# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 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 2092480'
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             
;
2021-06-26 deposited with the CCDC.	2021-08-09 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            'C18 H21 Bi Br4 N4 O2'
_chemical_formula_weight         854.01

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      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                   15.1759(16)
_cell_length_b                   9.7830(12)
_cell_length_c                   16.7444(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2486.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    11462
_cell_measurement_theta_min      4.1630
_cell_measurement_theta_max      27.7910

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.282
_exptl_crystal_F_000             1584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    13.542
_shelx_estimated_absorpt_T_min   0.173
_shelx_estimated_absorpt_T_max   0.194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.51014
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45407
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_av_R_equivalents  0.1086
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.398
_diffrn_reflns_theta_max         28.428
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5632
_reflns_number_gt                4406
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_max     0.862
_reflns_Friedel_fraction_full    0.994

_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)+(0.0469P)²+3.9976P] 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   -0.035(14)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5632
_refine_ls_number_parameters     265
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1057
_refine_ls_wR_factor_gt          0.0915
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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 0.66171(3) 0.26772(4) 0.37533(4) 0.03492(15) Uani 1 1 d . . . . .
Br1 Br 0.66964(10) 0.07636(16) 0.24772(9) 0.0490(4) Uani 1 1 d . . . . .
Br2 Br 0.67955(11) 0.44196(16) 0.50860(9) 0.0503(4) Uani 1 1 d . . . . .
Br3 Br 0.53459(10) 0.10261(15) 0.45629(9) 0.0485(4) Uani 1 1 d . . . . .
Br4 Br 0.56845(12) 0.46401(18) 0.28719(10) 0.0603(4) Uani 1 1 d . . . . .
O1 O 0.7825(6) 0.1281(9) 0.4272(6) 0.042(2) Uani 1 1 d . . . . .
O2 O 0.7963(6) 0.3714(9) 0.3284(6) 0.041(2) Uani 1 1 d . . . . .
N1 N 0.8513(7) 0.1884(12) 0.4604(7) 0.034(2) Uani 1 1 d . . . . .
N2 N 0.8511(8) 0.2891(12) 0.2878(7) 0.039(3) Uani 1 1 d . . . . .
C1 C 0.8563(11) 0.1974(18) 0.5403(10) 0.052(4) Uani 1 1 d . . . . .
H1 H 0.809222 0.166889 0.571086 0.062 Uiso 1 1 calc R U . . .
C2 C 0.9287(13) 0.2503(16) 0.5773(11) 0.055(5) Uani 1 1 d . . . . .
H2 H 0.931171 0.256108 0.632700 0.066 Uiso 1 1 calc R U . . .
C3 C 0.9975(10) 0.2945(16) 0.5317(9) 0.048(4) Uani 1 1 d . . . . .
H3 H 1.047096 0.331269 0.556183 0.058 Uiso 1 1 calc R U . . .
C4 C 0.9942(10) 0.2852(15) 0.4499(9) 0.046(4) Uani 1 1 d . . . . .
H4 H 1.041553 0.314825 0.419163 0.055 Uiso 1 1 calc R U . . .
C5 C 0.9195(11) 0.2312(14) 0.4131(10) 0.038(4) Uani 1 1 d . . . . .
C6 C 0.9112(10) 0.2165(14) 0.3257(9) 0.035(3) Uani 1 1 d . . . . .
C7 C 0.9673(10) 0.1305(15) 0.2823(9) 0.047(3) Uani 1 1 d . . . . .
H7 H 1.009270 0.078017 0.308783 0.056 Uiso 1 1 calc R U . . .
C8 C 0.9604(12) 0.124(2) 0.2016(10) 0.064(5) Uani 1 1 d . . . . .
H8 H 0.996278 0.064846 0.172614 0.077 Uiso 1 1 calc R U . . .
C9 C 0.8997(12) 0.2052(18) 0.1631(10) 0.054(4) Uani 1 1 d . . . . .
H9 H 0.896054 0.205253 0.107627 0.064 Uiso 1 1 calc R U . . .
C10 C 0.8453(11) 0.2854(18) 0.2075(10) 0.051(4) Uani 1 1 d . . . . .
H10 H 0.803196 0.338875 0.181932 0.061 Uiso 1 1 calc R U . . .
N3 N 0.3132(12) 0.2602(14) 0.5587(11) 0.063(4) Uani 1 1 d . . . . .
N4 N 0.2676(11) 0.2330(13) 0.4416(10) 0.060(4) Uani 1 1 d . . . . .
C11 C 0.2481(15) 0.167(2) 0.5640(15) 0.081(6) Uani 1 1 d . . . . .
H11 H 0.227066 0.124587 0.610026 0.097 Uiso 1 1 calc R U . . .
C12 C 0.2204(13) 0.1471(18) 0.4898(16) 0.082(7) Uani 1 1 d . . . . .
H12 H 0.176928 0.086169 0.473582 0.098 Uiso 1 1 calc R U . . .
C13 C 0.3293(11) 0.2999(17) 0.4853(11) 0.051(4) Uani 1 1 d . . . . .
C14 C 0.359(2) 0.320(3) 0.6276(14) 0.119(10) Uani 1 1 d . . . . .
H14A H 0.331749 0.289185 0.676037 0.179 Uiso 1 1 calc R U . . .
H14B H 0.356052 0.417771 0.624694 0.179 Uiso 1 1 calc R U . . .
H14C H 0.419760 0.291694 0.627043 0.179 Uiso 1 1 calc R U . . .
C15 C 0.3902(11) 0.4023(16) 0.4574(13) 0.065(5) Uani 1 1 d . . . . .
H15A H 0.398575 0.469975 0.498168 0.098 Uiso 1 1 calc R U . . .
H15B H 0.366851 0.445026 0.410269 0.098 Uiso 1 1 calc R U . . .
H15C H 0.445631 0.360115 0.445002 0.098 Uiso 1 1 calc R U . . .
C16 C 0.2582(17) 0.252(2) 0.3528(15) 0.093(10) Uani 1 1 d . . . . .
H16A H 0.202857 0.211870 0.335980 0.111 Uiso 1 1 calc R U . . .
H16B H 0.255143 0.349400 0.341626 0.111 Uiso 1 1 calc R U . . .
C17 C 0.3280(15) 0.194(3) 0.3059(15) 0.086(7) Uani 1 1 d . . . . .
H17 H 0.343767 0.103773 0.315759 0.103 Uiso 1 1 calc R U . . .
C18 C 0.371(2) 0.261(3) 0.249(2) 0.132(13) Uani 1 1 d . . . . .
H18A H 0.357077 0.351847 0.237921 0.158 Uiso 1 1 calc R U . . .
H18B H 0.416022 0.218105 0.220757 0.158 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 2.413(10) . ?
Bi1 O1 2.445(10) . ?
Bi1 Br4 2.8050(16) . ?
Bi1 Br2 2.8211(17) . ?
Bi1 Br1 2.8434(16) . ?
Bi1 Br3 2.8581(16) . ?
O1 N1 1.322(14) . ?
O2 N2 1.342(15) . ?
N1 C1 1.34(2) . ?
N1 C5 1.368(19) . ?
N2 C6 1.319(18) . ?
N2 C10 1.35(2) . ?
C1 C2 1.36(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.36(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.37(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.39(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.476(18) . ?
C6 C7 1.40(2) . ?
C7 C8 1.36(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.38(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.36(2) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
N3 C13 1.31(2) . ?
N3 C11 1.35(3) . ?
N3 C14 1.47(3) . ?
N4 C13 1.36(2) . ?
N4 C12 1.37(2) . ?
N4 C16 1.50(3) . ?
C11 C12 1.32(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C15 1.44(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.44(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.33(4) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9300 . ?
C18 H18B 0.9300 . ?

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 73.5(3) . . ?
O2 Bi1 Br4 88.2(2) . . ?
O1 Bi1 Br4 161.3(2) . . ?
O2 Bi1 Br2 85.6(2) . . ?
O1 Bi1 Br2 89.1(2) . . ?
Br4 Bi1 Br2 92.92(5) . . ?
O2 Bi1 Br1 89.8(2) . . ?
O1 Bi1 Br1 82.4(2) . . ?
Br4 Bi1 Br1 94.40(5) . . ?
Br2 Bi1 Br1 171.18(5) . . ?
O2 Bi1 Br3 164.5(2) . . ?
O1 Bi1 Br3 91.3(2) . . ?
Br4 Bi1 Br3 107.21(6) . . ?
Br2 Bi1 Br3 91.78(5) . . ?
Br1 Bi1 Br3 90.74(5) . . ?
N1 O1 Bi1 119.5(7) . . ?
N2 O2 Bi1 115.9(7) . . ?
O1 N1 C1 119.5(12) . . ?
O1 N1 C5 119.3(12) . . ?
C1 N1 C5 120.9(13) . . ?
C6 N2 O2 120.5(12) . . ?
C6 N2 C10 120.8(13) . . ?
O2 N2 C10 118.7(12) . . ?
N1 C1 C2 121.5(16) . . ?
N1 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C3 C2 C1 118.8(17) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 120.7(16) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 119.6(15) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 118.4(14) . . ?
N1 C5 C6 118.7(16) . . ?
C4 C5 C6 122.9(16) . . ?
N2 C6 C7 119.6(14) . . ?
N2 C6 C5 118.9(15) . . ?
C7 C6 C5 121.5(14) . . ?
C8 C7 C6 119.9(15) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 119.4(17) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 118.9(16) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
N2 C10 C9 121.4(15) . . ?
N2 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C13 N3 C11 113.5(18) . . ?
C13 N3 C14 122(2) . . ?
C11 N3 C14 124(2) . . ?
C13 N4 C12 109.8(17) . . ?
C13 N4 C16 122.6(18) . . ?
C12 N4 C16 127.6(19) . . ?
C12 C11 N3 105.6(19) . . ?
C12 C11 H11 127.2 . . ?
N3 C11 H11 127.2 . . ?
C11 C12 N4 107.4(17) . . ?
C11 C12 H12 126.3 . . ?
N4 C12 H12 126.3 . . ?
N3 C13 N4 103.6(16) . . ?
N3 C13 C15 129.0(18) . . ?
N4 C13 C15 127.0(17) . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 N4 115(2) . . ?
C17 C16 H16A 108.5 . . ?
N4 C16 H16A 108.5 . . ?
C17 C16 H16B 108.5 . . ?
N4 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C18 C17 C16 124(3) . . ?
C18 C17 H17 118.0 . . ?
C16 C17 H17 118.0 . . ?
C17 C18 H18A 120.0 . . ?
C17 C18 H18B 120.0 . . ?
H18A C18 H18B 120.0 . . ?

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 98.8(13) . . . . ?
Bi1 O1 N1 C5 -86.2(13) . . . . ?
Bi1 O2 N2 C6 -88.5(14) . . . . ?
Bi1 O2 N2 C10 93.5(13) . . . . ?
O1 N1 C1 C2 175.4(14) . . . . ?
C5 N1 C1 C2 1(2) . . . . ?
N1 C1 C2 C3 0(3) . . . . ?
C1 C2 C3 C4 0(2) . . . . ?
C2 C3 C4 C5 1(2) . . . . ?
O1 N1 C5 C4 -175.3(12) . . . . ?
C1 N1 C5 C4 0(2) . . . . ?
O1 N1 C5 C6 4(2) . . . . ?
C1 N1 C5 C6 178.8(14) . . . . ?
C3 C4 C5 N1 0(2) . . . . ?
C3 C4 C5 C6 -179.3(14) . . . . ?
O2 N2 C6 C7 179.6(12) . . . . ?
C10 N2 C6 C7 -3(2) . . . . ?
O2 N2 C6 C5 -2(2) . . . . ?
C10 N2 C6 C5 175.6(15) . . . . ?
N1 C5 C6 N2 66.1(19) . . . . ?
C4 C5 C6 N2 -114.8(18) . . . . ?
N1 C5 C6 C7 -115.8(17) . . . . ?
C4 C5 C6 C7 63(2) . . . . ?
N2 C6 C7 C8 1(2) . . . . ?
C5 C6 C7 C8 -177.2(17) . . . . ?
C6 C7 C8 C9 2(3) . . . . ?
C7 C8 C9 C10 -3(3) . . . . ?
C6 N2 C10 C9 1(2) . . . . ?
O2 N2 C10 C9 179.2(16) . . . . ?
C8 C9 C10 N2 2(3) . . . . ?
C13 N3 C11 C12 -1(2) . . . . ?
C14 N3 C11 C12 176(2) . . . . ?
N3 C11 C12 N4 -2(2) . . . . ?
C13 N4 C12 C11 4(2) . . . . ?
C16 N4 C12 C11 -177.7(18) . . . . ?
C11 N3 C13 N4 3(2) . . . . ?
C14 N3 C13 N4 -173.3(18) . . . . ?
C11 N3 C13 C15 176.5(17) . . . . ?
C14 N3 C13 C15 0(3) . . . . ?
C12 N4 C13 N3 -4.4(19) . . . . ?
C16 N4 C13 N3 177.3(16) . . . . ?
C12 N4 C13 C15 -177.8(17) . . . . ?
C16 N4 C13 C15 4(3) . . . . ?
C13 N4 C16 C17 71(2) . . . . ?
C12 N4 C16 C17 -107(3) . . . . ?
N4 C16 C17 C18 -130(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 Br1 0.93 3.10 3.691(16) 122.7 4_655 yes
C2 H2 Br1 0.93 3.02 3.642(18) 125.4 4_655 yes
C4 H4 Br4 0.93 3.12 3.835(15) 135.1 3_565 yes
C7 H7 Br1 0.93 3.04 3.723(14) 131.4 3 yes
C7 H7 Br3 0.93 3.06 3.838(15) 142.1 3 yes
C9 H9 Br2 0.93 3.07 3.675(16) 124.2 4_654 yes
C9 H9 Br3 0.93 2.92 3.740(16) 147.5 4_654 yes
C10 H10 Br2 0.93 3.08 3.685(17) 124.0 4_654 yes
C12 H12 Br3 0.93 2.86 3.773(18) 168.7 3_455 yes
C15 H15B O2 0.96 2.50 3.41(2) 157.1 3_465 yes
C15 H15C Br3 0.96 2.86 3.661(17) 141.0 . yes

_refine_diff_density_max         2.268
_refine_diff_density_min         -1.510
_refine_diff_density_rms         0.183


_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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 2092481'
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             
;
2021-06-26 deposited with the CCDC.	2021-08-09 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            'C18 H21 Bi Cl4 N4 O2'
_chemical_formula_weight         676.17

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                   14.9967(16)
_cell_length_b                   9.4857(12)
_cell_length_c                   16.3613(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2327.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    4204
_cell_measurement_theta_min      3.5350
_cell_measurement_theta_max      28.1360

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.930
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    8.056
_shelx_estimated_absorpt_T_min   0.211
_shelx_estimated_absorpt_T_max   0.296
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.16068
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13952
_diffrn_reflns_av_unetI/netI     0.0758
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.147
_diffrn_reflns_theta_max         29.730
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.902
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.831
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             5504
_reflns_number_gt                4056
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.782
_reflns_Friedel_fraction_max     0.755
_reflns_Friedel_fraction_full    0.952

_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)+(0.0358P)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   -0.031(11)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5504
_refine_ls_number_parameters     265
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.0890
_refine_ls_wR_factor_gt          0.0716
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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 0.66330(2) 0.27040(4) 0.37499(6) 0.03100(12) Uani 1 1 d . . . . .
Cl1 Cl 0.6715(2) 0.0863(4) 0.24980(18) 0.0458(7) Uani 1 1 d . . . . .
Cl2 Cl 0.6822(2) 0.4367(4) 0.50644(18) 0.0470(8) Uani 1 1 d . . . . .
Cl3 Cl 0.54094(19) 0.1086(3) 0.45001(18) 0.0447(7) Uani 1 1 d . . . . .
Cl4 Cl 0.5704(2) 0.4609(4) 0.2939(2) 0.0561(8) Uani 1 1 d . . . . .
O1 O 0.7859(5) 0.1269(8) 0.4263(4) 0.0337(17) Uani 1 1 d . . . . .
O2 O 0.8005(5) 0.3782(9) 0.3258(4) 0.0384(19) Uani 1 1 d . . . . .
N1 N 0.8552(6) 0.1872(11) 0.4622(5) 0.031(2) Uani 1 1 d . . . . .
N2 N 0.8555(6) 0.2930(11) 0.2847(6) 0.035(2) Uani 1 1 d . . . . .
C1 C 0.8585(8) 0.1965(15) 0.5439(7) 0.039(3) Uani 1 1 d . . . . .
H1 H 0.810503 0.164878 0.574900 0.046 Uiso 1 1 calc R U . . .
C2 C 0.9312(10) 0.2516(14) 0.5818(9) 0.046(4) Uani 1 1 d . . . . .
H2 H 0.932890 0.256453 0.638542 0.055 Uiso 1 1 calc R U . . .
C3 C 1.0032(8) 0.3009(14) 0.5364(6) 0.044(3) Uani 1 1 d . . . . .
H3 H 1.053061 0.339537 0.561728 0.053 Uiso 1 1 calc R U . . .
C4 C 0.9980(8) 0.2904(12) 0.4522(7) 0.039(3) Uani 1 1 d . . . . .
H4 H 1.045221 0.322584 0.420422 0.047 Uiso 1 1 calc R U . . .
C5 C 0.9249(11) 0.2337(14) 0.4150(9) 0.030(4) Uani 1 1 d . . . . .
C6 C 0.9164(11) 0.2153(14) 0.3247(9) 0.030(3) Uani 1 1 d . . . . .
C7 C 0.9730(8) 0.1280(14) 0.2828(7) 0.044(3) Uani 1 1 d . . . . .
H7 H 1.015350 0.075157 0.310736 0.053 Uiso 1 1 calc R U . . .
C8 C 0.9667(9) 0.1186(15) 0.1976(7) 0.054(4) Uani 1 1 d . . . . .
H8 H 1.004370 0.059360 0.168405 0.065 Uiso 1 1 calc R U . . .
C9 C 0.9055(11) 0.1964(18) 0.1592(10) 0.056(4) Uani 1 1 d . . . . .
H9 H 0.900634 0.190617 0.102605 0.067 Uiso 1 1 calc R U . . .
C10 C 0.8491(9) 0.2855(16) 0.2020(8) 0.046(4) Uani 1 1 d . . . . .
H10 H 0.807244 0.339792 0.174314 0.055 Uiso 1 1 calc R U . . .
N3 N 0.3076(9) 0.2578(12) 0.5763(7) 0.053(3) Uani 1 1 d . . . . .
N4 N 0.2646(7) 0.2234(11) 0.4535(7) 0.044(3) Uani 1 1 d . . . . .
C11 C 0.2403(10) 0.1610(17) 0.5803(9) 0.061(4) Uani 1 1 d . . . . .
H11 H 0.217115 0.119223 0.627096 0.073 Uiso 1 1 calc R U . . .
C12 C 0.2150(9) 0.1390(14) 0.5044(9) 0.055(3) Uani 1 1 d . . . . .
H12 H 0.170824 0.076476 0.487825 0.066 Uiso 1 1 calc R U . . .
C13 C 0.3217(9) 0.2965(15) 0.4991(9) 0.045(3) Uani 1 1 d . . . . .
C14 C 0.3489(12) 0.326(2) 0.6485(10) 0.095(6) Uani 1 1 d . . . . .
H14A H 0.346145 0.263482 0.694406 0.143 Uiso 1 1 calc R U . . .
H14B H 0.317350 0.411574 0.661055 0.143 Uiso 1 1 calc R U . . .
H14C H 0.410115 0.348085 0.636641 0.143 Uiso 1 1 calc R U . . .
C15 C 0.3865(8) 0.3994(14) 0.4706(8) 0.055(4) Uani 1 1 d . . . . .
H15A H 0.375281 0.488573 0.496313 0.083 Uiso 1 1 calc R U . . .
H15B H 0.381542 0.409478 0.412379 0.083 Uiso 1 1 calc R U . . .
H15C H 0.445527 0.367972 0.484225 0.083 Uiso 1 1 calc R U . . .
C16 C 0.2548(9) 0.2394(14) 0.3638(14) 0.061(4) Uani 1 1 d . . . . .
H16A H 0.200888 0.191531 0.346413 0.073 Uiso 1 1 calc R U . . .
H16B H 0.248175 0.338655 0.350895 0.073 Uiso 1 1 calc R U . . .
C17 C 0.3298(10) 0.183(2) 0.3185(9) 0.065(4) Uani 1 1 d . . . . .
H17 H 0.347451 0.090716 0.328053 0.077 Uiso 1 1 calc R U . . .
C18 C 0.3744(15) 0.2592(19) 0.2636(11) 0.082(6) Uani 1 1 d . . . . .
H18A H 0.357741 0.351904 0.253246 0.098 Uiso 1 1 calc R U . . .
H18B H 0.422249 0.219539 0.235709 0.098 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 O2 2.434(8) . ?
Bi1 O1 2.437(7) . ?
Bi1 Cl4 2.639(3) . ?
Bi1 Cl2 2.682(3) . ?
Bi1 Cl3 2.689(3) . ?
Bi1 Cl1 2.695(3) . ?
O1 N1 1.324(11) . ?
O2 N2 1.337(12) . ?
N1 C1 1.340(15) . ?
N1 C5 1.371(17) . ?
N2 C6 1.343(18) . ?
N2 C10 1.359(15) . ?
C1 C2 1.360(19) . ?
C1 H1 0.9300 . ?
C2 C3 1.391(19) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(15) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.493(14) . ?
C6 C7 1.370(18) . ?
C7 C8 1.399(16) . ?
C7 H7 0.9300 . ?
C8 C9 1.33(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.39(2) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
N3 C13 1.332(18) . ?
N3 C11 1.366(19) . ?
N3 C14 1.484(19) . ?
N4 C13 1.331(17) . ?
N4 C12 1.373(16) . ?
N4 C16 1.48(3) . ?
C11 C12 1.315(18) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C15 1.455(19) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.45(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.33(2) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9300 . ?
C18 H18B 0.9300 . ?

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 73.2(2) . . ?
O2 Bi1 Cl4 89.6(2) . . ?
O1 Bi1 Cl4 162.51(19) . . ?
O2 Bi1 Cl2 85.91(19) . . ?
O1 Bi1 Cl2 88.44(19) . . ?
Cl4 Bi1 Cl2 93.22(10) . . ?
O2 Bi1 Cl3 165.34(19) . . ?
O1 Bi1 Cl3 92.22(18) . . ?
Cl4 Bi1 Cl3 105.09(10) . . ?
Cl2 Bi1 Cl3 92.39(10) . . ?
O2 Bi1 Cl1 89.02(19) . . ?
O1 Bi1 Cl1 82.26(18) . . ?
Cl4 Bi1 Cl1 94.91(11) . . ?
Cl2 Bi1 Cl1 170.38(9) . . ?
Cl3 Bi1 Cl1 90.45(9) . . ?
N1 O1 Bi1 120.3(7) . . ?
N2 O2 Bi1 115.7(7) . . ?
O1 N1 C1 119.9(9) . . ?
O1 N1 C5 119.2(10) . . ?
C1 N1 C5 120.8(11) . . ?
O2 N2 C6 120.4(10) . . ?
O2 N2 C10 119.3(10) . . ?
C6 N2 C10 120.3(11) . . ?
N1 C1 C2 120.6(12) . . ?
N1 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C1 C2 C3 120.5(13) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 117.6(12) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C5 C4 C3 121.2(12) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 N1 119.2(13) . . ?
C4 C5 C6 123.8(15) . . ?
N1 C5 C6 117.0(16) . . ?
N2 C6 C7 120.5(13) . . ?
N2 C6 C5 118.4(14) . . ?
C7 C6 C5 120.9(15) . . ?
C6 C7 C8 119.7(12) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 118.8(13) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 121.2(14) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
N2 C10 C9 119.5(13) . . ?
N2 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C13 N3 C11 110.4(12) . . ?
C13 N3 C14 124.6(14) . . ?
C11 N3 C14 124.4(14) . . ?
C13 N4 C12 108.2(11) . . ?
C13 N4 C16 124.4(12) . . ?
C12 N4 C16 127.3(11) . . ?
C12 C11 N3 105.9(13) . . ?
C12 C11 H11 127.0 . . ?
N3 C11 H11 127.0 . . ?
C11 C12 N4 108.9(12) . . ?
C11 C12 H12 125.6 . . ?
N4 C12 H12 125.6 . . ?
N3 C13 N4 106.6(12) . . ?
N3 C13 C15 126.5(13) . . ?
N4 C13 C15 126.9(13) . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 N4 113.1(13) . . ?
C17 C16 H16A 109.0 . . ?
N4 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
N4 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C18 C17 C16 122.4(19) . . ?
C18 C17 H17 118.8 . . ?
C16 C17 H17 118.8 . . ?
C17 C18 H18A 120.0 . . ?
C17 C18 H18B 120.0 . . ?
H18A C18 H18B 120.0 . . ?

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 96.3(11) . . . . ?
Bi1 O1 N1 C5 -86.6(11) . . . . ?
Bi1 O2 N2 C6 -87.3(12) . . . . ?
Bi1 O2 N2 C10 92.6(11) . . . . ?
O1 N1 C1 C2 176.7(12) . . . . ?
C5 N1 C1 C2 0(2) . . . . ?
N1 C1 C2 C3 1(2) . . . . ?
C1 C2 C3 C4 -1(2) . . . . ?
C2 C3 C4 C5 0.0(18) . . . . ?
C3 C4 C5 N1 0.3(19) . . . . ?
C3 C4 C5 C6 -178.0(13) . . . . ?
O1 N1 C5 C4 -177.2(11) . . . . ?
C1 N1 C5 C4 -0.2(19) . . . . ?
O1 N1 C5 C6 1.2(19) . . . . ?
C1 N1 C5 C6 178.3(13) . . . . ?
O2 N2 C6 C7 -179.9(11) . . . . ?
C10 N2 C6 C7 0(2) . . . . ?
O2 N2 C6 C5 -4(2) . . . . ?
C10 N2 C6 C5 176.2(13) . . . . ?
C4 C5 C6 N2 -112.7(18) . . . . ?
N1 C5 C6 N2 68.9(18) . . . . ?
C4 C5 C6 C7 63(2) . . . . ?
N1 C5 C6 C7 -115.2(17) . . . . ?
N2 C6 C7 C8 -1(2) . . . . ?
C5 C6 C7 C8 -176.5(14) . . . . ?
C6 C7 C8 C9 0(2) . . . . ?
C7 C8 C9 C10 0(2) . . . . ?
O2 N2 C10 C9 -179.4(13) . . . . ?
C6 N2 C10 C9 0(2) . . . . ?
C8 C9 C10 N2 -1(3) . . . . ?
C13 N3 C11 C12 1.4(17) . . . . ?
C14 N3 C11 C12 172.5(14) . . . . ?
N3 C11 C12 N4 -1.3(16) . . . . ?
C13 N4 C12 C11 0.9(16) . . . . ?
C16 N4 C12 C11 -176.0(12) . . . . ?
C11 N3 C13 N4 -0.8(16) . . . . ?
C14 N3 C13 N4 -171.9(13) . . . . ?
C11 N3 C13 C15 178.7(13) . . . . ?
C14 N3 C13 C15 8(2) . . . . ?
C12 N4 C13 N3 0.0(15) . . . . ?
C16 N4 C13 N3 177.0(11) . . . . ?
C12 N4 C13 C15 -179.6(13) . . . . ?
C16 N4 C13 C15 -3(2) . . . . ?
C13 N4 C16 C17 71.3(17) . . . . ?
C12 N4 C16 C17 -112.3(16) . . . . ?
N4 C16 C17 C18 -126.6(17) . . . . ?

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 Cl1 0.93 2.97 3.556(13) 122.4 4_655 yes
C2 H2 Cl1 0.93 2.89 3.520(15) 125.9 4_655 yes
C4 H4 Cl4 0.93 2.94 3.668(12) 136.1 3_565 yes
C7 H7 Cl1 0.93 2.97 3.645(12) 130.7 3 yes
C7 H7 Cl3 0.93 2.89 3.683(13) 143.4 3 yes
C9 H9 Cl3 0.93 2.76 3.612(16) 153.2 4_654 yes
C10 H10 Cl2 0.93 2.90 3.538(13) 126.8 4_654 yes
C12 H12 Cl3 0.93 2.69 3.623(14) 176.4 3_455 yes
C15 H15C Cl3 0.96 2.90 3.617(13) 132.3 . yes

_refine_diff_density_max         1.594
_refine_diff_density_min         -1.484
_refine_diff_density_rms         0.175


_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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 2092482'
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             
;
2021-06-26 deposited with the CCDC.	2021-08-09 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 H19 Bi Cl4 N4 O2'
_chemical_formula_weight         662.14

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                   14.6337(9)
_cell_length_b                   9.4088(5)
_cell_length_c                   16.1330(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2221.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    7365
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      28.33

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.980
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   0.202
_exptl_transmission_factor_max   0.430
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    8.439
_shelx_estimated_absorpt_T_min   0.283
_shelx_estimated_absorpt_T_max   0.486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15732
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_av_R_equivalents  0.0392
_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       21
_diffrn_reflns_theta_min         2.165
_diffrn_reflns_theta_max         28.276
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             5089
_reflns_number_gt                4516
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_max     0.843
_reflns_Friedel_fraction_full    0.930

_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)+(0.0090P)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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00176(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.238(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5089
_refine_ls_number_parameters     256
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0249
_refine_ls_wR_factor_ref         0.0509
_refine_ls_wR_factor_gt          0.0483
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.990
_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 0.31350(2) 0.23745(2) 0.62216(9) 0.02933(8) Uani 1 1 d . . . . .
Cl1 Cl 0.30417(14) 0.40129(19) 0.75647(12) 0.0446(4) Uani 1 1 d . . . . .
Cl2 Cl 0.29774(13) 0.0727(2) 0.48715(13) 0.0466(5) Uani 1 1 d . . . . .
Cl3 Cl 0.42154(15) 0.4246(2) 0.54685(14) 0.0548(6) Uani 1 1 d . . . . .
Cl4 Cl 0.42350(13) 0.0525(2) 0.70565(14) 0.0474(5) Uani 1 1 d . . . . .
O1 O 0.1867(3) 0.3770(5) 0.5764(3) 0.0349(11) Uani 1 1 d . . . . .
O2 O 0.1778(3) 0.1166(5) 0.6704(3) 0.0354(11) Uani 1 1 d . . . . .
N1 N 0.1182(4) 0.3118(6) 0.5371(4) 0.0329(12) Uani 1 1 d . . . . .
N2 N 0.1184(4) 0.1957(6) 0.7134(4) 0.0309(12) Uani 1 1 d . . . . .
C1 C 0.1187(6) 0.3064(8) 0.4534(4) 0.0407(17) Uani 1 1 d . . . . .
H1 H 0.168561 0.342069 0.424278 0.049 Uiso 1 1 calc R U . . .
C2 C 0.0456(9) 0.2479(9) 0.4104(10) 0.047(3) Uani 1 1 d . . . . .
H2 H 0.044892 0.245657 0.352736 0.056 Uiso 1 1 calc R U . . .
C3 C -0.0252(5) 0.1941(9) 0.4554(5) 0.0475(19) Uani 1 1 d . . . . .
H3 H -0.074654 0.153523 0.427981 0.057 Uiso 1 1 calc R U . . .
C4 C -0.0249(5) 0.1986(7) 0.5406(5) 0.0383(16) Uani 1 1 d . . . . .
H4 H -0.074158 0.162369 0.570211 0.046 Uiso 1 1 calc R U . . .
C5 C 0.0481(9) 0.2565(7) 0.5818(10) 0.032(3) Uani 1 1 d . . . . .
C6 C 0.0528(9) 0.2684(9) 0.6725(9) 0.028(3) Uani 1 1 d . . . . .
C7 C -0.0098(5) 0.3478(7) 0.7178(5) 0.0384(16) Uani 1 1 d . . . . .
H7 H -0.056534 0.396210 0.690734 0.046 Uiso 1 1 calc R U . . .
C8 C -0.0026(5) 0.3546(8) 0.8029(4) 0.0454(19) Uani 1 1 d . . . . .
H8 H -0.042461 0.410441 0.833764 0.055 Uiso 1 1 calc R U . . .
C9 C 0.0649(8) 0.2771(10) 0.8411(9) 0.044(3) Uani 1 1 d . . . . .
H9 H 0.069494 0.278370 0.898572 0.052 Uiso 1 1 calc R U . . .
C10 C 0.1249(5) 0.1989(9) 0.7963(5) 0.0405(17) Uani 1 1 d . . . . .
H10 H 0.170520 0.147508 0.823002 0.049 Uiso 1 1 calc R U . . .
N3 N 0.6498(5) 0.1988(8) 0.4589(4) 0.0474(17) Uani 1 1 d . . . . .
N4 N 0.7244(5) 0.2337(6) 0.3451(4) 0.0414(14) Uani 1 1 d . . . . .
C11 C 0.7045(6) 0.3140(9) 0.4710(6) 0.054(2) Uani 1 1 d . . . . .
H11 H 0.708731 0.367739 0.519212 0.065 Uiso 1 1 calc R U . . .
C12 C 0.7509(6) 0.3355(8) 0.4008(5) 0.050(2) Uani 1 1 d . . . . .
H12 H 0.793658 0.406921 0.391435 0.060 Uiso 1 1 calc R U . . .
C13 C 0.6641(5) 0.1509(8) 0.3835(5) 0.0439(18) Uani 1 1 d . . . . .
H13 H 0.636246 0.071298 0.360506 0.053 Uiso 1 1 calc R U . . .
C14 C 0.5922(6) 0.1323(9) 0.5217(6) 0.068(3) Uani 1 1 d . . . . .
H14A H 0.564955 0.204516 0.555708 0.102 Uiso 1 1 calc R U . . .
H14B H 0.628696 0.070600 0.555607 0.102 Uiso 1 1 calc R U . . .
H14C H 0.544994 0.078013 0.495114 0.102 Uiso 1 1 calc R U . . .
C15 C 0.7521(6) 0.2234(8) 0.2575(5) 0.050(2) Uani 1 1 d . . . . .
H15A H 0.725548 0.302016 0.226921 0.061 Uiso 1 1 calc R U . . .
H15B H 0.728129 0.135888 0.234253 0.061 Uiso 1 1 calc R U . . .
C16 C 0.8525(7) 0.2258(10) 0.2470(6) 0.052(2) Uani 1 1 d . . . . .
H16 H 0.886125 0.146950 0.263642 0.063 Uiso 1 1 calc R U . . .
C17 C 0.8957(6) 0.3344(9) 0.2153(6) 0.062(2) Uani 1 1 d . . . . .
H17A H 0.863293 0.414252 0.198272 0.075 Uiso 1 1 calc R U . . .
H17B H 0.958969 0.331894 0.209699 0.075 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 2.390(5) . ?
Bi1 O2 2.417(5) . ?
Bi1 Cl3 2.660(2) . ?
Bi1 Cl1 2.663(2) . ?
Bi1 Cl2 2.683(2) . ?
Bi1 Cl4 2.727(2) . ?
O1 N1 1.335(7) . ?
O2 N2 1.339(7) . ?
N1 C1 1.351(9) . ?
N1 C5 1.357(15) . ?
N2 C10 1.341(9) . ?
N2 C6 1.351(14) . ?
C1 C2 1.389(15) . ?
C2 C3 1.363(16) . ?
C3 C4 1.375(10) . ?
C4 C5 1.371(15) . ?
C5 C6 1.470(10) . ?
C6 C7 1.389(14) . ?
C7 C8 1.379(10) . ?
C8 C9 1.373(14) . ?
C9 C10 1.354(15) . ?
N3 C13 1.313(10) . ?
N3 C11 1.361(12) . ?
N3 C14 1.459(11) . ?
N4 C13 1.331(10) . ?
N4 C12 1.370(9) . ?
N4 C15 1.473(11) . ?
C11 C12 1.336(11) . ?
C15 C16 1.479(13) . ?
C16 C17 1.306(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Bi1 O2 73.73(14) . . ?
O1 Bi1 Cl3 87.53(12) . . ?
O2 Bi1 Cl3 161.22(13) . . ?
O1 Bi1 Cl1 83.87(12) . . ?
O2 Bi1 Cl1 88.20(13) . . ?
Cl3 Bi1 Cl1 91.09(6) . . ?
O1 Bi1 Cl2 90.00(13) . . ?
O2 Bi1 Cl2 85.34(12) . . ?
Cl3 Bi1 Cl2 93.59(9) . . ?
Cl1 Bi1 Cl2 172.13(5) . . ?
O1 Bi1 Cl4 164.06(13) . . ?
O2 Bi1 Cl4 91.48(12) . . ?
Cl3 Bi1 Cl4 107.29(6) . . ?
Cl1 Bi1 Cl4 89.88(8) . . ?
Cl2 Bi1 Cl4 94.76(6) . . ?
N1 O1 Bi1 118.5(4) . . ?
N2 O2 Bi1 116.0(4) . . ?
O1 N1 C1 119.2(6) . . ?
O1 N1 C5 119.4(8) . . ?
C1 N1 C5 121.3(9) . . ?
O2 N2 C10 118.9(6) . . ?
O2 N2 C6 119.3(8) . . ?
C10 N2 C6 121.7(8) . . ?
N1 C1 C2 120.7(9) . . ?
C3 C2 C1 117.8(13) . . ?
C2 C3 C4 121.3(9) . . ?
C5 C4 C3 120.0(10) . . ?
N1 C5 C4 118.9(13) . . ?
N1 C5 C6 117.7(14) . . ?
C4 C5 C6 123.3(14) . . ?
N2 C6 C7 119.0(12) . . ?
N2 C6 C5 118.7(12) . . ?
C7 C6 C5 122.3(13) . . ?
C8 C7 C6 119.8(9) . . ?
C9 C8 C7 118.5(9) . . ?
C10 C9 C8 121.0(12) . . ?
N2 C10 C9 119.9(9) . . ?
C13 N3 C11 108.2(7) . . ?
C13 N3 C14 126.0(8) . . ?
C11 N3 C14 125.5(8) . . ?
C13 N4 C12 107.0(7) . . ?
C13 N4 C15 126.2(7) . . ?
C12 N4 C15 126.7(7) . . ?
C12 C11 N3 107.3(7) . . ?
C11 C12 N4 107.8(7) . . ?
N3 C13 N4 109.7(7) . . ?
N4 C15 C16 112.4(7) . . ?
C17 C16 C15 122.6(8) . . ?

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 -93.8(6) . . . . ?
Bi1 O1 N1 C5 88.4(7) . . . . ?
Bi1 O2 N2 C10 -92.9(6) . . . . ?
Bi1 O2 N2 C6 88.1(7) . . . . ?
O1 N1 C1 C2 -175.6(7) . . . . ?
C5 N1 C1 C2 2.2(12) . . . . ?
N1 C1 C2 C3 -1.4(13) . . . . ?
C1 C2 C3 C4 0.7(14) . . . . ?
C2 C3 C4 C5 -0.8(13) . . . . ?
O1 N1 C5 C4 175.5(6) . . . . ?
C1 N1 C5 C4 -2.3(12) . . . . ?
O1 N1 C5 C6 -1.6(13) . . . . ?
C1 N1 C5 C6 -179.4(9) . . . . ?
C3 C4 C5 N1 1.6(12) . . . . ?
C3 C4 C5 C6 178.5(9) . . . . ?
O2 N2 C6 C7 178.6(7) . . . . ?
C10 N2 C6 C7 -0.4(13) . . . . ?
O2 N2 C6 C5 0.8(14) . . . . ?
C10 N2 C6 C5 -178.2(10) . . . . ?
N1 C5 C6 N2 -66.7(11) . . . . ?
C4 C5 C6 N2 116.3(14) . . . . ?
N1 C5 C6 C7 115.6(14) . . . . ?
C4 C5 C6 C7 -61.4(12) . . . . ?
N2 C6 C7 C8 1.9(13) . . . . ?
C5 C6 C7 C8 179.6(10) . . . . ?
C6 C7 C8 C9 -2.6(12) . . . . ?
C7 C8 C9 C10 1.9(14) . . . . ?
O2 N2 C10 C9 -179.4(8) . . . . ?
C6 N2 C10 C9 -0.3(12) . . . . ?
C8 C9 C10 N2 -0.5(15) . . . . ?
C13 N3 C11 C12 0.9(10) . . . . ?
C14 N3 C11 C12 175.4(8) . . . . ?
N3 C11 C12 N4 0.3(10) . . . . ?
C13 N4 C12 C11 -1.4(9) . . . . ?
C15 N4 C12 C11 174.6(7) . . . . ?
C11 N3 C13 N4 -1.8(9) . . . . ?
C14 N3 C13 N4 -176.3(8) . . . . ?
C12 N4 C13 N3 2.0(9) . . . . ?
C15 N4 C13 N3 -174.0(7) . . . . ?
C13 N4 C15 C16 -131.7(8) . . . . ?
C12 N4 C15 C16 53.1(10) . . . . ?
N4 C15 C16 C17 -108.9(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 H1 Cl1 0.93 2.79 3.487(7) 132.3 4_554 yes
C4 H4 Cl4 0.93 2.98 3.639(8) 129.4 3_455 yes
C7 H7 Cl1 0.93 2.98 3.657(7) 130.4 3_465 yes
C7 H7 Cl3 0.93 2.89 3.633(8) 138.2 3_465 yes
C9 H9 Cl3 0.93 2.76 3.603(15) 150.9 4 yes
C10 H10 Cl2 0.93 2.78 3.488(8) 133.8 4 yes
C11 H11 O1 0.93 2.59 3.379(9) 142.5 3_565 yes
C13 H13 Cl4 0.93 2.89 3.679(8) 143.3 2_654 yes
C14 H14A Cl3 0.96 2.95 3.737(9) 139.8 . yes
C14 H14B O2 0.96 2.65 3.578(10) 161.7 3 yes
C15 H15A Cl1 0.97 2.87 3.626(8) 136.0 2_664 yes
C15 H15B Cl4 0.97 2.88 3.746(8) 149.7 2_654 yes

_refine_diff_density_max         0.688
_refine_diff_density_min         -1.006
_refine_diff_density_rms         0.084


_exptl_crystal_preparation       Luminescent
