# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_wc-01-1015
_database_code_depnum_ccdc_archive 'CCDC 2333072'
loop_
_audit_author_name
_audit_author_address
wc
;Zhongkai University of agriculture and engineering
China
;
_audit_update_record             
;
2024-02-15 deposited with the CCDC.	2024-02-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        wc
_chemical_name_common            wc
_chemical_melting_point          unknow
_chemical_formula_moiety         C13H14ClNO4S
_chemical_formula_sum            'C13 H14 Cl N O4 S'
_chemical_formula_weight         315.76

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'
Cl Cl 0.3639 0.7018 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   5.5934(2)
_cell_length_b                   10.4137(3)
_cell_length_c                   12.5612(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.969(3)
_cell_angle_gamma                90
_cell_volume                     724.60(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       crystal
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    3.803
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7965
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.553
_diffrn_reflns_theta_max         75.687
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             2842
_reflns_number_gt                2840
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.849
_reflns_Friedel_fraction_max     0.924
_reflns_Friedel_fraction_full    0.965

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0569P)²+0.3879P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.035(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.027(18)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2842
_refine_ls_number_parameters     184
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0824
_refine_ls_wR_factor_gt          0.0824
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.037
_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
S10 S -0.30635(12) 0.44187(6) 0.38930(5) 0.0146(2) Uani 1 1 d . . . . .
Cl7 Cl 0.99089(14) 0.56782(7) 0.83408(6) 0.0231(2) Uani 1 1 d . . . . .
O18 O -0.0712(3) 0.3732(2) 0.04433(16) 0.0145(4) Uani 1 1 d . . . . .
H18 H 0.008912 0.322953 0.010689 0.022 Uiso 1 1 calc R U . . .
O15 O -0.0587(3) 0.7053(2) 0.08678(16) 0.0144(4) Uani 1 1 d . . . . .
O19 O 0.2842(3) 0.3999(2) 0.14926(17) 0.0163(4) Uani 1 1 d . . . . .
O20 O 0.0917(5) 0.2872(2) 0.5119(2) 0.0320(6) Uani 1 1 d . . . . .
N13 N -0.2823(4) 0.5543(2) 0.15398(18) 0.0118(5) Uani 1 1 d . . . . .
H13 H -0.427538 0.526827 0.161847 0.014 Uiso 1 1 calc R U . . .
C1 C 0.7378(6) 0.5205(3) 0.7465(2) 0.0181(6) Uani 1 1 d . . . . .
C9 C -0.0497(6) 0.5021(3) 0.4776(2) 0.0152(6) Uani 1 1 d . . . . .
H9A H 0.041855 0.560594 0.436059 0.018 Uiso 1 1 calc R U . . .
H9B H -0.109172 0.553478 0.534822 0.018 Uiso 1 1 calc R U . . .
C14 C -0.2608(5) 0.6572(3) 0.0933(2) 0.0116(5) Uani 1 1 d . . . . .
C12 C -0.0747(5) 0.4865(3) 0.2073(2) 0.0101(5) Uani 1 1 d . . . . .
H12 H 0.034215 0.548339 0.251429 0.012 Uiso 1 1 calc R U . . .
C2 C 0.5882(6) 0.6140(3) 0.6938(2) 0.0180(6) Uani 1 1 d . . . . .
H2 H 0.622715 0.702512 0.705930 0.022 Uiso 1 1 calc R U . . .
C17 C 0.0664(5) 0.4176(2) 0.1287(2) 0.0106(5) Uani 1 1 d . . . . .
C8 C 0.1225(6) 0.4004(3) 0.5304(2) 0.0179(6) Uani 1 1 d . . . . .
C11 C -0.1561(5) 0.3822(3) 0.2806(2) 0.0122(5) Uani 1 1 d . . . . .
H11A H -0.012775 0.332142 0.311707 0.015 Uiso 1 1 calc R U . . .
H11B H -0.266765 0.322873 0.236306 0.015 Uiso 1 1 calc R U . . .
C16 C -0.4875(5) 0.7121(3) 0.0329(3) 0.0230(7) Uani 1 1 d . . . . .
H16A H -0.492781 0.804718 0.046014 0.035 Uiso 1 1 calc R U . . .
H16B H -0.627791 0.670958 0.057415 0.035 Uiso 1 1 calc R U . . .
H16C H -0.490396 0.696366 -0.044178 0.035 Uiso 1 1 calc R U . . .
C4 C 0.3362(5) 0.4458(3) 0.6059(2) 0.0165(6) Uani 1 1 d . . . . .
C3 C 0.3881(5) 0.5761(3) 0.6235(2) 0.0157(6) Uani 1 1 d . . . . .
H3 H 0.285117 0.639159 0.586721 0.019 Uiso 1 1 calc R U . . .
C6 C 0.6914(6) 0.3903(3) 0.7307(2) 0.0224(7) Uani 1 1 d . . . . .
H6 H 0.795476 0.327732 0.767460 0.027 Uiso 1 1 calc R U . . .
C5 C 0.4906(6) 0.3535(3) 0.6602(3) 0.0220(7) Uani 1 1 d . . . . .
H5 H 0.456817 0.264853 0.648492 0.026 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
S10 C9 1.801(3) . ?
S10 C11 1.809(3) . ?
Cl7 C1 1.739(3) . ?
O18 C17 1.305(3) . ?
O18 H18 0.8400 . ?
O15 C14 1.249(4) . ?
O19 C17 1.224(3) . ?
O20 C8 1.209(4) . ?
N13 C14 1.330(4) . ?
N13 C12 1.442(3) . ?
N13 H13 0.8800 . ?
C1 C6 1.390(5) . ?
C1 C2 1.390(5) . ?
C9 C8 1.520(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C14 C16 1.497(4) . ?
C12 C17 1.526(4) . ?
C12 C11 1.533(4) . ?
C12 H12 1.0000 . ?
C2 C3 1.384(4) . ?
C2 H2 0.9500 . ?
C8 C4 1.496(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C4 C3 1.399(4) . ?
C4 C5 1.404(4) . ?
C3 H3 0.9500 . ?
C6 C5 1.384(5) . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?

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
C9 S10 C11 99.79(13) . . ?
C17 O18 H18 109.5 . . ?
C14 N13 C12 122.0(2) . . ?
C14 N13 H13 119.0 . . ?
C12 N13 H13 119.0 . . ?
C6 C1 C2 121.8(3) . . ?
C6 C1 Cl7 119.1(3) . . ?
C2 C1 Cl7 119.1(2) . . ?
C8 C9 S10 115.4(2) . . ?
C8 C9 H9A 108.4 . . ?
S10 C9 H9A 108.4 . . ?
C8 C9 H9B 108.4 . . ?
S10 C9 H9B 108.4 . . ?
H9A C9 H9B 107.5 . . ?
O15 C14 N13 121.0(3) . . ?
O15 C14 C16 121.7(3) . . ?
N13 C14 C16 117.4(2) . . ?
N13 C12 C17 112.7(2) . . ?
N13 C12 C11 109.8(2) . . ?
C17 C12 C11 106.2(2) . . ?
N13 C12 H12 109.4 . . ?
C17 C12 H12 109.4 . . ?
C11 C12 H12 109.4 . . ?
C3 C2 C1 119.0(3) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
O19 C17 O18 125.2(2) . . ?
O19 C17 C12 121.5(2) . . ?
O18 C17 C12 113.1(2) . . ?
O20 C8 C4 120.7(3) . . ?
O20 C8 C9 122.0(3) . . ?
C4 C8 C9 117.3(3) . . ?
C12 C11 S10 114.70(19) . . ?
C12 C11 H11A 108.6 . . ?
S10 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
S10 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C3 C4 C5 119.2(3) . . ?
C3 C4 C8 122.5(3) . . ?
C5 C4 C8 118.4(3) . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C6 C1 118.7(3) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?

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
C11 S10 C9 C8 -69.3(2) . . . . ?
C12 N13 C14 O15 -5.6(4) . . . . ?
C12 N13 C14 C16 174.0(3) . . . . ?
C14 N13 C12 C17 -68.1(3) . . . . ?
C14 N13 C12 C11 173.8(2) . . . . ?
C6 C1 C2 C3 -0.2(5) . . . . ?
Cl7 C1 C2 C3 179.4(2) . . . . ?
N13 C12 C17 O19 150.5(2) . . . . ?
C11 C12 C17 O19 -89.3(3) . . . . ?
N13 C12 C17 O18 -34.4(3) . . . . ?
C11 C12 C17 O18 85.9(3) . . . . ?
S10 C9 C8 O20 1.9(4) . . . . ?
S10 C9 C8 C4 -179.0(2) . . . . ?
N13 C12 C11 S10 -63.0(2) . . . . ?
C17 C12 C11 S10 174.91(17) . . . . ?
C9 S10 C11 C12 -75.4(2) . . . . ?
O20 C8 C4 C3 175.1(3) . . . . ?
C9 C8 C4 C3 -4.0(4) . . . . ?
O20 C8 C4 C5 -4.3(5) . . . . ?
C9 C8 C4 C5 176.6(3) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C5 C4 C3 C2 -0.4(4) . . . . ?
C8 C4 C3 C2 -179.8(3) . . . . ?
C2 C1 C6 C5 0.1(5) . . . . ?
Cl7 C1 C6 C5 -179.5(2) . . . . ?
C1 C6 C5 C4 -0.1(5) . . . . ?
C3 C4 C5 C6 0.3(5) . . . . ?
C8 C4 C5 C6 179.7(3) . . . . ?

_refine_diff_density_max         0.341
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.058

