#------------------------------------------------------------------------------
#$Date: 2022-06-06 04:58:33 +0300 (Mon, 06 Jun 2022) $
#$Revision: 275814 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/14/7061460.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7061460
loop_
_publ_author_name
'Mannarsamy, Maruthupandi'
'Nandeshwar, Muneshwar'
'Veerapathiran, Sabari'
'Mandal, Suman'
'Harijan, Dinesh'
'Subramaniyam, Kalaivanan'
'Muduli, Gopendra'
'Prabusankar, Ganesan'
_publ_section_title
;
 Dinuclear complexes, a one dimensional chain and a two dimensional layer
 of bismuth(iii) chalcogenones for C--S cross coupling reactions
;
_journal_issue                   21
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10256
_journal_page_last               10263
_journal_paper_doi               10.1039/D2NJ01151D
_journal_volume                  46
_journal_year                    2022
_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
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-12-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-12-17 deposited with the CCDC.	2022-04-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.4866(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6327(2)
_cell_length_b                   10.36708(17)
_cell_length_c                   17.0092(3)
_cell_measurement_reflns_used    3679
_cell_measurement_temperature    293
_cell_measurement_theta_max      69.9710
_cell_measurement_theta_min      4.3650
_cell_volume                     1806.85(6)
_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)'
_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_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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_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
_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_restrained_S_all      1.0235
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0346
_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
_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_threshold_expression     I>=2u(I)
_cod_data_source_file            d2nj01151d2.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 7061460--7061465.cif.'
_cod_original_cell_volume        1806.84(6)
_cod_database_code               7061460
_publ_section_exptl
;
Any special experimental details
;
_chemical_oxdiff_formula         C12H16N2SBiBr3
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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)
;
_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
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
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_
_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'
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) . . ?
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) . ?
