# Electronic Supplementary Material (ESI) for RSC Medicinal Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 2131905'
loop_
_audit_author_name
_audit_author_address
'Dongyan Yang'
;Zhongkai University of Agriculture and Engineering
China
;
_audit_update_record             
;
2021-12-31 deposited with the CCDC.	2022-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H19 Cl2 N3 O5 S'
_chemical_formula_weight         472.33

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.9695(16)
_cell_length_b                   8.2413(16)
_cell_length_c                   16.800(3)
_cell_angle_alpha                83.69(3)
_cell_angle_beta                 88.28(3)
_cell_angle_gamma                77.67(3)
_cell_volume                     1071.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    3045
_cell_measurement_theta_min      2.4396
_cell_measurement_theta_max      27.8346

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.437
_shelx_estimated_absorpt_T_min   0.918
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.8259
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11105
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.440
_diffrn_reflns_theta_max         27.855
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5030
_reflns_number_gt                3461
_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       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0943P)²] 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         5030
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1676
_refine_ls_wR_factor_gt          0.1497
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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 0.53162(11) 0.12567(9) 0.07199(5) 0.0574(2) Uani 1 1 d . . . . .
Cl1 Cl 0.93864(11) 0.20893(9) -0.06529(5) 0.0632(3) Uani 1 1 d . . . . .
Cl2 Cl 0.78702(8) 0.52232(8) 0.04101(4) 0.04034(19) Uani 1 1 d . . . . .
O1 O 0.3560(2) 0.3095(2) 0.18969(11) 0.0447(5) Uani 1 1 d . . . . .
O2 O 0.3631(2) 0.6214(2) 0.21979(10) 0.0394(4) Uani 1 1 d . . . . .
O3 O 0.5723(2) 0.29761(19) 0.36373(10) 0.0375(4) Uani 1 1 d . . . . .
O4 O 0.3013(2) 0.3462(2) 0.41059(11) 0.0440(4) Uani 1 1 d . . . . .
O5 O 0.3485(2) 0.8237(2) 0.42918(10) 0.0379(4) Uani 1 1 d . . . . .
N1 N 0.6892(4) 0.0881(3) 0.00604(17) 0.0636(7) Uani 1 1 d . . . . .
N2 N 0.4701(2) 0.5543(3) 0.15846(12) 0.0368(5) Uani 1 1 d . . . . .
N3 N 0.3290(2) 0.6590(2) 0.42811(12) 0.0328(4) Uani 1 1 d . . . . .
C1 C 0.7668(4) 0.2147(3) -0.00189(16) 0.0477(7) Uani 1 1 d . . . . .
C2 C 0.7022(3) 0.3487(3) 0.04428(14) 0.0367(5) Uani 1 1 d . . . . .
C3 C 0.5663(3) 0.3156(3) 0.09085(15) 0.0363(5) Uani 1 1 d . . . . .
C4 C 0.4563(3) 0.4056(3) 0.14953(15) 0.0368(5) Uani 1 1 d . . . . .
C5 C 0.1710(3) 0.3791(4) 0.1962(2) 0.0539(8) Uani 1 1 d . . . . .
H5A H 0.131460 0.460215 0.149121 0.065 Uiso 1 1 calc R U . . .
H5B H 0.145876 0.437128 0.245117 0.065 Uiso 1 1 calc R U . . .
C6 C 0.0813(4) 0.2339(4) 0.2000(2) 0.0625(9) Uani 1 1 d . . . . .
H6 H 0.105013 0.161884 0.155046 0.075 Uiso 1 1 calc R U . . .
C7 C -0.0918(3) 0.2581(3) 0.23491(16) 0.0443(6) Uani 1 1 d . . . . .
H7A H -0.175434 0.202774 0.212261 0.053 Uiso 1 1 calc R U . . .
H7B H -0.141686 0.367847 0.253877 0.053 Uiso 1 1 calc R U . . .
C8 C 0.0563(4) 0.1509(4) 0.2791(2) 0.0686(10) Uani 1 1 d . . . . .
H8A H 0.098712 0.193538 0.325767 0.082 Uiso 1 1 calc R U . . .
H8B H 0.064979 0.028543 0.284171 0.082 Uiso 1 1 calc R U . . .
C9 C 0.4213(3) 0.7682(3) 0.23750(16) 0.0397(6) Uani 1 1 d . . . . .
H9A H 0.334593 0.833690 0.271518 0.048 Uiso 1 1 calc R U . . .
H9B H 0.432507 0.839199 0.186945 0.048 Uiso 1 1 calc R U . . .
C10 C 0.5909(3) 0.7230(3) 0.27980(14) 0.0313(5) Uani 1 1 d . . . . .
C11 C 0.7356(3) 0.7703(3) 0.24539(16) 0.0384(6) Uani 1 1 d . . . . .
H11 H 0.727196 0.833390 0.194286 0.046 Uiso 1 1 calc R U . . .
C12 C 0.8931(3) 0.7272(3) 0.28425(17) 0.0421(6) Uani 1 1 d . . . . .
H12 H 0.991195 0.760035 0.259611 0.051 Uiso 1 1 calc R U . . .
C13 C 0.9061(3) 0.6369(3) 0.35839(17) 0.0415(6) Uani 1 1 d . . . . .
H13 H 1.013039 0.609390 0.385419 0.050 Uiso 1 1 calc R U . . .
C14 C 0.7635(3) 0.5854(3) 0.39428(15) 0.0360(5) Uani 1 1 d . . . . .
H14 H 0.773680 0.521496 0.445193 0.043 Uiso 1 1 calc R U . . .
C15 C 0.6063(3) 0.6281(3) 0.35518(14) 0.0296(5) Uani 1 1 d . . . . .
C16 C 0.4533(3) 0.5700(3) 0.39260(13) 0.0284(5) Uani 1 1 d . . . . .
C17 C 0.4305(3) 0.3943(3) 0.39052(14) 0.0316(5) Uani 1 1 d . . . . .
C18 C 0.5611(4) 0.1259(3) 0.35814(18) 0.0464(6) Uani 1 1 d . . . . .
H18A H 0.532064 0.074963 0.410833 0.070 Uiso 1 1 calc R U . . .
H18B H 0.671783 0.063269 0.340104 0.070 Uiso 1 1 calc R U . . .
H18C H 0.471799 0.123285 0.319710 0.070 Uiso 1 1 calc R U . . .
C19 C 0.1985(3) 0.9139(3) 0.46649(17) 0.0468(7) Uani 1 1 d . . . . .
H19A H 0.097502 0.917415 0.433972 0.070 Uiso 1 1 calc R U . . .
H19B H 0.211761 1.028050 0.471018 0.070 Uiso 1 1 calc R U . . .
H19C H 0.183719 0.857961 0.520001 0.070 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
S1 N1 1.651(3) . ?
S1 C3 1.710(3) . ?
Cl1 C1 1.705(3) . ?
Cl2 C2 1.703(2) . ?
O1 C4 1.357(3) . ?
O1 C5 1.468(3) . ?
O2 N2 1.402(3) . ?
O2 C9 1.447(3) . ?
O3 C17 1.333(3) . ?
O3 C18 1.451(3) . ?
O4 C17 1.206(3) . ?
O5 N3 1.401(2) . ?
O5 C19 1.432(3) . ?
N1 C1 1.315(4) . ?
N2 C4 1.279(3) . ?
N3 C16 1.275(3) . ?
C1 C2 1.417(4) . ?
C2 C3 1.374(4) . ?
C3 C4 1.457(4) . ?
C5 C6 1.514(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C8 1.455(5) . ?
C6 C7 1.465(4) . ?
C6 H6 1.0000 . ?
C7 C8 1.479(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.502(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.386(3) . ?
C10 C15 1.407(3) . ?
C11 C12 1.391(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.374(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.394(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.391(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.499(3) . ?
C16 C17 1.502(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
N1 S1 C3 95.82(13) . . ?
C4 O1 C5 118.46(19) . . ?
N2 O2 C9 106.49(17) . . ?
C17 O3 C18 115.06(18) . . ?
N3 O5 C19 107.70(18) . . ?
C1 N1 S1 108.6(2) . . ?
C4 N2 O2 112.1(2) . . ?
C16 N3 O5 112.44(18) . . ?
N1 C1 C2 117.2(3) . . ?
N1 C1 Cl1 119.1(2) . . ?
C2 C1 Cl1 123.7(2) . . ?
C3 C2 C1 110.2(2) . . ?
C3 C2 Cl2 126.6(2) . . ?
C1 C2 Cl2 123.3(2) . . ?
C2 C3 C4 133.5(2) . . ?
C2 C3 S1 108.3(2) . . ?
C4 C3 S1 118.22(19) . . ?
N2 C4 O1 129.7(3) . . ?
N2 C4 C3 118.7(2) . . ?
O1 C4 C3 111.6(2) . . ?
O1 C5 C6 106.9(2) . . ?
O1 C5 H5A 110.3 . . ?
C6 C5 H5A 110.3 . . ?
O1 C5 H5B 110.3 . . ?
C6 C5 H5B 110.3 . . ?
H5A C5 H5B 108.6 . . ?
C8 C6 C7 60.9(2) . . ?
C8 C6 C5 116.8(3) . . ?
C7 C6 C5 117.3(3) . . ?
C8 C6 H6 116.7 . . ?
C7 C6 H6 116.7 . . ?
C5 C6 H6 116.7 . . ?
C6 C7 C8 59.2(2) . . ?
C6 C7 H7A 117.9 . . ?
C8 C7 H7A 117.9 . . ?
C6 C7 H7B 117.9 . . ?
C8 C7 H7B 117.9 . . ?
H7A C7 H7B 115.0 . . ?
C6 C8 C7 59.9(2) . . ?
C6 C8 H8A 117.8 . . ?
C7 C8 H8A 117.8 . . ?
C6 C8 H8B 117.8 . . ?
C7 C8 H8B 117.8 . . ?
H8A C8 H8B 114.9 . . ?
O2 C9 C10 111.71(19) . . ?
O2 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
O2 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C15 118.5(2) . . ?
C11 C10 C9 121.2(2) . . ?
C15 C10 C9 120.2(2) . . ?
C10 C11 C12 121.3(2) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 119.7(2) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.5(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 119.7(2) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C10 120.3(2) . . ?
C14 C15 C16 120.0(2) . . ?
C10 C15 C16 119.7(2) . . ?
N3 C16 C15 125.9(2) . . ?
N3 C16 C17 112.25(19) . . ?
C15 C16 C17 121.82(18) . . ?
O4 C17 O3 124.2(2) . . ?
O4 C17 C16 124.6(2) . . ?
O3 C17 C16 111.14(18) . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O5 C19 H19A 109.5 . . ?
O5 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O5 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C3 S1 N1 C1 0.1(2) . . . . ?
C9 O2 N2 C4 165.76(19) . . . . ?
C19 O5 N3 C16 177.0(2) . . . . ?
S1 N1 C1 C2 -0.5(3) . . . . ?
S1 N1 C1 Cl1 178.82(15) . . . . ?
N1 C1 C2 C3 0.8(3) . . . . ?
Cl1 C1 C2 C3 -178.49(19) . . . . ?
N1 C1 C2 Cl2 -179.8(2) . . . . ?
Cl1 C1 C2 Cl2 0.9(3) . . . . ?
C1 C2 C3 C4 178.6(2) . . . . ?
Cl2 C2 C3 C4 -0.8(4) . . . . ?
C1 C2 C3 S1 -0.7(3) . . . . ?
Cl2 C2 C3 S1 179.94(14) . . . . ?
N1 S1 C3 C2 0.4(2) . . . . ?
N1 S1 C3 C4 -179.00(19) . . . . ?
O2 N2 C4 O1 0.2(3) . . . . ?
O2 N2 C4 C3 -176.79(19) . . . . ?
C5 O1 C4 N2 52.5(4) . . . . ?
C5 O1 C4 C3 -130.4(3) . . . . ?
C2 C3 C4 N2 7.5(4) . . . . ?
S1 C3 C4 N2 -173.36(17) . . . . ?
C2 C3 C4 O1 -170.0(2) . . . . ?
S1 C3 C4 O1 9.2(3) . . . . ?
C4 O1 C5 C6 149.7(3) . . . . ?
O1 C5 C6 C8 89.1(3) . . . . ?
O1 C5 C6 C7 158.4(3) . . . . ?
C5 C6 C7 C8 -107.0(4) . . . . ?
C5 C6 C8 C7 107.8(3) . . . . ?
N2 O2 C9 C10 -71.5(2) . . . . ?
O2 C9 C10 C11 117.1(2) . . . . ?
O2 C9 C10 C15 -61.7(3) . . . . ?
C15 C10 C11 C12 -0.6(3) . . . . ?
C9 C10 C11 C12 -179.4(2) . . . . ?
C10 C11 C12 C13 -0.4(4) . . . . ?
C11 C12 C13 C14 1.3(4) . . . . ?
C12 C13 C14 C15 -1.0(4) . . . . ?
C13 C14 C15 C10 -0.1(3) . . . . ?
C13 C14 C15 C16 178.7(2) . . . . ?
C11 C10 C15 C14 0.9(3) . . . . ?
C9 C10 C15 C14 179.7(2) . . . . ?
C11 C10 C15 C16 -177.89(19) . . . . ?
C9 C10 C15 C16 0.9(3) . . . . ?
O5 N3 C16 C15 0.0(3) . . . . ?
O5 N3 C16 C17 -179.15(17) . . . . ?
C14 C15 C16 N3 103.2(3) . . . . ?
C10 C15 C16 N3 -78.0(3) . . . . ?
C14 C15 C16 C17 -77.7(3) . . . . ?
C10 C15 C16 C17 101.1(2) . . . . ?
C18 O3 C17 O4 1.3(3) . . . . ?
C18 O3 C17 C16 -178.83(19) . . . . ?
N3 C16 C17 O4 8.8(3) . . . . ?
C15 C16 C17 O4 -170.4(2) . . . . ?
N3 C16 C17 O3 -170.99(19) . . . . ?
C15 C16 C17 O3 9.8(3) . . . . ?

_refine_diff_density_max         0.978
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_shelxl_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2131906'
loop_
_audit_author_name
_audit_author_address
'Dongyan Yang'
;Zhongkai University of Agriculture and Engineering
China
;
_audit_update_record             
;
2021-12-31 deposited with the CCDC.	2022-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H19 Cl2 N3 O5 S'
_chemical_formula_weight         472.33

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.6714(17)
_cell_length_b                   10.866(2)
_cell_length_c                   11.901(2)
_cell_angle_alpha                85.84(3)
_cell_angle_beta                 79.04(3)
_cell_angle_gamma                71.60(3)
_cell_volume                     1044.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    2739
_cell_measurement_theta_min      1.7431
_cell_measurement_theta_max      27.9664

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.448
_shelx_estimated_absorpt_T_min   0.916
_shelx_estimated_absorpt_T_max   0.948
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.7273
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9891
_diffrn_reflns_av_unetI/netI     0.0814
_diffrn_reflns_av_R_equivalents  0.0656
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.743
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_full        25.019
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3664
_reflns_number_gt                2429
_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       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0689P)²] 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         3664
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1399
_refine_ls_wR_factor_gt          0.1332
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_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
S1 S 0.35665(9) 0.80497(8) 0.33960(7) 0.0306(2) Uani 1 1 d . . . . .
Cl1 Cl 0.45516(10) 0.61328(8) 0.64773(6) 0.0382(3) Uani 1 1 d . . . . .
Cl2 Cl 0.14590(12) 0.57000(10) 0.55259(8) 0.0537(3) Uani 1 1 d . . . . .
O1 O 0.6285(3) 0.8145(2) 0.56433(18) 0.0448(6) Uani 1 1 d . . . . .
O2 O 0.6358(2) 0.86101(18) 0.27125(15) 0.0237(5) Uani 1 1 d . . . . .
O3 O 0.2551(2) 0.72731(19) 0.10592(17) 0.0297(5) Uani 1 1 d . . . . .
O4 O 0.3393(2) 0.52315(18) 0.17456(17) 0.0273(5) Uani 1 1 d . . . . .
O5 O 0.8066(2) 0.49790(17) 0.07280(16) 0.0237(5) Uani 1 1 d . . . . .
N1 N 0.2240(3) 0.7257(3) 0.3888(2) 0.0353(7) Uani 1 1 d . . . . .
N2 N 0.6954(3) 0.8441(2) 0.3752(2) 0.0288(6) Uani 1 1 d . . . . .
N3 N 0.6415(3) 0.5049(2) 0.10834(19) 0.0198(5) Uani 1 1 d . . . . .
C1 C 0.2598(4) 0.6663(3) 0.4831(3) 0.0320(8) Uani 1 1 d . . . . .
C2 C 0.3955(3) 0.6828(3) 0.5241(2) 0.0266(7) Uani 1 1 d . . . . .
C3 C 0.4643(3) 0.7616(3) 0.4499(2) 0.0241(7) Uani 1 1 d . . . . .
C4 C 0.6015(3) 0.8098(3) 0.4686(3) 0.0287(7) Uani 1 1 d . . . . .
C5 C 0.8170(4) 0.9078(4) 0.3849(3) 0.0469(10) Uani 1 1 d . . . . .
H5A H 0.805255 0.928341 0.466356 0.056 Uiso 1 1 calc R U . . .
H5B H 0.928518 0.845588 0.361882 0.056 Uiso 1 1 calc R U . . .
C6 C 0.8069(5) 1.0254(4) 0.3179(3) 0.0503(10) Uani 1 1 d . . . . .
H6 H 0.694676 1.091020 0.328188 0.060 Uiso 1 1 calc R U . . .
C7 C 0.9123(5) 1.0313(4) 0.2045(3) 0.0598(12) Uani 1 1 d . . . . .
H7A H 0.863373 1.095502 0.147497 0.072 Uiso 1 1 calc R U . . .
H7B H 0.990183 0.948765 0.171782 0.072 Uiso 1 1 calc R U . . .
C8 C 0.9482(4) 1.0818(3) 0.3076(3) 0.0404(9) Uani 1 1 d . . . . .
H8A H 0.920551 1.176848 0.314403 0.049 Uiso 1 1 calc R U . . .
H8B H 1.047514 1.029934 0.338718 0.049 Uiso 1 1 calc R U . . .
C9 C 0.7337(3) 0.7553(3) 0.1928(2) 0.0236(7) Uani 1 1 d . . . . .
H9A H 0.712896 0.673055 0.221161 0.028 Uiso 1 1 calc R U . . .
H9B H 0.852938 0.743571 0.186546 0.028 Uiso 1 1 calc R U . . .
C10 C 0.6826(3) 0.7915(3) 0.0789(2) 0.0211(6) Uani 1 1 d . . . . .
C11 C 0.7278(3) 0.8919(3) 0.0159(2) 0.0252(7) Uani 1 1 d . . . . .
H11 H 0.787450 0.936683 0.047255 0.030 Uiso 1 1 calc R U . . .
C12 C 0.6879(3) 0.9274(3) -0.0910(3) 0.0314(8) Uani 1 1 d . . . . .
H12 H 0.720552 0.995759 -0.132426 0.038 Uiso 1 1 calc R U . . .
C13 C 0.6004(4) 0.8640(3) -0.1382(3) 0.0308(7) Uani 1 1 d . . . . .
H13 H 0.574178 0.887774 -0.212345 0.037 Uiso 1 1 calc R U . . .
C14 C 0.5511(4) 0.7653(3) -0.0762(2) 0.0262(7) Uani 1 1 d . . . . .
H14 H 0.488705 0.722882 -0.107461 0.031 Uiso 1 1 calc R U . . .
C15 C 0.5924(3) 0.7282(3) 0.0309(2) 0.0203(6) Uani 1 1 d . . . . .
C16 C 0.5446(3) 0.6165(3) 0.0892(2) 0.0211(6) Uani 1 1 d . . . . .
C17 C 0.3618(3) 0.6307(3) 0.1231(2) 0.0218(6) Uani 1 1 d . . . . .
C18 C 0.1685(3) 0.5260(3) 0.2138(3) 0.0337(8) Uani 1 1 d . . . . .
H18A H 0.113426 0.596361 0.268602 0.051 Uiso 1 1 calc R U . . .
H18B H 0.166049 0.443062 0.251065 0.051 Uiso 1 1 calc R U . . .
H18C H 0.111269 0.540630 0.148271 0.051 Uiso 1 1 calc R U . . .
C19 C 0.9078(3) 0.3699(3) 0.0987(3) 0.0278(7) Uani 1 1 d . . . . .
H19A H 0.898922 0.358308 0.181886 0.042 Uiso 1 1 calc R U . . .
H19B H 1.023090 0.359084 0.063870 0.042 Uiso 1 1 calc R U . . .
H19C H 0.870329 0.305164 0.068077 0.042 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
S1 N1 1.644(3) . ?
S1 C3 1.707(3) . ?
Cl1 C2 1.698(3) . ?
Cl2 C1 1.723(3) . ?
O1 C4 1.213(3) . ?
O2 N2 1.407(3) . ?
O2 C9 1.467(3) . ?
O3 C17 1.195(3) . ?
O4 C17 1.332(3) . ?
O4 C18 1.457(3) . ?
O5 N3 1.393(3) . ?
O5 C19 1.438(3) . ?
N1 C1 1.293(4) . ?
N2 C4 1.351(4) . ?
N2 C5 1.457(4) . ?
N3 C16 1.272(3) . ?
C1 C2 1.422(4) . ?
C2 C3 1.372(4) . ?
C3 C4 1.501(4) . ?
C5 C6 1.444(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.489(5) . ?
C6 C8 1.516(5) . ?
C6 H6 1.0000 . ?
C7 C8 1.502(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.492(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.395(4) . ?
C10 C15 1.407(4) . ?
C11 C12 1.377(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.488(4) . ?
C16 C17 1.520(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
N1 S1 C3 95.46(14) . . ?
N2 O2 C9 110.59(19) . . ?
C17 O4 C18 116.1(2) . . ?
N3 O5 C19 108.53(18) . . ?
C1 N1 S1 109.2(2) . . ?
C4 N2 O2 117.6(2) . . ?
C4 N2 C5 121.6(3) . . ?
O2 N2 C5 117.0(2) . . ?
C16 N3 O5 111.9(2) . . ?
N1 C1 C2 117.4(3) . . ?
N1 C1 Cl2 119.9(2) . . ?
C2 C1 Cl2 122.7(2) . . ?
C3 C2 C1 109.6(3) . . ?
C3 C2 Cl1 127.6(2) . . ?
C1 C2 Cl1 122.8(2) . . ?
C2 C3 C4 125.2(3) . . ?
C2 C3 S1 108.4(2) . . ?
C4 C3 S1 126.2(2) . . ?
O1 C4 N2 121.8(3) . . ?
O1 C4 C3 120.7(3) . . ?
N2 C4 C3 117.5(3) . . ?
C6 C5 N2 115.8(3) . . ?
C6 C5 H5A 108.3 . . ?
N2 C5 H5A 108.3 . . ?
C6 C5 H5B 108.3 . . ?
N2 C5 H5B 108.3 . . ?
H5A C5 H5B 107.4 . . ?
C5 C6 C7 123.9(4) . . ?
C5 C6 C8 117.8(3) . . ?
C7 C6 C8 60.0(2) . . ?
C5 C6 H6 114.7 . . ?
C7 C6 H6 114.7 . . ?
C8 C6 H6 114.7 . . ?
C6 C7 C8 60.9(2) . . ?
C6 C7 H7A 117.7 . . ?
C8 C7 H7A 117.7 . . ?
C6 C7 H7B 117.7 . . ?
C8 C7 H7B 117.7 . . ?
H7A C7 H7B 114.8 . . ?
C7 C8 C6 59.1(2) . . ?
C7 C8 H8A 117.9 . . ?
C6 C8 H8A 117.9 . . ?
C7 C8 H8B 117.9 . . ?
C6 C8 H8B 117.9 . . ?
H8A C8 H8B 115.0 . . ?
O2 C9 C10 107.3(2) . . ?
O2 C9 H9A 110.3 . . ?
C10 C9 H9A 110.3 . . ?
O2 C9 H9B 110.3 . . ?
C10 C9 H9B 110.3 . . ?
H9A C9 H9B 108.5 . . ?
C11 C10 C15 118.0(3) . . ?
C11 C10 C9 118.8(2) . . ?
C15 C10 C9 123.2(2) . . ?
C12 C11 C10 121.4(3) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 120.4(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C14 119.4(3) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C10 120.3(3) . . ?
C14 C15 C16 117.6(3) . . ?
C10 C15 C16 122.0(2) . . ?
N3 C16 C15 126.7(2) . . ?
N3 C16 C17 115.0(2) . . ?
C15 C16 C17 118.2(2) . . ?
O3 C17 O4 125.8(3) . . ?
O3 C17 C16 123.2(3) . . ?
O4 C17 C16 111.0(2) . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O5 C19 H19A 109.5 . . ?
O5 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O5 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C3 S1 N1 C1 -1.3(3) . . . . ?
C9 O2 N2 C4 -108.7(3) . . . . ?
C9 O2 N2 C5 92.9(3) . . . . ?
C19 O5 N3 C16 179.2(2) . . . . ?
S1 N1 C1 C2 1.4(4) . . . . ?
S1 N1 C1 Cl2 -177.79(17) . . . . ?
N1 C1 C2 C3 -0.7(4) . . . . ?
Cl2 C1 C2 C3 178.5(2) . . . . ?
N1 C1 C2 Cl1 178.9(2) . . . . ?
Cl2 C1 C2 Cl1 -2.0(4) . . . . ?
C1 C2 C3 C4 175.0(3) . . . . ?
Cl1 C2 C3 C4 -4.5(5) . . . . ?
C1 C2 C3 S1 -0.3(3) . . . . ?
Cl1 C2 C3 S1 -179.85(18) . . . . ?
N1 S1 C3 C2 0.9(2) . . . . ?
N1 S1 C3 C4 -174.3(3) . . . . ?
O2 N2 C4 O1 -167.3(3) . . . . ?
C5 N2 C4 O1 -9.9(5) . . . . ?
O2 N2 C4 C3 14.4(4) . . . . ?
C5 N2 C4 C3 171.8(3) . . . . ?
C2 C3 C4 O1 -22.2(5) . . . . ?
S1 C3 C4 O1 152.3(3) . . . . ?
C2 C3 C4 N2 156.1(3) . . . . ?
S1 C3 C4 N2 -29.5(4) . . . . ?
C4 N2 C5 C6 -128.7(3) . . . . ?
O2 N2 C5 C6 28.8(4) . . . . ?
N2 C5 C6 C7 -98.1(4) . . . . ?
N2 C5 C6 C8 -169.0(3) . . . . ?
C5 C6 C7 C8 -105.0(4) . . . . ?
C5 C6 C8 C7 115.1(4) . . . . ?
N2 O2 C9 C10 -170.5(2) . . . . ?
O2 C9 C10 C11 70.8(3) . . . . ?
O2 C9 C10 C15 -110.0(3) . . . . ?
C15 C10 C11 C12 -0.9(4) . . . . ?
C9 C10 C11 C12 178.3(3) . . . . ?
C10 C11 C12 C13 0.3(4) . . . . ?
C11 C12 C13 C14 0.9(4) . . . . ?
C12 C13 C14 C15 -1.5(4) . . . . ?
C13 C14 C15 C10 1.0(4) . . . . ?
C13 C14 C15 C16 -176.3(3) . . . . ?
C11 C10 C15 C14 0.2(4) . . . . ?
C9 C10 C15 C14 -178.9(2) . . . . ?
C11 C10 C15 C16 177.4(2) . . . . ?
C9 C10 C15 C16 -1.8(4) . . . . ?
O5 N3 C16 C15 3.0(4) . . . . ?
O5 N3 C16 C17 178.6(2) . . . . ?
C14 C15 C16 N3 111.0(3) . . . . ?
C10 C15 C16 N3 -66.2(4) . . . . ?
C14 C15 C16 C17 -64.5(3) . . . . ?
C10 C15 C16 C17 118.4(3) . . . . ?
C18 O4 C17 O3 -0.7(4) . . . . ?
C18 O4 C17 C16 178.5(2) . . . . ?
N3 C16 C17 O3 -176.5(3) . . . . ?
C15 C16 C17 O3 -0.5(4) . . . . ?
N3 C16 C17 O4 4.3(3) . . . . ?
C15 C16 C17 O4 -179.8(2) . . . . ?

_refine_diff_density_max         1.068
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.078

