . ?
C8 C9 C10 C13 178.8(2) . . . . ?
C9 C10 C11 C12 0.6(4) . . . . ?
C9 C10 C13 N2 -59.1(3) . . . . ?
C10 C11 C12 C7 0.7(4) . . . . ?
C11 C10 C13 N2 121.2(2) . . . . ?
C12 C7 C8 C9 0.3(4) . . . . ?
C13 N2 C14 C15 179.4(2) . . . . ?
C13 N2 C18 C17 -179.3(2) . . . . ?
C13 C10 C11 C12 -179.7(2) . . . . ?
C14 N2 C13 C10 107.2(3) . . . . ?
C14 N2 C18 C17 -2.3(4) . . . . ?
C14 C15 C16 C17 -1.2(4) . . . . ?
C15 C16 C17 C18 1.3(4) . . . . ?
C16 C17 C18 N2 0.4(4) . . . . ?
C18 N2 C13 C10 -75.7(3) . . . . ?
C18 N2 C14 C15 2.4(4) . . . . ?
C19 N3 C23 C22 0.6(5) . . . . ?
C19 N3 C24 C25 -149.2(3) . . . . ?
C19 C20 C21 C22 1.4(5) . . . . ?
C20 C21 C22 C23 -0.4(5) . . . . ?
C21 C22 C23 N3 -0.5(5) . . . . ?
C23 N3 C19 C20 0.4(4) . . . . ?
C23 N3 C24 C25 33.4(4) . . . . ?
C24 N3 C19 C20 -176.9(3) . . . . ?
C24 N3 C23 C22 177.9(3) . . . . ?
C24 C25 C26 C27 -180.0(3) . . . . ?
C25 C26 C27 C25 0.4(5) . . . 2_656 ?
C27 C25 C26 C27 -0.4(5) 2_656 . . . ?
C102 N101 C101 O101 178.6(6) . . . . ?
C103 N101 C101 O101 4.7(12) . . . . ?
C112 N111 C111 O111 -177.5(9) . . . . ?
C113 N111 C111 O111 -4.7(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_pyxk_bibr_4_1_dmso
_database_code_depnum_ccdc_archive 'CCDC 2341093'
loop_
_audit_author_name
_audit_author_address
'Petr Buikin'
;N S Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-05-15 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_audit_creation_date             2024-02-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'Bi Br4.083 Cl1.917, Bi0.5 Br2.207 Cl0.793, Bi0.5 Br2.199 Cl0.801, 6(C9 H9 N)'
_chemical_formula_sum            'C54 H54 Bi2 Br8.49 Cl3.51 N6'
_chemical_formula_weight         2007.85
_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 0.0033 0.0016 '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'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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                   12.790(3)
_cell_length_b                   14.769(4)
_cell_length_c                   19.156(5)
_cell_angle_alpha                67.593(5)
_cell_angle_beta                 73.276(5)
_cell_angle_gamma                80.529(7)
_cell_volume                     3197.5(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    140
_cell_measurement_theta_max      24.349
_cell_measurement_theta_min      2.166
_shelx_estimated_absorpt_T_max   0.474
_shelx_estimated_absorpt_T_min   0.290
_exptl_absorpt_coefficient_mu    10.987
_exptl_absorpt_correction_T_max  0.4926
_exptl_absorpt_correction_T_min  0.2652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1477 before and 0.0512 after correction.
The Ratio of minimum to maximum transmission is 0.1532.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    ?
_exptl_crystal_density_diffrn    2.085
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1886
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_unetI/netI     0.0744
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            40876
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         1.186
_diffrn_ambient_temperature      140
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9665
_reflns_number_total             12597
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         3.971
_refine_diff_density_min         -2.588
_refine_diff_density_rms         0.196
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     718
_refine_ls_number_reflns         12597
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0181P)²+35.3205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1182
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 Cl4B-Bi1
 2.7 with sigma of 0.02
 Cl5A-Bi1
 2.7 with sigma of 0.02
 Cl6B-Bi1
 2.7 with sigma of 0.02
2. Restrained planarity
 Cl1A, Cl3A, Cl4B, Cl6B, Bi1
 with sigma of 0.1
3. Uiso/Uaniso restraints and constraints
Uanis(Cl2A) = Uanis(Br2B)
Uanis(Br5) = Uanis(Cl5A)
Uanis(Cl7A) = Uanis(Br7B)
Uanis(Cl) = Uanis(Br)
Uanis(Cl1) = Uanis(Br10)
Uanis(Cl6B) = Uanis(Br6A)
Uanis(Cl9B) = Uanis(Br9A)
Uanis(Br8B) = Uanis(Cl8A)
Uanis(Br2) = Uanis(Cl2)
Uanis(Br3B) = Uanis(Cl3A)
Uanis(Cl4B) = Uanis(Br4A)
Uanis(Br1B) = Uanis(Cl1A)
4. Others
 Sof(Br2B)=1-FVAR(1)
 Sof(Cl2A)=FVAR(1)
 Sof(Cl5A)=1-FVAR(2)
 Sof(Br5)=FVAR(2)
 Sof(Br7B)=1-FVAR(3)
 Sof(Cl7A)=FVAR(3)
 Sof(Br)=1-FVAR(4)
 Sof(Cl)=FVAR(4)
 Sof(Cl1)=1-FVAR(5)
 Sof(Br10)=FVAR(5)
 Sof(Cl6B)=1-FVAR(6)
 Sof(Br6A)=FVAR(6)
 Sof(Br8B)=1-FVAR(7)
 Sof(Cl8A)=FVAR(7)
 Sof(Cl9B)=1-FVAR(8)
 Sof(Br9A)=FVAR(8)
 Sof(Br2)=1-FVAR(9)
 Sof(Cl2)=FVAR(9)
 Sof(Br3B)=1-FVAR(10)
 Sof(Cl3A)=FVAR(10)
 Sof(Cl4B)=1-FVAR(11)
 Sof(Br4A)=FVAR(11)
 Sof(Br1B)=1-FVAR(12)
 Sof(Cl1A)=FVAR(12)
5.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C15(H15A,H15B), C22(H22A,H22B), C33(H33A,H33B), C42(H42A,H42B),
 C49(H49A,H49B)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C13(H13), C14(H14), C17(H17), C18(H18), C20(H20), C21(H21), C23(H23),
  C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30),
 C31(H31), C32(H32), C35(H35), C36(H36), C37(H37), C38(H38), C39(H39), C40(H40),
  C41(H41), C44(H44), C45(H45), C47(H47), C48(H48), C50(H50), C51(H51),
 C52(H52), C53(H53), C54(H54)
;
_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
Bi1 Bi 1.49081(3) -0.01731(2) 0.25023(2) 0.02582(11) Uani 1 1 d D . . . .
Br1B Br 1.6485(3) -0.0782(3) 0.1348(4) 0.0362(6) Uani 0.898(7) 1 d . . P A 1
Br2B Br 1.3693(6) -0.1865(6) 0.2934(4) 0.0196(11) Uani 0.408(7) 1 d . . P A 1
Br3B Br 1.3677(2) 0.08295(13) 0.13854(15) 0.0309(5) Uani 0.819(7) 1 d . . P A 1
Cl4B Cl 1.352(5) 0.050(3) 0.358(3) 0.0437(7) Uani 0.201(8) 1 d D . P A 2
Br5 Br 1.6048(18) 0.1534(12) 0.2029(17) 0.0320(18) Uani 0.444(7) 1 d . . P A 1
Cl6B Cl 1.620(2) -0.0907(14) 0.3537(14) 0.0408(7) Uani 0.285(8) 1 d D . P A 2
Bi2 Bi 1.000000 -0.500000 0.500000 0.02172(12) Uani 1 2 d S . P . .
Br7B Br 0.8914(2) -0.6167(2) 0.45841(15) 0.0257(7) Uani 0.594(8) 1 d . . P B 1
Br8B Br 1.10567(14) -0.40672(12) 0.34010(10) 0.0301(5) Uani 0.795(8) 1 d . . P
B 1
Cl9B Cl 0.828(4) -0.343(4) 0.497(3) 0.0260(6) Uani 0.182(7) 1 d . . P B 2
Bi3 Bi 1.000000 0.500000 0.000000 0.02596(13) Uani 1 2 d S . P . .
Br10 Br 1.15078(13) 0.61268(10) -0.12716(11) 0.0357(6) Uani 0.687(6) 1 d . . P
C 1
Br2 Br 1.16656(14) 0.34301(12) 0.01451(8) 0.0309(5) Uani 0.880(7) 1 d . . P C 1
Br Br 0.92747(19) 0.42993(18) -0.09576(14) 0.0324(7) Uani 0.632(8) 1 d . . P C
1
N1 N 1.3438(6) -0.2776(5) 0.0349(4) 0.0301(18) Uani 1 1 d . . . . .
C1 C 1.2919(8) -0.3068(7) 0.1106(6) 0.037(2) Uani 1 1 d . . . . .
H1 H 1.252182 -0.364425 0.133913 0.044 Uiso 1 1 calc R U . . .
C2 C 1.2961(9) -0.2538(7) 0.1541(6) 0.037(2) Uani 1 1 d . . . . .
H2 H 1.260264 -0.274032 0.207983 0.044 Uiso 1 1 calc R U . . .
C3 C 1.3541(9) -0.1694(8) 0.1182(6) 0.044(3) Uani 1 1 d . . . . .
H3 H 1.356769 -0.130978 0.147654 0.053 Uiso 1 1 calc R U . . .
C4 C 1.4071(9) -0.1410(8) 0.0410(6) 0.041(3) Uani 1 1 d . . . . .
H4 H 1.447868 -0.084052 0.016690 0.049 Uiso 1 1 calc R U . . .
C5 C 1.4002(9) -0.1962(7) -0.0002(6) 0.039(2) Uani 1 1 d . . . . .
H5 H 1.435552 -0.177035 -0.054127 0.047 Uiso 1 1 calc R U . . .
C6 C 1.3382(8) -0.3369(7) -0.0130(5) 0.035(2) Uani 1 1 d . . . . .
H6A H 1.264741 -0.362661 0.004434 0.042 Uiso 1 1 calc R U . . .
H6B H 1.349618 -0.293962 -0.068444 0.042 Uiso 1 1 calc R U . . .
C7 C 1.4226(8) -0.4199(7) -0.0049(5) 0.030(2) Uani 1 1 d . . . . .
C8 C 1.3891(8) -0.5154(7) 0.0246(6) 0.035(2) Uani 1 1 d . . . . .
H8 H 1.313371 -0.526656 0.041784 0.042 Uiso 1 1 calc R U . . .
C9 C 1.4669(8) -0.5950(8) 0.0289(6) 0.037(2) Uani 1 1 d . . . . .
H9 H 1.443436 -0.659749 0.048499 0.045 Uiso 1 1 calc R U . . .
N2 N 0.9326(7) 0.1404(6) 0.0460(5) 0.041(2) Uani 1 1 d . . . . .
N3 N 1.0474(7) -0.1485(5) 0.4384(5) 0.041(2) Uani 1 1 d . . . . .
C10 C 1.0177(10) 0.1773(8) -0.0145(8) 0.054(3) Uani 1 1 d . . . . .
H10 H 1.068784 0.213204 -0.009727 0.064 Uiso 1 1 calc R U . . .
C11 C 1.0302(11) 0.1626(9) -0.0832(8) 0.066(4) Uani 1 1 d . . . . .
H11 H 1.090562 0.187238 -0.125987 0.079 Uiso 1 1 calc R U . . .
C12 C 0.9535(11) 0.1113(8) -0.0893(8) 0.061(4) Uani 1 1 d . . . . .
H12 H 0.959432 0.101934 -0.136681 0.073 Uiso 1 1 calc R U . . .
C13 C 0.8702(11) 0.0748(9) -0.0264(9) 0.065(4) Uani 1 1 d . . . . .
H13 H 0.818103 0.038274 -0.029393 0.079 Uiso 1 1 calc R U . . .
C14 C 0.8603(9) 0.0896(8) 0.0396(8) 0.054(3) Uani 1 1 d . . . . .
H14 H 0.800944 0.063691 0.082983 0.065 Uiso 1 1 calc R U . . .
C15 C 0.9186(10) 0.1598(8) 0.1192(7) 0.052(3) Uani 1 1 d . . . . .
H15A H 0.840542 0.177880 0.138570 0.063 Uiso 1 1 calc R U . . .
H15B H 0.961145 0.216379 0.107464 0.063 Uiso 1 1 calc R U . . .
C16 C 0.9557(9) 0.0717(7) 0.1832(7) 0.046(3) Uani 1 1 d . . . . .
C17 C 1.0617(9) 0.0600(8) 0.1903(7) 0.049(3) Uani 1 1 d . . . . .
H17 H 1.112619 0.106738 0.154334 0.059 Uiso 1 1 calc R U . . .
C18 C 1.0947(9) -0.0177(8) 0.2482(7) 0.047(3) Uani 1 1 d . . . . .
H18 H 1.168700 -0.024480 0.251093 0.056 Uiso 1 1 calc R U . . .
C19 C 1.0221(8) -0.0879(7) 0.3037(6) 0.041(3) Uani 1 1 d . . . . .
C20 C 0.9147(9) -0.0766(9) 0.2969(8) 0.059(4) Uani 1 1 d . . . . .
H20 H 0.863679 -0.123137 0.332989 0.071 Uiso 1 1 calc R U . . .
C21 C 0.8812(10) 0.0037(9) 0.2365(8) 0.064(4) Uani 1 1 d . . . . .
H21 H 0.807768 0.011174 0.232361 0.077 Uiso 1 1 calc R U . . .
C22 C 1.0579(8) -0.1726(7) 0.3675(6) 0.043(3) Uani 1 1 d . . . . .
H22A H 1.135104 -0.192953 0.348110 0.051 Uiso 1 1 calc R U . . .
H22B H 1.013111 -0.228649 0.381848 0.051 Uiso 1 1 calc R U . . .
C23 C 1.1350(8) -0.1251(8) 0.4514(7) 0.044(3) Uani 1 1 d . . . . .
H23 H 1.203040 -0.120723 0.413849 0.053 Uiso 1 1 calc R U . . .
C24 C 1.1285(10) -0.1074(8) 0.5173(6) 0.048(3) Uani 1 1 d . . . . .
H24 H 1.191976 -0.090890 0.525117 0.058 Uiso 1 1 calc R U . . .
C25 C 1.0311(10) -0.1131(8) 0.5728(7) 0.054(3) Uani 1 1 d . . . . .
H25 H 1.025779 -0.102541 0.619618 0.065 Uiso 1 1 calc R U . . .
C26 C 0.9429(11) -0.1347(7) 0.5572(8) 0.057(4) Uani 1 1 d . . . . .
H26 H 0.873837 -0.136678 0.593381 0.068 Uiso 1 1 calc R U . . .
C27 C 0.9497(9) -0.1537(7) 0.4910(8) 0.054(3) Uani 1 1 d . . . . .
H27 H 0.886889 -0.170227 0.482344 0.065 Uiso 1 1 calc R U . . .
N4 N 0.6345(7) 0.2802(7) 0.4498(5) 0.042(2) Uani 1 1 d . . . . .
C28 C 0.5954(11) 0.1987(11) 0.4525(9) 0.070(4) Uani 1 1 d . . . . .
H28 H 0.548108 0.158911 0.498544 0.084 Uiso 1 1 calc R U . . .
C29 C 0.6283(12) 0.1752(12) 0.3831(8) 0.072(4) Uani 1 1 d . . . . .
H29 H 0.607846 0.117274 0.381407 0.087 Uiso 1 1 calc R U . . .
C30 C 0.6910(12) 0.2411(12) 0.3195(8) 0.073(4) Uani 1 1 d . . . . .
H30 H 0.709647 0.230532 0.271358 0.087 Uiso 1 1 calc R U . . .
C31 C 0.7277(12) 0.3200(16) 0.3213(9) 0.099(6) Uani 1 1 d . . . . .
H31 H 0.775639 0.361184 0.276635 0.118 Uiso 1 1 calc R U . . .
C32 C 0.6957(10) 0.3391(13) 0.3865(7) 0.077(5) Uani 1 1 d . . . . .
H32 H 0.717494 0.396957 0.387465 0.093 Uiso 1 1 calc R U . . .
C33 C 0.6080(11) 0.3086(10) 0.5201(6) 0.061(4) Uani 1 1 d . . . . .
H33A H 0.559972 0.260171 0.563717 0.074 Uiso 1 1 calc R U . . .
H33B H 0.676506 0.305800 0.535335 0.074 Uiso 1 1 calc R U . . .
C34 C 0.5535(10) 0.4075(8) 0.5084(6) 0.044(3) Uani 1 1 d . . . . .
C35 C 0.6025(10) 0.4817(11) 0.5121(8) 0.064(4) Uani 1 1 d . . . . .
H35 H 0.673820 0.469257 0.520723 0.077 Uiso 1 1 calc R U . . .
C36 C 0.5504(9) 0.5732(10) 0.5036(7) 0.053(3) Uani 1 1 d . . . . .
H36 H 0.586084 0.623052 0.506038 0.064 Uiso 1 1 calc R U . . .
N5 N 0.6820(6) 0.6534(5) 0.2166(4) 0.0313(18) Uani 1 1 d . . . . .
N6 N 0.2756(7) 0.3106(5) 0.2889(4) 0.0305(18) Uani 1 1 d . . . . .
C37 C 0.6592(9) 0.6882(7) 0.2752(6) 0.040(3) Uani 1 1 d . . . . .
H37 H 0.591043 0.723062 0.286911 0.048 Uiso 1 1 calc R U . . .
C38 C 0.7334(10) 0.6737(9) 0.3178(6) 0.052(3) Uani 1 1 d . . . . .
H38 H 0.716183 0.698712 0.358998 0.062 Uiso 1 1 calc R U . . .
C39 C 0.8311(9) 0.6243(8) 0.3026(6) 0.043(3) Uani 1 1 d . . . . .
H39 H 0.882168 0.614100 0.332838 0.051 Uiso 1 1 calc R U . . .
C40 C 0.8550(9) 0.5892(8) 0.2424(6) 0.044(3) Uani 1 1 d . . . . .
H40 H 0.923167 0.554408 0.230419 0.052 Uiso 1 1 calc R U . . .
C41 C 0.7797(8) 0.6046(7) 0.1996(6) 0.038(2) Uani 1 1 d . . . . .
H41 H 0.796335 0.580919 0.157752 0.045 Uiso 1 1 calc R U . . .
C42 C 0.5988(8) 0.6650(7) 0.1741(5) 0.032(2) Uani 1 1 d . . . . .
H42A H 0.634487 0.675904 0.118575 0.038 Uiso 1 1 calc R U . . .
H42B H 0.548359 0.722685 0.177014 0.038 Uiso 1 1 calc R U . . .
C43 C 0.5351(8) 0.5734(6) 0.2096(5) 0.029(2) Uani 1 1 d . . . . .
C44 C 0.5645(8) 0.4992(8) 0.1790(5) 0.036(2) Uani 1 1 d . . . . .
H44 H 0.622220 0.506862 0.133359 0.043 Uiso 1 1 calc R U . . .
C45 C 0.5092(8) 0.4133(7) 0.2155(6) 0.037(2) Uani 1 1 d . . . . .
H45 H 0.528011 0.362914 0.193793 0.045 Uiso 1 1 calc R U . . .
C46 C 0.4278(8) 0.4007(7) 0.2825(5) 0.032(2) Uani 1 1 d . . . . .
C47 C 0.3973(8) 0.4748(7) 0.3126(6) 0.036(2) Uani 1 1 d . . . . .
H47 H 0.340064 0.466164 0.358592 0.043 Uiso 1 1 calc R U . . .
C48 C 0.4500(9) 0.5626(7) 0.2757(6) 0.042(3) Uani 1 1 d . . . . .
H48 H 0.427756 0.614345 0.295776 0.050 Uiso 1 1 calc R U . . .
C49 C 0.3670(8) 0.3071(7) 0.3224(6) 0.037(2) Uani 1 1 d . . . . .
H49A H 0.418677 0.250786 0.317514 0.044 Uiso 1 1 calc R U . . .
H49B H 0.338357 0.296485 0.378597 0.044 Uiso 1 1 calc R U . . .
C50 C 0.2887(9) 0.2697(7) 0.2358(5) 0.034(2) Uani 1 1 d . . . . .
H50 H 0.356097 0.235490 0.221177 0.041 Uiso 1 1 calc R U . . .
C51 C 0.2049(9) 0.2767(7) 0.2019(6) 0.040(3) Uani 1 1 d . . . . .
H51 H 0.214758 0.248029 0.163452 0.048 Uiso 1 1 calc R U . . .
C52 C 0.1070(10) 0.3251(8) 0.2236(6) 0.047(3) Uani 1 1 d . . . . .
H52 H 0.048642 0.330109 0.200582 0.056 Uiso 1 1 calc R U . . .
C53 C 0.0946(10) 0.3668(8) 0.2797(6) 0.049(3) Uani 1 1 d . . . . .
H53 H 0.027708 0.401041 0.295277 0.059 Uiso 1 1 calc R U . . .
C54 C 0.1793(9) 0.3579(8) 0.3121(6) 0.047(3) Uani 1 1 d . . . . .
H54 H 0.170876 0.384958 0.351293 0.056 Uiso 1 1 calc R U . . .
Cl2A Cl 1.3811(12) -0.1786(11) 0.3054(8) 0.0196(11) Uani 0.592(7) 1 d . . P A 2
Cl5A Cl 1.591(4) 0.152(2) 0.204(3) 0.0320(18) Uani 0.556(7) 1 d D . P A 2
Cl7A Cl 0.9144(10) -0.6045(9) 0.4366(6) 0.0257(7) Uani 0.406(8) 1 d . . P B 2
Cl Cl 0.9161(10) 0.4089(9) -0.0687(6) 0.0324(7) Uani 0.368(8) 1 d . . P C 2
Cl1 Cl 1.1341(8) 0.6131(6) -0.1629(7) 0.0357(6) Uani 0.313(6) 1 d . . P C 2
Br6A Br 1.6157(3) -0.11476(18) 0.36421(19) 0.0408(7) Uani 0.715(8) 1 d . . P A
1
Cl8A Cl 1.1296(17) -0.3957(15) 0.3502(12) 0.0301(5) Uani 0.205(8) 1 d . . P B 2
Br9A Br 0.8242(3) -0.3521(3) 0.4876(2) 0.0260(6) Uani 0.818(7) 1 d . . P B 1
Cl2 Cl 1.182(3) 0.358(3) -0.008(2) 0.0309(5) Uani 0.120(7) 1 d . . P C 2
Cl3A Cl 1.359(3) 0.0625(19) 0.149(2) 0.0309(5) Uani 0.181(7) 1 d . . P A 2
Br4A Br 1.3400(4) 0.0413(3) 0.3702(2) 0.0437(7) Uani 0.799(8) 1 d . . P A 1
Cl1A Cl 1.632(9) -0.081(6) 0.137(9) 0.0362(6) Uani 0.102(7) 1 d . . P A 2


_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
Bi1 Br1B 2.849(6) . ?
Bi1 Br2B 2.882(7) . ?
Bi1 Br3B 2.830(3) . ?
Bi1 Cl4B 2.70(2) . ?
Bi1 Br5 2.830(10) . ?
Bi1 Cl6B 2.740(17) . ?
Bi1 Cl2A 2.663(14) . ?
Bi1 Cl5A 2.721(19) . ?
Bi1 Br6A 2.872(3) . ?
Bi1 Cl3A 2.74(4) . ?
Bi1 Br4A 2.858(2) . ?
Bi1 Cl1A 2.76(15) . ?
Bi2 Br7B 2.829(3) . ?
Bi2 Br7B 2.829(3) 2_746 ?
Bi2 Br8B 2.8496(18) . ?
Bi2 Br8B 2.8495(18) 2_746 ?
Bi2 Cl9B 2.92(5) 2_746 ?
Bi2 Cl9B 2.92(5) . ?
Bi2 Cl7A 2.794(13) . ?
Bi2 Cl7A 2.794(13) 2_746 ?
Bi2 Cl8A 2.84(2) . ?
Bi2 Cl8A 2.84(2) 2_746 ?
Bi2 Br9A 2.860(4) 2_746 ?
Bi2 Br9A 2.860(4) . ?
Bi3 Br10 2.7720(15) . ?
Bi3 Br10 2.7720(15) 2_765 ?
Bi3 Br2 2.8662(18) 2_765 ?
Bi3 Br2 2.8662(18) . ?
Bi3 Br 2.835(2) 2_765 ?
Bi3 Br 2.835(2) . ?
Bi3 Cl 2.708(12) 2_765 ?
Bi3 Cl 2.708(12) . ?
Bi3 Cl1 3.059(10) . ?
Bi3 Cl1 3.059(10) 2_765 ?
Bi3 Cl2 2.88(4) 2_765 ?
Bi3 Cl2 2.88(4) . ?
N1 C1 1.340(12) . ?
N1 C5 1.346(12) . ?
N1 C6 1.509(12) . ?
C1 H1 0.9500 . ?
C1 C2 1.359(14) . ?
C2 H2 0.9500 . ?
C2 C3 1.391(14) . ?
C3 H3 0.9500 . ?
C3 C4 1.366(14) . ?
C4 H4 0.9500 . ?
C4 C5 1.359(14) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.487(13) . ?
C7 C8 1.395(12) . ?
C7 C9 1.381(13) 2_845 ?
C8 H8 0.9500 . ?
C8 C9 1.402(14) . ?
C9 H9 0.9500 . ?
N2 C10 1.346(14) . ?
N2 C14 1.340(14) . ?
N2 C15 1.493(14) . ?
N3 C22 1.497(14) . ?
N3 C23 1.338(13) . ?
N3 C27 1.352(13) . ?
C10 H10 0.9500 . ?
C10 C11 1.374(17) . ?
C11 H11 0.9500 . ?
C11 C12 1.388(18) . ?
C12 H12 0.9500 . ?
C12 C13 1.354(18) . ?
C13 H13 0.9500 . ?
C13 C14 1.331(18) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.528(15) . ?
C16 C17 1.377(15) . ?
C16 C21 1.390(15) . ?
C17 H17 0.9500 . ?
C17 C18 1.367(15) . ?
C18 H18 0.9500 . ?
C18 C19 1.406(14) . ?
C19 C20 1.394(15) . ?
C19 C22 1.494(14) . ?
C20 H20 0.9500 . ?
C20 C21 1.414(16) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23 0.9500 . ?
C23 C24 1.362(16) . ?
C24 H24 0.9500 . ?
C24 C25 1.375(15) . ?
C25 H25 0.9500 . ?
C25 C26 1.360(17) . ?
C26 H26 0.9500 . ?
C26 C27 1.377(17) . ?
C27 H27 0.9500 . ?
N4 C28 1.355(16) . ?
N4 C32 1.309(15) . ?
N4 C33 1.493(14) . ?
C28 H28 0.9500 . ?
C28 C29 1.430(18) . ?
C29 H29 0.9500 . ?
C29 C30 1.367(19) . ?
C30 H30 0.9500 . ?
C30 C31 1.34(2) . ?
C31 H31 0.9500 . ?
C31 C32 1.321(18) . ?
C32 H32 0.9500 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.475(16) . ?
C34 C35 1.382(16) . ?
C34 C36 1.378(15) 2_666 ?
C35 H35 0.9500 . ?
C35 C36 1.376(17) . ?
C36 H36 0.9500 . ?
N5 C37 1.345(12) . ?
N5 C41 1.355(12) . ?
N5 C42 1.470(11) . ?
N6 C49 1.473(12) . ?
N6 C50 1.329(11) . ?
N6 C54 1.357(12) . ?
C37 H37 0.9500 . ?
C37 C38 1.364(14) . ?
C38 H38 0.9500 . ?
C38 C39 1.354(15) . ?
C39 H39 0.9500 . ?
C39 C40 1.377(14) . ?
C40 H40 0.9500 . ?
C40 C41 1.375(14) . ?
C41 H41 0.9500 . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C42 C43 1.516(12) . ?
C43 C44 1.383(13) . ?
C43 C48 1.388(13) . ?
C44 H44 0.9500 . ?
C44 C45 1.391(14) . ?
C45 H45 0.9500 . ?
C45 C46 1.371(13) . ?
C46 C47 1.375(13) . ?
C46 C49 1.518(13) . ?
C47 H47 0.9500 . ?
C47 C48 1.396(13) . ?
C48 H48 0.9500 . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C50 H50 0.9500 . ?
C50 C51 1.377(14) . ?
C51 H51 0.9500 . ?
C51 C52 1.372(15) . ?
C52 H52 0.9500 . ?
C52 C53 1.391(14) . ?
C53 H53 0.9500 . ?
C53 C54 1.362(15) . ?
C54 H54 0.9500 . ?

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
Br1B Bi1 Br2B 90.17(16) . . ?
Br1B Bi1 Br6A 92.17(15) . . ?
Br1B Bi1 Br4A 177.32(18) . . ?
Br3B Bi1 Br1B 88.64(14) . . ?
Br3B Bi1 Br2B 87.66(14) . . ?
Br3B Bi1 Br5 89.8(5) . . ?
Br3B Bi1 Br6A 178.62(8) . . ?
Br3B Bi1 Br4A 93.94(15) . . ?
Cl4B Bi1 Cl6B 85.9(17) . . ?
Cl4B Bi1 Cl5A 84.4(16) . . ?
Cl4B Bi1 Cl3A 92.1(18) . . ?
Cl4B Bi1 Cl1A 178(2) . . ?
Br5 Bi1 Br1B 89.8(6) . . ?
Br5 Bi1 Br2B 177.5(6) . . ?
Br5 Bi1 Br6A 89.1(5) . . ?
Br5 Bi1 Br4A 89.5(6) . . ?
Cl6B Bi1 Cl1A 95(3) . . ?
Cl2A Bi1 Cl4B 90.6(11) . . ?
Cl2A Bi1 Cl6B 94.6(5) . . ?
Cl2A Bi1 Cl5A 175.0(12) . . ?
Cl2A Bi1 Cl3A 86.8(5) . . ?
Cl2A Bi1 Cl1A 90.4(11) . . ?
Cl5A Bi1 Cl6B 84.9(12) . . ?
Cl5A Bi1 Cl3A 93.6(12) . . ?
Cl5A Bi1 Cl1A 94.6(16) . . ?
Br6A Bi1 Br2B 93.45(14) . . ?
Cl3A Bi1 Cl6B 177.6(9) . . ?
Cl3A Bi1 Cl1A 87(3) . . ?
Br4A Bi1 Br2B 90.68(17) . . ?
Br4A Bi1 Br6A 85.25(16) . . ?
Br7B Bi2 Br7B 180.0 2_746 . ?
Br7B Bi2 Br8B 90.00(6) . . ?
Br7B Bi2 Br8B 90.00(6) . 2_746 ?
Br7B Bi2 Br8B 90.00(6) 2_746 2_746 ?
Br7B Bi2 Br8B 90.00(6) 2_746 . ?
Br7B Bi2 Cl9B 83.6(8) . 2_746 ?
Br7B Bi2 Cl9B 96.4(8) 2_746 2_746 ?
Br7B Bi2 Cl8A 99.3(4) 2_746 2_746 ?
Br7B Bi2 Cl8A 80.7(4) . 2_746 ?
Br7B Bi2 Br9A 91.51(8) . . ?
Br7B Bi2 Br9A 88.49(8) 2_746 . ?
Br7B Bi2 Br9A 88.49(8) . 2_746 ?
Br7B Bi2 Br9A 91.51(8) 2_746 2_746 ?
Br8B Bi2 Br8B 180.0 2_746 . ?
Br8B Bi2 Cl9B 87.2(10) . 2_746 ?
Br8B Bi2 Cl9B 92.8(10) 2_746 2_746 ?
Br8B Bi2 Br9A 89.23(8) 2_746 . ?
Br8B Bi2 Br9A 90.77(9) 2_746 2_746 ?
Br8B Bi2 Br9A 90.77(9) . . ?
Br8B Bi2 Br9A 89.23(8) . 2_746 ?
Cl7A Bi2 Cl9B 98.4(8) . . ?
Cl7A Bi2 Cl9B 81.6(8) 2_746 . ?
Cl7A Bi2 Cl7A 180.0 2_746 . ?
Cl7A Bi2 Cl8A 89.3(4) 2_746 . ?
Cl7A Bi2 Cl8A 90.8(4) . . ?
Cl8A Bi2 Cl9B 85.7(11) 2_746 . ?
Cl8A Bi2 Cl9B 94.3(11) . . ?
Br9A Bi2 Cl9B 5.3(8) 2_746 2_746 ?
Br9A Bi2 Cl9B 174.7(8) . 2_746 ?
Br9A Bi2 Br9A 180.0 2_746 . ?
Br10 Bi3 Br10 180.0 2_765 . ?
Br10 Bi3 Br2 87.04(5) . . ?
Br10 Bi3 Br2 87.04(5) 2_765 2_765 ?
Br10 Bi3 Br2 92.96(5) 2_765 . ?
Br10 Bi3 Br2 92.96(5) . 2_765 ?
Br10 Bi3 Br 91.43(7) 2_765 2_765 ?
Br10 Bi3 Br 88.57(7) 2_765 . ?
Br10 Bi3 Br 91.43(7) . . ?
Br10 Bi3 Br 88.57(7) . 2_765 ?
Br10 Bi3 Cl1 165.9(2) . 2_765 ?
Br10 Bi3 Cl1 14.1(2) 2_765 2_765 ?
Br10 Bi3 Cl2 79.3(7) 2_765 2_765 ?
Br10 Bi3 Cl2 100.7(7) . 2_765 ?
Br2 Bi3 Br2 180.0 2_765 . ?
Br2 Bi3 Cl1 90.02(17) . 2_765 ?
Br2 Bi3 Cl1 89.99(17) 2_765 2_765 ?
Br2 Bi3 Cl2 8.2(7) 2_765 2_765 ?
Br2 Bi3 Cl2 171.8(7) . 2_765 ?
Br Bi3 Br2 88.46(6) . . ?
Br Bi3 Br2 91.54(6) 2_765 . ?
Br Bi3 Br2 88.46(6) 2_765 2_765 ?
Br Bi3 Br2 91.54(6) . 2_765 ?
Br Bi3 Br 180.0 2_765 . ?
Br Bi3 Cl1 77.7(2) 2_765 2_765 ?
Br Bi3 Cl1 102.3(2) . 2_765 ?
Br Bi3 Cl2 94.0(8) . 2_765 ?
Br Bi3 Cl2 86.0(8) 2_765 2_765 ?
Cl Bi3 Cl1 92.9(3) 2_765 . ?
Cl Bi3 Cl1 87.1(3) . . ?
Cl Bi3 Cl2 95.1(9) . 2_765 ?
Cl Bi3 Cl2 84.9(9) . . ?
Cl Bi3 Cl2 95.1(9) 2_765 . ?
Cl Bi3 Cl2 84.9(9) 2_765 2_765 ?
Cl1 Bi3 Cl1 180.0 2_765 . ?
Cl2 Bi3 Cl1 98.2(7) 2_765 . ?
Cl2 Bi3 Cl1 81.8(7) . . ?
Cl2 Bi3 Cl2 180.0 . 2_765 ?
C1 N1 C5 121.8(9) . . ?
C1 N1 C6 119.4(8) . . ?
C5 N1 C6 118.8(8) . . ?
N1 C1 H1 120.1 . . ?
N1 C1 C2 119.8(9) . . ?
C2 C1 H1 120.1 . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.7(10) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.7(10) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.5(10) . . ?
C5 C4 H4 120.7 . . ?
N1 C5 C4 120.5(9) . . ?
N1 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
N1 C6 H6A 109.4 . . ?
N1 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 N1 111.0(8) . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C8 C7 C6 118.9(9) . . ?
C9 C7 C6 121.9(9) 2_845 . ?
C9 C7 C8 119.1(9) 2_845 . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.2(9) . . ?
C9 C8 H8 119.9 . . ?
C7 C9 C8 120.7(9) 2_845 . ?
C7 C9 H9 119.7 2_845 . ?
C8 C9 H9 119.7 . . ?
C10 N2 C15 118.7(10) . . ?
C14 N2 C10 120.5(11) . . ?
C14 N2 C15 120.8(10) . . ?
C23 N3 C22 120.3(9) . . ?
C23 N3 C27 119.9(11) . . ?
C27 N3 C22 119.8(10) . . ?
N2 C10 H10 120.2 . . ?
N2 C10 C11 119.5(11) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.3(12) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 120.6 . . ?
C13 C12 C11 118.8(13) . . ?
C13 C12 H12 120.6 . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.8(13) . . ?
C14 C13 H13 119.6 . . ?
N2 C14 H14 119.4 . . ?
C13 C14 N2 121.1(12) . . ?
C13 C14 H14 119.4 . . ?
N2 C15 H15A 109.0 . . ?
N2 C15 H15B 109.0 . . ?
N2 C15 C16 112.9(8) . . ?
H15A C15 H15B 107.8 . . ?
C16 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
C17 C16 C15 120.9(10) . . ?
C17 C16 C21 119.2(11) . . ?
C21 C16 C15 119.9(11) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 121.1(11) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 H18 119.1 . . ?
C17 C18 C19 121.7(11) . . ?
C19 C18 H18 119.1 . . ?
C18 C19 C22 121.8(10) . . ?
C20 C19 C18 117.5(10) . . ?
C20 C19 C22 120.7(9) . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.5(10) . . ?
C21 C20 H20 119.8 . . ?
C16 C21 C20 120.0(11) . . ?
C16 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
N3 C22 H22A 109.1 . . ?
N3 C22 H22B 109.1 . . ?
C19 C22 N3 112.5(8) . . ?
C19 C22 H22A 109.1 . . ?
C19 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?
N3 C23 H23 119.3 . . ?
N3 C23 C24 121.4(10) . . ?
C24 C23 H23 119.3 . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C25 120.7(12) . . ?
C25 C24 H24 119.7 . . ?
C24 C25 H25 121.7 . . ?
C26 C25 C24 116.7(12) . . ?
C26 C25 H25 121.7 . . ?
C25 C26 H26 118.7 . . ?
C25 C26 C27 122.6(12) . . ?
C27 C26 H26 118.7 . . ?
N3 C27 C26 118.7(12) . . ?
N3 C27 H27 120.6 . . ?
C26 C27 H27 120.6 . . ?
C28 N4 C33 120.9(10) . . ?
C32 N4 C28 123.1(12) . . ?
C32 N4 C33 115.9(11) . . ?
N4 C28 H28 121.5 . . ?
N4 C28 C29 117.0(13) . . ?
C29 C28 H28 121.5 . . ?
C28 C29 H29 122.0 . . ?
C30 C29 C28 116.0(14) . . ?
C30 C29 H29 122.0 . . ?
C29 C30 H30 118.2 . . ?
C31 C30 C29 123.5(15) . . ?
C31 C30 H30 118.2 . . ?
C30 C31 H31 120.7 . . ?
C32 C31 C30 118.6(17) . . ?
C32 C31 H31 120.7 . . ?
N4 C32 C31 121.5(17) . . ?
N4 C32 H32 119.2 . . ?
C31 C32 H32 119.2 . . ?
N4 C33 H33A 108.8 . . ?
N4 C33 H33B 108.8 . . ?
H33A C33 H33B 107.7 . . ?
C34 C33 N4 113.7(9) . . ?
C34 C33 H33A 108.8 . . ?
C34 C33 H33B 108.8 . . ?
C35 C34 C33 121.4(11) . . ?
C36 C34 C33 120.2(11) 2_666 . ?
C36 C34 C35 118.3(11) 2_666 . ?
C34 C35 H35 119.2 . . ?
C36 C35 C34 121.6(11) . . ?
C36 C35 H35 119.2 . . ?
C34 C36 H36 119.9 2_666 . ?
C35 C36 C34 120.1(11) . 2_666 ?
C35 C36 H36 119.9 . . ?
C37 N5 C41 119.7(9) . . ?
C37 N5 C42 119.6(8) . . ?
C41 N5 C42 120.7(8) . . ?
C50 N6 C49 120.1(8) . . ?
C50 N6 C54 121.1(9) . . ?
C54 N6 C49 118.7(8) . . ?
N5 C37 H37 119.9 . . ?
N5 C37 C38 120.3(10) . . ?
C38 C37 H37 119.9 . . ?
C37 C38 H38 119.4 . . ?
C39 C38 C37 121.3(10) . . ?
C39 C38 H38 119.4 . . ?
C38 C39 H39 120.7 . . ?
C38 C39 C40 118.6(10) . . ?
C40 C39 H39 120.7 . . ?
C39 C40 H40 120.2 . . ?
C41 C40 C39 119.6(10) . . ?
C41 C40 H40 120.2 . . ?
N5 C41 C40 120.6(9) . . ?
N5 C41 H41 119.7 . . ?
C40 C41 H41 119.7 . . ?
N5 C42 H42A 109.8 . . ?
N5 C42 H42B 109.8 . . ?
N5 C42 C43 109.5(7) . . ?
H42A C42 H42B 108.2 . . ?
C43 C42 H42A 109.8 . . ?
C43 C42 H42B 109.8 . . ?
C44 C43 C42 120.7(9) . . ?
C44 C43 C48 120.1(9) . . ?
C48 C43 C42 119.1(9) . . ?
C43 C44 H44 120.2 . . ?
C43 C44 C45 119.6(9) . . ?
C45 C44 H44 120.2 . . ?
C44 C45 H45 119.8 . . ?
C46 C45 C44 120.5(9) . . ?
C46 C45 H45 119.8 . . ?
C45 C46 C47 120.1(9) . . ?
C45 C46 C49 120.7(9) . . ?
C47 C46 C49 119.2(9) . . ?
C46 C47 H47 119.9 . . ?
C46 C47 C48 120.3(9) . . ?
C48 C47 H47 119.9 . . ?
C43 C48 C47 119.3(9) . . ?
C43 C48 H48 120.3 . . ?
C47 C48 H48 120.3 . . ?
N6 C49 C46 112.2(8) . . ?
N6 C49 H49A 109.2 . . ?
N6 C49 H49B 109.2 . . ?
C46 C49 H49A 109.2 . . ?
C46 C49 H49B 109.2 . . ?
H49A C49 H49B 107.9 . . ?
N6 C50 H50 119.9 . . ?
N6 C50 C51 120.2(9) . . ?
C51 C50 H50 119.9 . . ?
C50 C51 H51 120.0 . . ?
C52 C51 C50 119.9(9) . . ?
C52 C51 H51 120.0 . . ?
C51 C52 H52 120.5 . . ?
C51 C52 C53 119.0(10) . . ?
C53 C52 H52 120.5 . . ?
C52 C53 H53 120.3 . . ?
C54 C53 C52 119.3(10) . . ?
C54 C53 H53 120.3 . . ?
N6 C54 C53 120.4(10) . . ?
N6 C54 H54 119.8 . . ?
C53 C54 H54 119.8 . . ?

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 C1 C2 C3 0.6(15) . . . . ?
N1 C6 C7 C8 120.2(9) . . . . ?
N1 C6 C7 C9 -62.6(11) . . . 2_845 ?
C1 N1 C5 C4 0.6(15) . . . . ?
C1 N1 C6 C7 -84.3(11) . . . . ?
C1 C2 C3 C4 -1.0(16) . . . . ?
C2 C3 C4 C5 1.2(16) . . . . ?
C3 C4 C5 N1 -1.0(16) . . . . ?
C5 N1 C1 C2 -0.4(15) . . . . ?
C5 N1 C6 C7 96.3(10) . . . . ?
C6 N1 C1 C2 -179.8(9) . . . . ?
C6 N1 C5 C4 -180.0(9) . . . . ?
C6 C7 C8 C9 176.5(9) . . . . ?
C7 C8 C9 C7 0.7(16) . . . 2_845 ?
C9 C7 C8 C9 -0.7(16) 2_845 . . . ?
N2 C10 C11 C12 1.1(18) . . . . ?
N2 C15 C16 C17 90.7(13) . . . . ?
N2 C15 C16 C21 -91.1(13) . . . . ?
N3 C23 C24 C25 0.0(16) . . . . ?
C10 N2 C14 C13 -0.4(16) . . . . ?
C10 N2 C15 C16 -102.6(11) . . . . ?
C10 C11 C12 C13 -1.8(18) . . . . ?
C11 C12 C13 C14 1.5(18) . . . . ?
C12 C13 C14 N2 -0.3(18) . . . . ?
C14 N2 C10 C11 0.0(16) . . . . ?
C14 N2 C15 C16 79.2(12) . . . . ?
C15 N2 C10 C11 -178.1(10) . . . . ?
C15 N2 C14 C13 177.7(10) . . . . ?
C15 C16 C17 C18 178.9(10) . . . . ?
C15 C16 C21 C20 -178.5(12) . . . . ?
C16 C17 C18 C19 -1.1(18) . . . . ?
C17 C16 C21 C20 0(2) . . . . ?
C17 C18 C19 C20 1.1(17) . . . . ?
C17 C18 C19 C22 -179.6(11) . . . . ?
C18 C19 C20 C21 -0.8(19) . . . . ?
C18 C19 C22 N3 88.2(12) . . . . ?
C19 C20 C21 C16 0(2) . . . . ?
C20 C19 C22 N3 -92.6(13) . . . . ?
C21 C16 C17 C18 0.7(18) . . . . ?
C22 N3 C23 C24 -176.9(9) . . . . ?
C22 N3 C27 C26 177.7(9) . . . . ?
C22 C19 C20 C21 179.9(12) . . . . ?
C23 N3 C22 C19 -99.4(11) . . . . ?
C23 N3 C27 C26 -0.1(14) . . . . ?
C23 C24 C25 C26 -1.6(16) . . . . ?
C24 C25 C26 C27 2.4(16) . . . . ?
C25 C26 C27 N3 -1.6(16) . . . . ?
C27 N3 C22 C19 82.8(11) . . . . ?
C27 N3 C23 C24 0.9(15) . . . . ?
N4 C28 C29 C30 -3.8(19) . . . . ?
N4 C33 C34 C35 -115.9(12) . . . . ?
N4 C33 C34 C36 66.7(15) . . . 2_666 ?
C28 N4 C32 C31 -3(2) . . . . ?
C28 N4 C33 C34 -122.2(12) . . . . ?
C28 C29 C30 C31 5(2) . . . . ?
C29 C30 C31 C32 -5(3) . . . . ?
C30 C31 C32 N4 4(2) . . . . ?
C32 N4 C28 C29 3.2(18) . . . . ?
C32 N4 C33 C34 56.9(15) . . . . ?
C33 N4 C28 C29 -177.8(11) . . . . ?
C33 N4 C32 C31 177.7(13) . . . . ?
C33 C34 C35 C36 -177.9(11) . . . . ?
C34 C35 C36 C34 0(2) . . . 2_666 ?
C36 C34 C35 C36 0(2) 2_666 . . . ?
N5 C37 C38 C39 0.0(18) . . . . ?
N5 C42 C43 C44 -94.8(10) . . . . ?
N5 C42 C43 C48 81.9(11) . . . . ?
N6 C50 C51 C52 -0.8(15) . . . . ?
C37 N5 C41 C40 1.0(15) . . . . ?
C37 N5 C42 C43 -94.4(10) . . . . ?
C37 C38 C39 C40 0.5(18) . . . . ?
C38 C39 C40 C41 -0.2(17) . . . . ?
C39 C40 C41 N5 -0.5(16) . . . . ?
C41 N5 C37 C38 -0.7(15) . . . . ?
C41 N5 C42 C43 82.9(11) . . . . ?
C42 N5 C37 C38 176.6(10) . . . . ?
C42 N5 C41 C40 -176.3(9) . . . . ?
C42 C43 C44 C45 176.0(8) . . . . ?
C42 C43 C48 C47 -174.5(9) . . . . ?
C43 C44 C45 C46 -1.7(15) . . . . ?
C44 C43 C48 C47 2.3(16) . . . . ?
C44 C45 C46 C47 2.5(15) . . . . ?
C44 C45 C46 C49 179.8(9) . . . . ?
C45 C46 C47 C48 -0.9(16) . . . . ?
C45 C46 C49 N6 -84.7(11) . . . . ?
C46 C47 C48 C43 -1.5(16) . . . . ?
C47 C46 C49 N6 92.6(11) . . . . ?
C48 C43 C44 C45 -0.8(15) . . . . ?
C49 N6 C50 C51 -177.1(9) . . . . ?
C49 N6 C54 C53 176.9(10) . . . . ?
C49 C46 C47 C48 -178.3(9) . . . . ?
C50 N6 C49 C46 97.4(10) . . . . ?
C50 N6 C54 C53 -1.9(16) . . . . ?
C50 C51 C52 C53 0.2(16) . . . . ?
C51 C52 C53 C54 -0.5(17) . . . . ?
C52 C53 C54 N6 1.3(18) . . . . ?
C54 N6 C49 C46 -81.3(11) . . . . ?
C54 N6 C50 C51 1.6(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

_vrf_PLAT971_pyxk_bibr_4_1_dmso  
;
PROBLEM: Large positive calculated residual density near bismuth atom.
RESPONSE: The problem is related to the strong absorption and low quality of the 
crystalline samples.
;
_vrf_PLAT234_pyxk_bibr_4_1_dmso  
;
PROBLEM: Large Hirshfeld difference (carbon atoms).
RESPONSE: The problem is related to the strong absorption and low quality of the 
crystalline samples.
;
_vrf_PLAT973_pyxk_bibr_4_1_dmso  
;
PROBLEM: Positive calculated residual density near bismuth atom.
RESPONSE: The problem is related to the strong absorption and low quality of the 
crystalline samples.
;
####################################################################### 
# 
# 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_kotov143
_database_code_depnum_ccdc_archive 'CCDC 2349774'
loop_
_audit_author_name
_audit_author_address
'Petr Buikin'
;N S Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-05-15 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_audit_creation_date             2024-04-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '4(Bi I6), 6(C18 H18 N2), 4(C3 H7 N O)'
_chemical_formula_sum            'C120 H136 Bi4 I24 N16 O4'
_chemical_formula_weight         5747.96
_chemical_absolute_configuration ?
_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 0.0033 0.0016 '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'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   22.399(2)
_cell_length_b                   21.812(2)
_cell_length_c                   32.531(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     15894(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    137650
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      26.311
_cell_measurement_theta_min      1.566
_shelx_estimated_absorpt_T_max   0.712
_shelx_estimated_absorpt_T_min   0.200
_exptl_absorpt_coefficient_mu    9.126
_exptl_absorpt_correction_T_max  0.698
_exptl_absorpt_correction_T_min  0.379
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.402
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             10416
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            216605
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         1.446
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.959
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                26987
_reflns_number_total             31241
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         2.579
_refine_diff_density_min         -5.851
_refine_diff_density_rms         0.355
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.503(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     756
_refine_ls_number_reflns         31241
_refine_ls_number_restraints     313
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0751
_refine_ls_restrained_S_all      1.198
_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)+1080.9854P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1617
_refine_ls_wR_factor_ref         0.1753
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.49742
 0.50258
2. Restrained distances
 O201-C201
 1.2 with sigma of 0.01
 O221-C221
 1.2 with sigma of 0.01
 N221-C222 = N221-C223
 1.45 with sigma of 0.01
 C221-C222
 2.6 with sigma of 0.02
 N221-C221
 1.35 with sigma of 0.01
 C221-C222 = C221-C223
 2.45 with sigma of 0.02
 O231-C231
 1.2 with sigma of 0.01
 N231-C232 = N231-C233
 1.45 with sigma of 0.01
 C231-C232
 2.6 with sigma of 0.02
 O221-N221
 2.26 with sigma of 0.02
 N231-C231
 1.35 with sigma of 0.01
 C231-C232 = C231-C233
 2.45 with sigma of 0.02
 O231-N231
 2.26 with sigma of 0.02
 N201-C202 = N201-C203
 1.45 with sigma of 0.01
 C201-C202
 2.6 with sigma of 0.02
 N201-C201
 1.35 with sigma of 0.01
 C201-C202 = C201-C203
 2.45 with sigma of 0.02
 O201-N201
 2.26 with sigma of 0.02
 O211-C211
 1.2 with sigma of 0.01
 N211-C212 = N211-C213
 1.45 with sigma of 0.01
 C211-C212
 2.6 with sigma of 0.02
 N211-C211
 1.35 with sigma of 0.01
 C211-C212 = C211-C213
 2.45 with sigma of 0.02
 O211-N211
 2.26 with sigma of 0.02
 C6-N1 = C6-C7 = C13-C10 = C13-N2 = C24-N3 = C24-C25 = C31-C28 = C31-N4
 1.54 with sigma of 0.01
 C42-N5 = C42-C43 = C49-C46 = C49-N6 = C60-N7 = C60-C61 = C67-C64 = C67-N8
 1.54 with sigma of 0.01
 C78-N9 = C78-C79 = C85-C82 = C85-N10 = C96-N11 = C96-C97 = C103-C100 = C103-N12
 1.54 with sigma of 0.01
 C6-C1 = C6-C5 = C6-C8 = C6-C12 = C13-C9 = C13-C11 = C13-C14 = C13-C18
 2.5 with sigma of 0.02
 C24-C19 = C24-C23 = C24-C26 = C24-C30 = C31-C27 = C31-C29 = C31-C32 = C31-C36
 2.5 with sigma of 0.02
 C42-C37 = C42-C41 = C42-C44 = C42-C48 = C49-C45 = C49-C47 = C49-C50 = C49-C54
 2.5 with sigma of 0.02
 C60-C55 = C60-C59 = C60-C62 = C60-C66 = C67-C63 = C67-C65 = C67-C68 = C67-C72
 2.5 with sigma of 0.02
 C78-C73 = C78-C79 = C78-C80 = C78-C84 = C85-C81 = C85-C83 = C85-C86 = C85-C90
 2.5 with sigma of 0.02
 C96-C91 = C96-C95 = C96-C98 = C96-C102 = C103-C99 = C103-C101 = C103-C104
 2.5 with sigma of 0.02
 C103-C108
 2.5 with sigma of 0.02
 O231-C231 \\sim O1-C111
 with sigma of 0.02
 N231-C231 \\sim N14-C111
 with sigma of 0.02
 N231-C232 \\sim N14-C1L
 with sigma of 0.02
 N231-C233 \\sim N14-C1K
 with sigma of 0.02
 O231-N231 \\sim O1-N14
 with sigma of 0.04
 C231-C232 \\sim C111-C1L
 with sigma of 0.04
 C231-C233 \\sim C111-C1K
 with sigma of 0.04
 C232-C233 \\sim C1L-C1K
 with sigma of 0.04
 O221-C221 \\sim O2-C110
 with sigma of 0.02
 N221-C221 \\sim N13-C110
 with sigma of 0.02
 N221-C222 \\sim N13-C1J
 with sigma of 0.02
 N221-C223 \\sim N13-C1I
 with sigma of 0.02
 O221-N221 \\sim O2-N13
 with sigma of 0.04
 C221-C222 \\sim C110-C1J
 with sigma of 0.04
 C221-C223 \\sim C110-C1I
 with sigma of 0.04
 C222-C223 \\sim C1J-C1I
 with sigma of 0.04
 N3-C19 \\sim N3A-C19A
 with sigma of 0.02
 N3-C23 \\sim N3A-C23A
 with sigma of 0.02
 N3-C24 \\sim N3A-C24A
 with sigma of 0.02
 C19-C20 \\sim C19A-C20A
 with sigma of 0.02
 C20-C21 \\sim C20A-C21A
 with sigma of 0.02
 C21-C22 \\sim C21A-C22A
 with sigma of 0.02
 C22-C23 \\sim C22A-C23A
 with sigma of 0.02
 N4-C32 \\sim N4A-C32A
 with sigma of 0.02
 N4-C36 \\sim N4A-C36A
 with sigma of 0.02
 N4-C31 \\sim N4A-C31A
 with sigma of 0.02
 C32-C33 \\sim C32A-C33A
 with sigma of 0.02
 C33-C34 \\sim C33A-C34A
 with sigma of 0.02
 C34-C35 \\sim C34A-C35A
 with sigma of 0.02
 C35-C36 \\sim C35A-C36A
 with sigma of 0.02
 C25-C26 \\sim C25A-C26A
 with sigma of 0.02
 C25-C30 \\sim C25A-C30A
 with sigma of 0.02
 C25-C24 \\sim C25A-C24A
 with sigma of 0.02
 C26-C27 \\sim C26A-C27A
 with sigma of 0.02
 C27-C28 \\sim C27A-C28A
 with sigma of 0.02
 C28-C29 \\sim C28A-C29A
 with sigma of 0.02
 C28-C31 \\sim C28A-C31A
 with sigma of 0.02
 C29-C30 \\sim C29A-C30A
 with sigma of 0.02
 N3-C20 \\sim N3A-C20A
 with sigma of 0.04
 N3-C22 \\sim N3A-C22A
 with sigma of 0.04
 N3-C25 \\sim N3A-C25A
 with sigma of 0.04
 C19-C21 \\sim C19A-C21A
 with sigma of 0.04
 C19-C23 \\sim C19A-C23A
 with sigma of 0.04
 C19-C24 \\sim C19A-C24A
 with sigma of 0.04
 C20-C22 \\sim C20A-C22A
 with sigma of 0.04
 C21-C23 \\sim C21A-C23A
 with sigma of 0.04
 C23-C24 \\sim C23A-C24A
 with sigma of 0.04
 N4-C33 \\sim N4A-C33A
 with sigma of 0.04
 N4-C35 \\sim N4A-C35A
 with sigma of 0.04
 N4-C28 \\sim N4A-C28A
 with sigma of 0.04
 C32-C34 \\sim C32A-C34A
 with sigma of 0.04
 C32-C36 \\sim C32A-C36A
 with sigma of 0.04
 C32-C31 \\sim C32A-C31A
 with sigma of 0.04
 C33-C35 \\sim C33A-C35A
 with sigma of 0.04
 C34-C36 \\sim C34A-C36A
 with sigma of 0.04
 C36-C31 \\sim C36A-C31A
 with sigma of 0.04
 C25-C27 \\sim C25A-C27A
 with sigma of 0.04
 C25-C29 \\sim C25A-C29A
 with sigma of 0.04
 C26-C28 \\sim C26A-C28A
 with sigma of 0.04
 C26-C30 \\sim C26A-C30A
 with sigma of 0.04
 C26-C24 \\sim C26A-C24A
 with sigma of 0.04
 C27-C29 \\sim C27A-C29A
 with sigma of 0.04
 C27-C31 \\sim C27A-C31A
 with sigma of 0.04
 C28-C30 \\sim C28A-C30A
 with sigma of 0.04
 C29-C31 \\sim C29A-C31A
 with sigma of 0.04
 C30-C24 \\sim C30A-C24A
 with sigma of 0.04
 N12-C104 \\sim N12A-C1A
 with sigma of 0.02
 N12-C108 \\sim N12A-C1B
 with sigma of 0.02
 N12-C103 \\sim N12A-C1C
 with sigma of 0.02
 C104-C105 \\sim C1A-C1D
 with sigma of 0.02
 C105-C106 \\sim C1D-C1G
 with sigma of 0.02
 C106-C107 \\sim C1G-C1E
 with sigma of 0.02
 C107-C108 \\sim C1E-C1B
 with sigma of 0.02
 N11-C91 \\sim N11A-C91A
 with sigma of 0.02
 N11-C95 \\sim N11A-C95A
 with sigma of 0.02
 N11-C96 \\sim N11A-C96A
 with sigma of 0.02
 C91-C92 \\sim C91A-C92A
 with sigma of 0.02
 C92-C93 \\sim C92A-C93A
 with sigma of 0.02
 C93-C94 \\sim C93A-C94A
 with sigma of 0.02
 C94-C95 \\sim C94A-C95A
 with sigma of 0.02
 C97-C98 \\sim C97A-C98A
 with sigma of 0.02
 C97-C102 \\sim C97A-C109
 with sigma of 0.02
 C97-C96 \\sim C97A-C96A
 with sigma of 0.02
 C98-C99 \\sim C98A-C99A
 with sigma of 0.02
 C99-C100 \\sim C99A-C1F
 with sigma of 0.02
 C100-C101 \\sim C1F-C1H
 with sigma of 0.02
 C100-C103 \\sim C1F-C1C
 with sigma of 0.02
 C101-C102 \\sim C1H-C109
 with sigma of 0.02
 N12-C105 \\sim N12A-C1D
 with sigma of 0.04
 N12-C107 \\sim N12A-C1E
 with sigma of 0.04
 N12-C100 \\sim N12A-C1F
 with sigma of 0.04
 C104-C106 \\sim C1A-C1G
 with sigma of 0.04
 C104-C108 \\sim C1A-C1B
 with sigma of 0.04
 C104-C103 \\sim C1A-C1C
 with sigma of 0.04
 C105-C107 \\sim C1D-C1E
 with sigma of 0.04
 C106-C108 \\sim C1G-C1B
 with sigma of 0.04
 C108-C103 \\sim C1B-C1C
 with sigma of 0.04
 N11-C92 \\sim N11A-C92A
 with sigma of 0.04
 N11-C94 \\sim N11A-C94A
 with sigma of 0.04
 N11-C97 \\sim N11A-C97A
 with sigma of 0.04
 C91-C93 \\sim C91A-C93A
 with sigma of 0.04
 C91-C95 \\sim C91A-C95A
 with sigma of 0.04
 C91-C96 \\sim C91A-C96A
 with sigma of 0.04
 C92-C94 \\sim C92A-C94A
 with sigma of 0.04
 C93-C95 \\sim C93A-C95A
 with sigma of 0.04
 C95-C96 \\sim C95A-C96A
 with sigma of 0.04
 C97-C99 \\sim C97A-C99A
 with sigma of 0.04
 C97-C101 \\sim C97A-C1H
 with sigma of 0.04
 C98-C100 \\sim C98A-C1F
 with sigma of 0.04
 C98-C102 \\sim C98A-C109
 with sigma of 0.04
 C98-C96 \\sim C98A-C96A
 with sigma of 0.04
 C99-C101 \\sim C99A-C1H
 with sigma of 0.04
 C99-C103 \\sim C99A-C1C
 with sigma of 0.04
 C100-C102 \\sim C1F-C109
 with sigma of 0.04
 C101-C103 \\sim C1H-C1C
 with sigma of 0.04
 C102-C96 \\sim C109-C96A
 with sigma of 0.04
3. Restrained planarity
 O221, N221, C221, C222, C223
 with sigma of 0.001
 O231, N231, C231, C232, C233
 with sigma of 0.001
 O201, N201, C201, C202, C203
 with sigma of 0.001
 O211, N211, C211, C212, C213
 with sigma of 0.001
4. Uiso/Uaniso restraints and constraints
Uanis(I11A) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(I11B) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(I20B) \\sim Ueq, Uanis(I20A) \\sim Ueq, Uanis(I21B) \\sim Ueq,
Uanis(I21A) \\sim Ueq, Uanis(Bi4B) \\sim Ueq, Uanis(Bi4A) \\sim Ueq: with sigma
of 0.002 and sigma for terminal atoms of 0.004
Uanis(C6) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C13) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C19) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C32A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C24A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C31A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(I12A) = Uanis(I12B)
Uanis(O231) = Uanis(N231) = Uanis(C231) = Uanis(C232) = Uanis(C233) =
Uanis(C1K) = Uanis(C111) = Uanis(O1) = Uanis(N14) = Uanis(C1L)
Uanis(I5A) = Uanis(I5B)
Uanis(I10A) = Uanis(I10B)
Uanis(I11A) = Uanis(I11B)
Uanis(I6B) = Uanis(I6A)
Uanis(I19A) = Uanis(I19B)
Uanis(C1I) = Uanis(O221) = Uanis(C221) = Uanis(N221) = Uanis(C222) =
Uanis(C223) = Uanis(N13) = Uanis(C110) = Uanis(C1J) = Uanis(O2)
Uanis(I16A) = Uanis(I16B)
Uanis(I24B) = Uanis(I24A)
Uanis(I23A) = Uanis(I23B)
Uanis(I22A) = Uanis(I22B)
Uanis(I18A) = Uanis(I18B)
Uanis(Bi4A) = Uanis(Bi4B)
Uanis(I21A) = Uanis(I21B)
Uanis(I17B) = Uanis(I17A)
Uanis(I20B) = Uanis(I20A)
Uanis(I15A) = Uanis(I15B)
Uanis(Bi3A) = Uanis(Bi3B)
Uanis(C54) = Uanis(C53) = Uanis(C52) = Uanis(C51) = Uanis(C50) = Uanis(N6)
Uanis(C45) = Uanis(C46) = Uanis(C47) = Uanis(C48) = Uanis(C43) = Uanis(C44)
Uanis(C49) = Uanis(C42)
Uanis(N5) = Uanis(C41) = Uanis(C40) = Uanis(C39) = Uanis(C38) = Uanis(C37)
Uanis(C73) = Uanis(C74) = Uanis(C75) = Uanis(C76) = Uanis(C77) = Uanis(N9)
Uanis(C78) = Uanis(C85)
Uanis(C80) = Uanis(C81) = Uanis(C82) = Uanis(C83) = Uanis(C84) = Uanis(C79)
Uanis(N10) = Uanis(C90) = Uanis(C89) = Uanis(C88) = Uanis(C87) = Uanis(C86)
Uanis(N8) = Uanis(C72) = Uanis(C71) = Uanis(C70) = Uanis(C69) = Uanis(C68)
Uanis(C67) = Uanis(C60)
Uanis(C61) = Uanis(C66) = Uanis(C65) = Uanis(C64) = Uanis(C63) = Uanis(C62)
Uanis(N7) = Uanis(C55) = Uanis(C56) = Uanis(C57) = Uanis(C58) = Uanis(C59)
Uanis(N2) = Uanis(C18) = Uanis(C17) = Uanis(C16) = Uanis(C15) = Uanis(C14)
Uanis(C13) = Uanis(C6)
Uanis(C10) = Uanis(C11) = Uanis(C12) = Uanis(C7) = Uanis(C8) = Uanis(C9)
Uanis(N1) = Uanis(C5) = Uanis(C4) = Uanis(C3) = Uanis(C2) = Uanis(C1)
Uanis(N4) = Uanis(C32) = Uanis(C33) = Uanis(C34) = Uanis(C35) = Uanis(C36) =
Uanis(N4A) = Uanis(C32A) = Uanis(C36A) = Uanis(C33A) = Uanis(C35A) = Uanis(C34A)
Uanis(C25) = Uanis(C26) = Uanis(C27) = Uanis(C28) = Uanis(C29) = Uanis(C30) =
Uanis(C25A) = Uanis(C26A) = Uanis(C30A) = Uanis(C27A) = Uanis(C29A) =
Uanis(C28A)
Uanis(N3) = Uanis(C19) = Uanis(C20) = Uanis(C21) = Uanis(C22) = Uanis(C23) =
Uanis(N3A) = Uanis(C19A) = Uanis(C23A) = Uanis(C20A) = Uanis(C22A) = Uanis(C21A)
Uanis(C24A) = Uanis(C24) = Uanis(C31A) = Uanis(C31)
Uanis(N11) = Uanis(C91) = Uanis(C92) = Uanis(C93) = Uanis(C94) = Uanis(C95) =
Uanis(N11A) = Uanis(C91A) = Uanis(C95A) = Uanis(C92A) = Uanis(C94A) =
Uanis(C93A)
Uanis(C97) = Uanis(C98) = Uanis(C99) = Uanis(C100) = Uanis(C101) = Uanis(C102)
= Uanis(C109) = Uanis(C1F) = Uanis(C99A) = Uanis(C1H) = Uanis(C98A) =
Uanis(C97A)
Uanis(N12) = Uanis(C104) = Uanis(C105) = Uanis(C106) = Uanis(C107) =
Uanis(C108) = Uanis(C103) = Uanis(N12A) = Uanis(C1A) = Uanis(C1B) = Uanis(C1C)
= Uanis(C1D) = Uanis(C1E) = Uanis(C1G)
Uanis(C100) = Uanis(C1F) = Uanis(C97A) = Uanis(C97)
Uanis(C96A) = Uanis(C96) = Uanis(C1C) = Uanis(C103)
Uanis(C212) = Uanis(N211) = Uanis(C211) = Uanis(O211) = Uanis(C213)
Uanis(C203) = Uanis(N201) = Uanis(C201) = Uanis(O201) = Uanis(C202)
5. Others
 Sof(I11B)=Sof(I12B)=Sof(I10A)=1-FVAR(1)
 Sof(I10B)=Sof(I12A)=Sof(I11A)=FVAR(1)
 Sof(I6B)=Sof(I5A)=1-FVAR(2)
 Sof(I5B)=Sof(I6A)=FVAR(2)
 Sof(Bi3B)=Sof(I15B)=Sof(I16A)=Sof(I18A)=Sof(I17A)=1-FVAR(3)
 Sof(I16B)=Sof(I17B)=Sof(I18B)=Sof(I15A)=Sof(Bi3A)=FVAR(3)
 Sof(I20B)=Sof(I24B)=Sof(I19A)=Sof(I23A)=Sof(I22A)=Sof(Bi4A)=Sof(I21A)=1-FVAR(4)
 Sof(Bi4B)=Sof(I19B)=Sof(I21B)=Sof(I22B)=Sof(I23B)=Sof(I24A)=Sof(I20A)=FVAR(4)
 Sof(C24A)=Sof(H24C)=Sof(H24D)=Sof(N3A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=
 Sof(H20A)=Sof(C21A)=Sof(H21A)=Sof(C22A)=Sof(H22A)=Sof(C23A)=Sof(H23A)=
 Sof(C29A)=Sof(H29A)=Sof(C30A)=Sof(H30A)=Sof(C25A)=Sof(C26A)=Sof(H26A)=
 Sof(C27A)=Sof(H27A)=Sof(C28A)=Sof(C31A)=Sof(H31C)=Sof(H31D)=Sof(N4A)=Sof(C36A)=
 Sof(H36A)=Sof(C35A)=Sof(H35A)=Sof(C34A)=Sof(H34A)=Sof(C33A)=Sof(H33A)=
 Sof(C32A)=Sof(H32A)=1-FVAR(5)
 Sof(N3)=Sof(C19)=Sof(H19)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21)=Sof(C22)=
 Sof(H22)=Sof(C23)=Sof(H23)=Sof(N4)=Sof(C36)=Sof(H36)=Sof(C35)=Sof(H35)=
 Sof(C34)=Sof(H34)=Sof(C33)=Sof(H33)=Sof(C32)=Sof(H32)=Sof(C29)=Sof(H29)=
 Sof(C30)=Sof(H30)=Sof(C25)=Sof(C26)=Sof(H26)=Sof(C27)=Sof(H27)=Sof(C28)=
 Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(C31)=Sof(H31A)=Sof(H31B)=FVAR(5)
 Sof(O2)=Sof(C110)=Sof(H110)=Sof(N13)=Sof(C1I)=Sof(H1IA)=Sof(H1IB)=Sof(H1IC)=
 Sof(C1J)=Sof(H1JA)=Sof(H1JB)=Sof(H1JC)=1-FVAR(6)
 Sof(O221)=Sof(N221)=Sof(C221)=Sof(H221)=Sof(C222)=Sof(H22B)=Sof(H22C)=
 Sof(H22D)=Sof(C223)=Sof(H22E)=Sof(H22F)=Sof(H22G)=FVAR(6)
 Sof(C111)=Sof(H111)=Sof(O1)=Sof(N14)=Sof(C1K)=Sof(H1KA)=Sof(H1KB)=Sof(H1KC)=
 Sof(C1L)=Sof(H1LA)=Sof(H1LB)=Sof(H1LC)=1-FVAR(7)
 Sof(O231)=Sof(N231)=Sof(C231)=Sof(H231)=Sof(C232)=Sof(H23B)=Sof(H23C)=
 Sof(H23D)=Sof(C233)=Sof(H23E)=Sof(H23F)=Sof(H23G)=FVAR(7)
 Fixed Sof: N12(0.5) C104(0.5) H104(0.5) C105(0.5) H105(0.5) C106(0.5)
 H106(0.5) C107(0.5) H107(0.5) C108(0.5) H108(0.5) C92(0.5) H92(0.5) C91(0.5)
 H91(0.5) N11(0.5) C95(0.5) H95(0.5) C94(0.5) H94(0.5) C93(0.5) H93(0.5)
 C102(0.5) H102(0.5) C97(0.5) C98(0.5) H98(0.5) C99(0.5) H99(0.5) C100(0.5)
 C101(0.5) H101(0.5) C96(0.5) H96A(0.5) H96B(0.5) C103(0.5) H10A(0.5) H10B(0.5)
 C109(0.5) H109(0.5) C97A(0.5) C98A(0.5) H98A(0.5) C99A(0.5) H99A(0.5) C1F(0.5)
 C1H(0.5) H1H(0.5) N12A(0.5) C1A(0.5) H1A(0.5) C1D(0.5) H1D(0.5) C1G(0.5)
 H1G(0.5) C1E(0.5) H1E(0.5) C1B(0.5) H1B(0.5) C1C(0.5) H1CA(0.5) H1CB(0.5)
 C96A(0.5) H96C(0.5) H96D(0.5) C92A(0.5) H92A(0.5) C91A(0.5) H91A(0.5)
 N11A(0.5) C95A(0.5) H95A(0.5) C94A(0.5) H94A(0.5) C93A(0.5) H93A(0.5)
6.a Riding coordinates:
 C222(H22B,H22C,H22D), C223(H22E,H22F,H22G), C232(H23B,H23C,H23D), C233(H23E,
 H23F,H23G), C1I(H1IA,H1IB,H1IC), C1J(H1JA,H1JB,H1JC), C1K(H1KA,H1KB,H1KC),
 C1L(H1LA,H1LB,H1LC)
6.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C13(H13A,H13B), C24(H24A,H24B), C31(H31A,H31B), C42(H42A,H42B),
 C49(H49A,H49B), C60(H60A,H60B), C67(H67A,H67B), C78(H78A,H78B), C85(H85A,H85B),
  C96(H96A,H96B), C103(H10A,H10B), C24A(H24C,H24D), C31A(H31C,H31D), C1C(H1CA,
 H1CB), C96A(H96C,H96D)
6.c Me refined with riding coordinates:
 C202(H20B,H20C,H20D), C203(H20E,H20F,H20G), C212(H21B,H21C,H21D), C213(H21E,
 H21F,H21G)
6.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C36(H36),
  C35(H35), C34(H34), C33(H33), C32(H32), C37(H37), C38(H38), C39(H39),
 C40(H40), C41(H41), C50(H50), C51(H51), C52(H52), C53(H53), C54(H54), C55(H55),
  C56(H56), C57(H57), C58(H58), C59(H59), C68(H68), C69(H69), C70(H70),
 C71(H71), C72(H72), C73(H73), C74(H74), C75(H75), C76(H76), C77(H77), C86(H86),
  C87(H87), C88(H88), C89(H89), C90(H90), C104(H104), C105(H105), C106(H106),
 C107(H107), C108(H108), C8(H8), C9(H9), C11(H11), C12(H12), C29(H29), C30(H30),
  C26(H26), C27(H27), C44(H44), C45(H45), C47(H47), C48(H48), C62(H62),
 C63(H63), C65(H65), C66(H66), C80(H80), C81(H81), C83(H83), C84(H84), C92(H92),
  C91(H91), C95(H95), C94(H94), C93(H93), C102(H102), C98(H98), C99(H99),
 C101(H101), C201(H201), C211(H211), C221(H221), C231(H231), C19A(H19A),
 C20A(H20A), C21A(H21A), C22A(H22A), C23A(H23A), C29A(H29A), C30A(H30A),
 C26A(H26A), C27A(H27A), C36A(H36A), C35A(H35A), C34A(H34A), C33A(H33A),
 C32A(H32A), C109(H109), C98A(H98A), C99A(H99A), C1H(H1H), C1A(H1A), C1D(H1D),
 C1G(H1G), C1E(H1E), C1B(H1B), C92A(H92A), C91A(H91A), C95A(H95A), C94A(H94A),
 C93A(H93A), C110(H110), C111(H111)
6.e Fitted hexagon refined as free rotating group:
 N1(C1,C2,C3,C4,C5), N2(C14,C15,C16,C17,C18), N3(C19,C20,C21,C22,C23), N4(C36,
 C35,C34,C33,C32), N5(C37,C38,C39,C40,C41), N6(C50,C51,C52,C53,C54), N7(C55,C56,
 C57,C58,C59), N8(C68,C69,C70,C71,C72), N9(C73,C74,C75,C76,C77), N10(C86,C87,
 C88,C89,C90), N12(C104,C105,C106,C107,C108), C7(C8,C9,C10,C11,C12), C29(C30,
 C25,C26,C27,C28), C43(C44,C45,C46,C47,C48), C61(C62,C63,C64,C65,C66), C79(C80,
 C81,C82,C83,C84), C92(C91,N11,C95,C94,C93), C102(C97,C98,C99,C100,C101),
 N3A(C19A,C20A,C21A,C22A,C23A), C29A(C30A,C25A,C26A,C27A,C28A), N4A(C36A,C35A,
 C34A,C33A,C32A), C109(C97A,C98A,C99A,C1F,C1H), N12A(C1A,C1D,C1G,C1E,C1B),
 C92A(C91A,N11A,C95A,C94A,C93A)
;
_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
Bi1 Bi 0.52551(7) 0.25269(6) 0.7096(3) 0.0276(3) Uani 1 1 d . . . . .
Bi2 Bi 0.72856(6) 0.25504(6) 0.9687(3) 0.0249(3) Uani 1 1 d . . . . .
Bi3B Bi 0.5157(4) 0.7522(4) 0.7256(3) 0.0248(10) Uani 0.568(5) 1 d . . P A 1
Bi4B Bi 0.7332(3) 0.7479(3) 0.9560(3) 0.0192(7) Uani 0.487(4) 1 d . U P B 1
I1 I 0.42164(11) 0.29428(11) 0.6557(3) 0.0253(5) Uani 1 1 d . . . . .
I2 I 0.48144(10) 0.34876(11) 0.7737(3) 0.0261(5) Uani 1 1 d . . . . .
I3 I 0.60890(10) 0.34975(10) 0.6734(3) 0.0239(4) Uani 1 1 d . . . . .
I4 I 0.44674(12) 0.15276(11) 0.7506(3) 0.0324(5) Uani 1 1 d . . . . .
I5B I 0.5555(4) 0.1720(4) 0.6342(4) 0.0338(13) Uani 0.527(8) 1 d . . P C 1
I6B I 0.6261(4) 0.2000(4) 0.7608(4) 0.0350(12) Uani 0.473(8) 1 d . . P C 2
I7 I 0.69463(9) 0.33031(10) 1.0447(3) 0.0212(4) Uani 1 1 d . . . . .
I8 I 0.61792(10) 0.30960(11) 0.9226(3) 0.0259(5) Uani 1 1 d . . . . .
I9 I 0.65079(12) 0.14934(12) 1.0010(3) 0.0345(6) Uani 1 1 d . . . . .
I10B I 0.8014(11) 0.3679(8) 0.9266(8) 0.0272(17) Uani 0.434(6) 1 d . . P D 1
I11B I 0.8357(5) 0.2080(6) 1.0139(3) 0.0209(13) Uani 0.566(6) 1 d . U P D 2
I12B I 0.7581(2) 0.1822(3) 0.8899(3) 0.0398(11) Uani 0.566(6) 1 d . . P D 2
I13 I 0.58680(12) 0.64566(11) 0.6866(3) 0.0297(5) Uani 1 1 d . . . . .
I14 I 0.41127(12) 0.70849(11) 0.6711(3) 0.0287(5) Uani 1 1 d . . . . .
I15B I 0.4859(7) 0.6686(5) 0.7983(5) 0.0238(16) Uani 0.568(5) 1 d . . P A 1
I16B I 0.4495(5) 0.8687(5) 0.7528(4) 0.0378(14) Uani 0.432(5) 1 d . . P A 2
I17B I 0.5577(6) 0.8316(5) 0.6395(3) 0.0411(13) Uani 0.432(5) 1 d . . P A 2
I18B I 0.6347(3) 0.8157(3) 0.7585(3) 0.0336(9) Uani 0.432(5) 1 d . . P A 2
I19B I 0.7628(2) 0.8349(2) 0.8837(3) 0.0355(8) Uani 0.487(4) 1 d . . P B 1
I20B I 0.6205(8) 0.7204(6) 0.9101(5) 0.0162(15) Uani 0.513(4) 1 d . U P B 2
I21B I 0.6913(5) 0.6575(6) 1.0234(4) 0.0161(13) Uani 0.487(4) 1 d . U P B 1
I22B I 0.8110(9) 0.6453(9) 0.9168(5) 0.0229(18) Uani 0.487(4) 1 d . . P B 1
I23B I 0.8389(8) 0.7945(10) 1.0112(6) 0.029(2) Uani 0.487(4) 1 d . . P B 1
I24B I 0.6415(3) 0.8494(3) 1.0066(3) 0.0332(10) Uani 0.513(4) 1 d . . P B 2
N1 N 0.5782(8) 0.3466(10) 0.5373(7) 0.034(3) Uani 1 1 d DG . . . .
C1 C 0.5541(9) 0.3659(10) 0.5001(7) 0.034(3) Uani 1 1 d DG . . . .
H1 H 0.573719 0.396664 0.484464 0.041 Uiso 1 1 calc R U . . .
C2 C 0.5012(9) 0.3403(12) 0.4858(6) 0.034(3) Uani 1 1 d G . . . .
H2 H 0.484702 0.353484 0.460399 0.041 Uiso 1 1 calc R U . . .
C3 C 0.4724(8) 0.2953(11) 0.5087(7) 0.034(3) Uani 1 1 d G . . . .
H3 H 0.436259 0.277770 0.498926 0.041 Uiso 1 1 calc R U . . .
C4 C 0.4965(9) 0.2760(10) 0.5459(7) 0.034(3) Uani 1 1 d G . . . .
H4 H 0.476833 0.245236 0.561518 0.041 Uiso 1 1 calc R U . . .
C5 C 0.5494(9) 0.3016(11) 0.5602(6) 0.034(3) Uani 1 1 d DG . . . .
H5 H 0.565850 0.288416 0.585584 0.041 Uiso 1 1 calc R U . . .
N2 N 0.5872(8) 0.6649(9) 0.5513(6) 0.031(3) Uani 1 1 d DG . . . .
C14 C 0.5692(9) 0.6533(10) 0.5111(6) 0.031(3) Uani 1 1 d DG . . . .
H14 H 0.591155 0.625381 0.494530 0.038 Uiso 1 1 calc R U . . .
C15 C 0.5191(10) 0.6825(11) 0.4952(6) 0.031(3) Uani 1 1 d G . . . .
H15 H 0.506824 0.674575 0.467799 0.038 Uiso 1 1 calc R U . . .
C16 C 0.4871(8) 0.7233(10) 0.5195(7) 0.031(3) Uani 1 1 d G . . . .
H16 H 0.452814 0.743285 0.508648 0.038 Uiso 1 1 calc R U . . .
C17 C 0.5051(9) 0.7349(9) 0.5596(7) 0.031(3) Uani 1 1 d G . . . .
H17 H 0.483133 0.762801 0.576228 0.038 Uiso 1 1 calc R U . . .
C18 C 0.5552(9) 0.7057(10) 0.5755(6) 0.031(3) Uani 1 1 d DG . . . .
H18 H 0.567462 0.713606 0.602960 0.038 Uiso 1 1 calc R U . . .
N3 N 0.8232(18) -0.1560(19) 0.6410(14) 0.033(5) Uani 0.46(3) 1 d DG . P E 1
C19 C 0.798(2) -0.201(2) 0.6161(15) 0.033(5) Uani 0.46(3) 1 d DG U P E 1
H19 H 0.817145 -0.212207 0.591100 0.040 Uiso 0.46(3) 1 calc R U P E 1
C20 C 0.745(2) -0.229(2) 0.6278(17) 0.033(5) Uani 0.46(3) 1 d DG . P E 1
H20 H 0.728123 -0.260110 0.610728 0.040 Uiso 0.46(3) 1 calc R U P E 1
C21 C 0.7174(19) -0.213(2) 0.6643(17) 0.033(5) Uani 0.46(3) 1 d DG . P E 1
H21 H 0.681304 -0.232381 0.672284 0.040 Uiso 0.46(3) 1 calc R U P E 1
C22 C 0.743(2) -0.168(2) 0.6892(14) 0.033(5) Uani 0.46(3) 1 d DG . P E 1
H22 H 0.723507 -0.156747 0.714213 0.040 Uiso 0.46(3) 1 calc R U P E 1
C23 C 0.795(2) -0.140(2) 0.6776(13) 0.033(5) Uani 0.46(3) 1 d DG . P E 1
H23 H 0.812529 -0.108843 0.694585 0.040 Uiso 0.46(3) 1 calc R U P E 1
N4 N 0.830(2) 0.161(2) 0.6356(12) 0.023(4) Uani 0.46(3) 1 d DG . P E 1
C36 C 0.794(2) 0.193(2) 0.6084(12) 0.023(4) Uani 0.46(3) 1 d DG . P E 1
H36 H 0.804393 0.195739 0.580258 0.028 Uiso 0.46(3) 1 calc R U P E 1
C35 C 0.741(2) 0.220(2) 0.6226(14) 0.023(4) Uani 0.46(3) 1 d DG . P E 1
H35 H 0.716250 0.241135 0.604014 0.028 Uiso 0.46(3) 1 calc R U P E 1
C34 C 0.7257(18) 0.215(2) 0.6638(15) 0.023(4) Uani 0.46(3) 1 d DG . P E 1
H34 H 0.689954 0.233257 0.673429 0.028 Uiso 0.46(3) 1 calc R U P E 1
C33 C 0.762(2) 0.183(2) 0.6909(12) 0.023(4) Uani 0.46(3) 1 d DG . P E 1
H33 H 0.751800 0.179982 0.719088 0.028 Uiso 0.46(3) 1 calc R U P E 1
C32 C 0.815(2) 0.156(2) 0.6768(12) 0.023(4) Uani 0.46(3) 1 d DG . P E 1
H32 H 0.839943 0.134585 0.695333 0.028 Uiso 0.46(3) 1 calc R U P E 1
N5 N 0.7108(10) 0.3427(13) 0.7977(7) 0.049(5) Uani 1 1 d DG . . . .
C37 C 0.7461(11) 0.3077(14) 0.8239(6) 0.049(5) Uani 1 1 d DG . . . .
H37 H 0.735009 0.302983 0.851928 0.058 Uiso 1 1 calc R U . . .
C38 C 0.7975(11) 0.2796(14) 0.8091(7) 0.049(5) Uani 1 1 d G . . . .
H38 H 0.821535 0.255684 0.827050 0.058 Uiso 1 1 calc R U . . .
C39 C 0.8136(10) 0.2865(14) 0.7681(8) 0.049(5) Uani 1 1 d G . . . .
H39 H 0.848770 0.267293 0.758044 0.058 Uiso 1 1 calc R U . . .
C40 C 0.7784(11) 0.3215(15) 0.7419(6) 0.049(5) Uani 1 1 d G . . . .
H40 H 0.789479 0.326201 0.713915 0.058 Uiso 1 1 calc R U . . .
C41 C 0.7270(11) 0.3496(14) 0.7567(6) 0.049(5) Uani 1 1 d DG . . . .
H41 H 0.702953 0.373500 0.738792 0.058 Uiso 1 1 calc R U . . .
N6 N 0.7168(8) 0.6689(10) 0.7880(7) 0.044(4) Uani 1 1 d DG . . . .
C50 C 0.7379(10) 0.6627(11) 0.7480(7) 0.044(4) Uani 1 1 d DG . . . .
H50 H 0.715711 0.639603 0.728459 0.053 Uiso 1 1 calc R U . . .
C51 C 0.7913(11) 0.6902(12) 0.7366(7) 0.044(4) Uani 1 1 d G . . . .
H51 H 0.805685 0.685983 0.709247 0.053 Uiso 1 1 calc R U . . .
C52 C 0.8237(9) 0.7240(11) 0.7651(9) 0.044(4) Uani 1 1 d G . . . .
H52 H 0.860227 0.742791 0.757339 0.053 Uiso 1 1 calc R U . . .
C53 C 0.8027(10) 0.7302(11) 0.8051(8) 0.044(4) Uani 1 1 d G . . . .
H53 H 0.824795 0.753221 0.824644 0.053 Uiso 1 1 calc R U . . .
C54 C 0.7492(10) 0.7026(11) 0.8165(6) 0.044(4) Uani 1 1 d DG . . . .
H54 H 0.734820 0.706842 0.843857 0.053 Uiso 1 1 calc R U . . .
N7 N 0.5329(9) -0.1509(10) 0.8895(7) 0.046(4) Uani 1 1 d DG . . . .
C55 C 0.4945(10) -0.1834(11) 0.8640(6) 0.046(4) Uani 1 1 d DG . . . .
H55 H 0.502204 -0.185543 0.835273 0.055 Uiso 1 1 calc R U . . .
C56 C 0.4449(9) -0.2127(11) 0.8804(8) 0.046(4) Uani 1 1 d G . . . .
H56 H 0.418610 -0.234887 0.862959 0.055 Uiso 1 1 calc R U . . .
C57 C 0.4336(10) -0.2095(11) 0.9224(8) 0.046(4) Uani 1 1 d G . . . .
H57 H 0.399680 -0.229514 0.933608 0.055 Uiso 1 1 calc R U . . .
C58 C 0.4720(11) -0.1770(12) 0.9479(7) 0.046(4) Uani 1 1 d G . . . .
H58 H 0.464343 -0.174797 0.976570 0.055 Uiso 1 1 calc R U . . .
C59 C 0.5217(10) -0.1477(11) 0.9314(7) 0.046(4) Uani 1 1 d DG . . . .
H59 H 0.547937 -0.125452 0.948884 0.055 Uiso 1 1 calc R U . . .
N8 N 0.5370(8) 0.1718(10) 0.8854(6) 0.032(3) Uani 1 1 d DG . . . .
C68 C 0.5120(9) 0.1639(10) 0.9241(6) 0.032(3) Uani 1 1 d DG . . . .
H68 H 0.531925 0.139629 0.944077 0.038 Uiso 1 1 calc R U . . .
C69 C 0.4578(9) 0.1915(11) 0.9336(6) 0.032(3) Uani 1 1 d G . . . .
H69 H 0.440690 0.186128 0.960070 0.038 Uiso 1 1 calc R U . . .
C70 C 0.4286(8) 0.2271(11) 0.9044(7) 0.032(3) Uani 1 1 d G . . . .
H70 H 0.391598 0.245958 0.910854 0.038 Uiso 1 1 calc R U . . .
C71 C 0.4537(9) 0.2350(10) 0.8656(6) 0.032(3) Uani 1 1 d G . . . .
H71 H 0.433741 0.259290 0.845645 0.038 Uiso 1 1 calc R U . . .
C72 C 0.5079(9) 0.2074(11) 0.8561(5) 0.032(3) Uani 1 1 d DG . . . .
H72 H 0.524976 0.212791 0.829652 0.038 Uiso 1 1 calc R U . . .
N9 N 0.3954(7) 0.5216(9) 0.4782(6) 0.028(3) Uani 1 1 d DG . . . .
C73 C 0.4244(6) 0.4850(9) 0.4494(7) 0.028(3) Uani 1 1 d DG . . . .
H73 H 0.466748 0.484503 0.448302 0.034 Uiso 1 1 calc R U . . .
C74 C 0.3913(8) 0.4493(9) 0.4223(6) 0.028(3) Uani 1 1 d G . . . .
H74 H 0.411135 0.424347 0.402685 0.034 Uiso 1 1 calc R U . . .
C75 C 0.3293(8) 0.4501(9) 0.4240(6) 0.028(3) Uani 1 1 d G . . . .
H75 H 0.306755 0.425694 0.405503 0.034 Uiso 1 1 calc R U . . .
C76 C 0.3004(6) 0.4867(10) 0.4528(7) 0.028(3) Uani 1 1 d G . . . .
H76 H 0.257987 0.487197 0.453939 0.034 Uiso 1 1 calc R U . . .
C77 C 0.3334(7) 0.5224(9) 0.4799(6) 0.028(3) Uani 1 1 d G . . . .
H77 H 0.313599 0.547354 0.499556 0.034 Uiso 1 1 calc R U . . .
N10 N 0.4298(8) 0.4894(8) 0.7026(7) 0.027(3) Uani 1 1 d DG . . . .
C86 C 0.4326(8) 0.5442(8) 0.7244(7) 0.027(3) Uani 1 1 d DG . . . .
H86 H 0.466381 0.570179 0.721558 0.033 Uiso 1 1 calc R U . . .
C87 C 0.3861(9) 0.5608(8) 0.7503(7) 0.027(3) Uani 1 1 d G . . . .
H87 H 0.387986 0.598247 0.765218 0.033 Uiso 1 1 calc R U . . .
C88 C 0.3366(8) 0.5228(9) 0.7545(7) 0.027(3) Uani 1 1 d G . . . .
H88 H 0.304823 0.534160 0.772201 0.033 Uiso 1 1 calc R U . . .
C89 C 0.3338(8) 0.4680(8) 0.7327(7) 0.027(3) Uani 1 1 d G . . . .
H89 H 0.300054 0.442003 0.735524 0.033 Uiso 1 1 calc R U . . .
C90 C 0.3804(9) 0.4513(7) 0.7068(7) 0.027(3) Uani 1 1 d DG . . . .
H90 H 0.378449 0.413934 0.691863 0.033 Uiso 1 1 calc R U . . .
N12 N 0.653(2) 0.983(3) 0.7023(17) 0.074(8) Uani 0.5 1 d DG . P F 1
C104 C 0.591(2) 0.978(3) 0.703(2) 0.074(8) Uani 0.5 1 d DG . P F 1
H104 H 0.571420 0.949460 0.686102 0.089 Uiso 0.5 1 calc R U P F 1
C105 C 0.559(2) 1.016(3) 0.730(2) 0.074(8) Uani 0.5 1 d DG . P F 1
H105 H 0.516297 1.012510 0.730219 0.089 Uiso 0.5 1 calc R U P F 1
C106 C 0.588(3) 1.057(3) 0.755(2) 0.074(8) Uani 0.5 1 d DG . P F 1
H106 H 0.565359 1.083030 0.772613 0.089 Uiso 0.5 1 calc R U P F 1
C107 C 0.650(3) 1.062(3) 0.754(2) 0.074(8) Uani 0.5 1 d DG . P F 1
H107 H 0.669544 1.090501 0.770889 0.089 Uiso 0.5 1 calc R U P F 1
C108 C 0.682(2) 1.024(3) 0.7275(19) 0.074(8) Uani 0.5 1 d DG . P F 1
H108 H 0.724668 1.027452 0.726771 0.089 Uiso 0.5 1 calc R U P F 1
C7 C 0.6368(10) 0.4396(5) 0.5540(7) 0.024(3) Uani 1 1 d DG . . . .
C8 C 0.6722(10) 0.4739(6) 0.5275(6) 0.024(3) Uani 1 1 d DG . . . .
H8 H 0.695158 0.453947 0.506895 0.029 Uiso 1 1 calc R U . . .
C9 C 0.6742(10) 0.5373(6) 0.5312(7) 0.024(3) Uani 1 1 d DG . . . .
H9 H 0.698417 0.560773 0.513111 0.029 Uiso 1 1 calc R U . . .
C10 C 0.6406(10) 0.5665(5) 0.5614(7) 0.024(3) Uani 1 1 d DG . . . .
C11 C 0.6051(11) 0.5322(6) 0.5878(7) 0.024(3) Uani 1 1 d DG . . . .
H11 H 0.582226 0.552175 0.608445 0.029 Uiso 1 1 calc R U . . .
C12 C 0.6032(11) 0.4688(6) 0.5841(7) 0.024(3) Uani 1 1 d DG . . . .
H12 H 0.578966 0.445348 0.602230 0.029 Uiso 1 1 calc R U . . .
C29 C 0.866(2) 0.0301(16) 0.5915(12) 0.029(5) Uani 0.46(3) 1 d DG . P E 1
H29 H 0.853008 0.050137 0.567234 0.035 Uiso 0.46(3) 1 calc R U P E 1
C30 C 0.865(2) -0.0335(16) 0.5941(11) 0.029(5) Uani 0.46(3) 1 d DG . P E 1
H30 H 0.850477 -0.056921 0.571519 0.035 Uiso 0.46(3) 1 calc R U P E 1
C25 C 0.884(2) -0.0627(13) 0.6296(12) 0.029(5) Uani 0.46(3) 1 d DG . P E 1
C26 C 0.905(2) -0.0284(15) 0.6625(12) 0.029(5) Uani 0.46(3) 1 d DG . P E 1
H26 H 0.918517 -0.048354 0.686821 0.035 Uiso 0.46(3) 1 calc R U P E 1
C27 C 0.907(2) 0.0352(14) 0.6600(12) 0.029(5) Uani 0.46(3) 1 d DG . P E 1
H27 H 0.921049 0.058704 0.682537 0.035 Uiso 0.46(3) 1 calc R U P E 1
C28 C 0.887(2) 0.0645(12) 0.6245(13) 0.029(5) Uani 0.46(3) 1 d DG . P E 1
C43 C 0.6598(13) 0.4462(9) 0.8092(9) 0.055(5) Uani 1 1 d DG . . . .
C44 C 0.7043(12) 0.4807(11) 0.8280(9) 0.055(5) Uani 1 1 d DG . . . .
H44 H 0.734006 0.461030 0.844066 0.067 Uiso 1 1 calc R U . . .
C45 C 0.7053(12) 0.5441(11) 0.8232(9) 0.055(5) Uani 1 1 d DG . . . .
H45 H 0.735642 0.567627 0.836040 0.067 Uiso 1 1 calc R U . . .
C46 C 0.6618(13) 0.5729(9) 0.7996(9) 0.055(5) Uani 1 1 d DG . . . .
C47 C 0.6173(13) 0.5384(10) 0.7808(9) 0.055(5) Uani 1 1 d DG . . . .
H47 H 0.587567 0.558079 0.764722 0.067 Uiso 1 1 calc R U . . .
C48 C 0.6163(13) 0.4751(10) 0.7856(9) 0.055(5) Uani 1 1 d DG . . . .
H48 H 0.585930 0.451482 0.772748 0.067 Uiso 1 1 calc R U . . .
C61 C 0.5865(10) -0.0549(6) 0.8767(9) 0.035(4) Uani 1 1 d DG . . . .
C62 C 0.6303(10) -0.0241(7) 0.8988(9) 0.035(4) Uani 1 1 d DG . . . .
H62 H 0.659422 -0.046511 0.913757 0.042 Uiso 1 1 calc R U . . .
C63 C 0.6315(10) 0.0396(7) 0.8990(9) 0.035(4) Uani 1 1 d DG . . . .
H63 H 0.661419 0.060748 0.914055 0.042 Uiso 1 1 calc R U . . .
C64 C 0.5889(10) 0.0725(6) 0.8770(9) 0.035(4) Uani 1 1 d DG . . . .
C65 C 0.5451(9) 0.0416(8) 0.8549(9) 0.035(4) Uani 1 1 d DG . . . .
H65 H 0.515982 0.064064 0.839964 0.042 Uiso 1 1 calc R U . . .
C66 C 0.5439(9) -0.0221(8) 0.8548(9) 0.035(4) Uani 1 1 d DG . . . .
H66 H 0.513984 -0.043196 0.839665 0.042 Uiso 1 1 calc R U . . .
C79 C 0.4319(10) 0.5345(6) 0.5504(5) 0.019(3) Uani 1 1 d DG . . . .
C80 C 0.4337(10) 0.4720(6) 0.5587(5) 0.019(3) Uani 1 1 d DG . . . .
H80 H 0.425479 0.443325 0.537487 0.023 Uiso 1 1 calc R U . . .
C81 C 0.4476(10) 0.4515(5) 0.5980(5) 0.019(3) Uani 1 1 d DG . . . .
H81 H 0.448857 0.408789 0.603659 0.023 Uiso 1 1 calc R U . . .
C82 C 0.4597(10) 0.4935(7) 0.6291(5) 0.019(3) Uani 1 1 d DG . . . .
C83 C 0.4579(10) 0.5560(6) 0.6208(5) 0.019(3) Uani 1 1 d DG . . . .
H83 H 0.466186 0.584675 0.642027 0.023 Uiso 1 1 calc R U . . .
C84 C 0.4440(9) 0.5765(5) 0.5815(5) 0.019(3) Uani 1 1 d DG . . . .
H84 H 0.442809 0.619212 0.575854 0.023 Uiso 1 1 calc R U . . .
C92 C 0.629(2) 0.9340(19) 0.4394(17) 0.048(6) Uani 0.5 1 d DG . P F 1
H92 H 0.628366 0.893810 0.428159 0.058 Uiso 0.5 1 calc R U P F 1
C91 C 0.6765(19) 0.9517(18) 0.4644(16) 0.048(6) Uani 0.5 1 d DG . P F 1
H91 H 0.707832 0.923684 0.470338 0.058 Uiso 0.5 1 calc R U P F 1
N11 N 0.6780(19) 1.0105(19) 0.4809(14) 0.048(6) Uani 0.5 1 d DG . P F 1
C95 C 0.632(2) 1.0516(18) 0.4723(16) 0.048(6) Uani 0.5 1 d DG . P F 1
H95 H 0.633161 1.091795 0.483506 0.058 Uiso 0.5 1 calc R U P F 1
C94 C 0.5850(19) 1.034(2) 0.4472(17) 0.048(6) Uani 0.5 1 d DG . P F 1
H94 H 0.553694 1.061922 0.441327 0.058 Uiso 0.5 1 calc R U P F 1
C93 C 0.5836(19) 0.975(2) 0.4308(16) 0.048(6) Uani 0.5 1 d DG . P F 1
H93 H 0.551296 0.962930 0.413654 0.058 Uiso 0.5 1 calc R U P F 1
C102 C 0.709(3) 0.947(2) 0.5586(11) 0.060(8) Uani 0.5 1 d DG . P F 1
H102 H 0.713881 0.918278 0.536848 0.072 Uiso 0.5 1 calc R U P F 1
C97 C 0.713(3) 1.009(2) 0.5510(11) 0.060(8) Uani 0.5 1 d DG . P F 1
C98 C 0.705(3) 1.0510(18) 0.5829(13) 0.060(8) Uani 0.5 1 d DG . P F 1
H98 H 0.708079 1.093750 0.577640 0.072 Uiso 0.5 1 calc R U P F 1
C99 C 0.693(3) 1.0302(19) 0.6224(13) 0.060(8) Uani 0.5 1 d DG . P F 1
H99 H 0.687558 1.058654 0.644128 0.072 Uiso 0.5 1 calc R U P F 1
C100 C 0.689(3) 0.968(2) 0.6300(11) 0.060(8) Uani 0.5 1 d DG . P F 1
C101 C 0.696(3) 0.9259(18) 0.5981(13) 0.060(8) Uani 0.5 1 d DG . P F 1
H101 H 0.693360 0.883182 0.603337 0.072 Uiso 0.5 1 calc R U P F 1
C6 C 0.6386(8) 0.3699(7) 0.5509(8) 0.020(5) Uani 1 1 d D U . . .
H6A H 0.669452 0.357380 0.530754 0.024 Uiso 1 1 calc R U . . .
H6B H 0.649058 0.352109 0.577901 0.024 Uiso 1 1 calc R U . . .
C13 C 0.6446(9) 0.6358(7) 0.5668(8) 0.020(5) Uani 1 1 d D U . . .
H13A H 0.650365 0.645910 0.596204 0.024 Uiso 1 1 calc R U . . .
H13B H 0.679060 0.652049 0.551189 0.024 Uiso 1 1 calc R U . . .
C24 C 0.8858(17) -0.1326(13) 0.6315(17) 0.028(7) Uani 0.46(3) 1 d D . P E 1
H24A H 0.899604 -0.149409 0.604894 0.033 Uiso 0.46(3) 1 calc R U P E 1
H24B H 0.913870 -0.146099 0.653196 0.033 Uiso 0.46(3) 1 calc R U P E 1
C31 C 0.889(2) 0.1343(13) 0.6212(17) 0.028(7) Uani 0.46(3) 1 d D . P E 1
H31A H 0.922399 0.150405 0.638339 0.033 Uiso 0.46(3) 1 calc R U P E 1
H31B H 0.896998 0.146386 0.592305 0.033 Uiso 0.46(3) 1 calc R U P E 1
C42 C 0.6569(11) 0.3769(9) 0.8144(9) 0.043(7) Uani 1 1 d D . . . .
H42A H 0.652688 0.367455 0.844024 0.052 Uiso 1 1 calc R U . . .
H42B H 0.620632 0.361555 0.800325 0.052 Uiso 1 1 calc R U . . .
C49 C 0.6562(10) 0.6425(9) 0.7990(10) 0.043(7) Uani 1 1 d D . . . .
H49A H 0.626135 0.655212 0.778373 0.052 Uiso 1 1 calc R U . . .
H49B H 0.643457 0.657678 0.826258 0.052 Uiso 1 1 calc R U . . .
C60 C 0.5904(11) -0.1243(8) 0.8723(10) 0.051(9) Uani 1 1 d D . . . .
H60A H 0.595069 -0.135757 0.843048 0.061 Uiso 1 1 calc R U . . .
H60B H 0.625184 -0.140225 0.887793 0.061 Uiso 1 1 calc R U . . .
C67 C 0.5962(9) 0.1419(8) 0.8748(11) 0.051(9) Uani 1 1 d D . . . .
H67A H 0.627355 0.155413 0.894346 0.061 Uiso 1 1 calc R U . . .
H67B H 0.608679 0.154009 0.846719 0.061 Uiso 1 1 calc R U . . .
C78 C 0.4337(12) 0.5642(9) 0.5036(5) 0.025(5) Uani 1 1 d D . . . .
H78A H 0.417110 0.606279 0.503552 0.030 Uiso 1 1 calc R U . . .
H78B H 0.475047 0.565477 0.492940 0.030 Uiso 1 1 calc R U . . .
C85 C 0.4775(9) 0.4714(10) 0.6718(5) 0.025(5) Uani 1 1 d D . . . .
H85A H 0.482322 0.426315 0.671620 0.030 Uiso 1 1 calc R U . . .
H85B H 0.516140 0.489994 0.679729 0.030 Uiso 1 1 calc R U . . .
C96 C 0.730(2) 1.031(3) 0.5079(11) 0.074(8) Uani 0.5 1 d D . P F 1
H96A H 0.734941 1.075752 0.507106 0.089 Uiso 0.5 1 calc R U P F 1
H96B H 0.767666 1.011144 0.498862 0.089 Uiso 0.5 1 calc R U P F 1
C103 C 0.690(3) 0.942(2) 0.6737(12) 0.074(8) Uani 0.5 1 d D . P F 1
H10A H 0.674111 0.899977 0.673955 0.089 Uiso 0.5 1 calc R U P F 1
H10B H 0.731971 0.940798 0.683564 0.089 Uiso 0.5 1 calc R U P F 1
O201 O 0.4423(9) 0.4756(9) 0.9597(7) 0.057(5) Uani 1 1 d D . . . .
N201 N 0.4263(7) 0.4655(6) 0.8918(7) 0.057(5) Uani 1 1 d D . . . .
C201 C 0.4128(8) 0.4870(6) 0.9298(7) 0.057(5) Uani 1 1 d D . . . .
H201 H 0.378484 0.512166 0.932972 0.069 Uiso 1 1 calc R U . . .
C202 C 0.4769(12) 0.4265(13) 0.8815(11) 0.057(5) Uani 1 1 d D . . . .
H20B H 0.476435 0.417616 0.851941 0.086 Uiso 1 1 calc R U . . .
H20C H 0.514130 0.447691 0.888544 0.086 Uiso 1 1 calc R U . . .
H20D H 0.474270 0.388108 0.896956 0.086 Uiso 1 1 calc R U . . .
C203 C 0.3889(13) 0.4808(13) 0.8567(9) 0.057(5) Uani 1 1 d D . . . .
H20E H 0.405247 0.461542 0.831895 0.086 Uiso 1 1 calc R U . . .
H20F H 0.348290 0.465833 0.861455 0.086 Uiso 1 1 calc R U . . .
H20G H 0.388149 0.525417 0.853042 0.086 Uiso 1 1 calc R U . . .
O211 O 0.7478(9) 0.6175(10) 0.6586(5) 0.051(4) Uani 1 1 d D . . . .
N211 N 0.7606(6) 0.5191(9) 0.6406(4) 0.051(4) Uani 1 1 d D . . . .
C211 C 0.7727(7) 0.5798(9) 0.6381(4) 0.051(4) Uani 1 1 d D . . . .
H211 H 0.802273 0.593129 0.619178 0.062 Uiso 1 1 calc R U . . .
C212 C 0.7881(12) 0.4701(12) 0.6173(8) 0.051(4) Uani 1 1 d D . . . .
H21B H 0.770663 0.430754 0.625517 0.077 Uiso 1 1 calc R U . . .
H21C H 0.781127 0.476805 0.587904 0.077 Uiso 1 1 calc R U . . .
H21D H 0.831162 0.469553 0.622682 0.077 Uiso 1 1 calc R U . . .
C213 C 0.7155(12) 0.4966(15) 0.6693(9) 0.051(4) Uani 1 1 d D . . . .
H21E H 0.712675 0.451843 0.667047 0.077 Uiso 1 1 calc R U . . .
H21F H 0.726865 0.507714 0.697400 0.077 Uiso 1 1 calc R U . . .
H21G H 0.676829 0.514966 0.662622 0.077 Uiso 1 1 calc R U . . .
O221 O 0.5106(9) -0.1137(15) 0.5078(7) 0.056(7) Uani 0.63(3) 1 d D . P G 1
N221 N 0.5154(6) -0.0289(12) 0.5470(6) 0.056(7) Uani 0.63(3) 1 d D . P G 1
C221 C 0.5279(7) -0.0885(12) 0.5385(6) 0.056(7) Uani 0.63(3) 1 d D . P G 1
H221 H 0.551117 -0.111238 0.557592 0.068 Uiso 0.63(3) 1 calc R U P G 1
C222 C 0.5339(14) 0.0056(18) 0.5828(10) 0.056(7) Uani 0.63(3) 1 d D . P G 1
H22B H 0.535724 -0.021420 0.606870 0.084 Uiso 0.63(3) 1 d R U P G 1
H22C H 0.505034 0.038490 0.587870 0.084 Uiso 0.63(3) 1 d R U P G 1
H22D H 0.573434 0.023460 0.577891 0.084 Uiso 0.63(3) 1 d R U P G 1
C223 C 0.4797(15) 0.0049(19) 0.5172(12) 0.056(7) Uani 0.63(3) 1 d D . P G 1
H22E H 0.505526 0.029715 0.499495 0.084 Uiso 0.63(3) 1 d R U P G 1
H22F H 0.451646 0.031605 0.531774 0.084 Uiso 0.63(3) 1 d R U P G 1
H22G H 0.457476 -0.024555 0.500385 0.084 Uiso 0.63(3) 1 d R U P G 1
O231 O 0.3119(12) 0.0193(12) 0.7220(9) 0.098(12) Uani 0.67(3) 1 d D . P H 1
N231 N 0.3302(8) 0.0407(8) 0.7886(8) 0.098(12) Uani 0.67(3) 1 d D . P H 1
C231 C 0.3406(8) 0.0113(8) 0.7527(8) 0.098(12) Uani 0.67(3) 1 d D . P H 1
H231 H 0.372367 -0.017510 0.751782 0.117 Uiso 0.67(3) 1 calc R U P H 1
C232 C 0.3618(17) 0.0345(18) 0.8273(9) 0.098(12) Uani 0.67(3) 1 d D . P H 1
H23B H 0.335400 0.016234 0.848004 0.146 Uiso 0.67(3) 1 d R U P H 1
H23C H 0.374860 0.075064 0.836764 0.146 Uiso 0.67(3) 1 d R U P H 1
H23D H 0.396710 0.008144 0.823344 0.146 Uiso 0.67(3) 1 d R U P H 1
C233 C 0.2822(15) 0.0851(16) 0.7919(16) 0.098(12) Uani 0.67(3) 1 d D . P H 1
H23E H 0.297826 0.126881 0.789021 0.146 Uiso 0.67(3) 1 d R U P H 1
H23F H 0.263085 0.080671 0.818801 0.146 Uiso 0.67(3) 1 d R U P H 1
H23G H 0.252806 0.077341 0.770171 0.146 Uiso 0.67(3) 1 d R U P H 1
I16A I 0.4340(4) 0.8553(3) 0.7640(3) 0.0378(14) Uani 0.568(5) 1 d . . P A 1
I18A I 0.6239(2) 0.7947(2) 0.7727(3) 0.0336(9) Uani 0.568(5) 1 d . . P A 1
I12A I 0.7682(3) 0.1590(4) 0.9052(4) 0.0398(11) Uani 0.434(6) 1 d . . P D 1
I5A I 0.5711(4) 0.1627(5) 0.6461(4) 0.0338(13) Uani 0.473(8) 1 d . . P C 2
I19A I 0.7669(2) 0.8546(2) 0.9063(3) 0.0355(8) Uani 0.513(4) 1 d . . P B 2
I24A I 0.6642(3) 0.8554(3) 0.9945(3) 0.0332(10) Uani 0.487(4) 1 d . . P B 1
I17A I 0.5563(4) 0.8386(4) 0.6562(3) 0.0411(13) Uani 0.568(5) 1 d . . P A 1
I6A I 0.6297(4) 0.2222(3) 0.7702(4) 0.0350(12) Uani 0.527(8) 1 d . . P C 1
I23A I 0.8276(8) 0.7917(9) 1.0215(6) 0.029(2) Uani 0.513(4) 1 d . . P B 2
I15A I 0.4916(10) 0.6829(8) 0.7926(7) 0.0238(16) Uani 0.432(5) 1 d . . P A 2
I22A I 0.8041(8) 0.6532(8) 0.9269(5) 0.0229(18) Uani 0.513(4) 1 d . . P B 2
Bi4A Bi 0.7249(2) 0.7534(3) 0.9669(3) 0.0192(7) Uani 0.513(4) 1 d . U P B 2
I21A I 0.6824(5) 0.6633(5) 1.0323(4) 0.0161(13) Uani 0.513(4) 1 d . U P B 2
I20A I 0.6239(8) 0.7096(6) 0.9044(5) 0.0162(15) Uani 0.487(4) 1 d . U P B 1
I10A I 0.8069(8) 0.3537(6) 0.9321(6) 0.0272(17) Uani 0.566(6) 1 d . . P D 2
Bi3A Bi 0.5221(6) 0.7609(5) 0.7160(4) 0.0248(10) Uani 0.432(5) 1 d . . P A 2
I11A I 0.8322(7) 0.2048(8) 1.0247(4) 0.0209(13) Uani 0.434(6) 1 d . U P D 1
C24A C 0.3950(18) 0.1361(15) 0.6128(18) 0.028(7) Uani 0.54(3) 1 d D U P E 2
H24C H 0.430054 0.152621 0.627629 0.033 Uiso 0.54(3) 1 calc R U P E 2
H24D H 0.399892 0.145431 0.583170 0.033 Uiso 0.54(3) 1 calc R U P E 2
N3A N 0.3389(16) 0.1658(17) 0.6287(13) 0.033(5) Uani 0.54(3) 1 d DG . P E 2
C19A C 0.3082(19) 0.2064(19) 0.6033(12) 0.033(5) Uani 0.54(3) 1 d DG . P E 2
H19A H 0.321555 0.213219 0.575985 0.040 Uiso 0.54(3) 1 calc R U P E 2
C20A C 0.2581(18) 0.2369(19) 0.6180(14) 0.033(5) Uani 0.54(3) 1 d DG . P E 2
H20A H 0.237167 0.264603 0.600702 0.040 Uiso 0.54(3) 1 calc R U P E 2
C21A C 0.2386(17) 0.2269(19) 0.6580(14) 0.033(5) Uani 0.54(3) 1 d DG . P E 2
H21A H 0.204364 0.247724 0.668051 0.040 Uiso 0.54(3) 1 calc R U P E 2
C22A C 0.269(2) 0.186(2) 0.6833(11) 0.033(5) Uani 0.54(3) 1 d DG . P E 2
H22A H 0.255949 0.179461 0.710684 0.040 Uiso 0.54(3) 1 calc R U P E 2
C23A C 0.3194(18) 0.1558(18) 0.6687(12) 0.033(5) Uani 0.54(3) 1 d DG . P E 2
H23A H 0.340338 0.128077 0.685968 0.040 Uiso 0.54(3) 1 calc R U P E 2
C29A C 0.3514(19) -0.0309(15) 0.5989(15) 0.029(5) Uani 0.54(3) 1 d DG . P E 2
H29A H 0.324059 -0.054395 0.583099 0.035 Uiso 0.54(3) 1 calc R U P E 2
C30A C 0.3515(18) 0.0327(15) 0.5958(14) 0.029(5) Uani 0.54(3) 1 d DG . P E 2
H30A H 0.324238 0.052593 0.577798 0.035 Uiso 0.54(3) 1 calc R U P E 2
C25A C 0.3914(17) 0.0671(11) 0.6189(14) 0.029(5) Uani 0.54(3) 1 d DG . P E 2
C26A C 0.4313(18) 0.0380(14) 0.6452(14) 0.029(5) Uani 0.54(3) 1 d DG . P E 2
H26A H 0.458559 0.061534 0.661061 0.035 Uiso 0.54(3) 1 calc R U P E 2
C27A C 0.4312(17) -0.0256(14) 0.6484(14) 0.029(5) Uani 0.54(3) 1 d DG . P E 2
H27A H 0.458381 -0.045454 0.666363 0.035 Uiso 0.54(3) 1 calc R U P E 2
C28A C 0.3912(18) -0.0600(11) 0.6252(14) 0.029(5) Uani 0.54(3) 1 d DG . P E 2
C31A C 0.3915(19) -0.1299(15) 0.6267(18) 0.028(7) Uani 0.54(3) 1 d D U P E 2
H31C H 0.399303 -0.146339 0.598857 0.033 Uiso 0.54(3) 1 calc R U P E 2
H31D H 0.423939 -0.144047 0.645085 0.033 Uiso 0.54(3) 1 calc R U P E 2
N4A N 0.3330(18) -0.1537(17) 0.6420(12) 0.023(4) Uani 0.54(3) 1 d DG . P E 2
C36A C 0.298(2) -0.1929(18) 0.6188(11) 0.023(4) Uani 0.54(3) 1 d DG . P E 2
H36A H 0.308864 -0.203098 0.591515 0.028 Uiso 0.54(3) 1 calc R U P E 2
C35A C 0.2455(18) -0.2172(18) 0.6355(13) 0.023(4) Uani 0.54(3) 1 d DG . P E 2
H35A H 0.221344 -0.243966 0.619654 0.028 Uiso 0.54(3) 1 calc R U P E 2
C34A C 0.2290(15) -0.2022(18) 0.6755(13) 0.023(4) Uani 0.54(3) 1 d DG . P E 2
H34A H 0.193447 -0.218800 0.686888 0.028 Uiso 0.54(3) 1 calc R U P E 2
C33A C 0.2644(18) -0.1630(19) 0.6987(10) 0.023(4) Uani 0.54(3) 1 d DG . P E 2
H33A H 0.253069 -0.152767 0.725984 0.028 Uiso 0.54(3) 1 calc R U P E 2
C32A C 0.3164(18) -0.1387(18) 0.6820(11) 0.023(4) Uani 0.54(3) 1 d DG U P E 2
H32A H 0.340590 -0.111898 0.697845 0.028 Uiso 0.54(3) 1 calc R U P E 2
C109 C 0.715(3) 0.939(2) 0.5757(14) 0.060(8) Uani 0.5 1 d DG . P I 2
H109 H 0.719140 0.898919 0.564905 0.072 Uiso 0.5 1 calc R U P I 2
C97A C 0.715(3) 0.989(3) 0.5494(11) 0.060(8) Uani 0.5 1 d DG . P I 2
C98A C 0.710(3) 1.048(2) 0.5653(14) 0.060(8) Uani 0.5 1 d DG . P I 2
H98A H 0.709893 1.082625 0.547304 0.072 Uiso 0.5 1 calc R U P I 2
C99A C 0.704(3) 1.057(2) 0.6074(15) 0.060(8) Uani 0.5 1 d DG . P I 2
H99A H 0.700021 1.097219 0.618241 0.072 Uiso 0.5 1 calc R U P I 2
C1F C 0.704(3) 1.007(3) 0.6337(11) 0.060(8) Uani 0.5 1 d DG . P I 2
C1H C 0.709(3) 0.948(2) 0.6179(13) 0.060(8) Uani 0.5 1 d DG . P I 2
H1H H 0.709268 0.913513 0.635844 0.072 Uiso 0.5 1 calc R U P I 2
N12A N 0.654(2) 1.005(2) 0.7019(17) 0.074(8) Uani 0.5 1 d DG . P I 2
C1A C 0.638(3) 0.954(2) 0.7246(19) 0.074(8) Uani 0.5 1 d DG . P I 2
H1A H 0.665314 0.921890 0.728893 0.089 Uiso 0.5 1 calc R U P I 2
C1D C 0.580(3) 0.950(3) 0.741(2) 0.074(8) Uani 0.5 1 d DG . P I 2
H1D H 0.569137 0.915188 0.756615 0.089 Uiso 0.5 1 calc R U P I 2
C1G C 0.540(2) 0.997(3) 0.735(2) 0.074(8) Uani 0.5 1 d DG . P I 2
H1G H 0.500717 0.994709 0.746042 0.089 Uiso 0.5 1 calc R U P I 2
C1E C 0.556(2) 1.049(3) 0.712(2) 0.074(8) Uani 0.5 1 d DG . P I 2
H1E H 0.528473 1.080932 0.707746 0.089 Uiso 0.5 1 calc R U P I 2
C1B C 0.613(3) 1.053(2) 0.6956(18) 0.074(8) Uani 0.5 1 d DG . P I 2
H1B H 0.624650 1.087635 0.680023 0.089 Uiso 0.5 1 calc R U P I 2
C1C C 0.714(2) 1.011(3) 0.6801(13) 0.074(8) Uani 0.5 1 d D . P I 2
H1CA H 0.741195 0.978293 0.689273 0.089 Uiso 0.5 1 calc R U P I 2
H1CB H 0.732530 1.051268 0.686925 0.089 Uiso 0.5 1 calc R U P I 2
C96A C 0.737(2) 0.976(3) 0.5060(13) 0.074(8) Uani 0.5 1 d D . P I 2
H96C H 0.772625 1.001366 0.499198 0.089 Uiso 0.5 1 calc R U P I 2
H96D H 0.748147 0.932128 0.502996 0.089 Uiso 0.5 1 calc R U P I 2
C92A C 0.5923(19) 0.965(2) 0.4460(17) 0.048(6) Uani 0.5 1 d DG . P I 2
H92A H 0.559790 0.937102 0.442763 0.058 Uiso 0.5 1 calc R U P I 2
C91A C 0.637(2) 0.952(2) 0.4741(16) 0.048(6) Uani 0.5 1 d DG . P I 2
H91A H 0.635471 0.915515 0.490189 0.058 Uiso 0.5 1 calc R U P I 2
N11A N 0.685(2) 0.992(2) 0.4788(14) 0.048(6) Uani 0.5 1 d DG . P I 2
C95A C 0.687(2) 1.045(2) 0.4554(17) 0.048(6) Uani 0.5 1 d DG . P I 2
H95A H 0.719843 1.072990 0.458584 0.058 Uiso 0.5 1 calc R U P I 2
C94A C 0.642(2) 1.058(2) 0.4272(16) 0.048(6) Uani 0.5 1 d DG . P I 2
H94A H 0.644162 1.094579 0.411159 0.058 Uiso 0.5 1 calc R U P I 2
C93A C 0.595(2) 1.018(3) 0.4225(16) 0.048(6) Uani 0.5 1 d DG . P I 2
H93A H 0.564136 1.026636 0.403247 0.058 Uiso 0.5 1 calc R U P I 2
O2 O 0.566(4) 0.001(3) 0.588(2) 0.056(7) Uani 0.37(3) 1 d D . P G 2
C110 C 0.561(4) 0.055(3) 0.579(3) 0.056(7) Uani 0.37(3) 1 d D . P G 2
H110 H 0.582140 0.087209 0.592301 0.068 Uiso 0.37(3) 1 calc R U P G 2
N13 N 0.522(4) 0.066(3) 0.547(2) 0.056(7) Uani 0.37(3) 1 d D . P G 2
C1I C 0.497(5) 0.008(4) 0.533(3) 0.056(7) Uani 0.37(3) 1 d D . P G 2
H1IA H 0.509830 -0.025358 0.550734 0.084 Uiso 0.37(3) 1 d R U P G 2
H1IB H 0.510250 0.000082 0.504604 0.084 Uiso 0.37(3) 1 d R U P G 2
H1IC H 0.453060 0.010722 0.533214 0.084 Uiso 0.37(3) 1 d R U P G 2
C1J C 0.495(5) 0.121(4) 0.533(3) 0.056(7) Uani 0.37(3) 1 d D . P G 2
H1JA H 0.467210 0.111822 0.509931 0.084 Uiso 0.37(3) 1 d R U P G 2
H1JB H 0.525680 0.149232 0.522941 0.084 Uiso 0.37(3) 1 d R U P G 2
H1JC H 0.472400 0.140192 0.555151 0.084 Uiso 0.37(3) 1 d R U P G 2
C111 C 0.288(6) -0.088(5) 0.790(4) 0.098(12) Uani 0.33(3) 1 d D . P H 2
H111 H 0.303484 -0.125131 0.801735 0.117 Uiso 0.33(3) 1 calc R U P H 2
O1 O 0.255(5) -0.090(6) 0.761(3) 0.098(12) Uani 0.33(3) 1 d D . P H 2
N14 N 0.302(4) -0.032(5) 0.807(3) 0.098(12) Uani 0.33(3) 1 d D . P H 2
C1K C 0.251(6) 0.009(7) 0.812(4) 0.098(12) Uani 0.33(3) 1 d D . P H 2
H1KA H 0.214102 -0.014164 0.811371 0.146 Uiso 0.33(3) 1 d R U P H 2
H1KB H 0.251832 0.039326 0.789951 0.146 Uiso 0.33(3) 1 d R U P H 2
H1KC H 0.254492 0.030496 0.838761 0.146 Uiso 0.33(3) 1 d R U P H 2
C1L C 0.342(6) -0.023(8) 0.842(4) 0.098(12) Uani 0.33(3) 1 d D . P H 2
H1LA H 0.380528 -0.007150 0.832000 0.146 Uiso 0.33(3) 1 d R U P H 2
H1LB H 0.348228 -0.061970 0.855980 0.146 Uiso 0.33(3) 1 d R U P H 2
H1LC H 0.323798 0.006660 0.860450 0.146 Uiso 0.33(3) 1 d R U P H 2


_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
Bi1 I1 3.051(3) . ?
Bi1 I2 3.115(3) . ?
Bi1 I3 3.060(3) . ?
Bi1 I4 3.104(3) . ?
Bi1 I5B 3.093(9) . ?
Bi1 I6B 3.028(10) . ?
Bi1 I5A 3.027(10) . ?
Bi1 I6A 3.126(9) . ?
Bi2 I7 3.064(3) . ?
Bi2 I8 3.132(3) . ?
Bi2 I9 3.074(3) . ?
Bi2 I10B 3.256(19) . ?
Bi2 I11B 2.996(12) . ?
Bi2 I12B 3.090(6) . ?
Bi2 I12A 3.075(7) . ?
Bi2 I10A 3.023(15) . ?
Bi2 I11A 3.149(16) . ?
Bi3B I13 3.090(10) . ?
Bi3B I14 3.086(10) . ?
Bi3B I15B 3.061(9) . ?
Bi3B I16A 3.158(12) . ?
Bi3B I18A 3.014(11) . ?
Bi3B I17A 3.077(8) . ?
Bi4B I19B 3.096(8) . ?
Bi4B I21B 3.096(13) . ?
Bi4B I22B 3.110(14) . ?
Bi4B I23B 3.14(2) . ?
Bi4B I24A 3.075(8) . ?
Bi4B I20A 3.085(19) . ?
I13 Bi3A 3.056(13) . ?
I14 Bi3A 3.099(14) . ?
I16B Bi3A 3.099(17) . ?
I17B Bi3A 3.036(12) . ?
I18B Bi3A 3.113(16) . ?
I20B Bi4A 3.066(18) . ?
I24B Bi4A 3.089(8) . ?
N1 C1 1.3900 . ?
N1 C5 1.3900 . ?
N1 C6 1.512(11) . ?
C1 H1 0.9500 . ?
C1 C2 1.3900 . ?
C2 H2 0.9500 . ?
C2 C3 1.3900 . ?
C3 H3 0.9500 . ?
C3 C4 1.3900 . ?
C4 H4 0.9500 . ?
C4 C5 1.3900 . ?
C5 H5 0.9500 . ?
N2 C14 1.3900 . ?
N2 C18 1.3900 . ?
N2 C13 1.519(11) . ?
C14 H14 0.9500 . ?
C14 C15 1.3900 . ?
C15 H15 0.9500 . ?
C15 C16 1.3900 . ?
C16 H16 0.9500 . ?
C16 C17 1.3900 . ?
C17 H17 0.9500 . ?
C17 C18 1.3900 . ?
C18 H18 0.9500 . ?
N3 C19 1.3900 . ?
N3 C23 1.3900 . ?
N3 C24 1.523(12) . ?
C19 H19 0.9500 . ?
C19 C20 1.3900 . ?
C20 H20 0.9500 . ?
C20 C21 1.3900 . ?
C21 H21 0.9500 . ?
C21 C22 1.3900 . ?
C22 H22 0.9500 . ?
C22 C23 1.3900 . ?
C23 H23 0.9500 . ?
N4 C36 1.3900 . ?
N4 C32 1.3900 . ?
N4 C31 1.518(12) . ?
C36 H36 0.9500 . ?
C36 C35 1.3900 . ?
C35 H35 0.9500 . ?
C35 C34 1.3900 . ?
C34 H34 0.9500 . ?
C34 C33 1.3900 . ?
C33 H33 0.9500 . ?
C33 C32 1.3900 . ?
C32 H32 0.9500 . ?
N5 C37 1.3900 . ?
N5 C41 1.3900 . ?
N5 C42 1.522(12) . ?
C37 H37 0.9500 . ?
C37 C38 1.3900 . ?
C38 H38 0.9500 . ?
C38 C39 1.3900 . ?
C39 H39 0.9500 . ?
C39 C40 1.3900 . ?
C40 H40 0.9500 . ?
C40 C41 1.3900 . ?
C41 H41 0.9500 . ?
N6 C50 1.3900 . ?
N6 C54 1.3900 . ?
N6 C49 1.516(12) . ?
C50 H50 0.9500 . ?
C50 C51 1.3900 . ?
C51 H51 0.9500 . ?
C51 C52 1.3900 . ?
C52 H52 0.9500 . ?
C52 C53 1.3900 . ?
C53 H53 0.9500 . ?
C53 C54 1.3900 . ?
C54 H54 0.9500 . ?
N7 C55 1.3900 . ?
N7 C59 1.3900 . ?
N7 C60 1.518(12) . ?
C55 H55 0.9500 . ?
C55 C56 1.3900 . ?
C56 H56 0.9500 . ?
C56 C57 1.3900 . ?
C57 H57 0.9500 . ?
C57 C58 1.3900 . ?
C58 H58 0.9500 . ?
C58 C59 1.3900 . ?
C59 H59 0.9500 . ?
N8 C68 1.3900 . ?
N8 C72 1.3900 . ?
N8 C67 1.518(12) . ?
C68 H68 0.9500 . ?
C68 C69 1.3900 . ?
C69 H69 0.9500 . ?
C69 C70 1.3900 . ?
C70 H70 0.9500 . ?
C70 C71 1.3900 . ?
C71 H71 0.9500 . ?
C71 C72 1.3900 . ?
C72 H72 0.9500 . ?
N9 C73 1.3900 . ?
N9 C77 1.3900 . ?
N9 C78 1.511(12) . ?
C73 H73 0.9500 . ?
C73 C74 1.3900 . ?
C74 H74 0.9500 . ?
C74 C75 1.3900 . ?
C75 H75 0.9500 . ?
C75 C76 1.3900 . ?
C76 H76 0.9500 . ?
C76 C77 1.3900 . ?
C77 H77 0.9500 . ?
N10 C86 1.3900 . ?
N10 C90 1.3900 . ?
N10 C85 1.517(11) . ?
C86 H86 0.9500 . ?
C86 C87 1.3900 . ?
C87 H87 0.9500 . ?
C87 C88 1.3900 . ?
C88 H88 0.9500 . ?
C88 C89 1.3900 . ?
C89 H89 0.9500 . ?
C89 C90 1.3900 . ?
C90 H90 0.9500 . ?
N12 C104 1.3900 . ?
N12 C108 1.3900 . ?
N12 C103 1.523(12) . ?
C104 H104 0.9500 . ?
C104 C105 1.3900 . ?
C105 H105 0.9500 . ?
C105 C106 1.3900 . ?
C106 H106 0.9500 . ?
C106 C107 1.3900 . ?
C107 H107 0.9500 . ?
C107 C108 1.3900 . ?
C108 H108 0.9500 . ?
C7 C8 1.3900 . ?
C7 C12 1.3900 . ?
C7 C6 1.524(11) . ?
C8 H8 0.9500 . ?
C8 C9 1.3900 . ?
C9 H9 0.9500 . ?
C9 C10 1.3900 . ?
C10 C11 1.3900 . ?
C10 C13 1.525(11) . ?
C11 H11 0.9500 . ?
C11 C12 1.3900 . ?
C12 H12 0.9500 . ?
C29 H29 0.9500 . ?
C29 C30 1.3900 . ?
C29 C28 1.3900 . ?
C30 H30 0.9500 . ?
C30 C25 1.3900 . ?
C25 C26 1.3900 . ?
C25 C24 1.526(12) . ?
C26 H26 0.9500 . ?
C26 C27 1.3900 . ?
C27 H27 0.9500 . ?
C27 C28 1.3900 . ?
C28 C31 1.527(12) . ?
C43 C44 1.3900 . ?
C43 C48 1.3900 . ?
C43 C42 1.523(12) . ?
C44 H44 0.9500 . ?
C44 C45 1.3900 . ?
C45 H45 0.9500 . ?
C45 C46 1.3900 . ?
C46 C47 1.3900 . ?
C46 C49 1.524(12) . ?
C47 H47 0.9500 . ?
C47 C48 1.3900 . ?
C48 H48 0.9500 . ?
C61 C62 1.3900 . ?
C61 C66 1.3900 . ?
C61 C60 1.522(12) . ?
C62 H62 0.9500 . ?
C62 C63 1.3900 . ?
C63 H63 0.9500 . ?
C63 C64 1.3900 . ?
C64 C65 1.3900 . ?
C64 C67 1.524(12) . ?
C65 H65 0.9500 . ?
C65 C66 1.3900 . ?
C66 H66 0.9500 . ?
C79 C80 1.3900 . ?
C79 C84 1.3900 . ?
C79 C78 1.655(11) . ?
C80 H80 0.9500 . ?
C80 C81 1.3900 . ?
C81 H81 0.9500 . ?
C81 C82 1.3900 . ?
C82 C83 1.3900 . ?
C82 C85 1.524(11) . ?
C83 H83 0.9500 . ?
C83 C84 1.3900 . ?
C84 H84 0.9500 . ?
C92 H92 0.9500 . ?
C92 C91 1.3900 . ?
C92 C93 1.3900 . ?
C91 H91 0.9500 . ?
C91 N11 1.3900 . ?
N11 C95 1.3900 . ?
N11 C96 1.525(12) . ?
C95 H95 0.9500 . ?
C95 C94 1.3900 . ?
C94 H94 0.9500 . ?
C94 C93 1.3900 . ?
C93 H93 0.9500 . ?
C102 H102 0.9500 . ?
C102 C97 1.3900 . ?
C102 C101 1.3900 . ?
C97 C98 1.3900 . ?
C97 C96 1.525(12) . ?
C98 H98 0.9500 . ?
C98 C99 1.3900 . ?
C99 H99 0.9500 . ?
C99 C100 1.3900 . ?
C100 C101 1.3900 . ?
C100 C103 1.527(12) . ?
C101 H101 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C60 H60A 0.9900 . ?
C60 H60B 0.9900 . ?
C67 H67A 0.9900 . ?
C67 H67B 0.9900 . ?
C78 H78A 0.9900 . ?
C78 H78B 0.9900 . ?
C85 H85A 0.9900 . ?
C85 H85B 0.9900 . ?
C96 H96A 0.9900 . ?
C96 H96B 0.9900 . ?
C103 H10A 0.9900 . ?
C103 H10B 0.9900 . ?
O201 C201 1.202(13) . ?
N201 C201 1.357(12) . ?
N201 C202 1.457(13) . ?
N201 C203 1.455(13) . ?
C201 H201 0.9500 . ?
C202 H20B 0.9800 . ?
C202 H20C 0.9800 . ?
C202 H20D 0.9800 . ?
C203 H20E 0.9800 . ?
C203 H20F 0.9800 . ?
C203 H20G 0.9800 . ?
O211 C211 1.196(13) . ?
N211 C211 1.355(12) . ?
N211 C212 1.448(13) . ?
N211 C213 1.459(13) . ?
C211 H211 0.9500 . ?
C212 H21B 0.9800 . ?
C212 H21C 0.9800 . ?
C212 H21D 0.9800 . ?
C213 H21E 0.9800 . ?
C213 H21F 0.9800 . ?
C213 H21G 0.9800 . ?
O221 C221 1.205(13) . ?
N221 C221 1.359(13) . ?
N221 C222 1.449(13) . ?
N221 C223 1.455(13) . ?
C221 H221 0.9500 . ?
C222 H22B 0.9801 . ?
C222 H22C 0.9799 . ?
C222 H22D 0.9797 . ?
C223 H22E 0.9800 . ?
C223 H22F 0.9797 . ?
C223 H22G 0.9799 . ?
O231 C231 1.200(13) . ?
N231 C231 1.353(12) . ?
N231 C232 1.451(13) . ?
N231 C233 1.452(13) . ?
C231 H231 0.9500 . ?
C232 H23B 0.9802 . ?
C232 H23C 0.9801 . ?
C232 H23D 0.9798 . ?
C233 H23E 0.9799 . ?
C233 H23F 0.9801 . ?
C233 H23G 0.9797 . ?
I19A Bi4A 3.108(7) . ?
I23A Bi4A 3.02(2) . ?
I15A Bi3A 3.093(15) . ?
I22A Bi4A 3.101(13) . ?
Bi4A I21A 3.048(12) . ?
C24A H24C 0.9900 . ?
C24A H24D 0.9900 . ?
C24A N3A 1.51(2) . ?
C24A C25A 1.52(2) . ?
N3A C19A 1.3900 . ?
N3A C23A 1.3900 . ?
C19A H19A 0.9500 . ?
C19A C20A 1.3900 . ?
C20A H20A 0.9500 . ?
C20A C21A 1.3900 . ?
C21A H21A 0.9500 . ?
C21A C22A 1.3900 . ?
C22A H22A 0.9500 . ?
C22A C23A 1.3900 . ?
C23A H23A 0.9500 . ?
C29A H29A 0.9500 . ?
C29A C30A 1.3900 . ?
C29A C28A 1.3900 . ?
C30A H30A 0.9500 . ?
C30A C25A 1.3900 . ?
C25A C26A 1.3900 . ?
C26A H26A 0.9500 . ?
C26A C27A 1.3900 . ?
C27A H27A 0.9500 . ?
C27A C28A 1.3900 . ?
C28A C31A 1.53(2) . ?
C31A H31C 0.9900 . ?
C31A H31D 0.9900 . ?
C31A N4A 1.50(2) . ?
N4A C36A 1.3900 . ?
N4A C32A 1.3900 . ?
C36A H36A 0.9500 . ?
C36A C35A 1.3900 . ?
C35A H35A 0.9500 . ?
C35A C34A 1.3900 . ?
C34A H34A 0.9500 . ?
C34A C33A 1.3900 . ?
C33A H33A 0.9500 . ?
C33A C32A 1.3900 . ?
C32A H32A 0.9500 . ?
C109 H109 0.9500 . ?
C109 C97A 1.3900 . ?
C109 C1H 1.3900 . ?
C97A C98A 1.3900 . ?
C97A C96A 1.52(3) . ?
C98A H98A 0.9500 . ?
C98A C99A 1.3900 . ?
C99A H99A 0.9500 . ?
C99A C1F 1.3900 . ?
C1F C1H 1.3900 . ?
C1F C1C 1.53(3) . ?
C1H H1H 0.9500 . ?
N12A C1A 1.3900 . ?
N12A C1B 1.3900 . ?
N12A C1C 1.52(3) . ?
C1A H1A 0.9500 . ?
C1A C1D 1.3900 . ?
C1D H1D 0.9500 . ?
C1D C1G 1.3900 . ?
C1G H1G 0.9500 . ?
C1G C1E 1.3900 . ?
C1E H1E 0.9500 . ?
C1E C1B 1.3900 . ?
C1B H1B 0.9500 . ?
C1C H1CA 0.9900 . ?
C1C H1CB 0.9900 . ?
C96A H96C 0.9900 . ?
C96A H96D 0.9900 . ?
C96A N11A 1.52(3) . ?
C92A H92A 0.9500 . ?
C92A C91A 1.3900 . ?
C92A C93A 1.3900 . ?
C91A H91A 0.9500 . ?
C91A N11A 1.3900 . ?
N11A C95A 1.3900 . ?
C95A H95A 0.9500 . ?
C95A C94A 1.3900 . ?
C94A H94A 0.9500 . ?
C94A C93A 1.3900 . ?
C93A H93A 0.9500 . ?
O2 C110 1.23(3) . ?
C110 H110 0.9500 . ?
C110 N13 1.38(3) . ?
N13 C1I 1.45(3) . ?
N13 C1J 1.43(3) . ?
C1I H1IA 0.9801 . ?
C1I H1IB 0.9795 . ?
C1I H1IC 0.9800 . ?
C1J H1JA 0.9799 . ?
C1J H1JB 0.9799 . ?
C1J H1JC 0.9801 . ?
C111 H111 0.9500 . ?
C111 O1 1.21(3) . ?
C111 N14 1.37(3) . ?
N14 C1K 1.46(3) . ?
N14 C1L 1.46(3) . ?
C1K H1KA 0.9800 . ?
C1K H1KB 0.9796 . ?
C1K H1KC 0.9806 . ?
C1L H1LA 0.9803 . ?
C1L H1LB 0.9800 . ?
C1L H1LC 0.9799 . ?

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
I1 Bi1 I2 86.71(7) . . ?
I1 Bi1 I3 92.20(7) . . ?
I1 Bi1 I4 91.25(8) . . ?
I1 Bi1 I5B 83.08(15) . . ?
I1 Bi1 I6A 174.13(16) . . ?
I2 Bi1 I6A 87.61(16) . . ?
I3 Bi1 I2 89.18(7) . . ?
I3 Bi1 I4 176.47(9) . . ?
I3 Bi1 I5B 87.46(19) . . ?
I3 Bi1 I6A 86.24(16) . . ?
I4 Bi1 I2 90.30(8) . . ?
I4 Bi1 I6A 90.25(16) . . ?
I5B Bi1 I2 169.11(16) . . ?
I5B Bi1 I4 93.67(19) . . ?
I5B Bi1 I6A 102.5(2) . . ?
I6B Bi1 I1 174.98(17) . . ?
I6B Bi1 I2 97.08(18) . . ?
I6B Bi1 I3 91.14(18) . . ?
I6B Bi1 I4 85.46(18) . . ?
I5A Bi1 I1 93.31(17) . . ?
I5A Bi1 I2 178.0(2) . . ?
I5A Bi1 I3 88.8(2) . . ?
I5A Bi1 I4 91.7(2) . . ?
I5A Bi1 I6B 83.0(3) . . ?
I7 Bi2 I8 89.22(7) . . ?
I7 Bi2 I9 89.19(8) . . ?
I7 Bi2 I10B 93.4(5) . . ?
I7 Bi2 I12B 177.35(14) . . ?
I7 Bi2 I12A 168.41(18) . . ?
I7 Bi2 I11A 84.4(3) . . ?
I8 Bi2 I10B 84.7(3) . . ?
I8 Bi2 I11A 173.2(2) . . ?
I9 Bi2 I8 90.00(7) . . ?
I9 Bi2 I10B 174.1(4) . . ?
I9 Bi2 I12B 91.10(13) . . ?
I9 Bi2 I12A 83.25(16) . . ?
I9 Bi2 I11A 87.7(3) . . ?
I11B Bi2 I7 89.2(2) . . ?
I11B Bi2 I8 177.7(3) . . ?
I11B Bi2 I9 91.7(2) . . ?
I11B Bi2 I12B 93.4(2) . . ?
I11B Bi2 I10A 88.4(3) . . ?
I12B Bi2 I8 88.14(13) . . ?
I12A Bi2 I8 99.52(17) . . ?
I12A Bi2 I10B 95.0(5) . . ?
I12A Bi2 I11A 86.5(3) . . ?
I10A Bi2 I7 94.6(4) . . ?
I10A Bi2 I8 90.0(2) . . ?
I10A Bi2 I9 176.2(4) . . ?
I10A Bi2 I12B 85.1(4) . . ?
I11A Bi2 I10B 97.9(5) . . ?
I13 Bi3B I16A 175.5(4) . . ?
I14 Bi3B I13 85.6(2) . . ?
I14 Bi3B I16A 90.4(3) . . ?
I15B Bi3B I13 89.0(4) . . ?
I15B Bi3B I14 95.4(4) . . ?
I15B Bi3B I16A 89.5(4) . . ?
I15B Bi3B I17A 174.9(5) . . ?
I18A Bi3B I13 91.5(3) . . ?
I18A Bi3B I14 175.4(3) . . ?
I18A Bi3B I15B 88.0(4) . . ?
I18A Bi3B I16A 92.6(3) . . ?
I18A Bi3B I17A 87.0(3) . . ?
I17A Bi3B I13 90.4(2) . . ?
I17A Bi3B I14 89.6(2) . . ?
I17A Bi3B I16A 91.5(3) . . ?
I19B Bi4B I21B 173.9(3) . . ?
I19B Bi4B I22B 90.6(4) . . ?
I19B Bi4B I23B 94.3(3) . . ?
I21B Bi4B I22B 90.1(4) . . ?
I21B Bi4B I23B 91.7(4) . . ?
I22B Bi4B I23B 92.6(5) . . ?
I24A Bi4B I19B 87.1(2) . . ?
I24A Bi4B I21B 92.6(2) . . ?
I24A Bi4B I22B 175.9(5) . . ?
I24A Bi4B I23B 84.2(4) . . ?
I24A Bi4B I20A 91.6(3) . . ?
I20A Bi4B I19B 85.5(3) . . ?
I20A Bi4B I21B 88.4(4) . . ?
I20A Bi4B I22B 91.5(5) . . ?
I20A Bi4B I23B 175.9(5) . . ?
C1 N1 C5 120.0 . . ?
C1 N1 C6 120.0(12) . . ?
C5 N1 C6 119.8(11) . . ?
N1 C1 H1 120.0 . . ?
N1 C1 C2 120.0 . . ?
C2 C1 H1 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
N1 C5 H5 120.0 . . ?
C4 C5 N1 120.0 . . ?
C4 C5 H5 120.0 . . ?
C14 N2 C18 120.0 . . ?
C14 N2 C13 118.8(11) . . ?
C18 N2 C13 121.0(11) . . ?
N2 C14 H14 120.0 . . ?
C15 C14 N2 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.0 . . ?
C18 C17 H17 120.0 . . ?
N2 C18 H18 120.0 . . ?
C17 C18 N2 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 N3 C23 120.0 . . ?
C19 N3 C24 119.3(14) . . ?
C23 N3 C24 119.9(14) . . ?
N3 C19 H19 120.0 . . ?
C20 C19 N3 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.0 . . ?
C23 C22 H22 120.0 . . ?
N3 C23 H23 120.0 . . ?
C22 C23 N3 120.0 . . ?
C22 C23 H23 120.0 . . ?
C36 N4 C32 120.0 . . ?
C36 N4 C31 120.7(13) . . ?
C32 N4 C31 119.3(13) . . ?
N4 C36 H36 120.0 . . ?
N4 C36 C35 120.0 . . ?
C35 C36 H36 120.0 . . ?
C36 C35 H35 120.0 . . ?
C34 C35 C36 120.0 . . ?
C34 C35 H35 120.0 . . ?
C35 C34 H34 120.0 . . ?
C35 C34 C33 120.0 . . ?
C33 C34 H34 120.0 . . ?
C34 C33 H33 120.0 . . ?
C32 C33 C34 120.0 . . ?
C32 C33 H33 120.0 . . ?
N4 C32 H32 120.0 . . ?
C33 C32 N4 120.0 . . ?
C33 C32 H32 120.0 . . ?
C37 N5 C41 120.0 . . ?
C37 N5 C42 120.1(12) . . ?
C41 N5 C42 119.8(12) . . ?
N5 C37 H37 120.0 . . ?
C38 C37 N5 120.0 . . ?
C38 C37 H37 120.0 . . ?
C37 C38 H38 120.0 . . ?
C37 C38 C39 120.0 . . ?
C39 C38 H38 120.0 . . ?
C38 C39 H39 120.0 . . ?
C40 C39 C38 120.0 . . ?
C40 C39 H39 120.0 . . ?
C39 C40 H40 120.0 . . ?
C39 C40 C41 120.0 . . ?
C41 C40 H40 120.0 . . ?
N5 C41 H41 120.0 . . ?
C40 C41 N5 120.0 . . ?
C40 C41 H41 120.0 . . ?
C50 N6 C54 120.0 . . ?
C50 N6 C49 119.2(13) . . ?
C54 N6 C49 120.7(13) . . ?
N6 C50 H50 120.0 . . ?
N6 C50 C51 120.0 . . ?
C51 C50 H50 120.0 . . ?
C50 C51 H51 120.0 . . ?
C52 C51 C50 120.0 . . ?
C52 C51 H51 120.0 . . ?
C51 C52 H52 120.0 . . ?
C51 C52 C53 120.0 . . ?
C53 C52 H52 120.0 . . ?
C52 C53 H53 120.0 . . ?
C54 C53 C52 120.0 . . ?
C54 C53 H53 120.0 . . ?
N6 C54 H54 120.0 . . ?
C53 C54 N6 120.0 . . ?
C53 C54 H54 120.0 . . ?
C55 N7 C59 120.0 . . ?
C55 N7 C60 120.0(13) . . ?
C59 N7 C60 119.7(13) . . ?
N7 C55 H55 120.0 . . ?
N7 C55 C56 120.0 . . ?
C56 C55 H55 120.0 . . ?
C55 C56 H56 120.0 . . ?
C55 C56 C57 120.0 . . ?
C57 C56 H56 120.0 . . ?
C56 C57 H57 120.0 . . ?
C58 C57 C56 120.0 . . ?
C58 C57 H57 120.0 . . ?
C57 C58 H58 120.0 . . ?
C57 C58 C59 120.0 . . ?
C59 C58 H58 120.0 . . ?
N7 C59 H59 120.0 . . ?
C58 C59 N7 120.0 . . ?
C58 C59 H59 120.0 . . ?
C68 N8 C72 120.0 . . ?
C68 N8 C67 120.3(12) . . ?
C72 N8 C67 119.7(12) . . ?
N8 C68 H68 120.0 . . ?
C69 C68 N8 120.0 . . ?
C69 C68 H68 120.0 . . ?
C68 C69 H69 120.0 . . ?
C68 C69 C70 120.0 . . ?
C70 C69 H69 120.0 . . ?
C69 C70 H70 120.0 . . ?
C69 C70 C71 120.0 . . ?
C71 C70 H70 120.0 . . ?
C70 C71 H71 120.0 . . ?
C72 C71 C70 120.0 . . ?
C72 C71 H71 120.0 . . ?
N8 C72 H72 120.0 . . ?
C71 C72 N8 120.0 . . ?
C71 C72 H72 120.0 . . ?
C73 N9 C77 120.0 . . ?
C73 N9 C78 117.1(13) . . ?
C77 N9 C78 122.5(14) . . ?
N9 C73 H73 120.0 . . ?
N9 C73 C74 120.0 . . ?
C74 C73 H73 120.0 . . ?
C73 C74 H74 120.0 . . ?
C73 C74 C75 120.0 . . ?
C75 C74 H74 120.0 . . ?
C74 C75 H75 120.0 . . ?
C76 C75 C74 120.0 . . ?
C76 C75 H75 120.0 . . ?
C75 C76 H76 120.0 . . ?
C75 C76 C77 120.0 . . ?
C77 C76 H76 120.0 . . ?
N9 C77 H77 120.0 . . ?
C76 C77 N9 120.0 . . ?
C76 C77 H77 120.0 . . ?
C86 N10 C90 120.0 . . ?
C86 N10 C85 121.8(11) . . ?
C90 N10 C85 118.1(11) . . ?
N10 C86 H86 120.0 . . ?
C87 C86 N10 120.0 . . ?
C87 C86 H86 120.0 . . ?
C86 C87 H87 120.0 . . ?
C86 C87 C88 120.0 . . ?
C88 C87 H87 120.0 . . ?
C87 C88 H88 120.0 . . ?
C87 C88 C89 120.0 . . ?
C89 C88 H88 120.0 . . ?
C88 C89 H89 120.0 . . ?
C88 C89 C90 120.0 . . ?
C90 C89 H89 120.0 . . ?
N10 C90 H90 120.0 . . ?
C89 C90 N10 120.0 . . ?
C89 C90 H90 120.0 . . ?
C104 N12 C108 120.0 . . ?
C104 N12 C103 121.1(15) . . ?
C108 N12 C103 118.9(15) . . ?
N12 C104 H104 120.0 . . ?
C105 C104 N12 120.0 . . ?
C105 C104 H104 120.0 . . ?
C104 C105 H105 120.0 . . ?
C104 C105 C106 120.0 . . ?
C106 C105 H105 120.0 . . ?
C105 C106 H106 120.0 . . ?
C107 C106 C105 120.0 . . ?
C107 C106 H106 120.0 . . ?
C106 C107 H107 120.0 . . ?
C108 C107 C106 120.0 . . ?
C108 C107 H107 120.0 . . ?
N12 C108 H108 120.0 . . ?
C107 C108 N12 120.00(5) . . ?
C107 C108 H108 120.0 . . ?
C8 C7 C12 120.0 . . ?
C8 C7 C6 118.7(11) . . ?
C12 C7 C6 121.2(11) . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C11 120.0 . . ?
C9 C10 C13 120.3(11) . . ?
C11 C10 C13 119.6(11) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.0 . . ?
C7 C12 H12 120.0 . . ?
C11 C12 C7 120.0 . . ?
C11 C12 H12 120.0 . . ?
C30 C29 H29 120.0 . . ?
C30 C29 C28 120.0 . . ?
C28 C29 H29 120.0 . . ?
C29 C30 H30 120.0 . . ?
C29 C30 C25 120.0 . . ?
C25 C30 H30 120.0 . . ?
C30 C25 C24 120.0(14) . . ?
C26 C25 C30 120.0 . . ?
C26 C25 C24 119.9(14) . . ?
C25 C26 H26 120.0 . . ?
C25 C26 C27 120.0 . . ?
C27 C26 H26 120.0 . . ?
C26 C27 H27 120.0 . . ?
C28 C27 C26 120.0 . . ?
C28 C27 H27 120.0 . . ?
C29 C28 C31 119.6(13) . . ?
C27 C28 C29 120.0 . . ?
C27 C28 C31 120.4(13) . . ?
C44 C43 C48 120.0 . . ?
C44 C43 C42 121.3(13) . . ?
C48 C43 C42 118.7(13) . . ?
C43 C44 H44 120.0 . . ?
C43 C44 C45 120.0 . . ?
C45 C44 H44 120.0 . . ?
C44 C45 H45 120.0 . . ?
C44 C45 C46 120.0 . . ?
C46 C45 H45 120.0 . . ?
C45 C46 C49 121.0(13) . . ?
C47 C46 C45 120.0 . . ?
C47 C46 C49 118.4(13) . . ?
C46 C47 H47 120.0 . . ?
C46 C47 C48 120.0 . . ?
C48 C47 H47 120.0 . . ?
C43 C48 H48 120.0 . . ?
C47 C48 C43 120.0 . . ?
C47 C48 H48 120.0 . . ?
C62 C61 C66 120.0 . . ?
C62 C61 C60 119.3(12) . . ?
C66 C61 C60 120.3(12) . . ?
C61 C62 H62 120.0 . . ?
C61 C62 C63 120.0 . . ?
C63 C62 H62 120.0 . . ?
C62 C63 H63 120.0 . . ?
C62 C63 C64 120.0 . . ?
C64 C63 H63 120.0 . . ?
C63 C64 C67 117.6(12) . . ?
C65 C64 C63 120.0 . . ?
C65 C64 C67 122.1(12) . . ?
C64 C65 H65 120.0 . . ?
C66 C65 C64 120.0 . . ?
C66 C65 H65 120.0 . . ?
C61 C66 H66 120.0 . . ?
C65 C66 C61 120.0 . . ?
C65 C66 H66 120.0 . . ?
C80 C79 C84 120.0 . . ?
C80 C79 C78 124.1(10) . . ?
C84 C79 C78 114.0(9) . . ?
C79 C80 H80 120.0 . . ?
C81 C80 C79 120.0 . . ?
C81 C80 H80 120.0 . . ?
C80 C81 H81 120.0 . . ?
C80 C81 C82 120.0 . . ?
C82 C81 H81 120.0 . . ?
C81 C82 C85 120.4(10) . . ?
C83 C82 C81 120.0 . . ?
C83 C82 C85 119.6(10) . . ?
C82 C83 H83 120.0 . . ?
C82 C83 C84 120.0 . . ?
C84 C83 H83 120.0 . . ?
C79 C84 H84 120.0 . . ?
C83 C84 C79 120.0 . . ?
C83 C84 H84 120.0 . . ?
C91 C92 H92 120.0 . . ?
C91 C92 C93 120.0 . . ?
C93 C92 H92 120.0 . . ?
C92 C91 H91 120.0 . . ?
C92 C91 N11 120.0 . . ?
N11 C91 H91 120.0 . . ?
C91 N11 C95 120.0 . . ?
C91 N11 C96 120.3(15) . . ?
C95 N11 C96 119.7(15) . . ?
N11 C95 H95 120.0 . . ?
C94 C95 N11 120.0 . . ?
C94 C95 H95 120.0 . . ?
C95 C94 H94 120.0 . . ?
C95 C94 C93 120.0 . . ?
C93 C94 H94 120.0 . . ?
C92 C93 H93 120.0 . . ?
C94 C93 C92 120.0 . . ?
C94 C93 H93 120.0 . . ?
C97 C102 H102 120.0 . . ?
C97 C102 C101 120.0 . . ?
C101 C102 H102 120.0 . . ?
C102 C97 C96 118.8(15) . . ?
C98 C97 C102 120.0 . . ?
C98 C97 C96 121.1(15) . . ?
C97 C98 H98 120.0 . . ?
C99 C98 C97 120.0 . . ?
C99 C98 H98 120.0 . . ?
C98 C99 H99 120.0 . . ?
C98 C99 C100 120.0 . . ?
C100 C99 H99 120.0 . . ?
C99 C100 C103 121.3(17) . . ?
C101 C100 C99 120.0 . . ?
C101 C100 C103 117.1(15) . . ?
C102 C101 H101 120.0 . . ?
C100 C101 C102 120.0 . . ?
C100 C101 H101 120.0 . . ?
N1 C6 C7 109.3(16) . . ?
N1 C6 H6A 109.8 . . ?
N1 C6 H6B 109.8 . . ?
C7 C6 H6A 109.8 . . ?
C7 C6 H6B 109.8 . . ?
H6A C6 H6B 108.3 . . ?
N2 C13 C10 109.0(16) . . ?
N2 C13 H13A 109.9 . . ?
N2 C13 H13B 109.9 . . ?
C10 C13 H13A 109.9 . . ?
C10 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
N3 C24 C25 109(3) . . ?
N3 C24 H24A 109.9 . . ?
N3 C24 H24B 109.9 . . ?
C25 C24 H24A 109.9 . . ?
C25 C24 H24B 109.9 . . ?
H24A C24 H24B 108.3 . . ?
N4 C31 C28 109(3) . . ?
N4 C31 H31A 109.8 . . ?
N4 C31 H31B 109.8 . . ?
C28 C31 H31A 109.8 . . ?
C28 C31 H31B 109.8 . . ?
H31A C31 H31B 108.2 . . ?
N5 C42 C43 114(2) . . ?
N5 C42 H42A 108.7 . . ?
N5 C42 H42B 108.7 . . ?
C43 C42 H42A 108.7 . . ?
C43 C42 H42B 108.7 . . ?
H42A C42 H42B 107.6 . . ?
N6 C49 C46 108.0(18) . . ?
N6 C49 H49A 110.1 . . ?
N6 C49 H49B 110.1 . . ?
C46 C49 H49A 110.1 . . ?
C46 C49 H49B 110.1 . . ?
H49A C49 H49B 108.4 . . ?
N7 C60 C61 107.2(18) . . ?
N7 C60 H60A 110.3 . . ?
N7 C60 H60B 110.3 . . ?
C61 C60 H60A 110.3 . . ?
C61 C60 H60B 110.3 . . ?
H60A C60 H60B 108.5 . . ?
N8 C67 C64 108.8(17) . . ?
N8 C67 H67A 109.9 . . ?
N8 C67 H67B 109.9 . . ?
C64 C67 H67A 109.9 . . ?
C64 C67 H67B 109.9 . . ?
H67A C67 H67B 108.3 . . ?
N9 C78 C79 104.4(13) . . ?
N9 C78 H78A 110.9 . . ?
N9 C78 H78B 110.9 . . ?
C79 C78 H78A 110.9 . . ?
C79 C78 H78B 110.9 . . ?
H78A C78 H78B 108.9 . . ?
N10 C85 C82 109.7(17) . . ?
N10 C85 H85A 109.7 . . ?
N10 C85 H85B 109.7 . . ?
C82 C85 H85A 109.7 . . ?
C82 C85 H85B 109.7 . . ?
H85A C85 H85B 108.2 . . ?
N11 C96 C97 104(3) . . ?
N11 C96 H96A 110.9 . . ?
N11 C96 H96B 110.9 . . ?
C97 C96 H96A 110.9 . . ?
C97 C96 H96B 110.9 . . ?
H96A C96 H96B 108.9 . . ?
N12 C103 C100 110(3) . . ?
N12 C103 H10A 109.6 . . ?
N12 C103 H10B 109.6 . . ?
C100 C103 H10A 109.6 . . ?
C100 C103 H10B 109.6 . . ?
H10A C103 H10B 108.1 . . ?
C201 N201 C202 125.8(17) . . ?
C201 N201 C203 120.6(17) . . ?
C203 N201 C202 114(2) . . ?
O201 C201 N201 122.9(17) . . ?
O201 C201 H201 118.5 . . ?
N201 C201 H201 118.5 . . ?
N201 C202 H20B 109.5 . . ?
N201 C202 H20C 109.5 . . ?
N201 C202 H20D 109.5 . . ?
H20B C202 H20C 109.5 . . ?
H20B C202 H20D 109.5 . . ?
H20C C202 H20D 109.5 . . ?
N201 C203 H20E 109.5 . . ?
N201 C203 H20F 109.5 . . ?
N201 C203 H20G 109.5 . . ?
H20E C203 H20F 109.5 . . ?
H20E C203 H20G 109.5 . . ?
H20F C203 H20G 109.5 . . ?
C211 N211 C212 127.2(16) . . ?
C211 N211 C213 120.4(16) . . ?
C212 N211 C213 112(2) . . ?
O211 C211 N211 123.0(17) . . ?
O211 C211 H211 118.5 . . ?
N211 C211 H211 118.5 . . ?
N211 C212 H21B 109.5 . . ?
N211 C212 H21C 109.5 . . ?
N211 C212 H21D 109.5 . . ?
H21B C212 H21C 109.5 . . ?
H21B C212 H21D 109.5 . . ?
H21C C212 H21D 109.5 . . ?
N211 C213 H21E 109.5 . . ?
N211 C213 H21F 109.5 . . ?
N211 C213 H21G 109.5 . . ?
H21E C213 H21F 109.5 . . ?
H21E C213 H21G 109.5 . . ?
H21F C213 H21G 109.5 . . ?
C221 N221 C222 126.9(18) . . ?
C221 N221 C223 117.5(19) . . ?
C222 N221 C223 116(3) . . ?
O221 C221 N221 123(2) . . ?
O221 C221 H221 118.7 . . ?
N221 C221 H221 118.7 . . ?
N221 C222 H22B 110.0 . . ?
N221 C222 H22C 109.0 . . ?
N221 C222 H22D 109.4 . . ?
H22B C222 H22C 109.5 . . ?
H22B C222 H22D 109.5 . . ?
H22C C222 H22D 109.5 . . ?
N221 C223 H22E 110.3 . . ?
N221 C223 H22F 109.4 . . ?
N221 C223 H22G 108.7 . . ?
H22E C223 H22F 109.5 . . ?
H22E C223 H22G 109.5 . . ?
H22F C223 H22G 109.5 . . ?
C231 N231 C232 128.5(18) . . ?
C231 N231 C233 120(2) . . ?
C232 N231 C233 111(3) . . ?
O231 C231 N231 123.9(19) . . ?
O231 C231 H231 118.0 . . ?
N231 C231 H231 118.0 . . ?
N231 C232 H23B 109.8 . . ?
N231 C232 H23C 109.5 . . ?
N231 C232 H23D 109.2 . . ?
H23B C232 H23C 109.5 . . ?
H23B C232 H23D 109.5 . . ?
H23C C232 H23D 109.5 . . ?
N231 C233 H23E 110.4 . . ?
N231 C233 H23F 108.8 . . ?
N231 C233 H23G 109.2 . . ?
H23E C233 H23F 109.4 . . ?
H23E C233 H23G 109.5 . . ?
H23F C233 H23G 109.5 . . ?
I20B Bi4A I24B 87.1(3) . . ?
I20B Bi4A I19A 90.8(3) . . ?
I20B Bi4A I22A 91.0(4) . . ?
I24B Bi4A I19A 88.1(2) . . ?
I24B Bi4A I22A 177.6(4) . . ?
I23A Bi4A I20B 177.4(5) . . ?
I23A Bi4A I24B 91.6(4) . . ?
I23A Bi4A I19A 86.9(3) . . ?
I23A Bi4A I22A 90.3(5) . . ?
I23A Bi4A I21A 90.4(4) . . ?
I22A Bi4A I19A 93.5(4) . . ?
I21A Bi4A I20B 91.8(4) . . ?
I21A Bi4A I24B 87.5(2) . . ?
I21A Bi4A I19A 174.8(3) . . ?
I21A Bi4A I22A 91.0(4) . . ?
I13 Bi3A I14 85.9(3) . . ?
I13 Bi3A I16B 173.7(3) . . ?
I13 Bi3A I18B 94.1(4) . . ?
I13 Bi3A I15A 84.5(5) . . ?
I14 Bi3A I16B 92.4(4) . . ?
I14 Bi3A I18B 178.1(3) . . ?
I16B Bi3A I18B 87.9(4) . . ?
I17B Bi3A I13 92.1(4) . . ?
I17B Bi3A I14 90.6(4) . . ?
I17B Bi3A I16B 93.9(4) . . ?
I17B Bi3A I18B 87.5(4) . . ?
I17B Bi3A I15A 176.5(7) . . ?
I15A Bi3A I14 89.9(5) . . ?
I15A Bi3A I16B 89.5(5) . . ?
I15A Bi3A I18B 91.9(5) . . ?
H24C C24A H24D 108.2 . . ?
N3A C24A H24C 109.7 . . ?
N3A C24A H24D 109.7 . . ?
N3A C24A C25A 110(3) . . ?
C25A C24A H24C 109.7 . . ?
C25A C24A H24D 109.7 . . ?
C19A N3A C24A 119(2) . . ?
C19A N3A C23A 120.0 . . ?
C23A N3A C24A 121(2) . . ?
N3A C19A H19A 120.0 . . ?
N3A C19A C20A 120.0 . . ?
C20A C19A H19A 120.0 . . ?
C19A C20A H20A 120.0 . . ?
C21A C20A C19A 120.0 . . ?
C21A C20A H20A 120.0 . . ?
C20A C21A H21A 120.0 . . ?
C22A C21A C20A 120.0 . . ?
C22A C21A H21A 120.0 . . ?
C21A C22A H22A 120.0 . . ?
C21A C22A C23A 120.0 . . ?
C23A C22A H22A 120.0 . . ?
N3A C23A H23A 120.0 . . ?
C22A C23A N3A 120.0 . . ?
C22A C23A H23A 120.0 . . ?
C30A C29A H29A 120.0 . . ?
C30A C29A C28A 120.0 . . ?
C28A C29A H29A 120.0 . . ?
C29A C30A H30A 120.0 . . ?
C29A C30A C25A 120.0 . . ?
C25A C30A H30A 120.0 . . ?
C30A C25A C24A 120(2) . . ?
C30A C25A C26A 120.0 . . ?
C26A C25A C24A 120(2) . . ?
C25A C26A H26A 120.0 . . ?
C27A C26A C25A 120.0 . . ?
C27A C26A H26A 120.0 . . ?
C26A C27A H27A 120.0 . . ?
C26A C27A C28A 120.0 . . ?
C28A C27A H27A 120.0 . . ?
C29A C28A C31A 119(2) . . ?
C27A C28A C29A 120.0 . . ?
C27A C28A C31A 121(2) . . ?
C28A C31A H31C 109.5 . . ?
C28A C31A H31D 109.5 . . ?
H31C C31A H31D 108.1 . . ?
N4A C31A C28A 111(3) . . ?
N4A C31A H31C 109.5 . . ?
N4A C31A H31D 109.5 . . ?
C36A N4A C31A 122(2) . . ?
C36A N4A C32A 120.0 . . ?
C32A N4A C31A 118(2) . . ?
N4A C36A H36A 120.0 . . ?
C35A C36A N4A 120.0 . . ?
C35A C36A H36A 120.0 . . ?
C36A C35A H35A 120.0 . . ?
C34A C35A C36A 120.0 . . ?
C34A C35A H35A 120.0 . . ?
C35A C34A H34A 120.0 . . ?
C35A C34A C33A 120.0 . . ?
C33A C34A H34A 120.0 . . ?
C34A C33A H33A 120.0 . . ?
C32A C33A C34A 120.0 . . ?
C32A C33A H33A 120.0 . . ?
N4A C32A H32A 120.0 . . ?
C33A C32A N4A 120.0 . . ?
C33A C32A H32A 120.0 . . ?
C97A C109 H109 120.0 . . ?
C97A C109 C1H 120.0 . . ?
C1H C109 H109 120.0 . . ?
C109 C97A C98A 120.0 . . ?
C109 C97A C96A 115(3) . . ?
C98A C97A C96A 123(3) . . ?
C97A C98A H98A 120.0 . . ?
C99A C98A C97A 120.0 . . ?
C99A C98A H98A 120.0 . . ?
C98A C99A H99A 120.0 . . ?
C1F C99A C98A 120.0 . . ?
C1F C99A H99A 120.0 . . ?
C99A C1F C1C 124(3) . . ?
C1H C1F C99A 120.0 . . ?
C1H C1F C1C 114(3) . . ?
C109 C1H H1H 120.0 . . ?
C1F C1H C109 120.0 . . ?
C1F C1H H1H 120.0 . . ?
C1A N12A C1B 120.0 . . ?
C1A N12A C1C 123(3) . . ?
C1B N12A C1C 116(3) . . ?
N12A C1A H1A 120.0 . . ?
C1D C1A N12A 120.0 . . ?
C1D C1A H1A 120.0 . . ?
C1A C1D H1D 120.0 . . ?
C1G C1D C1A 120.0 . . ?
C1G C1D H1D 120.0 . . ?
C1D C1G H1G 120.0 . . ?
C1D C1G C1E 120.0 . . ?
C1E C1G H1G 120.0 . . ?
C1G C1E H1E 120.0 . . ?
C1B C1E C1G 120.0 . . ?
C1B C1E H1E 120.0 . . ?
N12A C1B H1B 120.0 . . ?
C1E C1B N12A 120.0 . . ?
C1E C1B H1B 120.0 . . ?
C1F C1C H1CA 110.0 . . ?
C1F C1C H1CB 110.0 . . ?
N12A C1C C1F 109(4) . . ?
N12A C1C H1CA 110.0 . . ?
N12A C1C H1CB 110.0 . . ?
H1CA C1C H1CB 108.3 . . ?
C97A C96A H96C 110.9 . . ?
C97A C96A H96D 110.9 . . ?
H96C C96A H96D 108.9 . . ?
N11A C96A C97A 104(4) . . ?
N11A C96A H96C 110.9 . . ?
N11A C96A H96D 110.9 . . ?
C91A C92A H92A 120.0 . . ?
C91A C92A C93A 120.0 . . ?
C93A C92A H92A 120.0 . . ?
C92A C91A H91A 120.0 . . ?
N11A C91A C92A 120.0 . . ?
N11A C91A H91A 120.0 . . ?
C91A N11A C96A 121(3) . . ?
C95A N11A C96A 119(3) . . ?
C95A N11A C91A 120.0 . . ?
N11A C95A H95A 120.0 . . ?
C94A C95A N11A 120.0 . . ?
C94A C95A H95A 120.0 . . ?
C95A C94A H94A 120.0 . . ?
C95A C94A C93A 120.0 . . ?
C93A C94A H94A 120.0 . . ?
C92A C93A H93A 120.0 . . ?
C94A C93A C92A 120.0 . . ?
C94A C93A H93A 120.0 . . ?
O2 C110 H110 123.3 . . ?
O2 C110 N13 113(5) . . ?
N13 C110 H110 123.3 . . ?
C110 N13 C1I 110(4) . . ?
C110 N13 C1J 131(5) . . ?
C1J N13 C1I 118(4) . . ?
N13 C1I H1IA 109.9 . . ?
N13 C1I H1IB 109.4 . . ?
N13 C1I H1IC 109.1 . . ?
H1IA C1I H1IB 109.5 . . ?
H1IA C1I H1IC 109.5 . . ?
H1IB C1I H1IC 109.5 . . ?
N13 C1J H1JA 109.8 . . ?
N13 C1J H1JB 109.4 . . ?
N13 C1J H1JC 109.2 . . ?
H1JA C1J H1JB 109.5 . . ?
H1JA C1J H1JC 109.4 . . ?
H1JB C1J H1JC 109.5 . . ?
O1 C111 H111 120.9 . . ?
O1 C111 N14 118(6) . . ?
N14 C111 H111 120.9 . . ?
C111 N14 C1K 115(5) . . ?
C111 N14 C1L 125(6) . . ?
C1L N14 C1K 107(5) . . ?
N14 C1K H1KA 109.5 . . ?
N14 C1K H1KB 108.5 . . ?
N14 C1K H1KC 110.3 . . ?
H1KA C1K H1KB 109.5 . . ?
H1KA C1K H1KC 109.4 . . ?
H1KB C1K H1KC 109.5 . . ?
N14 C1L H1LA 110.0 . . ?
N14 C1L H1LB 109.6 . . ?
N14 C1L H1LC 108.8 . . ?
H1LA C1L H1LB 109.5 . . ?
H1LA C1L H1LC 109.5 . . ?
H1LB C1L H1LC 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 C1 C2 C3 0.0 . . . . ?
C1 N1 C5 C4 0.0 . . . . ?
C1 N1 C6 C7 59(2) . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 N1 0.0 . . . . ?
C5 N1 C1 C2 0.0 . . . . ?
C5 N1 C6 C7 -126.9(16) . . . . ?
N2 C14 C15 C16 0.0 . . . . ?
C14 N2 C18 C17 0.0 . . . . ?
C14 N2 C13 C10 -56(2) . . . . ?
C14 C15 C16 C17 0.0 . . . . ?
C15 C16 C17 C18 0.0 . . . . ?
C16 C17 C18 N2 0.0 . . . . ?
C18 N2 C14 C15 0.0 . . . . ?
C18 N2 C13 C10 128.4(16) . . . . ?
N3 C19 C20 C21 0.0 . . . . ?
C19 N3 C23 C22 0.0 . . . . ?
C19 N3 C24 C25 128(3) . . . . ?
C19 C20 C21 C22 0.0 . . . . ?
C20 C21 C22 C23 0.0 . . . . ?
C21 C22 C23 N3 0.0 . . . . ?
C23 N3 C19 C20 0.0 . . . . ?
C23 N3 C24 C25 -61(4) . . . . ?
N4 C36 C35 C34 0.0 . . . . ?
C36 N4 C32 C33 0.0 . . . . ?
C36 N4 C31 C28 -116(3) . . . . ?
C36 C35 C34 C33 0.0 . . . . ?
C35 C34 C33 C32 0.0 . . . . ?
C34 C33 C32 N4 0.0 . . . . ?
C32 N4 C36 C35 0.0 . . . . ?
C32 N4 C31 C28 68(4) . . . . ?
N5 C37 C38 C39 0.0 . . . . ?
C37 N5 C41 C40 0.0 . . . . ?
C37 N5 C42 C43 119(2) . . . . ?
C37 C38 C39 C40 0.0 . . . . ?
C38 C39 C40 C41 0.0 . . . . ?
C39 C40 C41 N5 0.0 . . . . ?
C41 N5 C37 C38 0.0 . . . . ?
C41 N5 C42 C43 -57(3) . . . . ?
N6 C50 C51 C52 0.0 . . . . ?
C50 N6 C54 C53 0.0 . . . . ?
C50 N6 C49 C46 72(2) . . . . ?
C50 C51 C52 C53 0.0 . . . . ?
C51 C52 C53 C54 0.0 . . . . ?
C52 C53 C54 N6 0.0 . . . . ?
C54 N6 C50 C51 0.0 . . . . ?
C54 N6 C49 C46 -112.9(19) . . . . ?
N7 C55 C56 C57 0.0 . . . . ?
C55 N7 C59 C58 0.0 . . . . ?
C55 N7 C60 C61 117.3(19) . . . . ?
C55 C56 C57 C58 0.0 . . . . ?
C56 C57 C58 C59 0.0 . . . . ?
C57 C58 C59 N7 0.0 . . . . ?
C59 N7 C55 C56 0.0 . . . . ?
C59 N7 C60 C61 -69(2) . . . . ?
N8 C68 C69 C70 0.0 . . . . ?
C68 N8 C72 C71 0.0 . . . . ?
C68 N8 C67 C64 63(3) . . . . ?
C68 C69 C70 C71 0.0 . . . . ?
C69 C70 C71 C72 0.0 . . . . ?
C70 C71 C72 N8 0.0 . . . . ?
C72 N8 C68 C69 0.0 . . . . ?
C72 N8 C67 C64 -117.3(19) . . . . ?
N9 C73 C74 C75 0.0 . . . . ?
C73 N9 C77 C76 0.0 . . . . ?
C73 N9 C78 C79 -109.8(17) . . . . ?
C73 C74 C75 C76 0.0 . . . . ?
C74 C75 C76 C77 0.0 . . . . ?
C75 C76 C77 N9 0.0 . . . . ?
C77 N9 C73 C74 0.0 . . . . ?
C77 N9 C78 C79 77(2) . . . . ?
N10 C86 C87 C88 0.0 . . . . ?
C86 N10 C90 C89 0.0 . . . . ?
C86 N10 C85 C82 -92.0(18) . . . . ?
C86 C87 C88 C89 0.0 . . . . ?
C87 C88 C89 C90 0.0 . . . . ?
C88 C89 C90 N10 0.0 . . . . ?
C90 N10 C86 C87 0.0 . . . . ?
C90 N10 C85 C82 83.8(18) . . . . ?
N12 C104 C105 C106 0.0 . . . . ?
C104 N12 C108 C107 0.0 . . . . ?
C104 N12 C103 C100 79(6) . . . . ?
C104 C105 C106 C107 0.0 . . . . ?
C105 C106 C107 C108 0.0 . . . . ?
C106 C107 C108 N12 0.0 . . . . ?
C108 N12 C104 C105 0.0 . . . . ?
C108 N12 C103 C100 -101(5) . . . . ?
C7 C8 C9 C10 0.0 . . . . ?
C8 C7 C12 C11 0.0 . . . . ?
C8 C7 C6 N1 -115.3(18) . . . . ?
C8 C9 C10 C11 0.0 . . . . ?
C8 C9 C10 C13 177(2) . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
C9 C10 C13 N2 107.7(18) . . . . ?
C10 C11 C12 C7 0.0 . . . . ?
C11 C10 C13 N2 -75(2) . . . . ?
C12 C7 C8 C9 0.0 . . . . ?
C12 C7 C6 N1 69(2) . . . . ?
C29 C30 C25 C26 0.0 . . . . ?
C29 C30 C25 C24 -177(4) . . . . ?
C29 C28 C31 N4 89(3) . . . . ?
C30 C29 C28 C27 0.0 . . . . ?
C30 C29 C28 C31 179(4) . . . . ?
C30 C25 C26 C27 0.0 . . . . ?
C30 C25 C24 N3 -81(4) . . . . ?
C25 C26 C27 C28 0.0 . . . . ?
C26 C25 C24 N3 102(3) . . . . ?
C26 C27 C28 C29 0.0 . . . . ?
C26 C27 C28 C31 -179(4) . . . . ?
C27 C28 C31 N4 -92(3) . . . . ?
C28 C29 C30 C25 0.0 . . . . ?
C43 C44 C45 C46 0.0 . . . . ?
C44 C43 C48 C47 0.0 . . . . ?
C44 C43 C42 N5 -62(3) . . . . ?
C44 C45 C46 C47 0.0 . . . . ?
C44 C45 C46 C49 171(3) . . . . ?
C45 C46 C47 C48 0.0 . . . . ?
C45 C46 C49 N6 54(3) . . . . ?
C46 C47 C48 C43 0.0 . . . . ?
C47 C46 C49 N6 -135.4(18) . . . . ?
C48 C43 C44 C45 0.0 . . . . ?
C48 C43 C42 N5 119(2) . . . . ?
C61 C62 C63 C64 0.0 . . . . ?
C62 C61 C66 C65 0.0 . . . . ?
C62 C61 C60 N7 122.6(19) . . . . ?
C62 C63 C64 C65 0.0 . . . . ?
C62 C63 C64 C67 -174(2) . . . . ?
C63 C64 C65 C66 0.0 . . . . ?
C63 C64 C67 N8 -131.5(18) . . . . ?
C64 C65 C66 C61 0.0 . . . . ?
C65 C64 C67 N8 55(3) . . . . ?
C66 C61 C62 C63 0.0 . . . . ?
C66 C61 C60 N7 -65(2) . . . . ?
C79 C80 C81 C82 0.0 . . . . ?
C80 C79 C84 C83 0.0 . . . . ?
C80 C79 C78 N9 39(2) . . . . ?
C80 C81 C82 C83 0.0 . . . . ?
C80 C81 C82 C85 -177(2) . . . . ?
C81 C82 C83 C84 0.0 . . . . ?
C81 C82 C85 N10 -115.0(15) . . . . ?
C82 C83 C84 C79 0.0 . . . . ?
C83 C82 C85 N10 67.5(19) . . . . ?
C84 C79 C80 C81 0.0 . . . . ?
C84 C79 C78 N9 -156.6(14) . . . . ?
C92 C91 N11 C95 0.0 . . . . ?
C92 C91 N11 C96 -179(4) . . . . ?
C91 C92 C93 C94 0.0 . . . . ?
C91 N11 C95 C94 0.0 . . . . ?
C91 N11 C96 C97 -86(4) . . . . ?
N11 C95 C94 C93 0.0 . . . . ?
C95 N11 C96 C97 95(4) . . . . ?
C95 C94 C93 C92 0.0 . . . . ?
C93 C92 C91 N11 0.0 . . . . ?
C102 C97 C98 C99 0.0 . . . . ?
C102 C97 C96 N11 65(4) . . . . ?
C97 C102 C101 C100 0.0 . . . . ?
C97 C98 C99 C100 0.0 . . . . ?
C98 C97 C96 N11 -118(4) . . . . ?
C98 C99 C100 C101 0.0 . . . . ?
C98 C99 C100 C103 165(6) . . . . ?
C99 C100 C101 C102 0.0 . . . . ?
C99 C100 C103 N12 42(6) . . . . ?
C101 C102 C97 C98 0.0 . . . . ?
C101 C102 C97 C96 176(6) . . . . ?
C101 C100 C103 N12 -153(3) . . . . ?
C6 N1 C1 C2 174(2) . . . . ?
C6 N1 C5 C4 -174(2) . . . . ?
C6 C7 C8 C9 -176(2) . . . . ?
C6 C7 C12 C11 176(2) . . . . ?
C13 N2 C14 C15 -176(2) . . . . ?
C13 N2 C18 C17 176(2) . . . . ?
C13 C10 C11 C12 -177(2) . . . . ?
C24 N3 C19 C20 170(4) . . . . ?
C24 N3 C23 C22 -170(4) . . . . ?
C24 C25 C26 C27 177(4) . . . . ?
C31 N4 C36 C35 -177(4) . . . . ?
C31 N4 C32 C33 177(4) . . . . ?
C42 N5 C37 C38 -176(3) . . . . ?
C42 N5 C41 C40 176(3) . . . . ?
C42 C43 C44 C45 -179(3) . . . . ?
C42 C43 C48 C47 179(3) . . . . ?
C49 N6 C50 C51 175(2) . . . . ?
C49 N6 C54 C53 -175(2) . . . . ?
C49 C46 C47 C48 -171(3) . . . . ?
C60 N7 C55 C56 174(2) . . . . ?
C60 N7 C59 C58 -174(2) . . . . ?
C60 C61 C62 C63 172(2) . . . . ?
C60 C61 C66 C65 -172(2) . . . . ?
C67 N8 C68 C69 180(2) . . . . ?
C67 N8 C72 C71 -180(2) . . . . ?
C67 C64 C65 C66 174(2) . . . . ?
C78 N9 C73 C74 -173.7(18) . . . . ?
C78 N9 C77 C76 173.4(19) . . . . ?
C78 C79 C80 C81 163(2) . . . . ?
C78 C79 C84 C83 -164.9(19) . . . . ?
C85 N10 C86 C87 176(2) . . . . ?
C85 N10 C90 C89 -175.9(19) . . . . ?
C85 C82 C83 C84 177(2) . . . . ?
C96 N11 C95 C94 179(4) . . . . ?
C96 C97 C98 C99 -176(6) . . . . ?
C103 N12 C104 C105 -180(6) . . . . ?
C103 N12 C108 C107 180(6) . . . . ?
C103 C100 C101 C102 -166(6) . . . . ?
C202 N201 C201 O201 0.00(5) . . . . ?
C203 N201 C201 O201 180.00(5) . . . . ?
C212 N211 C211 O211 180.00(5) . . . . ?
C213 N211 C211 O211 0.00(5) . . . . ?
C222 N221 C221 O221 180.00(5) . . . . ?
C223 N221 C221 O221 0.00(5) . . . . ?
C232 N231 C231 O231 180.00(6) . . . . ?
C233 N231 C231 O231 0.00(5) . . . . ?
C24A N3A C19A C20A -177(4) . . . . ?
C24A N3A C23A C22A 177(4) . . . . ?
C24A C25A C26A C27A -175(4) . . . . ?
N3A C24A C25A C30A 69(4) . . . . ?
N3A C24A C25A C26A -116(3) . . . . ?
N3A C19A C20A C21A 0.0 . . . . ?
C19A N3A C23A C22A 0.0 . . . . ?
C19A C20A C21A C22A 0.0 . . . . ?
C20A C21A C22A C23A 0.0 . . . . ?
C21A C22A C23A N3A 0.0 . . . . ?
C23A N3A C19A C20A 0.0 . . . . ?
C29A C30A C25A C24A 175(4) . . . . ?
C29A C30A C25A C26A 0.0 . . . . ?
C29A C28A C31A N4A -63(4) . . . . ?
C30A C29A C28A C27A 0.0 . . . . ?
C30A C29A C28A C31A -178(4) . . . . ?
C30A C25A C26A C27A 0.0 . . . . ?
C25A C24A N3A C19A -129(3) . . . . ?
C25A C24A N3A C23A 54(5) . . . . ?
C25A C26A C27A C28A 0.0 . . . . ?
C26A C27A C28A C29A 0.0 . . . . ?
C26A C27A C28A C31A 178(4) . . . . ?
C27A C28A C31A N4A 119(3) . . . . ?
C28A C29A C30A C25A 0.0 . . . . ?
C28A C31A N4A C36A 121(3) . . . . ?
C28A C31A N4A C32A -63(4) . . . . ?
C31A N4A C36A C35A 175(4) . . . . ?
C31A N4A C32A C33A -176(4) . . . . ?
N4A C36A C35A C34A 0.0 . . . . ?
C36A N4A C32A C33A 0.0 . . . . ?
C36A C35A C34A C33A 0.0 . . . . ?
C35A C34A C33A C32A 0.0 . . . . ?
C34A C33A C32A N4A 0.0 . . . . ?
C32A N4A C36A C35A 0.0 . . . . ?
C109 C97A C98A C99A 0.0 . . . . ?
C109 C97A C96A N11A 120(4) . . . . ?
C97A C109 C1H C1F 0.0 . . . . ?
C97A C98A C99A C1F 0.0 . . . . ?
C97A C96A N11A C91A -80(5) . . . . ?
C97A C96A N11A C95A 107(4) . . . . ?
C98A C97A C96A N11A -75(5) . . . . ?
C98A C99A C1F C1H 0.0 . . . . ?
C98A C99A C1F C1C 163(5) . . . . ?
C99A C1F C1H C109 0.0 . . . . ?
C99A C1F C1C N12A 103(5) . . . . ?
C1H C109 C97A C98A 0.0 . . . . ?
C1H C109 C97A C96A 165(5) . . . . ?
C1H C1F C1C N12A -93(5) . . . . ?
N12A C1A C1D C1G 0.0 . . . . ?
C1A N12A C1B C1E 0.0 . . . . ?
C1A N12A C1C C1F 109(5) . . . . ?
C1A C1D C1G C1E 0.0 . . . . ?
C1D C1G C1E C1B 0.0 . . . . ?
C1G C1E C1B N12A 0.0 . . . . ?
C1B N12A C1A C1D 0.0 . . . . ?
C1B N12A C1C C1F -67(5) . . . . ?
C1C C1F C1H C109 -165(5) . . . . ?
C1C N12A C1A C1D -175(6) . . . . ?
C1C N12A C1B C1E 176(5) . . . . ?
C96A C97A C98A C99A -164(6) . . . . ?
C96A N11A C95A C94A 174(5) . . . . ?
C92A C91A N11A C96A -174(5) . . . . ?
C92A C91A N11A C95A 0.0 . . . . ?
C91A C92A C93A C94A 0.0 . . . . ?
C91A N11A C95A C94A 0.0 . . . . ?
N11A C95A C94A C93A 0.0 . . . . ?
C95A C94A C93A C92A 0.0 . . . . ?
C93A C92A C91A N11A 0.0 . . . . ?
O2 C110 N13 C1I 0(14) . . . . ?
O2 C110 N13 C1J 167(11) . . . . ?
O1 C111 N14 C1K 46(17) . . . . ?
O1 C111 N14 C1L -179(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.49742
2 0.50258

_vrf_PLAT972_kotov143            
;
PROBLEM: Large negative calculated residual density near bismuth atoms.
RESPONSE: The problem is related to the very strong absorption of the 
crystalline samples. All checked crystals were twins.
;
_vrf_PLAT971_kotov143            
;
PROBLEM: Large positive calculated residual density near bismuth atoms.
RESPONSE: The problem is related to the strong absorption of the 
crystalline samples. All checked crystals were twins.
;
_vrf_PLAT342_kotov143            
;
PROBLEM: Low Bond Precision on C-C Bonds. 
RESPONSE: The problem is related to the strong absorption of the 
crystalline samples. All checked crystals were twins.
;
####################################################################### 
# 
# 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_shelx_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 2341098'
loop_
_audit_author_name
_audit_author_address
'Petr Buikin'
;N S Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-05-22 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_audit_creation_date             2024-05-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi I6, I, 2(C18 H18 N2), 3[C3NOH7]'
_chemical_formula_sum            'C45 H57 Bi I7 N7 O3'
_chemical_formula_weight         1841.25
_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 0.0033 0.0016 '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'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   17.3495(14)
_cell_length_b                   14.7084(12)
_cell_length_c                   13.8354(11)
_cell_angle_alpha                90
_cell_angle_beta                 121.690(2)
_cell_angle_gamma                90
_cell_volume                     3004.2(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9992
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.97
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   0.694
_shelx_estimated_absorpt_T_min   0.506
_exptl_absorpt_coefficient_mu    6.571
_exptl_absorpt_correction_T_max  0.182
_exptl_absorpt_correction_T_min  0.032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.035
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1708
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 0.71065   17.348   14.716   13.824   90.004  121.680   90.007
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20006
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_min         2.365
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker AXS D8 VENTURE PHOTON III C14 IuS 3.0'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3189
_reflns_number_total             3441
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.427
_refine_diff_density_min         -0.713
_refine_diff_density_rms         0.138
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         3441
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0417
_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)+(0.0731P)²+8.7703P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1213
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C13-C1 \\sim C12-C1
 with sigma of 0.02
 C8-C00A \\sim C7-C00A
 with sigma of 0.02
 C2A-C007 \\sim C4A-C007
 with sigma of 0.02
 C2-C0 \\sim C4-C0
 with sigma of 0.02
 C1-C007 \\sim C00A-C0
 with sigma of 0.02
 N0-C00A \\sim N1-C1
 with sigma of 0.02
 Bi01-I005 \\sim Bi01-I1
 with sigma of 0.02
 C4A-C2A_$1 \\sim C2A_$1-C007_$1 \\sim C4A_$1-C007_$1 \\sim C4A_$1-C2A
 with sigma of 0.02
 C2-C0 \\sim C4_$1-C2 \\sim C4-C0 \\sim C4-C2_$1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C0) = Uanis(C007)
Uanis(C4) = Uanis(C4A)
Uanis(C2A) = Uanis(C2)
Uanis(N0) = Uanis(N1)
Uanis(C8) = Uanis(C13)
Uanis(C3) = Uanis(C9)
Uanis(C5) = Uanis(C10)
Uanis(C11) = Uanis(C6)
Uanis(C7) = Uanis(C12)
Uanis(C4A) = Uanis(C4)
Uanis(C2) = Uanis(C2A)
Uanis(C1) = Uanis(C00A)
Uanis(C007) = Uanis(C0)
4. Others
 Sof(I0)=0.5*(1-FVAR(2))
 Sof(I004)=0.5*FVAR(2)
 Sof(I1)=0.5*(1-FVAR(3))
 Sof(I005)=0.5*FVAR(3)
 Fixed Sof: C007(0.5) C00A(0.5) H00A(0.5) H00B(0.5) C8(0.5) H8(0.5) C3(0.5)
 H3(0.5) C5(0.5) H5(0.5) C6(0.5) H6(0.5) C7(0.5) H7(0.5) N0(0.5) C2(0.5)
 H2(0.5) C4(0.5) H4(0.5) C2A(0.5) H2A(0.5) C4A(0.5) H4A(0.5) C0(0.5) C1(0.5)
 H1A(0.5) H1B(0.5) C13(0.5) H13(0.5) C9(0.5) H9(0.5) C10(0.5) H10(0.5) C11(0.5)
 H11(0.5) C12(0.5) H12(0.5) N1(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B), C1(H1A,H1B)
5.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C3(H3), C5(H5), C6(H6), C7(H7), C2(H2), C4(H4), C2A(H2A), C4A(H4A),
 C13(H13), C9(H9), C10(H10), C11(H11), C12(H12)
5.c Fitted hexagon refined as free rotating group:
 C8(C3,C5,C6,C7,N0), C13(C9,C10,C11,C12,N1)
;
_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
Bi01 Bi 0.5000 0.5000 0.5000 0.06295(16) Uani 1 4 d DS T P . .
I002 I 0.29794(3) 0.5000 0.42742(4) 0.06502(17) Uani 1 2 d S T P A .
I003 I 0.0000 0.5000 0.0000 0.0857(3) Uani 1 4 d S T P . .
I004 I 0.5000 0.7037(6) 0.5000 0.064(2) Uani 0.38(4) 2 d S T P A 1
I005 I 0.4476(2) 0.5000 0.2512(4) 0.062(4) Uani 0.34(6) 2 d DS T P A 1
C007 C 0.2472(18) 0.705(3) 0.081(2) 0.079(3) Uani 0.5 1 d D . P B 1
C00A C 0.2526(10) 0.6569(12) 0.1937(12) 0.070(4) Uani 0.5 1 d D . P C 2
H00A H 0.2237 0.5962 0.1725 0.084 Uiso 0.5 1 calc R U P C 2
H00B H 0.3178 0.6485 0.2512 0.084 Uiso 0.5 1 calc R U P C 2
C8 C 0.2497(7) 0.7941(7) 0.2942(10) 0.083(3) Uani 0.5 1 d DG . P C 2
H8 H 0.3017 0.8160 0.2954 0.100 Uiso 0.5 1 calc R U P C 2
C3 C 0.2127(8) 0.8442(6) 0.3454(10) 0.088(3) Uani 0.5 1 d G . P C 2
H3 H 0.2394 0.9003 0.3815 0.106 Uiso 0.5 1 calc R U P C 2
C5 C 0.1366(9) 0.8122(9) 0.3437(11) 0.095(2) Uani 0.5 1 d G . P C 2
H5 H 0.1114 0.8464 0.3787 0.114 Uiso 0.5 1 calc R U P C 2
C6 C 0.0975(7) 0.7301(9) 0.2908(12) 0.099(6) Uani 0.5 1 d G . P C 2
H6 H 0.0455 0.7082 0.2897 0.119 Uiso 0.5 1 calc R U P C 2
C7 C 0.1345(7) 0.6800(7) 0.2397(11) 0.095(5) Uani 0.5 1 d DG . P C 2
H7 H 0.1078 0.6239 0.2036 0.114 Uiso 0.5 1 calc R U P C 2
N0 N 0.2106(7) 0.7120(7) 0.2414(10) 0.0692(19) Uani 0.5 1 d DG . P C 2
C2 C 0.1678(15) 0.7473(13) -0.0086(16) 0.110(4) Uani 0.5 1 d D . P C 2
H2 H 0.1121 0.7513 -0.0112 0.132 Uiso 0.5 1 calc R U P C 2
C4 C 0.330(2) 0.715(2) 0.103(3) 0.126(7) Uani 0.5 1 d D . P C 2
H4 H 0.3834 0.6975 0.1717 0.151 Uiso 0.5 1 calc R U P C 2
C2A C 0.1779(15) 0.6986(13) -0.0243(17) 0.110(4) Uani 0.5 1 d D . P B 1
H2A H 0.1253 0.6650 -0.0421 0.132 Uiso 0.5 1 calc R U P B 1
C4A C 0.316(2) 0.7591(19) 0.105(3) 0.126(7) Uani 0.5 1 d D . P B 1
H4A H 0.3618 0.7682 0.1822 0.151 Uiso 0.5 1 calc R U P B 1
C0 C 0.2419(16) 0.704(3) 0.089(2) 0.079(3) Uani 0.5 1 d D . P C 2
C1 C 0.2169(10) 0.6499(13) 0.1493(11) 0.070(4) Uani 0.5 1 d D . P B 1
H1A H 0.1641 0.6121 0.0964 0.084 Uiso 0.5 1 calc R U P B 1
H1B H 0.2666 0.6083 0.2012 0.084 Uiso 0.5 1 calc R U P B 1
C13 C 0.2604(5) 0.7482(7) 0.3146(9) 0.083(3) Uani 0.5 1 d DG . P B 1
H13 H 0.3222 0.7399 0.3382 0.100 Uiso 0.5 1 calc R U P B 1
C9 C 0.2378(7) 0.8017(8) 0.3789(8) 0.088(3) Uani 0.5 1 d G . P B 1
H9 H 0.2841 0.8300 0.4464 0.106 Uiso 0.5 1 calc R U P B 1
C10 C 0.1474(8) 0.8138(9) 0.3445(10) 0.095(2) Uani 0.5 1 d G . P B 1
H10 H 0.1319 0.8504 0.3884 0.114 Uiso 0.5 1 calc R U P B 1
C11 C 0.0796(6) 0.7724(10) 0.2457(11) 0.099(6) Uani 0.5 1 d G . P B 1
H11 H 0.0179 0.7807 0.2222 0.119 Uiso 0.5 1 calc R U P B 1
C12 C 0.1023(6) 0.7189(9) 0.1814(9) 0.095(5) Uani 0.5 1 d DG . P B 1
H12 H 0.0560 0.6906 0.1139 0.114 Uiso 0.5 1 calc R U P B 1
N1 N 0.1926(7) 0.7068(7) 0.2158(9) 0.0692(19) Uani 0.5 1 d DG . P B 1
I0 I 0.4886(3) 0.7141(6) 0.4751(10) 0.0761(10) Uani 0.31(2) 1 d . . P A 2
I1 I 0.4469(2) 0.5183(5) 0.2549(4) 0.0842(16) Uani 0.33(3) 1 d D . P A 2


_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
Bi01 I002 3.0983(6) . ?
Bi01 I002 3.0984(6) 5_666 ?
Bi01 I004 2.997(9) . ?
Bi01 I004 2.997(9) 5_666 ?
Bi01 I005 3.064(5) . ?
Bi01 I005 3.064(5) 5_666 ?
Bi01 I0 3.163(9) 6_565 ?
Bi01 I0 3.163(9) . ?
Bi01 I1 3.023(5) 6_565 ?
Bi01 I1 3.023(5) . ?
Bi01 I1 3.023(5) 5_666 ?
Bi01 I1 3.023(5) 2_656 ?
C007 C2A 1.319(18) . ?
C007 C4A 1.319(18) . ?
C007 C1 1.530(14) . ?
C00A H00A 0.9900 . ?
C00A H00B 0.9900 . ?
C00A N0 1.459(12) . ?
C00A C0 1.531(14) . ?
C8 H8 0.9500 . ?
C8 C3 1.3900 . ?
C8 N0 1.3900 . ?
C3 H3 0.9500 . ?
C3 C5 1.3900 . ?
C5 H5 0.9500 . ?
C5 C6 1.3900 . ?
C6 H6 0.9500 . ?
C6 C7 1.3900 . ?
C7 H7 0.9500 . ?
C7 N0 1.3900 . ?
C2 H2 0.9500 . ?
C2 C4 1.446(16) 7_565 ?
C2 C0 1.433(18) . ?
C4 C2 1.446(16) 7_565 ?
C4 H4 0.9500 . ?
C4 C0 1.434(18) . ?
C2A H2A 0.9500 . ?
C2A C4A 1.334(17) 7_565 ?
C4A C2A 1.334(17) 7_565 ?
C4A H4A 0.9500 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 N1 1.461(12) . ?
C13 H13 0.9500 . ?
C13 C9 1.3900 . ?
C13 N1 1.3900 . ?
C9 H9 0.9500 . ?
C9 C10 1.3900 . ?
C10 H10 0.9500 . ?
C10 C11 1.3900 . ?
C11 H11 0.9500 . ?
C11 C12 1.3900 . ?
C12 H12 0.9500 . ?
C12 N1 1.3900 . ?
I0 I0 0.59(2) 2_656 ?
I1 I1 0.539(16) 6_565 ?

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
I002 Bi01 I002 180.0 . 5_666 ?
I002 Bi01 I0 91.75(9) 5_666 6_565 ?
I002 Bi01 I0 91.75(9) 5_666 . ?
I002 Bi01 I0 88.25(9) . 6_565 ?
I002 Bi01 I0 88.25(9) . . ?
I004 Bi01 I002 90.000(1) 5_666 . ?
I004 Bi01 I002 90.000(1) 5_666 5_666 ?
I004 Bi01 I002 90.000(1) . 5_666 ?
I004 Bi01 I002 90.000(1) . . ?
I004 Bi01 I004 180.0 . 5_666 ?
I004 Bi01 I005 90.0 . 5_666 ?
I004 Bi01 I005 90.0 . . ?
I004 Bi01 I005 90.000(1) 5_666 . ?
I004 Bi01 I005 90.000(1) 5_666 5_666 ?
I005 Bi01 I002 88.95(7) 5_666 . ?
I005 Bi01 I002 88.95(7) . 5_666 ?
I005 Bi01 I002 91.05(7) 5_666 5_666 ?
I005 Bi01 I002 91.05(7) . . ?
I005 Bi01 I005 180.0 5_666 . ?
I0 Bi01 I0 169.4(4) . 6_565 ?
I1 Bi01 I002 90.58(7) 6_565 . ?
I1 Bi01 I002 89.42(7) . 5_666 ?
I1 Bi01 I002 90.58(7) 5_666 5_666 ?
I1 Bi01 I002 89.42(7) 2_656 . ?
I1 Bi01 I002 89.42(7) 6_565 5_666 ?
I1 Bi01 I002 90.58(7) . . ?
I1 Bi01 I002 90.58(7) 2_656 5_666 ?
I1 Bi01 I002 89.42(7) 5_666 . ?
I1 Bi01 I0 89.9(3) 2_656 . ?
I1 Bi01 I0 89.9(3) 5_666 6_565 ?
I1 Bi01 I0 79.9(3) 6_565 6_565 ?
I1 Bi01 I0 79.9(3) . . ?
I1 Bi01 I0 100.1(3) 2_656 6_565 ?
I1 Bi01 I0 90.1(3) . 6_565 ?
I1 Bi01 I0 90.1(3) 6_565 . ?
I1 Bi01 I0 100.1(3) 5_666 . ?
I1 Bi01 I1 10.2(3) 2_656 5_666 ?
I1 Bi01 I1 169.8(3) 6_565 5_666 ?
I1 Bi01 I1 10.2(3) 6_565 . ?
I1 Bi01 I1 169.8(3) 2_656 . ?
I1 Bi01 I1 180.0 5_666 . ?
I1 Bi01 I1 180.0 6_565 2_656 ?
C2A C007 C4A 120(2) . . ?
C2A C007 C1 103.6(18) . . ?
C4A C007 C1 136(2) . . ?
H00A C00A H00B 108.2 . . ?
N0 C00A H00A 109.7 . . ?
N0 C00A H00B 109.7 . . ?
N0 C00A C0 110(2) . . ?
C0 C00A H00A 109.7 . . ?
C0 C00A H00B 109.7 . . ?
C3 C8 H8 120.0 . . ?
C3 C8 N0 120.0 . . ?
N0 C8 H8 120.0 . . ?
C8 C3 H3 120.0 . . ?
C8 C3 C5 120.0 . . ?
C5 C3 H3 120.0 . . ?
C3 C5 H5 120.0 . . ?
C6 C5 C3 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 120.0 . . ?
N0 C7 C6 120.0 . . ?
N0 C7 H7 120.0 . . ?
C8 N0 C00A 119.9(7) . . ?
C7 N0 C00A 120.0(7) . . ?
C7 N0 C8 120.0 . . ?
C4 C2 H2 117.2 7_565 . ?
C0 C2 H2 117.2 . . ?
C0 C2 C4 125.7(15) . 7_565 ?
C2 C4 H4 121.6 7_565 . ?
C0 C4 C2 117(2) . 7_565 ?
C0 C4 H4 121.6 . . ?
C007 C2A H2A 121.2 . . ?
C007 C2A C4A 118(2) . 7_565 ?
C4A C2A H2A 121.2 7_565 . ?
C007 C4A C2A 122(3) . 7_565 ?
C007 C4A H4A 118.9 . . ?
C2A C4A H4A 118.9 7_565 . ?
C2 C0 C00A 134.0(19) . . ?
C2 C0 C4 116.5(17) . . ?
C4 C0 C00A 109.0(18) . . ?
C007 C1 H1A 109.0 . . ?
C007 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
N1 C1 C007 113(2) . . ?
N1 C1 H1A 109.0 . . ?
N1 C1 H1B 109.0 . . ?
C9 C13 H13 120.0 . . ?
C9 C13 N1 120.0 . . ?
N1 C13 H13 120.0 . . ?
C13 C9 H9 120.0 . . ?
C13 C9 C10 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 120.0 . . ?
N1 C12 C11 120.0 . . ?
N1 C12 H12 120.0 . . ?
C13 N1 C1 119.7(6) . . ?
C12 N1 C1 120.3(6) . . ?
C12 N1 C13 120.0 . . ?
I0 I0 Bi01 84.68(19) 2_656 . ?
I1 I1 Bi01 84.88(16) 6_565 . ?

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
C007 C1 N1 C13 -75.0(15) . . . . ?
C007 C1 N1 C12 105.6(15) . . . . ?
C8 C3 C5 C6 0.0 . . . . ?
C3 C8 N0 C00A -176.3(12) . . . . ?
C3 C8 N0 C7 0.0 . . . . ?
C3 C5 C6 C7 0.0 . . . . ?
C5 C6 C7 N0 0.0 . . . . ?
C6 C7 N0 C00A 176.3(12) . . . . ?
C6 C7 N0 C8 0.0 . . . . ?
N0 C00A C0 C2 -46(5) . . . . ?
N0 C00A C0 C4 125(3) . . . . ?
N0 C8 C3 C5 0.0 . . . . ?
C2 C4 C0 C00A 176(3) 7_565 . . . ?
C2 C4 C0 C2 -11(5) 7_565 . . . ?
C4 C2 C0 C00A -177(4) 7_565 . . . ?
C4 C2 C0 C4 12(6) 7_565 . . . ?
C2A C007 C4A C2A -7(6) . . . 7_565 ?
C2A C007 C1 N1 -106(3) . . . . ?
C4A C007 C2A C4A 6(5) . . . 7_565 ?
C4A C007 C1 N1 66(5) . . . . ?
C0 C00A N0 C8 -70.0(17) . . . . ?
C0 C00A N0 C7 113.7(17) . . . . ?
C1 C007 C2A C4A 180(2) . . . 7_565 ?
C1 C007 C4A C2A -178(4) . . . 7_565 ?
C13 C9 C10 C11 0.0 . . . . ?
C9 C13 N1 C1 -179.4(12) . . . . ?
C9 C13 N1 C12 0.0 . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
C10 C11 C12 N1 0.0 . . . . ?
C11 C12 N1 C1 179.4(13) . . . . ?
C11 C12 N1 C13 0.0 . . . . ?
N1 C13 C9 C10 0.0 . . . . ?

_smtbx_masks_special_details     
;
A solvent mask was calculated and 250 electrons were 
found in a volume of 882Å³ in 1 void per unit cell. 
This is consistent with the presence of 
3[C3NOH7] per formula unit 
which account for 240 electrons 
per unit cell.
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.661 0.000 -0.661 440.8 125.4 '3 C3NOH7'
2 -0.814 0.500 -0.314 440.8 125.4 '3 C3NOH7'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
