# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2064474'
loop_
_audit_author_name
_audit_author_address
'Andrey Ilyukhin'
;Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2021-02-22 deposited with the CCDC.	2021-08-31 downloaded from the CCDC.
;

_audit_creation_date             2018-11-19T22:52:57-00:00
_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, Bi Br5'
_chemical_formula_sum            'C18 H18 Bi Br5 N2'
_chemical_formula_weight         870.87
_chemical_absolute_configuration unk

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

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'I 4'
_symmetry_space_group_name_Hall  'I 4'
_symmetry_Int_Tables_number      79
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-y, x, z'
'y, -x, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-y+1/2, x+1/2, z+1/2'
'y+1/2, -x+1/2, z+1/2'

_cell_length_a                   12.890(2)
_cell_length_b                   12.890(2)
_cell_length_c                   13.861(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2303.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5313
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      32.89

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

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    2.512
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1592
_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 0.71073   12.934   12.907   13.904   89.980   89.910   90.022
;

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

_exptl_absorpt_coefficient_mu    16.336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_T_min  0.0123
_exptl_absorpt_correction_T_max  0.0551

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

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_number            16399
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.158
_diffrn_reflns_theta_max         31.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     1
_reflns_Friedel_coverage         0.93
_reflns_number_total             3837
_reflns_number_gt                3570
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0300P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3837
_refine_ls_number_parameters     122
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0276
_refine_ls_wR_factor_ref         0.0657
_refine_ls_wR_factor_gt          0.0641
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.466(9)
_refine_diff_density_max         2.487
_refine_diff_density_min         -1.088
_refine_diff_density_rms         0.162

#----------------------------------------------------------------------------#
#                   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'
N N 0.0061 0.0033 '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'
Bi Bi -4.1077 10.2566 '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
Bi1 Bi 0.5 0.5 0.32216(3) 0.02065(11) Uani 1 4 d S T P . .
Bi2 Bi 0.5 0.5 -0.12255(3) 0.02317(13) Uani 1 4 d S T P . .
Br1 Br 0.28247(5) 0.46430(5) 0.32020(5) 0.02253(13) Uani 1 1 d . . . . .
Br2 Br 0.5 0.5 0.51707(11) 0.0249(3) Uani 1 4 d S T P . .
Br3 Br 0.28477(6) 0.46369(6) -0.15012(5) 0.02612(17) Uani 1 1 d . . . . .
Br4 Br 0.5 0.5 0.07165(12) 0.0376(4) Uani 1 4 d S T P . .
N1 N 0.6479(4) 0.7543(3) 0.5857(4) 0.0196(10) Uani 1 1 d . . . . .
C1 C 0.6962(7) 0.7459(6) 0.5004(4) 0.0235(16) Uani 1 1 d . . . . .
H1A H 0.657795 0.74728 0.441878 0.028 Uiso 1 1 calc R U . . .
C2 C 0.8057(7) 0.7351(7) 0.4990(5) 0.0291(18) Uani 1 1 d . . . . .
H2A H 0.841438 0.729459 0.43928 0.035 Uiso 1 1 calc R U . . .
C3 C 0.8596(5) 0.7327(5) 0.5840(6) 0.0291(15) Uani 1 1 d . . . . .
H3A H 0.933125 0.727481 0.583772 0.035 Uiso 1 1 calc R U . . .
C4 C 0.8055(7) 0.7379(7) 0.6712(6) 0.0325(19) Uani 1 1 d . . . . .
H4A H 0.8415 0.734022 0.730888 0.039 Uiso 1 1 calc R U . . .
C5 C 0.7001(7) 0.7486(6) 0.6693(5) 0.0292(17) Uani 1 1 d . . . . .
H5A H 0.662915 0.752166 0.728422 0.035 Uiso 1 1 calc R U . . .
C6 C 0.5349(4) 0.7767(4) 0.5862(6) 0.0215(11) Uani 1 1 d . . . . .
H6A H 0.502558 0.745644 0.644211 0.026 Uiso 1 1 calc R U . . .
H6B H 0.501977 0.745606 0.528502 0.026 Uiso 1 1 calc R U . . .
C7 C 0.5174(4) 0.8934(4) 0.5862(5) 0.0189(10) Uani 1 1 d . . . . .
C8 C 0.5086(6) 0.9459(6) 0.4992(4) 0.0206(14) Uani 1 1 d . . . . .
H8A H 0.514165 0.909302 0.439966 0.025 Uiso 1 1 calc R U . . .
C9 C 0.5087(5) 0.9463(6) 0.6727(4) 0.0217(14) Uani 1 1 d . . . . .
H9A H 0.514515 0.90991 0.732008 0.026 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
Bi1 Br2 2.7017(17) . ?
Bi1 Br1 2.8416(8) 2_665 ?
Bi1 Br1 2.8416(8) 3_655 ?
Bi1 Br1 2.8416(8) . ?
Bi1 Br1 2.8416(8) 4_565 ?
Bi2 Br4 2.6918(18) . ?
Bi2 Br3 2.8394(9) . ?
Bi2 Br3 2.8394(9) 3_655 ?
Bi2 Br3 2.8394(9) 2_665 ?
Bi2 Br3 2.8394(9) 4_565 ?
N1 C1 1.341(8) . ?
N1 C5 1.341(9) . ?
N1 C6 1.486(7) . ?
C1 C2 1.418(13) . ?
C1 H1A 0.95 . ?
C2 C3 1.369(12) . ?
C2 H2A 0.95 . ?
C3 C4 1.396(12) . ?
C3 H3A 0.95 . ?
C4 C5 1.367(14) . ?
C4 H4A 0.95 . ?
C5 H5A 0.95 . ?
C6 C7 1.521(7) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C7 C9 1.383(9) . ?
C7 C8 1.388(9) . ?
C8 C8 1.411(15) 2_675 ?
C8 H8A 0.95 . ?
C9 C9 1.402(15) 2_675 ?
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
Br2 Bi1 Br1 90.548(17) . 2_665 ?
Br2 Bi1 Br1 90.548(16) . 3_655 ?
Br1 Bi1 Br1 90 2_665 3_655 ?
Br2 Bi1 Br1 90.548(16) . . ?
Br1 Bi1 Br1 178.90(3) 2_665 . ?
Br1 Bi1 Br1 90 3_655 . ?
Br2 Bi1 Br1 90.548(16) . 4_565 ?
Br1 Bi1 Br1 90 2_665 4_565 ?
Br1 Bi1 Br1 178.90(3) 3_655 4_565 ?
Br1 Bi1 Br1 90 . 4_565 ?
Br4 Bi2 Br3 97.736(18) . . ?
Br4 Bi2 Br3 97.737(18) . 3_655 ?
Br3 Bi2 Br3 88.962(5) . 3_655 ?
Br4 Bi2 Br3 97.737(18) . 2_665 ?
Br3 Bi2 Br3 164.53(4) . 2_665 ?
Br3 Bi2 Br3 88.962(5) 3_655 2_665 ?
Br4 Bi2 Br3 97.737(18) . 4_565 ?
Br3 Bi2 Br3 88.961(5) . 4_565 ?
Br3 Bi2 Br3 164.53(4) 3_655 4_565 ?
Br3 Bi2 Br3 88.962(5) 2_665 4_565 ?
C1 N1 C5 121.7(5) . . ?
C1 N1 C6 118.4(6) . . ?
C5 N1 C6 119.9(6) . . ?
N1 C1 C2 118.8(7) . . ?
N1 C1 H1A 120.6 . . ?
C2 C1 H1A 120.6 . . ?
C3 C2 C1 119.7(7) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C2 C3 C4 119.4(6) . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 H3A 120.3 . . ?
C5 C4 C3 119.0(7) . . ?
C5 C4 H4A 120.5 . . ?
C3 C4 H4A 120.5 . . ?
N1 C5 C4 121.3(7) . . ?
N1 C5 H5A 119.3 . . ?
C4 C5 H5A 119.3 . . ?
N1 C6 C7 109.8(4) . . ?
N1 C6 H6A 109.7 . . ?
C7 C6 H6A 109.7 . . ?
N1 C6 H6B 109.7 . . ?
C7 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C9 C7 C8 120.4(5) . . ?
C9 C7 C6 120.0(6) . . ?
C8 C7 C6 119.6(6) . . ?
C7 C8 C8 119.6(4) . 2_675 ?
C7 C8 H8A 120.2 . . ?
C8 C8 H8A 120.2 2_675 . ?
C7 C9 C9 120.0(4) . 2_675 ?
C7 C9 H9A 120 . . ?
C9 C9 H9A 120 2_675 . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1A Br1 0.95 3.04 3.912(8) 154.2 4_565 yes
C2 H2A Br3 0.95 2.89 3.677(9) 140.9 7_655 yes
C4 H4A Br1 0.95 2.86 3.661(8) 142.4 7_655 yes
C5 H5A Br3 0.95 3.11 3.966(9) 151.2 4_566 yes
C6 H6A Br3 0.99 2.92 3.851(7) 156.8 4_566 yes
C6 H6B Br1 0.99 2.95 3.874(8) 155.6 4_565 yes

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 2064477'
loop_
_audit_author_name
_audit_author_address
'Andrey Ilyukhin'
;Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2021-02-22 deposited with the CCDC.	2021-08-31 downloaded from the CCDC.
;

_audit_creation_date             2018-11-14T00:04:14-00:00
_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(I3)'
_chemical_formula_sum            'C18 H18 I6 N2'
_chemical_formula_weight         1023.74

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_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                   9.3297(2)
_cell_length_b                   8.3343(2)
_cell_length_c                   16.1878(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.1760(10)
_cell_angle_gamma                90
_cell_volume                     1255.37(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9953
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      33.18

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

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    2.708
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             916
_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 0.71081    9.349    8.352   16.212   90.002   94.169   90.010
;

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

_exptl_absorpt_coefficient_mu    7.43
_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  0.1769
_exptl_absorpt_correction_T_max  0.2693

#----------------------------------------------------------------------------#
#                   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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_number            17611
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.282
_diffrn_reflns_theta_max         33.201
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.9
_diffrn_reflns_Laue_measured_fraction_full 0.98
_diffrn_reflns_Laue_measured_fraction_max 0.9
_diffrn_reflns_point_group_measured_fraction_full 0.98
_diffrn_reflns_point_group_measured_fraction_max 0.9
_reflns_Friedel_coverage         0
_reflns_number_total             4328
_reflns_number_gt                4084
_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-2018/1 (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+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4328
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0235
_refine_ls_R_factor_gt           0.021
_refine_ls_wR_factor_ref         0.0506
_refine_ls_wR_factor_gt          0.0497
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_restrained_S_all      1.152
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.724
_refine_diff_density_min         -0.839
_refine_diff_density_rms         0.115

#----------------------------------------------------------------------------#
#                   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'
N N 0.0061 0.0033 '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'

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 0.21863(2) 0.48802(2) 0.20388(2) 0.02532(4) Uani 1 1 d . . . . .
I2 I 0.45818(2) 0.63781(2) 0.12212(2) 0.02138(4) Uani 1 1 d . . . . .
I3 I 0.69863(2) 0.75122(2) 0.03666(2) 0.02834(5) Uani 1 1 d . . . . .
C1 C -0.1944(3) 0.3740(3) 0.18015(15) 0.0246(4) Uani 1 1 d . . . . .
H1A H -0.110984 0.439069 0.188619 0.03 Uiso 1 1 calc R U . . .
C2 C -0.2876(3) 0.3613(3) 0.24191(16) 0.0287(5) Uani 1 1 d . . . . .
H2A H -0.268917 0.417266 0.292682 0.034 Uiso 1 1 calc R U . . .
C3 C -0.4090(3) 0.2661(3) 0.22935(16) 0.0267(5) Uani 1 1 d . . . . .
H3A H -0.473803 0.254971 0.271629 0.032 Uiso 1 1 calc R U . . .
C4 C -0.4347(3) 0.1873(3) 0.15448(16) 0.0255(5) Uani 1 1 d . . . . .
H4A H -0.518206 0.122852 0.144636 0.031 Uiso 1 1 calc R U . . .
C5 C -0.3386(2) 0.2029(3) 0.09431(14) 0.0218(4) Uani 1 1 d . . . . .
H5A H -0.355614 0.148489 0.042966 0.026 Uiso 1 1 calc R U . . .
C6 C -0.1171(2) 0.3097(3) 0.04193(14) 0.0212(4) Uani 1 1 d . . . . .
H6A H -0.037008 0.38159 0.06115 0.025 Uiso 1 1 calc R U . . .
H6B H -0.166829 0.358026 -0.008132 0.025 Uiso 1 1 calc R U . . .
C7 C -0.0576(2) 0.1484(3) 0.02024(14) 0.0190(4) Uani 1 1 d . . . . .
C8 C 0.0305(2) 0.0644(3) 0.07876(14) 0.0206(4) Uani 1 1 d . . . . .
H8A H 0.051611 0.10826 0.132435 0.025 Uiso 1 1 calc R U . . .
C9 C 0.0875(2) -0.0838(3) 0.05849(14) 0.0212(4) Uani 1 1 d . . . . .
H9A H 0.14697 -0.141023 0.098514 0.025 Uiso 1 1 calc R U . . .
N1 N -0.21976(19) 0.2956(2) 0.10801(12) 0.0183(3) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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
I1 I2 2.9556(2) . ?
I2 I3 2.8796(2) . ?
C1 N1 1.344(3) . ?
C1 C2 1.376(4) . ?
C2 C3 1.386(4) . ?
C3 C4 1.384(4) . ?
C4 C5 1.377(3) . ?
C5 N1 1.356(3) . ?
C6 N1 1.492(3) . ?
C6 C7 1.505(3) . ?
C7 C9 1.393(3) 3 ?
C7 C8 1.397(3) . ?
C8 C9 1.393(3) . ?

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
I3 I2 I1 174.110(7) . . ?
N1 C1 C2 120.9(2) . . ?
C1 C2 C3 119.4(2) . . ?
C4 C3 C2 119.2(2) . . ?
C5 C4 C3 119.6(2) . . ?
N1 C5 C4 120.3(2) . . ?
N1 C6 C7 111.37(18) . . ?
C9 C7 C8 119.7(2) 3 . ?
C9 C7 C6 120.4(2) 3 . ?
C8 C7 C6 119.9(2) . . ?
C9 C8 C7 120.1(2) . . ?
C7 C9 C8 120.3(2) 3 . ?
C1 N1 C5 120.6(2) . . ?
C1 N1 C6 120.21(19) . . ?
C5 N1 C6 119.17(19) . . ?

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 0.1(4) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C3 C4 C5 N1 -0.4(4) . . . . ?
N1 C6 C7 C9 115.4(2) . . . 3 ?
N1 C6 C7 C8 -65.9(3) . . . . ?
C9 C7 C8 C9 -0.3(4) 3 . . . ?
C6 C7 C8 C9 -179.0(2) . . . . ?
C7 C8 C9 C7 0.3(4) . . . 3 ?
C2 C1 N1 C5 0.4(3) . . . . ?
C2 C1 N1 C6 -179.5(2) . . . . ?
C4 C5 N1 C1 -0.3(3) . . . . ?
C4 C5 N1 C6 179.7(2) . . . . ?
C7 C6 N1 C1 120.5(2) . . . . ?
C7 C6 N1 C5 -59.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1A I1 0.95 3.09 3.960(2) 152.3 . yes
C2 H2A I3 0.95 3.12 3.734(3) 124.2 2_545 yes
C5 H5A I2 0.95 3.3 3.836(2) 118.1 3_565 yes

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2064476'
loop_
_audit_author_name
_audit_author_address
'Andrey Ilyukhin'
;Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2021-02-22 deposited with the CCDC.	2021-08-31 downloaded from the CCDC.
;

_audit_creation_date             2020-12-20T13:29:42-00:00
_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         '3(C13 H13 I N), Bi I6'
_chemical_formula_sum            'C39 H39 Bi I9 N3'
_chemical_formula_weight         1900.81
_chemical_absolute_configuration ad

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_Int_Tables_number      1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   9.6600(19)
_cell_length_b                   11.240(2)
_cell_length_c                   12.280(2)
_cell_angle_alpha                100.32(3)
_cell_angle_beta                 90.33(3)
_cell_angle_gamma                113.41(3)
_cell_volume                     1199.4(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1065
_cell_measurement_theta_min      3.8
_cell_measurement_theta_max      33

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

_exptl_crystal_description       prizm
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    2.632
_exptl_crystal_F_000             854
_exptl_special_details           
;
;

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

_exptl_absorpt_coefficient_mu    10.733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scala (Evans, 2005)'
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_T_max  0.9

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

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.79312
_diffrn_radiation_type           synchrotron
_diffrn_measurement_device_type  'MAR CCD'
_diffrn_measurement_method       'φ scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_number            30176
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.573
_diffrn_reflns_theta_max         30.951
_diffrn_reflns_theta_full        28.416
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.98
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.948
_reflns_Friedel_fraction_full    0.937
_reflns_Friedel_fraction_max     0.922
_reflns_Friedel_coverage         0.947
_reflns_number_total             10417
_reflns_number_gt                10272
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       Automar
_computing_cell_refinement       iMosflm
_computing_data_reduction        iMosflm
_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_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²+4.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         10417
_refine_ls_number_parameters     470
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_ref         0.0819
_refine_ls_wR_factor_gt          0.0816
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.210(7)
_refine_diff_density_max         1.062
_refine_diff_density_min         -1.515
_refine_diff_density_rms         0.196

#----------------------------------------------------------------------------#
#                   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 0.0043 0.0021 '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'
N N 0.0081 0.0042 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.2743 2.2097 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -8.6467 7.7905 '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
Bi1 Bi 0.50000(5) 0.50000(4) 0.50000(4) 0.01897(9) Uani 1 1 d . . . . .
I1 I 0.65250(7) 0.36923(6) 0.62210(5) 0.02427(14) Uani 1 1 d . . . . .
I2 I 0.20183(7) 0.37281(6) 0.60283(5) 0.02254(14) Uani 1 1 d . . . . .
I3 I 0.38224(7) 0.24138(6) 0.31867(5) 0.02154(14) Uani 1 1 d . . . . .
I4 I 0.61502(7) 0.74938(6) 0.68579(5) 0.02283(14) Uani 1 1 d . . . . .
I5 I 0.80097(7) 0.62169(6) 0.39087(5) 0.02273(14) Uani 1 1 d . . . . .
I6 I 0.34610(7) 0.64074(6) 0.36928(5) 0.02329(14) Uani 1 1 d . . . . .
I7 I 1.15542(8) -0.12472(7) 1.22087(6) 0.02543(15) Uani 1 1 d . . . . .
I8 I 0.81745(8) 0.13506(7) 0.74811(6) 0.02678(15) Uani 1 1 d . . . . .
I9 I 0.22721(9) -0.95011(7) 0.91079(6) 0.03022(16) Uani 1 1 d . . . . .
N1 N 1.1408(11) -0.1980(9) 0.6294(8) 0.0245(18) Uani 1 1 d . . . . .
N2 N 0.8800(11) 0.2113(10) 1.3499(7) 0.0250(19) Uani 1 1 d . . . . .
N3 N 0.6584(10) -0.1613(8) 1.1171(7) 0.0219(17) Uani 1 1 d . . . . .
C1 C 1.2912(14) -0.1438(13) 0.6208(10) 0.029(2) Uani 1 1 d . . . . .
H1A H 1.350279 -0.191897 0.630949 0.035 Uiso 1 1 calc R U . . .
C2 C 1.3593(13) -0.0199(12) 0.5975(10) 0.028(2) Uani 1 1 d . . . . .
H2A H 1.465149 0.017197 0.590517 0.034 Uiso 1 1 calc R U . . .
C3 C 1.2746(12) 0.0512(11) 0.5842(8) 0.025(2) Uani 1 1 d . . . . .
H3A H 1.321061 0.137407 0.56828 0.029 Uiso 1 1 calc R U . . .
C4 C 1.1187(13) -0.0063(10) 0.5945(9) 0.025(2) Uani 1 1 d . . . . .
H4A H 1.057682 0.040348 0.584817 0.03 Uiso 1 1 calc R U . . .
C5 C 1.0538(13) -0.1322(10) 0.6190(8) 0.022(2) Uani 1 1 d . . . . .
H5A H 0.948615 -0.171219 0.628293 0.027 Uiso 1 1 calc R U . . .
C6 C 1.0709(14) -0.3344(11) 0.6538(9) 0.028(2) Uani 1 1 d . . . . .
H6A H 1.127606 -0.386055 0.619771 0.034 Uiso 1 1 calc R U . . .
H6B H 0.965361 -0.378901 0.619677 0.034 Uiso 1 1 calc R U . . .
C7 C 1.0713(14) -0.3324(11) 0.7774(9) 0.026(2) Uani 1 1 d . . . . .
C8 C 1.1952(13) -0.3359(11) 0.8344(9) 0.025(2) Uani 1 1 d . . . . .
H8A H 1.278871 -0.339338 0.795747 0.029 Uiso 1 1 calc R U . . .
C9 C 1.1952(13) -0.3343(11) 0.9488(9) 0.025(2) Uani 1 1 d . . . . .
H9A H 1.279429 -0.335747 0.987893 0.029 Uiso 1 1 calc R U . . .
C10 C 1.0720(13) -0.3304(10) 1.0052(8) 0.024(2) Uani 1 1 d . . . . .
C11 C 0.9488(13) -0.3308(11) 0.9463(9) 0.026(2) Uani 1 1 d . . . . .
H11A H 0.863271 -0.330647 0.984042 0.031 Uiso 1 1 calc R U . . .
C12 C 0.9484(13) -0.3312(10) 0.8336(10) 0.027(2) Uani 1 1 d . . . . .
H12A H 0.863333 -0.330736 0.794807 0.032 Uiso 1 1 calc R U . . .
C13 C 1.0723(15) -0.3286(10) 1.1280(10) 0.028(2) Uani 1 1 d . . . . .
H13A H 1.137856 -0.371072 1.149201 0.033 Uiso 1 1 calc R U . . .
H13B H 0.968281 -0.379287 1.146629 0.033 Uiso 1 1 calc R U . . .
C14 C 0.7321(13) 0.1748(12) 1.3673(9) 0.028(2) Uani 1 1 d . . . . .
H14A H 0.685571 0.233888 1.361447 0.034 Uiso 1 1 calc R U . . .
C15 C 0.6465(15) 0.0524(17) 1.3936(11) 0.041(3) Uani 1 1 d . . . . .
H15A H 0.542187 0.027449 1.404565 0.049 Uiso 1 1 calc R U . . .
C16 C 0.7152(15) -0.0313(12) 1.4034(9) 0.032(3) Uani 1 1 d . . . . .
H16A H 0.659788 -0.113808 1.424147 0.038 Uiso 1 1 calc R U . . .
C17 C 0.8656(16) 0.0050(12) 1.3828(10) 0.032(2) Uani 1 1 d . . . . .
H17A H 0.913756 -0.05348 1.386424 0.038 Uiso 1 1 calc R U . . .
C18 C 0.9441(13) 0.1266(11) 1.3572(9) 0.025(2) Uani 1 1 d . . . . .
H18A H 1.04782 0.151916 1.344175 0.03 Uiso 1 1 calc R U . . .
C19 C 0.9663(15) 0.3407(11) 1.3205(9) 0.030(2) Uani 1 1 d . . . . .
H19A H 1.074263 0.371352 1.346583 0.036 Uiso 1 1 calc R U . . .
H19B H 0.928829 0.405808 1.359277 0.036 Uiso 1 1 calc R U . . .
C20 C 0.9531(14) 0.3354(11) 1.1971(9) 0.027(2) Uani 1 1 d . . . . .
C21 C 1.0681(13) 0.3268(12) 1.1321(10) 0.028(2) Uani 1 1 d . . . . .
H21A H 1.154022 0.321506 1.165253 0.033 Uiso 1 1 calc R U . . .
C22 C 1.0575(13) 0.3261(12) 1.0186(9) 0.029(2) Uani 1 1 d . . . . .
H22A H 1.136854 0.319837 0.975792 0.035 Uiso 1 1 calc R U . . .
C23 C 0.9345(13) 0.3341(11) 0.9662(9) 0.024(2) Uani 1 1 d . . . . .
C24 C 0.8193(14) 0.3450(11) 1.0323(9) 0.024(2) Uani 1 1 d . . . . .
H24A H 0.734727 0.352447 0.999313 0.029 Uiso 1 1 calc R U . . .
C25 C 0.8287(13) 0.3448(11) 1.1460(10) 0.026(2) Uani 1 1 d . . . . .
H25A H 0.749719 0.351021 1.18918 0.031 Uiso 1 1 calc R U . . .
C26 C 0.9264(14) 0.3358(11) 0.8461(9) 0.027(2) Uani 1 1 d . . . . .
H26A H 1.029923 0.379224 0.823385 0.032 Uiso 1 1 calc R U . . .
H26B H 0.868441 0.387604 0.831639 0.032 Uiso 1 1 calc R U . . .
C27 C 0.7758(13) -0.0946(10) 1.0612(9) 0.026(2) Uani 1 1 d . . . . .
H27A H 0.863128 -0.113861 1.058177 0.032 Uiso 1 1 calc R U . . .
C28 C 0.7676(13) 0.0019(11) 1.0086(9) 0.028(2) Uani 1 1 d . . . . .
H28A H 0.850687 0.051577 0.971478 0.034 Uiso 1 1 calc R U . . .
C29 C 0.6375(14) 0.0254(11) 1.0107(10) 0.031(2) Uani 1 1 d . . . . .
H29A H 0.62721 0.085901 0.969651 0.037 Uiso 1 1 calc R U . . .
C30 C 0.5214(14) -0.0401(11) 1.0731(10) 0.030(2) Uani 1 1 d . . . . .
H30A H 0.435305 -0.019216 1.080377 0.036 Uiso 1 1 calc R U . . .
C31 C 0.5337(12) -0.1370(11) 1.1248(9) 0.029(2) Uani 1 1 d . . . . .
H31A H 0.454001 -0.185255 1.165143 0.034 Uiso 1 1 calc R U . . .
C32 C 0.6579(12) -0.2760(10) 1.1592(9) 0.023(2) Uani 1 1 d . . . . .
H32A H 0.609831 -0.280116 1.230196 0.028 Uiso 1 1 calc R U . . .
H32B H 0.763574 -0.265062 1.174001 0.028 Uiso 1 1 calc R U . . .
C33 C 0.5729(12) -0.4046(11) 1.0768(8) 0.022(2) Uani 1 1 d . . . . .
C34 C 0.5459(12) -0.4108(12) 0.9626(9) 0.025(2) Uani 1 1 d . . . . .
H34A H 0.579355 -0.331589 0.934192 0.03 Uiso 1 1 calc R U . . .
C35 C 0.4718(14) -0.5301(11) 0.8924(9) 0.028(2) Uani 1 1 d . . . . .
H35A H 0.450168 -0.53251 0.816247 0.033 Uiso 1 1 calc R U . . .
C36 C 0.4275(12) -0.6480(10) 0.9308(8) 0.024(2) Uani 1 1 d . . . . .
C37 C 0.4580(13) -0.6408(11) 1.0447(9) 0.029(2) Uani 1 1 d . . . . .
H37A H 0.430827 -0.720362 1.072023 0.034 Uiso 1 1 calc R U . . .
C38 C 0.5259(12) -0.5222(10) 1.1168(8) 0.023(2) Uani 1 1 d . . . . .
H38A H 0.54103 -0.519623 1.193788 0.027 Uiso 1 1 calc R U . . .
C39 C 0.3582(16) -0.7765(11) 0.8455(9) 0.033(3) Uani 1 1 d . . . . .
H39A H 0.440836 -0.791814 0.8065 0.04 Uiso 1 1 calc R U . . .
H39B H 0.292138 -0.765599 0.789568 0.04 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
Bi1 I1 3.0106(11) . ?
Bi1 I2 3.0580(13) . ?
Bi1 I4 3.0824(15) . ?
Bi1 I5 3.1083(13) . ?
Bi1 I3 3.1187(15) . ?
Bi1 I6 3.1687(11) . ?
I7 C13 2.188(10) . ?
I8 C26 2.184(11) . ?
I9 C39 2.160(12) . ?
N1 C5 1.341(15) . ?
N1 C1 1.347(15) . ?
N1 C6 1.496(14) . ?
N2 C18 1.340(15) . ?
N2 C14 1.350(15) . ?
N2 C19 1.473(15) . ?
N3 C31 1.337(15) . ?
N3 C27 1.356(14) . ?
N3 C32 1.471(13) . ?
C1 C2 1.367(17) . ?
C1 H1A 0.95 . ?
C2 C3 1.378(18) . ?
C2 H2A 0.95 . ?
C3 C4 1.400(16) . ?
C3 H3A 0.95 . ?
C4 C5 1.392(15) . ?
C4 H4A 0.95 . ?
C5 H5A 0.95 . ?
C6 C7 1.515(14) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C7 C12 1.380(17) . ?
C7 C8 1.401(17) . ?
C8 C9 1.401(15) . ?
C8 H8A 0.95 . ?
C9 C10 1.392(16) . ?
C9 H9A 0.95 . ?
C10 C11 1.388(16) . ?
C10 C13 1.505(15) . ?
C11 C12 1.383(16) . ?
C11 H11A 0.95 . ?
C12 H12A 0.95 . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 C15 1.39(2) . ?
C14 H14A 0.95 . ?
C15 C16 1.37(2) . ?
C15 H15A 0.95 . ?
C16 C17 1.383(19) . ?
C16 H16A 0.95 . ?
C17 C18 1.370(16) . ?
C17 H17A 0.95 . ?
C18 H18A 0.95 . ?
C19 C20 1.509(15) . ?
C19 H19A 0.99 . ?
C19 H19B 0.99 . ?
C20 C21 1.396(17) . ?
C20 C25 1.401(18) . ?
C21 C22 1.395(16) . ?
C21 H21A 0.95 . ?
C22 C23 1.390(17) . ?
C22 H22A 0.95 . ?
C23 C24 1.412(16) . ?
C23 C26 1.480(15) . ?
C24 C25 1.399(15) . ?
C24 H24A 0.95 . ?
C25 H25A 0.95 . ?
C26 H26A 0.99 . ?
C26 H26B 0.99 . ?
C27 C28 1.385(16) . ?
C27 H27A 0.95 . ?
C28 C29 1.383(18) . ?
C28 H28A 0.95 . ?
C29 C30 1.394(16) . ?
C29 H29A 0.95 . ?
C30 C31 1.397(16) . ?
C30 H30A 0.95 . ?
C31 H31A 0.95 . ?
C32 C33 1.520(14) . ?
C32 H32A 0.99 . ?
C32 H32B 0.99 . ?
C33 C38 1.397(15) . ?
C33 C34 1.409(14) . ?
C34 C35 1.367(16) . ?
C34 H34A 0.95 . ?
C35 C36 1.393(15) . ?
C35 H35A 0.95 . ?
C36 C37 1.409(15) . ?
C36 C39 1.521(14) . ?
C37 C38 1.367(15) . ?
C37 H37A 0.95 . ?
C38 H38A 0.95 . ?
C39 H39A 0.99 . ?
C39 H39B 0.99 . ?

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 92.26(3) . . ?
I1 Bi1 I4 91.45(3) . . ?
I2 Bi1 I4 93.09(4) . . ?
I1 Bi1 I5 87.39(3) . . ?
I2 Bi1 I5 178.38(2) . . ?
I4 Bi1 I5 88.51(4) . . ?
I1 Bi1 I3 86.84(3) . . ?
I2 Bi1 I3 85.75(4) . . ?
I4 Bi1 I3 177.89(2) . . ?
I5 Bi1 I3 92.64(4) . . ?
I1 Bi1 I6 178.77(3) . . ?
I2 Bi1 I6 88.97(3) . . ?
I4 Bi1 I6 88.44(3) . . ?
I5 Bi1 I6 91.38(3) . . ?
I3 Bi1 I6 93.30(3) . . ?
C5 N1 C1 121.8(10) . . ?
C5 N1 C6 119.6(10) . . ?
C1 N1 C6 118.5(10) . . ?
C18 N2 C14 118.8(10) . . ?
C18 N2 C19 121.4(10) . . ?
C14 N2 C19 119.8(10) . . ?
C31 N3 C27 122.5(10) . . ?
C31 N3 C32 117.7(9) . . ?
C27 N3 C32 119.3(9) . . ?
N1 C1 C2 120.4(12) . . ?
N1 C1 H1A 119.8 . . ?
C2 C1 H1A 119.8 . . ?
C1 C2 C3 120.1(11) . . ?
C1 C2 H2A 119.9 . . ?
C3 C2 H2A 119.9 . . ?
C2 C3 C4 118.7(11) . . ?
C2 C3 H3A 120.7 . . ?
C4 C3 H3A 120.7 . . ?
C5 C4 C3 119.5(11) . . ?
C5 C4 H4A 120.3 . . ?
C3 C4 H4A 120.3 . . ?
N1 C5 C4 119.5(11) . . ?
N1 C5 H5A 120.3 . . ?
C4 C5 H5A 120.3 . . ?
N1 C6 C7 112.0(9) . . ?
N1 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
N1 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C12 C7 C8 119.8(10) . . ?
C12 C7 C6 120.4(11) . . ?
C8 C7 C6 119.8(11) . . ?
C7 C8 C9 119.6(11) . . ?
C7 C8 H8A 120.2 . . ?
C9 C8 H8A 120.2 . . ?
C10 C9 C8 120.2(10) . . ?
C10 C9 H9A 119.9 . . ?
C8 C9 H9A 119.9 . . ?
C11 C10 C9 119.1(10) . . ?
C11 C10 C13 120.8(11) . . ?
C9 C10 C13 120.1(11) . . ?
C12 C11 C10 121.1(11) . . ?
C12 C11 H11A 119.4 . . ?
C10 C11 H11A 119.4 . . ?
C7 C12 C11 120.1(11) . . ?
C7 C12 H12A 119.9 . . ?
C11 C12 H12A 119.9 . . ?
C10 C13 I7 110.1(7) . . ?
C10 C13 H13A 109.6 . . ?
I7 C13 H13A 109.6 . . ?
C10 C13 H13B 109.6 . . ?
I7 C13 H13B 109.6 . . ?
H13A C13 H13B 108.2 . . ?
N2 C14 C15 121.4(12) . . ?
N2 C14 H14A 119.3 . . ?
C15 C14 H14A 119.3 . . ?
C16 C15 C14 118.9(12) . . ?
C16 C15 H15A 120.6 . . ?
C14 C15 H15A 120.6 . . ?
C15 C16 C17 119.5(11) . . ?
C15 C16 H16A 120.2 . . ?
C17 C16 H16A 120.2 . . ?
C18 C17 C16 118.9(12) . . ?
C18 C17 H17A 120.6 . . ?
C16 C17 H17A 120.6 . . ?
N2 C18 C17 122.4(12) . . ?
N2 C18 H18A 118.8 . . ?
C17 C18 H18A 118.8 . . ?
N2 C19 C20 112.4(9) . . ?
N2 C19 H19A 109.1 . . ?
C20 C19 H19A 109.1 . . ?
N2 C19 H19B 109.1 . . ?
C20 C19 H19B 109.1 . . ?
H19A C19 H19B 107.9 . . ?
C21 C20 C25 118.5(10) . . ?
C21 C20 C19 120.6(11) . . ?
C25 C20 C19 120.9(11) . . ?
C22 C21 C20 120.3(11) . . ?
C22 C21 H21A 119.8 . . ?
C20 C21 H21A 119.8 . . ?
C23 C22 C21 122.1(11) . . ?
C23 C22 H22A 119 . . ?
C21 C22 H22A 119 . . ?
C22 C23 C24 117.6(10) . . ?
C22 C23 C26 121.4(10) . . ?
C24 C23 C26 121.0(11) . . ?
C25 C24 C23 120.6(11) . . ?
C25 C24 H24A 119.7 . . ?
C23 C24 H24A 119.7 . . ?
C24 C25 C20 120.9(11) . . ?
C24 C25 H25A 119.6 . . ?
C20 C25 H25A 119.6 . . ?
C23 C26 I8 110.9(8) . . ?
C23 C26 H26A 109.5 . . ?
I8 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
I8 C26 H26B 109.5 . . ?
H26A C26 H26B 108.1 . . ?
N3 C27 C28 119.5(10) . . ?
N3 C27 H27A 120.2 . . ?
C28 C27 H27A 120.2 . . ?
C29 C28 C27 119.4(10) . . ?
C29 C28 H28A 120.3 . . ?
C27 C28 H28A 120.3 . . ?
C28 C29 C30 119.8(11) . . ?
C28 C29 H29A 120.1 . . ?
C30 C29 H29A 120.1 . . ?
C29 C30 C31 118.8(11) . . ?
C29 C30 H30A 120.6 . . ?
C31 C30 H30A 120.6 . . ?
N3 C31 C30 119.7(10) . . ?
N3 C31 H31A 120.2 . . ?
C30 C31 H31A 120.2 . . ?
N3 C32 C33 111.6(9) . . ?
N3 C32 H32A 109.3 . . ?
C33 C32 H32A 109.3 . . ?
N3 C32 H32B 109.3 . . ?
C33 C32 H32B 109.3 . . ?
H32A C32 H32B 108 . . ?
C38 C33 C34 119.1(10) . . ?
C38 C33 C32 117.5(9) . . ?
C34 C33 C32 123.3(10) . . ?
C35 C34 C33 120.4(10) . . ?
C35 C34 H34A 119.8 . . ?
C33 C34 H34A 119.8 . . ?
C34 C35 C36 121.0(10) . . ?
C34 C35 H35A 119.5 . . ?
C36 C35 H35A 119.5 . . ?
C35 C36 C37 118.1(10) . . ?
C35 C36 C39 117.6(9) . . ?
C37 C36 C39 124.2(10) . . ?
C38 C37 C36 121.5(10) . . ?
C38 C37 H37A 119.2 . . ?
C36 C37 H37A 119.2 . . ?
C37 C38 C33 119.8(10) . . ?
C37 C38 H38A 120.1 . . ?
C33 C38 H38A 120.1 . . ?
C36 C39 I9 115.5(7) . . ?
C36 C39 H39A 108.4 . . ?
I9 C39 H39A 108.4 . . ?
C36 C39 H39B 108.4 . . ?
I9 C39 H39B 108.4 . . ?
H39A C39 H39B 107.5 . . ?

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
C5 N1 C1 C2 -2.0(17) . . . . ?
C6 N1 C1 C2 179.3(10) . . . . ?
N1 C1 C2 C3 0.9(17) . . . . ?
C1 C2 C3 C4 -0.3(16) . . . . ?
C2 C3 C4 C5 0.7(15) . . . . ?
C1 N1 C5 C4 2.4(16) . . . . ?
C6 N1 C5 C4 -178.9(10) . . . . ?
C3 C4 C5 N1 -1.8(15) . . . . ?
C5 N1 C6 C7 -89.7(13) . . . . ?
C1 N1 C6 C7 89.0(13) . . . . ?
N1 C6 C7 C12 92.4(13) . . . . ?
N1 C6 C7 C8 -89.5(13) . . . . ?
C12 C7 C8 C9 -1.8(16) . . . . ?
C6 C7 C8 C9 -179.9(10) . . . . ?
C7 C8 C9 C10 0.6(16) . . . . ?
C8 C9 C10 C11 1.2(16) . . . . ?
C8 C9 C10 C13 -180.0(10) . . . . ?
C9 C10 C11 C12 -1.7(17) . . . . ?
C13 C10 C11 C12 179.4(10) . . . . ?
C8 C7 C12 C11 1.3(17) . . . . ?
C6 C7 C12 C11 179.4(10) . . . . ?
C10 C11 C12 C7 0.5(17) . . . . ?
C11 C10 C13 I7 -86.8(11) . . . . ?
C9 C10 C13 I7 94.4(11) . . . . ?
C18 N2 C14 C15 0.7(17) . . . . ?
C19 N2 C14 C15 179.0(11) . . . . ?
N2 C14 C15 C16 0.9(19) . . . . ?
C14 C15 C16 C17 -2.5(19) . . . . ?
C15 C16 C17 C18 2.5(18) . . . . ?
C14 N2 C18 C17 -0.7(16) . . . . ?
C19 N2 C18 C17 -179.0(11) . . . . ?
C16 C17 C18 N2 -0.9(18) . . . . ?
C18 N2 C19 C20 91.5(13) . . . . ?
C14 N2 C19 C20 -86.8(13) . . . . ?
N2 C19 C20 C21 -99.6(13) . . . . ?
N2 C19 C20 C25 83.1(14) . . . . ?
C25 C20 C21 C22 -0.7(17) . . . . ?
C19 C20 C21 C22 -178.0(11) . . . . ?
C20 C21 C22 C23 0.2(18) . . . . ?
C21 C22 C23 C24 0.8(17) . . . . ?
C21 C22 C23 C26 178.8(11) . . . . ?
C22 C23 C24 C25 -1.3(16) . . . . ?
C26 C23 C24 C25 -179.3(11) . . . . ?
C23 C24 C25 C20 0.8(17) . . . . ?
C21 C20 C25 C24 0.2(17) . . . . ?
C19 C20 C25 C24 177.5(10) . . . . ?
C22 C23 C26 I8 89.5(12) . . . . ?
C24 C23 C26 I8 -92.6(11) . . . . ?
C31 N3 C27 C28 -0.7(16) . . . . ?
C32 N3 C27 C28 171.4(10) . . . . ?
N3 C27 C28 C29 -2.3(16) . . . . ?
C27 C28 C29 C30 5.3(17) . . . . ?
C28 C29 C30 C31 -5.5(17) . . . . ?
C27 N3 C31 C30 0.5(16) . . . . ?
C32 N3 C31 C30 -171.7(10) . . . . ?
C29 C30 C31 N3 2.6(17) . . . . ?
C31 N3 C32 C33 79.3(12) . . . . ?
C27 N3 C32 C33 -93.2(11) . . . . ?
N3 C32 C33 C38 -162.1(9) . . . . ?
N3 C32 C33 C34 20.9(14) . . . . ?
C38 C33 C34 C35 1.4(17) . . . . ?
C32 C33 C34 C35 178.4(11) . . . . ?
C33 C34 C35 C36 -2.9(18) . . . . ?
C34 C35 C36 C37 1.5(17) . . . . ?
C34 C35 C36 C39 -174.7(12) . . . . ?
C35 C36 C37 C38 1.5(17) . . . . ?
C39 C36 C37 C38 177.4(12) . . . . ?
C36 C37 C38 C33 -3.0(18) . . . . ?
C34 C33 C38 C37 1.6(16) . . . . ?
C32 C33 C38 C37 -175.7(10) . . . . ?
C35 C36 C39 I9 -160.7(9) . . . . ?
C37 C36 C39 I9 23.4(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1A I4 0.95 2.99 3.894(13) 160.7 1_645 yes
C5 H5A I4 0.95 3.11 4.044(11) 169.8 1_545 yes
C6 H6A I2 0.99 3.04 3.925(12) 149.3 1_645 yes
C6 H6B I1 0.99 3.22 4.050(12) 142.2 1_545 yes
C6 H6B I5 0.99 3.22 3.972(12) 133.8 1_545 yes
C13 H13A I6 0.99 3.31 4.110(13) 139 1_646 yes
C14 H14A I3 0.95 3.01 3.806(12) 142.2 1_556 yes
C18 H18A I3 0.95 3.01 3.963(12) 176.2 1_656 yes
C19 H19A I6 0.99 3.08 3.822(12) 132.4 1_656 yes
C19 H19B I5 0.99 3.1 4.039(13) 158.8 1_556 yes
C26 H26A I2 0.99 3.19 3.979(12) 137.8 1_655 yes
C26 H26B I1 0.99 3.23 3.973(12) 133.3 . yes
C28 H28A I8 0.95 3.11 3.724(11) 124 . yes
C30 H30A I7 0.95 3.15 3.836(12) 130.4 1_455 yes
C30 H30A I9 0.95 3.28 4.001(12) 134.3 1_565 yes
C31 H31A I7 0.95 3.27 3.893(11) 125.4 1_455 yes
C32 H32A I6 0.99 3 3.914(10) 154.2 1_546 yes
C32 H32B I5 0.99 3.23 3.703(11) 111.3 1_546 yes
C39 H39B I2 0.99 3.28 4.210(13) 156.8 1_545 yes

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2064475'
loop_
_audit_author_name
_audit_author_address
'Andrey Ilyukhin'
;Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2021-02-22 deposited with the CCDC.	2021-08-31 downloaded from the CCDC.
;

_audit_creation_date             2020-12-20T14:31:36-00:00
_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         'Bi I5, 2(C9 H9 N)'
_chemical_formula_sum            'C18 H18 Bi I5 N2'
_chemical_formula_weight         1105.82
_chemical_absolute_configuration ad

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

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'I 4'
_symmetry_space_group_name_Hall  'I 4'
_symmetry_Int_Tables_number      79
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-y, x, z'
'y, -x, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-y+1/2, x+1/2, z+1/2'
'y+1/2, -x+1/2, z+1/2'

_cell_length_a                   13.1552(19)
_cell_length_b                   13.1552(19)
_cell_length_c                   14.799(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2561.2(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2310
_cell_measurement_theta_min      4.1
_cell_measurement_theta_max      31.9

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

_exptl_crystal_description       prizm
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.025
_exptl_crystal_size_min          0.025
_exptl_crystal_density_diffrn    2.868
_exptl_crystal_F_000             1952
_exptl_special_details           
;
;

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

_exptl_absorpt_coefficient_mu    13.661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scala (Evans, 2005)'
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_T_max  0.91

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

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.79312
_diffrn_radiation_type           synchrotron
_diffrn_measurement_device_type  'MAR CCD'
_diffrn_measurement_method       'φ scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_number            11591
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.312
_diffrn_reflns_theta_max         30.956
_diffrn_reflns_theta_full        28.416
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_coverage         0.927
_reflns_number_total             2940
_reflns_number_gt                2686
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       Automar
_computing_cell_refinement       iMosflm
_computing_data_reduction        iMosflm
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²+6.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2940
_refine_ls_number_parameters     135
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0856
_refine_ls_wR_factor_gt          0.084
_refine_ls_goodness_of_fit_ref   1.266
_refine_ls_restrained_S_all      1.265
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.465(15)
_refine_diff_density_max         0.995
_refine_diff_density_min         -1.47
_refine_diff_density_rms         0.197

#----------------------------------------------------------------------------#
#                   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 0.0043 0.0021 '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'
N N 0.0081 0.0042 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.2743 2.2097 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -8.6467 7.7905 '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
Bi1 Bi 0.5 0.5 0.32594(18) 0.0236(5) Uani 0.770(8) 4 d S T P A 1
Bi2 Bi 0.5 0.5 -0.11699(18) 0.0241(5) Uani 0.770(8) 4 d S T P A 1
I1 I 0.27121(6) 0.46418(6) 0.31424(8) 0.0260(2) Uani 0.770(8) 1 d . . P A 1
I2 I 0.5 0.5 0.52151(19) 0.0253(7) Uani 0.770(8) 4 d S T P A 1
I3 I 0.27306(6) 0.46379(6) -0.15122(8) 0.0268(3) Uani 0.770(8) 1 d . . P A 1
I4 I 0.5 0.5 0.0841(7) 0.039(3) Uani 0.770(8) 4 d S T P A 1
N1 N 0.6448(5) 0.7573(5) 0.5818(7) 0.0210(14) Uani 1 1 d . . . . .
C1 C 0.6949(11) 0.7480(13) 0.5019(7) 0.029(3) Uani 1 1 d . . . . .
H1A H 0.658444 0.751649 0.446584 0.035 Uiso 1 1 calc R U . . .
C2 C 0.7972(14) 0.7334(13) 0.5011(10) 0.041(5) Uani 1 1 d . . . . .
H2A H 0.831924 0.726693 0.445126 0.049 Uiso 1 1 calc R U . . .
C3 C 0.8502(7) 0.7284(6) 0.5801(11) 0.0298(19) Uani 1 1 d . . . . .
H3A H 0.921906 0.720325 0.578835 0.036 Uiso 1 1 calc R U . . .
C4 C 0.7997(9) 0.7350(9) 0.6626(9) 0.019(3) Uani 1 1 d . . . . .
H4A H 0.835581 0.730241 0.718151 0.023 Uiso 1 1 calc R U . . .
C5 C 0.6930(11) 0.7491(10) 0.6607(9) 0.026(3) Uani 1 1 d . . . . .
H5A H 0.655817 0.752653 0.715576 0.031 Uiso 1 1 calc R U . . .
C6 C 0.5335(6) 0.7816(6) 0.5819(9) 0.0234(16) Uani 1 1 d . . . . .
H6A H 0.501382 0.751941 0.636373 0.028 Uiso 1 1 calc R U . . .
H6B H 0.501019 0.750962 0.528085 0.028 Uiso 1 1 calc R U . . .
C7 C 0.5167(6) 0.8959(6) 0.5812(9) 0.0229(16) Uani 1 1 d . . . . .
C8 C 0.5070(10) 0.9463(10) 0.5011(7) 0.025(3) Uani 1 1 d . . . . .
H8A H 0.509401 0.910037 0.445662 0.03 Uiso 1 1 calc R U . . .
C9 C 0.5092(10) 0.9490(10) 0.6636(8) 0.026(3) Uani 1 1 d . . . . .
H9A H 0.516936 0.913772 0.719167 0.031 Uiso 1 1 calc R U . . .
Bi1B Bi 0.5 0.5 0.2844(8) 0.025(2) Uani 0.230(8) 4 d S T P A 2
Bi2B Bi 0.5 0.5 -0.1585(9) 0.0252(19) Uani 0.230(8) 4 d S T P A 2
I1B I 0.27121(6) 0.46418(6) 0.31424(8) 0.0260(2) Uani 0.230(8) 1 d . . P A 2
I2B I 0.5 0.5 0.6421(6) 0.028(2) Uani 0.230(8) 4 d S T P A 2
I3B I 0.27306(6) 0.46379(6) -0.15122(8) 0.0268(3) Uani 0.230(8) 1 d . . P A 2
I4B I 0.5 0.5 0.067(3) 0.021(3) Uani 0.230(8) 4 d S T P A 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 I2 2.894(4) . ?
Bi1 I1 3.0513(9) . ?
Bi1 I1 3.0513(9) 4_565 ?
Bi1 I1 3.0514(9) 2_665 ?
Bi1 I1 3.0514(9) 3_655 ?
Bi2 I4 2.976(11) . ?
Bi2 I3 3.0654(10) . ?
Bi2 I3 3.0654(10) 3_655 ?
Bi2 I3 3.0654(10) 2_665 ?
Bi2 I3 3.0654(10) 4_565 ?
N1 C5 1.333(17) . ?
N1 C1 1.360(15) . ?
N1 C6 1.499(10) . ?
C1 C2 1.36(3) . ?
C2 C3 1.36(2) . ?
C3 C4 1.39(2) . ?
C4 C5 1.416(19) . ?
C6 C7 1.520(10) . ?
C7 C8 1.364(17) . ?
C7 C9 1.409(17) . ?
C8 C8 1.42(3) 2_675 ?
C9 C9 1.36(3) 2_675 ?
Bi1B I1B 3.078(2) . ?
Bi1B I4B 3.22(4) . ?
Bi2B I2B 2.950(16) 1_554 ?
Bi2B I3B 3.0252(10) . ?
Bi2B I4B 3.33(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I2 Bi1 I1 93.25(7) . . ?
I2 Bi1 I1 93.25(7) . 4_565 ?
I1 Bi1 I1 89.816(8) . 4_565 ?
I2 Bi1 I1 93.25(7) . 2_665 ?
I1 Bi1 I1 173.49(14) . 2_665 ?
I1 Bi1 I1 89.817(8) 4_565 2_665 ?
I2 Bi1 I1 93.25(7) . 3_655 ?
I1 Bi1 I1 89.815(8) . 3_655 ?
I1 Bi1 I1 173.49(14) 4_565 3_655 ?
I1 Bi1 I1 89.816(8) 2_665 3_655 ?
I4 Bi2 I3 99.51(7) . . ?
I4 Bi2 I3 99.51(7) . 3_655 ?
I3 Bi2 I3 88.43(2) . 3_655 ?
I4 Bi2 I3 99.51(7) . 2_665 ?
I3 Bi2 I3 160.97(14) . 2_665 ?
I3 Bi2 I3 88.43(2) 3_655 2_665 ?
I4 Bi2 I3 99.51(7) . 4_565 ?
I3 Bi2 I3 88.43(2) . 4_565 ?
I3 Bi2 I3 160.97(14) 3_655 4_565 ?
I3 Bi2 I3 88.43(2) 2_665 4_565 ?
C5 N1 C1 121.6(8) . . ?
C5 N1 C6 118.8(10) . . ?
C1 N1 C6 119.6(10) . . ?
C2 C1 N1 120.0(12) . . ?
C1 C2 C3 120.4(13) . . ?
C2 C3 C4 120.4(9) . . ?
C3 C4 C5 117.6(12) . . ?
N1 C5 C4 120.0(12) . . ?
N1 C6 C7 110.7(6) . . ?
C8 C7 C9 120.3(8) . . ?
C8 C7 C6 120.1(11) . . ?
C9 C7 C6 119.6(11) . . ?
C7 C8 C8 119.6(7) . 2_675 ?
C9 C9 C7 120.0(7) 2_675 . ?
I1B Bi1B I4B 98.3(2) . . ?
I2B Bi2B I3B 92.1(3) 1_554 . ?
I2B Bi2B I4B 180 1_554 . ?
I3B Bi2B I4B 87.9(3) . . ?
Bi1B I4B Bi2B 180 . . ?

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
C5 N1 C1 C2 -2.3(19) . . . . ?
C6 N1 C1 C2 175.2(14) . . . . ?
N1 C1 C2 C3 0(3) . . . . ?
C1 C2 C3 C4 2(2) . . . . ?
C2 C3 C4 C5 -1.3(14) . . . . ?
C1 N1 C5 C4 3.0(14) . . . . ?
C6 N1 C5 C4 -174.5(10) . . . . ?
C3 C4 C5 N1 -1.2(18) . . . . ?
C5 N1 C6 C7 89.0(12) . . . . ?
C1 N1 C6 C7 -88.5(14) . . . . ?
N1 C6 C7 C8 91.3(12) . . . . ?
N1 C6 C7 C9 -90.1(12) . . . . ?
C9 C7 C8 C8 2.5(18) . . . 2_675 ?
C6 C7 C8 C8 -178.9(13) . . . 2_675 ?
C8 C7 C9 C9 0.8(18) . . . 2_675 ?
C6 C7 C9 C9 -177.8(14) . . . 2_675 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1A I1 0.95 3.23 4.122(13) 156.4 4_565 yes
C2 H2A I3 0.95 3.1 3.904(16) 143 7_655 yes
C4 H4A I1 0.95 3.04 3.861(11) 145.4 7_655 yes
C5 H5A I3 0.95 3.22 4.115(14) 157.3 4_566 yes
C6 H6A I3 0.99 3.2 4.118(13) 155 4_566 yes
C6 H6A I2B 0.99 3.32 3.835(8) 114.7 . yes
C6 H6B I1 0.99 3.21 4.124(13) 153.4 4_565 yes
C6 H6B I2 0.99 3.3 3.836(8) 115.6 . yes

