# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_j
_database_code_depnum_ccdc_archive 'CCDC 2174243'
loop_
_audit_author_name
_audit_author_address
'Yi-Min Jiang'
;Fuzhou university
China
;
_audit_update_record             
;
2022-05-23 deposited with the CCDC.	2022-08-23 downloaded from the CCDC.
;
_audit_creation_date             2022-05-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H12 Cl2 O S'
_chemical_formula_sum            'C14 H12 Cl2 O S'
_chemical_formula_weight         299.20
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
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'

_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.
;
_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                   5.7105(4)
_cell_length_b                   13.5285(8)
_cell_length_c                   9.2312(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.574(2)
_cell_angle_gamma                90
_cell_volume                     710.88(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7346
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.911
_cell_measurement_theta_min      2.677
_shelx_estimated_absorpt_T_max   0.944
_shelx_estimated_absorpt_T_min   0.944
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0956 before and 0.0482 after correction.
The Ratio of minimum to maximum transmission is 0.9531.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            18959
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.250
_diffrn_reflns_theta_min         2.213
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.876
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.946
_reflns_number_gt                2753
_reflns_number_total             3421
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 1109 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3421
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0329
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0352P)²+0.0644P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0700
_refine_ls_wR_factor_ref         0.0746
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.5975(5) 0.6380(2) 0.7376(3) 0.0569(7) Uani 1 1 d . . . . .
H1 H 0.457631 0.672746 0.720198 0.068 Uiso 1 1 calc R U . . .
C2 C 0.6609(6) 0.6019(3) 0.8748(4) 0.0667(9) Uani 1 1 d . . . . .
H2 H 0.562886 0.612106 0.949132 0.080 Uiso 1 1 calc R U . . .
C3 C 0.8674(6) 0.5510(3) 0.9024(4) 0.0703(9) Uani 1 1 d . . . . .
H3 H 0.909469 0.526292 0.994906 0.084 Uiso 1 1 calc R U . . .
C4 C 1.0101(6) 0.5370(3) 0.7929(4) 0.0750(10) Uani 1 1 d . . . . .
H4 H 1.150680 0.502901 0.811091 0.090 Uiso 1 1 calc R U . . .
C5 C 0.9484(5) 0.5730(3) 0.6550(4) 0.0644(8) Uani 1 1 d . . . . .
H5 H 1.048601 0.563434 0.581623 0.077 Uiso 1 1 calc R U . . .
C6 C 0.7410(5) 0.6227(2) 0.6253(3) 0.0472(6) Uani 1 1 d . . . . .
C7 C 0.6628(5) 0.6601(2) 0.4758(3) 0.0515(7) Uani 1 1 d . . . . .
H7 H 0.496190 0.677799 0.474276 0.062 Uiso 1 1 calc R U . . .
C8 C 0.6911(5) 0.5855(2) 0.3550(3) 0.0491(6) Uani 1 1 d . . . . .
H8A H 0.854261 0.565533 0.355240 0.059 Uiso 1 1 calc R U . . .
H8B H 0.644047 0.615055 0.261422 0.059 Uiso 1 1 calc R U . . .
C9 C 0.5868(5) 0.41083(19) 0.2293(3) 0.0440(6) Uani 1 1 d . . . . .
C10 C 0.8003(5) 0.3610(2) 0.2374(3) 0.0511(7) Uani 1 1 d . . . . .
H10 H 0.902041 0.364558 0.321062 0.061 Uiso 1 1 calc R U . . .
C11 C 0.8590(5) 0.3064(2) 0.1204(4) 0.0559(7) Uani 1 1 d . . . . .
H11 H 1.001980 0.273274 0.123580 0.067 Uiso 1 1 calc R U . . .
C12 C 0.7053(5) 0.3012(2) -0.0016(4) 0.0575(7) Uani 1 1 d . . . . .
C13 C 0.4914(6) 0.3490(2) -0.0087(4) 0.0600(8) Uani 1 1 d . . . . .
H13 H 0.387803 0.343757 -0.091284 0.072 Uiso 1 1 calc R U . . .
C14 C 0.4332(5) 0.4047(2) 0.1083(3) 0.0526(7) Uani 1 1 d . . . . .
H14 H 0.290274 0.437885 0.104803 0.063 Uiso 1 1 calc R U . . .
Cl1 Cl 0.82580(19) 0.76974(6) 0.43334(10) 0.0806(3) Uani 1 1 d . . . . .
Cl2 Cl 0.78071(19) 0.23123(9) -0.14829(11) 0.0960(4) Uani 1 1 d . . . . .
O1 O 0.2607(3) 0.51222(18) 0.3535(3) 0.0696(6) Uani 1 1 d . . . . .
S1 S 0.50813(12) 0.47864(5) 0.38500(8) 0.05142(19) 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 H1 0.9300 . ?
C1 C2 1.378(5) . ?
C1 C6 1.386(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.372(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.361(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.371(4) . ?
C6 C7 1.504(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.522(4) . ?
C7 Cl1 1.811(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 S1 1.818(3) . ?
C9 C10 1.390(4) . ?
C9 C14 1.367(4) . ?
C9 S1 1.792(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.372(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.373(5) . ?
C12 C13 1.379(5) . ?
C12 Cl2 1.734(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.379(4) . ?
C14 H14 0.9300 . ?
O1 S1 1.490(2) . ?

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 H1 119.8 . . ?
C2 C1 C6 120.4(3) . . ?
C6 C1 H1 119.8 . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.2(3) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C7 119.1(3) . . ?
C5 C6 C1 118.4(3) . . ?
C5 C6 C7 122.5(3) . . ?
C6 C7 H7 108.2 . . ?
C6 C7 C8 114.1(2) . . ?
C6 C7 Cl1 110.71(19) . . ?
C8 C7 H7 108.2 . . ?
C8 C7 Cl1 107.34(19) . . ?
Cl1 C7 H7 108.2 . . ?
C7 C8 H8A 110.0 . . ?
C7 C8 H8B 110.0 . . ?
C7 C8 S1 108.64(18) . . ?
H8A C8 H8B 108.3 . . ?
S1 C8 H8A 110.0 . . ?
S1 C8 H8B 110.0 . . ?
C10 C9 S1 118.7(2) . . ?
C14 C9 C10 121.1(3) . . ?
C14 C9 S1 120.1(2) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 C9 119.2(3) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.6(3) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 121.3(3) . . ?
C11 C12 Cl2 119.1(2) . . ?
C13 C12 Cl2 119.6(3) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 C12 119.2(3) . . ?
C14 C13 H13 120.4 . . ?
C9 C14 C13 119.6(3) . . ?
C9 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C9 S1 C8 95.80(12) . . ?
O1 S1 C8 105.97(14) . . ?
O1 S1 C9 107.11(13) . . ?

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
C1 C2 C3 C4 0.4(5) . . . . ?
C1 C6 C7 C8 -133.7(3) . . . . ?
C1 C6 C7 Cl1 105.1(3) . . . . ?
C2 C1 C6 C5 -1.4(5) . . . . ?
C2 C1 C6 C7 177.9(3) . . . . ?
C2 C3 C4 C5 -0.3(6) . . . . ?
C3 C4 C5 C6 -0.6(6) . . . . ?
C4 C5 C6 C1 1.5(5) . . . . ?
C4 C5 C6 C7 -177.8(3) . . . . ?
C5 C6 C7 C8 45.6(4) . . . . ?
C5 C6 C7 Cl1 -75.6(3) . . . . ?
C6 C1 C2 C3 0.4(5) . . . . ?
C6 C7 C8 S1 62.0(3) . . . . ?
C7 C8 S1 C9 -179.7(2) . . . . ?
C7 C8 S1 O1 70.7(2) . . . . ?
C9 C10 C11 C12 -0.7(4) . . . . ?
C10 C9 C14 C13 -0.7(4) . . . . ?
C10 C9 S1 C8 79.0(2) . . . . ?
C10 C9 S1 O1 -172.3(2) . . . . ?
C10 C11 C12 C13 -0.5(5) . . . . ?
C10 C11 C12 Cl2 -179.5(2) . . . . ?
C11 C12 C13 C14 1.2(5) . . . . ?
C12 C13 C14 C9 -0.6(4) . . . . ?
C14 C9 C10 C11 1.4(4) . . . . ?
C14 C9 S1 C8 -104.3(2) . . . . ?
C14 C9 S1 O1 4.4(3) . . . . ?
Cl1 C7 C8 S1 -174.89(15) . . . . ?
Cl2 C12 C13 C14 -179.8(2) . . . . ?
S1 C9 C10 C11 178.1(2) . . . . ?
S1 C9 C14 C13 -177.3(2) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
