#------------------------------------------------------------------------------
#$Date: 2024-10-06 12:17:42 +0300 (Sun, 06 Oct 2024) $
#$Revision: 295337 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/00/7160042.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_7160042
loop_
_publ_author_name
'Wang, Zixiu'
'Huang, Yan'
'Deng, Dandan'
'Li, Shan'
'Yu, Yimei'
'Ye, Yifei'
'Chen, Yi'
'Lei, Jian'
_publ_section_title
;
 Facile synthesis and antifungal evaluation of hypervalent
 organoantimony(iii) and organobismuth(iii) thioates with tridentate
 C,N,C-coordinating ligands
;
_journal_issue                   35
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              7164
_journal_page_last               7172
_journal_paper_doi               10.1039/D4OB00702F
_journal_volume                  22
_journal_year                    2024
_chemical_formula_sum            'C28 H25 Bi Cl3 N S'
_chemical_formula_weight         722.880
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_date             2023-11-22
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI
svn.r6439)

;
_audit_update_record
;
2024-03-03 deposited with the CCDC.	2024-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                92.032(2)
_cell_angle_beta                 100.634(3)
_cell_angle_gamma                108.806(3)
_cell_formula_units_Z            2
_cell_length_a                   10.3272(4)
_cell_length_b                   11.2900(4)
_cell_length_c                   12.5870(3)
_cell_volume                     1358.24(8)
_refine_ls_R_factor_all          0.052
_cod_data_source_file            d4ob00702f2.cif
_cod_data_source_block           hy-1
_cod_depositor_comments
'Adding full bibliography for 7160041--7160043.cif.'
_cod_original_cell_volume        1358.2(1)
_cod_original_sg_symbol_Hall     -P_1
_cod_database_code               7160042
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_attached_hydrogens
_atom_site_calc_flag
_atom_site_thermal_displace_type
_atom_site_U_iso_or_equiv
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.7055(0) 0.6508(0) 0.6015(0) 1.000 2 i ? d Uani 0.04925(14) ? ?
S1 S 0.9009(3) 0.5485(2) 0.6367(2) 1.000 2 i ? d Uani 0.0660(6) ? ?
N1 N 0.5768(7) 0.8076(6) 0.5052(6) 1.000 2 i ? d Uani 0.0473(16) ? ?
C1 C 0.5018(9) 0.8385(8) 0.5798(7) 1.000 2 i ? d Uani 0.0491(19) ? ?
C2 C 0.5599(9) 0.9415(9) 0.6542(8) 1.000 2 i ? d Uani 0.057(2) ? ?
H2 H 0.6485 0.9964 0.6524 1.000 2 i ? calc Uiso 0.06800 ? ?
C3 C 0.4918(11) 0.9678(11) 0.7329(9) 1.000 2 i ? d Uani 0.067(3) ? ?
H3 H 0.5350 1.0382 0.7833 1.000 2 i ? calc Uiso 0.08100 ? ?
C4 C 0.3594(12) 0.8882(13) 0.7354(10) 1.000 2 i ? d Uani 0.078(3) ? ?
H4 H 0.3120 0.9049 0.7870 1.000 2 i ? calc Uiso 0.09400 ? ?
C5 C 0.2984(12) 0.7836(12) 0.6605(11) 1.000 2 i ? d Uani 0.081(3) ? ?
H5 H 0.2106 0.7283 0.6639 1.000 2 i ? calc Uiso 0.09700 ? ?
C6 C 0.3639(10) 0.7591(9) 0.5812(10) 1.000 2 i ? d Uani 0.066(3) ? ?
H6 H 0.3183 0.6911 0.5287 1.000 2 i ? calc Uiso 0.07900 ? ?
C7 C 0.4968(9) 0.7235(8) 0.4063(8) 1.000 2 i ? d Uani 0.058(2) ? ?
H7A H 0.4572 0.7705 0.3544 1.000 2 i ? calc Uiso 0.06900 ? ?
H7B H 0.4202 0.6567 0.4244 1.000 2 i ? calc Uiso 0.06900 ? ?
C8 C 0.5871(9) 0.6665(8) 0.3548(8) 1.000 2 i ? d Uani 0.056(2) ? ?
C9 C 0.5705(13) 0.6508(11) 0.2426(9) 1.000 2 i ? d Uani 0.078(3) ? ?
H9 H 0.5065 0.6798 0.1989 1.000 2 i ? calc Uiso 0.09400 ? ?
C10 C 0.6473(17) 0.5929(12) 0.1949(10) 1.000 2 i ? d Uani 0.092(4) ? ?
H10 H 0.6333 0.5813 0.1196 1.000 2 i ? calc Uiso 0.11000 ? ?
C11 C 0.7451(14) 0.5521(11) 0.2589(10) 1.000 2 i ? d Uani 0.080(3) ? ?
H11 H 0.7981 0.5142 0.2269 1.000 2 i ? calc Uiso 0.09700 ? ?
C12 C 0.7638(11) 0.5682(9) 0.3717(8) 1.000 2 i ? d Uani 0.063(2) ? ?
H12 H 0.8299 0.5410 0.4148 1.000 2 i ? calc Uiso 0.07600 ? ?
C13 C 0.6862(9) 0.6238(7) 0.4202(8) 1.000 2 i ? d Uani 0.052(2) ? ?
C14 C 0.6949(8) 0.9131(7) 0.4852(7) 1.000 2 i ? d Uani 0.0468(18) ? ?
H14A H 0.6674 0.9875 0.4804 1.000 2 i ? calc Uiso 0.05600 ? ?
H14B H 0.7151 0.8936 0.4157 1.000 2 i ? calc Uiso 0.05600 ? ?
C15 C 0.8263(8) 0.9424(7) 0.5716(7) 1.000 2 i ? d Uani 0.0430(17) ? ?
C16 C 0.9183(9) 1.0657(8) 0.5930(8) 1.000 2 i ? d Uani 0.054(2) ? ?
H16 H 0.8980 1.1282 0.5540 1.000 2 i ? calc Uiso 0.06500 ? ?
C17 C 1.0402(10) 1.0961(9) 0.6723(9) 1.000 2 i ? d Uani 0.067(3) ? ?
H17 H 1.1008 1.1788 0.6866 1.000 2 i ? calc Uiso 0.08100 ? ?
C18 C 1.0705(10) 1.0051(11) 0.7288(10) 1.000 2 i ? d Uani 0.073(3) ? ?
H18 H 1.1514 1.0264 0.7826 1.000 2 i ? calc Uiso 0.08800 ? ?
C19 C 0.9826(10) 0.8802(9) 0.7078(8) 1.000 2 i ? d Uani 0.061(2) ? ?
H19 H 1.0061 0.8185 0.7461 1.000 2 i ? calc Uiso 0.07300 ? ?
C20 C 0.8583(8) 0.8477(8) 0.6285(7) 1.000 2 i ? d Uani 0.0468(18) ? ?
C21 C 0.8654(9) 0.4660(9) 0.7517(8) 1.000 2 i ? d Uani 0.055(2) ? ?
C22 C 0.8686(11) 0.3441(9) 0.7517(9) 1.000 2 i ? d Uani 0.069(3) ? ?
H22 H 0.8847 0.3061 0.6910 1.000 2 i ? calc Uiso 0.08300 ? ?
C23 C 0.8482(13) 0.2792(11) 0.8411(12) 1.000 2 i ? d Uani 0.084(4) ? ?
H23 H 0.8521 0.1980 0.8396 1.000 2 i ? calc Uiso 0.10100 ? ?
C24 C 0.8222(13) 0.3300(14) 0.9324(12) 1.000 2 i ? d Uani 0.088(4) ? ?
C25 C 0.8382(12) 0.5160(11) 0.8425(10) 1.000 2 i ? d Uani 0.074(3) ? ?
H25 H 0.8333 0.5969 0.8439 1.000 2 i ? calc Uiso 0.08900 ? ?
C26 C 0.8182(14) 0.4514(14) 0.9309(10) 1.000 2 i ? d Uani 0.089(4) ? ?
H26 H 0.8016 0.4895 0.9913 1.000 2 i ? calc Uiso 0.10600 ? ?
C27 C 0.8061(17) 0.2637(19) 1.0349(14) 1.000 2 i ? d Uani 0.143(8) ? ?
H27A H 0.7156 0.2540 1.0498 1.000 2 i ? calc Uiso 0.21400 ? ?
H27B H 0.8772 0.3130 1.0949 1.000 2 i ? calc Uiso 0.21400 ? ?
H27C H 0.8154 0.1824 1.0245 1.000 2 i ? calc Uiso 0.21400 ? ?
Cl1 Cl 0.727(6) 0.035(4) 1.045(5) 0.211(9) 2 i ? d Uani 0.323(18) A 2
Cl2 Cl 0.801(3) -0.121(3) 0.904(2) 0.211(9) 2 i ? d Uani 0.134(8) A 2
Cl3 Cl 0.545(4) -0.215(4) 0.984(4) 0.211(9) 2 i ? d Uani 0.230(14) A 2
C29 C 0.664(5) -0.093(4) 0.959(5) 0.211(9) 2 i ? d Uani 0.159(18) A 2
H29 H 0.6129 -0.0657 0.8965 0.211(9) 2 i ? calc Uiso 0.19000 A 2
Cl4 Cl 0.8472(7) 0.8355(11) 0.9828(9) 0.789(9) 2 i ? d Uani 0.198(5) A 1
Cl5 Cl 0.5779(6) 0.6864(5) 0.8792(5) 0.789(9) 2 i ? d Uani 0.124(2) A 1
Cl6 Cl 0.6061(6) 0.8943(6) 1.0213(5) 0.789(9) 2 i ? d Uani 0.128(2) A 1
C28 C 0.683(3) 0.822(2) 0.932(2) 0.789(9) 2 i ? d Uani 0.156(9) A 1
H28 H 0.6887 0.8739 0.8712 0.789(9) 2 i ? calc Uiso 0.18700 A 1
loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_radius_bond
Bi ? ?
S ? ?
N ? ?
C ? ?
H ? ?
Cl ? ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
S1 Bi1 N1 . . . 154.50(16) no
C13 Bi1 S1 . . . 91.5(2) no
C13 Bi1 N1 . . . 71.0(3) no
C20 Bi1 S1 . . . 93.6(2) no
C20 Bi1 N1 . . . 71.1(2) no
C20 Bi1 C13 . . . 96.9(3) no
C21 S1 Bi1 . . . 102.6(3) no
C1 N1 Bi1 . . . 106.6(5) no
C1 N1 C7 . . . 118.3(7) no
C1 N1 C14 . . . 115.1(7) no
C7 N1 Bi1 . . . 97.7(5) no
C7 N1 C14 . . . 113.1(7) no
C14 N1 Bi1 . . . 102.8(4) no
C2 C1 N1 . . . 121.9(8) no
C2 C1 C6 . . . 117.6(9) no
C6 C1 N1 . . . 120.4(8) no
C1 C2 H2 . . . 118.70 no
C1 C2 C3 . . . 122.5(9) no
C3 C2 H2 . . . 118.70 no
C2 C3 H3 . . . 120.40 no
C4 C3 C2 . . . 119.3(11) no
C4 C3 H3 . . . 120.40 no
C3 C4 H4 . . . 120.40 no
C3 C4 C5 . . . 119.2(11) no
C5 C4 H4 . . . 120.40 no
C4 C5 H5 . . . 119.20 no
C6 C5 C4 . . . 121.7(11) no
C6 C5 H5 . . . 119.20 no
C1 C6 H6 . . . 120.20 no
C5 C6 C1 . . . 119.6(11) no
C5 C6 H6 . . . 120.20 no
N1 C7 H7A . . . 109.30 no
N1 C7 H7B . . . 109.30 no
N1 C7 C8 . . . 111.8(7) no
H7A C7 H7B . . . 107.90 no
C8 C7 H7A . . . 109.30 no
C8 C7 H7B . . . 109.30 no
C9 C8 C7 . . . 120.8(9) no
C9 C8 C13 . . . 118.9(9) no
C13 C8 C7 . . . 120.3(8) no
C8 C9 H9 . . . 119.40 no
C10 C9 C8 . . . 121.1(11) no
C10 C9 H9 . . . 119.40 no
C9 C10 H10 . . . 120.00 no
C9 C10 C11 . . . 120.0(11) no
C11 C10 H10 . . . 120.00 no
C10 C11 H11 . . . 120.20 no
C10 C11 C12 . . . 119.5(11) no
C12 C11 H11 . . . 120.20 no
C11 C12 H12 . . . 119.50 no
C13 C12 C11 . . . 121.(1) no
C13 C12 H12 . . . 119.50 no
C8 C13 Bi1 . . . 116.8(7) no
C12 C13 Bi1 . . . 123.7(7) no
C12 C13 C8 . . . 119.5(9) no
N1 C14 H14A . . . 108.80 no
N1 C14 H14B . . . 108.80 no
N1 C14 C15 . . . 113.9(6) no
H14A C14 H14B . . . 107.70 no
C15 C14 H14A . . . 108.80 no
C15 C14 H14B . . . 108.80 no
C16 C15 C14 . . . 119.0(7) no
C16 C15 C20 . . . 119.8(8) no
C20 C15 C14 . . . 121.2(7) no
C15 C16 H16 . . . 119.80 no
C17 C16 C15 . . . 120.5(9) no
C17 C16 H16 . . . 119.80 no
C16 C17 H17 . . . 120.10 no
C18 C17 C16 . . . 119.9(9) no
C18 C17 H17 . . . 120.10 no
C17 C18 H18 . . . 119.40 no
C17 C18 C19 . . . 121.2(9) no
C19 C18 H18 . . . 119.40 no
C18 C19 H19 . . . 120.10 no
C18 C19 C20 . . . 119.7(9) no
C20 C19 H19 . . . 120.10 no
C15 C20 Bi1 . . . 120.1(6) no
C15 C20 C19 . . . 118.8(8) no
C19 C20 Bi1 . . . 120.9(6) no
C22 C21 S1 . . . 118.5(8) no
C25 C21 S1 . . . 124.3(8) no
C25 C21 C22 . . . 117.2(10) no
C21 C22 H22 . . . 119.80 no
C23 C22 C21 . . . 120.3(11) no
C23 C22 H22 . . . 119.80 no
C22 C23 H23 . . . 118.80 no
C24 C23 C22 . . . 122.4(11) no
C24 C23 H23 . . . 118.80 no
C23 C24 C26 . . . 116.6(12) no
C23 C24 C27 . . . 123.9(15) no
C26 C24 C27 . . . 119.3(15) no
C21 C25 H25 . . . 118.90 no
C26 C25 C21 . . . 122.3(11) no
C26 C25 H25 . . . 118.90 no
C24 C26 H26 . . . 119.40 no
C25 C26 C24 . . . 121.2(12) no
C25 C26 H26 . . . 119.40 no
C24 C27 H27A . . . 109.50 no
C24 C27 H27B . . . 109.50 no
C24 C27 H27C . . . 109.50 no
H27A C27 H27B . . . 109.50 no
H27A C27 H27C . . . 109.50 no
H27B C27 H27C . . . 109.50 no
Cl1 C29 Cl2 . . . 111.(3) no
Cl1 C29 H29 . . . 102.00 no
Cl2 C29 H29 . . . 102.00 no
Cl3 C29 Cl1 . . . 120.(3) no
Cl3 C29 Cl2 . . . 116.(3) no
Cl3 C29 H29 . . . 102.00 no
Cl4 C28 Cl6 . . . 113.9(15) no
Cl4 C28 H28 . . . 104.10 no
Cl5 C28 Cl4 . . . 117.5(16) no
Cl5 C28 Cl6 . . . 111.2(14) no
Cl5 C28 H28 . . . 104.10 no
Cl6 C28 H28 . . . 104.10 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Bi1 S1 . . 2.610(2) no
Bi1 N1 . . 2.728(6) no
Bi1 C13 . . 2.254(9) no
Bi1 C20 . . 2.244(8) no
S1 C21 . . 1.781(10) no
N1 C1 . . 1.422(11) no
N1 C7 . . 1.471(11) no
N1 C14 . . 1.472(10) no
C1 C2 . . 1.363(13) no
C1 C6 . . 1.421(12) no
C2 H2 . . 0.9300 no
C2 C3 . . 1.391(13) no
C3 H3 . . 0.9300 no
C3 C4 . . 1.379(16) no
C4 H4 . . 0.9300 no
C4 C5 . . 1.379(18) no
C5 H5 . . 0.9300 no
C5 C6 . . 1.371(16) no
C6 H6 . . 0.9300 no
C7 H7A . . 0.9700 no
C7 H7B . . 0.9700 no
C7 C8 . . 1.511(13) no
C8 C9 . . 1.389(14) no
C8 C13 . . 1.411(13) no
C9 H9 . . 0.9300 no
C9 C10 . . 1.378(18) no
C10 H10 . . 0.9300 no
C10 C11 . . 1.380(18) no
C11 H11 . . 0.9300 no
C11 C12 . . 1.395(15) no
C12 H12 . . 0.9300 no
C12 C13 . . 1.374(13) no
C14 H14A . . 0.9700 no
C14 H14B . . 0.9700 no
C14 C15 . . 1.508(11) no
C15 C16 . . 1.393(12) no
C15 C20 . . 1.400(11) no
C16 H16 . . 0.9300 no
C16 C17 . . 1.390(14) no
C17 H17 . . 0.9300 no
C17 C18 . . 1.355(16) no
C18 H18 . . 0.9300 no
C18 C19 . . 1.394(14) no
C19 H19 . . 0.9300 no
C19 C20 . . 1.406(12) no
C21 C22 . . 1.387(13) no
C21 C25 . . 1.370(15) no
C22 H22 . . 0.9300 no
C22 C23 . . 1.376(16) no
C23 H23 . . 0.9300 no
C23 C24 . . 1.374(19) no
C24 C26 . . 1.385(19) no
C24 C27 . . 1.522(18) no
C25 H25 . . 0.9300 no
C25 C26 . . 1.363(16) no
C26 H26 . . 0.9300 no
C27 H27A . . 0.9600 no
C27 H27B . . 0.9600 no
C27 H27C . . 0.9600 no
Cl1 C29 . . 1.65(3) no
Cl2 C29 . . 1.79(3) no
Cl3 C29 . . 1.61(3) no
C29 H29 . . 0.9800 no
Cl4 C28 . . 1.65(3) no
Cl5 C28 . . 1.60(2) no
Cl6 C28 . . 1.79(2) no
C28 H28 . . 0.9800 no
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Bi1 S1 C21 C22 . . . . 135.3(7) no
Bi1 S1 C21 C25 . . . . -46.4(9) no
Bi1 N1 C1 C2 . . . . 91.4(8) no
Bi1 N1 C1 C6 . . . . -86.4(8) no
Bi1 N1 C7 C8 . . . . -47.9(8) no
Bi1 N1 C14 C15 . . . . -34.5(7) no
S1 C21 C22 C23 . . . . 177.0(8) no
S1 C21 C25 C26 . . . . -176.8(10) no
N1 C1 C2 C3 . . . . -175.1(8) no
N1 C1 C6 C5 . . . . 173.6(9) no
N1 C7 C8 C9 . . . . -141.1(9) no
N1 C7 C8 C13 . . . . 41.3(11) no
N1 C14 C15 C16 . . . . -149.9(7) no
N1 C14 C15 C20 . . . . 31.4(11) no
C1 N1 C7 C8 . . . . -161.5(7) no
C1 N1 C14 C15 . . . . 81.0(8) no
C1 C2 C3 C4 . . . . -1.0(15) no
C2 C1 C6 C5 . . . . -4.3(14) no
C2 C3 C4 C5 . . . . 0.7(15) no
C3 C4 C5 C6 . . . . -2.4(17) no
C4 C5 C6 C1 . . . . 4.2(16) no
C6 C1 C2 C3 . . . . 2.8(13) no
C7 N1 C1 C2 . . . . -159.9(8) no
C7 N1 C1 C6 . . . . 22.2(11) no
C7 N1 C14 C15 . . . . -138.8(7) no
C7 C8 C9 C10 . . . . -176.6(11) no
C7 C8 C13 Bi1 . . . . -1.8(10) no
C7 C8 C13 C12 . . . . 177.7(8) no
C8 C9 C10 C11 . . . . -2.(2) no
C9 C8 C13 Bi1 . . . . -179.4(7) no
C9 C8 C13 C12 . . . . 0.1(13) no
C9 C10 C11 C12 . . . . 1.(2) no
C10 C11 C12 C13 . . . . 0.2(17) no
C11 C12 C13 Bi1 . . . . 178.8(8) no
C11 C12 C13 C8 . . . . -0.7(14) no
C13 C8 C9 C10 . . . . 1.0(16) no
C14 N1 C1 C2 . . . . -21.8(11) no
C14 N1 C1 C6 . . . . 160.4(8) no
C14 N1 C7 C8 . . . . 59.5(9) no
C14 C15 C16 C17 . . . . 179.8(8) no
C14 C15 C20 Bi1 . . . . -4.8(10) no
C14 C15 C20 C19 . . . . 179.7(8) no
C15 C16 C17 C18 . . . . 0.5(15) no
C16 C15 C20 Bi1 . . . . 176.5(6) no
C16 C15 C20 C19 . . . . 1.0(12) no
C16 C17 C18 C19 . . . . 1.1(17) no
C17 C18 C19 C20 . . . . -1.5(16) no
C18 C19 C20 Bi1 . . . . -175.0(8) no
C18 C19 C20 C15 . . . . 0.4(14) no
C20 C15 C16 C17 . . . . -1.5(13) no
C21 C22 C23 C24 . . . . 0.9(18) no
C21 C25 C26 C24 . . . . -1.(2) no
C22 C21 C25 C26 . . . . 1.5(17) no
C22 C23 C24 C26 . . . . -0.4(19) no
C22 C23 C24 C27 . . . . -176.9(12) no
C23 C24 C26 C25 . . . . 0.(2) no
C25 C21 C22 C23 . . . . -1.4(15) no
C27 C24 C26 C25 . . . . 177.1(12) no
