# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_nk1146
_database_code_depnum_ccdc_archive 'CCDC 2493623'
loop_
_audit_author_name
_audit_author_address
'Nikita Korobeynikov'
;Nikolaev Institute of Inorganic Chemistry of SB RAS (NIIC SB RAS)
Russia
;
_audit_update_record             
;
2025-10-07 deposited with the CCDC.	2026-01-05 downloaded from the CCDC.
;
_audit_creation_date             2024-02-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl4 Sb, I2, 2(C5 H5 Br N), Cl'
_chemical_formula_sum            'C10 H10 Br2 Cl5 I2 N2 Sb'
_chemical_formula_weight         870.82
_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'
Cl Cl 0.1484 0.1585 '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'
Sb Sb -0.5866 1.5461 '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                   14.9208(3)
_cell_length_b                   7.09130(10)
_cell_length_c                   20.9159(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.3950(10)
_cell_angle_gamma                90
_cell_volume                     2194.66(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8348
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      30.06
_cell_measurement_theta_min      2.75
_shelx_estimated_absorpt_T_max   0.865
_shelx_estimated_absorpt_T_min   0.538
_exptl_absorpt_coefficient_mu    8.317
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1110 before and 0.0586 after correction.
The Ratio of minimum to maximum transmission is 0.7281.
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    2.636
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.085
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.018
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            27773
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.548
_diffrn_reflns_theta_min         1.584
_diffrn_ambient_temperature      150.00
_diffrn_detector                 PIXEL
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Incoatec HELIOS multilayer mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec IuS3.0 microfocus X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4944
_reflns_number_total             6700
_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       ?
_computing_data_collection       ?
_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  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.811
_refine_diff_density_min         -1.463
_refine_diff_density_rms         0.160
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         6700
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0335
_refine_ls_restrained_S_all      1.025
_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)+(0.0197P)²+1.1494P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0598
_refine_ls_wR_factor_ref         0.0657
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C6(H6), C8(H8), C9(H9), C1(H1A), C10(H10), C5(H5), C3(H3),
 C4(H4)
;
_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
Sb1 Sb 0.74070(2) 0.73992(3) 0.64473(2) 0.01743(6) Uani 1 1 d . . . . .
I1 I 0.35027(2) 0.72601(3) 0.61200(2) 0.02331(6) Uani 1 1 d . . . . .
I2 I 0.16598(2) 0.71757(4) 0.59968(2) 0.03761(8) Uani 1 1 d . . . . .
Br1 Br 1.06941(3) 0.23407(6) 0.50286(2) 0.03682(11) Uani 1 1 d . . . . .
Br2 Br 0.35530(3) 0.21878(7) 0.72019(2) 0.04165(12) Uani 1 1 d . . . . .
Cl2 Cl 0.73370(6) 0.53007(11) 0.55370(4) 0.02009(18) Uani 1 1 d . . . . .
Cl4 Cl 0.73861(6) 1.01221(12) 0.56986(5) 0.0249(2) Uani 1 1 d . . . . .
Cl5 Cl 0.90676(6) 0.74120(13) 0.65755(4) 0.02504(19) Uani 1 1 d . . . . .
Cl3 Cl 0.74377(6) 0.39642(14) 0.71321(4) 0.0270(2) Uani 1 1 d . . . . .
Cl1 Cl 0.54330(7) 0.74673(14) 0.62885(5) 0.0319(2) Uani 1 1 d . . . . .
N1 N 0.9118(2) 0.2596(4) 0.64668(16) 0.0292(8) Uani 1 1 d . . . . .
H1 H 0.853905 0.276364 0.649061 0.035 Uiso 1 1 calc R U . . .
N2 N 0.5700(2) 0.2588(4) 0.62051(16) 0.0269(7) Uani 1 1 d . . . . .
H2 H 0.628608 0.273769 0.630685 0.032 Uiso 1 1 calc R U . . .
C7 C 0.4271(3) 0.2275(5) 0.65249(18) 0.0237(8) Uani 1 1 d . . . . .
C6 C 0.5185(3) 0.2505(5) 0.66827(19) 0.0255(8) Uani 1 1 d . . . . .
H6 H 0.544626 0.260405 0.712027 0.031 Uiso 1 1 calc R U . . .
C8 C 0.3894(3) 0.2157(5) 0.58870(19) 0.0253(8) Uani 1 1 d . . . . .
H8 H 0.325942 0.202165 0.577807 0.030 Uiso 1 1 calc R U . . .
C9 C 0.4455(3) 0.2239(5) 0.54087(19) 0.0252(8) Uani 1 1 d . . . . .
H9 H 0.420871 0.214560 0.496774 0.030 Uiso 1 1 calc R U . . .
C2 C 1.0295(3) 0.2329(5) 0.58459(18) 0.0225(8) Uani 1 1 d . . . . .
C1 C 0.9393(3) 0.2571(5) 0.58838(19) 0.0254(8) Uani 1 1 d . . . . .
H1A H 0.897331 0.271692 0.550519 0.031 Uiso 1 1 calc R U . . .
C10 C 0.5369(3) 0.2455(5) 0.5578(2) 0.0277(9) Uani 1 1 d . . . . .
H10 H 0.576269 0.251039 0.525609 0.033 Uiso 1 1 calc R U . . .
C5 C 0.9672(3) 0.2380(5) 0.7014(2) 0.0360(10) Uani 1 1 d . . . . .
H5 H 0.944166 0.238825 0.741678 0.043 Uiso 1 1 calc R U . . .
C3 C 1.0890(3) 0.2124(6) 0.6397(2) 0.0381(11) Uani 1 1 d . . . . .
H3 H 1.151667 0.196519 0.637304 0.046 Uiso 1 1 calc R U . . .
C4 C 1.0568(3) 0.2149(6) 0.6990(2) 0.0408(11) Uani 1 1 d . . . . .
H4 H 1.097295 0.200478 0.737597 0.049 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sb1 Cl2 2.4083(9) . ?
Sb1 Cl4 2.4837(9) . ?
Sb1 Cl5 2.4577(9) . ?
Sb1 Cl3 2.8231(9) . ?
I1 I2 2.7293(4) . ?
Br1 C2 1.881(4) . ?
Br2 C7 1.883(4) . ?
N1 H1 0.8800 . ?
N1 C1 1.336(5) . ?
N1 C5 1.332(5) . ?
N2 H2 0.8800 . ?
N2 C6 1.337(5) . ?
N2 C10 1.344(5) . ?
C7 C6 1.371(5) . ?
C7 C8 1.382(5) . ?
C6 H6 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.385(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.373(5) . ?
C2 C1 1.369(5) . ?
C2 C3 1.368(6) . ?
C1 H1A 0.9500 . ?
C10 H10 0.9500 . ?
C5 H5 0.9500 . ?
C5 C4 1.354(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(6) . ?
C4 H4 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
Cl2 Sb1 Cl4 89.21(3) . . ?
Cl2 Sb1 Cl5 91.66(3) . . ?
Cl2 Sb1 Cl3 82.19(3) . . ?
Cl4 Sb1 Cl3 171.38(3) . . ?
Cl5 Sb1 Cl4 89.80(3) . . ?
Cl5 Sb1 Cl3 89.86(3) . . ?
C1 N1 H1 118.2 . . ?
C5 N1 H1 118.2 . . ?
C5 N1 C1 123.6(4) . . ?
C6 N2 H2 118.2 . . ?
C6 N2 C10 123.5(4) . . ?
C10 N2 H2 118.2 . . ?
C6 C7 Br2 117.9(3) . . ?
C6 C7 C8 120.5(4) . . ?
C8 C7 Br2 121.6(3) . . ?
N2 C6 C7 118.3(4) . . ?
N2 C6 H6 120.8 . . ?
C7 C6 H6 120.8 . . ?
C7 C8 H8 120.4 . . ?
C7 C8 C9 119.1(4) . . ?
C9 C8 H8 120.4 . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.4(4) . . ?
C10 C9 H9 120.3 . . ?
C1 C2 Br1 118.7(3) . . ?
C3 C2 Br1 121.3(3) . . ?
C3 C2 C1 120.0(4) . . ?
N1 C1 C2 118.3(4) . . ?
N1 C1 H1A 120.8 . . ?
C2 C1 H1A 120.8 . . ?
N2 C10 C9 119.2(4) . . ?
N2 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
N1 C5 H5 120.4 . . ?
N1 C5 C4 119.2(4) . . ?
C4 C5 H5 120.4 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.4(4) . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 119.5(4) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C2 C1 N1 -178.8(3) . . . . ?
Br1 C2 C3 C4 179.1(3) . . . . ?
Br2 C7 C6 N2 -179.3(3) . . . . ?
Br2 C7 C8 C9 179.7(3) . . . . ?
N1 C5 C4 C3 -0.6(6) . . . . ?
C7 C8 C9 C10 -0.7(5) . . . . ?
C6 N2 C10 C9 0.6(5) . . . . ?
C6 C7 C8 C9 1.2(6) . . . . ?
C8 C7 C6 N2 -0.9(5) . . . . ?
C8 C9 C10 N2 -0.2(5) . . . . ?
C2 C3 C4 C5 -0.1(7) . . . . ?
C1 N1 C5 C4 1.0(6) . . . . ?
C1 C2 C3 C4 0.5(6) . . . . ?
C10 N2 C6 C7 -0.1(5) . . . . ?
C5 N1 C1 C2 -0.7(6) . . . . ?
C3 C2 C1 N1 -0.1(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_nk1203
_database_code_depnum_ccdc_archive 'CCDC 2493625'
loop_
_audit_author_name
_audit_author_address
'Nikita Korobeynikov'
;Nikolaev Institute of Inorganic Chemistry of SB RAS (NIIC SB RAS)
Russia
;
_audit_update_record             
;
2025-10-31 deposited with the CCDC.	2026-01-05 downloaded from the CCDC.
;
_audit_creation_date             2025-10-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl4 Sb, I2, Cl, 2(C5 H5 Cl N)'
_chemical_formula_sum            'C10 H10 Cl7 I2 N2 Sb'
_chemical_formula_weight         781.90
_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'
Cl Cl 0.1484 0.1585 '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'
Sb Sb -0.5866 1.5461 '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                   14.5435(3)
_cell_length_b                   7.1608(2)
_cell_length_c                   20.8200(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.1310(10)
_cell_angle_gamma                90
_cell_volume                     2155.86(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7152
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      29.47
_cell_measurement_theta_min      2.82
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.609
_exptl_absorpt_coefficient_mu    5.007
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0827 before and 0.0541 after correction.
The Ratio of minimum to maximum transmission is 0.7779.
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    2.409
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            27709
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.569
_diffrn_reflns_theta_min         1.629
_diffrn_ambient_temperature      150.00
_diffrn_detector                 PIXEL
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Incoatec HELIOS multilayer mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec IuS3.0 microfocus X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5125
_reflns_number_total             6592
_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       ?
_computing_data_collection       ?
_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  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.827
_refine_diff_density_min         -1.006
_refine_diff_density_rms         0.153
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         6592
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.057
_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)+(0.0139P)²+0.1400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0526
_refine_ls_wR_factor_ref         0.0579
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C3(H3), C4(H4), C5(H5), C1(H1A), C6(H6), C10(H10), C8(H8),
 C9(H9)
;
_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
Sb1 Sb 0.74199(2) 0.24944(3) 0.64345(2) 0.01947(5) Uani 1 1 d . . . . .
I1 I 0.34128(2) 0.28088(3) 0.61142(2) 0.02680(6) Uani 1 1 d . . . . .
I2 I 0.15291(2) 0.30767(4) 0.60124(2) 0.03943(7) Uani 1 1 d . . . . .
Cl4 Cl 0.73711(5) 0.46251(11) 0.55369(3) 0.02325(16) Uani 1 1 d . . . . .
Cl5 Cl 0.91183(6) 0.25289(12) 0.65517(4) 0.02794(18) Uani 1 1 d . . . . .
Cl3 Cl 0.74079(6) 0.58683(12) 0.71468(4) 0.03034(19) Uani 1 1 d . . . . .
Cl2 Cl 0.74098(6) -0.01712(11) 0.56763(4) 0.02833(18) Uani 1 1 d . . . . .
Cl1 Cl 0.53998(6) 0.24553(13) 0.62755(4) 0.0338(2) Uani 1 1 d . . . . .
Cl7 Cl 0.42317(8) 0.29402(16) 0.98660(5) 0.0510(3) Uani 1 1 d . . . . .
Cl6 Cl 0.34829(8) 0.79185(16) 0.71367(5) 0.0526(3) Uani 1 1 d . . . . .
N1 N 0.5669(2) 0.7314(4) 0.62240(14) 0.0316(7) Uani 1 1 d . . . . .
H1 H 0.626122 0.709702 0.633123 0.038 Uiso 1 1 calc R U . . .
N2 N 0.5880(2) 0.2346(4) 0.85199(14) 0.0321(7) Uani 1 1 d . . . . .
H2 H 0.646653 0.206768 0.850478 0.038 Uiso 1 1 calc R U . . .
C3 C 0.3846(2) 0.7920(5) 0.58856(16) 0.0287(8) Uani 1 1 d . . . . .
H3 H 0.320484 0.812356 0.576884 0.034 Uiso 1 1 calc R U . . .
C4 C 0.4444(2) 0.7785(4) 0.54221(16) 0.0272(7) Uani 1 1 d . . . . .
H4 H 0.421863 0.790373 0.497857 0.033 Uiso 1 1 calc R U . . .
C5 C 0.5361(3) 0.7480(5) 0.55970(17) 0.0303(8) Uani 1 1 d . . . . .
H5 H 0.577777 0.738588 0.527715 0.036 Uiso 1 1 calc R U . . .
C7 C 0.4654(2) 0.2855(5) 0.91280(17) 0.0296(8) Uani 1 1 d . . . . .
C2 C 0.4196(2) 0.7753(5) 0.65272(16) 0.0290(8) Uani 1 1 d . . . . .
C1 C 0.5115(3) 0.7463(5) 0.66924(17) 0.0309(8) Uani 1 1 d . . . . .
H1A H 0.535771 0.736883 0.713327 0.037 Uiso 1 1 calc R U . . .
C6 C 0.5567(2) 0.2438(5) 0.90956(17) 0.0303(8) Uani 1 1 d . . . . .
H6 H 0.596905 0.221858 0.947827 0.036 Uiso 1 1 calc R U . . .
C10 C 0.5362(3) 0.2649(5) 0.79681(18) 0.0399(10) Uani 1 1 d . . . . .
H10 H 0.562024 0.256887 0.756874 0.048 Uiso 1 1 calc R U . . .
C8 C 0.4090(3) 0.3183(6) 0.8566(2) 0.0439(10) Uani 1 1 d . . . . .
H8 H 0.345581 0.347838 0.858134 0.053 Uiso 1 1 calc R U . . .
C9 C 0.4448(3) 0.3080(6) 0.79823(19) 0.0479(11) Uani 1 1 d . . . . .
H9 H 0.406338 0.330637 0.759182 0.057 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
Sb1 Cl4 2.4077(7) . ?
Sb1 Cl5 2.4562(8) . ?
Sb1 Cl3 2.8359(9) . ?
Sb1 Cl2 2.4760(8) . ?
I1 I2 2.7319(3) . ?
Cl7 C7 1.716(3) . ?
Cl6 C2 1.727(4) . ?
N1 H1 0.8800 . ?
N1 C5 1.339(4) . ?
N1 C1 1.334(4) . ?
N2 H2 0.8800 . ?
N2 C6 1.329(4) . ?
N2 C10 1.323(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.369(5) . ?
C3 C2 1.383(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.362(5) . ?
C5 H5 0.9500 . ?
C7 C6 1.369(5) . ?
C7 C8 1.376(5) . ?
C2 C1 1.360(5) . ?
C1 H1A 0.9500 . ?
C6 H6 0.9500 . ?
C10 H10 0.9500 . ?
C10 C9 1.369(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.374(5) . ?
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
Cl4 Sb1 Cl5 90.96(3) . . ?
Cl4 Sb1 Cl3 82.22(3) . . ?
Cl4 Sb1 Cl2 89.77(3) . . ?
Cl5 Sb1 Cl3 90.10(3) . . ?
Cl5 Sb1 Cl2 90.49(3) . . ?
Cl2 Sb1 Cl3 171.98(3) . . ?
C5 N1 H1 118.7 . . ?
C1 N1 H1 118.7 . . ?
C1 N1 C5 122.7(3) . . ?
C6 N2 H2 118.1 . . ?
C10 N2 H2 118.1 . . ?
C10 N2 C6 123.9(3) . . ?
C4 C3 H3 120.7 . . ?
C4 C3 C2 118.6(3) . . ?
C2 C3 H3 120.7 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
N1 C5 C4 119.4(3) . . ?
N1 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C6 C7 Cl7 119.6(3) . . ?
C6 C7 C8 119.3(3) . . ?
C8 C7 Cl7 121.2(3) . . ?
C3 C2 Cl6 121.1(3) . . ?
C1 C2 Cl6 118.4(3) . . ?
C1 C2 C3 120.5(3) . . ?
N1 C1 C2 118.8(3) . . ?
N1 C1 H1A 120.6 . . ?
C2 C1 H1A 120.6 . . ?
N2 C6 C7 118.9(3) . . ?
N2 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
N2 C10 H10 120.6 . . ?
N2 C10 C9 118.9(4) . . ?
C9 C10 H10 120.6 . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.7(4) . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 119.5(4) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?

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
N1 H1 Cl3 0.88 2.42 3.181(3) 145.7 . yes
N2 H2 Cl3 0.88 2.39 3.160(3) 145.7 2_646 yes

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
Cl7 C7 C6 N2 178.9(3) . . . . ?
Cl7 C7 C8 C9 -179.2(3) . . . . ?
Cl6 C2 C1 N1 179.3(3) . . . . ?
N2 C10 C9 C8 -0.2(6) . . . . ?
C3 C4 C5 N1 0.0(5) . . . . ?
C3 C2 C1 N1 -1.0(5) . . . . ?
C4 C3 C2 Cl6 179.7(3) . . . . ?
C4 C3 C2 C1 0.1(5) . . . . ?
C5 N1 C1 C2 1.6(5) . . . . ?
C7 C8 C9 C10 0.1(6) . . . . ?
C2 C3 C4 C5 0.4(5) . . . . ?
C1 N1 C5 C4 -1.1(5) . . . . ?
C6 N2 C10 C9 -0.1(6) . . . . ?
C6 C7 C8 C9 0.3(6) . . . . ?
C10 N2 C6 C7 0.5(5) . . . . ?
C8 C7 C6 N2 -0.6(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_nk1025
_database_code_depnum_ccdc_archive 'CCDC 2493624'
loop_
_audit_author_name
_audit_author_address
'Nikita Korobeynikov'
;Nikolaev Institute of Inorganic Chemistry of SB RAS (NIIC SB RAS)
Russia
;
_audit_update_record             
;
2025-10-21 deposited with the CCDC.	2026-01-05 downloaded from the CCDC.
;
_audit_creation_date             2025-10-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi Cl5, I2, 2(C5 H5 Br N)'
_chemical_formula_sum            'C10 H10 Bi Br2 Cl5 I2 N2'
_chemical_formula_weight         958.05
_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'
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'

_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                   14.8900(5)
_cell_length_b                   7.1531(2)
_cell_length_c                   20.9598(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.1090(10)
_cell_angle_gamma                90
_cell_volume                     2210.10(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6510
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      28.17
_cell_measurement_theta_min      2.76
_shelx_estimated_absorpt_T_max   0.754
_shelx_estimated_absorpt_T_min   0.154
_exptl_absorpt_coefficient_mu    14.988
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4195
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1088 before and 0.0485 after correction.
The Ratio of minimum to maximum transmission is 0.5626.
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    2.879
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            24399
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.309
_diffrn_reflns_theta_min         1.804
_diffrn_ambient_temperature      150.00
_diffrn_detector                 PIXEL
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Incoatec HELIOS multilayer mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec IuS3.0 microfocus X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4321
_reflns_number_total             5492
_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       ?
_computing_data_collection       ?
_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  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.030
_refine_diff_density_min         -1.496
_refine_diff_density_rms         0.188
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         5492
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0163P)²+2.7793P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0570
_refine_ls_wR_factor_ref         0.0606
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C10(H10), C6(H6), C1(H1A), C9(H9), C8(H8), C3(H3), C5(H5),
 C4(H4)
;
_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 0.74402(2) 0.27050(3) 0.64817(2) 0.01678(6) Uani 1 1 d . . . . .
I1 I 0.35101(2) 0.26895(5) 0.61481(2) 0.02351(9) Uani 1 1 d . . . . .
I2 I 0.16748(3) 0.27084(6) 0.60336(2) 0.03863(11) Uani 1 1 d . . . . .
Br1 Br 1.06776(4) 0.76024(9) 0.49875(3) 0.03641(16) Uani 1 1 d . . . . .
Br2 Br 0.35250(4) 0.77262(9) 0.71527(3) 0.03753(16) Uani 1 1 d . . . . .
Cl4 Cl 0.73517(9) 0.48761(17) 0.55235(6) 0.0202(3) Uani 1 1 d . . . . .
Cl3 Cl 0.74587(9) 0.62071(19) 0.71669(6) 0.0238(3) Uani 1 1 d . . . . .
Cl2 Cl 0.73808(9) -0.01322(17) 0.57243(7) 0.0241(3) Uani 1 1 d . . . . .
Cl5 Cl 0.91969(9) 0.26355(19) 0.66139(6) 0.0255(3) Uani 1 1 d . . . . .
Cl1 Cl 0.55163(9) 0.2569(2) 0.63465(7) 0.0305(3) Uani 1 1 d . . . . .
N2 N 0.5697(3) 0.7460(6) 0.6184(2) 0.0251(10) Uani 1 1 d . . . . .
H2 H 0.628812 0.736875 0.629147 0.030 Uiso 1 1 calc R U . . .
N1 N 0.9138(3) 0.7479(6) 0.6435(2) 0.0280(11) Uani 1 1 d . . . . .
H1 H 0.855465 0.740267 0.646387 0.034 Uiso 1 1 calc R U . . .
C10 C 0.5359(4) 0.7561(7) 0.5559(3) 0.0275(13) Uani 1 1 d . . . . .
H10 H 0.575507 0.752639 0.524122 0.033 Uiso 1 1 calc R U . . .
C6 C 0.5170(4) 0.7492(7) 0.6653(3) 0.0252(12) Uani 1 1 d . . . . .
H6 H 0.542736 0.739927 0.709272 0.030 Uiso 1 1 calc R U . . .
C1 C 0.9391(4) 0.7485(7) 0.5849(3) 0.0273(13) Uani 1 1 d . . . . .
H1A H 0.895582 0.740096 0.547185 0.033 Uiso 1 1 calc R U . . .
C7 C 0.4247(4) 0.7662(7) 0.6481(3) 0.0229(12) Uani 1 1 d . . . . .
C2 C 1.0305(4) 0.7618(7) 0.5809(3) 0.0242(12) Uani 1 1 d . . . . .
C9 C 0.4437(4) 0.7717(7) 0.5375(3) 0.0262(12) Uani 1 1 d . . . . .
H9 H 0.419181 0.778308 0.493192 0.031 Uiso 1 1 calc R U . . .
C8 C 0.3875(4) 0.7774(7) 0.5844(3) 0.0248(12) Uani 1 1 d . . . . .
H8 H 0.323697 0.788923 0.572755 0.030 Uiso 1 1 calc R U . . .
C3 C 1.0920(4) 0.7740(9) 0.6361(3) 0.0367(15) Uani 1 1 d . . . . .
H3 H 1.155081 0.783252 0.633780 0.044 Uiso 1 1 calc R U . . .
C5 C 0.9718(4) 0.7581(8) 0.6980(3) 0.0335(14) Uani 1 1 d . . . . .
H5 H 0.950177 0.755272 0.738539 0.040 Uiso 1 1 calc R U . . .
C4 C 1.0609(5) 0.7725(10) 0.6952(3) 0.0455(18) Uani 1 1 d . . . . .
H4 H 1.102604 0.781771 0.733750 0.055 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 Cl4 2.5274(12) . ?
Bi1 Cl3 2.8859(13) . ?
Bi1 Cl3 3.0121(12) 2_646 ?
Bi1 Cl2 2.5703(13) . ?
Bi1 Cl5 2.5918(13) . ?
Bi1 Cl1 2.8402(14) . ?
I1 I2 2.7093(5) . ?
Br1 C2 1.881(5) . ?
Br2 C7 1.889(5) . ?
N2 H2 0.8800 . ?
N2 C10 1.337(7) . ?
N2 C6 1.342(7) . ?
N1 H1 0.8800 . ?
N1 C1 1.336(7) . ?
N1 C5 1.333(8) . ?
C10 H10 0.9500 . ?
C10 C9 1.377(8) . ?
C6 H6 0.9500 . ?
C6 C7 1.375(8) . ?
C1 H1A 0.9500 . ?
C1 C2 1.378(8) . ?
C7 C8 1.374(7) . ?
C2 C3 1.375(8) . ?
C9 H9 0.9500 . ?
C9 C8 1.378(7) . ?
C8 H8 0.9500 . ?
C3 H3 0.9500 . ?
C3 C4 1.381(8) . ?
C5 H5 0.9500 . ?
C5 C4 1.340(9) . ?
C4 H4 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
Cl4 Bi1 Cl3 162.91(4) . 2_646 ?
Cl4 Bi1 Cl3 81.83(4) . . ?
Cl4 Bi1 Cl2 90.06(4) . . ?
Cl4 Bi1 Cl5 92.03(4) . . ?
Cl4 Bi1 Cl1 90.17(4) . . ?
Cl3 Bi1 Cl3 81.087(17) . 2_646 ?
Cl2 Bi1 Cl3 107.02(4) . 2_646 ?
Cl2 Bi1 Cl3 171.83(4) . . ?
Cl2 Bi1 Cl5 89.84(4) . . ?
Cl2 Bi1 Cl1 88.00(4) . . ?
Cl5 Bi1 Cl3 88.67(4) . 2_646 ?
Cl5 Bi1 Cl3 91.42(4) . . ?
Cl5 Bi1 Cl1 176.91(4) . . ?
Cl1 Bi1 Cl3 91.03(4) . . ?
Cl1 Bi1 Cl3 89.86(4) . 2_646 ?
Bi1 Cl3 Bi1 140.58(5) . 2_656 ?
C10 N2 H2 118.7 . . ?
C10 N2 C6 122.6(5) . . ?
C6 N2 H2 118.7 . . ?
C1 N1 H1 118.1 . . ?
C5 N1 H1 118.1 . . ?
C5 N1 C1 123.7(5) . . ?
N2 C10 H10 120.0 . . ?
N2 C10 C9 120.1(5) . . ?
C9 C10 H10 120.0 . . ?
N2 C6 H6 120.8 . . ?
N2 C6 C7 118.4(5) . . ?
C7 C6 H6 120.8 . . ?
N1 C1 H1A 121.1 . . ?
N1 C1 C2 117.7(5) . . ?
C2 C1 H1A 121.1 . . ?
C6 C7 Br2 117.4(4) . . ?
C8 C7 Br2 121.9(4) . . ?
C8 C7 C6 120.7(5) . . ?
C1 C2 Br1 118.5(4) . . ?
C3 C2 Br1 121.6(4) . . ?
C3 C2 C1 119.9(5) . . ?
C10 C9 H9 120.5 . . ?
C10 C9 C8 119.0(5) . . ?
C8 C9 H9 120.5 . . ?
C7 C8 C9 119.2(5) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.1(6) . . ?
C4 C3 H3 120.4 . . ?
N1 C5 H5 120.3 . . ?
N1 C5 C4 119.5(6) . . ?
C4 C5 H5 120.3 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(6) . . ?
C5 C4 H4 120.0 . . ?

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
Br1 C2 C3 C4 -179.3(5) . . . . ?
Br2 C7 C8 C9 -179.9(4) . . . . ?
N2 C10 C9 C8 0.3(8) . . . . ?
N2 C6 C7 Br2 -179.4(4) . . . . ?
N2 C6 C7 C8 0.8(8) . . . . ?
N1 C1 C2 Br1 179.3(4) . . . . ?
N1 C1 C2 C3 -0.1(8) . . . . ?
N1 C5 C4 C3 -0.9(10) . . . . ?
C10 N2 C6 C7 -0.9(8) . . . . ?
C10 C9 C8 C7 -0.4(8) . . . . ?
C6 N2 C10 C9 0.4(8) . . . . ?
C6 C7 C8 C9 -0.1(8) . . . . ?
C1 N1 C5 C4 0.9(9) . . . . ?
C1 C2 C3 C4 0.1(9) . . . . ?
C2 C3 C4 C5 0.4(10) . . . . ?
C5 N1 C1 C2 -0.4(8) . . . . ?

_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_nk1204
_database_code_depnum_ccdc_archive 'CCDC 2493626'
loop_
_audit_author_name
_audit_author_address
'Nikita Korobeynikov'
;Nikolaev Institute of Inorganic Chemistry of SB RAS (NIIC SB RAS)
Russia
;
_audit_update_record             
;
2025-10-31 deposited with the CCDC.	2026-01-05 downloaded from the CCDC.
;
_audit_creation_date             2025-10-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi Cl5, I2, 2(C5 H5 Cl N)'
_chemical_formula_sum            'C10 H10 Bi Cl7 I2 N2'
_chemical_formula_weight         869.13
_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'
Cl Cl 0.1484 0.1585 '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'

_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                   14.5781(2)
_cell_length_b                   7.20570(10)
_cell_length_c                   20.8721(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.3120(10)
_cell_angle_gamma                90
_cell_volume                     2174.69(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9943
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      31.46
_cell_measurement_theta_min      2.99
_shelx_estimated_absorpt_T_max   0.781
_shelx_estimated_absorpt_T_min   0.332
_exptl_absorpt_coefficient_mu    11.802
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.4861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1011 before and 0.0551 after correction.
The Ratio of minimum to maximum transmission is 0.6514.
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    2.655
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.022
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            29267
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.539
_diffrn_reflns_theta_min         1.967
_diffrn_ambient_temperature      150.00
_diffrn_detector                 PIXEL
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Incoatec HELIOS multilayer mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec IuS3.0 microfocus X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5933
_reflns_number_total             7246
_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       ?
_computing_data_collection       ?
_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  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.763
_refine_diff_density_min         -1.904
_refine_diff_density_rms         0.169
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         7246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0274
_refine_ls_restrained_S_all      1.029
_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)+(0.0148P)²+1.4094P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0512
_refine_ls_wR_factor_ref         0.0544
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C6(H6), C10(H10), C9(H9), C1(H1A), C8(H8), C5(H5), C3(H3),
 C4(H4)
;
_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 0.25383(2) 1.24002(2) 0.35279(2) 0.01580(3) Uani 1 1 d . . . . .
I1 I 0.65665(2) 1.22342(3) 0.38520(2) 0.02520(5) Uani 1 1 d . . . . .
I2 I 0.84336(2) 1.20870(4) 0.39201(2) 0.03998(7) Uani 1 1 d . . . . .
Cl4 Cl 0.26129(6) 1.01936(11) 0.44764(4) 0.01983(15) Uani 1 1 d . . . . .
Cl3 Cl 0.25546(6) 0.89486(12) 0.28210(4) 0.02484(17) Uani 1 1 d . . . . .
Cl2 Cl 0.25961(6) 1.51864(11) 0.42985(4) 0.02438(17) Uani 1 1 d . . . . .
Cl5 Cl 0.07433(6) 1.24217(12) 0.34037(4) 0.02574(17) Uani 1 1 d . . . . .
Cl1 Cl 0.44900(6) 1.25114(13) 0.36563(4) 0.02937(19) Uani 1 1 d . . . . .
Cl6 Cl 0.65025(8) 0.71610(16) 0.29161(5) 0.0437(3) Uani 1 1 d . . . . .
Cl7 Cl 0.57466(9) 1.21782(17) 0.00755(6) 0.0526(3) Uani 1 1 d . . . . .
N2 N 0.4318(2) 0.7641(4) 0.38068(15) 0.0261(6) Uani 1 1 d . . . . .
H2 H 0.372153 0.781728 0.369412 0.031 Uiso 1 1 calc R U . . .
N1 N 0.4142(2) 1.2612(4) 0.14250(15) 0.0282(7) Uani 1 1 d . . . . .
H1 H 0.355022 1.281154 0.144231 0.034 Uiso 1 1 calc R U . . .
C6 C 0.4870(3) 0.7528(5) 0.33401(17) 0.0257(7) Uani 1 1 d . . . . .
H6 H 0.462263 0.762420 0.289769 0.031 Uiso 1 1 calc R U . . .
C10 C 0.4633(3) 0.7497(5) 0.44370(18) 0.0274(8) Uani 1 1 d . . . . .
H10 H 0.421887 0.757319 0.475236 0.033 Uiso 1 1 calc R U . . .
C9 C 0.5560(3) 0.7238(5) 0.46206(18) 0.0260(7) Uani 1 1 d . . . . .
H9 H 0.579277 0.713244 0.506528 0.031 Uiso 1 1 calc R U . . .
C2 C 0.5353(3) 1.2240(5) 0.08169(18) 0.0285(8) Uani 1 1 d . . . . .
C1 C 0.4438(3) 1.2542(5) 0.08482(18) 0.0285(8) Uani 1 1 d . . . . .
H1A H 0.401854 1.269899 0.046502 0.034 Uiso 1 1 calc R U . . .
C7 C 0.5800(3) 0.7271(5) 0.35186(17) 0.0245(7) Uani 1 1 d . . . . .
C8 C 0.6152(3) 0.7131(5) 0.41590(18) 0.0274(8) Uani 1 1 d . . . . .
H8 H 0.679657 0.696186 0.428166 0.033 Uiso 1 1 calc R U . . .
C5 C 0.4701(3) 1.2393(5) 0.1980(2) 0.0393(10) Uani 1 1 d . . . . .
H5 H 0.445928 1.244941 0.238091 0.047 Uiso 1 1 calc R U . . .
C3 C 0.5953(3) 1.2020(6) 0.1376(2) 0.0422(11) Uani 1 1 d . . . . .
H3 H 0.659338 1.182138 0.135830 0.051 Uiso 1 1 calc R U . . .
C4 C 0.5612(3) 1.2092(7) 0.1963(2) 0.0502(12) Uani 1 1 d . . . . .
H4 H 0.601664 1.193115 0.235368 0.060 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 Cl4 2.5308(8) . ?
Bi1 Cl3 2.8934(8) . ?
Bi1 Cl3 3.0153(8) 2 ?
Bi1 Cl2 2.5672(8) . ?
Bi1 Cl5 2.5965(8) . ?
Bi1 Cl1 2.8249(9) . ?
I1 I2 2.7095(4) . ?
Cl6 C7 1.722(4) . ?
Cl7 C2 1.718(4) . ?
N2 H2 0.8800 . ?
N2 C6 1.343(5) . ?
N2 C10 1.341(5) . ?
N1 H1 0.8800 . ?
N1 C1 1.331(5) . ?
N1 C5 1.337(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.373(5) . ?
C10 H10 0.9500 . ?
C10 C9 1.369(5) . ?
C9 H9 0.9500 . ?
C9 C8 1.375(5) . ?
C2 C1 1.361(5) . ?
C2 C3 1.375(6) . ?
C1 H1A 0.9500 . ?
C7 C8 1.373(5) . ?
C8 H8 0.9500 . ?
C5 H5 0.9500 . ?
C5 C4 1.351(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(6) . ?
C4 H4 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
Cl4 Bi1 Cl3 162.79(2) . 2 ?
Cl4 Bi1 Cl3 81.75(2) . . ?
Cl4 Bi1 Cl2 90.37(3) . . ?
Cl4 Bi1 Cl5 91.39(3) . . ?
Cl4 Bi1 Cl1 90.06(3) . . ?
Cl3 Bi1 Cl3 81.042(10) . 2 ?
Cl2 Bi1 Cl3 106.84(3) . 2 ?
Cl2 Bi1 Cl3 171.87(3) . . ?
Cl2 Bi1 Cl5 90.58(3) . . ?
Cl2 Bi1 Cl1 88.05(3) . . ?
Cl5 Bi1 Cl3 88.84(2) . 2 ?
Cl5 Bi1 Cl3 91.60(3) . . ?
Cl5 Bi1 Cl1 178.01(3) . . ?
Cl1 Bi1 Cl3 89.95(2) . . ?
Cl1 Bi1 Cl3 90.18(2) . 2 ?
Bi1 Cl3 Bi1 142.36(3) . 2_545 ?
C6 N2 H2 118.5 . . ?
C10 N2 H2 118.5 . . ?
C10 N2 C6 123.0(3) . . ?
C1 N1 H1 118.4 . . ?
C1 N1 C5 123.1(3) . . ?
C5 N1 H1 118.4 . . ?
N2 C6 H6 120.8 . . ?
N2 C6 C7 118.3(3) . . ?
C7 C6 H6 120.8 . . ?
N2 C10 H10 120.4 . . ?
N2 C10 C9 119.2(4) . . ?
C9 C10 H10 120.4 . . ?
C10 C9 H9 120.1 . . ?
C10 C9 C8 119.8(3) . . ?
C8 C9 H9 120.1 . . ?
C1 C2 Cl7 119.3(3) . . ?
C1 C2 C3 119.9(3) . . ?
C3 C2 Cl7 120.8(3) . . ?
N1 C1 C2 118.8(3) . . ?
N1 C1 H1A 120.6 . . ?
C2 C1 H1A 120.6 . . ?
C6 C7 Cl6 117.8(3) . . ?
C6 C7 C8 120.5(3) . . ?
C8 C7 Cl6 121.6(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 C9 119.2(3) . . ?
C7 C8 H8 120.4 . . ?
N1 C5 H5 120.3 . . ?
N1 C5 C4 119.3(4) . . ?
C4 C5 H5 120.3 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.2(4) . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 119.6(4) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?

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
Cl6 C7 C8 C9 179.7(3) . . . . ?
Cl7 C2 C1 N1 -179.1(3) . . . . ?
Cl7 C2 C3 C4 179.5(3) . . . . ?
N2 C6 C7 Cl6 -179.1(2) . . . . ?
N2 C6 C7 C8 0.1(5) . . . . ?
N2 C10 C9 C8 0.0(5) . . . . ?
N1 C5 C4 C3 0.2(7) . . . . ?
C6 N2 C10 C9 0.5(5) . . . . ?
C6 C7 C8 C9 0.4(5) . . . . ?
C10 N2 C6 C7 -0.6(5) . . . . ?
C10 C9 C8 C7 -0.5(5) . . . . ?
C2 C3 C4 C5 -0.6(7) . . . . ?
C1 N1 C5 C4 0.2(6) . . . . ?
C1 C2 C3 C4 0.6(6) . . . . ?
C5 N1 C1 C2 -0.2(5) . . . . ?
C3 C2 C1 N1 -0.2(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
