# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_20200771
_database_code_depnum_ccdc_archive 'CCDC 2018442'
loop_
_audit_author_name
_audit_author_address
'Zhiyong Wu'
;Henan Agricultural University
China
;
_audit_update_record             
;
2020-07-23 deposited with the CCDC.	2020-08-24 downloaded from the CCDC.
;
_audit_creation_date             2020-07-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H12 N2 O S'
_chemical_formula_sum            'C14 H12 N2 O S'
_chemical_formula_weight         256.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H15N2O4
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.7203(9)
_cell_length_b                   5.3408(3)
_cell_length_c                   16.4985(9)
_cell_angle_alpha                90
_cell_angle_beta                 106.533(6)
_cell_angle_gamma                90
_cell_volume                     1243.46(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1419
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6360
_cell_measurement_theta_min      5.5710
_shelx_estimated_absorpt_T_max   0.826
_shelx_estimated_absorpt_T_min   0.732
_exptl_absorpt_coefficient_mu    2.215
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4561
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.067
_diffrn_reflns_theta_max         67.067
_diffrn_reflns_theta_min         5.581
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00  -5.00   1.00    1.00    --  -33.50 -77.00  60.00   98
  2  ω    -52.00  35.00   1.00    1.00    --  -33.50  57.00   0.00   87
  3  ω     57.00 110.00   1.00    1.00    --   36.47 178.00 -90.00   53
  4  ω     -4.00  77.00   1.00    1.00    --   36.47 -99.00-120.00   81
  5  ω    -32.00  55.00   1.00    1.00    --   36.47 -57.00 -90.00   87
  6  ω     -4.00  57.00   1.00    1.00    --   36.47 -37.00-180.00   61
  7  ω    -25.00  52.00   1.00    1.00    --   36.47 -37.00 -60.00   77
  8  ω     40.00  71.00   1.00    1.50    --  108.00 -94.00 -60.00   31
  9  ω     70.00 171.00   1.00    1.50    --  108.00  15.00 120.00  101
 10  ω     67.00 112.00   1.00    1.50    --  108.00 -30.00-120.00   45
 11  ω     85.00 137.00   1.00    1.50    --  108.00 -77.00  30.00   52
 12  ω     62.00 109.00   1.00    1.50    --  108.00-111.00 150.00   47
 13  ω    109.00 168.00   1.00    1.50    --  108.00  61.00   0.00   59
 14  ω     88.00 115.00   1.00    1.50    --  108.00  45.00  60.00   27
 15  ω     46.00 128.00   1.00    1.50    --  108.00 -61.00 -30.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0996591000
_diffrn_orient_matrix_UB_12      -0.0158966000
_diffrn_orient_matrix_UB_13      -0.0124596000
_diffrn_orient_matrix_UB_21      -0.0430878000
_diffrn_orient_matrix_UB_22      0.0357054000
_diffrn_orient_matrix_UB_23      -0.0959618000
_diffrn_orient_matrix_UB_31      0.0110012000
_diffrn_orient_matrix_UB_32      0.2857625000
_diffrn_orient_matrix_UB_33      0.0112868000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1695
_reflns_number_total             2222
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0454
_refine_ls_restrained_S_all      1.038
_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)+(0.0516P)²+0.3496P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1234
_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:
 C1(H1A), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_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 0.67106(5) -0.02809(14) 0.80793(4) 0.0502(2) Uani 1 1 d . . . . .
O1 O 1.08988(14) -0.0008(4) 0.88501(15) 0.0708(7) Uani 1 1 d . . . . .
N1 N 0.54648(15) 0.3927(4) 0.61218(13) 0.0410(5) Uani 1 1 d . . . . .
H1 H 0.510(2) 0.513(5) 0.5882(19) 0.061(10) Uiso 1 1 d . . . . .
N2 N 0.57870(14) 0.2245(4) 0.48806(12) 0.0399(5) Uani 1 1 d . . . . .
C1 C 0.57232(17) 0.3337(5) 0.69647(15) 0.0428(6) Uani 1 1 d . . . . .
H1A H 0.5542 0.4225 0.7378 0.051 Uiso 1 1 calc R . . . .
C2 C 0.62844(17) 0.1258(5) 0.71084(15) 0.0403(6) Uani 1 1 d . . . . .
C3 C 0.63978(16) 0.0498(5) 0.63082(15) 0.0359(5) Uani 1 1 d . . . . .
C4 C 0.58767(16) 0.2236(5) 0.57124(15) 0.0360(5) Uani 1 1 d . . . . .
C5 C 0.68603(17) -0.1404(5) 0.60133(16) 0.0428(6) Uani 1 1 d . . . . .
H5 H 0.7217 -0.2601 0.6377 0.051 Uiso 1 1 calc R . . . .
C6 C 0.67682(19) -0.1445(5) 0.51571(16) 0.0459(6) Uani 1 1 d . . . . .
H6 H 0.7061 -0.2704 0.4933 0.055 Uiso 1 1 calc R . . . .
C7 C 0.62444(18) 0.0369(5) 0.46299(16) 0.0458(6) Uani 1 1 d . . . . .
H7 H 0.6207 0.0278 0.4058 0.055 Uiso 1 1 calc R . . . .
C8 C 0.79621(18) -0.0177(5) 0.82798(15) 0.0419(6) Uani 1 1 d . . . . .
C9 C 0.8485(2) -0.2030(6) 0.87775(18) 0.0551(8) Uani 1 1 d . . . . .
H9 H 0.8176 -0.3313 0.8973 0.066 Uiso 1 1 calc R . . . .
C10 C 0.9466(2) -0.2020(6) 0.89933(19) 0.0598(8) Uani 1 1 d . . . . .
H10 H 0.9809 -0.3266 0.9343 0.072 Uiso 1 1 calc R . . . .
C11 C 0.9934(2) -0.0174(6) 0.86917(18) 0.0522(7) Uani 1 1 d . . . . .
C12 C 0.9416(2) 0.1683(6) 0.81792(19) 0.0589(8) Uani 1 1 d . . . . .
H12 H 0.9726 0.2929 0.7967 0.071 Uiso 1 1 calc R . . . .
C13 C 0.8437(2) 0.1691(5) 0.79820(18) 0.0543(7) Uani 1 1 d . . . . .
H13 H 0.8094 0.2963 0.7646 0.065 Uiso 1 1 calc R . . . .
C14 C 1.1451(2) -0.1996(7) 0.9316(2) 0.0781(11) Uani 1 1 d . . . . .
H14A H 1.1249 -0.3555 0.9031 0.117 Uiso 1 1 calc GR . . . .
H14B H 1.1370 -0.2055 0.9872 0.117 Uiso 1 1 calc GR . . . .
H14C H 1.2107 -0.1722 0.9357 0.117 Uiso 1 1 calc GR . . . .


_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 C2 1.750(2) . ?
S1 C8 1.777(3) . ?
O1 C11 1.372(3) . ?
O1 C14 1.422(4) . ?
N1 H1 0.86(3) . ?
N1 C1 1.370(3) . ?
N1 C4 1.368(3) . ?
N2 C4 1.341(3) . ?
N2 C7 1.337(3) . ?
C1 H1A 0.9300 . ?
C1 C2 1.364(4) . ?
C2 C3 1.435(3) . ?
C3 C4 1.410(3) . ?
C3 C5 1.386(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.381(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.373(3) . ?
C8 C13 1.386(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.385(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.374(4) . ?
C11 C12 1.383(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.384(4) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C2 S1 C8 103.78(12) . . ?
C11 O1 C14 117.1(3) . . ?
C1 N1 H1 127(2) . . ?
C4 N1 H1 125(2) . . ?
C4 N1 C1 108.4(2) . . ?
C7 N2 C4 113.7(2) . . ?
N1 C1 H1A 125.0 . . ?
C2 C1 N1 110.1(2) . . ?
C2 C1 H1A 125.0 . . ?
C1 C2 S1 125.7(2) . . ?
C1 C2 C3 107.1(2) . . ?
C3 C2 S1 127.2(2) . . ?
C4 C3 C2 105.8(2) . . ?
C5 C3 C2 136.7(2) . . ?
C5 C3 C4 117.5(2) . . ?
N1 C4 C3 108.7(2) . . ?
N2 C4 N1 125.1(2) . . ?
N2 C4 C3 126.3(2) . . ?
C3 C5 H5 121.4 . . ?
C6 C5 C3 117.1(2) . . ?
C6 C5 H5 121.4 . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C7 120.5(2) . . ?
C7 C6 H6 119.7 . . ?
N2 C7 C6 124.8(2) . . ?
N2 C7 H7 117.6 . . ?
C6 C7 H7 117.6 . . ?
C9 C8 S1 117.6(2) . . ?
C9 C8 C13 118.5(3) . . ?
C13 C8 S1 123.9(2) . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.1(3) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H10 119.9 . . ?
O1 C11 C10 125.1(3) . . ?
O1 C11 C12 115.5(3) . . ?
C10 C11 C12 119.4(3) . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.1(3) . . ?
C13 C12 H12 120.0 . . ?
C8 C13 H13 119.6 . . ?
C12 C13 C8 120.8(3) . . ?
C12 C13 H13 119.6 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N2 0.86(3) 2.08(3) 2.928(3) 171(3) 3_666

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 C2 C3 C4 175.99(19) . . . . ?
S1 C2 C3 C5 -3.6(4) . . . . ?
S1 C8 C9 C10 -177.2(2) . . . . ?
S1 C8 C13 C12 178.5(2) . . . . ?
O1 C11 C12 C13 -179.9(3) . . . . ?
N1 C1 C2 S1 -175.43(18) . . . . ?
N1 C1 C2 C3 0.7(3) . . . . ?
C1 N1 C4 N2 -179.4(2) . . . . ?
C1 N1 C4 C3 1.0(3) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C1 C2 C3 C5 -179.6(3) . . . . ?
C2 S1 C8 C9 -153.3(2) . . . . ?
C2 S1 C8 C13 28.4(3) . . . . ?
C2 C3 C4 N1 -0.6(3) . . . . ?
C2 C3 C4 N2 179.9(2) . . . . ?
C2 C3 C5 C6 179.3(3) . . . . ?
C3 C5 C6 C7 0.8(4) . . . . ?
C4 N1 C1 C2 -1.1(3) . . . . ?
C4 N2 C7 C6 0.0(4) . . . . ?
C4 C3 C5 C6 -0.3(3) . . . . ?
C5 C3 C4 N1 179.1(2) . . . . ?
C5 C3 C4 N2 -0.4(4) . . . . ?
C5 C6 C7 N2 -0.7(4) . . . . ?
C7 N2 C4 N1 -178.8(2) . . . . ?
C7 N2 C4 C3 0.6(3) . . . . ?
C8 S1 C2 C1 -121.5(2) . . . . ?
C8 S1 C2 C3 63.2(2) . . . . ?
C8 C9 C10 C11 -1.7(5) . . . . ?
C9 C8 C13 C12 0.2(4) . . . . ?
C9 C10 C11 O1 -178.6(3) . . . . ?
C9 C10 C11 C12 0.7(5) . . . . ?
C10 C11 C12 C13 0.7(5) . . . . ?
C11 C12 C13 C8 -1.2(5) . . . . ?
C13 C8 C9 C10 1.2(4) . . . . ?
C14 O1 C11 C10 4.5(4) . . . . ?
C14 O1 C11 C12 -174.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.168
_oxdiff_exptl_absorpt_empirical_full_min 0.840
