# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2006826'
loop_
_audit_author_name
_audit_author_address
'Kai-kai Wang'
;xinxiang university
China
;
_audit_update_record             
;
2020-05-31 deposited with the CCDC.	2020-07-29 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            'C17 H15 Cl N2 O2 S'
_chemical_formula_weight         346.82

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'
Cl Cl 0.1484 0.1585 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   10.768(2)
_cell_length_b                   10.433(2)
_cell_length_c                   14.800(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.502(3)
_cell_angle_gamma                90
_cell_volume                     1616.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4094
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      27.65

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.376
_shelx_estimated_absorpt_T_min   0.909
_shelx_estimated_absorpt_T_max   0.922
_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            8288
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_av_R_equivalents  0.0158
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.756
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        25.242
_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             2990
_reflns_number_gt                2411
_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)+(0.0538P)²+0.8333P] 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_number_reflns         2990
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1106
_refine_ls_wR_factor_gt          0.1041
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
C1 C 0.8683(2) 0.9028(2) 0.54108(16) 0.0556(6) Uani 1 1 d . . . . .
H1 H 0.8649 0.9429 0.4844 0.067 Uiso 1 1 calc R U . . .
C2 C 0.7887(2) 0.9416(2) 0.59635(17) 0.0562(6) Uani 1 1 d . . . . .
H2 H 0.7301 1.0072 0.5766 0.067 Uiso 1 1 calc R U . . .
C3 C 0.7959(2) 0.8834(2) 0.68066(15) 0.0477(5) Uani 1 1 d . . . . .
H3 H 0.7423 0.9108 0.7178 0.057 Uiso 1 1 calc R U . . .
C4 C 0.88113(18) 0.78495(18) 0.71132(13) 0.0372(4) Uani 1 1 d . . . . .
C5 C 0.95997(19) 0.7456(2) 0.65475(14) 0.0420(5) Uani 1 1 d . . . . .
H5 H 1.0179 0.6793 0.6739 0.050 Uiso 1 1 calc R U . . .
C6 C 0.9530(2) 0.8042(2) 0.57032(15) 0.0508(5) Uani 1 1 d . . . . .
H6 H 1.0061 0.7768 0.5327 0.061 Uiso 1 1 calc R U . . .
C7 C 0.8892(2) 0.7217(2) 0.80430(14) 0.0447(5) Uani 1 1 d . . . . .
H7A H 0.9779 0.7013 0.8315 0.054 Uiso 1 1 calc R U . . .
H7B H 0.8618 0.7831 0.8449 0.054 Uiso 1 1 calc R U . . .
C8 C 0.67535(18) 0.61966(19) 0.77182(14) 0.0397(4) Uani 1 1 d . . . . .
H8A H 0.6517 0.6635 0.7125 0.048 Uiso 1 1 calc R U . . .
H8B H 0.6415 0.6666 0.8173 0.048 Uiso 1 1 calc R U . . .
C9 C 0.62812(18) 0.48015(18) 0.76354(13) 0.0359(4) Uani 1 1 d . . . . .
C10 C 0.74756(18) 0.39963(19) 0.76088(15) 0.0410(5) Uani 1 1 d . . . . .
H10 H 0.7793 0.3573 0.8209 0.049 Uiso 1 1 calc R U . . .
C11 C 0.84286(18) 0.50006(19) 0.74598(15) 0.0402(5) Uani 1 1 d . . . . .
H11A H 0.9302 0.4708 0.7682 0.048 Uiso 1 1 calc R U . . .
H11B H 0.8288 0.5241 0.6811 0.048 Uiso 1 1 calc R U . . .
C12 C 0.52477(17) 0.44943(17) 0.67937(13) 0.0341(4) Uani 1 1 d . . . . .
C13 C 0.40806(19) 0.51136(18) 0.65345(14) 0.0389(4) Uani 1 1 d . . . . .
H13 H 0.3877 0.5785 0.6888 0.047 Uiso 1 1 calc R U . . .
C14 C 0.3230(2) 0.4710(2) 0.57404(15) 0.0458(5) Uani 1 1 d . . . . .
C15 C 0.3518(2) 0.3730(2) 0.51975(15) 0.0500(5) Uani 1 1 d . . . . .
H15 H 0.2925 0.3478 0.4664 0.060 Uiso 1 1 calc R U . . .
C16 C 0.4686(2) 0.3127(2) 0.54466(14) 0.0473(5) Uani 1 1 d . . . . .
H16 H 0.4893 0.2475 0.5079 0.057 Uiso 1 1 calc R U . . .
C17 C 0.55491(19) 0.35036(18) 0.62525(14) 0.0390(4) Uani 1 1 d . . . . .
Cl1 Cl 0.17332(6) 0.54226(8) 0.54265(5) 0.0769(2) Uani 1 1 d . . . . .
N1 N 0.81329(15) 0.60458(16) 0.80211(11) 0.0393(4) Uani 1 1 d . . . . .
N2 N 0.57756(17) 0.44331(18) 0.84900(12) 0.0463(4) Uani 1 1 d . . . . .
O1 O 0.5164(2) 0.5206(2) 0.87921(15) 0.0860(7) Uani 1 1 d . . . . .
O2 O 0.5937(3) 0.3380(2) 0.8775(2) 0.1319(12) Uani 1 1 d . . . . .
S1 S 0.70435(6) 0.28020(5) 0.66989(5) 0.05517(19) 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 C2 1.377(3) . ?
C1 C6 1.376(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.374(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(3) . ?
C4 C7 1.510(3) . ?
C5 C6 1.377(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.466(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N1 1.456(2) . ?
C8 C9 1.537(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C12 1.499(3) . ?
C9 N2 1.538(2) . ?
C9 C10 1.544(3) . ?
C10 C11 1.518(3) . ?
C10 S1 1.814(2) . ?
C10 H10 0.9800 . ?
C11 N1 1.451(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.385(3) . ?
C12 C17 1.392(3) . ?
C13 C14 1.376(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.379(3) . ?
C14 Cl1 1.737(2) . ?
C15 C16 1.378(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.387(3) . ?
C16 H16 0.9300 . ?
C17 S1 1.751(2) . ?
N2 O2 1.175(3) . ?
N2 O1 1.192(3) . ?

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 C1 C6 119.5(2) . . ?
C2 C1 H1 120.3 . . ?
C6 C1 H1 120.3 . . ?
C3 C2 C1 119.9(2) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 121.3(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 118.38(19) . . ?
C3 C4 C7 121.08(18) . . ?
C5 C4 C7 120.54(19) . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C1 C6 C5 120.6(2) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
N1 C7 C4 115.52(16) . . ?
N1 C7 H7A 108.4 . . ?
C4 C7 H7A 108.4 . . ?
N1 C7 H7B 108.4 . . ?
C4 C7 H7B 108.4 . . ?
H7A C7 H7B 107.5 . . ?
N1 C8 C9 102.53(15) . . ?
N1 C8 H8A 111.3 . . ?
C9 C8 H8A 111.3 . . ?
N1 C8 H8B 111.3 . . ?
C9 C8 H8B 111.3 . . ?
H8A C8 H8B 109.2 . . ?
C12 C9 C8 115.88(16) . . ?
C12 C9 N2 107.06(15) . . ?
C8 C9 N2 110.20(15) . . ?
C12 C9 C10 108.88(16) . . ?
C8 C9 C10 104.78(15) . . ?
N2 C9 C10 109.99(15) . . ?
C11 C10 C9 102.91(15) . . ?
C11 C10 S1 115.55(14) . . ?
C9 C10 S1 108.77(13) . . ?
C11 C10 H10 109.8 . . ?
C9 C10 H10 109.8 . . ?
S1 C10 H10 109.8 . . ?
N1 C11 C10 100.92(15) . . ?
N1 C11 H11A 111.6 . . ?
C10 C11 H11A 111.6 . . ?
N1 C11 H11B 111.6 . . ?
C10 C11 H11B 111.6 . . ?
H11A C11 H11B 109.4 . . ?
C13 C12 C17 120.37(18) . . ?
C13 C12 C9 125.45(17) . . ?
C17 C12 C9 114.18(17) . . ?
C14 C13 C12 118.25(18) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
C13 C14 C15 121.9(2) . . ?
C13 C14 Cl1 119.22(17) . . ?
C15 C14 Cl1 118.82(17) . . ?
C16 C15 C14 119.88(19) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 119.13(19) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C16 C17 C12 120.41(19) . . ?
C16 C17 S1 125.32(16) . . ?
C12 C17 S1 114.25(15) . . ?
C8 N1 C11 104.44(15) . . ?
C8 N1 C7 116.08(16) . . ?
C11 N1 C7 116.33(16) . . ?
O2 N2 O1 123.0(2) . . ?
O2 N2 C9 118.58(19) . . ?
O1 N2 C9 118.18(18) . . ?
C17 S1 C10 92.68(9) . . ?

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 C1 C2 C3 1.1(4) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C2 C3 C4 C7 179.7(2) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C7 C4 C5 C6 -179.50(18) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C3 C4 C7 N1 94.9(2) . . . . ?
C5 C4 C7 N1 -85.4(2) . . . . ?
N1 C8 C9 C12 -137.17(16) . . . . ?
N1 C8 C9 N2 101.10(17) . . . . ?
N1 C8 C9 C10 -17.18(19) . . . . ?
C12 C9 C10 C11 112.34(17) . . . . ?
C8 C9 C10 C11 -12.2(2) . . . . ?
N2 C9 C10 C11 -130.64(16) . . . . ?
C12 C9 C10 S1 -10.70(18) . . . . ?
C8 C9 C10 S1 -135.26(14) . . . . ?
N2 C9 C10 S1 106.32(15) . . . . ?
C9 C10 C11 N1 37.30(19) . . . . ?
S1 C10 C11 N1 155.69(13) . . . . ?
C8 C9 C12 C13 -55.9(2) . . . . ?
N2 C9 C12 C13 67.5(2) . . . . ?
C10 C9 C12 C13 -173.65(17) . . . . ?
C8 C9 C12 C17 123.50(18) . . . . ?
N2 C9 C12 C17 -113.12(18) . . . . ?
C10 C9 C12 C17 5.8(2) . . . . ?
C17 C12 C13 C14 0.9(3) . . . . ?
C9 C12 C13 C14 -179.71(18) . . . . ?
C12 C13 C14 C15 -1.0(3) . . . . ?
C12 C13 C14 Cl1 177.23(14) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
Cl1 C14 C15 C16 -178.21(17) . . . . ?
C14 C15 C16 C17 1.0(3) . . . . ?
C15 C16 C17 C12 -1.1(3) . . . . ?
C15 C16 C17 S1 177.23(16) . . . . ?
C13 C12 C17 C16 0.1(3) . . . . ?
C9 C12 C17 C16 -179.30(17) . . . . ?
C13 C12 C17 S1 -178.39(14) . . . . ?
C9 C12 C17 S1 2.2(2) . . . . ?
C9 C8 N1 C11 42.34(18) . . . . ?
C9 C8 N1 C7 171.84(15) . . . . ?
C10 C11 N1 C8 -50.62(18) . . . . ?
C10 C11 N1 C7 -179.97(16) . . . . ?
C4 C7 N1 C8 -64.1(2) . . . . ?
C4 C7 N1 C11 59.4(2) . . . . ?
C12 C9 N2 O2 88.4(3) . . . . ?
C8 C9 N2 O2 -144.7(3) . . . . ?
C10 C9 N2 O2 -29.7(3) . . . . ?
C12 C9 N2 O1 -86.6(2) . . . . ?
C8 C9 N2 O1 40.3(3) . . . . ?
C10 C9 N2 O1 155.3(2) . . . . ?
C16 C17 S1 C10 174.01(18) . . . . ?
C12 C17 S1 C10 -7.55(16) . . . . ?
C11 C10 S1 C17 -104.74(15) . . . . ?
C9 C10 S1 C17 10.35(14) . . . . ?

_refine_diff_density_max         0.375
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.042

