# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_wsz
_audit_block_doi                 10.5517/ccdc.csd.cc21921h
_database_code_depnum_ccdc_archive 'CCDC 1885545'
loop_
_audit_author_name
_audit_author_address
'Shengzheng Wang'
;fourth military medical university
China
;
_audit_update_record             
;
2018-12-15 deposited with the CCDC.	2019-03-14 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            'C25 H17 Cl3 N2 O2 S'
_chemical_formula_weight         515.81

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'

_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                   13.0109(8)
_cell_length_b                   11.5329(5)
_cell_length_c                   16.1284(9)
_cell_angle_alpha                90
_cell_angle_beta                 109.629(6)
_cell_angle_gamma                90
_cell_volume                     2279.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5341
_cell_measurement_theta_min      4.8140
_cell_measurement_theta_max      73.0740

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    4.721
_shelx_estimated_absorpt_T_min   0.484
_shelx_estimated_absorpt_T_max   0.519
_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      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  bruker-CCd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12658
_diffrn_reflns_av_unetI/netI     0.0658
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.607
_diffrn_reflns_theta_max         65.999
_diffrn_reflns_theta_full        65.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3976
_reflns_number_gt                3460
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0678P)²+64.4932P] 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         3976
_refine_ls_number_parameters     320
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.1366
_refine_ls_R_factor_gt           0.1264
_refine_ls_wR_factor_ref         0.3380
_refine_ls_wR_factor_gt          0.3338
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.004
_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 0.35530(12) 0.60495(14) 0.16474(9) 0.0225(4) Uani 1 1 d . . . . .
Cl1 Cl 0.54632(13) 0.41916(14) 0.35164(10) 0.0305(4) Uani 1 1 d . . . . .
O2 O 0.6234(3) 0.7105(4) 0.3369(3) 0.0239(11) Uani 1 1 d . . . . .
O1 O 0.4152(4) 0.5800(4) 0.0098(3) 0.0287(12) Uani 1 1 d . . . . .
N2 N 0.4400(4) 0.7106(4) 0.3164(3) 0.0186(12) Uani 1 1 d . . . . .
N1 N 0.5307(4) 0.7276(5) 0.0040(3) 0.0266(13) Uani 1 1 d . . . . .
H1 H 0.5019 0.7463 -0.0520 0.032 Uiso 1 1 calc R U . . .
C16 C 0.4999(5) 0.6206(6) 0.2049(4) 0.0207(14) Uani 1 1 d . . . . .
C15 C 0.6461(5) 0.7333(5) 0.1473(4) 0.0206(14) Uani 1 1 d . . . . .
C17 C 0.5300(5) 0.6849(5) 0.2913(4) 0.0198(14) Uani 1 1 d . . . . .
C10 C 0.6225(5) 0.7823(6) 0.0644(4) 0.0255(15) Uani 1 1 d . . . . .
C7 C 0.5738(5) 0.5283(5) 0.1882(4) 0.0214(14) Uani 1 1 d . . . . .
H7 H 0.5333 0.4633 0.1500 0.026 Uiso 1 1 calc R U . . .
C19 C 0.2431(5) 0.6873(6) 0.2727(4) 0.0224(15) Uani 1 1 d . . . . .
C9 C 0.4932(5) 0.6428(6) 0.0439(4) 0.0256(15) Uani 1 1 d . . . . .
C20 C 0.2406(5) 0.7370(6) 0.3510(4) 0.0271(16) Uani 1 1 d . . . . .
H20 H 0.3056 0.7649 0.3938 0.032 Uiso 1 1 calc R U . . .
C8 C 0.5646(5) 0.6415(5) 0.1402(4) 0.0199(14) Uani 1 1 d . . . . .
C14 C 0.7371(5) 0.7753(6) 0.2156(4) 0.0246(15) Uani 1 1 d . . . . .
H14 H 0.7573 0.7427 0.2729 0.030 Uiso 1 1 calc R U . . .
C18 C 0.3498(5) 0.6736(6) 0.2598(4) 0.0210(14) Uani 1 1 d . . . . .
C13 C 0.7966(5) 0.8654(6) 0.1973(5) 0.0296(17) Uani 1 1 d . . . . .
H13 H 0.8580 0.8944 0.2433 0.036 Uiso 1 1 calc R U . . .
C21 C 0.1398(5) 0.7450(6) 0.3650(5) 0.0299(16) Uani 1 1 d . . . . .
H21 H 0.1363 0.7784 0.4178 0.036 Uiso 1 1 calc R U . . .
C1 C 0.6721(5) 0.4416(6) 0.3369(4) 0.0260(15) Uani 1 1 d . . . . .
C24 C 0.1476(5) 0.6475(7) 0.2103(5) 0.0312(17) Uani 1 1 d . . . . .
H24 H 0.1500 0.6122 0.1578 0.037 Uiso 1 1 calc R U . . .
C5 C 0.7778(5) 0.4995(6) 0.2489(5) 0.0305(17) Uani 1 1 d . . . . .
H5 H 0.7835 0.5314 0.1963 0.037 Uiso 1 1 calc R U . . .
C12 C 0.7701(6) 0.9141(6) 0.1153(5) 0.0350(19) Uani 1 1 d . . . . .
H12 H 0.8131 0.9756 0.1053 0.042 Uiso 1 1 calc R U . . .
C6 C 0.6741(5) 0.4905(5) 0.2590(4) 0.0231(15) Uani 1 1 d . . . . .
C11 C 0.6798(6) 0.8736(6) 0.0462(4) 0.0319(17) Uani 1 1 d . . . . .
H11 H 0.6589 0.9076 -0.0107 0.038 Uiso 1 1 calc R U . . .
C22 C 0.0466(5) 0.7045(7) 0.3026(5) 0.0349(18) Uani 1 1 d . . . . .
H22 H -0.0207 0.7080 0.3136 0.042 Uiso 1 1 calc R U . . .
C2 C 0.7646(6) 0.4049(6) 0.4030(5) 0.0352(19) Uani 1 1 d . . . . .
H2 H 0.7597 0.3711 0.4553 0.042 Uiso 1 1 calc R U . . .
C23 C 0.0487(5) 0.6592(7) 0.2245(5) 0.0361(19) Uani 1 1 d . . . . .
H23 H -0.0171 0.6359 0.1804 0.043 Uiso 1 1 calc R U . . .
C4 C 0.8700(5) 0.4628(7) 0.3141(6) 0.042(2) Uani 1 1 d . . . . .
H4 H 0.9386 0.4682 0.3055 0.050 Uiso 1 1 calc R U . . .
C3 C 0.8650(6) 0.4183(7) 0.3914(6) 0.043(2) Uani 1 1 d . . . . .
H3 H 0.9301 0.3967 0.4370 0.052 Uiso 1 1 calc R U . . .
Cl2 Cl 0.8979(3) 0.7580(3) 0.4610(2) 0.0723(9) Uani 0.821(4) 1 d . U P A 1
Cl3 Cl 0.8636(3) 0.9879(3) 0.5216(2) 0.0801(12) Uani 0.821(4) 1 d . U P A 1
C25 C 0.8074(9) 0.8554(10) 0.4760(8) 0.0534(7) Uani 0.821(4) 1 d . U P A 1
H25A H 0.7711 0.8200 0.5148 0.064 Uiso 0.821(4) 1 calc R U P A 1
H25B H 0.7505 0.8705 0.4184 0.064 Uiso 0.821(4) 1 calc R U P A 1
Cl3A Cl 0.7938(12) 0.9423(13) 0.5287(8) 0.063(4) Uani 0.179(4) 1 d . U P A 2
Cl2A Cl 0.9452(13) 0.8372(19) 0.4574(10) 0.084(5) Uani 0.179(4) 1 d . U P A 2
C25A C 0.898(4) 0.947(5) 0.487(3) 0.0534(7) Uani 0.179(4) 1 d . U P A 2
H25C H 0.8741 0.9994 0.4349 0.064 Uiso 0.179(4) 1 calc R U P A 2
H25D H 0.9599 0.9864 0.5312 0.064 Uiso 0.179(4) 1 calc R U P A 2


_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 C18 1.748(6) . ?
S1 C16 1.781(6) . ?
Cl1 C1 1.750(7) . ?
O2 C17 1.227(7) . ?
O1 C9 1.217(8) . ?
N2 C18 1.294(7) . ?
N2 C17 1.394(8) . ?
N1 C9 1.349(9) . ?
N1 C10 1.411(8) . ?
N1 H1 0.8800 . ?
C16 C17 1.510(8) . ?
C16 C7 1.518(9) . ?
C16 C8 1.563(9) . ?
C15 C10 1.388(9) . ?
C15 C14 1.405(8) . ?
C15 C8 1.476(9) . ?
C10 C11 1.377(10) . ?
C7 C6 1.482(8) . ?
C7 C8 1.503(9) . ?
C7 H7 1.0000 . ?
C19 C24 1.387(9) . ?
C19 C20 1.397(9) . ?
C19 C18 1.480(9) . ?
C9 C8 1.519(8) . ?
C20 C21 1.407(10) . ?
C20 H20 0.9500 . ?
C14 C13 1.385(10) . ?
C14 H14 0.9500 . ?
C13 C12 1.371(10) . ?
C13 H13 0.9500 . ?
C21 C22 1.372(9) . ?
C21 H21 0.9500 . ?
C1 C2 1.379(9) . ?
C1 C6 1.385(9) . ?
C24 C23 1.387(10) . ?
C24 H24 0.9500 . ?
C5 C4 1.370(10) . ?
C5 C6 1.416(10) . ?
C5 H5 0.9500 . ?
C12 C11 1.400(9) . ?
C12 H12 0.9500 . ?
C11 H11 0.9500 . ?
C22 C23 1.373(11) . ?
C22 H22 0.9500 . ?
C2 C3 1.390(12) . ?
C2 H2 0.9500 . ?
C23 H23 0.9500 . ?
C4 C3 1.370(13) . ?
C4 H4 0.9500 . ?
C3 H3 0.9500 . ?
Cl2 C25 1.702(12) . ?
Cl3 C25 1.746(12) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
Cl3A C25A 1.71(6) . ?
Cl2A C25A 1.55(6) . ?
C25A H25C 0.9900 . ?
C25A H25D 0.9900 . ?

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
C18 S1 C16 89.2(3) . . ?
C18 N2 C17 112.1(5) . . ?
C9 N1 C10 110.7(5) . . ?
C9 N1 H1 124.7 . . ?
C10 N1 H1 124.7 . . ?
C17 C16 C7 121.6(5) . . ?
C17 C16 C8 120.6(5) . . ?
C7 C16 C8 58.4(4) . . ?
C17 C16 S1 107.4(4) . . ?
C7 C16 S1 121.3(4) . . ?
C8 C16 S1 120.9(4) . . ?
C10 C15 C14 118.1(6) . . ?
C10 C15 C8 107.3(5) . . ?
C14 C15 C8 134.6(6) . . ?
O2 C17 N2 122.3(5) . . ?
O2 C17 C16 124.7(6) . . ?
N2 C17 C16 113.0(5) . . ?
C11 C10 C15 123.8(6) . . ?
C11 C10 N1 126.0(6) . . ?
C15 C10 N1 110.2(6) . . ?
C6 C7 C8 123.4(5) . . ?
C6 C7 C16 121.1(5) . . ?
C8 C7 C16 62.3(4) . . ?
C6 C7 H7 113.6 . . ?
C8 C7 H7 113.6 . . ?
C16 C7 H7 113.6 . . ?
C24 C19 C20 120.3(6) . . ?
C24 C19 C18 121.0(6) . . ?
C20 C19 C18 118.6(5) . . ?
O1 C9 N1 126.6(6) . . ?
O1 C9 C8 125.9(6) . . ?
N1 C9 C8 107.4(5) . . ?
C19 C20 C21 118.5(6) . . ?
C19 C20 H20 120.7 . . ?
C21 C20 H20 120.7 . . ?
C15 C8 C7 130.8(5) . . ?
C15 C8 C9 104.4(5) . . ?
C7 C8 C9 116.8(5) . . ?
C15 C8 C16 126.4(5) . . ?
C7 C8 C16 59.3(4) . . ?
C9 C8 C16 113.7(5) . . ?
C13 C14 C15 118.4(6) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 H14 120.8 . . ?
N2 C18 C19 122.5(6) . . ?
N2 C18 S1 118.3(5) . . ?
C19 C18 S1 119.3(4) . . ?
C12 C13 C14 122.4(6) . . ?
C12 C13 H13 118.8 . . ?
C14 C13 H13 118.8 . . ?
C22 C21 C20 120.1(7) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C2 C1 C6 123.3(7) . . ?
C2 C1 Cl1 117.5(6) . . ?
C6 C1 Cl1 119.1(5) . . ?
C19 C24 C23 120.1(7) . . ?
C19 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C4 C5 C6 120.8(7) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C13 C12 C11 120.2(7) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C1 C6 C5 116.3(6) . . ?
C1 C6 C7 122.6(6) . . ?
C5 C6 C7 121.1(6) . . ?
C10 C11 C12 117.1(6) . . ?
C10 C11 H11 121.5 . . ?
C12 C11 H11 121.5 . . ?
C23 C22 C21 121.1(7) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C1 C2 C3 118.5(7) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C22 C23 C24 119.6(6) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C3 C4 C5 121.2(7) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C4 C3 C2 119.9(6) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
Cl2 C25 Cl3 115.2(7) . . ?
Cl2 C25 H25A 108.5 . . ?
Cl3 C25 H25A 108.5 . . ?
Cl2 C25 H25B 108.5 . . ?
Cl3 C25 H25B 108.5 . . ?
H25A C25 H25B 107.5 . . ?
Cl2A C25A Cl3A 123(4) . . ?
Cl2A C25A H25C 106.7 . . ?
Cl3A C25A H25C 106.7 . . ?
Cl2A C25A H25D 106.7 . . ?
Cl3A C25A H25D 106.7 . . ?
H25C C25A H25D 106.6 . . ?

_refine_diff_density_max         1.656
_refine_diff_density_min         -1.009
_refine_diff_density_rms         0.184



