# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_20201225d
_database_code_depnum_ccdc_archive 'CCDC 2072337'
loop_
_audit_author_name
_audit_author_address
'Min Shao'
;Shanghai University
China
;
_audit_update_record             
;
2021-03-23 deposited with the CCDC.	2021-05-14 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H16 Cl N O S'
_chemical_formula_iupac          ?
_chemical_formula_weight         401.89
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_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                   10.7761(5)
_cell_length_b                   8.5009(4)
_cell_length_c                   11.6925(5)
_cell_angle_alpha                90
_cell_angle_beta                 112.539(2)
_cell_angle_gamma                90
_cell_volume                     989.30(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7894
_cell_measurement_theta_min      4.09
_cell_measurement_theta_max      66.69
_cell_measurement_temperature    150.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416

_exptl_absorpt_coefficient_mu    2.801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
;
_exptl_absorpt_correction_T_min  0.5592
_exptl_absorpt_correction_T_max  0.7528

_exptl_special_details           
;
;

_diffrn_ambient_temperature      150.(2)

_diffrn_source                   ?
_diffrn_source_type              ?
_diffrn_source_power             ?
_diffrn_source_current           ?
_diffrn_source_voltage           ?

_diffrn_radiation_probe          ?
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device       'Bruker APEX-II CCD'
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            8458
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_theta_min         4.09
_diffrn_reflns_theta_max         66.69
_diffrn_reflns_theta_full        66.69
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
;

_reflns_number_total             3205
_reflns_number_gt                3168
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_max     0.831
_reflns_Friedel_fraction_full    0.831

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0227
_refine_ls_wR_factor_gt          0.0607
_refine_ls_wR_factor_ref         0.0609
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_number_reflns         3205
_refine_ls_number_parameters     253
_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)+(0.0321P)²+0.0491P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.194
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1308 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.064(5)


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'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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 -0.01827(6) 0.90422(8) -0.00360(5) 0.04757(18) Uani d . . . 1 . .
S S1 0.54053(4) 0.68663(6) 0.73185(4) 0.02805(14) Uani d . . . 1 . .
O O1 0.28897(13) 0.66325(19) 0.71666(12) 0.0317(3) Uani d . . . 1 . .
N N1 0.47903(15) 0.45739(19) 0.56724(14) 0.0227(3) Uani d . . . 1 . .
C C1 0.35580(18) 0.4767(2) 0.59015(16) 0.0221(4) Uani d . . . 1 . .
C C2 0.37368(17) 0.6141(2) 0.68304(16) 0.0240(4) Uani d . . . 1 . .
C C3 0.57306(18) 0.5486(2) 0.63129(16) 0.0218(4) Uani d . . . 1 . .
C C4 0.70799(19) 0.5464(2) 0.62620(17) 0.0244(4) Uani d . . . 1 . .
C C5 0.8115(2) 0.6412(3) 0.7037(2) 0.0322(5) Uani d . . . 1 . .
H H5 0.796417 0.709393 0.76145 0.039 Uiso calc U . R 1 . .
C C6 0.9379(2) 0.6355(3) 0.6961(2) 0.0393(5) Uani d . . . 1 . .
H H6 1.008864 0.699758 0.748987 0.047 Uiso calc U . R 1 . .
C C7 0.9596(2) 0.5370(3) 0.6122(2) 0.0398(5) Uani d . . . 1 . .
H H7 1.045068 0.534943 0.606196 0.048 Uiso calc U . R 1 . .
C C8 0.8571(2) 0.4405(3) 0.5362(2) 0.0336(5) Uani d . . . 1 . .
H H8 0.873069 0.371147 0.479555 0.04 Uiso calc U . R 1 . .
C C9 0.7319(2) 0.4456(2) 0.54302(18) 0.0274(4) Uani d . . . 1 . .
H H9 0.661807 0.379943 0.490661 0.033 Uiso calc U . R 1 . .
C C10 0.24275(19) 0.5175(2) 0.47482(17) 0.0246(4) Uani d . . . 1 . .
C C11 0.14959(19) 0.5549(2) 0.38383(16) 0.0250(4) Uani d . . . 1 . .
C C12 0.03895(19) 0.6061(2) 0.27469(17) 0.0238(4) Uani d . . . 1 . .
C C13 0.06080(19) 0.7183(2) 0.19780(17) 0.0254(4) Uani d . . . 1 . .
H H13 0.148053 0.760393 0.216399 0.03 Uiso calc U . R 1 . .
C C14 -0.0462(2) 0.7676(2) 0.09418(18) 0.0285(4) Uani d . . . 1 . .
C C15 -0.1746(2) 0.7098(3) 0.06587(18) 0.0322(5) Uani d . . . 1 . .
H H15 -0.247296 0.746449 -0.005195 0.039 Uiso calc U . R 1 . .
C C16 -0.1956(2) 0.5985(3) 0.14197(19) 0.0323(5) Uani d . . . 1 . .
H H16 -0.283309 0.557654 0.122763 0.039 Uiso calc U . R 1 . .
C C17 -0.0902(2) 0.5454(3) 0.24637(18) 0.0287(4) Uani d . . . 1 . .
H H17 -0.105485 0.468285 0.29833 0.034 Uiso calc U . R 1 . .
C C18 0.32522(18) 0.3228(2) 0.64657(17) 0.0250(4) Uani d . . . 1 . .
H H18A 0.24801 0.34151 0.67091 0.03 Uiso calc U . R 1 . .
H H18B 0.298994 0.239615 0.582431 0.03 Uiso calc U . R 1 . .
C C19 0.44299(19) 0.2655(2) 0.75799(17) 0.0250(4) Uani d . . . 1 . .
C C20 0.5314(2) 0.1553(3) 0.74448(19) 0.0327(5) Uani d . . . 1 . .
H H20 0.51768 0.116168 0.664442 0.039 Uiso calc U . R 1 . .
C C21 0.6397(2) 0.1016(3) 0.8467(2) 0.0418(5) Uani d . . . 1 . .
H H21 0.699623 0.02624 0.836192 0.05 Uiso calc U . R 1 . .
C C22 0.6606(2) 0.1572(3) 0.9634(2) 0.0449(6) Uani d . . . 1 . .
H H22 0.734867 0.120729 1.033259 0.054 Uiso calc U . R 1 . .
C C23 0.5726(3) 0.2667(3) 0.9783(2) 0.0424(6) Uani d . . . 1 . .
H H23 0.586278 0.304468 1.058704 0.051 Uiso calc U . R 1 . .
C C24 0.4650(2) 0.3214(3) 0.87661(19) 0.0324(5) Uani d . . . 1 . .
H H24 0.405785 0.397343 0.887551 0.039 Uiso calc U . R 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 C14 . 1.735(2) ?
S1 C2 . 1.7753(18) ?
S1 C3 . 1.788(2) ?
O1 C2 . 1.199(2) ?
N1 C3 . 1.268(3) ?
N1 C1 . 1.461(2) ?
C1 C10 . 1.471(2) ?
C1 C18 . 1.556(3) ?
C1 C2 . 1.556(3) ?
C3 C4 . 1.478(3) ?
C4 C9 . 1.392(3) ?
C4 C5 . 1.393(3) ?
C5 C6 . 1.399(3) ?
C5 H5 . 0.95 ?
C6 C7 . 1.377(4) ?
C6 H6 . 0.95 ?
C7 C8 . 1.389(3) ?
C7 H7 . 0.95 ?
C8 C9 . 1.383(3) ?
C8 H8 . 0.95 ?
C9 H9 . 0.95 ?
C10 C11 . 1.192(3) ?
C11 C12 . 1.440(3) ?
C12 C13 . 1.392(3) ?
C12 C17 . 1.400(3) ?
C13 C14 . 1.379(3) ?
C13 H13 . 0.95 ?
C14 C15 . 1.383(3) ?
C15 C16 . 1.375(3) ?
C15 H15 . 0.95 ?
C16 C17 . 1.386(3) ?
C16 H16 . 0.95 ?
C17 H17 . 0.95 ?
C18 C19 . 1.509(3) ?
C18 H18A . 0.99 ?
C18 H18B . 0.99 ?
C19 C20 . 1.388(3) ?
C19 C24 . 1.398(3) ?
C20 C21 . 1.390(3) ?
C20 H20 . 0.95 ?
C21 C22 . 1.379(4) ?
C21 H21 . 0.95 ?
C22 C23 . 1.386(4) ?
C22 H22 . 0.95 ?
C23 C24 . 1.385(3) ?
C23 H23 . 0.95 ?
C24 H24 . 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
C2 S1 C3 . . 89.45(9) ?
C3 N1 C1 . . 113.57(16) ?
N1 C1 C10 . . 110.49(15) ?
N1 C1 C18 . . 109.77(15) ?
C10 C1 C18 . . 110.58(15) ?
N1 C1 C2 . . 109.52(15) ?
C10 C1 C2 . . 107.47(15) ?
C18 C1 C2 . . 108.96(15) ?
O1 C2 C1 . . 125.75(17) ?
O1 C2 S1 . . 125.34(15) ?
C1 C2 S1 . . 108.92(13) ?
N1 C3 C4 . . 122.97(18) ?
N1 C3 S1 . . 118.43(14) ?
C4 C3 S1 . . 118.60(14) ?
C9 C4 C5 . . 119.59(19) ?
C9 C4 C3 . . 118.98(18) ?
C5 C4 C3 . . 121.42(19) ?
C4 C5 C6 . . 119.7(2) ?
C4 C5 H5 . . 120.2 ?
C6 C5 H5 . . 120.2 ?
C7 C6 C5 . . 120.1(2) ?
C7 C6 H6 . . 119.9 ?
C5 C6 H6 . . 119.9 ?
C6 C7 C8 . . 120.3(2) ?
C6 C7 H7 . . 119.8 ?
C8 C7 H7 . . 119.8 ?
C9 C8 C7 . . 119.9(2) ?
C9 C8 H8 . . 120.0 ?
C7 C8 H8 . . 120.0 ?
C8 C9 C4 . . 120.39(19) ?
C8 C9 H9 . . 119.8 ?
C4 C9 H9 . . 119.8 ?
C11 C10 C1 . . 177.5(2) ?
C10 C11 C12 . . 177.8(2) ?
C13 C12 C17 . . 119.94(17) ?
C13 C12 C11 . . 119.49(17) ?
C17 C12 C11 . . 120.56(18) ?
C14 C13 C12 . . 118.96(18) ?
C14 C13 H13 . . 120.5 ?
C12 C13 H13 . . 120.5 ?
C13 C14 C15 . . 121.67(19) ?
C13 C14 Cl1 . . 118.97(16) ?
C15 C14 Cl1 . . 119.36(16) ?
C16 C15 C14 . . 119.13(18) ?
C16 C15 H15 . . 120.4 ?
C14 C15 H15 . . 120.4 ?
C15 C16 C17 . . 120.77(18) ?
C15 C16 H16 . . 119.6 ?
C17 C16 H16 . . 119.6 ?
C16 C17 C12 . . 119.52(19) ?
C16 C17 H17 . . 120.2 ?
C12 C17 H17 . . 120.2 ?
C19 C18 C1 . . 113.11(15) ?
C19 C18 H18A . . 109.0 ?
C1 C18 H18A . . 109.0 ?
C19 C18 H18B . . 109.0 ?
C1 C18 H18B . . 109.0 ?
H18A C18 H18B . . 107.8 ?
C20 C19 C24 . . 118.67(18) ?
C20 C19 C18 . . 120.42(18) ?
C24 C19 C18 . . 120.91(19) ?
C19 C20 C21 . . 120.7(2) ?
C19 C20 H20 . . 119.6 ?
C21 C20 H20 . . 119.6 ?
C22 C21 C20 . . 120.2(2) ?
C22 C21 H21 . . 119.9 ?
C20 C21 H21 . . 119.9 ?
C21 C22 C23 . . 119.6(2) ?
C21 C22 H22 . . 120.2 ?
C23 C22 H22 . . 120.2 ?
C24 C23 C22 . . 120.4(2) ?
C24 C23 H23 . . 119.8 ?
C22 C23 H23 . . 119.8 ?
C23 C24 C19 . . 120.4(2) ?
C23 C24 H24 . . 119.8 ?
C19 C24 H24 . . 119.8 ?

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
C3 N1 C1 C10 . . . . 121.68(17) ?
C3 N1 C1 C18 . . . . -116.11(17) ?
C3 N1 C1 C2 . . . . 3.5(2) ?
N1 C1 C2 O1 . . . . 176.84(18) ?
C10 C1 C2 O1 . . . . 56.8(2) ?
C18 C1 C2 O1 . . . . -63.1(2) ?
N1 C1 C2 S1 . . . . -3.31(18) ?
C10 C1 C2 S1 . . . . -123.37(14) ?
C18 C1 C2 S1 . . . . 116.78(14) ?
C3 S1 C2 O1 . . . . -178.26(18) ?
C3 S1 C2 C1 . . . . 1.89(13) ?
C1 N1 C3 C4 . . . . 178.09(16) ?
C1 N1 C3 S1 . . . . -2.2(2) ?
C2 S1 C3 N1 . . . . 0.05(16) ?
C2 S1 C3 C4 . . . . 179.81(15) ?
N1 C3 C4 C9 . . . . 3.4(3) ?
S1 C3 C4 C9 . . . . -176.36(14) ?
N1 C3 C4 C5 . . . . -175.80(18) ?
S1 C3 C4 C5 . . . . 4.4(3) ?
C9 C4 C5 C6 . . . . 0.7(3) ?
C3 C4 C5 C6 . . . . 179.93(19) ?
C4 C5 C6 C7 . . . . 0.2(3) ?
C5 C6 C7 C8 . . . . -1.2(3) ?
C6 C7 C8 C9 . . . . 1.3(3) ?
C7 C8 C9 C4 . . . . -0.3(3) ?
C5 C4 C9 C8 . . . . -0.7(3) ?
C3 C4 C9 C8 . . . . -179.88(17) ?
C17 C12 C13 C14 . . . . -0.2(3) ?
C11 C12 C13 C14 . . . . -179.40(17) ?
C12 C13 C14 C15 . . . . 0.9(3) ?
C12 C13 C14 Cl1 . . . . -178.56(15) ?
C13 C14 C15 C16 . . . . -1.1(3) ?
Cl1 C14 C15 C16 . . . . 178.37(16) ?
C14 C15 C16 C17 . . . . 0.5(3) ?
C15 C16 C17 C12 . . . . 0.2(3) ?
C13 C12 C17 C16 . . . . -0.4(3) ?
C11 C12 C17 C16 . . . . 178.87(19) ?
N1 C1 C18 C19 . . . . 52.0(2) ?
C10 C1 C18 C19 . . . . 174.11(16) ?
C2 C1 C18 C19 . . . . -68.0(2) ?
C1 C18 C19 C20 . . . . -93.9(2) ?
C1 C18 C19 C24 . . . . 86.4(2) ?
C24 C19 C20 C21 . . . . -0.1(3) ?
C18 C19 C20 C21 . . . . -179.74(19) ?
C19 C20 C21 C22 . . . . 0.1(3) ?
C20 C21 C22 C23 . . . . 0.2(4) ?
C21 C22 C23 C24 . . . . -0.6(4) ?
C22 C23 C24 C19 . . . . 0.7(3) ?
C20 C19 C24 C23 . . . . -0.3(3) ?
C18 C19 C24 C23 . . . . 179.33(19) ?

