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

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 2210164'
loop_
_audit_author_name
_audit_author_address
'Jie Mu'
;Southeast University
China
;
_audit_update_record             
;
2022-09-29 deposited with the CCDC.	2022-12-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'Bi2 Br9, 2(C6 H16 P), C4 H12 N'
_chemical_formula_sum            'C16 H44 Bi2 Br9 N P2'
_chemical_formula_weight         1449.61

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   23.4595(7)
_cell_length_b                   8.4198(2)
_cell_length_c                   19.3390(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.700(3)
_cell_angle_gamma                90
_cell_volume                     3807.08(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    11773
_cell_measurement_theta_min      2.2050
_cell_measurement_theta_max      29.4510

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.529
_exptl_crystal_F_000             2632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    18.770
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41773
_diffrn_reflns_av_unetI/netI     0.1614
_diffrn_reflns_av_R_equivalents  0.1359
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.113
_diffrn_reflns_theta_max         31.223
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.855
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.855
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             10587
_reflns_number_gt                5923
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1020P)²+33.2480P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00059(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         10587
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1769
_refine_ls_R_factor_gt           0.0945
_refine_ls_wR_factor_ref         0.2282
_refine_ls_wR_factor_gt          0.1966
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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 0.33180(2) 0.96422(3) 0.61585(2) 0.02772(6) Uani 1 1 d . . . . .
Bi2 Bi 0.16306(2) 1.02249(3) 0.63105(2) 0.03034(6) Uani 1 1 d . . . . .
Br6 Br 0.26818(3) 1.21187(8) 0.69365(3) 0.03730(18) Uani 1 1 d . . . . .
Br5 Br 0.23337(3) 1.01372(8) 0.50606(3) 0.03826(19) Uani 1 1 d . . . . .
Br4 Br 0.24484(3) 0.74275(8) 0.67660(4) 0.0428(2) Uani 1 1 d . . . . .
Br1 Br 0.41163(3) 0.92516(10) 0.72426(4) 0.0478(2) Uani 1 1 d . . . . .
Br7 Br 0.10878(4) 1.04570(10) 0.74977(4) 0.0555(2) Uani 1 1 d . . . . .
Br3 Br 0.38966(3) 1.20366(10) 0.55792(4) 0.0573(2) Uani 1 1 d . . . . .
Br2 Br 0.37471(3) 0.72444(10) 0.54080(4) 0.0593(2) Uani 1 1 d . . . . .
Br9 Br 0.11623(3) 1.29457(10) 0.58092(5) 0.0641(3) Uani 1 1 d . . . . .
Br8 Br 0.08260(4) 0.82906(12) 0.57189(5) 0.0777(3) Uani 1 1 d . . . . .
P2 P 0.10134(7) 0.9779(2) 0.32842(10) 0.0342(5) Uani 1 1 d . . . . .
P1 P 0.40379(7) 0.4583(2) 0.82464(10) 0.0363(5) Uani 1 1 d . . . . .
C8 C 0.1746(3) 1.0255(9) 0.3153(4) 0.048(2) Uani 1 1 d . . . . .
H8A H 0.1957 1.0409 0.3595 0.073 Uiso 1 1 calc R U . . .
H8B H 0.1758 1.1210 0.2884 0.073 Uiso 1 1 calc R U . . .
H8C H 0.1913 0.9399 0.2911 0.073 Uiso 1 1 calc R U . . .
N1 N 0.2557(3) 0.4599(7) 0.5537(3) 0.057(2) Uani 1 1 d . . . . .
H1D H 0.2924 0.4646 0.5453 0.068 Uiso 1 1 calc R U . . .
H1E H 0.2446 0.3588 0.5542 0.068 Uiso 1 1 calc R U . . .
H1F H 0.2511 0.5040 0.5947 0.068 Uiso 1 1 calc R U . . .
C13 C 0.2214(3) 0.5450(8) 0.4997(4) 0.040(2) Uani 1 1 d . . . . .
H13A H 0.2407 0.6427 0.4891 0.048 Uiso 1 1 calc R U . . .
H13B H 0.1849 0.5730 0.5166 0.048 Uiso 1 1 calc R U . . .
C10 C 0.0991(3) 0.7946(8) 0.3735(3) 0.0364(19) Uani 1 1 d . . . . .
H10A H 0.1191 0.7152 0.3483 0.044 Uiso 1 1 calc R U . . .
H10B H 0.1196 0.8069 0.4187 0.044 Uiso 1 1 calc R U . . .
C14 C 0.2108(3) 0.4483(8) 0.4339(4) 0.042(2) Uani 1 1 d . . . . .
H14A H 0.1949 0.3465 0.4457 0.050 Uiso 1 1 calc R U . . .
H14B H 0.1824 0.5026 0.4032 0.050 Uiso 1 1 calc R U . . .
C2 C 0.3322(3) 0.5237(10) 0.8282(5) 0.067(3) Uani 1 1 d . . . . .
H2A H 0.3079 0.4685 0.7938 0.100 Uiso 1 1 calc R U . . .
H2B H 0.3300 0.6358 0.8193 0.100 Uiso 1 1 calc R U . . .
H2C H 0.3198 0.5021 0.8734 0.100 Uiso 1 1 calc R U . . .
C12 C 0.0390(3) 0.5719(10) 0.4184(4) 0.057(3) Uani 1 1 d . . . . .
H12A H 0.0579 0.4957 0.3912 0.086 Uiso 1 1 calc R U . . .
H12B H 0.0002 0.5393 0.4221 0.086 Uiso 1 1 calc R U . . .
H12C H 0.0586 0.5787 0.4639 0.086 Uiso 1 1 calc R U . . .
C11 C 0.0396(3) 0.7335(8) 0.3834(4) 0.046(2) Uani 1 1 d . . . . .
H11A H 0.0182 0.7266 0.3384 0.055 Uiso 1 1 calc R U . . .
H11B H 0.0203 0.8094 0.4111 0.055 Uiso 1 1 calc R U . . .
C4 C 0.4087(3) 0.2673(9) 0.8628(3) 0.044(2) Uani 1 1 d . . . . .
H4A H 0.3920 0.2723 0.9071 0.053 Uiso 1 1 calc R U . . .
H4B H 0.3855 0.1949 0.8334 0.053 Uiso 1 1 calc R U . . .
C6 C 0.4686(4) 0.0386(9) 0.9086(5) 0.066(3) Uani 1 1 d . . . . .
H6A H 0.4413 -0.0295 0.8837 0.100 Uiso 1 1 calc R U . . .
H6B H 0.4590 0.0494 0.9557 0.100 Uiso 1 1 calc R U . . .
H6C H 0.5061 -0.0068 0.9081 0.100 Uiso 1 1 calc R U . . .
C5 C 0.4678(3) 0.1974(10) 0.8750(5) 0.060(3) Uani 1 1 d . . . . .
H5A H 0.4844 0.1885 0.8309 0.072 Uiso 1 1 calc R U . . .
H5B H 0.4915 0.2694 0.9040 0.072 Uiso 1 1 calc R U . . .
C15 C 0.2628(3) 0.4197(9) 0.3955(4) 0.062(3) Uani 1 1 d . . . . .
H15A H 0.2534 0.3446 0.3582 0.074 Uiso 1 1 calc R U . . .
H15B H 0.2925 0.3728 0.4268 0.074 Uiso 1 1 calc R U . . .
C1 C 0.4194(3) 0.4436(11) 0.7351(4) 0.063(3) Uani 1 1 d . . . . .
H1A H 0.3915 0.3767 0.7104 0.095 Uiso 1 1 calc R U . . .
H1B H 0.4568 0.3988 0.7326 0.095 Uiso 1 1 calc R U . . .
H1C H 0.4182 0.5475 0.7146 0.095 Uiso 1 1 calc R U . . .
C16 C 0.2850(4) 0.5705(11) 0.3655(4) 0.071(3) Uani 1 1 d . . . . .
H16A H 0.2590 0.6053 0.3276 0.107 Uiso 1 1 calc R U . . .
H16B H 0.3219 0.5513 0.3493 0.107 Uiso 1 1 calc R U . . .
H16C H 0.2881 0.6512 0.4007 0.107 Uiso 1 1 calc R U . . .
C9 C 0.0737(4) 1.1283(10) 0.3802(5) 0.074(3) Uani 1 1 d . . . . .
H9A H 0.0950 1.1302 0.4248 0.112 Uiso 1 1 calc R U . . .
H9B H 0.0342 1.1069 0.3859 0.112 Uiso 1 1 calc R U . . .
H9C H 0.0771 1.2293 0.3579 0.112 Uiso 1 1 calc R U . . .
C7 C 0.0619(4) 0.9635(11) 0.2447(4) 0.071(3) Uani 1 1 d . . . . .
H7A H 0.0761 1.0409 0.2139 0.106 Uiso 1 1 calc R U . . .
H7B H 0.0221 0.9829 0.2495 0.106 Uiso 1 1 calc R U . . .
H7C H 0.0666 0.8591 0.2261 0.106 Uiso 1 1 calc R U . . .
C3 C 0.4510(3) 0.5910(10) 0.8700(4) 0.065(3) Uani 1 1 d . . . . .
H3A H 0.4439 0.6967 0.8527 0.098 Uiso 1 1 calc R U . . .
H3B H 0.4897 0.5614 0.8634 0.098 Uiso 1 1 calc R U . . .
H3C H 0.4451 0.5875 0.9185 0.098 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 2.7144(7) . ?
Bi1 Br3 2.7223(8) . ?
Bi1 Br2 2.7267(9) . ?
Bi1 Br6 3.0344(7) . ?
Bi1 Br5 3.0349(7) . ?
Bi1 Br4 3.0679(8) . ?
Bi2 Br8 2.6778(9) . ?
Bi2 Br9 2.6871(8) . ?
Bi2 Br7 2.7221(8) . ?
Bi2 Br5 3.0368(7) . ?
Bi2 Br6 3.0985(7) . ?
Bi2 Br4 3.1188(7) . ?
P2 C9 1.769(9) . ?
P2 C10 1.775(7) . ?
P2 C7 1.801(8) . ?
P2 C8 1.802(7) . ?
P1 C3 1.756(8) . ?
P1 C4 1.770(8) . ?
P1 C2 1.775(7) . ?
P1 C1 1.803(8) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
N1 C13 1.455(9) . ?
N1 H1D 0.8900 . ?
N1 H1E 0.8900 . ?
N1 H1F 0.8900 . ?
C13 C14 1.513(10) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C10 C11 1.513(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C14 C15 1.498(11) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C12 C11 1.520(11) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C4 C5 1.507(10) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C6 C5 1.486(11) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C15 C16 1.506(12) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 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 Br3 94.12(2) . . ?
Br1 Bi1 Br2 93.44(2) . . ?
Br3 Bi1 Br2 96.37(3) . . ?
Br1 Bi1 Br6 92.09(2) . . ?
Br3 Bi1 Br6 88.70(2) . . ?
Br2 Bi1 Br6 172.21(2) . . ?
Br1 Bi1 Br5 173.86(2) . . ?
Br3 Bi1 Br5 89.25(2) . . ?
Br2 Bi1 Br5 91.27(2) . . ?
Br6 Bi1 Br5 82.853(19) . . ?
Br1 Bi1 Br4 93.95(2) . . ?
Br3 Bi1 Br4 167.78(2) . . ?
Br2 Bi1 Br4 92.29(2) . . ?
Br6 Bi1 Br4 81.851(19) . . ?
Br5 Bi1 Br4 81.932(19) . . ?
Br8 Bi2 Br9 96.39(3) . . ?
Br8 Bi2 Br7 92.40(3) . . ?
Br9 Bi2 Br7 92.14(3) . . ?
Br8 Bi2 Br5 93.15(3) . . ?
Br9 Bi2 Br5 88.06(2) . . ?
Br7 Bi2 Br5 174.39(2) . . ?
Br8 Bi2 Br6 172.11(3) . . ?
Br9 Bi2 Br6 89.48(2) . . ?
Br7 Bi2 Br6 92.63(2) . . ?
Br5 Bi2 Br6 81.764(19) . . ?
Br8 Bi2 Br4 93.28(3) . . ?
Br9 Bi2 Br4 165.83(2) . . ?
Br7 Bi2 Br4 97.79(2) . . ?
Br5 Bi2 Br4 81.072(19) . . ?
Br6 Bi2 Br4 80.028(18) . . ?
Bi1 Br6 Bi2 81.991(17) . . ?
Bi1 Br5 Bi2 83.004(18) . . ?
Bi1 Br4 Bi2 81.129(17) . . ?
C9 P2 C10 108.5(4) . . ?
C9 P2 C7 111.8(4) . . ?
C10 P2 C7 110.4(4) . . ?
C9 P2 C8 108.5(4) . . ?
C10 P2 C8 109.2(3) . . ?
C7 P2 C8 108.3(4) . . ?
C3 P1 C4 110.7(4) . . ?
C3 P1 C2 110.1(4) . . ?
C4 P1 C2 107.1(4) . . ?
C3 P1 C1 110.7(4) . . ?
C4 P1 C1 109.1(4) . . ?
C2 P1 C1 109.0(4) . . ?
P2 C8 H8A 109.5 . . ?
P2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
P2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C13 N1 H1D 109.5 . . ?
C13 N1 H1E 109.5 . . ?
H1D N1 H1E 109.5 . . ?
C13 N1 H1F 109.5 . . ?
H1D N1 H1F 109.5 . . ?
H1E N1 H1F 109.5 . . ?
N1 C13 C14 112.4(6) . . ?
N1 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
N1 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C11 C10 P2 115.0(4) . . ?
C11 C10 H10A 108.5 . . ?
P2 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
P2 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C15 C14 C13 114.8(6) . . ?
C15 C14 H14A 108.6 . . ?
C13 C14 H14A 108.6 . . ?
C15 C14 H14B 108.6 . . ?
C13 C14 H14B 108.6 . . ?
H14A C14 H14B 107.5 . . ?
P1 C2 H2A 109.5 . . ?
P1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
P1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C11 C12 113.8(6) . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C5 C4 P1 116.6(5) . . ?
C5 C4 H4A 108.2 . . ?
P1 C4 H4A 108.2 . . ?
C5 C4 H4B 108.2 . . ?
P1 C4 H4B 108.2 . . ?
H4A C4 H4B 107.3 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C6 C5 C4 113.5(7) . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C4 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C14 C15 C16 112.1(7) . . ?
C14 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
P1 C1 H1A 109.5 . . ?
P1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
P1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
P2 C9 H9A 109.5 . . ?
P2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
P2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
P2 C7 H7A 109.5 . . ?
P2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
P2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
P1 C3 H3A 109.5 . . ?
P1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
P1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 P2 C10 C11 66.2(6) . . . . ?
C7 P2 C10 C11 -56.7(6) . . . . ?
C8 P2 C10 C11 -175.6(5) . . . . ?
N1 C13 C14 C15 -68.5(8) . . . . ?
P2 C10 C11 C12 176.6(5) . . . . ?
C3 P1 C4 C5 -51.4(7) . . . . ?
C2 P1 C4 C5 -171.5(6) . . . . ?
C1 P1 C4 C5 70.7(6) . . . . ?
P1 C4 C5 C6 178.7(6) . . . . ?
C13 C14 C15 C16 -67.2(8) . . . . ?

_refine_diff_density_max         3.415
_refine_diff_density_min         -3.410
_refine_diff_density_rms         0.371



####################################################################### 
# 
# 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_new
_database_code_depnum_ccdc_archive 'CCDC 2210178'
loop_
_audit_author_name
_audit_author_address
'Jie Mu'
;Southeast University
China
;
_audit_update_record             
;
2022-10-22 deposited with the CCDC.	2022-12-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'Bi2 Br9, 2(C6 P), C4 N'
_chemical_formula_sum            'C16 Bi2 Br9 N P2'
_chemical_formula_weight         1405.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
C C 0.0033 0.0016 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P m c n'
_space_group_name_Hall           '-P 2n 2a'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   23.522(2)
_cell_length_b                   8.5667(6)
_cell_length_c                   19.7659(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3982.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    363(2)
_cell_measurement_reflns_used    3010
_cell_measurement_theta_min      2.2430
_cell_measurement_theta_max      24.5450
_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.344
_exptl_crystal_F_000             2456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    17.939
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      363(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25171
_diffrn_reflns_av_unetI/netI     0.1138
_diffrn_reflns_av_R_equivalents  0.1158
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.732
_diffrn_reflns_theta_max         30.836
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.819
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.819
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.819
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5236
_reflns_number_gt                2259
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0972P)²+31.0799P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00030(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5236
_refine_ls_number_parameters     98
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.2491
_refine_ls_R_factor_gt           0.1098
_refine_ls_wR_factor_ref         0.2725
_refine_ls_wR_factor_gt          0.2160
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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 0.66438(2) 0.46884(4) 0.37339(2) 0.07976(10) Uani 1 1 d . . . . .
Br6 Br 0.7500 0.22719(14) 0.32069(6) 0.0932(4) Uani 1 2 d S T P . .
Br5 Br 0.7500 0.51208(17) 0.48656(6) 0.0962(5) Uani 1 2 d S T P . .
Br4 Br 0.7500 0.69229(15) 0.30088(6) 0.1052(5) Uani 1 2 d S T P . .
Br1 Br 0.59500(5) 0.43181(15) 0.26437(5) 0.1294(4) Uani 1 1 d . . . . .
Br2 Br 0.60340(6) 0.71328(16) 0.42179(6) 0.1529(5) Uani 1 1 d . . . . .
Br3 Br 0.61008(5) 0.25023(17) 0.44636(7) 0.1630(5) Uani 1 1 d . . . . .
P1 P 0.59647(14) 0.9618(3) 0.17156(14) 0.1115(9) Uani 1 1 d . . . . .
C1 C 0.5792(5) 0.9508(11) 0.2590(5) 0.1115(9) Uani 1 1 d . . . . .
C3 C 0.5531(5) 1.1045(12) 0.1319(5) 0.1115(9) Uani 1 1 d . . . . .
C2 C 0.6699(5) 1.0159(11) 0.1705(5) 0.1115(9) Uani 1 1 d . . . . .
N1 N 0.7500 -0.0804(14) 0.4299(5) 0.246(7) Uani 1 2 d DS T P . .
C7 C 0.7500 0.0193(13) 0.4906(3) 0.246(7) Uani 1 2 d DS T P . .
C10 C 0.7500 0.1492(9) 0.6226(10) 0.246(7) Uani 1 2 d DS T P . .
C8 C 0.7143(4) -0.023(3) 0.5520(4) 0.246(7) Uani 0.5 1 d D . P . .
C9 C 0.7500 -0.0271(9) 0.6167(3) 0.246(7) Uani 1 2 d DS T P . .
C6 C 0.5412(5) 0.5536(11) 0.0836(5) 0.1115(9) Uani 1 1 d . . . . .
C4 C 0.5957(3) 0.7686(11) 0.1276(4) 0.1115(9) Uani 1 1 d D . . . .
C5 C 0.5360(3) 0.7098(11) 0.1179(4) 0.1115(9) Uani 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 Br3 2.6868(14) . ?
Bi1 Br2 2.7124(14) . ?
Bi1 Br1 2.7216(11) . ?
Bi1 Br5 3.0326(9) . ?
Bi1 Br6 3.0703(10) . ?
Bi1 Br4 3.1264(10) . ?
Br6 Bi1 3.0703(10) 7_755 ?
Br5 Bi1 3.0326(9) 7_755 ?
Br4 Bi1 3.1263(10) 7_755 ?
P1 C3 1.774(11) . ?
P1 C1 1.777(10) . ?
P1 C2 1.788(11) . ?
P1 C4 1.869(10) . ?
N1 C7 1.473(11) . ?
C7 C8 1.519(10) . ?
C7 C8 1.520(10) 7_755 ?
C10 C9 1.516(10) . ?
C8 C9 1.531(9) . ?
C8 C8 1.68(2) 7_755 ?
C9 C8 1.531(9) 7_755 ?
C6 C5 1.505(14) . ?
C4 C5 1.504(9) . ?

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
Br3 Bi1 Br2 95.59(4) . . ?
Br3 Bi1 Br1 93.37(4) . . ?
Br2 Bi1 Br1 92.99(4) . . ?
Br3 Bi1 Br5 90.28(4) . . ?
Br2 Bi1 Br5 89.81(4) . . ?
Br1 Bi1 Br5 175.16(3) . . ?
Br3 Bi1 Br6 91.37(4) . . ?
Br2 Bi1 Br6 170.77(4) . . ?
Br1 Bi1 Br6 92.64(3) . . ?
Br5 Bi1 Br6 84.09(3) . . ?
Br3 Bi1 Br4 168.26(3) . . ?
Br2 Bi1 Br4 91.70(4) . . ?
Br1 Bi1 Br4 95.43(3) . . ?
Br5 Bi1 Br4 80.53(3) . . ?
Br6 Bi1 Br4 80.49(3) . . ?
Bi1 Br6 Bi1 81.98(3) 7_755 . ?
Bi1 Br5 Bi1 83.22(3) 7_755 . ?
Bi1 Br4 Bi1 80.21(3) 7_755 . ?
C3 P1 C1 109.6(5) . . ?
C3 P1 C2 111.8(5) . . ?
C1 P1 C2 104.2(5) . . ?
C3 P1 C4 113.5(4) . . ?
C1 P1 C4 113.7(4) . . ?
C2 P1 C4 103.5(4) . . ?
N1 C7 C8 120.8(10) . . ?
N1 C7 C8 120.8(10) . 7_755 ?
C8 C7 C8 67.0(8) . 7_755 ?
C7 C8 C9 111.7(7) . . ?
C7 C8 C8 56.5(4) . 7_755 ?
C9 C8 C8 56.8(4) . 7_755 ?
C10 C9 C8 92.4(11) . 7_755 ?
C10 C9 C8 92.4(11) . . ?
C8 C9 C8 66.5(8) 7_755 . ?
C5 C4 P1 111.4(6) . . ?
C4 C5 C6 106.3(7) . . ?

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 C7 C8 C9 126.9(11) . . . . ?
C8 C7 C8 C9 13.6(18) 7_755 . . . ?
N1 C7 C8 C8 113.2(11) . . . 7_755 ?
C7 C8 C9 C10 78.0(14) . . . . ?
C8 C8 C9 C10 91.6(7) 7_755 . . . ?
C7 C8 C9 C8 -13.6(18) . . . 7_755 ?
C3 P1 C4 C5 -53.4(8) . . . . ?
C1 P1 C4 C5 72.8(8) . . . . ?
C2 P1 C4 C5 -174.8(7) . . . . ?
P1 C4 C5 C6 -178.9(6) . . . . ?

_refine_diff_density_max         1.476
_refine_diff_density_min         -1.072
_refine_diff_density_rms         0.244



