# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_c
_database_code_depnum_ccdc_archive 'CCDC 1909092'
loop_
_audit_author_name
_audit_author_address
'Hui Hui Li'
;Southeast University
China
;
_audit_update_record             
;
2019-09-16 deposited with the CCDC.	2020-01-06 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         ?
_chemical_formula_sum            'C6 H21 Bi Cl9 N3'
_chemical_formula_weight         663.29

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.1810(2)
_cell_length_b                   11.7216(4)
_cell_length_c                   11.8724(3)
_cell_angle_alpha                104.188(2)
_cell_angle_beta                 93.217(2)
_cell_angle_gamma                108.402(3)
_cell_volume                     1036.24(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    8310
_cell_measurement_theta_min      2.6320
_cell_measurement_theta_max      31.3740

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.126
_exptl_crystal_F_000             628
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    9.659
_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      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku, SCXmini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16819
_diffrn_reflns_av_unetI/netI     0.0665
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.652
_diffrn_reflns_theta_max         31.650
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.819
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.819
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.819
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6989
_reflns_number_gt                4380
_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)+(0.0435P)²] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6989
_refine_ls_number_parameters     175
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.0916
_refine_ls_wR_factor_gt          0.0865
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.001
_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 0.15760(2) 0.33319(2) 0.21098(2) 0.03428(8) Uani 1 1 d . . . . .
Cl1 Cl 0.0190(2) 0.51436(17) 0.29321(14) 0.0575(4) Uani 1 1 d . . . . .
Cl2 Cl 0.1840(3) 0.3027(2) 0.42313(14) 0.0674(5) Uani 1 1 d . . . . .
Cl3 Cl -0.1582(2) 0.16035(17) 0.15791(17) 0.0629(4) Uani 1 1 d . . . . .
Cl4 Cl 0.2909(2) 0.15288(15) 0.11943(15) 0.0538(4) Uani 1 1 d . . . . .
Cl5 Cl 0.1007(2) 0.36039(14) -0.01374(12) 0.0466(3) Uani 1 1 d . . . . .
Cl6 Cl 0.49742(18) 0.50244(14) 0.26720(13) 0.0461(3) Uani 1 1 d . . . . .
Cl7 Cl 0.6605(3) 0.1592(2) 0.55348(18) 0.0789(6) Uani 1 1 d . . . . .
C1 C 0.6379(17) 0.2884(10) 0.4008(10) 0.121(4) Uani 1 1 d . . . . .
H1A H 0.7384 0.2867 0.3617 0.145 Uiso 1 1 calc DR U . . .
H1B H 0.5507 0.2875 0.3414 0.145 Uiso 1 1 calc R U . . .
C2 C 0.5725(14) 0.1681(9) 0.4199(8) 0.098(3) Uani 1 1 d . . . . .
H2A H 0.5963 0.1080 0.3567 0.118 Uiso 1 1 calc R U . . .
H2B H 0.4472 0.1443 0.4166 0.118 Uiso 1 1 calc R U . . .
N1 N 0.681(2) 0.3905(9) 0.4650(7) 0.191(7) Uani 1 1 d . . . . .
H1C H 0.5919 0.4014 0.5002 0.287 Uiso 1 1 calc R U . . .
H1D H 0.7159 0.4462 0.4244 0.287 Uiso 1 1 calc R U . . .
H1E H 0.7688 0.4009 0.5189 0.287 Uiso 1 1 calc DR U . . .
Cl9 Cl 0.4174(3) 0.88228(18) 0.13688(16) 0.0693(5) Uani 1 1 d . . . . .
C6 C 0.3787(9) 0.7249(6) 0.1434(5) 0.0523(15) Uani 1 1 d . . . . .
H6A H 0.4486 0.7259 0.2126 0.063 Uiso 1 1 calc R U . . .
H6B H 0.2571 0.6864 0.1499 0.063 Uiso 1 1 calc R U . . .
C5 C 0.4222(8) 0.6507(6) 0.0385(5) 0.0442(13) Uani 1 1 d . . . . .
H5A H 0.4120 0.5692 0.0484 0.053 Uiso 1 1 calc R U . . .
H5B H 0.5422 0.6918 0.0302 0.053 Uiso 1 1 calc R U . . .
N3 N 0.3092(7) 0.6342(5) -0.0688(4) 0.0486(12) Uani 1 1 d . . . . .
H3A H 0.1996 0.5923 -0.0636 0.073 Uiso 1 1 calc R U . . .
H3B H 0.3430 0.5915 -0.1304 0.073 Uiso 1 1 calc R U . . .
H3C H 0.3165 0.7089 -0.0776 0.073 Uiso 1 1 calc R U . . .
Cl8 Cl 0.2371(3) 0.0978(3) 0.6275(2) 0.1020(8) Uani 1 1 d . . . . .
C4 C 0.0898(14) 0.1688(10) 0.6747(7) 0.093(3) Uani 1 1 d . . . . .
H4A H 0.1484 0.2474 0.7342 0.111 Uiso 1 1 calc R U . . .
H4B H 0.0344 0.1862 0.6096 0.111 Uiso 1 1 calc R U . . .
C3 C -0.0484(10) 0.0795(11) 0.7264(7) 0.086(3) Uani 1 1 d . . . . .
H3D H -0.1475 0.1079 0.7352 0.103 Uiso 1 1 calc R U . . .
H3E H -0.0888 -0.0037 0.6721 0.103 Uiso 1 1 calc R U . . .
N2 N 0.0207(8) 0.0737(6) 0.8403(5) 0.0610(14) Uani 1 1 d . . . . .
H2C H 0.1185 0.0559 0.8343 0.092 Uiso 1 1 calc R U . . .
H2D H -0.0572 0.0144 0.8629 0.092 Uiso 1 1 calc R U . . .
H2E H 0.0431 0.1472 0.8931 0.092 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 Cl2 2.6356(15) . ?
Bi1 Cl3 2.6577(17) . ?
Bi1 Cl4 2.7021(14) . ?
Bi1 Cl1 2.7163(14) . ?
Bi1 Cl6 2.7875(15) . ?
Bi1 Cl5 2.7943(13) . ?
Cl7 C2 1.745(8) . ?
C1 N1 1.181(12) . ?
C1 C2 1.422(14) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
N1 H1C 0.8900 . ?
N1 H1D 0.8900 . ?
N1 H1E 0.8900 . ?
Cl9 C6 1.792(7) . ?
C6 C5 1.466(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C5 N3 1.466(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 H3C 0.8900 . ?
Cl8 C4 1.715(8) . ?
C4 C3 1.548(13) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C3 N2 1.462(9) . ?
C3 H3D 0.9700 . ?
C3 H3E 0.9700 . ?
N2 H2C 0.8900 . ?
N2 H2D 0.8900 . ?
N2 H2E 0.8900 . ?

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 Bi1 Cl3 90.05(6) . . ?
Cl2 Bi1 Cl4 93.31(5) . . ?
Cl3 Bi1 Cl4 88.90(5) . . ?
Cl2 Bi1 Cl1 89.16(6) . . ?
Cl3 Bi1 Cl1 90.53(6) . . ?
Cl4 Bi1 Cl1 177.47(5) . . ?
Cl2 Bi1 Cl6 88.56(6) . . ?
Cl3 Bi1 Cl6 176.35(4) . . ?
Cl4 Bi1 Cl6 87.80(5) . . ?
Cl1 Bi1 Cl6 92.83(5) . . ?
Cl2 Bi1 Cl5 175.39(5) . . ?
Cl3 Bi1 Cl5 85.98(5) . . ?
Cl4 Bi1 Cl5 88.97(5) . . ?
Cl1 Bi1 Cl5 88.53(5) . . ?
Cl6 Bi1 Cl5 95.54(4) . . ?
N1 C1 C2 132.3(12) . . ?
N1 C1 H1A 104.2 . . ?
C2 C1 H1A 104.2 . . ?
N1 C1 H1B 104.2 . . ?
C2 C1 H1B 104.2 . . ?
H1A C1 H1B 105.5 . . ?
C1 C2 Cl7 114.2(7) . . ?
C1 C2 H2A 108.7 . . ?
Cl7 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
Cl7 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C1 N1 H1C 109.5 . . ?
C1 N1 H1D 109.5 . . ?
H1C N1 H1D 109.5 . . ?
C1 N1 H1E 109.5 . . ?
H1C N1 H1E 109.5 . . ?
H1D N1 H1E 109.5 . . ?
C5 C6 Cl9 111.1(4) . . ?
C5 C6 H6A 109.4 . . ?
Cl9 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
Cl9 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C6 C5 N3 112.6(5) . . ?
C6 C5 H5A 109.1 . . ?
N3 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
N3 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C5 N3 H3A 109.5 . . ?
C5 N3 H3B 109.5 . . ?
H3A N3 H3B 109.5 . . ?
C5 N3 H3C 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C3 C4 Cl8 108.2(7) . . ?
C3 C4 H4A 110.1 . . ?
Cl8 C4 H4A 110.1 . . ?
C3 C4 H4B 110.1 . . ?
Cl8 C4 H4B 110.1 . . ?
H4A C4 H4B 108.4 . . ?
N2 C3 C4 112.0(7) . . ?
N2 C3 H3D 109.2 . . ?
C4 C3 H3D 109.2 . . ?
N2 C3 H3E 109.2 . . ?
C4 C3 H3E 109.2 . . ?
H3D C3 H3E 107.9 . . ?
C3 N2 H2C 109.5 . . ?
C3 N2 H2D 109.5 . . ?
H2C N2 H2D 109.5 . . ?
C3 N2 H2E 109.5 . . ?
H2C N2 H2E 109.5 . . ?
H2D N2 H2E 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 Cl7 -35(2) . . . . ?
Cl9 C6 C5 N3 -64.9(6) . . . . ?
Cl8 C4 C3 N2 73.1(9) . . . . ?

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
N2 H2E Cl5 0.89 2.35 3.218(6) 164.3 1_556
N2 H2D Cl4 0.89 2.33 3.204(6) 167.7 2_556
N2 H2C Cl3 0.89 2.68 3.281(6) 126.0 2_556
C3 H3D Cl9 0.97 2.77 3.605(8) 145.2 2_566
C3 H3D Cl7 0.97 2.89 3.543(8) 125.8 1_455
N3 H3C Cl3 0.89 2.60 3.380(5) 146.6 2_565
N3 H3B Cl6 0.89 2.41 3.284(5) 166.0 2_665
N3 H3A Cl5 0.89 2.84 3.561(5) 139.5 2_565
N3 H3A Cl5 0.89 2.80 3.367(6) 122.7 .
N3 H3A Cl1 0.89 2.93 3.363(5) 112.0 2_565
C5 H5B Cl4 0.97 2.94 3.677(6) 134.0 2_665
C5 H5A Cl5 0.97 2.83 3.466(6) 124.2 .
C6 H6A Cl8 0.97 2.94 3.707(7) 136.5 2_666
C6 H6A Cl6 0.97 2.98 3.637(7) 125.7 .
N1 H1E Cl1 0.89 2.52 3.378(10) 161.2 2_666
N1 H1D Cl6 0.89 2.84 3.444(9) 126.1 .
N1 H1D Cl2 0.89 2.88 3.301(9) 110.5 2_666
N1 H1C Cl6 0.89 2.94 3.680(13) 141.5 2_666
C1 H1A Cl3 0.97 2.83 3.654(14) 142.9 1_655
N2 H2E Cl5 0.89 2.35 3.218(6) 164.3 1_556
N2 H2D Cl4 0.89 2.33 3.204(6) 167.7 2_556
N2 H2C Cl3 0.89 2.68 3.281(6) 126.0 2_556
C3 H3D Cl9 0.97 2.77 3.605(8) 145.2 2_566
C3 H3D Cl7 0.97 2.89 3.543(8) 125.8 1_455
N3 H3C Cl3 0.89 2.60 3.380(5) 146.6 2_565
N3 H3B Cl6 0.89 2.41 3.284(5) 166.0 2_665
N3 H3A Cl5 0.89 2.84 3.561(5) 139.5 2_565
N3 H3A Cl5 0.89 2.80 3.367(6) 122.7 .
N3 H3A Cl1 0.89 2.93 3.363(5) 112.0 2_565
C5 H5B Cl4 0.97 2.94 3.677(6) 134.0 2_665
C5 H5A Cl5 0.97 2.83 3.466(6) 124.2 .
C6 H6A Cl8 0.97 2.94 3.707(7) 136.5 2_666
C6 H6A Cl6 0.97 2.98 3.637(7) 125.7 .
N1 H1E Cl1 0.89 2.52 3.378(10) 161.2 2_666
N1 H1D Cl6 0.89 2.84 3.444(9) 126.1 .
N1 H1D Cl2 0.89 2.88 3.301(9) 110.5 2_666
N1 H1C Cl6 0.89 2.94 3.680(13) 141.5 2_666
C1 H1A Cl3 0.97 2.83 3.654(14) 142.9 1_655
C1 H1A Cl3 0.97 2.83 3.654(14) 142.9 1_655
N1 H1C Cl6 0.89 2.94 3.680(13) 141.5 2_666
N1 H1D Cl2 0.89 2.88 3.301(9) 110.5 2_666
N1 H1D Cl6 0.89 2.84 3.444(9) 126.1 .
N1 H1E Cl1 0.89 2.52 3.378(10) 161.2 2_666
C6 H6A Cl6 0.97 2.98 3.637(7) 125.7 .
C6 H6A Cl8 0.97 2.94 3.707(7) 136.5 2_666
C5 H5A Cl5 0.97 2.83 3.466(6) 124.2 .
C5 H5A Cl6 0.97 3.00 3.685(6) 128.9 .
C5 H5B Cl4 0.97 2.94 3.677(6) 134.0 2_665
N3 H3A Cl1 0.89 2.93 3.363(5) 112.0 2_565
N3 H3A Cl5 0.89 2.80 3.367(6) 122.7 .
N3 H3A Cl5 0.89 2.84 3.561(5) 139.5 2_565
N3 H3B Cl6 0.89 2.41 3.284(5) 166.0 2_665
N3 H3C Cl3 0.89 2.60 3.380(5) 146.6 2_565
C4 H4B Cl2 0.97 3.00 3.711(8) 131.3 .
C4 H4B Cl7 0.97 2.99 3.677(9) 128.6 1_455
C3 H3D Cl7 0.97 2.89 3.543(8) 125.8 1_455
C3 H3D Cl9 0.97 2.77 3.605(8) 145.2 2_566
N2 H2C Cl3 0.89 2.68 3.281(6) 126.0 2_556
N2 H2D Cl4 0.89 2.33 3.204(6) 167.7 2_556
N2 H2E Cl5 0.89 2.35 3.218(6) 164.3 1_556
C1 H1A Cl3 0.97 2.83 3.654(14) 142.9 1_655
N1 H1C Cl6 0.89 2.94 3.680(13) 141.5 2_666
N1 H1D Cl2 0.89 2.88 3.301(9) 110.5 2_666
N1 H1D Cl6 0.89 2.84 3.444(9) 126.1 .
N1 H1E Cl1 0.89 2.52 3.378(10) 161.2 2_666
C6 H6A Cl6 0.97 2.98 3.637(7) 125.7 .
C6 H6A Cl8 0.97 2.94 3.707(7) 136.5 2_666
C5 H5A Cl5 0.97 2.83 3.466(6) 124.2 .
C5 H5B Cl4 0.97 2.94 3.677(6) 134.0 2_665
N3 H3A Cl1 0.89 2.93 3.363(5) 112.0 2_565
N3 H3A Cl5 0.89 2.80 3.367(6) 122.7 .
N3 H3A Cl5 0.89 2.84 3.561(5) 139.5 2_565
N3 H3B Cl6 0.89 2.41 3.284(5) 166.0 2_665
N3 H3C Cl3 0.89 2.60 3.380(5) 146.6 2_565
C3 H3D Cl7 0.97 2.89 3.543(8) 125.8 1_455
C3 H3D Cl9 0.97 2.77 3.605(8) 145.2 2_566
N2 H2C Cl3 0.89 2.68 3.281(6) 126.0 2_556
N2 H2D Cl4 0.89 2.33 3.204(6) 167.7 2_556
N2 H2E Cl5 0.89 2.35 3.218(6) 164.3 1_556

_refine_diff_density_max         1.021
_refine_diff_density_min         -1.399
_refine_diff_density_rms         0.172

####################################################################### 
# 
# 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 1909100'
loop_
_audit_author_name
_audit_author_address
'Hui Hui Li'
;Southeast University
China
;
_audit_update_record             
;
2019-09-16 deposited with the CCDC.	2020-01-06 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         ?
_chemical_formula_sum            'C6 H21 Bi Br6 Cl3 N3'
_chemical_formula_weight         929.99

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.3218(2)
_cell_length_b                   12.1968(3)
_cell_length_c                   12.2353(4)
_cell_angle_alpha                104.697(2)
_cell_angle_beta                 108.110(2)
_cell_angle_gamma                93.253(2)
_cell_volume                     1129.25(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    289(2)
_cell_measurement_reflns_used    7470
_cell_measurement_theta_min      2.6010
_cell_measurement_theta_max      31.3980

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.735
_exptl_crystal_F_000             844
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    18.769
_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      289(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku, SCXmini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19802
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.604
_diffrn_reflns_theta_max         31.508
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.826
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.826
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.826
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7521
_reflns_number_gt                4477
_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)+(0.0503P)²+4.4780P] 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       0.00051(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7521
_refine_ls_number_parameters     176
_refine_ls_number_restraints     102
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1142
_refine_ls_wR_factor_gt          0.1056
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_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
Cl3 Cl 0.7309(3) 0.1258(3) 0.0915(3) 0.0803(8) Uani 1 1 d . U . . .
Bi1 Bi 0.34247(3) 0.28980(2) 0.66943(3) 0.03411(11) Uani 1 1 d . U . . .
Br1 Br 0.39637(10) 0.51966(6) 0.63890(7) 0.04315(19) Uani 1 1 d . U . . .
Br2 Br -0.00312(10) 0.23107(7) 0.49562(8) 0.0448(2) Uani 1 1 d . U . . .
Br3 Br 0.19501(11) 0.38241(8) 0.84861(8) 0.0512(2) Uani 1 1 d . U . . .
Br4 Br 0.66793(11) 0.35056(9) 0.84787(9) 0.0555(2) Uani 1 1 d . U . . .
Br5 Br 0.48728(12) 0.20599(8) 0.48666(9) 0.0552(2) Uani 1 1 d . U . . .
Br6 Br 0.31444(14) 0.07179(7) 0.69995(10) 0.0630(3) Uani 1 1 d . U . . .
Cl2 Cl 0.9227(3) 0.64564(15) 0.88198(17) 0.0441(4) Uani 1 1 d . U . . .
Cl1 Cl 0.1553(4) 1.0524(2) 0.1604(2) 0.0740(7) Uani 1 1 d . U . . .
N2 N 0.8106(9) 0.4405(6) 0.6406(7) 0.0451(16) Uani 1 1 d . U . . .
H2A H 0.8173 0.4368 0.7135 0.068 Uiso 1 1 calc R U . . .
H2B H 0.8431 0.3782 0.6024 0.068 Uiso 1 1 calc R U . . .
H2C H 0.7032 0.4448 0.5995 0.068 Uiso 1 1 calc R U . . .
C3 C 0.9228(10) 0.5427(7) 0.6508(8) 0.0445(18) Uani 1 1 d . U . . .
H3D H 0.9107 0.5492 0.5714 0.053 Uiso 1 1 calc R U . . .
H3E H 1.0409 0.5353 0.6896 0.053 Uiso 1 1 calc R U . . .
N3 N 0.5116(11) 0.3362(7) 0.0714(7) 0.067(2) Uani 1 1 d . U . . .
H3A H 0.5264 0.3874 0.1413 0.100 Uiso 1 1 calc R U . . .
H3B H 0.4383 0.3569 0.0125 0.100 Uiso 1 1 calc R U . . .
H3C H 0.6114 0.3326 0.0591 0.100 Uiso 1 1 calc R U . . .
N1 N 0.1630(18) 0.9711(8) 0.3878(11) 0.110(4) Uani 1 1 d . U . . .
H1A H 0.1032 1.0269 0.3721 0.132 Uiso 1 1 calc R U . A 1
H1B H 0.2715 1.0009 0.4304 0.132 Uiso 1 1 calc R U . A 1
H1C H 0.1195 0.9355 0.4296 0.132 Uiso 1 1 calc R U . A 1
C4 C 0.8783(12) 0.6489(7) 0.7227(8) 0.052(2) Uani 1 1 d . U . . .
H4A H 0.7583 0.6537 0.6868 0.063 Uiso 1 1 calc R U . . .
H4B H 0.9451 0.7161 0.7216 0.063 Uiso 1 1 calc R U . . .
C5 C 0.4434(15) 0.2228(10) 0.0734(15) 0.098(4) Uani 1 1 d . U . . .
H5A H 0.4037 0.1711 -0.0074 0.118 Uiso 1 1 calc R U . B 2
H5B H 0.3463 0.2299 0.1014 0.118 Uiso 1 1 calc R U . B 2
C2 C 0.069(2) 0.9215(11) 0.1697(14) 0.102(4) Uani 1 1 d . U . . .
H2D H -0.0507 0.9240 0.1619 0.122 Uiso 1 1 calc R U . C 1
H2E H 0.0726 0.8606 0.1024 0.122 Uiso 1 1 calc R U . C 1
C6' C 0.591(2) 0.1679(9) 0.1626(14) 0.112(5) Uani 1 1 d . U . D 2
H6'A H 0.5378 0.1030 0.1777 0.135 Uiso 1 1 calc R U . D 2
H6'B H 0.6490 0.2250 0.2387 0.135 Uiso 1 1 calc R U . D 2
C1 C 0.155(2) 0.8933(10) 0.2809(14) 0.104(4) Uani 1 1 d . U . E 1
H1D H 0.0981 0.8199 0.2766 0.125 Uiso 1 1 calc R U . E 1
H1E H 0.2711 0.8834 0.2839 0.125 Uiso 1 1 calc R U . E 1


_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
Cl3 C6' 1.688(13) . ?
Bi1 Br6 2.7842(9) . ?
Bi1 Br4 2.8154(9) . ?
Bi1 Br5 2.8554(9) . ?
Bi1 Br3 2.8567(9) . ?
Bi1 Br2 2.9150(8) . ?
Bi1 Br1 2.9484(8) . ?
Cl2 C4 1.878(9) . ?
Cl1 C2 1.759(13) . ?
N2 C3 1.469(10) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
C3 C4 1.505(12) . ?
C3 H3D 0.9700 . ?
C3 H3E 0.9700 . ?
N3 C5 1.474(14) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 H3C 0.8900 . ?
N1 C1 1.389(17) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6' 1.67(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C2 C1 1.46(2) . ?
C2 H2D 0.9700 . ?
C2 H2E 0.9700 . ?
C6' H6'A 0.9700 . ?
C6' H6'B 0.9700 . ?
C1 H1D 0.9700 . ?
C1 H1E 0.9700 . ?

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
Br6 Bi1 Br4 90.89(3) . . ?
Br6 Bi1 Br5 89.59(3) . . ?
Br4 Bi1 Br5 91.55(3) . . ?
Br6 Bi1 Br3 92.85(3) . . ?
Br4 Bi1 Br3 89.10(3) . . ?
Br5 Bi1 Br3 177.47(3) . . ?
Br6 Bi1 Br2 88.93(3) . . ?
Br4 Bi1 Br2 176.68(3) . . ?
Br5 Bi1 Br2 91.76(3) . . ?
Br3 Bi1 Br2 87.60(3) . . ?
Br6 Bi1 Br1 176.16(3) . . ?
Br4 Bi1 Br1 86.17(3) . . ?
Br5 Bi1 Br1 88.03(3) . . ?
Br3 Bi1 Br1 89.57(3) . . ?
Br2 Bi1 Br1 94.14(2) . . ?
C3 N2 H2A 109.5 . . ?
C3 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C3 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
N2 C3 C4 110.5(7) . . ?
N2 C3 H3D 109.5 . . ?
C4 C3 H3D 109.5 . . ?
N2 C3 H3E 109.5 . . ?
C4 C3 H3E 109.5 . . ?
H3D C3 H3E 108.1 . . ?
C5 N3 H3A 109.5 . . ?
C5 N3 H3B 109.5 . . ?
H3A N3 H3B 109.5 . . ?
C5 N3 H3C 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C3 C4 Cl2 110.5(6) . . ?
C3 C4 H4A 109.6 . . ?
Cl2 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
Cl2 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
N3 C5 C6' 111.5(10) . . ?
N3 C5 H5A 109.3 . . ?
C6' C5 H5A 109.3 . . ?
N3 C5 H5B 109.3 . . ?
C6' C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C1 C2 Cl1 114.7(10) . . ?
C1 C2 H2D 108.6 . . ?
Cl1 C2 H2D 108.6 . . ?
C1 C2 H2E 108.6 . . ?
Cl1 C2 H2E 108.6 . . ?
H2D C2 H2E 107.6 . . ?
C5 C6' Cl3 107.3(9) . . ?
C5 C6' H6'A 110.3 . . ?
Cl3 C6' H6'A 110.3 . . ?
C5 C6' H6'B 110.3 . . ?
Cl3 C6' H6'B 110.3 . . ?
H6'A C6' H6'B 108.5 . . ?
N1 C1 C2 117.2(13) . . ?
N1 C1 H1D 108.0 . . ?
C2 C1 H1D 108.0 . . ?
N1 C1 H1E 108.0 . . ?
C2 C1 H1E 108.0 . . ?
H1D C1 H1E 107.3 . . ?

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
N2 C3 C4 Cl2 65.2(8) . . . . ?
N3 C5 C6' Cl3 -73.3(12) . . . . ?
Cl1 C2 C1 N1 58.2(19) . . . . ?

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
C1 H1E Br4 0.97 3.06 3.613(14) 117.9 2_666
C1 H1D Br3 0.97 3.08 3.952(15) 151.0 2_566
C6' H6'A Br6 0.97 3.01 3.732(11) 132.1 2_656
C5 H5B Cl1 0.97 2.98 3.653(14) 127.9 1_545
C5 H5B Cl2 0.97 2.81 3.647(12) 145.5 2_666
C4 H4B Br2 0.97 3.06 3.728(9) 127.5 2_666
N1 H1C Br2 0.89 2.68 3.533(10) 161.3 2_566
N1 H1B Br5 0.89 2.79 3.505(10) 137.9 1_565
N1 H1A Br2 0.89 2.91 3.635(12) 140.3 1_565
N3 H3C Br4 0.89 2.83 3.410(9) 124.6 1_554
N3 H3B Br3 0.89 2.47 3.343(8) 168.5 1_554
N3 H3A Br1 0.89 2.50 3.353(9) 161.9 2_666
C3 H3E Br3 0.97 3.08 3.782(8) 130.8 1_655
C3 H3D Br2 0.97 3.12 3.784(8) 127.2 2_666
C3 H3D Br1 0.97 2.90 3.571(8) 126.9 2_666
N2 H2C Br5 0.89 3.07 3.494(7) 111.2 .
N2 H2C Br1 0.89 2.93 3.488(7) 122.6 2_666
N2 H2C Br1 0.89 2.90 3.627(7) 140.4 .
N2 H2B Br2 0.89 2.58 3.455(7) 166.5 1_655
N2 H2A Cl2 0.89 2.73 3.182(7) 112.6 .
N2 H2A Br4 0.89 2.71 3.491(7) 146.8 .
N2 H2A Br4 0.89 2.71 3.491(7) 146.8 .
N2 H2A Br4 0.89 2.71 3.491(7) 146.8 .
N2 H2A Cl2 0.89 2.73 3.182(7) 112.6 .
N2 H2B Br2 0.89 2.58 3.455(7) 166.5 1_655
N2 H2C Br1 0.89 2.90 3.627(7) 140.4 .
N2 H2C Br1 0.89 2.93 3.488(7) 122.6 2_666
N2 H2C Br5 0.89 3.07 3.494(7) 111.2 .
C3 H3D Br1 0.97 2.90 3.571(8) 126.9 2_666
C3 H3D Br2 0.97 3.12 3.784(8) 127.2 2_666
C3 H3E Br3 0.97 3.08 3.782(8) 130.8 1_655
N3 H3A Br1 0.89 2.50 3.353(9) 161.9 2_666
N3 H3B Br3 0.89 2.47 3.343(8) 168.5 1_554
N3 H3C Br4 0.89 2.83 3.410(9) 124.6 1_554
N1 H1A Br2 0.89 2.91 3.635(12) 140.3 1_565
N1 H1B Br5 0.89 2.79 3.505(10) 137.9 1_565
N1 H1C Br2 0.89 2.68 3.533(10) 161.3 2_566
C4 H4B Br2 0.97 3.06 3.728(9) 127.5 2_666
C5 H5B Cl2 0.97 2.81 3.647(12) 145.5 2_666
C5 H5B Cl1 0.97 2.98 3.653(14) 127.9 1_545
C6' H6'A Br6 0.97 3.01 3.732(11) 132.1 2_656
C1 H1D Br3 0.97 3.08 3.952(15) 151.0 2_566
C1 H1E Br4 0.97 3.06 3.613(14) 117.9 2_666

_refine_diff_density_max         1.990
_refine_diff_density_min         -1.238
_refine_diff_density_rms         0.191

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1912574'
loop_
_audit_author_name
_audit_author_address
'Hui Hui Li'
;Southeast University
China
;
_audit_update_record             
;
2019-09-16 deposited with the CCDC.	2020-01-06 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         ?
_chemical_formula_sum            'C6 H24 Bi Cl6 N3'
_chemical_formula_weight         559.96

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

_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, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   21.1620(15)
_cell_length_b                   7.9735(5)
_cell_length_c                   11.8046(7)
_cell_angle_alpha                90
_cell_angle_beta                 104.186(7)
_cell_angle_gamma                90
_cell_volume                     1931.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2820
_cell_measurement_theta_min      1.8970
_cell_measurement_theta_max      24.3200

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.926
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    9.945
_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      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku, SCXmini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10006
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.985
_diffrn_reflns_theta_max         29.825
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2959
_reflns_number_gt                2332
_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)+(0.0820P)²+6.2619P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2959
_refine_ls_number_parameters     90
_refine_ls_number_restraints     64
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1427
_refine_ls_wR_factor_gt          0.1350
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.056
_refine_ls_shift/su_mean         0.004

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 0.16908(2) 0.0000 0.21726(3) 0.04435(16) Uani 1 2 d S TU P . .
Cl1 Cl 0.25722(13) 0.2417(4) 0.2762(3) 0.0824(8) Uani 1 1 d . U . . .
Cl2 Cl 0.07546(14) 0.2426(4) 0.1490(4) 0.1025(11) Uani 1 1 d . U . . .
Cl4 Cl 0.1831(2) 0.0000 -0.0088(3) 0.140(3) Uani 1 2 d S TU P . .
Cl5 Cl 0.1520(3) 0.0000 0.4289(4) 0.1095(17) Uani 1 2 d S TU P . .
N2 N 0.3271(6) 1.0000 -0.0465(10) 0.070(3) Uani 1 2 d S TU P . .
H2A H 0.3338 1.1013 -0.0730 0.106 Uiso 0.5 1 d R U P . .
H2B H 0.2850 0.9741 -0.0702 0.106 Uiso 0.5 1 d R U P . .
H2C H 0.3505 0.9246 -0.0739 0.106 Uiso 0.5 1 d R U P . .
C3 C 0.34919(3) 1.0000 0.0783(3) 0.135(9) Uani 1 2 d DS TU P . .
H3A H 0.3311 0.9017 0.1071 0.162 Uiso 0.5 1 d R U P . .
H3B H 0.3311 1.0983 0.1071 0.162 Uiso 0.5 1 d R U P . .
C4 C 0.42129(3) 1.0000 0.1310(3) 0.135(9) Uani 1 2 d DS TU P . .
H4A H 0.4382 0.8907 0.1213 0.203 Uiso 0.5 1 d R U P . .
H4B H 0.4316 1.0282 0.2125 0.203 Uiso 0.5 1 d R U P . .
H4C H 0.4405 1.0811 0.0895 0.203 Uiso 0.5 1 d R U P . .
C6 C 0.08497(4) 0.5000 0.49270(8) 0.192(13) Uani 1 2 d DS TU P . .
H3E H 0.1073 0.4590 0.5609 0.288 Uiso 0.5 1 d R U P . .
H3D H 0.0500 0.4365 0.4649 0.288 Uiso 0.5 1 d R U P . .
H3C H 0.0725 0.6044 0.5026 0.288 Uiso 0.5 1 d R U P . .
C5 C 0.13768(4) 0.5000 0.42781(8) 0.186(13) Uani 1 2 d DS TU P . .
H5A H 0.1232 0.5969 0.3786 0.223 Uiso 0.5 1 d R U P . .
H5B H 0.1232 0.4031 0.3786 0.223 Uiso 0.5 1 d R U P . .
N3 N 0.1888(10) 0.5000 0.4449(19) 0.177(8) Uani 1 2 d S TU P . .
H6A H 0.2013 0.4119 0.3994 0.266 Uiso 0.5 1 d R U P . .
H6B H 0.2090 0.4820 0.5262 0.266 Uiso 0.5 1 d R U P . .
H6C H 0.2026 0.6061 0.4209 0.266 Uiso 0.5 1 d R U P . .
C2 C 0.06589(9) 0.15046(11) 0.66118(11) 0.198(14) Uani 0.5 1 d D U P . .
H1C H 0.0660 0.1189 0.5880 0.297 Uiso 0.5 1 d R U P . .
H1D H 0.0370 0.2341 0.6584 0.297 Uiso 0.5 1 d R U P . .
H1E H 0.1059 0.1862 0.6984 0.297 Uiso 0.5 1 d R U P . .
C1 C 0.04820(9) 0.0000 0.72321(11) 0.177(8) Uani 1 2 d DS TU P . .
H1A H 0.0840 -0.0750 0.7258 0.213 Uiso 0.5 1 d R U P . .
H1B H 0.0104 -0.0554 0.6768 0.213 Uiso 0.5 1 d R U P . .
N1 N 0.0408(7) 0.0000 0.8407(12) 0.093(4) Uani 1 2 d S TU P . .
H2D H 0.0804 0.0351 0.8944 0.140 Uiso 0.5 1 d R U P . .
H2E H 0.0296 -0.1110 0.8606 0.140 Uiso 0.5 1 d R U P . .
H2F H 0.0062 0.0760 0.8451 0.140 Uiso 0.5 1 d R U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 Cl5 2.611(4) . ?
Bi1 Cl1 2.654(2) . ?
Bi1 Cl1 2.654(2) 6 ?
Bi1 Cl2 2.745(3) . ?
Bi1 Cl2 2.745(3) 6 ?
Bi1 Cl4 2.756(4) . ?
N2 C3 1.431(13) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
C3 C4 1.50000(13) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C6 C5 1.50000(11) . ?
C6 H3E 0.8900 . ?
C6 H3D 0.8900 . ?
C6 H3C 0.8900 . ?
C5 N3 1.05(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
N3 H6A 0.9600 . ?
N3 H6B 0.9600 . ?
N3 H6C 0.9600 . ?
C2 C1 1.50000(7) . ?
C2 C2 2.3994(17) 6 ?
C2 H1C 0.9000 . ?
C2 H1D 0.9000 . ?
C2 H1E 0.9000 . ?
C1 C2 1.49998(7) 6 ?
C1 N1 1.433(14) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
N1 H2D 0.9600 . ?
N1 H2E 0.9600 . ?
N1 H2F 0.9599 . ?

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
Cl5 Bi1 Cl1 90.12(12) . . ?
Cl5 Bi1 Cl1 90.12(12) . 6 ?
Cl1 Bi1 Cl1 93.16(13) . 6 ?
Cl5 Bi1 Cl2 91.26(13) . . ?
Cl1 Bi1 Cl2 88.59(11) . . ?
Cl1 Bi1 Cl2 177.77(9) 6 . ?
Cl5 Bi1 Cl2 91.26(13) . 6 ?
Cl1 Bi1 Cl2 177.77(9) . 6 ?
Cl1 Bi1 Cl2 88.59(11) 6 6 ?
Cl2 Bi1 Cl2 89.62(15) . 6 ?
Cl5 Bi1 Cl4 178.27(14) . . ?
Cl1 Bi1 Cl4 91.06(9) . . ?
Cl1 Bi1 Cl4 91.06(9) 6 . ?
Cl2 Bi1 Cl4 87.52(11) . . ?
Cl2 Bi1 Cl4 87.52(11) 6 . ?
C3 N2 H2A 108.8 . . ?
C3 N2 H2B 111.9 . . ?
H2A N2 H2B 109.5 . . ?
C3 N2 H2C 107.7 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
N2 C3 C4 118.0(5) . . ?
N2 C3 H3A 107.7 . . ?
C4 C3 H3A 107.6 . . ?
N2 C3 H3B 107.7 . . ?
C4 C3 H3B 107.6 . . ?
H3A C3 H3B 107.8 . . ?
C3 C4 H4A 108.8 . . ?
C3 C4 H4B 112.0 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 107.6 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C5 C6 H3E 99.6 . . ?
C5 C6 H3D 117.9 . . ?
H3E C6 H3D 109.5 . . ?
C5 C6 H3C 110.4 . . ?
H3E C6 H3C 109.5 . . ?
H3D C6 H3C 109.5 . . ?
N3 C5 C6 139.6(12) . . ?
N3 C5 H5A 105.9 . . ?
C6 C5 H5A 98.1 . . ?
N3 C5 H5B 105.9 . . ?
C6 C5 H5B 98.1 . . ?
H5A C5 H5B 105.6 . . ?
C5 N3 H6A 107.7 . . ?
C5 N3 H6B 112.2 . . ?
H6A N3 H6B 109.5 . . ?
C5 N3 H6C 108.5 . . ?
H6A N3 H6C 109.5 . . ?
H6B N3 H6C 109.5 . . ?
C1 C2 C2 36.89(5) . 6 ?
C1 C2 H1C 107.7 . . ?
C2 C2 H1C 73.8 6 . ?
C1 C2 H1D 111.2 . . ?
C2 C2 H1D 137.8 6 . ?
H1C C2 H1D 109.5 . . ?
C1 C2 H1E 109.4 . . ?
C2 C2 H1E 108.4 6 . ?
H1C C2 H1E 109.5 . . ?
H1D C2 H1E 109.5 . . ?
C2 C1 C2 106.22(11) 6 . ?
C2 C1 N1 124.89(13) 6 . ?
C2 C1 N1 124.89(14) . . ?
C2 C1 H1A 39.4 6 . ?
C2 C1 H1A 102.9 . . ?
N1 C1 H1A 104.0 . . ?
C2 C1 H1B 68.1 6 . ?
C2 C1 H1B 111.2 . . ?
N1 C1 H1B 106.2 . . ?
H1A C1 H1B 105.9 . . ?
C1 N1 H2D 110.7 . . ?
C1 N1 H2E 109.2 . . ?
H2D N1 H2E 109.5 . . ?
C1 N1 H2F 108.5 . . ?
H2D N1 H2F 109.5 . . ?
H2E N1 H2F 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
C2 C2 C1 N1 158.3(7) 6 . . . ?

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
N3 H6C Cl1 0.96 2.59 3.423(17) 145.7 6_565
N3 H6B Cl5 0.96 2.86 3.33(2) 111.3 7_556
N3 H6B Cl1 0.96 2.88 3.743(19) 149.5 7_556
N3 H6A Cl1 0.96 2.49 3.423(17) 164.0 .
C5 H5B Cl2 0.97 2.94 3.828(5) 152.2 .
C5 H5A Cl2 0.97 2.94 3.828(4) 152.2 6_565
N2 H2C Cl2 0.89 2.45 3.340(10) 173.3 4
N2 H2B Cl4 0.89 2.45 3.186(13) 140.7 1_565
N2 H2A Cl2 0.89 2.62 3.340(10) 138.1 7_565
N2 H2A Cl1 0.89 2.96 3.523(10) 122.7 7_565
N2 H2A Cl1 0.89 2.96 3.523(10) 122.7 7_565
N2 H2A Cl2 0.89 2.62 3.340(10) 138.1 7_565
N2 H2B Cl4 0.89 2.45 3.186(13) 140.7 1_565
N2 H2C Cl2 0.89 2.45 3.340(10) 173.3 4
C5 H5A Cl2 0.97 2.94 3.828(4) 152.2 6_565
C5 H5B Cl2 0.97 2.94 3.828(5) 152.2 .
N3 H6A Cl1 0.96 2.49 3.423(17) 164.0 .
N3 H6B Cl1 0.96 2.88 3.743(19) 149.5 7_556
N3 H6B Cl5 0.96 2.86 3.33(2) 111.3 7_556
N3 H6C Cl1 0.96 2.59 3.423(17) 145.7 6_565

_refine_diff_density_max         0.848
_refine_diff_density_min         -2.307
_refine_diff_density_rms         0.285

_vrf_PLAT242_a                   
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of        Bi1 Check 
RESPONSE: ...Author Response :The alert is due to the disordered structure
;
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1909094'
loop_
_audit_author_name
_audit_author_address
'Hui Hui Li'
;Southeast University
China
;
_audit_update_record             
;
2019-09-16 deposited with the CCDC.	2020-01-06 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         ?
_chemical_formula_sum            'C6 H21 Bi Cl9 N3'
_chemical_formula_weight         663.29

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'
N N 0.0061 0.0033 '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'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

_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, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   22.520(2)
_cell_length_b                   8.2945(5)
_cell_length_c                   12.1353(11)
_cell_angle_alpha                90
_cell_angle_beta                 106.123(9)
_cell_angle_gamma                90
_cell_volume                     2177.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    403(2)
_cell_measurement_reflns_used    2582
_cell_measurement_theta_min      2.6140
_cell_measurement_theta_max      31.5090

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.023
_exptl_crystal_F_000             1256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    9.192
_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      403(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku, SCXmini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7517
_diffrn_reflns_av_unetI/netI     0.0683
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.630
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_full        24.993
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             2068
_reflns_number_gt                1385
_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)+(0.1421P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2068
_refine_ls_number_parameters     131
_refine_ls_number_restraints     81
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0619
_refine_ls_wR_factor_ref         0.2138
_refine_ls_wR_factor_gt          0.1782
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_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
Bi01 Bi 0.16696(3) 0.5000 0.70462(6) 0.0967(4) Uani 1 2 d S T P . .
Cl05 Cl 0.1746(4) 0.5000 0.4813(8) 0.209(5) Uani 1 2 d S T P . .
Cl7 Cl 0.0797(2) 0.2715(7) 0.6410(7) 0.174(2) Uani 1 1 d . . . . .
Cl8 Cl 0.1559(4) 0.5000 0.9161(7) 0.148(2) Uani 1 2 d S T P . .
Cl9 Cl 0.2537(2) 0.7380(5) 0.7624(5) 0.1357(15) Uani 1 1 d . . . . .
Cl1 Cl 0.0573(5) 0.0000 0.3475(11) 0.222(5) Uani 1 2 d DS T P . .
Cl3 Cl 0.4260(17) 0.5000 -0.001(7) 0.79(5) Uani 1 2 d DS T P . .
C1 C 0.1345(9) 0.0000 0.365(2) 0.193(16) Uani 1 2 d DS TU P . .
H1D H 0.1410 0.0418 0.2952 0.231 Uiso 0.5 1 d R U P . .
H1E H 0.1484 -0.1099 0.3717 0.231 Uiso 0.5 1 d R U P . .
C2 C 0.1741(11) 0.091(4) 0.460(2) 0.28(3) Uani 0.5 1 d D U P . .
H2D H 0.1560 0.1945 0.4649 0.334 Uiso 0.5 1 d R U P . .
H2E H 0.2140 0.1079 0.4479 0.334 Uiso 0.5 1 d R U P . .
Cl2 Cl 0.9421(16) 0.340(4) 0.874(2) 0.39(2) Uani 0.5 1 d D U P A -1
C3 C 0.923(2) 0.532(4) 0.835(3) 0.26(3) Uani 0.5 1 d D U P A -1
H3A H 0.8824 0.5332 0.7812 0.308 Uiso 0.5 1 calc R U P A -1
H3B H 0.9212 0.5926 0.9020 0.308 Uiso 0.5 1 calc R U P A -1
C4 C 0.966(3) 0.619(4) 0.781(3) 0.30(3) Uani 0.5 1 d D U P A -1
H4A H 0.9879 0.7072 0.7588 0.360 Uiso 0.5 1 d R U P A -1
H4B H 0.9946 0.5316 0.8059 0.360 Uiso 0.5 1 d R U P A -1
N2 N 0.9631(12) 0.541(4) 0.667(2) 0.127(14) Uani 0.5 1 d D U P A -1
H2A H 0.9783 0.5098 0.6090 0.191 Uiso 0.5 1 d R U P A -1
H2B H 0.9430 0.4577 0.6879 0.191 Uiso 0.5 1 d R U P A -1
H2C H 0.9367 0.6235 0.6434 0.216 Uiso 0.5 1 d R U P A -1
C5 C 0.396(4) 0.466(14) 0.111(5) 0.32(5) Uani 0.5 1 d D U P . .
H5A H 0.4110 0.4684 0.1932 0.388 Uiso 0.5 1 d R U P . .
H5B H 0.3835 0.3572 0.0886 0.388 Uiso 0.5 1 d R U P . .
C6 C 0.335(3) 0.545(13) 0.102(6) 0.25(4) Uani 0.5 1 d D U P . .
H6A H 0.3480 0.6553 0.1001 0.304 Uiso 0.5 1 d R U P . .
H6B H 0.3090 0.5369 0.1520 0.304 Uiso 0.5 1 d R U P . .
N1 N 0.180(2) 0.0000 0.569(2) 0.202(15) Uani 1 2 d DS TU P . .
H1A H 0.2043 0.0563 0.6283 0.303 Uiso 0.5 1 d R U P . .
H1B H 0.1427 -0.0147 0.5807 0.303 Uiso 0.5 1 d R U P . .
H1C H 0.1976 -0.0965 0.5647 0.303 Uiso 0.5 1 d R U P . .
N3 N 0.294(4) 0.5000 -0.014(8) 0.91(18) Uani 1 2 d DS TU P . .
H3D H 0.2604 0.5610 -0.0428 1.364 Uiso 0.5 1 d R U P . .
H3E H 0.3195 0.5000 -0.0595 1.364 Uiso 1 2 d R U P . .
H3C H 0.2828 0.3965 -0.0107 1.364 Uiso 0.5 1 d R U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi01 Cl8 2.647(7) . ?
Bi01 Cl7 2.684(5) 6_565 ?
Bi01 Cl7 2.684(5) . ?
Bi01 Cl9 2.728(4) . ?
Bi01 Cl9 2.728(4) 6_565 ?
Bi01 Cl05 2.763(9) . ?
Cl1 C1 1.692(18) . ?
Cl3 C5 1.69(2) 6_565 ?
Cl3 C5 1.69(2) . ?
C1 C2 1.460(18) . ?
C1 C2 1.460(18) 6 ?
C1 H1D 0.9600 . ?
C1 H1E 0.9600 . ?
C2 C2 1.51(7) 6 ?
C2 N1 1.50(2) . ?
C2 H2D 0.9602 . ?
C2 H2E 0.9598 . ?
Cl2 C3 1.69(2) . ?
C3 C4 1.49(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N2 1.51(2) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9599 . ?
N2 H2A 0.9000 . ?
N2 H2B 0.9001 . ?
N2 H2C 0.9000 . ?
C5 C5 0.6(2) 6_565 ?
C5 C6 1.35(6) 6_565 ?
C5 C6 1.50(2) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C6 C6 0.8(2) 6_565 ?
C6 C5 1.35(6) 6_565 ?
C6 N3 1.50(2) . ?
C6 H6A 0.9599 . ?
C6 H6B 0.9601 . ?
N1 C2 1.50(2) 6 ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
N1 H1C 0.9001 . ?
N3 C6 1.50(2) 6_565 ?
N3 H3D 0.9001 . ?
N3 H3E 0.8976 . ?
N3 H3C 0.9000 . ?

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
Cl8 Bi01 Cl7 91.2(2) . 6_565 ?
Cl8 Bi01 Cl7 91.2(2) . . ?
Cl7 Bi01 Cl7 89.8(3) 6_565 . ?
Cl8 Bi01 Cl9 90.2(2) . . ?
Cl7 Bi01 Cl9 88.7(2) 6_565 . ?
Cl7 Bi01 Cl9 178.01(17) . . ?
Cl8 Bi01 Cl9 90.23(19) . 6_565 ?
Cl7 Bi01 Cl9 178.01(17) 6_565 6_565 ?
Cl7 Bi01 Cl9 88.7(2) . 6_565 ?
Cl9 Bi01 Cl9 92.7(2) . 6_565 ?
Cl8 Bi01 Cl05 178.2(2) . . ?
Cl7 Bi01 Cl05 87.6(2) 6_565 . ?
Cl7 Bi01 Cl05 87.6(2) . . ?
Cl9 Bi01 Cl05 90.99(18) . . ?
Cl9 Bi01 Cl05 90.99(18) 6_565 . ?
C5 Cl3 C5 19(8) 6_565 . ?
C2 C1 C2 62(3) . 6 ?
C2 C1 Cl1 118.6(16) . . ?
C2 C1 Cl1 118.6(16) 6 . ?
C2 C1 H1D 107.4 . . ?
C2 C1 H1D 132.3 6 . ?
Cl1 C1 H1D 107.2 . . ?
C2 C1 H1E 107.9 . . ?
C2 C1 H1E 47.6 6 . ?
Cl1 C1 H1E 108.0 . . ?
H1D C1 H1E 107.2 . . ?
C1 C2 C2 58.9(14) . 6 ?
C1 C2 N1 109.0(18) . . ?
C2 C2 N1 59.8(13) 6 . ?
C1 C2 H2D 109.5 . . ?
C2 C2 H2D 153.4 6 . ?
N1 C2 H2D 109.2 . . ?
C1 C2 H2E 110.3 . . ?
C2 C2 H2E 98.4 6 . ?
N1 C2 H2E 110.5 . . ?
H2D C2 H2E 108.2 . . ?
C4 C3 Cl2 116(2) . . ?
C4 C3 H3A 108.2 . . ?
Cl2 C3 H3A 108.2 . . ?
C4 C3 H3B 108.2 . . ?
Cl2 C3 H3B 108.2 . . ?
H3A C3 H3B 107.4 . . ?
C3 C4 N2 109.0(19) . . ?
C3 C4 H4A 158.9 . . ?
N2 C4 H4A 88.2 . . ?
C3 C4 H4B 87.2 . . ?
N2 C4 H4B 79.8 . . ?
H4A C4 H4B 108.4 . . ?
C4 N2 H2A 154.9 . . ?
C4 N2 H2B 88.1 . . ?
H2A N2 H2B 109.5 . . ?
C4 N2 H2C 79.6 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C5 C5 C6 94(9) 6_565 6_565 ?
C5 C5 C6 64(4) 6_565 . ?
C6 C5 C6 30(9) 6_565 . ?
C5 C5 Cl3 80(4) 6_565 . ?
C6 C5 Cl3 124(4) 6_565 . ?
C6 C5 Cl3 115(2) . . ?
C5 C5 H5A 88.7 6_565 . ?
C6 C5 H5A 98.0 6_565 . ?
C6 C5 H5A 96.6 . . ?
Cl3 C5 H5A 136.6 . . ?
C5 C5 H5B 159.6 6_565 . ?
C6 C5 H5B 72.4 6_565 . ?
C6 C5 H5B 101.3 . . ?
Cl3 C5 H5B 94.8 . . ?
H5A C5 H5B 107.8 . . ?
C6 C6 C5 86(8) 6_565 6_565 ?
C6 C6 N3 76(4) 6_565 . ?
C5 C6 N3 114(4) 6_565 . ?
C6 C6 C5 64(4) 6_565 . ?
C5 C6 C5 22(10) 6_565 . ?
N3 C6 C5 105.8(19) . . ?
C6 C6 H6A 162.0 6_565 . ?
C5 C6 H6A 76.0 6_565 . ?
N3 C6 H6A 109.2 . . ?
C5 C6 H6A 98.2 . . ?
C6 C6 H6B 85.9 6_565 . ?
C5 C6 H6B 137.0 6_565 . ?
N3 C6 H6B 104.6 . . ?
C5 C6 H6B 129.2 . . ?
H6A C6 H6B 108.9 . . ?
C2 N1 C2 60(3) 6 . ?
C2 N1 H1A 148.3 6 . ?
C2 N1 H1A 109.2 . . ?
C2 N1 H1B 102.1 6 . ?
C2 N1 H1B 110.2 . . ?
H1A N1 H1B 109.5 . . ?
C2 N1 H1C 55.3 6 . ?
C2 N1 H1C 109.0 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C6 N3 C6 29(9) . 6_565 ?
C6 N3 H3D 117.2 . . ?
C6 N3 H3D 137.6 6_565 . ?
C6 N3 H3E 104.3 . . ?
C6 N3 H3E 104.3 6_565 . ?
H3D N3 H3E 112.0 . . ?
C6 N3 H3C 107.7 . . ?
C6 N3 H3C 80.1 6_565 . ?
H3D N3 H3C 109.5 . . ?
H3E N3 H3C 105.4 . . ?

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
Cl1 C1 C2 C2 109.2(13) . . . 6 ?
C2 C1 C2 N1 -34(3) 6 . . . ?
Cl1 C1 C2 N1 75(3) . . . . ?
Cl2 C3 C4 N2 66(4) . . . . ?
C5 Cl3 C5 C6 88(13) 6_565 . . 6_565 ?
C5 Cl3 C5 C6 55(7) 6_565 . . . ?
C5 C5 C6 C6 179.998(4) 6_565 . . 6_565 ?
Cl3 C5 C6 C6 116(8) . . . 6_565 ?
C6 C5 C6 C5 180.002(5) 6_565 . . 6_565 ?
Cl3 C5 C6 C5 -64(8) . . . 6_565 ?
C5 C5 C6 N3 115(7) 6_565 . . . ?
C6 C5 C6 N3 -65(7) 6_565 . . . ?
Cl3 C5 C6 N3 51(10) . . . . ?
C1 C2 N1 C2 34(3) . . . 6 ?
C5 C6 N3 C6 79(11) 6_565 . . 6_565 ?
C5 C6 N3 C6 57(6) . . . 6_565 ?

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
N3 H3E Cl3 0.90 2.30 2.93(11) 126.4 .
N3 H3D Cl9 0.90 2.75 3.27(7) 118.2 1_554
N3 H3D Cl8 0.90 2.32 2.99(10) 131.2 1_554
N1 H1C Cl9 0.90 2.75 3.29(2) 119.5 1_545
N1 H1B Cl7 0.90 2.77 3.47(3) 135.7 6
N1 H1B Cl7 0.90 2.96 3.47(3) 117.6 .
N1 H1A Cl9 0.90 2.41 3.29(2) 165.8 6_565
C6 H6B Cl9 0.96 2.71 3.43(5) 132.0 7_566
C6 H6A Cl8 0.96 2.87 3.79(11) 161.2 7_566
C5 H5A Cl7 0.96 2.80 3.51(6) 131.8 7_556
N2 H2A Cl7 0.90 2.96 3.53(3) 122.4 1_655
C4 H4A Cl1 0.96 2.81 3.50(4) 129.7 5_666
C4 H4A Cl7 0.96 2.83 3.56(4) 133.7 6_665
C2 H2E Cl05 0.96 2.58 3.37(3) 139.9 7_556
C2 H2D Cl05 0.96 2.57 3.40(3) 145.5 .
N3 H3E Cl3 0.90 2.30 2.93(11) 126.4 .
N1 H1C Cl9 0.90 2.75 3.29(2) 119.5 1_545
N1 H1B Cl7 0.90 2.96 3.47(3) 117.6 .
C2 H2D Cl05 0.96 2.57 3.40(3) 145.5 .
C2 H2D Cl05 0.96 2.57 3.40(3) 145.5 .
C2 H2E Cl05 0.96 2.58 3.37(3) 139.9 7_556
C4 H4A Cl7 0.96 2.83 3.56(4) 133.7 6_665
C4 H4A Cl1 0.96 2.81 3.50(4) 129.7 5_666
N2 H2A Cl7 0.90 2.96 3.53(3) 122.4 1_655
C5 H5A Cl7 0.96 2.80 3.51(6) 131.8 7_556
C6 H6A Cl8 0.96 2.87 3.79(11) 161.2 7_566
C6 H6B Cl9 0.96 2.71 3.43(5) 132.0 7_566
N1 H1A Cl9 0.90 2.41 3.29(2) 165.8 6_565
N1 H1B Cl7 0.90 2.96 3.47(3) 117.6 .
N1 H1B Cl7 0.90 2.77 3.47(3) 135.7 6
N1 H1C Cl9 0.90 2.75 3.29(2) 119.5 1_545
N3 H3D Cl8 0.90 2.32 2.99(10) 131.2 1_554
N3 H3D Cl9 0.90 2.75 3.27(7) 118.2 1_554
N3 H3E Cl3 0.90 2.30 2.93(11) 126.4 .

_refine_diff_density_max         1.080
_refine_diff_density_min         -1.162
_refine_diff_density_rms         0.269

_vrf_PLAT242_5                   
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of       Bi01 Check 
RESPONSE: ...Author Response :The alert is due to the disordered structure
;
_vrf_PLAT260_5                   
;
PROBLEM: Large Average Ueq of Residue Including       Cl3      0.572 Check 
RESPONSE: ...Author Response :The alert is due to the disordered structure
;
####################################################################### 
# 
# 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_aaa
_database_code_depnum_ccdc_archive 'CCDC 1914044'
loop_
_audit_author_name
_audit_author_address
'Hui Hui Li'
;Southeast University
China
;
_audit_update_record             
;
2019-09-16 deposited with the CCDC.	2020-01-06 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         ?
_chemical_formula_sum            'C6 H24 Bi Br6 N3'
_chemical_formula_weight         826.66

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 2yc'

_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, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   11.7730(3)
_cell_length_b                   8.0673(2)
_cell_length_c                   22.7281(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.720(2)
_cell_angle_gamma                90
_cell_volume                     2097.04(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    9253
_cell_measurement_theta_min      1.8630
_cell_measurement_theta_max      31.6900

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.618
_exptl_crystal_F_000             1496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    19.827
_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      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku, SCXmini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17426
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.845
_diffrn_reflns_theta_max         31.702
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.827
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.827
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.827
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7102
_reflns_number_gt                4743
_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)+(0.1359P)²] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7102
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0693
_refine_ls_wR_factor_ref         0.1826
_refine_ls_wR_factor_gt          0.1751
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 0.28565(2) 0.26709(4) 0.58566(2) 0.02012(13) Uani 1 1 d . . . . .
Br2 Br 0.35211(9) 0.02480(12) 0.68089(4) 0.0308(2) Uani 1 1 d . . . . .
Br3 Br 0.52224(8) 0.21316(12) 0.56664(4) 0.0278(2) Uani 1 1 d . . . . .
Br4 Br 0.20506(8) 0.01543(11) 0.49847(4) 0.0285(2) Uani 1 1 d . . . . .
Br5 Br 0.37521(8) 0.52209(11) 0.67393(4) 0.0278(2) Uani 1 1 d . . . . .
Br6 Br 0.23415(7) 0.51262(11) 0.49377(4) 0.0260(2) Uani 1 1 d . . . . .
Br7 Br 0.06286(8) 0.30205(13) 0.60579(5) 0.0341(2) Uani 1 1 d . . . . .
N3 N 0.5408(7) 0.2099(10) 0.4229(4) 0.0298(16) Uani 1 1 d . . . . .
H3A H 0.5415 0.0981 0.4284 0.045 Uiso 1 1 calc R U . . .
H3B H 0.5781 0.2599 0.4581 0.045 Uiso 1 1 calc R U . . .
H3C H 0.5782 0.2353 0.3933 0.045 Uiso 1 1 calc R U . . .
N1 N 0.3506(7) 0.2920(11) 0.7915(4) 0.0367(19) Uani 1 1 d . . . . .
H1A H 0.3910 0.2670 0.8298 0.055 Uiso 1 1 calc R U . . .
H1B H 0.3838 0.3813 0.7778 0.055 Uiso 1 1 calc R U . . .
H1C H 0.3523 0.2037 0.7668 0.055 Uiso 1 1 calc R U . . .
C5 C 0.4165(9) 0.2700(13) 0.4047(5) 0.039(2) Uani 1 1 d . . . . .
H4A H 0.4150 0.3926 0.4068 0.046 Uiso 1 1 calc R U . . .
H4B H 0.3719 0.2256 0.4331 0.046 Uiso 1 1 calc R U . . .
C3 C 0.0817(11) 0.7877(16) 0.6155(5) 0.048(3) Uani 1 1 d . . . . .
H5A H 0.1022 0.9057 0.6121 0.057 Uiso 1 1 calc R U . . .
H5B H 0.1546 0.7266 0.6334 0.057 Uiso 1 1 calc R U . . .
C1 C 0.2259(12) 0.331(2) 0.7918(6) 0.062(3) Uani 1 1 d . . . . .
H2A H 0.2242 0.4172 0.8227 0.074 Uiso 1 1 calc R U . . .
H2B H 0.1851 0.3760 0.7518 0.074 Uiso 1 1 calc R U . . .
C4 C 0.0014(16) 0.774(2) 0.6563(8) 0.079(5) Uani 1 1 d . . . . .
H3D H -0.0718 0.8316 0.6384 0.119 Uiso 1 1 calc R U . . .
H3E H 0.0377 0.8239 0.6956 0.119 Uiso 1 1 calc R U . . .
H3F H -0.0150 0.6566 0.6621 0.119 Uiso 1 1 calc R U . . .
N2 N 0.0311(7) 0.7224(11) 0.5556(4) 0.0333(18) Uani 1 1 d . . . . .
H8A H -0.0016 0.6217 0.5589 0.050 Uiso 1 1 calc R U . . .
H8B H 0.0881 0.7114 0.5349 0.050 Uiso 1 1 calc R U . . .
H8C H -0.0248 0.7933 0.5353 0.050 Uiso 1 1 calc R U . . .
C6 C 0.3596(10) 0.2135(15) 0.3404(6) 0.051(3) Uani 1 1 d . . . . .
H2C H 0.3956 0.2720 0.3117 0.076 Uiso 1 1 calc R U . . .
H2D H 0.2757 0.2384 0.3312 0.076 Uiso 1 1 calc R U . . .
H2E H 0.3708 0.0938 0.3370 0.076 Uiso 1 1 calc R U . . .
C2 C 0.1665(12) 0.185(2) 0.8049(7) 0.068(4) Uani 1 1 d . . . . .
H1D H 0.1723 0.0977 0.7758 0.101 Uiso 1 1 calc R U . . .
H1E H 0.0840 0.2107 0.8020 0.101 Uiso 1 1 calc R U . . .
H1F H 0.2027 0.1466 0.8460 0.101 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 Br7 2.7816(10) . ?
Bi1 Br6 2.8376(8) . ?
Bi1 Br4 2.8386(9) . ?
Bi1 Br2 2.8833(9) . ?
Bi1 Br5 2.8922(9) . ?
Bi1 Br3 2.9506(9) . ?
N3 C5 1.504(12) . ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
N3 H3C 0.9100 . ?
N1 C1 1.503(16) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
C5 C6 1.527(16) . ?
C5 H4A 0.9900 . ?
C5 H4B 0.9900 . ?
C3 N2 1.451(14) . ?
C3 C4 1.48(2) . ?
C3 H5A 0.9900 . ?
C3 H5B 0.9900 . ?
C1 C2 1.44(2) . ?
C1 H2A 0.9900 . ?
C1 H2B 0.9900 . ?
C4 H3D 0.9800 . ?
C4 H3E 0.9800 . ?
C4 H3F 0.9800 . ?
N2 H8A 0.9100 . ?
N2 H8B 0.9100 . ?
N2 H8C 0.9100 . ?
C6 H2C 0.9800 . ?
C6 H2D 0.9800 . ?
C6 H2E 0.9800 . ?
C2 H1D 0.9800 . ?
C2 H1E 0.9800 . ?
C2 H1F 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
Br7 Bi1 Br6 90.29(3) . . ?
Br7 Bi1 Br4 90.87(3) . . ?
Br6 Bi1 Br4 90.44(3) . . ?
Br7 Bi1 Br2 92.52(3) . . ?
Br6 Bi1 Br2 176.59(3) . . ?
Br4 Bi1 Br2 91.46(3) . . ?
Br7 Bi1 Br5 90.96(3) . . ?
Br6 Bi1 Br5 89.61(3) . . ?
Br4 Bi1 Br5 178.17(3) . . ?
Br2 Bi1 Br5 88.40(3) . . ?
Br7 Bi1 Br3 177.17(3) . . ?
Br6 Bi1 Br3 92.26(3) . . ?
Br4 Bi1 Br3 87.88(3) . . ?
Br2 Bi1 Br3 84.98(3) . . ?
Br5 Bi1 Br3 90.29(3) . . ?
C5 N3 H3A 109.5 . . ?
C5 N3 H3B 109.5 . . ?
H3A N3 H3B 109.5 . . ?
C5 N3 H3C 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
N3 C5 C6 110.1(9) . . ?
N3 C5 H4A 109.6 . . ?
C6 C5 H4A 109.6 . . ?
N3 C5 H4B 109.6 . . ?
C6 C5 H4B 109.6 . . ?
H4A C5 H4B 108.1 . . ?
N2 C3 C4 112.4(11) . . ?
N2 C3 H5A 109.1 . . ?
C4 C3 H5A 109.1 . . ?
N2 C3 H5B 109.1 . . ?
C4 C3 H5B 109.1 . . ?
H5A C3 H5B 107.8 . . ?
C2 C1 N1 110.5(13) . . ?
C2 C1 H2A 109.6 . . ?
N1 C1 H2A 109.6 . . ?
C2 C1 H2B 109.6 . . ?
N1 C1 H2B 109.6 . . ?
H2A C1 H2B 108.1 . . ?
C3 C4 H3D 109.5 . . ?
C3 C4 H3E 109.5 . . ?
H3D C4 H3E 109.5 . . ?
C3 C4 H3F 109.5 . . ?
H3D C4 H3F 109.5 . . ?
H3E C4 H3F 109.5 . . ?
C3 N2 H8A 109.5 . . ?
C3 N2 H8B 109.5 . . ?
H8A N2 H8B 109.5 . . ?
C3 N2 H8C 109.5 . . ?
H8A N2 H8C 109.5 . . ?
H8B N2 H8C 109.5 . . ?
C5 C6 H2C 109.5 . . ?
C5 C6 H2D 109.5 . . ?
H2C C6 H2D 109.5 . . ?
C5 C6 H2E 109.5 . . ?
H2C C6 H2E 109.5 . . ?
H2D C6 H2E 109.5 . . ?
C1 C2 H1D 109.5 . . ?
C1 C2 H1E 109.5 . . ?
H1D C2 H1E 109.5 . . ?
C1 C2 H1F 109.5 . . ?
H1D C2 H1F 109.5 . . ?
H1E C2 H1F 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
C2 H1E Br7 0.98 3.11 3.860(15) 134.8 2_556
C6 H2C Br5 0.98 3.12 3.859(12) 133.4 3_666
N2 H8C Br4 0.91 2.59 3.477(8) 165.5 3_566
N2 H8B Br6 0.91 2.68 3.484(9) 148.4 .
N2 H8B Br4 0.91 3.02 3.567(9) 120.1 1_565
N2 H8A Br7 0.91 2.82 3.570(9) 140.0 .
N2 H8A Br6 0.91 2.92 3.598(8) 132.1 3_566
C3 H5B Br5 0.99 3.03 4.015(13) 173.5 .
C3 H5A Br2 0.99 3.14 3.710(11) 118.2 1_565
C5 H4B Br3 0.99 3.13 3.623(12) 112.2 .
N1 H1C Br2 0.91 2.43 3.316(9) 164.9 .
N1 H1B Br5 0.91 3.01 3.645(8) 128.2 2_656
N1 H1B Br5 0.91 2.60 3.323(8) 136.9 .
N1 H1A Br3 0.91 2.37 3.278(8) 173.5 2_656
N3 H3C Br5 0.91 2.62 3.396(8) 143.5 3_666
N3 H3C Br2 0.91 2.93 3.486(8) 121.0 3_656
N3 H3B Br6 0.91 2.88 3.638(8) 141.5 3_666
N3 H3B Br3 0.91 2.73 3.325(8) 124.4 .
N3 H3A Br3 0.91 2.63 3.513(8) 163.4 3_656

_refine_diff_density_max         2.203
_refine_diff_density_min         -2.604
_refine_diff_density_rms         0.573

####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1912575'
loop_
_audit_author_name
_audit_author_address
'Hui Hui Li'
;Southeast University
China
;
_audit_update_record             
;
2019-09-16 deposited with the CCDC.	2020-01-06 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         ?
_chemical_formula_sum            'C6 H24 Bi Br6 N3'
_chemical_formula_weight         826.66

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

_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, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   22.444(3)
_cell_length_b                   8.1886(8)
_cell_length_c                   11.9852(14)
_cell_angle_alpha                90
_cell_angle_beta                 104.248(13)
_cell_angle_gamma                90
_cell_volume                     2134.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1680
_cell_measurement_theta_min      2.2970
_cell_measurement_theta_max      22.8500

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.572
_exptl_crystal_F_000             1496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    19.475
_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      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku, SCXmini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8129
_diffrn_reflns_av_unetI/netI     0.0911
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.872
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2025
_reflns_number_gt                1257
_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)+(0.0862P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2025
_refine_ls_number_parameters     84
_refine_ls_number_restraints     70
_refine_ls_R_factor_all          0.1184
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.1646
_refine_ls_wR_factor_gt          0.1347
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.056
_refine_ls_shift/su_mean         0.003

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 0.16718(4) 0.0000 0.21675(7) 0.0406(3) Uani 1 2 d S TU P . .
Br1 Br 0.25646(8) 0.2461(2) 0.27886(16) 0.0678(6) Uani 1 1 d . U . . .
Br2 Br 0.07399(9) 0.2495(2) 0.14302(19) 0.0787(7) Uani 1 1 d . U . . .
Br4 Br 0.18283(13) 0.0000 -0.0176(2) 0.1066(14) Uani 1 2 d S TU P . .
Br5 Br 0.14865(15) 0.0000 0.4371(2) 0.0888(10) Uani 1 2 d S TU P . .
N2 N 0.3277(7) 0.0000 -0.0377(15) 0.065(6) Uani 1 2 d S TU P . .
H2A H 0.3344 0.1013 -0.0643 0.098 Uiso 0.5 1 d R U P . .
H2B H 0.2856 -0.0259 -0.0615 0.098 Uiso 0.5 1 d R U P . .
H2C H 0.3512 -0.0754 -0.0652 0.098 Uiso 0.5 1 d R U P . .
C3 C 0.34997(3) 0.0000 0.0910(4) 0.127(12) Uani 1 2 d DS TU P . .
H3A H 0.3319 -0.0983 0.1199 0.152 Uiso 0.5 1 d R U P . .
H3B H 0.3319 0.0983 0.1199 0.152 Uiso 0.5 1 d R U P . .
C4 C 0.41831(3) 0.0000 0.1391(4) 0.138(15) Uani 1 2 d DS TU P . .
H4A H 0.4352 -0.1093 0.1294 0.208 Uiso 0.5 1 d R U P . .
H4B H 0.4286 0.0282 0.2207 0.208 Uiso 0.5 1 d R U P . .
H4C H 0.4375 0.0811 0.0976 0.208 Uiso 0.5 1 d R U P . .
C6 C 0.08750(4) 0.5000 0.49786(7) 0.180(16) Uani 1 2 d DS TU P . .
H3E H 0.1098 0.4590 0.5661 0.269 Uiso 0.5 1 d R U P . .
H3D H 0.0525 0.4365 0.4701 0.269 Uiso 0.5 1 d R U P . .
H3C H 0.0750 0.6044 0.5078 0.269 Uiso 0.5 1 d R U P . .
C5 C 0.13260(4) 0.5000 0.42398(7) 0.155(14) Uani 1 2 d DS TU P . .
H5A H 0.1182 0.5969 0.3748 0.186 Uiso 0.5 1 d R U P . .
H5B H 0.1182 0.4031 0.3748 0.186 Uiso 0.5 1 d R U P . .
N3 N 0.1848(12) 0.5000 0.453(2) 0.138(8) Uani 1 2 d S TU P . .
H6A H 0.1979 0.4035 0.4197 0.206 Uiso 0.5 1 d R U P . .
H6B H 0.2028 0.5000 0.5340 0.206 Uiso 1 2 d R U P . .
H6C H 0.1978 0.5949 0.4178 0.206 Uiso 0.5 1 d R U P . .
C2 C 0.06411(6) 0.14270(11) 0.66416(11) 0.138(8) Uani 0.5 1 d D U P . .
H1C H 0.0642 0.1111 0.5910 0.206 Uiso 0.5 1 d R U P . .
H1D H 0.0352 0.2264 0.6613 0.206 Uiso 0.5 1 d R U P . .
H1E H 0.1042 0.1784 0.7014 0.206 Uiso 0.5 1 d R U P . .
C1 C 0.03842(6) 0.0000 0.71542(11) 0.138(8) Uani 1 2 d DS TU P . .
H1A H 0.0742 -0.0750 0.7180 0.165 Uiso 0.5 1 d R U P . .
H1B H 0.0006 -0.0554 0.6690 0.165 Uiso 0.5 1 d R U P . .
N1 N 0.0411(9) 0.0000 0.8422(18) 0.087(7) Uani 1 2 d S TU P . .
H2D H 0.0807 0.0351 0.8959 0.131 Uiso 0.5 1 d R U P . .
H2E H 0.0300 -0.1110 0.8622 0.131 Uiso 0.5 1 d R U P . .
H2F H 0.0066 0.0760 0.8466 0.131 Uiso 0.5 1 d R U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 Br5 2.772(3) . ?
Bi1 Br1 2.8101(17) . ?
Bi1 Br1 2.8101(17) 6 ?
Bi1 Br2 2.9015(18) . ?
Bi1 Br2 2.9015(18) 6 ?
Bi1 Br4 2.915(3) . ?
N2 C3 1.500(18) . ?
N2 H2A 0.9138 . ?
N2 H2B 0.9412 . ?
N2 H2C 0.9232 . ?
C3 C4 1.5000(2) . ?
C3 H3A 1.0008 . ?
C3 H3B 1.0008 . ?
C4 H4A 0.9906 . ?
C4 H4B 0.9749 . ?
C4 H4C 0.9902 . ?
C6 C5 1.50000(18) . ?
C6 H3E 0.9114 . ?
C6 H3D 0.9317 . ?
C6 H3C 0.9167 . ?
C5 N3 1.14(3) . ?
C5 H5A 0.9942 . ?
C5 H5B 0.9942 . ?
N3 H6A 0.9600 . ?
N3 H6B 0.9599 . ?
N3 H6C 0.9600 . ?
C2 C1 1.50000(11) . ?
C2 H1C 0.9146 . ?
C2 H1D 0.9382 . ?
C2 H1E 0.9462 . ?
C1 C2 1.50000(11) 6 ?
C1 N1 1.51(2) . ?
C1 H1A 1.0060 . ?
C1 H1B 1.0020 . ?
N1 H2D 1.0024 . ?
N1 H2E 0.9875 . ?
N1 H2F 1.0048 . ?

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
Br5 Bi1 Br1 90.69(6) . . ?
Br5 Bi1 Br1 90.69(6) . 6 ?
Br1 Bi1 Br1 91.64(8) . 6 ?
Br5 Bi1 Br2 91.39(7) . . ?
Br1 Bi1 Br2 89.39(6) . . ?
Br1 Bi1 Br2 177.67(6) 6 . ?
Br5 Bi1 Br2 91.39(7) . 6 ?
Br1 Bi1 Br2 177.67(6) . 6 ?
Br1 Bi1 Br2 89.39(6) 6 6 ?
Br2 Bi1 Br2 89.51(8) . 6 ?
Br5 Bi1 Br4 178.35(8) . . ?
Br1 Bi1 Br4 90.46(6) . . ?
Br1 Bi1 Br4 90.46(6) 6 . ?
Br2 Bi1 Br4 87.44(6) . . ?
Br2 Bi1 Br4 87.44(6) 6 . ?
C3 N2 H2A 108.4 . . ?
C3 N2 H2B 111.5 . . ?
H2A N2 H2B 109.8 . . ?
C3 N2 H2C 107.0 . . ?
H2A N2 H2C 109.0 . . ?
H2B N2 H2C 111.1 . . ?
N2 C3 C4 116.5(7) . . ?
N2 C3 H3A 107.1 . . ?
C4 C3 H3A 109.3 . . ?
N2 C3 H3B 107.1 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 107.1 . . ?
C3 C4 H4A 109.9 . . ?
C3 C4 H4B 110.7 . . ?
H4A C4 H4B 109.2 . . ?
C3 C4 H4C 109.7 . . ?
H4A C4 H4C 108.7 . . ?
H4B C4 H4C 108.6 . . ?
C5 C6 H3E 103.2 . . ?
C5 C6 H3D 114.9 . . ?
H3E C6 H3D 110.1 . . ?
C5 C6 H3C 110.4 . . ?
H3E C6 H3C 110.2 . . ?
H3D C6 H3C 108.0 . . ?
N3 C5 C6 128.1(14) . . ?
N3 C5 H5A 109.9 . . ?
C6 C5 H5A 100.5 . . ?
N3 C5 H5B 109.9 . . ?
C6 C5 H5B 100.5 . . ?
H5A C5 H5B 105.9 . . ?
C5 N3 H6A 105.8 . . ?
C5 N3 H6B 116.8 . . ?
H6A N3 H6B 108.8 . . ?
C5 N3 H6C 105.6 . . ?
H6A N3 H6C 109.5 . . ?
H6B N3 H6C 110.1 . . ?
C1 C2 H1C 105.3 . . ?
C1 C2 H1D 104.6 . . ?
H1C C2 H1D 109.7 . . ?
C1 C2 H1E 117.6 . . ?
H1C C2 H1E 108.2 . . ?
H1D C2 H1E 111.1 . . ?
C2 C1 C2 102.34(11) 6 . ?
C2 C1 N1 119.3(3) 6 . ?
C2 C1 N1 119.3(3) . . ?
C2 C1 H1A 32.0 6 . ?
C2 C1 H1A 95.9 . . ?
N1 C1 H1A 97.8 . . ?
C2 C1 H1B 77.2 6 . ?
C2 C1 H1B 118.9 . . ?
N1 C1 H1B 112.3 . . ?
H1A C1 H1B 107.6 . . ?
C1 N1 H2D 117.2 . . ?
C1 N1 H2E 107.1 . . ?
H2D N1 H2E 110.2 . . ?
C1 N1 H2F 102.3 . . ?
H2D N1 H2F 111.2 . . ?
H2E N1 H2F 108.3 . . ?

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
N1 H2F Br2 1.00 2.33 3.332(16) 179.4 2_556
N1 H2E Br2 0.99 2.58 3.332(16) 132.8 5_556
N1 H2D Br4 1.00 2.29 3.211(18) 152.3 1_556
C2 H1E Br1 0.95 3.14 4.020(2) 155.4 7_556
C2 H1C Br5 0.91 3.09 3.862(3) 143.4 .
N3 H6C Br1 0.96 2.70 3.59(2) 154.7 6_565
N3 H6B Br1 0.96 2.99 3.75(2) 137.6 4_556
N3 H6B Br1 0.96 2.99 3.75(2) 137.6 7_556
N3 H6A Br1 0.96 2.71 3.59(2) 153.0 .
C5 H5B Br2 0.99 2.99 3.886(2) 150.8 .
C5 H5A Br2 0.99 2.99 3.886(2) 150.8 6_565
C3 H3B Br1 1.00 3.09 3.983(4) 149.2 .
C3 H3A Br1 1.00 3.09 3.983(4) 149.2 6
N2 H2C Br2 0.92 2.55 3.470(15) 172.0 4_545
N2 H2B Br4 0.94 2.50 3.319(17) 145.8 .
N2 H2A Br2 0.91 2.75 3.470(15) 136.4 7
N2 H2A Br1 0.91 3.12 3.682(14) 121.3 7

_refine_diff_density_max         1.280
_refine_diff_density_min         -1.834
_refine_diff_density_rms         0.352

####################################################################### 
# 
# 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_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1964786'
loop_
_audit_author_name
_audit_author_address
'Hui Hui Li'
;Southeast University
China
;
_audit_update_record             
;
2019-12-30 deposited with the CCDC.	2020-01-06 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         ?
_chemical_formula_sum            'C6 H24 Bi I6 N3'
_chemical_formula_weight         1108.66

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 '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                   8.9520(3)
_cell_length_b                   29.5398(8)
_cell_length_c                   11.8481(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.269(3)
_cell_angle_gamma                90
_cell_volume                     3128.02(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7152
_cell_measurement_theta_min      1.9260
_cell_measurement_theta_max      22.9440

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.354
_exptl_crystal_F_000             1928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    11.550
_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      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku, SCXmini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23170
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.854
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5498
_reflns_number_gt                3902
_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)+(0.7000P)²] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5497
_refine_ls_number_parameters     151
_refine_ls_number_restraints     142
_refine_ls_R_factor_all          0.2550
_refine_ls_R_factor_gt           0.2278
_refine_ls_wR_factor_ref         0.6567
_refine_ls_wR_factor_gt          0.6230
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.099
_refine_ls_shift/su_mean         0.023

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 0.82037(18) 0.12718(6) 0.33602(14) 0.0518(8) Uani 1 1 d . U . . .
I2 I 1.0531(4) 0.05409(11) 0.2765(3) 0.0611(10) Uani 1 1 d . U . . .
I3 I 0.5673(4) 0.06230(13) 0.2453(3) 0.0684(11) Uani 1 1 d . U . . .
I4 I 0.8217(4) 0.08073(13) 0.5673(3) 0.0713(12) Uani 1 1 d . U . . .
I5 I 0.8401(5) 0.16947(14) 0.0965(3) 0.0765(12) Uani 1 1 d . U . . .
I6 I 0.5844(5) 0.19471(15) 0.4002(4) 0.0849(13) Uani 1 1 d . U . . .
I7 I 1.0712(5) 0.19216(16) 0.4138(4) 0.0879(14) Uani 1 1 d . U . . .
N1 N 0.782(5) 0.9727(17) 0.405(4) 0.075(11) Uani 1 1 d D U . . .
H1A H 0.8574 0.9742 0.4575 0.113 Uiso 1 1 calc R U . . .
H1B H 0.7648 1.0001 0.3762 0.113 Uiso 1 1 calc R U . . .
H1C H 0.8065 0.9539 0.3504 0.113 Uiso 1 1 calc R U . . .
N2 N 0.814(11) 0.063(3) 1.010(8) 0.15(2) Uani 1 1 d D U . . .
H2A H 0.8780 0.0786 0.9698 0.228 Uiso 1 1 calc R U . . .
H2B H 0.8644 0.0447 1.0576 0.228 Uiso 1 1 calc R U . . .
H2C H 0.7599 0.0824 1.0484 0.228 Uiso 1 1 calc R U . . .
C2 C 0.648(5) 0.90521(19) 0.451(4) 0.058(10) Uani 1 1 d D U . . .
H2D H 0.6282 0.8958 0.3740 0.087 Uiso 1 1 calc R U . . .
H2E H 0.5717 0.8932 0.4967 0.087 Uiso 1 1 calc R U . . .
H2F H 0.7438 0.8942 0.4785 0.087 Uiso 1 1 calc R U . . .
C1 C 0.646(6) 0.95593(19) 0.457(5) 0.090(14) Uani 1 1 d D U . . .
H1D H 0.5574 0.9677 0.4163 0.108 Uiso 1 1 calc R U . . .
H1E H 0.6456 0.9658 0.5350 0.108 Uiso 1 1 calc R U . . .
C4 C 0.5675(9) 0.038(3) 0.8627(11) 0.17(2) Uani 1 1 d D U . . .
H4A H 0.5748 0.0604 0.8040 0.254 Uiso 1 1 calc R U . . .
H4B H 0.4887 0.0466 0.9103 0.254 Uiso 1 1 calc R U . . .
H4C H 0.5459 0.0092 0.8294 0.254 Uiso 1 1 calc R U . . .
C3 C 0.7129(9) 0.036(3) 0.9319(11) 0.171(19) Uani 1 1 d D U . . .
H3A H 0.6983 0.0091 0.9769 0.205 Uiso 1 1 calc R U . . .
H3B H 0.7810 0.0266 0.8757 0.205 Uiso 1 1 calc R U . . .
N3 N 0.269(6) 0.1425(15) 0.169(4) 0.073(11) Uani 1 1 d D U . . .
H3C H 0.3198 0.1456 0.2355 0.110 Uiso 1 1 calc R U . . .
H3D H 0.2771 0.1141 0.1450 0.110 Uiso 1 1 calc R U . . .
H3E H 0.1728 0.1489 0.1775 0.110 Uiso 1 1 calc R U . . .
C6 C 0.2353(13) 0.2159(3) 0.087(7) 0.13(2) Uani 1 1 d D U . . .
H6A H 0.2714 0.2375 0.0348 0.194 Uiso 1 1 calc R U . . .
H6B H 0.2412 0.2286 0.1620 0.194 Uiso 1 1 calc R U . . .
H6C H 0.1332 0.2084 0.0660 0.194 Uiso 1 1 calc R U . . .
C5 C 0.3294(13) 0.1739(3) 0.086(4) 0.105(16) Uani 1 1 d D U . . .
H5A H 0.3236 0.1604 0.0112 0.126 Uiso 1 1 calc R U . . .
H5B H 0.4332 0.1809 0.1066 0.126 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 I6 3.034(4) . ?
Bi1 I7 3.056(5) . ?
Bi1 I4 3.064(4) . ?
Bi1 I3 3.112(4) . ?
Bi1 I2 3.109(4) . ?
Bi1 I5 3.115(4) . ?
N1 C1 1.48(2) . ?
N2 C3 1.49(2) . ?
C2 C1 1.5000(3) . ?
C4 C3 1.4999(6) . ?
N3 C5 1.480(19) . ?
C6 C5 1.5001(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I6 Bi1 I7 91.24(14) . . ?
I6 Bi1 I4 92.14(12) . . ?
I7 Bi1 I4 92.66(12) . . ?
I6 Bi1 I3 89.31(12) . . ?
I7 Bi1 I3 177.33(12) . . ?
I4 Bi1 I3 89.93(11) . . ?
I6 Bi1 I2 177.03(12) . . ?
I7 Bi1 I2 90.81(12) . . ?
I4 Bi1 I2 85.62(10) . . ?
I3 Bi1 I2 88.74(10) . . ?
I6 Bi1 I5 92.36(12) . . ?
I7 Bi1 I5 86.79(12) . . ?
I4 Bi1 I5 175.47(12) . . ?
I3 Bi1 I5 90.58(11) . . ?
I2 Bi1 I5 89.90(11) . . ?
N1 C1 C2 108(4) . . ?
N2 C3 C4 142(8) . . ?
N3 C5 C6 106(4) . . ?

_refine_diff_density_max         2.629
_refine_diff_density_min         -2.962
_refine_diff_density_rms         1.054

_vrf_PLAT082_a                   
;
PROBLEM: High R1 Value ..................................       0.23 Report
RESPONSE:  ...Author Response :The alarm is due to poor crystal data
;
_vrf_PLAT084_a                   
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.66 Report
RESPONSE: ...Author Response :The alarm is due to poor crystal data
;
_vrf_PLAT602_a                   
;
PROBLEM: VERY LARGE Solvent Accessible VOID(S) in Structure        ! Info  
RESPONSE: ...Author Response :The alarm is due to the possible presence of a 
                              cavity in the structure itself
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1973779'
loop_
_audit_author_name
_audit_author_address
'Hui Hui Li'
;Southeast University
China
;
_audit_update_record             
;
2019-12-23 deposited with the CCDC.	2020-01-06 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         ?
_chemical_formula_sum            'C6  Bi Cl3 I6 N3'
_chemical_formula_weight         1190.82

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'
N N 0.0061 0.0033 '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'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

_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, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   26.2181(14)
_cell_length_b                   8.6303(4)
_cell_length_c                   13.2652(7)
_cell_angle_alpha                90
_cell_angle_beta                 110.247(4)
_cell_angle_gamma                90
_cell_volume                     2816.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    373(2)
_cell_measurement_reflns_used    5127
_cell_measurement_theta_min      2.7020
_cell_measurement_theta_max      29.5760

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.809
_exptl_crystal_F_000             2036
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    13.116
_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      373(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku, SCXmini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11426
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.501
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_full        24.993
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2660
_reflns_number_gt                2204
_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)+(0.5000P)²] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2658
_refine_ls_number_parameters     115
_refine_ls_number_restraints     191
_refine_ls_R_factor_all          0.1714
_refine_ls_R_factor_gt           0.1628
_refine_ls_wR_factor_ref         0.5364
_refine_ls_wR_factor_gt          0.5177
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_restrained_S_all      1.140
_refine_ls_shift/su_max          0.014
_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 0.32808(5) 1.0000 0.30205(9) 0.0574(9) Uani 1 2 d S TU P . .
I3 I 0.24187(10) 1.2538(3) 0.2365(2) 0.0853(11) Uani 1 1 d . U . . .
I4 I 0.33701(17) 1.0000 0.0786(3) 0.0911(13) Uani 1 2 d S TU P . .
I5 I 0.41901(11) 0.7499(3) 0.3791(3) 0.0892(11) Uani 1 1 d . U . . .
I7 I 0.32267(17) 1.0000 0.5319(3) 0.140(2) Uani 1 2 d S TU P . .
C2 C -0.00376(2) 0.5000 0.25366(2) 0.089(9) Uani 1 2 d DS TU P B .
Cl2 Cl 0.0497(3) 0.0000 0.3249(5) 0.0433(16) Uani 1 2 d DS TU P A .
N2 N 0.147(3) 0.0000 0.213(3) 0.130(17) Uani 1 2 d DS TU P . .
C3 C 0.12312(2) 0.0000 0.41285(2) 0.089(9) Uani 1 2 d DS TU P . .
Cl3 Cl 0.0771(6) -0.069(3) 1.0049(14) 0.096(5) Uani 0.5 1 d D U P . .
C5 C 0.15045(2) 0.0000 1.05181(2) 0.107(10) Uani 1 2 d DS TU P . .
C6 C 0.18803(2) 0.0000 0.98846(2) 0.115(12) Uani 1 2 d DS TU P . .
N3 N 0.201(3) 0.0000 0.889(4) 0.142(18) Uani 1 2 d DS TU P . .
N1 N 0.0280(17) 0.5000 0.3697(16) 0.089(10) Uani 1 2 d DS TU P . .
C1 C 0.01879(2) 0.5000 0.16402(2) 0.090(9) Uani 1 2 d DS TU P . .
C4 C 0.13111(2) 0.0000 0.30622(2) 0.099(10) Uani 1 2 d DS TU P A 1
Cl1 Cl 0.0842(4) 0.4414(16) 0.1494(7) 0.067(4) Uani 0.5 1 d D U P B 1


_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 I3 3.050(2) 6_575 ?
Bi1 I3 3.050(2) . ?
Bi1 I4 3.053(3) . ?
Bi1 I7 3.101(4) . ?
Bi1 I5 3.115(2) . ?
Bi1 I5 3.115(2) 6_575 ?
C2 N1 1.475(19) . ?
C2 C1 1.50000(7) . ?
Cl2 C3 1.874(6) . ?
N2 C4 1.437(14) . ?
C3 C4 1.50000(7) . ?
Cl3 Cl3 1.18(4) 6 ?
Cl3 C5 1.898(13) . ?
C5 C6 1.50000(6) . ?
C5 Cl3 1.898(13) 6 ?
C6 N3 1.48(2) . ?
C1 Cl1 1.862(9) 6_565 ?
C1 Cl1 1.862(9) . ?
Cl1 Cl1 1.01(3) 6_565 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I3 Bi1 I3 91.81(11) 6_575 . ?
I3 Bi1 I4 91.22(8) 6_575 . ?
I3 Bi1 I4 91.22(8) . . ?
I3 Bi1 I7 89.94(8) 6_575 . ?
I3 Bi1 I7 89.94(8) . . ?
I4 Bi1 I7 178.33(10) . . ?
I3 Bi1 I5 90.19(9) 6_575 . ?
I3 Bi1 I5 177.23(8) . . ?
I4 Bi1 I5 90.65(8) . . ?
I7 Bi1 I5 88.14(8) . . ?
I3 Bi1 I5 177.23(8) 6_575 6_575 ?
I3 Bi1 I5 90.19(9) . 6_575 ?
I4 Bi1 I5 90.65(8) . 6_575 ?
I7 Bi1 I5 88.14(8) . 6_575 ?
I5 Bi1 I5 87.75(11) . 6_575 ?
N1 C2 C1 126.4(18) . . ?
C4 C3 Cl2 82.1(2) . . ?
Cl3 Cl3 C5 71.8(7) 6 . ?
C6 C5 Cl3 127.1(5) . 6 ?
C6 C5 Cl3 127.1(6) . . ?
Cl3 C5 Cl3 36.3(14) 6 . ?
N3 C6 C5 154(3) . . ?
C2 C1 Cl1 135.4(3) . 6_565 ?
C2 C1 Cl1 135.5(3) . . ?
Cl1 C1 Cl1 31.5(9) 6_565 . ?
N2 C4 C3 172(3) . . ?
Cl1 Cl1 C1 74.2(4) 6_565 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl3 Cl3 C5 C6 -104.4(6) 6 . . . ?
Cl3 C5 C6 N3 -23.0(9) 6 . . . ?
Cl3 C5 C6 N3 23.0(9) . . . . ?
N1 C2 C1 Cl1 -22.8(6) . . . 6_565 ?
N1 C2 C1 Cl1 22.8(6) . . . . ?
C2 C1 Cl1 Cl1 -106.7(5) . . . 6_565 ?

_refine_diff_density_max         4.470
_refine_diff_density_min         -4.095
_refine_diff_density_rms         0.804

_vrf_PLAT084_2                   
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.54 Report
RESPONSE: ...Author Response :The alarm is due to poor crystal data
;
_vrf_PLAT082_2                   
;
PROBLEM: High R1 Value ..................................       0.16 Report
RESPONSE: ...Author Response :The alarm is due to poor crystal data
;
####################################################################### 
# 
# 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_SS
_database_code_depnum_ccdc_archive 'CCDC 1964787'
loop_
_audit_author_name
_audit_author_address
'Hui Hui Li'
;Southeast University
China
;
_audit_update_record             
;
2019-12-31 deposited with the CCDC.	2020-01-06 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         ?
_chemical_formula_sum            'C6  Bi Cl3 I6 N3'
_chemical_formula_weight         1190.82

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.57010(10)
_cell_length_b                   12.4903(2)
_cell_length_c                   12.9228(2)
_cell_angle_alpha                103.9430(10)
_cell_angle_beta                 108.8150(10)
_cell_angle_gamma                93.0350(10)
_cell_volume                     1257.88(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11554
_cell_measurement_theta_min      2.0600
_cell_measurement_theta_max      31.7790

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.144
_exptl_crystal_F_000             1018
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    14.682
_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      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku, SCXmini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19829
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.697
_diffrn_reflns_theta_max         31.659
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.823
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.823
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.823
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8487
_reflns_number_gt                6100
_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)+(0.0505P)²+8.4674P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6983
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.1098
_refine_ls_wR_factor_gt          0.0971
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.001
_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 0.15578(3) 0.20850(2) 0.82655(2) 0.01026(8) Uani 1 1 d . . . . .
I3 I 0.00668(6) 0.29804(4) 1.01075(4) 0.01404(11) Uani 1 1 d . . . . .
I4 I 0.10824(6) -0.03064(4) 0.86221(4) 0.01289(11) Uani 1 1 d . . . . .
I5 I 0.31622(6) 0.11694(4) 0.64647(4) 0.01536(11) Uani 1 1 d . . . . .
I6 I 0.51471(6) 0.26507(4) 1.00563(4) 0.01261(10) Uani 1 1 d . . . . .
I10 I -0.18476(6) 0.14785(4) 0.64201(4) 0.01453(11) Uani 1 1 d . . . . .
I12 I 0.18923(6) 0.43884(4) 0.79480(4) 0.01468(11) Uani 1 1 d . . . . .
Cl1 Cl 0.4095(2) 0.15546(13) 0.37486(14) 0.0124(3) Uani 1 1 d . . . . .
C1 C 0.3837(11) 0.1596(7) 0.2257(7) 0.0205(16) Uani 1 1 d . . . . .
C2 C 0.4278(9) 0.0538(6) 0.1623(7) 0.0150(14) Uani 1 1 d . . . . .
N1 N 0.3126(8) -0.0472(5) 0.1496(6) 0.0156(13) Uani 1 1 d . . . . .
Cl2 Cl 0.3466(3) 0.44582(15) 0.33827(17) 0.0206(4) Uani 1 1 d . . . . .
C4 C 0.4251(12) 0.5800(7) 0.3303(7) 0.0249(18) Uani 1 1 d . . . . .
C5 C 0.3283(11) 0.6036(6) 0.2182(7) 0.0192(16) Uani 1 1 d . . . . .
N2 N 0.3507(9) 0.5208(6) 0.1189(6) 0.0191(14) Uani 1 1 d . . . . .
Cl4 Cl 0.7665(2) 0.37207(17) 0.41143(19) 0.0225(4) Uani 1 1 d . . . . .
C10 C 1.0626(11) 0.2847(7) 0.4400(8) 0.0263(18) Uani 1 1 d . . . . .
C11 C 0.9465(12) 0.3449(7) 0.3654(8) 0.0282(19) Uani 1 1 d . . . . .
N3 N 0.9836(10) 0.1710(6) 0.4290(6) 0.0227(15) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 I12 3.0142(5) . ?
Bi1 I10 3.0306(5) . ?
Bi1 I3 3.0627(5) . ?
Bi1 I5 3.0922(5) . ?
Bi1 I6 3.1156(5) . ?
Bi1 I4 3.1553(5) . ?
Cl1 C1 1.882(8) . ?
C1 C2 1.514(11) . ?
C2 N1 1.502(9) . ?
Cl2 C4 1.811(9) . ?
C4 C5 1.527(12) . ?
C5 N2 1.515(10) . ?
Cl4 C11 1.843(10) . ?
C10 N3 1.495(11) . ?
C10 C11 1.514(12) . ?

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
I12 Bi1 I10 91.062(15) . . ?
I12 Bi1 I3 89.233(14) . . ?
I10 Bi1 I3 92.089(14) . . ?
I12 Bi1 I5 91.452(14) . . ?
I10 Bi1 I5 89.592(14) . . ?
I3 Bi1 I5 178.173(15) . . ?
I12 Bi1 I6 89.118(14) . . ?
I10 Bi1 I6 176.691(15) . . ?
I3 Bi1 I6 91.217(14) . . ?
I5 Bi1 I6 87.101(14) . . ?
I12 Bi1 I4 177.763(15) . . ?
I10 Bi1 I4 87.823(14) . . ?
I3 Bi1 I4 88.870(14) . . ?
I5 Bi1 I4 90.480(14) . . ?
I6 Bi1 I4 92.107(13) . . ?
C2 C1 Cl1 110.2(5) . . ?
N1 C2 C1 111.7(6) . . ?
C5 C4 Cl2 111.8(6) . . ?
N2 C5 C4 110.8(7) . . ?
N3 C10 C11 112.4(7) . . ?
C10 C11 Cl4 110.5(6) . . ?

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
Cl1 C1 C2 N1 63.1(8) . . . . ?
Cl2 C4 C5 N2 -64.1(8) . . . . ?
N3 C10 C11 Cl4 64.7(9) . . . . ?

_refine_diff_density_max         2.591
_refine_diff_density_min         -2.849
_refine_diff_density_rms         0.388

####################################################################### 
# 
# 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_aaa_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1914043'
loop_
_audit_author_name
_audit_author_address
'Hui Hui Li'
;Southeast University
China
;
_audit_update_record             
;
2019-09-16 deposited with the CCDC.	2020-01-06 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         ?
_chemical_formula_sum            'C6 H24 Bi Cl6 N3'
_chemical_formula_weight         559.96

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'
N N 0.0061 0.0033 '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'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 2yc'

_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, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   11.5267(3)
_cell_length_b                   7.8653(2)
_cell_length_c                   21.5333(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.831(2)
_cell_angle_gamma                90
_cell_volume                     1895.62(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    12009
_cell_measurement_theta_min      1.9480
_cell_measurement_theta_max      31.9210

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.962
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    10.131
_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      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku, SCXmini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20862
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.819
_diffrn_reflns_theta_max         31.772
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.835
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.835
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6463
_reflns_number_gt                4641
_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)+(0.0372P)²] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6463
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0282
_refine_ls_wR_factor_ref         0.0684
_refine_ls_wR_factor_gt          0.0665
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.004
_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 0.28607(2) 0.22378(2) 0.58385(2) 0.02021(5) Uani 1 1 d . . . . .
Cl4 Cl 0.23236(8) -0.01398(11) 0.49150(4) 0.03034(19) Uani 1 1 d . . . . .
Cl5 Cl 0.34817(9) 0.45615(12) 0.67980(4) 0.0330(2) Uani 1 1 d . . . . .
Cl6 Cl 0.20214(8) 0.47231(11) 0.49912(4) 0.03019(19) Uani 1 1 d . . . . .
Cl7 Cl 0.51640(8) 0.28821(12) 0.56662(4) 0.02962(19) Uani 1 1 d . . . . .
Cl8 Cl 0.37637(8) -0.02281(11) 0.67227(4) 0.02864(18) Uani 1 1 d . . . . .
Cl1 Cl 0.07302(8) 0.18422(14) 0.60539(5) 0.0356(2) Uani 1 1 d . . . . .
N1 N 0.3494(3) 0.1954(4) 0.79289(16) 0.0333(7) Uani 1 1 d . . . . .
H2A H 0.3478 0.2813 0.7644 0.050 Uiso 1 1 calc R U . . .
H2B H 0.3838 0.1020 0.7799 0.050 Uiso 1 1 calc R U . . .
H2C H 0.3926 0.2285 0.8321 0.050 Uiso 1 1 calc R U . . .
C1 C 0.2248(4) 0.1537(6) 0.7966(2) 0.0470(11) Uani 1 1 d . . . . .
H1A H 0.2268 0.0677 0.8304 0.056 Uiso 1 1 calc R U . . .
H1B H 0.1803 0.1051 0.7553 0.056 Uiso 1 1 calc R U . . .
C5 C 0.5844(4) 0.7557(6) 0.5988(2) 0.0400(10) Uani 1 1 d . . . . .
H10A H 0.5913 0.8802 0.5938 0.048 Uiso 1 1 calc R U . . .
H10B H 0.6308 0.6993 0.5714 0.048 Uiso 1 1 calc R U . . .
C6 C 0.6351(4) 0.7078(5) 0.6671(2) 0.0396(10) Uani 1 1 d . . . . .
H2D H 0.5938 0.7713 0.6946 0.059 Uiso 1 1 calc R U . . .
H2E H 0.7205 0.7352 0.6790 0.059 Uiso 1 1 calc R U . . .
H2F H 0.6243 0.5856 0.6725 0.059 Uiso 1 1 calc R U . . .
C3 C 0.9149(5) 0.2915(7) 0.3822(2) 0.0532(13) Uani 1 1 d . . . . .
H8A H 0.8398 0.2300 0.3633 0.064 Uiso 1 1 calc R U . . .
H8B H 0.8949 0.4132 0.3851 0.064 Uiso 1 1 calc R U . . .
C2 C 0.1623(4) 0.3121(7) 0.8114(3) 0.0565(14) Uani 1 1 d . . . . .
H3A H 0.2022 0.3539 0.8540 0.085 Uiso 1 1 calc R U . . .
H3B H 0.0788 0.2853 0.8103 0.085 Uiso 1 1 calc R U . . .
H3C H 0.1653 0.3997 0.7795 0.085 Uiso 1 1 calc R U . . .
C4 C 0.9954(7) 0.2741(7) 0.3400(3) 0.076(2) Uani 1 1 d . . . . .
H7A H 1.0585 0.3602 0.3509 0.114 Uiso 1 1 calc R U . . .
H7B H 0.9507 0.2899 0.2956 0.114 Uiso 1 1 calc R U . . .
H7C H 1.0314 0.1605 0.3451 0.114 Uiso 1 1 calc R U . . .
N3 N 0.4567(3) 0.7047(4) 0.57765(16) 0.0272(7) Uani 1 1 d . . . . .
H11A H 0.4508 0.5896 0.5800 0.041 Uiso 1 1 calc R U . . .
H11B H 0.4269 0.7390 0.5366 0.041 Uiso 1 1 calc R U . . .
H11C H 0.4144 0.7542 0.6034 0.041 Uiso 1 1 calc R U . . .
N2 N 0.9642(3) 0.2266(4) 0.44614(19) 0.0359(8) Uani 1 1 d . . . . .
H1C H 0.9940 0.1204 0.4436 0.054 Uiso 1 1 calc R U . . .
H1D H 0.9058 0.2224 0.4680 0.054 Uiso 1 1 calc R U . . .
H1E H 1.0239 0.2965 0.4669 0.054 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 2.6242(9) . ?
Bi1 Cl6 2.6911(9) . ?
Bi1 Cl4 2.6920(9) . ?
Bi1 Cl5 2.7229(9) . ?
Bi1 Cl8 2.7427(8) . ?
Bi1 Cl7 2.8133(9) . ?
N1 C1 1.494(6) . ?
N1 H2A 0.9100 . ?
N1 H2B 0.9100 . ?
N1 H2C 0.9100 . ?
C1 C2 1.511(7) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C5 N3 1.487(5) . ?
C5 C6 1.495(7) . ?
C5 H10A 0.9900 . ?
C5 H10B 0.9900 . ?
C6 H2D 0.9800 . ?
C6 H2E 0.9800 . ?
C6 H2F 0.9800 . ?
C3 C4 1.451(8) . ?
C3 N2 1.451(6) . ?
C3 H8A 0.9900 . ?
C3 H8B 0.9900 . ?
C2 H3A 0.9800 . ?
C2 H3B 0.9800 . ?
C2 H3C 0.9800 . ?
C4 H7A 0.9800 . ?
C4 H7B 0.9800 . ?
C4 H7C 0.9800 . ?
N3 H11A 0.9100 . ?
N3 H11B 0.9100 . ?
N3 H11C 0.9100 . ?
N2 H1C 0.9100 . ?
N2 H1D 0.9100 . ?
N2 H1E 0.9100 . ?

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 Cl6 90.35(3) . . ?
Cl1 Bi1 Cl4 89.34(3) . . ?
Cl6 Bi1 Cl4 91.25(3) . . ?
Cl1 Bi1 Cl5 91.88(3) . . ?
Cl6 Bi1 Cl5 90.78(3) . . ?
Cl4 Bi1 Cl5 177.62(3) . . ?
Cl1 Bi1 Cl8 90.54(3) . . ?
Cl6 Bi1 Cl8 178.30(3) . . ?
Cl4 Bi1 Cl8 90.21(3) . . ?
Cl5 Bi1 Cl8 87.74(3) . . ?
Cl1 Bi1 Cl7 175.68(3) . . ?
Cl6 Bi1 Cl7 88.70(3) . . ?
Cl4 Bi1 Cl7 94.89(3) . . ?
Cl5 Bi1 Cl7 83.92(3) . . ?
Cl8 Bi1 Cl7 90.31(3) . . ?
C1 N1 H2A 109.5 . . ?
C1 N1 H2B 109.5 . . ?
H2A N1 H2B 109.5 . . ?
C1 N1 H2C 109.5 . . ?
H2A N1 H2C 109.5 . . ?
H2B N1 H2C 109.5 . . ?
N1 C1 C2 110.1(4) . . ?
N1 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.2 . . ?
N3 C5 C6 111.0(4) . . ?
N3 C5 H10A 109.4 . . ?
C6 C5 H10A 109.4 . . ?
N3 C5 H10B 109.4 . . ?
C6 C5 H10B 109.4 . . ?
H10A C5 H10B 108.0 . . ?
C5 C6 H2D 109.5 . . ?
C5 C6 H2E 109.5 . . ?
H2D C6 H2E 109.5 . . ?
C5 C6 H2F 109.5 . . ?
H2D C6 H2F 109.5 . . ?
H2E C6 H2F 109.5 . . ?
C4 C3 N2 113.3(5) . . ?
C4 C3 H8A 108.9 . . ?
N2 C3 H8A 108.9 . . ?
C4 C3 H8B 108.9 . . ?
N2 C3 H8B 108.9 . . ?
H8A C3 H8B 107.7 . . ?
C1 C2 H3A 109.5 . . ?
C1 C2 H3B 109.5 . . ?
H3A C2 H3B 109.5 . . ?
C1 C2 H3C 109.5 . . ?
H3A C2 H3C 109.5 . . ?
H3B C2 H3C 109.5 . . ?
C3 C4 H7A 109.5 . . ?
C3 C4 H7B 109.5 . . ?
H7A C4 H7B 109.5 . . ?
C3 C4 H7C 109.5 . . ?
H7A C4 H7C 109.5 . . ?
H7B C4 H7C 109.5 . . ?
C5 N3 H11A 109.5 . . ?
C5 N3 H11B 109.5 . . ?
H11A N3 H11B 109.5 . . ?
C5 N3 H11C 109.5 . . ?
H11A N3 H11C 109.5 . . ?
H11B N3 H11C 109.5 . . ?
C3 N2 H1C 109.5 . . ?
C3 N2 H1D 109.5 . . ?
H1C N2 H1D 109.5 . . ?
C3 N2 H1E 109.5 . . ?
H1C N2 H1E 109.5 . . ?
H1D N2 H1E 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
N2 H1E Cl6 0.91 2.44 3.326(4) 165.8 1_655
N2 H1D Cl6 0.91 2.87 3.429(4) 121.0 3_666
N2 H1D Cl4 0.91 2.58 3.345(4) 142.4 3_656
N2 H1C Cl1 0.91 2.66 3.410(3) 140.7 3_656
N2 H1C Cl4 0.91 2.89 3.556(4) 130.8 1_655
N3 H11C Cl8 0.91 2.40 3.241(3) 153.2 1_565
N3 H11B Cl7 0.91 2.47 3.195(3) 136.8 3_666
N3 H11B Cl4 0.91 2.95 3.568(3) 126.6 1_565
N3 H11A Cl7 0.91 2.53 3.367(3) 154.0 .
N3 H11A Cl5 0.91 2.89 3.397(3) 116.9 .
C2 H3B Cl1 0.98 2.92 3.729(5) 140.8 2_556
C3 H8A Cl8 0.99 2.92 3.902(6) 170.8 3_656
C6 H2D Cl8 0.98 2.93 3.682(5) 134.7 1_565
N1 H2C Cl7 0.91 2.23 3.137(3) 172.8 2_656
N1 H2B Cl8 0.91 2.88 3.516(3) 128.1 2_656
N1 H2B Cl8 0.91 2.50 3.190(3) 132.9 .
N1 H2A Cl5 0.91 2.28 3.181(4) 169.0 .

_refine_diff_density_max         1.132
_refine_diff_density_min         -1.860
_refine_diff_density_rms         0.169

_vrf_PLAT242_a                   
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of        Bi1 Check 
RESPONSE: ......Author Response :The alert is due to the disordered structure
;
####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1909102'
loop_
_audit_author_name
_audit_author_address
'Hui Hui Li'
;Southeast University
China
;
_audit_update_record             
;
2019-09-16 deposited with the CCDC.	2020-01-06 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         ?
_chemical_formula_sum            'C6 H21 Bi Br6 Cl3 N3'
_chemical_formula_weight         929.99

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'
N N 0.0061 0.0033 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

_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, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   24.290(2)
_cell_length_b                   8.2740(7)
_cell_length_c                   12.4821(9)
_cell_angle_alpha                90
_cell_angle_beta                 108.894(7)
_cell_angle_gamma                90
_cell_volume                     2373.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    420(2)
_cell_measurement_reflns_used    1706
_cell_measurement_theta_min      1.7950
_cell_measurement_theta_max      25.7090

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.603
_exptl_crystal_F_000             1688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    17.860
_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      420(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku, SCXmini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6798
_diffrn_reflns_av_unetI/netI     0.0750
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.772
_diffrn_reflns_theta_max         29.869
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.776
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.776
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.776
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3636
_reflns_number_gt                1492
_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)+(0.1123P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3636
_refine_ls_number_parameters     122
_refine_ls_number_restraints     89
_refine_ls_R_factor_all          0.1209
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.1969
_refine_ls_wR_factor_gt          0.1672
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_restrained_S_all      0.966
_refine_ls_shift/su_max          0.000
_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
Bi01 Bi 0.16909(3) 0.5000 0.70155(5) 0.0753(3) Uani 1 2 d S T P . .
Br05 Br 0.17712(11) 0.5000 0.47356(18) 0.1638(15) Uani 1 2 d S T P . .
Br7 Br 0.08002(7) 0.2574(2) 0.62580(15) 0.1136(6) Uani 1 1 d . . . . .
Br8 Br 0.15906(12) 0.5000 0.91928(17) 0.1184(8) Uani 1 2 d S T P . .
Br9 Br 0.25508(7) 0.7470(2) 0.76702(14) 0.1069(5) Uani 1 1 d . . . . .
Cl1 Cl 0.0554(3) 0.0000 0.3381(6) 0.149(3) Uani 1 2 d DS T P . .
N2 N 0.9647(10) 0.5000 0.6470(19) 0.189(9) Uani 1 2 d DS TU P . .
H2A H 0.9811 0.4421 0.6042 0.284 Uiso 0.5 1 d R U P . .
H2B H 0.9303 0.4557 0.6432 0.284 Uiso 0.5 1 d R U P . .
H2C H 0.9591 0.6022 0.6211 0.284 Uiso 0.5 1 d R U P . .
Cl3 Cl 0.4288(7) 0.5000 0.0108(18) 0.387(13) Uani 1 2 d DS T P . .
C1 C 0.1252(8) 0.0000 0.3356(18) 0.199(14) Uani 1 2 d DS TU P . .
H1D H 0.1255 0.0491 0.2661 0.239 Uiso 0.5 1 d R U P . .
H1E H 0.1365 -0.1107 0.3333 0.239 Uiso 0.5 1 d R U P . .
C2 C 0.1700(10) 0.080(4) 0.429(2) 0.196(15) Uani 0.5 1 d D U P . .
H2D H 0.1602 0.1922 0.4326 0.235 Uiso 0.5 1 d R U P . .
H2E H 0.2063 0.0755 0.4134 0.235 Uiso 0.5 1 d R U P . .
C4 C 1.0028(9) 0.5000 0.767(2) 0.204(10) Uani 1 2 d DS TU P . .
H4A H 1.0397 0.5474 0.7728 0.245 Uiso 0.5 1 d R U P . .
H4B H 1.0091 0.3917 0.7963 0.245 Uiso 0.5 1 d R U P . .
C3 C 0.9706(12) 0.604(4) 0.830(3) 0.207(17) Uani 0.5 1 d D U P . .
H3D H 0.9575 0.7036 0.7901 0.248 Uiso 0.5 1 d R U P . .
H3E H 0.9974 0.6296 0.9029 0.248 Uiso 0.5 1 d R U P . .
C5 C 0.410(2) 0.439(8) 0.123(4) 0.59(8) Uani 0.5 1 d D U P . .
H5A H 0.4441 0.4491 0.1884 0.712 Uiso 0.5 1 d R U P . .
H5B H 0.3996 0.3266 0.1146 0.712 Uiso 0.5 1 d R U P . .
C6 C 0.3612(17) 0.533(7) 0.144(3) 0.31(4) Uani 0.5 1 d D U P . .
H6A H 0.3692 0.6465 0.1467 0.373 Uiso 0.5 1 d R U P . .
H6B H 0.3560 0.5000 0.2139 0.373 Uiso 1 2 d R U P . .
N1 N 0.1759(7) 0.0000 0.5378(17) 0.139(8) Uani 1 2 d DS TU P . .
H1A H 0.2040 0.0501 0.5932 0.209 Uiso 0.5 1 d R U P . .
H1B H 0.1420 0.0000 0.5525 0.209 Uiso 1 2 d R U P . .
H1C H 0.1856 -0.1044 0.5344 0.209 Uiso 0.5 1 d R U P . .
Cl2 Cl 0.9150(6) 0.5000 0.8460(12) 0.411(14) Uani 1 2 d DS TU P . .
N3 N 0.3090(16) 0.5000 0.047(4) 0.32(3) Uani 1 2 d DS TU P . .
H3A H 0.2783 0.5539 0.0549 0.483 Uiso 0.5 1 d R U P . .
H3B H 0.3149 0.5306 -0.0174 0.483 Uiso 0.5 1 d R U P . .
H3C H 0.3019 0.3931 0.0451 0.483 Uiso 0.5 1 d R U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi01 Br8 2.8062(19) . ?
Bi01 Br9 2.8465(15) . ?
Bi01 Br9 2.8465(15) 6_565 ?
Bi01 Br7 2.8775(16) . ?
Bi01 Br7 2.8776(16) 6_565 ?
Bi01 Br05 2.915(2) . ?
Cl1 C1 1.704(18) . ?
N2 C4 1.486(18) . ?
N2 H2A 0.8999 . ?
N2 H2B 0.8999 . ?
N2 H2C 0.9000 . ?
Cl3 C5 1.68(2) . ?
Cl3 C5 1.68(2) 6_565 ?
C1 C2 1.468(17) . ?
C1 C2 1.468(17) 6 ?
C1 H1D 0.9600 . ?
C1 H1E 0.9600 . ?
C2 C2 1.33(7) 6 ?
C2 N1 1.482(18) . ?
C2 H2D 0.9600 . ?
C2 H2E 0.9600 . ?
C4 C3 1.533(18) 6_565 ?
C4 C3 1.533(18) . ?
C4 H4A 0.9602 . ?
C4 H4B 0.9600 . ?
C3 Cl2 1.668(18) . ?
C3 C3 1.72(6) 6_565 ?
C3 H3D 0.9599 . ?
C3 H3E 0.9602 . ?
C5 C5 1.01(13) 6_565 ?
C5 C6 1.32(3) 6_565 ?
C5 C6 1.51(2) . ?
C5 H5A 0.9601 . ?
C5 H5B 0.9600 . ?
C6 C6 0.54(11) 6_565 ?
C6 C5 1.32(3) 6_565 ?
C6 N3 1.464(19) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9617 . ?
N1 C2 1.482(18) 6 ?
N1 H1A 0.9001 . ?
N1 H1B 0.8987 . ?
N1 H1C 0.9000 . ?
Cl2 C3 1.668(18) 6_565 ?
N3 C6 1.46(2) 6_565 ?
N3 H3A 0.8998 . ?
N3 H3B 0.9000 . ?
N3 H3C 0.9000 . ?

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
Br8 Bi01 Br9 90.44(5) . . ?
Br8 Bi01 Br9 90.44(5) . 6_565 ?
Br9 Bi01 Br9 91.79(7) . 6_565 ?
Br8 Bi01 Br7 91.51(5) . . ?
Br9 Bi01 Br7 177.45(5) . . ?
Br9 Bi01 Br7 89.83(6) 6_565 . ?
Br8 Bi01 Br7 91.51(5) . 6_565 ?
Br9 Bi01 Br7 89.83(6) . 6_565 ?
Br9 Bi01 Br7 177.45(5) 6_565 6_565 ?
Br7 Bi01 Br7 88.47(8) . 6_565 ?
Br8 Bi01 Br05 178.92(7) . . ?
Br9 Bi01 Br05 90.31(5) . . ?
Br9 Bi01 Br05 90.31(5) 6_565 . ?
Br7 Bi01 Br05 87.71(5) . . ?
Br7 Bi01 Br05 87.71(5) 6_565 . ?
C4 N2 H2A 110.4 . . ?
C4 N2 H2B 108.4 . . ?
H2A N2 H2B 109.5 . . ?
C4 N2 H2C 109.6 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C5 Cl3 C5 35(5) . 6_565 ?
C2 C1 C2 54(3) . 6 ?
C2 C1 Cl1 118.2(16) . . ?
C2 C1 Cl1 118.2(16) 6 . ?
C2 C1 H1D 107.5 . . ?
C2 C1 H1D 133.2 6 . ?
Cl1 C1 H1D 108.4 . . ?
C2 C1 H1E 108.1 . . ?
C2 C1 H1E 56.2 6 . ?
Cl1 C1 H1E 107.3 . . ?
H1D C1 H1E 106.9 . . ?
C2 C2 C1 63.0(14) 6 . ?
C2 C2 N1 63.3(14) 6 . ?
C1 C2 N1 110.5(16) . . ?
C2 C2 H2D 164.4 6 . ?
C1 C2 H2D 110.2 . . ?
N1 C2 H2D 109.7 . . ?
C2 C2 H2E 87.5 6 . ?
C1 C2 H2E 108.5 . . ?
N1 C2 H2E 109.9 . . ?
H2D C2 H2E 108.0 . . ?
N2 C4 C3 105.1(16) . 6_565 ?
N2 C4 C3 105.1(16) . . ?
C3 C4 C3 68(2) 6_565 . ?
N2 C4 H4A 109.5 . . ?
C3 C4 H4A 144.1 6_565 . ?
C3 C4 H4A 110.6 . . ?
N2 C4 H4B 110.7 . . ?
C3 C4 H4B 48.0 6_565 . ?
C3 C4 H4B 112.2 . . ?
H4A C4 H4B 108.7 . . ?
C4 C3 Cl2 109.8(16) . . ?
C4 C3 C3 55.9(12) . 6_565 ?
Cl2 C3 C3 59.0(11) . 6_565 ?
C4 C3 H3D 111.0 . . ?
Cl2 C3 H3D 111.2 . . ?
C3 C3 H3D 149.2 6_565 . ?
C4 C3 H3E 107.9 . . ?
Cl2 C3 H3E 108.8 . . ?
C3 C3 H3E 102.8 6_565 . ?
H3D C3 H3E 108.0 . . ?
C5 C5 C6 80(5) 6_565 6_565 ?
C5 C5 C6 59(2) 6_565 . ?
C6 C5 C6 21(5) 6_565 . ?
C5 C5 Cl3 72(2) 6_565 . ?
C6 C5 Cl3 128(3) 6_565 . ?
C6 C5 Cl3 115(2) . . ?
C5 C5 H5A 84.9 6_565 . ?
C6 C5 H5A 113.1 6_565 . ?
C6 C5 H5A 108.1 . . ?
Cl3 C5 H5A 107.3 . . ?
C5 C5 H5B 165.3 6_565 . ?
C6 C5 H5B 88.0 6_565 . ?
C6 C5 H5B 108.3 . . ?
Cl3 C5 H5B 109.9 . . ?
H5A C5 H5B 107.6 . . ?
C6 C6 C5 100(5) 6_565 6_565 ?
C6 C6 N3 79(2) 6_565 . ?
C5 C6 N3 118(2) 6_565 . ?
C6 C6 C5 59(2) 6_565 . ?
C5 C6 C5 41(6) 6_565 . ?
N3 C6 C5 106.3(19) . . ?
C6 C6 H6A 168.9 6_565 . ?
C5 C6 H6A 69.4 6_565 . ?
N3 C6 H6A 108.8 . . ?
C5 C6 H6A 110.4 . . ?
C6 C6 H6B 73.7 6_565 . ?
C5 C6 H6B 128.6 6_565 . ?
N3 C6 H6B 111.3 . . ?
C5 C6 H6B 110.9 . . ?
H6A C6 H6B 109.0 . . ?
C2 N1 C2 53(3) . 6 ?
C2 N1 H1A 108.9 . . ?
C2 N1 H1A 137.5 6 . ?
C2 N1 H1B 111.5 . . ?
C2 N1 H1B 111.5 6 . ?
H1A N1 H1B 111.1 . . ?
C2 N1 H1C 109.7 . . ?
C2 N1 H1C 58.3 6 . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 106.3 . . ?
C3 Cl2 C3 62(2) . 6_565 ?
C6 N3 C6 21(4) . 6_565 ?
C6 N3 H3A 110.3 . . ?
C6 N3 H3A 122.0 6_565 . ?
C6 N3 H3B 109.9 . . ?
C6 N3 H3B 116.4 6_565 . ?
H3A N3 H3B 109.5 . . ?
C6 N3 H3C 108.2 . . ?
C6 N3 H3C 87.1 6_565 . ?
H3A N3 H3C 109.5 . . ?
H3B N3 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
Cl1 C1 C2 C2 105.8(10) . . . 6 ?
C2 C1 C2 N1 -43(3) 6 . . . ?
Cl1 C1 C2 N1 63(3) . . . . ?
N2 C4 C3 Cl2 76(2) . . . . ?
C3 C4 C3 Cl2 -25(3) 6_565 . . . ?
N2 C4 C3 C3 100.5(11) . . . 6_565 ?
C5 Cl3 C5 C6 61(8) 6_565 . . 6_565 ?
C5 Cl3 C5 C6 42(4) 6_565 . . . ?
C5 C5 C6 C6 179.997(12) 6_565 . . 6_565 ?
Cl3 C5 C6 C6 132(5) . . . 6_565 ?
C6 C5 C6 C5 180.003(13) 6_565 . . 6_565 ?
Cl3 C5 C6 C5 -48(5) . . . 6_565 ?
C5 C5 C6 N3 114(3) 6_565 . . . ?
C6 C5 C6 N3 -66(3) 6_565 . . . ?
Cl3 C5 C6 N3 66(5) . . . . ?
C1 C2 N1 C2 43(3) . . . 6 ?
C4 C3 Cl2 C3 24(3) . . . 6_565 ?
C5 C6 N3 C6 96(6) 6_565 . . 6_565 ?
C5 C6 N3 C6 53(3) . . . 6_565 ?

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
N3 H3A Br9 0.90 3.08 3.81(3) 139.7 7_566
N3 H3A Br8 0.90 2.88 3.47(4) 124.8 1_554
N1 H1C Br9 0.90 3.10 3.564(15) 114.1 1_545
N1 H1B Br7 0.90 2.92 3.581(15) 131.5 6
N1 H1B Br7 0.90 2.92 3.581(15) 131.5 .
N1 H1A Br9 0.90 2.71 3.564(15) 159.8 6_565
C6 H6B Br7 0.96 2.99 3.66(5) 128.0 7_556
C6 H6A Br8 0.96 3.06 3.94(5) 154.7 7_566
C6 H6A Br7 0.96 2.86 3.33(5) 111.7 4_556
C5 H5B Br8 0.96 3.02 3.96(7) 168.1 7_556
C5 H5A Cl1 0.96 2.78 3.71(6) 165.4 3
C3 H3D Cl1 0.96 2.89 3.83(4) 166.4 5_666
C4 H4A Br8 0.96 2.91 3.65(2) 135.1 1_655
C4 H4A Br7 0.96 2.85 3.579(17) 133.9 6_665
C2 H2E Br9 0.96 3.06 3.75(2) 130.2 4_546
C2 H2E Br05 0.96 2.80 3.58(3) 139.0 7_556
C2 H2D Br05 0.96 2.60 3.51(3) 157.9 .
N2 H2C Br7 0.90 3.14 3.795(19) 131.5 5_666
N2 H2B Br05 0.90 2.57 3.28(2) 136.6 5_666
N2 H2A Br7 0.90 2.79 3.52(2) 140.1 1_655

_refine_diff_density_max         1.080
_refine_diff_density_min         -1.075
_refine_diff_density_rms         0.185

_vrf_PLAT260_1                   
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PROBLEM: Large Average Ueq of Residue Including       Cl3      0.405 Check 
RESPONSE: ...Author Response :The alert is due to the disordered structure
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