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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Ligand-precursor
_database_code_depnum_ccdc_archive 'CCDC 2073386'
loop_
_audit_author_name
_audit_author_address
'Shigeru Shimada'
;National Institute of Advanced Industrial Science and Technology (AIST)
Japan
;
_audit_update_record             
;
2021-03-26 deposited with the CCDC.	2021-05-18 downloaded from the CCDC.
;
_audit_creation_date             2021-02-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6257)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
s-shimada@aist.go.jp
_chemical_name_common            ?
_chemical_name_systematic        
2,2'-((2-bromophenyl)(methoxy)methylene)bis(benzo[d]thiazole)
_chemical_formula_moiety         'C22 H15 Br N2 O S2'
_chemical_formula_sum            'C22 H15 Br N2 O S2'
_chemical_formula_weight         467.39
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H15 Br N2 O S2'
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'
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'
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      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   29.9380(7)
_cell_length_b                   18.6991(4)
_cell_length_c                   13.9399(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7803.7(3)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    10897
_cell_measurement_temperature    153
_cell_measurement_theta_max      28.7360
_cell_measurement_theta_min      1.8600
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.337
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             3776
_exptl_crystal_recrystallization_method 'crystallized from benzene'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11834
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.866
_diffrn_reflns_theta_min         1.945
_diffrn_ambient_temperature      153
_diffrn_detector                 'Bruker APEX area detector'
_diffrn_detector_area_resol_mean 8.366
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

 # Type Start End Width tₑₓₚ ω θ κ φ Frames
#--------------------------------------------------------------------------
 1 ω 2.30 183.91 0.30 9.99 -- 28.00 73.65 -25.70 606
 2 ω 2.30 132.66 0.30 9.99 -- 28.00 73.65 64.30 435
 3 ω 2.30 71.23 0.30 9.99 -- 28.00 73.65 154.30 230
 4 ω 2.30 17.28 0.30 9.99 -- 28.00 73.65 -25.70 50
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0188993000
_diffrn_orient_matrix_UB_12      0.0113824000
_diffrn_orient_matrix_UB_13      0.0266269000
_diffrn_orient_matrix_UB_21      -0.0127099000
_diffrn_orient_matrix_UB_22      -0.0284170000
_diffrn_orient_matrix_UB_23      -0.0197668000
_diffrn_orient_matrix_UB_31      0.0065279000
_diffrn_orient_matrix_UB_32      -0.0224045000
_diffrn_orient_matrix_UB_33      0.0385964000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.822
_reflns_Friedel_fraction_full    0.930
_reflns_Friedel_fraction_max     0.879
_reflns_number_gt                4177
_reflns_number_total             4352
_reflns_odcompleteness_completeness 98.28
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.82
_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       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.962
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 
;
 Flack x determined using 1778 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.015(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4352
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      1.050
_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)+(0.0626P)²+29.5270P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1022
_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.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C17(H17), C18(H18), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_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
Br1 Br 0.50488(2) 0.81578(3) 0.37077(4) 0.03709(16) Uani 1 1 d . . . . .
S1 S 0.54754(7) 0.60203(9) 0.66523(11) 0.0508(4) Uani 1 1 d . . . . .
S2 S 0.60322(4) 0.78383(6) 0.52848(8) 0.0261(2) Uani 1 1 d . . . . .
O1 O 0.51821(11) 0.72467(19) 0.5683(2) 0.0269(7) Uani 1 1 d . . . . .
N1 N 0.57757(18) 0.5601(2) 0.5004(3) 0.0353(11) Uani 1 1 d . . . . .
N2 N 0.59597(12) 0.70264(19) 0.3786(3) 0.0231(7) Uani 1 1 d . . . . .
C1 C 0.48788(16) 0.7191(2) 0.3544(4) 0.0265(9) Uani 1 1 d . . . . .
C2 C 0.45825(17) 0.7047(3) 0.2803(4) 0.0333(10) Uani 1 1 d . . . . .
H2 H 0.448767 0.741406 0.240215 0.040 Uiso 1 1 calc R U . . .
C3 C 0.44288(19) 0.6362(3) 0.2662(4) 0.0404(13) Uani 1 1 d . . . . .
H3 H 0.423023 0.626338 0.216604 0.048 Uiso 1 1 calc R U . . .
C4 C 0.45718(19) 0.5821(3) 0.3262(5) 0.0398(12) Uani 1 1 d . . . . .
H4 H 0.446782 0.535731 0.317353 0.048 Uiso 1 1 calc R U . . .
C5 C 0.48696(17) 0.5968(3) 0.3995(4) 0.0317(10) Uani 1 1 d . . . . .
H5 H 0.495956 0.559988 0.439993 0.038 Uiso 1 1 calc R U . . .
C6 C 0.50366(15) 0.6649(3) 0.4140(3) 0.0230(8) Uani 1 1 d . . . . .
C7 C 0.53636(15) 0.6798(2) 0.4958(3) 0.0232(9) Uani 1 1 d . . . . .
C8 C 0.55350(15) 0.6112(3) 0.5437(3) 0.0261(9) Uani 1 1 d . . . . .
C9 C 0.5748(3) 0.5221(3) 0.6602(5) 0.0464(14) Uani 1 1 d . . . . .
C10 C 0.5868(3) 0.4746(5) 0.7351(6) 0.067(2) Uani 1 1 d . . . . .
H10 H 0.579345 0.484614 0.798395 0.080 Uiso 1 1 calc R U . . .
C11 C 0.6095(2) 0.4142(4) 0.7122(5) 0.0532(17) Uani 1 1 d . . . . .
H11 H 0.617028 0.381985 0.760417 0.064 Uiso 1 1 calc R U . . .
C12 C 0.62180(19) 0.3995(3) 0.6176(6) 0.0491(15) Uani 1 1 d . . . . .
H12 H 0.637923 0.358207 0.604071 0.059 Uiso 1 1 calc R U . . .
C13 C 0.6105(2) 0.4447(3) 0.5450(5) 0.0432(14) Uani 1 1 d . . . . .
H13 H 0.618002 0.434018 0.481845 0.052 Uiso 1 1 calc R U . . .
C14 C 0.58730(17) 0.5079(3) 0.5677(5) 0.0346(11) Uani 1 1 d . . . . .
C15 C 0.57731(15) 0.7184(2) 0.4587(3) 0.0229(8) Uani 1 1 d . . . . .
C16 C 0.64316(15) 0.7933(3) 0.4394(3) 0.0242(9) Uani 1 1 d . . . . .
C17 C 0.67955(17) 0.8385(3) 0.4350(4) 0.0334(11) Uani 1 1 d . . . . .
H17 H 0.685721 0.870195 0.484697 0.040 Uiso 1 1 calc R U . . .
C18 C 0.70665(17) 0.8354(3) 0.3544(4) 0.0350(11) Uani 1 1 d . . . . .
H18 H 0.731636 0.864800 0.350108 0.042 Uiso 1 1 calc R U . . .
C19 C 0.69659(17) 0.7884(3) 0.2795(4) 0.0331(10) Uani 1 1 d . . . . .
H19 H 0.714822 0.788084 0.225530 0.040 Uiso 1 1 calc R U . . .
C20 C 0.66107(17) 0.7431(3) 0.2828(4) 0.0290(10) Uani 1 1 d . . . . .
H20 H 0.655231 0.711664 0.232676 0.035 Uiso 1 1 calc R U . . .
C21 C 0.63345(15) 0.7452(2) 0.3644(3) 0.0232(8) Uani 1 1 d . . . . .
C22 C 0.47217(17) 0.7137(3) 0.5917(4) 0.0351(11) Uani 1 1 d . . . . .
H22A H 0.453752 0.732611 0.541396 0.053 Uiso 1 1 calc R U . . .
H22B H 0.465363 0.737621 0.650850 0.053 Uiso 1 1 calc R U . . .
H22C H 0.466519 0.663396 0.598624 0.053 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
Br1 C1 1.893(5) . ?
S1 C8 1.712(5) . ?
S1 C9 1.705(7) . ?
S2 C15 1.746(5) . ?
S2 C16 1.733(5) . ?
O1 C7 1.421(6) . ?
O1 C22 1.431(6) . ?
N1 C8 1.339(6) . ?
N1 C14 1.385(7) . ?
N2 C15 1.283(6) . ?
N2 C21 1.390(6) . ?
C1 C2 1.387(7) . ?
C1 C6 1.392(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.376(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.380(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(7) . ?
C6 C7 1.528(6) . ?
C7 C8 1.535(6) . ?
C7 C15 1.514(6) . ?
C9 C10 1.417(9) . ?
C9 C14 1.368(9) . ?
C10 H10 0.9300 . ?
C10 C11 1.356(11) . ?
C11 H11 0.9300 . ?
C11 C12 1.396(11) . ?
C12 H12 0.9300 . ?
C12 C13 1.361(9) . ?
C13 H13 0.9300 . ?
C13 C14 1.408(8) . ?
C16 C17 1.381(7) . ?
C16 C21 1.409(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.387(8) . ?
C18 H18 0.9300 . ?
C18 C19 1.397(8) . ?
C19 H19 0.9300 . ?
C19 C20 1.360(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.406(7) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C9 S1 C8 89.8(3) . . ?
C16 S2 C15 88.8(2) . . ?
C7 O1 C22 116.5(4) . . ?
C8 N1 C14 108.1(4) . . ?
C15 N2 C21 110.1(4) . . ?
C2 C1 Br1 116.5(4) . . ?
C2 C1 C6 121.3(5) . . ?
C6 C1 Br1 122.1(4) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.1(5) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.4(5) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.2(5) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.6(5) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C7 122.0(4) . . ?
C5 C6 C1 117.4(4) . . ?
C5 C6 C7 120.5(4) . . ?
O1 C7 C6 113.1(4) . . ?
O1 C7 C8 108.2(4) . . ?
O1 C7 C15 105.7(4) . . ?
C6 C7 C8 112.7(4) . . ?
C15 C7 C6 110.5(4) . . ?
C15 C7 C8 106.0(4) . . ?
N1 C8 S1 115.5(4) . . ?
N1 C8 C7 125.4(4) . . ?
C7 C8 S1 118.6(4) . . ?
C10 C9 S1 129.8(6) . . ?
C14 C9 S1 109.8(4) . . ?
C14 C9 C10 120.2(6) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 C9 118.4(7) . . ?
C11 C10 H10 120.8 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.2(6) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.0(6) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 120.8 . . ?
C12 C13 C14 118.4(7) . . ?
C14 C13 H13 120.8 . . ?
N1 C14 C13 122.9(6) . . ?
C9 C14 N1 116.4(5) . . ?
C9 C14 C13 120.6(6) . . ?
N2 C15 S2 116.9(3) . . ?
N2 C15 C7 122.8(4) . . ?
C7 C15 S2 120.2(3) . . ?
C17 C16 S2 129.7(4) . . ?
C17 C16 C21 121.4(4) . . ?
C21 C16 S2 108.9(3) . . ?
C16 C17 H17 120.9 . . ?
C16 C17 C18 118.1(5) . . ?
C18 C17 H17 120.9 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.3(5) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 118.8 . . ?
C20 C19 C18 122.4(5) . . ?
C20 C19 H19 118.8 . . ?
C19 C20 H20 121.0 . . ?
C19 C20 C21 118.0(5) . . ?
C21 C20 H20 121.0 . . ?
N2 C21 C16 115.2(4) . . ?
N2 C21 C20 125.0(4) . . ?
C20 C21 C16 119.8(4) . . ?
O1 C22 H22A 109.5 . . ?
O1 C22 H22B 109.5 . . ?
O1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
Br1 C1 C2 C3 -177.4(4) . . . . ?
Br1 C1 C6 C5 176.0(4) . . . . ?
Br1 C1 C6 C7 -0.9(7) . . . . ?
S1 C9 C10 C11 -178.6(7) . . . . ?
S1 C9 C14 N1 2.5(7) . . . . ?
S1 C9 C14 C13 179.9(5) . . . . ?
S2 C16 C17 C18 -179.9(4) . . . . ?
S2 C16 C21 N2 -0.5(5) . . . . ?
S2 C16 C21 C20 179.5(3) . . . . ?
O1 C7 C8 S1 0.5(5) . . . . ?
O1 C7 C8 N1 -171.4(5) . . . . ?
O1 C7 C15 S2 20.9(5) . . . . ?
O1 C7 C15 N2 -162.9(4) . . . . ?
C1 C2 C3 C4 0.0(9) . . . . ?
C1 C6 C7 O1 63.9(6) . . . . ?
C1 C6 C7 C8 -172.9(4) . . . . ?
C1 C6 C7 C15 -54.5(6) . . . . ?
C2 C1 C6 C5 -3.1(8) . . . . ?
C2 C1 C6 C7 179.9(5) . . . . ?
C2 C3 C4 C5 -0.4(10) . . . . ?
C3 C4 C5 C6 -1.0(9) . . . . ?
C4 C5 C6 C1 2.7(8) . . . . ?
C4 C5 C6 C7 179.7(5) . . . . ?
C5 C6 C7 O1 -113.0(5) . . . . ?
C5 C6 C7 C8 10.2(6) . . . . ?
C5 C6 C7 C15 128.6(5) . . . . ?
C6 C1 C2 C3 1.8(8) . . . . ?
C6 C7 C8 S1 -125.4(4) . . . . ?
C6 C7 C8 N1 62.7(6) . . . . ?
C6 C7 C15 S2 143.6(3) . . . . ?
C6 C7 C15 N2 -40.2(6) . . . . ?
C8 S1 C9 C10 177.7(8) . . . . ?
C8 S1 C9 C14 1.1(5) . . . . ?
C8 N1 C14 C9 -5.8(7) . . . . ?
C8 N1 C14 C13 177.0(5) . . . . ?
C8 C7 C15 S2 -93.9(4) . . . . ?
C8 C7 C15 N2 82.3(5) . . . . ?
C9 S1 C8 N1 -4.6(5) . . . . ?
C9 S1 C8 C7 -177.4(4) . . . . ?
C9 C10 C11 C12 1.5(13) . . . . ?
C10 C9 C14 N1 -174.5(7) . . . . ?
C10 C9 C14 C13 2.9(10) . . . . ?
C10 C11 C12 C13 -1.4(11) . . . . ?
C11 C12 C13 C14 1.9(9) . . . . ?
C12 C13 C14 N1 174.5(6) . . . . ?
C12 C13 C14 C9 -2.7(9) . . . . ?
C14 N1 C8 S1 6.6(6) . . . . ?
C14 N1 C8 C7 178.8(4) . . . . ?
C14 C9 C10 C11 -2.2(13) . . . . ?
C15 S2 C16 C17 179.3(5) . . . . ?
C15 S2 C16 C21 -0.4(3) . . . . ?
C15 N2 C21 C16 1.6(5) . . . . ?
C15 N2 C21 C20 -178.5(4) . . . . ?
C15 C7 C8 S1 113.6(4) . . . . ?
C15 C7 C8 N1 -58.4(6) . . . . ?
C16 S2 C15 N2 1.5(4) . . . . ?
C16 S2 C15 C7 177.9(4) . . . . ?
C16 C17 C18 C19 1.0(8) . . . . ?
C17 C16 C21 N2 179.7(4) . . . . ?
C17 C16 C21 C20 -0.3(7) . . . . ?
C17 C18 C19 C20 -1.5(8) . . . . ?
C18 C19 C20 C21 1.0(7) . . . . ?
C19 C20 C21 N2 179.9(4) . . . . ?
C19 C20 C21 C16 -0.2(7) . . . . ?
C21 N2 C15 S2 -2.0(5) . . . . ?
C21 N2 C15 C7 -178.3(4) . . . . ?
C21 C16 C17 C18 -0.2(7) . . . . ?
C22 O1 C7 C6 38.1(5) . . . . ?
C22 O1 C7 C8 -87.5(5) . . . . ?
C22 O1 C7 C15 159.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.084
_oxdiff_exptl_absorpt_empirical_full_min 0.892
####################################################################### 
# 
# 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_LBiCl2
_database_code_depnum_ccdc_archive 'CCDC 2073387'
loop_
_audit_author_name
_audit_author_address
'Shigeru Shimada'
;National Institute of Advanced Industrial Science and Technology (AIST)
Japan
;
_audit_update_record             
;
2021-03-26 deposited with the CCDC.	2021-05-18 downloaded from the CCDC.
;
_audit_creation_date             2020-04-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
s-shimada@aist.go.jp
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H15 Bi Cl2 N2 O S2'
_chemical_formula_sum            'C22 H15 Bi Cl2 N2 O S2'
_chemical_formula_weight         667.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H15 Bi1 Cl2 N2 O1 S1'
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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9561(2)
_cell_length_b                   10.6585(2)
_cell_length_c                   11.9387(2)
_cell_angle_alpha                102.1600(10)
_cell_angle_beta                 92.451(2)
_cell_angle_gamma                106.506(2)
_cell_volume                     1061.75(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6414
_cell_measurement_temperature    153
_cell_measurement_theta_max      28.6310
_cell_measurement_theta_min      1.7510
_shelx_estimated_absorpt_T_max   0.668
_shelx_estimated_absorpt_T_min   0.260
_exptl_absorpt_coefficient_mu    8.769
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.087
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             636
_exptl_crystal_recrystallization_method 'Crystallized from THF-d8'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0092
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6322
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         1.755
_diffrn_ambient_temperature      153
_diffrn_detector                 'Bruker APEX area detector'
_diffrn_detector_area_resol_mean 8.366
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      2.31 183.92   0.30    9.99    --   28.00  73.62 -25.69  606
  2  ω      2.31 132.67   0.30    9.99    --   28.00  73.62  64.31  435
  3  ω      2.31  71.24   0.30    9.99    --   28.00  73.62 154.31  230
  4  ω      2.31  17.29   0.30    9.99    --   28.00  73.62 -25.69   50
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0103237000
_diffrn_orient_matrix_UB_12      -0.0144927000
_diffrn_orient_matrix_UB_13      -0.0610970000
_diffrn_orient_matrix_UB_21      0.0277167000
_diffrn_orient_matrix_UB_22      0.0697693000
_diffrn_orient_matrix_UB_23      0.0017659000
_diffrn_orient_matrix_UB_31      0.0776597000
_diffrn_orient_matrix_UB_32      -0.0039072000
_diffrn_orient_matrix_UB_33      -0.0015893000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4158
_reflns_number_total             4255
_reflns_odcompleteness_completeness 98.13
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4255
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0169
_refine_ls_R_factor_gt           0.0163
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0241P)²+1.3203P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0401
_refine_ls_wR_factor_ref         0.0404
_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.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C17(H17), C18(H18), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_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 0.50806(2) 0.30481(2) 0.81295(2) 0.01427(4) Uani 1 1 d . . . . .
Cl1 Cl 0.23390(8) 0.13818(7) 0.80679(6) 0.02305(14) Uani 1 1 d . . . . .
Cl2 Cl 0.43141(10) 0.52184(7) 0.85784(7) 0.02674(16) Uani 1 1 d . . . . .
S1 S 0.88581(8) 0.09304(7) 0.65694(6) 0.02007(14) Uani 1 1 d . . . . .
S2 S 1.02097(8) 0.48621(7) 0.65302(6) 0.01975(14) Uani 1 1 d . . . . .
O1 O 0.8359(2) 0.25680(19) 0.49464(17) 0.0192(4) Uani 1 1 d . . . . .
N1 N 0.6145(3) 0.1124(2) 0.7062(2) 0.0155(5) Uani 1 1 d . . . . .
N2 N 0.7898(3) 0.4307(2) 0.7738(2) 0.0159(5) Uani 1 1 d . . . . .
C1 C 0.4712(3) 0.2984(3) 0.6249(2) 0.0167(5) Uani 1 1 d . . . . .
C2 C 0.3311(4) 0.3157(3) 0.5860(3) 0.0217(6) Uani 1 1 d . . . . .
H2 H 0.252031 0.317919 0.636284 0.026 Uiso 1 1 calc R U . . .
C3 C 0.3062(4) 0.3296(3) 0.4744(3) 0.0258(7) Uani 1 1 d . . . . .
H3 H 0.209693 0.339736 0.448091 0.031 Uiso 1 1 calc R U . . .
C4 C 0.4214(4) 0.3287(3) 0.4019(3) 0.0253(6) Uani 1 1 d . . . . .
H4 H 0.406528 0.342399 0.326678 0.030 Uiso 1 1 calc R U . . .
C5 C 0.5583(4) 0.3079(3) 0.4388(2) 0.0211(6) Uani 1 1 d . . . . .
H5 H 0.636830 0.306337 0.387927 0.025 Uiso 1 1 calc R U . . .
C6 C 0.5840(3) 0.2890(3) 0.5495(2) 0.0155(5) Uani 1 1 d . . . . .
C7 C 0.7413(3) 0.2689(3) 0.5854(2) 0.0145(5) Uani 1 1 d . . . . .
C8 C 0.7269(3) 0.1537(3) 0.6457(2) 0.0150(5) Uani 1 1 d . . . . .
C9 C 0.7930(3) 0.0019(3) 0.7519(2) 0.0177(5) Uani 1 1 d . . . . .
C10 C 0.8456(4) -0.0791(3) 0.8116(3) 0.0244(6) Uani 1 1 d . . . . .
H10 H 0.944952 -0.092929 0.802294 0.029 Uiso 1 1 calc R U . . .
C11 C 0.7490(4) -0.1385(3) 0.8845(3) 0.0267(7) Uani 1 1 d . . . . .
H11 H 0.782973 -0.193323 0.926949 0.032 Uiso 1 1 calc R U . . .
C12 C 0.6016(4) -0.1198(3) 0.8974(3) 0.0231(6) Uani 1 1 d . . . . .
H12 H 0.536726 -0.163473 0.947367 0.028 Uiso 1 1 calc R U . . .
C13 C 0.5492(3) -0.0396(3) 0.8392(2) 0.0192(6) Uani 1 1 d . . . . .
H13 H 0.449132 -0.027061 0.848251 0.023 Uiso 1 1 calc R U . . .
C14 C 0.6471(3) 0.0229(3) 0.7666(2) 0.0157(5) Uani 1 1 d . . . . .
C15 C 0.8377(3) 0.3936(3) 0.6748(2) 0.0148(5) Uani 1 1 d . . . . .
C16 C 1.0377(3) 0.5861(3) 0.7911(2) 0.0172(5) Uani 1 1 d . . . . .
C17 C 1.1626(3) 0.6944(3) 0.8491(3) 0.0223(6) Uani 1 1 d . . . . .
H17 H 1.254386 0.725528 0.813302 0.027 Uiso 1 1 calc R U . . .
C18 C 1.1487(4) 0.7551(3) 0.9606(3) 0.0259(7) Uani 1 1 d . . . . .
H18 H 1.231701 0.830261 1.001939 0.031 Uiso 1 1 calc R U . . .
C19 C 1.0157(4) 0.7084(3) 1.0134(3) 0.0234(6) Uani 1 1 d . . . . .
H19 H 1.010645 0.751451 1.090764 0.028 Uiso 1 1 calc R U . . .
C20 C 0.8903(4) 0.6010(3) 0.9566(2) 0.0208(6) Uani 1 1 d . . . . .
H20 H 0.799453 0.569800 0.993217 0.025 Uiso 1 1 calc R U . . .
C21 C 0.9024(3) 0.5403(3) 0.8435(2) 0.0160(5) Uani 1 1 d . . . . .
C22 C 0.7870(4) 0.1325(3) 0.4073(2) 0.0246(6) Uani 1 1 d . . . . .
H22A H 0.801963 0.151960 0.331210 0.037 Uiso 1 1 calc R U . . .
H22B H 0.676114 0.086672 0.410031 0.037 Uiso 1 1 calc R U . . .
H22C H 0.849896 0.074558 0.421428 0.037 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 Cl1 2.5768(7) . ?
Bi1 Cl2 2.5536(7) . ?
Bi1 N1 2.618(2) . ?
Bi1 N2 2.613(2) . ?
Bi1 C1 2.239(3) . ?
S1 C8 1.734(3) . ?
S1 C9 1.734(3) . ?
S2 C15 1.721(3) . ?
S2 C16 1.739(3) . ?
O1 C7 1.410(3) . ?
O1 C22 1.443(3) . ?
N1 C8 1.293(4) . ?
N1 C14 1.395(3) . ?
N2 C15 1.296(4) . ?
N2 C21 1.387(3) . ?
C1 C2 1.393(4) . ?
C1 C6 1.392(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.375(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.377(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.397(4) . ?
C6 C7 1.541(4) . ?
C7 C8 1.527(4) . ?
C7 C15 1.525(4) . ?
C9 C10 1.392(4) . ?
C9 C14 1.399(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.376(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.400(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.373(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.394(4) . ?
C16 C17 1.388(4) . ?
C16 C21 1.398(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.380(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.387(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.381(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.392(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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
Cl1 Bi1 N1 91.65(5) . . ?
Cl1 Bi1 N2 165.91(5) . . ?
Cl2 Bi1 Cl1 97.90(2) . . ?
Cl2 Bi1 N1 160.84(5) . . ?
Cl2 Bi1 N2 92.31(5) . . ?
N2 Bi1 N1 75.87(7) . . ?
C1 Bi1 Cl1 91.94(7) . . ?
C1 Bi1 Cl2 88.87(7) . . ?
C1 Bi1 N1 74.17(9) . . ?
C1 Bi1 N2 78.52(9) . . ?
C9 S1 C8 89.14(13) . . ?
C15 S2 C16 88.66(13) . . ?
C7 O1 C22 116.8(2) . . ?
C8 N1 Bi1 113.24(17) . . ?
C8 N1 C14 110.9(2) . . ?
C14 N1 Bi1 119.28(17) . . ?
C15 N2 Bi1 119.26(17) . . ?
C15 N2 C21 111.1(2) . . ?
C21 N2 Bi1 129.65(18) . . ?
C2 C1 Bi1 116.5(2) . . ?
C6 C1 Bi1 123.7(2) . . ?
C6 C1 C2 119.6(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.3(3) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 118.6(3) . . ?
C1 C6 C7 122.9(2) . . ?
C5 C6 C7 118.3(2) . . ?
O1 C7 C6 113.7(2) . . ?
O1 C7 C8 109.9(2) . . ?
O1 C7 C15 104.9(2) . . ?
C8 C7 C6 114.5(2) . . ?
C15 C7 C6 108.8(2) . . ?
C15 C7 C8 104.2(2) . . ?
N1 C8 S1 116.1(2) . . ?
N1 C8 C7 124.2(2) . . ?
C7 C8 S1 118.6(2) . . ?
C10 C9 S1 129.5(2) . . ?
C10 C9 C14 120.9(3) . . ?
C14 C9 S1 109.6(2) . . ?
C9 C10 H10 121.1 . . ?
C11 C10 C9 117.9(3) . . ?
C11 C10 H10 121.1 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.3(3) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.2(3) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 H13 121.0 . . ?
C12 C13 C14 118.0(3) . . ?
C14 C13 H13 121.0 . . ?
N1 C14 C9 114.3(2) . . ?
C13 C14 N1 125.0(3) . . ?
C13 C14 C9 120.7(3) . . ?
N2 C15 S2 116.6(2) . . ?
N2 C15 C7 121.7(2) . . ?
C7 C15 S2 121.6(2) . . ?
C17 C16 S2 128.7(2) . . ?
C17 C16 C21 121.3(3) . . ?
C21 C16 S2 109.9(2) . . ?
C16 C17 H17 121.2 . . ?
C18 C17 C16 117.5(3) . . ?
C18 C17 H17 121.2 . . ?
C17 C18 H18 119.4 . . ?
C17 C18 C19 121.3(3) . . ?
C19 C18 H18 119.4 . . ?
C18 C19 H19 119.1 . . ?
C20 C19 C18 121.8(3) . . ?
C20 C19 H19 119.1 . . ?
C19 C20 H20 121.3 . . ?
C19 C20 C21 117.4(3) . . ?
C21 C20 H20 121.3 . . ?
N2 C21 C16 113.8(2) . . ?
N2 C21 C20 125.5(3) . . ?
C20 C21 C16 120.7(3) . . ?
O1 C22 H22A 109.5 . . ?
O1 C22 H22B 109.5 . . ?
O1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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 N1 C8 S1 135.78(14) . . . . ?
Bi1 N1 C8 C7 -32.3(3) . . . . ?
Bi1 N1 C14 C9 -132.2(2) . . . . ?
Bi1 N1 C14 C13 45.9(3) . . . . ?
Bi1 N2 C15 S2 177.10(11) . . . . ?
Bi1 N2 C15 C7 -6.8(3) . . . . ?
Bi1 N2 C21 C16 -176.49(18) . . . . ?
Bi1 N2 C21 C20 5.2(4) . . . . ?
Bi1 C1 C2 C3 172.1(2) . . . . ?
Bi1 C1 C6 C5 -169.7(2) . . . . ?
Bi1 C1 C6 C7 5.8(4) . . . . ?
S1 C9 C10 C11 178.6(2) . . . . ?
S1 C9 C14 N1 -1.9(3) . . . . ?
S1 C9 C14 C13 180.0(2) . . . . ?
S2 C16 C17 C18 -178.1(2) . . . . ?
S2 C16 C21 N2 -1.0(3) . . . . ?
S2 C16 C21 C20 177.5(2) . . . . ?
O1 C7 C8 S1 34.3(3) . . . . ?
O1 C7 C8 N1 -157.9(2) . . . . ?
O1 C7 C15 S2 0.0(3) . . . . ?
O1 C7 C15 N2 -175.9(2) . . . . ?
C1 C2 C3 C4 -1.1(5) . . . . ?
C1 C6 C7 O1 177.7(2) . . . . ?
C1 C6 C7 C8 50.2(3) . . . . ?
C1 C6 C7 C15 -65.9(3) . . . . ?
C2 C1 C6 C5 5.0(4) . . . . ?
C2 C1 C6 C7 -179.5(2) . . . . ?
C2 C3 C4 C5 2.9(5) . . . . ?
C3 C4 C5 C6 -0.7(5) . . . . ?
C4 C5 C6 C1 -3.2(4) . . . . ?
C4 C5 C6 C7 -178.9(3) . . . . ?
C5 C6 C7 O1 -6.8(3) . . . . ?
C5 C6 C7 C8 -134.3(3) . . . . ?
C5 C6 C7 C15 109.6(3) . . . . ?
C6 C1 C2 C3 -2.9(4) . . . . ?
C6 C7 C8 S1 163.68(18) . . . . ?
C6 C7 C8 N1 -28.5(4) . . . . ?
C6 C7 C15 S2 -122.0(2) . . . . ?
C6 C7 C15 N2 62.1(3) . . . . ?
C8 S1 C9 C10 -177.4(3) . . . . ?
C8 S1 C9 C14 0.9(2) . . . . ?
C8 N1 C14 C9 2.1(3) . . . . ?
C8 N1 C14 C13 -179.8(3) . . . . ?
C8 C7 C15 S2 115.5(2) . . . . ?
C8 C7 C15 N2 -60.4(3) . . . . ?
C9 S1 C8 N1 0.3(2) . . . . ?
C9 S1 C8 C7 169.1(2) . . . . ?
C9 C10 C11 C12 0.8(5) . . . . ?
C10 C9 C14 N1 176.5(2) . . . . ?
C10 C9 C14 C13 -1.6(4) . . . . ?
C10 C11 C12 C13 -1.1(5) . . . . ?
C11 C12 C13 C14 0.1(4) . . . . ?
C12 C13 C14 N1 -176.6(3) . . . . ?
C12 C13 C14 C9 1.3(4) . . . . ?
C14 N1 C8 S1 -1.4(3) . . . . ?
C14 N1 C8 C7 -169.5(2) . . . . ?
C14 C9 C10 C11 0.5(4) . . . . ?
C15 S2 C16 C17 178.9(3) . . . . ?
C15 S2 C16 C21 0.4(2) . . . . ?
C15 N2 C21 C16 1.1(3) . . . . ?
C15 N2 C21 C20 -177.2(3) . . . . ?
C15 C7 C8 S1 -77.6(2) . . . . ?
C15 C7 C8 N1 90.2(3) . . . . ?
C16 S2 C15 N2 0.2(2) . . . . ?
C16 S2 C15 C7 -175.9(2) . . . . ?
C16 C17 C18 C19 0.9(5) . . . . ?
C17 C16 C21 N2 -179.5(3) . . . . ?
C17 C16 C21 C20 -1.1(4) . . . . ?
C17 C18 C19 C20 -1.2(5) . . . . ?
C18 C19 C20 C21 0.2(5) . . . . ?
C19 C20 C21 N2 179.1(3) . . . . ?
C19 C20 C21 C16 0.9(4) . . . . ?
C21 N2 C15 S2 -0.8(3) . . . . ?
C21 N2 C15 C7 175.3(2) . . . . ?
C21 C16 C17 C18 0.2(4) . . . . ?
C22 O1 C7 C6 -72.9(3) . . . . ?
C22 O1 C7 C8 56.9(3) . . . . ?
C22 O1 C7 C15 168.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.286
_oxdiff_exptl_absorpt_empirical_full_min 0.794
####################################################################### 
# 
# 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_L'BiBr3
_database_code_depnum_ccdc_archive 'CCDC 2073390'
loop_
_audit_author_name
_audit_author_address
'Shigeru Shimada'
;National Institute of Advanced Industrial Science and Technology (AIST)
Japan
;
_audit_update_record             
;
2021-03-26 deposited with the CCDC.	2021-05-18 downloaded from the CCDC.
;
_audit_creation_date             2021-02-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
s-shimada@aist.go.jp
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H15 Bi Br4 N2 O S2'
_chemical_formula_sum            'C22 H15 Bi Br4 N2 O S2'
_chemical_formula_weight         916.10
_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'
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'
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'
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                   11.1267(6)
_cell_length_b                   14.9545(9)
_cell_length_c                   15.4839(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.4860(10)
_cell_angle_gamma                90
_cell_volume                     2574.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7580
_cell_measurement_temperature    153.15
_cell_measurement_theta_max      28.143
_cell_measurement_theta_min      2.283
_shelx_estimated_absorpt_T_max   0.241
_shelx_estimated_absorpt_T_min   0.199
_exptl_absorpt_coefficient_mu    13.240
_exptl_absorpt_correction_T_max  0.2414
_exptl_absorpt_correction_T_min  0.1991
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS; Sheldrick 1996'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.364
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1696
_exptl_crystal_recrystallization_method 'Crystallized from C6DD6'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15295
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         28.281
_diffrn_reflns_theta_min         1.894
_diffrn_ambient_temperature      153.15
_diffrn_detector                 'Bruker APEX area detector'
_diffrn_detector_area_resol_mean 8.366
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5217
_reflns_number_total             5815
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.015
_refine_diff_density_min         -0.709
_refine_diff_density_rms         0.114
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         5815
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0219
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0194P)²+2.0374P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0473
_refine_ls_wR_factor_ref         0.0485
_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.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C17(H17), C18(H18), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_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 0.86376(2) 0.31822(2) 0.39571(2) 0.01780(4) Uani 1 1 d . . . . .
Br1 Br 1.09174(3) 0.34137(3) 0.44991(3) 0.03280(9) Uani 1 1 d . . . . .
Br2 Br 0.74777(4) 0.40809(3) 0.51574(3) 0.03860(10) Uani 1 1 d . . . . .
Br3 Br 0.81973(3) 0.16252(2) 0.46910(2) 0.03012(9) Uani 1 1 d . . . . .
Br4 Br 1.09077(3) 0.38015(2) 0.12305(3) 0.03173(9) Uani 1 1 d . . . . .
S1 S 0.89672(8) 0.17849(5) 0.08979(5) 0.02077(17) Uani 1 1 d . . . . .
S2 S 0.56558(7) 0.30730(6) 0.12648(5) 0.02158(17) Uani 1 1 d . . . . .
O1 O 0.7989(2) 0.35035(15) 0.07135(14) 0.0227(5) Uani 1 1 d . . . . .
N1 N 0.9275(2) 0.22646(18) 0.24998(16) 0.0173(6) Uani 1 1 d . . . . .
N2 N 0.6718(2) 0.29705(18) 0.27754(17) 0.0174(6) Uani 1 1 d . . . . .
C1 C 0.9938(3) 0.4380(2) 0.2042(2) 0.0230(7) Uani 1 1 d . . . . .
C2 C 1.0498(3) 0.5036(2) 0.2557(2) 0.0293(8) Uani 1 1 d . . . . .
H2 H 1.133450 0.514847 0.251701 0.035 Uiso 1 1 calc R U . . .
C3 C 0.9834(3) 0.5522(2) 0.3123(3) 0.0309(8) Uani 1 1 d . . . . .
H3 H 1.021966 0.594336 0.350141 0.037 Uiso 1 1 calc R U . . .
C4 C 0.8605(3) 0.5394(2) 0.3137(2) 0.0298(8) Uani 1 1 d . . . . .
H4 H 0.813424 0.575851 0.349457 0.036 Uiso 1 1 calc R U . . .
C5 C 0.8059(3) 0.4732(2) 0.2630(2) 0.0239(7) Uani 1 1 d . . . . .
H5 H 0.721218 0.465449 0.264382 0.029 Uiso 1 1 calc R U . . .
C6 C 0.8715(3) 0.4177(2) 0.2101(2) 0.0175(6) Uani 1 1 d . . . . .
C7 C 0.8143(3) 0.3384(2) 0.1616(2) 0.0171(7) Uani 1 1 d . . . . .
C8 C 0.8829(3) 0.2522(2) 0.1749(2) 0.0169(6) Uani 1 1 d . . . . .
C9 C 0.9718(3) 0.1053(2) 0.1604(2) 0.0184(7) Uani 1 1 d . . . . .
C10 C 1.0221(3) 0.0221(2) 0.1427(2) 0.0248(7) Uani 1 1 d . . . . .
H10 H 1.014969 -0.003310 0.086440 0.030 Uiso 1 1 calc R U . . .
C11 C 1.0828(3) -0.0220(2) 0.2100(2) 0.0271(8) Uani 1 1 d . . . . .
H11 H 1.119408 -0.078061 0.199492 0.033 Uiso 1 1 calc R U . . .
C12 C 1.0911(3) 0.0142(2) 0.2926(2) 0.0254(8) Uani 1 1 d . . . . .
H12 H 1.132622 -0.018036 0.337583 0.031 Uiso 1 1 calc R U . . .
C13 C 1.0403(3) 0.0959(2) 0.3110(2) 0.0238(7) Uani 1 1 d . . . . .
H13 H 1.045435 0.119839 0.367847 0.029 Uiso 1 1 calc R U . . .
C14 C 0.9810(3) 0.1424(2) 0.2433(2) 0.0178(6) Uani 1 1 d . . . . .
C15 C 0.6886(3) 0.3166(2) 0.1971(2) 0.0165(6) Uani 1 1 d . . . . .
C16 C 0.4799(3) 0.2752(2) 0.2120(2) 0.0190(7) Uani 1 1 d . . . . .
C17 C 0.3580(3) 0.2539(2) 0.2115(2) 0.0248(8) Uani 1 1 d . . . . .
H17 H 0.309771 0.254280 0.159406 0.030 Uiso 1 1 calc R U . . .
C18 C 0.3102(3) 0.2326(3) 0.2888(2) 0.0304(8) Uani 1 1 d . . . . .
H18 H 0.226932 0.218995 0.290318 0.036 Uiso 1 1 calc R U . . .
C19 C 0.3808(3) 0.2302(2) 0.3655(2) 0.0284(8) Uani 1 1 d . . . . .
H19 H 0.344769 0.214775 0.417997 0.034 Uiso 1 1 calc R U . . .
C20 C 0.5020(3) 0.2500(2) 0.3664(2) 0.0251(8) Uani 1 1 d . . . . .
H20 H 0.549914 0.247927 0.418652 0.030 Uiso 1 1 calc R U . . .
C21 C 0.5525(3) 0.2733(2) 0.2883(2) 0.0173(6) Uani 1 1 d . . . . .
C22 C 0.7697(4) 0.4391(2) 0.0412(2) 0.0338(9) Uani 1 1 d . . . . .
H22A H 0.745336 0.436942 -0.020351 0.051 Uiso 1 1 calc R U . . .
H22B H 0.840268 0.477855 0.049510 0.051 Uiso 1 1 calc R U . . .
H22C H 0.703413 0.463038 0.073951 0.051 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 Br1 2.6597(4) . ?
Bi1 Br2 2.6709(4) . ?
Bi1 Br3 2.6459(4) . ?
Bi1 N1 2.760(3) . ?
Bi1 N2 2.769(3) . ?
Br4 C1 1.899(3) . ?
S1 C8 1.730(3) . ?
S1 C9 1.735(3) . ?
S2 C15 1.721(3) . ?
S2 C16 1.732(3) . ?
O1 C7 1.411(4) . ?
O1 C22 1.440(4) . ?
N1 C8 1.303(4) . ?
N1 C14 1.397(4) . ?
N2 C15 1.300(4) . ?
N2 C21 1.392(4) . ?
C1 C2 1.395(5) . ?
C1 C6 1.401(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.378(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.396(5) . ?
C6 C7 1.528(4) . ?
C7 C8 1.508(4) . ?
C7 C15 1.560(4) . ?
C9 C10 1.396(4) . ?
C9 C14 1.399(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.385(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.388(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.398(4) . ?
C16 C17 1.392(4) . ?
C16 C21 1.403(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.369(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.395(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.381(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.399(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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
Br1 Bi1 Br2 101.418(14) . . ?
Br1 Bi1 N1 92.71(5) . . ?
Br1 Bi1 N2 157.05(6) . . ?
Br2 Bi1 N1 165.51(5) . . ?
Br2 Bi1 N2 97.77(6) . . ?
Br3 Bi1 Br1 99.839(12) . . ?
Br3 Bi1 Br2 92.288(14) . . ?
Br3 Bi1 N1 88.43(6) . . ?
Br3 Bi1 N2 91.80(6) . . ?
N1 Bi1 N2 67.73(8) . . ?
C8 S1 C9 88.77(15) . . ?
C15 S2 C16 89.17(15) . . ?
C7 O1 C22 116.9(3) . . ?
C8 N1 Bi1 118.8(2) . . ?
C8 N1 C14 110.3(3) . . ?
C14 N1 Bi1 129.29(19) . . ?
C15 N2 Bi1 117.9(2) . . ?
C15 N2 C21 110.5(3) . . ?
C21 N2 Bi1 131.48(19) . . ?
C2 C1 Br4 116.5(3) . . ?
C2 C1 C6 121.8(3) . . ?
C6 C1 Br4 121.7(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.7(3) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.0 . . ?
C4 C5 C6 122.0(3) . . ?
C6 C5 H5 119.0 . . ?
C1 C6 C7 121.4(3) . . ?
C5 C6 C1 116.4(3) . . ?
C5 C6 C7 122.2(3) . . ?
O1 C7 C6 114.8(3) . . ?
O1 C7 C8 106.4(3) . . ?
O1 C7 C15 107.7(2) . . ?
C6 C7 C15 110.5(3) . . ?
C8 C7 C6 113.5(3) . . ?
C8 C7 C15 103.3(2) . . ?
N1 C8 S1 116.6(2) . . ?
N1 C8 C7 123.1(3) . . ?
C7 C8 S1 120.1(2) . . ?
C10 C9 S1 128.6(3) . . ?
C10 C9 C14 121.3(3) . . ?
C14 C9 S1 110.1(2) . . ?
C9 C10 H10 121.2 . . ?
C11 C10 C9 117.6(3) . . ?
C11 C10 H10 121.2 . . ?
C10 C11 H11 119.3 . . ?
C10 C11 C12 121.3(3) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 119.2 . . ?
C13 C12 C11 121.5(3) . . ?
C13 C12 H12 119.2 . . ?
C12 C13 H13 121.0 . . ?
C12 C13 C14 118.0(3) . . ?
C14 C13 H13 121.0 . . ?
N1 C14 C9 114.2(3) . . ?
N1 C14 C13 125.5(3) . . ?
C13 C14 C9 120.3(3) . . ?
N2 C15 S2 116.6(2) . . ?
N2 C15 C7 123.6(3) . . ?
C7 C15 S2 119.5(2) . . ?
C17 C16 S2 128.9(3) . . ?
C17 C16 C21 121.6(3) . . ?
C21 C16 S2 109.5(2) . . ?
C16 C17 H17 121.2 . . ?
C18 C17 C16 117.7(3) . . ?
C18 C17 H17 121.2 . . ?
C17 C18 H18 119.2 . . ?
C17 C18 C19 121.6(3) . . ?
C19 C18 H18 119.2 . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 121.1(3) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 120.9 . . ?
C19 C20 C21 118.3(3) . . ?
C21 C20 H20 120.9 . . ?
N2 C21 C16 114.3(3) . . ?
N2 C21 C20 126.0(3) . . ?
C20 C21 C16 119.7(3) . . ?
O1 C22 H22A 109.5 . . ?
O1 C22 H22B 109.5 . . ?
O1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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 N1 C8 S1 -165.40(13) . . . . ?
Bi1 N1 C8 C7 10.2(4) . . . . ?
Bi1 N1 C14 C9 163.6(2) . . . . ?
Bi1 N1 C14 C13 -16.6(4) . . . . ?
Bi1 N2 C15 S2 -177.24(13) . . . . ?
Bi1 N2 C15 C7 8.8(4) . . . . ?
Bi1 N2 C21 C16 176.2(2) . . . . ?
Bi1 N2 C21 C20 -2.9(5) . . . . ?
Br4 C1 C2 C3 176.1(3) . . . . ?
Br4 C1 C6 C5 -171.1(2) . . . . ?
Br4 C1 C6 C7 9.5(4) . . . . ?
S1 C9 C10 C11 177.1(3) . . . . ?
S1 C9 C14 N1 0.9(3) . . . . ?
S1 C9 C14 C13 -178.8(2) . . . . ?
S2 C16 C17 C18 -178.3(3) . . . . ?
S2 C16 C21 N2 0.1(4) . . . . ?
S2 C16 C21 C20 179.2(3) . . . . ?
O1 C7 C8 S1 -14.3(3) . . . . ?
O1 C7 C8 N1 170.2(3) . . . . ?
O1 C7 C15 S2 2.3(3) . . . . ?
O1 C7 C15 N2 176.2(3) . . . . ?
C1 C2 C3 C4 -4.0(5) . . . . ?
C1 C6 C7 O1 -72.4(4) . . . . ?
C1 C6 C7 C8 50.2(4) . . . . ?
C1 C6 C7 C15 165.6(3) . . . . ?
C2 C1 C6 C5 6.9(5) . . . . ?
C2 C1 C6 C7 -172.6(3) . . . . ?
C2 C3 C4 C5 4.8(6) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
C4 C5 C6 C1 -6.1(5) . . . . ?
C4 C5 C6 C7 173.3(3) . . . . ?
C5 C6 C7 O1 108.2(4) . . . . ?
C5 C6 C7 C8 -129.2(3) . . . . ?
C5 C6 C7 C15 -13.8(4) . . . . ?
C6 C1 C2 C3 -2.0(5) . . . . ?
C6 C7 C8 S1 -141.4(2) . . . . ?
C6 C7 C8 N1 43.1(4) . . . . ?
C6 C7 C15 S2 128.4(2) . . . . ?
C6 C7 C15 N2 -57.8(4) . . . . ?
C8 S1 C9 C10 -178.1(3) . . . . ?
C8 S1 C9 C14 -0.1(2) . . . . ?
C8 N1 C14 C9 -1.6(4) . . . . ?
C8 N1 C14 C13 178.2(3) . . . . ?
C8 C7 C15 S2 -110.0(3) . . . . ?
C8 C7 C15 N2 63.9(4) . . . . ?
C9 S1 C8 N1 -0.9(3) . . . . ?
C9 S1 C8 C7 -176.6(3) . . . . ?
C9 C10 C11 C12 1.4(5) . . . . ?
C10 C9 C14 N1 179.1(3) . . . . ?
C10 C9 C14 C13 -0.6(5) . . . . ?
C10 C11 C12 C13 -0.6(5) . . . . ?
C11 C12 C13 C14 -0.8(5) . . . . ?
C12 C13 C14 N1 -178.3(3) . . . . ?
C12 C13 C14 C9 1.4(5) . . . . ?
C14 N1 C8 S1 1.5(3) . . . . ?
C14 N1 C8 C7 177.1(3) . . . . ?
C14 C9 C10 C11 -0.8(5) . . . . ?
C15 S2 C16 C17 179.0(3) . . . . ?
C15 S2 C16 C21 -0.5(2) . . . . ?
C15 N2 C21 C16 0.5(4) . . . . ?
C15 N2 C21 C20 -178.6(3) . . . . ?
C15 C7 C8 S1 98.9(3) . . . . ?
C15 C7 C8 N1 -76.5(4) . . . . ?
C16 S2 C15 N2 0.8(3) . . . . ?
C16 S2 C15 C7 175.0(3) . . . . ?
C16 C17 C18 C19 -1.2(6) . . . . ?
C17 C16 C21 N2 -179.4(3) . . . . ?
C17 C16 C21 C20 -0.3(5) . . . . ?
C17 C18 C19 C20 0.4(6) . . . . ?
C18 C19 C20 C21 0.5(6) . . . . ?
C19 C20 C21 N2 178.5(3) . . . . ?
C19 C20 C21 C16 -0.5(5) . . . . ?
C21 N2 C15 S2 -0.9(4) . . . . ?
C21 N2 C15 C7 -174.8(3) . . . . ?
C21 C16 C17 C18 1.2(5) . . . . ?
C22 O1 C7 C6 -35.1(4) . . . . ?
C22 O1 C7 C8 -161.5(3) . . . . ?
C22 O1 C7 C15 88.4(3) . . . . ?

_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_L2BiCl
_database_code_depnum_ccdc_archive 'CCDC 2073391'
loop_
_audit_author_name
_audit_author_address
'Shigeru Shimada'
;National Institute of Advanced Industrial Science and Technology (AIST)
Japan
;
_audit_update_record             
;
2021-03-26 deposited with the CCDC.	2021-05-18 downloaded from the CCDC.
;
_audit_creation_date             2020-04-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
s-shimada@aist.go.jp
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C44 H30 Bi Cl N4 O2 S4'
_chemical_formula_sum            'C44 H30 Bi Cl N4 O2 S4'
_chemical_formula_weight         1019.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C44 H30 Bi1 Cl1 N4 O2 S4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Cl Cl 0.1484 0.1585 '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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.3209(3)
_cell_length_b                   13.3170(3)
_cell_length_c                   14.6867(3)
_cell_angle_alpha                110.088(2)
_cell_angle_beta                 104.112(2)
_cell_angle_gamma                107.625(2)
_cell_volume                     1987.42(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9470
_cell_measurement_temperature    153
_cell_measurement_theta_max      28.4790
_cell_measurement_theta_min      1.7970
_shelx_estimated_absorpt_T_max   0.870
_shelx_estimated_absorpt_T_min   0.674
_exptl_absorpt_coefficient_mu    4.757
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1004
_exptl_crystal_recrystallization_method 'crystallized from THF-d8.'
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12258
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.732
_diffrn_reflns_theta_min         1.602
_diffrn_ambient_temperature      153
_diffrn_detector                 'Bruker APEX area detector'
_diffrn_detector_area_resol_mean 8.366
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      2.31 183.92   0.30   14.99    --   28.00  73.62 -25.69  606
  2  ω      2.31 132.67   0.30   14.99    --   28.00  73.62  64.31  435
  3  ω      2.31  71.24   0.30   14.99    --   28.00  73.62 154.31  230
  4  ω      2.31  17.29   0.30   14.99    --   28.00  73.62 -25.69   50
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0391476000
_diffrn_orient_matrix_UB_12      -0.0337869000
_diffrn_orient_matrix_UB_13      -0.0541384000
_diffrn_orient_matrix_UB_21      0.0525440000
_diffrn_orient_matrix_UB_22      0.0100141000
_diffrn_orient_matrix_UB_23      -0.0133664000
_diffrn_orient_matrix_UB_31      0.0020547000
_diffrn_orient_matrix_UB_32      -0.0517786000
_diffrn_orient_matrix_UB_33      0.0022631000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7782
_reflns_number_total             8277
_reflns_odcompleteness_completeness 97.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.67
_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       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.740
_refine_diff_density_min         -0.910
_refine_diff_density_rms         0.126
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         8277
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0350
_refine_ls_restrained_S_all      1.066
_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)+(0.0326P)²+5.7098P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0781
_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.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C17(H17), C18(H18), C19(H19), C20(H20), C24(H24), C25(H25), C26(H26), C27(H27),
  C32(H32), C33(H33), C34(H34), C35(H35), C39(H39), C40(H40), C41(H41), C42(H42)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C44(H44A,H44B,H44C)
;
_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 0.80825(2) 0.81416(2) 0.32642(2) 0.01682(5) Uani 1 1 d . . . . .
Cl1 Cl 1.03091(11) 0.91220(12) 0.34034(12) 0.0370(3) Uani 1 1 d . . . . .
S1 S 0.97563(11) 1.07294(12) 0.18095(10) 0.0303(3) Uani 1 1 d . . . . .
S2 S 0.59651(11) 1.11732(10) 0.17058(9) 0.0227(2) Uani 1 1 d . . . . .
S3 S 0.46190(10) 0.47714(10) 0.33049(9) 0.0226(2) Uani 1 1 d . . . . .
S4 S 0.87937(11) 0.54131(11) 0.53490(10) 0.0276(3) Uani 1 1 d . . . . .
O1 O 0.8272(3) 1.0119(3) 0.2983(2) 0.0193(6) Uani 1 1 d . . . . .
O2 O 0.8086(3) 0.7085(3) 0.4679(2) 0.0191(6) Uani 1 1 d . . . . .
N1 N 0.7819(3) 1.0944(3) 0.0893(3) 0.0216(8) Uani 1 1 d . . . . .
N2 N 0.5742(4) 0.9710(3) 0.2515(3) 0.0232(8) Uani 1 1 d . . . . .
N3 N 0.5899(3) 0.6482(3) 0.3016(3) 0.0177(7) Uani 1 1 d . . . . .
N4 N 0.6419(3) 0.4202(3) 0.4326(3) 0.0214(8) Uani 1 1 d . . . . .
C1 C 0.7103(4) 0.7752(4) 0.1561(3) 0.0172(8) Uani 1 1 d . . . . .
C2 C 0.6501(4) 0.6569(4) 0.0803(4) 0.0238(10) Uani 1 1 d . . . . .
H2 H 0.659814 0.598189 0.099973 0.029 Uiso 1 1 calc R U . . .
C3 C 0.5769(4) 0.6229(4) -0.0224(4) 0.0262(10) Uani 1 1 d . . . . .
H3 H 0.538611 0.542105 -0.072644 0.031 Uiso 1 1 calc R U . . .
C4 C 0.5597(5) 0.7066(4) -0.0516(4) 0.0285(11) Uani 1 1 d . . . . .
H4 H 0.508462 0.683819 -0.121728 0.034 Uiso 1 1 calc R U . . .
C5 C 0.6177(4) 0.8243(4) 0.0221(4) 0.0243(10) Uani 1 1 d . . . . .
H5 H 0.606151 0.882254 0.002197 0.029 Uiso 1 1 calc R U . . .
C6 C 0.6924(4) 0.8583(4) 0.1247(3) 0.0181(8) Uani 1 1 d . . . . .
C7 C 0.7487(4) 0.9919(4) 0.2001(3) 0.0166(8) Uani 1 1 d . . . . .
C8 C 0.8242(4) 1.0586(4) 0.1547(3) 0.0183(8) Uani 1 1 d . . . . .
C9 C 0.9841(4) 1.1356(4) 0.0957(4) 0.0256(10) Uani 1 1 d . . . . .
C10 C 1.0810(5) 1.1748(5) 0.0647(5) 0.0383(13) Uani 1 1 d . . . . .
H10 H 1.156961 1.170879 0.092432 0.046 Uiso 1 1 calc R U . . .
C11 C 1.0637(5) 1.2189(5) -0.0067(4) 0.0369(13) Uani 1 1 d . . . . .
H11 H 1.129282 1.247553 -0.027291 0.044 Uiso 1 1 calc R U . . .
C12 C 0.9519(5) 1.2224(5) -0.0495(4) 0.0334(12) Uani 1 1 d . . . . .
H12 H 0.941927 1.252573 -0.099391 0.040 Uiso 1 1 calc R U . . .
C13 C 0.8551(5) 1.1825(5) -0.0202(4) 0.0324(11) Uani 1 1 d . . . . .
H13 H 0.778384 1.184054 -0.050247 0.039 Uiso 1 1 calc R U . . .
C14 C 0.8719(4) 1.1400(4) 0.0541(3) 0.0215(9) Uani 1 1 d . . . . .
C15 C 0.6400(4) 1.0216(4) 0.2099(3) 0.0183(8) Uani 1 1 d . . . . .
C16 C 0.4780(4) 1.0880(4) 0.2142(4) 0.0237(9) Uani 1 1 d . . . . .
C17 C 0.3871(5) 1.1317(5) 0.2125(4) 0.0303(11) Uani 1 1 d . . . . .
H17 H 0.384969 1.186577 0.185243 0.036 Uiso 1 1 calc R U . . .
C18 C 0.3013(5) 1.0916(5) 0.2518(4) 0.0339(12) Uani 1 1 d . . . . .
H18 H 0.239539 1.120379 0.252221 0.041 Uiso 1 1 calc R U . . .
C19 C 0.3028(5) 1.0101(5) 0.2910(4) 0.0353(12) Uani 1 1 d . . . . .
H19 H 0.241335 0.983659 0.316427 0.042 Uiso 1 1 calc R U . . .
C20 C 0.3913(5) 0.9674(5) 0.2936(4) 0.0307(11) Uani 1 1 d . . . . .
H20 H 0.392687 0.912766 0.321313 0.037 Uiso 1 1 calc R U . . .
C21 C 0.4796(4) 1.0067(4) 0.2540(4) 0.0232(9) Uani 1 1 d . . . . .
C22 C 0.8726(5) 1.1277(4) 0.3836(4) 0.0279(10) Uani 1 1 d . . . . .
H22A H 0.803412 1.139862 0.399418 0.042 Uiso 1 1 calc R U . . .
H22B H 0.912899 1.187389 0.363401 0.042 Uiso 1 1 calc R U . . .
H22C H 0.932343 1.134885 0.446020 0.042 Uiso 1 1 calc R U . . .
C23 C 0.8254(4) 0.6391(4) 0.2726(4) 0.0206(9) Uani 1 1 d . . . . .
C24 C 0.8726(4) 0.6080(5) 0.1956(4) 0.0267(10) Uani 1 1 d . . . . .
H24 H 0.907601 0.664406 0.173123 0.032 Uiso 1 1 calc R U . . .
C25 C 0.8700(5) 0.4972(5) 0.1510(4) 0.0326(11) Uani 1 1 d . . . . .
H25 H 0.900846 0.477407 0.097180 0.039 Uiso 1 1 calc R U . . .
C26 C 0.8221(5) 0.4149(5) 0.1848(4) 0.0312(11) Uani 1 1 d . . . . .
H26 H 0.819561 0.338266 0.154184 0.037 Uiso 1 1 calc R U . . .
C27 C 0.7780(4) 0.4453(4) 0.2635(4) 0.0255(10) Uani 1 1 d . . . . .
H27 H 0.746058 0.389469 0.287522 0.031 Uiso 1 1 calc R U . . .
C28 C 0.7800(4) 0.5566(4) 0.3079(3) 0.0170(8) Uani 1 1 d . . . . .
C29 C 0.7290(4) 0.5879(4) 0.3946(3) 0.0178(8) Uani 1 1 d . . . . .
C30 C 0.5995(4) 0.5778(4) 0.3424(3) 0.0166(8) Uani 1 1 d . . . . .
C31 C 0.3829(4) 0.5341(4) 0.2622(4) 0.0225(9) Uani 1 1 d . . . . .
C32 C 0.2557(4) 0.4976(5) 0.2166(4) 0.0302(11) Uani 1 1 d . . . . .
H32 H 0.199048 0.436347 0.223093 0.036 Uiso 1 1 calc R U . . .
C33 C 0.2156(5) 0.5532(5) 0.1620(5) 0.0371(13) Uani 1 1 d . . . . .
H33 H 0.129306 0.528934 0.128900 0.045 Uiso 1 1 calc R U . . .
C34 C 0.2982(5) 0.6446(5) 0.1538(4) 0.0346(12) Uani 1 1 d . . . . .
H34 H 0.267116 0.681708 0.115767 0.042 Uiso 1 1 calc R U . . .
C35 C 0.4239(4) 0.6823(4) 0.1999(4) 0.0256(10) Uani 1 1 d . . . . .
H35 H 0.479936 0.745378 0.194985 0.031 Uiso 1 1 calc R U . . .
C36 C 0.4667(4) 0.6249(4) 0.2541(3) 0.0208(9) Uani 1 1 d . . . . .
C37 C 0.7340(4) 0.5127(4) 0.4507(3) 0.0197(9) Uani 1 1 d . . . . .
C38 C 0.8096(5) 0.4144(4) 0.5463(4) 0.0254(10) Uani 1 1 d . . . . .
C39 C 0.8641(5) 0.3637(5) 0.6016(4) 0.0314(11) Uani 1 1 d . . . . .
H39 H 0.950825 0.398685 0.640585 0.038 Uiso 1 1 calc R U . . .
C40 C 0.7877(5) 0.2612(5) 0.5976(4) 0.0330(12) Uani 1 1 d . . . . .
H40 H 0.822268 0.224300 0.633835 0.040 Uiso 1 1 calc R U . . .
C41 C 0.6610(5) 0.2109(5) 0.5415(4) 0.0334(12) Uani 1 1 d . . . . .
H41 H 0.610557 0.141257 0.541888 0.040 Uiso 1 1 calc R U . . .
C42 C 0.6060(5) 0.2586(4) 0.4853(4) 0.0287(11) Uani 1 1 d . . . . .
H42 H 0.519335 0.222083 0.445970 0.034 Uiso 1 1 calc R U . . .
C43 C 0.6819(4) 0.3627(4) 0.4880(3) 0.0208(9) Uani 1 1 d . . . . .
C44 C 0.7684(5) 0.7598(4) 0.5484(4) 0.0258(10) Uani 1 1 d . . . . .
H44A H 0.688340 0.759097 0.516197 0.039 Uiso 1 1 calc R U . . .
H44B H 0.829238 0.841442 0.595915 0.039 Uiso 1 1 calc R U . . .
H44C H 0.760091 0.714146 0.588314 0.039 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 Cl1 2.5781(11) . ?
Bi1 O1 2.753(3) . ?
Bi1 N3 2.761(4) . ?
Bi1 C1 2.289(4) . ?
Bi1 C23 2.284(4) . ?
S1 C8 1.746(4) . ?
S1 C9 1.733(5) . ?
S2 C15 1.736(4) . ?
S2 C16 1.725(5) . ?
S3 C30 1.738(4) . ?
S3 C31 1.738(5) . ?
S4 C37 1.751(4) . ?
S4 C38 1.735(5) . ?
O1 C7 1.410(5) . ?
O1 C22 1.439(5) . ?
O2 C29 1.430(5) . ?
O2 C44 1.431(5) . ?
N1 C8 1.282(6) . ?
N1 C14 1.398(6) . ?
N2 C15 1.295(6) . ?
N2 C21 1.389(6) . ?
N3 C30 1.292(5) . ?
N3 C36 1.392(6) . ?
N4 C37 1.287(6) . ?
N4 C43 1.396(5) . ?
C1 C2 1.399(6) . ?
C1 C6 1.391(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.379(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(6) . ?
C6 C7 1.548(6) . ?
C7 C8 1.519(6) . ?
C7 C15 1.532(6) . ?
C9 C10 1.398(7) . ?
C9 C14 1.396(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.371(8) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(8) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.392(6) . ?
C16 C17 1.408(6) . ?
C16 C21 1.398(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.380(7) . ?
C18 H18 0.9500 . ?
C18 C19 1.395(8) . ?
C19 H19 0.9500 . ?
C19 C20 1.373(7) . ?
C20 H20 0.9500 . ?
C20 C21 1.404(6) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.391(6) . ?
C23 C28 1.397(6) . ?
C24 H24 0.9500 . ?
C24 C25 1.379(7) . ?
C25 H25 0.9500 . ?
C25 C26 1.387(8) . ?
C26 H26 0.9500 . ?
C26 C27 1.384(7) . ?
C27 H27 0.9500 . ?
C27 C28 1.388(6) . ?
C28 C29 1.540(6) . ?
C29 C30 1.534(6) . ?
C29 C37 1.505(6) . ?
C31 C32 1.394(6) . ?
C31 C36 1.395(6) . ?
C32 H32 0.9500 . ?
C32 C33 1.368(8) . ?
C33 H33 0.9500 . ?
C33 C34 1.394(8) . ?
C34 H34 0.9500 . ?
C34 C35 1.377(7) . ?
C35 H35 0.9500 . ?
C35 C36 1.397(6) . ?
C38 C39 1.397(7) . ?
C38 C43 1.402(7) . ?
C39 H39 0.9500 . ?
C39 C40 1.375(7) . ?
C40 H40 0.9500 . ?
C40 C41 1.388(8) . ?
C41 H41 0.9500 . ?
C41 C42 1.375(7) . ?
C42 H42 0.9500 . ?
C42 C43 1.399(6) . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?

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
Cl1 Bi1 O1 73.82(7) . . ?
Cl1 Bi1 N3 161.36(8) . . ?
O1 Bi1 N3 123.80(10) . . ?
C1 Bi1 Cl1 96.82(11) . . ?
C1 Bi1 O1 65.70(12) . . ?
C1 Bi1 N3 86.70(13) . . ?
C23 Bi1 Cl1 87.43(11) . . ?
C23 Bi1 O1 147.70(13) . . ?
C23 Bi1 N3 74.15(13) . . ?
C23 Bi1 C1 91.48(15) . . ?
C9 S1 C8 88.6(2) . . ?
C16 S2 C15 88.8(2) . . ?
C30 S3 C31 88.7(2) . . ?
C38 S4 C37 88.5(2) . . ?
C7 O1 Bi1 116.2(2) . . ?
C7 O1 C22 116.0(3) . . ?
C22 O1 Bi1 123.6(3) . . ?
C29 O2 C44 115.0(3) . . ?
C8 N1 C14 110.4(4) . . ?
C15 N2 C21 110.0(4) . . ?
C30 N3 Bi1 116.5(3) . . ?
C30 N3 C36 111.1(4) . . ?
C36 N3 Bi1 132.4(3) . . ?
C37 N4 C43 110.2(4) . . ?
C2 C1 Bi1 117.3(3) . . ?
C6 C1 Bi1 124.8(3) . . ?
C6 C1 C2 117.4(4) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 C1 121.8(4) . . ?
C3 C2 H2 119.1 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.8(4) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.4(4) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.7(4) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C7 123.5(4) . . ?
C5 C6 C1 120.9(4) . . ?
C5 C6 C7 115.5(4) . . ?
O1 C7 C6 108.1(3) . . ?
O1 C7 C8 109.3(3) . . ?
O1 C7 C15 110.6(3) . . ?
C8 C7 C6 108.1(3) . . ?
C8 C7 C15 114.0(3) . . ?
C15 C7 C6 106.5(3) . . ?
N1 C8 S1 116.7(3) . . ?
N1 C8 C7 125.1(4) . . ?
C7 C8 S1 117.8(3) . . ?
C10 C9 S1 129.5(4) . . ?
C14 C9 S1 109.6(3) . . ?
C14 C9 C10 120.9(5) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 C9 118.4(5) . . ?
C11 C10 H10 120.8 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.2(5) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(5) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.6 . . ?
C12 C13 C14 118.8(5) . . ?
C14 C13 H13 120.6 . . ?
C9 C14 N1 114.8(4) . . ?
C13 C14 N1 125.2(4) . . ?
C13 C14 C9 119.9(4) . . ?
N2 C15 S2 116.6(3) . . ?
N2 C15 C7 117.3(4) . . ?
C7 C15 S2 126.1(3) . . ?
C17 C16 S2 129.7(4) . . ?
C21 C16 S2 109.7(3) . . ?
C21 C16 C17 120.6(4) . . ?
C16 C17 H17 121.3 . . ?
C18 C17 C16 117.5(5) . . ?
C18 C17 H17 121.3 . . ?
C17 C18 H18 119.1 . . ?
C17 C18 C19 121.8(5) . . ?
C19 C18 H18 119.1 . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.3(5) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 121.0 . . ?
C19 C20 C21 118.0(5) . . ?
C21 C20 H20 121.0 . . ?
N2 C21 C16 114.9(4) . . ?
N2 C21 C20 124.3(4) . . ?
C16 C21 C20 120.8(4) . . ?
O1 C22 H22A 109.5 . . ?
O1 C22 H22B 109.5 . . ?
O1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 Bi1 119.7(3) . . ?
C24 C23 C28 118.0(4) . . ?
C28 C23 Bi1 122.0(3) . . ?
C23 C24 H24 119.2 . . ?
C25 C24 C23 121.7(5) . . ?
C25 C24 H24 119.2 . . ?
C24 C25 H25 120.1 . . ?
C24 C25 C26 119.8(5) . . ?
C26 C25 H25 120.1 . . ?
C25 C26 H26 120.3 . . ?
C27 C26 C25 119.4(5) . . ?
C27 C26 H26 120.3 . . ?
C26 C27 H27 119.6 . . ?
C26 C27 C28 120.8(4) . . ?
C28 C27 H27 119.6 . . ?
C23 C28 C29 120.0(4) . . ?
C27 C28 C23 120.2(4) . . ?
C27 C28 C29 119.8(4) . . ?
O2 C29 C28 106.1(3) . . ?
O2 C29 C30 109.0(3) . . ?
O2 C29 C37 108.7(3) . . ?
C30 C29 C28 107.1(3) . . ?
C37 C29 C28 110.7(3) . . ?
C37 C29 C30 114.8(3) . . ?
N3 C30 S3 116.1(3) . . ?
N3 C30 C29 118.1(4) . . ?
C29 C30 S3 125.7(3) . . ?
C32 C31 S3 128.5(4) . . ?
C32 C31 C36 121.6(4) . . ?
C36 C31 S3 109.8(3) . . ?
C31 C32 H32 121.3 . . ?
C33 C32 C31 117.5(5) . . ?
C33 C32 H32 121.3 . . ?
C32 C33 H33 119.2 . . ?
C32 C33 C34 121.6(5) . . ?
C34 C33 H33 119.2 . . ?
C33 C34 H34 119.4 . . ?
C35 C34 C33 121.3(5) . . ?
C35 C34 H34 119.4 . . ?
C34 C35 H35 121.0 . . ?
C34 C35 C36 118.0(5) . . ?
C36 C35 H35 121.0 . . ?
N3 C36 C31 114.2(4) . . ?
N3 C36 C35 125.7(4) . . ?
C31 C36 C35 120.0(4) . . ?
N4 C37 S4 116.8(3) . . ?
N4 C37 C29 125.1(4) . . ?
C29 C37 S4 117.6(3) . . ?
C39 C38 S4 128.9(4) . . ?
C39 C38 C43 121.6(5) . . ?
C43 C38 S4 109.5(3) . . ?
C38 C39 H39 121.2 . . ?
C40 C39 C38 117.5(5) . . ?
C40 C39 H39 121.2 . . ?
C39 C40 H40 119.4 . . ?
C39 C40 C41 121.1(5) . . ?
C41 C40 H40 119.4 . . ?
C40 C41 H41 119.0 . . ?
C42 C41 C40 122.1(5) . . ?
C42 C41 H41 119.0 . . ?
C41 C42 H42 121.1 . . ?
C41 C42 C43 117.9(5) . . ?
C43 C42 H42 121.1 . . ?
N4 C43 C38 114.9(4) . . ?
N4 C43 C42 125.2(4) . . ?
C42 C43 C38 119.8(4) . . ?
O2 C44 H44A 109.5 . . ?
O2 C44 H44B 109.5 . . ?
O2 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 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 O1 C7 C6 -12.5(4) . . . . ?
Bi1 O1 C7 C8 -130.0(3) . . . . ?
Bi1 O1 C7 C15 103.7(3) . . . . ?
Bi1 N3 C30 S3 177.79(18) . . . . ?
Bi1 N3 C30 C29 -3.5(5) . . . . ?
Bi1 N3 C36 C31 -177.7(3) . . . . ?
Bi1 N3 C36 C35 3.6(7) . . . . ?
Bi1 C1 C2 C3 172.7(3) . . . . ?
Bi1 C1 C6 C5 -171.1(3) . . . . ?
Bi1 C1 C6 C7 6.5(6) . . . . ?
Bi1 C23 C24 C25 -171.5(4) . . . . ?
Bi1 C23 C28 C27 171.8(3) . . . . ?
Bi1 C23 C28 C29 -6.7(6) . . . . ?
S1 C9 C10 C11 178.3(4) . . . . ?
S1 C9 C14 N1 -0.1(5) . . . . ?
S1 C9 C14 C13 -177.2(4) . . . . ?
S2 C16 C17 C18 179.1(4) . . . . ?
S2 C16 C21 N2 1.2(5) . . . . ?
S2 C16 C21 C20 -179.4(4) . . . . ?
S3 C31 C32 C33 -176.8(4) . . . . ?
S3 C31 C36 N3 -0.3(5) . . . . ?
S3 C31 C36 C35 178.5(4) . . . . ?
S4 C38 C39 C40 -179.6(4) . . . . ?
S4 C38 C43 N4 2.4(5) . . . . ?
S4 C38 C43 C42 179.9(4) . . . . ?
O1 C7 C8 S1 33.8(4) . . . . ?
O1 C7 C8 N1 -154.2(4) . . . . ?
O1 C7 C15 S2 126.0(3) . . . . ?
O1 C7 C15 N2 -53.9(5) . . . . ?
O2 C29 C30 S3 -130.2(3) . . . . ?
O2 C29 C30 N3 51.2(5) . . . . ?
O2 C29 C37 S4 -44.4(4) . . . . ?
O2 C29 C37 N4 144.2(4) . . . . ?
C1 C2 C3 C4 -1.4(7) . . . . ?
C1 C6 C7 O1 5.7(5) . . . . ?
C1 C6 C7 C8 123.9(4) . . . . ?
C1 C6 C7 C15 -113.2(4) . . . . ?
C2 C1 C6 C5 0.1(6) . . . . ?
C2 C1 C6 C7 177.7(4) . . . . ?
C2 C3 C4 C5 1.0(7) . . . . ?
C3 C4 C5 C6 -0.1(7) . . . . ?
C4 C5 C6 C1 -0.4(7) . . . . ?
C4 C5 C6 C7 -178.3(4) . . . . ?
C5 C6 C7 O1 -176.6(4) . . . . ?
C5 C6 C7 C8 -58.3(5) . . . . ?
C5 C6 C7 C15 64.5(5) . . . . ?
C6 C1 C2 C3 0.8(6) . . . . ?
C6 C7 C8 S1 -83.6(4) . . . . ?
C6 C7 C8 N1 88.4(5) . . . . ?
C6 C7 C15 S2 -116.8(4) . . . . ?
C6 C7 C15 N2 63.3(5) . . . . ?
C8 S1 C9 C10 -178.1(5) . . . . ?
C8 S1 C9 C14 -0.3(4) . . . . ?
C8 N1 C14 C9 0.7(6) . . . . ?
C8 N1 C14 C13 177.6(5) . . . . ?
C8 C7 C15 S2 2.3(5) . . . . ?
C8 C7 C15 N2 -177.6(4) . . . . ?
C9 S1 C8 N1 0.7(4) . . . . ?
C9 S1 C8 C7 173.4(3) . . . . ?
C9 C10 C11 C12 -1.5(9) . . . . ?
C10 C9 C14 N1 177.9(5) . . . . ?
C10 C9 C14 C13 0.8(8) . . . . ?
C10 C11 C12 C13 0.7(9) . . . . ?
C11 C12 C13 C14 0.8(8) . . . . ?
C12 C13 C14 N1 -178.3(5) . . . . ?
C12 C13 C14 C9 -1.6(8) . . . . ?
C14 N1 C8 S1 -0.9(5) . . . . ?
C14 N1 C8 C7 -173.0(4) . . . . ?
C14 C9 C10 C11 0.7(8) . . . . ?
C15 S2 C16 C17 -179.6(5) . . . . ?
C15 S2 C16 C21 -0.8(4) . . . . ?
C15 N2 C21 C16 -1.1(6) . . . . ?
C15 N2 C21 C20 179.5(5) . . . . ?
C15 C7 C8 S1 158.3(3) . . . . ?
C15 C7 C8 N1 -29.7(6) . . . . ?
C16 S2 C15 N2 0.2(4) . . . . ?
C16 S2 C15 C7 -179.7(4) . . . . ?
C16 C17 C18 C19 -0.7(8) . . . . ?
C17 C16 C21 N2 -179.8(4) . . . . ?
C17 C16 C21 C20 -0.4(7) . . . . ?
C17 C18 C19 C20 1.0(9) . . . . ?
C18 C19 C20 C21 -1.0(8) . . . . ?
C19 C20 C21 N2 -180.0(5) . . . . ?
C19 C20 C21 C16 0.7(7) . . . . ?
C21 N2 C15 S2 0.5(5) . . . . ?
C21 N2 C15 C7 -179.7(4) . . . . ?
C21 C16 C17 C18 0.4(7) . . . . ?
C22 O1 C7 C6 -170.4(3) . . . . ?
C22 O1 C7 C8 72.2(4) . . . . ?
C22 O1 C7 C15 -54.2(5) . . . . ?
C23 C24 C25 C26 -1.6(8) . . . . ?
C23 C28 C29 O2 -39.1(5) . . . . ?
C23 C28 C29 C30 77.2(5) . . . . ?
C23 C28 C29 C37 -156.9(4) . . . . ?
C24 C23 C28 C27 -2.6(7) . . . . ?
C24 C23 C28 C29 178.9(4) . . . . ?
C24 C25 C26 C27 -0.3(8) . . . . ?
C25 C26 C27 C28 0.7(8) . . . . ?
C26 C27 C28 C23 0.8(7) . . . . ?
C26 C27 C28 C29 179.3(4) . . . . ?
C27 C28 C29 O2 142.3(4) . . . . ?
C27 C28 C29 C30 -101.3(5) . . . . ?
C27 C28 C29 C37 24.6(6) . . . . ?
C28 C23 C24 C25 3.1(7) . . . . ?
C28 C29 C30 S3 115.5(4) . . . . ?
C28 C29 C30 N3 -63.1(5) . . . . ?
C28 C29 C37 S4 71.7(4) . . . . ?
C28 C29 C37 N4 -99.7(5) . . . . ?
C30 S3 C31 C32 177.6(5) . . . . ?
C30 S3 C31 C36 -0.2(3) . . . . ?
C30 N3 C36 C31 0.8(5) . . . . ?
C30 N3 C36 C35 -177.8(4) . . . . ?
C30 C29 C37 S4 -166.8(3) . . . . ?
C30 C29 C37 N4 21.7(6) . . . . ?
C31 S3 C30 N3 0.7(4) . . . . ?
C31 S3 C30 C29 -177.9(4) . . . . ?
C31 C32 C33 C34 -1.3(8) . . . . ?
C32 C31 C36 N3 -178.3(4) . . . . ?
C32 C31 C36 C35 0.5(7) . . . . ?
C32 C33 C34 C35 0.4(9) . . . . ?
C33 C34 C35 C36 0.9(8) . . . . ?
C34 C35 C36 N3 177.3(4) . . . . ?
C34 C35 C36 C31 -1.3(7) . . . . ?
C36 N3 C30 S3 -1.0(5) . . . . ?
C36 N3 C30 C29 177.7(4) . . . . ?
C36 C31 C32 C33 0.8(7) . . . . ?
C37 S4 C38 C39 177.5(5) . . . . ?
C37 S4 C38 C43 -1.7(4) . . . . ?
C37 N4 C43 C38 -1.9(6) . . . . ?
C37 N4 C43 C42 -179.2(4) . . . . ?
C37 C29 C30 S3 -7.9(5) . . . . ?
C37 C29 C30 N3 173.5(4) . . . . ?
C38 S4 C37 N4 0.7(4) . . . . ?
C38 S4 C37 C29 -171.5(4) . . . . ?
C38 C39 C40 C41 -0.7(8) . . . . ?
C39 C38 C43 N4 -176.8(4) . . . . ?
C39 C38 C43 C42 0.6(7) . . . . ?
C39 C40 C41 C42 1.7(8) . . . . ?
C40 C41 C42 C43 -1.5(8) . . . . ?
C41 C42 C43 N4 177.5(4) . . . . ?
C41 C42 C43 C38 0.3(7) . . . . ?
C43 N4 C37 S4 0.5(5) . . . . ?
C43 N4 C37 C29 172.1(4) . . . . ?
C43 C38 C39 C40 -0.5(7) . . . . ?
C44 O2 C29 C28 172.6(3) . . . . ?
C44 O2 C29 C30 57.6(4) . . . . ?
C44 O2 C29 C37 -68.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.181
_oxdiff_exptl_absorpt_empirical_full_min 0.822
####################################################################### 
# 
# 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_LBiCl2-THF
_database_code_depnum_ccdc_archive 'CCDC 2073388'
loop_
_audit_author_name
_audit_author_address
'Shigeru Shimada'
;National Institute of Advanced Industrial Science and Technology (AIST)
Japan
;
_audit_update_record             
;
2021-03-26 deposited with the CCDC.	2021-05-18 downloaded from the CCDC.
;
_audit_creation_date             2021-02-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
s-shimada@aist.go.jp
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H15 Bi Cl2 N2 O S2, C4 H8 O'
_chemical_formula_sum            'C26 H23 Bi Cl2 N2 O2 S2'
_chemical_formula_weight         739.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         C26H23Bi1Cl2N2O2S2
_chemical_oxdiff_usercomment     BBTMMP-BiCl2-THF
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Cl Cl 0.1484 0.1585 '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'

_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                   12.0405(4)
_cell_length_b                   18.2862(8)
_cell_length_c                   12.2047(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.387(3)
_cell_angle_gamma                90
_cell_volume                     2634.27(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9116
_cell_measurement_temperature    153
_cell_measurement_theta_max      28.5780
_cell_measurement_theta_min      2.0410
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53334
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.865
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1432
_exptl_crystal_recrystallization_method 'recrystallized from THF'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14444
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.034
_diffrn_ambient_temperature      153
_diffrn_detector                 'Bruker APEX area detector'
_diffrn_detector_area_resol_mean 8.366
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

 # Type Start End Width tₑₓₚ ω θ κ φ Frames
#--------------------------------------------------------------------------
 1 ω 2.31 183.92 0.30 1.99 -- 28.00 73.62 -25.69 606
 2 ω 2.31 132.67 0.30 1.98 -- 28.00 73.62 64.31 435
 3 ω 2.31 71.24 0.30 1.98 -- 28.00 73.62 154.31 230
 4 ω 2.31 17.29 0.30 1.99 -- 28.00 73.62 -25.69 50
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0109960000
_diffrn_orient_matrix_UB_12      0.0302221000
_diffrn_orient_matrix_UB_13      0.0325788000
_diffrn_orient_matrix_UB_21      0.0286621000
_diffrn_orient_matrix_UB_22      0.0234348000
_diffrn_orient_matrix_UB_23      -0.0316374000
_diffrn_orient_matrix_UB_31      -0.0516585000
_diffrn_orient_matrix_UB_32      0.0064597000
_diffrn_orient_matrix_UB_33      -0.0381238000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4927
_reflns_number_total             5373
_reflns_odcompleteness_completeness 99.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         2.326
_refine_diff_density_min         -1.113
_refine_diff_density_rms         0.155
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         5373
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.177
_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)+(0.0426P)²+10.7600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.0982
_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.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C17(H17), C18(H18), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_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 0.13605(2) 0.55297(2) 0.86379(2) 0.02360(9) Uani 1 1 d . . . . .
Cl1 Cl 0.06062(15) 0.68560(10) 0.83424(16) 0.0383(4) Uani 1 1 d . . . . .
Cl2 Cl 0.13583(15) 0.55024(11) 1.07340(14) 0.0400(4) Uani 1 1 d . . . . .
S1 S 0.32049(16) 0.51810(11) 0.52310(14) 0.0364(4) Uani 1 1 d . . . . .
S2 S 0.35942(15) 0.35390(10) 0.74989(14) 0.0312(4) Uani 1 1 d . . . . .
O1 O 0.4759(4) 0.4888(3) 0.7150(4) 0.0338(11) Uani 1 1 d . . . . .
O2 O 0.3128(7) 0.4002(5) 0.3338(6) 0.078(2) Uani 1 1 d . . . . .
N1 N 0.1931(5) 0.5539(3) 0.6615(4) 0.0250(11) Uani 1 1 d . . . . .
N2 N 0.2603(4) 0.4382(3) 0.8697(4) 0.0253(11) Uani 1 1 d . . . . .
C22 C 0.5728(6) 0.4592(4) 0.7927(7) 0.0443(19) Uani 1 1 d . . . . .
H22A H 0.561421 0.465143 0.867872 0.066 Uiso 1 1 calc R U . . .
H22B H 0.640175 0.484777 0.784053 0.066 Uiso 1 1 calc R U . . .
H22C H 0.580790 0.408167 0.777513 0.066 Uiso 1 1 calc R U . . .
C1 C 0.3143(5) 0.5971(4) 0.8948(5) 0.0260(13) Uani 1 1 d . . . . .
C2 C 0.3357(6) 0.6569(4) 0.9665(5) 0.0317(14) Uani 1 1 d . . . . .
H2 H 0.280346 0.673150 1.004211 0.038 Uiso 1 1 calc R U . . .
C3 C 0.4399(7) 0.6923(4) 0.9816(6) 0.0406(18) Uani 1 1 d . . . . .
H3 H 0.455370 0.731235 1.031286 0.049 Uiso 1 1 calc R U . . .
C4 C 0.5191(6) 0.6697(4) 0.9236(6) 0.0390(17) Uani 1 1 d . . . . .
H4 H 0.587457 0.694737 0.931362 0.047 Uiso 1 1 calc R U . . .
C5 C 0.4990(6) 0.6100(4) 0.8534(6) 0.0323(15) Uani 1 1 d . . . . .
H5 H 0.554195 0.595147 0.814570 0.039 Uiso 1 1 calc R U . . .
C6 C 0.3977(5) 0.5719(4) 0.8397(5) 0.0248(13) Uani 1 1 d . . . . .
C7 C 0.3789(5) 0.5071(3) 0.7572(5) 0.0247(13) Uani 1 1 d . . . . .
C8 C 0.2909(5) 0.5291(4) 0.6553(5) 0.0252(13) Uani 1 1 d . . . . .
C9 C 0.1869(6) 0.5540(4) 0.4692(5) 0.0352(16) Uani 1 1 d . . . . .
C10 C 0.1374(7) 0.5676(5) 0.3578(6) 0.049(2) Uani 1 1 d . . . . .
H10 H 0.175028 0.556067 0.300461 0.059 Uiso 1 1 calc R U . . .
C11 C 0.0322(8) 0.5982(5) 0.3358(6) 0.050(2) Uani 1 1 d . . . . .
H11 H -0.000667 0.609722 0.262334 0.061 Uiso 1 1 calc R U . . .
C12 C -0.0276(7) 0.6127(4) 0.4201(6) 0.0427(19) Uani 1 1 d . . . . .
H12 H -0.100635 0.631664 0.402144 0.051 Uiso 1 1 calc R U . . .
C13 C 0.0220(6) 0.5989(4) 0.5316(6) 0.0336(15) Uani 1 1 d . . . . .
H13 H -0.016401 0.609621 0.588642 0.040 Uiso 1 1 calc R U . . .
C14 C 0.1285(6) 0.5691(3) 0.5551(5) 0.0269(14) Uani 1 1 d . . . . .
C15 C 0.3315(5) 0.4382(3) 0.8017(5) 0.0261(14) Uani 1 1 d . . . . .
C16 C 0.2681(5) 0.3142(4) 0.8271(5) 0.0296(14) Uani 1 1 d . . . . .
C17 C 0.2429(6) 0.2405(4) 0.8361(6) 0.0363(16) Uani 1 1 d . . . . .
H17 H 0.273811 0.204783 0.796765 0.044 Uiso 1 1 calc R U . . .
C18 C 0.1705(7) 0.2229(4) 0.9054(7) 0.0419(18) Uani 1 1 d . . . . .
H18 H 0.150661 0.174182 0.912609 0.050 Uiso 1 1 calc R U . . .
C19 C 0.1254(6) 0.2769(4) 0.9659(6) 0.0369(16) Uani 1 1 d . . . . .
H19 H 0.077674 0.263016 1.013584 0.044 Uiso 1 1 calc R U . . .
C20 C 0.1502(6) 0.3498(4) 0.9564(6) 0.0333(15) Uani 1 1 d . . . . .
H20 H 0.118794 0.385694 0.994935 0.040 Uiso 1 1 calc R U . . .
C21 C 0.2239(5) 0.3670(4) 0.8868(5) 0.0268(14) Uani 1 1 d . . . . .
C23 C 0.2204(9) 0.3672(7) 0.2676(11) 0.081(3) Uani 1 1 d . . . . .
H23A H 0.216270 0.380360 0.189864 0.097 Uiso 1 1 calc R U . . .
H23B H 0.151131 0.383015 0.289679 0.097 Uiso 1 1 calc R U . . .
C24 C 0.2352(10) 0.2844(8) 0.2828(12) 0.103(5) Uani 1 1 d . . . . .
H24A H 0.180076 0.264679 0.323139 0.124 Uiso 1 1 calc R U . . .
H24B H 0.226224 0.260043 0.211000 0.124 Uiso 1 1 calc R U . . .
C25 C 0.3528(10) 0.2746(7) 0.3485(10) 0.084(4) Uani 1 1 d . . . . .
H25A H 0.356871 0.234213 0.400613 0.101 Uiso 1 1 calc R U . . .
H25B H 0.406186 0.266317 0.299780 0.101 Uiso 1 1 calc R U . . .
C26 C 0.3743(11) 0.3451(7) 0.4077(9) 0.093(4) Uani 1 1 d . . . . .
H26A H 0.347660 0.343589 0.477628 0.112 Uiso 1 1 calc R U . . .
H26B H 0.454729 0.355980 0.423627 0.112 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 Cl1 2.5898(17) . ?
Bi1 Cl2 2.5592(16) . ?
Bi1 N1 2.690(5) . ?
Bi1 N2 2.570(5) . ?
Bi1 C1 2.254(6) . ?
S1 C8 1.731(6) . ?
S1 C9 1.742(7) . ?
S2 C15 1.725(6) . ?
S2 C16 1.742(7) . ?
O1 C22 1.454(8) . ?
O1 C7 1.407(7) . ?
O2 C23 1.378(13) . ?
O2 C26 1.453(13) . ?
N1 C8 1.278(8) . ?
N1 C14 1.403(8) . ?
N2 C15 1.306(8) . ?
N2 C21 1.403(8) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C1 C2 1.392(9) . ?
C1 C6 1.393(9) . ?
C2 H2 0.9300 . ?
C2 C3 1.392(10) . ?
C3 H3 0.9300 . ?
C3 C4 1.359(11) . ?
C4 H4 0.9300 . ?
C4 C5 1.380(10) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(9) . ?
C6 C7 1.541(9) . ?
C7 C8 1.521(9) . ?
C7 C15 1.527(9) . ?
C9 C10 1.395(10) . ?
C9 C14 1.400(10) . ?
C10 H10 0.9300 . ?
C10 C11 1.363(12) . ?
C11 H11 0.9300 . ?
C11 C12 1.393(12) . ?
C12 H12 0.9300 . ?
C12 C13 1.397(9) . ?
C13 H13 0.9300 . ?
C13 C14 1.369(10) . ?
C16 C17 1.391(10) . ?
C16 C21 1.378(9) . ?
C17 H17 0.9300 . ?
C17 C18 1.368(10) . ?
C18 H18 0.9300 . ?
C18 C19 1.405(10) . ?
C19 H19 0.9300 . ?
C19 C20 1.376(10) . ?
C20 H20 0.9300 . ?
C20 C21 1.381(9) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.533(17) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.494(15) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.475(17) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?

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
Cl1 Bi1 N1 90.69(12) . . ?
Cl2 Bi1 Cl1 95.05(6) . . ?
Cl2 Bi1 N1 165.54(12) . . ?
Cl2 Bi1 N2 94.10(12) . . ?
N2 Bi1 Cl1 162.69(13) . . ?
N2 Bi1 N1 77.19(16) . . ?
C1 Bi1 Cl1 89.10(17) . . ?
C1 Bi1 Cl2 91.61(16) . . ?
C1 Bi1 N1 75.19(19) . . ?
C1 Bi1 N2 76.0(2) . . ?
C8 S1 C9 87.9(3) . . ?
C15 S2 C16 89.1(3) . . ?
C7 O1 C22 117.8(5) . . ?
C23 O2 C26 108.3(9) . . ?
C8 N1 Bi1 117.2(4) . . ?
C8 N1 C14 111.4(5) . . ?
C14 N1 Bi1 130.9(4) . . ?
C15 N2 Bi1 115.7(4) . . ?
C15 N2 C21 111.0(5) . . ?
C21 N2 Bi1 124.4(4) . . ?
O1 C22 H22A 109.5 . . ?
O1 C22 H22B 109.5 . . ?
O1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C2 C1 Bi1 116.0(5) . . ?
C2 C1 C6 120.2(6) . . ?
C6 C1 Bi1 123.6(5) . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.9(7) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.8(7) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.6(7) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.0(7) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C7 122.9(6) . . ?
C5 C6 C1 118.4(6) . . ?
C5 C6 C7 118.5(6) . . ?
O1 C7 C6 113.4(5) . . ?
O1 C7 C8 105.0(5) . . ?
O1 C7 C15 109.2(5) . . ?
C8 C7 C6 108.6(5) . . ?
C8 C7 C15 105.1(5) . . ?
C15 C7 C6 114.7(5) . . ?
N1 C8 S1 117.3(5) . . ?
N1 C8 C7 123.1(5) . . ?
C7 C8 S1 119.6(5) . . ?
C10 C9 S1 128.3(6) . . ?
C10 C9 C14 120.9(7) . . ?
C14 C9 S1 110.8(5) . . ?
C9 C10 H10 121.1 . . ?
C11 C10 C9 117.8(8) . . ?
C11 C10 H10 121.1 . . ?
C10 C11 H11 119.0 . . ?
C10 C11 C12 121.9(7) . . ?
C12 C11 H11 119.0 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.0(7) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.7 . . ?
C14 C13 C12 118.6(7) . . ?
C14 C13 H13 120.7 . . ?
C9 C14 N1 112.6(6) . . ?
C13 C14 N1 126.7(6) . . ?
C13 C14 C9 120.6(6) . . ?
N2 C15 S2 115.7(5) . . ?
N2 C15 C7 124.4(6) . . ?
C7 C15 S2 119.6(5) . . ?
C17 C16 S2 128.2(5) . . ?
C21 C16 S2 110.1(5) . . ?
C21 C16 C17 121.6(6) . . ?
C16 C17 H17 121.5 . . ?
C18 C17 C16 116.9(7) . . ?
C18 C17 H17 121.5 . . ?
C17 C18 H18 119.4 . . ?
C17 C18 C19 121.3(7) . . ?
C19 C18 H18 119.4 . . ?
C18 C19 H19 119.2 . . ?
C20 C19 C18 121.6(7) . . ?
C20 C19 H19 119.2 . . ?
C19 C20 H20 121.7 . . ?
C19 C20 C21 116.7(6) . . ?
C21 C20 H20 121.7 . . ?
C16 C21 N2 114.1(6) . . ?
C16 C21 C20 121.8(7) . . ?
C20 C21 N2 124.1(6) . . ?
O2 C23 H23A 110.2 . . ?
O2 C23 H23B 110.2 . . ?
O2 C23 C24 107.5(9) . . ?
H23A C23 H23B 108.5 . . ?
C24 C23 H23A 110.2 . . ?
C24 C23 H23B 110.2 . . ?
C23 C24 H24A 110.8 . . ?
C23 C24 H24B 110.8 . . ?
H24A C24 H24B 108.8 . . ?
C25 C24 C23 105.0(10) . . ?
C25 C24 H24A 110.8 . . ?
C25 C24 H24B 110.8 . . ?
C24 C25 H25A 111.3 . . ?
C24 C25 H25B 111.3 . . ?
H25A C25 H25B 109.2 . . ?
C26 C25 C24 102.4(11) . . ?
C26 C25 H25A 111.3 . . ?
C26 C25 H25B 111.3 . . ?
O2 C26 C25 106.5(8) . . ?
O2 C26 H26A 110.4 . . ?
O2 C26 H26B 110.4 . . ?
C25 C26 H26A 110.4 . . ?
C25 C26 H26B 110.4 . . ?
H26A C26 H26B 108.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Bi1 N1 C8 S1 171.5(3) . . . . ?
Bi1 N1 C8 C7 -6.6(8) . . . . ?
Bi1 N1 C14 C9 -172.0(4) . . . . ?
Bi1 N1 C14 C13 11.3(10) . . . . ?
Bi1 N2 C15 S2 -147.7(3) . . . . ?
Bi1 N2 C15 C7 25.3(8) . . . . ?
Bi1 N2 C21 C16 144.1(4) . . . . ?
Bi1 N2 C21 C20 -35.6(8) . . . . ?
Bi1 C1 C2 C3 -173.5(5) . . . . ?
Bi1 C1 C6 C5 170.8(5) . . . . ?
Bi1 C1 C6 C7 -4.4(8) . . . . ?
S1 C9 C10 C11 -178.1(7) . . . . ?
S1 C9 C14 N1 2.0(8) . . . . ?
S1 C9 C14 C13 179.0(5) . . . . ?
S2 C16 C17 C18 178.0(6) . . . . ?
S2 C16 C21 N2 1.2(7) . . . . ?
S2 C16 C21 C20 -179.0(5) . . . . ?
O1 C7 C8 S1 6.6(7) . . . . ?
O1 C7 C8 N1 -175.4(6) . . . . ?
O1 C7 C15 S2 -24.7(7) . . . . ?
O1 C7 C15 N2 162.6(6) . . . . ?
O2 C23 C24 C25 -9.1(15) . . . . ?
C22 O1 C7 C6 66.7(7) . . . . ?
C22 O1 C7 C8 -174.8(6) . . . . ?
C22 O1 C7 C15 -62.6(7) . . . . ?
C1 C2 C3 C4 2.1(11) . . . . ?
C1 C6 C7 O1 -177.3(5) . . . . ?
C1 C6 C7 C8 66.4(7) . . . . ?
C1 C6 C7 C15 -50.8(8) . . . . ?
C2 C1 C6 C5 -3.5(9) . . . . ?
C2 C1 C6 C7 -178.6(6) . . . . ?
C2 C3 C4 C5 -2.8(11) . . . . ?
C3 C4 C5 C6 0.3(11) . . . . ?
C4 C5 C6 C1 2.8(10) . . . . ?
C4 C5 C6 C7 178.2(6) . . . . ?
C5 C6 C7 O1 7.6(8) . . . . ?
C5 C6 C7 C8 -108.7(6) . . . . ?
C5 C6 C7 C15 134.0(6) . . . . ?
C6 C1 C2 C3 1.1(10) . . . . ?
C6 C7 C8 S1 128.2(5) . . . . ?
C6 C7 C8 N1 -53.8(8) . . . . ?
C6 C7 C15 S2 -153.3(4) . . . . ?
C6 C7 C15 N2 34.0(8) . . . . ?
C8 S1 C9 C10 178.1(8) . . . . ?
C8 S1 C9 C14 -2.2(6) . . . . ?
C8 N1 C14 C9 -0.5(8) . . . . ?
C8 N1 C14 C13 -177.2(7) . . . . ?
C8 C7 C15 S2 87.5(6) . . . . ?
C8 C7 C15 N2 -85.2(7) . . . . ?
C9 S1 C8 N1 2.1(6) . . . . ?
C9 S1 C8 C7 -179.8(6) . . . . ?
C9 C10 C11 C12 -3.0(13) . . . . ?
C10 C9 C14 N1 -178.2(7) . . . . ?
C10 C9 C14 C13 -1.3(11) . . . . ?
C10 C11 C12 C13 2.8(13) . . . . ?
C11 C12 C13 C14 -1.8(12) . . . . ?
C12 C13 C14 N1 177.5(7) . . . . ?
C12 C13 C14 C9 1.0(11) . . . . ?
C14 N1 C8 S1 -1.3(7) . . . . ?
C14 N1 C8 C7 -179.3(6) . . . . ?
C14 C9 C10 C11 2.2(12) . . . . ?
C15 S2 C16 C17 -177.5(7) . . . . ?
C15 S2 C16 C21 -0.5(5) . . . . ?
C15 N2 C21 C16 -1.6(8) . . . . ?
C15 N2 C21 C20 178.7(6) . . . . ?
C15 C7 C8 S1 -108.6(5) . . . . ?
C15 C7 C8 N1 69.4(8) . . . . ?
C16 S2 C15 N2 -0.5(5) . . . . ?
C16 S2 C15 C7 -173.8(5) . . . . ?
C16 C17 C18 C19 -1.0(12) . . . . ?
C17 C16 C21 N2 178.6(6) . . . . ?
C17 C16 C21 C20 -1.7(10) . . . . ?
C17 C18 C19 C20 1.4(12) . . . . ?
C18 C19 C20 C21 -1.7(11) . . . . ?
C19 C20 C21 N2 -178.4(6) . . . . ?
C19 C20 C21 C16 1.9(10) . . . . ?
C21 N2 C15 S2 1.3(7) . . . . ?
C21 N2 C15 C7 174.2(6) . . . . ?
C21 C16 C17 C18 1.2(11) . . . . ?
C23 O2 C26 C25 28.3(14) . . . . ?
C23 C24 C25 C26 25.1(14) . . . . ?
C24 C25 C26 O2 -32.6(14) . . . . ?
C26 O2 C23 C24 -11.4(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.562
_oxdiff_exptl_absorpt_empirical_full_min 0.708

####################################################################### 
# 
# 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_Rearranged-L
_database_code_depnum_ccdc_archive 'CCDC 2073389'
loop_
_audit_author_name
_audit_author_address
'Shigeru Shimada'
;National Institute of Advanced Industrial Science and Technology (AIST)
Japan
;
_audit_update_record             
;
2021-03-26 deposited with the CCDC.	2021-05-18 downloaded from the CCDC.
;
_audit_creation_date             2020-04-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
Benzo[d]thiazol-2-yl(2-(benzo[d]thiazol-2-yl)phenyl)methanol
_chemical_formula_moiety         'C21 H14 N2 O S2'
_chemical_formula_sum            'C21 H14 N2 O S2'
_chemical_formula_weight         374.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H14 N2 O S2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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/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                   13.7303(6)
_cell_length_b                   8.2843(4)
_cell_length_c                   15.1051(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.425(4)
_cell_angle_gamma                90
_cell_volume                     1710.45(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6751
_cell_measurement_temperature    153
_cell_measurement_theta_max      28.9750
_cell_measurement_theta_min      2.7060
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.324
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95442
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             776
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.025
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10543
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.873
_diffrn_reflns_theta_min         2.709
_diffrn_ambient_temperature      153
_diffrn_detector                 'Bruker APEX area detector'
_diffrn_detector_area_resol_mean 8.366
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      2.30 183.91   0.30    9.99    --   28.00  73.65 -25.70  606
  2  ω      2.30 132.66   0.30    9.99    --   28.00  73.65  64.30  435
  3  ω      2.30  71.23   0.30    9.99    --   28.00  73.65 154.30  230
  4  ω      2.30  17.28   0.30    9.99    --   28.00  73.65 -25.70   50
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0506718000
_diffrn_orient_matrix_UB_12      -0.0181683000
_diffrn_orient_matrix_UB_13      0.0023935000
_diffrn_orient_matrix_UB_21      -0.0103980000
_diffrn_orient_matrix_UB_22      -0.0822111000
_diffrn_orient_matrix_UB_23      0.0082630000
_diffrn_orient_matrix_UB_31      -0.0042345000
_diffrn_orient_matrix_UB_32      -0.0155673000
_diffrn_orient_matrix_UB_33      -0.0463689000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3326
_reflns_number_total             4008
_reflns_odcompleteness_completeness 98.05
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.82
_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       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4008
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0658
_refine_ls_restrained_S_all      1.166
_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)+(0.0270P)²+2.8385P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1240
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C19(H19), C5(H5), C20(H20), C17(H17), C4(H4), C3(H3), C10(H10),
 C18(H18), C13(H13), C11(H11), C12(H12)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
S2 S 0.56759(5) 0.08571(9) 0.70855(5) 0.02370(18) Uani 1 1 d . . . . .
S1 S 0.11707(5) 0.53186(9) 0.54632(5) 0.02432(18) Uani 1 1 d . . . . .
O1 O 0.24399(15) 0.2718(3) 0.55300(13) 0.0264(5) Uani 1 1 d . . . . .
H1 H 0.291277 0.226191 0.534952 0.040 Uiso 1 1 calc R U . . .
N2 N 0.44382(16) 0.1986(3) 0.58457(15) 0.0202(5) Uani 1 1 d . . . . .
N1 N 0.20144(17) 0.5929(3) 0.70304(16) 0.0224(5) Uani 1 1 d . . . . .
C15 C 0.45078(19) 0.1524(3) 0.66691(18) 0.0190(6) Uani 1 1 d . . . . .
C14 C 0.1303(2) 0.7107(3) 0.6851(2) 0.0222(6) Uani 1 1 d . . . . .
C1 C 0.37169(19) 0.1522(3) 0.72578(18) 0.0190(6) Uani 1 1 d . . . . .
C7 C 0.2747(2) 0.3611(3) 0.63076(17) 0.0194(6) Uani 1 1 d . . . . .
H7 H 0.338116 0.410122 0.622291 0.023 Uiso 1 1 calc R U . . .
C8 C 0.20218(19) 0.4951(3) 0.63741(18) 0.0195(6) Uani 1 1 d . . . . .
C16 C 0.6089(2) 0.1192(3) 0.60567(18) 0.0209(6) Uani 1 1 d . . . . .
C6 C 0.28857(19) 0.2522(3) 0.71186(18) 0.0184(5) Uani 1 1 d . . . . .
C21 C 0.5320(2) 0.1818(3) 0.54812(18) 0.0188(6) Uani 1 1 d . . . . .
C2 C 0.3809(2) 0.0514(3) 0.80035(19) 0.0233(6) Uani 1 1 d . . . . .
H2 H 0.434941 -0.016461 0.809185 0.028 Uiso 1 1 calc R U . . .
C19 C 0.6394(2) 0.1912(4) 0.4331(2) 0.0269(7) Uani 1 1 d . . . . .
H19 H 0.651027 0.215329 0.374857 0.032 Uiso 1 1 calc R U . . .
C9 C 0.0765(2) 0.6976(3) 0.6018(2) 0.0221(6) Uani 1 1 d . . . . .
C5 C 0.2193(2) 0.2459(3) 0.77231(18) 0.0209(6) Uani 1 1 d . . . . .
H5 H 0.163270 0.309060 0.762760 0.025 Uiso 1 1 calc R U . . .
C20 C 0.5485(2) 0.2192(4) 0.46050(19) 0.0241(6) Uani 1 1 d . . . . .
H20 H 0.498697 0.262246 0.421517 0.029 Uiso 1 1 calc R U . . .
C17 C 0.7007(2) 0.0907(4) 0.5777(2) 0.0260(6) Uani 1 1 d . . . . .
H17 H 0.751053 0.048288 0.616352 0.031 Uiso 1 1 calc R U . . .
C4 C 0.2310(2) 0.1480(4) 0.84663(19) 0.0245(6) Uani 1 1 d . . . . .
H4 H 0.183957 0.148309 0.887074 0.029 Uiso 1 1 calc R U . . .
C3 C 0.3121(2) 0.0499(4) 0.86114(19) 0.0253(6) Uani 1 1 d . . . . .
H3 H 0.320168 -0.016086 0.911085 0.030 Uiso 1 1 calc R U . . .
C10 C 0.0038(2) 0.8095(4) 0.5748(2) 0.0294(7) Uani 1 1 d . . . . .
H10 H -0.032024 0.800833 0.519617 0.035 Uiso 1 1 calc R U . . .
C18 C 0.7149(2) 0.1271(4) 0.4910(2) 0.0272(7) Uani 1 1 d . . . . .
H18 H 0.775743 0.108780 0.470599 0.033 Uiso 1 1 calc R U . . .
C13 C 0.1101(2) 0.8352(4) 0.7423(2) 0.0317(7) Uani 1 1 d . . . . .
H13 H 0.144254 0.843894 0.798260 0.038 Uiso 1 1 calc R U . . .
C11 C -0.0133(2) 0.9326(4) 0.6319(2) 0.0344(8) Uani 1 1 d . . . . .
H11 H -0.060761 1.009295 0.614690 0.041 Uiso 1 1 calc R U . . .
C12 C 0.0389(2) 0.9449(4) 0.7147(3) 0.0377(8) Uani 1 1 d . . . . .
H12 H 0.025337 1.029173 0.752302 0.045 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
S2 C15 1.756(3) . ?
S2 C16 1.726(3) . ?
S1 C8 1.746(3) . ?
S1 C9 1.729(3) . ?
O1 H1 0.8200 . ?
O1 C7 1.418(3) . ?
N2 C15 1.296(3) . ?
N2 C21 1.383(3) . ?
N1 C14 1.389(4) . ?
N1 C8 1.281(4) . ?
C15 C1 1.467(4) . ?
C14 C9 1.402(4) . ?
C14 C13 1.390(4) . ?
C1 C6 1.410(4) . ?
C1 C2 1.398(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.500(4) . ?
C7 C6 1.519(4) . ?
C16 C21 1.402(4) . ?
C16 C17 1.387(4) . ?
C6 C5 1.381(4) . ?
C21 C20 1.398(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.372(4) . ?
C19 C18 1.396(4) . ?
C9 C10 1.394(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.382(4) . ?
C20 H20 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.376(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.379(4) . ?
C3 H3 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.369(5) . ?
C18 H18 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.370(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.386(5) . ?
C12 H12 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
C16 S2 C15 89.64(13) . . ?
C9 S1 C8 88.80(14) . . ?
C7 O1 H1 109.5 . . ?
C15 N2 C21 111.4(2) . . ?
C8 N1 C14 110.5(2) . . ?
N2 C15 S2 114.8(2) . . ?
N2 C15 C1 126.2(2) . . ?
C1 C15 S2 119.1(2) . . ?
N1 C14 C9 115.0(3) . . ?
N1 C14 C13 125.3(3) . . ?
C13 C14 C9 119.7(3) . . ?
C6 C1 C15 122.9(2) . . ?
C2 C1 C15 118.2(2) . . ?
C2 C1 C6 118.8(3) . . ?
O1 C7 H7 107.8 . . ?
O1 C7 C8 107.1(2) . . ?
O1 C7 C6 111.3(2) . . ?
C8 C7 H7 107.8 . . ?
C8 C7 C6 114.8(2) . . ?
C6 C7 H7 107.8 . . ?
N1 C8 S1 116.5(2) . . ?
N1 C8 C7 125.0(2) . . ?
C7 C8 S1 118.4(2) . . ?
C21 C16 S2 109.0(2) . . ?
C17 C16 S2 129.2(2) . . ?
C17 C16 C21 121.8(3) . . ?
C1 C6 C7 120.5(2) . . ?
C5 C6 C1 118.5(3) . . ?
C5 C6 C7 121.0(2) . . ?
N2 C21 C16 115.2(2) . . ?
N2 C21 C20 125.5(2) . . ?
C20 C21 C16 119.3(3) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 C1 121.7(3) . . ?
C3 C2 H2 119.1 . . ?
C20 C19 H19 119.4 . . ?
C20 C19 C18 121.2(3) . . ?
C18 C19 H19 119.4 . . ?
C14 C9 S1 109.3(2) . . ?
C10 C9 S1 129.9(2) . . ?
C10 C9 C14 120.9(3) . . ?
C6 C5 H5 119.2 . . ?
C6 C5 C4 121.7(3) . . ?
C4 C5 H5 119.2 . . ?
C21 C20 H20 120.6 . . ?
C19 C20 C21 118.8(3) . . ?
C19 C20 H20 120.6 . . ?
C16 C17 H17 121.1 . . ?
C18 C17 C16 117.8(3) . . ?
C18 C17 H17 121.1 . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H4 119.8 . . ?
C2 C3 C4 118.9(3) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C9 C10 H10 120.9 . . ?
C11 C10 C9 118.1(3) . . ?
C11 C10 H10 120.9 . . ?
C19 C18 H18 119.4 . . ?
C17 C18 C19 121.1(3) . . ?
C17 C18 H18 119.4 . . ?
C14 C13 H13 120.6 . . ?
C12 C13 C14 118.8(3) . . ?
C12 C13 H13 120.6 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.2(3) . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 121.3(3) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?

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
S2 C15 C1 C6 156.6(2) . . . . ?
S2 C15 C1 C2 -21.5(3) . . . . ?
S2 C16 C21 N2 -1.3(3) . . . . ?
S2 C16 C21 C20 179.8(2) . . . . ?
S2 C16 C17 C18 179.5(2) . . . . ?
S1 C9 C10 C11 -179.1(2) . . . . ?
O1 C7 C8 S1 -10.8(3) . . . . ?
O1 C7 C8 N1 174.0(3) . . . . ?
O1 C7 C6 C1 76.0(3) . . . . ?
O1 C7 C6 C5 -102.4(3) . . . . ?
N2 C15 C1 C6 -23.1(4) . . . . ?
N2 C15 C1 C2 158.8(3) . . . . ?
N2 C21 C20 C19 -177.9(3) . . . . ?
N1 C14 C9 S1 0.3(3) . . . . ?
N1 C14 C9 C10 -179.0(3) . . . . ?
N1 C14 C13 C12 178.7(3) . . . . ?
C15 S2 C16 C21 1.4(2) . . . . ?
C15 S2 C16 C17 -177.7(3) . . . . ?
C15 N2 C21 C16 0.4(3) . . . . ?
C15 N2 C21 C20 179.2(3) . . . . ?
C15 C1 C6 C7 3.1(4) . . . . ?
C15 C1 C6 C5 -178.4(2) . . . . ?
C15 C1 C2 C3 176.9(3) . . . . ?
C14 N1 C8 S1 -0.3(3) . . . . ?
C14 N1 C8 C7 174.9(3) . . . . ?
C14 C9 C10 C11 0.1(4) . . . . ?
C14 C13 C12 C11 0.6(5) . . . . ?
C1 C6 C5 C4 1.9(4) . . . . ?
C1 C2 C3 C4 1.5(4) . . . . ?
C7 C6 C5 C4 -179.7(3) . . . . ?
C8 S1 C9 C14 -0.4(2) . . . . ?
C8 S1 C9 C10 178.8(3) . . . . ?
C8 N1 C14 C9 0.0(3) . . . . ?
C8 N1 C14 C13 179.9(3) . . . . ?
C8 C7 C6 C1 -162.2(2) . . . . ?
C8 C7 C6 C5 19.4(4) . . . . ?
C16 S2 C15 N2 -1.3(2) . . . . ?
C16 S2 C15 C1 178.9(2) . . . . ?
C16 C21 C20 C19 0.9(4) . . . . ?
C16 C17 C18 C19 0.2(5) . . . . ?
C6 C1 C2 C3 -1.3(4) . . . . ?
C6 C7 C8 S1 -134.9(2) . . . . ?
C6 C7 C8 N1 49.9(4) . . . . ?
C6 C5 C4 C3 -1.7(4) . . . . ?
C21 N2 C15 S2 0.8(3) . . . . ?
C21 N2 C15 C1 -179.4(3) . . . . ?
C21 C16 C17 C18 0.5(4) . . . . ?
C2 C1 C6 C7 -178.8(2) . . . . ?
C2 C1 C6 C5 -0.4(4) . . . . ?
C9 S1 C8 N1 0.5(2) . . . . ?
C9 S1 C8 C7 -175.1(2) . . . . ?
C9 C14 C13 C12 -1.4(5) . . . . ?
C9 C10 C11 C12 -0.9(5) . . . . ?
C5 C4 C3 C2 0.0(4) . . . . ?
C20 C19 C18 C17 -0.3(5) . . . . ?
C17 C16 C21 N2 177.9(3) . . . . ?
C17 C16 C21 C20 -1.0(4) . . . . ?
C10 C11 C12 C13 0.6(5) . . . . ?
C18 C19 C20 C21 -0.2(4) . . . . ?
C13 C14 C9 S1 -179.6(2) . . . . ?
C13 C14 C9 C10 1.1(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.089
_oxdiff_exptl_absorpt_empirical_full_min 0.943

####################################################################### 
# 
# 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_LBiCl2-acetone
_database_code_depnum_ccdc_archive 'CCDC 2073586'
loop_
_audit_author_name
_audit_author_address
'Shigeru Shimada'
;National Institute of Advanced Industrial Science and Technology (AIST)
Japan
;
_audit_update_record             
;
2021-03-27 deposited with the CCDC.	2021-05-18 downloaded from the CCDC.
;
_audit_creation_date             2020-04-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
s-shimada@aist.go.jp
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H15 Bi Cl2 N2 O S2, C3 H6 O'
_chemical_formula_sum            'C25 H21 Bi Cl2 N2 O2 S2'
_chemical_formula_weight         725.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C25 H21 Bi1 Cl2 N2 O2 S2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Cl Cl 0.1484 0.1585 '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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8807(2)
_cell_length_b                   9.9946(2)
_cell_length_c                   15.0274(3)
_cell_angle_alpha                87.839(2)
_cell_angle_beta                 85.579(2)
_cell_angle_gamma                69.106(2)
_cell_volume                     1242.33(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7290
_cell_measurement_temperature    153
_cell_measurement_theta_max      28.7310
_cell_measurement_theta_min      2.1720
_shelx_estimated_absorpt_T_max   0.806
_shelx_estimated_absorpt_T_min   0.492
_exptl_absorpt_coefficient_mu    7.506
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77384
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.939
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             700
_exptl_crystal_recrystallization_method 
'Crystallized from CHCl3. Washed with toluene/acetone and kept in this solvent.'
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7600
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.732
_diffrn_reflns_theta_min         2.181
_diffrn_ambient_temperature      153
_diffrn_detector                 'Bruker APEX area detector'
_diffrn_detector_area_resol_mean 8.366
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      2.31 183.92   0.30    4.99    --   28.00  73.62 -25.69  606
  2  ω      2.31 132.67   0.30    4.99    --   28.00  73.62  64.31  435
  3  ω      2.31  71.24   0.30    4.99    --   28.00  73.62 154.31  230
  4  ω      2.31  17.29   0.30    4.99    --   28.00  73.62 -25.69   50
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0837679000
_diffrn_orient_matrix_UB_12      0.0385776000
_diffrn_orient_matrix_UB_13      -0.0028959000
_diffrn_orient_matrix_UB_21      -0.0134507000
_diffrn_orient_matrix_UB_22      -0.0653539000
_diffrn_orient_matrix_UB_23      -0.0035780000
_diffrn_orient_matrix_UB_31      -0.0120380000
_diffrn_orient_matrix_UB_32      -0.0034296000
_diffrn_orient_matrix_UB_33      0.0471198000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4942
_reflns_number_total             5172
_reflns_odcompleteness_completeness 97.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.67
_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       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         2.325
_refine_diff_density_min         -0.670
_refine_diff_density_rms         0.128
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         5172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0273
_refine_ls_restrained_S_all      1.029
_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)+(0.0249P)²+4.7741P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0604
_refine_ls_wR_factor_ref         0.0613
_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.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C17(H17), C18(H18), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_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 0.34738(2) 0.29898(2) 0.24335(2) 0.01623(5) Uani 1 1 d . . . . .
Cl1 Cl 0.46574(15) 0.03821(11) 0.30054(8) 0.0285(2) Uani 1 1 d . . . . .
Cl2 Cl 0.16234(14) 0.25019(13) 0.13589(8) 0.0296(3) Uani 1 1 d . . . . .
S1 S 0.76496(14) 0.49949(12) 0.33071(7) 0.0214(2) Uani 1 1 d . . . . .
S2 S 0.41217(14) 0.76057(11) 0.18933(7) 0.0217(2) Uani 1 1 d . . . . .
O1 O 0.7253(4) 0.5443(3) 0.1478(2) 0.0236(7) Uani 1 1 d . . . . .
O2 O 0.1438(5) 0.3136(4) 0.4285(3) 0.0377(9) Uani 1 1 d . . . . .
N1 N 0.5759(4) 0.3580(4) 0.3179(2) 0.0179(7) Uani 1 1 d . . . . .
N2 N 0.3156(4) 0.5483(4) 0.1762(2) 0.0177(7) Uani 1 1 d . . . . .
C1 C 0.5481(5) 0.2532(4) 0.1364(3) 0.0175(8) Uani 1 1 d . . . . .
C2 C 0.5826(6) 0.1297(5) 0.0864(3) 0.0234(9) Uani 1 1 d . . . . .
H2 H 0.513138 0.075963 0.093561 0.028 Uiso 1 1 calc R U . . .
C3 C 0.7173(6) 0.0845(5) 0.0265(3) 0.0281(10) Uani 1 1 d . . . . .
H3 H 0.738882 0.001414 -0.008230 0.034 Uiso 1 1 calc R U . . .
C4 C 0.8198(6) 0.1614(5) 0.0176(3) 0.0264(10) Uani 1 1 d . . . . .
H4 H 0.914825 0.128850 -0.021275 0.032 Uiso 1 1 calc R U . . .
C5 C 0.7841(5) 0.2854(5) 0.0653(3) 0.0220(9) Uani 1 1 d . . . . .
H5 H 0.855018 0.337799 0.058511 0.026 Uiso 1 1 calc R U . . .
C6 C 0.6466(5) 0.3353(5) 0.1230(3) 0.0192(9) Uani 1 1 d . . . . .
C7 C 0.6169(5) 0.4731(5) 0.1747(3) 0.0182(8) Uani 1 1 d . . . . .
C8 C 0.6449(5) 0.4359(4) 0.2724(3) 0.0160(8) Uani 1 1 d . . . . .
C9 C 0.7168(5) 0.4154(4) 0.4261(3) 0.0181(8) Uani 1 1 d . . . . .
C10 C 0.7678(6) 0.4132(5) 0.5118(3) 0.0221(9) Uani 1 1 d . . . . .
H10 H 0.835031 0.464016 0.525686 0.027 Uiso 1 1 calc R U . . .
C11 C 0.7155(6) 0.3335(5) 0.5751(3) 0.0247(10) Uani 1 1 d . . . . .
H11 H 0.748532 0.329103 0.634154 0.030 Uiso 1 1 calc R U . . .
C12 C 0.6164(6) 0.2593(5) 0.5562(3) 0.0249(10) Uani 1 1 d . . . . .
H12 H 0.584058 0.205011 0.601963 0.030 Uiso 1 1 calc R U . . .
C13 C 0.5644(6) 0.2634(5) 0.4716(3) 0.0231(9) Uani 1 1 d . . . . .
H13 H 0.496088 0.213121 0.458508 0.028 Uiso 1 1 calc R U . . .
C14 C 0.6148(5) 0.3435(4) 0.4058(3) 0.0175(8) Uani 1 1 d . . . . .
C15 C 0.4445(5) 0.5808(5) 0.1748(3) 0.0186(8) Uani 1 1 d . . . . .
C16 C 0.2059(6) 0.7962(5) 0.1971(3) 0.0208(9) Uani 1 1 d . . . . .
C17 C 0.0805(6) 0.9261(5) 0.2096(3) 0.0242(10) Uani 1 1 d . . . . .
H17 H 0.101041 1.012423 0.214689 0.029 Uiso 1 1 calc R U . . .
C18 C -0.0749(6) 0.9261(5) 0.2144(3) 0.0307(11) Uani 1 1 d . . . . .
H18 H -0.162965 1.013756 0.223779 0.037 Uiso 1 1 calc R U . . .
C19 C -0.1053(6) 0.7999(5) 0.2057(3) 0.0288(10) Uani 1 1 d . . . . .
H19 H -0.213769 0.802974 0.209259 0.035 Uiso 1 1 calc R U . . .
C20 C 0.0195(6) 0.6704(5) 0.1922(3) 0.0236(9) Uani 1 1 d . . . . .
H20 H -0.001872 0.584768 0.185770 0.028 Uiso 1 1 calc R U . . .
C21 C 0.1769(5) 0.6686(4) 0.1881(3) 0.0182(8) Uani 1 1 d . . . . .
C22 C 0.7161(6) 0.6052(6) 0.0587(3) 0.0294(11) Uani 1 1 d . . . . .
H22A H 0.822198 0.566367 0.026165 0.044 Uiso 1 1 calc R U . . .
H22B H 0.683291 0.709561 0.062311 0.044 Uiso 1 1 calc R U . . .
H22C H 0.636617 0.581057 0.027376 0.044 Uiso 1 1 calc R U . . .
C23 C 0.1330(6) 0.2033(5) 0.4586(3) 0.0299(11) Uani 1 1 d . . . . .
C24 C 0.0604(7) 0.1181(5) 0.4081(4) 0.0331(11) Uani 1 1 d . . . . .
H24A H -0.036145 0.113119 0.442085 0.050 Uiso 1 1 calc R U . . .
H24B H 0.139231 0.021110 0.398842 0.050 Uiso 1 1 calc R U . . .
H24C H 0.030589 0.164306 0.350081 0.050 Uiso 1 1 calc R U . . .
C25 C 0.1888(8) 0.1486(7) 0.5479(4) 0.0481(15) Uani 1 1 d . . . . .
H25A H 0.280438 0.058000 0.541295 0.072 Uiso 1 1 calc R U . . .
H25B H 0.100504 0.132826 0.584653 0.072 Uiso 1 1 calc R U . . .
H25C H 0.222456 0.218776 0.576622 0.072 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 Cl1 2.5792(11) . ?
Bi1 Cl2 2.5662(11) . ?
Bi1 N1 2.641(3) . ?
Bi1 N2 2.581(3) . ?
Bi1 C1 2.237(4) . ?
S1 C8 1.726(4) . ?
S1 C9 1.736(4) . ?
S2 C15 1.735(4) . ?
S2 C16 1.732(5) . ?
O1 C7 1.415(5) . ?
O1 C22 1.445(5) . ?
O2 C23 1.209(6) . ?
N1 C8 1.298(5) . ?
N1 C14 1.381(5) . ?
N2 C15 1.295(6) . ?
N2 C21 1.386(6) . ?
C1 C2 1.394(6) . ?
C1 C6 1.397(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.379(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(6) . ?
C6 C7 1.536(6) . ?
C7 C8 1.518(5) . ?
C7 C15 1.526(6) . ?
C9 C10 1.394(6) . ?
C9 C14 1.397(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.377(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.387(7) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.395(6) . ?
C16 C17 1.384(6) . ?
C16 C21 1.402(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.376(7) . ?
C18 H18 0.9500 . ?
C18 C19 1.394(7) . ?
C19 H19 0.9500 . ?
C19 C20 1.381(6) . ?
C20 H20 0.9500 . ?
C20 C21 1.388(6) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.494(7) . ?
C23 C25 1.482(7) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?

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
Cl1 Bi1 N1 89.78(8) . . ?
Cl1 Bi1 N2 163.51(8) . . ?
Cl2 Bi1 Cl1 95.17(4) . . ?
Cl2 Bi1 N1 166.16(8) . . ?
Cl2 Bi1 N2 94.37(8) . . ?
N2 Bi1 N1 78.03(11) . . ?
C1 Bi1 Cl1 90.13(11) . . ?
C1 Bi1 Cl2 91.12(11) . . ?
C1 Bi1 N1 75.92(13) . . ?
C1 Bi1 N2 76.25(13) . . ?
C8 S1 C9 88.9(2) . . ?
C16 S2 C15 89.2(2) . . ?
C7 O1 C22 117.4(3) . . ?
C8 N1 Bi1 117.7(3) . . ?
C8 N1 C14 111.4(3) . . ?
C14 N1 Bi1 129.6(3) . . ?
C15 N2 Bi1 114.6(3) . . ?
C15 N2 C21 111.5(4) . . ?
C21 N2 Bi1 124.2(3) . . ?
C2 C1 Bi1 117.3(3) . . ?
C2 C1 C6 119.5(4) . . ?
C6 C1 Bi1 123.0(3) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.7(4) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.5(4) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(4) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.4(4) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C7 122.9(4) . . ?
C5 C6 C1 118.8(4) . . ?
C5 C6 C7 118.1(4) . . ?
O1 C7 C6 114.0(4) . . ?
O1 C7 C8 104.5(3) . . ?
O1 C7 C15 108.8(3) . . ?
C8 C7 C6 109.3(3) . . ?
C8 C7 C15 104.9(3) . . ?
C15 C7 C6 114.6(3) . . ?
N1 C8 S1 115.9(3) . . ?
N1 C8 C7 122.0(4) . . ?
C7 C8 S1 122.1(3) . . ?
C10 C9 S1 128.4(3) . . ?
C10 C9 C14 121.9(4) . . ?
C14 C9 S1 109.7(3) . . ?
C9 C10 H10 121.8 . . ?
C11 C10 C9 116.5(4) . . ?
C11 C10 H10 121.8 . . ?
C10 C11 H11 118.7 . . ?
C10 C11 C12 122.6(4) . . ?
C12 C11 H11 118.7 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.7(4) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.9 . . ?
C12 C13 C14 118.2(4) . . ?
C14 C13 H13 120.9 . . ?
N1 C14 C9 114.1(4) . . ?
N1 C14 C13 125.8(4) . . ?
C13 C14 C9 120.1(4) . . ?
N2 C15 S2 115.6(3) . . ?
N2 C15 C7 125.2(4) . . ?
C7 C15 S2 118.6(3) . . ?
C17 C16 S2 128.9(4) . . ?
C17 C16 C21 121.6(4) . . ?
C21 C16 S2 109.5(3) . . ?
C16 C17 H17 121.1 . . ?
C18 C17 C16 117.8(4) . . ?
C18 C17 H17 121.1 . . ?
C17 C18 H18 119.4 . . ?
C17 C18 C19 121.2(4) . . ?
C19 C18 H18 119.4 . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.1(5) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 120.8 . . ?
C19 C20 C21 118.3(4) . . ?
C21 C20 H20 120.8 . . ?
N2 C21 C16 114.2(4) . . ?
N2 C21 C20 125.8(4) . . ?
C20 C21 C16 120.0(4) . . ?
O1 C22 H22A 109.5 . . ?
O1 C22 H22B 109.5 . . ?
O1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O2 C23 C24 121.3(5) . . ?
O2 C23 C25 121.2(5) . . ?
C25 C23 C24 117.5(5) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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 N1 C8 S1 168.29(18) . . . . ?
Bi1 N1 C8 C7 -9.5(5) . . . . ?
Bi1 N1 C14 C9 -165.8(3) . . . . ?
Bi1 N1 C14 C13 15.7(6) . . . . ?
Bi1 N2 C15 S2 -146.6(2) . . . . ?
Bi1 N2 C15 C7 24.2(5) . . . . ?
Bi1 N2 C21 C16 143.0(3) . . . . ?
Bi1 N2 C21 C20 -36.5(5) . . . . ?
Bi1 C1 C2 C3 -172.1(3) . . . . ?
Bi1 C1 C6 C5 169.4(3) . . . . ?
Bi1 C1 C6 C7 -5.9(6) . . . . ?
S1 C9 C10 C11 -177.8(3) . . . . ?
S1 C9 C14 N1 -1.0(5) . . . . ?
S1 C9 C14 C13 177.7(3) . . . . ?
S2 C16 C17 C18 -179.3(3) . . . . ?
S2 C16 C21 N2 0.4(4) . . . . ?
S2 C16 C21 C20 179.9(3) . . . . ?
O1 C7 C8 S1 8.4(5) . . . . ?
O1 C7 C8 N1 -173.9(4) . . . . ?
O1 C7 C15 S2 -25.7(4) . . . . ?
O1 C7 C15 N2 163.7(4) . . . . ?
C1 C2 C3 C4 1.3(7) . . . . ?
C1 C6 C7 O1 -176.8(4) . . . . ?
C1 C6 C7 C8 66.8(5) . . . . ?
C1 C6 C7 C15 -50.6(5) . . . . ?
C2 C1 C6 C5 -5.1(6) . . . . ?
C2 C1 C6 C7 179.7(4) . . . . ?
C2 C3 C4 C5 -2.8(7) . . . . ?
C3 C4 C5 C6 0.3(7) . . . . ?
C4 C5 C6 C1 3.6(6) . . . . ?
C4 C5 C6 C7 179.1(4) . . . . ?
C5 C6 C7 O1 8.0(5) . . . . ?
C5 C6 C7 C8 -108.5(4) . . . . ?
C5 C6 C7 C15 134.2(4) . . . . ?
C6 C1 C2 C3 2.7(6) . . . . ?
C6 C7 C8 S1 130.8(3) . . . . ?
C6 C7 C8 N1 -51.5(5) . . . . ?
C6 C7 C15 S2 -154.6(3) . . . . ?
C6 C7 C15 N2 34.8(6) . . . . ?
C8 S1 C9 C10 -179.7(4) . . . . ?
C8 S1 C9 C14 0.9(3) . . . . ?
C8 N1 C14 C9 0.5(5) . . . . ?
C8 N1 C14 C13 -178.1(4) . . . . ?
C8 C7 C15 S2 85.6(4) . . . . ?
C8 C7 C15 N2 -85.0(5) . . . . ?
C9 S1 C8 N1 -0.6(3) . . . . ?
C9 S1 C8 C7 177.2(4) . . . . ?
C9 C10 C11 C12 -0.4(7) . . . . ?
C10 C9 C14 N1 179.6(4) . . . . ?
C10 C9 C14 C13 -1.7(7) . . . . ?
C10 C11 C12 C13 -0.5(7) . . . . ?
C11 C12 C13 C14 0.3(7) . . . . ?
C12 C13 C14 N1 179.3(4) . . . . ?
C12 C13 C14 C9 0.8(6) . . . . ?
C14 N1 C8 S1 0.2(5) . . . . ?
C14 N1 C8 C7 -177.6(4) . . . . ?
C14 C9 C10 C11 1.5(6) . . . . ?
C15 S2 C16 C17 -179.6(4) . . . . ?
C15 S2 C16 C21 0.1(3) . . . . ?
C15 N2 C21 C16 -0.9(5) . . . . ?
C15 N2 C21 C20 179.7(4) . . . . ?
C15 C7 C8 S1 -106.0(4) . . . . ?
C15 C7 C8 N1 71.7(5) . . . . ?
C16 S2 C15 N2 -0.6(3) . . . . ?
C16 S2 C15 C7 -172.1(3) . . . . ?
C16 C17 C18 C19 -0.9(7) . . . . ?
C17 C16 C21 N2 -179.8(4) . . . . ?
C17 C16 C21 C20 -0.4(6) . . . . ?
C17 C18 C19 C20 0.1(7) . . . . ?
C18 C19 C20 C21 0.6(7) . . . . ?
C19 C20 C21 N2 179.0(4) . . . . ?
C19 C20 C21 C16 -0.4(6) . . . . ?
C21 N2 C15 S2 1.0(5) . . . . ?
C21 N2 C15 C7 171.8(4) . . . . ?
C21 C16 C17 C18 1.0(6) . . . . ?
C22 O1 C7 C6 66.4(5) . . . . ?
C22 O1 C7 C8 -174.4(4) . . . . ?
C22 O1 C7 C15 -62.8(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.301
_oxdiff_exptl_absorpt_empirical_full_min 0.811
