# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_ptz-ph-1cl
_database_code_depnum_ccdc_archive 'CCDC 2112070'
loop_
_audit_author_name
_audit_author_address
'Yang Jie'
;Tianjin University
China
;
_audit_update_record             
;
2021-09-27 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;
_audit_creation_date             2021-09-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H12 Cl N S'
_chemical_formula_sum            'C18 H12 Cl N S'
_chemical_formula_weight         309.80
_chemical_melting_point          ?
_chemical_oxdiff_formula         C18H12SNCl
_chemical_oxdiff_usercomment     'C H S N Cl'
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'
S S 0.3331 0.5567 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   9.5771(2)
_cell_length_b                   24.0661(4)
_cell_length_c                   12.7927(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.267(2)
_cell_angle_gamma                90
_cell_volume                     2947.78(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    11286
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.1580
_cell_measurement_theta_min      4.5980
_shelx_estimated_absorpt_T_max   0.719
_shelx_estimated_absorpt_T_min   0.638
_exptl_absorpt_coefficient_mu    3.531
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21191
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.255
_diffrn_reflns_theta_min         3.673
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1975
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  28.00   1.00    3.68    --  -40.87  37.00 150.00   92
  2  ω    -73.00  24.00   1.00    3.68    --  -40.87  77.00-120.00   97
  3  ω   -114.00 -17.00   1.00    3.68    --  -40.87 -37.00 -30.00   97
  4  ω     44.00  69.00   1.00    3.68    --   40.87 -77.00-120.00   25
  5  ω     59.00  90.00   1.00    3.68    --   40.87-125.00  90.00   31
  6  ω     34.00 118.00   1.00   14.74    --  105.32 -61.00   0.00   84
  7  ω     78.00 117.00   1.00   14.74    --  105.32-125.00 150.00   39
  8  ω     24.00 106.00   1.00   14.74    --  105.32 -94.00 -60.00   82
  9  ω     30.00 117.00   1.00   14.74    --  105.32 -30.00  60.00   87
 10  ω     32.00 116.00   1.00   14.74    --  105.32-125.00 -60.00   84
 11  ω     91.00 123.00   1.00   14.74    --  105.32 -45.00 120.00   32
 12  ω     41.00 101.00   1.00   14.74    --  105.32 -94.00   0.00   60
 13  ω    117.00 143.00   1.00   14.74    --  105.32 125.00  90.00   26
 14  ω    103.00 166.00   1.00   14.74    --  105.32 125.00 -30.00   63
 15  ω     90.00 177.00   1.00   14.74    --  105.32  45.00  90.00   87
 16  ω     32.00 151.00   1.00   14.74    --  105.32 -15.00 -90.00  119
 17  ω     33.00  98.00   1.00   14.74    --  105.32 -94.00 150.00   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1082291000
_diffrn_orient_matrix_UB_12      0.0444021000
_diffrn_orient_matrix_UB_13      0.0293250000
_diffrn_orient_matrix_UB_21      0.0944536000
_diffrn_orient_matrix_UB_22      0.0183412000
_diffrn_orient_matrix_UB_23      0.0928122000
_diffrn_orient_matrix_UB_31      0.0724432000
_diffrn_orient_matrix_UB_32      0.0422860000
_diffrn_orient_matrix_UB_33      -0.0710269000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5255
_reflns_number_total             5849
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5849
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0402
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0544P)²+0.9378P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1108
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1'(H1'), C2'(H2'), C3'(H3'), C4'(H4'), C9'(H9'), C10'(H10'), C11'(H11'),
 C12'(H12'), C14'(H14'), C15'(H15'), C17'(H17'), C18'(H18'), C1(H1), C2(H2),
 C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15),
 C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Cl1' Cl 0.69476(9) 0.53857(3) 1.23685(5) 0.0964(2) Uani 1 1 d . . . . .
S1' S 0.69244(6) 0.72413(2) 0.64278(4) 0.06710(16) Uani 1 1 d . . . . .
N1' N 0.62239(15) 0.65721(6) 0.83290(11) 0.0470(3) Uani 1 1 d . . . . .
C1' C 0.6117(2) 0.56862(8) 0.73728(15) 0.0544(4) Uani 1 1 d . . . . .
H1' H 0.5985 0.5495 0.7995 0.065 Uiso 1 1 calc R . . . .
C2' C 0.6149(2) 0.53937(10) 0.64404(16) 0.0637(5) Uani 1 1 d . . . . .
H2' H 0.6052 0.5009 0.6446 0.076 Uiso 1 1 calc R . . . .
C3' C 0.6324(2) 0.56670(11) 0.55037(17) 0.0673(5) Uani 1 1 d . . . . .
H3' H 0.6326 0.5471 0.4878 0.081 Uiso 1 1 calc R . . . .
C4' C 0.6494(2) 0.62345(10) 0.55114(15) 0.0623(5) Uani 1 1 d . . . . .
H4' H 0.6602 0.6422 0.4883 0.075 Uiso 1 1 calc R . . . .
C5' C 0.65063(18) 0.65316(9) 0.64442(14) 0.0520(4) Uani 1 1 d . . . . .
C6' C 0.62769(16) 0.62597(8) 0.73937(13) 0.0459(4) Uani 1 1 d . . . . .
C7' C 0.56466(17) 0.71151(7) 0.83164(14) 0.0469(4) Uani 1 1 d . . . . .
C8' C 0.5860(2) 0.74623(8) 0.74559(16) 0.0554(4) Uani 1 1 d . . . . .
C9' C 0.5289(3) 0.79910(9) 0.7428(2) 0.0709(6) Uani 1 1 d . . . . .
H9' H 0.5419 0.8216 0.6847 0.085 Uiso 1 1 calc R . . . .
C10' C 0.4534(3) 0.81858(9) 0.8251(2) 0.0773(7) Uani 1 1 d . . . . .
H10' H 0.4176 0.8545 0.8236 0.093 Uiso 1 1 calc R . . . .
C11' C 0.4305(2) 0.78446(9) 0.9102(2) 0.0694(6) Uani 1 1 d . . . . .
H11' H 0.3784 0.7974 0.9656 0.083 Uiso 1 1 calc R . . . .
C12' C 0.4850(2) 0.73100(8) 0.91336(16) 0.0558(4) Uani 1 1 d . . . . .
H12' H 0.4682 0.7082 0.9704 0.067 Uiso 1 1 calc R . . . .
C13' C 0.63511(16) 0.62898(7) 0.93187(12) 0.0418(3) Uani 1 1 d . . . . .
C14' C 0.75751(17) 0.63481(7) 0.98909(13) 0.0463(4) Uani 1 1 d . . . . .
H14' H 0.8280 0.6575 0.9642 0.056 Uiso 1 1 calc R . . . .
C15' C 0.77697(19) 0.60718(9) 1.08346(14) 0.0547(4) Uani 1 1 d . . . . .
H15' H 0.8602 0.6108 1.1217 0.066 Uiso 1 1 calc R . . . .
C16' C 0.6708(2) 0.57434(8) 1.11945(14) 0.0540(4) Uani 1 1 d . . . . .
C17' C 0.5464(2) 0.56931(8) 1.06519(15) 0.0571(5) Uani 1 1 d . . . . .
H17' H 0.4748 0.5478 1.0917 0.069 Uiso 1 1 calc R . . . .
C18' C 0.52846(19) 0.59658(8) 0.97079(15) 0.0527(4) Uani 1 1 d . . . . .
H18' H 0.4446 0.5932 0.9333 0.063 Uiso 1 1 calc R . . . .
Cl1 Cl 0.84683(8) 0.44570(3) 0.51932(4) 0.0851(2) Uani 1 1 d . . . . .
S1 S 0.80678(6) 0.28629(2) -0.10801(4) 0.05984(14) Uani 1 1 d . . . . .
N1 N 0.86834(14) 0.34658(6) 0.09565(10) 0.0429(3) Uani 1 1 d . . . . .
C1 C 1.00245(19) 0.26922(7) 0.17194(14) 0.0503(4) Uani 1 1 d . . . . .
H1 H 1.0159 0.2894 0.2333 0.060 Uiso 1 1 calc R . . . .
C2 C 1.0573(2) 0.21604(8) 0.16433(18) 0.0606(5) Uani 1 1 d . . . . .
H2 H 1.1054 0.2006 0.2212 0.073 Uiso 1 1 calc R . . . .
C3 C 1.0412(2) 0.18598(8) 0.07310(19) 0.0646(5) Uani 1 1 d . . . . .
H3 H 1.0778 0.1503 0.0683 0.078 Uiso 1 1 calc R . . . .
C4 C 0.9706(2) 0.20928(8) -0.01074(17) 0.0596(5) Uani 1 1 d . . . . .
H4 H 0.9622 0.1897 -0.0732 0.072 Uiso 1 1 calc R . . . .
C5 C 0.91186(18) 0.26157(7) -0.00319(13) 0.0473(4) Uani 1 1 d . . . . .
C6 C 0.92766(16) 0.29259(7) 0.08882(12) 0.0410(3) Uani 1 1 d . . . . .
C7 C 0.85569(15) 0.38118(7) 0.00694(12) 0.0411(3) Uani 1 1 d . . . . .
C8 C 0.83855(17) 0.35779(8) -0.09316(13) 0.0458(4) Uani 1 1 d . . . . .
C9 C 0.83587(19) 0.39131(9) -0.18167(14) 0.0556(4) Uani 1 1 d . . . . .
H9 H 0.8315 0.3751 -0.2476 0.067 Uiso 1 1 calc R . . . .
C10 C 0.8397(2) 0.44841(9) -0.17259(16) 0.0614(5) Uani 1 1 d . . . . .
H10 H 0.8373 0.4708 -0.2319 0.074 Uiso 1 1 calc R . . . .
C11 C 0.8471(2) 0.47188(8) -0.07425(16) 0.0586(5) Uani 1 1 d . . . . .
H11 H 0.8457 0.5103 -0.0673 0.070 Uiso 1 1 calc R . . . .
C12 C 0.85673(18) 0.43882(7) 0.01453(14) 0.0492(4) Uani 1 1 d . . . . .
H12 H 0.8640 0.4555 0.0800 0.059 Uiso 1 1 calc R . . . .
C13 C 0.86579(16) 0.37174(6) 0.19770(12) 0.0391(3) Uani 1 1 d . . . . .
C14 C 0.74670(17) 0.36658(8) 0.25516(13) 0.0466(4) Uani 1 1 d . . . . .
H14 H 0.6705 0.3471 0.2276 0.056 Uiso 1 1 calc R . . . .
C15 C 0.73934(19) 0.39010(8) 0.35370(14) 0.0530(4) Uani 1 1 d . . . . .
H15 H 0.6585 0.3870 0.3922 0.064 Uiso 1 1 calc R . . . .
C16 C 0.8536(2) 0.41817(7) 0.39365(13) 0.0497(4) Uani 1 1 d . . . . .
C17 C 0.9746(2) 0.42349(7) 0.33824(14) 0.0514(4) Uani 1 1 d . . . . .
H17 H 1.0512 0.4424 0.3666 0.062 Uiso 1 1 calc R . . . .
C18 C 0.98000(18) 0.40011(7) 0.23950(14) 0.0479(4) Uani 1 1 d . . . . .
H18 H 1.0608 0.4035 0.2010 0.057 Uiso 1 1 calc R . . . .


_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' C16' 1.7418(18) . ?
S1' C5' 1.755(2) . ?
S1' C8' 1.764(2) . ?
N1' C6' 1.415(2) . ?
N1' C7' 1.419(2) . ?
N1' C13' 1.440(2) . ?
C1' H1' 0.9300 . ?
C1' C2' 1.386(3) . ?
C1' C6' 1.389(3) . ?
C2' H2' 0.9300 . ?
C2' C3' 1.380(3) . ?
C3' H3' 0.9300 . ?
C3' C4' 1.375(3) . ?
C4' H4' 0.9300 . ?
C4' C5' 1.391(3) . ?
C5' C6' 1.401(2) . ?
C7' C8' 1.401(3) . ?
C7' C12' 1.389(3) . ?
C8' C9' 1.385(3) . ?
C9' H9' 0.9300 . ?
C9' C10' 1.373(4) . ?
C10' H10' 0.9300 . ?
C10' C11' 1.386(4) . ?
C11' H11' 0.9300 . ?
C11' C12' 1.389(3) . ?
C12' H12' 0.9300 . ?
C13' C14' 1.375(2) . ?
C13' C18' 1.386(2) . ?
C14' H14' 0.9300 . ?
C14' C15' 1.387(2) . ?
C15' H15' 0.9300 . ?
C15' C16' 1.375(3) . ?
C16' C17' 1.371(3) . ?
C17' H17' 0.9300 . ?
C17' C18' 1.382(3) . ?
C18' H18' 0.9300 . ?
Cl1 C16 1.7413(16) . ?
S1 C5 1.7621(19) . ?
S1 C8 1.7572(18) . ?
N1 C6 1.422(2) . ?
N1 C7 1.411(2) . ?
N1 C13 1.4398(19) . ?
C1 H1 0.9300 . ?
C1 C2 1.388(3) . ?
C1 C6 1.388(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(3) . ?
C5 C6 1.399(2) . ?
C7 C8 1.405(2) . ?
C7 C12 1.391(2) . ?
C8 C9 1.390(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.380(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.380(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.388(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(2) . ?
C13 C18 1.387(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.385(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.375(3) . ?
C16 C17 1.378(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.385(2) . ?
C18 H18 0.9300 . ?

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
C5' S1' C8' 98.55(9) . . ?
C6' N1' C7' 120.06(14) . . ?
C6' N1' C13' 119.27(14) . . ?
C7' N1' C13' 118.04(14) . . ?
C2' C1' H1' 119.4 . . ?
C2' C1' C6' 121.11(18) . . ?
C6' C1' H1' 119.4 . . ?
C1' C2' H2' 119.6 . . ?
C3' C2' C1' 120.7(2) . . ?
C3' C2' H2' 119.6 . . ?
C2' C3' H3' 120.5 . . ?
C4' C3' C2' 118.9(2) . . ?
C4' C3' H3' 120.5 . . ?
C3' C4' H4' 119.5 . . ?
C3' C4' C5' 121.02(19) . . ?
C5' C4' H4' 119.5 . . ?
C4' C5' S1' 119.20(15) . . ?
C4' C5' C6' 120.34(19) . . ?
C6' C5' S1' 120.34(15) . . ?
C1' C6' N1' 122.57(15) . . ?
C1' C6' C5' 117.82(17) . . ?
C5' C6' N1' 119.61(16) . . ?
C8' C7' N1' 119.66(17) . . ?
C12' C7' N1' 121.51(16) . . ?
C12' C7' C8' 118.82(17) . . ?
C7' C8' S1' 120.20(15) . . ?
C9' C8' S1' 119.48(17) . . ?
C9' C8' C7' 120.3(2) . . ?
C8' C9' H9' 119.7 . . ?
C10' C9' C8' 120.6(2) . . ?
C10' C9' H9' 119.7 . . ?
C9' C10' H10' 120.2 . . ?
C9' C10' C11' 119.7(2) . . ?
C11' C10' H10' 120.2 . . ?
C10' C11' H11' 119.8 . . ?
C10' C11' C12' 120.4(2) . . ?
C12' C11' H11' 119.8 . . ?
C7' C12' H12' 119.9 . . ?
C11' C12' C7' 120.2(2) . . ?
C11' C12' H12' 119.9 . . ?
C14' C13' N1' 118.32(14) . . ?
C14' C13' C18' 119.50(15) . . ?
C18' C13' N1' 122.18(15) . . ?
C13' C14' H14' 119.6 . . ?
C13' C14' C15' 120.72(16) . . ?
C15' C14' H14' 119.6 . . ?
C14' C15' H15' 120.6 . . ?
C16' C15' C14' 118.73(17) . . ?
C16' C15' H15' 120.6 . . ?
C15' C16' Cl1' 119.24(16) . . ?
C17' C16' Cl1' 119.30(15) . . ?
C17' C16' C15' 121.46(16) . . ?
C16' C17' H17' 120.3 . . ?
C16' C17' C18' 119.37(16) . . ?
C18' C17' H17' 120.3 . . ?
C13' C18' H18' 119.9 . . ?
C17' C18' C13' 120.17(17) . . ?
C17' C18' H18' 119.9 . . ?
C8 S1 C5 98.84(8) . . ?
C6 N1 C13 117.07(13) . . ?
C7 N1 C6 121.17(13) . . ?
C7 N1 C13 118.57(13) . . ?
C2 C1 H1 119.7 . . ?
C2 C1 C6 120.64(18) . . ?
C6 C1 H1 119.7 . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.5(2) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.36(18) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.71(18) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 S1 118.72(14) . . ?
C4 C5 C6 120.51(18) . . ?
C6 C5 S1 120.62(14) . . ?
C1 C6 N1 121.56(15) . . ?
C1 C6 C5 118.22(16) . . ?
C5 C6 N1 120.22(15) . . ?
C8 C7 N1 120.19(15) . . ?
C12 C7 N1 122.17(14) . . ?
C12 C7 C8 117.62(15) . . ?
C7 C8 S1 120.48(13) . . ?
C9 C8 S1 118.70(14) . . ?
C9 C8 C7 120.64(17) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.63(17) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.5 . . ?
C11 C10 C9 119.04(18) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.84(19) . . ?
C12 C11 H11 119.6 . . ?
C7 C12 H12 119.5 . . ?
C11 C12 C7 120.96(17) . . ?
C11 C12 H12 119.5 . . ?
C14 C13 N1 118.51(14) . . ?
C14 C13 C18 119.63(15) . . ?
C18 C13 N1 121.85(14) . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.58(16) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 120.6 . . ?
C16 C15 C14 118.88(16) . . ?
C16 C15 H15 120.6 . . ?
C15 C16 Cl1 118.98(14) . . ?
C15 C16 C17 121.74(16) . . ?
C17 C16 Cl1 119.24(15) . . ?
C16 C17 H17 120.7 . . ?
C16 C17 C18 118.69(16) . . ?
C18 C17 H17 120.7 . . ?
C13 C18 H18 119.8 . . ?
C17 C18 C13 120.46(16) . . ?
C17 C18 H18 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1' C16' C17' C18' -178.45(15) . . . . ?
S1' C5' C6' N1' 7.3(2) . . . . ?
S1' C5' C6' C1' -172.38(14) . . . . ?
S1' C8' C9' C10' -175.70(17) . . . . ?
N1' C7' C8' S1' -3.7(2) . . . . ?
N1' C7' C8' C9' 179.27(16) . . . . ?
N1' C7' C12' C11' 179.63(17) . . . . ?
N1' C13' C14' C15' -178.05(16) . . . . ?
N1' C13' C18' C17' 178.66(17) . . . . ?
C1' C2' C3' C4' 1.3(3) . . . . ?
C2' C1' C6' N1' 178.83(17) . . . . ?
C2' C1' C6' C5' -1.5(3) . . . . ?
C2' C3' C4' C5' 0.7(3) . . . . ?
C3' C4' C5' S1' 172.77(16) . . . . ?
C3' C4' C5' C6' -3.1(3) . . . . ?
C4' C5' C6' N1' -176.86(15) . . . . ?
C4' C5' C6' C1' 3.5(2) . . . . ?
C5' S1' C8' C7' 34.74(16) . . . . ?
C5' S1' C8' C9' -148.16(16) . . . . ?
C6' N1' C7' C8' -36.6(2) . . . . ?
C6' N1' C7' C12' 142.39(16) . . . . ?
C6' N1' C13' C14' 107.13(18) . . . . ?
C6' N1' C13' C18' -73.1(2) . . . . ?
C6' C1' C2' C3' -0.9(3) . . . . ?
C7' N1' C6' C1' -145.69(17) . . . . ?
C7' N1' C6' C5' 34.7(2) . . . . ?
C7' N1' C13' C14' -91.21(19) . . . . ?
C7' N1' C13' C18' 88.6(2) . . . . ?
C7' C8' C9' C10' 1.4(3) . . . . ?
C8' S1' C5' C4' 147.48(15) . . . . ?
C8' S1' C5' C6' -36.62(16) . . . . ?
C8' C7' C12' C11' -1.4(3) . . . . ?
C8' C9' C10' C11' -1.9(3) . . . . ?
C9' C10' C11' C12' 0.8(3) . . . . ?
C10' C11' C12' C7' 0.9(3) . . . . ?
C12' C7' C8' S1' 177.35(13) . . . . ?
C12' C7' C8' C9' 0.3(3) . . . . ?
C13' N1' C6' C1' 15.6(2) . . . . ?
C13' N1' C6' C5' -164.07(15) . . . . ?
C13' N1' C7' C8' 161.93(15) . . . . ?
C13' N1' C7' C12' -19.1(2) . . . . ?
C13' C14' C15' C16' -0.8(3) . . . . ?
C14' C13' C18' C17' -1.5(3) . . . . ?
C14' C15' C16' Cl1' 179.04(15) . . . . ?
C14' C15' C16' C17' -1.2(3) . . . . ?
C15' C16' C17' C18' 1.8(3) . . . . ?
C16' C17' C18' C13' -0.4(3) . . . . ?
C18' C13' C14' C15' 2.2(3) . . . . ?
Cl1 C16 C17 C18 178.27(14) . . . . ?
S1 C5 C6 N1 -5.2(2) . . . . ?
S1 C5 C6 C1 174.96(13) . . . . ?
S1 C8 C9 C10 170.43(15) . . . . ?
N1 C7 C8 S1 9.5(2) . . . . ?
N1 C7 C8 C9 -175.43(15) . . . . ?
N1 C7 C12 C11 178.59(16) . . . . ?
N1 C13 C14 C15 -179.98(16) . . . . ?
N1 C13 C18 C17 -179.49(16) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C1 C6 N1 178.81(16) . . . . ?
C2 C1 C6 C5 -1.3(3) . . . . ?
C2 C3 C4 C5 -2.2(3) . . . . ?
C3 C4 C5 S1 -173.26(16) . . . . ?
C3 C4 C5 C6 2.3(3) . . . . ?
C4 C5 C6 N1 179.29(15) . . . . ?
C4 C5 C6 C1 -0.6(2) . . . . ?
C5 S1 C8 C7 -35.93(15) . . . . ?
C5 S1 C8 C9 148.87(14) . . . . ?
C6 N1 C7 C8 29.5(2) . . . . ?
C6 N1 C7 C12 -151.79(16) . . . . ?
C6 N1 C13 C14 -95.15(18) . . . . ?
C6 N1 C13 C18 83.99(19) . . . . ?
C6 C1 C2 C3 1.5(3) . . . . ?
C7 N1 C6 C1 148.00(15) . . . . ?
C7 N1 C6 C5 -31.8(2) . . . . ?
C7 N1 C13 C14 104.81(17) . . . . ?
C7 N1 C13 C18 -76.1(2) . . . . ?
C7 C8 C9 C10 -4.8(3) . . . . ?
C8 S1 C5 C4 -150.64(15) . . . . ?
C8 S1 C5 C6 33.75(15) . . . . ?
C8 C7 C12 C11 -2.7(2) . . . . ?
C8 C9 C10 C11 0.4(3) . . . . ?
C9 C10 C11 C12 2.8(3) . . . . ?
C10 C11 C12 C7 -1.6(3) . . . . ?
C12 C7 C8 S1 -169.30(13) . . . . ?
C12 C7 C8 C9 5.8(2) . . . . ?
C13 N1 C6 C1 -11.5(2) . . . . ?
C13 N1 C6 C5 168.67(14) . . . . ?
C13 N1 C7 C8 -171.29(14) . . . . ?
C13 N1 C7 C12 7.4(2) . . . . ?
C13 C14 C15 C16 -0.7(3) . . . . ?
C14 C13 C18 C17 -0.4(3) . . . . ?
C14 C15 C16 Cl1 -177.79(14) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C16 C17 C18 C13 -0.3(3) . . . . ?
C18 C13 C14 C15 0.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.294
_oxdiff_exptl_absorpt_empirical_full_min 0.795
####################################################################### 
# 
# 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_cs-cl3-ch2cl2-pe-l-1
_database_code_depnum_ccdc_archive 'CCDC 2075007'
loop_
_audit_author_name
_audit_author_address
'Yang Jie'
;Tianjin University
China
;
_audit_update_record             
;
2021-09-27 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;
_audit_creation_date             2021-09-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H10 Cl3 N S'
_chemical_formula_sum            'C18 H10 Cl3 N S'
_chemical_formula_weight         378.68
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H S N Cl'
_chemical_oxdiff_usercomment     'C H S N Cl'
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'
S S 0.3331 0.5567 '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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.99106(17)
_cell_length_b                   15.1047(2)
_cell_length_c                   10.99953(19)
_cell_angle_alpha                90
_cell_angle_beta                 95.6373(16)
_cell_angle_gamma                90
_cell_volume                     1651.93(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3938
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.9230
_cell_measurement_theta_min      4.9700
_shelx_estimated_absorpt_T_max   0.638
_shelx_estimated_absorpt_T_min   0.458
_exptl_absorpt_coefficient_mu    6.172
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5909
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.002
_diffrn_reflns_theta_min         4.990
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1975
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -78.00 -15.00   1.00    1.00    --  -41.12 -57.00   0.00   63
  2  ω    -29.00  -4.00   1.00    1.00    --  -41.12 125.00-150.00   25
  3  ω    -37.00  -2.00   1.00    1.00    --  -41.12 125.00-180.00   35
  4  ω    -65.00  31.00   1.00    1.00    --  -41.12  57.00 150.00   96
  5  ω   -107.00 -82.00   1.00    1.00    --  -41.12 -57.00   0.00   25
  6  ω     32.00 125.00   1.00    3.95    --  105.32 -30.00 -90.00   93
  7  ω     79.00 172.00   1.00    3.95    --  105.32  30.00-120.00   93
  8  ω    107.00 176.00   1.00    3.95    --  105.32  45.00 -60.00   69
  9  ω    139.00 174.00   1.00    3.95    --  105.32  45.00 -30.00   35
 10  ω     50.00 136.00   1.00    3.95    --  105.32 -77.00 -90.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0710663000
_diffrn_orient_matrix_UB_12      -0.0476003000
_diffrn_orient_matrix_UB_13      0.0996121000
_diffrn_orient_matrix_UB_21      -0.1247566000
_diffrn_orient_matrix_UB_22      -0.0144449000
_diffrn_orient_matrix_UB_23      -0.0918031000
_diffrn_orient_matrix_UB_31      0.0582776000
_diffrn_orient_matrix_UB_32      -0.0890205000
_diffrn_orient_matrix_UB_33      -0.0382224000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2906
_reflns_number_total             3220
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.0058(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0457
_refine_ls_restrained_S_all      1.054
_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)+(0.0721P)²+0.3310P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1233
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Cl1 Cl 0.10485(6) 0.40982(4) 0.53686(7) 0.0590(2) Uani 1 1 d . . . . .
Cl2 Cl 0.23006(6) 0.57227(4) 0.40862(7) 0.0582(2) Uani 1 1 d . . . . .
Cl3 Cl 0.49831(6) 0.54201(4) 0.28592(6) 0.0565(2) Uani 1 1 d . . . . .
S1 S 0.64544(6) 0.17850(5) 0.67064(5) 0.0552(2) Uani 1 1 d . . . . .
N1 N 0.49769(17) 0.21963(12) 0.42801(17) 0.0386(4) Uani 1 1 d . . . . .
C1 C 0.3224(2) 0.10809(16) 0.4429(3) 0.0543(6) Uani 1 1 d . . . . .
H1 H 0.2858 0.1222 0.3643 0.065 Uiso 1 1 calc R . . . .
C2 C 0.2617(3) 0.04501(18) 0.5105(4) 0.0677(8) Uani 1 1 d . . . . .
H2 H 0.1827 0.0178 0.4780 0.081 Uiso 1 1 calc R . . . .
C3 C 0.3176(3) 0.02252(18) 0.6251(4) 0.0740(10) Uani 1 1 d . . . . .
H3 H 0.2753 -0.0193 0.6702 0.089 Uiso 1 1 calc R . . . .
C4 C 0.4357(3) 0.06116(19) 0.6744(3) 0.0630(7) Uani 1 1 d . . . . .
H4 H 0.4744 0.0440 0.7511 0.076 Uiso 1 1 calc R . . . .
C5 C 0.4970(2) 0.12625(15) 0.6085(2) 0.0449(5) Uani 1 1 d . . . . .
C6 C 0.4387(2) 0.15017(13) 0.4937(2) 0.0393(4) Uani 1 1 d . . . . .
C7 C 0.6405(2) 0.21410(13) 0.4268(2) 0.0364(4) Uani 1 1 d . . . . .
C8 C 0.7205(2) 0.19669(14) 0.5343(2) 0.0410(5) Uani 1 1 d . . . . .
C9 C 0.8597(2) 0.19175(18) 0.5344(3) 0.0550(6) Uani 1 1 d . . . . .
H9 H 0.9131 0.1792 0.6064 0.066 Uiso 1 1 calc R . . . .
C10 C 0.9181(3) 0.20560(19) 0.4270(3) 0.0607(7) Uani 1 1 d . . . . .
H10 H 1.0113 0.2048 0.4275 0.073 Uiso 1 1 calc R . . . .
C11 C 0.8388(3) 0.22047(17) 0.3198(3) 0.0550(6) Uani 1 1 d . . . . .
H11 H 0.8785 0.2286 0.2476 0.066 Uiso 1 1 calc R . . . .
C12 C 0.7002(2) 0.22345(16) 0.3184(2) 0.0466(5) Uani 1 1 d . . . . .
H12 H 0.6469 0.2317 0.2451 0.056 Uiso 1 1 calc R . . . .
C13 C 0.4353(2) 0.30356(13) 0.42402(18) 0.0339(4) Uani 1 1 d . . . . .
C14 C 0.3149(2) 0.31622(13) 0.47490(19) 0.0367(4) Uani 1 1 d . . . . .
H14 H 0.2754 0.2692 0.5126 0.044 Uiso 1 1 calc R . . . .
C15 C 0.2533(2) 0.39842(14) 0.46974(19) 0.0383(4) Uani 1 1 d . . . . .
C16 C 0.3075(2) 0.47000(13) 0.4128(2) 0.0391(4) Uani 1 1 d . . . . .
C17 C 0.4263(2) 0.45661(14) 0.36132(19) 0.0386(4) Uani 1 1 d . . . . .
C18 C 0.4916(2) 0.37539(14) 0.36660(19) 0.0373(4) Uani 1 1 d . . . . .
H18 H 0.5724 0.3687 0.3322 0.045 Uiso 1 1 calc R . . . .


_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 C15 1.729(2) . ?
Cl2 C16 1.726(2) . ?
Cl3 C17 1.728(2) . ?
S1 C5 1.758(3) . ?
S1 C8 1.763(2) . ?
N1 C6 1.433(3) . ?
N1 C7 1.431(3) . ?
N1 C13 1.412(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.385(4) . ?
C1 C6 1.392(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.370(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.398(3) . ?
C5 C6 1.385(3) . ?
C7 C8 1.386(3) . ?
C7 C12 1.391(3) . ?
C8 C9 1.392(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.384(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.374(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.389(3) . ?
C13 C18 1.401(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.384(3) . ?
C15 C16 1.386(3) . ?
C16 C17 1.379(3) . ?
C17 C18 1.388(3) . ?
C18 H18 0.9300 . ?

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
C5 S1 C8 98.75(11) . . ?
C7 N1 C6 114.98(16) . . ?
C13 N1 C6 118.07(16) . . ?
C13 N1 C7 119.34(17) . . ?
C2 C1 H1 120.3 . . ?
C2 C1 C6 119.4(3) . . ?
C6 C1 H1 120.3 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.7(3) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 S1 120.7(2) . . ?
C6 C5 S1 120.04(17) . . ?
C6 C5 C4 119.3(2) . . ?
C1 C6 N1 120.0(2) . . ?
C5 C6 N1 119.6(2) . . ?
C5 C6 C1 120.4(2) . . ?
C8 C7 N1 119.68(19) . . ?
C8 C7 C12 119.4(2) . . ?
C12 C7 N1 120.9(2) . . ?
C7 C8 S1 119.83(16) . . ?
C7 C8 C9 120.2(2) . . ?
C9 C8 S1 119.93(19) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.7(3) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.1(2) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C7 C12 H12 120.0 . . ?
C11 C12 C7 120.0(2) . . ?
C11 C12 H12 120.0 . . ?
C14 C13 N1 120.57(18) . . ?
C14 C13 C18 118.51(18) . . ?
C18 C13 N1 120.91(18) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.38(19) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 Cl1 117.90(17) . . ?
C14 C15 C16 121.78(19) . . ?
C16 C15 Cl1 120.32(16) . . ?
C15 C16 Cl2 121.06(16) . . ?
C17 C16 Cl2 121.47(16) . . ?
C17 C16 C15 117.47(18) . . ?
C16 C17 Cl3 120.21(16) . . ?
C16 C17 C18 122.18(19) . . ?
C18 C17 Cl3 117.61(16) . . ?
C13 C18 H18 120.2 . . ?
C17 C18 C13 119.68(19) . . ?
C17 C18 H18 120.2 . . ?

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
Cl1 C15 C16 Cl2 0.7(3) . . . . ?
Cl1 C15 C16 C17 179.83(16) . . . . ?
Cl2 C16 C17 Cl3 -2.2(3) . . . . ?
Cl2 C16 C17 C18 178.33(16) . . . . ?
Cl3 C17 C18 C13 -178.37(15) . . . . ?
S1 C5 C6 N1 -2.0(3) . . . . ?
S1 C5 C6 C1 178.89(18) . . . . ?
S1 C8 C9 C10 179.7(2) . . . . ?
N1 C7 C8 S1 1.7(3) . . . . ?
N1 C7 C8 C9 -179.6(2) . . . . ?
N1 C7 C12 C11 178.1(2) . . . . ?
N1 C13 C14 C15 -179.37(19) . . . . ?
N1 C13 C18 C17 178.37(19) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C2 C1 C6 N1 -176.0(2) . . . . ?
C2 C1 C6 C5 3.1(4) . . . . ?
C2 C3 C4 C5 2.2(5) . . . . ?
C3 C4 C5 S1 178.4(2) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
C4 C5 C6 N1 177.2(2) . . . . ?
C4 C5 C6 C1 -1.9(3) . . . . ?
C5 S1 C8 C7 33.35(19) . . . . ?
C5 S1 C8 C9 -145.35(19) . . . . ?
C6 N1 C7 C8 -46.0(3) . . . . ?
C6 N1 C7 C12 132.1(2) . . . . ?
C6 N1 C13 C14 -4.6(3) . . . . ?
C6 N1 C13 C18 176.77(19) . . . . ?
C6 C1 C2 C3 -1.7(4) . . . . ?
C7 N1 C6 C1 -134.7(2) . . . . ?
C7 N1 C6 C5 46.2(3) . . . . ?
C7 N1 C13 C14 -152.66(19) . . . . ?
C7 N1 C13 C18 28.7(3) . . . . ?
C7 C8 C9 C10 0.9(4) . . . . ?
C8 S1 C5 C4 147.6(2) . . . . ?
C8 S1 C5 C6 -33.2(2) . . . . ?
C8 C7 C12 C11 -3.8(3) . . . . ?
C8 C9 C10 C11 -2.7(4) . . . . ?
C9 C10 C11 C12 1.2(4) . . . . ?
C10 C11 C12 C7 2.0(4) . . . . ?
C12 C7 C8 S1 -176.43(17) . . . . ?
C12 C7 C8 C9 2.3(3) . . . . ?
C13 N1 C6 C1 75.9(3) . . . . ?
C13 N1 C6 C5 -103.2(2) . . . . ?
C13 N1 C7 C8 103.0(2) . . . . ?
C13 N1 C7 C12 -78.9(3) . . . . ?
C13 C14 C15 Cl1 -179.10(16) . . . . ?
C13 C14 C15 C16 1.0(3) . . . . ?
C14 C13 C18 C17 -0.3(3) . . . . ?
C14 C15 C16 Cl2 -179.37(17) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C15 C16 C17 Cl3 178.66(16) . . . . ?
C15 C16 C17 C18 -0.8(3) . . . . ?
C16 C17 C18 C13 1.1(3) . . . . ?
C18 C13 C14 C15 -0.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.294
_oxdiff_exptl_absorpt_empirical_full_min 0.545
####################################################################### 
# 
# 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_cs-cl2-20200110
_database_code_depnum_ccdc_archive 'CCDC 2075006'
loop_
_audit_author_name
_audit_author_address
'Yang Jie'
;Tianjin University
China
;
_audit_update_record             
;
2021-09-27 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;
_audit_creation_date             2021-09-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H11 Cl2 N S'
_chemical_formula_sum            'C18 H11 Cl2 N S'
_chemical_formula_weight         344.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H S N Cl'
_chemical_oxdiff_usercomment     'C H S N Cl'
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'
S S 0.3331 0.5567 '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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   8.10551(13)
_cell_length_b                   18.1086(3)
_cell_length_c                   10.68992(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1569.06(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5781
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.0510
_cell_measurement_theta_min      4.7760
_shelx_estimated_absorpt_T_max   0.640
_shelx_estimated_absorpt_T_min   0.507
_exptl_absorpt_coefficient_mu    4.907
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0120
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10245
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.261
_diffrn_reflns_theta_min         4.804
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1975
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -38.00 -12.00   1.00    1.88    --  -41.12 125.00 -90.00   26
  2  ω    -80.00 -53.00   1.00    1.88    --  -41.12 125.00 -90.00   27
  3  ω   -116.00 -17.00   1.00    1.88    --  -41.12 -37.00 -90.00   99
  4  ω   -115.00 -29.00   1.00    1.88    --  -41.12 -37.00-180.00   86
  5  ω      2.00  49.00   1.00    1.88    --   41.12 -99.00  60.00   47
  6  ω      4.00  72.00   1.00    1.88    --   41.12 -99.00 150.00   68
  7  ω     82.00 177.00   1.00    7.50    --  105.32  30.00 120.00   95
  8  ω     67.00 122.00   1.00    7.50    --  105.32 -30.00 -60.00   55
  9  ω     29.00  67.00   1.00    7.50    --  105.32 -30.00-150.00   38
 10  ω    113.00 170.00   1.00    7.50    --  105.32 125.00 -30.00   57
 11  ω     40.00  66.00   1.00    7.50    --  105.32 -94.00-180.00   26
 12  ω    110.00 169.00   1.00    7.50    --  105.32 125.00 120.00   59
 13  ω     40.00  74.00   1.00    7.50    --  105.32-125.00   0.00   34
 14  ω     41.00 101.00   1.00    7.50    --  105.32 -94.00  60.00   60
 15  ω     95.00 178.00   1.00    7.50    --  105.32 125.00   0.00   83
 16  ω     88.00 117.00   1.00    7.50    --  105.32-125.00   0.00   29
 17  ω    102.00 168.00   1.00    7.50    --  105.32  30.00-180.00   66
 18  ω     75.00 117.00   1.00    7.50    --  105.32-125.00-180.00   42
 19  ω     31.00  82.00   1.00    7.50    --  105.32 -94.00 -60.00   51
 20  ω     39.00 124.00   1.00    7.50    --  105.32 -45.00  60.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1893482000
_diffrn_orient_matrix_UB_12      0.0033816000
_diffrn_orient_matrix_UB_13      -0.0114795000
_diffrn_orient_matrix_UB_21      -0.0063614000
_diffrn_orient_matrix_UB_22      0.0562921000
_diffrn_orient_matrix_UB_23      0.1079321000
_diffrn_orient_matrix_UB_31      0.0156537000
_diffrn_orient_matrix_UB_32      0.0636990000
_diffrn_orient_matrix_UB_33      -0.0947558000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1471
_reflns_number_total             1609
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1609
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0296
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0417P)²+0.4139P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0828
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C8(H8)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
Cl1 Cl 0.03364(5) 0.60160(2) 0.66487(5) 0.06533(16) Uani 1 1 d . . . . .
S1 S 0.46308(7) 0.7500 0.19656(6) 0.06010(18) Uani 1 2 d S T P . .
N1 N 0.5070(2) 0.7500 0.47285(17) 0.0496(4) Uani 1 2 d S T P . .
C1 C 0.6375(2) 0.62803(10) 0.48173(17) 0.0606(4) Uani 1 1 d . . . . .
H1 H 0.6551 0.6341 0.5671 0.073 Uiso 1 1 calc R . . . .
C2 C 0.6860(2) 0.56339(10) 0.4229(2) 0.0692(5) Uani 1 1 d . . . . .
H2 H 0.7336 0.5255 0.4691 0.083 Uiso 1 1 calc R . . . .
C3 C 0.6638(2) 0.55527(10) 0.2962(2) 0.0671(5) Uani 1 1 d . . . . .
H3 H 0.6951 0.5115 0.2574 0.080 Uiso 1 1 calc R . . . .
C4 C 0.5956(2) 0.61132(10) 0.22607(18) 0.0601(4) Uani 1 1 d . . . . .
H4 H 0.5833 0.6058 0.1401 0.072 Uiso 1 1 calc R . . . .
C5 C 0.54495(16) 0.67632(9) 0.28462(15) 0.0486(3) Uani 1 1 d . . . . .
C6 C 0.56273(17) 0.68353(8) 0.41326(15) 0.0477(3) Uani 1 1 d . . . . .
C7 C 0.3535(2) 0.7500 0.53370(17) 0.0423(4) Uani 1 2 d S T P . .
C8 C 0.27644(18) 0.68371(8) 0.56605(13) 0.0457(3) Uani 1 1 d . . . . .
H8 H 0.3257 0.6388 0.5464 0.055 Uiso 1 1 calc R . . . .
C9 C 0.12663(19) 0.68540(8) 0.62733(13) 0.0474(3) Uani 1 1 d . . . . .
C10 C 0.0471(3) 0.7500 0.6597(2) 0.0516(5) Uani 1 2 d S T P . .
H10 H -0.062(3) 0.7500 0.705(2) 0.061(7) Uiso 1 2 d S T P . .


_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 C9 1.7412(15) . ?
S1 C5 1.7626(16) . ?
S1 C5 1.7626(16) 8_575 ?
N1 C6 1.4348(17) 8_575 ?
N1 C6 1.4348(17) . ?
N1 C7 1.404(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.386(3) . ?
C1 C6 1.383(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.378(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.395(2) . ?
C5 C6 1.389(2) . ?
C7 C8 1.3969(17) . ?
C7 C8 1.3969(17) 8_575 ?
C8 H8 0.9300 . ?
C8 C9 1.380(2) . ?
C9 C10 1.3801(19) . ?
C10 C9 1.3800(19) 8_575 ?
C10 H10 1.01(3) . ?

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
C5 S1 C5 98.39(10) 8_575 . ?
C6 N1 C6 114.05(16) 8_575 . ?
C7 N1 C6 118.99(9) . 8_575 ?
C7 N1 C6 118.99(9) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C6 C1 C2 119.84(18) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.05(17) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.68(17) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.70(17) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 S1 120.65(13) . . ?
C6 C5 S1 119.79(12) . . ?
C6 C5 C4 119.55(15) . . ?
C1 C6 N1 120.83(16) . . ?
C1 C6 C5 120.08(14) . . ?
C5 C6 N1 119.06(14) . . ?
C8 C7 N1 120.74(9) 8_575 . ?
C8 C7 N1 120.74(9) . . ?
C8 C7 C8 118.50(18) . 8_575 ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.48(14) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 Cl1 118.10(12) . . ?
C8 C9 C10 123.31(14) . . ?
C10 C9 Cl1 118.59(12) . . ?
C9 C10 C9 115.92(19) 8_575 . ?
C9 C10 H10 122.04(10) . . ?
C9 C10 H10 122.04(9) 8_575 . ?

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
Cl1 C9 C10 C9 -179.88(10) . . . 8_575 ?
S1 C5 C6 N1 2.73(19) . . . . ?
S1 C5 C6 C1 -175.46(12) . . . . ?
N1 C7 C8 C9 179.13(16) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C2 C1 C6 N1 178.12(16) . . . . ?
C2 C1 C6 C5 -3.7(2) . . . . ?
C2 C3 C4 C5 -1.5(3) . . . . ?
C3 C4 C5 S1 178.06(13) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C4 C5 C6 N1 -178.68(14) . . . . ?
C4 C5 C6 C1 3.1(2) . . . . ?
C5 S1 C5 C4 -144.55(10) 8_575 . . . ?
C5 S1 C5 C6 34.03(15) 8_575 . . . ?
C6 N1 C6 C1 129.40(16) 8_575 . . . ?
C6 N1 C6 C5 -48.8(2) 8_575 . . . ?
C6 N1 C7 C8 17.2(3) . . . . ?
C6 N1 C7 C8 -17.2(3) 8_575 . . 8_575 ?
C6 N1 C7 C8 -164.37(16) . . . 8_575 ?
C6 N1 C7 C8 164.37(16) 8_575 . . . ?
C6 C1 C2 C3 1.7(3) . . . . ?
C7 N1 C6 C1 -81.9(2) . . . . ?
C7 N1 C6 C5 99.90(18) . . . . ?
C7 C8 C9 Cl1 179.47(13) . . . . ?
C7 C8 C9 C10 -0.3(2) . . . . ?
C8 C7 C8 C9 0.7(3) 8_575 . . . ?
C8 C9 C10 C9 -0.1(3) . . . 8_575 ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.096
_oxdiff_exptl_absorpt_empirical_full_min 0.887
####################################################################### 
# 
# 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_cs-cl3-ch2cl2-pe-2020-01-10
_database_code_depnum_ccdc_archive 'CCDC 2075011'
loop_
_audit_author_name
_audit_author_address
'Yang Jie'
;Tianjin University
China
;
_audit_update_record             
;
2021-09-27 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;
_audit_creation_date             2021-09-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H10 Cl3 N S'
_chemical_formula_sum            'C18 H10 Cl3 N S'
_chemical_formula_weight         378.68
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H S N Cl'
_chemical_oxdiff_usercomment     'C H S N Cl'
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'
S S 0.3331 0.5567 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   17.3207(4)
_cell_length_b                   15.5108(3)
_cell_length_c                   12.5458(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.208(2)
_cell_angle_gamma                90
_cell_volume                     3252.49(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6688
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.2350
_cell_measurement_theta_min      3.6290
_shelx_estimated_absorpt_T_max   0.573
_shelx_estimated_absorpt_T_min   0.453
_exptl_absorpt_coefficient_mu    6.269
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42005
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10863
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.624
_diffrn_reflns_theta_min         3.888
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1975
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -128.00  46.00   1.00    3.22    --  -40.87   0.00 -30.00  174
  2  ω    -22.00   6.00   1.00    3.22    --  -40.87  37.00   0.00   28
  3  ω     35.00  77.00   1.00    3.22    --   40.87-125.00  30.00   42
  4  ω     16.00  63.00   1.00    3.22    --   40.87 -99.00-120.00   47
  5  ω     28.00  87.00   1.00    3.22    --   40.87-125.00 150.00   59
  6  ω    105.00 137.00   1.00   12.90    --  105.32 125.00-150.00   32
  7  ω     39.00 115.00   1.00   12.90    --  105.32 -61.00-180.00   76
  8  ω     39.00 138.00   1.00   12.90    --  105.32 -77.00 -60.00   99
  9  ω     95.00 138.00   1.00   12.90    --  105.32 125.00  60.00   43
 10  ω     33.00 130.00   1.00   12.90    --  105.32 -45.00  60.00   97
 11  ω     88.00 147.00   1.00   12.90    --  105.32  45.00 150.00   59
 12  ω     76.00 116.00   1.00   12.90    --  105.32-125.00 -60.00   40
 13  ω     29.00 134.00   1.00   12.90    --  105.32 -30.00 -90.00  105
 14  ω    113.00 141.00   1.00   12.90    --  105.32 125.00-180.00   28
 15  ω     66.00 117.00   1.00   12.90    --  105.32-125.00 120.00   51
 16  ω     38.00 157.00   1.00   12.90    --  105.32 -15.00 120.00  119
 17  ω     61.00 104.00   1.00   12.90    --  105.32 -94.00 150.00   43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0378677000
_diffrn_orient_matrix_UB_12      0.0330399000
_diffrn_orient_matrix_UB_13      0.0904545000
_diffrn_orient_matrix_UB_21      0.0380069000
_diffrn_orient_matrix_UB_22      -0.0757866000
_diffrn_orient_matrix_UB_23      0.0749650000
_diffrn_orient_matrix_UB_31      0.0749880000
_diffrn_orient_matrix_UB_32      0.0550560000
_diffrn_orient_matrix_UB_33      0.0488081000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2979
_reflns_number_total             3230
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0533P)²+2.9938P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1011
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Cl1 Cl 0.51801(4) 0.90204(4) 0.58438(6) 0.06502(19) Uani 1 1 d . . . . .
Cl2 Cl 0.38292(3) 0.78280(4) 0.62538(5) 0.06017(18) Uani 1 1 d . . . . .
Cl3 Cl 0.40669(3) 0.58097(4) 0.62424(5) 0.05915(18) Uani 1 1 d . . . . .
S1 S 0.80205(3) 0.51242(4) 0.49074(4) 0.04783(15) Uani 1 1 d . . . . .
N1 N 0.67227(9) 0.62978(11) 0.53044(12) 0.0372(3) Uani 1 1 d . . . . .
C1 C 0.74854(13) 0.66677(14) 0.71838(17) 0.0464(5) Uani 1 1 d . . . . .
H1 H 0.7051 0.6977 0.7289 0.056 Uiso 1 1 calc R . . . .
C2 C 0.81795(16) 0.66083(17) 0.80347(18) 0.0574(6) Uani 1 1 d . . . . .
H2 H 0.8199 0.6863 0.8713 0.069 Uiso 1 1 calc R . . . .
C3 C 0.88407(15) 0.61781(17) 0.78916(19) 0.0591(6) Uani 1 1 d . . . . .
H3 H 0.9310 0.6157 0.8460 0.071 Uiso 1 1 calc R . . . .
C4 C 0.87993(13) 0.57802(15) 0.68987(19) 0.0509(5) Uani 1 1 d . . . . .
H4 H 0.9246 0.5498 0.6791 0.061 Uiso 1 1 calc R . . . .
C5 C 0.80949(11) 0.57967(12) 0.60538(15) 0.0376(4) Uani 1 1 d . . . . .
C6 C 0.74321(11) 0.62694(12) 0.61743(14) 0.0350(4) Uani 1 1 d . . . . .
C7 C 0.67370(11) 0.62150(12) 0.41858(14) 0.0348(4) Uani 1 1 d . . . . .
C8 C 0.73329(11) 0.57265(12) 0.39051(15) 0.0378(4) Uani 1 1 d . . . . .
C9 C 0.73496(14) 0.56447(15) 0.28107(18) 0.0510(5) Uani 1 1 d . . . . .
H9 H 0.7768 0.5348 0.2639 0.061 Uiso 1 1 calc R . . . .
C10 C 0.67540(17) 0.59972(17) 0.19752(18) 0.0598(6) Uani 1 1 d . . . . .
H10 H 0.6760 0.5925 0.1242 0.072 Uiso 1 1 calc R . . . .
C11 C 0.61516(15) 0.64561(18) 0.22361(18) 0.0588(6) Uani 1 1 d . . . . .
H11 H 0.5742 0.6685 0.1674 0.071 Uiso 1 1 calc R . . . .
C12 C 0.61473(13) 0.65819(15) 0.33316(17) 0.0482(5) Uani 1 1 d . . . . .
H12 H 0.5747 0.6914 0.3496 0.058 Uiso 1 1 calc R . . . .
C13 C 0.60288(10) 0.66823(12) 0.55344(14) 0.0345(4) Uani 1 1 d . . . . .
C14 C 0.59376(12) 0.75697(12) 0.55496(16) 0.0396(4) Uani 1 1 d . . . . .
H14 H 0.6326 0.7931 0.5401 0.048 Uiso 1 1 calc R . . . .
C15 C 0.52657(12) 0.79140(12) 0.57867(15) 0.0387(4) Uani 1 1 d . . . . .
C16 C 0.46725(11) 0.73830(13) 0.59903(14) 0.0375(4) Uani 1 1 d . . . . .
C17 C 0.47766(11) 0.64983(13) 0.59754(14) 0.0370(4) Uani 1 1 d . . . . .
C18 C 0.54534(11) 0.61433(12) 0.57530(14) 0.0368(4) Uani 1 1 d . . . . .
H18 H 0.5519 0.5548 0.5751 0.044 Uiso 1 1 calc R . . . .


_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 C15 1.726(2) . ?
Cl2 C16 1.7240(18) . ?
Cl3 C17 1.7264(18) . ?
S1 C5 1.754(2) . ?
S1 C8 1.757(2) . ?
N1 C6 1.414(2) . ?
N1 C7 1.416(2) . ?
N1 C13 1.437(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.386(3) . ?
C1 C6 1.390(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.391(3) . ?
C5 C6 1.403(3) . ?
C7 C8 1.398(3) . ?
C7 C12 1.393(3) . ?
C8 C9 1.387(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.376(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.372(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.390(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.386(3) . ?
C13 C18 1.382(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.382(3) . ?
C15 C16 1.392(3) . ?
C16 C17 1.385(3) . ?
C17 C18 1.388(3) . ?
C18 H18 0.9300 . ?

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
C5 S1 C8 99.26(9) . . ?
C6 N1 C7 121.64(15) . . ?
C6 N1 C13 117.46(15) . . ?
C7 N1 C13 118.02(15) . . ?
C2 C1 H1 119.7 . . ?
C2 C1 C6 120.6(2) . . ?
C6 C1 H1 119.7 . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.0(2) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.2(2) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.6(2) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 S1 118.37(16) . . ?
C4 C5 C6 120.42(19) . . ?
C6 C5 S1 120.86(15) . . ?
C1 C6 N1 121.73(17) . . ?
C1 C6 C5 118.01(18) . . ?
C5 C6 N1 120.19(16) . . ?
C8 C7 N1 120.33(17) . . ?
C12 C7 N1 121.69(17) . . ?
C12 C7 C8 117.93(17) . . ?
C7 C8 S1 120.97(14) . . ?
C9 C8 S1 118.27(16) . . ?
C9 C8 C7 120.51(19) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.3(2) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.7(2) . . ?
C12 C11 H11 119.7 . . ?
C7 C12 H12 119.7 . . ?
C11 C12 C7 120.7(2) . . ?
C11 C12 H12 119.7 . . ?
C14 C13 N1 121.28(16) . . ?
C18 C13 N1 118.25(16) . . ?
C18 C13 C14 120.47(17) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.48(17) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 Cl1 118.66(15) . . ?
C14 C15 C16 120.98(18) . . ?
C16 C15 Cl1 120.36(15) . . ?
C15 C16 Cl2 120.11(16) . . ?
C17 C16 Cl2 121.28(15) . . ?
C17 C16 C15 118.61(16) . . ?
C16 C17 Cl3 120.56(15) . . ?
C16 C17 C18 121.04(16) . . ?
C18 C17 Cl3 118.39(15) . . ?
C13 C18 C17 119.40(17) . . ?
C13 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?

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
Cl1 C15 C16 Cl2 2.3(2) . . . . ?
Cl1 C15 C16 C17 -177.73(14) . . . . ?
Cl2 C16 C17 Cl3 -1.0(2) . . . . ?
Cl2 C16 C17 C18 179.42(14) . . . . ?
Cl3 C17 C18 C13 179.85(14) . . . . ?
S1 C5 C6 N1 -8.2(2) . . . . ?
S1 C5 C6 C1 168.82(15) . . . . ?
S1 C8 C9 C10 170.29(19) . . . . ?
N1 C7 C8 S1 5.9(2) . . . . ?
N1 C7 C8 C9 -179.92(18) . . . . ?
N1 C7 C12 C11 -176.8(2) . . . . ?
N1 C13 C14 C15 -179.27(17) . . . . ?
N1 C13 C18 C17 -179.86(16) . . . . ?
C1 C2 C3 C4 -2.0(4) . . . . ?
C2 C1 C6 N1 178.0(2) . . . . ?
C2 C1 C6 C5 1.1(3) . . . . ?
C2 C3 C4 C5 -1.2(4) . . . . ?
C3 C4 C5 S1 -168.86(19) . . . . ?
C3 C4 C5 C6 4.4(3) . . . . ?
C4 C5 C6 N1 178.75(18) . . . . ?
C4 C5 C6 C1 -4.2(3) . . . . ?
C5 S1 C8 C7 -32.78(17) . . . . ?
C5 S1 C8 C9 152.94(17) . . . . ?
C6 N1 C7 C8 29.9(3) . . . . ?
C6 N1 C7 C12 -152.77(19) . . . . ?
C6 N1 C13 C14 79.4(2) . . . . ?
C6 N1 C13 C18 -100.0(2) . . . . ?
C6 C1 C2 C3 2.1(4) . . . . ?
C7 N1 C6 C1 154.41(18) . . . . ?
C7 N1 C6 C5 -28.7(3) . . . . ?
C7 N1 C13 C14 -81.7(2) . . . . ?
C7 N1 C13 C18 98.9(2) . . . . ?
C7 C8 C9 C10 -4.0(3) . . . . ?
C8 S1 C5 C4 -152.92(16) . . . . ?
C8 S1 C5 C6 33.89(16) . . . . ?
C8 C7 C12 C11 0.6(3) . . . . ?
C8 C9 C10 C11 2.0(4) . . . . ?
C9 C10 C11 C12 1.3(4) . . . . ?
C10 C11 C12 C7 -2.6(4) . . . . ?
C12 C7 C8 S1 -171.48(16) . . . . ?
C12 C7 C8 C9 2.7(3) . . . . ?
C13 N1 C6 C1 -6.0(3) . . . . ?
C13 N1 C6 C5 170.94(16) . . . . ?
C13 N1 C7 C8 -169.80(16) . . . . ?
C13 N1 C7 C12 7.5(3) . . . . ?
C13 C14 C15 Cl1 177.99(15) . . . . ?
C13 C14 C15 C16 -1.2(3) . . . . ?
C14 C13 C18 C17 0.8(3) . . . . ?
C14 C15 C16 Cl2 -178.55(15) . . . . ?
C14 C15 C16 C17 1.4(3) . . . . ?
C15 C16 C17 Cl3 179.04(14) . . . . ?
C15 C16 C17 C18 -0.6(3) . . . . ?
C16 C17 C18 C13 -0.5(3) . . . . ?
C18 C13 C14 C15 0.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.342
_oxdiff_exptl_absorpt_empirical_full_min 0.572
