# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2203869'
loop_
_audit_author_name
_audit_author_address
'chen rongxiang'
;xinxiang university
China
;
_audit_update_record             
;
2022-08-28 deposited with the CCDC.	2022-10-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H13 N3 O2 S'
_chemical_formula_weight         287.33

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   8.3551(8)
_cell_length_b                   11.7955(11)
_cell_length_c                   14.7480(13)
_cell_angle_alpha                90
_cell_angle_beta                 104.633(2)
_cell_angle_gamma                90
_cell_volume                     1406.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2983
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      26.70

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    0.235
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.946
_exptl_absorpt_correction_type   none
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7002
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.055
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2466
_reflns_number_gt                2034
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0691P)²+0.4080P] 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_number_reflns         2466
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1137
_refine_ls_wR_factor_gt          0.1073
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_refine_ls_shift/su_max          0.002
_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 0.09772(6) 0.18082(4) 0.38374(4) 0.0472(2) Uani 1 1 d . . . . .
O2 O -0.03410(18) 0.21067(15) 0.30547(12) 0.0688(5) Uani 1 1 d . . . . .
N3 N 0.2445(2) 0.13162(14) 0.33652(11) 0.0427(4) Uani 1 1 d . . . . .
O1 O 0.0737(2) 0.09693(13) 0.44839(12) 0.0687(5) Uani 1 1 d . . . . .
N2 N 0.3754(2) 0.07289(13) 0.39887(11) 0.0449(4) Uani 1 1 d . . . . .
C13 C 0.4694(2) 0.15923(15) 0.28294(13) 0.0380(4) Uani 1 1 d . . . . .
N1 N 0.6486(3) 0.0310(2) 0.40255(19) 0.0641(6) Uani 1 1 d . . . . .
C8 C 0.3051(2) 0.19142(15) 0.26988(12) 0.0387(4) Uani 1 1 d . . . . .
C5 C 0.1759(2) 0.30472(15) 0.44359(13) 0.0390(4) Uani 1 1 d . . . . .
C14 C 0.5044(2) 0.08574(16) 0.36451(13) 0.0409(4) Uani 1 1 d . . . . .
C12 C 0.5641(3) 0.20212(18) 0.22584(14) 0.0496(5) Uani 1 1 d . . . . .
H12 H 0.6729 0.1789 0.2329 0.060 Uiso 1 1 calc R U . . .
C9 C 0.2313(3) 0.26938(18) 0.20193(14) 0.0502(5) Uani 1 1 d . . . . .
H9 H 0.1214 0.2910 0.1935 0.060 Uiso 1 1 calc R U . . .
C4 C 0.2894(3) 0.29734(17) 0.52980(14) 0.0495(5) Uani 1 1 d . . . . .
H4 H 0.3235 0.2269 0.5561 0.059 Uiso 1 1 calc R U . . .
C2 C 0.3025(3) 0.50078(18) 0.53862(15) 0.0542(5) Uani 1 1 d . . . . .
C10 C 0.3281(3) 0.31349(19) 0.14746(15) 0.0587(6) Uani 1 1 d . . . . .
H10 H 0.2830 0.3672 0.1020 0.070 Uiso 1 1 calc R U . . .
C3 C 0.3510(3) 0.39515(19) 0.57614(15) 0.0551(6) Uani 1 1 d . . . . .
H3 H 0.4272 0.3902 0.6341 0.066 Uiso 1 1 calc R U . . .
C6 C 0.1270(3) 0.40912(19) 0.40457(15) 0.0586(6) Uani 1 1 d . . . . .
H6 H 0.0512 0.4141 0.3465 0.070 Uiso 1 1 calc R U . . .
C11 C 0.4919(3) 0.2799(2) 0.15863(15) 0.0584(6) Uani 1 1 d . . . . .
H11 H 0.5532 0.3105 0.1200 0.070 Uiso 1 1 calc R U . . .
C7 C 0.1910(3) 0.50593(19) 0.45206(17) 0.0671(7) Uani 1 1 d . . . . .
H7 H 0.1585 0.5763 0.4252 0.080 Uiso 1 1 calc R U . . .
C1 C 0.3693(4) 0.6076(2) 0.5913(2) 0.0853(9) Uani 1 1 d . . . . .
H1C H 0.3234 0.6160 0.6444 0.128 Uiso 1 1 calc R U . . .
H1D H 0.3394 0.6719 0.5507 0.128 Uiso 1 1 calc R U . . .
H1E H 0.4876 0.6028 0.6124 0.128 Uiso 1 1 calc R U . . .
H1A H 0.718(4) 0.054(3) 0.384(2) 0.077(10) Uiso 1 1 d . . . . .
H1B H 0.669(4) 0.003(3) 0.457(2) 0.091(10) 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 O1 1.4230(16) . ?
S1 O2 1.4237(17) . ?
S1 N3 1.6605(16) . ?
S1 C5 1.7464(18) . ?
N3 C8 1.404(2) . ?
N3 N2 1.419(2) . ?
N2 C14 1.310(2) . ?
C13 C12 1.388(3) . ?
C13 C8 1.390(3) . ?
C13 C14 1.451(3) . ?
N1 C14 1.357(3) . ?
N1 H1A 0.75(3) . ?
N1 H1B 0.84(3) . ?
C8 C9 1.385(3) . ?
C5 C6 1.377(3) . ?
C5 C4 1.384(3) . ?
C12 C11 1.373(3) . ?
C12 H12 0.9300 . ?
C9 C10 1.378(3) . ?
C9 H9 0.9300 . ?
C4 C3 1.373(3) . ?
C4 H4 0.9300 . ?
C2 C7 1.378(3) . ?
C2 C3 1.382(3) . ?
C2 C1 1.511(3) . ?
C10 C11 1.394(3) . ?
C10 H10 0.9300 . ?
C3 H3 0.9300 . ?
C6 C7 1.375(3) . ?
C6 H6 0.9300 . ?
C11 H11 0.9300 . ?
C7 H7 0.9300 . ?
C1 H1C 0.9600 . ?
C1 H1D 0.9600 . ?
C1 H1E 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
O1 S1 O2 120.27(11) . . ?
O1 S1 N3 106.37(9) . . ?
O2 S1 N3 104.39(9) . . ?
O1 S1 C5 109.95(9) . . ?
O2 S1 C5 108.47(10) . . ?
N3 S1 C5 106.45(8) . . ?
C8 N3 N2 110.09(15) . . ?
C8 N3 S1 123.59(13) . . ?
N2 N3 S1 115.40(12) . . ?
C14 N2 N3 105.51(15) . . ?
C12 C13 C8 120.69(18) . . ?
C12 C13 C14 133.97(18) . . ?
C8 C13 C14 105.25(16) . . ?
C14 N1 H1A 112(2) . . ?
C14 N1 H1B 122(2) . . ?
H1A N1 H1B 119(3) . . ?
C9 C8 C13 121.71(18) . . ?
C9 C8 N3 131.79(19) . . ?
C13 C8 N3 106.50(16) . . ?
C6 C5 C4 120.16(18) . . ?
C6 C5 S1 120.24(15) . . ?
C4 C5 S1 119.59(15) . . ?
N2 C14 N1 121.1(2) . . ?
N2 C14 C13 112.13(17) . . ?
N1 C14 C13 126.8(2) . . ?
C11 C12 C13 117.9(2) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 H12 121.1 . . ?
C10 C9 C8 116.9(2) . . ?
C10 C9 H9 121.5 . . ?
C8 C9 H9 121.5 . . ?
C3 C4 C5 119.23(19) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C7 C2 C3 118.16(19) . . ?
C7 C2 C1 121.0(2) . . ?
C3 C2 C1 120.8(2) . . ?
C9 C10 C11 121.8(2) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C4 C3 C2 121.5(2) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C7 C6 C5 119.6(2) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C12 C11 C10 121.0(2) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C6 C7 C2 121.3(2) . . ?
C6 C7 H7 119.3 . . ?
C2 C7 H7 119.3 . . ?
C2 C1 H1C 109.5 . . ?
C2 C1 H1D 109.5 . . ?
H1C C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
H1C C1 H1E 109.5 . . ?
H1D C1 H1E 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
O1 S1 N3 C8 -178.98(15) . . . . ?
O2 S1 N3 C8 52.87(17) . . . . ?
C5 S1 N3 C8 -61.75(16) . . . . ?
O1 S1 N3 N2 -38.47(15) . . . . ?
O2 S1 N3 N2 -166.62(13) . . . . ?
C5 S1 N3 N2 78.75(14) . . . . ?
C8 N3 N2 C14 -7.1(2) . . . . ?
S1 N3 N2 C14 -152.73(13) . . . . ?
C12 C13 C8 C9 -2.0(3) . . . . ?
C14 C13 C8 C9 175.00(17) . . . . ?
C12 C13 C8 N3 178.56(16) . . . . ?
C14 C13 C8 N3 -4.48(19) . . . . ?
N2 N3 C8 C9 -172.17(19) . . . . ?
S1 N3 C8 C9 -29.9(3) . . . . ?
N2 N3 C8 C13 7.24(19) . . . . ?
S1 N3 C8 C13 149.52(14) . . . . ?
O1 S1 C5 C6 -143.54(18) . . . . ?
O2 S1 C5 C6 -10.2(2) . . . . ?
N3 S1 C5 C6 101.63(18) . . . . ?
O1 S1 C5 C4 37.56(19) . . . . ?
O2 S1 C5 C4 170.91(16) . . . . ?
N3 S1 C5 C4 -77.26(17) . . . . ?
N3 N2 C14 N1 -173.84(19) . . . . ?
N3 N2 C14 C13 4.2(2) . . . . ?
C12 C13 C14 N2 176.5(2) . . . . ?
C8 C13 C14 N2 0.2(2) . . . . ?
C12 C13 C14 N1 -5.6(4) . . . . ?
C8 C13 C14 N1 178.0(2) . . . . ?
C8 C13 C12 C11 2.2(3) . . . . ?
C14 C13 C12 C11 -173.7(2) . . . . ?
C13 C8 C9 C10 0.2(3) . . . . ?
N3 C8 C9 C10 179.53(19) . . . . ?
C6 C5 C4 C3 0.7(3) . . . . ?
S1 C5 C4 C3 179.58(17) . . . . ?
C8 C9 C10 C11 1.3(3) . . . . ?
C5 C4 C3 C2 -0.1(3) . . . . ?
C7 C2 C3 C4 -0.8(4) . . . . ?
C1 C2 C3 C4 178.9(2) . . . . ?
C4 C5 C6 C7 -0.4(3) . . . . ?
S1 C5 C6 C7 -179.26(19) . . . . ?
C13 C12 C11 C10 -0.8(3) . . . . ?
C9 C10 C11 C12 -1.0(3) . . . . ?
C5 C6 C7 C2 -0.6(4) . . . . ?
C3 C2 C7 C6 1.2(4) . . . . ?
C1 C2 C7 C6 -178.6(3) . . . . ?

_refine_diff_density_max         0.250
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.044

