# 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. 
# 
#######################################################################

data_20220603_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2256590'
loop_
_audit_author_name
_audit_author_address
li
;Zhejiang Sci Tech University
China
;
_audit_update_record             
;
2023-04-15 deposited with the CCDC.	2023-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18 N2 O2 S'
_chemical_formula_weight         374.44

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   7.817(3)
_cell_length_b                   12.371(5)
_cell_length_c                   19.295(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1865.8(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4484
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      26.58

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.193
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11468
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.955
_diffrn_reflns_theta_max         27.473
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4197
_reflns_number_gt                3703
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_max     0.976
_reflns_Friedel_fraction_full    0.992

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0600P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1399 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4197
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0981
_refine_ls_wR_factor_gt          0.0937
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.51925(7) 0.17908(4) 0.69559(3) 0.03674(16) Uani 1 1 d . . . . .
O2 O 0.5877(3) 0.26663(15) 0.73495(9) 0.0503(5) Uani 1 1 d . . . . .
O3 O 0.3598(2) 0.13188(16) 0.71464(9) 0.0532(5) Uani 1 1 d . . . . .
N1 N 0.7341(3) 0.36071(16) 0.47895(10) 0.0377(5) Uani 1 1 d . . . . .
N2 N 0.4990(3) 0.21700(15) 0.61584(9) 0.0354(4) Uani 1 1 d . . . . .
C1 C 0.7340(4) 0.0834(2) 0.51389(14) 0.0498(7) Uani 1 1 d . . . . .
H1 H 0.774090 0.088755 0.559148 0.060 Uiso 1 1 calc R U . . .
C2 C 0.7429(5) -0.0145(2) 0.47969(18) 0.0695(10) Uani 1 1 d . . . . .
H2 H 0.790663 -0.074234 0.501644 0.083 Uiso 1 1 calc R U . . .
C3 C 0.6816(5) -0.0237(3) 0.4136(2) 0.0770(11) Uani 1 1 d . . . . .
H3 H 0.686171 -0.089872 0.390805 0.092 Uiso 1 1 calc R U . . .
C4 C 0.6141(5) 0.0640(3) 0.38109(16) 0.0713(10) Uani 1 1 d . . . . .
H4 H 0.572051 0.057500 0.336184 0.086 Uiso 1 1 calc R U . . .
C5 C 0.6074(4) 0.1634(2) 0.41464(14) 0.0525(7) Uani 1 1 d . . . . .
H5 H 0.563023 0.223342 0.391749 0.063 Uiso 1 1 calc R U . . .
C6 C 0.6663(3) 0.17355(19) 0.48175(11) 0.0364(5) Uani 1 1 d . . . . .
C7 C 0.6652(3) 0.28195(17) 0.51573(11) 0.0334(5) Uani 1 1 d . . . . .
C8 C 0.5967(3) 0.40312(19) 0.60925(12) 0.0418(6) Uani 1 1 d . . . . .
H8 H 0.549666 0.416946 0.652619 0.050 Uiso 1 1 calc R U . . .
C9 C 0.6735(3) 0.48698(19) 0.57167(13) 0.0414(6) Uani 1 1 d . . . . .
C10 C 0.7388(3) 0.46295(19) 0.50554(13) 0.0391(5) Uani 1 1 d . . . . .
C11 C 0.8089(4) 0.5462(2) 0.46443(15) 0.0530(7) Uani 1 1 d . . . . .
H11 H 0.852219 0.531018 0.420610 0.064 Uiso 1 1 calc R U . . .
C12 C 0.8126(5) 0.6493(2) 0.48956(17) 0.0626(8) Uani 1 1 d . . . . .
H12 H 0.859988 0.704075 0.462711 0.075 Uiso 1 1 calc R U . . .
C13 C 0.7468(5) 0.6739(2) 0.55451(16) 0.0644(8) Uani 1 1 d . . . . .
H13 H 0.748537 0.745036 0.570006 0.077 Uiso 1 1 calc R U . . .
C14 C 0.6801(4) 0.5959(2) 0.59564(16) 0.0579(8) Uani 1 1 d . . . . .
H14 H 0.638717 0.613368 0.639419 0.069 Uiso 1 1 calc R U . . .
C15 C 0.6735(3) 0.07573(18) 0.69592(12) 0.0350(5) Uani 1 1 d . . . . .
C16 C 0.8465(3) 0.1021(2) 0.69234(14) 0.0450(6) Uani 1 1 d . . . . .
H16 H 0.880659 0.174053 0.693355 0.054 Uiso 1 1 calc R U . . .
C17 C 0.9665(4) 0.0211(2) 0.68731(13) 0.0529(7) Uani 1 1 d . . . . .
H17 H 1.081894 0.038890 0.684410 0.063 Uiso 1 1 calc R U . . .
C18 C 0.9174(4) -0.0868(2) 0.68650(14) 0.0536(7) Uani 1 1 d . . . . .
C19 C 0.7462(4) -0.1114(2) 0.69226(15) 0.0513(6) Uani 1 1 d . . . . .
H19 H 0.712284 -0.183398 0.693273 0.062 Uiso 1 1 calc R U . . .
C20 C 0.6237(3) -0.03088(19) 0.69658(13) 0.0414(5) Uani 1 1 d . . . . .
H20 H 0.508443 -0.048776 0.699900 0.050 Uiso 1 1 calc R U . . .
C21 C 1.0485(5) -0.1757(3) 0.6794(2) 0.0900(12) Uani 1 1 d . . . . .
H21A H 1.142617 -0.161735 0.710101 0.135 Uiso 1 1 calc R U . . .
H21B H 1.089169 -0.178161 0.632502 0.135 Uiso 1 1 calc R U . . .
H21C H 0.997052 -0.243746 0.691157 0.135 Uiso 1 1 calc R U . . .
C22 C 0.5908(3) 0.30136(17) 0.58238(11) 0.0330(5) Uani 1 1 d . . . . .
H2C H 0.424(4) 0.181(2) 0.5939(16) 0.051(8) Uiso 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 O3 1.4247(19) . ?
S1 O2 1.4271(18) . ?
S1 N2 1.6164(19) . ?
S1 C15 1.758(2) . ?
N1 C7 1.320(3) . ?
N1 C10 1.365(3) . ?
N2 C22 1.422(3) . ?
N2 H2C 0.84(3) . ?
C1 C6 1.381(4) . ?
C1 C2 1.381(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.368(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.360(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.493(3) . ?
C7 C22 1.432(3) . ?
C8 C22 1.362(3) . ?
C8 C9 1.401(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.406(4) . ?
C9 C14 1.426(3) . ?
C10 C11 1.411(4) . ?
C11 C12 1.365(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.388(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.353(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C20 1.375(3) . ?
C15 C16 1.392(3) . ?
C16 C17 1.376(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.390(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.377(4) . ?
C18 C21 1.509(4) . ?
C19 C20 1.384(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
O3 S1 O2 120.12(12) . . ?
O3 S1 N2 106.20(11) . . ?
O2 S1 N2 108.85(11) . . ?
O3 S1 C15 107.53(12) . . ?
O2 S1 C15 107.03(12) . . ?
N2 S1 C15 106.37(10) . . ?
C7 N1 C10 119.5(2) . . ?
C22 N2 S1 126.58(16) . . ?
C22 N2 H2C 120(2) . . ?
S1 N2 H2C 113(2) . . ?
C6 C1 C2 120.8(3) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 118.4(2) . . ?
C5 C6 C7 119.4(2) . . ?
C1 C6 C7 122.0(2) . . ?
N1 C7 C22 121.6(2) . . ?
N1 C7 C6 115.12(19) . . ?
C22 C7 C6 123.21(19) . . ?
C22 C8 C9 120.1(2) . . ?
C22 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C10 117.9(2) . . ?
C8 C9 C14 123.2(2) . . ?
C10 C9 C14 118.8(2) . . ?
N1 C10 C9 121.8(2) . . ?
N1 C10 C11 118.4(2) . . ?
C9 C10 C11 119.8(2) . . ?
C12 C11 C10 119.4(3) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 121.2(3) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C12 121.1(3) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C9 119.8(3) . . ?
C13 C14 H14 120.1 . . ?
C9 C14 H14 120.1 . . ?
C20 C15 C16 120.0(2) . . ?
C20 C15 S1 120.22(19) . . ?
C16 C15 S1 119.72(19) . . ?
C17 C16 C15 119.7(2) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 120.8(3) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C19 C18 C17 118.7(3) . . ?
C19 C18 C21 120.4(3) . . ?
C17 C18 C21 120.9(3) . . ?
C18 C19 C20 121.2(2) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C15 C20 C19 119.6(2) . . ?
C15 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C8 C22 N2 121.5(2) . . ?
C8 C22 C7 118.9(2) . . ?
N2 C22 C7 119.33(18) . . ?

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
O3 S1 N2 C22 154.07(19) . . . . ?
O2 S1 N2 C22 23.4(2) . . . . ?
C15 S1 N2 C22 -91.6(2) . . . . ?
C6 C1 C2 C3 -1.1(5) . . . . ?
C1 C2 C3 C4 0.9(6) . . . . ?
C2 C3 C4 C5 0.3(6) . . . . ?
C3 C4 C5 C6 -1.3(5) . . . . ?
C4 C5 C6 C1 1.0(4) . . . . ?
C4 C5 C6 C7 177.3(3) . . . . ?
C2 C1 C6 C5 0.1(4) . . . . ?
C2 C1 C6 C7 -176.0(3) . . . . ?
C10 N1 C7 C22 1.7(4) . . . . ?
C10 N1 C7 C6 179.9(2) . . . . ?
C5 C6 C7 N1 -49.7(3) . . . . ?
C1 C6 C7 N1 126.4(3) . . . . ?
C5 C6 C7 C22 128.5(3) . . . . ?
C1 C6 C7 C22 -55.4(3) . . . . ?
C22 C8 C9 C10 1.7(4) . . . . ?
C22 C8 C9 C14 178.2(3) . . . . ?
C7 N1 C10 C9 0.6(4) . . . . ?
C7 N1 C10 C11 -178.3(2) . . . . ?
C8 C9 C10 N1 -2.3(4) . . . . ?
C14 C9 C10 N1 -179.0(3) . . . . ?
C8 C9 C10 C11 176.6(3) . . . . ?
C14 C9 C10 C11 0.0(4) . . . . ?
N1 C10 C11 C12 179.0(3) . . . . ?
C9 C10 C11 C12 0.1(5) . . . . ?
C10 C11 C12 C13 -0.7(5) . . . . ?
C11 C12 C13 C14 1.4(6) . . . . ?
C12 C13 C14 C9 -1.4(6) . . . . ?
C8 C9 C14 C13 -175.8(3) . . . . ?
C10 C9 C14 C13 0.7(5) . . . . ?
O3 S1 C15 C20 15.3(2) . . . . ?
O2 S1 C15 C20 145.6(2) . . . . ?
N2 S1 C15 C20 -98.2(2) . . . . ?
O3 S1 C15 C16 -167.6(2) . . . . ?
O2 S1 C15 C16 -37.3(2) . . . . ?
N2 S1 C15 C16 78.9(2) . . . . ?
C20 C15 C16 C17 2.0(4) . . . . ?
S1 C15 C16 C17 -175.1(2) . . . . ?
C15 C16 C17 C18 -0.7(4) . . . . ?
C16 C17 C18 C19 -1.3(4) . . . . ?
C16 C17 C18 C21 178.7(3) . . . . ?
C17 C18 C19 C20 2.0(4) . . . . ?
C21 C18 C19 C20 -177.9(3) . . . . ?
C16 C15 C20 C19 -1.3(4) . . . . ?
S1 C15 C20 C19 175.8(2) . . . . ?
C18 C19 C20 C15 -0.8(4) . . . . ?
C9 C8 C22 N2 -173.6(2) . . . . ?
C9 C8 C22 C7 0.4(4) . . . . ?
S1 N2 C22 C8 -53.3(3) . . . . ?
S1 N2 C22 C7 132.7(2) . . . . ?
N1 C7 C22 C8 -2.2(4) . . . . ?
C6 C7 C22 C8 179.7(2) . . . . ?
N1 C7 C22 N2 171.9(2) . . . . ?
C6 C7 C22 N2 -6.1(3) . . . . ?

_refine_diff_density_max         0.171
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.055

