# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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 2044901'
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             
;
2020-11-17 deposited with the CCDC.	2020-12-22 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            'C16 H19 Bi Cl4 N4 O2'
_chemical_formula_weight         650.13

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   14.6969(12)
_cell_length_b                   9.1488(9)
_cell_length_c                   16.2644(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2186.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    3994
_cell_measurement_theta_min      3.5850
_cell_measurement_theta_max      28.8060

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.975
_exptl_crystal_F_000             1240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    8.569
_shelx_estimated_absorpt_T_min   0.360
_shelx_estimated_absorpt_T_max   0.426
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.69809
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      290(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            14023
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.226
_diffrn_reflns_theta_max         30.168
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5575
_reflns_number_gt                4113
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.807
_reflns_Friedel_fraction_max     0.795
_reflns_Friedel_fraction_full    0.989

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_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+3.5000P] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.446(15)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5575
_refine_ls_number_parameters     284
_refine_ls_number_restraints     148
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0774
_refine_ls_wR_factor_gt          0.0637
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.552
_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 0.17303(2) 0.25956(3) 0.37789(15) 0.03191(10) Uani 1 1 d . U . . .
Cl1 Cl 0.1869(2) 0.0846(3) 0.24868(18) 0.0457(7) Uani 1 1 d . . . . .
Cl2 Cl 0.1916(2) 0.4327(3) 0.51051(19) 0.0481(8) Uani 1 1 d . . . . .
Cl3 Cl 0.0593(3) 0.0777(4) 0.4580(2) 0.0663(10) Uani 1 1 d . . . . .
Cl4 Cl 0.0717(3) 0.4527(4) 0.2916(2) 0.0700(11) Uani 1 1 d . . . . .
O1 O 0.2997(5) 0.1192(8) 0.4282(5) 0.0378(19) Uani 1 1 d . . . . .
O2 O 0.3055(5) 0.3860(8) 0.3310(5) 0.041(2) Uani 1 1 d . . . . .
N1 N 0.3655(6) 0.1880(10) 0.4660(6) 0.034(2) Uani 1 1 d . . . . .
N2 N 0.3662(6) 0.3042(11) 0.2898(6) 0.036(2) Uani 1 1 d . . . . .
C1 C 0.3648(9) 0.1961(16) 0.5478(8) 0.043(3) Uani 1 1 d . . . . .
H1A H 0.316443 0.155443 0.576703 0.052 Uiso 1 1 calc R U . . .
C2 C 0.435(2) 0.2641(15) 0.5908(18) 0.051(6) Uani 1 1 d . . . . .
H2A H 0.434365 0.266157 0.647942 0.061 Uiso 1 1 calc R U . . .
C3 C 0.5038(9) 0.3277(14) 0.5478(7) 0.051(3) Uani 1 1 d . . . . .
H3A H 0.549760 0.377537 0.575327 0.062 Uiso 1 1 calc R U . . .
C4 C 0.5051(8) 0.3177(13) 0.4630(7) 0.042(3) Uani 1 1 d . . . . .
H4A H 0.553264 0.354705 0.432183 0.051 Uiso 1 1 calc R U . . .
C5 C 0.431(2) 0.2501(11) 0.4260(14) 0.035(6) Uani 1 1 d . . . . .
C6 C 0.435(2) 0.2351(14) 0.3349(14) 0.034(6) Uani 1 1 d . . . . .
C7 C 0.4967(8) 0.1550(13) 0.2897(8) 0.047(3) Uani 1 1 d . . . . .
H7A H 0.541155 0.101848 0.317283 0.056 Uiso 1 1 calc R U . . .
C8 C 0.4948(9) 0.1507(14) 0.2050(8) 0.053(3) Uani 1 1 d . . . . .
H8A H 0.538736 0.099542 0.175542 0.063 Uiso 1 1 calc R U . . .
C9 C 0.426(2) 0.2248(17) 0.1653(18) 0.047(5) Uani 1 1 d . . . . .
H9A H 0.422518 0.221279 0.108180 0.057 Uiso 1 1 calc R U . . .
C10 C 0.3633(9) 0.3014(15) 0.2065(7) 0.041(3) Uani 1 1 d . . . . .
H10A H 0.318196 0.352379 0.178419 0.049 Uiso 1 1 calc R U . . .
N4 N 0.720(2) 0.2394(19) 0.6730(12) 0.118(10) Uani 1 1 d D . . . .
C11 C 0.7590(17) 0.174(2) 0.5508(13) 0.117(7) Uani 1 1 d D U . . .
H11A H 0.764943 0.125588 0.500682 0.140 Uiso 1 1 d R U . A .
C12 C 0.6973(16) 0.150(2) 0.6112(13) 0.115(7) Uani 1 1 d D U . . .
H12A H 0.652415 0.078809 0.609004 0.138 Uiso 1 1 d R U . . .
C13 C 0.7893(15) 0.317(2) 0.6520(15) 0.132(11) Uani 1 1 d D . . . .
H13A H 0.815740 0.371605 0.693993 0.159 Uiso 1 1 d R U . A .
N3 N 0.8144(19) 0.272(3) 0.5794(13) 0.078(7) Uani 0.68(3) 1 d D U P A 1
C14 C 0.890(3) 0.329(6) 0.533(2) 0.16(2) Uani 0.68(3) 1 d D U P A 1
H14A H 0.921590 0.400047 0.565725 0.243 Uiso 0.68(3) 1 calc R U P A 1
H14B H 0.930422 0.250328 0.519528 0.243 Uiso 0.68(3) 1 calc R U P A 1
H14C H 0.867858 0.373714 0.483788 0.243 Uiso 0.68(3) 1 calc R U P A 1
C15 C 0.661(2) 0.255(4) 0.7414(17) 0.156(14) Uani 0.68(3) 1 d D U P A 1
H15A H 0.612684 0.183528 0.733437 0.188 Uiso 0.68(3) 1 calc R U P A 1
H15B H 0.632660 0.350146 0.735838 0.188 Uiso 0.68(3) 1 calc R U P A 1
C16 C 0.688(3) 0.242(4) 0.8261(18) 0.180(19) Uani 0.68(3) 1 d D U P A 1
H16A H 0.745678 0.193672 0.829253 0.270 Uiso 0.68(3) 1 calc R U P A 1
H16B H 0.643220 0.187256 0.855819 0.270 Uiso 0.68(3) 1 calc R U P A 1
H16C H 0.693124 0.338303 0.849661 0.270 Uiso 0.68(3) 1 calc R U P A 1
N3B N 0.807(6) 0.286(9) 0.575(3) 0.127(17) Uani 0.32(3) 1 d D U P A 2
C14B C 0.876(7) 0.353(12) 0.527(4) 0.13(3) Uani 0.32(3) 1 d D U P A 2
H14D H 0.902198 0.433405 0.557344 0.194 Uiso 0.32(3) 1 calc R U P A 2
H14E H 0.923141 0.282800 0.515447 0.194 Uiso 0.32(3) 1 calc R U P A 2
H14F H 0.851005 0.388509 0.476643 0.194 Uiso 0.32(3) 1 calc R U P A 2
C15B C 0.689(5) 0.223(8) 0.7552(18) 0.136(17) Uani 0.32(3) 1 d D U P A 2
H15C H 0.683443 0.320810 0.778077 0.163 Uiso 0.32(3) 1 calc R U P A 2
H15D H 0.736901 0.174478 0.785698 0.163 Uiso 0.32(3) 1 calc R U P A 2
C16B C 0.603(4) 0.146(8) 0.773(4) 0.16(3) Uani 0.32(3) 1 d D U P A 2
H16D H 0.567101 0.203484 0.810148 0.240 Uiso 0.32(3) 1 calc R U P A 2
H16E H 0.616936 0.053340 0.798762 0.240 Uiso 0.32(3) 1 calc R U P A 2
H16F H 0.570470 0.129409 0.723286 0.240 Uiso 0.32(3) 1 calc R U P A 2


_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 2.389(8) . ?
Bi1 O1 2.405(7) . ?
Bi1 Cl1 2.650(3) . ?
Bi1 Cl2 2.690(3) . ?
Bi1 Cl3 2.694(4) . ?
Bi1 Cl4 2.704(4) . ?
O1 N1 1.309(11) . ?
O2 N2 1.344(12) . ?
N1 C5 1.30(3) . ?
N1 C1 1.331(14) . ?
N2 C10 1.355(14) . ?
N2 C6 1.40(3) . ?
C1 C2 1.39(3) . ?
C2 C3 1.36(3) . ?
C3 C4 1.383(15) . ?
C4 C5 1.38(3) . ?
C5 C6 1.490(14) . ?
C6 C7 1.38(3) . ?
C7 C8 1.377(16) . ?
C8 C9 1.38(3) . ?
C9 C10 1.34(3) . ?
N4 C13 1.28(3) . ?
N4 C12 1.34(2) . ?
N4 C15B 1.422(13) . ?
N4 C15 1.424(12) . ?
C11 N3 1.30(2) . ?
C11 N3B 1.31(2) . ?
C11 C12 1.35(3) . ?
C13 N3 1.30(2) . ?
C13 N3B 1.31(2) . ?
N3 C14 1.434(13) . ?
C15 C16 1.44(2) . ?
N3B C14B 1.429(13) . ?
C15B C16B 1.48(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
O2 Bi1 O1 74.7(2) . . ?
O2 Bi1 Cl1 88.7(2) . . ?
O1 Bi1 Cl1 83.52(19) . . ?
O2 Bi1 Cl2 83.6(2) . . ?
O1 Bi1 Cl2 87.9(2) . . ?
Cl1 Bi1 Cl2 169.70(7) . . ?
O2 Bi1 Cl3 163.5(2) . . ?
O1 Bi1 Cl3 89.2(2) . . ?
Cl1 Bi1 Cl3 93.35(10) . . ?
Cl2 Bi1 Cl3 92.23(12) . . ?
O2 Bi1 Cl4 88.1(2) . . ?
O1 Bi1 Cl4 162.2(2) . . ?
Cl1 Bi1 Cl4 91.48(12) . . ?
Cl2 Bi1 Cl4 95.00(10) . . ?
Cl3 Bi1 Cl4 108.22(12) . . ?
N1 O1 Bi1 118.4(6) . . ?
N2 O2 Bi1 115.5(6) . . ?
C5 N1 O1 121.8(12) . . ?
C5 N1 C1 118.8(13) . . ?
O1 N1 C1 119.4(10) . . ?
O2 N2 C10 119.2(10) . . ?
O2 N2 C6 118.0(13) . . ?
C10 N2 C6 122.6(14) . . ?
N1 C1 C2 121.4(17) . . ?
C3 C2 C1 119(2) . . ?
C2 C3 C4 119.6(16) . . ?
C3 C4 C5 116.8(15) . . ?
N1 C5 C4 124.2(18) . . ?
N1 C5 C6 119(2) . . ?
C4 C5 C6 116(3) . . ?
C7 C6 N2 115.8(18) . . ?
C7 C6 C5 127(3) . . ?
N2 C6 C5 117(3) . . ?
C8 C7 C6 122.4(14) . . ?
C7 C8 C9 117.9(16) . . ?
C10 C9 C8 122(2) . . ?
C9 C10 N2 119.4(16) . . ?
C13 N4 C12 110(2) . . ?
C13 N4 C15B 124(2) . . ?
C12 N4 C15B 124(2) . . ?
C13 N4 C15 130(2) . . ?
C12 N4 C15 119(2) . . ?
N3 C11 C12 105.6(16) . . ?
N3B C11 C12 105.2(17) . . ?
N4 C12 C11 106.2(19) . . ?
N4 C13 N3 107(2) . . ?
N4 C13 N3B 107(2) . . ?
C11 N3 C13 111(2) . . ?
C11 N3 C14 123.1(17) . . ?
C13 N3 C14 125.4(18) . . ?
N4 C15 C16 125(3) . . ?
C11 N3B C13 111(3) . . ?
C11 N3B C14B 124(2) . . ?
C13 N3B C14B 125(2) . . ?
N4 C15B C16B 121(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 C5 -84.1(13) . . . . ?
Bi1 O1 N1 C1 95.2(11) . . . . ?
Bi1 O2 N2 C10 95.3(11) . . . . ?
Bi1 O2 N2 C6 -90.1(13) . . . . ?
C5 N1 C1 C2 -3(2) . . . . ?
O1 N1 C1 C2 178.0(14) . . . . ?
N1 C1 C2 C3 2(3) . . . . ?
C1 C2 C3 C4 -3(3) . . . . ?
C2 C3 C4 C5 4(2) . . . . ?
O1 N1 C5 C4 -176.5(12) . . . . ?
C1 N1 C5 C4 4(2) . . . . ?
O1 N1 C5 C6 -4(3) . . . . ?
C1 N1 C5 C6 177.0(18) . . . . ?
C3 C4 C5 N1 -5(2) . . . . ?
C3 C4 C5 C6 -177.9(15) . . . . ?
O2 N2 C6 C7 -178.7(12) . . . . ?
C10 N2 C6 C7 -4(2) . . . . ?
O2 N2 C6 C5 4(3) . . . . ?
C10 N2 C6 C5 178.4(18) . . . . ?
N1 C5 C6 C7 -110(4) . . . . ?
C4 C5 C6 C7 63.9(18) . . . . ?
N1 C5 C6 N2 67.4(14) . . . . ?
C4 C5 C6 N2 -119(3) . . . . ?
N2 C6 C7 C8 4(2) . . . . ?
C5 C6 C7 C8 -179(2) . . . . ?
C6 C7 C8 C9 -3(2) . . . . ?
C7 C8 C9 C10 1(3) . . . . ?
C8 C9 C10 N2 -2(3) . . . . ?
O2 N2 C10 C9 177.4(14) . . . . ?
C6 N2 C10 C9 3(2) . . . . ?
C13 N4 C12 C11 2(3) . . . . ?
C15B N4 C12 C11 -163(5) . . . . ?
C15 N4 C12 C11 171(2) . . . . ?
N3 C11 C12 N4 0(3) . . . . ?
N3B C11 C12 N4 -8(6) . . . . ?
C12 N4 C13 N3 -4(3) . . . . ?
C15 N4 C13 N3 -172(3) . . . . ?
C12 N4 C13 N3B 4(7) . . . . ?
C15B N4 C13 N3B 169(7) . . . . ?
C12 C11 N3 C13 -3(3) . . . . ?
C12 C11 N3 C14 -179(4) . . . . ?
N4 C13 N3 C11 5(3) . . . . ?
N4 C13 N3 C14 -179(4) . . . . ?
C13 N4 C15 C16 -63(5) . . . . ?
C12 N4 C15 C16 130(3) . . . . ?
C12 C11 N3B C13 11(10) . . . . ?
C12 C11 N3B C14B -176(11) . . . . ?
N4 C13 N3B C11 -10(10) . . . . ?
N4 C13 N3B C14B 178(11) . . . . ?
C13 N4 C15B C16B 173(6) . . . . ?
C12 N4 C15B C16B -24(10) . . . . ?

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 H1A Cl1 0.93 2.87 3.507(13) 126.6 4 yes
C2 H2A Cl1 0.93 2.94 3.53(3) 123.3 4 yes
C2 H2A Cl4 0.93 2.90 3.70(3) 145.0 4 yes
C4 H4A Cl4 0.93 2.90 3.624(12) 135.8 3_565 yes
C7 H7A Cl1 0.93 2.96 3.614(11) 128.9 3 yes
C7 H7A Cl3 0.93 2.83 3.588(14) 139.5 3 yes
C9 H9A Cl3 0.93 2.79 3.64(3) 152.5 4_554 yes
C10 H10A Cl2 0.93 2.83 3.501(11) 129.8 4_554 yes
C11 H11A O1 0.93 2.58 3.393(19) 146.0 3 yes
C13 H13A Cl4 0.93 2.80 3.71(2) 166.0 2_665 yes
C14^a H14B^a Cl3 0.96 2.66 3.60(6) 166.9 1_655 yes
C16^a H16C^a O2 0.96 2.54 3.40(3) 149.3 2_665 yes
C14B^b H14E^b Cl3 0.96 2.90 3.85(13) 172.7 1_655 yes
C15B^b H15D^b Cl1 0.97 2.69 3.36(9) 126.4 2_655 yes

_refine_diff_density_max         1.974
_refine_diff_density_min         -1.846
_refine_diff_density_rms         0.154

####################################################################### 
# 
# 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_try
_database_code_depnum_ccdc_archive 'CCDC 2044902'
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             
;
2020-11-17 deposited with the CCDC.	2020-12-22 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            'C16 H19 Bi Cl4 N4 O2'
_chemical_formula_weight         650.13

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   14.4947(7)
_cell_length_b                   9.0474(6)
_cell_length_c                   16.1935(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2123.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5157
_cell_measurement_theta_min      2.5640
_cell_measurement_theta_max      31.9200

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.033
_exptl_crystal_F_000             1240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    8.825
_shelx_estimated_absorpt_T_min   0.351
_shelx_estimated_absorpt_T_max   0.472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.72762
_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            18014
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.251
_diffrn_reflns_theta_max         32.276
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             6679
_reflns_number_gt                5364
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_max     0.820
_reflns_Friedel_fraction_full    0.975

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0310P)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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.537(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6679
_refine_ls_number_parameters     247
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0798
_refine_ls_wR_factor_gt          0.0698
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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 0.16862(2) 0.25799(3) 0.37800(15) 0.01348(7) Uani 1 1 d . . . . .
Cl1 Cl 0.18649(15) 0.0783(2) 0.24910(13) 0.0185(5) Uani 1 1 d . . . . .
Cl2 Cl 0.19034(15) 0.4342(2) 0.50925(13) 0.0194(5) Uani 1 1 d . . . . .
Cl3 Cl 0.04991(19) 0.0768(3) 0.45951(14) 0.0328(6) Uani 1 1 d . . . . .
Cl4 Cl 0.06936(18) 0.4566(3) 0.28822(14) 0.0312(6) Uani 1 1 d . . . . .
O1 O 0.2950(4) 0.1163(7) 0.4276(4) 0.0184(14) Uani 1 1 d . . . . .
O2 O 0.3007(4) 0.3859(7) 0.3305(4) 0.0178(14) Uani 1 1 d . . . . .
N1 N 0.3624(5) 0.1880(8) 0.4667(4) 0.0136(14) Uani 1 1 d . . . . .
N2 N 0.3638(5) 0.3061(8) 0.2892(4) 0.0159(15) Uani 1 1 d . . . . .
C1 C 0.3613(7) 0.1931(10) 0.5498(5) 0.0174(18) Uani 1 1 d . . . . .
H1A H 0.311696 0.148294 0.578938 0.021 Uiso 1 1 calc R U . . .
C2 C 0.4315(11) 0.2632(9) 0.5941(9) 0.014(2) Uani 1 1 d . U . . .
H2A H 0.430955 0.265324 0.652786 0.017 Uiso 1 1 calc R U . . .
C3 C 0.5020(6) 0.3293(10) 0.5497(5) 0.0194(19) Uani 1 1 d . . . . .
H3A H 0.549887 0.379884 0.578099 0.023 Uiso 1 1 calc R U . . .
C4 C 0.5032(6) 0.3223(10) 0.4639(5) 0.0184(18) Uani 1 1 d . . . . .
H4A H 0.552660 0.364696 0.433531 0.022 Uiso 1 1 calc R U . . .
C5 C 0.4302(12) 0.2517(8) 0.4227(11) 0.014(3) Uani 1 1 d . . . . .
C6 C 0.4324(14) 0.2354(11) 0.3315(11) 0.019(4) Uani 1 1 d . . . . .
C7 C 0.4969(7) 0.1585(10) 0.2903(5) 0.0205(19) Uani 1 1 d . . . . .
H7A H 0.543989 0.108086 0.319810 0.025 Uiso 1 1 calc R U . . .
C8 C 0.4950(7) 0.1527(10) 0.2051(5) 0.0206(19) Uani 1 1 d . . . . .
H8A H 0.540792 0.100484 0.174913 0.025 Uiso 1 1 calc R U . . .
C9 C 0.4233(12) 0.2261(12) 0.1648(11) 0.023(3) Uani 1 1 d . . . . .
H9A H 0.419590 0.221460 0.106322 0.027 Uiso 1 1 calc R U . . .
C10 C 0.3600(6) 0.3023(11) 0.2061(5) 0.0172(18) Uani 1 1 d . . . . .
H10A H 0.312625 0.353545 0.177362 0.021 Uiso 1 1 calc R U . . .
N3 N 0.8048(12) 0.2754(12) 0.5947(10) 0.043(3) Uani 1 1 d . . . . .
N4 N 0.6977(14) 0.2229(13) 0.6820(10) 0.048(4) Uani 1 1 d . . . . .
C11 C 0.7523(10) 0.1757(15) 0.5577(8) 0.050(3) Uani 1 1 d . . . . .
H11A H 0.760240 0.135910 0.503870 0.061 Uiso 1 1 calc R U . . .
C12 C 0.6856(9) 0.1427(15) 0.6117(7) 0.049(3) Uani 1 1 d . . . . .
H12A H 0.637222 0.073841 0.602431 0.058 Uiso 1 1 calc R U . . .
C13 C 0.7706(11) 0.3020(16) 0.6727(9) 0.057(4) Uani 1 1 d . . . . .
H13A H 0.796392 0.367234 0.712516 0.068 Uiso 1 1 calc R U . . .
C14 C 0.8837(9) 0.3496(15) 0.5556(9) 0.069(4) Uani 1 1 d . . . . .
H14A H 0.920429 0.399862 0.597896 0.104 Uiso 1 1 calc R U . . .
H14B H 0.861181 0.422225 0.515446 0.104 Uiso 1 1 calc R U . . .
H14C H 0.922050 0.276175 0.527264 0.104 Uiso 1 1 calc R U . . .
C15 C 0.6388(14) 0.208(2) 0.7557(9) 0.095(6) Uani 1 1 d . . . . .
H15A H 0.584031 0.271999 0.748551 0.114 Uiso 1 1 calc R U . . .
H15B H 0.616638 0.104486 0.758782 0.114 Uiso 1 1 calc R U . . .
C16 C 0.6810(11) 0.2438(13) 0.8316(10) 0.066(5) Uani 1 1 d . . . . .
H16A H 0.736063 0.182432 0.839275 0.099 Uiso 1 1 calc R U . . .
H16B H 0.637559 0.225620 0.876829 0.099 Uiso 1 1 calc R U . . .
H16C H 0.698766 0.348316 0.831378 0.099 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 2.366(6) . ?
Bi1 O1 2.375(6) . ?
Bi1 Cl1 2.659(3) . ?
Bi1 Cl2 2.676(3) . ?
Bi1 Cl3 2.718(3) . ?
Bi1 Cl4 2.722(3) . ?
O1 N1 1.333(9) . ?
O2 N2 1.343(9) . ?
N1 C5 1.344(19) . ?
N1 C1 1.348(10) . ?
N2 C10 1.348(10) . ?
N2 C6 1.367(19) . ?
C1 C2 1.397(16) . ?
C2 C3 1.385(17) . ?
C3 C4 1.392(11) . ?
C4 C5 1.404(17) . ?
C5 C6 1.484(9) . ?
C6 C7 1.34(2) . ?
C7 C8 1.382(11) . ?
C8 C9 1.395(19) . ?
C9 C10 1.328(18) . ?
N3 C11 1.324(19) . ?
N3 C13 1.38(2) . ?
N3 C14 1.47(2) . ?
N4 C13 1.29(2) . ?
N4 C12 1.362(19) . ?
N4 C15 1.47(2) . ?
C11 C12 1.337(17) . ?
C15 C16 1.41(2) . ?

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 75.52(17) . . ?
O2 Bi1 Cl1 88.00(17) . . ?
O1 Bi1 Cl1 81.97(15) . . ?
O2 Bi1 Cl2 82.61(15) . . ?
O1 Bi1 Cl2 87.84(17) . . ?
Cl1 Bi1 Cl2 167.61(5) . . ?
O2 Bi1 Cl3 164.82(18) . . ?
O1 Bi1 Cl3 89.91(17) . . ?
Cl1 Bi1 Cl3 94.25(7) . . ?
Cl2 Bi1 Cl3 92.76(11) . . ?
O2 Bi1 Cl4 86.06(17) . . ?
O1 Bi1 Cl4 160.77(18) . . ?
Cl1 Bi1 Cl4 92.05(11) . . ?
Cl2 Bi1 Cl4 95.34(7) . . ?
Cl3 Bi1 Cl4 108.83(9) . . ?
N1 O1 Bi1 117.6(5) . . ?
N2 O2 Bi1 116.7(5) . . ?
O1 N1 C5 119.6(9) . . ?
O1 N1 C1 118.8(7) . . ?
C5 N1 C1 121.6(9) . . ?
O2 N2 C10 118.9(7) . . ?
O2 N2 C6 119.8(10) . . ?
C10 N2 C6 121.2(10) . . ?
N1 C1 C2 121.3(10) . . ?
C3 C2 C1 117.8(12) . . ?
C2 C3 C4 120.5(9) . . ?
C3 C4 C5 119.0(11) . . ?
N1 C5 C4 119.7(14) . . ?
N1 C5 C6 120.0(16) . . ?
C4 C5 C6 120.1(19) . . ?
C7 C6 N2 120.0(14) . . ?
C7 C6 C5 124.1(17) . . ?
N2 C6 C5 115.9(16) . . ?
C6 C7 C8 120.2(11) . . ?
C7 C8 C9 117.6(11) . . ?
C10 C9 C8 121.8(14) . . ?
C9 C10 N2 119.2(11) . . ?
C11 N3 C13 109.1(15) . . ?
C11 N3 C14 124.3(15) . . ?
C13 N3 C14 126.5(14) . . ?
C13 N4 C12 107.7(17) . . ?
C13 N4 C15 128.5(16) . . ?
C12 N4 C15 123.6(17) . . ?
N3 C11 C12 105.8(14) . . ?
C11 C12 N4 109.6(15) . . ?
N4 C13 N3 107.8(13) . . ?
C16 C15 N4 115.6(18) . . ?

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 C5 -84.4(9) . . . . ?
Bi1 O1 N1 C1 96.4(8) . . . . ?
Bi1 O2 N2 C10 94.6(8) . . . . ?
Bi1 O2 N2 C6 -88.1(10) . . . . ?
O1 N1 C1 C2 178.2(9) . . . . ?
C5 N1 C1 C2 -1.0(15) . . . . ?
N1 C1 C2 C3 1.0(16) . . . . ?
C1 C2 C3 C4 -1.6(15) . . . . ?
C2 C3 C4 C5 2.2(15) . . . . ?
O1 N1 C5 C4 -177.6(8) . . . . ?
C1 N1 C5 C4 1.7(15) . . . . ?
O1 N1 C5 C6 -3.2(16) . . . . ?
C1 N1 C5 C6 176.1(11) . . . . ?
C3 C4 C5 N1 -2.3(15) . . . . ?
C3 C4 C5 C6 -176.6(11) . . . . ?
O2 N2 C6 C7 -178.3(10) . . . . ?
C10 N2 C6 C7 -1.0(17) . . . . ?
O2 N2 C6 C5 1.0(18) . . . . ?
C10 N2 C6 C5 178.3(11) . . . . ?
N1 C5 C6 C7 -112(2) . . . . ?
C4 C5 C6 C7 62.2(12) . . . . ?
N1 C5 C6 N2 68.6(10) . . . . ?
C4 C5 C6 N2 -117.1(18) . . . . ?
N2 C6 C7 C8 1.1(18) . . . . ?
C5 C6 C7 C8 -178.2(13) . . . . ?
C6 C7 C8 C9 -1.3(16) . . . . ?
C7 C8 C9 C10 1.6(17) . . . . ?
C8 C9 C10 N2 -1.6(17) . . . . ?
O2 N2 C10 C9 178.6(9) . . . . ?
C6 N2 C10 C9 1.3(16) . . . . ?
C13 N3 C11 C12 0.9(16) . . . . ?
C14 N3 C11 C12 -176.2(12) . . . . ?
N3 C11 C12 N4 0.0(14) . . . . ?
C13 N4 C12 C11 -1.0(16) . . . . ?
C15 N4 C12 C11 -177.0(14) . . . . ?
C12 N4 C13 N3 1.5(18) . . . . ?
C15 N4 C13 N3 177.2(13) . . . . ?
C11 N3 C13 N4 -1.5(19) . . . . ?
C14 N3 C13 N4 175.5(11) . . . . ?
C13 N4 C15 C16 -22(2) . . . . ?
C12 N4 C15 C16 152.8(15) . . . . ?

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 H1A Cl1 0.95 2.83 3.460(9) 124.9 4 yes
C2 H2A Cl1 0.95 2.86 3.467(15) 122.5 4 yes
C2 H2A Cl4 0.95 2.79 3.597(14) 142.9 4 yes
C4 H4A Cl2 0.95 2.97 3.571(9) 122.8 3_565 yes
C4 H4A Cl4 0.95 2.87 3.607(9) 135.7 3_565 yes
C7 H7A Cl1 0.95 2.90 3.548(10) 126.3 3 yes
C7 H7A Cl3 0.95 2.81 3.554(9) 135.4 3 yes
C9 H9A Cl2 0.95 2.95 3.550(16) 122.2 4_554 yes
C9 H9A Cl3 0.95 2.75 3.610(17) 151.0 4_554 yes
C10 H10A Cl2 0.95 2.82 3.481(9) 127.6 4_554 yes
C11 H11A O1 0.95 2.64 3.435(15) 141.2 3 yes
C12 H12A Cl3 0.95 2.97 3.726(14) 137.6 3 yes
C13 H13A Cl4 0.95 2.80 3.694(15) 157.5 2_665 yes
C14 H14B Cl2 0.98 2.80 3.499(14) 129.0 3_565 yes
C14 H14C Cl3 0.98 2.81 3.784(15) 172.8 1_655 yes
C15 H15A Cl4 0.99 2.85 3.800(17) 160.2 4 yes
C16 H16C O2 0.98 2.40 3.361(13) 165.0 2_665 yes

_refine_diff_density_max         1.392
_refine_diff_density_min         -1.699
_refine_diff_density_rms         0.201

####################################################################### 
# 
# 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 2044904'
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             
;
2020-11-17 deposited with the CCDC.	2020-12-22 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            'C17 H21 Bi Cl4 N4 O2'
_chemical_formula_weight         664.16

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   16.2874(6)
_cell_length_b                   16.3137(6)
_cell_length_c                   17.1361(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4553.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    27048
_cell_measurement_theta_min      2.0750
_cell_measurement_theta_max      32.1250

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.938
_exptl_crystal_F_000             2544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    8.234
_shelx_estimated_absorpt_T_min   0.233
_shelx_estimated_absorpt_T_max   0.277
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.30881
_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            69454
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.129
_diffrn_reflns_theta_max         25.023
_diffrn_reflns_theta_full        25.023
_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             4013
_reflns_number_gt                3610
_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-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)+(0.0286P)²+11.1895P] 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         4013
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0205
_refine_ls_wR_factor_ref         0.0531
_refine_ls_wR_factor_gt          0.0494
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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 0.15919(2) 0.73559(2) 0.34645(2) 0.00965(6) Uani 1 1 d . . . . .
Cl1 Cl 0.17446(5) 0.61789(5) 0.23987(5) 0.01720(19) Uani 1 1 d . . . . .
Cl2 Cl 0.18368(6) 0.85890(6) 0.44881(5) 0.0217(2) Uani 1 1 d . . . . .
Cl3 Cl 0.04721(5) 0.82644(5) 0.27091(5) 0.01779(19) Uani 1 1 d . . . . .
Cl4 Cl 0.05304(5) 0.64304(5) 0.42581(5) 0.01682(19) Uani 1 1 d . . . . .
O1 O 0.27858(14) 0.78056(15) 0.27605(14) 0.0152(5) Uani 1 1 d . . . . .
O2 O 0.26987(14) 0.67961(15) 0.42075(15) 0.0148(5) Uani 1 1 d . . . . .
N1 N 0.33386(16) 0.82229(19) 0.31826(18) 0.0122(6) Uani 1 1 d . . . . .
N2 N 0.33130(16) 0.64344(18) 0.38274(18) 0.0120(6) Uani 1 1 d . . . . .
C1 C 0.3341(2) 0.9044(2) 0.3154(2) 0.0157(8) Uani 1 1 d . . . . .
H1 H 0.295822 0.932061 0.282942 0.019 Uiso 1 1 calc R U . . .
C2 C 0.3891(2) 0.9487(2) 0.3587(2) 0.0165(8) Uani 1 1 d . . . . .
H2 H 0.389434 1.006884 0.355935 0.020 Uiso 1 1 calc R U . . .
C3 C 0.4441(2) 0.9082(2) 0.4064(2) 0.0176(8) Uani 1 1 d . . . . .
H3 H 0.481081 0.938201 0.438427 0.021 Uiso 1 1 calc R U . . .
C4 C 0.4448(2) 0.8231(2) 0.4071(2) 0.0146(8) Uani 1 1 d . . . . .
H4 H 0.483392 0.794540 0.438407 0.018 Uiso 1 1 calc R U . . .
C5 C 0.3893(2) 0.7802(2) 0.3622(2) 0.0125(7) Uani 1 1 d . . . . .
C6 C 0.3935(2) 0.6902(2) 0.3532(2) 0.0130(7) Uani 1 1 d . . . . .
C7 C 0.4603(2) 0.6522(2) 0.3204(3) 0.0234(9) Uani 1 1 d . . . . .
H7 H 0.504670 0.684171 0.301206 0.028 Uiso 1 1 calc R U . . .
C8 C 0.4636(2) 0.5672(2) 0.3150(3) 0.0275(10) Uani 1 1 d . . . . .
H8 H 0.509488 0.540719 0.292010 0.033 Uiso 1 1 calc R U . . .
C9 C 0.3983(2) 0.5221(2) 0.3440(2) 0.0201(9) Uani 1 1 d . . . . .
H9 H 0.398970 0.463937 0.340608 0.024 Uiso 1 1 calc R U . . .
C10 C 0.3328(2) 0.5613(2) 0.3777(2) 0.0158(8) Uani 1 1 d . . . . .
H10 H 0.288142 0.530203 0.397548 0.019 Uiso 1 1 calc R U . . .
N3 N 0.33392(19) 0.6744(2) 0.60073(19) 0.0206(7) Uani 1 1 d . . . . .
N4 N 0.26152(19) 0.5658(2) 0.58092(19) 0.0190(7) Uani 1 1 d . . . . .
C11 C 0.3877(2) 0.6098(3) 0.5934(2) 0.0277(10) Uani 1 1 d . . . . .
H11 H 0.445817 0.612806 0.596403 0.033 Uiso 1 1 calc R U . . .
C12 C 0.3433(2) 0.5420(3) 0.5814(3) 0.0256(9) Uani 1 1 d . . . . .
H12 H 0.363788 0.487943 0.574578 0.031 Uiso 1 1 calc R U . . .
C13 C 0.2574(2) 0.6466(2) 0.5930(2) 0.0170(8) Uani 1 1 d . . . . .
C14 C 0.3563(3) 0.7608(3) 0.6104(3) 0.0294(10) Uani 1 1 d . . . . .
H14A H 0.346058 0.790295 0.561574 0.044 Uiso 1 1 calc R U . . .
H14B H 0.414627 0.764850 0.623922 0.044 Uiso 1 1 calc R U . . .
H14C H 0.323197 0.784966 0.652258 0.044 Uiso 1 1 calc R U . . .
C15 C 0.1821(2) 0.6967(2) 0.5963(2) 0.0199(8) Uani 1 1 d . . . . .
H15A H 0.144408 0.679437 0.554795 0.030 Uiso 1 1 calc R U . . .
H15B H 0.196248 0.754587 0.589078 0.030 Uiso 1 1 calc R U . . .
H15C H 0.155491 0.689378 0.647105 0.030 Uiso 1 1 calc R U . . .
C16 C 0.1912(2) 0.5112(2) 0.5669(2) 0.0227(9) Uani 1 1 d . . . . .
H16A H 0.210947 0.460605 0.541119 0.027 Uiso 1 1 calc R U . . .
H16B H 0.152379 0.538603 0.530948 0.027 Uiso 1 1 calc R U . . .
C17 C 0.1466(2) 0.4884(3) 0.6408(3) 0.0249(9) Uani 1 1 d . . . . .
H17A H 0.100286 0.452482 0.628198 0.037 Uiso 1 1 calc R U . . .
H17B H 0.126200 0.538236 0.666278 0.037 Uiso 1 1 calc R U . . .
H17C H 0.184320 0.459814 0.676086 0.037 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 2.388(2) . ?
Bi1 O1 2.403(2) . ?
Bi1 Cl1 2.6617(9) . ?
Bi1 Cl4 2.6679(9) . ?
Bi1 Cl3 2.6831(9) . ?
Bi1 Cl2 2.6987(9) . ?
O1 N1 1.341(4) . ?
O2 N2 1.332(4) . ?
N1 C1 1.340(5) . ?
N1 C5 1.361(5) . ?
N2 C10 1.342(5) . ?
N2 C6 1.365(4) . ?
C1 C2 1.370(5) . ?
C2 C3 1.381(5) . ?
C3 C4 1.388(5) . ?
C4 C5 1.378(5) . ?
C5 C6 1.477(5) . ?
C6 C7 1.374(5) . ?
C7 C8 1.390(6) . ?
C8 C9 1.385(6) . ?
C9 C10 1.372(5) . ?
N3 C13 1.333(5) . ?
N3 C11 1.376(5) . ?
N3 C14 1.464(5) . ?
N4 C13 1.335(5) . ?
N4 C12 1.387(5) . ?
N4 C16 1.470(5) . ?
C11 C12 1.337(6) . ?
C13 C15 1.476(5) . ?
C16 C17 1.507(6) . ?

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 76.91(8) . . ?
O2 Bi1 Cl1 91.11(6) . . ?
O1 Bi1 Cl1 78.47(6) . . ?
O2 Bi1 Cl4 90.06(6) . . ?
O1 Bi1 Cl4 162.37(6) . . ?
Cl1 Bi1 Cl4 90.12(3) . . ?
O2 Bi1 Cl3 168.95(6) . . ?
O1 Bi1 Cl3 98.00(6) . . ?
Cl1 Bi1 Cl3 97.52(3) . . ?
Cl4 Bi1 Cl3 96.78(3) . . ?
O2 Bi1 Cl2 80.04(6) . . ?
O1 Bi1 Cl2 88.80(6) . . ?
Cl1 Bi1 Cl2 165.92(3) . . ?
Cl4 Bi1 Cl2 100.74(3) . . ?
Cl3 Bi1 Cl2 90.13(3) . . ?
N1 O1 Bi1 115.31(19) . . ?
N2 O2 Bi1 118.4(2) . . ?
O1 N1 C1 119.3(3) . . ?
O1 N1 C5 119.2(3) . . ?
C1 N1 C5 121.5(3) . . ?
O2 N2 C10 119.2(3) . . ?
O2 N2 C6 119.4(3) . . ?
C10 N2 C6 121.4(3) . . ?
N1 C1 C2 120.7(3) . . ?
C1 C2 C3 119.5(4) . . ?
C2 C3 C4 119.2(3) . . ?
C5 C4 C3 119.9(3) . . ?
N1 C5 C4 119.2(3) . . ?
N1 C5 C6 118.3(3) . . ?
C4 C5 C6 122.2(3) . . ?
N2 C6 C7 119.1(3) . . ?
N2 C6 C5 118.9(3) . . ?
C7 C6 C5 121.9(3) . . ?
C6 C7 C8 120.5(4) . . ?
C9 C8 C7 118.5(4) . . ?
C10 C9 C8 119.9(4) . . ?
N2 C10 C9 120.5(3) . . ?
C13 N3 C11 108.9(3) . . ?
C13 N3 C14 124.9(3) . . ?
C11 N3 C14 126.1(3) . . ?
C13 N4 C12 108.9(3) . . ?
C13 N4 C16 125.7(3) . . ?
C12 N4 C16 125.3(3) . . ?
C12 C11 N3 107.7(3) . . ?
C11 C12 N4 106.7(4) . . ?
N3 C13 N4 107.8(3) . . ?
N3 C13 C15 125.7(4) . . ?
N4 C13 C15 126.5(3) . . ?
N4 C16 C17 112.8(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 -98.5(3) . . . . ?
Bi1 O1 N1 C5 82.5(3) . . . . ?
Bi1 O2 N2 C10 -99.7(3) . . . . ?
Bi1 O2 N2 C6 83.7(3) . . . . ?
O1 N1 C1 C2 179.1(3) . . . . ?
C5 N1 C1 C2 -2.0(5) . . . . ?
N1 C1 C2 C3 -0.7(6) . . . . ?
C1 C2 C3 C4 2.6(5) . . . . ?
C2 C3 C4 C5 -1.9(5) . . . . ?
O1 N1 C5 C4 -178.4(3) . . . . ?
C1 N1 C5 C4 2.7(5) . . . . ?
O1 N1 C5 C6 8.1(5) . . . . ?
C1 N1 C5 C6 -170.8(3) . . . . ?
C3 C4 C5 N1 -0.7(5) . . . . ?
C3 C4 C5 C6 172.5(3) . . . . ?
O2 N2 C6 C7 174.1(3) . . . . ?
C10 N2 C6 C7 -2.5(5) . . . . ?
O2 N2 C6 C5 -2.0(5) . . . . ?
C10 N2 C6 C5 -178.6(3) . . . . ?
N1 C5 C6 N2 -72.3(4) . . . . ?
C4 C5 C6 N2 114.5(4) . . . . ?
N1 C5 C6 C7 111.7(4) . . . . ?
C4 C5 C6 C7 -61.6(5) . . . . ?
N2 C6 C7 C8 2.0(6) . . . . ?
C5 C6 C7 C8 178.0(4) . . . . ?
C6 C7 C8 C9 -0.5(7) . . . . ?
C7 C8 C9 C10 -0.5(6) . . . . ?
O2 N2 C10 C9 -175.1(3) . . . . ?
C6 N2 C10 C9 1.5(6) . . . . ?
C8 C9 C10 N2 0.0(6) . . . . ?
C13 N3 C11 C12 -0.2(5) . . . . ?
C14 N3 C11 C12 -176.6(4) . . . . ?
N3 C11 C12 N4 0.4(5) . . . . ?
C13 N4 C12 C11 -0.4(5) . . . . ?
C16 N4 C12 C11 177.9(4) . . . . ?
C11 N3 C13 N4 -0.1(4) . . . . ?
C14 N3 C13 N4 176.4(4) . . . . ?
C11 N3 C13 C15 -179.3(4) . . . . ?
C14 N3 C13 C15 -2.9(6) . . . . ?
C12 N4 C13 N3 0.3(4) . . . . ?
C16 N4 C13 N3 -178.0(3) . . . . ?
C12 N4 C13 C15 179.6(4) . . . . ?
C16 N4 C13 C15 1.3(6) . . . . ?
C13 N4 C16 C17 -79.4(5) . . . . ?
C12 N4 C16 C17 102.6(4) . . . . ?

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
C2 H2 Cl1 0.95 2.88 3.583(4) 131.3 8_665 yes
C2 H2 Cl4 0.95 2.69 3.501(4) 143.5 8_665 yes
C4 H4 Cl4 0.95 2.78 3.409(4) 124.3 4_566 yes
C7 H7 Cl3 0.95 2.72 3.540(4) 145.1 6_656 yes
C9 H9 Cl2 0.95 2.86 3.477(4) 123.5 8_655 yes
C9 H9 Cl3 0.95 2.69 3.541(4) 149.7 8_655 yes
C10 H10 Cl2 0.95 2.97 3.530(4) 119.4 8_655 yes
C11 H11 Cl3 0.95 2.98 3.639(4) 127.6 4_566 yes
C14 H14B Cl4 0.98 2.84 3.622(4) 137.3 4_566 yes
C14 H14C O1 0.98 2.48 3.180(5) 127.8 7_576 yes
C15 H15A Cl4 0.98 2.73 3.703(4) 172.2 . yes
C15 H15B Cl2 0.98 2.95 3.659(4) 129.9 . yes
C15 H15C Cl3 0.98 2.77 3.731(4) 166.7 7_576 yes
C16 H16A Cl2 0.99 2.86 3.797(4) 157.5 8_655 yes
C16 H16B Cl4 0.99 2.96 3.942(4) 171.1 . yes
C17 H17C Cl1 0.98 2.84 3.792(4) 162.9 2_565 yes

_refine_diff_density_max         1.449
_refine_diff_density_min         -1.481
_refine_diff_density_rms         0.112

####################################################################### 
# 
# 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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2044903'
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             
;
2020-11-17 deposited with the CCDC.	2020-12-22 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            'C17 H21 Bi Cl4 N4 O2'
_chemical_formula_weight         664.16

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   16.4032(6)
_cell_length_b                   16.4094(6)
_cell_length_c                   17.3812(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4678.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    22593
_cell_measurement_theta_min      2.9740
_cell_measurement_theta_max      29.9280

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.886
_exptl_crystal_F_000             2544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    8.014
_shelx_estimated_absorpt_T_min   0.239
_shelx_estimated_absorpt_T_max   0.284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.56893
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      290(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            85265
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.111
_diffrn_reflns_theta_max         30.251
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6753
_reflns_number_gt                4969
_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)+(0.0220P)²+8.7000P] 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         6753
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0276
_refine_ls_wR_factor_ref         0.0633
_refine_ls_wR_factor_gt          0.0536
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 0.16135(2) 0.73793(2) 0.34739(2) 0.02896(5) Uani 1 1 d . . . . .
Cl1 Cl 0.17560(6) 0.61951(6) 0.24376(6) 0.0480(2) Uani 1 1 d . . . . .
Cl2 Cl 0.18221(8) 0.86017(6) 0.44868(7) 0.0595(3) Uani 1 1 d . . . . .
Cl3 Cl 0.05263(7) 0.82737(6) 0.27050(6) 0.0488(2) Uani 1 1 d . . . . .
Cl4 Cl 0.05592(6) 0.64759(6) 0.42588(6) 0.0499(2) Uani 1 1 d . . . . .
O1 O 0.28096(15) 0.78343(16) 0.27829(14) 0.0393(6) Uani 1 1 d . . . . .
O2 O 0.27298(15) 0.68270(16) 0.42044(14) 0.0379(6) Uani 1 1 d . . . . .
N1 N 0.33576(17) 0.82395(18) 0.31988(17) 0.0321(6) Uani 1 1 d . . . . .
N2 N 0.33363(17) 0.64648(17) 0.38302(17) 0.0315(6) Uani 1 1 d . . . . .
C1 C 0.3362(2) 0.9060(2) 0.3187(3) 0.0429(9) Uani 1 1 d . . . . .
H1 H 0.298607 0.933745 0.288435 0.051 Uiso 1 1 calc R U . . .
C2 C 0.3912(3) 0.9486(2) 0.3614(2) 0.0473(10) Uani 1 1 d . . . . .
H2 H 0.391476 1.005268 0.359888 0.057 Uiso 1 1 calc R U . . .
C3 C 0.4457(3) 0.9080(2) 0.4064(3) 0.0493(10) Uani 1 1 d . . . . .
H3 H 0.482143 0.936760 0.437169 0.059 Uiso 1 1 calc R U . . .
C4 C 0.4466(2) 0.8241(2) 0.4060(2) 0.0388(8) Uani 1 1 d . . . . .
H4 H 0.484715 0.795969 0.435396 0.047 Uiso 1 1 calc R U . . .
C5 C 0.3912(2) 0.7819(2) 0.3623(2) 0.0310(7) Uani 1 1 d . . . . .
C6 C 0.3944(2) 0.6921(2) 0.3530(2) 0.0333(7) Uani 1 1 d . . . . .
C7 C 0.4595(2) 0.6542(2) 0.3190(3) 0.0517(11) Uani 1 1 d . . . . .
H7 H 0.502119 0.685289 0.299426 0.062 Uiso 1 1 calc R U . . .
C8 C 0.4624(3) 0.5705(3) 0.3135(3) 0.0619(13) Uani 1 1 d . . . . .
H8 H 0.506442 0.544692 0.290277 0.074 Uiso 1 1 calc R U . . .
C9 C 0.3990(3) 0.5260(2) 0.3431(3) 0.0522(11) Uani 1 1 d . . . . .
H9 H 0.399274 0.469481 0.339482 0.063 Uiso 1 1 calc R U . . .
C10 C 0.3356(2) 0.5649(2) 0.3779(2) 0.0419(9) Uani 1 1 d . . . . .
H10 H 0.292983 0.534403 0.398432 0.050 Uiso 1 1 calc R U . . .
N3 N 0.3358(2) 0.6737(3) 0.6018(2) 0.0546(10) Uani 1 1 d . . . . .
N4 N 0.2631(2) 0.5670(2) 0.5838(2) 0.0565(10) Uani 1 1 d . . . . .
C11 C 0.3875(3) 0.6082(4) 0.5956(3) 0.0755(16) Uani 1 1 d . . . . .
H11 H 0.444071 0.610221 0.598374 0.091 Uiso 1 1 calc R U . . .
C12 C 0.3431(3) 0.5416(4) 0.5851(3) 0.0745(16) Uani 1 1 d . . . . .
H12 H 0.362058 0.488527 0.579663 0.089 Uiso 1 1 calc R U . . .
C13 C 0.2601(3) 0.6477(3) 0.5948(2) 0.0454(10) Uani 1 1 d . . . . .
C14 C 0.3591(4) 0.7591(3) 0.6106(4) 0.0825(18) Uani 1 1 d . . . . .
H14A H 0.340086 0.789608 0.566974 0.124 Uiso 1 1 calc R U . . .
H14B H 0.417376 0.763158 0.613782 0.124 Uiso 1 1 calc R U . . .
H14C H 0.335133 0.780661 0.656650 0.124 Uiso 1 1 calc R U . . .
C15 C 0.1865(3) 0.6983(3) 0.5972(3) 0.0564(11) Uani 1 1 d . . . . .
H15A H 0.152569 0.685601 0.553799 0.085 Uiso 1 1 calc R U . . .
H15B H 0.201630 0.754748 0.595386 0.085 Uiso 1 1 calc R U . . .
H15C H 0.157158 0.687567 0.643869 0.085 Uiso 1 1 calc R U . . .
C16 C 0.1922(3) 0.5126(3) 0.5673(3) 0.0704(14) Uani 1 1 d . . . . .
H16A H 0.153860 0.540674 0.534169 0.084 Uiso 1 1 calc R U . . .
H16B H 0.210986 0.464170 0.540638 0.084 Uiso 1 1 calc R U . . .
C17 C 0.1516(4) 0.4891(4) 0.6390(4) 0.0794(17) Uani 1 1 d . . . . .
H17A H 0.106042 0.454408 0.627455 0.119 Uiso 1 1 calc R U . . .
H17B H 0.132736 0.537006 0.665130 0.119 Uiso 1 1 calc R U . . .
H17C H 0.189357 0.460320 0.671290 0.119 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 2.406(3) . ?
Bi1 O1 2.419(3) . ?
Bi1 Cl4 2.6551(10) . ?
Bi1 Cl1 2.6599(10) . ?
Bi1 Cl3 2.6683(10) . ?
Bi1 Cl2 2.6908(11) . ?
O1 N1 1.331(4) . ?
O2 N2 1.329(4) . ?
N1 C1 1.346(5) . ?
N1 C5 1.358(4) . ?
N2 C10 1.343(5) . ?
N2 C6 1.351(4) . ?
C1 C2 1.362(6) . ?
C2 C3 1.363(6) . ?
C3 C4 1.377(6) . ?
C4 C5 1.372(5) . ?
C5 C6 1.483(5) . ?
C6 C7 1.370(5) . ?
C7 C8 1.378(6) . ?
C8 C9 1.371(6) . ?
C9 C10 1.361(6) . ?
N3 C13 1.319(5) . ?
N3 C11 1.373(7) . ?
N3 C14 1.461(6) . ?
N4 C13 1.339(6) . ?
N4 C12 1.376(6) . ?
N4 C16 1.493(6) . ?
C11 C12 1.326(8) . ?
C13 C15 1.465(6) . ?
C16 C17 1.464(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
O2 Bi1 O1 76.17(8) . . ?
O2 Bi1 Cl4 90.81(6) . . ?
O1 Bi1 Cl4 162.92(7) . . ?
O2 Bi1 Cl1 90.88(7) . . ?
O1 Bi1 Cl1 79.51(6) . . ?
Cl4 Bi1 Cl1 89.85(3) . . ?
O2 Bi1 Cl3 168.61(7) . . ?
O1 Bi1 Cl3 97.10(7) . . ?
Cl4 Bi1 Cl3 97.42(3) . . ?
Cl1 Bi1 Cl3 96.98(3) . . ?
O2 Bi1 Cl2 80.72(7) . . ?
O1 Bi1 Cl2 89.52(7) . . ?
Cl4 Bi1 Cl2 99.37(4) . . ?
Cl1 Bi1 Cl2 167.55(4) . . ?
Cl3 Bi1 Cl2 90.15(3) . . ?
N1 O1 Bi1 115.61(19) . . ?
N2 O2 Bi1 118.7(2) . . ?
O1 N1 C1 119.6(3) . . ?
O1 N1 C5 119.5(3) . . ?
C1 N1 C5 120.8(3) . . ?
O2 N2 C10 119.8(3) . . ?
O2 N2 C6 119.5(3) . . ?
C10 N2 C6 120.7(3) . . ?
N1 C1 C2 120.6(4) . . ?
C1 C2 C3 119.8(4) . . ?
C2 C3 C4 119.5(4) . . ?
C5 C4 C3 120.0(4) . . ?
N1 C5 C4 119.2(3) . . ?
N1 C5 C6 117.9(3) . . ?
C4 C5 C6 122.6(3) . . ?
N2 C6 C7 119.3(3) . . ?
N2 C6 C5 118.9(3) . . ?
C7 C6 C5 121.7(3) . . ?
C6 C7 C8 120.6(4) . . ?
C9 C8 C7 118.6(4) . . ?
C10 C9 C8 119.8(4) . . ?
N2 C10 C9 121.0(4) . . ?
C13 N3 C11 108.8(4) . . ?
C13 N3 C14 124.5(5) . . ?
C11 N3 C14 126.7(5) . . ?
C13 N4 C12 109.4(4) . . ?
C13 N4 C16 126.1(4) . . ?
C12 N4 C16 124.3(4) . . ?
C12 C11 N3 108.4(5) . . ?
C11 C12 N4 106.0(5) . . ?
N3 C13 N4 107.3(4) . . ?
N3 C13 C15 126.2(4) . . ?
N4 C13 C15 126.5(4) . . ?
C17 C16 N4 110.4(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
Bi1 O1 N1 C1 -97.8(3) . . . . ?
Bi1 O1 N1 C5 83.0(3) . . . . ?
Bi1 O2 N2 C10 -99.1(3) . . . . ?
Bi1 O2 N2 C6 83.4(3) . . . . ?
O1 N1 C1 C2 179.3(3) . . . . ?
C5 N1 C1 C2 -1.5(6) . . . . ?
N1 C1 C2 C3 -0.7(6) . . . . ?
C1 C2 C3 C4 2.4(6) . . . . ?
C2 C3 C4 C5 -1.9(6) . . . . ?
O1 N1 C5 C4 -178.9(3) . . . . ?
C1 N1 C5 C4 1.9(5) . . . . ?
O1 N1 C5 C6 7.1(5) . . . . ?
C1 N1 C5 C6 -172.1(3) . . . . ?
C3 C4 C5 N1 -0.2(6) . . . . ?
C3 C4 C5 C6 173.5(4) . . . . ?
O2 N2 C6 C7 175.6(4) . . . . ?
C10 N2 C6 C7 -1.9(6) . . . . ?
O2 N2 C6 C5 -0.4(5) . . . . ?
C10 N2 C6 C5 -177.9(3) . . . . ?
N1 C5 C6 N2 -72.8(4) . . . . ?
C4 C5 C6 N2 113.4(4) . . . . ?
N1 C5 C6 C7 111.3(4) . . . . ?
C4 C5 C6 C7 -62.5(5) . . . . ?
N2 C6 C7 C8 1.7(7) . . . . ?
C5 C6 C7 C8 177.6(4) . . . . ?
C6 C7 C8 C9 -0.3(8) . . . . ?
C7 C8 C9 C10 -0.9(8) . . . . ?
O2 N2 C10 C9 -176.8(4) . . . . ?
C6 N2 C10 C9 0.7(6) . . . . ?
C8 C9 C10 N2 0.7(7) . . . . ?
C13 N3 C11 C12 -0.3(6) . . . . ?
C14 N3 C11 C12 -177.2(5) . . . . ?
N3 C11 C12 N4 0.8(7) . . . . ?
C13 N4 C12 C11 -1.1(6) . . . . ?
C16 N4 C12 C11 175.2(5) . . . . ?
C11 N3 C13 N4 -0.4(5) . . . . ?
C14 N3 C13 N4 176.6(4) . . . . ?
C11 N3 C13 C15 -179.3(4) . . . . ?
C14 N3 C13 C15 -2.3(7) . . . . ?
C12 N4 C13 N3 0.9(5) . . . . ?
C16 N4 C13 N3 -175.3(4) . . . . ?
C12 N4 C13 C15 179.8(5) . . . . ?
C16 N4 C13 C15 3.6(7) . . . . ?
C13 N4 C16 C17 -83.6(6) . . . . ?
C12 N4 C16 C17 100.7(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
_geom_hbond_publ_flag
C2 H2 Cl1 0.93 2.97 3.639(4) 130.5 8_665 yes
C2 H2 Cl4 0.93 2.74 3.559(4) 147.3 8_665 yes
C4 H4 Cl4 0.93 2.83 3.460(4) 125.6 4_566 yes
C7 H7 Cl3 0.93 2.76 3.582(4) 148.3 6_656 yes
C9 H9 Cl2 0.93 2.93 3.542(4) 124.3 8_655 yes
C9 H9 Cl3 0.93 2.74 3.585(4) 151.8 8_655 yes
C14 H14B Cl4 0.96 2.79 3.629(6) 146.4 4_566 yes
C14 H14C O1 0.96 2.52 3.260(7) 133.6 7_576 yes
C15 H15A Cl4 0.96 2.80 3.761(5) 179.0 . yes
C15 H15C Cl3 0.96 2.80 3.752(5) 171.0 7_576 yes
C16 H16B Cl2 0.97 2.92 3.840(6) 158.4 8_655 yes
C17 H17C Cl1 0.96 2.87 3.811(6) 168.7 2_565 yes

_refine_diff_density_max         1.053
_refine_diff_density_min         -1.245
_refine_diff_density_rms         0.130

