# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2129448'
loop_
_audit_author_name
_audit_author_address
'Prabu Sankar Ganesan'
;Indian Institute of Technology Hyderabad
India
;
_audit_update_record             
;
2021-12-17 deposited with the CCDC.	2022-04-22 downloaded from the CCDC.
;
_audit_creation_date             2021-12-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
loop_
_audit_author_email
prabu@chy.iith.ac.in
_publ_section_exptl              
;
Any special experimental details
;
_chemical_formula_moiety         'C12 H16 Bi Cl3 N2 O S'
_chemical_formula_sum            'C12 H16 Bi Cl3 N2 O S'
_chemical_formula_weight         551.68
_chemical_oxdiff_formula         C12H16N2SBiBr3
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.36843 0.69943 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Bi -3.68252 9.31182 33.36890 12.95100 16.58770 6.46920 0.70400 2.92380 8.79370
48.00930 13.5782003403
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.33537 0.55136 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   10.6327(2)
_cell_length_b                   10.36708(17)
_cell_length_c                   17.0092(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.4866(19)
_cell_angle_gamma                90
_cell_volume                     1806.84(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3679
_cell_measurement_temperature    293
_cell_measurement_theta_max      69.9710
_cell_measurement_theta_min      4.3650
_exptl_absorpt_coefficient_mu    24.290
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.0279
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1033.3057
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6672
_diffrn_reflns_theta_full        69.9389
_diffrn_reflns_theta_max         69.94
_diffrn_reflns_theta_min         4.31
_diffrn_ambient_temperature      293.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1293
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9854
_diffrn_measured_fraction_theta_max 0.9854
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     30.00  56.00   1.00    1.00    --    0.00  57.00-180.00   26
  2  ω     25.00  59.00   1.00    1.00    --    0.00  57.00 -90.00   34
  3  ω     -5.00  20.00   1.00    1.00    --    0.00 -87.00 -58.00   25
  4  ω     -6.00  19.00   1.00    1.00    --    0.00  57.00 -90.00   25
  5  ω     34.00  75.00   1.00    1.00    --   54.00 -57.00  90.00   41
  6  ω     39.00 110.00   1.00    1.00    --   54.00  57.00 120.00   71
  7  ω     24.00 106.00   1.00    1.00    --   54.00-125.00  90.00   82
  8  ω    -14.00  12.00   1.00    1.00    --   54.00 -57.00  90.00   26
  9  ω     41.00 118.00   1.00    1.00    --   54.00  77.00 -30.00   77
 10  ω     88.00 125.00   1.00    1.00    --  108.00  50.00 -60.00   37
 11  ω     37.00 129.00   1.00    1.00    --  108.00 -50.00-150.00   92
 12  ω     93.00 174.00   1.00    1.00    --  108.00  63.00  30.00   81
 13  ω    100.00 149.00   1.00    1.00    --  108.00 111.00 -60.00   49
 14  ω    133.00 175.00   1.00    1.00    --  108.00  63.00   0.00   42
 15  ω     85.00 115.00   1.00    1.00    --  108.00  63.00   0.00   30
 16  ω     81.00 112.00   1.00    1.00    --  108.00-111.00 -90.00   31
 17  ω    104.00 138.00   1.00    1.00    --  108.00 111.00-150.00   34
 18  ω     42.00 106.00   1.00    1.00    --  108.00-111.00  30.00   64
 19  ω     42.00  97.00   1.00    1.00    --  108.00 -91.00-150.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0991907000
_diffrn_orient_matrix_UB_12      -0.0104110000
_diffrn_orient_matrix_UB_13      0.0843356000
_diffrn_orient_matrix_UB_21      -0.0220725000
_diffrn_orient_matrix_UB_22      -0.1469097000
_diffrn_orient_matrix_UB_23      -0.0002377000
_diffrn_orient_matrix_UB_31      0.1107649000
_diffrn_orient_matrix_UB_32      -0.0200102000
_diffrn_orient_matrix_UB_33      -0.0414927000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                3031
_reflns_number_total             3365
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.1878
_refine_diff_density_min         -2.0355
_refine_diff_density_rms         0.2295
_refine_ls_d_res_high            0.8207
_refine_ls_d_res_low             10.2466
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0235
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    26
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3365
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0346
_refine_ls_restrained_S_all      1.0235
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0519P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0908
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b), C9(H9a,H9b)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C4(H4), C5(H5)
2.d Idealised Me refined as rotating group:
 C11(H11a,H11b,H11c), C12(H12a,H12b,H12c)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3a)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
Bi1 Bi 0.04127(2) 0.68501(2) 0.064728(13) 0.02602(12) Uani 1.000000 .
S1 S 0.05073(14) 0.52938(15) 0.18752(9) 0.0268(3) Uani 1.000000 .
Cl3 Cl 0.17419(15) 0.49079(18) -0.00478(10) 0.0399(4) Uani 1.000000 .
Cl1 Cl -0.11139(18) 0.84693(18) 0.11066(11) 0.0433(4) Uani 1.000000 .
C1 C 0.1917(6) 0.5696(6) 0.2612(3) 0.0238(12) Uani 1.000000 .
C7 C 0.3938(6) 0.5667(6) 0.3418(4) 0.0311(14) Uani 1.000000 .
N1 N 0.3095(5) 0.5136(5) 0.2719(3) 0.0273(11) Uani 1.000000 .
C2 C 0.3228(6) 0.6565(6) 0.3725(4) 0.0282(13) Uani 1.000000 .
C6 C 0.5255(6) 0.5440(8) 0.3811(4) 0.0409(17) Uani 1.000000 .
H6 H 0.5745(6) 0.4829(8) 0.3622(4) 0.049(2) Uiso 1.000000 R
C3 C 0.3775(7) 0.7294(7) 0.4417(4) 0.0396(16) Uani 1.000000 .
H3 H 0.3291(7) 0.7896(7) 0.4618(4) 0.047(2) Uiso 1.000000 R
N2 N 0.1959(5) 0.6553(5) 0.3212(3) 0.0255(11) Uani 1.000000 .
C4 C 0.5082(8) 0.7072(8) 0.4789(5) 0.051(2) Uani 1.000000 .
H4 H 0.5498(8) 0.7540(8) 0.5252(5) 0.061(3) Uiso 1.000000 R
C5 C 0.5774(7) 0.6168(9) 0.4485(5) 0.052(2) Uani 1.000000 .
H5 H 0.6649(7) 0.6047(9) 0.4756(5) 0.062(2) Uiso 1.000000 R
C8 C 0.0882(7) 0.7382(7) 0.3279(4) 0.0349(15) Uani 1.000000 .
H8a H 0.1234(7) 0.8130(7) 0.3607(4) 0.0419(18) Uiso 1.000000 R
H8b H 0.0421(7) 0.7685(7) 0.2740(4) 0.0419(18) Uiso 1.000000 R
C9 C -0.0069(7) 0.6713(7) 0.3655(5) 0.0426(18) Uani 1.000000 .
H9a H -0.0798(7) 0.7284(7) 0.3642(5) 0.051(2) Uiso 1.000000 R
H9b H -0.0407(7) 0.5950(7) 0.3339(5) 0.051(2) Uiso 1.000000 R
O3 O 0.0538(7) 0.6351(6) 0.4478(3) 0.0525(14) Uani 1.000000 .
H3a H 0.068(9) 0.5573(17) 0.4500(10) 0.079(2) Uiso 1.000000 GR
C10 C 0.3419(7) 0.4142(7) 0.2182(4) 0.0389(16) Uani 1.000000 .
H10 H 0.2643(7) 0.4025(7) 0.1724(4) 0.047(2) Uiso 1.000000 R
C11 C 0.4505(7) 0.4590(9) 0.1829(5) 0.054(2) Uani 1.000000 .
H11a H 0.430(3) 0.543(3) 0.159(3) 0.081(3) Uiso 1.000000 GR
H11b H 0.5305(14) 0.464(6) 0.2255(8) 0.081(3) Uiso 1.000000 GR
H11c H 0.461(4) 0.399(3) 0.142(3) 0.081(3) Uiso 1.000000 GR
C12 C 0.3681(9) 0.2853(8) 0.2632(6) 0.058(2) Uani 1.000000 .
H12a H 0.449(4) 0.290(2) 0.305(3) 0.086(3) Uiso 1.000000 GR
H12b H 0.298(4) 0.267(3) 0.287(4) 0.086(3) Uiso 1.000000 GR
H12c H 0.373(7) 0.2182(13) 0.2253(10) 0.086(3) Uiso 1.000000 GR
Cl2 Cl 0.2443(2) 0.7976(2) 0.14737(14) 0.0601(6) Uani 1.000000 .


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 S1 2.6198(15) . ?
Bi1 Cl3 2.8917(16) 3_565 ?
Bi1 Cl3 2.8882(17) . ?
Bi1 Cl1 2.5962(17) . ?
Bi1 Cl2 2.5255(18) . ?
S1 C1 1.729(6) . ?
C1 N1 1.348(7) . ?
C1 N2 1.345(7) . ?
C7 N1 1.397(8) . ?
C7 C2 1.385(9) . ?
C7 C6 1.401(9) . ?
N1 C10 1.477(8) . ?
C2 C3 1.388(9) . ?
C2 N2 1.398(8) . ?
C6 C5 1.360(10) . ?
C3 C4 1.385(11) . ?
N2 C8 1.461(8) . ?
C4 C5 1.375(12) . ?
C8 C9 1.502(10) . ?
C9 O3 1.427(9) . ?
C10 C11 1.510(10) . ?
C10 C12 1.527(11) . ?

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
Cl3 Bi1 S1 88.75(5) . . ?
Cl3 Bi1 S1 75.59(5) 3_565 . ?
Cl1 Bi1 S1 93.00(5) . . ?
Cl1 Bi1 Cl3 170.95(5) . . ?
Cl1 Bi1 Cl3 90.77(6) . 3_565 ?
Cl2 Bi1 S1 89.76(6) . . ?
Cl2 Bi1 Cl3 96.39(7) . . ?
Cl2 Bi1 Cl3 165.14(6) . 3_565 ?
Cl2 Bi1 Cl1 92.51(8) . . ?
C1 S1 Bi1 105.7(2) . . ?
N1 C1 S1 126.1(5) . . ?
N2 C1 S1 123.8(4) . . ?
N2 C1 N1 109.9(5) . . ?
C2 C7 N1 107.2(5) . . ?
C6 C7 N1 132.2(6) . . ?
C6 C7 C2 120.6(6) . . ?
C7 N1 C1 107.9(5) . . ?
C10 N1 C1 125.3(5) . . ?
C10 N1 C7 126.8(5) . . ?
C3 C2 C7 122.6(6) . . ?
N2 C2 C7 106.9(5) . . ?
N2 C2 C3 130.5(6) . . ?
C5 C6 C7 115.9(7) . . ?
C4 C3 C2 116.0(7) . . ?
C2 N2 C1 108.1(5) . . ?
C8 N2 C1 125.4(5) . . ?
C8 N2 C2 126.4(5) . . ?
C5 C4 C3 120.9(7) . . ?
C4 C5 C6 123.9(7) . . ?
C9 C8 N2 113.1(6) . . ?
O3 C9 C8 111.0(6) . . ?
C11 C10 N1 111.1(6) . . ?
C12 C10 N1 110.0(6) . . ?
C12 C10 C11 114.3(7) . . ?

_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 3.135
_oxdiff_exptl_absorpt_empirical_full_min 0.522
####################################################################### 
# 
# 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_IV
_database_code_depnum_ccdc_archive 'CCDC 2129451'
loop_
_audit_author_name
_audit_author_address
'Prabu Sankar Ganesan'
;Indian Institute of Technology Hyderabad
India
;
_audit_update_record             
;
2021-12-17 deposited with the CCDC.	2022-04-22 downloaded from the CCDC.
;
_audit_creation_date             2021-12-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
loop_
_audit_author_email
prabu@chy.iith.ac.in
_chemical_formula_moiety         'C19 H13 N S'
_chemical_formula_sum            'C19 H13 N S'
_chemical_formula_weight         287.39
_chemical_oxdiff_formula         C19H12NS
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.33537 0.55136 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   7.4635(8)
_cell_length_b                   22.1889(13)
_cell_length_c                   9.3494(9)
_cell_angle_alpha                90
_cell_angle_beta                 110.628(12)
_cell_angle_gamma                90
_cell_volume                     1449.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1194
_cell_measurement_temperature    293
_cell_measurement_theta_max      68.3190
_cell_measurement_theta_min      3.9900
_exptl_absorpt_coefficient_mu    1.894
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.3172
_exptl_crystal_description       irregular
_exptl_crystal_F_000             602.8531
_exptl_crystal_size_max          0.67
_exptl_crystal_size_mid          0.62
_exptl_crystal_size_min          0.52
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2122
_diffrn_reflns_theta_full        69.6717
_diffrn_reflns_theta_max         69.67
_diffrn_reflns_theta_min         3.98
_diffrn_ambient_temperature      293.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1293
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.4750
_diffrn_measured_fraction_theta_max 0.4750
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00   2.00   1.00    1.40    --    0.00  77.00  30.00   27
  2  ω    -22.00  37.00   1.00    1.40    --    0.00  57.00-180.00   59
  3  ω     36.00  71.00   1.00    1.40    --    0.00  77.00  30.00   35
  4  ω     30.00 109.00   1.00    5.59    --   54.00  77.00  60.00   79
  5  ω     49.00 112.00   1.00    5.59    --   54.00  57.00-180.00   63
  6  ω     78.00 116.00   1.00    5.59    --   54.00  57.00 -60.00   38
  7  ω    -10.00  17.00   1.00    5.59    --   54.00 -57.00-150.00   27
  8  ω      7.00  85.00   1.00    5.59    --   54.00 -77.00 -60.00   78
  9  ω    116.00 141.00   1.00    5.59    --  108.00 178.00  90.00   25
 10  ω     49.00  74.00   1.00    5.59    --  108.00-111.00  30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1981654000
_diffrn_orient_matrix_UB_12      0.0088504000
_diffrn_orient_matrix_UB_13      -0.1246848000
_diffrn_orient_matrix_UB_21      -0.0914570000
_diffrn_orient_matrix_UB_22      0.0049112000
_diffrn_orient_matrix_UB_23      0.1238570000
_diffrn_orient_matrix_UB_31      0.0321901000
_diffrn_orient_matrix_UB_32      0.0686942000
_diffrn_orient_matrix_UB_33      0.0070021000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              25
_reflns_limit_k_min              0
_reflns_limit_l_max              8
_reflns_limit_l_min              0
_reflns_number_gt                1147
_reflns_number_total             1301
_reflns_odcompleteness_completeness 44.01
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.1205
_refine_diff_density_min         -0.1652
_refine_diff_density_rms         0.0309
_refine_ls_d_res_high            0.8221
_refine_ls_d_res_low             11.0945
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0969
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    26
_refine_ls_number_parameters     191
_refine_ls_number_reflns         1301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0339
_refine_ls_restrained_S_all      1.0969
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0501P)²+0.2326P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0939
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C1(H1), C4(H4), C8(H8), C5(H5), C16(H16), C19(H19), C6(H6), C3(H3),
 C7(H7), C2(H2), C17(H17), C18(H18)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
S1 S 0.15031(10) 0.62471(3) 0.68360(9) 0.0796(4) Uani 1.000000 .
N1 N 0.2556(3) 0.47094(9) 0.3927(3) 0.0633(6) Uani 1.000000 .
C10 C 0.2525(3) 0.50876(12) 0.6365(3) 0.0591(7) Uani 1.000000 .
C12 C 0.2131(3) 0.52695(11) 0.3357(3) 0.0590(7) Uani 1.000000 .
C14 C 0.3726(4) 0.66003(10) 0.7752(3) 0.0597(7) Uani 1.000000 .
C11 C 0.1875(3) 0.57681(10) 0.4228(3) 0.0578(7) Uani 1.000000 .
C13 C 0.2045(3) 0.56632(11) 0.5748(3) 0.0583(7) Uani 1.000000 .
C9 C 0.2769(3) 0.46216(11) 0.5390(3) 0.0589(7) Uani 1.000000 .
C15 C 0.5434(5) 0.64324(12) 0.7613(3) 0.0664(8) Uani 1.000000 .
H15 H 0.5475(5) 0.61027(12) 0.7011(3) 0.0797(10) Uiso 1.000000 R
C1 C 0.3225(4) 0.40303(12) 0.5986(4) 0.0763(9) Uani 1.000000 .
H1 H 0.3363(4) 0.37238(12) 0.5354(4) 0.0915(10) Uiso 1.000000 R
C4 C 0.2804(4) 0.49355(15) 0.7907(3) 0.0771(9) Uani 1.000000 .
H4 H 0.2677(4) 0.52312(15) 0.8569(3) 0.0925(11) Uiso 1.000000 R
C8 C 0.1923(4) 0.53611(14) 0.1803(3) 0.0747(8) Uani 1.000000 .
H8 H 0.2055(4) 0.50369(14) 0.1217(3) 0.0897(10) Uiso 1.000000 R
C5 C 0.1471(4) 0.63410(12) 0.3499(4) 0.0743(9) Uani 1.000000 .
H5 H 0.1309(4) 0.66740(12) 0.4046(4) 0.0891(10) Uiso 1.000000 R
C16 C 0.7074(5) 0.67496(14) 0.8360(4) 0.0869(10) Uani 1.000000 .
H16 H 0.8219(5) 0.66369(14) 0.8250(4) 0.1043(11) Uiso 1.000000 R
C19 C 0.3704(5) 0.70840(11) 0.8687(3) 0.0850(9) Uani 1.000000 .
H19 H 0.2564(5) 0.71987(11) 0.8802(3) 0.1020(11) Uiso 1.000000 R
C6 C 0.1320(4) 0.64076(15) 0.2029(4) 0.0888(10) Uani 1.000000 .
H6 H 0.1070(4) 0.67869(15) 0.1579(4) 0.1065(12) Uiso 1.000000 R
C3 C 0.3255(4) 0.43632(17) 0.8421(4) 0.0894(10) Uani 1.000000 .
H3 H 0.3431(4) 0.42720(17) 0.9432(4) 0.1073(12) Uiso 1.000000 R
C7 C 0.1534(4) 0.59145(17) 0.1167(4) 0.0889(10) Uani 1.000000 .
H7 H 0.1408(4) 0.59687(17) 0.0150(4) 0.1066(12) Uiso 1.000000 R
C2 C 0.3460(4) 0.39061(15) 0.7447(5) 0.0889(10) Uani 1.000000 .
H2 H 0.3759(4) 0.35158(15) 0.7817(5) 0.1067(12) Uiso 1.000000 R
C17 C 0.7038(6) 0.72363(15) 0.9275(4) 0.1066(12) Uani 1.000000 .
H17 H 0.8148(6) 0.74541(15) 0.9771(4) 0.1279(14) Uiso 1.000000 R
C18 C 0.5355(7) 0.73925(14) 0.9439(4) 0.1066(11) Uani 1.000000 .
H18 H 0.5329(7) 0.77132(14) 1.0072(4) 0.1279(14) Uiso 1.000000 R


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
S1 C14 1.760(3) . ?
S1 C13 1.779(2) . ?
N1 C12 1.345(3) . ?
N1 C9 1.334(3) . ?
C10 C13 1.395(3) . ?
C10 C9 1.432(3) . ?
C10 C4 1.422(4) . ?
C12 C11 1.426(3) . ?
C12 C8 1.421(4) . ?
C14 C15 1.378(4) . ?
C14 C19 1.388(3) . ?
C11 C13 1.401(3) . ?
C11 C5 1.423(3) . ?
C9 C1 1.419(3) . ?
C15 C16 1.370(4) . ?
C1 C2 1.343(4) . ?
C4 C3 1.357(4) . ?
C8 C7 1.350(4) . ?
C5 C6 1.348(4) . ?
C16 C17 1.384(4) . ?
C19 C18 1.368(4) . ?
C6 C7 1.401(4) . ?
C3 C2 1.407(4) . ?
C17 C18 1.363(5) . ?

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
C13 S1 C14 103.72(13) . . ?
C9 N1 C12 117.9(2) . . ?
C9 C10 C13 118.0(2) . . ?
C4 C10 C13 124.1(3) . . ?
C4 C10 C9 117.9(2) . . ?
C11 C12 N1 123.4(2) . . ?
C8 C12 N1 117.6(2) . . ?
C8 C12 C11 119.0(2) . . ?
C15 C14 S1 125.4(2) . . ?
C19 C14 S1 115.6(2) . . ?
C19 C14 C15 119.0(3) . . ?
C13 C11 C12 117.9(2) . . ?
C5 C11 C12 117.9(3) . . ?
C5 C11 C13 124.2(2) . . ?
C10 C13 S1 120.5(2) . . ?
C11 C13 S1 120.08(19) . . ?
C11 C13 C10 119.3(2) . . ?
C10 C9 N1 123.5(2) . . ?
C1 C9 N1 117.6(2) . . ?
C1 C9 C10 118.9(3) . . ?
C16 C15 C14 120.2(3) . . ?
C2 C1 C9 121.1(3) . . ?
C3 C4 C10 120.7(3) . . ?
C7 C8 C12 120.6(3) . . ?
C6 C5 C11 120.9(3) . . ?
C17 C16 C15 120.5(3) . . ?
C18 C19 C14 120.2(3) . . ?
C7 C6 C5 121.0(3) . . ?
C2 C3 C4 121.0(3) . . ?
C6 C7 C8 120.5(3) . . ?
C3 C2 C1 120.3(3) . . ?
C18 C17 C16 119.2(3) . . ?
C17 C18 C19 120.9(3) . . ?

_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 1.649
_oxdiff_exptl_absorpt_empirical_full_min 0.741
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2129449'
loop_
_audit_author_name
_audit_author_address
'Prabu Sankar Ganesan'
;Indian Institute of Technology Hyderabad
India
;
_audit_update_record             
;
2021-12-17 deposited with the CCDC.	2022-04-22 downloaded from the CCDC.
;
_audit_creation_date             2021-12-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
loop_
_audit_author_email
prabu@chy.iith.ac.in
_chemical_formula_moiety         'C12 H15 Bi Br3 N2 O Se'
_chemical_formula_sum            'C12 H15 Bi Br3 N2 O Se'
_chemical_formula_weight         730.92
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Bi -3.98376 10.58997 33.36890 12.95100 16.58770 6.46920 0.70400 2.92380 8.79370
48.00930 13.5782003403
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Se -0.08110 2.30834 17.00060 5.81960 3.97310 4.35430 2.40980 0.27260 15.23720
43.81630 2.84089994431
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.6380(4)
_cell_length_b                   11.3080(4)
_cell_length_c                   13.1866(7)
_cell_angle_alpha                77.900(4)
_cell_angle_beta                 78.288(4)
_cell_angle_gamma                84.332(4)
_cell_volume                     1088.56(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2168
_cell_measurement_temperature    293
_cell_measurement_theta_max      26.9010
_cell_measurement_theta_min      3.6750
_exptl_absorpt_coefficient_mu    15.271
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.2298
_exptl_crystal_description       plate
_exptl_crystal_F_000             653.4063
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_diffrn_reflns_av_R_equivalents  0.0798
_diffrn_reflns_av_unetI/netI     0.1136
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8154
_diffrn_reflns_theta_full        29.1034
_diffrn_reflns_theta_max         29.10
_diffrn_reflns_theta_min         2.90
_diffrn_ambient_temperature      293.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0309
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.8161
_diffrn_measured_fraction_theta_max 0.8161
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.00  84.00   1.00   22.00    --   16.95  77.00 -60.00   97
  2  ω    -20.00  59.00   1.00   22.00    --   16.95 -99.00-180.00   79
  3  ω    -75.00 -47.00   1.00   22.00    --  -18.98 124.00  16.00   28
  4  ω    -46.00  46.00   1.00   22.00    --  -18.98  77.00  60.00   92
  5  ω    -88.00 -16.00   1.00   22.00    --  -18.98 -57.00-180.00   72
  6  ω     -6.00  50.00   1.00   22.00    --  -18.98  57.00 -30.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0215779000
_diffrn_orient_matrix_UB_12      0.0134207000
_diffrn_orient_matrix_UB_13      0.0514381000
_diffrn_orient_matrix_UB_21      0.0133443000
_diffrn_orient_matrix_UB_22      0.0620757000
_diffrn_orient_matrix_UB_23      -0.0217056000
_diffrn_orient_matrix_UB_31      -0.0915529000
_diffrn_orient_matrix_UB_32      0.0097999000
_diffrn_orient_matrix_UB_33      -0.0043996000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -9
_reflns_limit_k_max              14
_reflns_limit_k_min              -13
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                3210
_reflns_number_total             4770
_reflns_odcompleteness_completeness 96.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         3.4867
_refine_diff_density_min         -3.9716
_refine_diff_density_rms         0.4034
_refine_ls_d_res_high            0.7306
_refine_ls_d_res_low             7.0340
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   0.9272
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     185
_refine_ls_number_reflns         4770
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0578
_refine_ls_restrained_S_all      0.9272
_refine_ls_shift/su_max          2.3081
_refine_ls_shift/su_mean         0.0125
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0566P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1321
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11a,H11b)
2.c Aromatic/amide H refined with riding coordinates:
 C1aa(H1aa), C6(H6), C12(H12), C4(H4), C3(H3)
2.d Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C9(H9a,H9b,H9c)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
Bi1 Bi 0.27939(5) 0.95490(3) 0.93234(3) 0.03689(16) Uani 1.000000 .
Br2 Br 0.57582(16) 1.12131(10) 0.86121(9) 0.0490(3) Uani 1.000000 .
Se1 Se 0.51447(16) 0.75691(10) 0.90877(9) 0.0453(3) Uani 1.000000 .
Br3 Br -0.02344(16) 0.81870(11) 1.01141(12) 0.0606(4) Uani 1.000000 .
Br1 Br 0.20755(19) 0.99100(12) 0.73723(11) 0.0618(4) Uani 1.000000 .
N1 N 0.3788(12) 0.6667(7) 0.7549(7) 0.038(2) Uani 1.000000 .
N2 N 0.6000(12) 0.7849(8) 0.6814(7) 0.045(2) Uani 1.000000 .
C1 C 0.4946(13) 0.7363(9) 0.7749(8) 0.035(2) Uani 1.000000 .
C7 C 0.5471(16) 0.7452(10) 0.6001(10) 0.047(3) Uani 1.000000 .
C2 C 0.4057(16) 0.6700(10) 0.6470(9) 0.045(3) Uani 1.000000 .
C11 C 0.2409(17) 0.5987(10) 0.8344(10) 0.056(3) Uani 1.000000 .
H11a H 0.1982(17) 0.6441(10) 0.8903(10) 0.067(4) Uiso 1.000000 R
H11b H 0.1404(17) 0.5923(10) 0.8016(10) 0.067(4) Uiso 1.000000 R
C8 C 0.7540(18) 0.8610(11) 0.6718(11) 0.060(3) Uani 1.000000 .
H8 H 0.7579(18) 0.8731(11) 0.7427(11) 0.072(4) Uiso 1.000000 R
O1 O 0.3438(16) 0.4057(8) 0.8024(8) 0.083(3) Uani 1.000000 .
H1 H 0.41(2) 0.347(9) 0.821(6) 0.124(5) Uiso 1.000000 GR
C1aa C 0.528(2) 0.7130(13) 0.4337(12) 0.075(4) Uani 1.000000 .
H1aa H 0.570(2) 0.7265(13) 0.3611(12) 0.090(5) Uiso 1.000000 R
C6 C 0.6047(19) 0.7663(11) 0.4921(10) 0.061(4) Uani 1.000000 .
H6 H 0.6968(19) 0.8177(11) 0.4607(10) 0.073(4) Uiso 1.000000 R
C12 C 0.3038(19) 0.4762(11) 0.8814(11) 0.070(4) Uani 1.000000 .
H12 H 0.3153(19) 0.4497(11) 0.9516(11) 0.084(5) Uiso 1.000000 R
C10 C 0.723(2) 0.9846(12) 0.6045(12) 0.084(5) Uani 1.000000 .
H10a H 0.713(13) 0.9754(14) 0.535(3) 0.126(7) Uiso 1.000000 GR
H10b H 0.614(7) 1.023(4) 0.636(4) 0.126(7) Uiso 1.000000 GR
H10c H 0.821(6) 1.033(3) 0.599(6) 0.126(7) Uiso 1.000000 GR
C4 C 0.385(2) 0.6364(15) 0.4774(13) 0.080(5) Uani 1.000000 .
H4 H 0.332(2) 0.6017(15) 0.4340(13) 0.097(6) Uiso 1.000000 R
C3 C 0.3251(18) 0.6134(11) 0.5864(11) 0.063(4) Uani 1.000000 .
H3 H 0.2335(18) 0.5616(11) 0.6175(11) 0.075(5) Uiso 1.000000 R
C9 C 0.9268(18) 0.7938(13) 0.6329(14) 0.092(5) Uani 1.000000 .
H9a H 0.951(8) 0.727(6) 0.687(4) 0.138(8) Uiso 1.000000 GR
H9b H 0.916(6) 0.764(9) 0.571(6) 0.138(8) Uiso 1.000000 GR
H9c H 1.023(3) 0.848(3) 0.615(9) 0.138(8) Uiso 1.000000 GR


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 Br2 2.9642(12) . ?
Bi1 Br2 3.0704(12) 2_677 ?
Bi1 Se1 2.7576(11) . ?
Bi1 Br3 2.8037(13) . ?
Bi1 Br1 2.6788(13) . ?
Se1 C1 1.867(10) . ?
N1 C1 1.338(13) . ?
N1 C2 1.389(13) . ?
N1 C11 1.474(14) . ?
N2 C1 1.367(13) . ?
N2 C7 1.389(13) . ?
N2 C8 1.495(15) . ?
C7 C2 1.401(17) . ?
C7 C6 1.379(16) . ?
C2 C3 1.385(15) . ?
C11 C12 1.471(16) . ?
C8 C10 1.516(17) . ?
C8 C9 1.507(17) . ?
O1 C12 1.409(14) . ?
C1aa C6 1.322(17) . ?
C1aa C4 1.41(2) . ?
C4 C3 1.39(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Se1 Bi1 Br2 91.33(4) . . ?
Se1 Bi1 Br2 73.73(3) . 2_677 ?
Br3 Bi1 Br2 173.29(3) . . ?
Br3 Bi1 Br2 93.16(4) . 2_677 ?
Br3 Bi1 Se1 94.85(4) . . ?
Br1 Bi1 Br2 168.32(4) . 2_677 ?
Br1 Bi1 Br2 91.77(4) . . ?
Br1 Bi1 Se1 94.88(4) . . ?
Br1 Bi1 Br3 90.30(5) . . ?
C1 Se1 Bi1 101.2(3) . . ?
C2 N1 C1 109.5(10) . . ?
C11 N1 C1 125.6(9) . . ?
C11 N1 C2 124.9(10) . . ?
C7 N2 C1 108.7(10) . . ?
C8 N2 C1 124.5(10) . . ?
C8 N2 C7 126.7(10) . . ?
N1 C1 Se1 125.3(8) . . ?
N2 C1 Se1 126.1(8) . . ?
N2 C1 N1 108.5(9) . . ?
C2 C7 N2 106.5(11) . . ?
C6 C7 N2 133.3(13) . . ?
C6 C7 C2 120.2(11) . . ?
C7 C2 N1 106.7(10) . . ?
C3 C2 N1 132.6(13) . . ?
C3 C2 C7 120.7(12) . . ?
C12 C11 N1 114.0(10) . . ?
C10 C8 N2 109.9(11) . . ?
C9 C8 N2 109.7(10) . . ?
C9 C8 C10 114.4(12) . . ?
C4 C1aa C6 122.4(15) . . ?
C1aa C6 C7 119.4(15) . . ?
O1 C12 C11 108.6(11) . . ?
C3 C4 C1aa 119.2(13) . . ?
C4 C3 C2 118.0(15) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 0.500 240.8 45.4 ?


_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 4.643
_oxdiff_exptl_absorpt_empirical_full_min 0.535
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 2129450'
loop_
_audit_author_name
_audit_author_address
'Prabu Sankar Ganesan'
;Indian Institute of Technology Hyderabad
India
;
_audit_update_record             
;
2021-12-17 deposited with the CCDC.	2022-04-22 downloaded from the CCDC.
;
_audit_creation_date             2021-12-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
loop_
_audit_author_email
prabu@chy.iith.ac.in
_chemical_formula_moiety         'C48 H64 Bi2 Br6 N8 O4 S4'
_chemical_formula_sum            'C48 H64 Bi2 Br6 N8 O4 S4'
_chemical_formula_weight         1842.74
_chemical_oxdiff_formula         C28H32BiBr3N2OS
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Bi -3.68252 9.31182 33.36890 12.95100 16.58770 6.46920 0.70400 2.92380 8.79370
48.00930 13.5782003403
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.33537 0.55136 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.67402 1.33011 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   9.28018(15)
_cell_length_b                   23.7009(3)
_cell_length_c                   14.4183(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.9584(15)
_cell_angle_gamma                90
_cell_volume                     3159.41(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5425
_cell_measurement_temperature    293
_cell_measurement_theta_max      69.9770
_cell_measurement_theta_min      3.6060
_exptl_absorpt_coefficient_mu    16.853
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.9369
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1743.2135
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.0776
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11869
_diffrn_reflns_theta_full        70.0092
_diffrn_reflns_theta_max         70.01
_diffrn_reflns_theta_min         3.60
_diffrn_ambient_temperature      293.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1293
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9811
_diffrn_measured_fraction_theta_max 0.9811
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -11.00  20.00   1.00    1.00    --    0.00 -57.00 -60.00   31
  2  ω    -63.00 -29.00   1.00    1.00    --    0.00 -57.00  90.00   34
  3  ω    -11.00  16.00   1.00    1.00    --    0.00 -57.00  90.00   27
  4  ω    -17.00  71.00   1.00    1.56    --   54.00 -77.00 -30.00   88
  5  ω     32.00 117.00   1.00    1.56    --   54.00  57.00  90.00   85
  6  ω     42.00 122.00   1.00    1.56    --   54.00  57.00-150.00   80
  7  ω     27.00  52.00   1.00    1.56    --   54.00 -99.00-150.00   25
  8  ω     83.00 108.00   1.00    1.56    --   54.00  57.00 120.00   25
  9  ω     92.00 175.00   1.00    1.56    --  108.00  63.00  60.00   83
 10  ω    110.00 136.00   1.00    1.56    --  108.00  50.00 -30.00   26
 11  ω     37.00 129.00   1.00    1.56    --  108.00 -38.00 -90.00   92
 12  ω     37.00 140.00   1.00    1.56    --  108.00 -77.00 -60.00  103
 13  ω    147.00 173.00   1.00    1.56    --  108.00  50.00 -30.00   26
 14  ω     62.00 143.00   1.00    1.56    --  108.00 178.00-180.00   81
 15  ω     44.00 128.00   1.00    1.56    --  108.00 -50.00 120.00   84
 16  ω     90.00 116.00   1.00    1.56    --  108.00 -25.00  30.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0115447000
_diffrn_orient_matrix_UB_12      -0.0601397000
_diffrn_orient_matrix_UB_13      0.0393372000
_diffrn_orient_matrix_UB_21      0.1470428000
_diffrn_orient_matrix_UB_22      -0.0150760000
_diffrn_orient_matrix_UB_23      -0.0355425000
_diffrn_orient_matrix_UB_31      0.0774864000
_diffrn_orient_matrix_UB_32      0.0196152000
_diffrn_orient_matrix_UB_33      0.0931858000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -11
_reflns_limit_k_max              28
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              -8
_reflns_number_gt                4693
_reflns_number_total             5874
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.8415
_refine_diff_density_min         -2.8296
_refine_diff_density_rms         0.2674
_refine_ls_d_res_high            0.8203
_refine_ls_d_res_low             12.2843
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   0.9798
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    52
_refine_ls_number_parameters     332
_refine_ls_number_reflns         5874
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0544
_refine_ls_restrained_S_all      0.9798
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0764P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1286
_refine_ls_wR_factor_ref         0.1402
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b), C9(H9a,H9b), C20(H20a,H20b), C21(H21a,H21b)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C15(H15), C16(H16), C17(H17), C5(H5), C4(H4), C18(H18)
2.d Idealised Me refined as rotating group:
 C11(H11a,H11b,H11c), C23(H23a,H23b,H23c), C12(H12a,H12b,H12c), C24(H24a,H24b,
 H24c)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
Bi1 Bi 0.98597(3) 0.035208(10) 0.64343(2) 0.03373(14) Uani 1.000000 .
Br2 Br 1.19641(11) 0.03531(4) 0.49083(7) 0.0501(3) Uani 1.000000 .
Br1 Br 0.79139(12) 0.03471(4) 0.77207(9) 0.0581(3) Uani 1.000000 .
Br3 Br 1.18988(12) 0.08382(4) 0.76637(9) 0.0622(3) Uani 1.000000 .
C11 C 0.9701(13) -0.0817(6) 0.9616(11) 0.092(4) Uani 1.000000 .
H11a H 1.034(6) -0.083(4) 1.018(3) 0.139(7) Uiso 1.000000 GR
H11b H 0.961(11) -0.0432(11) 0.941(3) 0.139(7) Uiso 1.000000 GR
H11c H 0.877(5) -0.096(3) 0.974(6) 0.139(7) Uiso 1.000000 GR
S1 S 1.0805(2) -0.07523(7) 0.68155(17) 0.0450(5) Uani 1.000000 .
S2 S 0.8594(3) 0.13710(8) 0.56160(18) 0.0523(6) Uani 1.000000 .
N2 N 0.6471(8) 0.1636(3) 0.6749(5) 0.0422(17) Uani 1.000000 .
N4 N 1.1711(8) -0.0925(3) 0.8645(5) 0.0405(16) Uani 1.000000 .
N1 N 0.8479(9) 0.2122(3) 0.7054(6) 0.053(2) Uani 1.000000 .
C7 C 1.2962(9) -0.0886(3) 0.9248(6) 0.0405(19) Uani 1.000000 .
C2 C 1.4027(9) -0.0658(3) 0.8730(6) 0.0399(19) Uani 1.000000 .
N3 N 1.3389(8) -0.0570(2) 0.7839(5) 0.0408(16) Uani 1.000000 .
C8 C 1.4113(10) -0.0327(3) 0.7074(7) 0.048(2) Uani 1.000000 .
H8a H 1.3394(10) -0.0157(3) 0.6632(7) 0.058(3) Uiso 1.000000 R
H8b H 1.4762(10) -0.0031(3) 0.7316(7) 0.058(3) Uiso 1.000000 R
C6 C 1.3262(11) -0.1018(4) 1.0168(7) 0.051(2) Uani 1.000000 .
H6 H 1.2558(11) -0.1171(4) 1.0515(7) 0.061(3) Uiso 1.000000 R
C3 C 1.5421(10) -0.0562(3) 0.9118(7) 0.049(2) Uani 1.000000 .
H3 H 1.6127(10) -0.0417(3) 0.8764(7) 0.058(3) Uiso 1.000000 R
C19 C 0.7452(10) 0.2328(3) 0.7644(8) 0.053(3) Uani 1.000000 .
C14 C 0.6204(10) 0.2011(3) 0.7454(7) 0.044(2) Uani 1.000000 .
C10 C 1.0305(10) -0.1165(4) 0.8875(8) 0.057(3) Uani 1.000000 .
H10 H 0.9633(10) -0.1134(4) 0.8315(8) 0.069(3) Uiso 1.000000 R
C15 C 0.4997(12) 0.2109(4) 0.7913(8) 0.060(3) Uani 1.000000 .
H15 H 0.4157(12) 0.1899(4) 0.7787(8) 0.072(3) Uiso 1.000000 R
C16 C 0.5080(12) 0.2535(5) 0.8573(8) 0.071(3) Uani 1.000000 .
H16 H 0.4283(12) 0.2609(5) 0.8903(8) 0.085(4) Uiso 1.000000 R
C22 C 0.9925(13) 0.2346(5) 0.6945(13) 0.097(5) Uani 1.000000 .
H22 H 1.0395(13) 0.2083(5) 0.6542(13) 0.117(6) Uiso 1.000000 R
C17 C 0.6306(14) 0.2849(5) 0.8749(10) 0.085(4) Uani 1.000000 .
H17 H 0.6310(14) 0.3135(5) 0.9191(10) 0.102(5) Uiso 1.000000 R
C23 C 0.9831(18) 0.2899(7) 0.6458(15) 0.172(11) Uani 1.000000 .
H23a H 0.924(17) 0.315(3) 0.678(8) 0.258(16) Uiso 1.000000 GR
H23b H 1.078(3) 0.306(4) 0.645(12) 0.258(16) Uiso 1.000000 GR
H23c H 0.94(2) 0.2847(14) 0.583(4) 0.258(16) Uiso 1.000000 GR
C1 C 1.1987(9) -0.0740(3) 0.7793(6) 0.0353(17) Uani 1.000000 .
C13 C 0.7840(9) 0.1715(3) 0.6499(7) 0.041(2) Uani 1.000000 .
C5 C 1.4667(12) -0.0913(4) 1.0572(7) 0.059(3) Uani 1.000000 .
H5 H 1.4896(12) -0.0994(4) 1.1199(7) 0.071(3) Uiso 1.000000 R
C4 C 1.5725(11) -0.0689(4) 1.0047(8) 0.058(3) Uani 1.000000 .
H4 H 1.6650(11) -0.0624(4) 1.0328(8) 0.070(3) Uiso 1.000000 R
C18 C 0.7545(12) 0.2761(5) 0.8297(9) 0.073(4) Uani 1.000000 .
H18 H 0.8378(12) 0.2976(5) 0.8421(9) 0.087(4) Uiso 1.000000 R
C12 C 1.0465(15) -0.1787(5) 0.9106(11) 0.096(5) Uani 1.000000 .
H12a H 1.112(10) -0.1832(6) 0.965(5) 0.144(7) Uiso 1.000000 GR
H12b H 0.954(3) -0.1941(12) 0.922(8) 0.144(7) Uiso 1.000000 GR
H12c H 1.084(12) -0.1981(10) 0.859(3) 0.144(7) Uiso 1.000000 GR
O1 O 1.4131(16) -0.1212(5) 0.6254(9) 0.125(4) Uani 1.000000 .
H1 H 1.354(17) -0.111(2) 0.583(11) 0.187(6) Uiso 1.000000 GR
C9 C 1.4974(12) -0.0761(5) 0.6567(8) 0.069(3) Uani 1.000000 .
H9a H 1.5374(12) -0.0581(5) 0.6042(8) 0.083(4) Uiso 1.000000 R
H9b H 1.5774(12) -0.0897(5) 0.6986(8) 0.083(4) Uiso 1.000000 R
C20 C 0.5359(10) 0.1275(3) 0.6279(8) 0.055(3) Uani 1.000000 .
H20a H 0.5813(10) 0.1000(3) 0.5900(8) 0.066(3) Uiso 1.000000 R
H20b H 0.4862(10) 0.1072(3) 0.6741(8) 0.066(3) Uiso 1.000000 R
O2 O 0.4988(15) 0.1960(4) 0.5063(8) 0.121(4) Uani 1.000000 .
H2 H 0.532(18) 0.1763(10) 0.466(8) 0.181(6) Uiso 1.000000 GR
C21 C 0.4269(13) 0.1615(4) 0.5668(9) 0.075(4) Uani 1.000000 .
H21a H 0.3615(13) 0.1362(4) 0.5309(9) 0.090(5) Uiso 1.000000 R
H21b H 0.3702(13) 0.1848(4) 0.6053(9) 0.090(5) Uiso 1.000000 R
C24 C 1.0822(15) 0.2358(7) 0.7863(15) 0.156(10) Uani 1.000000 .
H24a H 1.050(13) 0.207(5) 0.826(5) 0.234(14) Uiso 1.000000 GR
H24b H 1.182(3) 0.230(8) 0.7763(19) 0.234(14) Uiso 1.000000 GR
H24c H 1.072(15) 0.272(3) 0.815(6) 0.234(14) Uiso 1.000000 GR


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 Br2 3.0655(11) . ?
Bi1 Br2 2.9731(10) 3_756 ?
Bi1 Br1 2.6981(11) . ?
Bi1 Br3 2.7333(10) . ?
Bi1 S1 2.8000(19) . ?
Bi1 S2 2.892(2) . ?
C11 C10 1.497(15) . ?
S1 C1 1.710(8) . ?
S2 C13 1.712(9) . ?
N2 C14 1.390(11) . ?
N2 C13 1.363(11) . ?
N2 C20 1.460(10) . ?
N4 C7 1.391(10) . ?
N4 C10 1.486(11) . ?
N4 C1 1.350(11) . ?
N1 C19 1.418(13) . ?
N1 C22 1.464(13) . ?
N1 C13 1.356(11) . ?
C7 C2 1.398(12) . ?
C7 C6 1.368(13) . ?
C2 N3 1.383(11) . ?
C2 C3 1.383(12) . ?
N3 C8 1.458(11) . ?
N3 C1 1.358(10) . ?
C8 C9 1.527(14) . ?
C6 C5 1.404(14) . ?
C3 C4 1.378(14) . ?
C19 C14 1.388(12) . ?
C19 C18 1.391(13) . ?
C14 C15 1.369(14) . ?
C10 C12 1.516(14) . ?
C15 C16 1.385(15) . ?
C16 C17 1.364(16) . ?
C22 C23 1.49(2) . ?
C22 C24 1.50(2) . ?
C17 C18 1.386(17) . ?
C5 C4 1.396(15) . ?
O1 C9 1.378(15) . ?
C20 C21 1.516(13) . ?
O2 C21 1.404(16) . ?

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 93.90(3) . 3_756 ?
Br1 Bi1 Br2 177.57(3) . . ?
Br3 Bi1 Br2 169.27(3) . 3_756 ?
Br3 Bi1 Br2 90.97(3) . . ?
Br3 Bi1 Br1 91.32(4) . . ?
S1 Bi1 Br2 75.72(5) . 3_756 ?
S1 Bi1 Br2 86.18(6) . . ?
S1 Bi1 Br1 94.47(6) . . ?
S1 Bi1 Br3 94.54(5) . . ?
S2 Bi1 Br2 90.89(5) . 3_756 ?
S2 Bi1 Br2 88.16(5) . . ?
S2 Bi1 Br1 90.68(6) . . ?
S2 Bi1 Br3 98.43(6) . . ?
S2 Bi1 S1 165.93(7) . . ?
C1 S1 Bi1 108.3(2) . . ?
C13 S2 Bi1 105.8(3) . . ?
C13 N2 C14 109.5(7) . . ?
C20 N2 C14 123.4(8) . . ?
C20 N2 C13 126.6(8) . . ?
C10 N4 C7 126.0(8) . . ?
C1 N4 C7 109.5(7) . . ?
C1 N4 C10 124.5(8) . . ?
C22 N1 C19 127.5(8) . . ?
C13 N1 C19 108.5(7) . . ?
C13 N1 C22 123.6(10) . . ?
C2 C7 N4 106.4(8) . . ?
C6 C7 N4 132.8(9) . . ?
C6 C7 C2 120.8(9) . . ?
N3 C2 C7 106.8(7) . . ?
C3 C2 C7 121.9(9) . . ?
C3 C2 N3 131.3(9) . . ?
C8 N3 C2 125.1(7) . . ?
C1 N3 C2 109.3(7) . . ?
C1 N3 C8 125.6(8) . . ?
C9 C8 N3 113.0(7) . . ?
C5 C6 C7 117.8(9) . . ?
C4 C3 C2 117.6(9) . . ?
C14 C19 N1 106.7(8) . . ?
C18 C19 N1 130.9(9) . . ?
C18 C19 C14 122.4(10) . . ?
C19 C14 N2 107.0(8) . . ?
C15 C14 N2 131.9(9) . . ?
C15 C14 C19 121.1(9) . . ?
N4 C10 C11 109.8(9) . . ?
C12 C10 C11 114.5(12) . . ?
C12 C10 N4 110.4(9) . . ?
C16 C15 C14 117.2(10) . . ?
C17 C16 C15 121.4(11) . . ?
C23 C22 N1 110.8(12) . . ?
C24 C22 N1 110.8(14) . . ?
C24 C22 C23 113.9(12) . . ?
C18 C17 C16 122.9(11) . . ?
N4 C1 S1 125.9(6) . . ?
N3 C1 S1 126.1(7) . . ?
N3 C1 N4 108.0(7) . . ?
N2 C13 S2 125.5(6) . . ?
N1 C13 S2 126.2(7) . . ?
N1 C13 N2 108.2(8) . . ?
C4 C5 C6 121.0(10) . . ?
C5 C4 C3 121.0(10) . . ?
C17 C18 C19 115.1(10) . . ?
O1 C9 C8 111.9(10) . . ?
C21 C20 N2 111.6(7) . . ?
O2 C21 C20 109.9(11) . . ?

_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 3.257
_oxdiff_exptl_absorpt_empirical_full_min 0.230
####################################################################### 
# 
# 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_V
_database_code_depnum_ccdc_archive 'CCDC 2129452'
loop_
_audit_author_name
_audit_author_address
'Prabusankar Ganesan'
;Indian Institute of Technology Hyderabad
India
;
_audit_update_record             
;
2022-04-12 deposited with the CCDC.	2022-04-22 downloaded from the CCDC.
;
_audit_creation_date             2022-04-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
loop_
_audit_author_email
prabu@chy.iith.ac.in
_chemical_formula_moiety         'C19 H12 Cl N S'
_chemical_formula_sum            'C19 H12 Cl N S'
_chemical_formula_weight         321.83
_chemical_oxdiff_formula         C16H20N3S
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/c 1'
_space_group_name_Hall           '-C 2yc (x,y,-x+z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z+1/2
6 -x+1/2,y+1/2,-z+1
7 -x+1/2,-y+1/2,-z+1/2
8 x+1/2,-y+1/2,z

_symmetry_Int_Tables_number      15
_cell_length_a                   25.360(3)
_cell_length_b                   7.5833(5)
_cell_length_c                   33.138(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.162(11)
_cell_angle_gamma                90
_cell_volume                     5982.3(10)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    802
_cell_measurement_temperature    293
_cell_measurement_theta_max      18.8360
_cell_measurement_theta_min      2.6110
_exptl_absorpt_coefficient_mu    0.389
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.4292
_exptl_crystal_description       irregular
_exptl_crystal_F_000             2661.1969
_exptl_crystal_size_max          0.077
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.062
_diffrn_reflns_av_R_equivalents  0.1147
_diffrn_reflns_av_unetI/netI     0.3028
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            12375
_diffrn_reflns_theta_full        29.0862
_diffrn_reflns_theta_max         29.09
_diffrn_reflns_theta_min         2.49
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1293
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.8494
_diffrn_measured_fraction_theta_max 0.8494
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     67.00  95.00   1.00   10.94    --   19.48 178.00-180.00   28
  2  ω    -20.00  84.00   1.00   10.94    --   19.48   0.00-180.00  104
  3  ω     12.00  92.00   1.00   10.94    --   19.48  38.00-150.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0149489000
_diffrn_orient_matrix_UB_12      0.0137148000
_diffrn_orient_matrix_UB_13      0.0142964000
_diffrn_orient_matrix_UB_21      0.0233233000
_diffrn_orient_matrix_UB_22      0.0465019000
_diffrn_orient_matrix_UB_23      0.0141878000
_diffrn_orient_matrix_UB_31      -0.0109898000
_diffrn_orient_matrix_UB_32      0.0799776000
_diffrn_orient_matrix_UB_33      -0.0106936000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              31
_reflns_limit_h_min              -33
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              42
_reflns_limit_l_min              0
_reflns_number_gt                1409
_reflns_number_total             6817
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         2.0951
_refine_diff_density_min         -1.2456
_refine_diff_density_rms         0.3136
_refine_ls_d_res_high            0.7310
_refine_ls_d_res_low             8.1881
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   0.9540
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    48
_refine_ls_number_parameters     398
_refine_ls_number_reflns         6817
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.3443
_refine_ls_R_factor_gt           0.0800
_refine_ls_restrained_S_all      0.9540
_refine_ls_shift/su_max          2.0818
_refine_ls_shift/su_mean         0.4192
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.1791
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C38(H38), C37(H37), C35(H35), C34(H34), C23(H23), C22(H22), C21(H21),
 C20(H20), C24(H24), C25(H25), C26(H26), C27(H27), C15(H15), C16(H16), C18(H18),
  C19(H19), C4(H4), C3(H3), C2(H2), C1(H1), C5(H5), C6(H6), C7(H7), C8(H8)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
S2 S 0.46927(10) 0.4225(3) 0.58557(7) 0.0644(7) Uani 1.000000 .
S1 S 0.78856(11) 0.1700(3) 0.66664(8) 0.0703(8) Uani 1.000000 .
Cl Cl 0.43853(10) -0.2179(3) 0.69526(8) 0.0858(9) Uani 1.000000 .
Cl1 Cl 0.80754(11) -0.4745(3) 0.55462(9) 0.0922(9) Uani 1.000000 .
N1 N 0.7532(3) -0.0553(8) 0.7834(2) 0.0472(18) Uani 1.000000 .
N2 N 0.5043(3) 0.1980(9) 0.4681(2) 0.053(2) Uani 1.000000 .
C19 C 0.7839(3) -0.1898(10) 0.6477(2) 0.051(2) Uani 1.000000 .
C34 C 0.4676(3) 0.0609(10) 0.6036(2) 0.047(2) Uani 1.000000 .
C29 C 0.4389(4) 0.2666(10) 0.5061(3) 0.047(2) Uani 1.000000 .
C38 C 0.4467(3) 0.2698(10) 0.6505(2) 0.055(2) Uani 1.000000 .
C13 C 0.7748(3) 0.0769(9) 0.7120(2) 0.042(2) Uani 1.000000 .
C33 C 0.4614(3) 0.2343(10) 0.6147(2) 0.046(2) Uani 1.000000 .
C15 C 0.8119(3) 0.0098(10) 0.6024(3) 0.056(2) Uani 1.000000 .
C35 C 0.4604(3) -0.0762(10) 0.6283(3) 0.052(2) Uani 1.000000 .
C12 C 0.8057(4) -0.0530(10) 0.7829(3) 0.048(2) Uani 1.000000 .
C14 C 0.7957(3) -0.0189(10) 0.6372(2) 0.046(2) Uani 1.000000 .
C30 C 0.5376(3) 0.3282(10) 0.5398(3) 0.044(2) Uani 1.000000 .
C16 C 0.8157(3) -0.1306(11) 0.5765(3) 0.066(3) Uani 1.000000 .
C37 C 0.4410(3) 0.1322(11) 0.6764(3) 0.067(3) Uani 1.000000 .
C18 C 0.7893(3) -0.3309(11) 0.6229(3) 0.059(2) Uani 1.000000 .
C31 C 0.5462(4) 0.2584(10) 0.5028(3) 0.049(2) Uani 1.000000 .
C28 C 0.4529(4) 0.1993(11) 0.4706(3) 0.054(2) Uani 1.000000 .
C32 C 0.4833(4) 0.3285(9) 0.5412(3) 0.046(2) Uani 1.000000 .
C9 C 0.7114(4) 0.0046(10) 0.7493(3) 0.046(2) Uani 1.000000 .
C10 C 0.7202(3) 0.0714(9) 0.7120(3) 0.042(2) Uani 1.000000 .
C36 C 0.4476(3) -0.0413(11) 0.6646(3) 0.053(2) Uani 1.000000 .
C1 C 0.6558(4) -0.0048(10) 0.7512(3) 0.059(3) Uani 1.000000 .
C24 C 0.5856(4) 0.3870(10) 0.5743(3) 0.057(2) Uani 1.000000 .
C11 C 0.8193(4) 0.0132(10) 0.7464(3) 0.048(2) Uani 1.000000 .
C27 C 0.6009(4) 0.2526(12) 0.5012(3) 0.071(3) Uani 1.000000 .
C8 C 0.8498(4) -0.1185(11) 0.8189(3) 0.071(3) Uani 1.000000 .
C20 C 0.4094(4) 0.1325(10) 0.4335(3) 0.068(3) Uani 1.000000 .
C23 C 0.3820(4) 0.2543(11) 0.5035(3) 0.065(3) Uani 1.000000 .
C17 C 0.8043(3) -0.2973(11) 0.5875(3) 0.055(2) Uani 1.000000 .
C5 C 0.8764(4) 0.0119(11) 0.7497(3) 0.070(3) Uani 1.000000 .
C4 C 0.6716(4) 0.1317(10) 0.6777(3) 0.060(3) Uani 1.000000 .
C3 C 0.6198(4) 0.1209(11) 0.6798(3) 0.071(3) Uani 1.000000 .
C7 C 0.9023(5) -0.1196(12) 0.8201(3) 0.085(3) Uani 1.000000 .
C25 C 0.6374(4) 0.3810(11) 0.5706(3) 0.070(3) Uani 1.000000 .
C26 C 0.6457(4) 0.3106(12) 0.5331(4) 0.075(3) Uani 1.000000 .
C2 C 0.6121(4) 0.0536(11) 0.7159(4) 0.073(3) Uani 1.000000 .
C22 C 0.3419(4) 0.1885(13) 0.4692(4) 0.085(3) Uani 1.000000 .
C21 C 0.3557(5) 0.1256(11) 0.4329(3) 0.086(3) Uani 1.000000 .
C6 C 0.9174(4) -0.0562(14) 0.7857(4) 0.088(4) Uani 1.000000 .
H38 H 0.4407(3) 0.3855(10) 0.6572(2) 0.066(3) Uiso 1.000000 R
H37 H 0.4330(3) 0.1551(11) 0.7012(3) 0.080(3) Uiso 1.000000 R
H35 H 0.4642(3) -0.1921(10) 0.6205(3) 0.063(3) Uiso 1.000000 R
H34 H 0.4768(3) 0.0374(10) 0.5793(2) 0.056(3) Uiso 1.000000 R
H23 H 0.3723(4) 0.2935(11) 0.5266(3) 0.078(3) Uiso 1.000000 R
H22 H 0.3050(4) 0.1831(13) 0.4686(4) 0.102(4) Uiso 1.000000 R
H21 H 0.3276(5) 0.0801(11) 0.4090(3) 0.103(4) Uiso 1.000000 R
H20 H 0.4180(4) 0.0938(10) 0.4099(3) 0.082(3) Uiso 1.000000 R
H24 H 0.5816(4) 0.4296(10) 0.5994(3) 0.068(3) Uiso 1.000000 R
H25 H 0.6682(4) 0.4235(11) 0.5930(3) 0.084(3) Uiso 1.000000 R
H26 H 0.6813(4) 0.3057(12) 0.5310(4) 0.090(4) Uiso 1.000000 R
H27 H 0.6059(4) 0.2062(12) 0.4768(3) 0.085(4) Uiso 1.000000 R
H15 H 0.8202(3) 0.1235(10) 0.5960(3) 0.067(3) Uiso 1.000000 R
H16 H 0.8258(3) -0.1121(11) 0.5524(3) 0.079(3) Uiso 1.000000 R
H18 H 0.7830(3) -0.4457(11) 0.6300(3) 0.071(3) Uiso 1.000000 R
H19 H 0.7725(3) -0.2083(10) 0.6712(2) 0.061(3) Uiso 1.000000 R
H4 H 0.6761(4) 0.1797(10) 0.6533(3) 0.072(3) Uiso 1.000000 R
H3 H 0.5890(4) 0.1591(11) 0.6568(3) 0.085(4) Uiso 1.000000 R
H2 H 0.5758(4) 0.0472(11) 0.7165(4) 0.087(4) Uiso 1.000000 R
H1 H 0.6495(4) -0.0486(10) 0.7753(3) 0.071(3) Uiso 1.000000 R
H5 H 0.8865(4) 0.0576(11) 0.7274(3) 0.084(4) Uiso 1.000000 R
H6 H 0.9546(4) -0.0600(14) 0.7871(4) 0.105(4) Uiso 1.000000 R
H7 H 0.9302(5) -0.1636(12) 0.8443(3) 0.102(4) Uiso 1.000000 R
H8 H 0.8415(4) -0.1616(11) 0.8423(3) 0.085(3) Uiso 1.000000 R


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 C33 1.772(7) . ?
S2 C32 1.778(8) . ?
S1 C13 1.801(7) . ?
S1 C14 1.778(8) . ?
Cl C36 1.743(8) . ?
Cl1 C17 1.750(7) . ?
N1 C12 1.338(9) . ?
N1 C9 1.336(9) . ?
N2 C31 1.349(9) . ?
N2 C28 1.337(9) . ?
C19 C14 1.401(9) . ?
C19 C18 1.386(9) . ?
C34 C33 1.389(9) . ?
C34 C35 1.374(9) . ?
C29 C28 1.433(10) . ?
C29 C32 1.393(10) . ?
C29 C23 1.420(10) . ?
C38 C33 1.388(9) . ?
C38 C37 1.389(9) . ?
C13 C10 1.386(9) . ?
C13 C11 1.385(10) . ?
C15 C14 1.367(9) . ?
C15 C16 1.391(9) . ?
C35 C36 1.377(9) . ?
C12 C11 1.454(10) . ?
C12 C8 1.415(10) . ?
C30 C31 1.419(10) . ?
C30 C32 1.393(10) . ?
C30 C24 1.424(10) . ?
C16 C17 1.373(10) . ?
C37 C36 1.399(10) . ?
C18 C17 1.376(9) . ?
C31 C27 1.406(10) . ?
C28 C20 1.431(11) . ?
C9 C10 1.422(9) . ?
C9 C1 1.433(10) . ?
C10 C4 1.433(10) . ?
C1 C2 1.377(11) . ?
C24 C25 1.362(10) . ?
C11 C5 1.413(10) . ?
C27 C26 1.332(11) . ?
C8 C7 1.321(11) . ?
C20 C21 1.357(11) . ?
C23 C22 1.335(11) . ?
C5 C6 1.384(12) . ?
C4 C3 1.344(10) . ?
C3 C2 1.374(10) . ?
C7 C6 1.405(12) . ?
C25 C26 1.433(11) . ?
C22 C21 1.442(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C32 S2 C33 102.7(4) . . ?
C14 S1 C13 103.2(3) . . ?
C9 N1 C12 119.2(7) . . ?
C28 N2 C31 116.2(7) . . ?
C18 C19 C14 119.5(7) . . ?
C35 C34 C33 120.6(7) . . ?
C32 C29 C28 116.6(8) . . ?
C23 C29 C28 117.4(8) . . ?
C23 C29 C32 125.8(8) . . ?
C37 C38 C33 119.8(8) . . ?
C10 C13 S1 119.5(6) . . ?
C11 C13 S1 119.1(6) . . ?
C11 C13 C10 121.3(8) . . ?
C34 C33 S2 125.0(6) . . ?
C38 C33 S2 115.0(6) . . ?
C38 C33 C34 119.9(7) . . ?
C16 C15 C14 120.1(7) . . ?
C36 C35 C34 119.7(8) . . ?
C11 C12 N1 122.5(8) . . ?
C8 C12 N1 118.9(9) . . ?
C8 C12 C11 118.6(9) . . ?
C19 C14 S1 122.5(6) . . ?
C15 C14 S1 116.8(6) . . ?
C15 C14 C19 120.7(7) . . ?
C32 C30 C31 118.5(8) . . ?
C24 C30 C31 117.9(8) . . ?
C24 C30 C32 123.6(8) . . ?
C17 C16 C15 118.4(8) . . ?
C36 C37 C38 119.2(8) . . ?
C17 C18 C19 118.4(8) . . ?
C30 C31 N2 123.6(8) . . ?
C27 C31 N2 116.9(9) . . ?
C27 C31 C30 119.4(9) . . ?
C29 C28 N2 125.2(8) . . ?
C20 C28 N2 115.0(9) . . ?
C20 C28 C29 119.7(9) . . ?
C29 C32 S2 119.4(7) . . ?
C30 C32 S2 120.7(7) . . ?
C30 C32 C29 119.7(8) . . ?
C10 C9 N1 122.7(8) . . ?
C1 C9 N1 116.9(8) . . ?
C1 C9 C10 120.4(8) . . ?
C9 C10 C13 117.8(7) . . ?
C4 C10 C13 125.1(8) . . ?
C4 C10 C9 117.0(8) . . ?
C35 C36 Cl 118.7(7) . . ?
C37 C36 Cl 120.5(7) . . ?
C37 C36 C35 120.7(8) . . ?
C2 C1 C9 117.5(9) . . ?
C25 C24 C30 120.1(8) . . ?
C12 C11 C13 116.4(8) . . ?
C5 C11 C13 126.0(9) . . ?
C5 C11 C12 117.5(8) . . ?
C26 C27 C31 122.8(10) . . ?
C7 C8 C12 121.5(10) . . ?
C21 C20 C28 119.9(10) . . ?
C22 C23 C29 122.4(9) . . ?
C16 C17 Cl1 118.9(7) . . ?
C18 C17 Cl1 118.3(7) . . ?
C18 C17 C16 122.8(7) . . ?
C6 C5 C11 121.0(10) . . ?
C3 C4 C10 121.8(9) . . ?
C2 C3 C4 120.2(9) . . ?
C6 C7 C8 121.8(11) . . ?
C26 C25 C24 121.6(9) . . ?
C25 C26 C27 118.2(9) . . ?
C3 C2 C1 123.0(9) . . ?
C21 C22 C23 120.1(10) . . ?
C22 C21 C20 120.4(10) . . ?
C7 C6 C5 119.5(10) . . ?

_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 1.386
_oxdiff_exptl_absorpt_empirical_full_min 0.676
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2129447'
loop_
_audit_author_name
_audit_author_address
'Prabusankar Ganesan'
;Indian Institute of Technology Hyderabad
India
;
_audit_update_record             
;
2022-04-12 deposited with the CCDC.	2022-04-22 downloaded from the CCDC.
;
_audit_creation_date             2022-04-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
loop_
_audit_author_email
prabu@chy.iith.ac.in
_chemical_name_systematic        ?
_chemical_formula_moiety         'C48 H64 Bi2 Cl6 N8 O4 Se4'
_chemical_formula_sum            'C48 H64 Bi2 Cl6 N8 O4 Se4'
_chemical_formula_weight         1763.61
_chemical_oxdiff_formula         'C30 N5 H30 O4 Se4 Bi2 Cl10'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Bi -3.98376 10.58997 33.36890 12.95100 16.58770 6.46920 0.70400 2.92380 8.79370
48.00930 13.5782003403
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Se -0.08110 2.30834 17.00060 5.81960 3.97310 4.35430 2.40980 0.27260 15.23720
43.81630 2.84089994431
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   9.148(2)
_cell_length_b                   23.974(5)
_cell_length_c                   14.150(3)
_cell_angle_alpha                90.00(3)
_cell_angle_beta                 95.19(3)
_cell_angle_gamma                90.00(3)
_cell_volume                     3090.5(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    15024
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      28.2980
_cell_measurement_theta_min      3.6930
_exptl_absorpt_coefficient_mu    8.347
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear pinkish pink'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   pinkish
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.8951
_exptl_crystal_description       block
_exptl_crystal_F_000             1674.4766
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            30790
_diffrn_reflns_theta_full        24.9974
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.89
_diffrn_ambient_temperature      298.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0309
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.9982
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -3.00   86.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       17.1097   57.0000   90.0000 89

#__ type_ start__ end____ width___ exp.time_
  2 omega   53.00   79.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       17.1097  178.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega   -9.00   84.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       17.1097   77.0000  150.0000 93

#__ type_ start__ end____ width___ exp.time_
  4 omega   -9.00   42.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       17.1097   77.0000  -60.0000 51

#__ type_ start__ end____ width___ exp.time_
  5 omega    9.00   36.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.9065   77.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega  -52.00  -26.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       17.1097  -57.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega  -20.00   53.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       17.1097  -99.0000    0.0000 73

#__ type_ start__ end____ width___ exp.time_
  8 omega  -16.00   40.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       17.1097  -77.0000 -150.0000 56

#__ type_ start__ end____ width___ exp.time_
  9 omega  -61.00    7.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.9065  -19.0000   30.0000 68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0093192000
_diffrn_orient_matrix_UB_12      -0.0289446000
_diffrn_orient_matrix_UB_13      0.0091444000
_diffrn_orient_matrix_UB_21      0.0006423000
_diffrn_orient_matrix_UB_22      0.0051355000
_diffrn_orient_matrix_UB_23      0.0493855000
_diffrn_orient_matrix_UB_31      -0.0772892000
_diffrn_orient_matrix_UB_32      -0.0034434000
_diffrn_orient_matrix_UB_33      -0.0030864000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -10
_reflns_limit_k_max              28
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              -8
_reflns_number_gt                5000
_reflns_number_total             5434
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         2.7354
_refine_diff_density_min         -1.5197
_refine_diff_density_rms         0.3930
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             7.0459
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0158
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    52
_refine_ls_number_parameters     326
_refine_ls_number_reflns         5434
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0490
_refine_ls_restrained_S_all      1.0156
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1359P)²+5.5381P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1495
_refine_ls_wR_factor_ref         0.1756
_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, All O(H) groups
2. Restrained distances
 C8-C9
 1.3 with sigma of 0.02
 C9-O1
 1.45 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C10(H10), C22(H22)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b), C9(H9a,H9b), C20(H20a,H20b), C21(H21a,H21b)
3.c Me refined with riding coordinates:
 C11(H11a,H11b,H11c), C12(H12a,H12b,H12c), C23(H23a,H23b,H23c), C24(H24a,H24b,
 H24c)
3.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C15(H15), C16(H16), C17(H17), C18(H18)
3.e Tetrahedral OH refined with riding coordinates:
 O1(H1), O2(H2)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
Bi1 Bi 0.52002(3) 0.464210(12) 0.860133(18) 0.0352(2) Uani 1.000000 .
Se1 Se 0.43078(10) 0.57809(4) 0.81769(6) 0.0476(3) Uani 1.000000 .
Se2 Se 0.65452(10) 0.36135(4) 0.95416(6) 0.0474(3) Uani 1.000000 .
Cl1 Cl 0.6867(3) 0.53376(10) 0.99221(17) 0.0519(6) Uani 1.000000 .
Cl2 Cl 0.7108(3) 0.46160(11) 0.7387(2) 0.0629(8) Uani 1.000000 .
Cl3 Cl 0.3241(3) 0.41677(13) 0.74255(18) 0.0656(7) Uani 1.000000 .
O1 O 0.0616(17) 0.6207(8) 0.8638(9) 0.192(9) Uani 1.000000 D
H1 H 0.0055(17) 0.6403(8) 0.8914(9) 0.287(13) Uiso 1.000000 R
O2 O 1.211(2) 0.3210(9) 0.8963(15) 0.210(9) Uani 1.000000 .
H2 H 1.267(2) 0.3047(9) 0.9360(15) 0.315(13) Uiso 1.000000 R
N1 N 0.1508(8) 0.5556(3) 0.7121(5) 0.0427(16) Uani 1.000000 .
N2 N 0.3090(7) 0.5949(3) 0.6249(5) 0.0412(15) Uani 1.000000 .
N3 N 0.8692(8) 0.3363(3) 0.8262(5) 0.0408(15) Uani 1.000000 .
N4 N 0.6712(8) 0.2855(3) 0.7971(5) 0.0452(17) Uani 1.000000 .
C1 C 0.2904(9) 0.5751(3) 0.7130(6) 0.0394(17) Uani 1.000000 .
C2 C 0.1773(10) 0.5879(4) 0.5667(6) 0.0436(19) Uani 1.000000 .
C3 C 0.1432(12) 0.6007(5) 0.4715(7) 0.057(2) Uani 1.000000 .
H3 H 0.2098(12) 0.6169(5) 0.4338(7) 0.069(3) Uiso 1.000000 R
C4 C 0.0006(12) 0.5870(5) 0.4380(7) 0.060(3) Uani 1.000000 .
H4 H -0.0289(12) 0.5945(5) 0.3746(7) 0.072(3) Uiso 1.000000 R
C5 C -0.1018(11) 0.5628(5) 0.4932(7) 0.059(3) Uani 1.000000 .
H5 H -0.1962(11) 0.5552(5) 0.4663(7) 0.071(3) Uiso 1.000000 R
C6 C -0.0639(10) 0.5501(4) 0.5872(7) 0.048(2) Uani 1.000000 .
H6 H -0.1299(10) 0.5336(4) 0.6250(7) 0.058(2) Uiso 1.000000 R
C7 C 0.0782(9) 0.5634(4) 0.6222(6) 0.0401(18) Uani 1.000000 .
C8 C 0.0838(11) 0.5317(4) 0.7953(7) 0.053(3) Uani 1.000000 D
H8a H 0.0242(11) 0.4999(4) 0.7740(7) 0.064(3) Uiso 1.000000 R
H8b H 0.1620(11) 0.5181(4) 0.8403(7) 0.064(3) Uiso 1.000000 R
C9 C -0.004(2) 0.5687(7) 0.8431(11) 0.114(8) Uani 1.000000 D
H9a H -0.027(2) 0.5515(7) 0.9020(11) 0.137(9) Uiso 1.000000 R
H9b H -0.096(2) 0.5746(7) 0.8043(11) 0.137(9) Uiso 1.000000 R
C10 C 0.4429(11) 0.6211(5) 0.5976(7) 0.060(3) Uani 1.000000 .
H10 H 0.5159(11) 0.6191(5) 0.6526(7) 0.072(3) Uiso 1.000000 R
C11 C 0.4162(17) 0.6821(6) 0.5757(12) 0.104(5) Uani 1.000000 .
H11a H 0.5050(17) 0.6988(6) 0.5578(12) 0.155(8) Uiso 1.000000 R
H11b H 0.3406(17) 0.6856(6) 0.5244(12) 0.155(8) Uiso 1.000000 R
H11c H 0.3859(17) 0.7006(6) 0.6308(12) 0.155(8) Uiso 1.000000 R
C12 C 0.5014(18) 0.5857(8) 0.5179(13) 0.119(6) Uani 1.000000 .
H12a H 0.5897(18) 0.6023(8) 0.4989(13) 0.178(9) Uiso 1.000000 R
H12b H 0.5220(18) 0.5486(8) 0.5407(13) 0.178(9) Uiso 1.000000 R
H12c H 0.4289(18) 0.5843(8) 0.4645(13) 0.178(9) Uiso 1.000000 R
C13 C 0.7353(9) 0.3257(3) 0.8520(5) 0.0387(17) Uani 1.000000 .
C14 C 0.7713(9) 0.2671(4) 0.7359(6) 0.0446(19) Uani 1.000000 .
C15 C 0.7614(11) 0.2238(5) 0.6672(7) 0.061(3) Uani 1.000000 .
H15 H 0.6787(11) 0.2013(5) 0.6561(7) 0.073(3) Uiso 1.000000 R
C16 C 0.8864(13) 0.2175(5) 0.6172(9) 0.074(3) Uani 1.000000 .
H16 H 0.8869(13) 0.1895(5) 0.5719(9) 0.088(4) Uiso 1.000000 R
C17 C 1.0090(13) 0.2515(6) 0.6327(7) 0.069(3) Uani 1.000000 .
H17 H 1.0863(13) 0.2471(6) 0.5949(7) 0.083(4) Uiso 1.000000 R
C18 C 1.0193(11) 0.2909(4) 0.7013(7) 0.054(2) Uani 1.000000 .
H18 H 1.1042(11) 0.3120(4) 0.7137(7) 0.064(3) Uiso 1.000000 R
C19 C 0.8960(9) 0.2990(4) 0.7536(5) 0.0392(17) Uani 1.000000 .
C20 C 0.9824(10) 0.3748(4) 0.8719(7) 0.048(2) Uani 1.000000 .
H20a H 1.0351(10) 0.3924(4) 0.8233(7) 0.058(2) Uiso 1.000000 R
H20b H 0.9347(10) 0.4039(4) 0.9054(7) 0.058(2) Uiso 1.000000 R
C21 C 1.0904(11) 0.3438(5) 0.9409(9) 0.065(3) Uani 1.000000 .
H21a H 1.0393(11) 0.3138(5) 0.9701(9) 0.078(3) Uiso 1.000000 R
H21b H 1.1276(11) 0.3691(5) 0.9909(9) 0.078(3) Uiso 1.000000 R
C22 C 0.5241(12) 0.2612(6) 0.8122(9) 0.075(4) Uani 1.000000 .
H22 H 0.4782(12) 0.2852(6) 0.8570(9) 0.090(4) Uiso 1.000000 R
C23 C 0.4310(14) 0.2642(8) 0.7169(12) 0.114(6) Uani 1.000000 .
H23a H 0.4282(14) 0.3020(8) 0.6944(12) 0.172(9) Uiso 1.000000 R
H23b H 0.4732(14) 0.2407(8) 0.6717(12) 0.172(9) Uiso 1.000000 R
H23c H 0.3330(14) 0.2519(8) 0.7249(12) 0.172(9) Uiso 1.000000 R
C24 C 0.5349(19) 0.2069(8) 0.8514(13) 0.124(8) Uani 1.000000 .
H24a H 0.4384(19) 0.1931(8) 0.8597(13) 0.186(12) Uiso 1.000000 R
H24b H 0.5816(19) 0.1827(8) 0.8093(13) 0.186(12) Uiso 1.000000 R
H24c H 0.5919(19) 0.2082(8) 0.9117(13) 0.186(12) Uiso 1.000000 R


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 Se1 2.8970(12) . ?
Bi1 Se2 3.0114(13) . ?
Bi1 Cl1 2.843(2) . ?
Bi1 Cl1 2.942(3) 3_667 ?
Bi1 Cl2 2.558(3) . ?
Bi1 Cl3 2.595(2) . ?
Se1 C1 1.872(8) . ?
Se2 C13 1.887(8) . ?
O1 H1 0.8200 . ?
O1 C9 1.403(16) . ?
O2 H2 0.8200 . ?
O2 C21 1.431(19) . ?
N1 C1 1.359(11) . ?
N1 C7 1.393(11) . ?
N1 C8 1.491(11) . ?
N2 C1 1.359(10) . ?
N2 C2 1.406(11) . ?
N2 C10 1.459(11) . ?
N3 C13 1.334(11) . ?
N3 C19 1.402(10) . ?
N3 C20 1.490(11) . ?
N4 C13 1.339(11) . ?
N4 C14 1.388(11) . ?
N4 C22 1.500(12) . ?
C2 C3 1.390(13) . ?
C2 C7 1.383(12) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(15) . ?
C4 H4 0.9300 . ?
C4 C5 1.400(16) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(14) . ?
C6 H6 0.9300 . ?
C6 C7 1.386(13) . ?
C8 H8a 0.9700 . ?
C8 H8b 0.9700 . ?
C8 C9 1.409(14) . ?
C9 H9a 0.9700 . ?
C9 H9b 0.9700 . ?
C10 H10 0.9800 . ?
C10 C11 1.509(17) . ?
C10 C12 1.545(18) . ?
C11 H11a 0.9600 . ?
C11 H11b 0.9600 . ?
C11 H11c 0.9600 . ?
C12 H12a 0.9600 . ?
C12 H12b 0.9600 . ?
C12 H12c 0.9600 . ?
C14 C15 1.419(13) . ?
C14 C19 1.378(12) . ?
C15 H15 0.9300 . ?
C15 C16 1.406(15) . ?
C16 H16 0.9300 . ?
C16 C17 1.388(18) . ?
C17 H17 0.9300 . ?
C17 C18 1.351(15) . ?
C18 H18 0.9300 . ?
C18 C19 1.417(12) . ?
C20 H20a 0.9700 . ?
C20 H20b 0.9700 . ?
C20 C21 1.520(14) . ?
C21 H21a 0.9700 . ?
C21 H21b 0.9700 . ?
C22 H22 0.9800 . ?
C22 C23 1.53(2) . ?
C22 C24 1.41(2) . ?
C23 H23a 0.9600 . ?
C23 H23b 0.9600 . ?
C23 H23c 0.9600 . ?
C24 H24a 0.9600 . ?
C24 H24b 0.9600 . ?
C24 H24c 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
Se2 Bi1 Se1 163.64(3) . . ?
Cl1 Bi1 Se1 73.01(6) . . ?
Cl1 Bi1 Se1 86.82(5) 3_667 . ?
Cl1 Bi1 Se2 87.88(5) 3_667 . ?
Cl1 Bi1 Se2 90.94(6) . . ?
Cl2 Bi1 Se1 94.61(6) . . ?
Cl2 Bi1 Se2 90.02(7) . . ?
Cl2 Bi1 Cl1 176.95(8) . 3_667 ?
Cl2 Bi1 Cl1 95.62(9) . . ?
Cl3 Bi1 Se1 96.59(7) . . ?
Cl3 Bi1 Se2 98.94(7) . . ?
Cl3 Bi1 Cl1 90.65(8) . 3_667 ?
Cl3 Bi1 Cl1 167.62(9) . . ?
Cl3 Bi1 Cl2 91.86(10) . . ?
C1 Se1 Bi1 106.8(3) . . ?
C13 Se2 Bi1 101.9(2) . . ?
C9 O1 H1 109.5 . . ?
C21 O2 H2 109.5 . . ?
C7 N1 C1 109.4(7) . . ?
C8 N1 C1 125.3(7) . . ?
C8 N1 C7 125.2(7) . . ?
C2 N2 C1 108.8(7) . . ?
C10 N2 C1 124.8(7) . . ?
C10 N2 C2 126.3(7) . . ?
C19 N3 C13 107.7(7) . . ?
C20 N3 C13 128.3(7) . . ?
C20 N3 C19 123.5(7) . . ?
C14 N4 C13 108.2(7) . . ?
C22 N4 C13 123.3(7) . . ?
C22 N4 C14 128.1(7) . . ?
N1 C1 Se1 126.7(6) . . ?
N2 C1 Se1 125.4(6) . . ?
N2 C1 N1 107.9(7) . . ?
C3 C2 N2 130.3(8) . . ?
C7 C2 N2 106.8(7) . . ?
C7 C2 C3 122.9(9) . . ?
H3 C3 C2 123.1(6) . . ?
C4 C3 C2 113.7(9) . . ?
C4 C3 H3 123.1(6) . . ?
H4 C4 C3 117.9(6) . . ?
C5 C4 C3 124.3(9) . . ?
C5 C4 H4 117.9(6) . . ?
H5 C5 C4 119.7(6) . . ?
C6 C5 C4 120.6(9) . . ?
C6 C5 H5 119.7(6) . . ?
H6 C6 C5 121.9(6) . . ?
C7 C6 C5 116.1(9) . . ?
C7 C6 H6 121.9(5) . . ?
C2 C7 N1 107.0(7) . . ?
C6 C7 N1 130.5(8) . . ?
C6 C7 C2 122.5(8) . . ?
H8a C8 N1 108.4(5) . . ?
H8b C8 N1 108.4(5) . . ?
H8b C8 H8a 107.5 . . ?
C9 C8 N1 115.5(9) . . ?
C9 C8 H8a 108.4(8) . . ?
C9 C8 H8b 108.4(10) . . ?
C8 C9 O1 114.1(13) . . ?
H9a C9 O1 108.7(9) . . ?
H9a C9 C8 108.7(8) . . ?
H9b C9 O1 108.7(12) . . ?
H9b C9 C8 108.7(10) . . ?
H9b C9 H9a 107.6 . . ?
H10 C10 N2 107.3(5) . . ?
C11 C10 N2 110.3(9) . . ?
C11 C10 H10 107.3(8) . . ?
C12 C10 N2 108.1(10) . . ?
C12 C10 H10 107.3(9) . . ?
C12 C10 C11 116.2(12) . . ?
H11a C11 C10 109.5 . . ?
H11b C11 C10 109.5 . . ?
H11b C11 H11a 109.5 . . ?
H11c C11 C10 109.5 . . ?
H11c C11 H11a 109.5 . . ?
H11c C11 H11b 109.5 . . ?
H12a C12 C10 109.5 . . ?
H12b C12 C10 109.5 . . ?
H12b C12 H12a 109.5 . . ?
H12c C12 C10 109.5 . . ?
H12c C12 H12a 109.5 . . ?
H12c C12 H12b 109.5 . . ?
N3 C13 Se2 123.8(6) . . ?
N4 C13 Se2 126.1(6) . . ?
N4 C13 N3 110.1(7) . . ?
C15 C14 N4 130.9(8) . . ?
C19 C14 N4 107.0(7) . . ?
C19 C14 C15 122.1(8) . . ?
H15 C15 C14 122.7(6) . . ?
C16 C15 C14 114.7(10) . . ?
C16 C15 H15 122.7(7) . . ?
H16 C16 C15 118.6(7) . . ?
C17 C16 C15 122.7(10) . . ?
C17 C16 H16 118.6(6) . . ?
H17 C17 C16 119.1(6) . . ?
C18 C17 C16 121.8(10) . . ?
C18 C17 H17 119.1(7) . . ?
H18 C18 C17 121.2(7) . . ?
C19 C18 C17 117.6(10) . . ?
C19 C18 H18 121.2(5) . . ?
C14 C19 N3 106.9(7) . . ?
C18 C19 N3 132.1(8) . . ?
C18 C19 C14 121.0(8) . . ?
H20a C20 N3 109.4(5) . . ?
H20b C20 N3 109.4(5) . . ?
H20b C20 H20a 108.0 . . ?
C21 C20 N3 111.2(8) . . ?
C21 C20 H20a 109.4(6) . . ?
C21 C20 H20b 109.4(5) . . ?
C20 C21 O2 112.7(13) . . ?
H21a C21 O2 109.0(11) . . ?
H21a C21 C20 109.0(6) . . ?
H21b C21 O2 109.0(9) . . ?
H21b C21 C20 109.0(5) . . ?
H21b C21 H21a 107.813202019(18) . . ?
H22 C22 N4 107.8(5) . . ?
C23 C22 N4 107.0(11) . . ?
C23 C22 H22 107.8(7) . . ?
C24 C22 N4 112.4(11) . . ?
C24 C22 H22 107.8(8) . . ?
C24 C22 C23 113.8(13) . . ?
H23a C23 C22 109.5 . . ?
H23b C23 C22 109.5 . . ?
H23b C23 H23a 109.5 . . ?
H23c C23 C22 109.5 . . ?
H23c C23 H23a 109.5 . . ?
H23c C23 H23b 109.5 . . ?
H24a C24 C22 109.5 . . ?
H24b C24 C22 109.5 . . ?
H24b C24 H24a 109.5 . . ?
H24c C24 C22 109.5 . . ?
H24c C24 H24a 109.5 . . ?
H24c C24 H24b 109.5 . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.225 0.797 0.962 20.2 4.7 ?
2 0.275 0.297 0.538 20.2 4.0 ?
3 0.725 0.703 0.462 20.2 4.9 ?
4 0.775 0.203 0.038 20.2 4.2 ?


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
_restr_distance_diff
C8 C9 1 1.3000 0.0200 -0.1093
C9 O1 1 1.4500 0.0200 0.0470

