# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_ht05082
_database_code_depnum_ccdc_archive 'CCDC 2452111'
loop_
_audit_author_name
_audit_author_address
'hunter clinton'
;swust
China
;
_audit_update_record             
;
2025-05-18 deposited with the CCDC.	2025-12-23 downloaded from the CCDC.
;
_audit_creation_date             2025-05-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
# start Validation Reply Form
_vrf_PLAT420_ht05082             
;
PROBLEM: D-H Bond Without Acceptor  O6       --H6B      .     Please Check
RESPONSE: Water molecules that would act as H-bond acceptors are not modeled.
;
# end Validation Reply Form
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H2 Bi F4 O6, H2 O'
_chemical_formula_sum            'C8 H4 Bi F4 O7'
_chemical_formula_weight         497.09
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.3680(4)
_cell_length_b                   11.6173(3)
_cell_length_c                   7.3026(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.5260(10)
_cell_angle_gamma                90
_cell_volume                     1131.95(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4468
_cell_measurement_temperature    305.00
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      3.563
_shelx_estimated_absorpt_T_max   0.651
_shelx_estimated_absorpt_T_min   0.202
_exptl_absorpt_coefficient_mu    15.664
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1019 before and 0.0687 after correction.
The Ratio of minimum to maximum transmission is 0.7405.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.917
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             908
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12253
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         3.300
_diffrn_ambient_temperature      305.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'BrukerD8 Venture'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.6
_diffrn_source_power             0.08
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2232
_reflns_number_total             2524
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.991
_refine_diff_density_min         -0.994
_refine_diff_density_rms         0.210
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2524
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0287
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0429P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0789
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O6(H6A,H6B)
2.b Rotating group:
 O5(H5A,H5B)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.48992(2) 0.41123(2) 0.20358(2) 0.02258(10) Uani 1 1 d . . . . .
F1 F 0.8314(4) 0.4022(3) 0.5785(8) 0.0537(13) Uani 1 1 d . . . . .
F2 F 0.9973(3) 0.5060(5) 0.7218(8) 0.0710(17) Uani 1 1 d . . . . .
F3 F 1.0083(3) 0.7384(5) 0.7394(8) 0.0686(15) Uani 1 1 d . . . . .
F4 F 0.8551(3) 0.8674(4) 0.6135(6) 0.0476(10) Uani 1 1 d . . . . .
O1 O 0.6436(3) 0.5178(4) 0.2798(5) 0.0331(10) Uani 1 1 d . . . . .
O2 O 0.6071(3) 0.4677(3) 0.5611(5) 0.0290(9) Uani 1 1 d . . . . .
O3 O 0.5833(3) 0.7280(4) 0.4845(6) 0.0343(10) Uani 1 1 d . . . . .
O4 O 0.6791(3) 0.8719(4) 0.4089(5) 0.0294(9) Uani 1 1 d . . . . .
O5 O 0.6368(4) 0.2574(4) 0.2105(7) 0.0480(12) Uani 1 1 d . . . . .
H5A H 0.686086 0.285047 0.157082 0.072 Uiso 1 1 d R U . . .
H5B H 0.618195 0.199587 0.145558 0.072 Uiso 1 1 d R U . . .
O7 O 0.4519(4) 0.5769(3) 0.0716(5) 0.0279(9) Uani 1 1 d . . . . .
C1 C 0.6603(4) 0.5191(5) 0.4497(8) 0.0250(11) Uani 1 1 d . . . . .
C2 C 0.7520(5) 0.5822(4) 0.5241(8) 0.0220(11) Uani 1 1 d . . . . .
C3 C 0.8330(5) 0.5189(5) 0.5880(9) 0.0318(13) Uani 1 1 d . . . . .
C4 C 0.9206(5) 0.5697(6) 0.6594(10) 0.0394(16) Uani 1 1 d . . . . .
C5 C 0.9256(5) 0.6872(6) 0.6658(10) 0.0394(15) Uani 1 1 d . . . . .
C6 C 0.8452(5) 0.7520(5) 0.6020(8) 0.0303(13) Uani 1 1 d . . . . .
C7 C 0.7571(4) 0.7023(5) 0.5323(7) 0.0225(11) Uani 1 1 d . . . . .
C8 C 0.6673(4) 0.7726(5) 0.4723(7) 0.0252(11) Uani 1 1 d . . . . .
O6 O 0.7794(7) 0.3862(8) 0.0356(16) 0.102(3) Uani 1 1 d G . . . .
H6A H 0.773480 0.456252 0.066731 0.152 Uiso 1 1 d G U . . .
H6B H 0.831858 0.384719 -0.024467 0.152 Uiso 1 1 d G 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 Bi1 3.6421(4) 3_665 ?
Bi1 O1 2.434(4) . ?
Bi1 O2 2.624(4) 3_666 ?
Bi1 O3 2.686(4) 2_645 ?
Bi1 O4 2.400(4) 2_645 ?
Bi1 O5 2.653(5) . ?
Bi1 O7 2.203(4) 3_665 ?
Bi1 O7 2.198(4) . ?
F1 C3 1.358(7) . ?
F2 C4 1.323(7) . ?
F3 C5 1.339(8) . ?
F4 C6 1.349(7) . ?
O1 C1 1.247(7) . ?
O2 C1 1.263(7) . ?
O3 C8 1.245(7) . ?
O4 C8 1.257(7) . ?
O5 H5A 0.8499 . ?
O5 H5B 0.8501 . ?
C1 C2 1.501(8) . ?
C2 C3 1.368(8) . ?
C2 C7 1.398(7) . ?
C3 C4 1.385(9) . ?
C4 C5 1.367(9) . ?
C5 C6 1.370(9) . ?
C6 C7 1.380(8) . ?
C7 C8 1.494(8) . ?
O6 H6A 0.8500 . ?
O6 H6B 0.8500 . ?

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 Bi1 78.16(10) . 3_665 ?
O1 Bi1 O2 91.25(14) . 3_666 ?
O1 Bi1 O3 142.79(14) . 2_645 ?
O1 Bi1 O5 74.06(15) . . ?
O2 Bi1 Bi1 107.19(9) 3_666 3_665 ?
O2 Bi1 O3 125.48(13) 3_666 2_645 ?
O2 Bi1 O5 138.02(14) 3_666 . ?
O3 Bi1 Bi1 94.27(10) 2_645 3_665 ?
O4 Bi1 Bi1 86.77(10) 2_645 3_665 ?
O4 Bi1 O1 159.84(15) 2_645 . ?
O4 Bi1 O2 80.41(13) 2_645 3_666 ?
O4 Bi1 O3 50.81(13) 2_645 2_645 ?
O4 Bi1 O5 123.93(15) 2_645 . ?
O5 Bi1 Bi1 107.78(11) . 3_665 ?
O5 Bi1 O3 73.84(15) . 2_645 ?
O7 Bi1 Bi1 34.11(10) 3_665 3_665 ?
O7 Bi1 Bi1 34.19(11) . 3_665 ?
O7 Bi1 O1 80.60(15) 3_665 . ?
O7 Bi1 O1 79.84(15) . . ?
O7 Bi1 O2 73.01(14) . 3_666 ?
O7 Bi1 O2 141.28(13) 3_665 3_666 ?
O7 Bi1 O3 73.80(14) 3_665 2_645 ?
O7 Bi1 O3 113.76(15) . 2_645 ?
O7 Bi1 O4 80.18(15) . 2_645 ?
O7 Bi1 O4 94.42(16) 3_665 2_645 ?
O7 Bi1 O5 138.51(16) . . ?
O7 Bi1 O5 75.96(15) 3_665 . ?
O7 Bi1 O7 68.30(17) . 3_665 ?
C1 O1 Bi1 109.3(4) . . ?
C1 O2 Bi1 119.3(3) . 3_666 ?
C8 O3 Bi1 86.3(3) . 2_655 ?
C8 O4 Bi1 99.5(3) . 2_655 ?
Bi1 O5 H5A 109.3 . . ?
Bi1 O5 H5B 109.3 . . ?
H5A O5 H5B 104.5 . . ?
Bi1 O7 Bi1 111.70(17) . 3_665 ?
O1 C1 O2 124.2(5) . . ?
O1 C1 C2 117.2(5) . . ?
O2 C1 C2 118.5(5) . . ?
C3 C2 C1 118.2(5) . . ?
C3 C2 C7 119.1(6) . . ?
C7 C2 C1 122.7(5) . . ?
F1 C3 C2 120.7(6) . . ?
F1 C3 C4 117.1(6) . . ?
C2 C3 C4 122.2(6) . . ?
F2 C4 C3 120.7(6) . . ?
F2 C4 C5 120.8(6) . . ?
C5 C4 C3 118.5(6) . . ?
F3 C5 C4 119.6(6) . . ?
F3 C5 C6 120.3(7) . . ?
C4 C5 C6 120.1(6) . . ?
F4 C6 C5 116.9(6) . . ?
F4 C6 C7 121.1(5) . . ?
C5 C6 C7 122.0(6) . . ?
C2 C7 C8 119.8(5) . . ?
C6 C7 C2 118.1(5) . . ?
C6 C7 C8 122.1(5) . . ?
O3 C8 O4 122.8(5) . . ?
O3 C8 C7 117.6(5) . . ?
O4 C8 C7 119.6(5) . . ?
H6A O6 H6B 104.5 . . ?

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 C1 O2 3.1(7) . . . . ?
Bi1 O1 C1 C2 -179.4(4) . . . . ?
Bi1 O2 C1 O1 -116.2(5) 3_666 . . . ?
Bi1 O2 C1 C2 66.4(6) 3_666 . . . ?
Bi1 O3 C8 O4 7.4(5) 2_655 . . . ?
Bi1 O3 C8 C7 -171.1(4) 2_655 . . . ?
Bi1 O4 C8 O3 -8.4(6) 2_655 . . . ?
Bi1 O4 C8 C7 170.1(4) 2_655 . . . ?
F1 C3 C4 F2 -2.6(10) . . . . ?
F1 C3 C4 C5 178.1(7) . . . . ?
F2 C4 C5 F3 -1.4(12) . . . . ?
F2 C4 C5 C6 -179.4(7) . . . . ?
F3 C5 C6 F4 1.6(10) . . . . ?
F3 C5 C6 C7 -177.2(6) . . . . ?
F4 C6 C7 C2 179.9(5) . . . . ?
F4 C6 C7 C8 -2.2(9) . . . . ?
O1 C1 C2 C3 -105.2(7) . . . . ?
O1 C1 C2 C7 75.5(7) . . . . ?
O2 C1 C2 C3 72.4(7) . . . . ?
O2 C1 C2 C7 -106.9(6) . . . . ?
C1 C2 C3 F1 2.1(9) . . . . ?
C1 C2 C3 C4 -179.8(6) . . . . ?
C1 C2 C7 C6 -179.6(5) . . . . ?
C1 C2 C7 C8 2.5(8) . . . . ?
C2 C3 C4 F2 179.3(6) . . . . ?
C2 C3 C4 C5 0.0(11) . . . . ?
C2 C7 C8 O3 27.2(8) . . . . ?
C2 C7 C8 O4 -151.4(5) . . . . ?
C3 C2 C7 C6 1.2(9) . . . . ?
C3 C2 C7 C8 -176.8(5) . . . . ?
C3 C4 C5 F3 177.9(7) . . . . ?
C3 C4 C5 C6 -0.1(11) . . . . ?
C4 C5 C6 F4 179.7(6) . . . . ?
C4 C5 C6 C7 0.8(11) . . . . ?
C5 C6 C7 C2 -1.3(9) . . . . ?
C5 C6 C7 C8 176.5(6) . . . . ?
C6 C7 C8 O3 -150.6(6) . . . . ?
C6 C7 C8 O4 30.8(8) . . . . ?
C7 C2 C3 F1 -178.6(6) . . . . ?
C7 C2 C3 C4 -0.5(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_database_code_depnum_ccdc_archive 'CCDC 2482351'
loop_
_audit_author_name
_audit_author_address
'Tao Huang'
;SWUST
China
;
_audit_update_record             
;
2025-08-23 deposited with the CCDC.	2025-12-23 downloaded from the CCDC.
;
_audit_creation_date             2024-09-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H21 Bi N3 O11'
_chemical_formula_sum            'C15 H21 Bi N3 O11'
_chemical_formula_weight         628.33
_chemical_melting_point          ?
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'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.3625(15)
_cell_length_b                   17.769(3)
_cell_length_c                   10.2592(13)
_cell_angle_alpha                90
_cell_angle_beta                 94.019(5)
_cell_angle_gamma                90
_cell_volume                     2066.3(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4659
_cell_measurement_temperature    293.00
_cell_measurement_theta_max      26.25
_cell_measurement_theta_min      2.30
_shelx_estimated_absorpt_T_max   0.546
_shelx_estimated_absorpt_T_min   0.401
_exptl_absorpt_coefficient_mu    8.596
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5439
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1181 before and 0.0592 after correction.
The Ratio of minimum to maximum transmission is 0.7295.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    2.020
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1212
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19284
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.562
_diffrn_reflns_theta_min         1.797
_diffrn_ambient_temperature      293.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE TXS PHOTON II'
_diffrn_measurement_method       'ω and φ shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   TXS
_diffrn_source_current           40.0
_diffrn_source_power             1.8
_diffrn_source_type              'Rotaing Anode'
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3390
_reflns_number_total             4761
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX5 V2023.9-2 (Bruker, 2023)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.549
_refine_diff_density_min         -1.005
_refine_diff_density_rms         0.143
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4761
_refine_ls_number_restraints     197
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0485
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0330P)²+8.1521P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.1074
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N3-C8 = N3-C9
 1.5 with sigma of 0.01
 C9-C8
 2.5 with sigma of 0.01
 O2A-O1A
 2.2 with sigma of 0.01
 O2-C1 \\sim O2A-C1 \\sim O1A-C1 \\sim O1-C1
 with sigma of 0.02
 N3A-C8A \\sim N3A-C9A \\sim N3-C9 \\sim N3-C8
 with sigma of 0.02
 N3A-C7 \\sim N3-C7
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O11 \\sim C7 \\sim N3 \\sim C8 \\sim C9: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 2A
C15 \\sim N1 \\sim C14 \\sim C13 \\sim O9: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
C12 \\sim N2 \\sim C10 \\sim C11 \\sim O10: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
C1 \\sim O1 \\sim O2 \\sim O1A \\sim O2A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
N3 \\sim C9 \\sim C8 \\sim N3A \\sim C9A \\sim C8A: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(O1A)=Sof(O2A)=1-FVAR(1)
 Sof(O1)=Sof(O2)=FVAR(1)
 Sof(H7B)=Sof(N3A)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(H9AC)=Sof(C8A)=Sof(H8AA)=
 Sof(H8AB)=Sof(H8AC)=1-FVAR(2)
 Sof(N3)=Sof(H7A)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(H9C)=Sof(C8)=Sof(H8A)=Sof(H8B)=
 Sof(H8C)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C10(H10), C7(H7A), C7(H7B)
5.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C11(H11A,H11B,H11C), C15(H15A,H15B,H15C), C14(H14A,H14B,
 H14C), C9(H9A,H9B,H9C), C8(H8A,H8B,H8C), C9A(H9AA,H9AB,H9AC), C8A(H8AA,H8AB,
 H8AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.15238(3) 0.48767(2) 0.26154(3) 0.04588(12) Uani 1 1 d . . . . .
O6 O -0.0590(5) 0.4290(3) 0.5911(5) 0.0545(15) Uani 1 1 d . . . . .
O5 O 0.0388(5) 0.4208(3) 0.4129(5) 0.0541(15) Uani 1 1 d . . . . .
O8 O -0.1488(5) 0.5223(4) -0.0171(5) 0.0567(15) Uani 1 1 d . . . . .
O7 O -0.0378(5) 0.4937(3) 0.1627(5) 0.0551(15) Uani 1 1 d . . . . .
O3 O 0.7046(6) 0.5739(4) 0.5565(7) 0.075(2) Uani 1 1 d . . . . .
O11 O 0.1608(6) 0.3539(4) 0.2024(6) 0.0724(18) Uani 1 1 d . U . . .
O4 O 0.3066(6) 0.5719(4) 0.3993(7) 0.076(2) Uani 1 1 d . . . . .
O9 O 0.1445(6) 0.6134(4) 0.1570(6) 0.0706(18) Uani 1 1 d . U . . .
C6 C -0.0055(7) 0.4566(5) 0.5013(8) 0.0446(19) Uani 1 1 d . . . . .
O10 O 0.3754(7) 0.4765(5) 0.1927(8) 0.097(2) Uani 1 1 d . U . . .
C3 C 0.3989(8) 0.5423(5) 0.4453(9) 0.059(2) Uani 1 1 d . . . . .
C5 C -0.0533(7) 0.5042(4) 0.0405(8) 0.0460(19) Uani 1 1 d . . . . .
N3 N 0.198(3) 0.2314(8) 0.253(3) 0.093(3) Uani 0.448(13) 1 d D U P A 1
C4 C 0.6078(9) 0.5427(6) 0.5333(9) 0.062(2) Uani 1 1 d . . . . .
C2 C 0.5061(8) 0.5791(6) 0.4795(9) 0.067(3) Uani 1 1 d . . . . .
N1 N 0.1755(11) 0.7351(6) 0.1279(11) 0.109(3) Uani 1 1 d . U . . .
N2 N 0.5329(9) 0.4267(6) 0.1051(11) 0.102(3) Uani 1 1 d . U . . .
C1 C 0.5094(13) 0.6582(7) 0.4602(14) 0.103(4) Uani 1 1 d D U . . .
C13 C 0.1899(12) 0.6704(7) 0.1863(12) 0.088(3) Uani 1 1 d . U . . .
H13 H 0.242632 0.669447 0.259869 0.105 Uiso 1 1 calc R U . . .
O1 O 0.4681(11) 0.6865(6) 0.3604(14) 0.140(5) Uani 0.883(13) 1 d D U P B 1
C10 C 0.4200(11) 0.4322(8) 0.1233(12) 0.096(3) Uani 1 1 d . U . . .
H10 H 0.369765 0.398456 0.077895 0.115 Uiso 1 1 calc R U . . .
O2 O 0.5462(13) 0.6988(6) 0.5506(15) 0.153(5) Uani 0.883(13) 1 d D U P B 1
C12 C 0.6180(10) 0.4759(8) 0.1798(15) 0.112(4) Uani 1 1 d . U . . .
H12A H 0.578869 0.521015 0.204706 0.168 Uiso 1 1 calc R U . . .
H12B H 0.681259 0.488640 0.126579 0.168 Uiso 1 1 calc R U . . .
H12C H 0.649178 0.449967 0.256781 0.168 Uiso 1 1 calc R U . . .
C7 C 0.1789(12) 0.3012(7) 0.2658(13) 0.097(3) Uani 1 1 d D U . . .
H7A H 0.180099 0.313728 0.353930 0.116 Uiso 0.448(13) 1 calc R U P A 1
H7B H 0.190622 0.313747 0.353790 0.116 Uiso 0.552(13) 1 calc R U P A 2
C11 C 0.5778(14) 0.3740(9) 0.0124(16) 0.145(5) Uani 1 1 d . U . . .
H11A H 0.513932 0.344386 -0.026236 0.218 Uiso 1 1 calc R U . . .
H11B H 0.635030 0.341572 0.056827 0.218 Uiso 1 1 calc R U . . .
H11C H 0.614279 0.401362 -0.054784 0.218 Uiso 1 1 calc R U . . .
C15 C 0.2301(18) 0.8026(9) 0.1676(19) 0.171(6) Uani 1 1 d . U . . .
H15A H 0.171802 0.841652 0.169470 0.257 Uiso 1 1 calc R U . . .
H15B H 0.287453 0.816055 0.107326 0.257 Uiso 1 1 calc R U . . .
H15C H 0.268424 0.796489 0.253360 0.257 Uiso 1 1 calc R U . . .
C14 C 0.1010(17) 0.7402(9) 0.0115(16) 0.169(6) Uani 1 1 d . U . . .
H14A H 0.120250 0.700675 -0.047167 0.253 Uiso 1 1 calc R U . . .
H14B H 0.112143 0.788081 -0.029055 0.253 Uiso 1 1 calc R U . . .
H14C H 0.020228 0.735211 0.032017 0.253 Uiso 1 1 calc R U . . .
C9 C 0.276(3) 0.1753(13) 0.325(3) 0.112(6) Uani 0.448(13) 1 d D U P A 1
H9A H 0.356709 0.187607 0.314413 0.168 Uiso 0.448(13) 1 calc R U P A 1
H9B H 0.258927 0.125919 0.290593 0.168 Uiso 0.448(13) 1 calc R U P A 1
H9C H 0.261329 0.176478 0.415977 0.168 Uiso 0.448(13) 1 calc R U P A 1
C8 C 0.115(3) 0.1969(15) 0.151(3) 0.119(6) Uani 0.448(13) 1 d D U P A 1
H8A H 0.037907 0.192607 0.184503 0.179 Uiso 0.448(13) 1 calc R U P A 1
H8B H 0.142507 0.147767 0.129671 0.179 Uiso 0.448(13) 1 calc R U P A 1
H8C H 0.109712 0.227956 0.074717 0.179 Uiso 0.448(13) 1 calc R U P A 1
O1A O 0.418(4) 0.690(4) 0.485(9) 0.135(7) Uani 0.117(13) 1 d D U P B 2
O2A O 0.604(3) 0.688(4) 0.438(10) 0.134(8) Uani 0.117(13) 1 d D U P B 2
N3A N 0.187(2) 0.2319(7) 0.249(2) 0.088(4) Uani 0.552(13) 1 d D U P A 2
C9A C 0.170(3) 0.1671(12) 0.332(3) 0.114(5) Uani 0.552(13) 1 d D U P A 2
H9AA H 0.225759 0.168540 0.406502 0.171 Uiso 0.552(13) 1 calc R U P A 2
H9AB H 0.180402 0.121716 0.283559 0.171 Uiso 0.552(13) 1 calc R U P A 2
H9AC H 0.091117 0.168206 0.361101 0.171 Uiso 0.552(13) 1 calc R U P A 2
C8A C 0.239(3) 0.2137(14) 0.128(2) 0.121(6) Uani 0.552(13) 1 d D U P A 2
H8AA H 0.183003 0.225067 0.055744 0.182 Uiso 0.552(13) 1 calc R U P A 2
H8AB H 0.257729 0.161102 0.126812 0.182 Uiso 0.552(13) 1 calc R U P A 2
H8AC H 0.308890 0.242866 0.120793 0.182 Uiso 0.552(13) 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 O6 2.414(5) 3_566 ?
Bi1 O5 2.402(5) . ?
Bi1 O8 2.511(5) 3_565 ?
Bi1 O7 2.324(6) . ?
Bi1 O3 2.627(6) 3_666 ?
Bi1 O11 2.457(7) . ?
Bi1 O4 2.638(6) . ?
Bi1 O9 2.477(6) . ?
Bi1 O10 2.685(8) . ?
O6 C6 1.240(9) . ?
O5 C6 1.243(9) . ?
O8 C5 1.241(9) . ?
O7 C5 1.268(9) . ?
O3 C4 1.241(11) . ?
O11 C7 1.149(13) . ?
O4 C3 1.236(10) . ?
O9 C13 1.166(13) . ?
C6 C6 1.547(18) 3_566 ?
O10 C10 1.198(14) . ?
C3 C4 1.529(14) 3_666 ?
C3 C2 1.405(12) . ?
C5 C5 1.524(16) 3_565 ?
N3 C7 1.268(17) . ?
N3 C9 1.493(9) . ?
N3 C8 1.487(9) . ?
C4 C2 1.404(12) . ?
C2 C1 1.419(16) . ?
N1 C13 1.302(14) . ?
N1 C15 1.398(17) . ?
N1 C14 1.417(17) . ?
N2 C10 1.313(14) . ?
N2 C12 1.477(15) . ?
N2 C11 1.453(16) . ?
C1 O1 1.205(12) . ?
C1 O2 1.226(13) . ?
C1 O1A 1.224(18) . ?
C1 O2A 1.230(19) . ?
C13 H13 0.9300 . ?
C10 H10 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C7 H7A 0.9300 . ?
C7 H7B 0.9300 . ?
C7 N3A 1.249(16) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
N3A C9A 1.454(15) . ?
N3A C8A 1.447(16) . ?
C9A H9AA 0.9600 . ?
C9A H9AB 0.9600 . ?
C9A H9AC 0.9600 . ?
C8A H8AA 0.9600 . ?
C8A H8AB 0.9600 . ?
C8A H8AC 0.9600 . ?

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
O6 Bi1 O8 133.76(19) 3_566 3_565 ?
O6 Bi1 O3 95.0(2) 3_566 3_666 ?
O6 Bi1 O11 140.7(2) 3_566 . ?
O6 Bi1 O4 67.8(2) 3_566 . ?
O6 Bi1 O9 73.4(2) 3_566 . ?
O6 Bi1 O10 132.4(2) 3_566 . ?
O5 Bi1 O6 67.61(19) . 3_566 ?
O5 Bi1 O8 129.70(19) . 3_565 ?
O5 Bi1 O3 70.6(2) . 3_666 ?
O5 Bi1 O11 73.3(2) . . ?
O5 Bi1 O4 107.5(2) . . ?
O5 Bi1 O9 136.2(2) . . ?
O5 Bi1 O10 133.9(2) . . ?
O8 Bi1 O3 130.2(2) 3_565 3_666 ?
O8 Bi1 O4 122.6(2) 3_565 . ?
O8 Bi1 O10 71.4(2) 3_565 . ?
O7 Bi1 O6 79.0(2) . 3_566 ?
O7 Bi1 O5 77.3(2) . . ?
O7 Bi1 O8 67.57(19) . 3_565 ?
O7 Bi1 O3 147.1(2) . 3_666 ?
O7 Bi1 O11 89.3(2) . . ?
O7 Bi1 O4 140.3(2) . . ?
O7 Bi1 O9 76.4(2) . . ?
O7 Bi1 O10 139.0(2) . . ?
O3 Bi1 O4 60.1(2) 3_666 . ?
O3 Bi1 O10 66.9(3) 3_666 . ?
O11 Bi1 O8 71.5(2) . 3_565 ?
O11 Bi1 O3 74.9(2) . 3_666 ?
O11 Bi1 O4 130.2(2) . . ?
O11 Bi1 O9 140.1(2) . . ?
O11 Bi1 O10 79.1(3) . . ?
O4 Bi1 O10 65.1(2) . . ?
O9 Bi1 O8 68.5(2) . 3_565 ?
O9 Bi1 O3 133.3(2) . 3_666 ?
O9 Bi1 O4 73.9(2) . . ?
O9 Bi1 O10 87.6(3) . . ?
C6 O6 Bi1 118.9(5) . 3_566 ?
C6 O5 Bi1 118.8(5) . . ?
C5 O8 Bi1 114.2(5) . 3_565 ?
C5 O7 Bi1 119.9(5) . . ?
C4 O3 Bi1 116.5(6) . 3_666 ?
C7 O11 Bi1 131.0(8) . . ?
C3 O4 Bi1 118.5(6) . . ?
C13 O9 Bi1 132.0(7) . . ?
O6 C6 O5 125.7(8) . . ?
O6 C6 C6 116.8(9) . 3_566 ?
O5 C6 C6 117.5(9) . 3_566 ?
C10 O10 Bi1 130.6(8) . . ?
O4 C3 C4 115.2(9) . 3_666 ?
O4 C3 C2 126.5(9) . . ?
C2 C3 C4 118.3(8) . 3_666 ?
O8 C5 O7 124.5(7) . . ?
O8 C5 C5 117.8(9) . 3_565 ?
O7 C5 C5 117.7(9) . 3_565 ?
C7 N3 C9 134(2) . . ?
C7 N3 C8 112(2) . . ?
C8 N3 C9 113.4(10) . . ?
O3 C4 C3 117.8(8) . 3_666 ?
O3 C4 C2 124.3(10) . . ?
C2 C4 C3 117.7(9) . 3_666 ?
C3 C2 C1 117.2(9) . . ?
C4 C2 C3 123.9(10) . . ?
C4 C2 C1 118.9(10) . . ?
C13 N1 C15 125.8(14) . . ?
C13 N1 C14 119.5(13) . . ?
C15 N1 C14 114.7(12) . . ?
C10 N2 C12 119.5(11) . . ?
C10 N2 C11 122.2(12) . . ?
C11 N2 C12 118.3(11) . . ?
O1 C1 C2 121.3(12) . . ?
O1 C1 O2 119.2(14) . . ?
O2 C1 C2 119.2(12) . . ?
O1A C1 C2 114(4) . . ?
O1A C1 O2A 127(3) . . ?
O2A C1 C2 119(3) . . ?
O9 C13 N1 127.5(13) . . ?
O9 C13 H13 116.3 . . ?
N1 C13 H13 116.3 . . ?
O10 C10 N2 126.2(13) . . ?
O10 C10 H10 116.9 . . ?
N2 C10 H10 116.9 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O11 C7 N3 139.6(19) . . ?
O11 C7 H7A 110.2 . . ?
O11 C7 H7B 111.2 . . ?
O11 C7 N3A 137.5(16) . . ?
N3 C7 H7A 110.2 . . ?
N3A C7 H7B 111.2 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 N3A C9A 133(2) . . ?
C7 N3A C8A 112.1(19) . . ?
C8A N3A C9A 114.0(17) . . ?
N3A C9A H9AA 109.5 . . ?
N3A C9A H9AB 109.5 . . ?
N3A C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
N3A C8A H8AA 109.5 . . ?
N3A C8A H8AB 109.5 . . ?
N3A C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Bi1 O6 C6 O5 -174.3(7) 3_566 . . . ?
Bi1 O6 C6 C6 5.0(12) 3_566 . . 3_566 ?
Bi1 O5 C6 O6 -174.7(6) . . . . ?
Bi1 O5 C6 C6 6.0(12) . . . 3_566 ?
Bi1 O8 C5 O7 -168.4(6) 3_565 . . . ?
Bi1 O8 C5 C5 13.2(11) 3_565 . . 3_565 ?
Bi1 O7 C5 O8 -165.7(6) . . . . ?
Bi1 O7 C5 C5 12.7(12) . . . 3_565 ?
Bi1 O3 C4 C3 -29.7(11) 3_666 . . 3_666 ?
Bi1 O3 C4 C2 155.3(8) 3_666 . . . ?
Bi1 O11 C7 N3 -171(3) . . . . ?
Bi1 O11 C7 N3A -179(2) . . . . ?
Bi1 O4 C3 C4 -24.4(11) . . . 3_666 ?
Bi1 O4 C3 C2 156.0(8) . . . . ?
Bi1 O9 C13 N1 -176.1(10) . . . . ?
Bi1 O10 C10 N2 -172.9(10) . . . . ?
O3 C4 C2 C3 175.5(10) . . . . ?
O3 C4 C2 C1 -5.8(17) . . . . ?
O11 C7 N3A C9A -154(3) . . . . ?
O11 C7 N3A C8A 34(4) . . . . ?
O4 C3 C2 C4 179.0(10) . . . . ?
O4 C3 C2 C1 0.3(17) . . . . ?
C3 C4 C2 C3 0.5(16) 3_666 . . . ?
C3 C4 C2 C1 179.2(10) 3_666 . . . ?
C3 C2 C1 O1 -45(2) . . . . ?
C3 C2 C1 O2 128.6(16) . . . . ?
C3 C2 C1 O1A 38(5) . . . . ?
C3 C2 C1 O2A -151(6) . . . . ?
C4 C3 C2 C4 -0.5(16) 3_666 . . . ?
C4 C3 C2 C1 -179.3(10) 3_666 . . . ?
C4 C2 C1 O1 135.7(16) . . . . ?
C4 C2 C1 O2 -50(2) . . . . ?
C4 C2 C1 O1A -141(5) . . . . ?
C4 C2 C1 O2A 30(6) . . . . ?
C12 N2 C10 O10 3(2) . . . . ?
C11 N2 C10 O10 -176.0(14) . . . . ?
C15 N1 C13 O9 178.7(16) . . . . ?
C14 N1 C13 O9 -3(2) . . . . ?
C9 N3 C7 O11 142(3) . . . . ?
C8 N3 C7 O11 -45(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU
####################################################################### 
# 
# 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_ht03052_sq
_database_code_depnum_ccdc_archive 'CCDC 2465596'
loop_
_audit_author_name
_audit_author_address
'hunter clinton'
;swust
China
;
_audit_update_record             
;
2025-06-19 deposited with the CCDC.	2025-12-23 downloaded from the CCDC.
;
_audit_creation_date             2025-03-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C33 H28 Bi N3 O7 S2'
_chemical_formula_sum            'C33 H28 Bi N3 O7 S2'
_chemical_formula_weight         851.68
_chemical_melting_point          ?
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'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.9683(4)
_cell_length_b                   16.8294(4)
_cell_length_c                   16.7130(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.4790(10)
_cell_angle_gamma                90
_cell_volume                     3646.38(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5621
_cell_measurement_temperature    301.00
_cell_measurement_theta_max      25.794
_cell_measurement_theta_min      2.357
_shelx_estimated_absorpt_T_max   0.585
_shelx_estimated_absorpt_T_min   0.521
_exptl_absorpt_coefficient_mu    4.996
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.5841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1101 before and 0.0759 after correction.
The Ratio of minimum to maximum transmission is 0.7832.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1672
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0815
_diffrn_reflns_av_unetI/netI     0.0731
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            36056
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.694
_diffrn_reflns_theta_min         2.306
_diffrn_ambient_temperature      301.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'BrukerD8 Venture'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.6
_diffrn_source_power             0.08
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6374
_reflns_number_total             9285
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.259
_refine_diff_density_min         -1.096
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     454
_refine_ls_number_reflns         9285
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0274P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0905
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C19-C20 \\sim C19-C31
 with sigma of 0.02
 C19-C24 \\sim C19-C34
 with sigma of 0.02
 C22-C21 \\sim C22-C32
 with sigma of 0.02
 C22-C23 \\sim C22-C33
 with sigma of 0.02
 C20-C21 \\sim C31-C32
 with sigma of 0.02
 C24-C23 \\sim C34-C33
 with sigma of 0.02
 C19-C21 \\sim C19-C32
 with sigma of 0.04
 C19-C23 \\sim C19-C33
 with sigma of 0.04
 C22-C20 \\sim C22-C31
 with sigma of 0.04
 C22-C24 \\sim C22-C34
 with sigma of 0.04
3. Others
 Sof(C31)=Sof(H31)=Sof(C32)=Sof(H32)=Sof(C33)=Sof(H33)=Sof(C34)=Sof(H34)=1-
 FVAR(1)
 Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21)=Sof(C23)=Sof(H23)=Sof(C24)=Sof(H24)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C14(H14),
 C15(H15), C16(H16), C17(H17), C18(H18), C26(H26), C27(H27), C29(H29), C30(H30),
  C31(H31), C32(H32), C33(H33), C34(H34), C35(H35), C20(H20), C21(H21),
 C23(H23), C24(H24)
4.b Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C37(H37A,H37B,H37C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.65087(2) 0.45817(2) 0.61152(2) 0.03987(7) Uani 1 1 d . . . . .
S1 S 0.56950(11) 0.44475(7) 0.79428(8) 0.0497(3) Uani 1 1 d . . . . .
S2 S 0.02850(11) 0.86147(8) 1.00555(8) 0.0522(3) Uani 1 1 d . . . . .
O1 O 0.6470(3) 0.4964(2) 0.7575(2) 0.0599(10) Uani 1 1 d . . . . .
O2 O 0.6086(3) 0.4032(2) 0.8633(2) 0.0747(13) Uani 1 1 d . . . . .
O3 O 0.5239(3) 0.3952(2) 0.7317(2) 0.0629(10) Uani 1 1 d . . . . .
O4 O 0.0748(3) 0.9343(2) 0.9776(3) 0.0719(12) Uani 1 1 d . . . . .
O5 O -0.0733(3) 0.84821(19) 0.9655(2) 0.0521(9) Uani 1 1 d . . . . .
O6 O 0.0252(3) 0.8536(3) 1.0906(2) 0.0810(14) Uani 1 1 d . . . . .
N1 N 0.7631(3) 0.4682(2) 0.4981(2) 0.0500(10) Uani 1 1 d . . . . .
N2 N 0.7774(4) 0.5667(3) 0.6282(3) 0.0567(12) Uani 1 1 d . . . . .
C1 C 0.7586(5) 0.4211(4) 0.4381(3) 0.0673(16) Uani 1 1 d . . . . .
H1 H 0.709777 0.380626 0.437492 0.081 Uiso 1 1 calc R U . . .
C2 C 0.8255(6) 0.4282(5) 0.3721(4) 0.079(2) Uani 1 1 d . . . . .
H2 H 0.821943 0.391500 0.330524 0.095 Uiso 1 1 calc R U . . .
C3 C 0.8925(6) 0.4870(4) 0.3704(4) 0.0713(18) Uani 1 1 d . . . . .
H3 H 0.935402 0.492571 0.327078 0.086 Uiso 1 1 calc R U . . .
C4 C 0.8989(5) 0.5413(4) 0.4341(4) 0.0660(16) Uani 1 1 d . . . . .
C5 C 0.9698(5) 0.6087(4) 0.4367(5) 0.083(2) Uani 1 1 d . . . . .
H5 H 1.013963 0.617575 0.394612 0.099 Uiso 1 1 calc R U . . .
C6 C 0.9712(6) 0.6582(4) 0.5002(4) 0.087(2) Uani 1 1 d . . . . .
H6 H 1.015901 0.701432 0.500145 0.104 Uiso 1 1 calc R U . . .
C7 C 0.9092(5) 0.6476(3) 0.5656(4) 0.0641(16) Uani 1 1 d . . . . .
C8 C 0.9067(6) 0.6980(4) 0.6316(5) 0.085(2) Uani 1 1 d . . . . .
H8 H 0.950702 0.741626 0.633595 0.103 Uiso 1 1 calc R U . . .
C9 C 0.8433(7) 0.6857(4) 0.6923(5) 0.094(2) Uani 1 1 d . . . . .
H9 H 0.841571 0.720383 0.735567 0.112 Uiso 1 1 calc R U . . .
C10 C 0.7789(5) 0.6179(4) 0.6881(4) 0.0729(18) Uani 1 1 d . . . . .
H10 H 0.734853 0.608758 0.730162 0.087 Uiso 1 1 calc R U . . .
C11 C 0.8389(4) 0.5820(3) 0.5658(3) 0.0552(14) Uani 1 1 d . . . . .
C12 C 0.8339(4) 0.5293(3) 0.4987(3) 0.0542(14) Uani 1 1 d . . . . .
C13 C 0.7674(4) 0.3666(3) 0.6541(3) 0.0504(13) Uani 1 1 d . . . . .
C14 C 0.8219(5) 0.3764(4) 0.7258(3) 0.0738(18) Uani 1 1 d . . . . .
H14 H 0.812411 0.422197 0.755819 0.089 Uiso 1 1 calc R U . . .
C15 C 0.8898(6) 0.3194(5) 0.7529(4) 0.099(3) Uani 1 1 d . . . . .
H15 H 0.926905 0.327463 0.800587 0.119 Uiso 1 1 calc R U . . .
C16 C 0.9032(6) 0.2522(5) 0.7115(5) 0.100(3) Uani 1 1 d . . . . .
H16 H 0.946951 0.212956 0.731978 0.120 Uiso 1 1 calc R U . . .
C17 C 0.8536(6) 0.2407(4) 0.6397(5) 0.088(2) Uani 1 1 d . . . . .
H17 H 0.866425 0.195330 0.609750 0.106 Uiso 1 1 calc R U . . .
C18 C 0.7824(5) 0.2982(3) 0.6110(4) 0.0667(16) Uani 1 1 d . . . . .
H18 H 0.745773 0.289854 0.563145 0.080 Uiso 1 1 calc R U . . .
C19 C 0.4729(4) 0.5103(3) 0.8270(3) 0.0489(13) Uani 1 1 d D . . . .
C22 C 0.3258(4) 0.6176(3) 0.8825(3) 0.0535(14) Uani 1 1 d D . . . .
C25 C 0.2496(4) 0.6743(3) 0.9138(3) 0.0538(14) Uani 1 1 d . . . . .
C26 C 0.1823(6) 0.7151(4) 0.8628(4) 0.098(3) Uani 1 1 d . . . . .
H26 H 0.183179 0.704634 0.808172 0.117 Uiso 1 1 calc R U . . .
C27 C 0.1146(6) 0.7705(4) 0.8908(4) 0.091(3) Uani 1 1 d . . . . .
H27 H 0.072611 0.798792 0.854895 0.109 Uiso 1 1 calc R U . . .
C28 C 0.1084(4) 0.7843(3) 0.9707(3) 0.0505(13) Uani 1 1 d . . . . .
C29 C 0.1709(5) 0.7430(3) 1.0223(3) 0.0641(16) Uani 1 1 d . . . . .
H29 H 0.166179 0.751332 1.077132 0.077 Uiso 1 1 calc R U . . .
C30 C 0.2418(5) 0.6884(3) 0.9941(3) 0.0609(15) Uani 1 1 d . . . . .
H30 H 0.284566 0.661192 1.030266 0.073 Uiso 1 1 calc R U . . .
C31 C 0.4001(17) 0.5399(15) 0.7790(10) 0.100(11) Uani 0.445(17) 1 d D . P A 2
H31 H 0.399520 0.527488 0.724756 0.120 Uiso 0.445(17) 1 calc R U P A 2
C32 C 0.3236(18) 0.5901(16) 0.8091(10) 0.107(11) Uani 0.445(17) 1 d D . P A 2
H32 H 0.268712 0.604482 0.775263 0.128 Uiso 0.445(17) 1 calc R U P A 2
C33 C 0.4157(12) 0.6010(12) 0.9315(8) 0.072(5) Uani 0.445(17) 1 d D . P A 2
H33 H 0.426331 0.626198 0.980533 0.086 Uiso 0.445(17) 1 calc R U P A 2
C34 C 0.4865(13) 0.5461(11) 0.9037(7) 0.067(5) Uani 0.445(17) 1 d D . P A 2
H34 H 0.543653 0.532652 0.935605 0.080 Uiso 0.445(17) 1 calc R U P A 2
O7 O 1.1568(7) 0.7685(6) 0.5905(6) 0.212(4) Uani 1 1 d . . . . .
N3 N 1.2670(7) 0.8264(5) 0.6704(5) 0.122(3) Uani 1 1 d . . . . .
C35 C 1.1783(9) 0.8085(6) 0.6454(8) 0.146(4) Uani 1 1 d . . . . .
H35 H 1.123689 0.829339 0.673646 0.175 Uiso 1 1 calc R U . . .
C36 C 1.3536(8) 0.7907(8) 0.6340(8) 0.196(6) Uani 1 1 d . . . . .
H36A H 1.343219 0.734346 0.630348 0.294 Uiso 1 1 calc R U . . .
H36B H 1.414724 0.801494 0.665693 0.294 Uiso 1 1 calc R U . . .
H36C H 1.361109 0.812287 0.581248 0.294 Uiso 1 1 calc R U . . .
C37 C 1.2801(11) 0.8802(8) 0.7380(8) 0.242(8) Uani 1 1 d . . . . .
H37A H 1.321117 0.924855 0.722551 0.362 Uiso 1 1 calc R U . . .
H37B H 1.314066 0.852799 0.781603 0.362 Uiso 1 1 calc R U . . .
H37C H 1.213759 0.898395 0.754365 0.362 Uiso 1 1 calc R U . . .
C20 C 0.4339(10) 0.5665(7) 0.7785(7) 0.049(4) Uani 0.555(17) 1 d D . P A 1
H20 H 0.456228 0.570671 0.726182 0.058 Uiso 0.555(17) 1 calc R U P A 1
C21 C 0.3590(10) 0.6193(7) 0.8067(6) 0.044(3) Uani 0.555(17) 1 d D . P A 1
H21 H 0.331165 0.656993 0.771650 0.053 Uiso 0.555(17) 1 calc R U P A 1
C23 C 0.3621(13) 0.5537(8) 0.9309(6) 0.067(5) Uani 0.555(17) 1 d D . P A 1
H23 H 0.337351 0.547719 0.982259 0.080 Uiso 0.555(17) 1 calc R U P A 1
C24 C 0.4338(12) 0.4999(8) 0.9030(6) 0.064(4) Uani 0.555(17) 1 d D . P A 1
H24 H 0.455471 0.457435 0.934788 0.077 Uiso 0.555(17) 1 calc R U P A 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 O1 2.526(4) . ?
Bi1 O5 2.455(3) 2_546 ?
Bi1 N1 2.426(4) . ?
Bi1 N2 2.467(4) . ?
Bi1 C13 2.260(5) . ?
S1 O1 1.474(4) . ?
S1 O2 1.431(4) . ?
S1 O3 1.452(4) . ?
S1 C19 1.767(5) . ?
S2 O4 1.448(4) . ?
S2 O5 1.481(4) . ?
S2 O6 1.429(4) . ?
S2 C28 1.769(5) . ?
N1 C1 1.278(7) . ?
N1 C12 1.378(6) . ?
N2 C10 1.320(7) . ?
N2 C11 1.354(6) . ?
C1 H1 0.9300 . ?
C1 C2 1.426(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.317(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.403(9) . ?
C4 C5 1.461(9) . ?
C4 C12 1.401(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.349(9) . ?
C6 H6 0.9300 . ?
C6 C7 1.384(8) . ?
C7 C8 1.392(9) . ?
C7 C11 1.432(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.339(9) . ?
C9 H9 0.9300 . ?
C9 C10 1.415(9) . ?
C10 H10 0.9300 . ?
C11 C12 1.429(7) . ?
C13 C14 1.385(8) . ?
C13 C18 1.374(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.371(9) . ?
C15 H15 0.9300 . ?
C15 C16 1.340(10) . ?
C16 H16 0.9300 . ?
C16 C17 1.360(11) . ?
C17 H17 0.9300 . ?
C17 C18 1.414(8) . ?
C18 H18 0.9300 . ?
C19 C31 1.321(14) . ?
C19 C34 1.422(12) . ?
C19 C20 1.337(11) . ?
C19 C24 1.391(10) . ?
C22 C25 1.479(7) . ?
C22 C32 1.311(14) . ?
C22 C33 1.435(13) . ?
C22 C21 1.349(10) . ?
C22 C23 1.418(10) . ?
C25 C26 1.386(8) . ?
C25 C30 1.369(7) . ?
C26 H26 0.9300 . ?
C26 C27 1.372(8) . ?
C27 H27 0.9300 . ?
C27 C28 1.360(7) . ?
C28 C29 1.360(7) . ?
C29 H29 0.9300 . ?
C29 C30 1.391(7) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C31 C32 1.406(14) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
C33 C34 1.391(13) . ?
C34 H34 0.9300 . ?
O7 C35 1.167(11) . ?
N3 C35 1.250(12) . ?
N3 C36 1.423(11) . ?
N3 C37 1.454(12) . ?
C35 H35 0.9300 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C20 H20 0.9300 . ?
C20 C21 1.408(12) . ?
C21 H21 0.9300 . ?
C23 H23 0.9300 . ?
C23 C24 1.386(12) . ?
C24 H24 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
O5 Bi1 O1 132.89(12) 2_546 . ?
O5 Bi1 N2 151.62(13) 2_546 . ?
N1 Bi1 O1 139.90(14) . . ?
N1 Bi1 O5 83.59(13) . 2_546 ?
N1 Bi1 N2 68.03(15) . . ?
N2 Bi1 O1 74.46(13) . . ?
C13 Bi1 O1 84.20(16) . . ?
C13 Bi1 O5 85.00(17) . 2_546 ?
C13 Bi1 N1 83.35(15) . . ?
C13 Bi1 N2 91.83(18) . . ?
O1 S1 C19 104.9(2) . . ?
O2 S1 O1 113.1(3) . . ?
O2 S1 O3 115.4(2) . . ?
O2 S1 C19 107.1(2) . . ?
O3 S1 O1 108.0(2) . . ?
O3 S1 C19 107.6(3) . . ?
O4 S2 O5 110.7(2) . . ?
O4 S2 C28 105.3(2) . . ?
O5 S2 C28 105.3(2) . . ?
O6 S2 O4 115.0(3) . . ?
O6 S2 O5 112.7(2) . . ?
O6 S2 C28 107.0(2) . . ?
S1 O1 Bi1 106.4(2) . . ?
S2 O5 Bi1 118.14(19) . 2_556 ?
C1 N1 Bi1 123.6(4) . . ?
C1 N1 C12 119.1(5) . . ?
C12 N1 Bi1 117.3(3) . . ?
C10 N2 Bi1 124.4(4) . . ?
C10 N2 C11 117.6(5) . . ?
C11 N2 Bi1 117.2(4) . . ?
N1 C1 H1 118.7 . . ?
N1 C1 C2 122.6(6) . . ?
C2 C1 H1 118.7 . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.6(6) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0(6) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 123.6(6) . . ?
C12 C4 C3 117.7(6) . . ?
C12 C4 C5 118.7(6) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.9(6) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 118.5 . . ?
C5 C6 C7 123.0(6) . . ?
C7 C6 H6 118.5 . . ?
C6 C7 C8 124.9(6) . . ?
C6 C7 C11 119.0(6) . . ?
C8 C7 C11 116.1(6) . . ?
C7 C8 H8 118.9 . . ?
C9 C8 C7 122.2(7) . . ?
C9 C8 H8 118.9 . . ?
C8 C9 H9 121.3 . . ?
C8 C9 C10 117.4(7) . . ?
C10 C9 H9 121.3 . . ?
N2 C10 C9 124.1(6) . . ?
N2 C10 H10 117.9 . . ?
C9 C10 H10 117.9 . . ?
N2 C11 C7 122.4(5) . . ?
N2 C11 C12 118.1(5) . . ?
C12 C11 C7 119.5(5) . . ?
N1 C12 C4 121.0(5) . . ?
N1 C12 C11 119.0(4) . . ?
C4 C12 C11 119.9(5) . . ?
C14 C13 Bi1 120.9(4) . . ?
C18 C13 Bi1 120.5(4) . . ?
C18 C13 C14 118.5(5) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.8(7) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.7(7) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C17 120.7(7) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 120.3 . . ?
C16 C17 C18 119.5(7) . . ?
C18 C17 H17 120.3 . . ?
C13 C18 C17 119.7(6) . . ?
C13 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C31 C19 S1 123.3(7) . . ?
C31 C19 C34 117.2(9) . . ?
C34 C19 S1 118.1(6) . . ?
C20 C19 S1 120.9(6) . . ?
C20 C19 C24 120.2(7) . . ?
C24 C19 S1 118.9(5) . . ?
C32 C22 C25 124.1(8) . . ?
C32 C22 C33 117.6(10) . . ?
C33 C22 C25 117.7(7) . . ?
C21 C22 C25 123.4(6) . . ?
C21 C22 C23 116.3(7) . . ?
C23 C22 C25 120.2(6) . . ?
C26 C25 C22 121.2(5) . . ?
C30 C25 C22 121.7(5) . . ?
C30 C25 C26 117.1(5) . . ?
C25 C26 H26 119.1 . . ?
C27 C26 C25 121.7(6) . . ?
C27 C26 H26 119.1 . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.3(6) . . ?
C28 C27 H27 119.8 . . ?
C27 C28 S2 119.9(4) . . ?
C29 C28 S2 120.7(4) . . ?
C29 C28 C27 119.1(5) . . ?
C28 C29 H29 119.6 . . ?
C28 C29 C30 120.7(5) . . ?
C30 C29 H29 119.6 . . ?
C25 C30 C29 120.9(5) . . ?
C25 C30 H30 119.6 . . ?
C29 C30 H30 119.6 . . ?
C19 C31 H31 119.7 . . ?
C19 C31 C32 120.6(14) . . ?
C32 C31 H31 119.7 . . ?
C22 C32 C31 123.3(14) . . ?
C22 C32 H32 118.4 . . ?
C31 C32 H32 118.4 . . ?
C22 C33 H33 120.9 . . ?
C34 C33 C22 118.2(11) . . ?
C34 C33 H33 120.9 . . ?
C19 C34 H34 119.5 . . ?
C33 C34 C19 121.0(11) . . ?
C33 C34 H34 119.5 . . ?
C35 N3 C36 119.0(9) . . ?
C35 N3 C37 119.8(11) . . ?
C36 N3 C37 121.2(11) . . ?
O7 C35 N3 127.0(12) . . ?
O7 C35 H35 116.5 . . ?
N3 C35 H35 116.5 . . ?
N3 C36 H36A 109.5 . . ?
N3 C36 H36B 109.5 . . ?
N3 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
N3 C37 H37A 109.5 . . ?
N3 C37 H37B 109.5 . . ?
N3 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C19 C20 H20 120.1 . . ?
C19 C20 C21 119.7(10) . . ?
C21 C20 H20 120.1 . . ?
C22 C21 C20 122.8(10) . . ?
C22 C21 H21 118.6 . . ?
C20 C21 H21 118.6 . . ?
C22 C23 H23 119.4 . . ?
C24 C23 C22 121.3(8) . . ?
C24 C23 H23 119.4 . . ?
C19 C24 H24 120.4 . . ?
C23 C24 C19 119.2(8) . . ?
C23 C24 H24 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Bi1 N1 C1 C2 -179.9(5) . . . . ?
Bi1 N1 C12 C4 -177.5(4) . . . . ?
Bi1 N1 C12 C11 1.1(7) . . . . ?
Bi1 N2 C10 C9 -171.9(6) . . . . ?
Bi1 N2 C11 C7 174.6(4) . . . . ?
Bi1 N2 C11 C12 -6.6(7) . . . . ?
Bi1 C13 C14 C15 177.6(5) . . . . ?
Bi1 C13 C18 C17 -178.3(5) . . . . ?
S1 C19 C31 C32 178.2(17) . . . . ?
S1 C19 C34 C33 177.1(12) . . . . ?
S1 C19 C20 C21 -178.3(9) . . . . ?
S1 C19 C24 C23 176.5(11) . . . . ?
S2 C28 C29 C30 -172.9(5) . . . . ?
O1 S1 C19 C31 80.5(18) . . . . ?
O1 S1 C19 C34 -85.5(10) . . . . ?
O1 S1 C19 C20 48.4(9) . . . . ?
O1 S1 C19 C24 -135.0(10) . . . . ?
O2 S1 O1 Bi1 126.8(2) . . . . ?
O2 S1 C19 C31 -159.0(18) . . . . ?
O2 S1 C19 C34 35.0(11) . . . . ?
O2 S1 C19 C20 168.9(8) . . . . ?
O2 S1 C19 C24 -14.5(10) . . . . ?
O3 S1 O1 Bi1 -2.2(3) . . . . ?
O3 S1 C19 C31 -34.3(18) . . . . ?
O3 S1 C19 C34 159.7(10) . . . . ?
O3 S1 C19 C20 -66.4(9) . . . . ?
O3 S1 C19 C24 110.2(10) . . . . ?
O4 S2 O5 Bi1 -12.0(3) . . . 2_556 ?
O4 S2 C28 C27 -66.1(6) . . . . ?
O4 S2 C28 C29 108.1(5) . . . . ?
O5 S2 C28 C27 51.0(6) . . . . ?
O5 S2 C28 C29 -134.8(5) . . . . ?
O6 S2 O5 Bi1 118.5(2) . . . 2_556 ?
O6 S2 C28 C27 171.1(6) . . . . ?
O6 S2 C28 C29 -14.7(6) . . . . ?
N1 C1 C2 C3 -2.6(11) . . . . ?
N2 C11 C12 N1 3.7(8) . . . . ?
N2 C11 C12 C4 -177.6(5) . . . . ?
C1 N1 C12 C4 1.4(8) . . . . ?
C1 N1 C12 C11 -180.0(6) . . . . ?
C1 C2 C3 C4 1.3(11) . . . . ?
C2 C3 C4 C5 -179.2(7) . . . . ?
C2 C3 C4 C12 1.2(10) . . . . ?
C3 C4 C5 C6 180.0(7) . . . . ?
C3 C4 C12 N1 -2.6(9) . . . . ?
C3 C4 C12 C11 178.8(6) . . . . ?
C4 C5 C6 C7 1.4(12) . . . . ?
C5 C4 C12 N1 177.8(6) . . . . ?
C5 C4 C12 C11 -0.9(9) . . . . ?
C5 C6 C7 C8 -178.7(7) . . . . ?
C5 C6 C7 C11 -1.0(11) . . . . ?
C6 C7 C8 C9 178.4(8) . . . . ?
C6 C7 C11 N2 178.5(6) . . . . ?
C6 C7 C11 C12 -0.3(9) . . . . ?
C7 C8 C9 C10 1.2(12) . . . . ?
C7 C11 C12 N1 -177.4(5) . . . . ?
C7 C11 C12 C4 1.2(9) . . . . ?
C8 C7 C11 N2 -3.6(9) . . . . ?
C8 C7 C11 C12 177.6(6) . . . . ?
C8 C9 C10 N2 -0.3(12) . . . . ?
C10 N2 C11 C7 4.5(9) . . . . ?
C10 N2 C11 C12 -176.7(6) . . . . ?
C11 N2 C10 C9 -2.5(11) . . . . ?
C11 C7 C8 C9 0.6(11) . . . . ?
C12 N1 C1 C2 1.3(9) . . . . ?
C12 C4 C5 C6 -0.4(10) . . . . ?
C13 C14 C15 C16 -1.4(12) . . . . ?
C14 C13 C18 C17 -1.1(9) . . . . ?
C14 C15 C16 C17 3.2(13) . . . . ?
C15 C16 C17 C18 -3.9(13) . . . . ?
C16 C17 C18 C13 2.8(11) . . . . ?
C18 C13 C14 C15 0.4(9) . . . . ?
C19 S1 O1 Bi1 -116.8(2) . . . . ?
C19 C31 C32 C22 8(4) . . . . ?
C19 C20 C21 C22 1.9(19) . . . . ?
C22 C25 C26 C27 -177.0(7) . . . . ?
C22 C25 C30 C29 178.9(6) . . . . ?
C22 C33 C34 C19 3(2) . . . . ?
C22 C23 C24 C19 2(2) . . . . ?
C25 C22 C32 C31 176.1(18) . . . . ?
C25 C22 C33 C34 178.3(12) . . . . ?
C25 C22 C21 C20 178.0(10) . . . . ?
C25 C22 C23 C24 -179.7(11) . . . . ?
C25 C26 C27 C28 -3.0(13) . . . . ?
C26 C25 C30 C29 -1.5(10) . . . . ?
C26 C27 C28 S2 174.9(7) . . . . ?
C26 C27 C28 C29 0.6(11) . . . . ?
C27 C28 C29 C30 1.3(10) . . . . ?
C28 S2 O5 Bi1 -125.3(2) . . . 2_556 ?
C28 C29 C30 C25 -0.8(10) . . . . ?
C30 C25 C26 C27 3.5(12) . . . . ?
C31 C19 C34 C33 10(2) . . . . ?
C32 C22 C25 C26 -14(2) . . . . ?
C32 C22 C25 C30 166.1(19) . . . . ?
C32 C22 C33 C34 -11(2) . . . . ?
C33 C22 C25 C26 156.8(12) . . . . ?
C33 C22 C25 C30 -23.7(13) . . . . ?
C33 C22 C32 C31 6(3) . . . . ?
C34 C19 C31 C32 -16(3) . . . . ?
C36 N3 C35 O7 -5(2) . . . . ?
C37 N3 C35 O7 177.3(15) . . . . ?
C20 C19 C24 C23 -6.9(18) . . . . ?
C21 C22 C25 C26 21.9(12) . . . . ?
C21 C22 C25 C30 -158.5(9) . . . . ?
C21 C22 C23 C24 4.7(19) . . . . ?
C23 C22 C25 C26 -153.2(11) . . . . ?
C23 C22 C25 C30 26.3(13) . . . . ?
C23 C22 C21 C20 -6.7(17) . . . . ?
C24 C19 C20 C21 5.1(17) . . . . ?

_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
