#------------------------------------------------------------------------------
#$Date: 2024-10-06 12:17:42 +0300 (Sun, 06 Oct 2024) $
#$Revision: 295337 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/00/7160041.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_7160041
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            'C24 H26 N S Sb'
_chemical_formula_weight         482.270
_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             2023-09-05
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI
svn.r6439)

;
_audit_update_record
;
2023-09-20 deposited with the CCDC.	2024-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                104.386(3)
_cell_angle_beta                 112.313(3)
_cell_angle_gamma                90.028(3)
_cell_formula_units_Z            2
_cell_length_a                   9.6728(3)
_cell_length_b                   10.3643(3)
_cell_length_c                   11.0212(2)
_cell_volume                     984.56(5)
_refine_ls_R_factor_all          0.121
_cod_data_source_file            d4ob00702f2.cif
_cod_data_source_block           sb0903
_cod_depositor_comments
'Adding full bibliography for 7160041--7160043.cif.'
_cod_original_cell_volume        984.6(1)
_cod_original_sg_symbol_Hall     -P_1
_cod_database_code               7160041
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
Sb1 Sb 0.3236(0) 0.6278(0) 0.6549(0) 1.000 2 i ? d Uani 0.06612(13) A -1
S1 S 0.2718(3) 0.5071(3) 0.8035(2) 1.000 2 i ? d Uani 0.1247(7) A -1
N1 N 0.4508(5) 0.8071(5) 0.5799(5) 1.000 2 i ? d Uani 0.0554(8) A -1
C1 C 0.3911(7) 0.9308(7) 0.7737(7) 1.000 2 i ? d Uani 0.0686(8) A -1
C2 C 0.3816(9) 1.0569(9) 0.8541(8) 1.000 2 i ? d Uani 0.0906(10) A -1
H2 H 0.4375 1.1323 0.8585 1.000 2 i ? calc Uiso 0.10900 A -1
C3 C 0.2898(10) 1.0702(11) 0.9270(9) 1.000 2 i ? d Uani 0.1076(10) A -1
H3 H 0.2840 1.1542 0.9789 1.000 2 i ? calc Uiso 0.12900 A -1
C4 C 0.2124(10) 0.9656(11) 0.9226(9) 1.000 2 i ? d Uani 0.1102(15) A -1
H4 H 0.1466 0.9774 0.9669 1.000 2 i ? calc Uiso 0.13200 A -1
C5 C 0.2246(8) 0.8312(12) 0.8512(8) 1.000 2 i ? d Uani 0.0937(10) A -1
H5 H 0.1750 0.7562 0.8547 1.000 2 i ? calc Uiso 0.11200 A -1
C6 C 0.3138(6) 0.8211(7) 0.7778(6) 1.000 2 i ? d Uani 0.0663(8) A -1
C7 C 0.5646(6) 0.6278(6) 0.7473(6) 1.000 2 i ? d Uani 0.0576(9) A -1
C8 C 0.6347(8) 0.5777(7) 0.8582(7) 1.000 2 i ? d Uani 0.0724(11) A -1
H8 H 0.5785 0.5450 0.8986 1.000 2 i ? calc Uiso 0.08700 A -1
C9 C 0.7895(8) 0.5764(8) 0.9088(7) 1.000 2 i ? d Uani 0.0763(11) A -1
H9 H 0.8354 0.5340 0.9769 1.000 2 i ? calc Uiso 0.09200 A -1
C10 C 0.8757(8) 0.6359(8) 0.8609(7) 1.000 2 i ? d Uani 0.0808(10) A -1
H10 H 0.9799 0.6421 0.9029 1.000 2 i ? calc Uiso 0.09700 A -1
C11 C 0.8086(7) 0.6878(8) 0.7488(7) 1.000 2 i ? d Uani 0.0813(12) A -1
H11 H 0.8666 0.7176 0.7085 1.000 2 i ? calc Uiso 0.09800 A -1
C12 C 0.6468(6) 0.6949(7) 0.6960(6) 1.000 2 i ? d Uani 0.0688(9) A -1
C13 C 0.5730(7) 0.7301(7) 0.5673(6) 1.000 2 i ? d Uani 0.0697(10) A -1
H13A H 0.6436 0.7832 0.5511 1.000 2 i ? calc Uiso 0.08400 A -1
H13B H 0.5340 0.6499 0.4921 1.000 2 i ? calc Uiso 0.08400 A -1
C14 C 0.3441(6) 0.8304(6) 0.4562(6) 1.000 2 i ? d Uani 0.0610(9) A -1
C15 C 0.2437(8) 0.9237(8) 0.4645(7) 1.000 2 i ? d Uani 0.0826(12) A -1
H15 H 0.2472 0.9746 0.5482 1.000 2 i ? calc Uiso 0.09900 A -1
C16 C 0.1356(10) 0.9390(9) 0.3412(8) 1.000 2 i ? d Uani 0.0980(18) A -1
H16 H 0.0682 1.0024 0.3444 1.000 2 i ? calc Uiso 0.11800 A -1
C17 C 0.1267(10) 0.8609(8) 0.2135(9) 1.000 2 i ? d Uani 0.0934(12) A -1
H17 H 0.0524 0.8701 0.1334 1.000 2 i ? calc Uiso 0.11200 A -1
C18 C 0.2244(11) 0.7759(9) 0.2103(9) 1.000 2 i ? d Uani 0.0958(13) A -1
H18 H 0.2233 0.7271 0.1267 1.000 2 i ? calc Uiso 0.11500 A -1
C19 C 0.3329(8) 0.7558(8) 0.3317(7) 1.000 2 i ? d Uani 0.0780(15) A -1
H19 H 0.3978 0.6905 0.3262 1.000 2 i ? calc Uiso 0.09400 A -1
C20 C 0.4967(6) 0.9272(6) 0.7027(6) 1.000 2 i ? d Uani 0.0638(10) A -1
H20A H 0.5981 0.9226 0.7652 1.000 2 i ? calc Uiso 0.07700 A -1
H20B H 0.4960 1.0086 0.6742 1.000 2 i ? calc Uiso 0.07700 A -1
C21 C 0.1168(6) 0.2792(4) 0.5855(5) 1.000 2 i ? d Uani 0.06612(13) A -1
H21A H 0.1600 0.3049 0.5286 1.000 2 i ? calc Uiso 0.09900 A -1
H21B H 0.0227 0.2256 0.5296 1.000 2 i ? calc Uiso 0.09900 A -1
H21C H 0.1841 0.2285 0.6400 1.000 2 i ? calc Uiso 0.09900 A -1
C22 C 0.0907(5) 0.4055(4) 0.6790(4) 1.000 2 i ? d Uani 0.06612(13) A -1
C23 C -0.0235(5) 0.3701(5) 0.7363(4) 1.000 2 i ? d Uani 0.06612(13) A -1
H23A H -0.0275 0.4467 0.8046 1.000 2 i ? calc Uiso 0.09900 A -1
H23B H 0.0073 0.2969 0.7760 1.000 2 i ? calc Uiso 0.09900 A -1
H23C H -0.1212 0.3449 0.6639 1.000 2 i ? calc Uiso 0.09900 A -1
C24 C 0.0296(6) 0.5071(4) 0.5947(4) 1.000 2 i ? d Uani 0.06612(13) A -1
H24A H 0.0793 0.5949 0.6472 1.000 2 i ? calc Uiso 0.09900 A -1
H24B H -0.0766 0.5075 0.5719 1.000 2 i ? calc Uiso 0.09900 A -1
H24C H 0.0480 0.4818 0.5127 1.000 2 i ? calc Uiso 0.09900 A -1
loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_radius_bond
Sb ? ?
S ? ?
N ? ?
C ? ?
H ? ?
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
C6 Sb1 S1 . . . 93.4(2) no
C6 Sb1 C7 . . . 96.4(2) no
C7 Sb1 S1 . . . 94.70(19) no
C22 S1 Sb1 . . . 99.64(17) no
C13 N1 C20 . . . 114.9(4) no
C14 N1 C13 . . . 116.2(5) no
C14 N1 C20 . . . 114.5(5) no
C2 C1 C20 . . . 116.5(7) no
C6 C1 C2 . . . 117.2(8) no
C6 C1 C20 . . . 126.0(6) no
C1 C2 H2 . . . 119.50 no
C3 C2 C1 . . . 120.9(9) no
C3 C2 H2 . . . 119.50 no
C2 C3 H3 . . . 120.00 no
C4 C3 C2 . . . 120.1(10) no
C4 C3 H3 . . . 120.00 no
C3 C4 H4 . . . 118.80 no
C3 C4 C5 . . . 122.5(10) no
C5 C4 H4 . . . 118.80 no
C4 C5 H5 . . . 122.00 no
C6 C5 C4 . . . 116.1(10) no
C6 C5 H5 . . . 122.00 no
C1 C6 Sb1 . . . 118.2(5) no
C5 C6 Sb1 . . . 118.8(6) no
C5 C6 C1 . . . 123.0(7) no
C8 C7 Sb1 . . . 122.7(5) no
C8 C7 C12 . . . 121.7(5) no
C12 C7 Sb1 . . . 115.3(4) no
C7 C8 H8 . . . 120.30 no
C7 C8 C9 . . . 119.4(7) no
C9 C8 H8 . . . 120.30 no
C8 C9 H9 . . . 119.30 no
C10 C9 C8 . . . 121.4(7) no
C10 C9 H9 . . . 119.30 no
C9 C10 H10 . . . 119.80 no
C9 C10 C11 . . . 120.4(7) no
C11 C10 H10 . . . 119.80 no
C10 C11 H11 . . . 120.40 no
C10 C11 C12 . . . 119.3(7) no
C12 C11 H11 . . . 120.40 no
C7 C12 C11 . . . 116.5(6) no
C7 C12 C13 . . . 121.0(5) no
C11 C12 C13 . . . 119.4(6) no
N1 C13 C12 . . . 106.6(6) no
N1 C13 H13A . . . 110.40 no
N1 C13 H13B . . . 110.40 no
C12 C13 H13A . . . 110.40 no
C12 C13 H13B . . . 110.40 no
H13A C13 H13B . . . 108.60 no
C15 C14 N1 . . . 119.1(6) no
C19 C14 N1 . . . 121.4(6) no
C19 C14 C15 . . . 119.4(6) no
C14 C15 H15 . . . 121.20 no
C14 C15 C16 . . . 117.6(7) no
C16 C15 H15 . . . 121.20 no
C15 C16 H16 . . . 119.00 no
C17 C16 C15 . . . 122.0(8) no
C17 C16 H16 . . . 119.00 no
C16 C17 H17 . . . 120.80 no
C18 C17 C16 . . . 118.4(8) no
C18 C17 H17 . . . 120.80 no
C17 C18 H18 . . . 119.40 no
C17 C18 C19 . . . 121.2(9) no
C19 C18 H18 . . . 119.40 no
C14 C19 C18 . . . 121.3(7) no
C14 C19 H19 . . . 119.40 no
C18 C19 H19 . . . 119.40 no
N1 C20 H20A . . . 109.60 no
N1 C20 H20B . . . 109.60 no
C1 C20 N1 . . . 110.4(5) no
C1 C20 H20A . . . 109.60 no
C1 C20 H20B . . . 109.60 no
H20A C20 H20B . . . 108.10 no
H21A C21 H21B . . . 109.50 no
H21A C21 H21C . . . 109.50 no
H21B C21 H21C . . . 109.50 no
C22 C21 H21A . . . 109.50 no
C22 C21 H21B . . . 109.50 no
C22 C21 H21C . . . 109.50 no
C21 C22 S1 . . . 112.0(3) no
C21 C22 C23 . . . 110.5(4) no
C21 C22 C24 . . . 108.3(4) no
C23 C22 S1 . . . 117.5(3) no
C24 C22 S1 . . . 97.8(3) no
C24 C22 C23 . . . 109.9(4) no
C22 C23 H23A . . . 109.50 no
C22 C23 H23B . . . 109.50 no
C22 C23 H23C . . . 109.50 no
H23A C23 H23B . . . 109.50 no
H23A C23 H23C . . . 109.50 no
H23B C23 H23C . . . 109.50 no
C22 C24 H24A . . . 109.50 no
C22 C24 H24B . . . 109.50 no
C22 C24 H24C . . 2_566 144.3(5) no
C22 C24 H24C . . . 109.50 no
H24A C24 H24B . . . 109.50 no
H24A C24 H24C . . 2_566 105.90 no
H24A C24 H24C . . . 109.50 no
H24B C24 H24C . . . 109.50 no
H24B C24 H24C . . 2_566 61.10 no
H24C C24 H24C . . 2_566 52.90 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
Sb1 S1 . . 2.478(3) no
Sb1 C6 . . 2.146(7) no
Sb1 C7 . . 2.161(5) no
S1 C22 . . 1.875(4) no
N1 C13 . . 1.457(8) no
N1 C14 . . 1.441(7) no
N1 C20 . . 1.512(7) no
C1 C2 . . 1.41(1) no
C1 C6 . . 1.379(11) no
C1 C20 . . 1.500(11) no
C2 H2 . . 0.9300 no
C2 C3 . . 1.393(14) no
C3 H3 . . 0.9300 no
C3 C4 . . 1.298(16) no
C4 H4 . . 0.9300 no
C4 C5 . . 1.449(15) no
C5 H5 . . 0.9300 no
C5 C6 . . 1.378(12) no
C7 C8 . . 1.383(9) no
C7 C12 . . 1.403(10) no
C8 H8 . . 0.9300 no
C8 C9 . . 1.387(10) no
C9 H9 . . 0.9300 no
C9 C10 . . 1.359(12) no
C10 H10 . . 0.9300 no
C10 C11 . . 1.399(11) no
C11 H11 . . 0.9300 no
C11 C12 . . 1.456(8) no
C12 C13 . . 1.465(9) no
C13 H13A . . 0.9700 no
C13 H13B . . 0.9700 no
C14 C15 . . 1.383(10) no
C14 C19 . . 1.361(10) no
C15 H15 . . 0.9300 no
C15 C16 . . 1.411(10) no
C16 H16 . . 0.9300 no
C16 C17 . . 1.409(13) no
C17 H17 . . 0.9300 no
C17 C18 . . 1.298(13) no
C18 H18 . . 0.9300 no
C18 C19 . . 1.417(11) no
C19 H19 . . 0.9300 no
C20 H20A . . 0.9700 no
C20 H20B . . 0.9700 no
C21 H21A . . 0.9600 no
C21 H21B . . 0.9600 no
C21 H21C . . 0.9600 no
C21 C22 . . 1.538(6) no
C22 C23 . . 1.549(6) no
C22 C24 . . 1.546(5) no
C23 H23A . . 0.9600 no
C23 H23B . . 0.9600 no
C23 H23C . . 0.9600 no
C24 H24A . . 0.9600 no
C24 H24B . . 0.9600 no
C24 H24C . 2_566 1.171(8) no
C24 H24C . . 0.9600 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
Sb1 S1 C22 C21 . . . . 80.8(4) no
Sb1 S1 C22 C23 . . . . -149.8(3) no
Sb1 S1 C22 C24 . . . . -32.5(3) no
Sb1 C7 C8 C9 . . . . 177.6(5) no
Sb1 C7 C12 C11 . . . . -175.5(5) no
Sb1 C7 C12 C13 . . . . -15.3(8) no
N1 C14 C15 C16 . . . . -176.7(7) no
N1 C14 C19 C18 . . . . 177.8(7) no
C1 C2 C3 C4 . . . . 0.6(13) no
C2 C1 C6 Sb1 . . . . 179.3(5) no
C2 C1 C6 C5 . . . . 3.(1) no
C2 C1 C20 N1 . . . . -156.4(6) no
C2 C3 C4 C5 . . . . 4.3(13) no
C3 C4 C5 C6 . . . . -5.4(12) no
C4 C5 C6 Sb1 . . . . -174.8(5) no
C4 C5 C6 C1 . . . . 1.5(10) no
C6 C1 C2 C3 . . . . -4.2(10) no
C6 C1 C20 N1 . . . . 30.2(8) no
C7 C8 C9 C10 . . . . 6.9(10) no
C7 C12 C13 N1 . . . . 54.7(8) no
C8 C7 C12 C11 . . . . 10.9(9) no
C8 C7 C12 C13 . . . . 171.0(6) no
C8 C9 C10 C11 . . . . -6.8(11) no
C9 C10 C11 C12 . . . . 8.7(11) no
C10 C11 C12 C7 . . . . -10.4(10) no
C10 C11 C12 C13 . . . . -171.0(7) no
C11 C12 C13 N1 . . . . -145.7(6) no
C12 C7 C8 C9 . . . . -9.2(10) no
C13 N1 C14 C15 . . . . -167.3(6) no
C13 N1 C14 C19 . . . . 17.5(9) no
C13 N1 C20 C1 . . . . -133.4(6) no
C14 N1 C13 C12 . . . . -168.3(5) no
C14 N1 C20 C1 . . . . 88.3(7) no
C14 C15 C16 C17 . . . . 1.3(14) no
C15 C14 C19 C18 . . . . 2.6(12) no
C15 C16 C17 C18 . . . . -2.3(15) no
C16 C17 C18 C19 . . . . 3.4(15) no
C17 C18 C19 C14 . . . . -3.7(14) no
C19 C14 C15 C16 . . . . -1.4(12) no
C20 N1 C13 C12 . . . . 54.2(7) no
C20 N1 C14 C15 . . . . -29.6(8) no
C20 N1 C14 C19 . . . . 155.3(7) no
C20 C1 C2 C3 . . . . -178.2(7) no
C20 C1 C6 Sb1 . . . . -7.3(8) no
C20 C1 C6 C5 . . . . 176.4(6) no
