# Electronic Supplementary Material (ESI) for ChemComm.
# 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 
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data_b220725c_0m
_database_code_depnum_ccdc_archive 'CCDC 2202373'
loop_
_audit_author_name
_audit_author_address
wang
;Suzhou university
China
;
_audit_update_record             
;
2022-08-19 deposited with the CCDC.	2024-04-08 downloaded from the CCDC.
;
_audit_creation_date             2022-07-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H18 N2 O S'
_chemical_formula_sum            'C23 H18 N2 O S'
_chemical_formula_weight         370.45
_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'
O O 0.0106 0.0060 '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'

_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                   8.2520(7)
_cell_length_b                   14.7387(13)
_cell_length_c                   15.4992(13)
_cell_angle_alpha                90
_cell_angle_beta                 96.548(3)
_cell_angle_gamma                90
_cell_volume                     1872.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6809
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.29
_cell_measurement_theta_min      2.65
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.946
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5561
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1643 before and 0.0744 after correction.
The Ratio of minimum to maximum transmission is 0.7458.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1125
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            37287
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.485
_diffrn_reflns_theta_min         2.646
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2237
_reflns_number_total             3469
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 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    ?
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3469
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0469
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0522P)²+0.0848P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1062
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C6(H6), C8(H8), C10(H10), C12(H12), C3(H3), C15(H15), C2(H2),
 C17(H17), C9(H9), C21(H21), C11(H11)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
S1 S 0.51551(7) 0.87647(4) 0.96906(4) 0.04475(19) Uani 1 1 d . . . . .
C1 C 0.5844(3) 0.95556(15) 0.81157(15) 0.0494(6) Uani 1 1 d . . . . .
H1 H 0.694067 0.939618 0.820996 0.059 Uiso 1 1 calc R U . . .
N2 N 0.2202(2) 0.93220(11) 0.92364(11) 0.0367(4) Uani 1 1 d . . . . .
C4 C -0.0793(3) 0.78387(16) 0.93167(14) 0.0513(6) Uani 1 1 d . . . . .
H4 H -0.027696 0.816483 0.891278 0.062 Uiso 1 1 calc R U . . .
C6 C 0.5229(3) 1.00008(16) 0.73744(16) 0.0579(7) Uani 1 1 d . . . . .
H6 H 0.591918 1.014494 0.696011 0.069 Uiso 1 1 calc R U . . .
C8 C 0.3600(3) 1.02398(15) 0.72310(15) 0.0546(6) Uani 1 1 d . . . . .
H8 H 0.321360 1.053928 0.672064 0.066 Uiso 1 1 calc R U . . .
C10 C 0.2813(3) 0.68697(15) 1.02297(14) 0.0498(6) Uani 1 1 d . . . . .
H10 H 0.237463 0.701369 0.966694 0.060 Uiso 1 1 calc R U . . .
C12 C 0.2539(3) 1.00425(14) 0.78300(13) 0.0453(6) Uani 1 1 d . . . . .
H12 H 0.144613 1.020773 0.773016 0.054 Uiso 1 1 calc R U . . .
C14 C -0.0461(2) 0.80177(14) 1.01919(13) 0.0383(5) Uani 1 1 d . . . . .
C16 C 0.3103(3) 0.88877(13) 0.98367(13) 0.0356(5) Uani 1 1 d . . . . .
C18 C 0.4786(3) 0.93485(13) 0.87231(13) 0.0378(5) Uani 1 1 d . . . . .
C20 C 0.3046(2) 0.75464(14) 1.08473(12) 0.0356(5) Uani 1 1 d . . . . .
C22 C -0.1264(2) 0.75337(14) 1.07868(13) 0.0379(5) Uani 1 1 d . . . . .
N1 N 0.0345(2) 0.85092(12) 1.15921(10) 0.0378(4) Uani 1 1 d . . . . .
C23 C 0.3138(2) 0.95926(13) 0.85842(13) 0.0352(5) Uani 1 1 d . . . . .
C3 C -0.1909(3) 0.71636(18) 0.90490(16) 0.0592(7) Uani 1 1 d . . . . .
H3 H -0.214042 0.703486 0.846038 0.071 Uiso 1 1 calc R U . . .
C13 C 0.0687(2) 0.86726(14) 1.06833(12) 0.0361(5) Uani 1 1 d . . . . .
H13 H 0.039217 0.929614 1.051054 0.043 Uiso 1 1 calc R U . . .
C7 C 0.2533(2) 0.85222(13) 1.06592(12) 0.0357(5) Uani 1 1 d . . . . .
H7 H 0.308373 0.888559 1.113474 0.043 Uiso 1 1 calc R U . . .
C15 C 0.3224(3) 0.59789(15) 1.04382(16) 0.0589(7) Uani 1 1 d . . . . .
H15 H 0.305645 0.552944 1.001636 0.071 Uiso 1 1 calc R U . . .
C2 C 0.4141(3) 0.64214(17) 1.18761(15) 0.0564(7) Uani 1 1 d . . . . .
H2 H 0.459684 0.627497 1.243529 0.068 Uiso 1 1 calc R U . . .
C17 C 0.3734(3) 0.73077(15) 1.16701(14) 0.0468(6) Uani 1 1 d . . . . .
H17 H 0.392618 0.775414 1.209343 0.056 Uiso 1 1 calc R U . . .
C9 C -0.2370(3) 0.68594(15) 1.05202(15) 0.0512(6) Uani 1 1 d . . . . .
H9 H -0.289386 0.653290 1.092082 0.061 Uiso 1 1 calc R U . . .
C19 C -0.0738(3) 0.78704(14) 1.16483(13) 0.0385(5) Uani 1 1 d . . . . .
C5 C -0.1266(3) 0.75878(16) 1.24877(14) 0.0574(7) Uani 1 1 d . . . . .
H5A H -0.228169 0.787740 1.256466 0.086 Uiso 1 1 calc R U . . .
H5B H -0.045394 0.776127 1.295167 0.086 Uiso 1 1 calc R U . . .
H5C H -0.140569 0.694124 1.249197 0.086 Uiso 1 1 calc R U . . .
C21 C 0.3877(3) 0.57577(16) 1.12633(16) 0.0567(7) Uani 1 1 d . . . . .
H21 H 0.413991 0.515824 1.140495 0.068 Uiso 1 1 calc R U . . .
C11 C -0.2676(3) 0.66839(17) 0.96430(17) 0.0590(7) Uani 1 1 d . . . . .
H11 H -0.341694 0.623173 0.945046 0.071 Uiso 1 1 calc R U . . .
O1 O 0.10950(18) 0.89775(10) 1.22218(9) 0.0485(4) Uani 1 1 d . . . . .


_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
S1 C16 1.743(2) . ?
S1 C18 1.726(2) . ?
C1 H1 0.9300 . ?
C1 C6 1.369(3) . ?
C1 C18 1.389(3) . ?
N2 C16 1.292(2) . ?
N2 C23 1.398(2) . ?
C4 H4 0.9300 . ?
C4 C14 1.378(3) . ?
C4 C3 1.387(3) . ?
C6 H6 0.9300 . ?
C6 C8 1.383(3) . ?
C8 H8 0.9300 . ?
C8 C12 1.378(3) . ?
C10 H10 0.9300 . ?
C10 C20 1.381(3) . ?
C10 C15 1.385(3) . ?
C12 H12 0.9300 . ?
C12 C23 1.385(3) . ?
C14 C22 1.392(3) . ?
C14 C13 1.498(3) . ?
C16 C7 1.508(3) . ?
C18 C23 1.400(3) . ?
C20 C7 1.518(3) . ?
C20 C17 1.381(3) . ?
C22 C9 1.381(3) . ?
C22 C19 1.444(3) . ?
N1 C13 1.487(2) . ?
N1 C19 1.307(3) . ?
N1 O1 1.294(2) . ?
C3 H3 0.9300 . ?
C3 C11 1.372(3) . ?
C13 H13 0.9800 . ?
C13 C7 1.544(3) . ?
C7 H7 0.9800 . ?
C15 H15 0.9300 . ?
C15 C21 1.369(3) . ?
C2 H2 0.9300 . ?
C2 C17 1.377(3) . ?
C2 C21 1.363(3) . ?
C17 H17 0.9300 . ?
C9 H9 0.9300 . ?
C9 C11 1.379(3) . ?
C19 C5 1.478(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C21 H21 0.9300 . ?
C11 H11 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
C18 S1 C16 89.04(10) . . ?
C6 C1 H1 120.9 . . ?
C6 C1 C18 118.2(2) . . ?
C18 C1 H1 120.9 . . ?
C16 N2 C23 110.00(17) . . ?
C14 C4 H4 120.6 . . ?
C14 C4 C3 118.8(2) . . ?
C3 C4 H4 120.6 . . ?
C1 C6 H6 119.4 . . ?
C1 C6 C8 121.2(2) . . ?
C8 C6 H6 119.4 . . ?
C6 C8 H8 119.4 . . ?
C12 C8 C6 121.3(2) . . ?
C12 C8 H8 119.4 . . ?
C20 C10 H10 119.6 . . ?
C20 C10 C15 120.8(2) . . ?
C15 C10 H10 119.6 . . ?
C8 C12 H12 120.8 . . ?
C8 C12 C23 118.5(2) . . ?
C23 C12 H12 120.8 . . ?
C4 C14 C22 119.9(2) . . ?
C4 C14 C13 131.8(2) . . ?
C22 C14 C13 108.33(17) . . ?
N2 C16 S1 116.46(15) . . ?
N2 C16 C7 125.18(18) . . ?
C7 C16 S1 118.30(15) . . ?
C1 C18 S1 129.51(18) . . ?
C1 C18 C23 121.0(2) . . ?
C23 C18 S1 109.51(15) . . ?
C10 C20 C7 122.51(18) . . ?
C10 C20 C17 117.79(19) . . ?
C17 C20 C7 119.68(18) . . ?
C14 C22 C19 108.71(18) . . ?
C9 C22 C14 121.3(2) . . ?
C9 C22 C19 130.0(2) . . ?
C19 N1 C13 112.61(16) . . ?
O1 N1 C13 120.12(16) . . ?
O1 N1 C19 127.27(17) . . ?
N2 C23 C18 115.00(18) . . ?
C12 C23 N2 124.99(19) . . ?
C12 C23 C18 119.98(19) . . ?
C4 C3 H3 119.6 . . ?
C11 C3 C4 120.7(2) . . ?
C11 C3 H3 119.6 . . ?
C14 C13 H13 110.0 . . ?
C14 C13 C7 117.62(17) . . ?
N1 C13 C14 101.53(16) . . ?
N1 C13 H13 110.0 . . ?
N1 C13 C7 107.09(15) . . ?
C7 C13 H13 110.0 . . ?
C16 C7 C20 113.18(16) . . ?
C16 C7 C13 111.90(16) . . ?
C16 C7 H7 106.1 . . ?
C20 C7 C13 112.70(16) . . ?
C20 C7 H7 106.1 . . ?
C13 C7 H7 106.1 . . ?
C10 C15 H15 119.9 . . ?
C21 C15 C10 120.2(2) . . ?
C21 C15 H15 119.9 . . ?
C17 C2 H2 119.9 . . ?
C21 C2 H2 119.9 . . ?
C21 C2 C17 120.2(2) . . ?
C20 C17 H17 119.4 . . ?
C2 C17 C20 121.3(2) . . ?
C2 C17 H17 119.4 . . ?
C22 C9 H9 121.0 . . ?
C11 C9 C22 118.1(2) . . ?
C11 C9 H9 121.0 . . ?
C22 C19 C5 129.0(2) . . ?
N1 C19 C22 108.76(18) . . ?
N1 C19 C5 122.3(2) . . ?
C19 C5 H5A 109.5 . . ?
C19 C5 H5B 109.5 . . ?
C19 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C15 C21 H21 120.2 . . ?
C2 C21 C15 119.6(2) . . ?
C2 C21 H21 120.2 . . ?
C3 C11 C9 121.2(2) . . ?
C3 C11 H11 119.4 . . ?
C9 C11 H11 119.4 . . ?

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
S1 C16 C7 C20 -50.5(2) . . . . ?
S1 C16 C7 C13 -179.21(13) . . . . ?
S1 C18 C23 N2 0.2(2) . . . . ?
S1 C18 C23 C12 -177.79(15) . . . . ?
C1 C6 C8 C12 0.3(4) . . . . ?
C1 C18 C23 N2 178.40(17) . . . . ?
C1 C18 C23 C12 0.4(3) . . . . ?
N2 C16 C7 C20 132.3(2) . . . . ?
N2 C16 C7 C13 3.6(3) . . . . ?
C4 C14 C22 C9 1.4(3) . . . . ?
C4 C14 C22 C19 -178.19(19) . . . . ?
C4 C14 C13 N1 178.1(2) . . . . ?
C4 C14 C13 C7 -65.4(3) . . . . ?
C4 C3 C11 C9 0.3(4) . . . . ?
C6 C1 C18 S1 177.40(17) . . . . ?
C6 C1 C18 C23 -0.4(3) . . . . ?
C6 C8 C12 C23 -0.3(3) . . . . ?
C8 C12 C23 N2 -177.87(19) . . . . ?
C8 C12 C23 C18 -0.1(3) . . . . ?
C10 C20 C7 C16 -49.1(3) . . . . ?
C10 C20 C7 C13 79.1(2) . . . . ?
C10 C20 C17 C2 -1.5(3) . . . . ?
C10 C15 C21 C2 -0.9(4) . . . . ?
C14 C4 C3 C11 0.2(4) . . . . ?
C14 C22 C9 C11 -0.8(3) . . . . ?
C14 C22 C19 N1 -1.2(2) . . . . ?
C14 C22 C19 C5 178.6(2) . . . . ?
C14 C13 C7 C16 80.7(2) . . . . ?
C14 C13 C7 C20 -48.2(2) . . . . ?
C16 S1 C18 C1 -177.9(2) . . . . ?
C16 S1 C18 C23 0.01(15) . . . . ?
C16 N2 C23 C12 177.47(18) . . . . ?
C16 N2 C23 C18 -0.4(2) . . . . ?
C18 S1 C16 N2 -0.29(16) . . . . ?
C18 S1 C16 C7 -177.69(15) . . . . ?
C18 C1 C6 C8 0.0(3) . . . . ?
C20 C10 C15 C21 -0.3(4) . . . . ?
C22 C14 C13 N1 -2.4(2) . . . . ?
C22 C14 C13 C7 113.99(19) . . . . ?
C22 C9 C11 C3 -0.1(3) . . . . ?
N1 C13 C7 C16 -165.88(16) . . . . ?
N1 C13 C7 C20 65.2(2) . . . . ?
C23 N2 C16 S1 0.5(2) . . . . ?
C23 N2 C16 C7 177.66(17) . . . . ?
C3 C4 C14 C22 -1.1(3) . . . . ?
C3 C4 C14 C13 178.3(2) . . . . ?
C13 C14 C22 C9 -178.15(19) . . . . ?
C13 C14 C22 C19 2.3(2) . . . . ?
C13 N1 C19 C22 -0.5(2) . . . . ?
C13 N1 C19 C5 179.74(18) . . . . ?
C7 C20 C17 C2 176.8(2) . . . . ?
C15 C10 C20 C7 -176.8(2) . . . . ?
C15 C10 C20 C17 1.4(3) . . . . ?
C17 C20 C7 C16 132.7(2) . . . . ?
C17 C20 C7 C13 -99.0(2) . . . . ?
C17 C2 C21 C15 0.8(4) . . . . ?
C9 C22 C19 N1 179.4(2) . . . . ?
C9 C22 C19 C5 -0.9(4) . . . . ?
C19 C22 C9 C11 178.7(2) . . . . ?
C19 N1 C13 C14 1.8(2) . . . . ?
C19 N1 C13 C7 -122.07(17) . . . . ?
C21 C2 C17 C20 0.4(4) . . . . ?
O1 N1 C13 C14 -178.36(16) . . . . ?
O1 N1 C13 C7 57.8(2) . . . . ?
O1 N1 C19 C22 179.67(17) . . . . ?
O1 N1 C19 C5 -0.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2202409'
loop_
_audit_author_name
_audit_author_address
wang
;Suzhou university
China
;
_audit_update_record             
;
2022-08-19 deposited with the CCDC.	2024-04-08 downloaded from the CCDC.
;
_audit_creation_date             2022-01-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H16 F N O S'
_chemical_formula_sum            'C23 H16 F N O S'
_chemical_formula_weight         373.43
_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'
F F 0.0171 0.0103 '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'
O O 0.0106 0.0060 '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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.5347(7)
_cell_length_b                   15.7748(8)
_cell_length_c                   19.3093(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.0108(16)
_cell_angle_gamma                90
_cell_volume                     3780.8(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9411
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.23
_cell_measurement_theta_min      2.24
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.927
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1289 before and 0.0598 after correction. The Ratio of minimum to maximum transmission is 0.9053. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            52411
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.547
_diffrn_reflns_theta_min         2.237
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3222
_reflns_number_total             4346
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.876
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4346
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0674
_refine_ls_restrained_S_all      1.050
_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)+(0.1226P)²+4.7031P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1992
_refine_ls_wR_factor_ref         0.2219
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C16(H16), C1(H1), C15(H15), C4(H4), C13(H13), C19(H19), C22(H22),
 C12(H12), C2(H2), C3(H3), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
S1 S 0.36013(6) 0.56856(5) 0.64976(4) 0.0567(3) Uani 1 1 d . . . . .
N1 N 0.26679(18) 0.49489(14) 0.53755(11) 0.0455(5) Uani 1 1 d . . . . .
C11 C 0.0989(2) 0.62874(15) 0.51173(12) 0.0395(5) Uani 1 1 d . . . . .
C23 C 0.3692(2) 0.45943(17) 0.55292(14) 0.0455(6) Uani 1 1 d . . . . .
C17 C 0.2510(2) 0.55079(16) 0.58424(13) 0.0413(6) Uani 1 1 d . . . . .
C5 C 0.1392(2) 0.59285(18) 0.71158(14) 0.0471(6) Uani 1 1 d . . . . .
C10 C 0.1514(2) 0.60040(16) 0.58177(13) 0.0427(6) Uani 1 1 d . . . . .
C9 C 0.1101(2) 0.62417(17) 0.63916(13) 0.0465(6) Uani 1 1 d . . . . .
H9 H 0.056556 0.665367 0.632681 0.056 Uiso 1 1 calc R . . . .
C18 C 0.4322(2) 0.49150(18) 0.61191(15) 0.0490(6) Uani 1 1 d . . . . .
C16 C 0.1557(2) 0.66656(16) 0.46337(14) 0.0469(6) Uani 1 1 d . . . . .
H16 H 0.230313 0.670707 0.472938 0.056 Uiso 1 1 calc R . . . .
C6 C 0.1629(2) 0.64703(19) 0.76862(14) 0.0488(6) Uani 1 1 d . . . . .
C1 C 0.1793(3) 0.6131(2) 0.83580(15) 0.0606(8) Uani 1 1 d . . . . .
H1 H 0.192010 0.649544 0.873934 0.073 Uiso 1 1 calc R . . . .
C15 C 0.1030(3) 0.69821(18) 0.40106(15) 0.0578(8) Uani 1 1 d . . . . .
H15 H 0.141047 0.724219 0.368880 0.069 Uiso 1 1 calc R . . . .
F1 F -0.0569(2) 0.7204(2) 0.32646(11) 0.1124(9) Uani 1 1 d . . . . .
C4 C 0.1353(3) 0.5069(2) 0.72354(17) 0.0618(8) Uani 1 1 d . . . . .
H4 H 0.119235 0.470426 0.685660 0.074 Uiso 1 1 calc R . . . .
C7 C 0.1743(2) 0.7405(2) 0.75804(16) 0.0577(7) Uani 1 1 d . . . . .
O1 O 0.2036(3) 0.76652(16) 0.70458(14) 0.0880(8) Uani 1 1 d . . . . .
C13 C -0.0646(3) 0.6520(2) 0.43286(18) 0.0686(9) Uani 1 1 d . . . . .
H13 H -0.138896 0.646852 0.421780 0.082 Uiso 1 1 calc R . . . .
C19 C 0.5361(2) 0.4613(2) 0.63421(17) 0.0591(8) Uani 1 1 d . . . . .
H19 H 0.577482 0.483084 0.673930 0.071 Uiso 1 1 calc R . . . .
C22 C 0.4102(3) 0.39675(19) 0.51463(17) 0.0592(8) Uani 1 1 d . . . . .
H22 H 0.369258 0.375002 0.474700 0.071 Uiso 1 1 calc R . . . .
C12 C -0.0114(2) 0.6207(2) 0.49551(15) 0.0528(7) Uani 1 1 d . . . . .
H12 H -0.050521 0.594082 0.526841 0.063 Uiso 1 1 calc R . . . .
C14 C -0.0052(3) 0.6904(2) 0.38815(16) 0.0673(9) Uani 1 1 d . . . . .
C2 C 0.1771(3) 0.5278(3) 0.84709(18) 0.0766(11) Uani 1 1 d . . . . .
H2 H 0.190638 0.506249 0.892289 0.092 Uiso 1 1 calc R . . . .
C3 C 0.1543(3) 0.4733(2) 0.7901(2) 0.0758(10) Uani 1 1 d . . . . .
H3 H 0.152065 0.414996 0.796870 0.091 Uiso 1 1 calc R . . . .
C20 C 0.5746(3) 0.3991(2) 0.59602(19) 0.0678(9) Uani 1 1 d . . . . .
H20 H 0.643447 0.377895 0.610059 0.081 Uiso 1 1 calc R . . . .
C21 C 0.5137(3) 0.3663(2) 0.5365(2) 0.0714(10) Uani 1 1 d . . . . .
H21 H 0.542199 0.323833 0.511051 0.086 Uiso 1 1 calc R . . . .
C8 C 0.1518(4) 0.8008(3) 0.8129(2) 0.0957(14) Uani 1 1 d . . . . .
H8A H 0.075564 0.802976 0.814332 0.143 Uiso 1 1 calc GR . . . .
H8B H 0.177088 0.856161 0.802435 0.143 Uiso 1 1 calc GR . . . .
H8C H 0.188031 0.782452 0.857424 0.143 Uiso 1 1 calc GR . . . .


_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
S1 C17 1.752(3) . ?
S1 C18 1.735(3) . ?
N1 C23 1.394(3) . ?
N1 C17 1.296(3) . ?
C11 C10 1.488(3) . ?
C11 C16 1.386(4) . ?
C11 C12 1.381(4) . ?
C23 C18 1.388(4) . ?
C23 C22 1.376(4) . ?
C17 C10 1.468(4) . ?
C5 C9 1.480(4) . ?
C5 C6 1.393(4) . ?
C5 C4 1.378(4) . ?
C10 C9 1.341(4) . ?
C18 C19 1.398(4) . ?
C16 C15 1.383(4) . ?
C6 C1 1.391(4) . ?
C6 C7 1.497(4) . ?
C1 C2 1.364(5) . ?
C15 C14 1.350(5) . ?
F1 C14 1.360(3) . ?
C4 C3 1.380(5) . ?
C7 O1 1.215(4) . ?
C7 C8 1.480(5) . ?
C13 C12 1.388(4) . ?
C13 C14 1.358(5) . ?
C19 C20 1.356(5) . ?
C22 C21 1.393(5) . ?
C2 C3 1.394(6) . ?
C20 C21 1.389(6) . ?

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
C18 S1 C17 89.06(13) . . ?
C17 N1 C23 110.5(2) . . ?
C16 C11 C10 122.6(2) . . ?
C12 C11 C10 118.7(2) . . ?
C12 C11 C16 118.6(2) . . ?
C18 C23 N1 115.5(2) . . ?
C22 C23 N1 125.1(3) . . ?
C22 C23 C18 119.4(3) . . ?
N1 C17 S1 115.57(19) . . ?
N1 C17 C10 123.5(2) . . ?
C10 C17 S1 120.86(19) . . ?
C6 C5 C9 122.6(3) . . ?
C4 C5 C9 118.5(3) . . ?
C4 C5 C6 118.7(3) . . ?
C17 C10 C11 117.1(2) . . ?
C9 C10 C11 119.6(2) . . ?
C9 C10 C17 123.2(2) . . ?
C10 C9 C5 127.9(2) . . ?
C23 C18 S1 109.3(2) . . ?
C23 C18 C19 121.8(3) . . ?
C19 C18 S1 128.8(3) . . ?
C15 C16 C11 120.9(3) . . ?
C5 C6 C7 120.6(2) . . ?
C1 C6 C5 119.3(3) . . ?
C1 C6 C7 120.1(3) . . ?
C2 C1 C6 121.6(3) . . ?
C14 C15 C16 118.3(3) . . ?
C5 C4 C3 121.9(3) . . ?
O1 C7 C6 119.7(3) . . ?
O1 C7 C8 120.0(3) . . ?
C8 C7 C6 120.3(3) . . ?
C14 C13 C12 118.3(3) . . ?
C20 C19 C18 117.8(3) . . ?
C23 C22 C21 119.2(3) . . ?
C11 C12 C13 120.6(3) . . ?
C15 C14 F1 118.3(3) . . ?
C15 C14 C13 123.3(3) . . ?
C13 C14 F1 118.4(3) . . ?
C1 C2 C3 119.2(3) . . ?
C4 C3 C2 119.2(3) . . ?
C19 C20 C21 121.6(3) . . ?
C20 C21 C22 120.2(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
