# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_429
_database_code_depnum_ccdc_archive 'CCDC 1891856'
loop_
_audit_author_name
_audit_author_address
YT
;fjirsm
China
;
_audit_update_record             
;
2019-01-18 deposited with the CCDC.	2019-05-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H24 Bi Br6 N3'
_chemical_formula_weight         862.75

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 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+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   29.2975(13)
_cell_length_b                   8.1370(3)
_cell_length_c                   22.1923(9)
_cell_angle_alpha                90
_cell_angle_beta                 126.2400(10)
_cell_angle_gamma                90
_cell_volume                     4267.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9309
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      27.51

_exptl_crystal_description       Flake
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.686
_exptl_crystal_F_000             3136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    19.494
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42653
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_av_R_equivalents  0.0729
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.276
_diffrn_reflns_theta_max         27.608
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4921
_reflns_number_gt                4444
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0340P)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         4921
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0228
_refine_ls_wR_factor_ref         0.0711
_refine_ls_wR_factor_gt          0.0575
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_restrained_S_all      1.160
_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 0.13663(2) 0.26962(2) 0.05269(2) 0.00854(6) Uani 1 1 d . . . . .
Br6 Br 0.24654(2) 0.21921(5) 0.18987(2) 0.01239(10) Uani 1 1 d . . . . .
Br2 Br 0.17156(2) 0.03102(5) -0.01166(2) 0.01431(11) Uani 1 1 d . . . . .
Br4 Br 0.09691(2) 0.00991(5) 0.09429(2) 0.01356(11) Uani 1 1 d . . . . .
Br1 Br 0.18320(2) 0.51524(6) 0.00855(3) 0.01661(11) Uani 1 1 d . . . . .
Br5 Br 0.11449(2) 0.51006(5) 0.12225(2) 0.01388(11) Uani 1 1 d . . . . .
Br3 Br 0.02480(2) 0.31232(6) -0.07701(2) 0.01295(10) Uani 1 1 d . . . . .
N3 N 0.27376(17) 0.2943(4) 0.3561(2) 0.0143(8) Uani 1 1 d . . . . .
H3A H 0.2878 0.2201 0.3939 0.021 Uiso 1 1 calc R U . . .
H3B H 0.2887 0.3952 0.3755 0.021 Uiso 1 1 calc R U . . .
H3C H 0.2831 0.2631 0.3253 0.021 Uiso 1 1 calc R U . . .
C7 C 0.2119(2) 0.3014(6) 0.3136(3) 0.0152(10) Uani 1 1 d . . . . .
H7 H 0.1924 0.3859 0.2731 0.018 Uiso 1 1 calc R U . . .
C8 C 0.1808(2) 0.1444(6) 0.2983(3) 0.0206(11) Uani 1 1 d . . . . .
H8A H 0.2033 0.0421 0.3188 0.025 Uiso 1 1 calc R U . . .
H8B H 0.1436 0.1322 0.2492 0.025 Uiso 1 1 calc R U . . .
C9 C 0.1853(2) 0.2656(6) 0.3525(3) 0.0182(10) Uani 1 1 d . . . . .
H9A H 0.1509 0.3281 0.3367 0.022 Uiso 1 1 calc R U . . .
H9B H 0.2106 0.2379 0.4063 0.022 Uiso 1 1 calc R U . . .
N1 N 0.31676(17) 0.2074(5) 0.1178(2) 0.0162(9) Uani 1 1 d . . . . .
H1A H 0.3207 0.2887 0.0930 0.024 Uiso 1 1 calc R U . . .
H1B H 0.2874 0.2316 0.1199 0.024 Uiso 1 1 calc R U . . .
H1C H 0.3098 0.1104 0.0934 0.024 Uiso 1 1 calc R U . . .
C1 C 0.3693(2) 0.1934(6) 0.1942(3) 0.0154(10) Uani 1 1 d . . . . .
H1 H 0.3669 0.1284 0.2305 0.018 Uiso 1 1 calc R U . . .
C4 C -0.0167(2) 0.1823(6) 0.1009(3) 0.0228(11) Uani 1 1 d . . . . .
H4 H -0.0187 0.0598 0.0962 0.027 Uiso 1 1 calc R U . . .
C6 C 0.0188(3) 0.2480(7) 0.1783(3) 0.0316(14) Uani 1 1 d . . . . .
H6A H 0.0395 0.3520 0.1872 0.038 Uiso 1 1 calc R U . . .
H6B H 0.0385 0.1682 0.2200 0.038 Uiso 1 1 calc R U . . .
N2 N -0.01677(17) 0.2721(5) 0.0437(2) 0.0156(9) Uani 1 1 d . . . . .
H2A H -0.0499 0.2530 -0.0019 0.023 Uiso 1 1 calc R U . . .
H2B H 0.0127 0.2375 0.0436 0.023 Uiso 1 1 calc R U . . .
H2C H -0.0132 0.3816 0.0538 0.023 Uiso 1 1 calc R U . . .
C2 C 0.4079(2) 0.3378(6) 0.2249(3) 0.0264(12) Uani 1 1 d . . . . .
H2 H 0.4286 0.3620 0.2788 0.032 Uiso 1 1 calc R U . . .
H3 H 0.3968 0.4355 0.1924 0.032 Uiso 1 1 calc R U . . .
C3 C 0.4237(2) 0.1848(7) 0.2033(3) 0.0267(12) Uani 1 1 d . . . . .
H5 H 0.4222 0.1885 0.1576 0.032 Uiso 1 1 calc R U . . .
H6 H 0.4541 0.1150 0.2440 0.032 Uiso 1 1 calc R U . . .
C5 C -0.0444(3) 0.2552(7) 0.1321(3) 0.0323(14) Uani 1 1 d . . . . .
H5A H -0.0637 0.1802 0.1455 0.039 Uiso 1 1 calc R U . . .
H5B H -0.0627 0.3637 0.1128 0.039 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 Br5 2.7955(5) . ?
Bi1 Br4 2.8182(5) . ?
Bi1 Br3 2.8267(5) . ?
Bi1 Br6 2.8662(5) . ?
Bi1 Br1 2.8976(5) . ?
Bi1 Br2 2.9299(5) . ?
N3 C7 1.468(6) . ?
C7 C8 1.488(7) . ?
C7 C9 1.494(7) . ?
C8 C9 1.499(7) . ?
N1 C1 1.473(6) . ?
C1 C3 1.486(7) . ?
C1 C2 1.489(7) . ?
C4 N2 1.465(6) . ?
C4 C5 1.467(8) . ?
C4 C6 1.484(7) . ?
C6 C5 1.495(9) . ?
C2 C3 1.500(8) . ?

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 Br4 93.924(15) . . ?
Br5 Bi1 Br3 88.204(14) . . ?
Br4 Bi1 Br3 88.356(14) . . ?
Br5 Bi1 Br6 89.732(13) . . ?
Br4 Bi1 Br6 88.101(14) . . ?
Br3 Bi1 Br6 175.770(14) . . ?
Br5 Bi1 Br1 90.759(14) . . ?
Br4 Bi1 Br1 174.936(14) . . ?
Br3 Bi1 Br1 93.721(14) . . ?
Br6 Bi1 Br1 89.997(14) . . ?
Br5 Bi1 Br2 174.165(14) . . ?
Br4 Bi1 Br2 89.633(14) . . ?
Br3 Bi1 Br2 96.530(14) . . ?
Br6 Bi1 Br2 85.760(13) . . ?
Br1 Bi1 Br2 85.545(14) . . ?
N3 C7 C8 118.0(4) . . ?
N3 C7 C9 119.3(4) . . ?
C8 C7 C9 60.4(3) . . ?
C7 C8 C9 60.0(3) . . ?
C7 C9 C8 59.6(3) . . ?
N1 C1 C3 117.8(4) . . ?
N1 C1 C2 117.4(4) . . ?
C3 C1 C2 60.6(4) . . ?
N2 C4 C5 119.3(5) . . ?
N2 C4 C6 117.6(5) . . ?
C5 C4 C6 60.9(4) . . ?
C4 C6 C5 59.0(4) . . ?
C1 C2 C3 59.6(3) . . ?
C1 C3 C2 59.8(3) . . ?
C4 C5 C6 60.2(4) . . ?

_refine_diff_density_max         1.317
_refine_diff_density_min         -2.345
_refine_diff_density_rms         0.355

_shelxl_version_number           2013-2



####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 1891857'
loop_
_audit_author_name
_audit_author_address
YT
;fjirsm
China
;
_audit_update_record             
;
2019-01-18 deposited with the CCDC.	2019-05-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H24 Bi Br6 N3'
_chemical_formula_weight         862.75

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           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                   22.2211(5)
_cell_length_b                   8.3379(2)
_cell_length_c                   12.2913(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.8660(10)
_cell_angle_gamma                90
_cell_volume                     2210.94(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    2371
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      27.40

_exptl_crystal_description       Flake
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.592
_exptl_crystal_F_000             1568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    18.811
_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      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22778
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_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         2.221
_diffrn_reflns_theta_max         27.514
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2717
_reflns_number_gt                2085
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0824P)²+7.9235P] 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         2717
_refine_ls_number_parameters     118
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1444
_refine_ls_wR_factor_gt          0.1297
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_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
Bi1 Bi 0.33105(2) 0.500000 0.27715(3) 0.04595(18) Uani 1 2 d S T P . .
Br1 Br 0.24447(5) 0.25154(13) 0.21340(10) 0.0775(3) Uani 1 1 d . . . . .
Br3 Br 0.42659(5) 0.73941(13) 0.35770(11) 0.0781(3) Uani 1 1 d . . . . .
Br4 Br 0.35051(8) 0.500000 0.06171(12) 0.0857(5) Uani 1 2 d S T P . .
Br2 Br 0.30864(7) 0.500000 0.50050(13) 0.0962(7) Uani 1 2 d S T P . .
C4 C 0.0700(12) 0.000000 0.2533(13) 0.170(12) Uani 1 2 d DS T P . .
H4 H 0.106359 -0.068040 0.256945 0.204 Uiso 0.5 1 d R U P . .
C5 C 0.0649(12) 0.144(2) 0.180(2) 0.155(19) Uani 0.5 1 d D . P . .
H5A H 0.048653 0.246282 0.197291 0.186 Uiso 0.5 1 d R U P . .
H5B H 0.098753 0.152042 0.142391 0.186 Uiso 0.5 1 d R U P . .
N1 N 0.1947(9) 0.500000 -0.0437(17) 0.158(10) Uani 1 2 d DS T P . .
H1A H 0.206557 0.536204 -0.103500 0.238 Uiso 0.5 1 calc R U P . .
H1B H 0.208784 0.400579 -0.028361 0.238 Uiso 0.5 1 calc R U P . .
H1C H 0.210060 0.563217 0.014671 0.238 Uiso 0.5 1 calc R U P . .
C3 C 0.0891(14) 0.500000 0.017(2) 0.212(10) Uani 1 2 d DS TU P . .
H3A H 0.090849 0.401950 0.060479 0.255 Uiso 0.5 1 d R U P . .
H3B H 0.090849 0.598050 0.060509 0.255 Uiso 0.5 1 d R U P . .
C6 C 0.0263(15) 0.000000 0.141(2) 0.25(3) Uani 1 2 d DS T P . .
H6B H 0.036135 -0.069990 0.084229 0.305 Uiso 0.5 1 d R U P . .
H6A H -0.017625 0.013570 0.135689 0.305 Uiso 0.5 1 d R U P . .
C2 C 0.0588(10) 0.500000 -0.105(2) 0.217(10) Uani 1 2 d DS TU P . .
H2D H 0.036960 0.598070 -0.132958 0.260 Uiso 0.5 1 d R U P . .
H2E H 0.036960 0.401930 -0.132958 0.260 Uiso 0.5 1 d R U P . .
C1 C 0.1268(9) 0.500000 -0.067(3) 0.214(10) Uani 1 2 d DS TU P . .
H1 H 0.126822 0.382460 -0.066883 0.257 Uiso 0.5 1 d R U P . .
N2 N 0.0476(6) 0.000000 0.3589(10) 0.078(4) Uani 1 2 d DS T P . .
H2A H 0.041718 0.100559 0.378282 0.117 Uiso 0.5 1 calc R U P . .
H2B H 0.075748 -0.046852 0.413385 0.117 Uiso 0.5 1 calc R U P . .
H2C H 0.012032 -0.053707 0.347658 0.117 Uiso 0.5 1 calc R U P . .
C8 C 0.0793(6) 0.500000 0.3783(18) 0.097(6) Uani 1 2 d DS T P . .
H8A H 0.062802 0.579090 0.321042 0.117 Uiso 0.5 1 d R U P . .
H8B H 0.052182 0.472110 0.426552 0.117 Uiso 0.5 1 d R U P . .
C7 C 0.1476(7) 0.500000 0.4257(12) 0.175(17) Uani 1 2 d DS T P . .
H7 H 0.170120 0.579050 0.391725 0.210 Uiso 0.5 1 d R U P . .
C9 C 0.1185(9) 0.365(3) 0.353(2) 0.21(3) Uani 0.5 1 d D . P . .
H9B H 0.115579 0.260304 0.385832 0.248 Uiso 0.5 1 d R U P . .
H9A H 0.127029 0.362734 0.279162 0.248 Uiso 0.5 1 d R U P . .
N3 N 0.1689(6) 0.500000 0.5505(10) 0.081(4) Uani 1 2 d DS T P . .
H3D H 0.141490 0.447882 0.579566 0.122 Uiso 0.5 1 calc R U P . .
H3C H 0.172376 0.600615 0.575389 0.122 Uiso 0.5 1 calc R U P . .
H3E H 0.205566 0.451502 0.570901 0.122 Uiso 0.5 1 calc 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 Br4 2.7835(15) . ?
Bi1 Br1 2.8080(10) . ?
Bi1 Br1 2.8080(10) 6_565 ?
Bi1 Br2 2.9052(15) . ?
Bi1 Br3 2.9093(10) 6_565 ?
Bi1 Br3 2.9093(10) . ?
C4 C6 1.489(10) . ?
C4 C5 1.493(10) . ?
C4 C5 1.493(10) 6 ?
C4 N2 1.497(10) . ?
C5 C6 1.489(10) . ?
N1 C1 1.467(10) . ?
C3 C1 1.481(10) . ?
C3 C2 1.495(10) . ?
C2 C1 1.472(10) . ?
C8 C7 1.489(10) . ?
C8 C9 1.502(10) . ?
C8 C9 1.502(10) 6_565 ?
C7 C9 1.486(10) 6_565 ?
C7 C9 1.486(10) . ?
C7 N3 1.492(10) . ?

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
Br4 Bi1 Br1 89.24(4) . . ?
Br4 Bi1 Br1 89.24(4) . 6_565 ?
Br1 Bi1 Br1 95.08(5) . 6_565 ?
Br4 Bi1 Br2 179.09(5) . . ?
Br1 Bi1 Br2 90.15(3) . . ?
Br1 Bi1 Br2 90.15(3) 6_565 . ?
Br4 Bi1 Br3 93.25(4) . 6_565 ?
Br1 Bi1 Br3 89.09(4) . 6_565 ?
Br1 Bi1 Br3 175.18(4) 6_565 6_565 ?
Br2 Bi1 Br3 87.41(3) . 6_565 ?
Br4 Bi1 Br3 93.25(4) . . ?
Br1 Bi1 Br3 175.18(4) . . ?
Br1 Bi1 Br3 89.09(4) 6_565 . ?
Br2 Bi1 Br3 87.41(3) . . ?
Br3 Bi1 Br3 86.65(5) 6_565 . ?
C6 C4 C5 59.9(5) . . ?
C6 C4 C5 59.9(5) . 6 ?
C5 C4 C5 107(2) . 6 ?
C6 C4 N2 122(2) . . ?
C5 C4 N2 122.3(16) . . ?
C5 C4 N2 122.3(16) 6 . ?
C6 C5 C4 59.9(5) . . ?
C1 C3 C2 59.3(5) . . ?
C5 C6 C5 108(2) . 6 ?
C5 C6 C4 60.2(5) . . ?
C5 C6 C4 60.2(5) 6 . ?
C1 C2 C3 59.9(5) . . ?
N1 C1 C2 173(3) . . ?
N1 C1 C3 126(3) . . ?
C2 C1 C3 60.8(5) . . ?
C7 C8 C9 59.6(5) . . ?
C7 C8 C9 59.6(5) . 6_565 ?
C9 C8 C9 97(2) . 6_565 ?
C9 C7 C9 99(2) 6_565 . ?
C9 C7 C8 60.6(5) 6_565 . ?
C9 C7 C8 60.6(5) . . ?
C9 C7 N3 127.1(15) 6_565 . ?
C9 C7 N3 127.1(15) . . ?
C8 C7 N3 116.4(15) . . ?
C7 C9 C8 59.8(5) . . ?

_refine_diff_density_max         1.515
_refine_diff_density_min         -1.876
_refine_diff_density_rms         0.346



