# 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_wf-77-b1
_audit_block_doi                 10.5517/ccdc.csd.cc26psmb
_database_code_depnum_ccdc_archive 'CCDC 2046732'
loop_
_audit_author_name
_audit_author_address
slimappleking
;UCAS
China
;
_audit_update_record             
;
2020-11-27 deposited with the CCDC.	2021-02-18 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            'C22 H16 Cl N0 O2 S'
_chemical_formula_weight         379.86

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'
Cl Cl 0.1484 0.1585 '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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   5.556(5)
_cell_length_b                   16.760(16)
_cell_length_c                   10.120(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.089(17)
_cell_angle_gamma                90
_cell_volume                     942.4(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2984
_cell_measurement_theta_min      3.1565
_cell_measurement_theta_max      27.6569

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             394
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.326
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Molybdenum
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7376
_diffrn_reflns_av_unetI/netI     0.0829
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.156
_diffrn_reflns_theta_max         27.514
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_point_group_measured_fraction_full 0.957
_reflns_number_total             4045
_reflns_number_gt                2762
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.873
_reflns_Friedel_fraction_max     0.901
_reflns_Friedel_fraction_full    0.933

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0391P)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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 899 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4045
_refine_ls_number_parameters     237
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.0994
_refine_ls_wR_factor_gt          0.0960
_refine_ls_goodness_of_fit_ref   0.867
_refine_ls_restrained_S_all      0.866
_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
Cl1 Cl 0.1834(5) 0.44396(13) 0.93014(17) 0.0895(8) Uani 1 1 d . . . . .
S1 S 0.8619(3) 0.36890(9) 0.25309(16) 0.0495(3) Uani 1 1 d . . . . .
O1 O 0.7990(12) 0.3055(3) 0.1666(5) 0.0804(17) Uani 1 1 d . . . . .
O2 O 1.1073(7) 0.3919(3) 0.2620(5) 0.0756(15) Uani 1 1 d . . . . .
C1 C 0.3052(13) 0.5045(4) 0.6942(6) 0.0522(16) Uani 1 1 d . . . . .
H1 H 0.425130 0.465761 0.692800 0.063 Uiso 1 1 calc R U . . .
C2 C 0.1536(15) 0.5105(4) 0.8006(6) 0.0582(17) Uani 1 1 d . . . . .
C3 C -0.0247(15) 0.5663(4) 0.8061(7) 0.070(2) Uani 1 1 d . . . . .
H3 H -0.125457 0.570023 0.879108 0.084 Uiso 1 1 calc R U . . .
C4 C -0.0510(16) 0.6181(5) 0.6974(8) 0.078(2) Uani 1 1 d . . . . .
H4 H -0.172166 0.656424 0.698571 0.093 Uiso 1 1 calc R U . . .
C5 C 0.0964(13) 0.6133(4) 0.5915(6) 0.0636(18) Uani 1 1 d . . . . .
H5 H 0.075673 0.647965 0.520671 0.076 Uiso 1 1 calc R U . . .
C6 C 0.2781(12) 0.5568(3) 0.5883(6) 0.0504(16) Uani 1 1 d . . . . .
C7 C 0.4373(12) 0.5483(4) 0.4747(6) 0.0544(18) Uani 1 1 d . . . . .
C8 C 0.5736(12) 0.5402(4) 0.3848(5) 0.0535(17) Uani 1 1 d . . . . .
C9 C 0.7402(11) 0.5302(3) 0.2725(6) 0.0559(17) Uani 1 1 d . . . . .
C10 C 0.6890(14) 0.4512(4) 0.2004(5) 0.0557(17) Uani 1 1 d . . . . .
H10A H 0.716872 0.459174 0.106696 0.067 Uiso 1 1 calc R U . . .
H10B H 0.520156 0.438233 0.211511 0.067 Uiso 1 1 calc R U . . .
C11 C 0.7131(12) 0.6011(4) 0.1764(6) 0.0479(15) Uani 1 1 d . . . . .
C12 C 0.5119(13) 0.6103(4) 0.0951(7) 0.0623(19) Uani 1 1 d . . . . .
H12 H 0.386055 0.573810 0.100065 0.075 Uiso 1 1 calc R U . . .
C13 C 0.4988(14) 0.6736(4) 0.0066(7) 0.0588(17) Uani 1 1 d . . . . .
H13 H 0.364789 0.679301 -0.047787 0.071 Uiso 1 1 calc R U . . .
C14 C 0.6826(14) 0.7275(4) -0.0006(6) 0.0559(17) Uani 1 1 d . . . . .
H14 H 0.673566 0.769145 -0.061088 0.067 Uiso 1 1 calc R U . . .
C15 C 0.8803(14) 0.7212(4) 0.0800(7) 0.064(2) Uani 1 1 d . . . . .
H15 H 1.003806 0.758555 0.076348 0.077 Uiso 1 1 calc R U . . .
C16 C 0.8907(13) 0.6562(4) 0.1690(7) 0.0549(16) Uani 1 1 d . . . . .
H16 H 1.023891 0.651068 0.224159 0.066 Uiso 1 1 calc R U . . .
C17 C 0.7623(11) 0.3426(3) 0.4128(6) 0.0469(15) Uani 1 1 d . . . . .
C18 C 0.8858(13) 0.3658(4) 0.5193(6) 0.0613(16) Uani 1 1 d . . . . .
H18 H 1.020784 0.398024 0.509161 0.074 Uiso 1 1 calc R U . . .
C19 C 0.814(2) 0.3419(5) 0.6475(7) 0.086(3) Uani 1 1 d . . . . .
H19 H 0.901430 0.356993 0.721696 0.104 Uiso 1 1 calc R U . . .
C20 C 0.6101(18) 0.2956(5) 0.6590(8) 0.080(2) Uani 1 1 d . . . . .
H20 H 0.558711 0.279242 0.742111 0.096 Uiso 1 1 calc R U . . .
C21 C 0.4849(17) 0.2740(5) 0.5510(8) 0.078(2) Uani 1 1 d . . . . .
H21 H 0.348055 0.242518 0.560214 0.094 Uiso 1 1 calc R U . . .
C22 C 0.5562(13) 0.2976(4) 0.4273(7) 0.0651(19) Uani 1 1 d . . . . .
H22 H 0.466052 0.283263 0.353526 0.078 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
Cl1 C2 1.729(7) . ?
S1 O2 1.420(4) . ?
S1 O1 1.420(5) . ?
S1 C10 1.763(7) . ?
S1 C17 1.765(6) . ?
C1 C2 1.372(8) . ?
C1 C6 1.393(8) . ?
C2 C3 1.363(10) . ?
C3 C4 1.409(10) . ?
C4 C5 1.353(9) . ?
C5 C6 1.384(9) . ?
C6 C7 1.459(8) . ?
C7 C8 1.192(8) . ?
C8 C9 1.476(7) . ?
C9 C10 1.538(8) . ?
C9 C11 1.543(9) . ?
C11 C16 1.353(9) . ?
C11 C12 1.395(9) . ?
C12 C13 1.391(9) . ?
C13 C14 1.365(9) . ?
C14 C15 1.371(9) . ?
C15 C16 1.415(9) . ?
C17 C18 1.334(8) . ?
C17 C22 1.379(8) . ?
C18 C19 1.416(9) . ?
C19 C20 1.377(12) . ?
C20 C21 1.345(12) . ?
C21 C22 1.371(9) . ?

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
O2 S1 O1 118.5(4) . . ?
O2 S1 C10 109.2(3) . . ?
O1 S1 C10 105.4(3) . . ?
O2 S1 C17 108.2(3) . . ?
O1 S1 C17 107.5(3) . . ?
C10 S1 C17 107.5(3) . . ?
C2 C1 C6 119.4(6) . . ?
C3 C2 C1 122.0(6) . . ?
C3 C2 Cl1 118.7(5) . . ?
C1 C2 Cl1 119.3(6) . . ?
C2 C3 C4 117.8(6) . . ?
C5 C4 C3 121.3(7) . . ?
C4 C5 C6 120.2(7) . . ?
C5 C6 C1 119.4(6) . . ?
C5 C6 C7 121.9(6) . . ?
C1 C6 C7 118.7(6) . . ?
C8 C7 C6 177.6(7) . . ?
C7 C8 C9 179.4(7) . . ?
C8 C9 C10 110.3(5) . . ?
C8 C9 C11 109.7(5) . . ?
C10 C9 C11 110.2(5) . . ?
C9 C10 S1 115.4(5) . . ?
C16 C11 C12 118.5(6) . . ?
C16 C11 C9 119.3(6) . . ?
C12 C11 C9 122.3(6) . . ?
C13 C12 C11 120.3(6) . . ?
C14 C13 C12 120.0(7) . . ?
C13 C14 C15 121.1(6) . . ?
C14 C15 C16 118.0(6) . . ?
C11 C16 C15 122.1(7) . . ?
C18 C17 C22 120.0(6) . . ?
C18 C17 S1 120.3(5) . . ?
C22 C17 S1 119.7(6) . . ?
C17 C18 C19 120.7(7) . . ?
C20 C19 C18 118.1(9) . . ?
C21 C20 C19 120.5(7) . . ?
C20 C21 C22 120.9(8) . . ?
C21 C22 C17 119.7(7) . . ?

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.046



