# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_szh_wmx2
_database_code_depnum_ccdc_archive 'CCDC 1973682'
loop_
_audit_author_name
_audit_author_address
'Yu-Hua Deng'
;Yunnan University
China
;
_audit_update_record             
;
2019-12-23 deposited with the CCDC.	2020-03-31 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C19 H14 Cl N O3 S'
_chemical_formula_sum            'C19 H14 Cl N O3 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         371.82
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.5623(3)
_cell_length_b                   8.7434(4)
_cell_length_c                   17.6707(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.868(2)
_cell_angle_gamma                90
_cell_volume                     853.22(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9832
_cell_measurement_theta_min      2.5185
_cell_measurement_theta_max      72.4424
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384

_exptl_absorpt_coefficient_mu    3.285
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.52
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            12452
_diffrn_reflns_av_R_equivalents  0.0647
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         72.44
_diffrn_reflns_theta_full        72.44
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21

_refine_special_details          
;
;

_reflns_number_total             3319
_reflns_number_gt                3179
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1071
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_number_reflns         3319
_refine_ls_number_parameters     226
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0491P)²+0.3939P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.315
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1384 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.121(11)

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service vV6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 1.00748(16) 0.98034(11) 0.96186(6) 0.0379(3) Uani d . . . 1 . .
N N1 0.1872(5) 0.1929(4) 0.70165(18) 0.0267(7) Uani d . . . 1 . .
S S1 0.37252(17) 0.01956(10) 0.81516(6) 0.0334(3) Uani d . . . 1 . .
O O1 0.0092(5) 0.2772(3) 0.58794(15) 0.0309(6) Uani d . . . 1 . .
O O2 0.4232(5) 0.1272(4) 0.60601(17) 0.0354(6) Uani d . . . 1 . .
O O3 -0.1393(5) 0.3520(3) 0.69574(16) 0.0307(6) Uani d . . . 1 . .
C C1 0.8356(7) 0.8232(5) 0.9273(2) 0.0284(8) Uani d . . . 1 . .
C C2 0.6396(7) 0.7786(5) 0.9632(2) 0.0278(8) Uani d . . . 1 . .
H H4 0.598237 0.833118 1.006285 0.033 Uiso calc U . R 1 . .
C C3 0.5044(6) 0.6536(4) 0.9356(2) 0.0263(7) Uani d . . . 1 . .
H H3 0.368571 0.62247 0.959643 0.032 Uiso calc U . R 1 . .
C C4 0.5665(7) 0.5724(4) 0.8723(2) 0.0264(8) Uani d . . . 1 . .
C C5 0.4315(7) 0.4417(5) 0.8437(2) 0.0274(8) Uani d . . . 1 . .
C C6 0.2025(7) 0.1931(5) 0.7849(2) 0.0285(8) Uani d . . . 1 . .
H H13 0.03588 0.18639 0.8005 0.034 Uiso calc U . R 1 . .
C C7 0.0036(6) 0.2836(4) 0.6624(2) 0.0249(7) Uani d . . . 1 . .
C C8 -0.1754(7) 0.3657(5) 0.5409(2) 0.0311(8) Uani d . . . 1 . .
H H9 -0.129547 0.475056 0.540347 0.037 Uiso calc U . R 1 . .
H H10 -0.333998 0.356755 0.560715 0.037 Uiso calc U . R 1 . .
C C9 -0.1874(7) 0.2983(4) 0.4624(2) 0.0275(8) Uani d . . . 1 . .
C C10 -0.3674(7) 0.1934(5) 0.4374(2) 0.0311(8) Uani d . . . 1 . .
H H8 -0.486735 0.167272 0.46939 0.037 Uiso calc U . R 1 . .
C C11 -0.3737(7) 0.1264(5) 0.3654(2) 0.0315(8) Uani d . . . 1 . .
H H5 -0.497534 0.055202 0.348323 0.038 Uiso calc U . R 1 . .
C C12 -0.1990(7) 0.1640(5) 0.3191(2) 0.0304(8) Uani d . . . 1 . .
H H1 -0.202495 0.118042 0.270222 0.036 Uiso calc U . R 1 . .
C C13 0.9005(7) 0.7459(5) 0.8636(2) 0.0283(8) Uani d . . . 1 . .
H H14 1.03495 0.779059 0.839451 0.034 Uiso calc U . R 1 . .
C C14 0.7658(7) 0.6198(5) 0.8363(2) 0.0288(8) Uani d . . . 1 . .
H H2 0.808205 0.565621 0.79319 0.035 Uiso calc U . R 1 . .
C C15 0.5251(7) 0.0225(6) 0.7303(2) 0.0343(8) Uani d . . . 1 . .
H H12 0.689208 0.066503 0.742169 0.041 Uiso calc U . R 1 . .
H H11 0.541388 -0.082982 0.711128 0.041 Uiso calc U . R 1 . .
C C16 0.3781(7) 0.1182(5) 0.6706(2) 0.0299(8) Uani d . . . 1 . .
C C17 -0.0187(7) 0.2686(5) 0.3436(2) 0.0312(8) Uani d . . . 1 . .
H H7 0.100676 0.294786 0.311561 0.037 Uiso calc U . R 1 . .
C C18 -0.0139(7) 0.3349(5) 0.4153(2) 0.0295(8) Uani d . . . 1 . .
H H6 0.109932 0.406221 0.432195 0.035 Uiso calc U . R 1 . .
C C19 0.3230(7) 0.3310(4) 0.8179(2) 0.0275(8) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 . 1.742(4) ?
N1 C7 . 1.409(5) ?
N1 C16 . 1.413(5) ?
N1 C6 . 1.463(5) ?
S1 C15 . 1.810(4) ?
S1 C6 . 1.834(4) ?
O1 C7 . 1.320(5) ?
O1 C8 . 1.463(5) ?
O2 C16 . 1.199(5) ?
O3 C7 . 1.204(5) ?
C1 C2 . 1.381(6) ?
C1 C13 . 1.397(6) ?
C2 C3 . 1.382(6) ?
C2 H4 . 0.95 ?
C3 C4 . 1.403(6) ?
C3 H3 . 0.95 ?
C4 C14 . 1.405(6) ?
C4 C5 . 1.426(5) ?
C5 C19 . 1.201(6) ?
C6 C19 . 1.466(5) ?
C6 H13 . 1.0 ?
C8 C9 . 1.502(6) ?
C8 H9 . 0.99 ?
C8 H10 . 0.99 ?
C9 C18 . 1.385(6) ?
C9 C10 . 1.390(6) ?
C10 C11 . 1.398(6) ?
C10 H8 . 0.95 ?
C11 C12 . 1.383(6) ?
C11 H5 . 0.95 ?
C12 C17 . 1.388(6) ?
C12 H1 . 0.95 ?
C13 C14 . 1.387(5) ?
C13 H14 . 0.95 ?
C14 H2 . 0.95 ?
C15 C16 . 1.509(6) ?
C15 H12 . 0.99 ?
C15 H11 . 0.99 ?
C17 C18 . 1.391(6) ?
C17 H7 . 0.95 ?
C18 H6 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 N1 C16 . . 127.1(3) ?
C7 N1 C6 . . 116.5(3) ?
C16 N1 C6 . . 115.8(3) ?
C15 S1 C6 . . 91.32(19) ?
C7 O1 C8 . . 116.4(3) ?
C2 C1 C13 . . 121.8(4) ?
C2 C1 Cl1 . . 119.5(3) ?
C13 C1 Cl1 . . 118.7(3) ?
C1 C2 C3 . . 119.2(4) ?
C1 C2 H4 . . 120.4 ?
C3 C2 H4 . . 120.4 ?
C2 C3 C4 . . 120.4(4) ?
C2 C3 H3 . . 119.8 ?
C4 C3 H3 . . 119.8 ?
C3 C4 C14 . . 119.6(4) ?
C3 C4 C5 . . 121.2(4) ?
C14 C4 C5 . . 119.2(4) ?
C19 C5 C4 . . 177.8(4) ?
N1 C6 C19 . . 111.8(3) ?
N1 C6 S1 . . 105.0(3) ?
C19 C6 S1 . . 111.6(3) ?
N1 C6 H13 . . 109.5 ?
C19 C6 H13 . . 109.5 ?
S1 C6 H13 . . 109.5 ?
O3 C7 O1 . . 127.2(3) ?
O3 C7 N1 . . 121.4(3) ?
O1 C7 N1 . . 111.4(3) ?
O1 C8 C9 . . 105.5(3) ?
O1 C8 H9 . . 110.6 ?
C9 C8 H9 . . 110.6 ?
O1 C8 H10 . . 110.6 ?
C9 C8 H10 . . 110.6 ?
H9 C8 H10 . . 108.8 ?
C18 C9 C10 . . 119.3(4) ?
C18 C9 C8 . . 120.5(4) ?
C10 C9 C8 . . 120.2(4) ?
C9 C10 C11 . . 120.3(4) ?
C9 C10 H8 . . 119.8 ?
C11 C10 H8 . . 119.8 ?
C12 C11 C10 . . 119.7(4) ?
C12 C11 H5 . . 120.1 ?
C10 C11 H5 . . 120.1 ?
C11 C12 C17 . . 120.3(4) ?
C11 C12 H1 . . 119.8 ?
C17 C12 H1 . . 119.8 ?
C14 C13 C1 . . 119.0(4) ?
C14 C13 H14 . . 120.5 ?
C1 C13 H14 . . 120.5 ?
C13 C14 C4 . . 120.0(4) ?
C13 C14 H2 . . 120.0 ?
C4 C14 H2 . . 120.0 ?
C16 C15 S1 . . 108.6(3) ?
C16 C15 H12 . . 110.0 ?
S1 C15 H12 . . 110.0 ?
C16 C15 H11 . . 110.0 ?
S1 C15 H11 . . 110.0 ?
H12 C15 H11 . . 108.3 ?
O2 C16 N1 . . 126.3(4) ?
O2 C16 C15 . . 123.0(4) ?
N1 C16 C15 . . 110.7(4) ?
C12 C17 C18 . . 119.6(4) ?
C12 C17 H7 . . 120.2 ?
C18 C17 H7 . . 120.2 ?
C9 C18 C17 . . 120.8(4) ?
C9 C18 H6 . . 119.6 ?
C17 C18 H6 . . 119.6 ?
C5 C19 C6 . . 176.9(4) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C13 C1 C2 C3 . . . . 0.3(6) ?
Cl1 C1 C2 C3 . . . . -179.8(3) ?
C1 C2 C3 C4 . . . . 0.5(6) ?
C2 C3 C4 C14 . . . . -0.8(5) ?
C2 C3 C4 C5 . . . . 179.0(3) ?
C7 N1 C6 C19 . . . . -78.7(4) ?
C16 N1 C6 C19 . . . . 93.1(4) ?
C7 N1 C6 S1 . . . . 160.1(3) ?
C16 N1 C6 S1 . . . . -28.1(4) ?
C15 S1 C6 N1 . . . . 26.8(3) ?
C15 S1 C6 C19 . . . . -94.5(3) ?
C8 O1 C7 O3 . . . . 1.5(6) ?
C8 O1 C7 N1 . . . . 179.3(3) ?
C16 N1 C7 O3 . . . . -174.0(4) ?
C6 N1 C7 O3 . . . . -3.3(5) ?
C16 N1 C7 O1 . . . . 8.1(5) ?
C6 N1 C7 O1 . . . . 178.8(3) ?
C7 O1 C8 C9 . . . . -160.6(3) ?
O1 C8 C9 C18 . . . . -78.6(4) ?
O1 C8 C9 C10 . . . . 98.8(4) ?
C18 C9 C10 C11 . . . . -0.3(6) ?
C8 C9 C10 C11 . . . . -177.7(4) ?
C9 C10 C11 C12 . . . . 0.4(6) ?
C10 C11 C12 C17 . . . . -0.4(6) ?
C2 C1 C13 C14 . . . . -0.7(6) ?
Cl1 C1 C13 C14 . . . . 179.4(3) ?
C1 C13 C14 C4 . . . . 0.4(6) ?
C3 C4 C14 C13 . . . . 0.3(5) ?
C5 C4 C14 C13 . . . . -179.4(3) ?
C6 S1 C15 C16 . . . . -20.4(3) ?
C7 N1 C16 O2 . . . . 4.6(6) ?
C6 N1 C16 O2 . . . . -166.1(4) ?
C7 N1 C16 C15 . . . . -175.6(3) ?
C6 N1 C16 C15 . . . . 13.6(5) ?
S1 C15 C16 O2 . . . . -172.2(3) ?
S1 C15 C16 N1 . . . . 8.1(4) ?
C11 C12 C17 C18 . . . . 0.3(6) ?
C10 C9 C18 C17 . . . . 0.2(6) ?
C8 C9 C18 C17 . . . . 177.6(4) ?
C12 C17 C18 C9 . . . . -0.3(6) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C8 H10 O2 1_455 0.99 2.60 3.357(5) 133.4 ?
C13 H14 S1 1_665 0.95 2.89 3.727(4) 148.3 ?

