# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_T9
_database_code_depnum_ccdc_archive 'CCDC 2210351'
loop_
_audit_author_name
_audit_author_address
P
;Hebei University
China
;
_audit_update_record             
;
2022-09-30 deposited with the CCDC.	2022-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H13 N O2 S'
_chemical_formula_weight         355.39

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   11.7823(9)
_cell_length_b                   17.2564(12)
_cell_length_c                   8.5563(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1739.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    7385
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      26.75

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.202
_shelx_estimated_absorpt_T_min   0.915
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.6880
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19380
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.093
_diffrn_reflns_theta_max         26.782
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             3566
_reflns_number_gt                3159
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.799
_reflns_Friedel_fraction_max     0.916
_reflns_Friedel_fraction_full    0.929

_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 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0229P)²+0.3890P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1261 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3566
_refine_ls_number_parameters     235
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0788
_refine_ls_wR_factor_gt          0.0732
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_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
O2 O -0.0050(2) 0.41350(14) 0.5513(4) 0.0929(8) Uani 1 1 d . . . . .
O1 O 0.42938(18) 0.78383(11) 0.4331(3) 0.0753(7) Uani 1 1 d . . . . .
S1 S 0.45808(7) 0.66340(6) 0.18699(11) 0.0752(3) Uani 1 1 d . . . . .
N1 N 0.6724(2) 0.71972(18) 0.2747(4) 0.0787(8) Uani 1 1 d . . . . .
C5 C 0.2869(3) 0.76248(19) 0.8799(4) 0.0777(10) Uani 1 1 d . . . . .
H5 H 0.298063 0.799564 0.957299 0.093 Uiso 1 1 calc R U . . .
C4 C 0.3405(3) 0.77000(16) 0.7386(4) 0.0625(8) Uani 1 1 d . . . . .
H4 H 0.386974 0.812530 0.719844 0.075 Uiso 1 1 calc R U . . .
C3 C 0.3254(2) 0.71411(14) 0.6229(3) 0.0470(6) Uani 1 1 d . . . . .
C8 C 0.2580(2) 0.64968(14) 0.6529(3) 0.0456(6) Uani 1 1 d . . . . .
C9 C 0.24368(18) 0.58460(13) 0.5338(3) 0.0408(5) Uani 1 1 d . . . . .
C15 C 0.32806(18) 0.58961(14) 0.3975(3) 0.0423(5) Uani 1 1 d . . . . .
C16 C 0.3427(2) 0.51869(15) 0.3011(3) 0.0464(6) Uani 1 1 d . . . . .
C21 C 0.4294(2) 0.46773(17) 0.3422(4) 0.0592(7) Uani 1 1 d . . . . .
H21 H 0.476311 0.479376 0.426353 0.071 Uiso 1 1 calc R U . . .
C20 C 0.4463(3) 0.40030(19) 0.2594(4) 0.0718(9) Uani 1 1 d . . . . .
H20 H 0.503574 0.366244 0.288958 0.086 Uiso 1 1 calc R U . . .
C19 C 0.3793(3) 0.38342(19) 0.1347(4) 0.0755(10) Uani 1 1 d . . . . .
H19 H 0.391036 0.337856 0.078914 0.091 Uiso 1 1 calc R U . . .
C7 C 0.2023(3) 0.64463(17) 0.7955(4) 0.0635(8) Uani 1 1 d . . . . .
H7 H 0.154418 0.602875 0.814950 0.076 Uiso 1 1 calc R U . . .
C6 C 0.2168(3) 0.70027(18) 0.9078(4) 0.0781(10) Uani 1 1 d . . . . .
H6 H 0.179203 0.695995 1.003042 0.094 Uiso 1 1 calc R U . . .
C14 C 0.2574(2) 0.50781(14) 0.6167(3) 0.0436(5) Uani 1 1 d . . . . .
H14 H 0.326144 0.497746 0.666069 0.052 Uiso 1 1 calc R U . . .
C13 C 0.1775(2) 0.45408(14) 0.6234(3) 0.0507(6) Uani 1 1 d . . . . .
H13 H 0.191858 0.408550 0.678095 0.061 Uiso 1 1 calc R U . . .
C12 C 0.0672(2) 0.46400(17) 0.5474(4) 0.0570(7) Uani 1 1 d . . . . .
C11 C 0.0485(2) 0.53789(17) 0.4692(4) 0.0563(7) Uani 1 1 d . . . . .
H11 H -0.021775 0.547059 0.423260 0.068 Uiso 1 1 calc R U . . .
C10 C 0.12668(19) 0.59229(15) 0.4607(3) 0.0483(6) Uani 1 1 d . . . . .
H10 H 0.109409 0.637711 0.407272 0.058 Uiso 1 1 calc R U . . .
C17 C 0.2753(2) 0.50150(19) 0.1751(4) 0.0610(7) Uani 1 1 d . . . . .
H17 H 0.217066 0.534907 0.145846 0.073 Uiso 1 1 calc R U . . .
C18 C 0.2948(3) 0.4331(2) 0.0908(4) 0.0744(9) Uani 1 1 d . . . . .
H18 H 0.250010 0.421494 0.004392 0.089 Uiso 1 1 calc R U . . .
C1 C 0.3839(2) 0.65555(16) 0.3674(3) 0.0473(6) Uani 1 1 d . . . . .
C2 C 0.3823(2) 0.72398(15) 0.4706(4) 0.0510(6) Uani 1 1 d . . . . .
C22 C 0.5840(3) 0.69814(17) 0.2460(3) 0.0552(7) 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
O2 C12 1.218(3) . ?
O1 C2 1.215(3) . ?
S1 C22 1.678(3) . ?
S1 C1 1.779(3) . ?
N1 C22 1.133(4) . ?
C5 C4 1.370(5) . ?
C5 C6 1.376(5) . ?
C5 H5 0.9300 . ?
C4 C3 1.393(4) . ?
C4 H4 0.9300 . ?
C3 C8 1.390(3) . ?
C3 C2 1.475(4) . ?
C8 C7 1.388(4) . ?
C8 C9 1.526(3) . ?
C9 C14 1.512(3) . ?
C9 C10 1.520(3) . ?
C9 C15 1.535(3) . ?
C15 C1 1.339(3) . ?
C15 C16 1.486(3) . ?
C16 C17 1.372(4) . ?
C16 C21 1.393(4) . ?
C21 C20 1.377(4) . ?
C21 H21 0.9300 . ?
C20 C19 1.359(5) . ?
C20 H20 0.9300 . ?
C19 C18 1.366(5) . ?
C19 H19 0.9300 . ?
C7 C6 1.369(4) . ?
C7 H7 0.9300 . ?
C6 H6 0.9300 . ?
C14 C13 1.323(3) . ?
C14 H14 0.9300 . ?
C13 C12 1.463(4) . ?
C13 H13 0.9300 . ?
C12 C11 1.457(4) . ?
C11 C10 1.317(4) . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?
C17 C18 1.402(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C1 C2 1.475(4) . ?

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
C22 S1 C1 101.56(13) . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C8 C3 C4 119.7(3) . . ?
C8 C3 C2 121.0(2) . . ?
C4 C3 C2 119.3(2) . . ?
C7 C8 C3 118.9(2) . . ?
C7 C8 C9 119.2(2) . . ?
C3 C8 C9 121.9(2) . . ?
C14 C9 C10 111.5(2) . . ?
C14 C9 C8 108.7(2) . . ?
C10 C9 C8 108.12(19) . . ?
C14 C9 C15 109.69(19) . . ?
C10 C9 C15 105.7(2) . . ?
C8 C9 C15 113.22(19) . . ?
C1 C15 C16 122.4(2) . . ?
C1 C15 C9 120.8(2) . . ?
C16 C15 C9 116.8(2) . . ?
C17 C16 C21 119.1(3) . . ?
C17 C16 C15 123.2(2) . . ?
C21 C16 C15 117.7(2) . . ?
C20 C21 C16 120.7(3) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?
C19 C20 C21 120.1(3) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C19 C18 120.3(3) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C6 C7 C8 120.9(3) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C7 C6 C5 120.0(3) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C13 C14 C9 124.0(2) . . ?
C13 C14 H14 118.0 . . ?
C9 C14 H14 118.0 . . ?
C14 C13 C12 122.1(2) . . ?
C14 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
O2 C12 C11 122.2(3) . . ?
O2 C12 C13 121.6(3) . . ?
C11 C12 C13 116.2(2) . . ?
C10 C11 C12 122.9(2) . . ?
C10 C11 H11 118.5 . . ?
C12 C11 H11 118.5 . . ?
C11 C10 C9 123.3(2) . . ?
C11 C10 H10 118.3 . . ?
C9 C10 H10 118.3 . . ?
C16 C17 C18 119.4(3) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C19 C18 C17 120.4(3) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C15 C1 C2 124.0(2) . . ?
C15 C1 S1 118.2(2) . . ?
C2 C1 S1 117.71(19) . . ?
O1 C2 C1 121.1(3) . . ?
O1 C2 C3 122.6(3) . . ?
C1 C2 C3 116.3(2) . . ?
N1 C22 S1 174.5(3) . . ?

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
C6 C5 C4 C3 -0.9(5) . . . . ?
C5 C4 C3 C8 -1.6(4) . . . . ?
C5 C4 C3 C2 179.0(3) . . . . ?
C4 C3 C8 C7 3.3(4) . . . . ?
C2 C3 C8 C7 -177.2(3) . . . . ?
C4 C3 C8 C9 -176.7(2) . . . . ?
C2 C3 C8 C9 2.8(3) . . . . ?
C7 C8 C9 C14 -46.1(3) . . . . ?
C3 C8 C9 C14 133.9(2) . . . . ?
C7 C8 C9 C10 75.1(3) . . . . ?
C3 C8 C9 C10 -104.9(3) . . . . ?
C7 C8 C9 C15 -168.2(2) . . . . ?
C3 C8 C9 C15 11.8(3) . . . . ?
C14 C9 C15 C1 -139.0(2) . . . . ?
C10 C9 C15 C1 100.7(3) . . . . ?
C8 C9 C15 C1 -17.4(3) . . . . ?
C14 C9 C15 C16 41.9(3) . . . . ?
C10 C9 C15 C16 -78.4(3) . . . . ?
C8 C9 C15 C16 163.4(2) . . . . ?
C1 C15 C16 C17 -91.9(3) . . . . ?
C9 C15 C16 C17 87.2(3) . . . . ?
C1 C15 C16 C21 88.1(3) . . . . ?
C9 C15 C16 C21 -92.7(3) . . . . ?
C17 C16 C21 C20 -1.1(4) . . . . ?
C15 C16 C21 C20 178.8(3) . . . . ?
C16 C21 C20 C19 1.1(5) . . . . ?
C21 C20 C19 C18 -0.1(5) . . . . ?
C3 C8 C7 C6 -2.8(5) . . . . ?
C9 C8 C7 C6 177.3(3) . . . . ?
C8 C7 C6 C5 0.3(6) . . . . ?
C4 C5 C6 C7 1.5(6) . . . . ?
C10 C9 C14 C13 0.5(3) . . . . ?
C8 C9 C14 C13 119.5(3) . . . . ?
C15 C9 C14 C13 -116.2(3) . . . . ?
C9 C14 C13 C12 1.0(4) . . . . ?
C14 C13 C12 O2 178.4(3) . . . . ?
C14 C13 C12 C11 -2.4(4) . . . . ?
O2 C12 C11 C10 -178.3(3) . . . . ?
C13 C12 C11 C10 2.5(4) . . . . ?
C12 C11 C10 C9 -1.2(4) . . . . ?
C14 C9 C10 C11 -0.4(4) . . . . ?
C8 C9 C10 C11 -119.8(3) . . . . ?
C15 C9 C10 C11 118.7(3) . . . . ?
C21 C16 C17 C18 0.1(4) . . . . ?
C15 C16 C17 C18 -179.8(3) . . . . ?
C20 C19 C18 C17 -0.9(5) . . . . ?
C16 C17 C18 C19 0.9(5) . . . . ?
C16 C15 C1 C2 -172.4(2) . . . . ?
C9 C15 C1 C2 8.5(4) . . . . ?
C16 C15 C1 S1 11.3(3) . . . . ?
C9 C15 C1 S1 -167.76(18) . . . . ?
C22 S1 C1 C15 -132.7(2) . . . . ?
C22 S1 C1 C2 50.8(2) . . . . ?
C15 C1 C2 O1 -175.8(3) . . . . ?
S1 C1 C2 O1 0.5(3) . . . . ?
C15 C1 C2 C3 6.9(4) . . . . ?
S1 C1 C2 C3 -176.78(18) . . . . ?
C8 C3 C2 O1 170.2(3) . . . . ?
C4 C3 C2 O1 -10.4(4) . . . . ?
C8 C3 C2 C1 -12.6(3) . . . . ?
C4 C3 C2 C1 166.9(2) . . . . ?

_refine_diff_density_max         0.175
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.028

