# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_1_a
_audit_block_doi                 10.5517/ccdc.csd.cc28c875
_database_code_depnum_ccdc_archive 'CCDC 2096196'
loop_
_audit_author_name
_audit_author_address
'Xiao-Qiang Hu' 'South Central University for Nationalities'
_audit_update_record             
;
2021-07-13 deposited with the CCDC.	2021-10-11 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            'C24 H25 Cl N2 O3 S'
_chemical_formula_weight         456.97

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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.877
_cell_length_b                   10.006
_cell_length_c                   27.938
_cell_angle_alpha                90
_cell_angle_beta                 98.68
_cell_angle_gamma                90
_cell_volume                     4664.1
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2623
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      18.56

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_F_000             1920
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.281
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34882
_diffrn_reflns_av_unetI/netI     0.0933
_diffrn_reflns_av_R_equivalents  0.1279
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.441
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4103
_reflns_number_gt                1908
_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)+(0.1068P)²+5.0415P] 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         4103
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2240
_refine_ls_R_factor_gt           0.1007
_refine_ls_wR_factor_ref         0.2598
_refine_ls_wR_factor_gt          0.2078
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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
C1 C 0.8529(3) 0.3815(3) 0.36855(17) 0.095(2) Uani 1 1 d G . . . .
H1 H 0.8642 0.4634 0.3554 0.114 Uiso 1 1 calc R U . . .
C2 C 0.9072(2) 0.3250(5) 0.40536(17) 0.099(2) Uani 1 1 d G . . . .
H2 H 0.9548 0.3691 0.4168 0.119 Uiso 1 1 calc R U . . .
C3 C 0.8904(3) 0.2025(5) 0.42502(14) 0.095(2) Uani 1 1 d G . . . .
C4 C 0.8193(4) 0.1365(4) 0.40787(17) 0.109(2) Uani 1 1 d G . . . .
H4 H 0.8080 0.0545 0.4210 0.130 Uiso 1 1 calc R U . . .
C5 C 0.7650(3) 0.1929(4) 0.37107(18) 0.096(2) Uani 1 1 d G . . . .
H5 H 0.7174 0.1488 0.3596 0.115 Uiso 1 1 calc R U . . .
C6 C 0.7818(3) 0.3155(4) 0.35140(14) 0.0777(16) Uani 1 1 d G . . . .
C7 C 0.6692(4) 0.2901(6) 0.2844(2) 0.0797(17) Uani 1 1 d . . . . .
H7A H 0.6955 0.2110 0.2742 0.096 Uiso 1 1 calc R U . . .
H7B H 0.6257 0.2625 0.3012 0.096 Uiso 1 1 calc R U . . .
C8 C 0.7491(3) 0.4836(5) 0.2862(2) 0.0745(16) Uani 1 1 d . . . . .
H8A H 0.7944 0.4593 0.2705 0.089 Uiso 1 1 calc R U . . .
H8B H 0.7625 0.5629 0.3058 0.089 Uiso 1 1 calc R U . . .
C9 C 0.6745(3) 0.5063(5) 0.2493(2) 0.0704(15) Uani 1 1 d . . . . .
H9 H 0.6883 0.5399 0.2187 0.084 Uiso 1 1 calc R U . . .
C10 C 0.6139(3) 0.5964(5) 0.2684(2) 0.0830(18) Uani 1 1 d . . . . .
H10A H 0.5649 0.6001 0.2454 0.100 Uiso 1 1 calc R U . . .
H10B H 0.6012 0.5613 0.2987 0.100 Uiso 1 1 calc R U . . .
C11 C 0.5869(2) 0.3257(4) 0.20383(13) 0.0709(15) Uani 1 1 d G . . . .
C12 C 0.5609(2) 0.4078(3) 0.16445(16) 0.0836(18) Uani 1 1 d G . . . .
H12 H 0.5772 0.4965 0.1647 0.100 Uiso 1 1 calc R U . . .
C13 C 0.5104(3) 0.3572(4) 0.12466(13) 0.0855(18) Uani 1 1 d G . . . .
H13 H 0.4930 0.4121 0.0983 0.103 Uiso 1 1 calc R U . . .
C14 C 0.4859(2) 0.2245(5) 0.12424(13) 0.0844(18) Uani 1 1 d G . . . .
C15 C 0.5119(2) 0.1424(3) 0.16362(16) 0.0841(18) Uani 1 1 d G . . . .
H15 H 0.4956 0.0536 0.1633 0.101 Uiso 1 1 calc R U . . .
C16 C 0.5624(2) 0.1930(3) 0.20342(13) 0.0712(15) Uani 1 1 d G . . . .
H16 H 0.5798 0.1380 0.2298 0.085 Uiso 1 1 calc R U . . .
C17 C 0.4318(5) 0.1657(8) 0.0799(2) 0.125(3) Uani 1 1 d . . . . .
H17A H 0.4635 0.1466 0.0549 0.188 Uiso 1 1 calc R U . . .
H17B H 0.3909 0.2292 0.0680 0.188 Uiso 1 1 calc R U . . .
H17C H 0.4074 0.0848 0.0890 0.188 Uiso 1 1 calc R U . . .
C18 C 0.6770(3) 0.7447(4) 0.37005(14) 0.0755(16) Uani 1 1 d G . . . .
C19 C 0.7587(3) 0.7705(4) 0.38069(19) 0.095(2) Uani 1 1 d G . . . .
H19 H 0.7830 0.8278 0.3611 0.114 Uiso 1 1 calc R U . . .
C20 C 0.8041(2) 0.7106(6) 0.4206(2) 0.109(2) Uani 1 1 d G . . . .
H20 H 0.8588 0.7278 0.4277 0.131 Uiso 1 1 calc R U . . .
C21 C 0.7678(4) 0.6249(5) 0.44990(16) 0.112(2) Uani 1 1 d G . . . .
C22 C 0.6861(4) 0.5991(5) 0.43926(18) 0.123(3) Uani 1 1 d G . . . .
H22 H 0.6618 0.5418 0.4589 0.148 Uiso 1 1 calc R U . . .
C23 C 0.6407(2) 0.6590(5) 0.39934(19) 0.099(2) Uani 1 1 d G . . . .
H23 H 0.5861 0.6418 0.3922 0.119 Uiso 1 1 calc R U . . .
C24 C 0.8173(6) 0.5563(10) 0.4934(3) 0.164(4) Uani 1 1 d . . . . .
H24A H 0.8068 0.4620 0.4921 0.246 Uiso 1 1 calc R U . . .
H24B H 0.8030 0.5924 0.5228 0.246 Uiso 1 1 calc R U . . .
H24C H 0.8733 0.5716 0.4927 0.246 Uiso 1 1 calc R U . . .
Cl1 Cl 0.95959(14) 0.1322(2) 0.47015(7) 0.1349(9) Uani 1 1 d . . . . .
N1 N 0.7262(3) 0.3740(4) 0.31552(18) 0.0774(13) Uani 1 1 d . . . . .
N2 N 0.6402(3) 0.3718(4) 0.24375(19) 0.0838(15) Uani 1 1 d . . . . .
O1 O 0.6483(2) 0.7292(3) 0.27592(13) 0.0789(11) Uani 1 1 d . . . . .
O2 O 0.5387(3) 0.7946(4) 0.31969(17) 0.1047(14) Uani 1 1 d . . . . .
O3 O 0.6517(3) 0.9443(4) 0.31099(16) 0.1042(14) Uani 1 1 d . . . . .
S1 S 0.62190(11) 0.81424(14) 0.31841(6) 0.0827(6) Uani 1 1 d . . . . .


_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
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C2 C3 1.3900 . ?
C3 C4 1.3900 . ?
C3 Cl1 1.734(4) . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C6 N1 1.394(6) . ?
C7 N2 1.424(7) . ?
C7 N1 1.461(7) . ?
C8 N1 1.455(7) . ?
C8 C9 1.518(7) . ?
C9 N2 1.464(6) . ?
C9 C10 1.520(7) . ?
C10 O1 1.453(6) . ?
C11 C12 1.3900 . ?
C11 C16 1.3900 . ?
C11 N2 1.401(6) . ?
C12 C13 1.3900 . ?
C13 C14 1.3900 . ?
C14 C15 1.3900 . ?
C14 C17 1.541(7) . ?
C15 C16 1.3900 . ?
C18 C19 1.3900 . ?
C18 C23 1.3900 . ?
C18 S1 1.740(4) . ?
C19 C20 1.3900 . ?
C20 C21 1.3900 . ?
C21 C22 1.3900 . ?
C21 C24 1.531(8) . ?
C22 C23 1.3900 . ?
O1 S1 1.578(4) . ?
O2 S1 1.424(4) . ?
O3 S1 1.421(4) . ?

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
C2 C1 C6 120.0 . . ?
C3 C2 C1 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 Cl1 119.3(4) . . ?
C4 C3 Cl1 120.6(4) . . ?
C3 C4 C5 120.0 . . ?
C4 C5 C6 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 N1 120.0(4) . . ?
C1 C6 N1 120.0(4) . . ?
N2 C7 N1 105.1(5) . . ?
N1 C8 C9 103.4(4) . . ?
N2 C9 C8 102.1(4) . . ?
N2 C9 C10 107.8(4) . . ?
C8 C9 C10 112.5(5) . . ?
O1 C10 C9 108.5(4) . . ?
C12 C11 C16 120.0 . . ?
C12 C11 N2 121.6(3) . . ?
C16 C11 N2 118.4(3) . . ?
C13 C12 C11 120.0 . . ?
C12 C13 C14 120.0 . . ?
C13 C14 C15 120.0 . . ?
C13 C14 C17 120.7(4) . . ?
C15 C14 C17 119.3(4) . . ?
C16 C15 C14 120.0 . . ?
C15 C16 C11 120.0 . . ?
C19 C18 C23 120.0 . . ?
C19 C18 S1 119.5(4) . . ?
C23 C18 S1 120.4(4) . . ?
C20 C19 C18 120.0 . . ?
C19 C20 C21 120.0 . . ?
C20 C21 C22 120.0 . . ?
C20 C21 C24 120.5(6) . . ?
C22 C21 C24 119.5(6) . . ?
C23 C22 C21 120.0 . . ?
C22 C23 C18 120.0 . . ?
C6 N1 C8 121.0(4) . . ?
C6 N1 C7 119.9(4) . . ?
C8 N1 C7 107.7(4) . . ?
C11 N2 C7 123.2(4) . . ?
C11 N2 C9 125.7(4) . . ?
C7 N2 C9 111.1(5) . . ?
C10 O1 S1 116.7(3) . . ?
O2 S1 O3 120.1(3) . . ?
O2 S1 O1 109.6(2) . . ?
O3 S1 O1 103.8(2) . . ?
O2 S1 C18 109.3(3) . . ?
O3 S1 C18 109.3(3) . . ?
O1 S1 C18 103.4(2) . . ?

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
C6 C1 C2 C3 0.0 . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C1 C2 C3 Cl1 178.9(3) . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
Cl1 C3 C4 C5 -178.8(3) . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C4 C5 C6 N1 -178.0(4) . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C2 C1 C6 N1 178.0(4) . . . . ?
N1 C8 C9 N2 -30.9(5) . . . . ?
N1 C8 C9 C10 84.3(5) . . . . ?
N2 C9 C10 O1 177.9(5) . . . . ?
C8 C9 C10 O1 66.2(6) . . . . ?
C16 C11 C12 C13 0.0 . . . . ?
N2 C11 C12 C13 177.5(4) . . . . ?
C11 C12 C13 C14 0.0 . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C12 C13 C14 C17 -178.4(5) . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C17 C14 C15 C16 178.4(5) . . . . ?
C14 C15 C16 C11 0.0 . . . . ?
C12 C11 C16 C15 0.0 . . . . ?
N2 C11 C16 C15 -177.6(4) . . . . ?
C23 C18 C19 C20 0.0 . . . . ?
S1 C18 C19 C20 -177.0(3) . . . . ?
C18 C19 C20 C21 0.0 . . . . ?
C19 C20 C21 C22 0.0 . . . . ?
C19 C20 C21 C24 178.9(5) . . . . ?
C20 C21 C22 C23 0.0 . . . . ?
C24 C21 C22 C23 -178.9(5) . . . . ?
C21 C22 C23 C18 0.0 . . . . ?
C19 C18 C23 C22 0.0 . . . . ?
S1 C18 C23 C22 177.0(3) . . . . ?
C5 C6 N1 C8 -165.0(4) . . . . ?
C1 C6 N1 C8 17.0(6) . . . . ?
C5 C6 N1 C7 -26.0(6) . . . . ?
C1 C6 N1 C7 156.0(4) . . . . ?
C9 C8 N1 C6 174.5(4) . . . . ?
C9 C8 N1 C7 31.1(5) . . . . ?
N2 C7 N1 C6 -162.3(4) . . . . ?
N2 C7 N1 C8 -18.5(6) . . . . ?
C12 C11 N2 C7 -178.9(4) . . . . ?
C16 C11 N2 C7 -1.3(6) . . . . ?
C12 C11 N2 C9 -0.2(7) . . . . ?
C16 C11 N2 C9 177.4(4) . . . . ?
N1 C7 N2 C11 176.5(4) . . . . ?
N1 C7 N2 C9 -2.4(6) . . . . ?
C8 C9 N2 C11 -157.9(5) . . . . ?
C10 C9 N2 C11 83.4(7) . . . . ?
C8 C9 N2 C7 20.9(6) . . . . ?
C10 C9 N2 C7 -97.8(5) . . . . ?
C9 C10 O1 S1 -148.6(4) . . . . ?
C10 O1 S1 O2 -39.7(4) . . . . ?
C10 O1 S1 O3 -169.2(4) . . . . ?
C10 O1 S1 C18 76.8(4) . . . . ?
C19 C18 S1 O2 -169.5(3) . . . . ?
C23 C18 S1 O2 13.4(3) . . . . ?
C19 C18 S1 O3 -36.2(3) . . . . ?
C23 C18 S1 O3 146.7(3) . . . . ?
C19 C18 S1 O1 73.8(3) . . . . ?
C23 C18 S1 O1 -103.3(3) . . . . ?

_refine_diff_density_max         0.211
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.048

