# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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. 
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data_220705sjt_0m
_database_code_depnum_ccdc_archive 'CCDC 2252236'
loop_
_audit_author_name
_audit_author_address
'Jiangtao Sun'
;Changzhou University
China
;
_audit_update_record             
;
2023-03-28 deposited with the CCDC.	2023-05-15 downloaded from the CCDC.
;
_audit_creation_date             2022-07-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H18 N2 O2 S'
_chemical_formula_sum            'C22 H18 N2 O2 S'
_chemical_formula_weight         374.44
_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 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 '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                   9.1365(2)
_cell_length_b                   21.8460(4)
_cell_length_c                   10.2421(2)
_cell_angle_alpha                90
_cell_angle_beta                 116.0440(10)
_cell_angle_gamma                90
_cell_volume                     1836.70(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9942
_cell_measurement_temperature    213.00
_cell_measurement_theta_max      54.974
_cell_measurement_theta_min      4.688
_shelx_estimated_absorpt_T_max   0.946
_shelx_estimated_absorpt_T_min   0.925
_exptl_absorpt_coefficient_mu    1.125
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1620 before and 0.0603 after correction.
The Ratio of minimum to maximum transmission is 0.7893.
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    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19091
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.949
_diffrn_reflns_theta_min         4.687
_diffrn_ambient_temperature      213.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.1995708
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3155
_reflns_number_total             3476
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.039
_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         3476
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0351
_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)+(0.0464P)²+0.6011P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0948
_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:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
2.d :
 C3(H3)
;
_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
S1 S 0.78822(4) 0.55601(2) 0.63521(4) 0.03192(12) Uani 1 1 d . . . . .
O1 O 0.67940(14) 0.51004(5) 0.64002(12) 0.0413(3) Uani 1 1 d . . . . .
O2 O 0.94636(13) 0.56289(5) 0.75283(12) 0.0444(3) Uani 1 1 d . . . . .
N1 N 0.69438(14) 0.62332(5) 0.62666(12) 0.0290(3) Uani 1 1 d . . . . .
N2 N 0.54991(14) 0.67054(5) 0.40022(12) 0.0305(3) Uani 1 1 d . . . . .
C1 C 0.52842(16) 0.62904(6) 0.50363(14) 0.0284(3) Uani 1 1 d . . . . .
H1 H 0.488554 0.588610 0.458273 0.034 Uiso 1 1 calc R U . . .
C2 C 0.41568(18) 0.65557(7) 0.55598(16) 0.0355(3) Uani 1 1 d . . . . .
C3 C 0.3223(2) 0.67832(9) 0.5921(2) 0.0543(5) Uani 1 1 d . . . . .
H3 H 0.247865 0.696463 0.620971 0.065 Uiso 1 1 calc R U . . .
C4 C 0.47089(16) 0.65895(6) 0.24989(14) 0.0275(3) Uani 1 1 d . . . . .
C5 C 0.54050(18) 0.67434(7) 0.15739(15) 0.0339(3) Uani 1 1 d . . . . .
H5 H 0.641978 0.694231 0.194160 0.041 Uiso 1 1 calc R U . . .
C6 C 0.4594(2) 0.66017(8) 0.01135(16) 0.0409(4) Uani 1 1 d . . . . .
H6 H 0.506161 0.671015 -0.050865 0.049 Uiso 1 1 calc R U . . .
C7 C 0.3111(2) 0.63039(8) -0.04499(17) 0.0424(4) Uani 1 1 d . . . . .
H7 H 0.257670 0.620633 -0.144383 0.051 Uiso 1 1 calc R U . . .
C8 C 0.24233(19) 0.61517(7) 0.04653(17) 0.0393(4) Uani 1 1 d . . . . .
H8 H 0.141710 0.594656 0.009251 0.047 Uiso 1 1 calc R U . . .
C9 C 0.31988(17) 0.62977(7) 0.19251(16) 0.0333(3) Uani 1 1 d . . . . .
H9 H 0.270600 0.619990 0.253384 0.040 Uiso 1 1 calc R U . . .
C10 C 0.69432(17) 0.70314(6) 0.47724(15) 0.0285(3) Uani 1 1 d . . . . .
C11 C 0.78073(16) 0.67660(6) 0.61358(14) 0.0284(3) Uani 1 1 d . . . . .
C12 C 0.92632(18) 0.69996(7) 0.71477(16) 0.0360(3) Uani 1 1 d . . . . .
H12 H 0.983193 0.681252 0.805994 0.043 Uiso 1 1 calc R U . . .
C13 C 0.9864(2) 0.75213(8) 0.67749(18) 0.0430(4) Uani 1 1 d . . . . .
H13 H 1.085825 0.769099 0.744035 0.052 Uiso 1 1 calc R U . . .
C14 C 0.9012(2) 0.77912(7) 0.54362(19) 0.0434(4) Uani 1 1 d . . . . .
H14 H 0.943792 0.814556 0.521022 0.052 Uiso 1 1 calc R U . . .
C15 C 0.7536(2) 0.75562(7) 0.44045(17) 0.0368(3) Uani 1 1 d . . . . .
H15 H 0.696582 0.774566 0.349548 0.044 Uiso 1 1 calc R U . . .
C16 C 0.80288(18) 0.54990(6) 0.47068(16) 0.0312(3) Uani 1 1 d . . . . .
C17 C 0.92772(19) 0.58010(7) 0.45404(19) 0.0396(4) Uani 1 1 d . . . . .
H17 H 1.010088 0.600461 0.532981 0.048 Uiso 1 1 calc R U . . .
C18 C 0.9285(2) 0.57962(7) 0.3196(2) 0.0449(4) Uani 1 1 d . . . . .
H18 H 1.011950 0.600324 0.307623 0.054 Uiso 1 1 calc R U . . .
C19 C 0.8095(2) 0.54941(7) 0.20190(19) 0.0414(4) Uani 1 1 d . . . . .
C20 C 0.6880(2) 0.51879(7) 0.22213(18) 0.0410(4) Uani 1 1 d . . . . .
H20 H 0.607215 0.497605 0.143678 0.049 Uiso 1 1 calc R U . . .
C21 C 0.68308(19) 0.51875(7) 0.35507(16) 0.0355(3) Uani 1 1 d . . . . .
H21 H 0.599767 0.497903 0.367013 0.043 Uiso 1 1 calc R U . . .
C22 C 0.8100(3) 0.55021(9) 0.0551(2) 0.0594(5) Uani 1 1 d . . . . .
H22A H 0.749025 0.515380 -0.001335 0.089 Uiso 1 1 calc R U . . .
H22B H 0.921368 0.547989 0.067383 0.089 Uiso 1 1 calc R U . . .
H22C H 0.760031 0.587765 0.004780 0.089 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
S1 O1 1.4292(11) . ?
S1 O2 1.4259(11) . ?
S1 N1 1.6850(12) . ?
S1 C16 1.7531(15) . ?
N1 C1 1.4916(17) . ?
N1 C11 1.4449(17) . ?
N2 C1 1.4714(17) . ?
N2 C4 1.4071(17) . ?
N2 C10 1.3986(17) . ?
C1 H1 0.9900 . ?
C1 C2 1.473(2) . ?
C2 C3 1.179(2) . ?
C3 H3 0.9400 . ?
C4 C5 1.394(2) . ?
C4 C9 1.394(2) . ?
C5 H5 0.9400 . ?
C5 C6 1.382(2) . ?
C6 H6 0.9400 . ?
C6 C7 1.381(2) . ?
C7 H7 0.9400 . ?
C7 C8 1.379(2) . ?
C8 H8 0.9400 . ?
C8 C9 1.382(2) . ?
C9 H9 0.9400 . ?
C10 C11 1.393(2) . ?
C10 C15 1.389(2) . ?
C11 C12 1.3760(19) . ?
C12 H12 0.9400 . ?
C12 C13 1.389(2) . ?
C13 H13 0.9400 . ?
C13 C14 1.377(2) . ?
C14 H14 0.9400 . ?
C14 C15 1.395(2) . ?
C15 H15 0.9400 . ?
C16 C17 1.391(2) . ?
C16 C21 1.388(2) . ?
C17 H17 0.9400 . ?
C17 C18 1.380(2) . ?
C18 H18 0.9400 . ?
C18 C19 1.386(2) . ?
C19 C20 1.387(2) . ?
C19 C22 1.506(2) . ?
C20 H20 0.9400 . ?
C20 C21 1.382(2) . ?
C21 H21 0.9400 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?

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
O1 S1 N1 105.62(6) . . ?
O1 S1 C16 109.12(7) . . ?
O2 S1 O1 120.48(7) . . ?
O2 S1 N1 104.81(6) . . ?
O2 S1 C16 110.09(7) . . ?
N1 S1 C16 105.56(6) . . ?
C1 N1 S1 114.98(9) . . ?
C11 N1 S1 114.95(9) . . ?
C11 N1 C1 104.37(10) . . ?
C4 N2 C1 120.68(11) . . ?
C10 N2 C1 107.38(11) . . ?
C10 N2 C4 127.77(11) . . ?
N1 C1 H1 110.5 . . ?
N2 C1 N1 104.61(10) . . ?
N2 C1 H1 110.5 . . ?
N2 C1 C2 110.81(11) . . ?
C2 C1 N1 109.85(11) . . ?
C2 C1 H1 110.5 . . ?
C3 C2 C1 176.96(18) . . ?
C2 C3 H3 180.0 . . ?
C5 C4 N2 122.15(13) . . ?
C9 C4 N2 118.75(12) . . ?
C9 C4 C5 119.08(13) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.59(14) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.29(14) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 120.5 . . ?
C8 C7 C6 119.08(14) . . ?
C8 C7 H7 120.5 . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.66(15) . . ?
C9 C8 H8 119.7 . . ?
C4 C9 H9 119.9 . . ?
C8 C9 C4 120.28(14) . . ?
C8 C9 H9 119.9 . . ?
C11 C10 N2 109.42(12) . . ?
C15 C10 N2 130.61(13) . . ?
C15 C10 C11 119.90(13) . . ?
C10 C11 N1 109.63(11) . . ?
C12 C11 N1 127.99(13) . . ?
C12 C11 C10 122.38(14) . . ?
C11 C12 H12 121.1 . . ?
C11 C12 C13 117.72(15) . . ?
C13 C12 H12 121.1 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.40(15) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 118.9 . . ?
C13 C14 C15 122.17(15) . . ?
C15 C14 H14 118.9 . . ?
C10 C15 C14 117.42(15) . . ?
C10 C15 H15 121.3 . . ?
C14 C15 H15 121.3 . . ?
C17 C16 S1 119.62(12) . . ?
C21 C16 S1 119.54(11) . . ?
C21 C16 C17 120.66(14) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 C16 118.83(15) . . ?
C18 C17 H17 120.6 . . ?
C17 C18 H18 119.1 . . ?
C17 C18 C19 121.73(15) . . ?
C19 C18 H18 119.1 . . ?
C18 C19 C20 118.25(15) . . ?
C18 C19 C22 121.20(16) . . ?
C20 C19 C22 120.55(16) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 C19 121.44(15) . . ?
C21 C20 H20 119.3 . . ?
C16 C21 H21 120.5 . . ?
C20 C21 C16 119.07(14) . . ?
C20 C21 H21 120.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
S1 N1 C1 N2 -106.08(10) . . . . ?
S1 N1 C1 C2 134.94(10) . . . . ?
S1 N1 C11 C10 112.37(11) . . . . ?
S1 N1 C11 C12 -67.22(16) . . . . ?
S1 C16 C17 C18 -173.90(12) . . . . ?
S1 C16 C21 C20 174.34(12) . . . . ?
O1 S1 N1 C1 -55.83(10) . . . . ?
O1 S1 N1 C11 -177.07(9) . . . . ?
O1 S1 C16 C17 -165.62(12) . . . . ?
O1 S1 C16 C21 19.08(14) . . . . ?
O2 S1 N1 C1 175.95(9) . . . . ?
O2 S1 N1 C11 54.71(11) . . . . ?
O2 S1 C16 C17 -31.32(14) . . . . ?
O2 S1 C16 C21 153.38(12) . . . . ?
N1 S1 C16 C17 81.28(13) . . . . ?
N1 S1 C16 C21 -94.02(13) . . . . ?
N1 C11 C12 C13 179.94(13) . . . . ?
N2 C4 C5 C6 178.04(13) . . . . ?
N2 C4 C9 C8 -177.03(13) . . . . ?
N2 C10 C11 N1 1.99(15) . . . . ?
N2 C10 C11 C12 -178.40(12) . . . . ?
N2 C10 C15 C14 177.61(14) . . . . ?
C1 N1 C11 C10 -14.50(14) . . . . ?
C1 N1 C11 C12 165.91(13) . . . . ?
C1 N2 C4 C5 -147.04(13) . . . . ?
C1 N2 C4 C9 31.36(19) . . . . ?
C1 N2 C10 C11 11.75(15) . . . . ?
C1 N2 C10 C15 -165.29(14) . . . . ?
C4 N2 C1 N1 138.52(12) . . . . ?
C4 N2 C1 C2 -103.16(14) . . . . ?
C4 N2 C10 C11 -145.03(13) . . . . ?
C4 N2 C10 C15 37.9(2) . . . . ?
C4 C5 C6 C7 -0.7(2) . . . . ?
C5 C4 C9 C8 1.4(2) . . . . ?
C5 C6 C7 C8 0.7(2) . . . . ?
C6 C7 C8 C9 0.4(2) . . . . ?
C7 C8 C9 C4 -1.5(2) . . . . ?
C9 C4 C5 C6 -0.3(2) . . . . ?
C10 N2 C1 N1 -20.23(13) . . . . ?
C10 N2 C1 C2 98.09(13) . . . . ?
C10 N2 C4 C5 7.0(2) . . . . ?
C10 N2 C4 C9 -174.60(13) . . . . ?
C10 C11 C12 C13 0.4(2) . . . . ?
C11 N1 C1 N2 20.76(12) . . . . ?
C11 N1 C1 C2 -98.21(12) . . . . ?
C11 C10 C15 C14 0.8(2) . . . . ?
C11 C12 C13 C14 0.3(2) . . . . ?
C12 C13 C14 C15 -0.4(2) . . . . ?
C13 C14 C15 C10 -0.1(2) . . . . ?
C15 C10 C11 N1 179.39(12) . . . . ?
C15 C10 C11 C12 -1.0(2) . . . . ?
C16 S1 N1 C1 59.70(10) . . . . ?
C16 S1 N1 C11 -61.54(11) . . . . ?
C16 C17 C18 C19 -0.7(2) . . . . ?
C17 C16 C21 C20 -0.9(2) . . . . ?
C17 C18 C19 C20 -0.4(2) . . . . ?
C17 C18 C19 C22 178.88(16) . . . . ?
C18 C19 C20 C21 0.9(2) . . . . ?
C19 C20 C21 C16 -0.2(2) . . . . ?
C21 C16 C17 C18 1.3(2) . . . . ?
C22 C19 C20 C21 -178.43(15) . . . . ?

_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_zt-20230413_auto
_database_code_depnum_ccdc_archive 'CCDC 2255981'
loop_
_audit_author_name
_audit_author_address
'Jiangtao Sun'
;Changzhou University
China
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-05-15 downloaded from the CCDC.
;
_audit_creation_date             2023-04-13
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H15 N3 O4 S'
_chemical_formula_sum            'C21 H15 N3 O4 S'
_chemical_formula_weight         405.42
_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 0.0181 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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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/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                   9.1583(2)
_cell_length_b                   21.8770(3)
_cell_length_c                   10.2542(2)
_cell_angle_alpha                90
_cell_angle_beta                 114.233(2)
_cell_angle_gamma                90
_cell_volume                     1873.46(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10337
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      76.9680
_cell_measurement_theta_min      5.1280
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.837
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12222
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.261
_diffrn_reflns_theta_min         5.144
_diffrn_ambient_temperature      301(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3517
_reflns_number_total             3785
_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 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0108(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3785
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.054
_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)+(0.0551P)²+0.4516P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1060
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C2(H2)
1.b Aromatic/amide H refined with riding coordinates:
 C22(H22), C15(H15), C25(H25), C23(H23), C26(H26), C8(H8), C11(H11), C5(H5),
 C13(H13), C14(H14), C12(H12), C7(H7), C6(H6)
1.c :
 C20(H20)
;
_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
S16 S 0.15874(4) 0.44565(2) 0.36894(4) 0.04470(15) Uani 1 1 d . . . . .
O18 O 0.04984(14) 0.49151(5) 0.37151(12) 0.0559(3) Uani 1 1 d . . . . .
O17 O 0.20486(16) 0.44059(6) 0.25283(13) 0.0598(3) Uani 1 1 d . . . . .
N1 N 0.15409(14) 0.32932(6) 0.59907(13) 0.0454(3) Uani 1 1 d . . . . .
N3 N 0.07569(14) 0.37836(6) 0.37767(12) 0.0428(3) Uani 1 1 d . . . . .
C2 C 0.03209(16) 0.37100(7) 0.50179(15) 0.0415(3) Uani 1 1 d . . . . .
H2 H 0.036097 0.410486 0.548284 0.050 Uiso 1 1 calc R U . . .
C10 C 0.22823(17) 0.34129(6) 0.74757(15) 0.0415(3) Uani 1 1 d . . . . .
O29 O 0.85971(17) 0.42650(8) 0.9202(2) 0.0974(5) Uani 1 1 d . . . . .
C9 C 0.22028(17) 0.29782(7) 0.51731(16) 0.0444(3) Uani 1 1 d . . . . .
N27 N 0.73670(18) 0.44658(7) 0.9206(2) 0.0671(4) Uani 1 1 d . . . . .
C4 C 0.17160(16) 0.32509(7) 0.38401(15) 0.0436(3) Uani 1 1 d . . . . .
C21 C 0.33334(17) 0.45016(6) 0.52991(16) 0.0429(3) Uani 1 1 d . . . . .
O28 O 0.72209(19) 0.46490(10) 1.02591(18) 0.1004(6) Uani 1 1 d . . . . .
C22 C 0.32762(18) 0.48007(7) 0.64683(17) 0.0470(3) Uani 1 1 d . . . . .
H22 H 0.235152 0.500389 0.638906 0.056 Uiso 1 1 calc R U . . .
C15 C 0.14131(19) 0.37184(7) 0.81162(17) 0.0493(4) Uani 1 1 d . . . . .
H15 H 0.034731 0.381998 0.757676 0.059 Uiso 1 1 calc R U . . .
C25 C 0.60370(19) 0.41963(8) 0.6666(2) 0.0556(4) Uani 1 1 d . . . . .
H25 H 0.696995 0.399820 0.674973 0.067 Uiso 1 1 calc R U . . .
C19 C -0.12888(19) 0.34415(8) 0.45277(18) 0.0520(4) Uani 1 1 d . . . . .
C23 C 0.46138(19) 0.47929(7) 0.77562(18) 0.0517(4) Uani 1 1 d . . . . .
H23 H 0.460559 0.498793 0.855902 0.062 Uiso 1 1 calc R U . . .
C24 C 0.59547(18) 0.44892(7) 0.78169(19) 0.0509(4) Uani 1 1 d . . . . .
C26 C 0.47046(19) 0.42019(7) 0.53801(19) 0.0515(4) Uani 1 1 d . . . . .
H26 H 0.472525 0.400792 0.458081 0.062 Uiso 1 1 calc R U . . .
C8 C 0.31549(19) 0.24559(8) 0.5479(2) 0.0570(4) Uani 1 1 d . . . . .
H8 H 0.348412 0.226134 0.635980 0.068 Uiso 1 1 calc R U . . .
C11 C 0.38586(18) 0.32485(7) 0.83076(17) 0.0504(4) Uani 1 1 d . . . . .
H11 H 0.445327 0.304065 0.789997 0.061 Uiso 1 1 calc R U . . .
C5 C 0.2140(2) 0.30271(8) 0.27877(19) 0.0564(4) Uani 1 1 d . . . . .
H5 H 0.179042 0.321477 0.189714 0.068 Uiso 1 1 calc R U . . .
C13 C 0.3689(2) 0.37069(9) 1.03717(19) 0.0632(5) Uani 1 1 d . . . . .
H13 H 0.416273 0.380540 1.133882 0.076 Uiso 1 1 calc R U . . .
C14 C 0.2127(2) 0.38712(9) 0.95499(18) 0.0581(4) Uani 1 1 d . . . . .
H14 H 0.154877 0.408646 0.996192 0.070 Uiso 1 1 calc R U . . .
C12 C 0.4539(2) 0.33962(9) 0.97485(19) 0.0604(4) Uani 1 1 d . . . . .
H12 H 0.559196 0.328266 1.030410 0.072 Uiso 1 1 calc R U . . .
C7 C 0.3594(2) 0.22363(9) 0.4425(2) 0.0680(5) Uani 1 1 d . . . . .
H7 H 0.424107 0.189101 0.461452 0.082 Uiso 1 1 calc R U . . .
C6 C 0.3106(2) 0.25117(9) 0.3105(2) 0.0683(5) Uani 1 1 d . . . . .
H6 H 0.342553 0.235130 0.242407 0.082 Uiso 1 1 calc R U . . .
C20 C -0.2554(2) 0.32152(11) 0.4171(3) 0.0792(6) Uani 1 1 d . . . . .
H20 H -0.355838 0.303567 0.388810 0.095 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
S16 O18 1.4224(12) . ?
S16 O17 1.4217(11) . ?
S16 N3 1.6761(13) . ?
S16 C21 1.7676(16) . ?
N1 C2 1.4697(18) . ?
N1 C10 1.4140(18) . ?
N1 C9 1.4008(18) . ?
N3 C2 1.4908(17) . ?
N3 C4 1.4447(18) . ?
C2 C19 1.471(2) . ?
C10 C15 1.393(2) . ?
C10 C11 1.389(2) . ?
O29 N27 1.211(2) . ?
C9 C4 1.387(2) . ?
C9 C8 1.393(2) . ?
N27 O28 1.210(2) . ?
N27 C24 1.480(2) . ?
C4 C5 1.378(2) . ?
C21 C22 1.386(2) . ?
C21 C26 1.389(2) . ?
C22 C23 1.385(2) . ?
C15 C14 1.383(2) . ?
C25 C24 1.372(2) . ?
C25 C26 1.381(2) . ?
C19 C20 1.172(3) . ?
C23 C24 1.375(2) . ?
C8 C7 1.385(3) . ?
C11 C12 1.386(2) . ?
C5 C6 1.387(3) . ?
C13 C14 1.377(3) . ?
C13 C12 1.373(3) . ?
C7 C6 1.377(3) . ?

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
O18 S16 N3 106.35(7) . . ?
O18 S16 C21 108.41(7) . . ?
O17 S16 O18 121.46(7) . . ?
O17 S16 N3 105.88(7) . . ?
O17 S16 C21 108.70(7) . . ?
N3 S16 C21 104.81(6) . . ?
C10 N1 C2 120.75(12) . . ?
C9 N1 C2 107.11(11) . . ?
C9 N1 C10 126.95(12) . . ?
C2 N3 S16 115.27(9) . . ?
C4 N3 S16 115.47(9) . . ?
C4 N3 C2 104.21(11) . . ?
N1 C2 N3 104.54(10) . . ?
N1 C2 C19 111.12(12) . . ?
C19 C2 N3 109.48(12) . . ?
C15 C10 N1 118.80(13) . . ?
C11 C10 N1 122.14(13) . . ?
C11 C10 C15 119.04(14) . . ?
C4 C9 N1 109.60(13) . . ?
C4 C9 C8 119.53(14) . . ?
C8 C9 N1 130.82(15) . . ?
O29 N27 C24 117.15(18) . . ?
O28 N27 O29 124.54(18) . . ?
O28 N27 C24 118.32(16) . . ?
C9 C4 N3 109.56(12) . . ?
C5 C4 N3 127.79(15) . . ?
C5 C4 C9 122.64(15) . . ?
C22 C21 S16 119.56(11) . . ?
C22 C21 C26 121.71(15) . . ?
C26 C21 S16 118.61(12) . . ?
C23 C22 C21 119.12(14) . . ?
C14 C15 C10 120.32(15) . . ?
C24 C25 C26 118.57(14) . . ?
C20 C19 C2 178.0(2) . . ?
C24 C23 C22 118.24(15) . . ?
C25 C24 N27 118.47(15) . . ?
C25 C24 C23 123.37(16) . . ?
C23 C24 N27 118.14(15) . . ?
C25 C26 C21 118.97(15) . . ?
C7 C8 C9 117.69(17) . . ?
C12 C11 C10 119.58(15) . . ?
C4 C5 C6 117.54(17) . . ?
C12 C13 C14 119.30(16) . . ?
C13 C14 C15 120.47(16) . . ?
C13 C12 C11 121.25(16) . . ?
C6 C7 C8 122.26(17) . . ?
C7 C6 C5 120.33(16) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
