# Electronic Supplementary Material (ESI) for Green 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_2
_database_code_depnum_ccdc_archive 'CCDC 2191796'
loop_
_audit_author_name
_audit_author_address
'Qiang Zhong'
;Huaibei Normal University
China
;
_audit_update_record             
;
2022-07-21 deposited with the CCDC.	2023-04-14 downloaded from the CCDC.
;
_audit_creation_date             2022-07-21
_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         'C21 H18 N2 O3 S'
_chemical_formula_sum            'C21 H19 N2 O3 S'
_chemical_formula_weight         379.44
_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 0.0033 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                   14.2948(8)
_cell_length_b                   8.5708(4)
_cell_length_c                   15.3612(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.345(5)
_cell_angle_gamma                90
_cell_volume                     1873.84(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5869
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.8230
_cell_measurement_theta_min      2.7210
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellowish
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cubic
_exptl_crystal_F_000             796
_exptl_crystal_recrystallization_method cubic
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.827
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17066
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.827
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.645
_diffrn_reflns_theta_min         2.724
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.827
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3013
_reflns_number_total             4789
_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 1.3 (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4789
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0517
_refine_ls_restrained_S_all      1.026
_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)+(0.1010P)²+0.0603P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1545
_refine_ls_wR_factor_ref         0.1746
_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:
 C3(H3), C4(H4), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14),
 C16(H16), C17(H17), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C21(H21A,H21B,H21C)
;
_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
C1 C 0.4889(2) 0.5333(3) 0.24762(16) 0.0886(8) Uani 1 1 d . . . . .
H1A H 0.505140 0.460539 0.203969 0.133 Uiso 1 1 calc R U . . .
H1B H 0.482353 0.635707 0.222415 0.133 Uiso 1 1 calc R U . . .
H1C H 0.430680 0.502565 0.268967 0.133 Uiso 1 1 calc R U . . .
C2 C 0.54575(13) 0.6194(2) 0.39095(12) 0.0532(4) Uani 1 1 d . . . . .
C3 C 0.47057(14) 0.7188(2) 0.39752(12) 0.0558(5) Uani 1 1 d . . . . .
H3 H 0.426831 0.735356 0.349709 0.067 Uiso 1 1 calc R U . . .
C4 C 0.46119(13) 0.7936(2) 0.47629(12) 0.0526(4) Uani 1 1 d . . . . .
H4 H 0.410440 0.860064 0.480700 0.063 Uiso 1 1 calc R U . . .
C5 C 0.52514(12) 0.77197(19) 0.54838(11) 0.0449(4) Uani 1 1 d . . . . .
C6 C 0.60176(12) 0.6734(2) 0.53954(12) 0.0525(4) Uani 1 1 d . . . . .
H6 H 0.646686 0.658750 0.586631 0.063 Uiso 1 1 calc R U . . .
C7 C 0.61111(14) 0.5984(2) 0.46226(13) 0.0584(5) Uani 1 1 d . . . . .
H7 H 0.662059 0.532472 0.457560 0.070 Uiso 1 1 calc R U . . .
C8 C 0.51355(12) 0.84822(19) 0.63169(11) 0.0452(4) Uani 1 1 d . . . . .
C9 C 0.42760(12) 0.87443(19) 0.67199(11) 0.0477(4) Uani 1 1 d . . . . .
C10 C 0.45392(14) 0.9495(2) 0.75105(12) 0.0543(4) Uani 1 1 d . . . . .
C11 C 0.33359(14) 0.8348(2) 0.65112(14) 0.0601(5) Uani 1 1 d . . . . .
H11 H 0.314579 0.783625 0.599091 0.072 Uiso 1 1 calc R U . . .
C12 C 0.26983(16) 0.8730(3) 0.70891(17) 0.0747(6) Uani 1 1 d . . . . .
H12 H 0.206891 0.847141 0.695962 0.090 Uiso 1 1 calc R U . . .
C13 C 0.29774(17) 0.9492(3) 0.78602(17) 0.0800(7) Uani 1 1 d . . . . .
H13 H 0.252543 0.974058 0.823567 0.096 Uiso 1 1 calc R U . . .
C14 C 0.38900(18) 0.9898(3) 0.80956(15) 0.0737(6) Uani 1 1 d . . . . .
H14 H 0.406837 1.041477 0.861719 0.088 Uiso 1 1 calc R U . . .
C15 C 0.63949(13) 0.8182(3) 0.89367(12) 0.0597(5) Uani 1 1 d . . . . .
C16 C 0.58759(15) 0.7847(3) 0.96279(13) 0.0619(5) Uani 1 1 d . . . . .
H16 H 0.545141 0.857264 0.980993 0.074 Uiso 1 1 calc R U . . .
C17 C 0.59918(16) 0.6430(3) 1.00450(15) 0.0696(6) Uani 1 1 d . . . . .
H17 H 0.564394 0.621112 1.051250 0.084 Uiso 1 1 calc R U . . .
C18 C 0.66163(16) 0.5319(3) 0.97845(16) 0.0722(6) Uani 1 1 d . . . . .
C19 C 0.71053(16) 0.5671(4) 0.90732(18) 0.0813(7) Uani 1 1 d . . . . .
H19 H 0.751268 0.493160 0.887659 0.098 Uiso 1 1 calc R U . . .
C20 C 0.70069(14) 0.7075(4) 0.86509(15) 0.0777(7) Uani 1 1 d . . . . .
H20 H 0.734669 0.728666 0.817689 0.093 Uiso 1 1 calc R U . . .
C21 C 0.6755(2) 0.3795(3) 1.0268(2) 0.1000(9) Uani 1 1 d . . . . .
H21A H 0.636270 0.377037 1.074232 0.150 Uiso 1 1 calc R U . . .
H21B H 0.740140 0.369653 1.049531 0.150 Uiso 1 1 calc R U . . .
H21C H 0.659042 0.294640 0.987570 0.150 Uiso 1 1 calc R U . . .
N1 N 0.58639(11) 0.90049(19) 0.68126(9) 0.0553(4) Uani 1 1 d . . . . .
N2 N 0.55094(13) 0.9696(2) 0.75382(10) 0.0613(4) Uani 1 1 d . . . . .
O1 O 0.56097(11) 0.53518(19) 0.31796(10) 0.0733(4) Uani 1 1 d . . . . .
O2 O 0.57577(14) 1.10203(18) 0.89497(10) 0.0849(5) Uani 1 1 d . . . . .
O3 O 0.71111(13) 1.0460(3) 0.81066(11) 0.1003(7) Uani 1 1 d . . . . .
S1 S 0.62530(4) 1.00027(7) 0.84173(3) 0.0702(2) 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
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 O1 1.422(3) . ?
C2 C3 1.383(3) . ?
C2 C7 1.384(3) . ?
C2 O1 1.368(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(2) . ?
C5 C6 1.400(2) . ?
C5 C8 1.460(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.367(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.444(2) . ?
C8 N1 1.310(2) . ?
C9 C10 1.395(3) . ?
C9 C11 1.394(3) . ?
C10 C14 1.394(3) . ?
C10 N2 1.394(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.370(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.379(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.366(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.381(3) . ?
C15 C20 1.389(3) . ?
C15 S1 1.755(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.376(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.389(3) . ?
C18 C19 1.384(4) . ?
C18 C21 1.507(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.368(4) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N1 N2 1.398(2) . ?
N2 S1 1.6599(17) . ?
O2 S1 1.4277(18) . ?
O3 S1 1.4127(17) . ?

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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
C3 C2 C7 119.63(17) . . ?
O1 C2 C3 124.69(18) . . ?
O1 C2 C7 115.67(17) . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.18(17) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.1 . . ?
C5 C4 C3 121.81(16) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C6 117.94(16) . . ?
C4 C5 C8 121.47(15) . . ?
C6 C5 C8 120.59(15) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.56(17) . . ?
C7 C6 H6 119.7 . . ?
C2 C7 H7 119.6 . . ?
C6 C7 C2 120.86(17) . . ?
C6 C7 H7 119.6 . . ?
C9 C8 C5 128.02(15) . . ?
N1 C8 C5 120.90(16) . . ?
N1 C8 C9 111.07(15) . . ?
C10 C9 C8 105.89(15) . . ?
C11 C9 C8 134.75(18) . . ?
C11 C9 C10 119.25(17) . . ?
C14 C10 C9 122.27(18) . . ?
N2 C10 C9 105.69(16) . . ?
N2 C10 C14 132.04(19) . . ?
C9 C11 H11 120.7 . . ?
C12 C11 C9 118.6(2) . . ?
C12 C11 H11 120.7 . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.9(2) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 118.6 . . ?
C14 C13 C12 122.7(2) . . ?
C14 C13 H13 118.6 . . ?
C10 C14 H14 121.9 . . ?
C13 C14 C10 116.3(2) . . ?
C13 C14 H14 121.9 . . ?
C16 C15 C20 120.0(2) . . ?
C16 C15 S1 119.14(17) . . ?
C20 C15 S1 120.86(18) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.5(2) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 H17 119.2 . . ?
C16 C17 C18 121.6(2) . . ?
C18 C17 H17 119.2 . . ?
C17 C18 C21 120.7(3) . . ?
C19 C18 C17 117.6(2) . . ?
C19 C18 C21 121.7(2) . . ?
C18 C19 H19 119.0 . . ?
C20 C19 C18 121.9(2) . . ?
C20 C19 H19 119.0 . . ?
C15 C20 H20 120.3 . . ?
C19 C20 C15 119.4(2) . . ?
C19 C20 H20 120.3 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C8 N1 N2 106.30(15) . . ?
C10 N2 N1 110.90(15) . . ?
C10 N2 S1 127.17(14) . . ?
N1 N2 S1 117.62(14) . . ?
C2 O1 C1 118.02(18) . . ?
N2 S1 C15 105.48(9) . . ?
O2 S1 C15 108.97(9) . . ?
O2 S1 N2 104.40(10) . . ?
O3 S1 C15 109.46(12) . . ?
O3 S1 N2 106.23(10) . . ?
O3 S1 O2 121.10(12) . . ?

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 C3 C4 C5 0.3(3) . . . . ?
C3 C2 C7 C6 0.8(3) . . . . ?
C3 C2 O1 C1 -8.5(3) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
C3 C4 C5 C8 -178.52(17) . . . . ?
C4 C5 C6 C7 -1.5(3) . . . . ?
C4 C5 C8 C9 38.6(3) . . . . ?
C4 C5 C8 N1 -142.78(18) . . . . ?
C5 C6 C7 C2 0.6(3) . . . . ?
C5 C8 C9 C10 179.27(17) . . . . ?
C5 C8 C9 C11 3.3(3) . . . . ?
C5 C8 N1 N2 178.43(15) . . . . ?
C6 C5 C8 C9 -140.96(18) . . . . ?
C6 C5 C8 N1 37.6(3) . . . . ?
C7 C2 C3 C4 -1.2(3) . . . . ?
C7 C2 O1 C1 170.49(19) . . . . ?
C8 C5 C6 C7 178.07(17) . . . . ?
C8 C9 C10 C14 -178.16(19) . . . . ?
C8 C9 C10 N2 1.9(2) . . . . ?
C8 C9 C11 C12 176.3(2) . . . . ?
C8 N1 N2 C10 4.1(2) . . . . ?
C8 N1 N2 S1 162.44(13) . . . . ?
C9 C8 N1 N2 -2.8(2) . . . . ?
C9 C10 C14 C13 1.1(3) . . . . ?
C9 C10 N2 N1 -3.7(2) . . . . ?
C9 C10 N2 S1 -159.49(15) . . . . ?
C9 C11 C12 C13 0.1(3) . . . . ?
C10 C9 C11 C12 0.8(3) . . . . ?
C10 N2 S1 C15 76.1(2) . . . . ?
C10 N2 S1 O2 -38.7(2) . . . . ?
C10 N2 S1 O3 -167.76(18) . . . . ?
C11 C9 C10 C14 -1.5(3) . . . . ?
C11 C9 C10 N2 178.58(17) . . . . ?
C11 C12 C13 C14 -0.5(4) . . . . ?
C12 C13 C14 C10 -0.2(4) . . . . ?
C14 C10 N2 N1 176.4(2) . . . . ?
C14 C10 N2 S1 20.6(3) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
C16 C15 C20 C19 -1.5(3) . . . . ?
C16 C15 S1 N2 -97.73(17) . . . . ?
C16 C15 S1 O2 13.86(19) . . . . ?
C16 C15 S1 O3 148.34(16) . . . . ?
C16 C17 C18 C19 -1.5(3) . . . . ?
C16 C17 C18 C21 178.0(2) . . . . ?
C17 C18 C19 C20 1.9(3) . . . . ?
C18 C19 C20 C15 -0.4(3) . . . . ?
C20 C15 C16 C17 1.9(3) . . . . ?
C20 C15 S1 N2 81.10(17) . . . . ?
C20 C15 S1 O2 -167.30(16) . . . . ?
C20 C15 S1 O3 -32.82(18) . . . . ?
C21 C18 C19 C20 -177.6(2) . . . . ?
N1 C8 C9 C10 0.6(2) . . . . ?
N1 C8 C9 C11 -175.4(2) . . . . ?
N1 N2 S1 C15 -78.32(16) . . . . ?
N1 N2 S1 O2 166.88(14) . . . . ?
N1 N2 S1 O3 37.82(19) . . . . ?
N2 C10 C14 C13 -178.9(2) . . . . ?
O1 C2 C3 C4 177.74(17) . . . . ?
O1 C2 C7 C6 -178.28(17) . . . . ?
S1 C15 C16 C17 -179.21(16) . . . . ?
S1 C15 C20 C19 179.63(16) . . . . ?

_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_2_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2222403'
loop_
_audit_author_name
_audit_author_address
'Qiang Zhong'
;Huaibei Normal Univeisity
China
;
_audit_update_record             
;
2022-11-27 deposited with the CCDC.	2023-04-14 downloaded from the CCDC.
;
_audit_creation_date             2022-11-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H18 N2 O2 S'
_chemical_formula_sum            'C19 H19 N3 O2 S'
_chemical_formula_weight         353.43
_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'
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                   11.349(8)
_cell_length_b                   10.096(7)
_cell_length_c                   15.893(11)
_cell_angle_alpha                90.00(3)
_cell_angle_beta                 97.84(4)
_cell_angle_gamma                90.00(3)
_cell_volume                     1804(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    888
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      27.34
_cell_measurement_theta_min      3.09
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0568 before and 0.0482 after correction.
The Ratio of minimum to maximum transmission is 0.9140.
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    1.301
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            72878
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.468
_diffrn_reflns_theta_min         2.587
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3506
_reflns_number_total             4089
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         4089
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.025
_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)+(0.0640P)²+0.4740P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1207
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All H(H) groups, All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C15(H15),
 C16(H16), C17(H17), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.30217(3) -0.62230(4) 0.36842(3) 0.04982(14) Uani 1 1 d . . . . .
O1 O 0.19537(11) -0.60917(15) 0.30990(9) 0.0740(4) Uani 1 1 d . . . . .
O2 O 0.34341(12) -0.51175(11) 0.42149(9) 0.0662(4) Uani 1 1 d . . . . .
N1 N 0.27736(12) -0.74961(14) 0.42724(9) 0.0498(3) Uani 1 1 d . . . . .
C20 C 0.35511(12) -0.80551(13) 0.49557(8) 0.0382(3) Uani 1 1 d . . . . .
N2 N 0.18887(15) -0.99313(16) 0.40126(10) 0.0656(4) Uani 1 1 d . . . . .
C1 C 0.6914(3) -0.7949(2) 0.16514(17) 0.0929(8) Uani 1 1 d . . . . .
H1A H 0.7096 -0.8866 0.1765 0.139 Uiso 1 1 calc GR . . . .
H1B H 0.7615 -0.7424 0.1808 0.139 Uiso 1 1 calc GR . . . .
H1C H 0.6640 -0.7834 0.1057 0.139 Uiso 1 1 calc GR . . . .
C2 C 0.59499(17) -0.75118(17) 0.21636(11) 0.0583(4) Uani 1 1 d . . . . .
C3 C 0.61625(18) -0.6535(2) 0.27795(14) 0.0708(5) Uani 1 1 d . . . . .
H3 H 0.6910 -0.6142 0.2877 0.085 Uiso 1 1 calc R . . . .
C4 C 0.52878(16) -0.61305(18) 0.32544(12) 0.0605(4) Uani 1 1 d . . . . .
H4 H 0.5449 -0.5480 0.3668 0.073 Uiso 1 1 calc R . . . .
C5 C 0.41733(13) -0.67074(14) 0.31045(9) 0.0434(3) Uani 1 1 d . . . . .
C6 C 0.39427(16) -0.76970(17) 0.24977(11) 0.0584(4) Uani 1 1 d . . . . .
H6 H 0.3198 -0.8096 0.2405 0.070 Uiso 1 1 calc R . . . .
C7 C 0.48260(18) -0.80840(18) 0.20337(11) 0.0622(4) Uani 1 1 d . . . . .
H7 H 0.4666 -0.8742 0.1625 0.075 Uiso 1 1 calc R . . . .
C8 C 0.45044(14) -0.73506(15) 0.53905(10) 0.0477(3) Uani 1 1 d . . . . .
H8 H 0.4671 -0.6500 0.5216 0.057 Uiso 1 1 calc R . . . .
C9 C 0.52022(15) -0.79147(18) 0.60804(10) 0.0550(4) Uani 1 1 d . . . . .
H9 H 0.5835 -0.7437 0.6365 0.066 Uiso 1 1 calc R . . . .
C10 C 0.49713(15) -0.91825(18) 0.63529(11) 0.0573(4) Uani 1 1 d . . . . .
H10 H 0.5446 -0.9554 0.6816 0.069 Uiso 1 1 calc R . . . .
C11 C 0.40268(14) -0.98884(15) 0.59284(10) 0.0489(3) Uani 1 1 d . . . . .
H11 H 0.3871 -1.0736 0.6114 0.059 Uiso 1 1 calc R . . . .
C12 C 0.32986(12) -0.93562(14) 0.52245(8) 0.0386(3) Uani 1 1 d . . . . .
C13 C 0.23150(13) -1.01854(14) 0.47834(10) 0.0450(3) Uani 1 1 d . . . . .
C14 C 0.18265(13) -1.12957(15) 0.52674(10) 0.0483(4) Uani 1 1 d . . . . .
C15 C 0.12403(19) -1.1010(2) 0.59574(14) 0.0721(5) Uani 1 1 d . . . . .
H15 H 0.1232 -1.0147 0.6162 0.086 Uiso 1 1 calc R . . . .
C16 C 0.0663(2) -1.2019(2) 0.63449(17) 0.0872(7) Uani 1 1 d . . . . .
H16 H 0.0252 -1.1823 0.6797 0.105 Uiso 1 1 calc R . . . .
C17 C 0.0702(2) -1.3304(2) 0.60571(18) 0.0867(7) Uani 1 1 d . . . . .
H17 H 0.0313 -1.3971 0.6314 0.104 Uiso 1 1 calc R . . . .
C18 C 0.1309(2) -1.3602(2) 0.53962(16) 0.0823(6) Uani 1 1 d . . . . .
H18 H 0.1349 -1.4474 0.5215 0.099 Uiso 1 1 calc R . . . .
C19 C 0.18718(18) -1.26040(17) 0.49912(13) 0.0631(5) Uani 1 1 d . . . . .
H19 H 0.2277 -1.2811 0.4538 0.076 Uiso 1 1 calc R . . . .
H1 H 0.2346(18) -0.805(2) 0.4005(12) 0.060(6) Uiso 1 1 d . . . . .
H2 H 0.1339(19) -1.047(2) 0.3840(13) 0.072 Uiso 1 1 d 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
S1 O1 1.4298(16) . ?
S1 O2 1.4381(16) . ?
S1 N1 1.6361(16) . ?
S1 C5 1.7676(18) . ?
N1 C20 1.419(2) . ?
N1 H1 0.82(2) . ?
C20 C8 1.396(2) . ?
C20 C12 1.422(2) . ?
N2 C13 1.280(2) . ?
N2 H2 0.85(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.515(3) . ?
C2 C3 1.387(3) . ?
C2 C7 1.390(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.388(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(2) . ?
C5 C6 1.389(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.380(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.384(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.388(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.384(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.404(2) . ?
C12 C13 1.492(2) . ?
C13 C14 1.507(2) . ?
C14 C15 1.388(3) . ?
C14 C19 1.395(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.399(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.378(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.366(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.396(3) . ?
C19 H19 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
O1 S1 O2 119.26(9) . . ?
O1 S1 N1 104.35(9) . . ?
O1 S1 C5 107.94(10) . . ?
O2 S1 N1 110.01(9) . . ?
O2 S1 C5 108.41(8) . . ?
N1 S1 C5 106.11(8) . . ?
S1 N1 H1 112.3(14) . . ?
C20 N1 S1 127.73(11) . . ?
C20 N1 H1 112.6(14) . . ?
N1 C20 C12 117.86(13) . . ?
C8 C20 N1 122.33(13) . . ?
C8 C20 C12 119.73(13) . . ?
C13 N2 H2 110.4(15) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 121.15(19) . . ?
C3 C2 C7 117.91(17) . . ?
C7 C2 C1 120.94(19) . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.64(18) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.17(17) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 S1 121.16(13) . . ?
C4 C5 C6 120.26(16) . . ?
C6 C5 S1 118.58(13) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.55(17) . . ?
C7 C6 H6 120.2 . . ?
C2 C7 H7 119.3 . . ?
C6 C7 C2 121.47(17) . . ?
C6 C7 H7 119.3 . . ?
C20 C8 H8 119.9 . . ?
C9 C8 C20 120.22(15) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 119.5 . . ?
C8 C9 C10 120.97(15) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.32(15) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.2 . . ?
C10 C11 C12 121.60(15) . . ?
C12 C11 H11 119.2 . . ?
C20 C12 C13 123.07(13) . . ?
C11 C12 C20 118.16(13) . . ?
C11 C12 C13 118.76(13) . . ?
N2 C13 C12 119.88(14) . . ?
N2 C13 C14 121.34(14) . . ?
C12 C13 C14 118.78(14) . . ?
C15 C14 C13 119.85(15) . . ?
C15 C14 C19 119.18(16) . . ?
C19 C14 C13 120.78(16) . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 120.00(19) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.1(2) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.31(19) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.4(2) . . ?
C19 C18 H18 119.8 . . ?
C14 C19 C18 120.0(2) . . ?
C14 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?

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 C20 C8 20.3(2) . . . . ?
S1 N1 C20 C12 -162.94(12) . . . . ?
S1 C5 C6 C7 179.55(13) . . . . ?
O1 S1 N1 C20 179.99(14) . . . . ?
O1 S1 C5 C4 136.21(15) . . . . ?
O1 S1 C5 C6 -44.56(15) . . . . ?
O2 S1 N1 C20 -50.96(16) . . . . ?
O2 S1 C5 C4 5.73(16) . . . . ?
O2 S1 C5 C6 -175.04(12) . . . . ?
N1 S1 C5 C4 -112.40(15) . . . . ?
N1 S1 C5 C6 66.83(14) . . . . ?
N1 C20 C8 C9 176.73(14) . . . . ?
N1 C20 C12 C11 -176.70(13) . . . . ?
N1 C20 C12 C13 4.5(2) . . . . ?
C20 C8 C9 C10 0.0(3) . . . . ?
C20 C12 C13 N2 20.9(2) . . . . ?
C20 C12 C13 C14 -157.89(13) . . . . ?
N2 C13 C14 C15 -113.6(2) . . . . ?
N2 C13 C14 C19 61.3(2) . . . . ?
C1 C2 C3 C4 -179.8(2) . . . . ?
C1 C2 C7 C6 179.81(18) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C2 C7 C6 0.2(3) . . . . ?
C3 C4 C5 S1 -179.53(15) . . . . ?
C3 C4 C5 C6 1.3(3) . . . . ?
C4 C5 C6 C7 -1.2(2) . . . . ?
C5 S1 N1 C20 66.10(16) . . . . ?
C5 C6 C7 C2 0.5(3) . . . . ?
C7 C2 C3 C4 -0.1(3) . . . . ?
C8 C20 C12 C11 0.2(2) . . . . ?
C8 C20 C12 C13 -178.60(13) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C10 C11 C12 C20 -0.4(2) . . . . ?
C10 C11 C12 C13 178.46(15) . . . . ?
C11 C12 C13 N2 -157.85(16) . . . . ?
C11 C12 C13 C14 23.4(2) . . . . ?
C12 C20 C8 C9 0.0(2) . . . . ?
C12 C13 C14 C15 65.2(2) . . . . ?
C12 C13 C14 C19 -119.91(18) . . . . ?
C13 C14 C15 C16 172.35(19) . . . . ?
C13 C14 C19 C18 -173.52(18) . . . . ?
C14 C15 C16 C17 1.8(4) . . . . ?
C15 C14 C19 C18 1.4(3) . . . . ?
C15 C16 C17 C18 0.4(4) . . . . ?
C16 C17 C18 C19 -1.6(4) . . . . ?
C17 C18 C19 C14 0.7(3) . . . . ?
C19 C14 C15 C16 -2.6(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
