# Supplementary Information (SI) for Materials Advances.
# 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_shs_556_mobo_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2kz1j4
_database_code_depnum_ccdc_archive 'CCDC 2382366'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.molstruc.2024.140857 2025
2 10.1039/d5ra06615h 2025
#Added by publCIF



_audit_update_record             
;
2024-09-06 deposited with the CCDC.	2025-12-17 downloaded from the CCDC.
;


_diffrn_radiation_monochromator  Mirror
# publcif _publ_body_element loop end
_audit_creation_date             2024-03-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl5 Sb, C8 H14 N2'
_chemical_formula_sum            'C8 H14 Cl5 N2 Sb'
_chemical_formula_weight         437.21
_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'
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                   10.8365(3)
_cell_length_b                   11.8067(3)
_cell_length_c                   12.0281(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.920(3)
_cell_angle_gamma                90
_cell_volume                     1472.31(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6819
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      2.5
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.758
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.972
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.797
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10523
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.797
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.376
_diffrn_reflns_theta_min         2.472
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.797
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3198
_reflns_number_total             3533
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         3533
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0218
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0138P)²+0.4328P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0420
_refine_ls_wR_factor_ref         0.0444
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb1 Sb 0.52588(2) 0.48666(2) 0.34826(2) 0.01165(5) Uani 1 1 d . . . . .
Cl1 Cl 0.38905(6) 0.38713(4) 0.17947(4) 0.01784(12) Uani 1 1 d . . . . .
Cl2 Cl 0.70719(6) 0.33591(4) 0.35403(5) 0.01717(12) Uani 1 1 d . . . . .
Cl3 Cl 0.35232(6) 0.64698(4) 0.30780(5) 0.02122(13) Uani 1 1 d . . . . .
Cl4 Cl 0.62614(5) 0.59689(4) 0.22820(4) 0.01591(11) Uani 1 1 d . . . . .
Cl5 Cl 0.66092(6) 0.64358(4) 0.53859(4) 0.01762(12) Uani 1 1 d . . . . .
N1 N 0.4117(2) 1.03734(14) 0.30768(16) 0.0173(4) Uani 1 1 d . . . . .
H1 H 0.334447 1.066170 0.276745 0.021 Uiso 1 1 calc R U . . .
N2 N 0.81256(18) 0.79198(13) 0.41481(15) 0.0128(4) Uani 1 1 d . . . . .
H2A H 0.810854 0.802526 0.339439 0.015 Uiso 1 1 calc R U . . .
H2B H 0.749605 0.741323 0.415846 0.015 Uiso 1 1 calc R U . . .
C1 C 0.4330(2) 0.92961(17) 0.28389(19) 0.0186(5) Uani 1 1 d . . . . .
H1A H 0.365794 0.885756 0.234229 0.022 Uiso 1 1 calc R U . . .
C2 C 0.5534(2) 0.88279(17) 0.33207(19) 0.0173(5) Uani 1 1 d . . . . .
H2 H 0.569057 0.806286 0.315799 0.021 Uiso 1 1 calc R U . . .
C3 C 0.6520(2) 0.94736(16) 0.40452(18) 0.0140(4) Uani 1 1 d . . . . .
C4 C 0.6249(2) 1.05996(17) 0.42612(19) 0.0164(5) Uani 1 1 d . . . . .
H4 H 0.690408 1.106211 0.474748 0.020 Uiso 1 1 calc R U . . .
C5 C 0.5036(2) 1.10341(17) 0.37694(19) 0.0182(5) Uani 1 1 d . . . . .
H5 H 0.484741 1.179540 0.391735 0.022 Uiso 1 1 calc R U . . .
C6 C 0.7844(2) 0.90155(16) 0.46347(18) 0.0148(5) Uani 1 1 d . . . . .
H6A H 0.849324 0.958081 0.456714 0.018 Uiso 1 1 calc R U . . .
H6B H 0.793481 0.891255 0.547152 0.018 Uiso 1 1 calc R U . . .
C7 C 0.9409(2) 0.74353(17) 0.48076(19) 0.0160(5) Uani 1 1 d . . . . .
H7A H 0.941244 0.725368 0.561194 0.019 Uiso 1 1 calc R U . . .
H7B H 1.009727 0.799842 0.484499 0.019 Uiso 1 1 calc R U . . .
C8 C 0.9665(2) 0.63720(18) 0.4206(2) 0.0230(5) Uani 1 1 d . . . . .
H8A H 0.963063 0.655062 0.340204 0.034 Uiso 1 1 calc R U . . .
H8B H 0.900990 0.580161 0.421057 0.034 Uiso 1 1 calc R U . . .
H8C H 1.052158 0.607570 0.461705 0.034 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 Cl1 2.4390(5) . ?
Sb1 Cl2 2.6370(5) . ?
Sb1 Cl3 2.6124(5) . ?
Sb1 Cl4 2.4234(5) . ?
Sb1 Cl5 2.9774(5) . ?
N1 H1 0.8800 . ?
N1 C1 1.338(3) . ?
N1 C5 1.346(3) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 C6 1.488(2) . ?
N2 C7 1.500(3) . ?
C1 H1A 0.9500 . ?
C1 C2 1.379(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.393(3) . ?
C3 C4 1.402(3) . ?
C3 C6 1.504(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.374(3) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.514(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Sb1 Cl2 87.966(18) . . ?
Cl1 Sb1 Cl3 87.919(18) . . ?
Cl1 Sb1 Cl5 169.572(17) . . ?
Cl2 Sb1 Cl5 101.777(17) . . ?
Cl3 Sb1 Cl2 169.894(19) . . ?
Cl3 Sb1 Cl5 81.863(17) . . ?
Cl4 Sb1 Cl1 91.837(19) . . ?
Cl4 Sb1 Cl2 85.315(18) . . ?
Cl4 Sb1 Cl3 85.596(19) . . ?
Cl4 Sb1 Cl5 85.340(16) . . ?
C1 N1 H1 118.6 . . ?
C1 N1 C5 122.7(2) . . ?
C5 N1 H1 118.6 . . ?
H2A N2 H2B 107.8 . . ?
C6 N2 H2A 109.0 . . ?
C6 N2 H2B 109.0 . . ?
C6 N2 C7 112.85(16) . . ?
C7 N2 H2A 109.0 . . ?
C7 N2 H2B 109.0 . . ?
N1 C1 H1A 120.3 . . ?
N1 C1 C2 119.5(2) . . ?
C2 C1 H1A 120.3 . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.2(2) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 118.1(2) . . ?
C2 C3 C6 123.44(18) . . ?
C4 C3 C6 118.42(19) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
N1 C5 C4 119.5(2) . . ?
N1 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
N2 C6 C3 113.83(17) . . ?
N2 C6 H6A 108.8 . . ?
N2 C6 H6B 108.8 . . ?
C3 C6 H6A 108.8 . . ?
C3 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
N2 C7 H7A 109.8 . . ?
N2 C7 H7B 109.8 . . ?
N2 C7 C8 109.53(17) . . ?
H7A C7 H7B 108.2 . . ?
C8 C7 H7A 109.8 . . ?
C8 C7 H7B 109.8 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

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 2.20 3.079(2) 175.8 2 yes
N2 H2A Cl2 0.91 2.31 3.2200(18) 176.0 2_655 yes
N2 H2B Cl4 0.91 2.83 3.4330(17) 124.5 . yes
N2 H2B Cl5 0.91 2.29 3.0676(19) 142.7 . 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
N1 C1 C2 C3 -0.2(3) . . . . ?
C1 N1 C5 C4 0.0(3) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C1 C2 C3 C6 177.9(2) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C2 C3 C6 N2 15.1(3) . . . . ?
C3 C4 C5 N1 -0.4(3) . . . . ?
C4 C3 C6 N2 -166.80(18) . . . . ?
C5 N1 C1 C2 0.3(3) . . . . ?
C6 N2 C7 C8 -175.75(18) . . . . ?
C6 C3 C4 C5 -177.7(2) . . . . ?
C7 N2 C6 C3 -175.55(17) . . . . ?



_olex2_submission_special_instructions 'No special instructions were received'



_publcif_funding_html            
;
;
####################################################################### 
# 
# 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_shs_559_mobo_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2l140t
_database_code_depnum_ccdc_archive 'CCDC 2384365'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/d5ra06614j 2025
#Added by publCIF



_audit_update_record             
;
2025-09-22 deposited with the CCDC.	2025-12-17 downloaded from the CCDC.
;
#Added by publCIF




_diffrn_radiation_monochromator  Mirror
# publcif _publ_body_element loop end
_audit_creation_date             2024-03-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi2 Br10, 2(H2 O), 2(C8 H14 N2)'
_chemical_formula_sum            'C16 H32 Bi2 Br10 N4 O2'
_chemical_formula_weight         1529.51
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.6409(2)
_cell_length_b                   12.0862(2)
_cell_length_c                   14.1356(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.685(3)
_cell_angle_gamma                90
_cell_volume                     1722.13(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8924
_cell_measurement_temperature    293
_cell_measurement_theta_max      30.2
_cell_measurement_theta_min      2.6
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    21.827
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.107a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    2.950
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11215
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.631
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2853
_reflns_number_total             3036
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would
 be possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.107a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.107a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.107a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.893
_refine_diff_density_min         -1.053
_refine_diff_density_rms         0.171
_refine_ls_extinction_coef       0.00152(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         3036
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0231
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0285P)²+1.9966P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0545
_refine_ls_wR_factor_ref         0.0553
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O1(H1B,H1C)
2.b Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C4(H4), C5(H5)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.20051(2) 0.48343(2) 0.59857(2) 0.01017(8) Uani 1 1 d . . . . .
Br1 Br 0.42518(4) 0.60690(4) 0.63256(4) 0.01428(12) Uani 1 1 d . . . . .
Br2 Br 0.33532(4) 0.34220(4) 0.75168(4) 0.01529(12) Uani 1 1 d . . . . .
Br3 Br 0.25221(4) 0.35304(4) 0.45761(4) 0.01499(12) Uani 1 1 d . . . . .
Br4 Br 0.05793(4) 0.64639(4) 0.43901(4) 0.01345(12) Uani 1 1 d . . . . .
Br5 Br 0.11876(4) 0.61733(4) 0.74600(3) 0.01366(12) Uani 1 1 d . . . . .
O1 O 0.0317(4) 0.3629(3) 0.8339(3) 0.0204(8) Uani 1 1 d G . . . .
H1B H 0.044809 0.392330 0.783227 0.031 Uiso 1 1 d G U . . .
H1C H 0.022224 0.293388 0.824947 0.031 Uiso 1 1 d G U . . .
N1 N 0.8422(4) 0.5486(4) 0.9866(3) 0.0187(9) Uani 1 1 d . . . . .
H1 H 0.874023 0.580355 1.043779 0.022 Uiso 1 1 calc R U . . .
N2 N 0.6263(4) 0.2887(3) 0.6955(3) 0.0137(9) Uani 1 1 d . . . . .
H2A H 0.556955 0.295520 0.717319 0.016 Uiso 1 1 calc R U . . .
H2B H 0.681940 0.239939 0.734359 0.016 Uiso 1 1 calc R U . . .
C1 C 0.8394(5) 0.6042(4) 0.9041(4) 0.0192(11) Uani 1 1 d . . . . .
H1A H 0.872389 0.675997 0.909382 0.023 Uiso 1 1 calc R U . . .
C2 C 0.7883(5) 0.5563(4) 0.8122(4) 0.0193(11) Uani 1 1 d . . . . .
H2 H 0.785270 0.595738 0.755024 0.023 Uiso 1 1 calc R U . . .
C3 C 0.7406(4) 0.4476(4) 0.8045(4) 0.0149(10) Uani 1 1 d . . . . .
C4 C 0.7450(5) 0.3928(4) 0.8916(4) 0.0187(11) Uani 1 1 d . . . . .
H4 H 0.712816 0.320903 0.888529 0.022 Uiso 1 1 calc R U . . .
C5 C 0.7966(5) 0.4444(5) 0.9826(4) 0.0204(11) Uani 1 1 d . . . . .
H5 H 0.799943 0.407376 1.041083 0.024 Uiso 1 1 calc R U . . .
C6 C 0.6941(5) 0.3976(4) 0.7029(4) 0.0174(11) Uani 1 1 d . . . . .
H6A H 0.633564 0.449109 0.658131 0.021 Uiso 1 1 calc R U . . .
H6B H 0.769922 0.388799 0.679655 0.021 Uiso 1 1 calc R U . . .
C7 C 0.5799(5) 0.2466(4) 0.5899(4) 0.0175(11) Uani 1 1 d . . . . .
H7A H 0.655408 0.239385 0.566045 0.021 Uiso 1 1 calc R U . . .
H7B H 0.519041 0.299692 0.547562 0.021 Uiso 1 1 calc R U . . .
C8 C 0.5116(5) 0.1362(5) 0.5824(4) 0.0226(12) Uani 1 1 d . . . . .
H8A H 0.475660 0.115004 0.513539 0.034 Uiso 1 1 calc R U . . .
H8B H 0.441094 0.141676 0.610899 0.034 Uiso 1 1 calc R U . . .
H8C H 0.574376 0.081523 0.618120 0.034 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 Br1 2.7271(5) . ?
Bi1 Br2 2.7688(5) . ?
Bi1 Br3 2.7310(5) . ?
Bi1 Br4 3.0612(5) 3_566 ?
Bi1 Br4 3.0126(5) . ?
Bi1 Br5 2.9800(5) . ?
O1 H1B 0.8504 . ?
O1 H1C 0.8505 . ?
N1 H1 0.8600 . ?
N1 C1 1.339(7) . ?
N1 C5 1.344(7) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 C6 1.489(6) . ?
N2 C7 1.502(6) . ?
C1 H1A 0.9300 . ?
C1 C2 1.366(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.400(7) . ?
C3 C4 1.385(7) . ?
C3 C6 1.489(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.376(7) . ?
C5 H5 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.507(7) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br1 Bi1 Br2 89.671(15) . . ?
Br1 Bi1 Br3 94.257(15) . . ?
Br1 Bi1 Br4 88.679(14) . . ?
Br1 Bi1 Br4 177.625(14) . 3_566 ?
Br1 Bi1 Br5 90.885(14) . . ?
Br2 Bi1 Br4 177.203(15) . . ?
Br2 Bi1 Br4 91.795(14) . 3_566 ?
Br2 Bi1 Br5 88.989(14) . . ?
Br3 Bi1 Br2 92.266(15) . . ?
Br3 Bi1 Br4 87.554(14) . 3_566 ?
Br3 Bi1 Br4 90.109(14) . . ?
Br3 Bi1 Br5 174.713(14) . . ?
Br4 Bi1 Br4 89.782(13) . 3_566 ?
Br5 Bi1 Br4 87.274(13) . 3_566 ?
Br5 Bi1 Br4 88.778(13) . . ?
Bi1 Br4 Bi1 90.218(13) . 3_566 ?
H1B O1 H1C 109.4 . . ?
C1 N1 H1 119.1 . . ?
C1 N1 C5 121.8(4) . . ?
C5 N1 H1 119.1 . . ?
H2A N2 H2B 108.0 . . ?
C6 N2 H2A 109.3 . . ?
C6 N2 H2B 109.3 . . ?
C6 N2 C7 111.5(4) . . ?
C7 N2 H2A 109.3 . . ?
C7 N2 H2B 109.3 . . ?
N1 C1 H1A 119.8 . . ?
N1 C1 C2 120.5(5) . . ?
C2 C1 H1A 119.8 . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.7(5) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 C6 117.1(4) . . ?
C4 C3 C2 118.1(5) . . ?
C4 C3 C6 124.7(5) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.3(5) . . ?
C5 C4 H4 119.9 . . ?
N1 C5 C4 119.6(5) . . ?
N1 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
N2 C6 C3 115.5(4) . . ?
N2 C6 H6A 108.4 . . ?
N2 C6 H6B 108.4 . . ?
C3 C6 H6A 108.4 . . ?
C3 C6 H6B 108.4 . . ?
H6A C6 H6B 107.5 . . ?
N2 C7 H7A 109.3 . . ?
N2 C7 H7B 109.3 . . ?
N2 C7 C8 111.5(4) . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

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
O1 H1C Br5 0.85 2.61 3.389(4) 152.6 2_546 yes
N1 H1 O1 0.86 1.83 2.684(6) 170.3 3_667 yes
N2 H2A Br2 0.89 2.62 3.494(4) 168.7 . yes
N2 H2B Br5 0.89 2.53 3.301(4) 145.6 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
N1 C1 C2 C3 -1.0(7) . . . . ?
C1 N1 C5 C4 -0.2(7) . . . . ?
C1 C2 C3 C4 1.2(7) . . . . ?
C1 C2 C3 C6 -176.3(4) . . . . ?
C2 C3 C4 C5 -0.9(7) . . . . ?
C2 C3 C6 N2 -171.5(4) . . . . ?
C3 C4 C5 N1 0.4(8) . . . . ?
C4 C3 C6 N2 11.2(7) . . . . ?
C5 N1 C1 C2 0.6(7) . . . . ?
C6 N2 C7 C8 179.9(4) . . . . ?
C6 C3 C4 C5 176.4(5) . . . . ?
C7 N2 C6 C3 178.5(4) . . . . ?








_olex2_submission_special_instructions 'No special instructions were received'



_publcif_funding_html            
;
;
####################################################################### 
# 
# 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_m43-rt-16h_auto
_database_code_depnum_ccdc_archive 'CCDC 2432091'
#Added by publCIF



_audit_update_record             
;
2025-03-18 deposited with the CCDC.	2025-12-17 downloaded from the CCDC.
;


_diffrn_radiation_monochromator  mirror
# publcif _publ_body_element loop end
_audit_creation_date             2025-03-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Bi Cl6), 3(C8 H14 N2)'
_chemical_formula_sum            'C24 H42 Bi2 Cl12 N6'
_chemical_formula_weight         1257.99
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   15.1677(3)
_cell_length_b                   11.9461(2)
_cell_length_c                   25.6539(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.092(2)
_cell_angle_gamma                90
_cell_volume                     4527.53(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    99611
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.5
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.495
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.107a (Rigaku Oxford Diffraction, 2025)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.846
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'Block, clear light colourless'
_exptl_crystal_F_000             2392
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            81638
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.446
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5402
_reflns_number_total             7995
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         7995
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0336
_refine_ls_restrained_S_all      1.012
_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)+(0.0156P)²+6.1510P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0508
_refine_ls_wR_factor_ref         0.0572
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 N6(H6A,H6B), C22(H22A,H22B), C23(H23A,H23B), N2(H2A,H2B), C6(H6C,H6D), C7(H7A,
 H7B), N4(H4A,H4B), C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 N5(H5), C17(H17), C18(H18), C20(H20), C21(H21), N1(H1), C1(H1A), C2(H2),
 C4(H4), C5(H5A), N3(H3), C9(H9), C10(H10), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C8(H8A,H8B,H8C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.76989(2) 0.49919(2) 0.38478(2) 0.03357(6) Uani 1 1 d . . . . .
Cl1 Cl 0.92112(10) 0.38093(13) 0.40663(6) 0.0502(4) Uani 1 1 d . . . . .
Cl2 Cl 0.61000(10) 0.61846(14) 0.37203(6) 0.0585(4) Uani 1 1 d . . . . .
Cl3 Cl 0.69064(11) 0.33298(12) 0.43873(6) 0.0506(4) Uani 1 1 d . . . . .
Cl4 Cl 0.71797(10) 0.36590(13) 0.29645(5) 0.0498(4) Uani 1 1 d . . . . .
Cl5 Cl 0.84997(10) 0.64517(13) 0.33351(6) 0.0523(4) Uani 1 1 d . . . . .
Cl6 Cl 0.81681(11) 0.61278(14) 0.47638(6) 0.0589(4) Uani 1 1 d . . . . .
Bi2 Bi 0.83551(2) 1.00584(2) 0.65941(2) 0.03735(7) Uani 1 1 d . . . . .
Cl7 Cl 0.87987(12) 0.89434(15) 0.74839(6) 0.0659(5) Uani 1 1 d . . . . .
Cl8 Cl 0.77310(10) 1.14634(13) 0.56956(6) 0.0547(4) Uani 1 1 d . . . . .
Cl9 Cl 0.76211(13) 1.16691(13) 0.71454(7) 0.0733(6) Uani 1 1 d . . . . .
Cl10 Cl 0.98508(10) 1.12001(12) 0.68185(6) 0.0491(4) Uani 1 1 d . . . . .
Cl11 Cl 0.91934(11) 0.86081(13) 0.60832(6) 0.0558(4) Uani 1 1 d . . . . .
Cl12 Cl 0.67516(12) 0.87501(17) 0.63548(9) 0.0877(6) Uani 1 1 d . . . . .
N5 N 0.6914(3) 1.0526(4) 0.8032(2) 0.0488(14) Uani 1 1 d . . . . .
H5 H 0.712369 1.083774 0.778326 0.059 Uiso 1 1 calc R U . . .
N6 N 0.5500(3) 0.7967(4) 0.91926(16) 0.0403(12) Uani 1 1 d . . . . .
H6A H 0.588351 0.749415 0.909178 0.048 Uiso 1 1 calc R U . . .
H6B H 0.500531 0.800716 0.892939 0.048 Uiso 1 1 calc R U . . .
C17 C 0.6784(4) 1.1150(5) 0.8439(3) 0.0531(17) Uani 1 1 d . . . . .
H17 H 0.692842 1.190767 0.844996 0.064 Uiso 1 1 calc R U . . .
C18 C 0.6445(4) 1.0697(5) 0.8835(2) 0.0475(16) Uani 1 1 d . . . . .
H18 H 0.634353 1.113905 0.911423 0.057 Uiso 1 1 calc R U . . .
C19 C 0.6251(4) 0.9555(4) 0.8818(2) 0.0354(14) Uani 1 1 d . . . . .
C20 C 0.6393(4) 0.8938(5) 0.8393(2) 0.0503(17) Uani 1 1 d . . . . .
H20 H 0.626075 0.817711 0.837314 0.060 Uiso 1 1 calc R U . . .
C21 C 0.6730(5) 0.9437(6) 0.7999(3) 0.0595(19) Uani 1 1 d . . . . .
H21 H 0.682858 0.901994 0.771099 0.071 Uiso 1 1 calc R U . . .
C22 C 0.5922(4) 0.9084(4) 0.9281(2) 0.0476(16) Uani 1 1 d . . . . .
H22A H 0.642996 0.904242 0.958770 0.057 Uiso 1 1 calc R U . . .
H22B H 0.548501 0.960005 0.937031 0.057 Uiso 1 1 calc R U . . .
C23 C 0.5251(4) 0.7528(5) 0.9686(2) 0.0489(16) Uani 1 1 d . . . . .
H23A H 0.578609 0.752103 0.997734 0.059 Uiso 1 1 calc R U . . .
H23B H 0.481235 0.802657 0.978585 0.059 Uiso 1 1 calc R U . . .
C24 C 0.4868(5) 0.6385(6) 0.9612(3) 0.076(2) Uani 1 1 d . . . . .
H24A H 0.433235 0.638953 0.932788 0.114 Uiso 1 1 calc R U . . .
H24B H 0.471698 0.613960 0.993691 0.114 Uiso 1 1 calc R U . . .
H24C H 0.530547 0.588410 0.952134 0.114 Uiso 1 1 calc R U . . .
N1 N 0.7461(4) -0.0516(5) 0.4319(2) 0.0590(15) Uani 1 1 d . . . . .
H1 H 0.727091 -0.079936 0.458120 0.071 Uiso 1 1 calc R U . . .
N2 N 0.8806(3) 0.1916(4) 0.30783(17) 0.0459(12) Uani 1 1 d . . . . .
H2A H 0.930944 0.185819 0.333459 0.055 Uiso 1 1 calc R U . . .
H2B H 0.845293 0.242601 0.318116 0.055 Uiso 1 1 calc R U . . .
C1 C 0.7449(5) -0.1140(6) 0.3891(3) 0.0649(19) Uani 1 1 d . . . . .
H1A H 0.723344 -0.187098 0.387436 0.078 Uiso 1 1 calc R U . . .
C2 C 0.7758(4) -0.0694(5) 0.3473(3) 0.0526(17) Uani 1 1 d . . . . .
H2 H 0.776352 -0.113321 0.317481 0.063 Uiso 1 1 calc R U . . .
C3 C 0.8059(4) 0.0385(5) 0.3490(2) 0.0433(15) Uani 1 1 d . . . . .
C4 C 0.8066(4) 0.0999(5) 0.3943(2) 0.0514(17) Uani 1 1 d . . . . .
H4 H 0.827978 0.173128 0.396959 0.062 Uiso 1 1 calc R U . . .
C5 C 0.7757(5) 0.0532(6) 0.4356(3) 0.062(2) Uani 1 1 d . . . . .
H5A H 0.775583 0.094838 0.466199 0.074 Uiso 1 1 calc R U . . .
C6 C 0.8338(4) 0.0834(5) 0.3012(2) 0.0520(16) Uani 1 1 d . . . . .
H6C H 0.873040 0.028822 0.289955 0.062 Uiso 1 1 calc R U . . .
H6D H 0.780120 0.090435 0.272471 0.062 Uiso 1 1 calc R U . . .
C7 C 0.9045(4) 0.2297(6) 0.2574(2) 0.0586(18) Uani 1 1 d . . . . .
H7A H 0.944897 0.175600 0.246906 0.070 Uiso 1 1 calc R U . . .
H7B H 0.849931 0.233295 0.229083 0.070 Uiso 1 1 calc R U . . .
C8 C 0.9490(5) 0.3418(6) 0.2636(3) 0.084(2) Uani 1 1 d . . . . .
H8A H 0.967760 0.360626 0.231378 0.125 Uiso 1 1 calc R U . . .
H8B H 1.000819 0.339938 0.293069 0.125 Uiso 1 1 calc R U . . .
H8C H 0.906919 0.397041 0.270338 0.125 Uiso 1 1 calc R U . . .
N3 N 0.6331(4) 0.4796(7) 0.5232(3) 0.089(3) Uani 1 1 d . . . . .
H3 H 0.652335 0.449144 0.497462 0.107 Uiso 1 1 calc R U . . .
N4 N 0.5031(3) 0.7327(4) 0.64451(18) 0.0502(13) Uani 1 1 d . . . . .
H4A H 0.451744 0.731667 0.619474 0.060 Uiso 1 1 calc R U . . .
H4B H 0.541592 0.778053 0.633381 0.060 Uiso 1 1 calc R U . . .
C9 C 0.6044(5) 0.5832(9) 0.5177(3) 0.087(3) Uani 1 1 d . . . . .
H9 H 0.605876 0.622685 0.486675 0.105 Uiso 1 1 calc R U . . .
C10 C 0.5719(4) 0.6341(6) 0.5579(3) 0.0642(19) Uani 1 1 d . . . . .
H10 H 0.550253 0.707133 0.554080 0.077 Uiso 1 1 calc R U . . .
C11 C 0.5723(4) 0.5738(6) 0.6037(2) 0.0491(17) Uani 1 1 d . . . . .
C12 C 0.6032(4) 0.4645(6) 0.6078(3) 0.069(2) Uani 1 1 d . . . . .
H12 H 0.602975 0.422428 0.638222 0.083 Uiso 1 1 calc R U . . .
C13 C 0.6337(5) 0.4198(7) 0.5667(4) 0.084(3) Uani 1 1 d . . . . .
H13 H 0.655246 0.346621 0.569025 0.101 Uiso 1 1 calc R U . . .
C14 C 0.5408(4) 0.6206(5) 0.6512(2) 0.0520(16) Uani 1 1 d . . . . .
H14A H 0.495452 0.570431 0.659314 0.062 Uiso 1 1 calc R U . . .
H14B H 0.591760 0.620652 0.681847 0.062 Uiso 1 1 calc R U . . .
C15 C 0.4846(4) 0.7775(6) 0.6954(3) 0.065(2) Uani 1 1 d . . . . .
H15A H 0.443032 0.727607 0.707650 0.079 Uiso 1 1 calc R U . . .
H15B H 0.540646 0.778993 0.722579 0.079 Uiso 1 1 calc R U . . .
C16 C 0.4455(6) 0.8913(7) 0.6889(3) 0.109(3) Uani 1 1 d . . . . .
H16A H 0.386703 0.888764 0.665144 0.164 Uiso 1 1 calc R U . . .
H16B H 0.484223 0.939817 0.674310 0.164 Uiso 1 1 calc R U . . .
H16C H 0.440093 0.919336 0.723149 0.164 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 Cl1 2.6437(15) . ?
Bi1 Cl2 2.7675(15) . ?
Bi1 Cl3 2.8384(14) . ?
Bi1 Cl4 2.7352(14) . ?
Bi1 Cl5 2.6402(14) . ?
Bi1 Cl6 2.6668(15) . ?
Bi2 Cl7 2.5965(16) . ?
Bi2 Cl8 2.8351(15) . ?
Bi2 Cl9 2.7667(15) . ?
Bi2 Cl10 2.5974(14) . ?
Bi2 Cl11 2.6630(14) . ?
Bi2 Cl12 2.8387(17) . ?
N5 H5 0.8600 . ?
N5 C17 1.333(7) . ?
N5 C21 1.329(7) . ?
N6 H6A 0.8900 . ?
N6 H6B 0.8900 . ?
N6 C22 1.474(6) . ?
N6 C23 1.496(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.352(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.395(7) . ?
C19 C20 1.372(7) . ?
C19 C22 1.499(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.369(7) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.480(8) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
N1 H1 0.8600 . ?
N1 C1 1.322(7) . ?
N1 C5 1.326(7) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 C6 1.467(7) . ?
N2 C7 1.492(6) . ?
C1 H1A 0.9300 . ?
C1 C2 1.372(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.364(8) . ?
C3 C4 1.373(7) . ?
C3 C6 1.484(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.371(8) . ?
C5 H5A 0.9300 . ?
C6 H6C 0.9700 . ?
C6 H6D 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.492(8) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
N3 H3 0.8600 . ?
N3 C9 1.310(10) . ?
N3 C13 1.323(10) . ?
N4 H4A 0.8900 . ?
N4 H4B 0.8900 . ?
N4 C14 1.452(7) . ?
N4 C15 1.495(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.379(9) . ?
C10 H10 0.9300 . ?
C10 C11 1.378(8) . ?
C11 C12 1.383(9) . ?
C11 C14 1.511(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.354(9) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.478(9) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
Cl1 Bi1 Cl2 174.37(4) . . ?
Cl1 Bi1 Cl3 88.04(5) . . ?
Cl1 Bi1 Cl4 86.43(5) . . ?
Cl1 Bi1 Cl6 92.26(5) . . ?
Cl2 Bi1 Cl3 87.78(5) . . ?
Cl4 Bi1 Cl2 96.99(5) . . ?
Cl4 Bi1 Cl3 85.56(4) . . ?
Cl5 Bi1 Cl1 89.06(5) . . ?
Cl5 Bi1 Cl2 95.21(5) . . ?
Cl5 Bi1 Cl3 176.79(5) . . ?
Cl5 Bi1 Cl4 92.89(5) . . ?
Cl5 Bi1 Cl6 92.39(5) . . ?
Cl6 Bi1 Cl2 83.91(5) . . ?
Cl6 Bi1 Cl3 89.10(5) . . ?
Cl6 Bi1 Cl4 174.53(5) . . ?
Cl7 Bi2 Cl8 172.21(5) . . ?
Cl7 Bi2 Cl9 87.80(5) . . ?
Cl7 Bi2 Cl10 92.02(5) . . ?
Cl7 Bi2 Cl11 92.37(5) . . ?
Cl7 Bi2 Cl12 86.93(6) . . ?
Cl8 Bi2 Cl12 92.19(5) . . ?
Cl9 Bi2 Cl8 84.54(5) . . ?
Cl9 Bi2 Cl12 93.97(6) . . ?
Cl10 Bi2 Cl8 89.05(5) . . ?
Cl10 Bi2 Cl9 87.36(5) . . ?
Cl10 Bi2 Cl11 87.72(5) . . ?
Cl10 Bi2 Cl12 178.27(5) . . ?
Cl11 Bi2 Cl8 95.38(5) . . ?
Cl11 Bi2 Cl9 175.08(5) . . ?
Cl11 Bi2 Cl12 90.95(6) . . ?
C17 N5 H5 118.9 . . ?
C21 N5 H5 118.9 . . ?
C21 N5 C17 122.2(6) . . ?
H6A N6 H6B 107.9 . . ?
C22 N6 H6A 109.3 . . ?
C22 N6 H6B 109.3 . . ?
C22 N6 C23 111.8(4) . . ?
C23 N6 H6A 109.3 . . ?
C23 N6 H6B 109.3 . . ?
N5 C17 H17 119.5 . . ?
N5 C17 C18 120.9(6) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 H18 120.6 . . ?
C17 C18 C19 118.7(6) . . ?
C19 C18 H18 120.6 . . ?
C18 C19 C22 116.6(5) . . ?
C20 C19 C18 118.8(5) . . ?
C20 C19 C22 124.6(5) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.3(6) . . ?
C21 C20 H20 119.8 . . ?
N5 C21 C20 119.1(6) . . ?
N5 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
N6 C22 C19 115.4(4) . . ?
N6 C22 H22A 108.4 . . ?
N6 C22 H22B 108.4 . . ?
C19 C22 H22A 108.4 . . ?
C19 C22 H22B 108.4 . . ?
H22A C22 H22B 107.5 . . ?
N6 C23 H23A 109.1 . . ?
N6 C23 H23B 109.1 . . ?
H23A C23 H23B 107.9 . . ?
C24 C23 N6 112.4(5) . . ?
C24 C23 H23A 109.1 . . ?
C24 C23 H23B 109.1 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 N1 H1 118.9 . . ?
C1 N1 C5 122.2(6) . . ?
C5 N1 H1 118.9 . . ?
H2A N2 H2B 107.9 . . ?
C6 N2 H2A 109.2 . . ?
C6 N2 H2B 109.2 . . ?
C6 N2 C7 112.0(4) . . ?
C7 N2 H2A 109.2 . . ?
C7 N2 H2B 109.2 . . ?
N1 C1 H1A 120.5 . . ?
N1 C1 C2 119.1(6) . . ?
C2 C1 H1A 120.5 . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 120.9(6) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 118.0(6) . . ?
C2 C3 C6 118.1(5) . . ?
C4 C3 C6 123.8(5) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.9(6) . . ?
C5 C4 H4 120.1 . . ?
N1 C5 C4 119.9(6) . . ?
N1 C5 H5A 120.1 . . ?
C4 C5 H5A 120.1 . . ?
N2 C6 C3 116.4(5) . . ?
N2 C6 H6C 108.2 . . ?
N2 C6 H6D 108.2 . . ?
C3 C6 H6C 108.2 . . ?
C3 C6 H6D 108.2 . . ?
H6C C6 H6D 107.3 . . ?
N2 C7 H7A 109.2 . . ?
N2 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 N2 112.0(5) . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C9 N3 H3 118.7 . . ?
C9 N3 C13 122.6(7) . . ?
C13 N3 H3 118.7 . . ?
H4A N4 H4B 107.9 . . ?
C14 N4 H4A 109.2 . . ?
C14 N4 H4B 109.2 . . ?
C14 N4 C15 112.0(5) . . ?
C15 N4 H4A 109.2 . . ?
C15 N4 H4B 109.2 . . ?
N3 C9 H9 119.9 . . ?
N3 C9 C10 120.2(8) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.8 . . ?
C11 C10 C9 118.3(7) . . ?
C11 C10 H10 120.8 . . ?
C10 C11 C12 119.5(6) . . ?
C10 C11 C14 123.6(6) . . ?
C12 C11 C14 116.9(6) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 119.0(8) . . ?
C13 C12 H12 120.5 . . ?
N3 C13 C12 120.3(8) . . ?
N3 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
N4 C14 C11 115.7(5) . . ?
N4 C14 H14A 108.3 . . ?
N4 C14 H14B 108.3 . . ?
C11 C14 H14A 108.3 . . ?
C11 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
N4 C15 H15A 109.1 . . ?
N4 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 N4 112.4(6) . . ?
C16 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
N5 H5 Cl9 0.86 2.19 3.049(5) 178.2 . yes
N6 H6A Cl8 0.89 2.39 3.187(5) 149.2 2_646 yes
N6 H6B Cl5 0.89 2.53 3.392(5) 164.5 4_576 yes
N2 H2A Cl11 0.89 2.48 3.357(5) 167.5 3_766 yes
N2 H2B Cl4 0.89 2.39 3.191(5) 149.5 . yes
N3 H3 Cl3 0.86 2.22 3.062(6) 166.2 . yes
N4 H4A Cl3 0.89 2.46 3.311(5) 161.5 3_666 yes
N4 H4B Cl12 0.89 2.32 3.167(5) 158.2 . 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
N5 C17 C18 C19 1.4(10) . . . . ?
C17 N5 C21 C20 0.2(10) . . . . ?
C17 C18 C19 C20 -1.3(9) . . . . ?
C17 C18 C19 C22 176.9(6) . . . . ?
C18 C19 C20 C21 0.7(9) . . . . ?
C18 C19 C22 N6 164.7(5) . . . . ?
C19 C20 C21 N5 -0.2(10) . . . . ?
C20 C19 C22 N6 -17.1(9) . . . . ?
C21 N5 C17 C18 -0.8(10) . . . . ?
C22 N6 C23 C24 -177.2(5) . . . . ?
C22 C19 C20 C21 -177.4(6) . . . . ?
C23 N6 C22 C19 176.0(5) . . . . ?
N1 C1 C2 C3 -1.3(10) . . . . ?
C1 N1 C5 C4 -0.1(11) . . . . ?
C1 C2 C3 C4 1.8(9) . . . . ?
C1 C2 C3 C6 -176.7(6) . . . . ?
C2 C3 C4 C5 -1.5(9) . . . . ?
C2 C3 C6 N2 -169.4(5) . . . . ?
C3 C4 C5 N1 0.7(10) . . . . ?
C4 C3 C6 N2 12.2(9) . . . . ?
C5 N1 C1 C2 0.5(11) . . . . ?
C6 N2 C7 C8 177.8(5) . . . . ?
C6 C3 C4 C5 177.0(6) . . . . ?
C7 N2 C6 C3 -179.2(5) . . . . ?
N3 C9 C10 C11 1.3(11) . . . . ?
C9 N3 C13 C12 0.6(12) . . . . ?
C9 C10 C11 C12 -1.3(10) . . . . ?
C9 C10 C11 C14 178.5(6) . . . . ?
C10 C11 C12 C13 1.1(10) . . . . ?
C10 C11 C14 N4 4.2(9) . . . . ?
C11 C12 C13 N3 -0.7(11) . . . . ?
C12 C11 C14 N4 -176.0(5) . . . . ?
C13 N3 C9 C10 -0.9(12) . . . . ?
C14 N4 C15 C16 -179.6(6) . . . . ?
C14 C11 C12 C13 -178.8(6) . . . . ?
C15 N4 C14 C11 -172.8(5) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 0.000 256.4 71.6 ?
2 0.500 0.000 0.500 256.4 71.6 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2




_olex2_submission_special_instructions 'No special instructions were received'



_publcif_funding_html            
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