# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_210318b
_database_code_depnum_ccdc_archive 'CCDC 2088908'
loop_
_audit_author_name
_audit_author_address
'Xiu Duan'
;Nanjing TechUniversity
China
;
_audit_update_record             
;
2021-06-09 deposited with the CCDC.	2021-10-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 N3 O S'
_chemical_formula_weight         361.45

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   7.2246(8)
_cell_length_b                   11.8631(11)
_cell_length_c                   20.815(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1784.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2431
_cell_measurement_theta_min      2.604
_cell_measurement_theta_max      23.917

_exptl_crystal_description       crystals
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      1.346
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9168
_exptl_absorpt_correction_T_max  0.9488
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8971
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_av_sigmaI/netI    0.0763
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3151
_reflns_number_gt                2247
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0686P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.23(13)
_refine_ls_number_reflns         3151
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1390
_refine_ls_wR_factor_gt          0.1279
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.1314(5) 0.3346(2) 0.34121(12) 0.0398(7) Uani 1 1 d . . .
N2 N 0.1255(5) 0.2659(2) 0.44761(11) 0.0398(8) Uani 1 1 d . . .
H2 H 0.1478 0.2047 0.4684 0.048 Uiso 1 1 calc R . .
N3 N 0.7819(6) 0.6564(4) 0.55399(18) 0.0903(15) Uani 1 1 d . . .
O1 O 0.1482(4) 0.1554(2) 0.55615(9) 0.0445(7) Uani 1 1 d . . .
S1 S 0.10859(17) 0.11912(8) 0.35020(4) 0.0496(3) Uani 1 1 d . . .
C1 C 0.1244(5) 0.2550(3) 0.38171(13) 0.0346(8) Uani 1 1 d . . .
C2 C 0.1271(6) 0.2931(3) 0.27985(15) 0.0393(9) Uani 1 1 d . . .
C3 C 0.1137(6) 0.1780(3) 0.27403(15) 0.0407(9) Uani 1 1 d . . .
C4 C 0.1056(6) 0.1261(3) 0.21519(17) 0.0547(11) Uani 1 1 d . . .
H4 H 0.0956 0.0481 0.2119 0.066 Uiso 1 1 calc R . .
C5 C 0.1126(7) 0.1925(4) 0.16148(16) 0.0557(11) Uani 1 1 d . . .
H5 H 0.1069 0.1592 0.1211 0.067 Uiso 1 1 calc R . .
C6 C 0.1278(6) 0.3073(3) 0.16648(15) 0.0528(11) Uani 1 1 d . . .
H6 H 0.1334 0.3510 0.1294 0.063 Uiso 1 1 calc R . .
C7 C 0.1350(6) 0.3582(3) 0.22521(15) 0.0481(10) Uani 1 1 d . . .
H7 H 0.1451 0.4362 0.2283 0.058 Uiso 1 1 calc R . .
C8 C 0.6829(6) 0.6364(4) 0.5145(2) 0.0548(11) Uani 1 1 d . . .
C9 C 0.5544(5) 0.6072(3) 0.46392(16) 0.0489(10) Uani 1 1 d . . .
H9A H 0.6132 0.5535 0.4353 0.059 Uiso 1 1 calc R . .
H9B H 0.5265 0.6743 0.4392 0.059 Uiso 1 1 calc R . .
C10 C 0.3766(6) 0.5575(3) 0.48809(14) 0.0433(9) Uani 1 1 d . . .
H10A H 0.3127 0.6124 0.5146 0.052 Uiso 1 1 calc R . .
H10B H 0.4032 0.4921 0.5145 0.052 Uiso 1 1 calc R . .
C11 C 0.2545(6) 0.5236(3) 0.43297(14) 0.0391(9) Uani 1 1 d . . .
H11A H 0.3213 0.4706 0.4061 0.047 Uiso 1 1 calc R . .
H11B H 0.2281 0.5898 0.4072 0.047 Uiso 1 1 calc R . .
C12 C 0.0725(5) 0.4703(3) 0.45329(15) 0.0376(9) Uani 1 1 d . . .
H12A H 0.0096 0.5208 0.4827 0.045 Uiso 1 1 calc R . .
H12B H -0.0055 0.4612 0.4157 0.045 Uiso 1 1 calc R . .
C13 C 0.0969(5) 0.3582(3) 0.48500(14) 0.0335(8) Uani 1 1 d . . .
C14 C 0.0948(5) 0.3481(3) 0.54932(14) 0.0371(9) Uani 1 1 d . . .
H14 H 0.0719 0.4129 0.5732 0.044 Uiso 1 1 calc R . .
C15 C 0.1248(6) 0.2461(3) 0.58390(14) 0.0372(9) Uani 1 1 d . . .
C16 C 0.1202(5) 0.2475(3) 0.65536(13) 0.0352(8) Uani 1 1 d . . .
C17 C 0.1337(6) 0.1480(3) 0.68781(15) 0.0505(11) Uani 1 1 d . . .
H17 H 0.1424 0.0810 0.6648 0.061 Uiso 1 1 calc R . .
C18 C 0.1349(6) 0.1444(4) 0.75382(16) 0.0619(13) Uani 1 1 d . . .
H18 H 0.1427 0.0756 0.7750 0.074 Uiso 1 1 calc R . .
C19 C 0.1245(6) 0.2421(4) 0.78820(15) 0.0539(11) Uani 1 1 d . . .
H19 H 0.1272 0.2402 0.8329 0.065 Uiso 1 1 calc R . .
C20 C 0.1103(7) 0.3417(4) 0.75708(16) 0.0603(12) Uani 1 1 d . . .
H20 H 0.1008 0.4082 0.7805 0.072 Uiso 1 1 calc R . .
C21 C 0.1096(6) 0.3453(3) 0.69108(15) 0.0513(11) Uani 1 1 d . . .
H21 H 0.1020 0.4145 0.6702 0.062 Uiso 1 1 calc R . .


_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
N1 C1 1.267(4) . ?
N1 C2 1.369(4) . ?
N2 C13 1.360(4) . ?
N2 C1 1.378(3) . ?
N2 H2 0.8600 . ?
N3 C8 1.115(5) . ?
O1 C15 1.233(4) . ?
S1 C3 1.733(3) . ?
S1 C1 1.744(3) . ?
C2 C3 1.375(5) . ?
C2 C7 1.376(4) . ?
C3 C4 1.372(4) . ?
C4 C5 1.368(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.364(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.446(6) . ?
C9 C10 1.500(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.502(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.519(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.495(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.344(4) . ?
C14 C15 1.424(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.488(4) . ?
C16 C17 1.364(5) . ?
C16 C21 1.380(5) . ?
C17 C18 1.375(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.364(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.351(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.374(4) . ?
C20 H20 0.9300 . ?
C21 H21 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
C1 N1 C2 110.6(3) . . ?
C13 N2 C1 130.1(3) . . ?
C13 N2 H2 114.9 . . ?
C1 N2 H2 114.9 . . ?
C3 S1 C1 88.29(15) . . ?
N1 C1 N2 126.3(3) . . ?
N1 C1 S1 116.2(2) . . ?
N2 C1 S1 117.5(2) . . ?
N1 C2 C3 116.2(3) . . ?
N1 C2 C7 124.6(3) . . ?
C3 C2 C7 119.2(3) . . ?
C4 C3 C2 121.8(3) . . ?
C4 C3 S1 129.4(3) . . ?
C2 C3 S1 108.8(3) . . ?
C5 C4 C3 118.0(4) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 120.7(3) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C2 119.4(4) . . ?
C6 C7 H7 120.3 . . ?
C2 C7 H7 120.3 . . ?
N3 C8 C9 178.4(5) . . ?
C8 C9 C10 113.5(3) . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 C11 110.6(3) . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C10 C11 C12 114.0(3) . . ?
C10 C11 H11A 108.7 . . ?
C12 C11 H11A 108.7 . . ?
C10 C11 H11B 108.7 . . ?
C12 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C13 C12 C11 113.0(3) . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 N2 120.0(3) . . ?
C14 C13 C12 121.2(3) . . ?
N2 C13 C12 118.8(3) . . ?
C13 C14 C15 125.3(3) . . ?
C13 C14 H14 117.4 . . ?
C15 C14 H14 117.4 . . ?
O1 C15 C14 121.7(3) . . ?
O1 C15 C16 118.8(3) . . ?
C14 C15 C16 119.5(3) . . ?
C17 C16 C21 117.7(3) . . ?
C17 C16 C15 118.9(3) . . ?
C21 C16 C15 123.3(3) . . ?
C16 C17 C18 121.4(4) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C19 C18 C17 119.9(4) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C20 C19 C18 119.7(3) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C21 120.5(4) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C16 120.8(4) . . ?
C20 C21 H21 119.6 . . ?
C16 C21 H21 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 N2 -179.9(4) . . . . ?
C2 N1 C1 S1 -0.8(4) . . . . ?
C13 N2 C1 N1 14.9(7) . . . . ?
C13 N2 C1 S1 -164.2(3) . . . . ?
C3 S1 C1 N1 0.4(3) . . . . ?
C3 S1 C1 N2 179.6(3) . . . . ?
C1 N1 C2 C3 0.9(5) . . . . ?
C1 N1 C2 C7 -179.2(4) . . . . ?
N1 C2 C3 C4 179.1(4) . . . . ?
C7 C2 C3 C4 -0.9(7) . . . . ?
N1 C2 C3 S1 -0.6(5) . . . . ?
C7 C2 C3 S1 179.5(3) . . . . ?
C1 S1 C3 C4 -179.5(5) . . . . ?
C1 S1 C3 C2 0.1(3) . . . . ?
C2 C3 C4 C5 0.5(7) . . . . ?
S1 C3 C4 C5 -179.9(4) . . . . ?
C3 C4 C5 C6 0.2(7) . . . . ?
C4 C5 C6 C7 -0.5(8) . . . . ?
C5 C6 C7 C2 0.1(7) . . . . ?
N1 C2 C7 C6 -179.4(4) . . . . ?
C3 C2 C7 C6 0.5(7) . . . . ?
N3 C8 C9 C10 58(16) . . . . ?
C8 C9 C10 C11 -177.0(3) . . . . ?
C9 C10 C11 C12 178.9(3) . . . . ?
C10 C11 C12 C13 -67.1(4) . . . . ?
C1 N2 C13 C14 176.4(4) . . . . ?
C1 N2 C13 C12 -5.0(6) . . . . ?
C11 C12 C13 C14 98.9(4) . . . . ?
C11 C12 C13 N2 -79.7(4) . . . . ?
N2 C13 C14 C15 1.5(6) . . . . ?
C12 C13 C14 C15 -177.1(4) . . . . ?
C13 C14 C15 O1 -3.2(7) . . . . ?
C13 C14 C15 C16 179.4(4) . . . . ?
O1 C15 C16 C17 -2.9(6) . . . . ?
C14 C15 C16 C17 174.6(4) . . . . ?
O1 C15 C16 C21 174.7(4) . . . . ?
C14 C15 C16 C21 -7.8(6) . . . . ?
C21 C16 C17 C18 0.7(6) . . . . ?
C15 C16 C17 C18 178.4(4) . . . . ?
C16 C17 C18 C19 -0.8(7) . . . . ?
C17 C18 C19 C20 1.0(7) . . . . ?
C18 C19 C20 C21 -1.2(7) . . . . ?
C19 C20 C21 C16 1.2(8) . . . . ?
C17 C16 C21 C20 -0.9(6) . . . . ?
C15 C16 C21 C20 -178.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.057
