# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_220905a
_database_code_depnum_ccdc_archive 'CCDC 2303358'
loop_
_audit_author_name
_audit_author_address
'Yi-Long Zhu'
;Nanjing Tech University
China
;
_audit_update_record             
;
2023-10-25 deposited with the CCDC.	2023-12-18 downloaded from the CCDC.
;
_audit_creation_date             2022-09-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H16 Cl N O2 S'
_chemical_formula_sum            'C16 H16 Cl N O2 S'
_chemical_formula_weight         321.81
_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'
Cl Cl 0.1484 0.1585 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5547(8)
_cell_length_b                   10.3453(11)
_cell_length_c                   11.0141(12)
_cell_angle_alpha                87.479(3)
_cell_angle_beta                 80.687(2)
_cell_angle_gamma                70.1750(10)
_cell_volume                     799.07(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1979
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.583
_cell_measurement_theta_min      2.827
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.906
_exptl_absorpt_coefficient_mu    0.373
_exptl_absorpt_correction_T_max  0.9637
_exptl_absorpt_correction_T_min  0.9061
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3910
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.010
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_min         2.793
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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                2054
_reflns_number_total             2735
_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       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2735
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0489
_refine_ls_restrained_S_all      1.088
_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)+(0.0809P)²+0.0594P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1372
_refine_ls_wR_factor_ref         0.1480
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C14(H14),
 C15(H15)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Cl1 Cl 0.38269(15) -0.21308(8) 0.51189(8) 0.0815(3) Uani 1 1 d . . . . .
N1 N 0.1964(4) 0.0841(2) 0.4834(2) 0.0582(7) Uani 1 1 d . . . . .
H1 H 0.255416 0.020417 0.429060 0.070 Uiso 1 1 calc R U . . .
O1 O -0.1284(3) 0.4832(2) 0.38321(17) 0.0626(6) Uani 1 1 d . . . . .
O2 O -0.0907(3) 0.3994(2) 0.16869(17) 0.0652(6) Uani 1 1 d . . . . .
S1 S -0.00590(10) 0.40767(7) 0.27560(6) 0.0494(2) Uani 1 1 d . . . . .
C1 C 0.1994(4) 0.0443(3) 0.6072(2) 0.0476(6) Uani 1 1 d . . . . .
C2 C 0.2836(4) -0.0945(3) 0.6339(3) 0.0505(7) Uani 1 1 d . . . . .
C3 C 0.2886(5) -0.1408(3) 0.7543(3) 0.0607(8) Uani 1 1 d . . . . .
H3 H 0.343968 -0.233806 0.769505 0.073 Uiso 1 1 calc R U . . .
C4 C 0.2106(5) -0.0477(3) 0.8513(3) 0.0613(8) Uani 1 1 d . . . . .
H4 H 0.213217 -0.077375 0.932152 0.074 Uiso 1 1 calc R U . . .
C5 C 0.1286(5) 0.0902(3) 0.8261(3) 0.0616(8) Uani 1 1 d . . . . .
H5 H 0.076581 0.153375 0.890834 0.074 Uiso 1 1 calc R U . . .
C6 C 0.1228(5) 0.1358(3) 0.7060(3) 0.0618(8) Uani 1 1 d . . . . .
H6 H 0.066769 0.228913 0.691442 0.074 Uiso 1 1 calc R U . . .
C7 C 0.1103(4) 0.2128(3) 0.4391(2) 0.0509(7) Uani 1 1 d . . . . .
H7 H 0.043465 0.283972 0.495121 0.061 Uiso 1 1 calc R U . . .
C8 C 0.1187(4) 0.2399(3) 0.3181(2) 0.0495(7) Uani 1 1 d . . . . .
C9 C 0.2237(5) 0.1364(3) 0.2158(3) 0.0686(9) Uani 1 1 d . . . . .
H9A H 0.352630 0.091074 0.229346 0.103 Uiso 1 1 calc R U . . .
H9B H 0.223846 0.182795 0.138333 0.103 Uiso 1 1 calc R U . . .
H9C H 0.161453 0.069651 0.214607 0.103 Uiso 1 1 calc R U . . .
C10 C 0.1711(4) 0.4855(3) 0.2294(2) 0.0428(6) Uani 1 1 d . . . . .
C11 C 0.2880(4) 0.4949(3) 0.3113(2) 0.0511(7) Uani 1 1 d . . . . .
H11 H 0.280674 0.454427 0.388244 0.061 Uiso 1 1 calc R U . . .
C12 C 0.4163(4) 0.5650(3) 0.2780(3) 0.0537(7) Uani 1 1 d . . . . .
H12 H 0.497757 0.568470 0.331783 0.064 Uiso 1 1 calc R U . . .
C13 C 0.4236(4) 0.6310(3) 0.1633(3) 0.0550(7) Uani 1 1 d . . . . .
C14 C 0.3083(4) 0.6175(3) 0.0821(3) 0.0563(7) Uani 1 1 d . . . . .
H14 H 0.316280 0.657128 0.004916 0.068 Uiso 1 1 calc R U . . .
C15 C 0.1808(4) 0.5461(3) 0.1131(2) 0.0483(7) Uani 1 1 d . . . . .
H15 H 0.103621 0.538839 0.057847 0.058 Uiso 1 1 calc R U . . .
C16 C 0.5580(5) 0.7124(3) 0.1312(4) 0.0805(10) Uani 1 1 d . . . . .
H16A H 0.687280 0.650849 0.121170 0.121 Uiso 1 1 calc R U . . .
H16B H 0.537782 0.777134 0.196214 0.121 Uiso 1 1 calc R U . . .
H16C H 0.533791 0.760806 0.055950 0.121 Uiso 1 1 calc R U . . .


_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
Cl1 C2 1.751(3) . ?
N1 H1 0.8600 . ?
N1 C1 1.408(3) . ?
N1 C7 1.375(4) . ?
O1 S1 1.4519(19) . ?
O2 S1 1.447(2) . ?
S1 C8 1.756(3) . ?
S1 C10 1.780(3) . ?
C1 C2 1.399(4) . ?
C1 C6 1.390(4) . ?
C2 C3 1.392(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.346(4) . ?
C8 C9 1.512(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.388(4) . ?
C10 C15 1.403(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.393(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.411(4) . ?
C13 C14 1.387(4) . ?
C13 C16 1.517(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.394(4) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C1 N1 H1 116.2 . . ?
C7 N1 H1 116.2 . . ?
C7 N1 C1 127.6(2) . . ?
O1 S1 C8 109.29(12) . . ?
O1 S1 C10 106.95(12) . . ?
O2 S1 O1 118.52(13) . . ?
O2 S1 C8 108.26(13) . . ?
O2 S1 C10 107.68(12) . . ?
C8 S1 C10 105.36(13) . . ?
C2 C1 N1 119.0(2) . . ?
C6 C1 N1 123.6(2) . . ?
C6 C1 C2 117.4(2) . . ?
C1 C2 Cl1 118.8(2) . . ?
C3 C2 Cl1 119.4(2) . . ?
C3 C2 C1 121.8(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.5 . . ?
C5 C4 C3 119.0(3) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.1(3) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.0(3) . . ?
C5 C6 H6 119.5 . . ?
N1 C7 H7 118.7 . . ?
C8 C7 N1 122.7(3) . . ?
C8 C7 H7 118.7 . . ?
C7 C8 S1 117.5(2) . . ?
C7 C8 C9 125.2(3) . . ?
C9 C8 S1 117.4(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 S1 120.05(19) . . ?
C11 C10 C15 120.7(2) . . ?
C15 C10 S1 119.1(2) . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.8(2) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.5(3) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C16 119.7(3) . . ?
C14 C13 C12 118.5(3) . . ?
C14 C13 C16 121.8(3) . . ?
C13 C14 H14 119.1 . . ?
C13 C14 C15 121.8(2) . . ?
C15 C14 H14 119.1 . . ?
C10 C15 H15 120.7 . . ?
C14 C15 C10 118.7(3) . . ?
C14 C15 H15 120.7 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
Cl1 C2 C3 C4 180.0(2) . . . . ?
N1 C1 C2 Cl1 0.2(4) . . . . ?
N1 C1 C2 C3 -179.0(3) . . . . ?
N1 C1 C6 C5 179.5(3) . . . . ?
N1 C7 C8 S1 177.7(2) . . . . ?
N1 C7 C8 C9 -1.0(5) . . . . ?
O1 S1 C8 C7 -10.7(3) . . . . ?
O1 S1 C8 C9 168.1(2) . . . . ?
O1 S1 C10 C11 57.5(2) . . . . ?
O1 S1 C10 C15 -117.6(2) . . . . ?
O2 S1 C8 C7 -141.1(2) . . . . ?
O2 S1 C8 C9 37.7(3) . . . . ?
O2 S1 C10 C11 -174.1(2) . . . . ?
O2 S1 C10 C15 10.8(3) . . . . ?
S1 C10 C11 C12 -175.1(2) . . . . ?
S1 C10 C15 C14 174.3(2) . . . . ?
C1 N1 C7 C8 179.1(3) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C2 C1 C6 C5 -0.6(4) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
C4 C5 C6 C1 -0.1(5) . . . . ?
C6 C1 C2 Cl1 -179.7(2) . . . . ?
C6 C1 C2 C3 1.1(4) . . . . ?
C7 N1 C1 C2 175.4(3) . . . . ?
C7 N1 C1 C6 -4.6(5) . . . . ?
C8 S1 C10 C11 -58.7(2) . . . . ?
C8 S1 C10 C15 126.1(2) . . . . ?
C10 S1 C8 C7 103.9(2) . . . . ?
C10 S1 C8 C9 -77.3(2) . . . . ?
C10 C11 C12 C13 2.3(4) . . . . ?
C11 C10 C15 C14 -0.8(4) . . . . ?
C11 C12 C13 C14 -3.7(4) . . . . ?
C11 C12 C13 C16 177.2(3) . . . . ?
C12 C13 C14 C15 2.8(4) . . . . ?
C13 C14 C15 C10 -0.6(4) . . . . ?
C15 C10 C11 C12 0.0(4) . . . . ?
C16 C13 C14 C15 -178.0(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
