# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_x
_database_code_depnum_ccdc_archive 'CCDC 2054396'
loop_
_audit_author_name
_audit_author_address
'Jiance Jin'
;Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian
China
;
_audit_update_record             
;
2021-01-07 deposited with the CCDC.	2021-04-15 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            'C20 H16 Bi2 Br6 N4 O4'
_chemical_formula_weight         1273.79

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.5836(5)
_cell_length_b                   9.5888(5)
_cell_length_c                   10.0923(6)
_cell_angle_alpha                67.643(6)
_cell_angle_beta                 88.319(5)
_cell_angle_gamma                61.421(5)
_cell_volume                     739.79(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6964
_cell_measurement_theta_min      2.2670
_cell_measurement_theta_max      29.4210

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.859
_exptl_crystal_F_000             572
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    20.012
_shelx_estimated_absorpt_T_min   0.065
_shelx_estimated_absorpt_T_max   0.108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.38029
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13912
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_av_R_equivalents  0.0878
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.222
_diffrn_reflns_theta_max         25.027
_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             2617
_reflns_number_gt                2397
_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)+2.8000P] 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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00153(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2617
_refine_ls_number_parameters     164
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0600
_refine_ls_wR_factor_gt          0.0570
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.028
_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 0.22323(3) 0.29570(3) 0.65060(3) 0.00768(11) Uani 1 1 d . . . . .
Br1 Br 0.37216(9) -0.04950(8) 0.82934(8) 0.01785(18) Uani 1 1 d . . . . .
Br2 Br 0.16703(8) 0.41123(8) 0.87217(7) 0.01179(17) Uani 1 1 d . . . . .
Br3 Br 0.10178(8) 0.66453(8) 0.43033(7) 0.01093(17) Uani 1 1 d . . . . .
O1 O 0.4600(5) 0.2953(6) 0.6602(5) 0.0115(11) Uani 1 1 d . . . . .
O2 O 0.3415(6) 0.2073(6) 0.4647(5) 0.0129(11) Uani 1 1 d . . . . .
N1 N 0.5977(7) 0.1601(7) 0.6601(6) 0.0088(12) Uani 1 1 d . . . . .
N2 N 0.3835(7) 0.3120(7) 0.3650(6) 0.0100(13) Uani 1 1 d . . . . .
C1 C 0.6948(9) 0.0383(9) 0.7890(8) 0.0176(17) Uani 1 1 d . . . . .
H1 H 0.661348 0.044617 0.877084 0.021 Uiso 1 1 calc R U . . .
C2 C 0.8434(9) -0.0963(9) 0.7930(8) 0.0164(17) Uani 1 1 d . . . . .
H2 H 0.911570 -0.184345 0.884109 0.020 Uiso 1 1 calc R U . . .
C3 C 0.8933(8) -0.1034(8) 0.6650(8) 0.0119(16) Uani 1 1 d . . . . .
H3 H 0.996417 -0.194636 0.667080 0.014 Uiso 1 1 calc R U . . .
C4 C 0.7906(8) 0.0247(8) 0.5330(8) 0.0095(14) Uani 1 1 d . U . . .
H4 H 0.823101 0.021737 0.443801 0.011 Uiso 1 1 calc R U . . .
C5 C 0.6403(8) 0.1572(8) 0.5318(7) 0.0062(14) Uani 1 1 d . U . . .
C6 C 0.5279(8) 0.2972(8) 0.3930(7) 0.0071(14) Uani 1 1 d . U . . .
C7 C 0.5721(8) 0.4050(8) 0.2898(7) 0.0104(15) Uani 1 1 d . . . . .
H7 H 0.673594 0.395187 0.308903 0.012 Uiso 1 1 calc R U . . .
C8 C 0.4673(9) 0.5271(9) 0.1588(8) 0.0149(16) Uani 1 1 d . . . . .
H8 H 0.494546 0.604778 0.088103 0.018 Uiso 1 1 calc R U . . .
C9 C 0.3244(9) 0.5353(9) 0.1314(8) 0.0148(16) Uani 1 1 d . . . . .
H9 H 0.253350 0.616363 0.040129 0.018 Uiso 1 1 calc R U . . .
C10 C 0.2828(8) 0.4257(8) 0.2364(8) 0.0138(16) Uani 1 1 d . . . . .
H10 H 0.183414 0.431023 0.217391 0.017 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 O1 2.272(4) . ?
Bi1 O2 2.385(5) . ?
Bi1 Br1 2.7085(7) . ?
Bi1 Br2 2.7859(8) . ?
Bi1 Br3 3.0061(7) . ?
Bi1 Br3 3.0479(7) 2_566 ?
O1 N1 1.336(7) . ?
O2 N2 1.333(7) . ?
N1 C1 1.341(8) . ?
N1 C5 1.352(9) . ?
N2 C10 1.340(8) . ?
N2 C6 1.349(8) . ?
C1 C2 1.379(10) . ?
C1 H1 0.9500 . ?
C2 C3 1.379(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.483(8) . ?
C6 C7 1.380(9) . ?
C7 C8 1.380(9) . ?
C7 H7 0.9500 . ?
C8 C9 1.364(9) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(10) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Bi1 O2 75.87(15) . . ?
O1 Bi1 Br1 91.58(11) . . ?
O2 Bi1 Br1 86.20(10) . . ?
O1 Bi1 Br2 86.59(12) . . ?
O2 Bi1 Br2 162.39(10) . . ?
Br1 Bi1 Br2 95.95(2) . . ?
O1 Bi1 Br3 81.98(11) . . ?
O2 Bi1 Br3 86.60(10) . . ?
Br1 Bi1 Br3 171.33(2) . . ?
Br2 Bi1 Br3 89.48(2) . . ?
O1 Bi1 Br3 168.09(12) . 2_566 ?
O2 Bi1 Br3 95.66(10) . 2_566 ?
Br1 Bi1 Br3 96.24(2) . 2_566 ?
Br2 Bi1 Br3 101.46(2) . 2_566 ?
Br3 Bi1 Br3 89.264(19) . 2_566 ?
Bi1 Br3 Bi1 90.736(19) . 2_566 ?
N1 O1 Bi1 120.6(3) . . ?
N2 O2 Bi1 116.6(3) . . ?
O1 N1 C1 117.8(6) . . ?
O1 N1 C5 119.6(5) . . ?
C1 N1 C5 122.4(6) . . ?
O2 N2 C10 118.7(5) . . ?
O2 N2 C6 119.7(5) . . ?
C10 N2 C6 121.5(6) . . ?
N1 C1 C2 119.6(7) . . ?
N1 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
C1 C2 C3 120.2(7) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 119.0(7) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 119.7(7) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
N1 C5 C4 119.1(6) . . ?
N1 C5 C6 119.6(6) . . ?
C4 C5 C6 121.3(6) . . ?
N2 C6 C7 119.9(6) . . ?
N2 C6 C5 118.7(6) . . ?
C7 C6 C5 121.3(6) . . ?
C8 C7 C6 119.4(6) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C9 C8 C7 119.5(7) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 120.1(7) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
N2 C10 C9 119.5(6) . . ?
N2 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Bi1 O1 N1 C1 -97.2(5) . . . . ?
Bi1 O1 N1 C5 87.8(6) . . . . ?
Bi1 O2 N2 C10 -98.3(6) . . . . ?
Bi1 O2 N2 C6 84.2(6) . . . . ?
O1 N1 C1 C2 -175.2(6) . . . . ?
C5 N1 C1 C2 -0.4(9) . . . . ?
N1 C1 C2 C3 1.4(10) . . . . ?
C1 C2 C3 C4 -1.2(9) . . . . ?
C2 C3 C4 C5 0.0(9) . . . . ?
O1 N1 C5 C4 173.9(5) . . . . ?
C1 N1 C5 C4 -0.8(9) . . . . ?
O1 N1 C5 C6 -4.6(8) . . . . ?
C1 N1 C5 C6 -179.3(5) . . . . ?
C3 C4 C5 N1 1.0(8) . . . . ?
C3 C4 C5 C6 179.4(5) . . . . ?
O2 N2 C6 C7 179.7(6) . . . . ?
C10 N2 C6 C7 2.3(10) . . . . ?
O2 N2 C6 C5 3.3(9) . . . . ?
C10 N2 C6 C5 -174.1(6) . . . . ?
N1 C5 C6 N2 -64.1(8) . . . . ?
C4 C5 C6 N2 117.4(7) . . . . ?
N1 C5 C6 C7 119.5(7) . . . . ?
C4 C5 C6 C7 -59.0(8) . . . . ?
N2 C6 C7 C8 0.0(10) . . . . ?
C5 C6 C7 C8 176.4(6) . . . . ?
C6 C7 C8 C9 -2.2(10) . . . . ?
C7 C8 C9 C10 2.1(11) . . . . ?
O2 N2 C10 C9 -179.9(6) . . . . ?
C6 N2 C10 C9 -2.4(10) . . . . ?
C8 C9 C10 N2 0.2(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 Br1 0.95 2.99 3.920(8) 167.6 2_657 yes
C2 H2 Br2 0.95 2.96 3.613(7) 127.4 2_657 yes
C7 H7 Br2 0.95 3.01 3.717(7) 131.9 2_666 yes
C10 H10 Br2 0.95 2.94 3.841(7) 158.1 2_566 yes

_refine_diff_density_max         1.977
_refine_diff_density_min         -2.134
_refine_diff_density_rms         0.235



####################################################################### 
# 
# 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_ck
_database_code_depnum_ccdc_archive 'CCDC 2054397'
loop_
_audit_author_name
_audit_author_address
'Jiance Jin'
;Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian
China
;
_audit_update_record             
;
2021-01-07 deposited with the CCDC.	2021-04-15 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            'C21 H17.50 Bi2 Br6 N4.50 O4'
_chemical_formula_weight         1294.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   16.702(3)
_cell_length_b                   13.373(3)
_cell_length_c                   27.508(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.96(3)
_cell_angle_gamma                90
_cell_volume                     6069(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9995
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      25.73

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.833
_exptl_crystal_F_000             4664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    19.519
_shelx_estimated_absorpt_T_min   0.056
_shelx_estimated_absorpt_T_max   0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.002
_exptl_absorpt_correction_T_max  0.008
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22722
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.582
_diffrn_reflns_theta_max         25.746
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5783
_reflns_number_gt                5189
_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)+(0.0350P)²+4.0000P] 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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.000149(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5783
_refine_ls_number_parameters     354
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0688
_refine_ls_wR_factor_gt          0.0666
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.040
_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 0.75420(2) 0.47439(2) 0.29231(2) 0.01189(8) Uani 1 1 d . . . . .
Bi2 Bi 0.71457(2) 0.50584(2) 0.43351(2) 0.01122(8) Uani 1 1 d . . . . .
Br1 Br 0.61679(3) 0.50568(4) 0.22202(2) 0.01877(14) Uani 1 1 d . . . . .
Br2 Br 0.77437(4) 0.28802(5) 0.26246(2) 0.02495(15) Uani 1 1 d . . . . .
Br3 Br 0.86674(3) 0.54604(5) 0.24042(2) 0.02476(16) Uani 1 1 d . . . . .
Br4 Br 0.86967(3) 0.47134(5) 0.38413(2) 0.02403(16) Uani 1 1 d . . . . .
Br5 Br 0.79052(4) 0.51013(5) 0.52989(2) 0.02368(16) Uani 1 1 d . . . . .
Br6 Br 0.55994(4) 0.51159(5) 0.44477(3) 0.02554(16) Uani 1 1 d . . . . .
O1 O 0.6727(2) 0.3965(3) 0.35238(14) 0.0154(9) Uani 1 1 d . . . . .
O2 O 0.7042(2) 0.3321(3) 0.45177(14) 0.0168(9) Uani 1 1 d . . . . .
O3 O 0.6925(2) 0.6060(3) 0.35164(13) 0.0148(8) Uani 1 1 d . . . . .
O4 O 0.7092(2) 0.6835(3) 0.44725(14) 0.0182(9) Uani 1 1 d . . . . .
N1 N 0.6210(3) 0.3198(4) 0.34831(16) 0.0132(10) Uani 1 1 d . . . . .
N2 N 0.7569(3) 0.2710(4) 0.43377(17) 0.0141(10) Uani 1 1 d . . . . .
N3 N 0.6378(3) 0.6797(4) 0.34474(16) 0.0126(10) Uani 1 1 d . . . . .
N4 N 0.7644(3) 0.7398(4) 0.42967(16) 0.0147(11) Uani 1 1 d . . . . .
C1 C 0.5457(3) 0.3324(5) 0.3229(2) 0.0189(13) Uani 1 1 d . . . . .
H1 H 0.531167 0.394686 0.307382 0.023 Uiso 1 1 calc R U . . .
C2 C 0.4898(3) 0.2564(5) 0.3193(2) 0.0242(15) Uani 1 1 d . . . . .
H2 H 0.437059 0.265799 0.301252 0.029 Uiso 1 1 calc R U . . .
C3 C 0.5113(3) 0.1651(5) 0.3422(2) 0.0235(14) Uani 1 1 d . . . . .
H3 H 0.473443 0.111793 0.340741 0.028 Uiso 1 1 calc R U . . .
C4 C 0.5896(3) 0.1546(5) 0.3673(2) 0.0193(13) Uani 1 1 d . . . . .
H4 H 0.605160 0.093094 0.383362 0.023 Uiso 1 1 calc R U . . .
C5 C 0.6453(3) 0.2312(4) 0.3695(2) 0.0147(12) Uani 1 1 d . . . . .
C6 C 0.7299(3) 0.2185(4) 0.3924(2) 0.0143(12) Uani 1 1 d . . . . .
C7 C 0.7822(4) 0.1539(4) 0.3738(2) 0.0183(13) Uani 1 1 d . . . . .
H7 H 0.764103 0.116400 0.344836 0.022 Uiso 1 1 calc R U . . .
C8 C 0.8612(4) 0.1440(5) 0.3976(2) 0.0224(14) Uani 1 1 d . . . . .
H8 H 0.897642 0.099871 0.385065 0.027 Uiso 1 1 calc R U . . .
C9 C 0.8865(4) 0.1989(5) 0.4397(2) 0.0265(15) Uani 1 1 d . . . . .
H9 H 0.940493 0.192673 0.456387 0.032 Uiso 1 1 calc R U . . .
C10 C 0.8336(3) 0.2621(5) 0.4574(2) 0.0188(13) Uani 1 1 d . . . . .
H10 H 0.850860 0.299935 0.486383 0.023 Uiso 1 1 calc R U . . .
C11 C 0.5618(3) 0.6597(5) 0.3221(2) 0.0178(13) Uani 1 1 d . . . . .
H11 H 0.547090 0.593268 0.312181 0.021 Uiso 1 1 calc R U . . .
C12 C 0.5056(3) 0.7352(5) 0.3135(2) 0.0235(15) Uani 1 1 d . . . . .
H12 H 0.451758 0.721000 0.298316 0.028 Uiso 1 1 calc R U . . .
C13 C 0.5279(4) 0.8323(5) 0.3271(2) 0.0283(16) Uani 1 1 d . . . . .
H13 H 0.490499 0.885824 0.319880 0.034 Uiso 1 1 calc R U . . .
C14 C 0.6056(4) 0.8497(5) 0.3513(2) 0.0248(15) Uani 1 1 d . . . . .
H14 H 0.621270 0.915631 0.361482 0.030 Uiso 1 1 calc R U . . .
C15 C 0.6600(3) 0.7734(4) 0.3607(2) 0.0145(12) Uani 1 1 d . . . . .
C16 C 0.7435(3) 0.7885(4) 0.3865(2) 0.0146(12) Uani 1 1 d . . . . .
C17 C 0.7972(3) 0.8514(4) 0.3695(2) 0.0169(13) Uani 1 1 d . . . . .
H17 H 0.782350 0.886237 0.339346 0.020 Uiso 1 1 calc R U . . .
C18 C 0.8734(4) 0.8640(5) 0.3966(2) 0.0221(14) Uani 1 1 d . . . . .
H18 H 0.911296 0.907377 0.384924 0.027 Uiso 1 1 calc R U . . .
C19 C 0.8948(3) 0.8142(5) 0.4404(2) 0.0226(14) Uani 1 1 d . . . . .
H19 H 0.946902 0.823239 0.459337 0.027 Uiso 1 1 calc R U . . .
C20 C 0.8389(3) 0.7504(5) 0.4565(2) 0.0193(13) Uani 1 1 d . . . . .
H20 H 0.852968 0.714277 0.486317 0.023 Uiso 1 1 calc R U . . .
N5 N 1.0011(10) 0.5636(9) 0.4958(6) 0.025(3) Uani 0.5 1 d D U P A -1
C21 C 1.0104(18) 0.4783(13) 0.501(2) 0.125(11) Uani 0.5 1 d D U P A -1
C22 C 0.9949(8) 0.3683(9) 0.5125(6) 0.047(4) Uani 0.5 1 d D U P A -1
H22A H 0.992335 0.328278 0.482467 0.070 Uiso 0.5 1 calc R U P A -1
H22C H 0.943487 0.362670 0.525246 0.070 Uiso 0.5 1 calc R U P A -1
H22D H 1.039132 0.343694 0.537300 0.070 Uiso 0.5 1 calc R U P A -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 O1 2.524(4) . ?
Bi1 Br2 2.6619(8) . ?
Bi1 Br3 2.7065(9) . ?
Bi1 O3 2.710(4) . ?
Bi1 Br1 2.7926(11) . ?
Bi1 Br4 2.9295(11) . ?
Bi2 O2 2.390(4) . ?
Bi2 O4 2.409(4) . ?
Bi2 O3 2.597(4) . ?
Bi2 Br6 2.6497(8) . ?
Bi2 O1 2.669(4) . ?
Bi2 Br5 2.7556(10) . ?
Bi2 Br4 3.1408(10) . ?
O1 N1 1.334(6) . ?
O2 N2 1.350(6) . ?
O3 N3 1.337(6) . ?
O4 N4 1.338(6) . ?
N1 C1 1.351(7) . ?
N1 C5 1.355(7) . ?
N2 C10 1.348(7) . ?
N2 C6 1.353(7) . ?
N3 C11 1.351(7) . ?
N3 C15 1.361(7) . ?
N4 C20 1.352(7) . ?
N4 C16 1.352(7) . ?
C1 C2 1.373(8) . ?
C2 C3 1.395(9) . ?
C3 C4 1.387(8) . ?
C4 C5 1.379(8) . ?
C5 C6 1.464(8) . ?
C6 C7 1.384(8) . ?
C7 C8 1.384(8) . ?
C8 C9 1.382(9) . ?
C9 C10 1.366(9) . ?
C11 C12 1.374(8) . ?
C12 C13 1.385(9) . ?
C13 C14 1.383(9) . ?
C14 C15 1.364(8) . ?
C15 C16 1.476(8) . ?
C16 C17 1.365(8) . ?
C17 C18 1.382(8) . ?
C18 C19 1.374(9) . ?
C19 C20 1.386(9) . ?
N5 C21 1.157(14) . ?
C21 C22 1.536(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
O1 Bi1 Br2 85.57(9) . . ?
O1 Bi1 Br3 168.88(8) . . ?
Br2 Bi1 Br3 92.12(3) . . ?
O1 Bi1 O3 65.11(13) . . ?
Br2 Bi1 O3 150.68(9) . . ?
Br3 Bi1 O3 116.63(9) . . ?
O1 Bi1 Br1 92.65(8) . . ?
Br2 Bi1 Br1 93.24(2) . . ?
Br3 Bi1 Br1 98.34(2) . . ?
O3 Bi1 Br1 88.34(7) . . ?
O1 Bi1 Br4 77.26(8) . . ?
Br2 Bi1 Br4 98.92(2) . . ?
Br3 Bi1 Br4 92.39(2) . . ?
O3 Bi1 Br4 75.57(7) . . ?
Br1 Bi1 Br4 163.47(2) . . ?
O2 Bi2 O4 156.97(14) . . ?
O2 Bi2 O3 132.74(13) . . ?
O4 Bi2 O3 67.90(13) . . ?
O2 Bi2 Br6 84.25(9) . . ?
O4 Bi2 Br6 83.81(9) . . ?
O3 Bi2 Br6 94.42(9) . . ?
O2 Bi2 O1 67.96(12) . . ?
O4 Bi2 O1 131.30(13) . . ?
O3 Bi2 O1 64.78(13) . . ?
Br6 Bi2 O1 88.88(8) . . ?
O2 Bi2 Br5 81.70(9) . . ?
O4 Bi2 Br5 81.46(9) . . ?
O3 Bi2 Br5 143.67(9) . . ?
Br6 Bi2 Br5 101.42(3) . . ?
O1 Bi2 Br5 146.87(9) . . ?
O2 Bi2 Br4 92.27(9) . . ?
O4 Bi2 Br4 105.43(10) . . ?
O3 Bi2 Br4 73.49(8) . . ?
Br6 Bi2 Br4 159.95(2) . . ?
O1 Bi2 Br4 71.59(8) . . ?
Br5 Bi2 Br4 97.59(3) . . ?
Bi1 Br4 Bi2 83.94(2) . . ?
N1 O1 Bi1 132.1(3) . . ?
N1 O1 Bi2 125.0(3) . . ?
Bi1 O1 Bi2 102.92(13) . . ?
N2 O2 Bi2 116.0(3) . . ?
N3 O3 Bi2 120.3(3) . . ?
N3 O3 Bi1 135.1(3) . . ?
Bi2 O3 Bi1 99.88(13) . . ?
N4 O4 Bi2 117.0(3) . . ?
O1 N1 C1 119.0(5) . . ?
O1 N1 C5 119.4(4) . . ?
C1 N1 C5 121.6(5) . . ?
C10 N2 O2 120.0(5) . . ?
C10 N2 C6 121.8(5) . . ?
O2 N2 C6 118.1(4) . . ?
O3 N3 C11 119.5(5) . . ?
O3 N3 C15 119.1(4) . . ?
C11 N3 C15 121.4(5) . . ?
O4 N4 C20 119.3(5) . . ?
O4 N4 C16 119.4(4) . . ?
C20 N4 C16 121.2(5) . . ?
N1 C1 C2 120.8(6) . . ?
C1 C2 C3 119.4(5) . . ?
C4 C3 C2 118.1(6) . . ?
C5 C4 C3 121.5(6) . . ?
N1 C5 C4 118.5(5) . . ?
N1 C5 C6 119.3(5) . . ?
C4 C5 C6 122.2(5) . . ?
N2 C6 C7 119.2(5) . . ?
N2 C6 C5 118.3(5) . . ?
C7 C6 C5 122.5(5) . . ?
C6 C7 C8 119.7(6) . . ?
C9 C8 C7 119.3(6) . . ?
C10 C9 C8 119.9(6) . . ?
N2 C10 C9 120.1(5) . . ?
N3 C11 C12 120.1(6) . . ?
C11 C12 C13 119.7(5) . . ?
C14 C13 C12 118.7(6) . . ?
C15 C14 C13 120.9(6) . . ?
N3 C15 C14 119.1(5) . . ?
N3 C15 C16 118.1(5) . . ?
C14 C15 C16 122.7(5) . . ?
N4 C16 C17 120.3(5) . . ?
N4 C16 C15 116.8(5) . . ?
C17 C16 C15 122.8(5) . . ?
C16 C17 C18 119.4(6) . . ?
C19 C18 C17 120.3(6) . . ?
C18 C19 C20 118.8(5) . . ?
N4 C20 C19 120.0(6) . . ?
N5 C21 C22 161(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
Bi1 O1 N1 C1 -75.6(6) . . . . ?
Bi2 O1 N1 C1 105.2(5) . . . . ?
Bi1 O1 N1 C5 104.2(5) . . . . ?
Bi2 O1 N1 C5 -75.1(5) . . . . ?
Bi2 O2 N2 C10 80.6(5) . . . . ?
Bi2 O2 N2 C6 -100.6(5) . . . . ?
Bi2 O3 N3 C11 -93.4(5) . . . . ?
Bi1 O3 N3 C11 56.9(6) . . . . ?
Bi2 O3 N3 C15 86.6(5) . . . . ?
Bi1 O3 N3 C15 -123.1(5) . . . . ?
Bi2 O4 N4 C20 -83.6(5) . . . . ?
Bi2 O4 N4 C16 99.3(5) . . . . ?
O1 N1 C1 C2 -177.8(5) . . . . ?
C5 N1 C1 C2 2.4(9) . . . . ?
N1 C1 C2 C3 0.2(9) . . . . ?
C1 C2 C3 C4 -1.1(9) . . . . ?
C2 C3 C4 C5 -0.4(9) . . . . ?
O1 N1 C5 C4 176.3(5) . . . . ?
C1 N1 C5 C4 -3.9(8) . . . . ?
O1 N1 C5 C6 -5.8(8) . . . . ?
C1 N1 C5 C6 173.9(5) . . . . ?
C3 C4 C5 N1 2.9(9) . . . . ?
C3 C4 C5 C6 -174.9(6) . . . . ?
C10 N2 C6 C7 0.1(8) . . . . ?
O2 N2 C6 C7 -178.6(5) . . . . ?
C10 N2 C6 C5 178.9(5) . . . . ?
O2 N2 C6 C5 0.1(8) . . . . ?
N1 C5 C6 N2 68.2(7) . . . . ?
C4 C5 C6 N2 -114.1(6) . . . . ?
N1 C5 C6 C7 -113.1(6) . . . . ?
C4 C5 C6 C7 64.7(8) . . . . ?
N2 C6 C7 C8 -0.2(9) . . . . ?
C5 C6 C7 C8 -178.9(6) . . . . ?
C6 C7 C8 C9 0.1(9) . . . . ?
C7 C8 C9 C10 -0.1(10) . . . . ?
O2 N2 C10 C9 178.7(5) . . . . ?
C6 N2 C10 C9 0.0(9) . . . . ?
C8 C9 C10 N2 0.0(10) . . . . ?
O3 N3 C11 C12 -178.1(5) . . . . ?
C15 N3 C11 C12 1.9(8) . . . . ?
N3 C11 C12 C13 1.5(9) . . . . ?
C11 C12 C13 C14 -3.1(10) . . . . ?
C12 C13 C14 C15 1.5(10) . . . . ?
O3 N3 C15 C14 176.4(5) . . . . ?
C11 N3 C15 C14 -3.6(8) . . . . ?
O3 N3 C15 C16 -1.9(7) . . . . ?
C11 N3 C15 C16 178.1(5) . . . . ?
C13 C14 C15 N3 1.8(9) . . . . ?
C13 C14 C15 C16 -179.9(6) . . . . ?
O4 N4 C16 C17 175.7(5) . . . . ?
C20 N4 C16 C17 -1.3(9) . . . . ?
O4 N4 C16 C15 -1.7(7) . . . . ?
C20 N4 C16 C15 -178.7(5) . . . . ?
N3 C15 C16 N4 -63.3(7) . . . . ?
C14 C15 C16 N4 118.4(7) . . . . ?
N3 C15 C16 C17 119.4(6) . . . . ?
C14 C15 C16 C17 -59.0(9) . . . . ?
N4 C16 C17 C18 0.7(9) . . . . ?
C15 C16 C17 C18 177.9(6) . . . . ?
C16 C17 C18 C19 -0.4(9) . . . . ?
C17 C18 C19 C20 0.7(9) . . . . ?
O4 N4 C20 C19 -175.4(5) . . . . ?
C16 N4 C20 C19 1.6(9) . . . . ?
C18 C19 C20 N4 -1.3(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
_geom_hbond_publ_flag
C1 H1 Br1 0.95 2.89 3.635(6) 136.4 2_655 yes
C4 H4 Br5 0.95 3.06 3.885(6) 146.6 7_656 yes
C7 H7 Br3 0.95 3.09 3.963(6) 153.1 4_645 yes
C11 H11 Br1 0.95 3.13 3.669(6) 117.9 . yes
C11 H11 Br1 0.95 2.99 3.671(6) 129.7 2_655 yes
C12 H12 Br1 0.95 3.12 3.733(7) 124.1 2_655 yes
C12 H12 Br2 0.95 3.11 3.962(6) 150.8 3_455 yes
C17 H17 Br1 0.95 3.02 3.713(6) 130.9 4_655 yes
C17 H17 Br2 0.95 3.10 3.738(6) 125.6 4_655 yes

_refine_diff_density_max         1.758
_refine_diff_density_min         -1.359
_refine_diff_density_rms         0.245



####################################################################### 
# 
# 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_x_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2054398'
loop_
_audit_author_name
_audit_author_address
'Jiance Jin'
;Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian
China
;
_audit_update_record             
;
2021-01-07 deposited with the CCDC.	2021-04-15 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            'C20 H30 Bi Br4 N3 O2'
_chemical_formula_weight         873.09

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   16.7831(7)
_cell_length_b                   10.2718(5)
_cell_length_c                   15.2355(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.446(4)
_cell_angle_gamma                90
_cell_volume                     2618.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8627
_cell_measurement_theta_min      2.2640
_cell_measurement_theta_max      29.4890

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.215
_exptl_crystal_F_000             1640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    12.858
_shelx_estimated_absorpt_T_min   0.113
_shelx_estimated_absorpt_T_max   0.206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.27592
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25174
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.327
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.026
_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             4624
_reflns_number_gt                4008
_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)+(0.0250P)²+3.6995P] 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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00017(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4624
_refine_ls_number_parameters     274
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_ref         0.0705
_refine_ls_wR_factor_gt          0.0649
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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 0.75185(2) 0.52126(2) 0.41448(2) 0.01087(9) Uani 1 1 d . . . . .
Br1 Br 0.88136(3) 0.34168(6) 0.43030(4) 0.01687(16) Uani 1 1 d . . . . .
Br2 Br 0.83723(3) 0.70585(6) 0.31993(4) 0.01528(16) Uani 1 1 d . . . . .
Br3 Br 0.66536(3) 0.34998(7) 0.29592(4) 0.01912(17) Uani 1 1 d . . . . .
Br4 Br 0.62047(3) 0.68744(6) 0.42354(4) 0.01612(16) Uani 1 1 d . . . . .
O1 O 0.8033(2) 0.6274(4) 0.5482(3) 0.0144(10) Uani 1 1 d . . . . .
O2 O 0.7002(2) 0.4041(4) 0.5338(3) 0.0147(10) Uani 1 1 d . . . . .
N1 N 0.8395(3) 0.5518(5) 0.6111(3) 0.0121(12) Uani 1 1 d . . . . .
N2 N 0.6637(3) 0.4679(5) 0.5961(3) 0.0118(12) Uani 1 1 d . . . . .
C1 C 0.9188(3) 0.5359(6) 0.6135(4) 0.0153(15) Uani 1 1 d . . . . .
H1 H 0.948637 0.576673 0.570707 0.018 Uiso 1 1 calc R U . . .
C2 C 0.9567(4) 0.4603(7) 0.6784(4) 0.0204(16) Uani 1 1 d . . . . .
H2 H 1.012975 0.449011 0.680615 0.025 Uiso 1 1 calc R U . . .
C3 C 0.9133(4) 0.4008(6) 0.7402(4) 0.0189(15) Uani 1 1 d . . . . .
H3 H 0.939425 0.347943 0.784819 0.023 Uiso 1 1 calc R U . . .
C4 C 0.8315(4) 0.4187(7) 0.7369(4) 0.0184(15) Uani 1 1 d . . . . .
H4 H 0.800967 0.378337 0.779266 0.022 Uiso 1 1 calc R U . . .
C5 C 0.7945(3) 0.4958(6) 0.6713(4) 0.0117(13) Uani 1 1 d . U . . .
C6 C 0.7079(4) 0.5216(6) 0.6654(4) 0.0118(14) Uani 1 1 d . . . . .
C7 C 0.6702(3) 0.5891(6) 0.7283(4) 0.0156(14) Uani 1 1 d . . . . .
H7 H 0.700686 0.628807 0.776212 0.019 Uiso 1 1 calc R U . . .
C8 C 0.5878(4) 0.5990(7) 0.7217(4) 0.0189(15) Uani 1 1 d . . . . .
H8 H 0.561399 0.646380 0.764458 0.023 Uiso 1 1 calc R U . . .
C9 C 0.5443(4) 0.5393(6) 0.6523(4) 0.0178(15) Uani 1 1 d . . . . .
H9 H 0.487564 0.543555 0.648038 0.021 Uiso 1 1 calc R U . . .
C10 C 0.5828(3) 0.4741(6) 0.5899(4) 0.0159(15) Uani 1 1 d . . . . .
H10 H 0.552864 0.433206 0.542102 0.019 Uiso 1 1 calc R U . . .
N3 N 0.7546(3) 0.0261(5) 0.5578(3) 0.0148(12) Uani 1 1 d . . . . .
C11 C 0.8059(4) 0.1160(7) 0.6179(5) 0.0282(18) Uani 1 1 d . . . . .
H11A H 0.776402 0.138723 0.669611 0.034 Uiso 1 1 calc R U . . .
H11B H 0.816025 0.197508 0.585985 0.034 Uiso 1 1 calc R U . . .
C12 C 0.8859(4) 0.0540(7) 0.6497(5) 0.0315(19) Uani 1 1 d . . . . .
H12A H 0.918391 0.117091 0.686286 0.038 Uiso 1 1 calc R U . . .
H12B H 0.876495 -0.023210 0.686379 0.038 Uiso 1 1 calc R U . . .
C13 C 0.9303(4) 0.0142(7) 0.5723(5) 0.0298(19) Uani 1 1 d . . . . .
H13A H 0.980572 -0.030058 0.593336 0.036 Uiso 1 1 calc R U . . .
H13B H 0.944245 0.092630 0.538978 0.036 Uiso 1 1 calc R U . . .
C14 C 0.8804(4) -0.0761(7) 0.5125(5) 0.0318(19) Uani 1 1 d . . . . .
H14A H 0.909556 -0.096687 0.460173 0.038 Uiso 1 1 calc R U . . .
H14B H 0.871475 -0.158562 0.543885 0.038 Uiso 1 1 calc R U . . .
C15 C 0.8015(4) -0.0164(7) 0.4834(4) 0.0272(18) Uani 1 1 d . . . . .
H15A H 0.769525 -0.080427 0.447102 0.033 Uiso 1 1 calc R U . . .
H15B H 0.810678 0.059851 0.445743 0.033 Uiso 1 1 calc R U . . .
C16 C 0.7267(3) -0.0892(6) 0.6078(4) 0.0157(14) Uani 1 1 d . . . . .
H16A H 0.773129 -0.137318 0.633845 0.024 Uiso 1 1 calc R U . . .
H16B H 0.694542 -0.146374 0.567578 0.024 Uiso 1 1 calc R U . . .
H16C H 0.694267 -0.059163 0.654596 0.024 Uiso 1 1 calc R U . . .
C17 C 0.6829(4) 0.1084(8) 0.5279(5) 0.0342(19) Uani 1 1 d . . . . .
H17A H 0.653602 0.128117 0.580292 0.041 Uiso 1 1 calc R U . . .
H17B H 0.702786 0.192139 0.506070 0.041 Uiso 1 1 calc R U . . .
C18 C 0.6253(4) 0.0556(8) 0.4598(5) 0.0348(19) Uani 1 1 d . . . . .
H18A H 0.608576 -0.032815 0.476609 0.042 Uiso 1 1 calc R U . . .
H18B H 0.650141 0.049567 0.403149 0.042 Uiso 1 1 calc R U . . .
C19 C 0.5521(4) 0.1463(7) 0.4500(4) 0.0217(16) Uani 1 1 d . . . . .
H19A H 0.522962 0.141888 0.504018 0.026 Uiso 1 1 calc R U . . .
H19B H 0.570060 0.237142 0.442752 0.026 Uiso 1 1 calc R U . . .
C20 C 0.4966(4) 0.1076(8) 0.3714(5) 0.036(2) Uani 1 1 d . . . . .
H20A H 0.523683 0.120507 0.317307 0.055 Uiso 1 1 calc R U . . .
H20B H 0.448315 0.161448 0.369352 0.055 Uiso 1 1 calc R U . . .
H20C H 0.481906 0.015711 0.376480 0.055 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 O2 2.398(4) . ?
Bi1 O1 2.410(4) . ?
Bi1 Br4 2.8003(6) . ?
Bi1 Br2 2.8361(7) . ?
Bi1 Br3 2.8387(7) . ?
Bi1 Br1 2.8468(6) . ?
O1 N1 1.341(6) . ?
O2 N2 1.340(6) . ?
N1 C1 1.337(7) . ?
N1 C5 1.362(8) . ?
N2 C10 1.355(7) . ?
N2 C6 1.360(7) . ?
C1 C2 1.374(9) . ?
C2 C3 1.377(9) . ?
C3 C4 1.382(8) . ?
C4 C5 1.384(8) . ?
C5 C6 1.473(8) . ?
C6 C7 1.377(8) . ?
C7 C8 1.382(8) . ?
C8 C9 1.381(8) . ?
C9 C10 1.366(9) . ?
N3 C15 1.494(8) . ?
N3 C16 1.503(8) . ?
N3 C17 1.513(8) . ?
N3 C11 1.520(8) . ?
C11 C12 1.530(10) . ?
C12 C13 1.499(10) . ?
C13 C14 1.508(9) . ?
C14 C15 1.494(9) . ?
C17 C18 1.466(10) . ?
C18 C19 1.539(9) . ?
C19 C20 1.512(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Bi1 O1 73.35(14) . . ?
O2 Bi1 Br4 86.33(10) . . ?
O1 Bi1 Br4 85.11(9) . . ?
O2 Bi1 Br2 161.32(10) . . ?
O1 Bi1 Br2 87.98(10) . . ?
Br4 Bi1 Br2 92.767(19) . . ?
O2 Bi1 Br3 88.52(10) . . ?
O1 Bi1 Br3 161.81(10) . . ?
Br4 Bi1 Br3 92.489(19) . . ?
Br2 Bi1 Br3 110.164(19) . . ?
O2 Bi1 Br1 85.95(10) . . ?
O1 Bi1 Br1 90.00(9) . . ?
Br4 Bi1 Br1 171.79(2) . . ?
Br2 Bi1 Br1 93.651(19) . . ?
Br3 Bi1 Br1 90.10(2) . . ?
N1 O1 Bi1 117.1(3) . . ?
N2 O2 Bi1 120.3(3) . . ?
C1 N1 O1 119.0(5) . . ?
C1 N1 C5 122.2(5) . . ?
O1 N1 C5 118.8(5) . . ?
O2 N2 C10 119.0(5) . . ?
O2 N2 C6 119.8(5) . . ?
C10 N2 C6 121.2(5) . . ?
N1 C1 C2 119.5(6) . . ?
C1 C2 C3 120.2(6) . . ?
C2 C3 C4 119.5(6) . . ?
C3 C4 C5 119.5(6) . . ?
N1 C5 C4 119.1(5) . . ?
N1 C5 C6 118.6(5) . . ?
C4 C5 C6 122.2(6) . . ?
N2 C6 C7 119.5(5) . . ?
N2 C6 C5 116.8(5) . . ?
C7 C6 C5 123.6(5) . . ?
C6 C7 C8 119.8(6) . . ?
C9 C8 C7 119.4(6) . . ?
C10 C9 C8 120.0(6) . . ?
N2 C10 C9 120.0(6) . . ?
C15 N3 C16 111.0(5) . . ?
C15 N3 C17 112.9(5) . . ?
C16 N3 C17 108.7(5) . . ?
C15 N3 C11 109.1(5) . . ?
C16 N3 C11 110.9(5) . . ?
C17 N3 C11 104.0(5) . . ?
N3 C11 C12 112.3(5) . . ?
C13 C12 C11 110.0(6) . . ?
C12 C13 C14 110.9(6) . . ?
C15 C14 C13 111.4(6) . . ?
C14 C15 N3 113.7(6) . . ?
C18 C17 N3 118.2(6) . . ?
C17 C18 C19 108.8(6) . . ?
C20 C19 C18 110.8(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
Bi1 O1 N1 C1 92.8(5) . . . . ?
Bi1 O1 N1 C5 -88.4(5) . . . . ?
Bi1 O2 N2 C10 97.5(5) . . . . ?
Bi1 O2 N2 C6 -84.4(5) . . . . ?
O1 N1 C1 C2 179.1(5) . . . . ?
C5 N1 C1 C2 0.3(9) . . . . ?
N1 C1 C2 C3 0.3(9) . . . . ?
C1 C2 C3 C4 -0.5(10) . . . . ?
C2 C3 C4 C5 0.2(9) . . . . ?
C1 N1 C5 C4 -0.7(9) . . . . ?
O1 N1 C5 C4 -179.4(5) . . . . ?
C1 N1 C5 C6 178.1(5) . . . . ?
O1 N1 C5 C6 -0.6(8) . . . . ?
C3 C4 C5 N1 0.4(9) . . . . ?
C3 C4 C5 C6 -178.4(6) . . . . ?
O2 N2 C6 C7 178.8(5) . . . . ?
C10 N2 C6 C7 -3.2(9) . . . . ?
O2 N2 C6 C5 -5.2(8) . . . . ?
C10 N2 C6 C5 172.8(5) . . . . ?
N1 C5 C6 N2 69.8(7) . . . . ?
C4 C5 C6 N2 -111.4(7) . . . . ?
N1 C5 C6 C7 -114.3(7) . . . . ?
C4 C5 C6 C7 64.5(9) . . . . ?
N2 C6 C7 C8 1.6(9) . . . . ?
C5 C6 C7 C8 -174.2(6) . . . . ?
C6 C7 C8 C9 0.8(10) . . . . ?
C7 C8 C9 C10 -1.7(10) . . . . ?
O2 N2 C10 C9 -179.6(6) . . . . ?
C6 N2 C10 C9 2.4(9) . . . . ?
C8 C9 C10 N2 0.1(10) . . . . ?
C15 N3 C11 C12 -54.5(7) . . . . ?
C16 N3 C11 C12 68.0(7) . . . . ?
C17 N3 C11 C12 -175.3(6) . . . . ?
N3 C11 C12 C13 56.7(7) . . . . ?
C11 C12 C13 C14 -56.1(8) . . . . ?
C12 C13 C14 C15 55.6(9) . . . . ?
C13 C14 C15 N3 -55.4(9) . . . . ?
C16 N3 C15 C14 -68.5(7) . . . . ?
C17 N3 C15 C14 169.2(6) . . . . ?
C11 N3 C15 C14 54.0(8) . . . . ?
C15 N3 C17 C18 54.5(8) . . . . ?
C16 N3 C17 C18 -69.0(8) . . . . ?
C11 N3 C17 C18 172.7(6) . . . . ?
N3 C17 C18 C19 171.8(6) . . . . ?
C17 C18 C19 C20 171.4(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
_geom_hbond_publ_flag
C1 H1 Br1 0.95 2.98 3.691(6) 133.2 3_766 yes
C2 H2 Br2 0.95 2.98 3.855(6) 154.6 3_766 yes
C7 H7 Br2 0.95 2.89 3.693(6) 143.2 4_576 yes
C9 H9 Br3 0.95 2.98 3.837(6) 151.5 3_666 yes
C9 H9 Br4 0.95 3.13 3.730(6) 122.6 3_666 yes
C11 H11A Br3 0.99 2.78 3.746(6) 164.3 4_566 yes
C11 H11B Br1 0.99 3.07 3.964(7) 150.8 . yes
C12 H12B Br2 0.99 2.88 3.853(7) 167.3 4_566 yes
C14 H14A Br2 0.99 3.12 3.717(7) 119.9 1_545 yes
C14 H14B O1 0.99 2.48 3.370(8) 149.1 1_545 yes
C16 H16A Br2 0.98 3.04 3.794(6) 135.1 4_566 yes
C16 H16B Br4 0.98 2.98 3.943(6) 169.5 1_545 yes
C16 H16C Br3 0.98 3.11 3.971(7) 148.0 4_566 yes
C17 H17B O2 0.99 2.22 3.052(9) 141.0 . yes
C18 H18A Br4 0.99 3.00 3.822(8) 141.7 1_545 yes

_refine_diff_density_max         1.386
_refine_diff_density_min         -1.426
_refine_diff_density_rms         0.190



