# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_sb0903
_audit_block_doi                 10.5517/ccdc.csd.cc2h26d6
_database_code_depnum_ccdc_archive 'CCDC 2296027'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D4OB00702F 2024
loop_
_audit_author_name
_audit_author_address
'Jian Lei'
;Gannan Medical University
China
;
_audit_update_record             
;
2023-09-20 deposited with the CCDC.	2024-08-15 downloaded from the CCDC.
;
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI
svn.r6439)

;
_audit_creation_date             2023-09-05
_chemical_formula_sum            'C24 H26 N S Sb'
_chemical_formula_weight         482.270
_refine_ls_R_factor_all          0.121
_cell_length_a                   9.6728(3)
_cell_length_b                   10.3643(3)
_cell_length_c                   11.0212(2)
_cell_angle_alpha                104.386(3)
_cell_angle_beta                 112.313(3)
_cell_angle_gamma                90.028(3)
_cell_volume                     984.6(1)
_cell_formula_units_Z            2
_symmetry_cell_setting           triclinic
_symmetry_int_tables_number      2
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  -P_1

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_radius_bond
Sb ? ?
S ? ?
N ? ?
C ? ?
H ? ?


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_
_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_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_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
####################################################################### 
# 
# 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_hy-1
_audit_block_doi                 10.5517/ccdc.csd.cc2jfxtq
_database_code_depnum_ccdc_archive 'CCDC 2337084'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D4OB00702F 2024
loop_
_audit_author_name
_audit_author_address
'Jian Lei'
;Gannan Medical University
China
;
_audit_update_record             
;
2024-03-03 deposited with the CCDC.	2024-08-15 downloaded from the CCDC.
;
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI
svn.r6439)

;
_audit_creation_date             2023-11-22
_chemical_formula_sum            'C28 H25 Bi Cl3 N S'
_chemical_formula_weight         722.880
_refine_ls_R_factor_all          0.052
_cell_length_a                   10.3272(4)
_cell_length_b                   11.2900(4)
_cell_length_c                   12.5870(3)
_cell_angle_alpha                92.032(2)
_cell_angle_beta                 100.634(3)
_cell_angle_gamma                108.806(3)
_cell_volume                     1358.2(1)
_cell_formula_units_Z            2
_symmetry_cell_setting           triclinic
_symmetry_int_tables_number      2
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  -P_1

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_radius_bond
Bi ? ?
S ? ?
N ? ?
C ? ?
H ? ?
Cl ? ?


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_
_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_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_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
####################################################################### 
# 
# 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_hy-2
_audit_block_doi                 10.5517/ccdc.csd.cc2jfxvr
_database_code_depnum_ccdc_archive 'CCDC 2337085'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D4OB00702F 2024
loop_
_audit_author_name
_audit_author_address
'Jian Lei'
;Gannan Medical University
China
;
_audit_update_record             
;
2024-03-03 deposited with the CCDC.	2024-08-15 downloaded from the CCDC.
;
_audit_creation_date             2023-11-21
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H21 Bi Cl N S'
_chemical_formula_sum            'C26 H21 Bi Cl N S'
_chemical_formula_weight         623.93
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Bi S Cl'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.0111 8.9310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.80600(10)
_cell_length_b                   13.52470(10)
_cell_length_c                   21.4223(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.2140(10)
_cell_angle_gamma                90
_cell_volume                     2248.35(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9877
_cell_measurement_temperature    293.00(10)
_cell_measurement_theta_max      73.8490
_cell_measurement_theta_min      4.1740
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    17.441
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54288
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.843
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12325
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.256
_diffrn_reflns_theta_min         3.872
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -82.00 -32.00   0.50    0.50    --    0.00 -19.00-150.00  100
  2  ω    -32.00  28.00   0.50    0.50    --    0.00 -82.00-120.00  120
  3  ω    -33.00  -8.00   0.50    0.50    --    0.00 -82.00 -60.00   50
  4  ω    -32.00  30.00   0.50    0.50    --    0.00 -82.00  60.00  124
  5  ω      7.00 108.00   0.50    0.50    --   95.80 -30.00-180.00  202
  6  ω    124.00 167.00   0.50    0.50    --   95.80  77.00-150.00   86
  7  ω    128.00 154.00   0.50    0.50    --   95.80  61.00 120.00   52
  8  ω     10.00  98.00   0.50    0.50    --   95.80 -45.00 -30.00  176
  9  ω      8.00  70.00   0.50    0.50    --   95.80 -45.00-180.00  124
 10  ω     76.00 111.00   0.50    0.50    --   95.80 -45.00-180.00   70
 11  ω     72.00 109.00   0.50    0.50    --   95.80  61.00 120.00   74
 12  ω     12.00 105.00   0.50    0.50    --   95.80 -30.00 -30.00  186
 13  ω     72.00 156.00   0.50    0.50    --   95.80  15.00-180.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0258601000
_diffrn_orient_matrix_UB_12      -0.0757143000
_diffrn_orient_matrix_UB_13      0.0518865000
_diffrn_orient_matrix_UB_21      0.1826903000
_diffrn_orient_matrix_UB_22      -0.0406236000
_diffrn_orient_matrix_UB_23      -0.0042724000
_diffrn_orient_matrix_UB_31      0.0731768000
_diffrn_orient_matrix_UB_32      0.0748060000
_diffrn_orient_matrix_UB_33      0.0502222000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4273
_reflns_number_total             4451
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.647
_refine_diff_density_min         -1.628
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0269
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0374P)²+2.6160P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0683
_refine_ls_wR_factor_ref         0.0691
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C25(H25),
  C26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.65138(2) 0.63473(2) 0.62759(2) 0.03934(7) Uani 1 1 d . . . . .
Cl1 Cl 0.10609(19) 1.07383(11) 0.58203(7) 0.0782(4) Uani 1 1 d . . . . .
S1 S 0.71955(17) 0.78085(10) 0.55398(7) 0.0672(3) Uani 1 1 d . . . . .
N1 N 0.7248(4) 0.4623(2) 0.69200(13) 0.0356(6) Uani 1 1 d . . . . .
C1 C 0.8184(4) 0.4357(3) 0.58451(18) 0.0421(8) Uani 1 1 d . . . . .
C2 C 0.8771(6) 0.3673(4) 0.5432(3) 0.0587(13) Uani 1 1 d . . . . .
H2 H 0.929677 0.307533 0.558597 0.070 Uiso 1 1 calc R U . . .
C3 C 0.8579(7) 0.3874(5) 0.4784(3) 0.0723(18) Uani 1 1 d . . . . .
H3 H 0.900538 0.341685 0.450238 0.087 Uiso 1 1 calc R U . . .
C4 C 0.7788(7) 0.4718(5) 0.4557(2) 0.0682(15) Uani 1 1 d . . . . .
H4 H 0.763005 0.484050 0.411766 0.082 Uiso 1 1 calc R U . . .
C5 C 0.7225(6) 0.5388(4) 0.49675(19) 0.0559(11) Uani 1 1 d . . . . .
H5 H 0.668179 0.597849 0.480828 0.067 Uiso 1 1 calc R U . . .
C6 C 0.7428(5) 0.5226(3) 0.56114(17) 0.0418(8) Uani 1 1 d . . . . .
C7 C 0.8479(5) 0.4131(3) 0.65418(19) 0.0421(8) Uani 1 1 d . . . . .
H7A H 0.839985 0.340680 0.660120 0.050 Uiso 1 1 calc R U . . .
H7B H 0.966242 0.433677 0.670186 0.050 Uiso 1 1 calc R U . . .
C8 C 0.5704(4) 0.4081(3) 0.69708(17) 0.0368(7) Uani 1 1 d . . . . .
C9 C 0.4991(6) 0.3517(3) 0.6459(2) 0.0489(10) Uani 1 1 d . . . . .
H9 H 0.555145 0.349427 0.608712 0.059 Uiso 1 1 calc R U . . .
C10 C 0.3478(6) 0.2992(4) 0.6489(2) 0.0561(11) Uani 1 1 d . . . . .
H10 H 0.300178 0.262051 0.613550 0.067 Uiso 1 1 calc R U . . .
C11 C 0.2651(5) 0.3006(3) 0.7032(2) 0.0543(11) Uani 1 1 d . . . . .
H11 H 0.161784 0.264315 0.705405 0.065 Uiso 1 1 calc R U . . .
C12 C 0.3349(6) 0.3551(3) 0.7532(2) 0.0544(11) Uani 1 1 d . . . . .
H12 H 0.279439 0.355953 0.790583 0.065 Uiso 1 1 calc R U . . .
C13 C 0.4855(5) 0.4095(3) 0.7509(2) 0.0467(9) Uani 1 1 d . . . . .
H13 H 0.530410 0.447654 0.786125 0.056 Uiso 1 1 calc R U . . .
C14 C 0.8106(6) 0.5067(3) 0.75009(18) 0.0467(9) Uani 1 1 d . . . . .
H14A H 0.865222 0.454040 0.777544 0.056 Uiso 1 1 calc R U . . .
H14B H 0.724027 0.540545 0.773046 0.056 Uiso 1 1 calc R U . . .
C15 C 0.9461(5) 0.5802(3) 0.73468(18) 0.0422(8) Uani 1 1 d . . . . .
C16 C 0.9115(5) 0.6469(3) 0.68522(18) 0.0385(8) Uani 1 1 d . . . . .
C17 C 1.0353(5) 0.7159(3) 0.6739(2) 0.0495(10) Uani 1 1 d . . . . .
H17 H 1.011837 0.762563 0.640999 0.059 Uiso 1 1 calc R U . . .
C18 C 1.1937(6) 0.7174(4) 0.7105(3) 0.0666(14) Uani 1 1 d . . . . .
H18 H 1.278556 0.764303 0.701769 0.080 Uiso 1 1 calc R U . . .
C19 C 1.2282(7) 0.6522(4) 0.7585(3) 0.0700(15) Uani 1 1 d . . . . .
H19 H 1.336331 0.654155 0.783519 0.084 Uiso 1 1 calc R U . . .
C20 C 1.1052(6) 0.5826(4) 0.7711(2) 0.0589(11) Uani 1 1 d . . . . .
H20 H 1.129662 0.536867 0.804545 0.071 Uiso 1 1 calc R U . . .
C21 C 0.5475(6) 0.8624(3) 0.5641(2) 0.0512(10) Uani 1 1 d . . . . .
C22 C 0.5786(6) 0.9607(4) 0.5797(2) 0.0562(11) Uani 1 1 d . . . . .
H22 H 0.694121 0.983529 0.586947 0.067 Uiso 1 1 calc R U . . .
C23 C 0.4456(6) 1.0261(4) 0.5848(2) 0.0575(11) Uani 1 1 d . . . . .
H23 H 0.469137 1.093314 0.595293 0.069 Uiso 1 1 calc R U . . .
C24 C 0.2768(6) 0.9927(3) 0.5746(2) 0.0532(10) Uani 1 1 d . . . . .
C25 C 0.2416(7) 0.8966(4) 0.5594(3) 0.0667(13) Uani 1 1 d . . . . .
H25 H 0.125683 0.874138 0.553035 0.080 Uiso 1 1 calc R U . . .
C26 C 0.3778(7) 0.8310(4) 0.5533(3) 0.0668(13) Uani 1 1 d . . . . .
H26 H 0.353597 0.764311 0.541529 0.080 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 S1 2.6186(12) . ?
Bi1 N1 2.739(3) . ?
Bi1 C6 2.248(4) . ?
Bi1 C16 2.265(4) . ?
Cl1 C24 1.747(5) . ?
S1 C21 1.769(5) . ?
N1 C7 1.480(4) . ?
N1 C8 1.424(4) . ?
N1 C14 1.476(4) . ?
C1 C2 1.391(6) . ?
C1 C6 1.385(6) . ?
C1 C7 1.517(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.405(8) . ?
C3 H3 0.9500 . ?
C3 C4 1.362(9) . ?
C4 H4 0.9500 . ?
C4 C5 1.368(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.400(6) . ?
C8 C13 1.390(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.385(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(7) . ?
C11 H11 0.9500 . ?
C11 C12 1.365(7) . ?
C12 H12 0.9500 . ?
C12 C13 1.392(6) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.514(6) . ?
C15 C16 1.395(6) . ?
C15 C20 1.394(5) . ?
C16 C17 1.383(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.390(7) . ?
C18 H18 0.9500 . ?
C18 C19 1.360(8) . ?
C19 H19 0.9500 . ?
C19 C20 1.391(8) . ?
C20 H20 0.9500 . ?
C21 C22 1.386(6) . ?
C21 C26 1.387(7) . ?
C22 H22 0.9500 . ?
C22 C23 1.377(7) . ?
C23 H23 0.9500 . ?
C23 C24 1.387(6) . ?
C24 C25 1.360(7) . ?
C25 H25 0.9500 . ?
C25 C26 1.402(8) . ?
C26 H26 0.9500 . ?

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
S1 Bi1 N1 154.29(7) . . ?
C6 Bi1 S1 91.64(11) . . ?
C6 Bi1 N1 71.41(12) . . ?
C6 Bi1 C16 93.83(13) . . ?
C16 Bi1 S1 92.58(11) . . ?
C16 Bi1 N1 70.18(12) . . ?
C21 S1 Bi1 100.99(14) . . ?
C7 N1 Bi1 102.7(2) . . ?
C8 N1 Bi1 110.1(2) . . ?
C8 N1 C7 114.6(3) . . ?
C8 N1 C14 117.1(3) . . ?
C14 N1 Bi1 97.4(2) . . ?
C14 N1 C7 112.5(3) . . ?
C2 C1 C7 117.8(4) . . ?
C6 C1 C2 119.4(4) . . ?
C6 C1 C7 122.7(3) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.5(5) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.7(4) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.3(5) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.6(5) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 Bi1 119.7(3) . . ?
C1 C6 C5 119.4(4) . . ?
C5 C6 Bi1 120.8(3) . . ?
N1 C7 C1 114.2(3) . . ?
N1 C7 H7A 108.7 . . ?
N1 C7 H7B 108.7 . . ?
C1 C7 H7A 108.7 . . ?
C1 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 N1 119.2(3) . . ?
C13 C8 N1 122.7(3) . . ?
C13 C8 C9 118.1(4) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.8(4) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.4(4) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.6 . . ?
C12 C11 C10 118.9(4) . . ?
C12 C11 H11 120.6 . . ?
C11 C12 H12 119.2 . . ?
C11 C12 C13 121.5(4) . . ?
C13 C12 H12 119.2 . . ?
C8 C13 C12 120.2(4) . . ?
C8 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
N1 C14 H14A 109.6 . . ?
N1 C14 H14B 109.6 . . ?
N1 C14 C15 110.3(3) . . ?
H14A C14 H14B 108.1 . . ?
C15 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
C16 C15 C14 120.5(3) . . ?
C20 C15 C14 119.7(4) . . ?
C20 C15 C16 119.8(4) . . ?
C15 C16 Bi1 117.1(3) . . ?
C17 C16 Bi1 123.7(3) . . ?
C17 C16 C15 119.1(4) . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.5(5) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.5(5) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 120.1(5) . . ?
C20 C19 H19 120.0 . . ?
C15 C20 H20 120.0 . . ?
C19 C20 C15 119.9(5) . . ?
C19 C20 H20 120.0 . . ?
C22 C21 S1 120.8(4) . . ?
C22 C21 C26 118.3(5) . . ?
C26 C21 S1 120.8(4) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 C21 121.4(4) . . ?
C23 C22 H22 119.3 . . ?
C22 C23 H23 120.3 . . ?
C22 C23 C24 119.3(4) . . ?
C24 C23 H23 120.3 . . ?
C23 C24 Cl1 120.1(4) . . ?
C25 C24 Cl1 119.0(4) . . ?
C25 C24 C23 120.9(5) . . ?
C24 C25 H25 120.3 . . ?
C24 C25 C26 119.4(5) . . ?
C26 C25 H25 120.3 . . ?
C21 C26 C25 120.7(5) . . ?
C21 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Bi1 S1 C21 C22 128.3(3) . . . . ?
Bi1 S1 C21 C26 -55.2(4) . . . . ?
Bi1 N1 C7 C1 -31.5(3) . . . . ?
Bi1 N1 C8 C9 80.0(4) . . . . ?
Bi1 N1 C8 C13 -99.3(3) . . . . ?
Bi1 N1 C14 C15 -49.7(3) . . . . ?
Bi1 C16 C17 C18 -178.5(3) . . . . ?
Cl1 C24 C25 C26 179.9(4) . . . . ?
S1 C21 C22 C23 177.0(4) . . . . ?
S1 C21 C26 C25 -178.0(4) . . . . ?
N1 C8 C9 C10 -179.1(4) . . . . ?
N1 C8 C13 C12 180.0(4) . . . . ?
N1 C14 C15 C16 43.5(5) . . . . ?
N1 C14 C15 C20 -138.0(4) . . . . ?
C1 C2 C3 C4 -1.6(7) . . . . ?
C2 C1 C6 Bi1 -179.0(3) . . . . ?
C2 C1 C6 C5 1.8(5) . . . . ?
C2 C1 C7 N1 -155.4(3) . . . . ?
C2 C3 C4 C5 2.0(7) . . . . ?
C3 C4 C5 C6 -0.5(7) . . . . ?
C4 C5 C6 Bi1 179.4(3) . . . . ?
C4 C5 C6 C1 -1.4(6) . . . . ?
C6 C1 C2 C3 -0.3(6) . . . . ?
C6 C1 C7 N1 27.4(5) . . . . ?
C7 N1 C8 C9 -35.1(5) . . . . ?
C7 N1 C8 C13 145.5(4) . . . . ?
C7 N1 C14 C15 57.3(4) . . . . ?
C7 C1 C2 C3 -177.6(4) . . . . ?
C7 C1 C6 Bi1 -1.8(5) . . . . ?
C7 C1 C6 C5 178.9(3) . . . . ?
C8 N1 C7 C1 87.9(4) . . . . ?
C8 N1 C14 C15 -166.9(3) . . . . ?
C8 C9 C10 C11 -0.8(7) . . . . ?
C9 C8 C13 C12 0.6(6) . . . . ?
C9 C10 C11 C12 0.5(7) . . . . ?
C10 C11 C12 C13 0.5(7) . . . . ?
C11 C12 C13 C8 -1.0(7) . . . . ?
C13 C8 C9 C10 0.3(6) . . . . ?
C14 N1 C7 C1 -135.2(3) . . . . ?
C14 N1 C8 C9 -170.0(4) . . . . ?
C14 N1 C8 C13 10.7(5) . . . . ?
C14 C15 C16 Bi1 -2.7(5) . . . . ?
C14 C15 C16 C17 177.3(3) . . . . ?
C14 C15 C20 C19 -177.8(4) . . . . ?
C15 C16 C17 C18 1.5(6) . . . . ?
C16 C15 C20 C19 0.7(6) . . . . ?
C16 C17 C18 C19 -1.2(7) . . . . ?
C17 C18 C19 C20 0.6(8) . . . . ?
C18 C19 C20 C15 -0.4(8) . . . . ?
C20 C15 C16 Bi1 178.8(3) . . . . ?
C20 C15 C16 C17 -1.2(6) . . . . ?
C21 C22 C23 C24 0.4(7) . . . . ?
C22 C21 C26 C25 -1.5(7) . . . . ?
C22 C23 C24 Cl1 179.0(3) . . . . ?
C22 C23 C24 C25 -0.2(7) . . . . ?
C23 C24 C25 C26 -0.9(7) . . . . ?
C24 C25 C26 C21 1.7(8) . . . . ?
C26 C21 C22 C23 0.4(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 1.482
_oxdiff_exptl_absorpt_empirical_full_min 0.822
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xray4
_audit_block_doi                 10.5517/ccdc.csd.cc274jc9
_database_code_depnum_ccdc_archive 'CCDC 2059930'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D1OB00959A 2021
2 10.1039/D4OB00702F 2024
loop_
_audit_author_name
_audit_author_address
'Jian Lei'
;Gannan Medical University
China
;
_audit_update_record             
;
2021-01-31 deposited with the CCDC.	2024-08-15 downloaded from the CCDC.
;
# This entry has been retracted
_audit_creation_date             2021-01-28
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H28 N S Sb'
_chemical_formula_sum            'C26 H28 N S Sb'
_chemical_formula_weight         508.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.7657(6)
_cell_length_b                   19.2142(13)
_cell_length_c                   13.3556(9)
_cell_angle_alpha                90
_cell_angle_beta                 101.451(7)
_cell_angle_gamma                90
_cell_volume                     2204.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3416
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.0860
_cell_measurement_theta_min      2.6220
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.359
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0783
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9478
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.991
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_min         1.882
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  21.00   1.00    5.60    --   11.90  38.00 120.00   32
  2  ω     57.00  84.00   1.00    5.60    --   11.90  38.00 120.00   27
  3  ω    -13.00  30.00   1.00    5.60    --  -11.27 -99.00  30.00   43
  4  ω    -61.00  44.00   1.00    5.60    --   11.90 -77.00-180.00  105
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0147471000
_diffrn_orient_matrix_UB_12      -0.0204360000
_diffrn_orient_matrix_UB_13      0.0450546000
_diffrn_orient_matrix_UB_21      0.0250495000
_diffrn_orient_matrix_UB_22      0.0302082000
_diffrn_orient_matrix_UB_23      0.0292231000
_diffrn_orient_matrix_UB_31      -0.0772975000
_diffrn_orient_matrix_UB_32      0.0059292000
_diffrn_orient_matrix_UB_33      0.0066320000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3135
_reflns_number_total             3884
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.097
_refine_diff_density_min         -0.887
_refine_diff_density_rms         0.133
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3884
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0304P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0939
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
3.a Ternary CH refined with riding coordinates:
 C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B),
 C13(H13A,H13B), C14(H14A,H14B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C16(H16), C17(H17), C18(H18), C19(H19),
 C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb1 Sb 0.61024(3) 0.63314(2) 0.51291(2) 0.01421(12) Uani 1 1 d . . . . .
S1 S 0.53290(13) 0.59864(7) 0.32636(9) 0.0215(3) Uani 1 1 d . . . . .
N1 N 0.6244(4) 0.69684(19) 0.6776(3) 0.0131(8) Uani 1 1 d . . . . .
C1 C 0.6615(5) 0.7394(2) 0.4815(3) 0.0134(10) Uani 1 1 d . U . . .
C2 C 0.6419(5) 0.7682(3) 0.3836(4) 0.0202(11) Uani 1 1 d . . . . .
H2 H 0.607141 0.740373 0.326716 0.024 Uiso 1 1 calc R U . . .
C3 C 0.6740(5) 0.8381(3) 0.3707(4) 0.0265(12) Uani 1 1 d . . . . .
H3 H 0.660544 0.856751 0.305274 0.032 Uiso 1 1 calc R U . . .
C4 C 0.7260(6) 0.8800(3) 0.4548(4) 0.0284(13) Uani 1 1 d . . . . .
H4 H 0.745346 0.927014 0.445989 0.034 Uiso 1 1 calc R U . . .
C5 C 0.7493(5) 0.8518(3) 0.5525(4) 0.0238(12) Uani 1 1 d . . . . .
H5 H 0.786994 0.879563 0.609015 0.029 Uiso 1 1 calc R U . . .
C6 C 0.7159(5) 0.7816(3) 0.5656(3) 0.0175(11) Uani 1 1 d . . . . .
C7 C 0.7440(5) 0.7505(2) 0.6710(3) 0.0182(11) Uani 1 1 d . . . . .
H7A H 0.846737 0.729639 0.686494 0.022 Uiso 1 1 calc R U . . .
H7B H 0.739882 0.786856 0.720898 0.022 Uiso 1 1 calc R U . . .
C8 C 0.6733(5) 0.6484(2) 0.7644(3) 0.0148(10) Uani 1 1 d . . . . .
H8 H 0.765783 0.624024 0.751766 0.018 Uiso 1 1 calc R U . . .
C9 C 0.7206(5) 0.6841(2) 0.8680(3) 0.0185(11) Uani 1 1 d . . . . .
H9A H 0.803855 0.716940 0.865583 0.022 Uiso 1 1 calc R U . . .
H9B H 0.632640 0.709889 0.883033 0.022 Uiso 1 1 calc R U . . .
C10 C 0.7745(5) 0.6316(2) 0.9518(3) 0.0203(11) Uani 1 1 d . . . . .
H10A H 0.801356 0.655520 1.016916 0.024 Uiso 1 1 calc R U . . .
H10B H 0.867158 0.608280 0.939478 0.024 Uiso 1 1 calc R U . . .
C11 C 0.6488(5) 0.5778(3) 0.9569(3) 0.0234(12) Uani 1 1 d . . . . .
H11A H 0.687167 0.543897 1.009716 0.028 Uiso 1 1 calc R U . . .
H11B H 0.558266 0.600403 0.973755 0.028 Uiso 1 1 calc R U . . .
C12 C 0.6038(6) 0.5414(3) 0.8543(3) 0.0232(12) Uani 1 1 d . . . . .
H12A H 0.520828 0.508506 0.856920 0.028 Uiso 1 1 calc R U . . .
H12B H 0.692600 0.515588 0.840739 0.028 Uiso 1 1 calc R U . . .
C13 C 0.5503(5) 0.5929(2) 0.7682(3) 0.0177(11) Uani 1 1 d . . . . .
H13A H 0.454796 0.615084 0.777737 0.021 Uiso 1 1 calc R U . . .
H13B H 0.528286 0.568135 0.703595 0.021 Uiso 1 1 calc R U . . .
C14 C 0.4700(5) 0.7308(2) 0.6743(3) 0.0149(10) Uani 1 1 d . . . . .
H14A H 0.477380 0.779636 0.657724 0.018 Uiso 1 1 calc R U . . .
H14B H 0.443599 0.727798 0.741358 0.018 Uiso 1 1 calc R U . . .
C15 C 0.3417(5) 0.6974(2) 0.5966(3) 0.0150(10) Uani 1 1 d . . . . .
C16 C 0.1885(5) 0.7152(3) 0.6008(3) 0.0192(11) Uani 1 1 d . . . . .
H16 H 0.168788 0.743816 0.652907 0.023 Uiso 1 1 calc R U . . .
C17 C 0.0659(5) 0.6903(3) 0.5277(3) 0.0231(12) Uani 1 1 d . . . . .
H17 H -0.035710 0.703254 0.529626 0.028 Uiso 1 1 calc R U . . .
C18 C 0.0951(5) 0.6464(3) 0.4523(3) 0.0199(11) Uani 1 1 d . . . . .
H18 H 0.012952 0.628872 0.403908 0.024 Uiso 1 1 calc R U . . .
C19 C 0.2460(5) 0.6282(2) 0.4486(3) 0.0152(10) Uani 1 1 d . . . . .
H19 H 0.264660 0.597985 0.398039 0.018 Uiso 1 1 calc R U . . .
C20 C 0.3709(5) 0.6546(2) 0.5195(3) 0.0145(10) Uani 1 1 d . . . . .
C21 C 0.7146(5) 0.5633(2) 0.3080(3) 0.0175(11) Uani 1 1 d . . . . .
C22 C 0.7886(5) 0.5106(2) 0.3686(4) 0.0223(11) Uani 1 1 d . . . . .
H22 H 0.745710 0.493433 0.421954 0.027 Uiso 1 1 calc R U . . .
C23 C 0.9266(6) 0.4829(3) 0.3506(4) 0.0268(12) Uani 1 1 d . . . . .
H23 H 0.976008 0.447341 0.391978 0.032 Uiso 1 1 calc R U . . .
C24 C 0.9910(6) 0.5082(3) 0.2711(4) 0.0290(13) Uani 1 1 d . . . . .
H24 H 1.084665 0.490362 0.259578 0.035 Uiso 1 1 calc R U . . .
C25 C 0.9152(6) 0.5597(3) 0.2095(4) 0.0265(12) Uani 1 1 d . . . . .
H25 H 0.955944 0.575792 0.154580 0.032 Uiso 1 1 calc R U . . .
C26 C 0.7791(5) 0.5877(3) 0.2283(3) 0.0227(11) Uani 1 1 d . . . . .
H26 H 0.730097 0.623446 0.187052 0.027 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sb1 S1 2.5369(12) . ?
Sb1 N1 2.499(3) . ?
Sb1 C1 2.150(5) . ?
Sb1 C20 2.157(4) . ?
S1 C21 1.792(4) . ?
N1 C7 1.486(5) . ?
N1 C8 1.482(5) . ?
N1 C14 1.495(5) . ?
C1 C2 1.398(6) . ?
C1 C6 1.390(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.390(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.399(7) . ?
C6 C7 1.504(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8 0.9800 . ?
C8 C9 1.527(6) . ?
C8 C13 1.524(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.511(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.522(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.518(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.519(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.512(6) . ?
C15 C16 1.397(6) . ?
C15 C20 1.382(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.386(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.377(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.378(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.393(6) . ?
C21 C22 1.376(7) . ?
C21 C26 1.383(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.385(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.386(7) . ?
C24 H24 0.9300 . ?
C24 C25 1.372(7) . ?
C25 H25 0.9300 . ?
C25 C26 1.377(6) . ?
C26 H26 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Sb1 S1 161.70(9) . . ?
C1 Sb1 S1 94.72(12) . . ?
C1 Sb1 N1 74.37(14) . . ?
C1 Sb1 C20 93.95(16) . . ?
C20 Sb1 S1 91.01(12) . . ?
C20 Sb1 N1 75.47(14) . . ?
C21 S1 Sb1 99.31(14) . . ?
C7 N1 Sb1 101.6(2) . . ?
C7 N1 C14 109.9(3) . . ?
C8 N1 Sb1 109.7(3) . . ?
C8 N1 C7 112.6(3) . . ?
C8 N1 C14 114.6(3) . . ?
C14 N1 Sb1 107.5(2) . . ?
C2 C1 Sb1 124.5(3) . . ?
C6 C1 Sb1 116.6(3) . . ?
C6 C1 C2 118.9(4) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.5(5) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.3(5) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.8(5) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 119.9(5) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 120.5(4) . . ?
C1 C6 C7 119.5(4) . . ?
C5 C6 C7 120.0(4) . . ?
N1 C7 C6 110.1(4) . . ?
N1 C7 H7A 109.6 . . ?
N1 C7 H7B 109.6 . . ?
C6 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
N1 C8 H8 106.6 . . ?
N1 C8 C9 114.3(4) . . ?
N1 C8 C13 111.6(4) . . ?
C9 C8 H8 106.6 . . ?
C13 C8 H8 106.6 . . ?
C13 C8 C9 110.6(4) . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 C8 111.1(4) . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
C9 C10 C11 111.3(4) . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C10 C11 H11A 109.8 . . ?
C10 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
C12 C11 C10 109.5(4) . . ?
C12 C11 H11A 109.8 . . ?
C12 C11 H11B 109.8 . . ?
C11 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C11 C12 C13 111.7(4) . . ?
H12A C12 H12B 107.9 . . ?
C13 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C8 C13 H13A 109.3 . . ?
C8 C13 H13B 109.3 . . ?
C12 C13 C8 111.5(4) . . ?
C12 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
N1 C14 H14A 109.1 . . ?
N1 C14 H14B 109.1 . . ?
N1 C14 C15 112.4(4) . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C16 C15 C14 117.3(4) . . ?
C20 C15 C14 122.8(4) . . ?
C20 C15 C16 119.8(4) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.3(4) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.7(4) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.0(4) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.5 . . ?
C18 C19 C20 120.9(4) . . ?
C20 C19 H19 119.5 . . ?
C15 C20 Sb1 118.0(3) . . ?
C15 C20 C19 119.1(4) . . ?
C19 C20 Sb1 122.9(3) . . ?
C22 C21 S1 121.8(4) . . ?
C22 C21 C26 119.0(4) . . ?
C26 C21 S1 119.2(4) . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120.5(4) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 120.1(5) . . ?
C24 C23 H23 120.0 . . ?
C23 C24 H24 120.3 . . ?
C25 C24 C23 119.3(4) . . ?
C25 C24 H24 120.3 . . ?
C24 C25 H25 119.8 . . ?
C24 C25 C26 120.5(5) . . ?
C26 C25 H25 119.8 . . ?
C21 C26 H26 119.7 . . ?
C25 C26 C21 120.6(5) . . ?
C25 C26 H26 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Sb1 S1 C21 C22 55.7(4) . . . . ?
Sb1 S1 C21 C26 -127.0(3) . . . . ?
Sb1 N1 C7 C6 43.3(4) . . . . ?
Sb1 N1 C8 C9 167.1(3) . . . . ?
Sb1 N1 C8 C13 -66.4(4) . . . . ?
Sb1 N1 C14 C15 20.4(4) . . . . ?
Sb1 C1 C2 C3 178.2(3) . . . . ?
Sb1 C1 C6 C5 -178.7(3) . . . . ?
Sb1 C1 C6 C7 3.4(5) . . . . ?
S1 C21 C22 C23 178.0(4) . . . . ?
S1 C21 C26 C25 -177.3(4) . . . . ?
N1 C8 C9 C10 -177.9(3) . . . . ?
N1 C8 C13 C12 177.4(3) . . . . ?
N1 C14 C15 C16 167.5(4) . . . . ?
N1 C14 C15 C20 -16.7(6) . . . . ?
C1 C2 C3 C4 0.1(7) . . . . ?
C1 C6 C7 N1 -36.3(5) . . . . ?
C2 C1 C6 C5 0.5(6) . . . . ?
C2 C1 C6 C7 -177.4(4) . . . . ?
C2 C3 C4 C5 1.3(7) . . . . ?
C3 C4 C5 C6 -1.8(7) . . . . ?
C4 C5 C6 C1 0.9(7) . . . . ?
C4 C5 C6 C7 178.8(4) . . . . ?
C5 C6 C7 N1 145.8(4) . . . . ?
C6 C1 C2 C3 -1.0(6) . . . . ?
C7 N1 C8 C9 54.8(5) . . . . ?
C7 N1 C8 C13 -178.7(4) . . . . ?
C7 N1 C14 C15 130.2(4) . . . . ?
C8 N1 C7 C6 160.6(4) . . . . ?
C8 N1 C14 C15 -101.8(4) . . . . ?
C8 C9 C10 C11 -57.6(5) . . . . ?
C9 C8 C13 C12 -54.1(5) . . . . ?
C9 C10 C11 C12 57.7(5) . . . . ?
C10 C11 C12 C13 -56.7(5) . . . . ?
C11 C12 C13 C8 55.8(5) . . . . ?
C13 C8 C9 C10 55.2(5) . . . . ?
C14 N1 C7 C6 -70.4(4) . . . . ?
C14 N1 C8 C9 -71.8(5) . . . . ?
C14 N1 C8 C13 54.6(5) . . . . ?
C14 C15 C16 C17 175.6(4) . . . . ?
C14 C15 C20 Sb1 1.4(6) . . . . ?
C14 C15 C20 C19 -177.5(4) . . . . ?
C15 C16 C17 C18 1.8(7) . . . . ?
C16 C15 C20 Sb1 177.1(3) . . . . ?
C16 C15 C20 C19 -1.8(7) . . . . ?
C16 C17 C18 C19 -1.2(7) . . . . ?
C17 C18 C19 C20 -0.9(7) . . . . ?
C18 C19 C20 Sb1 -176.4(3) . . . . ?
C18 C19 C20 C15 2.4(7) . . . . ?
C20 C15 C16 C17 -0.3(7) . . . . ?
C21 C22 C23 C24 -0.1(8) . . . . ?
C22 C21 C26 C25 0.2(7) . . . . ?
C22 C23 C24 C25 -1.3(8) . . . . ?
C23 C24 C25 C26 2.1(8) . . . . ?
C24 C25 C26 C21 -1.6(8) . . . . ?
C26 C21 C22 C23 0.7(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 1.567
_oxdiff_exptl_absorpt_empirical_full_min 0.602
####################################################################### 
# 
# 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_xray_3
_audit_block_doi                 10.5517/ccdc.csd.cc274jb8
_database_code_depnum_ccdc_archive 'CCDC 2059929'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D1OB00959A 2021
2 10.1039/D4OB00702F 2024
loop_
_audit_author_name
_audit_author_address
'Jian Lei'
;Gannan Medical University
China
;
_audit_update_record             
;
2021-01-31 deposited with the CCDC.	2024-08-15 downloaded from the CCDC.
;
# This entry has been retracted
_audit_creation_date             2021-01-28
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H30 N S Sb'
_chemical_formula_sum            'C30 H30 N S Sb'
_chemical_formula_weight         558.36
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.0684(5)
_cell_length_b                   16.7181(7)
_cell_length_c                   12.4529(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.279(4)
_cell_angle_gamma                90
_cell_volume                     2479.65(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6068
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      28.9950
_cell_measurement_theta_min      2.8110
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.216
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83328
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11697
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.057
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  14.00   1.00    1.50    --  -11.27 -99.00 120.00   34
  2  ω    -35.00  61.00   1.00    1.50    --  -11.27  57.00   0.00   96
  3  ω    -10.00  70.00   1.00    1.50    --   11.90  57.00 -90.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0374586000
_diffrn_orient_matrix_UB_12      -0.0325018000
_diffrn_orient_matrix_UB_13      -0.0134092000
_diffrn_orient_matrix_UB_21      -0.0371204000
_diffrn_orient_matrix_UB_22      0.0168338000
_diffrn_orient_matrix_UB_23      0.0324897000
_diffrn_orient_matrix_UB_31      -0.0275674000
_diffrn_orient_matrix_UB_32      0.0214560000
_diffrn_orient_matrix_UB_33      -0.0458524000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3783
_reflns_number_total             4374
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4374
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0270
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0210P)²+0.4181P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0546
_refine_ls_wR_factor_ref         0.0585
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C16(H16), C17(H17), C18(H18), C19(H19), C22(H22), C23(H23), C25(H25),
  C26(H26)
2.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb1 Sb 0.48423(2) 0.62174(2) 0.38799(2) 0.01595(7) Uani 1 1 d . . . . .
S1 S 0.28478(6) 0.62981(4) 0.29305(6) 0.02358(18) Uani 1 1 d . . . . .
N1 N 0.65910(17) 0.66858(13) 0.52682(17) 0.0175(5) Uani 1 1 d . . . . .
C1 C 0.4935(3) 0.62270(16) 0.7437(2) 0.0280(7) Uani 1 1 d . . . . .
H1 H 0.550260 0.620500 0.803761 0.034 Uiso 1 1 calc R U . . .
C2 C 0.3835(3) 0.62274(17) 0.7584(2) 0.0327(8) Uani 1 1 d . . . . .
H2 H 0.365863 0.620068 0.828267 0.039 Uiso 1 1 calc R U . . .
C3 C 0.2990(3) 0.62674(17) 0.6700(3) 0.0308(8) Uani 1 1 d . . . . .
H3 H 0.224344 0.627778 0.680307 0.037 Uiso 1 1 calc R U . . .
C4 C 0.3249(2) 0.62920(16) 0.5656(2) 0.0239(7) Uani 1 1 d . . . . .
H4 H 0.267244 0.631511 0.506394 0.029 Uiso 1 1 calc R U . . .
C5 C 0.4358(2) 0.62828(15) 0.5481(2) 0.0183(6) Uani 1 1 d . . . . .
C6 C 0.5208(2) 0.62591(16) 0.6397(2) 0.0226(7) Uani 1 1 d . . . . .
C7 C 0.6428(2) 0.62463(16) 0.6258(2) 0.0242(7) Uani 1 1 d . . . . .
H7A H 0.688049 0.648900 0.688850 0.029 Uiso 1 1 calc R U . . .
H7B H 0.667278 0.569702 0.620787 0.029 Uiso 1 1 calc R U . . .
C8 C 0.7600(2) 0.64884(16) 0.4848(2) 0.0193(6) Uani 1 1 d . . . . .
C9 C 0.7873(2) 0.56791(17) 0.4730(2) 0.0231(7) Uani 1 1 d . . . . .
H9 H 0.740601 0.528166 0.492737 0.028 Uiso 1 1 calc R U . . .
C10 C 0.8830(2) 0.54714(18) 0.4322(2) 0.0273(7) Uani 1 1 d . . . . .
H10 H 0.900762 0.493397 0.425804 0.033 Uiso 1 1 calc R U . . .
C11 C 0.9528(2) 0.60486(19) 0.4008(2) 0.0284(7) Uani 1 1 d . . . . .
H11 H 1.018025 0.590496 0.374736 0.034 Uiso 1 1 calc R U . . .
C12 C 0.9241(2) 0.68445(18) 0.4086(2) 0.0274(7) Uani 1 1 d . . . . .
H12 H 0.969581 0.723705 0.385489 0.033 Uiso 1 1 calc R U . . .
C13 C 0.8290(2) 0.70680(16) 0.4501(2) 0.0218(7) Uani 1 1 d . . . . .
H13 H 0.811199 0.760677 0.454808 0.026 Uiso 1 1 calc R U . . .
C14 C 0.6365(2) 0.75470(15) 0.5372(2) 0.0187(6) Uani 1 1 d . . . . .
H14A H 0.705971 0.782027 0.565674 0.022 Uiso 1 1 calc R U . . .
H14B H 0.584813 0.762175 0.588454 0.022 Uiso 1 1 calc R U . . .
C15 C 0.5870(2) 0.79104(15) 0.4290(2) 0.0147(6) Uani 1 1 d . . . . .
C16 C 0.6093(2) 0.87036(15) 0.4056(2) 0.0193(6) Uani 1 1 d . . . . .
H16 H 0.656688 0.900641 0.456217 0.023 Uiso 1 1 calc R U . . .
C17 C 0.5616(2) 0.90461(16) 0.3078(2) 0.0211(6) Uani 1 1 d . . . . .
H17 H 0.576551 0.957691 0.293052 0.025 Uiso 1 1 calc R U . . .
C18 C 0.4912(2) 0.85930(17) 0.2318(2) 0.0215(6) Uani 1 1 d . . . . .
H18 H 0.460710 0.881404 0.165008 0.026 Uiso 1 1 calc R U . . .
C19 C 0.4666(2) 0.78120(16) 0.2560(2) 0.0188(6) Uani 1 1 d . . . . .
H19 H 0.418194 0.751478 0.205575 0.023 Uiso 1 1 calc R U . . .
C20 C 0.5131(2) 0.74622(15) 0.3545(2) 0.0149(6) Uani 1 1 d . . . . .
C21 C 0.2829(2) 0.55846(16) 0.1875(2) 0.0189(6) Uani 1 1 d . . . . .
C22 C 0.3579(2) 0.55957(16) 0.1139(2) 0.0202(6) Uani 1 1 d . . . . .
H22 H 0.413988 0.598228 0.120473 0.024 Uiso 1 1 calc R U . . .
C23 C 0.3501(2) 0.50357(16) 0.0305(2) 0.0213(6) Uani 1 1 d . . . . .
H23 H 0.401708 0.505511 -0.017392 0.026 Uiso 1 1 calc R U . . .
C24 C 0.2670(2) 0.44436(16) 0.0165(2) 0.0186(6) Uani 1 1 d . . . . .
C25 C 0.1923(2) 0.44486(17) 0.0902(2) 0.0230(7) Uani 1 1 d . . . . .
H25 H 0.135510 0.406739 0.083423 0.028 Uiso 1 1 calc R U . . .
C26 C 0.1998(2) 0.50069(16) 0.1741(2) 0.0224(6) Uani 1 1 d . . . . .
H26 H 0.147968 0.499101 0.221888 0.027 Uiso 1 1 calc R U . . .
C27 C 0.2632(2) 0.38051(16) -0.0724(2) 0.0212(7) Uani 1 1 d . . . . .
C28 C 0.3485(2) 0.31386(17) -0.0291(2) 0.0313(8) Uani 1 1 d . . . . .
H28A H 0.421883 0.336854 -0.009615 0.047 Uiso 1 1 calc R U . . .
H28B H 0.350121 0.274314 -0.084761 0.047 Uiso 1 1 calc R U . . .
H28C H 0.326246 0.289223 0.033679 0.047 Uiso 1 1 calc R U . . .
C29 C 0.2968(2) 0.41535(19) -0.1759(2) 0.0275(7) Uani 1 1 d . . . . .
H29A H 0.246883 0.458369 -0.201880 0.041 Uiso 1 1 calc R U . . .
H29B H 0.292191 0.374438 -0.230489 0.041 Uiso 1 1 calc R U . . .
H29C H 0.372315 0.435161 -0.160268 0.041 Uiso 1 1 calc R U . . .
C30 C 0.1456(2) 0.34380(18) -0.0995(2) 0.0283(7) Uani 1 1 d . . . . .
H30A H 0.127101 0.317334 -0.036277 0.043 Uiso 1 1 calc R U . . .
H30B H 0.144247 0.305776 -0.157445 0.043 Uiso 1 1 calc R U . . .
H30C H 0.091781 0.385297 -0.121681 0.043 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sb1 S1 2.5084(7) . ?
Sb1 C5 2.169(3) . ?
Sb1 C20 2.162(3) . ?
S1 C21 1.772(3) . ?
N1 C7 1.475(3) . ?
N1 C8 1.439(3) . ?
N1 C14 1.475(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.368(4) . ?
C1 C6 1.388(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.390(4) . ?
C5 C6 1.407(4) . ?
C6 C7 1.510(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.406(4) . ?
C8 C13 1.391(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.379(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.378(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.382(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.384(4) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.510(3) . ?
C15 C16 1.393(4) . ?
C15 C20 1.397(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.384(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.390(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.383(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.392(3) . ?
C21 C22 1.388(4) . ?
C21 C26 1.383(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.390(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.400(4) . ?
C24 C25 1.387(4) . ?
C24 C27 1.533(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.393(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.553(4) . ?
C27 C29 1.527(4) . ?
C27 C30 1.533(4) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 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
C5 Sb1 S1 92.87(7) . . ?
C20 Sb1 S1 91.71(6) . . ?
C20 Sb1 C5 101.81(9) . . ?
C21 S1 Sb1 102.11(9) . . ?
C8 N1 C7 115.1(2) . . ?
C8 N1 C14 115.8(2) . . ?
C14 N1 C7 111.2(2) . . ?
C2 C1 H1 119.8 . . ?
C2 C1 C6 120.4(3) . . ?
C6 C1 H1 119.8 . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.1(3) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 Sb1 123.7(2) . . ?
C4 C5 C6 117.8(3) . . ?
C6 C5 Sb1 118.4(2) . . ?
C1 C6 C5 120.4(3) . . ?
C1 C6 C7 119.3(2) . . ?
C5 C6 C7 120.3(3) . . ?
N1 C7 C6 110.7(2) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C9 C8 N1 119.1(3) . . ?
C13 C8 N1 122.5(2) . . ?
C13 C8 C9 118.4(3) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.4(3) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.0(3) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.6 . . ?
C10 C11 C12 118.9(3) . . ?
C12 C11 H11 120.6 . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C13 121.2(3) . . ?
C13 C12 H12 119.4 . . ?
C8 C13 H13 119.9 . . ?
C12 C13 C8 120.1(3) . . ?
C12 C13 H13 119.9 . . ?
N1 C14 H14A 109.3 . . ?
N1 C14 H14B 109.3 . . ?
N1 C14 C15 111.5(2) . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C16 C15 C14 120.5(2) . . ?
C16 C15 C20 119.7(2) . . ?
C20 C15 C14 119.7(2) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.7(2) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.7(3) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.7(2) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.4 . . ?
C18 C19 C20 121.2(2) . . ?
C20 C19 H19 119.4 . . ?
C15 C20 Sb1 119.59(17) . . ?
C19 C20 Sb1 121.31(18) . . ?
C19 C20 C15 118.9(2) . . ?
C22 C21 S1 123.3(2) . . ?
C26 C21 S1 118.8(2) . . ?
C26 C21 C22 117.8(3) . . ?
C21 C22 H22 119.6 . . ?
C21 C22 C23 120.8(3) . . ?
C23 C22 H22 119.6 . . ?
C22 C23 H23 119.0 . . ?
C22 C23 C24 122.1(3) . . ?
C24 C23 H23 119.0 . . ?
C23 C24 C27 121.4(3) . . ?
C25 C24 C23 116.2(3) . . ?
C25 C24 C27 122.3(2) . . ?
C24 C25 H25 119.0 . . ?
C24 C25 C26 122.1(3) . . ?
C26 C25 H25 119.0 . . ?
C21 C26 C25 121.1(3) . . ?
C21 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C24 C27 C28 107.9(2) . . ?
C24 C27 C30 110.9(2) . . ?
C29 C27 C24 111.2(2) . . ?
C29 C27 C28 108.4(2) . . ?
C29 C27 C30 109.2(2) . . ?
C30 C27 C28 109.1(2) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Sb1 S1 C21 C22 -53.9(2) . . . . ?
Sb1 S1 C21 C26 129.13(19) . . . . ?
Sb1 C5 C6 C1 -174.2(2) . . . . ?
Sb1 C5 C6 C7 4.2(3) . . . . ?
S1 C21 C22 C23 -177.86(19) . . . . ?
S1 C21 C26 C25 177.9(2) . . . . ?
N1 C8 C9 C10 179.5(2) . . . . ?
N1 C8 C13 C12 -178.9(2) . . . . ?
N1 C14 C15 C16 -148.1(2) . . . . ?
N1 C14 C15 C20 35.7(3) . . . . ?
C1 C2 C3 C4 1.2(4) . . . . ?
C1 C6 C7 N1 -150.5(2) . . . . ?
C2 C1 C6 C5 -0.8(4) . . . . ?
C2 C1 C6 C7 -179.2(3) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C3 C4 C5 Sb1 174.6(2) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
C4 C5 C6 C1 1.5(4) . . . . ?
C4 C5 C6 C7 179.9(2) . . . . ?
C5 C6 C7 N1 31.1(4) . . . . ?
C6 C1 C2 C3 -0.6(4) . . . . ?
C7 N1 C8 C9 47.8(3) . . . . ?
C7 N1 C8 C13 -135.6(2) . . . . ?
C7 N1 C14 C15 -146.8(2) . . . . ?
C8 N1 C7 C6 -159.4(2) . . . . ?
C8 N1 C14 C15 79.3(3) . . . . ?
C8 C9 C10 C11 -1.0(4) . . . . ?
C9 C8 C13 C12 -2.2(4) . . . . ?
C9 C10 C11 C12 -1.3(4) . . . . ?
C10 C11 C12 C13 1.9(4) . . . . ?
C11 C12 C13 C8 -0.1(4) . . . . ?
C13 C8 C9 C10 2.8(4) . . . . ?
C14 N1 C7 C6 66.5(3) . . . . ?
C14 N1 C8 C9 179.8(2) . . . . ?
C14 N1 C8 C13 -3.6(3) . . . . ?
C14 C15 C16 C17 -178.2(2) . . . . ?
C14 C15 C20 Sb1 -6.3(3) . . . . ?
C14 C15 C20 C19 178.8(2) . . . . ?
C15 C16 C17 C18 -0.4(4) . . . . ?
C16 C15 C20 Sb1 177.42(19) . . . . ?
C16 C15 C20 C19 2.5(4) . . . . ?
C16 C17 C18 C19 2.0(4) . . . . ?
C17 C18 C19 C20 -1.4(4) . . . . ?
C18 C19 C20 Sb1 -175.7(2) . . . . ?
C18 C19 C20 C15 -0.9(4) . . . . ?
C20 C15 C16 C17 -1.9(4) . . . . ?
C21 C22 C23 C24 0.4(4) . . . . ?
C22 C21 C26 C25 0.7(4) . . . . ?
C22 C23 C24 C25 0.3(4) . . . . ?
C22 C23 C24 C27 -176.9(2) . . . . ?
C23 C24 C25 C26 -0.4(4) . . . . ?
C23 C24 C27 C28 81.7(3) . . . . ?
C23 C24 C27 C29 -37.1(3) . . . . ?
C23 C24 C27 C30 -158.8(2) . . . . ?
C24 C25 C26 C21 -0.1(4) . . . . ?
C25 C24 C27 C28 -95.4(3) . . . . ?
C25 C24 C27 C29 145.9(3) . . . . ?
C25 C24 C27 C30 24.1(3) . . . . ?
C26 C21 C22 C23 -0.9(4) . . . . ?
C27 C24 C25 C26 176.7(2) . . . . ?

_olex2_date_sample_data_collection 2021-01-28
_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 1.331
_oxdiff_exptl_absorpt_empirical_full_min 0.782
####################################################################### 
# 
# 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_xray-1
_audit_block_doi                 10.5517/ccdc.csd.cc274j97
_database_code_depnum_ccdc_archive 'CCDC 2059928'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D1OB00959A 2021
2 10.1039/D4OB00702F 2024
loop_
_audit_author_name
_audit_author_address
'Jian Lei'
;Gannan Medical University
China
;
_audit_update_record             
;
2021-01-31 deposited with the CCDC.	2024-08-15 downloaded from the CCDC.
;
# This entry has been retracted
_audit_creation_date             2021-01-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H24 N S Sb'
_chemical_formula_sum            'C27 H24 N S Sb'
_chemical_formula_weight         516.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.9614(5)
_cell_length_b                   15.2361(7)
_cell_length_c                   12.3334(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.953(4)
_cell_angle_gamma                90
_cell_volume                     2244.73(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4828
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.6570
_cell_measurement_theta_min      2.6720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.336
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73268
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10124
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.991
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_min         2.126
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  48.00   1.00    1.20    --   11.90   0.00-180.00  112
  2  ω     -1.00  87.00   1.00    1.20    --   11.90  19.00-150.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0362525000
_diffrn_orient_matrix_UB_12      0.0368361000
_diffrn_orient_matrix_UB_13      0.0047211000
_diffrn_orient_matrix_UB_21      0.0091152000
_diffrn_orient_matrix_UB_22      -0.0025900000
_diffrn_orient_matrix_UB_23      -0.0562447000
_diffrn_orient_matrix_UB_31      -0.0461288000
_diffrn_orient_matrix_UB_32      0.0283955000
_diffrn_orient_matrix_UB_33      -0.0112784000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3319
_reflns_number_total             3947
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.673
_refine_diff_density_min         -0.607
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3947
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0310
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0211P)²+1.0604P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0608
_refine_ls_wR_factor_ref         0.0665
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C25(H25),
  C26(H26)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb1 Sb 0.50055(2) 0.66191(2) 0.68292(2) 0.02182(9) Uani 1 1 d . . . . .
S1 S 0.32581(8) 0.68412(6) 0.78224(8) 0.0349(2) Uani 1 1 d . . . . .
N1 N 0.6412(2) 0.68455(16) 0.5323(2) 0.0207(6) Uani 1 1 d . . . . .
C1 C 0.4807(3) 0.6084(2) 0.4421(3) 0.0229(8) Uani 1 1 d . . . . .
C2 C 0.4150(2) 0.6289(2) 0.5288(3) 0.0210(7) Uani 1 1 d . . . . .
C3 C 0.2991(3) 0.6208(2) 0.5148(3) 0.0278(8) Uani 1 1 d . . . . .
H3 H 0.254052 0.634750 0.571526 0.033 Uiso 1 1 calc R U . . .
C4 C 0.2507(3) 0.5920(2) 0.4166(3) 0.0322(9) Uani 1 1 d . . . . .
H4 H 0.173214 0.587177 0.407942 0.039 Uiso 1 1 calc R U . . .
C5 C 0.3157(3) 0.5705(2) 0.3321(3) 0.0326(9) Uani 1 1 d . . . . .
H5 H 0.282749 0.550185 0.266861 0.039 Uiso 1 1 calc R U . . .
C6 C 0.4309(3) 0.5794(2) 0.3448(3) 0.0262(8) Uani 1 1 d . . . . .
H6 H 0.475287 0.565722 0.287364 0.031 Uiso 1 1 calc R U . . .
C7 C 0.6071(2) 0.6150(2) 0.4544(3) 0.0224(7) Uani 1 1 d . . . . .
H7A H 0.637827 0.559250 0.479502 0.027 Uiso 1 1 calc R U . . .
H7B H 0.636761 0.627811 0.384402 0.027 Uiso 1 1 calc R U . . .
C8 C 0.7576(3) 0.6805(2) 0.5706(3) 0.0213(7) Uani 1 1 d . . . . .
C9 C 0.8361(3) 0.6336(2) 0.5159(3) 0.0308(8) Uani 1 1 d . . . . .
H9 H 0.814643 0.603418 0.452681 0.037 Uiso 1 1 calc R U . . .
C10 C 0.9474(3) 0.6315(3) 0.5554(3) 0.0382(10) Uani 1 1 d . . . . .
H10 H 0.999601 0.599758 0.518153 0.046 Uiso 1 1 calc R U . . .
C11 C 0.9807(3) 0.6755(2) 0.6479(3) 0.0369(10) Uani 1 1 d . . . . .
H11 H 1.055097 0.674156 0.673662 0.044 Uiso 1 1 calc R U . . .
C12 C 0.9026(3) 0.7217(2) 0.7023(3) 0.0393(10) Uani 1 1 d . . . . .
H12 H 0.924564 0.751327 0.765806 0.047 Uiso 1 1 calc R U . . .
C13 C 0.7919(3) 0.7249(2) 0.6643(3) 0.0317(9) Uani 1 1 d . . . . .
H13 H 0.740284 0.757084 0.701893 0.038 Uiso 1 1 calc R U . . .
C14 C 0.6099(3) 0.7737(2) 0.4890(3) 0.0231(7) Uani 1 1 d . . . . .
H14A H 0.549449 0.767802 0.433922 0.028 Uiso 1 1 calc R U . . .
H14B H 0.673595 0.799120 0.454864 0.028 Uiso 1 1 calc R U . . .
C15 C 0.5736(3) 0.83438(19) 0.5767(3) 0.0211(7) Uani 1 1 d . . . . .
C16 C 0.5183(3) 0.8020(2) 0.6643(3) 0.0229(7) Uani 1 1 d . . . . .
C17 C 0.4859(3) 0.8597(2) 0.7444(3) 0.0280(8) Uani 1 1 d . . . . .
H17 H 0.450165 0.838354 0.804168 0.034 Uiso 1 1 calc R U . . .
C18 C 0.5068(3) 0.9490(2) 0.7354(3) 0.0346(9) Uani 1 1 d . . . . .
H18 H 0.484697 0.987263 0.788982 0.042 Uiso 1 1 calc R U . . .
C19 C 0.5596(3) 0.9808(2) 0.6479(3) 0.0330(9) Uani 1 1 d . . . . .
H19 H 0.573120 1.040694 0.641953 0.040 Uiso 1 1 calc R U . . .
C20 C 0.5928(3) 0.9242(2) 0.5684(3) 0.0284(8) Uani 1 1 d . . . . .
H20 H 0.628360 0.946186 0.508871 0.034 Uiso 1 1 calc R U . . .
C21 C 0.3275(3) 0.5827(2) 0.8540(3) 0.0270(8) Uani 1 1 d . . . . .
C22 C 0.3650(3) 0.5781(2) 0.9620(3) 0.0315(9) Uani 1 1 d . . . . .
H22 H 0.392416 0.628230 0.997121 0.038 Uiso 1 1 calc R U . . .
C23 C 0.3622(3) 0.5000(2) 1.0177(3) 0.0350(9) Uani 1 1 d . . . . .
H23 H 0.387531 0.498534 1.090245 0.042 Uiso 1 1 calc R U . . .
C24 C 0.3227(3) 0.4237(2) 0.9686(3) 0.0349(9) Uani 1 1 d . . . . .
C25 C 0.2861(3) 0.4285(3) 0.8613(3) 0.0411(10) Uani 1 1 d . . . . .
H25 H 0.259497 0.378110 0.826111 0.049 Uiso 1 1 calc R U . . .
C26 C 0.2881(3) 0.5067(2) 0.8045(3) 0.0373(9) Uani 1 1 d . . . . .
H26 H 0.262519 0.508040 0.732001 0.045 Uiso 1 1 calc R U . . .
C27 C 0.3187(4) 0.3381(2) 1.0304(4) 0.0556(12) Uani 1 1 d . . . . .
H27A H 0.268583 0.298200 0.992214 0.083 Uiso 1 1 calc R U . . .
H27B H 0.292689 0.348851 1.101567 0.083 Uiso 1 1 calc R U . . .
H27C H 0.392298 0.312855 1.036748 0.083 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sb1 S1 2.4995(9) . ?
Sb1 N1 2.592(3) . ?
Sb1 C2 2.171(3) . ?
Sb1 C16 2.158(3) . ?
S1 C21 1.780(3) . ?
N1 C7 1.474(4) . ?
N1 C8 1.449(4) . ?
N1 C14 1.500(4) . ?
C1 C2 1.394(4) . ?
C1 C6 1.385(4) . ?
C1 C7 1.515(4) . ?
C2 C3 1.394(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.372(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(4) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.382(5) . ?
C8 C13 1.384(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.393(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.365(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.372(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.383(4) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.504(4) . ?
C15 C16 1.386(5) . ?
C15 C20 1.392(4) . ?
C16 C17 1.392(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.389(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.367(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.380(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.385(5) . ?
C21 C26 1.382(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.374(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.383(5) . ?
C24 C25 1.375(5) . ?
C24 C27 1.513(5) . ?
C25 H25 0.9300 . ?
C25 C26 1.382(5) . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 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
S1 Sb1 N1 157.36(6) . . ?
C2 Sb1 S1 95.29(9) . . ?
C2 Sb1 N1 72.39(10) . . ?
C16 Sb1 S1 90.42(9) . . ?
C16 Sb1 N1 73.82(11) . . ?
C16 Sb1 C2 100.41(12) . . ?
C21 S1 Sb1 97.92(11) . . ?
C7 N1 Sb1 101.74(17) . . ?
C7 N1 C14 111.3(2) . . ?
C8 N1 Sb1 114.16(19) . . ?
C8 N1 C7 114.2(2) . . ?
C8 N1 C14 111.9(2) . . ?
C14 N1 Sb1 102.51(17) . . ?
C2 C1 C7 120.5(3) . . ?
C6 C1 C2 120.2(3) . . ?
C6 C1 C7 119.3(3) . . ?
C1 C2 Sb1 117.7(2) . . ?
C3 C2 Sb1 123.4(3) . . ?
C3 C2 C1 118.8(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.3(3) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C5 120.6(3) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
N1 C7 C1 110.7(3) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C9 C8 N1 122.0(3) . . ?
C9 C8 C13 118.7(3) . . ?
C13 C8 N1 119.3(3) . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.1(3) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.9(4) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.5 . . ?
C10 C11 C12 119.0(3) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C13 121.1(4) . . ?
C13 C12 H12 119.4 . . ?
C8 C13 H13 119.9 . . ?
C12 C13 C8 120.2(3) . . ?
C12 C13 H13 119.9 . . ?
N1 C14 H14A 109.2 . . ?
N1 C14 H14B 109.2 . . ?
N1 C14 C15 112.1(3) . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
C16 C15 C14 120.6(3) . . ?
C16 C15 C20 119.6(3) . . ?
C20 C15 C14 119.8(3) . . ?
C15 C16 Sb1 119.2(2) . . ?
C15 C16 C17 119.3(3) . . ?
C17 C16 Sb1 121.1(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.3(4) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.2(3) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 120.0(3) . . ?
C20 C19 H19 120.0 . . ?
C15 C20 H20 119.7 . . ?
C19 C20 C15 120.5(4) . . ?
C19 C20 H20 119.7 . . ?
C22 C21 S1 121.2(3) . . ?
C26 C21 S1 120.9(3) . . ?
C26 C21 C22 117.9(3) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 C21 120.7(3) . . ?
C23 C22 H22 119.7 . . ?
C22 C23 H23 119.2 . . ?
C22 C23 C24 121.7(3) . . ?
C24 C23 H23 119.2 . . ?
C23 C24 C27 121.5(4) . . ?
C25 C24 C23 117.5(3) . . ?
C25 C24 C27 121.0(4) . . ?
C24 C25 H25 119.3 . . ?
C24 C25 C26 121.4(4) . . ?
C26 C25 H25 119.3 . . ?
C21 C26 C25 120.9(3) . . ?
C21 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Sb1 S1 C21 C22 100.5(3) . . . . ?
Sb1 S1 C21 C26 -81.5(3) . . . . ?
Sb1 N1 C7 C1 41.1(3) . . . . ?
Sb1 N1 C8 C9 134.9(3) . . . . ?
Sb1 N1 C8 C13 -45.4(3) . . . . ?
Sb1 N1 C14 C15 35.5(3) . . . . ?
Sb1 C2 C3 C4 -174.3(2) . . . . ?
Sb1 C16 C17 C18 174.4(2) . . . . ?
S1 C21 C22 C23 177.7(3) . . . . ?
S1 C21 C26 C25 -177.9(3) . . . . ?
N1 C8 C9 C10 179.9(3) . . . . ?
N1 C8 C13 C12 179.9(3) . . . . ?
N1 C14 C15 C16 -32.8(4) . . . . ?
N1 C14 C15 C20 149.1(3) . . . . ?
C1 C2 C3 C4 0.6(5) . . . . ?
C2 C1 C6 C5 0.1(5) . . . . ?
C2 C1 C7 N1 -30.7(4) . . . . ?
C2 C3 C4 C5 0.4(5) . . . . ?
C3 C4 C5 C6 -1.2(5) . . . . ?
C4 C5 C6 C1 0.9(5) . . . . ?
C6 C1 C2 Sb1 174.3(2) . . . . ?
C6 C1 C2 C3 -0.9(5) . . . . ?
C6 C1 C7 N1 151.1(3) . . . . ?
C7 N1 C8 C9 18.3(4) . . . . ?
C7 N1 C8 C13 -161.9(3) . . . . ?
C7 N1 C14 C15 143.5(3) . . . . ?
C7 C1 C2 Sb1 -3.9(4) . . . . ?
C7 C1 C2 C3 -179.1(3) . . . . ?
C7 C1 C6 C5 178.3(3) . . . . ?
C8 N1 C7 C1 164.6(3) . . . . ?
C8 N1 C14 C15 -87.3(3) . . . . ?
C8 C9 C10 C11 -0.1(6) . . . . ?
C9 C8 C13 C12 -0.4(5) . . . . ?
C9 C10 C11 C12 0.4(6) . . . . ?
C10 C11 C12 C13 -0.6(6) . . . . ?
C11 C12 C13 C8 0.7(6) . . . . ?
C13 C8 C9 C10 0.1(5) . . . . ?
C14 N1 C7 C1 -67.5(3) . . . . ?
C14 N1 C8 C9 -109.3(3) . . . . ?
C14 N1 C8 C13 70.5(4) . . . . ?
C14 C15 C16 Sb1 6.7(4) . . . . ?
C14 C15 C16 C17 179.9(3) . . . . ?
C14 C15 C20 C19 179.6(3) . . . . ?
C15 C16 C17 C18 1.4(5) . . . . ?
C16 C15 C20 C19 1.5(5) . . . . ?
C16 C17 C18 C19 -0.2(5) . . . . ?
C17 C18 C19 C20 -0.3(5) . . . . ?
C18 C19 C20 C15 -0.4(5) . . . . ?
C20 C15 C16 Sb1 -175.2(2) . . . . ?
C20 C15 C16 C17 -2.0(4) . . . . ?
C21 C22 C23 C24 0.3(5) . . . . ?
C22 C21 C26 C25 0.1(5) . . . . ?
C22 C23 C24 C25 0.1(5) . . . . ?
C22 C23 C24 C27 -179.4(4) . . . . ?
C23 C24 C25 C26 -0.3(6) . . . . ?
C24 C25 C26 C21 0.3(6) . . . . ?
C26 C21 C22 C23 -0.4(5) . . . . ?
C27 C24 C25 C26 179.1(4) . . . . ?

_olex2_date_sample_data_collection 2021-01-25
_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 1.410
_oxdiff_exptl_absorpt_empirical_full_min 0.672
