# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_serc233-r1-rf
_database_code_depnum_ccdc_archive 'CCDC 2101061'
loop_
_audit_author_name
_audit_author_address
'Andryj M Borys'
;University of Kent
United Kingdom
;
_audit_update_record             
;
2021-08-03 deposited with the CCDC.	2021-11-23 downloaded from the CCDC.
;
_audit_creation_date             2018-06-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H9.96 Cl4.04 N2 S'
_chemical_formula_sum            'C15 H9.97 Cl4.03 N2 S'
_chemical_formula_weight         393.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'S1 N2 Cl4 C15 H20'
_chemical_oxdiff_usercomment     ABS-416
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3043(3)
_cell_length_b                   9.0923(3)
_cell_length_c                   12.6109(5)
_cell_angle_alpha                80.349(3)
_cell_angle_beta                 86.679(3)
_cell_angle_gamma                72.338(3)
_cell_volume                     786.73(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10009
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      75.6800
_cell_measurement_theta_min      5.1490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.097
_exptl_absorpt_correction_T_max  0.689
_exptl_absorpt_correction_T_min  0.272
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light orange'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             397
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 0 -1 0.1074
0 -5 1 0.0704
-4 0 1 0.1173
0 5 -1 0.0614
0 -1 8 0.0074
-5 -1 -1 0.1248
0 1 -8 0.0435

_exptl_crystal_size_max          0.267
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.053
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4.4266 -0.0859 -1.3739 0.0890 0.2541 0.9631
-0.1838 -5.4382 1.1326 0.3326 0.9411 -0.0604
-4.4747 -0.1708 1.4397 -0.0740 -0.2118 -0.9745
0.1511 5.4303 -1.1208 -0.3327 -0.9415 0.0533
-0.0046 -0.6786 7.8555 0.9648 0.0763 -0.2517
-4.7190 -1.2522 -0.5368 -0.2828 -0.0235 -0.9589
-0.0666 0.6593 -7.8588 -0.9685 -0.0766 0.2371

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15042
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.583
_diffrn_reflns_theta_min         3.555
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2887
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -20.00   1.00    1.00    --  -42.45 -38.00  60.00   95
  2  ω    -79.00  36.00   1.00    1.00    --  -42.45  19.00-120.00  115
  3  ω      1.00  82.00   1.00    1.00    --   42.45 -99.00 -60.00   81
  4  ω     23.00  97.00   1.00    1.00    --   42.45-125.00  30.00   74
  5  ω     23.00  97.00   1.00    1.00    --   42.45-125.00 -90.00   74
  6  ω     30.00 109.00   1.00    2.50    --  111.00 -94.00-150.00   79
  7  ω    100.00 178.00   1.00    2.50    --  111.00 111.00-150.00   78
  8  ω    100.00 178.00   1.00    2.50    --  111.00 111.00 -60.00   78
  9  ω     36.00 116.00   1.00    2.50    --  111.00-111.00 -30.00   80
 10  ω     36.00 116.00   1.00    2.50    --  111.00-111.00-180.00   80
 11  ω     37.00 142.00   1.00    2.50    --  111.00 -77.00   0.00  105
 12  ω     30.00 109.00   1.00    2.50    --  111.00 -94.00  60.00   79
 13  ω     40.00 135.00   1.00    2.50    --  111.00 -45.00  30.00   95
 14  ω     41.00 139.00   1.00    2.50    --  111.00 -61.00 -60.00   98
 15  ω     36.00 135.00   1.00    2.50    --  111.00 -30.00-180.00   99
 16  ω     83.00 178.00   1.00    2.50    --  111.00  61.00   0.00   95
 17  ω     37.00 142.00   1.00    2.50    --  111.00 -77.00-120.00  105
 18  ω     36.00 116.00   1.00    2.50    --  111.00-111.00   0.00   80
 19  ω     66.00 178.00   1.00    2.50    --  111.00  15.00  90.00  112
 20  ω     66.00 178.00   1.00    2.50    --  111.00  15.00-180.00  112
 21  ω     36.00 116.00   1.00    2.50    --  111.00-111.00  90.00   80
 22  ω     37.00 142.00   1.00    2.50    --  111.00 -77.00 120.00  105
 23  ω   -116.00 -11.00   1.00    1.00    --  -42.45 -77.00  90.00  105
 24  ω    -65.00  30.00   1.00    1.00    --  -42.45  38.00 120.00   95
 25  ω   -113.00 -16.00   1.00    1.00    --  -42.45 -57.00-120.00   97
 26  ω   -116.00 -11.00   1.00    1.00    --  -42.45 -77.00   0.00  105
 27  ω   -113.00 -16.00   1.00    1.00    --  -42.45 -57.00 150.00   97
 28  ω     87.00 178.00   1.00    2.50    --  111.00  45.00-150.00   91
 29  ω     83.00 178.00   1.00    2.50    --  111.00  61.00 120.00   95
 30  ω     66.00 178.00   1.00    2.50    --  111.00  15.00 -60.00  112
 31  ω     80.00 178.00   1.00    2.50    --  111.00  77.00 -90.00   98
 32  ω     80.00 178.00   1.00    2.50    --  111.00  77.00  60.00   98
 33  ω     80.00 178.00   1.00    2.50    --  111.00  77.00 150.00   98
 34  ω     83.00 178.00   1.00    2.50    --  111.00  61.00-120.00   95
 35  ω     80.00 178.00   1.00    2.50    --  111.00  77.00 -60.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0564637000
_diffrn_orient_matrix_UB_12      -0.0381698000
_diffrn_orient_matrix_UB_13      0.1195522000
_diffrn_orient_matrix_UB_21      0.0522881000
_diffrn_orient_matrix_UB_22      -0.1759623000
_diffrn_orient_matrix_UB_23      -0.0054536000
_diffrn_orient_matrix_UB_31      0.2075418000
_diffrn_orient_matrix_UB_32      -0.0025932000
_diffrn_orient_matrix_UB_33      -0.0321446000
_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                2792
_reflns_number_total             2891
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.290
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2891
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0360
_refine_ls_restrained_S_all      1.028
_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)+(0.0510P)²+0.9320P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.0950
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(H6)=1-FVAR(1)
 Sof(Cl5)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
3.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C15(H15), C14(H14), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   mixed
_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
Cl1 Cl 0.57693(8) 0.17027(6) 0.30395(5) 0.02765(15) Uani 1 1 d . . . . .
S1 S 0.25880(7) 0.32302(6) 0.32368(4) 0.02161(15) Uani 1 1 d . . . . .
Cl4 Cl 0.35933(9) 0.73701(7) -0.01306(4) 0.03141(16) Uani 1 1 d . . . . .
Cl3 Cl 0.14340(10) 1.08070(7) 0.08552(5) 0.03858(18) Uani 1 1 d . . . . .
Cl2 Cl 0.07679(9) 1.01780(6) 0.36710(5) 0.03238(16) Uani 1 1 d . . . . .
N2 N 0.2749(2) 0.5659(2) 0.45646(15) 0.0204(4) Uani 1 1 d . . . . .
N1 N 0.2149(3) 0.3224(2) 0.44633(16) 0.0236(4) Uani 1 1 d . . . . .
C2 C 0.2905(3) 0.6037(2) 0.34713(18) 0.0198(4) Uani 1 1 d . . . . .
C1 C 0.2407(3) 0.4352(2) 0.49965(18) 0.0202(4) Uani 1 1 d . . . . .
C6 C 0.3081(3) 0.5440(3) 0.16325(19) 0.0228(5) Uani 1 1 d . . . . .
H6 H 0.307(4) 0.471(4) 0.118(3) 0.027 Uiso 0.965(4) 1 d R . P A 1
C3 C 0.3110(3) 0.7537(2) 0.30430(18) 0.0217(4) Uani 1 1 d . . . . .
C4 C 0.3329(3) 0.7948(2) 0.19436(18) 0.0226(4) Uani 1 1 d . . . . .
C10 C 0.2172(3) 0.4045(2) 0.61776(18) 0.0218(4) Uani 1 1 d . . . . .
C7 C 0.2888(3) 0.5034(2) 0.27380(18) 0.0210(4) Uani 1 1 d . . . . .
C11 C 0.2192(3) 0.5188(3) 0.67951(18) 0.0228(5) Uani 1 1 d . . . . .
H11 H 0.234835 0.613438 0.645839 0.027 Uiso 1 1 calc R . . . .
C15 C 0.1920(3) 0.2632(3) 0.66961(19) 0.0239(5) Uani 1 1 d . . . . .
H15 H 0.189221 0.186841 0.629533 0.029 Uiso 1 1 calc R . . . .
C14 C 0.1712(3) 0.2366(3) 0.7807(2) 0.0279(5) Uani 1 1 d . . . . .
H14 H 0.155013 0.142374 0.814712 0.033 Uiso 1 1 calc R . . . .
C12 C 0.1981(3) 0.4918(3) 0.78986(19) 0.0264(5) Uani 1 1 d . . . . .
H12 H 0.199750 0.568148 0.830183 0.032 Uiso 1 1 calc R . . . .
C5 C 0.3316(3) 0.6872(3) 0.12490(18) 0.0240(5) Uani 1 1 d . . . . .
C8 C 0.3035(4) 0.8652(3) 0.38173(18) 0.0263(5) Uani 1 1 d . . . . .
H8A H 0.408468 0.910423 0.366728 0.032 Uiso 1 1 calc R . . . .
H8B H 0.316580 0.809603 0.454908 0.032 Uiso 1 1 calc R . . . .
C13 C 0.1743(3) 0.3503(3) 0.84121(19) 0.0280(5) Uani 1 1 d . . . . .
H13 H 0.160617 0.332098 0.915617 0.034 Uiso 1 1 calc R . . . .
C9 C 0.3624(4) 0.9498(3) 0.14637(19) 0.0293(5) Uani 1 1 d . . . . .
H9A H 0.463918 0.933773 0.092556 0.035 Uiso 1 1 calc R . . . .
H9B H 0.401059 0.995610 0.202166 0.035 Uiso 1 1 calc R . . . .
Cl5 Cl 0.250(2) 0.4320(19) 0.0836(13) 0.027(7) Uani 0.035(4) 1 d . . P A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 S1 2.3412(7) . ?
S1 N1 1.561(2) . ?
S1 C7 1.729(2) . ?
Cl4 C5 1.739(2) . ?
Cl3 C9 1.801(3) . ?
Cl2 C8 1.804(2) . ?
N2 C2 1.371(3) . ?
N2 C1 1.311(3) . ?
N1 C1 1.379(3) . ?
C2 C3 1.430(3) . ?
C2 C7 1.406(3) . ?
C1 C10 1.479(3) . ?
C6 H6 0.95(4) . ?
C6 C7 1.391(3) . ?
C6 C5 1.368(3) . ?
C6 Cl5 1.698(16) . ?
C3 C4 1.387(3) . ?
C3 C8 1.509(3) . ?
C4 C5 1.421(3) . ?
C4 C9 1.510(3) . ?
C10 C11 1.403(3) . ?
C10 C15 1.400(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.380(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.388(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.390(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.396(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C13 H13 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?

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
N1 S1 Cl1 108.14(7) . . ?
N1 S1 C7 106.24(10) . . ?
C7 S1 Cl1 97.94(7) . . ?
C1 N2 C2 120.96(18) . . ?
C1 N1 S1 122.09(16) . . ?
N2 C2 C3 118.35(18) . . ?
N2 C2 C7 124.10(19) . . ?
C7 C2 C3 117.5(2) . . ?
N2 C1 N1 127.1(2) . . ?
N2 C1 C10 118.33(19) . . ?
N1 C1 C10 114.55(19) . . ?
C7 C6 H6 119.1(18) . . ?
C7 C6 Cl5 117.1(6) . . ?
C5 C6 H6 122.6(18) . . ?
C5 C6 C7 118.3(2) . . ?
C5 C6 Cl5 123.1(6) . . ?
Cl5 C6 H6 13.2(19) . . ?
C2 C3 C8 118.00(19) . . ?
C4 C3 C2 120.20(19) . . ?
C4 C3 C8 121.78(19) . . ?
C3 C4 C5 119.3(2) . . ?
C3 C4 C9 121.8(2) . . ?
C5 C4 C9 118.9(2) . . ?
C11 C10 C1 119.70(19) . . ?
C15 C10 C1 121.2(2) . . ?
C15 C10 C11 119.1(2) . . ?
C2 C7 S1 118.29(17) . . ?
C6 C7 S1 118.90(17) . . ?
C6 C7 C2 122.8(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C15 H15 119.9 . . ?
C14 C15 C10 120.2(2) . . ?
C14 C15 H15 119.9 . . ?
C15 C14 H14 119.8 . . ?
C15 C14 C13 120.3(2) . . ?
C13 C14 H14 119.8 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.3(2) . . ?
C13 C12 H12 119.9 . . ?
C6 C5 Cl4 118.36(17) . . ?
C6 C5 C4 121.9(2) . . ?
C4 C5 Cl4 119.75(17) . . ?
Cl2 C8 H8A 109.9 . . ?
Cl2 C8 H8B 109.9 . . ?
C3 C8 Cl2 109.03(15) . . ?
C3 C8 H8A 109.9 . . ?
C3 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
C14 C13 C12 119.7(2) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
Cl3 C9 H9A 109.6 . . ?
Cl3 C9 H9B 109.6 . . ?
C4 C9 Cl3 110.11(17) . . ?
C4 C9 H9A 109.6 . . ?
C4 C9 H9B 109.6 . . ?
H9A C9 H9B 108.2 . . ?


_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 1.482
_oxdiff_exptl_absorpt_empirical_full_min 0.714


# start Validation Reply Form
_vrf_DIFMX02_serc233-r1-rf       
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*0.75
RESPONSE: The maximum residual electron density is located 0.616 Angstroms
from H9B. This is atributed to a very small percentage of partial 
chlorination at this position.
;
_vrf_PLAT041_serc233-r1-rf       
;
PROBLEM: Calc. and Reported SumFormula    Strings  Differ     Please Check
RESPONSE: Partial chlorination at C6 results in non-integer values of H
and Cl atoms in the calculated sum formula.
;
_vrf_PLAT094_serc233-r1-rf       
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       2.63 Report
RESPONSE: This is attributed to minor partial chlorination at various
positions that can not be explicity modelled. 
;
_vrf_PLAT097_serc233-r1-rf       
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.29 eA-3  
RESPONSE: This is attributed to minor partial chlorination at various
positions that can not be explicity modelled. 
;
_vrf_PLAT431_serc233-r1-rf       
;
PROBLEM: Short Inter HL..A Contact  Cl2      ..S1               3.38 Ang.  
RESPONSE: Weak intermolecular contacts between S1 and Cl2 of  the 
neighbouring molecule.
;
_vrf_PLAT779_serc233-r1-rf       
;
PROBLEM: Suspect or Irrelevant (Bond) Angle in CIF
RESPONSE: Partial occupancy of Cl5 at C6.
;

# end Validation Reply Form
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_serc027-r1-rf
_database_code_depnum_ccdc_archive 'CCDC 2101062'
loop_
_audit_author_name
_audit_author_address
'Andryj M Borys'
;University of Kent
United Kingdom
;
_audit_update_record             
;
2021-08-03 deposited with the CCDC.	2021-11-23 downloaded from the CCDC.
;
_audit_creation_date             2017-08-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H8 Cl4 N2 O S'
_chemical_formula_sum            'C14 H8 Cl4 N2 O S'
_chemical_formula_weight         394.08
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 N2 S1 Cl4 O1 H8'
_chemical_oxdiff_usercomment     ABS-092
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_symmetry_space_group_name_H-M_alt 'P -1'
_cell_length_a                   7.10603(16)
_cell_length_b                   7.22142(17)
_cell_length_c                   15.6955(4)
_cell_angle_alpha                83.2406(19)
_cell_angle_beta                 78.4301(19)
_cell_angle_gamma                71.106(2)
_cell_volume                     745.33(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10470
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.0600
_cell_measurement_theta_min      2.8610
_cell_oxdiff_angle_alpha         83.2406(19)
_cell_oxdiff_angle_beta          78.4301(19)
_cell_oxdiff_angle_gamma         71.106(2)
_cell_oxdiff_length_a            7.10603(16)
_cell_oxdiff_length_b            7.22142(17)
_cell_oxdiff_length_c            15.6955(4)
_cell_oxdiff_measurement_reflns_used 10470
_cell_oxdiff_volume              745.33(3)
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.544
_exptl_absorpt_correction_T_max  0.559
_exptl_absorpt_correction_T_min  0.202
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orangish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             396
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 -4 2 0.0577
-1 0 -10 0.1058
3 4 -3 0.0560
3 4 6 0.0552
0 -1 10 0.0593
-2 2 -6 0.0671
-4 0 -6 0.1113
-3 -4 -4 0.1053
-3 -3 4 0.0809
-2 -1 8 0.0771
2 4 5 0.0787
3 4 -2 0.0498
2 0 -9 0.0650

_exptl_crystal_size_max          0.367
_exptl_crystal_size_mid          0.197
_exptl_crystal_size_min          0.115
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.8792 -3.9380 2.2733 -0.0420 0.2344 0.9712
-0.6683 -0.0664 -10.1302 0.1821 -0.9793 -0.0884
2.8085 3.8775 -2.6734 0.0492 -0.2728 -0.9608
3.2198 3.7627 5.5178 -0.0981 0.5196 -0.8487
-0.0388 -0.8203 9.6774 -0.1742 0.9388 0.2972
-2.2690 2.1192 -6.4524 -0.5947 -0.7766 -0.2079
-3.8308 -0.0360 -6.3607 -0.5799 -0.7563 0.3029
-2.5565 -4.3677 -4.0367 0.2820 -0.3313 0.9004
-3.2250 -3.1410 3.6830 -0.2790 0.3246 0.9038
-2.1076 -0.5585 7.9424 -0.5828 0.6805 0.4442
2.1752 4.2217 5.3069 -0.3753 0.4403 -0.8156
3.2966 3.7354 -1.8211 0.1446 -0.1673 -0.9752
1.5991 -0.2629 -8.5699 0.6261 -0.7315 -0.2698

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14538
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.255
_diffrn_reflns_theta_min         2.878
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2887
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -16.00   1.00    1.00    --  -40.37 -38.00-150.00   99
  2  ω    -73.00  36.00   1.00    1.00    --  -40.37  77.00 -30.00  109
  3  ω   -115.00 -16.00   1.00    1.00    --  -40.37 -38.00 120.00   99
  4  ω      1.00  81.00   1.00    1.00    --   40.37 -99.00  90.00   80
  5  ω      1.00  81.00   1.00    1.00    --   40.37 -99.00  60.00   80
  6  ω     23.00  96.00   1.00    1.00    --   40.37-125.00-150.00   73
  7  ω     29.00 109.00   1.00    1.00    --  112.00 -94.00  60.00   80
  8  ω     86.00 178.00   1.00    1.00    --  112.00  45.00 -60.00   92
  9  ω     86.00 178.00   1.00    1.00    --  112.00  45.00-180.00   92
 10  ω     86.00 178.00   1.00    1.00    --  112.00  45.00-150.00   92
 11  ω     36.00 116.00   1.00    1.00    --  112.00-111.00 -90.00   80
 12  ω     36.00 145.00   1.00    1.00    --  112.00 -77.00 120.00  109
 13  ω    100.00 178.00   1.00    1.00    --  112.00 111.00 120.00   78
 14  ω     36.00 116.00   1.00    1.00    --  112.00-111.00 120.00   80
 15  ω     40.00 141.00   1.00    1.00    --  112.00 -61.00-120.00  101
 16  ω    100.00 178.00   1.00    1.00    --  112.00 111.00 150.00   78
 17  ω     36.00 116.00   1.00    1.00    --  112.00-111.00   0.00   80
 18  ω     37.00 117.00   1.00    1.00    --  112.00-115.00-117.00   80
 19  ω     29.00 109.00   1.00    1.00    --  112.00 -94.00 -90.00   80
 20  ω     79.00 178.00   1.00    1.00    --  112.00  77.00-120.00   99
 21  ω   -115.00 -16.00   1.00    1.00    --  -40.37 -38.00 -60.00   99
 22  ω   -117.00  -8.00   1.00    1.00    --  -40.37 -77.00  90.00  109
 23  ω    -34.00  65.00   1.00    1.00    --   40.37 -38.00-150.00   99
 24  ω      8.00 117.00   1.00    1.00    --   40.37  77.00 -90.00  109
 25  ω      8.00 117.00   1.00    1.00    --   40.37  77.00   0.00  109
 26  ω      4.00  33.00   1.00    1.00    --   40.37  88.00-158.51   29
 27  ω     59.00 178.00   1.00    1.00    --  112.00  15.00  90.00  119
 28  ω     79.00 178.00   1.00    1.00    --  112.00  77.00   0.00   99
 29  ω     79.00 178.00   1.00    1.00    --  112.00  77.00 120.00   99
 30  ω     79.00 178.00   1.00    1.00    --  112.00  77.00 -60.00   99
 31  ω     79.00 178.00   1.00    1.00    --  112.00  77.00  60.00   99
 32  ω     86.00 178.00   1.00    1.00    --  112.00  45.00 120.00   92
 33  ω     79.00 178.00   1.00    1.00    --  112.00  77.00-150.00   99
 34  ω     79.00 178.00   1.00    1.00    --  112.00  77.00  30.00   99
 35  ω     83.00 178.00   1.00    1.00    --  112.00  61.00  90.00   95
 36  ω     83.00 178.00   1.00    1.00    --  112.00  61.00 150.00   95
 37  ω     79.00 178.00   1.00    1.00    --  112.00  77.00 -30.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2032564000
_diffrn_orient_matrix_UB_12      -0.1554607000
_diffrn_orient_matrix_UB_13      -0.0303672000
_diffrn_orient_matrix_UB_21      0.0413911000
_diffrn_orient_matrix_UB_22      -0.0354161000
_diffrn_orient_matrix_UB_23      0.0941725000
_diffrn_orient_matrix_UB_31      -0.1053473000
_diffrn_orient_matrix_UB_32      -0.1599522000
_diffrn_orient_matrix_UB_33      0.0167278000
_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                2795
_reflns_number_total             2893
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2893
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0269
_refine_ls_restrained_S_all      1.055
_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)+(0.0504P)²+0.2877P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0769
_refine_ls_wR_factor_ref         0.0778
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: C15(0.5) H15A(0.5) H15B(0.5) H15C(0.5) C14(0.5) H14A(0.5)
 H14B(0.5) H14C(0.5)
3.a Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C)
;
_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
Cl2 Cl 0.29726(6) 0.64329(5) 0.94946(2) 0.02414(12) Uani 1 1 d . . . . .
S1 S 0.48992(6) 0.44259(5) 0.61529(2) 0.02007(11) Uani 1 1 d . . . . .
Cl1 Cl 0.77630(6) 0.52700(6) 0.56521(2) 0.02623(12) Uani 1 1 d . . . . .
Cl3 Cl 0.10309(6) 1.07694(6) 0.88642(3) 0.02791(12) Uani 1 1 d . . . . .
Cl4 Cl 0.07822(6) 1.18629(6) 0.68925(3) 0.03010(12) Uani 1 1 d . . . . .
O1 O 0.28833(18) 0.84393(18) 0.57490(8) 0.0254(3) Uani 1 1 d . . . . .
N2 N 0.4807(2) 0.37141(19) 0.81022(9) 0.0181(3) Uani 1 1 d . . . . .
N1 N 0.5484(2) 0.2413(2) 0.66878(9) 0.0216(3) Uani 1 1 d . . . . .
C2 C 0.3876(2) 0.5580(2) 0.78017(10) 0.0176(3) Uani 1 1 d . . . . .
C1 C 0.5538(2) 0.2292(2) 0.75680(10) 0.0183(3) Uani 1 1 d . . . . .
C6 C 0.2841(2) 0.8090(2) 0.66259(11) 0.0215(3) Uani 1 1 d . . . . .
C4 C 0.2057(2) 0.8981(2) 0.81229(11) 0.0206(3) Uani 1 1 d . . . . .
C7 C 0.3769(2) 0.6163(2) 0.69217(11) 0.0193(3) Uani 1 1 d . . . . .
C8 C 0.6467(2) 0.0280(2) 0.79239(11) 0.0186(3) Uani 1 1 d . . . . .
C5 C 0.1979(2) 0.9502(2) 0.72319(11) 0.0212(3) Uani 1 1 d . . . . .
C3 C 0.2953(2) 0.7065(2) 0.84056(10) 0.0188(3) Uani 1 1 d . . . . .
C9 C 0.6528(3) -0.0081(2) 0.88167(11) 0.0234(3) Uani 1 1 d . . . . .
C13 C 0.7305(3) -0.1279(2) 0.73780(11) 0.0230(3) Uani 1 1 d . . . . .
C10 C 0.7415(3) -0.1962(3) 0.91463(12) 0.0266(4) Uani 1 1 d . . . . .
C11 C 0.8253(3) -0.3501(2) 0.85976(12) 0.0264(4) Uani 1 1 d . . . . .
C12 C 0.8185(3) -0.3151(3) 0.77150(12) 0.0262(4) Uani 1 1 d . . . . .
C15 C 0.4018(6) 0.9676(5) 0.5276(2) 0.0311(8) Uani 0.5 1 d . . P A -2
H15A H 0.328803 1.102077 0.539000 0.047 Uiso 0.5 1 calc GR . P A -2
H15B H 0.421915 0.950477 0.466379 0.047 Uiso 0.5 1 calc GR . P A -2
H15C H 0.530459 0.932726 0.545991 0.047 Uiso 0.5 1 calc GR . P A -2
C14 C 0.0964(6) 0.9126(6) 0.5434(3) 0.0343(8) Uani 0.5 1 d . . P A -1
H14A H 0.034219 0.810303 0.553473 0.051 Uiso 0.5 1 calc GR . P A -1
H14B H 0.119597 0.947424 0.482145 0.051 Uiso 0.5 1 calc GR . P A -1
H14C H 0.008976 1.025232 0.573891 0.051 Uiso 0.5 1 calc GR . P A -1
H9 H 0.594(3) 0.095(3) 0.9178(15) 0.032(6) Uiso 1 1 d . . . . .
H13 H 0.730(4) -0.101(4) 0.6763(17) 0.041(6) Uiso 1 1 d . . . . .
H11 H 0.886(4) -0.477(4) 0.8824(15) 0.037(6) Uiso 1 1 d . . . . .
H12 H 0.871(4) -0.411(4) 0.7371(17) 0.046(7) Uiso 1 1 d . . . . .
H10 H 0.739(3) -0.214(3) 0.9742(15) 0.031(5) Uiso 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
Cl2 C3 1.7182(16) . ?
S1 Cl1 2.2759(6) . ?
S1 N1 1.5660(14) . ?
S1 C7 1.7291(16) . ?
Cl3 C4 1.7196(16) . ?
Cl4 C5 1.7154(16) . ?
O1 C6 1.366(2) . ?
O1 C15 1.438(4) . ?
O1 C14 1.458(4) . ?
N2 C2 1.369(2) . ?
N2 C1 1.308(2) . ?
N1 C1 1.382(2) . ?
C2 C7 1.405(2) . ?
C2 C3 1.419(2) . ?
C1 C8 1.481(2) . ?
C6 C7 1.401(2) . ?
C6 C5 1.382(2) . ?
C4 C5 1.412(2) . ?
C4 C3 1.384(2) . ?
C8 C9 1.402(2) . ?
C8 C13 1.395(2) . ?
C9 C10 1.386(2) . ?
C9 H9 0.92(2) . ?
C13 C12 1.384(2) . ?
C13 H13 0.96(3) . ?
C10 C11 1.387(3) . ?
C10 H10 0.93(2) . ?
C11 C12 1.386(3) . ?
C11 H11 0.94(2) . ?
C12 H12 0.87(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
N1 S1 Cl1 108.06(6) . . ?
N1 S1 C7 105.31(8) . . ?
C7 S1 Cl1 98.17(6) . . ?
C6 O1 C15 118.96(18) . . ?
C6 O1 C14 118.06(19) . . ?
C1 N2 C2 120.15(14) . . ?
C1 N1 S1 122.10(11) . . ?
N2 C2 C7 124.66(14) . . ?
N2 C2 C3 119.04(14) . . ?
C7 C2 C3 116.30(14) . . ?
N2 C1 N1 127.38(15) . . ?
N2 C1 C8 118.55(14) . . ?
N1 C1 C8 114.01(14) . . ?
O1 C6 C7 117.03(15) . . ?
O1 C6 C5 124.63(15) . . ?
C5 C6 C7 118.33(15) . . ?
C5 C4 Cl3 119.13(12) . . ?
C3 C4 Cl3 119.74(13) . . ?
C3 C4 C5 121.13(15) . . ?
C2 C7 S1 118.44(12) . . ?
C6 C7 S1 117.80(13) . . ?
C6 C7 C2 123.74(15) . . ?
C9 C8 C1 120.30(14) . . ?
C13 C8 C1 120.71(15) . . ?
C13 C8 C9 118.98(15) . . ?
C6 C5 Cl4 119.41(13) . . ?
C6 C5 C4 119.80(14) . . ?
C4 C5 Cl4 120.78(13) . . ?
C2 C3 Cl2 118.58(12) . . ?
C4 C3 Cl2 120.75(13) . . ?
C4 C3 C2 120.67(15) . . ?
C8 C9 H9 118.7(14) . . ?
C10 C9 C8 120.16(16) . . ?
C10 C9 H9 121.1(14) . . ?
C8 C13 H13 118.5(15) . . ?
C12 C13 C8 120.32(16) . . ?
C12 C13 H13 121.1(15) . . ?
C9 C10 C11 120.44(16) . . ?
C9 C10 H10 117.1(14) . . ?
C11 C10 H10 122.4(14) . . ?
C10 C11 H11 120.2(14) . . ?
C12 C11 C10 119.53(16) . . ?
C12 C11 H11 120.3(14) . . ?
C13 C12 C11 120.57(16) . . ?
C13 C12 H12 119.8(17) . . ?
C11 C12 H12 119.6(17) . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?


_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 1.887
_oxdiff_exptl_absorpt_empirical_full_min 0.576
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_jr0717b
_database_code_depnum_ccdc_archive 'CCDC 2101068'
loop_
_audit_author_name
_audit_author_address
'Andryj M Borys'
;University of Kent
United Kingdom
;
_audit_update_record             
;
2021-08-03 deposited with the CCDC.	2021-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 Cl4 N2 S'
_chemical_formula_sum            'C15 H10 Cl4 N2 S'
_chemical_formula_weight         392.11

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'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_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                   9.1703(4)
_cell_length_b                   13.7683(7)
_cell_length_c                   12.5807(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.799(3)
_cell_angle_gamma                90.00
_cell_volume                     1577.26(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    10392
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.632
_exptl_absorpt_correction_T_max  0.815
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'thin slice ω and φ scans'
_diffrn_reflns_number            11297
_diffrn_reflns_av_R_equivalents  0.1127
_diffrn_reflns_av_sigmaI/netI    0.0884
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         25.03
_reflns_number_total             2778
_reflns_number_gt                1977
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1247P)²+3.3075P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2778
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1020
_refine_ls_R_factor_gt           0.0738
_refine_ls_wR_factor_ref         0.2238
_refine_ls_wR_factor_gt          0.2026
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5770(5) 0.4234(3) 0.8531(4) 0.0333(11) Uani 1 1 d . . .
S1 S 0.62807(15) 0.52044(11) 0.80362(11) 0.0344(4) Uani 1 1 d . . .
Cl1 Cl 0.58167(19) 0.51019(12) 0.62338(12) 0.0478(5) Uani 1 1 d . . .
C1 C 0.5001(6) 0.6075(4) 0.8251(4) 0.0302(12) Uani 1 1 d . . .
C2 C 0.5267(6) 0.7062(4) 0.8021(4) 0.0331(13) Uani 1 1 d . . .
C3 C 0.4207(6) 0.7722(4) 0.8255(4) 0.0330(12) Uani 1 1 d . . .
C4 C 0.2986(6) 0.7422(4) 0.8726(5) 0.0349(13) Uani 1 1 d . . .
C5 C 0.2745(6) 0.6462(4) 0.8965(5) 0.0385(14) Uani 1 1 d . . .
C6 C 0.3763(6) 0.5757(4) 0.8708(4) 0.0310(12) Uani 1 1 d . . .
C7 C 0.6618(7) 0.7391(5) 0.7507(5) 0.0488(16) Uani 1 1 d . . .
H7A H 0.7329 0.6857 0.7532 0.073 Uiso 1 1 calc R . .
H7B H 0.7070 0.7950 0.7902 0.073 Uiso 1 1 calc R . .
H7C H 0.6321 0.7576 0.6761 0.073 Uiso 1 1 calc R . .
C8 C 0.1522(7) 0.6120(6) 0.9586(5) 0.0545(18) Uani 1 1 d . . .
H8A H 0.1329 0.6619 1.0119 0.065 Uiso 1 1 calc R . .
H8B H 0.1823 0.5514 0.9975 0.065 Uiso 1 1 calc R . .
Cl2 Cl 0.44281(19) 0.89292(11) 0.79545(13) 0.0482(5) Uani 1 1 d . . .
Cl3 Cl 0.17203(19) 0.82963(12) 0.90041(15) 0.0553(5) Uani 1 1 d . . .
Cl4 Cl -0.01265(18) 0.59045(15) 0.86861(15) 0.0610(6) Uani 1 1 d . . .
N2 N 0.3437(5) 0.4802(3) 0.8923(4) 0.0341(11) Uani 1 1 d . . .
C9 C 0.4374(6) 0.4123(4) 0.8796(4) 0.0329(12) Uani 1 1 d . . .
C10 C 0.3951(6) 0.3110(4) 0.9025(4) 0.0315(12) Uani 1 1 d . . .
C11 C 0.2607(6) 0.2898(5) 0.9392(5) 0.0406(14) Uani 1 1 d . . .
H11A H 0.1958 0.3412 0.9518 0.049 Uiso 1 1 calc R . .
C12 C 0.2211(7) 0.1949(5) 0.9576(5) 0.0489(17) Uani 1 1 d . . .
H12A H 0.1290 0.1812 0.9818 0.059 Uiso 1 1 calc R . .
C13 C 0.3159(8) 0.1203(5) 0.9407(5) 0.0494(17) Uani 1 1 d . . .
H13A H 0.2895 0.0550 0.9535 0.059 Uiso 1 1 calc R . .
C14 C 0.4479(8) 0.1404(5) 0.9054(5) 0.0501(16) Uani 1 1 d . . .
H14A H 0.5123 0.0885 0.8937 0.060 Uiso 1 1 calc R . .
C15 C 0.4896(7) 0.2342(5) 0.8865(5) 0.0431(15) Uani 1 1 d . . .
H15A H 0.5823 0.2467 0.8628 0.052 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
N1 C9 1.369(7) . ?
N1 S1 1.568(5) . ?
S1 C1 1.721(5) . ?
S1 Cl1 2.262(2) . ?
C1 C6 1.402(8) . ?
C1 C2 1.416(8) . ?
C2 C3 1.388(8) . ?
C2 C7 1.532(8) . ?
C3 C4 1.390(8) . ?
C3 Cl2 1.722(6) . ?
C4 C5 1.379(8) . ?
C4 Cl3 1.736(5) . ?
C5 C6 1.410(8) . ?
C5 C8 1.516(8) . ?
C6 N2 1.383(7) . ?
C8 Cl4 1.802(7) . ?
N2 C9 1.292(7) . ?
C9 C10 1.485(8) . ?
C10 C15 1.396(8) . ?
C10 C11 1.397(8) . ?
C11 C12 1.382(9) . ?
C12 C13 1.379(10) . ?
C13 C14 1.366(9) . ?
C14 C15 1.375(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
C9 N1 S1 121.6(4) . . ?
N1 S1 C1 106.8(3) . . ?
N1 S1 Cl1 108.38(19) . . ?
C1 S1 Cl1 98.62(19) . . ?
C6 C1 C2 123.4(5) . . ?
C6 C1 S1 116.6(4) . . ?
C2 C1 S1 119.9(4) . . ?
C3 C2 C1 116.3(5) . . ?
C3 C2 C7 121.2(5) . . ?
C1 C2 C7 122.5(5) . . ?
C2 C3 C4 121.0(5) . . ?
C2 C3 Cl2 118.8(4) . . ?
C4 C3 Cl2 120.2(4) . . ?
C5 C4 C3 122.4(5) . . ?
C5 C4 Cl3 119.5(4) . . ?
C3 C4 Cl3 118.1(4) . . ?
C4 C5 C6 118.8(5) . . ?
C4 C5 C8 123.8(6) . . ?
C6 C5 C8 117.0(6) . . ?
N2 C6 C1 125.6(5) . . ?
N2 C6 C5 116.4(5) . . ?
C1 C6 C5 118.0(5) . . ?
C5 C8 Cl4 110.1(4) . . ?
C9 N2 C6 120.1(5) . . ?
N2 C9 N1 127.1(5) . . ?
N2 C9 C10 117.5(5) . . ?
N1 C9 C10 115.2(5) . . ?
C15 C10 C11 118.4(5) . . ?
C15 C10 C9 120.2(5) . . ?
C11 C10 C9 121.4(5) . . ?
C12 C11 C10 120.8(6) . . ?
C13 C12 C11 119.7(6) . . ?
C14 C13 C12 119.9(6) . . ?
C13 C14 C15 121.5(6) . . ?
C14 C15 C10 119.8(6) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.450
_refine_diff_density_min         -0.668
_refine_diff_density_rms         0.142
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_jr0710
_database_code_depnum_ccdc_archive 'CCDC 2101066'
loop_
_audit_author_name
_audit_author_address
'Andryj M Borys'
;University of Kent
United Kingdom
;
_audit_update_record             
;
2021-08-03 deposited with the CCDC.	2021-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H6 Cl4 N2 S'
_chemical_formula_sum            'C13 H6 Cl4 N2 S'
_chemical_formula_weight         364.06

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'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_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                   14.4699(8)
_cell_length_b                   13.6411(7)
_cell_length_c                   16.045(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.564(2)
_cell_angle_gamma                90.00
_cell_volume                     2857.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    81408
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1456
_exptl_absorpt_coefficient_mu    0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.712
_exptl_absorpt_correction_T_max  0.840
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'thin slice ω and φ scans'
_diffrn_reflns_number            26565
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_av_sigmaI/netI    0.0628
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.81
_diffrn_reflns_theta_max         25.03
_reflns_number_total             5023
_reflns_number_gt                3443
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0374P)²+2.8105P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5023
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1119
_refine_ls_wR_factor_gt          0.0982
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.17946(8) 0.46545(7) -0.00344(7) 0.0541(3) Uani 1 1 d . . .
S1 S 0.35281(7) 0.46812(7) 0.09177(7) 0.0404(3) Uani 1 1 d . . .
C1 C 0.3523(3) 0.5575(3) 0.1680(3) 0.0367(9) Uani 1 1 d . . .
C2 C 0.3417(3) 0.6559(3) 0.1408(3) 0.0402(9) Uani 1 1 d . . .
H2A H 0.3319 0.6735 0.0803 0.048 Uiso 1 1 calc R . .
C3 C 0.3458(3) 0.7258(2) 0.2030(3) 0.0397(9) Uani 1 1 d . . .
C4 C 0.3613(3) 0.7008(3) 0.2930(3) 0.0393(10) Uani 1 1 d . . .
C5 C 0.3696(3) 0.6028(3) 0.3184(3) 0.0362(9) Uani 1 1 d . . .
C6 C 0.3653(3) 0.5276(2) 0.2561(3) 0.0348(9) Uani 1 1 d . . .
N1 N 0.3747(2) 0.4326(2) 0.2859(2) 0.0366(7) Uani 1 1 d . . .
C7 C 0.3812(3) 0.3622(3) 0.2334(3) 0.0353(9) Uani 1 1 d . . .
N2 N 0.3833(2) 0.3707(2) 0.1486(2) 0.0409(8) Uani 1 1 d . . .
C8 C 0.3949(3) 0.2602(3) 0.2689(3) 0.0368(9) Uani 1 1 d . . .
C9 C 0.4162(3) 0.2427(3) 0.3606(3) 0.0445(10) Uani 1 1 d . . .
H9A H 0.4228 0.2957 0.4012 0.053 Uiso 1 1 calc R . .
C10 C 0.4277(3) 0.1465(3) 0.3925(3) 0.0502(11) Uani 1 1 d . . .
H10A H 0.4423 0.1339 0.4552 0.060 Uiso 1 1 calc R . .
C11 C 0.4182(3) 0.0693(3) 0.3337(3) 0.0529(12) Uani 1 1 d . . .
H11A H 0.4254 0.0038 0.3557 0.063 Uiso 1 1 calc R . .
C12 C 0.3983(3) 0.0875(3) 0.2434(3) 0.0515(11) Uani 1 1 d . . .
H12A H 0.3926 0.0344 0.2033 0.062 Uiso 1 1 calc R . .
C13 C 0.3864(3) 0.1823(3) 0.2103(3) 0.0438(10) Uani 1 1 d . . .
H13A H 0.3725 0.1942 0.1477 0.053 Uiso 1 1 calc R . .
Cl2 Cl 0.33116(9) 0.84697(7) 0.16971(8) 0.0587(3) Uani 1 1 d . . .
Cl3 Cl 0.36828(8) 0.79009(7) 0.37065(7) 0.0485(3) Uani 1 1 d . . .
Cl4 Cl 0.38611(8) 0.57061(7) 0.42737(7) 0.0522(3) Uani 1 1 d . . .
Cl5 Cl 0.16549(8) 0.69907(10) 0.54090(8) 0.0669(4) Uani 1 1 d . . .
S2 S 0.33503(8) 0.68732(8) 0.60071(7) 0.0482(3) Uani 1 1 d . . .
C14 C 0.3587(3) 0.7304(3) 0.7098(3) 0.0421(10) Uani 1 1 d . . .
C15 C 0.3592(3) 0.8314(3) 0.7248(3) 0.0495(11) Uani 1 1 d . . .
H15A H 0.3454 0.8765 0.6757 0.059 Uiso 1 1 calc R . .
C16 C 0.3800(3) 0.8636(3) 0.8118(3) 0.0476(11) Uani 1 1 d . . .
C17 C 0.3973(3) 0.7969(3) 0.8837(3) 0.0443(10) Uani 1 1 d . . .
C18 C 0.3978(3) 0.6971(3) 0.8675(3) 0.0426(10) Uani 1 1 d . . .
C19 C 0.3775(3) 0.6603(3) 0.7790(3) 0.0406(10) Uani 1 1 d . . .
N3 N 0.3771(2) 0.5601(2) 0.7671(2) 0.0420(8) Uani 1 1 d . . .
C20 C 0.3698(3) 0.5245(3) 0.6893(3) 0.0433(10) Uani 1 1 d . . .
N4 N 0.3635(2) 0.5758(2) 0.6130(2) 0.0484(9) Uani 1 1 d . . .
C21 C 0.3725(3) 0.4161(3) 0.6807(3) 0.0431(10) Uani 1 1 d . . .
C22 C 0.3615(3) 0.3724(3) 0.5985(3) 0.0526(11) Uani 1 1 d . . .
H22A H 0.3533 0.4120 0.5470 0.063 Uiso 1 1 calc R . .
C23 C 0.3624(3) 0.2709(3) 0.5918(3) 0.0569(12) Uani 1 1 d . . .
H23A H 0.3546 0.2416 0.5354 0.068 Uiso 1 1 calc R . .
C24 C 0.3743(3) 0.2128(3) 0.6646(4) 0.0578(13) Uani 1 1 d . . .
H24A H 0.3757 0.1436 0.6592 0.069 Uiso 1 1 calc R . .
C25 C 0.3842(3) 0.2549(3) 0.7464(3) 0.0554(12) Uani 1 1 d . . .
H25A H 0.3914 0.2144 0.7970 0.066 Uiso 1 1 calc R . .
C26 C 0.3838(3) 0.3564(3) 0.7549(3) 0.0470(10) Uani 1 1 d . . .
H26A H 0.3913 0.3851 0.8115 0.056 Uiso 1 1 calc R . .
Cl6 Cl 0.38438(9) 0.98785(8) 0.83294(10) 0.0666(4) Uani 1 1 d . . .
Cl7 Cl 0.41618(8) 0.83921(8) 0.99069(8) 0.0575(3) Uani 1 1 d . . .
Cl8 Cl 0.42545(9) 0.61411(8) 0.95596(8) 0.0584(3) 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
Cl1 S1 2.3065(17) . ?
S1 N2 1.564(3) . ?
S1 C1 1.729(4) . ?
C1 C2 1.399(5) . ?
C1 C6 1.404(5) . ?
C2 C3 1.364(5) . ?
C3 C4 1.405(6) . ?
C3 Cl2 1.721(4) . ?
C4 C5 1.387(5) . ?
C4 Cl3 1.714(4) . ?
C5 C6 1.413(5) . ?
C5 Cl4 1.717(4) . ?
C6 N1 1.368(4) . ?
N1 C7 1.308(5) . ?
C7 N2 1.379(5) . ?
C7 C8 1.484(5) . ?
C8 C9 1.388(5) . ?
C8 C13 1.388(5) . ?
C9 C10 1.392(5) . ?
C10 C11 1.381(6) . ?
C11 C12 1.372(6) . ?
C12 C13 1.380(5) . ?
Cl5 S2 2.2211(17) . ?
S2 N4 1.567(4) . ?
S2 C14 1.735(4) . ?
C14 C15 1.397(5) . ?
C14 C19 1.400(5) . ?
C15 C16 1.368(6) . ?
C16 C17 1.404(6) . ?
C16 Cl6 1.725(4) . ?
C17 C18 1.387(5) . ?
C17 Cl7 1.717(4) . ?
C18 C19 1.413(5) . ?
C18 Cl8 1.722(4) . ?
C19 N3 1.380(5) . ?
N3 C20 1.299(5) . ?
C20 N4 1.379(5) . ?
C20 C21 1.488(5) . ?
C21 C22 1.392(6) . ?
C21 C26 1.392(6) . ?
C22 C23 1.390(6) . ?
C23 C24 1.359(6) . ?
C24 C25 1.383(6) . ?
C25 C26 1.391(6) . ?

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
N2 S1 C1 105.84(18) . . ?
N2 S1 Cl1 108.99(12) . . ?
C1 S1 Cl1 98.30(13) . . ?
C2 C1 C6 122.8(3) . . ?
C2 C1 S1 119.3(3) . . ?
C6 C1 S1 117.9(3) . . ?
C3 C2 C1 118.6(4) . . ?
C2 C3 C4 121.3(3) . . ?
C2 C3 Cl2 119.0(3) . . ?
C4 C3 Cl2 119.8(3) . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 Cl3 120.1(3) . . ?
C3 C4 Cl3 120.5(3) . . ?
C4 C5 C6 121.4(4) . . ?
C4 C5 Cl4 120.1(3) . . ?
C6 C5 Cl4 118.6(3) . . ?
N1 C6 C1 125.2(3) . . ?
N1 C6 C5 118.3(3) . . ?
C1 C6 C5 116.5(3) . . ?
C7 N1 C6 119.7(3) . . ?
N1 C7 N2 127.8(3) . . ?
N1 C7 C8 118.4(3) . . ?
N2 C7 C8 113.7(3) . . ?
C7 N2 S1 121.7(3) . . ?
C9 C8 C13 120.0(3) . . ?
C9 C8 C7 120.0(3) . . ?
C13 C8 C7 120.0(4) . . ?
C8 C9 C10 119.3(4) . . ?
C11 C10 C9 120.4(4) . . ?
C12 C11 C10 119.8(4) . . ?
C11 C12 C13 120.7(4) . . ?
C12 C13 C8 119.8(4) . . ?
N4 S2 C14 105.99(19) . . ?
N4 S2 Cl5 107.80(13) . . ?
C14 S2 Cl5 96.41(14) . . ?
C15 C14 C19 123.6(4) . . ?
C15 C14 S2 119.4(3) . . ?
C19 C14 S2 117.0(3) . . ?
C16 C15 C14 118.3(4) . . ?
C15 C16 C17 120.9(4) . . ?
C15 C16 Cl6 119.3(3) . . ?
C17 C16 Cl6 119.8(3) . . ?
C18 C17 C16 119.7(4) . . ?
C18 C17 Cl7 120.4(3) . . ?
C16 C17 Cl7 119.9(3) . . ?
C17 C18 C19 121.4(4) . . ?
C17 C18 Cl8 120.6(3) . . ?
C19 C18 Cl8 118.0(3) . . ?
N3 C19 C14 125.4(4) . . ?
N3 C19 C18 118.6(4) . . ?
C14 C19 C18 116.0(4) . . ?
C20 N3 C19 119.8(4) . . ?
N3 C20 N4 127.6(4) . . ?
N3 C20 C21 117.8(4) . . ?
N4 C20 C21 114.6(4) . . ?
C20 N4 S2 121.2(3) . . ?
C22 C21 C26 119.0(4) . . ?
C22 C21 C20 121.1(4) . . ?
C26 C21 C20 119.9(4) . . ?
C23 C22 C21 119.9(4) . . ?
C24 C23 C22 121.1(5) . . ?
C23 C24 C25 119.8(4) . . ?
C24 C25 C26 120.2(4) . . ?
C25 C26 C21 120.1(4) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.654
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.066
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_serc084-r1-rf
_database_code_depnum_ccdc_archive 'CCDC 2101072'
loop_
_audit_author_name
_audit_author_address
'Andryj M Borys'
;University of Kent
United Kingdom
;
_audit_update_record             
;
2021-08-03 deposited with the CCDC.	2021-11-23 downloaded from the CCDC.
;
_audit_creation_date             2018-06-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 Cl3 N2 S'
_chemical_formula_sum            'C15 H10 Cl3 N2 S'
_chemical_formula_weight         356.66
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H11 Cl3 N2 S1 '
_chemical_oxdiff_usercomment     'ABS-267 2,3-rad 150k'
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                   11.5111(15)
_cell_length_b                   7.7055(8)
_cell_length_c                   16.9368(18)
_cell_angle_alpha                90
_cell_angle_beta                 104.127(12)
_cell_angle_gamma                90
_cell_volume                     1456.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4990
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      74.8220
_cell_measurement_theta_min      4.1040
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.972
_exptl_absorpt_correction_T_max  0.867
_exptl_absorpt_correction_T_min  0.514
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark violet'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             724
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 0 -11 0.0128
0 -5 0 0.0624
-2 0 11 0.0129
-1 5 1 0.0669
-2 -1 -10 0.0194
7 0 -6 0.0208
2 1 9 0.0170
-7 0 4 0.0069

_exptl_crystal_size_max          0.132
_exptl_crystal_size_mid          0.041
_exptl_crystal_size_min          0.028
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.6986 -0.2315 -10.9654 0.0333 0.1282 0.9912
0.4462 -4.9956 -0.0288 -0.2282 -0.9570 0.1788
-1.6692 -0.1141 10.9728 -0.0491 -0.1945 -0.9797
-0.5397 4.9875 0.6440 0.2254 0.9458 -0.2337
-1.7695 -0.9412 -9.5162 0.4446 -0.1086 0.8891
7.0117 -0.2502 -6.1736 -0.8080 0.1916 0.5571
2.3026 0.9280 9.1116 -0.5074 0.1235 -0.8528
-7.3820 0.0673 4.3376 0.8977 -0.2135 -0.3855

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7614
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        65.973
_diffrn_reflns_theta_max         65.973
_diffrn_reflns_theta_min         4.210
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2774
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -114.00 -19.00   1.00   22.50    --  -41.76 -38.00  90.00   95
  2  ω   -120.00  -5.00   1.00   22.50    --  -41.76 -19.00 150.00  115
  3  ω      1.00  82.00   1.00   22.50    --   41.76 -99.00  60.00   81
  4  ω     27.00 109.00   1.00   95.00    --  108.25 -95.00  30.00   82
  5  ω     84.00 178.00   1.00   95.00    --  108.25  30.00  90.00   94
  6  ω     33.00 132.00   1.00   95.00    --  108.25 -30.00-150.00   99
  7  ω     84.00 178.00   1.00   95.00    --  108.25  45.00 -30.00   94
  8  ω     94.00 178.00   1.00   95.00    --  108.25 125.00 -90.00   84
  9  ω     27.00 109.00   1.00   95.00    --  108.25 -95.00  60.00   82
 10  ω     27.00 109.00   1.00   95.00    --  108.25 -95.00-120.00   82
 11  ω    -64.00 -35.00   1.00   22.50    --  -41.76  38.00 -90.00   29
 12  ω   -112.00 -15.00   1.00   22.50    --  -41.76 -57.00 -30.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1358606000
_diffrn_orient_matrix_UB_12      0.0336942000
_diffrn_orient_matrix_UB_13      -0.0247904000
_diffrn_orient_matrix_UB_21      0.0235589000
_diffrn_orient_matrix_UB_22      0.1937529000
_diffrn_orient_matrix_UB_23      -0.0121309000
_diffrn_orient_matrix_UB_31      -0.0008478000
_diffrn_orient_matrix_UB_32      -0.0353563000
_diffrn_orient_matrix_UB_33      -0.0897776000
_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                2325
_reflns_number_total             2532
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.577
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2532
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.053
_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)+(0.0720P)²+0.1350P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1076
_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 Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C12(H12), C6(H6), C3(H3), C5(H5), C4(H4)
;
_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
S1 S 0.40478(4) 0.30608(7) 0.39621(3) 0.02482(18) Uani 1 1 d . . . . .
Cl3 Cl 0.81479(4) -0.05766(6) 0.44627(3) 0.02971(17) Uani 1 1 d . . . . .
Cl1 Cl 0.61622(5) 0.08302(8) 0.74481(3) 0.03382(18) Uani 1 1 d . . . . .
Cl2 Cl 0.96422(4) 0.17725(9) 0.64906(3) 0.0439(2) Uani 1 1 d . . . . .
N2 N 0.46859(14) 0.3378(2) 0.57992(9) 0.0218(3) Uani 1 1 d . . . . .
N1 N 0.32422(14) 0.3905(2) 0.45315(9) 0.0238(4) Uani 1 1 d . . . . .
C8 C 0.54754(16) 0.2511(2) 0.54596(11) 0.0198(4) Uani 1 1 d . . . . .
C1 C 0.36449(16) 0.3957(2) 0.53407(11) 0.0209(4) Uani 1 1 d . . . . .
C13 C 0.53016(16) 0.2172(3) 0.46168(11) 0.0211(4) Uani 1 1 d . . . . .
C14 C 0.67772(17) 0.2383(3) 0.68647(11) 0.0261(4) Uani 1 1 d . . . . .
H14A H 0.642669 0.351307 0.690723 0.031 Uiso 1 1 calc R . . . .
H14B H 0.763444 0.247328 0.709087 0.031 Uiso 1 1 calc R . . . .
C2 C 0.28307(16) 0.4801(3) 0.57799(11) 0.0228(4) Uani 1 1 d . . . . .
C11 C 0.71296(17) 0.0581(2) 0.48558(12) 0.0234(4) Uani 1 1 d . . . . .
C9 C 0.65453(17) 0.1882(3) 0.59891(11) 0.0218(4) Uani 1 1 d . . . . .
C10 C 0.73568(17) 0.0900(3) 0.56935(12) 0.0244(4) Uani 1 1 d . . . . .
C7 C 0.17424(17) 0.5501(3) 0.53518(13) 0.0268(4) Uani 1 1 d . . . . .
H7 H 0.151177 0.540496 0.478772 0.032 Uiso 1 1 calc R . . . .
C12 C 0.61168(17) 0.1210(3) 0.43171(11) 0.0229(4) Uani 1 1 d . . . . .
H12 H 0.598393 0.099122 0.376225 0.027 Uiso 1 1 calc R . . . .
C6 C 0.10057(18) 0.6335(3) 0.57629(15) 0.0327(5) Uani 1 1 d . . . . .
H6 H 0.027953 0.679693 0.547448 0.039 Uiso 1 1 calc R . . . .
C3 C 0.31611(18) 0.4949(3) 0.66209(12) 0.0313(5) Uani 1 1 d . . . . .
H3 H 0.388350 0.448095 0.691210 0.038 Uiso 1 1 calc R . . . .
C15 C 0.84561(19) 0.0181(3) 0.62696(13) 0.0338(5) Uani 1 1 d . . . . .
H15A H 0.872705 -0.083863 0.603001 0.041 Uiso 1 1 calc R . . . .
H15B H 0.826014 -0.016854 0.677197 0.041 Uiso 1 1 calc R . . . .
C5 C 0.1343(2) 0.6487(3) 0.66034(15) 0.0372(5) Uani 1 1 d . . . . .
H5 H 0.084607 0.705474 0.687851 0.045 Uiso 1 1 calc R . . . .
C4 C 0.2417(2) 0.5795(4) 0.70297(15) 0.0407(6) Uani 1 1 d . . . . .
H4 H 0.264448 0.589422 0.759369 0.049 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
S1 N1 1.6278(17) . ?
S1 C13 1.7322(19) . ?
Cl3 C11 1.7303(19) . ?
Cl1 C14 1.803(2) . ?
Cl2 C15 1.805(3) . ?
N2 C8 1.363(3) . ?
N2 C1 1.335(2) . ?
N1 C1 1.336(3) . ?
C8 C13 1.417(3) . ?
C8 C9 1.420(3) . ?
C1 C2 1.482(3) . ?
C13 C12 1.386(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C9 1.492(3) . ?
C2 C7 1.394(3) . ?
C2 C3 1.386(3) . ?
C11 C10 1.400(3) . ?
C11 C12 1.381(3) . ?
C9 C10 1.387(3) . ?
C10 C15 1.503(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.380(3) . ?
C12 H12 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.386(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.388(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C5 H5 0.9300 . ?
C5 C4 1.378(4) . ?
C4 H4 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
N1 S1 C13 106.55(9) . . ?
C1 N2 C8 120.95(16) . . ?
C1 N1 S1 120.97(13) . . ?
N2 C8 C13 124.81(17) . . ?
N2 C8 C9 117.75(16) . . ?
C13 C8 C9 117.44(17) . . ?
N2 C1 N1 128.61(18) . . ?
N2 C1 C2 116.26(17) . . ?
N1 C1 C2 115.12(16) . . ?
C8 C13 S1 117.57(15) . . ?
C12 C13 S1 120.66(14) . . ?
C12 C13 C8 121.74(17) . . ?
Cl1 C14 H14A 109.2 . . ?
Cl1 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C9 C14 Cl1 111.99(14) . . ?
C9 C14 H14A 109.2 . . ?
C9 C14 H14B 109.2 . . ?
C7 C2 C1 120.47(18) . . ?
C3 C2 C1 120.23(17) . . ?
C3 C2 C7 119.27(19) . . ?
C10 C11 Cl3 120.25(15) . . ?
C12 C11 Cl3 117.95(15) . . ?
C12 C11 C10 121.78(18) . . ?
C8 C9 C14 117.18(17) . . ?
C10 C9 C8 120.99(17) . . ?
C10 C9 C14 121.79(17) . . ?
C11 C10 C15 120.85(18) . . ?
C9 C10 C11 119.06(17) . . ?
C9 C10 C15 120.09(18) . . ?
C2 C7 H7 119.9 . . ?
C6 C7 C2 120.17(19) . . ?
C6 C7 H7 119.9 . . ?
C13 C12 H12 120.5 . . ?
C11 C12 C13 118.93(17) . . ?
C11 C12 H12 120.5 . . ?
C7 C6 H6 119.8 . . ?
C7 C6 C5 120.3(2) . . ?
C5 C6 H6 119.8 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
Cl2 C15 H15A 109.4 . . ?
Cl2 C15 H15B 109.4 . . ?
C10 C15 Cl2 111.01(16) . . ?
C10 C15 H15A 109.4 . . ?
C10 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C6 C5 H5 120.2 . . ?
C4 C5 C6 119.7(2) . . ?
C4 C5 H5 120.2 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 H4 119.9 . . ?


_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 1.913
_oxdiff_exptl_absorpt_empirical_full_min 0.693
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
####################################################################### 
# 
# 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_serc010-r1-rf-fixed
_database_code_depnum_ccdc_archive 'CCDC 2101074'
loop_
_audit_author_name
_audit_author_address
'Andryj M Borys'
;University of Kent
United Kingdom
;
_audit_update_record             
;
2021-08-03 deposited with the CCDC.	2021-11-23 downloaded from the CCDC.
;
_audit_creation_date             2017-08-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H8 Cl4 N2 S'
_chemical_formula_sum            'C14 H8 Cl4 N2 S'
_chemical_formula_weight         378.08
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H8 Cl4 N2 S1 '
_chemical_oxdiff_usercomment     ortho-methylphenylbenzamidine-SOCl2/hexane
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_symmetry_space_group_name_H-M_alt 'P -1'
_cell_length_a                   8.9856(5)
_cell_length_b                   9.2182(3)
_cell_length_c                   9.3740(6)
_cell_angle_alpha                103.868(4)
_cell_angle_beta                 94.530(5)
_cell_angle_gamma                95.061(4)
_cell_volume                     746.84(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5879
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.6660
_cell_measurement_theta_min      4.8830
_cell_oxdiff_angle_alpha         103.868(4)
_cell_oxdiff_angle_beta          94.530(5)
_cell_oxdiff_angle_gamma         95.061(4)
_cell_oxdiff_length_a            8.9856(5)
_cell_oxdiff_length_b            9.2182(3)
_cell_oxdiff_length_c            9.3740(6)
_cell_oxdiff_measurement_reflns_used 5879
_cell_oxdiff_volume              746.84(7)
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.456
_exptl_absorpt_correction_T_max  0.507
_exptl_absorpt_correction_T_min  0.285
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orangish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             380
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-6 1 -1 0.0952
1 -6 2 0.0607
1 6 0 0.0532
-2 5 -3 0.0611
-2 -5 -1 0.0651
5 -2 3 0.1115
5 0 -4 0.0634
3 1 -6 0.0626
4 -1 4 0.1092
-4 0 5 0.0605

_exptl_crystal_recrystallization_method 
'Layering of dry hexane onto a saturated solution of the product in thionyl chloride.'
_exptl_crystal_size_max          0.239
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.119
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-5.7068 1.2524 -0.6894 0.6038 0.1782 0.7770
0.6076 -5.9822 1.5339 0.2725 -0.9162 -0.2939
0.5485 5.7407 -0.2301 -0.2847 0.9586 -0.0091
-2.0563 5.4245 -3.0431 -0.2161 0.7251 0.6538
-1.5804 -5.0312 -1.0053 0.2721 -0.9173 0.2908
4.9475 -1.5397 2.7881 -0.3002 -0.0877 -0.9498
4.6813 -0.0895 -3.9595 -0.9565 -0.2840 -0.0668
2.7218 0.6252 -5.5697 -0.8892 -0.2647 0.3732
3.7753 -0.9502 4.2812 -0.0323 0.1126 -0.9931
-3.7931 -0.2762 4.8907 0.9465 0.2814 -0.1581

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7792
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        65.382
_diffrn_reflns_theta_max         65.382
_diffrn_reflns_theta_min         4.886
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2887
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -113.00 -13.00   0.50    0.50    --  -41.14 -57.00 120.00  200
  2  ω    -69.00  32.00   0.50    0.50    --  -41.14  57.00 -90.00  202
  3  ω     23.00  97.00   0.50    0.50    --   41.14-125.00 -30.00  148
  4  ω      9.00 117.00   0.50    0.50    --   41.14  77.00  30.00  216
  5  ω     28.00 115.00   0.50    0.76    --  104.67-111.00 150.00  174
  6  ω    100.00 178.00   0.50    0.76    --  104.67 111.00  60.00  156
  7  ω     29.00 137.00   0.50    0.76    --  104.67 -77.00 150.00  216
  8  ω     28.00 133.00   0.50    0.76    --  104.67 -30.00 -90.00  210
  9  ω     72.00 178.00   0.50    0.76    --  104.67  77.00-150.00  212
 10  ω     22.00 108.00   0.50    0.76    --  104.67 -94.00  60.00  172
 11  ω     22.00 108.00   0.50    0.76    --  104.67 -94.00 -90.00  172
 12  ω     32.00 131.00   0.50    0.76    --  104.67 -45.00 150.00  198
 13  ω     22.00 108.00   0.50    0.76    --  104.67 -94.00   0.00  172
 14  ω     32.00 131.00   0.50    0.76    --  104.67 -45.00-180.00  198
 15  ω     23.00 157.00   0.50    0.76    --  104.67 -15.00  30.00  268
 16  ω   -113.00 -13.00   0.50    0.50    --  -41.14 -57.00-120.00  200
 17  ω    -33.00  66.00   0.50    0.50    --   41.14 -38.00 -30.00  198
 18  ω      9.00 117.00   0.50    0.50    --   41.14  77.00 -60.00  216
 19  ω    -33.00  66.00   0.50    0.50    --   41.14 -38.00  90.00  198
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1246967000
_diffrn_orient_matrix_UB_12      -0.0338747000
_diffrn_orient_matrix_UB_13      0.0949063000
_diffrn_orient_matrix_UB_21      -0.0018905000
_diffrn_orient_matrix_UB_22      0.1697901000
_diffrn_orient_matrix_UB_23      0.0656508000
_diffrn_orient_matrix_UB_31      -0.1199724000
_diffrn_orient_matrix_UB_32      0.0048733000
_diffrn_orient_matrix_UB_33      -0.1250943000
_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                2470
_reflns_number_total             2562
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    ?
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2562
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0267
_refine_ls_restrained_S_all      1.066
_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)+(0.0372P)²+0.4301P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0730
_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 Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C4(H4), C10(H10), C13(H13), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Cl3 Cl 0.97557(5) 0.93083(5) 0.79791(5) 0.03063(13) Uani 1 1 d . . . . .
S1 S 0.80647(5) 0.24456(5) 0.53648(5) 0.02761(13) Uani 1 1 d . . . . .
Cl2 Cl 1.12607(5) 0.70089(6) 0.94364(5) 0.03433(14) Uani 1 1 d . . . . .
Cl4 Cl 0.82566(6) 0.85672(6) 0.40294(5) 0.03500(14) Uani 1 1 d . . . . .
Cl1 Cl 0.65228(6) 0.19876(5) 0.70642(6) 0.03793(15) Uani 1 1 d . . . . .
N2 N 0.66736(17) 0.49139(17) 0.43054(17) 0.0236(3) Uani 1 1 d . . . . .
N1 N 0.70679(18) 0.23000(17) 0.38798(18) 0.0283(4) Uani 1 1 d . . . . .
C2 C 0.7768(2) 0.5351(2) 0.5474(2) 0.0222(4) Uani 1 1 d . . . . .
C7 C 0.8139(2) 0.6928(2) 0.6085(2) 0.0230(4) Uani 1 1 d . . . . .
C1 C 0.6378(2) 0.3499(2) 0.3595(2) 0.0235(4) Uani 1 1 d . . . . .
C6 C 0.9244(2) 0.7407(2) 0.7256(2) 0.0241(4) Uani 1 1 d . . . . .
C9 C 0.5218(2) 0.3101(2) 0.2314(2) 0.0242(4) Uani 1 1 d . . . . .
C8 C 0.7293(2) 0.7998(2) 0.5453(2) 0.0249(4) Uani 1 1 d . . . . .
H8A H 0.718439 0.889522 0.624891 0.030 Uiso 1 1 calc R . . . .
H8B H 0.627446 0.750840 0.503579 0.030 Uiso 1 1 calc R . . . .
C5 C 0.9969(2) 0.6378(2) 0.7894(2) 0.0257(4) Uani 1 1 d . . . . .
C3 C 0.8532(2) 0.4359(2) 0.6110(2) 0.0242(4) Uani 1 1 d . . . . .
C14 C 0.4684(2) 0.1597(2) 0.1656(2) 0.0299(4) Uani 1 1 d . . . . .
H14 H 0.508343 0.081666 0.201539 0.036 Uiso 1 1 calc R . . . .
C4 C 0.9617(2) 0.4857(2) 0.7320(2) 0.0272(4) Uani 1 1 d . . . . .
H4 H 1.010367 0.415871 0.773875 0.033 Uiso 1 1 calc R . . . .
C10 C 0.4629(2) 0.4234(2) 0.1769(2) 0.0292(4) Uani 1 1 d . . . . .
H10 H 0.498965 0.525666 0.220982 0.035 Uiso 1 1 calc R . . . .
C13 C 0.3571(2) 0.1248(2) 0.0479(2) 0.0361(5) Uani 1 1 d . . . . .
H13 H 0.320442 0.022810 0.003510 0.043 Uiso 1 1 calc R . . . .
C11 C 0.3519(2) 0.3876(3) 0.0587(2) 0.0356(5) Uani 1 1 d . . . . .
H11 H 0.312142 0.465192 0.021837 0.043 Uiso 1 1 calc R . . . .
C12 C 0.2992(2) 0.2384(3) -0.0055(2) 0.0370(5) Uani 1 1 d . . . . .
H12 H 0.223030 0.213902 -0.086308 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
Cl3 C6 1.7271(18) . ?
S1 Cl1 2.2811(7) . ?
S1 N1 1.5653(17) . ?
S1 C3 1.7339(18) . ?
Cl2 C5 1.7283(19) . ?
Cl4 C8 1.8016(19) . ?
N2 C2 1.370(2) . ?
N2 C1 1.308(2) . ?
N1 C1 1.383(2) . ?
C2 C7 1.427(3) . ?
C2 C3 1.404(3) . ?
C7 C6 1.380(3) . ?
C7 C8 1.497(3) . ?
C1 C9 1.479(3) . ?
C6 C5 1.414(3) . ?
C9 C14 1.400(3) . ?
C9 C10 1.394(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C5 C4 1.375(3) . ?
C3 C4 1.395(3) . ?
C14 H14 0.9500 . ?
C14 C13 1.385(3) . ?
C4 H4 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.387(3) . ?
C13 H13 0.9500 . ?
C13 C12 1.387(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(3) . ?
C12 H12 0.9500 . ?

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
N1 S1 Cl1 107.92(7) . . ?
N1 S1 C3 105.69(9) . . ?
C3 S1 Cl1 98.16(7) . . ?
C1 N2 C2 120.61(16) . . ?
C1 N1 S1 121.52(13) . . ?
N2 C2 C7 117.17(16) . . ?
N2 C2 C3 124.55(16) . . ?
C3 C2 C7 118.28(16) . . ?
C2 C7 C8 118.83(16) . . ?
C6 C7 C2 118.64(17) . . ?
C6 C7 C8 122.51(16) . . ?
N2 C1 N1 127.05(17) . . ?
N2 C1 C9 118.16(17) . . ?
N1 C1 C9 114.77(16) . . ?
C7 C6 Cl3 119.58(15) . . ?
C7 C6 C5 121.71(17) . . ?
C5 C6 Cl3 118.71(14) . . ?
C14 C9 C1 120.72(18) . . ?
C10 C9 C1 119.80(16) . . ?
C10 C9 C14 119.47(18) . . ?
Cl4 C8 H8A 109.5 . . ?
Cl4 C8 H8B 109.5 . . ?
C7 C8 Cl4 110.83(13) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C6 C5 Cl2 120.73(14) . . ?
C4 C5 Cl2 119.07(15) . . ?
C4 C5 C6 120.17(17) . . ?
C2 C3 S1 117.88(14) . . ?
C4 C3 S1 119.60(15) . . ?
C4 C3 C2 122.50(17) . . ?
C9 C14 H14 120.1 . . ?
C13 C14 C9 119.9(2) . . ?
C13 C14 H14 120.1 . . ?
C5 C4 C3 118.64(18) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.34(19) . . ?
C11 C10 H10 119.8 . . ?
C14 C13 H13 119.9 . . ?
C14 C13 C12 120.21(19) . . ?
C12 C13 H13 119.9 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.8(2) . . ?
C12 C11 H11 120.1 . . ?
C13 C12 H12 119.9 . . ?
C11 C12 C13 120.28(19) . . ?
C11 C12 H12 119.9 . . ?


_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 1.395
_oxdiff_exptl_absorpt_empirical_full_min 0.811

# start Validation Reply Form
_vrf_THETM01_serc010-r1-rf-fixed 
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.590
RESPONSE: Calculated sin(theta_max)/wavelength is 0.5896.
;
# end Validation Reply Form
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_serc232-r1-rf
_database_code_depnum_ccdc_archive 'CCDC 2101065'
loop_
_audit_author_name
_audit_author_address
'Andryj M Borys'
;University of Kent
United Kingdom
;
_audit_update_record             
;
2021-08-03 deposited with the CCDC.	2021-11-23 downloaded from the CCDC.
;
_audit_creation_date             2018-06-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H12 Cl4 N2 O S'
_chemical_formula_sum            'C16 H12 Cl4 N2 O S'
_chemical_formula_weight         422.14
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 O0.5 S1.5 Cl5 N2 H12'
_chemical_oxdiff_usercomment     ABS-326
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4264(7)
_cell_length_b                   11.9574(11)
_cell_length_c                   11.9660(9)
_cell_angle_alpha                115.075(9)
_cell_angle_beta                 91.228(8)
_cell_angle_gamma                95.201(8)
_cell_volume                     956.37(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3110
_cell_measurement_temperature    99.9(6)
_cell_measurement_theta_max      75.2470
_cell_measurement_theta_min      4.3620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.697
_exptl_absorpt_correction_T_max  0.804
_exptl_absorpt_correction_T_min  0.295
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark yellow'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             428
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 7 0 0.0083
0 -7 0 0.0285
5 1 -1 0.1981
0 -3 8 0.0184
-5 -1 1 0.2010
0 3 -8 0.0092

_exptl_crystal_size_max          0.415
_exptl_crystal_size_mid          0.042
_exptl_crystal_size_min          0.028
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0312 7.1692 -0.4688 0.5104 0.8345 0.2078
0.0997 -7.1988 0.4965 -0.5132 -0.8390 -0.1809
4.7206 0.8631 -0.6378 0.1669 -0.1032 0.9806
0.1614 -2.6202 7.7175 -0.8380 0.5125 0.1874
-4.7074 -0.9746 0.9688 -0.2027 0.1251 -0.9712
-0.1614 2.6202 -7.7175 0.8380 -0.5125 -0.1874

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6147
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         4.088
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2887
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00  -6.00   1.00   12.50    --  -42.45 125.00  90.00   78
  2  ω   -119.00  -8.00   1.00   12.50    --  -42.45 -19.00   0.00  111
  3  ω   -114.00 -41.00   1.00   12.50    --  -42.45 -38.00 -60.00   73
  4  ω     25.00  50.00   1.00   12.50    --   42.45-125.00 -90.00   25
  5  ω     36.00  96.00   1.00   12.50    --   42.45-125.00   0.00   60
  6  ω     82.00 123.00   1.00   37.50    --  111.00  77.00 -30.00   41
  7  ω     64.00 111.00   1.00   37.50    --  111.00-111.00 -60.00   47
  8  ω     47.00 104.00   1.00   37.50    --  111.00 -94.00  90.00   57
  9  ω     84.00 122.00   1.00   37.50    --  111.00  61.00  60.00   38
 10  ω     43.00 137.00   1.00   37.50    --  111.00 -61.00 150.00   94
 11  ω     76.00 103.00   1.00   37.50    --  111.00-111.00  60.00   27
 12  ω     56.00 102.00   1.00   37.50    --  111.00 -94.00 150.00   46
 13  ω     44.00  71.00   1.00   37.50    --  111.00-111.00  60.00   27
 14  ω    127.00 177.00   1.00   37.50    --  111.00  77.00 -30.00   50
 15  ω     36.00 133.00   1.00   37.50    --  111.00 -30.00  30.00   97
 16  ω     37.00 130.00   1.00   37.50    --  111.00 -77.00 -60.00   93
 17  ω    137.00 164.00   1.00   37.50    --  111.00 111.00  90.00   27
 18  ω     45.00 137.00   1.00   37.50    --  111.00 -15.00-180.00   92
 19  ω     89.00 176.00   1.00   37.50    --  111.00  30.00  30.00   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0116791000
_diffrn_orient_matrix_UB_12      0.0654763000
_diffrn_orient_matrix_UB_13      -0.0865942000
_diffrn_orient_matrix_UB_21      -0.0297331000
_diffrn_orient_matrix_UB_22      0.1236541000
_diffrn_orient_matrix_UB_23      0.1090144000
_diffrn_orient_matrix_UB_31      0.2063030000
_diffrn_orient_matrix_UB_32      0.0300649000
_diffrn_orient_matrix_UB_33      0.0301780000
_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             3403
_reflns_odcompleteness_completeness 99.79
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.812
_refine_diff_density_min         -0.836
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3403
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0546
_refine_ls_restrained_S_all      1.056
_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)+(0.0891P)²+0.7585P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1486
_refine_ls_wR_factor_ref         0.1565
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C6(H6), C13(H13), C4(H4)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_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
S1 S 0.79161(11) 0.35654(8) 0.23878(8) 0.0277(2) Uani 1 1 d . . . . .
Cl4 Cl 0.59357(11) 0.69464(8) 0.09023(8) 0.0325(2) Uani 1 1 d . . . . .
Cl3 Cl 0.73734(12) 0.96605(8) 0.36422(9) 0.0356(2) Uani 1 1 d . . . . .
Cl2 Cl 0.78425(13) 0.89984(10) 0.63007(9) 0.0432(3) Uani 1 1 d . . . . .
Cl1 Cl 0.52022(13) 0.24180(9) 0.15522(9) 0.0398(2) Uani 1 1 d . . . . .
O1 O 0.8799(4) 0.3472(3) 0.8957(3) 0.0365(6) Uani 1 1 d . . . . .
N2 N 0.7169(3) 0.5438(3) 0.4935(3) 0.0244(6) Uani 1 1 d . . . . .
N1 N 0.8362(4) 0.3528(3) 0.3659(3) 0.0303(7) Uani 1 1 d . . . . .
C9 C 0.6929(4) 0.5768(3) 0.3978(3) 0.0244(7) Uani 1 1 d . . . . .
C14 C 0.7217(4) 0.5010(3) 0.2748(3) 0.0257(7) Uani 1 1 d . . . . .
C3 C 0.7832(4) 0.5007(3) 0.7027(3) 0.0274(7) Uani 1 1 d . . . . .
H3 H 0.746693 0.576657 0.713007 0.033 Uiso 1 1 calc R . . . .
C7 C 0.8658(4) 0.2996(3) 0.5708(3) 0.0272(7) Uani 1 1 d . . . . .
H7 H 0.887424 0.240718 0.492649 0.033 Uiso 1 1 calc R . . . .
C11 C 0.6077(4) 0.7331(3) 0.3323(3) 0.0245(7) Uani 1 1 d . . . . .
C10 C 0.6349(4) 0.6960(3) 0.4261(3) 0.0247(7) Uani 1 1 d . . . . .
C1 C 0.7825(4) 0.4394(3) 0.4751(3) 0.0256(7) Uani 1 1 d . . . . .
C2 C 0.8115(4) 0.4122(3) 0.5835(3) 0.0252(7) Uani 1 1 d . . . . .
C12 C 0.6355(4) 0.6517(3) 0.2092(3) 0.0266(7) Uani 1 1 d . . . . .
C6 C 0.8888(4) 0.2729(3) 0.6721(3) 0.0280(7) Uani 1 1 d . . . . .
H6 H 0.923063 0.196268 0.661522 0.034 Uiso 1 1 calc R . . . .
C13 C 0.6944(4) 0.5368(3) 0.1788(3) 0.0275(7) Uani 1 1 d . . . . .
H13 H 0.715167 0.485037 0.097666 0.033 Uiso 1 1 calc R . . . .
C15 C 0.6025(5) 0.7761(3) 0.5582(3) 0.0281(7) Uani 1 1 d . . . . .
H15A H 0.592346 0.725439 0.603615 0.034 Uiso 1 1 calc R . . . .
H15B H 0.489127 0.811397 0.561519 0.034 Uiso 1 1 calc R . . . .
C16 C 0.5472(4) 0.8576(3) 0.3583(3) 0.0282(7) Uani 1 1 d . . . . .
H16A H 0.490977 0.889232 0.436635 0.034 Uiso 1 1 calc R . . . .
H16B H 0.457752 0.848878 0.294091 0.034 Uiso 1 1 calc R . . . .
C4 C 0.8083(4) 0.4771(4) 0.8044(4) 0.0311(8) Uani 1 1 d . . . . .
H4 H 0.791169 0.537384 0.882853 0.037 Uiso 1 1 calc R . . . .
C5 C 0.8599(4) 0.3621(3) 0.7900(3) 0.0285(7) Uani 1 1 d . . . . .
C8 C 0.9128(5) 0.2275(4) 0.8859(4) 0.0369(8) Uani 1 1 d . . . . .
H8A H 0.812223 0.167706 0.840268 0.055 Uiso 1 1 calc GR . . . .
H8B H 0.926935 0.230578 0.967170 0.055 Uiso 1 1 calc GR . . . .
H8C H 1.021255 0.203692 0.843756 0.055 Uiso 1 1 calc GR . . . .


_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
S1 Cl1 2.2789(12) . ?
S1 N1 1.570(3) . ?
S1 C14 1.726(3) . ?
Cl4 C12 1.736(4) . ?
Cl3 C16 1.808(3) . ?
Cl2 C15 1.806(4) . ?
O1 C5 1.357(4) . ?
O1 C8 1.431(4) . ?
N2 C9 1.373(4) . ?
N2 C1 1.314(4) . ?
N1 C1 1.374(5) . ?
C9 C14 1.398(5) . ?
C9 C10 1.429(5) . ?
C14 C13 1.402(5) . ?
C3 H3 0.9300 . ?
C3 C2 1.405(5) . ?
C3 C4 1.374(5) . ?
C7 H7 0.9300 . ?
C7 C2 1.387(5) . ?
C7 C6 1.389(5) . ?
C11 C10 1.387(5) . ?
C11 C12 1.412(5) . ?
C11 C16 1.499(5) . ?
C10 C15 1.499(5) . ?
C1 C2 1.481(5) . ?
C12 C13 1.380(5) . ?
C6 H6 0.9300 . ?
C6 C5 1.398(5) . ?
C13 H13 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C4 H4 0.9300 . ?
C4 C5 1.401(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

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
N1 S1 Cl1 108.85(12) . . ?
N1 S1 C14 105.86(17) . . ?
C14 S1 Cl1 97.49(11) . . ?
C5 O1 C8 118.2(3) . . ?
C1 N2 C9 120.7(3) . . ?
C1 N1 S1 121.8(3) . . ?
N2 C9 C14 124.0(3) . . ?
N2 C9 C10 117.9(3) . . ?
C14 C9 C10 118.1(3) . . ?
C9 C14 S1 118.8(3) . . ?
C9 C14 C13 122.7(3) . . ?
C13 C14 S1 118.5(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C4 C3 C2 121.2(3) . . ?
C2 C7 H7 119.2 . . ?
C2 C7 C6 121.6(3) . . ?
C6 C7 H7 119.2 . . ?
C10 C11 C12 119.6(3) . . ?
C10 C11 C16 121.5(3) . . ?
C12 C11 C16 118.9(3) . . ?
C9 C10 C15 117.7(3) . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 C15 122.4(3) . . ?
N2 C1 N1 127.3(3) . . ?
N2 C1 C2 117.8(3) . . ?
N1 C1 C2 114.9(3) . . ?
C3 C2 C1 120.3(3) . . ?
C7 C2 C3 118.2(3) . . ?
C7 C2 C1 121.5(3) . . ?
C11 C12 Cl4 120.0(3) . . ?
C13 C12 Cl4 117.9(3) . . ?
C13 C12 C11 122.1(3) . . ?
C7 C6 H6 120.3 . . ?
C7 C6 C5 119.4(3) . . ?
C5 C6 H6 120.3 . . ?
C14 C13 H13 121.2 . . ?
C12 C13 C14 117.6(3) . . ?
C12 C13 H13 121.2 . . ?
Cl2 C15 H15A 109.4 . . ?
Cl2 C15 H15B 109.4 . . ?
C10 C15 Cl2 111.4(2) . . ?
C10 C15 H15A 109.4 . . ?
C10 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
Cl3 C16 H16A 109.5 . . ?
Cl3 C16 H16B 109.5 . . ?
C11 C16 Cl3 110.7(2) . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
O1 C5 C6 124.8(3) . . ?
O1 C5 C4 115.6(3) . . ?
C6 C5 C4 119.6(3) . . ?
O1 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
O1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.233 0.000 0.000 150.7 60.2 ?


_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 1.742
_oxdiff_exptl_absorpt_empirical_full_min 0.521

# start Validation Reply Form
_vrf_PLAT230_serc232-r1-rf       
;
PROBLEM: Hirshfeld Test Diff for   Cl1      --S1        .        6.5 s.u.  
RESPONSE: Disorder due to thermal motion of Cl1 and S1 atoms are expected
along different axes.
;
_vrf_PLAT340_serc232-r1-rf       
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00513 Ang.  
RESPONSE: Weakly diffracting sample with highly disordered solvent
results in low bond precision in the C-C bonds.
;
# end Validation Reply Form
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_serc211-r1-rf
_database_code_depnum_ccdc_archive 'CCDC 2101070'
loop_
_audit_author_name
_audit_author_address
'Andryj M Borys'
;University of Kent
United Kingdom
;
_audit_update_record             
;
2021-08-03 deposited with the CCDC.	2021-11-23 downloaded from the CCDC.
;
_audit_creation_date             2018-06-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H9.88 Cl4.12 N2 S'
_chemical_formula_sum            'C15 H9.88 Cl4.12 N2 S'
_chemical_formula_weight         396.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'S1 N2 Cl4 C15 H10'
_chemical_oxdiff_usercomment     
'ABS-284 - Recrystallised (Partial chlorination)'
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                   7.8074(3)
_cell_length_b                   15.8724(4)
_cell_length_c                   13.5003(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.795(3)
_cell_angle_gamma                90
_cell_volume                     1609.82(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12836
_cell_measurement_temperature    100.0(6)
_cell_measurement_theta_max      74.5590
_cell_measurement_theta_min      4.3690
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.049
_exptl_absorpt_correction_T_max  0.833
_exptl_absorpt_correction_T_min  0.244
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark yellow'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       trapezoid
_exptl_crystal_F_000             800
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 4 8 0.0345
5 3 -2 0.1193
0 -4 -8 0.0179
-3 0 -5 0.0957
0 -10 1 0.0145
3 0 5 0.1027
0 10 -1 0.0101

_exptl_crystal_size_max          0.315
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.03
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0028 4.2972 7.6619 0.1509 0.6281 -0.7634
4.8900 2.7008 -2.4762 -0.1629 -0.6831 -0.7119
0.0157 -4.2911 -7.6702 -0.1514 -0.6300 0.7617
-3.3915 0.0647 -4.6721 -0.4593 0.1110 0.8813
-0.4487 -10.2499 0.6204 0.8490 -0.2026 0.4879
3.3769 -0.4008 4.6927 0.4872 -0.1176 -0.8654
0.2603 10.2477 -0.8792 -0.8740 0.2087 -0.4387

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22798
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.907
_diffrn_reflns_theta_min         4.398
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2887
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00  30.00   1.00   10.00    --  -42.45  38.00 -90.00   95
  2  ω   -113.00 -16.00   1.00   10.00    --  -42.45 -57.00 -30.00   97
  3  ω    -74.00  31.00   1.00   10.00    --  -42.45  77.00 -90.00  105
  4  ω    -69.00  28.00   1.00   10.00    --  -42.45  57.00 120.00   97
  5  ω     23.00  97.00   1.00   10.00    --   42.45-125.00-180.00   74
  6  ω     38.00 134.00   1.00   30.00    --  109.57 -45.00 150.00   96
  7  ω     28.00 109.00   1.00   30.00    --  109.57 -94.00  90.00   81
  8  ω     38.00 122.00   1.00   30.00    --  109.57-125.00 -90.00   84
  9  ω     36.00 141.00   1.00   30.00    --  109.57 -77.00 150.00  105
 10  ω     94.00 178.00   1.00   30.00    --  109.57 125.00 150.00   84
 11  ω     86.00 178.00   1.00   30.00    --  109.57  30.00-150.00   92
 12  ω     38.00 122.00   1.00   30.00    --  109.57-125.00  30.00   84
 13  ω     35.00 133.00   1.00   30.00    --  109.57 -30.00-120.00   98
 14  ω     98.00 178.00   1.00   30.00    --  109.57  85.00-140.00   80
 15  ω     94.00 178.00   1.00   30.00    --  109.57 125.00  60.00   84
 16  ω     86.00 178.00   1.00   30.00    --  109.57  30.00 120.00   92
 17  ω     38.00 134.00   1.00   30.00    --  109.57 -45.00  60.00   96
 18  ω   -113.00 -16.00   1.00   10.00    --  -42.45 -57.00-120.00   97
 19  ω   -116.00 -11.00   1.00   10.00    --  -42.45 -77.00-180.00  105
 20  ω   -113.00 -16.00   1.00   10.00    --  -42.45 -57.00  60.00   97
 21  ω   -116.00 -11.00   1.00   10.00    --  -42.45 -77.00  30.00  105
 22  ω      1.00  82.00   1.00   10.00    --   42.45 -99.00  30.00   81
 23  ω     86.00 178.00   1.00   30.00    --  109.57  30.00  60.00   92
 24  ω     64.00 178.00   1.00   30.00    --  109.57  15.00   0.00  114
 25  ω     82.00 178.00   1.00   30.00    --  109.57  61.00   0.00   96
 26  ω     82.00 178.00   1.00   30.00    --  109.57  61.00 150.00   96
 27  ω     86.00 178.00   1.00   30.00    --  109.57  30.00 -90.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0442674000
_diffrn_orient_matrix_UB_12      -0.0808354000
_diffrn_orient_matrix_UB_13      0.0650528000
_diffrn_orient_matrix_UB_21      -0.1225484000
_diffrn_orient_matrix_UB_22      0.0291048000
_diffrn_orient_matrix_UB_23      0.0656030000
_diffrn_orient_matrix_UB_31      -0.1582905000
_diffrn_orient_matrix_UB_32      -0.0451727000
_diffrn_orient_matrix_UB_33      -0.0743564000
_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                2898
_reflns_number_total             2931
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.163
_refine_diff_density_min         -0.735
_refine_diff_density_rms         0.117
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.318
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2931
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0744
_refine_ls_restrained_S_all      1.318
_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)+(0.0220P)²+12.6400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1732
_refine_ls_wR_factor_ref         0.1733
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(Cl4)=1-FVAR(1)
 Sof(H10)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C14(H14)
3.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C3(H3), C7(H7), C4(H4), C6(H6), C5(H5)
3.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_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
S1 S 0.84506(18) 0.39968(9) 0.40060(11) 0.0241(3) Uani 1 1 d . . . . .
Cl5 Cl 0.6242(2) 0.60272(10) 0.06882(11) 0.0324(4) Uani 1 1 d . . . . .
Cl2 Cl 0.7721(2) 0.74661(10) 0.49881(13) 0.0365(4) Uani 1 1 d . . . . .
Cl1 Cl 0.6129(2) 0.30808(9) 0.34394(14) 0.0351(4) Uani 1 1 d . . . . .
N2 N 0.7004(6) 0.5379(3) 0.5081(4) 0.0186(10) Uani 1 1 d . . . . .
N1 N 0.8770(6) 0.4125(3) 0.5193(4) 0.0246(11) Uani 1 1 d . . . . .
C1 C 0.7875(7) 0.4735(4) 0.5589(5) 0.0207(12) Uani 1 1 d . . . . .
C8 C 0.6892(7) 0.5495(3) 0.4064(4) 0.0195(11) Uani 1 1 d . . . . .
C12 C 0.7229(7) 0.5033(4) 0.2365(5) 0.0233(12) Uani 1 1 d . . . . .
C13 C 0.7420(7) 0.4902(4) 0.3422(4) 0.0210(12) Uani 1 1 d . . . . .
C2 C 0.8013(7) 0.4665(4) 0.6703(5) 0.0232(12) Uani 1 1 d . . . . .
C11 C 0.6515(7) 0.5802(4) 0.1973(5) 0.0242(12) Uani 1 1 d . . . . .
C10 C 0.6015(7) 0.6414(4) 0.2585(5) 0.0240(13) Uani 1 1 d . . . . .
H10 H 0.556113 0.692489 0.229190 0.029 Uiso 0.877(7) 1 calc R . P A 1
C9 C 0.6179(7) 0.6276(4) 0.3606(5) 0.0219(12) Uani 1 1 d . . . . .
C3 C 0.7318(8) 0.5308(4) 0.7186(5) 0.0272(13) Uani 1 1 d . . . . .
H3 H 0.680264 0.577994 0.681375 0.033 Uiso 1 1 calc R . . . .
C7 C 0.8829(7) 0.3968(4) 0.7269(5) 0.0251(13) Uani 1 1 d . . . . .
H7 H 0.930821 0.354234 0.695273 0.030 Uiso 1 1 calc R . . . .
C4 C 0.7401(8) 0.5241(4) 0.8213(5) 0.0291(14) Uani 1 1 d . . . . .
H4 H 0.691645 0.566371 0.853042 0.035 Uiso 1 1 calc R . . . .
C6 C 0.8919(8) 0.3917(4) 0.8305(5) 0.0312(14) Uani 1 1 d . . . . .
H6 H 0.946633 0.345434 0.868545 0.037 Uiso 1 1 calc R . . . .
C5 C 0.8203(8) 0.4545(4) 0.8784(5) 0.0314(14) Uani 1 1 d . . . . .
H5 H 0.825752 0.450341 0.947924 0.038 Uiso 1 1 calc R . . . .
C15 C 0.7767(8) 0.4371(4) 0.1710(5) 0.0287(13) Uani 1 1 d . . . . .
H15A H 0.872577 0.458034 0.145992 0.043 Uiso 1 1 calc GR . . . .
H15B H 0.677015 0.423601 0.113721 0.043 Uiso 1 1 calc GR . . . .
H15C H 0.814996 0.387320 0.211395 0.043 Uiso 1 1 calc GR . . . .
C14 C 0.5729(8) 0.6918(4) 0.4315(5) 0.0291(14) Uani 1 1 d . . . . .
H14 H 0.523094 0.662982 0.481590 0.035 Uiso 1 1 calc R . . . .
Cl3 Cl 0.4179(2) 0.76932(11) 0.36451(16) 0.0441(5) Uani 1 1 d . . . . .
Cl4 Cl 0.5106(15) 0.7300(7) 0.2167(9) 0.025(4) Uani 0.123(7) 1 d . . P A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 Cl1 2.287(2) . ?
S1 N1 1.567(5) . ?
S1 C13 1.729(6) . ?
Cl5 C11 1.726(6) . ?
Cl2 C14 1.798(7) . ?
N2 C1 1.313(7) . ?
N2 C8 1.365(7) . ?
N1 C1 1.383(7) . ?
C1 C2 1.483(8) . ?
C8 C13 1.415(8) . ?
C8 C9 1.428(8) . ?
C12 C13 1.408(8) . ?
C12 C11 1.386(8) . ?
C12 C15 1.505(8) . ?
C2 C3 1.398(8) . ?
C2 C7 1.396(8) . ?
C11 C10 1.398(9) . ?
C10 H10 0.9300 . ?
C10 C9 1.366(9) . ?
C10 Cl4 1.608(12) . ?
C9 C14 1.504(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(9) . ?
C7 H7 0.9300 . ?
C7 C6 1.384(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.393(9) . ?
C6 H6 0.9300 . ?
C6 C5 1.387(9) . ?
C5 H5 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C14 H14 0.9800 . ?
C14 Cl3 1.790(6) . ?

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
N1 S1 Cl1 108.4(2) . . ?
N1 S1 C13 106.5(3) . . ?
C13 S1 Cl1 98.51(19) . . ?
C1 N2 C8 120.8(5) . . ?
C1 N1 S1 122.0(4) . . ?
N2 C1 N1 126.0(5) . . ?
N2 C1 C2 118.2(5) . . ?
N1 C1 C2 115.7(5) . . ?
N2 C8 C13 125.3(5) . . ?
N2 C8 C9 117.6(5) . . ?
C13 C8 C9 117.1(5) . . ?
C13 C12 C15 121.5(5) . . ?
C11 C12 C13 115.9(5) . . ?
C11 C12 C15 122.6(6) . . ?
C8 C13 S1 116.8(4) . . ?
C12 C13 S1 119.5(4) . . ?
C12 C13 C8 123.7(5) . . ?
C3 C2 C1 119.2(5) . . ?
C7 C2 C1 120.7(5) . . ?
C7 C2 C3 120.1(6) . . ?
C12 C11 Cl5 119.5(5) . . ?
C12 C11 C10 122.3(6) . . ?
C10 C11 Cl5 118.2(5) . . ?
C11 C10 H10 119.3 . . ?
C11 C10 Cl4 124.6(6) . . ?
C9 C10 C11 121.4(5) . . ?
C9 C10 H10 119.3 . . ?
C9 C10 Cl4 113.9(6) . . ?
Cl4 C10 H10 6.2 . . ?
C8 C9 C14 116.3(5) . . ?
C10 C9 C8 119.6(5) . . ?
C10 C9 C14 124.0(5) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.7(6) . . ?
C4 C3 H3 120.1 . . ?
C2 C7 H7 120.3 . . ?
C6 C7 C2 119.3(6) . . ?
C6 C7 H7 120.3 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.7(6) . . ?
C5 C4 H4 119.7 . . ?
C7 C6 H6 119.6 . . ?
C7 C6 C5 120.9(6) . . ?
C5 C6 H6 119.6 . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.3(6) . . ?
C6 C5 H5 120.3 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
Cl2 C14 H14 109.2 . . ?
C9 C14 Cl2 109.3(4) . . ?
C9 C14 H14 109.2 . . ?
C9 C14 Cl3 112.8(5) . . ?
Cl3 C14 Cl2 107.2(3) . . ?
Cl3 C14 H14 109.2 . . ?


_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 1.425
_oxdiff_exptl_absorpt_empirical_full_min 0.603

# start Validation Reply Form
_vrf_PLAT077_serc211-r1-rf       
;
PROBLEM: Unitcell Contains Non-integer Number of Atoms ..     Please Check
RESPONSE: Partial chlorination at C10.
;
_vrf_PLAT340_serc211-r1-rf       
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0088 Ang.  
RESPONSE: Substitutional disorder due to partial chlorination at C10
results in low bond precision in the C-C bonds.
;
# end Validation Reply Form
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_serc256-r1-rf
_database_code_depnum_ccdc_archive 'CCDC 2101064'
loop_
_audit_author_name
_audit_author_address
'Andryj M Borys'
;University of Kent
United Kingdom
;
_audit_update_record             
;
2021-08-03 deposited with the CCDC.	2021-11-23 downloaded from the CCDC.
;
_audit_creation_date             2018-06-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 Cl4 N2 S'
_chemical_formula_sum            'C15 H10 Cl4 N2 S'
_chemical_formula_weight         392.11
_chemical_melting_point          ?
_chemical_oxdiff_formula         'S1 N2 Cl4 C15 H10'
_chemical_oxdiff_usercomment     ABS-551
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                   7.38990(10)
_cell_length_b                   10.5325(2)
_cell_length_c                   20.5855(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.598(2)
_cell_angle_gamma                90
_cell_volume                     1591.64(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10953
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      75.2570
_cell_measurement_theta_min      4.7080
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.949
_exptl_absorpt_correction_T_max  0.793
_exptl_absorpt_correction_T_min  0.317
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light orange'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             792
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 6 7 0.0163
5 0 -2 0.1913
0 -6 -7 0.0190
-5 0 2 0.1786
0 -4 11 0.0136
0 4 -11 0.0181

_exptl_crystal_size_max          0.377
_exptl_crystal_size_mid          0.042
_exptl_crystal_size_min          0.038
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0470 5.7773 7.0815 0.3328 0.9419 0.0462
4.7927 -0.1024 -2.1338 0.0071 0.0177 -0.9998
0.1422 -5.7707 -7.1525 -0.3319 -0.9394 -0.0856
-4.7864 0.1820 2.3897 0.0093 -0.0020 1.0000
-0.1265 -3.6364 11.2718 0.9414 -0.3326 0.0571
0.2849 3.6203 -11.3200 -0.9391 0.3317 -0.0901

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            19045
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.489
_diffrn_reflns_theta_min         4.324
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2887
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -113.00 -16.00   1.00    3.00    --  -42.70 -57.00  90.00   97
  2  ω    -69.00  27.00   1.00    3.00    --  -42.70  57.00-120.00   96
  3  ω    -65.00  30.00   1.00    3.00    --  -42.70  38.00  30.00   95
  4  ω      1.00  83.00   1.00    3.00    --   42.70 -99.00  30.00   82
  5  ω      1.00  83.00   1.00    3.00    --   42.70 -99.00 -60.00   82
  6  ω     31.00 156.00   1.00   12.50    --  111.00 -15.00   0.00  125
  7  ω     36.00 116.00   1.00   12.50    --  111.00-111.00-150.00   80
  8  ω     87.00 178.00   1.00   12.50    --  111.00  45.00  90.00   91
  9  ω     66.00 178.00   1.00   12.50    --  111.00  15.00-120.00  112
 10  ω    100.00 178.00   1.00   12.50    --  111.00 111.00 -90.00   78
 11  ω     87.00 178.00   1.00   12.50    --  111.00  45.00-180.00   91
 12  ω    100.00 178.00   1.00   12.50    --  111.00 111.00-150.00   78
 13  ω     36.00 116.00   1.00   12.50    --  111.00-111.00 -90.00   80
 14  ω     30.00 109.00   1.00   12.50    --  111.00 -94.00 -30.00   79
 15  ω     37.00 116.00   1.00   12.50    --  111.00-111.00  60.00   79
 16  ω     71.00 116.00   1.00   12.50    --  111.00-111.00 -30.00   45
 17  ω     52.00  83.00   1.00   12.50    --  111.00 -45.00 150.00   31
 18  ω     90.00 116.00   1.00   12.50    --  111.00-111.00 150.00   26
 19  ω    116.00 176.00   1.00   12.50    --  111.00 111.00  30.00   60
 20  ω     42.00  86.00   1.00   12.50    --  111.00 -45.00   0.00   44
 21  ω     94.00 135.00   1.00   12.50    --  111.00 -45.00   0.00   41
 22  ω     60.00  87.00   1.00   12.50    --  111.00 -94.00-150.00   27
 23  ω     31.00  69.00   1.00   12.50    --  111.00 -94.00 -60.00   38
 24  ω     31.00  60.00   1.00   12.50    --  111.00 -94.00  30.00   29
 25  ω     98.00 125.00   1.00   12.50    --  111.00  45.00 120.00   27
 26  ω    148.00 175.00   1.00   12.50    --  111.00  45.00 120.00   27
 27  ω     69.00 108.00   1.00   12.50    --  111.00 -77.00  30.00   39
 28  ω     69.00 107.00   1.00   12.50    --  111.00 -94.00 120.00   38
 29  ω     58.00 114.00   1.00   12.50    --  111.00-111.00  30.00   56
 30  ω     88.00 178.00   1.00   12.50    --  111.00  45.00   0.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0334482000
_diffrn_orient_matrix_UB_12      -0.0326049000
_diffrn_orient_matrix_UB_13      0.0733706000
_diffrn_orient_matrix_UB_21      0.0141451000
_diffrn_orient_matrix_UB_22      0.1425241000
_diffrn_orient_matrix_UB_23      0.0166349000
_diffrn_orient_matrix_UB_31      -0.2066450000
_diffrn_orient_matrix_UB_32      0.0045270000
_diffrn_orient_matrix_UB_33      0.0042072000
_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                3031
_reflns_number_total             3201
_reflns_odcompleteness_completeness 99.97
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.262
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.057
_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)+(0.0552P)²+3.3699P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1198
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C3(H3), C6(H6), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_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
S1 S 0.14967(9) 0.75980(6) 0.52057(3) 0.02383(17) Uani 1 1 d . . . . .
Cl1 Cl 0.41138(10) 0.84450(7) 0.57457(3) 0.03172(19) Uani 1 1 d . . . . .
Cl4 Cl 0.26055(11) 0.94928(8) 0.28505(4) 0.0362(2) Uani 1 1 d . . . . .
Cl3 Cl 0.34887(11) 0.67988(8) 0.23875(3) 0.0356(2) Uani 1 1 d . . . . .
Cl2 Cl 0.17832(11) 0.37081(8) 0.31840(4) 0.0425(2) Uani 1 1 d . . . . .
N2 N 0.2841(3) 0.5170(2) 0.46684(11) 0.0221(5) Uani 1 1 d . . . . .
N1 N 0.1363(3) 0.6227(2) 0.54952(12) 0.0255(5) Uani 1 1 d . . . . .
C2 C 0.2318(3) 0.4061(3) 0.56451(13) 0.0223(5) Uani 1 1 d . . . . .
C8 C 0.2710(3) 0.6203(3) 0.42611(13) 0.0213(5) Uani 1 1 d . . . . .
C12 C 0.2119(3) 0.8475(3) 0.40080(13) 0.0219(5) Uani 1 1 d . . . . .
C1 C 0.2211(3) 0.5223(3) 0.52323(13) 0.0214(5) Uani 1 1 d . . . . .
C7 C 0.1821(4) 0.4103(3) 0.62745(14) 0.0234(5) Uani 1 1 d . . . . .
H7 H 0.140698 0.485927 0.643741 0.028 Uiso 1 1 calc R . . . .
C13 C 0.2167(3) 0.7429(3) 0.44355(13) 0.0206(5) Uani 1 1 d . . . . .
C15 C 0.1576(4) 0.9806(3) 0.42083(15) 0.0274(6) Uani 1 1 d . . . . .
H15A H 0.056847 1.010100 0.391086 0.041 Uiso 1 1 calc GR . . . .
H15B H 0.259029 1.037189 0.419650 0.041 Uiso 1 1 calc GR . . . .
H15C H 0.122976 0.978086 0.464348 0.041 Uiso 1 1 calc GR . . . .
C3 C 0.2917(4) 0.2921(3) 0.53984(14) 0.0253(6) Uani 1 1 d . . . . .
H3 H 0.323457 0.288647 0.497454 0.030 Uiso 1 1 calc R . . . .
C6 C 0.1938(4) 0.3023(3) 0.66614(14) 0.0266(6) Uani 1 1 d . . . . .
H6 H 0.160442 0.305721 0.708313 0.032 Uiso 1 1 calc R . . . .
C11 C 0.2583(4) 0.8237(3) 0.33880(14) 0.0248(6) Uani 1 1 d . . . . .
C9 C 0.3163(4) 0.5997(3) 0.36166(14) 0.0237(5) Uani 1 1 d . . . . .
C10 C 0.3056(4) 0.7007(3) 0.31903(13) 0.0250(6) Uani 1 1 d . . . . .
C4 C 0.3038(4) 0.1841(3) 0.57836(16) 0.0278(6) Uani 1 1 d . . . . .
H4 H 0.344198 0.108292 0.561887 0.033 Uiso 1 1 calc R . . . .
C5 C 0.2554(4) 0.1887(3) 0.64194(15) 0.0288(6) Uani 1 1 d . . . . .
H5 H 0.264301 0.116293 0.667968 0.035 Uiso 1 1 calc R . . . .
C14 C 0.3746(4) 0.4687(3) 0.34361(16) 0.0296(6) Uani 1 1 d . . . . .
H14A H 0.446031 0.430027 0.380909 0.035 Uiso 1 1 calc R . . . .
H14B H 0.450436 0.474389 0.308276 0.035 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
S1 Cl1 2.2974(10) . ?
S1 N1 1.570(2) . ?
S1 C13 1.724(3) . ?
Cl4 C11 1.726(3) . ?
Cl3 C10 1.733(3) . ?
Cl2 C14 1.806(3) . ?
N2 C8 1.370(4) . ?
N2 C1 1.300(4) . ?
N1 C1 1.372(3) . ?
C2 C1 1.487(4) . ?
C2 C7 1.387(4) . ?
C2 C3 1.396(4) . ?
C8 C13 1.411(4) . ?
C8 C9 1.422(4) . ?
C12 C13 1.408(4) . ?
C12 C15 1.527(4) . ?
C12 C11 1.382(4) . ?
C7 H7 0.9300 . ?
C7 C6 1.385(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C3 H3 0.9300 . ?
C3 C4 1.383(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.393(4) . ?
C11 C10 1.414(4) . ?
C9 C10 1.376(4) . ?
C9 C14 1.505(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.397(4) . ?
C5 H5 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?

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
N1 S1 Cl1 105.06(10) . . ?
N1 S1 C13 106.95(13) . . ?
C13 S1 Cl1 99.80(9) . . ?
C1 N2 C8 120.4(2) . . ?
C1 N1 S1 120.5(2) . . ?
C7 C2 C1 120.3(3) . . ?
C7 C2 C3 119.7(3) . . ?
C3 C2 C1 119.9(2) . . ?
N2 C8 C13 125.0(2) . . ?
N2 C8 C9 116.2(2) . . ?
C13 C8 C9 118.8(3) . . ?
C13 C12 C15 122.5(2) . . ?
C11 C12 C13 116.4(3) . . ?
C11 C12 C15 121.1(3) . . ?
N2 C1 N1 127.7(3) . . ?
N2 C1 C2 118.3(2) . . ?
N1 C1 C2 113.9(2) . . ?
C2 C7 H7 119.8 . . ?
C6 C7 C2 120.3(3) . . ?
C6 C7 H7 119.8 . . ?
C8 C13 S1 116.7(2) . . ?
C12 C13 S1 120.3(2) . . ?
C12 C13 C8 123.0(2) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 120.0 . . ?
C7 C6 H6 120.0 . . ?
C7 C6 C5 120.1(3) . . ?
C5 C6 H6 120.0 . . ?
C12 C11 Cl4 118.3(2) . . ?
C12 C11 C10 121.9(3) . . ?
C10 C11 Cl4 119.8(2) . . ?
C8 C9 C14 118.4(3) . . ?
C10 C9 C8 118.3(3) . . ?
C10 C9 C14 123.3(3) . . ?
C11 C10 Cl3 118.0(2) . . ?
C9 C10 Cl3 120.4(2) . . ?
C9 C10 C11 121.5(3) . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.1(3) . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 119.6(3) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
Cl2 C14 H14A 109.5 . . ?
Cl2 C14 H14B 109.5 . . ?
C9 C14 Cl2 110.57(19) . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?


_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 1.363
_oxdiff_exptl_absorpt_empirical_full_min 0.597

# start Validation Reply Form
_vrf_PLAT094_serc256-r1-rf       
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       2.50 Report
RESPONSE: Small residual electron density in close proximity to the C12/15
methyl group potentially indicative of very minor partial chlorination at 
this position.
;
# end Validation Reply Form
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_serc079-r1-rf
_database_code_depnum_ccdc_archive 'CCDC 2101075'
loop_
_audit_author_name
_audit_author_address
'Andryj M Borys'
;University of Kent
United Kingdom
;
_audit_update_record             
;
2021-08-03 deposited with the CCDC.	2021-11-23 downloaded from the CCDC.
;
_audit_creation_date             2018-06-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C15 H10 Cl3 N2 S)'
_chemical_formula_sum            'C30 H20 Cl6 N4 S2'
_chemical_formula_weight         713.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'N4 S4 Cl6 C30 H20'
_chemical_oxdiff_usercomment     3,5-dimethyl-S-Radical
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9369(4)
_cell_length_b                   12.2664(4)
_cell_length_c                   13.3652(5)
_cell_angle_alpha                91.036(3)
_cell_angle_beta                 107.068(4)
_cell_angle_gamma                109.355(3)
_cell_volume                     1457.25(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    14186
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.1990
_cell_measurement_theta_min      3.8030
_shelx_estimated_absorpt_T_max   0.731
_shelx_estimated_absorpt_T_min   0.252
_exptl_absorpt_coefficient_mu    6.970
_exptl_absorpt_correction_T_max  0.759
_exptl_absorpt_correction_T_min  0.256
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark violet'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rhombohedral
_exptl_crystal_F_000             724
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-6 6 3 0.0738
0 -7 -1 0.0980
0 0 -8 0.0238
0 7 1 0.0650
6 -5 -3 0.0815
0 -1 8 0.0121

_exptl_crystal_size_max          0.273
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.048
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-5.5794 5.8470 3.0424 -0.2924 0.0370 0.9556
-0.1463 -7.1857 -1.0835 -0.6900 0.0913 -0.7180
0.4386 -0.1618 -8.3819 0.0241 0.9651 -0.2608
-0.1144 7.4146 0.6036 0.6703 -0.0160 0.7419
5.8144 -5.3348 -3.3630 0.3742 -0.0108 -0.9273
0.0007 -0.9980 8.0043 -0.0663 -0.9562 0.1141

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29597
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.061
_diffrn_reflns_theta_min         3.488
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2887
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -16.00   1.00    5.00    --  -40.39 -38.00  30.00   99
  2  ω   -120.00   1.00   1.00    5.00    --  -40.39 -19.00  90.00  121
  3  ω    -95.00  -2.00   1.00    5.00    --  -40.39 125.00-180.00   93
  4  ω      4.00  33.00   1.00    5.00    --   40.39  89.00  55.03   29
  5  ω     23.00  96.00   1.00    5.00    --   40.39-125.00   0.00   73
  6  ω     23.00  96.00   1.00    5.00    --   40.39-125.00-180.00   73
  7  ω     16.00 115.00   1.00    5.00    --   40.39  38.00 -30.00   99
  8  ω     36.00 116.00   1.00   17.50    --  112.00-111.00  30.00   80
  9  ω     40.00 141.00   1.00   17.50    --  112.00 -61.00  30.00  101
 10  ω     39.00 138.00   1.00   17.50    --  112.00 -45.00 166.81   99
 11  ω     36.00 116.00   1.00   17.50    --  112.00-111.00  60.00   80
 12  ω     57.00 151.00   1.00   17.50    --  112.00 178.00   0.00   94
 13  ω     57.00 151.00   1.00   17.50    --  112.00 178.00  90.00   94
 14  ω    100.00 178.00   1.00   17.50    --  112.00 111.00   0.00   78
 15  ω     36.00 116.00   1.00   17.50    --  112.00-111.00 -30.00   80
 16  ω     36.00 116.00   1.00   17.50    --  112.00-111.00-150.00   80
 17  ω     83.00 178.00   1.00   17.50    --  112.00  61.00-180.00   95
 18  ω     29.00 109.00   1.00   17.50    --  112.00 -94.00  30.00   80
 19  ω     36.00 116.00   1.00   17.50    --  112.00-111.00 -90.00   80
 20  ω     57.00 151.00   1.00   17.50    --  112.00 178.00 150.00   94
 21  ω     36.00 116.00   1.00   17.50    --  112.00-111.00-180.00   80
 22  ω     29.00 109.00   1.00   17.50    --  112.00 -94.00  60.00   80
 23  ω     57.00 151.00   1.00   17.50    --  112.00 178.00 -30.00   94
 24  ω     86.00 178.00   1.00   17.50    --  112.00  45.00 150.00   92
 25  ω     57.00 151.00   1.00   17.50    --  112.00 178.00  30.00   94
 26  ω     79.00 178.00   1.00   17.50    --  112.00  77.00-150.00   99
 27  ω     79.00 178.00   1.00   17.50    --  112.00  77.00  90.00   99
 28  ω     40.00 141.00   1.00   17.50    --  112.00 -61.00  90.00  101
 29  ω     83.00 178.00   1.00   17.50    --  112.00  61.00 120.00   95
 30  ω     83.00 178.00   1.00   17.50    --  112.00  61.00  60.00   95
 31  ω     84.00 178.00   1.00   17.50    --  112.00  30.00-180.00   94
 32  ω     26.00 178.00   1.00   17.50    --  112.00   5.00 -57.00  152
 33  ω     29.00 109.00   1.00   17.50    --  112.00 -94.00 120.00   80
 34  ω     29.00 109.00   1.00   17.50    --  112.00 -94.00  90.00   80
 35  ω     86.00 178.00   1.00   17.50    --  112.00  45.00 -60.00   92
 36  ω     39.00 138.00   1.00   17.50    --  112.00 -45.00-180.00   99
 37  ω     40.00 141.00   1.00   17.50    --  112.00 -61.00-150.00  101
 38  ω     36.00 145.00   1.00   17.50    --  112.00 -77.00-180.00  109
 39  ω     81.00 140.00   1.00   17.50    --  112.00 -26.00-169.80   59
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1510701000
_diffrn_orient_matrix_UB_12      0.0924662000
_diffrn_orient_matrix_UB_13      0.0032386000
_diffrn_orient_matrix_UB_21      -0.0645135000
_diffrn_orient_matrix_UB_22      0.0064988000
_diffrn_orient_matrix_UB_23      -0.1186400000
_diffrn_orient_matrix_UB_31      -0.0551742000
_diffrn_orient_matrix_UB_32      0.0970678000
_diffrn_orient_matrix_UB_33      0.0263586000
_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                5213
_reflns_number_total             5631
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.233
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.160
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         5631
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0679
_refine_ls_restrained_S_all      1.080
_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)+(0.1130P)²+3.1661P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1871
_refine_ls_wR_factor_ref         0.1907
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C29(H29A,H29B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C22(H22), C18(H18), C5(H5), C4(H4), C21(H21), C6(H6),
 C20(H20), C19(H19)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C30(H30A,H30B,H30C)
;
_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
S2 S 0.73823(10) 0.06256(7) 0.43970(7) 0.0257(2) Uani 1 1 d . . . . .
S1 S 0.97235(10) 0.27904(7) 0.45578(7) 0.0252(2) Uani 1 1 d . . . . .
Cl1 Cl 0.88169(11) 0.51168(8) 0.75960(7) 0.0318(2) Uani 1 1 d . . . . .
Cl4 Cl 0.30069(10) 0.23794(8) 0.41171(7) 0.0320(2) Uani 1 1 d . . . . .
Cl6 Cl 0.44562(12) 0.16247(9) 0.06406(7) 0.0363(3) Uani 1 1 d . . . . .
Cl3 Cl 1.19967(11) 0.22538(9) 0.86488(8) 0.0363(3) Uani 1 1 d . . . . .
Cl2 Cl 1.21619(12) 0.52161(10) 0.97589(8) 0.0428(3) Uani 1 1 d . . . . .
Cl5 Cl 0.08090(12) 0.12984(10) 0.14037(10) 0.0478(3) Uani 1 1 d . . . . .
N2 N 0.8302(3) 0.4248(3) 0.5443(2) 0.0258(6) Uani 1 1 d . . . . .
N4 N 0.5504(3) 0.1686(3) 0.5233(2) 0.0262(6) Uani 1 1 d . . . . .
N1 N 0.8643(3) 0.3452(3) 0.3914(2) 0.0260(6) Uani 1 1 d . . . . .
N3 N 0.7367(4) 0.0762(3) 0.5594(2) 0.0270(6) Uani 1 1 d . . . . .
C2 C 0.6981(4) 0.4520(3) 0.3709(3) 0.0248(7) Uani 1 1 d . . . . .
C23 C 0.5257(4) 0.1598(3) 0.4170(3) 0.0242(7) Uani 1 1 d . . . . .
C16 C 0.6513(4) 0.1299(3) 0.5858(3) 0.0249(7) Uani 1 1 d . . . . .
C1 C 0.8051(4) 0.4036(3) 0.4420(3) 0.0237(7) Uani 1 1 d . . . . .
C3 C 0.6245(4) 0.5093(3) 0.4148(3) 0.0275(7) Uani 1 1 d . . . . .
H3 H 0.644180 0.518676 0.487518 0.033 Uiso 1 1 calc R . . . .
C24 C 0.4105(4) 0.1940(3) 0.3520(3) 0.0268(7) Uani 1 1 d . . . . .
C8 C 0.9239(4) 0.3812(3) 0.6154(3) 0.0246(7) Uani 1 1 d . . . . .
C12 C 1.0756(4) 0.2546(3) 0.6643(3) 0.0261(7) Uani 1 1 d . . . . .
C9 C 0.9537(4) 0.4117(3) 0.7240(3) 0.0259(7) Uani 1 1 d . . . . .
C7 C 0.6700(4) 0.4399(3) 0.2619(3) 0.0270(7) Uani 1 1 d . . . . .
H7 H 0.719958 0.402795 0.232602 0.032 Uiso 1 1 calc R . . . .
C17 C 0.6702(4) 0.1419(3) 0.7002(3) 0.0284(8) Uani 1 1 d . . . . .
C13 C 0.9909(4) 0.3050(3) 0.5891(3) 0.0238(7) Uani 1 1 d . . . . .
C25 C 0.3830(4) 0.1962(3) 0.2446(3) 0.0283(8) Uani 1 1 d . . . . .
C27 C 0.5863(4) 0.1199(3) 0.2552(3) 0.0288(8) Uani 1 1 d . . . . .
C22 C 0.7729(4) 0.1025(3) 0.7720(3) 0.0292(8) Uani 1 1 d . . . . .
H22 H 0.829165 0.067421 0.747683 0.035 Uiso 1 1 calc R . . . .
C18 C 0.5855(5) 0.1937(3) 0.7384(3) 0.0297(8) Uani 1 1 d . . . . .
H18 H 0.516345 0.219776 0.691692 0.036 Uiso 1 1 calc R . . . .
C28 C 0.6077(4) 0.1201(3) 0.3640(3) 0.0250(7) Uani 1 1 d . . . . .
C26 C 0.4736(4) 0.1583(3) 0.1985(3) 0.0287(8) Uani 1 1 d . . . . .
C11 C 1.0960(4) 0.2863(3) 0.7690(3) 0.0271(7) Uani 1 1 d . . . . .
C10 C 1.0354(4) 0.3643(3) 0.8018(3) 0.0273(7) Uani 1 1 d . . . . .
C5 C 0.4929(4) 0.5392(3) 0.2411(3) 0.0301(8) Uani 1 1 d . . . . .
H5 H 0.423875 0.567902 0.197661 0.036 Uiso 1 1 calc R . . . .
C4 C 0.5215(4) 0.5523(3) 0.3494(3) 0.0306(8) Uani 1 1 d . . . . .
H4 H 0.471768 0.589887 0.378403 0.037 Uiso 1 1 calc R . . . .
C21 C 0.7911(5) 0.1152(3) 0.8785(3) 0.0346(9) Uani 1 1 d . . . . .
H21 H 0.859691 0.088915 0.925490 0.042 Uiso 1 1 calc R . . . .
C6 C 0.5673(4) 0.4833(3) 0.1973(3) 0.0294(8) Uani 1 1 d . . . . .
H6 H 0.548322 0.474930 0.124657 0.035 Uiso 1 1 calc R . . . .
C15 C 1.1383(5) 0.1685(3) 0.6317(3) 0.0317(8) Uani 1 1 d . . . . .
H15A H 1.116516 0.160961 0.556462 0.048 Uiso 1 1 calc GR . . . .
H15B H 1.092961 0.094181 0.652417 0.048 Uiso 1 1 calc GR . . . .
H15C H 1.245172 0.195637 0.665326 0.048 Uiso 1 1 calc GR . . . .
C20 C 0.7070(5) 0.1673(3) 0.9159(3) 0.0362(9) Uani 1 1 d . . . . .
H20 H 0.719608 0.175918 0.987728 0.043 Uiso 1 1 calc R . . . .
C19 C 0.6044(5) 0.2062(3) 0.8456(3) 0.0353(9) Uani 1 1 d . . . . .
H19 H 0.548098 0.240876 0.870391 0.042 Uiso 1 1 calc R . . . .
C14 C 1.0544(5) 0.3916(4) 0.9155(3) 0.0322(8) Uani 1 1 d . . . . .
H14A H 1.066665 0.326450 0.952495 0.039 Uiso 1 1 calc R . . . .
H14B H 0.964774 0.402615 0.921672 0.039 Uiso 1 1 calc R . . . .
C30 C 0.6861(5) 0.0832(4) 0.2060(3) 0.0368(9) Uani 1 1 d . . . . .
H30A H 0.766903 0.150891 0.202015 0.055 Uiso 1 1 calc GR . . . .
H30B H 0.628142 0.043211 0.136267 0.055 Uiso 1 1 calc GR . . . .
H30C H 0.726703 0.032157 0.248406 0.055 Uiso 1 1 calc GR . . . .
C29 C 0.2665(5) 0.2413(4) 0.1810(3) 0.0346(8) Uani 1 1 d . . . . .
H29A H 0.291795 0.268860 0.118964 0.041 Uiso 1 1 calc R . . . .
H29B H 0.266145 0.306702 0.222619 0.041 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
S2 N3 1.611(3) . ?
S2 C28 1.751(4) . ?
S1 N1 1.616(3) . ?
S1 C13 1.749(4) . ?
Cl1 C9 1.733(4) . ?
Cl4 C24 1.733(4) . ?
Cl6 C26 1.740(4) . ?
Cl3 C11 1.741(4) . ?
Cl2 C14 1.809(4) . ?
Cl5 C29 1.811(4) . ?
N2 C1 1.321(5) . ?
N2 C8 1.373(5) . ?
N4 C23 1.364(5) . ?
N4 C16 1.330(5) . ?
N1 C1 1.346(5) . ?
N3 C16 1.348(5) . ?
C2 C1 1.493(5) . ?
C2 C3 1.397(5) . ?
C2 C7 1.395(5) . ?
C23 C24 1.410(5) . ?
C23 C28 1.412(5) . ?
C16 C17 1.483(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.393(5) . ?
C24 C25 1.383(5) . ?
C8 C9 1.411(5) . ?
C8 C13 1.407(5) . ?
C12 C13 1.404(5) . ?
C12 C11 1.382(5) . ?
C12 C15 1.507(5) . ?
C9 C10 1.384(5) . ?
C7 H7 0.9300 . ?
C7 C6 1.389(5) . ?
C17 C22 1.401(6) . ?
C17 C18 1.403(6) . ?
C25 C26 1.413(6) . ?
C25 C29 1.494(5) . ?
C27 C28 1.406(5) . ?
C27 C26 1.385(6) . ?
C27 C30 1.513(5) . ?
C22 H22 0.9300 . ?
C22 C21 1.380(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.387(6) . ?
C11 C10 1.412(5) . ?
C10 C14 1.492(5) . ?
C5 H5 0.9300 . ?
C5 C4 1.385(6) . ?
C5 C6 1.392(6) . ?
C4 H4 0.9300 . ?
C21 H21 0.9300 . ?
C21 C20 1.394(6) . ?
C6 H6 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C20 H20 0.9300 . ?
C20 C19 1.389(6) . ?
C19 H19 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?

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
N3 S2 C28 106.87(17) . . ?
N1 S1 C13 106.92(17) . . ?
C1 N2 C8 120.6(3) . . ?
C16 N4 C23 120.4(3) . . ?
C1 N1 S1 120.7(3) . . ?
C16 N3 S2 121.0(3) . . ?
C3 C2 C1 119.1(3) . . ?
C7 C2 C1 121.1(3) . . ?
C7 C2 C3 119.8(3) . . ?
N4 C23 C24 119.0(3) . . ?
N4 C23 C28 125.7(3) . . ?
C24 C23 C28 115.3(3) . . ?
N4 C16 N3 128.8(3) . . ?
N4 C16 C17 116.9(3) . . ?
N3 C16 C17 114.2(3) . . ?
N2 C1 N1 129.1(3) . . ?
N2 C1 C2 116.6(3) . . ?
N1 C1 C2 114.3(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.8(4) . . ?
C4 C3 H3 120.1 . . ?
C23 C24 Cl4 117.6(3) . . ?
C25 C24 Cl4 118.9(3) . . ?
C25 C24 C23 123.5(3) . . ?
N2 C8 C9 118.4(3) . . ?
N2 C8 C13 125.3(3) . . ?
C13 C8 C9 116.3(3) . . ?
C13 C12 C15 121.2(3) . . ?
C11 C12 C13 116.7(3) . . ?
C11 C12 C15 122.0(3) . . ?
C8 C9 Cl1 117.6(3) . . ?
C10 C9 Cl1 119.5(3) . . ?
C10 C9 C8 122.9(3) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 C2 120.0(3) . . ?
C6 C7 H7 120.0 . . ?
C22 C17 C16 120.9(3) . . ?
C22 C17 C18 118.8(4) . . ?
C18 C17 C16 120.2(3) . . ?
C8 C13 S1 116.8(3) . . ?
C12 C13 S1 119.8(3) . . ?
C12 C13 C8 123.3(3) . . ?
C24 C25 C26 117.2(3) . . ?
C24 C25 C29 121.2(4) . . ?
C26 C25 C29 121.5(3) . . ?
C28 C27 C30 120.7(3) . . ?
C26 C27 C28 116.2(3) . . ?
C26 C27 C30 123.0(3) . . ?
C17 C22 H22 119.7 . . ?
C21 C22 C17 120.6(4) . . ?
C21 C22 H22 119.7 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.3(4) . . ?
C19 C18 H18 119.9 . . ?
C23 C28 S2 116.7(3) . . ?
C27 C28 S2 119.1(3) . . ?
C27 C28 C23 124.2(3) . . ?
C25 C26 Cl6 118.8(3) . . ?
C27 C26 Cl6 117.8(3) . . ?
C27 C26 C25 123.4(3) . . ?
C12 C11 Cl3 118.2(3) . . ?
C12 C11 C10 123.3(3) . . ?
C10 C11 Cl3 118.5(3) . . ?
C9 C10 C11 117.3(3) . . ?
C9 C10 C14 121.4(3) . . ?
C11 C10 C14 121.3(3) . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.1(3) . . ?
C6 C5 H5 120.0 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.2(4) . . ?
C5 C4 H4 119.9 . . ?
C22 C21 H21 119.9 . . ?
C22 C21 C20 120.3(4) . . ?
C20 C21 H21 119.9 . . ?
C7 C6 C5 120.1(3) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C20 H20 120.1 . . ?
C19 C20 C21 119.7(4) . . ?
C19 C20 H20 120.1 . . ?
C18 C19 C20 120.3(4) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
Cl2 C14 H14A 109.4 . . ?
Cl2 C14 H14B 109.4 . . ?
C10 C14 Cl2 111.2(3) . . ?
C10 C14 H14A 109.4 . . ?
C10 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
Cl5 C29 H29A 109.3 . . ?
Cl5 C29 H29B 109.3 . . ?
C25 C29 Cl5 111.6(3) . . ?
C25 C29 H29A 109.3 . . ?
C25 C29 H29B 109.3 . . ?
H29A C29 H29B 108.0 . . ?


_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 1.653
_oxdiff_exptl_absorpt_empirical_full_min 0.496

# start Validation Reply Form
_vrf_DIFMX02_serc079-r1-rf       
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*0.75
RESPONSE: Residual electron density located close to C15 and C30 which
indicate minor partial chlorination at these positions that could not be
accurately modelled.
;
_vrf_PLAT430_serc079-r1-rf       
;
PROBLEM: Short Inter D...A Contact  S1       ..S2               2.85 Ang.  
RESPONSE: Radicals dimerise in the solid-state through a short S-S contact.
;
_vrf_PLAT340_serc079-r1-rf       
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00567 Ang.  
RESPONSE: This error is attributed to substitutional disorder that could
not be accurately modelled.
;
# end Validation Reply Form
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
####################################################################### 
# 
# 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_serc095-r1-rf2
_database_code_depnum_ccdc_archive 'CCDC 2101069'
loop_
_audit_author_name
_audit_author_address
'Andryj M Borys'
;University of Kent
United Kingdom
;
_audit_update_record             
;
2021-08-03 deposited with the CCDC.	2021-11-23 downloaded from the CCDC.
;
_audit_creation_date             2018-06-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H10.42 Cl5.58 N2 O S'
_chemical_formula_sum            'C16 H10.42 Cl5.58 N2 O S'
_chemical_formula_weight         476.64
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 N2 O1 S1 Cl5.6 H11.4'
_chemical_oxdiff_usercomment     'ABS-281 2,3-Me-OMe'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.5698(7)
_cell_length_b                   16.562(2)
_cell_length_c                   16.941(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.510(12)
_cell_angle_gamma                90
_cell_volume                     1839.8(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1499
_cell_measurement_temperature    100.00(13)
_cell_measurement_theta_max      74.7970
_cell_measurement_theta_min      5.2120
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    9.110
_exptl_absorpt_correction_T_max  0.845
_exptl_absorpt_correction_T_min  0.657
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.721
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             957
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 -2 1 0.0083
1 10 -1 0.0108
-1 -10 1 0.0072
4 -3 -1 0.0027
0 1 11 0.0290
-4 2 1 0.0244
0 -1 -11 0.0254

_exptl_crystal_size_max          0.056
_exptl_crystal_size_mid          0.028
_exptl_crystal_size_min          0.018
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4.1336 -2.1905 1.0335 0.2063 -0.0283 0.9781
0.9798 10.4139 -1.1377 -0.1298 -0.9915 0.0091
-0.9798 -10.4139 1.1377 0.1298 0.9915 -0.0091
4.1466 -2.5282 -1.2516 0.0001 0.0092 1.0000
-0.0267 1.0441 10.9094 0.9880 -0.1293 -0.0844
-4.1644 2.3944 0.9464 -0.0277 0.0049 -0.9996
0.0820 -1.0750 -10.9129 -0.9868 0.1291 0.0976

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0882
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6606
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.077
_diffrn_reflns_theta_min         3.736
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2774
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -122.00 -20.00   1.00   50.00    --  -41.70 -19.00 -90.00  102
  2  ω     -4.00  65.00   1.00   50.00    --   41.70 -38.00  90.00   69
  3  ω     37.00  79.00   1.00   50.00    --   41.70-126.00 -40.00   42
  4  ω     37.00 131.00   1.00  150.00    --  108.32 -61.00 -30.00   94
  5  ω     35.00  93.00   1.00  150.00    --  108.32 -94.00 -90.00   58
  6  ω     72.00 100.00   1.00  150.00    --  108.32-110.00-140.00   28
  7  ω     84.00 177.00   1.00  150.00    --  108.32  45.00 120.00   93
  8  ω    102.00 175.00   1.00  150.00    --  108.32 111.00 -60.00   73
  9  ω    146.00 177.00   1.00  150.00    --  108.32 111.00  90.00   31
 10  ω     81.00 134.00   1.00  150.00    --  108.32 178.00-120.00   53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0245710000
_diffrn_orient_matrix_UB_12      -0.0048292000
_diffrn_orient_matrix_UB_13      0.0910870000
_diffrn_orient_matrix_UB_21      -0.0539600000
_diffrn_orient_matrix_UB_22      -0.0904943000
_diffrn_orient_matrix_UB_23      -0.0033206000
_diffrn_orient_matrix_UB_31      0.2267700000
_diffrn_orient_matrix_UB_32      -0.0210240000
_diffrn_orient_matrix_UB_33      -0.0051726000
_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                2475
_reflns_number_total             3350
_reflns_odcompleteness_completeness 99.85
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    ?
_refine_diff_density_max         0.770
_refine_diff_density_min         -0.958
_refine_diff_density_rms         0.136
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3350
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1319
_refine_ls_R_factor_gt           0.1055
_refine_ls_restrained_S_all      1.145
_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)+(0.0881P)²+16.6757P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2644
_refine_ls_wR_factor_ref         0.2818
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(Cl6)=1-FVAR(1)
 Sof(H6)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C3(H3), C4(H4), C13(H13)
3.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
S1 S 0.2515(3) 0.26782(14) 0.38372(14) 0.0357(6) Uani 1 1 d . . . . .
Cl5 Cl -0.2873(3) 0.45107(15) 0.52664(16) 0.0448(6) Uani 1 1 d . . . . .
Cl1 Cl 0.3707(5) 0.37809(18) 0.32244(18) 0.0575(8) Uani 1 1 d . . . . .
Cl2 Cl 0.3429(6) 0.24811(18) 0.72788(18) 0.0704(11) Uani 1 1 d . . . . .
O1 O 1.2887(9) 0.0598(4) 0.5164(4) 0.0364(15) Uani 1 1 d . . . . .
N2 N 0.4855(11) 0.2689(5) 0.5423(4) 0.0328(17) Uani 1 1 d . . . . .
N1 N 0.4420(11) 0.2145(5) 0.4104(4) 0.0347(17) Uani 1 1 d . . . . .
C14 C 0.1742(13) 0.3156(5) 0.4675(5) 0.0296(18) Uani 1 1 d . . . . .
C2 C 0.7385(13) 0.1818(5) 0.4931(5) 0.0300(19) Uani 1 1 d . . . . .
C5 C 1.1102(13) 0.0995(5) 0.5133(6) 0.034(2) Uani 1 1 d . . . . .
C1 C 0.5441(13) 0.2259(5) 0.4828(6) 0.034(2) Uani 1 1 d . . . . .
C6 C 1.0051(13) 0.1038(5) 0.4387(5) 0.0313(19) Uani 1 1 d . . . . .
H6 H 1.059797 0.079456 0.395240 0.038 Uiso 0.417(10) 1 calc R . P A 1
C7 C 0.8206(13) 0.1440(5) 0.4294(5) 0.032(2) Uani 1 1 d . . . . .
H7 H 0.751067 0.145691 0.379984 0.039 Uiso 1 1 calc R . . . .
C9 C 0.3020(13) 0.3095(5) 0.5382(6) 0.032(2) Uani 1 1 d . . . . .
C3 C 0.8441(13) 0.1772(6) 0.5681(6) 0.033(2) Uani 1 1 d . . . . .
H3 H 0.790187 0.201552 0.611617 0.040 Uiso 1 1 calc R . . . .
C4 C 1.0265(13) 0.1367(6) 0.5767(5) 0.0323(19) Uani 1 1 d . . . . .
H4 H 1.095170 0.134309 0.626294 0.039 Uiso 1 1 calc R . . . .
C13 C -0.0108(13) 0.3572(5) 0.4659(6) 0.033(2) Uani 1 1 d . . . . .
H13 H -0.096586 0.358058 0.420172 0.040 Uiso 1 1 calc R . . B 1
C11 C 0.0646(14) 0.3953(6) 0.6034(6) 0.038(2) Uani 1 1 d . . . . .
C12 C -0.0647(12) 0.3969(5) 0.5328(6) 0.034(2) Uani 1 1 d . . . . .
C10 C 0.2396(14) 0.3503(6) 0.6060(5) 0.036(2) Uani 1 1 d . . . . .
C8 C 1.3983(15) 0.0520(7) 0.5920(6) 0.044(2) Uani 1 1 d . . . . .
H8A H 1.523553 0.023541 0.585889 0.066 Uiso 1 1 calc GR . . . .
H8B H 1.316706 0.022626 0.627367 0.066 Uiso 1 1 calc GR . . . .
H8C H 1.427710 0.104724 0.613412 0.066 Uiso 1 1 calc GR . . . .
C15 C 0.3814(16) 0.3424(7) 0.6794(6) 0.047(3) Uani 1 1 d . . . . .
H15A H 0.356767 0.386392 0.715411 0.056 Uiso 1 1 calc R . . . .
H15B H 0.521724 0.346029 0.664960 0.056 Uiso 1 1 calc R . . . .
C16 C 0.0027(16) 0.4463(7) 0.6700(6) 0.045(3) Uani 1 1 d . . . . .
Cl6 Cl 1.0919(6) 0.0552(3) 0.3599(2) 0.0386(14) Uani 0.583(10) 1 d . . P A -1
Cl4 Cl 0.1808(5) 0.52249(18) 0.69705(18) 0.0612(8) Uani 1 1 d . . . C -1
Cl3 Cl -0.0522(5) 0.3884(2) 0.75139(19) 0.0662(9) Uani 1 1 d . . . D -1
H16 H -0.116(15) 0.468(6) 0.667(6) 0.03(2) Uiso 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
S1 Cl1 2.264(4) . ?
S1 N1 1.575(7) . ?
S1 C14 1.728(9) . ?
Cl5 C12 1.713(8) . ?
Cl2 C15 1.789(12) . ?
O1 C5 1.342(11) . ?
O1 C8 1.437(11) . ?
N2 C1 1.312(12) . ?
N2 C9 1.378(11) . ?
N1 C1 1.374(11) . ?
C14 C9 1.423(12) . ?
C14 C13 1.396(12) . ?
C2 C1 1.473(12) . ?
C2 C7 1.385(13) . ?
C2 C3 1.411(12) . ?
C5 C6 1.405(12) . ?
C5 C4 1.381(13) . ?
C6 H6 0.9300 . ?
C6 C7 1.383(12) . ?
C6 Cl6 1.687(10) . ?
C7 H7 0.9300 . ?
C9 C10 1.415(13) . ?
C3 H3 0.9300 . ?
C3 C4 1.373(12) . ?
C4 H4 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.376(14) . ?
C11 C12 1.424(12) . ?
C11 C10 1.369(14) . ?
C11 C16 1.486(14) . ?
C10 C15 1.514(12) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 Cl4 1.762(12) . ?
C16 Cl3 1.736(12) . ?
C16 H16 0.86(10) . ?

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
N1 S1 Cl1 107.0(3) . . ?
N1 S1 C14 106.8(4) . . ?
C14 S1 Cl1 97.7(3) . . ?
C5 O1 C8 117.8(8) . . ?
C1 N2 C9 121.6(8) . . ?
C1 N1 S1 121.0(7) . . ?
C9 C14 S1 118.0(7) . . ?
C13 C14 S1 120.6(7) . . ?
C13 C14 C9 121.3(8) . . ?
C7 C2 C1 120.5(8) . . ?
C7 C2 C3 118.9(8) . . ?
C3 C2 C1 120.6(8) . . ?
O1 C5 C6 116.1(8) . . ?
O1 C5 C4 125.2(8) . . ?
C4 C5 C6 118.7(8) . . ?
N2 C1 N1 127.6(8) . . ?
N2 C1 C2 118.1(8) . . ?
N1 C1 C2 114.3(8) . . ?
C5 C6 H6 119.8 . . ?
C5 C6 Cl6 121.1(7) . . ?
C7 C6 C5 120.3(8) . . ?
C7 C6 H6 119.8 . . ?
C7 C6 Cl6 118.5(7) . . ?
Cl6 C6 H6 3.7 . . ?
C2 C7 H7 119.7 . . ?
C6 C7 C2 120.7(8) . . ?
C6 C7 H7 119.7 . . ?
N2 C9 C14 123.1(8) . . ?
N2 C9 C10 119.2(8) . . ?
C10 C9 C14 117.6(8) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(9) . . ?
C4 C3 H3 120.0 . . ?
C5 C4 H4 119.3 . . ?
C3 C4 C5 121.4(8) . . ?
C3 C4 H4 119.3 . . ?
C14 C13 H13 120.4 . . ?
C12 C13 C14 119.2(8) . . ?
C12 C13 H13 120.4 . . ?
C12 C11 C16 116.7(9) . . ?
C10 C11 C12 119.6(9) . . ?
C10 C11 C16 123.6(9) . . ?
C13 C12 Cl5 117.5(7) . . ?
C13 C12 C11 120.8(8) . . ?
C11 C12 Cl5 121.6(8) . . ?
C9 C10 C15 115.6(8) . . ?
C11 C10 C9 121.2(8) . . ?
C11 C10 C15 123.2(9) . . ?
O1 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
O1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
Cl2 C15 H15A 109.5 . . ?
Cl2 C15 H15B 109.5 . . ?
C10 C15 Cl2 110.8(7) . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C11 C16 Cl4 113.4(7) . . ?
C11 C16 Cl3 111.6(8) . . ?
C11 C16 H16 119(6) . . ?
Cl4 C16 H16 108(7) . . ?
Cl3 C16 Cl4 110.8(6) . . ?
Cl3 C16 H16 93(7) . . ?


_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 1.254
_oxdiff_exptl_absorpt_empirical_full_min 0.761
# start Validation Reply Form
_vrf_PLAT077_serc095-r1-rf2      
;
PROBLEM: Unitcell Contains Non-integer Number of Atoms ..     Please Check
RESPONSE: Partial chlorination at C6.
;
_vrf_PLAT082_serc095-r1-rf2      
;
PROBLEM: High R1 Value ..................................       0.11 Report
RESPONSE: Small and weakly diffracting crystal with considerable disorder.
;
_vrf_PLAT084_serc095-r1-rf2      
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.28 Report
RESPONSE: Small and weakly diffracting crystal with considerable disorder.
;
_vrf_PLAT245_serc095-r1-rf2      
;
PROBLEM: U(iso) H16       Smaller than U(eq) C16       by      0.015 Ang**2
RESPONSE: H16 is likely to be disorder to due to evidence of mixed
chlorination/protonation and neighbouring sites.
;
_vrf_PLAT431_serc095-r1-rf2      
;
PROBLEM: Short Inter HL..A Contact  Cl3      ..N1               3.19 Ang.  
RESPONSE: Attributed to external packing forces.
;
# end Validation Reply Form
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_serc125-r1-rf
_database_code_depnum_ccdc_archive 'CCDC 2101077'
loop_
_audit_author_name
_audit_author_address
'Andryj M Borys'
;University of Kent
United Kingdom
;
_audit_update_record             
;
2021-08-03 deposited with the CCDC.	2021-11-23 downloaded from the CCDC.
;
_audit_creation_date             2018-08-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl4 Ga, C13 H6 Cl3 N2 S'
_chemical_formula_sum            'C13 H6 Cl7 Ga N2 S'
_chemical_formula_weight         540.13
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 N2 S1 Ga1 Cl7 H6'
_chemical_oxdiff_usercomment     ABS-499
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'
Ga Ga -1.2846 0.7763 '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                   9.5753(4)
_cell_length_b                   9.8718(4)
_cell_length_c                   20.0990(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.444(3)
_cell_angle_gamma                90
_cell_volume                     1894.16(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    27045
_cell_measurement_temperature    100.0(4)
_cell_measurement_theta_max      75.9050
_cell_measurement_theta_min      4.2510
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    12.113
_exptl_absorpt_correction_T_max  0.539
_exptl_absorpt_correction_T_min  0.152
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear blackish violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   blackish
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.894
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             1056
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 6 -6 0.0887
-1 0 -13 0.1025
1 -6 -6 0.0844
1 -6 6 0.0855
1 -2 12 0.0948
-1 5 9 0.0981
2 2 -12 0.0992
6 0 0 0.0324
-2 -2 12 0.0900
-6 0 0 0.0267

_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.209
_exptl_crystal_size_mid          0.197
_exptl_crystal_size_min          0.061
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.4969 5.5066 -5.6566 -0.2357 -0.6652 0.7085
-0.5038 0.0273 -12.8797 0.0960 0.2742 0.9569
1.0473 -5.5516 -6.2538 0.3280 0.9288 0.1727
1.4986 -5.5290 5.5669 0.2376 0.6703 -0.7030
0.8384 -1.5538 12.3663 -0.0149 -0.0448 -0.9989
-0.7520 4.7018 8.7904 -0.3042 -0.8620 -0.4054
1.5249 1.7664 -12.3348 0.3785 -0.0485 0.9243
6.1949 -0.2377 0.0986 0.9645 -0.1266 -0.2319
-2.0369 -1.7151 12.1126 -0.4558 0.0587 -0.8882
-6.2052 0.1999 0.1602 -0.9690 0.1272 0.2117

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1269
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            36088
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.051
_diffrn_reflns_theta_min         4.413
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2774
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    2.00    --  -41.96 -38.00  90.00   99
  2  ω   -122.00  -1.00   1.00    2.00    --  -41.96 -19.00 150.00  121
  3  ω    -96.00  -2.00   1.00    2.00    --  -41.96 125.00-120.00   94
  4  ω     23.00  98.00   1.00    2.00    --   41.96-125.00  60.00   75
  5  ω      1.00  83.00   1.00    2.00    --   41.96 -99.00  60.00   82
  6  ω     23.00  98.00   1.00    2.00    --   41.96-125.00-180.00   75
  7  ω     35.00 116.00   1.00    7.00    --  111.00-111.00 -60.00   81
  8  ω     78.00 178.00   1.00    7.00    --  111.00  77.00 -30.00  100
  9  ω     78.00 178.00   1.00    7.00    --  111.00  77.00  90.00  100
 10  ω     38.00 137.00   1.00    7.00    --  111.00 -45.00  30.00   99
 11  ω     78.00 178.00   1.00    7.00    --  111.00  77.00  60.00  100
 12  ω     28.00 109.00   1.00    7.00    --  111.00 -94.00-120.00   81
 13  ω    100.00 178.00   1.00    7.00    --  111.00 111.00  90.00   78
 14  ω     28.00 109.00   1.00    7.00    --  111.00 -94.00 150.00   81
 15  ω    100.00 178.00   1.00    7.00    --  111.00 111.00 -60.00   78
 16  ω     83.00 178.00   1.00    7.00    --  111.00  30.00 -90.00   95
 17  ω     28.00 109.00   1.00    7.00    --  111.00 -94.00 -30.00   81
 18  ω     83.00 178.00   1.00    7.00    --  111.00  30.00-180.00   95
 19  ω     39.00 140.00   1.00    7.00    --  111.00 -61.00-120.00  101
 20  ω     28.00 109.00   1.00    7.00    --  111.00 -94.00-150.00   81
 21  ω     35.00 116.00   1.00    7.00    --  111.00-111.00  30.00   81
 22  ω     28.00 109.00   1.00    7.00    --  111.00 -94.00  60.00   81
 23  ω     35.00 116.00   1.00    7.00    --  111.00-111.00 120.00   81
 24  ω     35.00 116.00   1.00    7.00    --  111.00-111.00-150.00   81
 25  ω     57.00 151.00   1.00    7.00    --  111.00 178.00 150.00   94
 26  ω     28.00 109.00   1.00    7.00    --  111.00 -94.00 120.00   81
 27  ω    100.00 178.00   1.00    7.00    --  111.00 111.00   0.00   78
 28  ω     28.00 109.00   1.00    7.00    --  111.00 -94.00  30.00   81
 29  ω   -116.00 -17.00   1.00    2.00    --  -41.96 -38.00  30.00   99
 30  ω   -115.00 -14.00   1.00    2.00    --  -41.96 -57.00 -30.00  101
 31  ω      9.00 118.00   1.00    2.00    --   41.96  77.00   0.00  109
 32  ω      9.00 118.00   1.00    2.00    --   41.96  77.00-180.00  109
 33  ω      7.00  35.00   1.00    2.00    --   41.96  86.00 103.25   28
 34  ω      9.00 118.00   1.00    2.00    --   41.96  77.00 -90.00  109
 35  ω     85.00 178.00   1.00    7.00    --  111.00  45.00  30.00   93
 36  ω     82.00 155.00   1.00    7.00    --  111.00  61.00 120.00   73
 37  ω     82.00 178.00   1.00    7.00    --  111.00  61.00-150.00   96
 38  ω     85.00 178.00   1.00    7.00    --  111.00  45.00 -60.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1553455000
_diffrn_orient_matrix_UB_12      -0.0145100000
_diffrn_orient_matrix_UB_13      -0.0135588000
_diffrn_orient_matrix_UB_21      -0.0258250000
_diffrn_orient_matrix_UB_22      -0.1489679000
_diffrn_orient_matrix_UB_23      -0.0205929000
_diffrn_orient_matrix_UB_31      -0.0345708000
_diffrn_orient_matrix_UB_32      0.0444373000
_diffrn_orient_matrix_UB_33      -0.0728471000
_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                3653
_reflns_number_total             3657
_reflns_odcompleteness_completeness 99.97
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.917
_refine_diff_density_min         -0.943
_refine_diff_density_rms         0.176
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3657
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0617
_refine_ls_restrained_S_all      1.135
_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)+(0.1050P)²+3.5470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1632
_refine_ls_wR_factor_ref         0.1632
_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:
 C12(H12), C3(H3), C4(H4), C7(H7), C6(H6), C5(H5)
;
_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
Ga1 Ga 0.22320(5) 0.46638(5) 0.77578(2) 0.02458(19) Uani 1 1 d . . . . .
Cl1 Cl 0.54545(10) 0.73307(9) 0.44724(4) 0.0270(2) Uani 1 1 d . . . . .
S1 S 0.61386(10) 0.55599(10) 0.69945(5) 0.0258(2) Uani 1 1 d . . . . .
Cl2 Cl 0.31827(10) 0.93653(9) 0.48927(5) 0.0295(2) Uani 1 1 d . . . . .
Cl5 Cl 0.38693(11) 0.60409(11) 0.81539(5) 0.0326(3) Uani 1 1 d . . . . .
Cl6 Cl 0.16806(10) 0.34004(10) 0.85833(5) 0.0335(3) Uani 1 1 d . . . . .
Cl4 Cl 0.31657(11) 0.33904(11) 0.70176(5) 0.0352(3) Uani 1 1 d . . . . .
Cl3 Cl 0.23771(12) 0.94200(12) 0.63737(5) 0.0386(3) Uani 1 1 d . . . . .
Cl7 Cl 0.04736(14) 0.57912(13) 0.73178(6) 0.0481(3) Uani 1 1 d . . . . .
N2 N 0.6616(3) 0.5644(3) 0.55408(16) 0.0226(6) Uani 1 1 d . . . . .
N1 N 0.7213(4) 0.4693(3) 0.66201(17) 0.0266(7) Uani 1 1 d . . . . .
C8 C 0.5668(4) 0.6488(4) 0.57493(17) 0.0206(7) Uani 1 1 d . . . . .
C13 C 0.5282(4) 0.6575(4) 0.64274(19) 0.0225(7) Uani 1 1 d . . . . .
C1 C 0.7344(4) 0.4803(4) 0.59599(19) 0.0227(7) Uani 1 1 d . . . . .
C10 C 0.3989(4) 0.8293(4) 0.54613(19) 0.0240(8) Uani 1 1 d . . . . .
C9 C 0.4986(4) 0.7395(4) 0.52751(18) 0.0217(7) Uani 1 1 d . . . . .
C2 C 0.8365(4) 0.3911(4) 0.5674(2) 0.0245(8) Uani 1 1 d . . . . .
C12 C 0.4255(4) 0.7486(4) 0.6617(2) 0.0267(8) Uani 1 1 d . . . . .
H12 H 0.400541 0.751601 0.705516 0.032 Uiso 1 1 calc R . . . .
C11 C 0.3636(4) 0.8320(4) 0.6144(2) 0.0272(8) Uani 1 1 d . . . . .
C3 C 0.8542(4) 0.3953(4) 0.4994(2) 0.0272(8) Uani 1 1 d . . . . .
H3 H 0.800814 0.455022 0.472140 0.033 Uiso 1 1 calc R . . . .
C4 C 0.9518(4) 0.3106(5) 0.4713(2) 0.0337(9) Uani 1 1 d . . . . .
H4 H 0.962750 0.311955 0.425766 0.040 Uiso 1 1 calc R . . . .
C7 C 0.9183(5) 0.3043(5) 0.6092(2) 0.0364(10) Uani 1 1 d . . . . .
H7 H 0.907268 0.302700 0.654795 0.044 Uiso 1 1 calc R . . . .
C6 C 1.0168(6) 0.2200(6) 0.5823(3) 0.0480(13) Uani 1 1 d . . . . .
H6 H 1.071697 0.161647 0.609596 0.058 Uiso 1 1 calc R . . . .
C5 C 1.0315(5) 0.2246(6) 0.5140(3) 0.0469(12) Uani 1 1 d . . . . .
H5 H 1.096934 0.168157 0.496253 0.056 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
Ga1 Cl5 2.1786(11) . ?
Ga1 Cl6 2.1732(11) . ?
Ga1 Cl4 2.1907(11) . ?
Ga1 Cl7 2.1506(12) . ?
Cl1 C9 1.709(4) . ?
S1 N1 1.574(3) . ?
S1 C13 1.683(4) . ?
Cl2 C10 1.699(4) . ?
Cl3 C11 1.712(4) . ?
N2 C8 1.324(5) . ?
N2 C1 1.339(5) . ?
N1 C1 1.347(5) . ?
C8 C13 1.442(5) . ?
C8 C9 1.428(5) . ?
C13 C12 1.407(5) . ?
C1 C2 1.466(5) . ?
C10 C9 1.376(5) . ?
C10 C11 1.439(5) . ?
C2 C3 1.391(6) . ?
C2 C7 1.397(6) . ?
C12 H12 0.9300 . ?
C12 C11 1.359(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.404(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.393(7) . ?
C7 H7 0.9300 . ?
C7 C6 1.399(6) . ?
C6 H6 0.9300 . ?
C6 C5 1.390(8) . ?
C5 H5 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
Cl5 Ga1 Cl4 106.63(4) . . ?
Cl6 Ga1 Cl5 106.84(4) . . ?
Cl6 Ga1 Cl4 108.98(5) . . ?
Cl7 Ga1 Cl5 110.22(5) . . ?
Cl7 Ga1 Cl6 112.47(5) . . ?
Cl7 Ga1 Cl4 111.43(5) . . ?
N1 S1 C13 107.61(18) . . ?
C8 N2 C1 121.8(3) . . ?
C1 N1 S1 122.8(3) . . ?
N2 C8 C13 124.7(3) . . ?
N2 C8 C9 118.2(3) . . ?
C9 C8 C13 117.1(3) . . ?
C8 C13 S1 117.2(3) . . ?
C12 C13 S1 120.7(3) . . ?
C12 C13 C8 122.0(3) . . ?
N2 C1 N1 125.9(3) . . ?
N2 C1 C2 117.1(3) . . ?
N1 C1 C2 117.0(3) . . ?
C9 C10 Cl2 120.5(3) . . ?
C9 C10 C11 119.4(3) . . ?
C11 C10 Cl2 120.1(3) . . ?
C8 C9 Cl1 117.8(3) . . ?
C10 C9 Cl1 121.3(3) . . ?
C10 C9 C8 120.9(3) . . ?
C3 C2 C1 120.2(4) . . ?
C3 C2 C7 120.3(4) . . ?
C7 C2 C1 119.4(4) . . ?
C13 C12 H12 120.9 . . ?
C11 C12 C13 118.3(4) . . ?
C11 C12 H12 120.9 . . ?
C10 C11 Cl3 119.4(3) . . ?
C12 C11 Cl3 118.3(3) . . ?
C12 C11 C10 122.3(3) . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.8(4) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 121.1 . . ?
C5 C4 C3 117.8(4) . . ?
C5 C4 H4 121.1 . . ?
C2 C7 H7 120.2 . . ?
C2 C7 C6 119.7(4) . . ?
C6 C7 H7 120.2 . . ?
C7 C6 H6 120.5 . . ?
C5 C6 C7 119.1(5) . . ?
C5 C6 H6 120.5 . . ?
C4 C5 H5 118.8 . . ?
C6 C5 C4 122.3(4) . . ?
C6 C5 H5 118.8 . . ?


_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 1.424
_oxdiff_exptl_absorpt_empirical_full_min 0.757

# start Validation Reply Form
_vrf_RINTA01_serc125-r1-rf       
;
PROBLEM: The value of Rint is greater than 0.12
RESPONSE: Unknown origin.
;
_vrf_PLAT341_serc125-r1-rf       
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00615 Ang.  
RESPONSE: Unknown origin.
;
_vrf_PLAT431_serc125-r1-rf       
;
PROBLEM: Short Inter HL..A Contact  Cl5      ..S1               3.34 Ang.  
RESPONSE: Close contact between the S cation and GaCl4 anion.
;
# end Validation Reply Form
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_abs-391-r1-rf
_database_code_depnum_ccdc_archive 'CCDC 2101073'
loop_
_audit_author_name
_audit_author_address
'Andryj M Borys'
;University of Kent
United Kingdom
;
_audit_update_record             
;
2021-08-03 deposited with the CCDC.	2021-11-23 downloaded from the CCDC.
;
_audit_creation_date             2018-06-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H8 Cl4 N2 O S'
_chemical_formula_sum            'C14 H8 Cl4 N2 O S'
_chemical_formula_weight         394.08
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 S1 N2 O1 Cl4 H8'
_chemical_oxdiff_usercomment     ABS-391
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0073(5)
_cell_length_b                   9.6628(6)
_cell_length_c                   12.0172(7)
_cell_angle_alpha                95.257(5)
_cell_angle_beta                 106.738(6)
_cell_angle_gamma                101.231(6)
_cell_volume                     754.78(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5355
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      74.9780
_cell_measurement_theta_min      4.5990
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.438
_exptl_absorpt_correction_T_max  0.781
_exptl_absorpt_correction_T_min  0.324
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             396
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 0 3 0.1078
0 -6 0 0.0172
5 -1 -3 0.1048
0 6 0 0.0204
-3 -3 1 0.0805
0 1 -8 0.0145
3 3 -2 0.0841
0 -1 7 0.0181

_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.035
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.5017 0.4166 2.8350 0.0153 0.5527 0.8333
-0.1430 -6.0787 0.4870 -0.0179 -0.7388 0.6737
4.5273 -0.8028 -2.8261 -0.0165 -0.6035 -0.7972
0.0278 6.1113 -0.4159 0.0183 0.7556 -0.6547
-3.4495 -2.9151 1.0582 -0.1767 0.0034 0.9843
0.1191 1.1419 -7.5219 -0.9908 0.0254 -0.1328
3.4592 3.0318 -1.8420 0.0732 -0.0008 -0.9973
-0.0337 -1.0683 7.4852 0.9938 -0.0255 0.1083

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11718
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.122
_diffrn_reflns_theta_min         3.890
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2887
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00  32.00   1.00    3.00    --  -42.20  77.00 -60.00  106
  2  ω   -112.00 -16.00   1.00    3.00    --  -42.20 -57.00  60.00   96
  3  ω    -69.00  28.00   1.00    3.00    --  -42.20  57.00-150.00   97
  4  ω      1.00  82.00   1.00    3.00    --   42.20 -99.00   0.00   81
  5  ω     11.00 116.00   1.00    3.00    --   42.20  77.00 150.00  105
  6  ω     31.00 156.00   1.00   11.00    --  111.00 -15.00-150.00  125
  7  ω     36.00 116.00   1.00   11.00    --  111.00-111.00-150.00   80
  8  ω     40.00 135.00   1.00   11.00    --  111.00 -45.00  30.00   95
  9  ω     36.00 116.00   1.00   11.00    --  111.00-111.00  60.00   80
 10  ω     30.00 109.00   1.00   11.00    --  111.00 -94.00-120.00   79
 11  ω     36.00 116.00   1.00   11.00    --  111.00-111.00 150.00   80
 12  ω     31.00 156.00   1.00   11.00    --  111.00 -15.00 -30.00  125
 13  ω     66.00 178.00   1.00   11.00    --  111.00  15.00-150.00  112
 14  ω    100.00 178.00   1.00   11.00    --  111.00 111.00-180.00   78
 15  ω     40.00 135.00   1.00   11.00    --  111.00 -45.00-120.00   95
 16  ω     30.00 109.00   1.00   11.00    --  111.00 -94.00 -90.00   79
 17  ω     41.00 139.00   1.00   11.00    --  111.00 -61.00 120.00   98
 18  ω     36.00 135.00   1.00   11.00    --  111.00 -30.00 120.00   99
 19  ω     36.00 116.00   1.00   11.00    --  111.00-111.00 -30.00   80
 20  ω     57.00 151.00   1.00   11.00    --  111.00 178.00 150.00   94
 21  ω     37.00 142.00   1.00   11.00    --  111.00 -77.00 -90.00  105
 22  ω   -112.00 -16.00   1.00    3.00    --  -42.20 -57.00   0.00   96
 23  ω   -112.00 -16.00   1.00    3.00    --  -42.20 -57.00-150.00   96
 24  ω   -116.00 -11.00   1.00    3.00    --  -42.20 -77.00 -60.00  105
 25  ω   -112.00 -16.00   1.00    3.00    --  -42.20 -57.00 150.00   96
 26  ω     11.00 116.00   1.00    3.00    --   42.20  77.00  60.00  105
 27  ω      1.00  82.00   1.00    3.00    --   42.20 -99.00  90.00   81
 28  ω     66.00 178.00   1.00   11.00    --  111.00  15.00  30.00  112
 29  ω     66.00 178.00   1.00   11.00    --  111.00  15.00 120.00  112
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0826065000
_diffrn_orient_matrix_UB_12      0.0118011000
_diffrn_orient_matrix_UB_13      0.1348244000
_diffrn_orient_matrix_UB_21      -0.1023898000
_diffrn_orient_matrix_UB_22      0.1250611000
_diffrn_orient_matrix_UB_23      0.0139857000
_diffrn_orient_matrix_UB_31      -0.1959457000
_diffrn_orient_matrix_UB_32      -0.1063545000
_diffrn_orient_matrix_UB_33      -0.0015969000
_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                2767
_reflns_number_total             2964
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.643
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2964
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.028
_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)+(0.0675P)²+0.4578P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1073
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C3(H3), C7(H7), C4(H4), C6(H6)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_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
Cl4 Cl 0.30010(8) 0.27632(6) 0.94623(5) 0.02623(16) Uani 1 1 d . . . . .
Cl3 Cl 0.23593(9) 0.05969(6) 0.72206(5) 0.02763(16) Uani 1 1 d . . . . .
Cl2 Cl 0.22925(9) 0.17002(6) 0.48421(5) 0.02679(16) Uani 1 1 d . . . . .
S1 S 0.27794(9) 0.70050(6) 0.68588(5) 0.02438(16) Uani 1 1 d . . . . .
Cl1 Cl 0.62249(9) 0.79798(6) 0.78474(5) 0.02974(17) Uani 1 1 d . . . . .
O1 O 0.1947(3) 0.72281(18) 0.01682(15) 0.0285(4) Uani 1 1 d . . . . .
N2 N 0.2575(3) 0.4742(2) 0.49079(17) 0.0214(4) Uani 1 1 d . . . . .
N1 N 0.2356(3) 0.7127(2) 0.55245(18) 0.0252(4) Uani 1 1 d . . . . .
C2 C 0.2372(3) 0.6413(2) 0.3559(2) 0.0212(4) Uani 1 1 d . . . . .
C9 C 0.2629(3) 0.4326(2) 0.5964(2) 0.0209(4) Uani 1 1 d . . . . .
C1 C 0.2490(3) 0.6053(2) 0.4735(2) 0.0214(4) Uani 1 1 d . . . . .
C13 C 0.2876(3) 0.4768(3) 0.8066(2) 0.0231(5) Uani 1 1 d . . . . .
H13 H 0.299722 0.540717 0.872447 0.028 Uiso 1 1 calc R . . . .
C3 C 0.2162(3) 0.5334(2) 0.2637(2) 0.0225(4) Uani 1 1 d . . . . .
H3 H 0.211147 0.440004 0.277968 0.027 Uiso 1 1 calc R . . . .
C11 C 0.2580(3) 0.2381(2) 0.7123(2) 0.0225(5) Uani 1 1 d . . . . .
C7 C 0.2444(3) 0.7812(2) 0.3320(2) 0.0237(5) Uani 1 1 d . . . . .
H7 H 0.257376 0.853888 0.391946 0.028 Uiso 1 1 calc R . . . .
C5 C 0.2109(3) 0.7042(3) 0.1298(2) 0.0237(5) Uani 1 1 d . . . . .
C14 C 0.2770(3) 0.5226(2) 0.6984(2) 0.0211(4) Uani 1 1 d . . . . .
C10 C 0.2510(3) 0.2854(2) 0.6064(2) 0.0217(4) Uani 1 1 d . . . . .
C4 C 0.2029(3) 0.5639(2) 0.1525(2) 0.0235(5) Uani 1 1 d . . . . .
H4 H 0.188634 0.491241 0.092266 0.028 Uiso 1 1 calc R . . . .
C6 C 0.2326(3) 0.8128(2) 0.2203(2) 0.0232(5) Uani 1 1 d . . . . .
H6 H 0.239152 0.906253 0.205879 0.028 Uiso 1 1 calc R . . . .
C12 C 0.2795(3) 0.3349(3) 0.8128(2) 0.0228(5) Uani 1 1 d . . . . .
C8 C 0.2058(5) 0.8649(3) -0.0105(2) 0.0360(6) Uani 1 1 d . . . . .
H8A H 0.198104 0.864090 -0.091642 0.054 Uiso 1 1 calc GR . . . .
H8B H 0.333002 0.926386 0.038550 0.054 Uiso 1 1 calc GR . . . .
H8C H 0.093795 0.899446 0.003260 0.054 Uiso 1 1 calc GR . . . .


_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
Cl4 C12 1.725(2) . ?
Cl3 C11 1.718(2) . ?
Cl2 C10 1.711(2) . ?
S1 Cl1 2.3205(8) . ?
S1 N1 1.564(2) . ?
S1 C14 1.738(2) . ?
O1 C5 1.361(3) . ?
O1 C8 1.434(3) . ?
N2 C9 1.358(3) . ?
N2 C1 1.312(3) . ?
N1 C1 1.377(3) . ?
C2 C1 1.470(3) . ?
C2 C3 1.404(3) . ?
C2 C7 1.402(3) . ?
C9 C14 1.404(3) . ?
C9 C10 1.427(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.399(3) . ?
C13 C12 1.371(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(3) . ?
C11 C10 1.382(3) . ?
C11 C12 1.410(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.386(3) . ?
C5 C4 1.401(3) . ?
C5 C6 1.393(3) . ?
C4 H4 0.9300 . ?
C6 H6 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

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
N1 S1 Cl1 108.79(8) . . ?
N1 S1 C14 106.78(11) . . ?
C14 S1 Cl1 98.20(8) . . ?
C5 O1 C8 117.72(19) . . ?
C1 N2 C9 121.1(2) . . ?
C1 N1 S1 121.61(17) . . ?
C3 C2 C1 119.7(2) . . ?
C7 C2 C1 121.9(2) . . ?
C7 C2 C3 118.4(2) . . ?
N2 C9 C14 125.4(2) . . ?
N2 C9 C10 118.5(2) . . ?
C14 C9 C10 116.1(2) . . ?
N2 C1 N1 126.7(2) . . ?
N2 C1 C2 118.0(2) . . ?
N1 C1 C2 115.2(2) . . ?
C14 C13 H13 121.0 . . ?
C12 C13 H13 121.0 . . ?
C12 C13 C14 118.0(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.9(2) . . ?
C4 C3 H3 119.5 . . ?
C10 C11 Cl3 120.14(18) . . ?
C10 C11 C12 120.5(2) . . ?
C12 C11 Cl3 119.32(17) . . ?
C2 C7 H7 119.5 . . ?
C6 C7 C2 120.9(2) . . ?
C6 C7 H7 119.5 . . ?
O1 C5 C4 115.5(2) . . ?
O1 C5 C6 124.7(2) . . ?
C6 C5 C4 119.7(2) . . ?
C9 C14 S1 116.78(17) . . ?
C13 C14 S1 119.30(18) . . ?
C13 C14 C9 123.9(2) . . ?
C9 C10 Cl2 118.14(17) . . ?
C11 C10 Cl2 121.20(18) . . ?
C11 C10 C9 120.7(2) . . ?
C3 C4 C5 120.2(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C7 C6 C5 119.8(2) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C13 C12 Cl4 119.00(19) . . ?
C13 C12 C11 120.8(2) . . ?
C11 C12 Cl4 120.20(18) . . ?
O1 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
O1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?


_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 1.960
_oxdiff_exptl_absorpt_empirical_full_min 0.668

# start Validation Reply Form
_vrf_PLAT230_abs-391-r1-rf       
;
PROBLEM: Hirshfeld Test Diff for   Cl1      --S1        .        6.3 s.u.  
RESPONSE: This error is likely to be caused by disorder of the S-Cl fragment,
with each atom expected to vibrate along different axes.
;
# end Validation Reply Form
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_abs-819-twin-r1_twin1_hklf4-rf
_database_code_depnum_ccdc_archive 'CCDC 2101071'
loop_
_audit_author_name
_audit_author_address
'Andryj M Borys'
;University of Kent
United Kingdom
;
_audit_update_record             
;
2021-08-03 deposited with the CCDC.	2021-11-23 downloaded from the CCDC.
;
_audit_creation_date             2018-06-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl, C14 H10 Cl4 N3 S, Cl H'
_chemical_formula_sum            'C14 H11 Cl6 N3 S'
_chemical_formula_weight         466.02
_chemical_melting_point          ?
_chemical_oxdiff_formula         'N3 S1 Cl6 C14 H111'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1354(2)
_cell_length_b                   9.2414(2)
_cell_length_c                   12.9459(6)
_cell_angle_alpha                90.608(3)
_cell_angle_beta                 101.838(3)
_cell_angle_gamma                105.699(2)
_cell_volume                     914.81(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11291
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      75.5540
_cell_measurement_theta_min      4.9550
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    9.662
_exptl_absorpt_correction_T_max  0.694
_exptl_absorpt_correction_T_min  0.174
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             468
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 6 0 0.0442
0 -6 0 0.0497
-5 2 2 0.2019
0 0 8 0.0193
5 -2 -2 0.1830
0 0 -8 0.0211

_exptl_crystal_size_max          0.393
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.043
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0164 5.7686 -0.4123 -0.0254 -0.9992 0.0317
0.0550 -5.7900 0.3708 0.0254 0.9986 -0.0453
-5.2571 1.8117 2.4210 0.0761 -0.0030 0.9971
-0.0810 -0.0610 8.2375 -0.9836 0.0249 0.1784
5.2775 -1.8261 -1.7437 -0.1588 0.0051 -0.9873
-0.0036 0.0903 -8.2111 0.9864 -0.0250 -0.1627

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17679
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.505
_diffrn_reflns_theta_min         3.497
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2887
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  32.00   1.00    1.50    --  -41.91  38.00-150.00   98
  2  ω   -116.00 -17.00   1.00    1.50    --  -41.91 -38.00  30.00   99
  3  ω    -96.00  -2.00   1.00    1.50    --  -41.91 125.00 -60.00   94
  4  ω    -32.00  66.00   1.00    1.50    --   41.91 -38.00-120.00   98
  5  ω     23.00  98.00   1.00    1.50    --   41.91-125.00 -90.00   75
  6  ω     37.00 117.00   1.00    3.00    --  112.00-115.00 -46.00   80
  7  ω     84.00 178.00   1.00    3.00    --  112.00  30.00-120.00   94
  8  ω     36.00 145.00   1.00    3.00    --  112.00 -77.00 -90.00  109
  9  ω     29.00 109.00   1.00    3.00    --  112.00 -94.00-150.00   80
 10  ω     36.00 140.00   1.00    3.00    --  112.00 -30.00 -90.00  104
 11  ω     57.00 151.00   1.00    3.00    --  112.00 178.00 -90.00   94
 12  ω     36.00 116.00   1.00    3.00    --  112.00-111.00   0.00   80
 13  ω     29.00 109.00   1.00    3.00    --  112.00 -94.00  60.00   80
 14  ω     29.00 109.00   1.00    3.00    --  112.00 -94.00 120.00   80
 15  ω    100.00 178.00   1.00    3.00    --  112.00 111.00   0.00   78
 16  ω     36.00 116.00   1.00    3.00    --  112.00-111.00  90.00   80
 17  ω     79.00 178.00   1.00    3.00    --  112.00  77.00   0.00   99
 18  ω    100.00 178.00   1.00    3.00    --  112.00 111.00  60.00   78
 19  ω     29.00 109.00   1.00    3.00    --  112.00 -94.00 -90.00   80
 20  ω     86.00 178.00   1.00    3.00    --  112.00  45.00 150.00   92
 21  ω     39.00 138.00   1.00    3.00    --  112.00 -45.00  60.00   99
 22  ω    100.00 178.00   1.00    3.00    --  112.00 111.00-150.00   78
 23  ω     59.00 178.00   1.00    3.00    --  112.00  15.00 -30.00  119
 24  ω   -118.00  -9.00   1.00    1.50    --  -41.91 -77.00-150.00  109
 25  ω   -118.00  -9.00   1.00    1.50    --  -41.91 -77.00  30.00  109
 26  ω   -118.00  -9.00   1.00    1.50    --  -41.91 -77.00 -60.00  109
 27  ω     64.00 124.00   1.00    1.50    --   41.91 170.00-173.00   60
 28  ω      9.00 118.00   1.00    1.50    --   41.91  77.00-150.00  109
 29  ω     14.00 114.00   1.00    1.50    --   41.91  57.00 150.00  100
 30  ω     84.00 178.00   1.00    3.00    --  112.00  30.00  90.00   94
 31  ω     83.00 178.00   1.00    3.00    --  112.00  61.00-120.00   95
 32  ω     79.00 178.00   1.00    3.00    --  112.00  77.00 -90.00   99
 33  ω     79.00 178.00   1.00    3.00    --  112.00  77.00  30.00   99
 34  ω     83.00 178.00   1.00    3.00    --  112.00  61.00 -30.00   95
 35  ω     79.00 178.00   1.00    3.00    --  112.00  77.00  90.00   99
 36  ω     79.00 130.00   1.00    3.00    --  112.00  77.00  60.00   51
 37  ω     83.00 178.00   1.00    3.00    --  112.00  61.00-180.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0742465000
_diffrn_orient_matrix_UB_12      -0.0127934000
_diffrn_orient_matrix_UB_13      -0.1202340000
_diffrn_orient_matrix_UB_21      -0.0584930000
_diffrn_orient_matrix_UB_22      -0.1729592000
_diffrn_orient_matrix_UB_23      0.0011653000
_diffrn_orient_matrix_UB_31      -0.1779123000
_diffrn_orient_matrix_UB_32      0.0074203000
_diffrn_orient_matrix_UB_33      0.0199692000
_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                3306
_reflns_number_total             3432
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.328
_refine_diff_density_min         -0.975
_refine_diff_density_rms         0.219
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.209
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3432
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1028
_refine_ls_R_factor_gt           0.1019
_refine_ls_restrained_S_all      1.209
_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)+36.6427P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2915
_refine_ls_wR_factor_ref         0.2917
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C11(H11), C5(H5), C6(H6), C3(H3A), C4(H4)
;
_atom_sites_solution_hydrogens   mixed
_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
Cl6 Cl 0.1488(3) 0.7459(3) 0.5225(2) 0.0251(6) Uani 1 1 d . . . . .
Cl1 Cl -0.0216(4) 0.3022(3) 0.0796(2) 0.0267(6) Uani 1 1 d . . . . .
S1 S -0.0408(3) 0.3704(3) 0.2421(2) 0.0184(6) Uani 1 1 d . . . . .
Cl3 Cl -0.3581(4) 0.8927(4) -0.0298(2) 0.0317(7) Uani 1 1 d . . . . .
Cl4 Cl -0.5939(3) 0.5756(4) 0.0942(2) 0.0265(7) Uani 1 1 d . . . . .
Cl2 Cl 0.0295(5) 1.0443(3) 0.3121(3) 0.0362(8) Uani 1 1 d . . . . .
Cl5 Cl 0.5066(5) 1.1504(4) 0.2940(3) 0.0443(9) Uani 1 1 d . . . . .
N2 N 0.1645(11) 0.6981(10) 0.2602(7) 0.0166(18) Uani 1 1 d . . . . .
N1 N 0.1483(12) 0.4438(10) 0.3080(7) 0.0187(19) Uani 1 1 d . . . . .
N3 N 0.7654(12) 0.7258(11) 0.4506(8) 0.024(2) Uani 1 1 d . . . . .
H3 H 0.874943 0.753704 0.479838 0.028 Uiso 1 1 calc R . . . .
C12 C -0.1260(13) 0.5204(12) 0.2072(8) 0.016(2) Uani 1 1 d . . . . .
C9 C -0.2623(14) 0.7601(13) 0.1475(8) 0.019(2) Uani 1 1 d . . . . .
C11 C -0.3043(14) 0.4926(13) 0.1686(9) 0.019(2) Uani 1 1 d . . . . .
H11 H -0.377987 0.394941 0.161385 0.023 Uiso 1 1 calc R . . . .
C2 C 0.4190(13) 0.6391(12) 0.3555(9) 0.018(2) Uani 1 1 d . . . . .
C1 C 0.2302(14) 0.5935(12) 0.3019(8) 0.018(2) Uani 1 1 d . . . . .
C7 C -0.0096(14) 0.6676(12) 0.2187(8) 0.018(2) Uani 1 1 d . . . . .
C8 C -0.0800(14) 0.7864(12) 0.1858(9) 0.019(2) Uani 1 1 d . . . . .
C5 C 0.6888(14) 0.5811(13) 0.4239(9) 0.021(2) Uani 1 1 d . . . . .
H5 H 0.752596 0.511091 0.437029 0.025 Uiso 1 1 calc R . . . .
C6 C 0.5136(14) 0.5349(12) 0.3765(8) 0.018(2) Uani 1 1 d . . . . .
H6 H 0.458602 0.433061 0.358480 0.022 Uiso 1 1 calc R . . . .
C3 C 0.5029(15) 0.7911(13) 0.3855(9) 0.023(2) Uani 1 1 d . . . . .
H3A H 0.441639 0.863080 0.373191 0.028 Uiso 1 1 calc R . . . .
C4 C 0.6774(15) 0.8324(13) 0.4336(10) 0.025(2) Uani 1 1 d . . . . .
H4 H 0.735316 0.933004 0.454555 0.030 Uiso 1 1 calc R . . . .
C10 C -0.3697(15) 0.6121(14) 0.1412(9) 0.022(2) Uani 1 1 d . . . . .
C14 C -0.3391(16) 0.8866(14) 0.1104(9) 0.024(2) Uani 1 1 d . . . . .
H14A H -0.264146 0.981604 0.145870 0.029 Uiso 1 1 calc R . . . .
H14B H -0.453311 0.870005 0.127137 0.029 Uiso 1 1 calc R . . . .
C13 C 0.0395(15) 0.9422(13) 0.1946(10) 0.024(2) Uani 1 1 d . . . . .
H13A H 0.005368 0.993987 0.132570 0.029 Uiso 1 1 calc R . . . .
H13B H 0.158346 0.937763 0.198408 0.029 Uiso 1 1 calc R . . . .
H5A H 0.741(16) 1.233(13) 0.323(9) 0.02(3) Uiso 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
Cl1 S1 2.238(4) . ?
S1 N1 1.562(9) . ?
S1 C12 1.735(11) . ?
Cl3 C14 1.793(12) . ?
Cl4 C10 1.738(11) . ?
Cl2 C13 1.808(13) . ?
Cl5 H5A 1.81(12) . ?
N2 C1 1.298(14) . ?
N2 C7 1.357(14) . ?
N1 C1 1.374(14) . ?
N3 H3 0.8600 . ?
N3 C5 1.322(15) . ?
N3 C4 1.361(15) . ?
C12 C11 1.384(15) . ?
C12 C7 1.418(15) . ?
C9 C8 1.416(15) . ?
C9 C10 1.401(17) . ?
C9 C14 1.507(15) . ?
C11 H11 0.9300 . ?
C11 C10 1.370(16) . ?
C2 C1 1.492(15) . ?
C2 C6 1.383(15) . ?
C2 C3 1.397(16) . ?
C7 C8 1.402(15) . ?
C8 C13 1.491(16) . ?
C5 H5 0.9300 . ?
C5 C6 1.377(15) . ?
C6 H6 0.9300 . ?
C3 H3A 0.9300 . ?
C3 C4 1.374(16) . ?
C4 H4 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

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
N1 S1 Cl1 108.2(4) . . ?
N1 S1 C12 105.1(5) . . ?
C12 S1 Cl1 96.9(4) . . ?
C1 N2 C7 120.4(9) . . ?
C1 N1 S1 120.6(8) . . ?
C5 N3 H3 118.7 . . ?
C5 N3 C4 122.5(10) . . ?
C4 N3 H3 118.7 . . ?
C11 C12 S1 119.2(8) . . ?
C11 C12 C7 122.3(10) . . ?
C7 C12 S1 118.5(8) . . ?
C8 C9 C14 121.2(10) . . ?
C10 C9 C8 118.3(10) . . ?
C10 C9 C14 120.5(10) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 C12 118.5(10) . . ?
C10 C11 H11 120.7 . . ?
C6 C2 C1 121.8(10) . . ?
C6 C2 C3 119.0(10) . . ?
C3 C2 C1 119.2(10) . . ?
N2 C1 N1 129.1(10) . . ?
N2 C1 C2 117.3(10) . . ?
N1 C1 C2 113.6(9) . . ?
N2 C7 C12 123.3(10) . . ?
N2 C7 C8 119.1(10) . . ?
C8 C7 C12 117.6(10) . . ?
C9 C8 C13 120.3(10) . . ?
C7 C8 C9 120.7(10) . . ?
C7 C8 C13 119.0(10) . . ?
N3 C5 H5 120.3 . . ?
N3 C5 C6 119.4(10) . . ?
C6 C5 H5 120.3 . . ?
C2 C6 H6 119.8 . . ?
C5 C6 C2 120.4(10) . . ?
C5 C6 H6 119.8 . . ?
C2 C3 H3A 120.6 . . ?
C4 C3 C2 118.8(11) . . ?
C4 C3 H3A 120.6 . . ?
N3 C4 C3 119.9(11) . . ?
N3 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C9 C10 Cl4 119.6(9) . . ?
C11 C10 Cl4 118.0(9) . . ?
C11 C10 C9 122.4(10) . . ?
Cl3 C14 H14A 109.9 . . ?
Cl3 C14 H14B 109.9 . . ?
C9 C14 Cl3 108.8(8) . . ?
C9 C14 H14A 109.9 . . ?
C9 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
Cl2 C13 H13A 109.7 . . ?
Cl2 C13 H13B 109.7 . . ?
C8 C13 Cl2 109.8(8) . . ?
C8 C13 H13A 109.7 . . ?
C8 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?


_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 1.432
_oxdiff_exptl_absorpt_empirical_full_min 0.613

# start Validation Reply Form
_vrf_DIFMX02_abs-819-twin-r1_twin1_hklf4-rf 
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*0.75
RESPONSE: Residual electron density located in close proximity to the 
pyridyl-proton which may indicate disorder of the HCl2 counteranion.
;
_vrf_PLAT305_abs-819-twin-r1_twin1_hklf4-rf 
;
PROBLEM: Isolated Hydrogen Atom   (Outside Bond Range ??)        H5A Check 
RESPONSE: This compound features the HCl2 anion where H5A is bound to Cl5
and Cl6.
;
_vrf_PLAT084_abs-819-twin-r1_twin1_hklf4-rf 
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.29 Report
RESPONSE: Twinned crystal with evidence of HCl2 anion disorder or
decomposition during data collection resulting in a high wR2 value.
;
_vrf_PLAT097_abs-819-twin-r1_twin1_hklf4-rf 
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.33 eA-3  
RESPONSE: Residual electron density located in close proximity to the 
pyridyl-proton which may indicate disorder of the HCl2 counteranion.
;
_vrf_PLAT431_abs-819-twin-r1_twin1_hklf4-rf 
;
PROBLEM: Short Inter HL..A Contact  Cl2      ..S1               3.32 Ang.  
RESPONSE: Weak S...Cl contacts between neighbouring molecules.
;
# end Validation Reply Form
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_serc094-r1-or-fe-rf1
_database_code_depnum_ccdc_archive 'CCDC 2101076'
loop_
_audit_author_name
_audit_author_address
'Andryj M Borys'
;University of Kent
United Kingdom
;
_audit_update_record             
;
2021-08-03 deposited with the CCDC.	2021-11-23 downloaded from the CCDC.
;
_audit_creation_date             2021-05-14
_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         'C12 H5.84 Cl2.16 N3 S'
_chemical_formula_sum            'C12 H5.84 Cl2.16 N3 S'
_chemical_formula_weight         300.84
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H5.84 Cl2.16 N3 S'
_chemical_oxdiff_usercomment     'ABS-261 radical/pyridine'
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'
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'
Cl Cl 0.3639 0.7018 '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                   7.4291(4)
_cell_length_b                   18.6148(9)
_cell_length_c                   9.0438(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.796(6)
_cell_angle_gamma                90
_cell_volume                     1190.83(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14710
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      76.0600
_cell_measurement_theta_min      5.0540
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.430
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.381
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark violet'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             628
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 6 0.0222
-5 1 0 0.1461
0 0 -6 0.0541
2 1 4 0.0653
0 -12 0 0.0262
-2 1 -4 0.0957
0 12 0 0.0271
5 -2 -1 0.1209

_exptl_crystal_size_max          0.304
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.053
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0434 0.2378 5.5675 -0.0843 0.4474 0.8903
-4.5317 0.8513 -0.2202 -0.1233 0.6672 -0.7346
0.0643 -0.2600 -5.6066 0.0879 -0.4669 -0.8799
2.2186 0.9997 4.1217 0.0977 0.0276 0.9948
0.0358 -12.0699 -0.2056 -0.9586 -0.2847 -0.0089
-2.2355 0.9035 -4.1100 0.0533 0.0172 -0.9984
-0.0358 12.0699 0.2056 0.9586 0.2847 0.0089
5.0069 -1.9960 -1.0104 0.0756 -0.8612 0.6141

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            23707
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.330
_diffrn_reflns_theta_min         4.751
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2774
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    6.50    --  -41.95 -38.00  30.00   99
  2  ω   -115.00 -14.00   1.00    6.50    --  -41.95 -57.00 -60.00  101
  3  ω    -66.00  32.00   1.00    6.50    --  -41.95  38.00-150.00   98
  4  ω     23.00  98.00   1.00    6.50    --   41.95-125.00  30.00   75
  5  ω      1.00  83.00   1.00    6.50    --   41.95 -99.00-120.00   82
  6  ω     28.00 109.00   1.00   27.50    --  111.00 -94.00  90.00   81
  7  ω     35.00 116.00   1.00   27.50    --  111.00-111.00 -30.00   81
  8  ω     35.00 144.00   1.00   27.50    --  111.00 -77.00 150.00  109
  9  ω     38.00 137.00   1.00   27.50    --  111.00 -45.00  60.00   99
 10  ω     38.00 137.00   1.00   27.50    --  111.00 -45.00-180.00   99
 11  ω     35.00 144.00   1.00   27.50    --  111.00 -77.00  30.00  109
 12  ω     28.00 109.00   1.00   27.50    --  111.00 -94.00  30.00   81
 13  ω     35.00 139.00   1.00   27.50    --  111.00 -30.00 120.00  104
 14  ω     83.00 178.00   1.00   27.50    --  111.00  30.00   0.00   95
 15  ω     35.00 116.00   1.00   27.50    --  111.00-111.00-180.00   81
 16  ω    100.00 178.00   1.00   27.50    --  111.00 111.00-180.00   78
 17  ω     35.00 144.00   1.00   27.50    --  111.00 -77.00-150.00  109
 18  ω     58.00 178.00   1.00   27.50    --  111.00  15.00 -30.00  120
 19  ω     35.00 116.00   1.00   27.50    --  111.00-111.00  30.00   81
 20  ω     58.00 178.00   1.00   27.50    --  111.00  15.00-150.00  120
 21  ω     28.00 109.00   1.00   27.50    --  111.00 -94.00 -60.00   81
 22  ω     35.00 116.00   1.00   27.50    --  111.00-111.00 -90.00   81
 23  ω     28.00 109.00   1.00   27.50    --  111.00 -94.00   0.00   81
 24  ω     29.00 164.00   1.00   27.50    --  111.00 -15.00 -30.00  135
 25  ω   -118.00  -9.00   1.00    6.50    --  -41.95 -77.00-180.00  109
 26  ω   -118.00  -9.00   1.00    6.50    --  -41.95 -77.00  90.00  109
 27  ω   -118.00  -9.00   1.00    6.50    --  -41.95 -77.00 -90.00  109
 28  ω      9.00 118.00   1.00    6.50    --   41.95  77.00  30.00  109
 29  ω    -30.00  70.00   1.00    6.50    --   41.95 -57.00  30.00  100
 30  ω      9.00 118.00   1.00    6.50    --   41.95  77.00  90.00  109
 31  ω     83.00 178.00   1.00   27.50    --  111.00  30.00  90.00   95
 32  ω     82.00 178.00   1.00   27.50    --  111.00  61.00-150.00   96
 33  ω     82.00 178.00   1.00   27.50    --  111.00  61.00 120.00   96
 34  ω     78.00 147.00   1.00   27.50    --  111.00  77.00-120.00   69
 35  ω     85.00 178.00   1.00   27.50    --  111.00  45.00  30.00   93
;
_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      0.0431329000
_diffrn_orient_matrix_UB_12      0.0798694000
_diffrn_orient_matrix_UB_13      -0.0188816000
_diffrn_orient_matrix_UB_21      -0.1470620000
_diffrn_orient_matrix_UB_22      0.0217747000
_diffrn_orient_matrix_UB_23      0.0805843000
_diffrn_orient_matrix_UB_31      0.1540976000
_diffrn_orient_matrix_UB_32      -0.0015067000
_diffrn_orient_matrix_UB_33      0.1587806000
_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                2478
_reflns_number_total             2489
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.912
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2489
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.093
_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)+(0.0485P)²+2.1077P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1183
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 H9-C9
 0.93 with sigma of 0.02
3. Restrained planarity
 C8, C9, C10, C11, C12, C7
 with sigma of 0.1
 H9, C9, C8, C7, C12, C11, C10
 with sigma of 0.1
4. Others
 Sof(Cl)=1-FVAR(1)
 Sof(H9)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C11(H11), C3(H3), C4(H4)
;
_atom_sites_solution_hydrogens   mixed
_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
S1 S 0.03039(9) 0.59627(3) 0.36405(7) 0.02929(18) Uani 1 1 d . . . . .
Cl1 Cl 0.53885(11) 0.43016(4) 0.77856(8) 0.0433(2) Uani 1 1 d . . . . .
Cl2 Cl 0.47842(11) 0.71132(4) 0.89656(9) 0.0425(2) Uani 1 1 d . . . . .
N2 N 0.2521(3) 0.45898(12) 0.4855(2) 0.0264(4) Uani 1 1 d . . . . .
N1 N 0.0162(3) 0.51880(12) 0.2772(2) 0.0287(5) Uani 1 1 d . . . . .
N3 N 0.0222(3) 0.26563(13) 0.0892(3) 0.0321(5) Uani 1 1 d . . . . .
C1 C 0.1238(4) 0.46329(14) 0.3451(3) 0.0252(5) Uani 1 1 d . . . . .
C2 C 0.0927(4) 0.39553(14) 0.2536(3) 0.0249(5) Uani 1 1 d . . . . .
C7 C 0.2964(3) 0.51881(14) 0.5768(3) 0.0268(5) Uani 1 1 d . . . . .
C6 C 0.1724(4) 0.33160(14) 0.3231(3) 0.0270(5) Uani 1 1 d . . . . .
H6 H 0.2507 0.3310 0.4254 0.032 Uiso 1 1 calc R . . . .
C5 C 0.1329(4) 0.26888(15) 0.2373(3) 0.0298(5) Uani 1 1 d . . . . .
H5 H 0.1862 0.2264 0.2851 0.036 Uiso 1 1 calc R . . . .
C12 C 0.2141(4) 0.58733(14) 0.5379(3) 0.0272(5) Uani 1 1 d . . . . .
C10 C 0.4095(4) 0.63790(16) 0.7740(3) 0.0326(6) Uani 1 1 d . . . . .
C11 C 0.2700(4) 0.64716(15) 0.6341(3) 0.0307(6) Uani 1 1 d . . . . .
H11 H 0.2149 0.6919 0.6047 0.037 Uiso 1 1 calc R . . . .
C9 C 0.4939(4) 0.57150(16) 0.8205(3) 0.0328(6) Uani 1 1 d D . . . .
C8 C 0.4375(4) 0.51324(15) 0.7230(3) 0.0307(6) Uani 1 1 d . . . . .
C3 C -0.0188(4) 0.39350(15) 0.0984(3) 0.0310(6) Uani 1 1 d . . . . .
H3 H -0.0716 0.4353 0.0469 0.037 Uiso 1 1 calc R . . . .
C4 C -0.0489(4) 0.32797(15) 0.0232(3) 0.0340(6) Uani 1 1 d . . . . .
H4 H -0.1236 0.3271 -0.0801 0.041 Uiso 1 1 calc R . . . .
Cl Cl 0.6747(5) 0.5614(2) 0.9843(4) 0.0330(15) Uani 0.165(4) 1 d . . P A 2
H9 H 0.586(3) 0.5648(19) 0.914(2) 0.025(9) Uiso 0.835(4) 1 d D . P A 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 N1 1.630(2) . ?
S1 C12 1.746(3) . ?
Cl1 C8 1.726(3) . ?
Cl2 C10 1.735(3) . ?
N2 C1 1.337(3) . ?
N2 C7 1.365(3) . ?
N1 C1 1.335(3) . ?
N3 C5 1.342(3) . ?
N3 C4 1.337(4) . ?
C1 C2 1.487(3) . ?
C2 C6 1.391(3) . ?
C2 C3 1.395(3) . ?
C7 C12 1.412(4) . ?
C7 C8 1.418(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.383(4) . ?
C5 H5 0.9300 . ?
C12 C11 1.396(4) . ?
C10 C11 1.380(4) . ?
C10 C9 1.392(4) . ?
C11 H11 0.9300 . ?
C9 C8 1.379(4) . ?
C9 Cl 1.679(4) . ?
C9 H9 0.92(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(4) . ?
C4 H4 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
N1 S1 C12 105.49(12) . . ?
C1 N2 C7 119.7(2) . . ?
C1 N1 S1 121.44(18) . . ?
C4 N3 C5 116.4(2) . . ?
N2 C1 C2 115.0(2) . . ?
N1 C1 N2 129.5(2) . . ?
N1 C1 C2 115.5(2) . . ?
C6 C2 C1 120.1(2) . . ?
C6 C2 C3 118.1(2) . . ?
C3 C2 C1 121.8(2) . . ?
N2 C7 C12 125.5(2) . . ?
N2 C7 C8 118.5(2) . . ?
C12 C7 C8 116.0(2) . . ?
C2 C6 H6 120.6 . . ?
C5 C6 C2 118.7(2) . . ?
C5 C6 H6 120.6 . . ?
N3 C5 C6 124.0(2) . . ?
N3 C5 H5 118.0 . . ?
C6 C5 H5 118.0 . . ?
C7 C12 S1 118.04(19) . . ?
C11 C12 S1 119.1(2) . . ?
C11 C12 C7 122.8(2) . . ?
C11 C10 Cl2 118.7(2) . . ?
C11 C10 C9 122.1(3) . . ?
C9 C10 Cl2 119.3(2) . . ?
C12 C11 H11 121.0 . . ?
C10 C11 C12 118.0(3) . . ?
C10 C11 H11 121.0 . . ?
C10 C9 Cl 122.1(3) . . ?
C10 C9 H9 123(2) . . ?
C8 C9 C10 119.0(3) . . ?
C8 C9 Cl 118.7(3) . . ?
C8 C9 H9 118(2) . . ?
C7 C8 Cl1 118.0(2) . . ?
C9 C8 Cl1 119.9(2) . . ?
C9 C8 C7 122.1(3) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 C2 118.5(2) . . ?
C4 C3 H3 120.8 . . ?
N3 C4 C3 124.3(2) . . ?
N3 C4 H4 117.8 . . ?
C3 C4 H4 117.8 . . ?

_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 2.759
_oxdiff_exptl_absorpt_empirical_full_min 0.710
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
####################################################################### 
# 
# 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_serc114-r2-rf
_database_code_depnum_ccdc_archive 'CCDC 2101078'
loop_
_audit_author_name
_audit_author_address
'Andryj M Borys'
;University of Kent
United Kingdom
;
_audit_update_record             
;
2021-08-03 deposited with the CCDC.	2021-11-23 downloaded from the CCDC.
;
_audit_creation_date             2018-06-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H6 Cl3 N2 S, C0.5 H Cl'
_chemical_formula_sum            'C13.50 H7 Cl4 N2 S'
_chemical_formula_weight         371.07
_chemical_melting_point          ?
_chemical_oxdiff_formula         'S1 N2 Cl4 C13.5 H8'
_chemical_oxdiff_usercomment     'ABS-410 100K'
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           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   16.7712(3)
_cell_length_b                   13.1359(2)
_cell_length_c                   13.0495(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2874.87(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    52319
_cell_measurement_temperature    100.0(7)
_cell_measurement_theta_max      76.1040
_cell_measurement_theta_min      4.7660
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.764
_exptl_absorpt_correction_T_max  0.569
_exptl_absorpt_correction_T_min  0.282
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark violet'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1488
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 -3 -8 0.1072
-8 6 0 0.0362
3 3 8 0.1362
8 -6 0 0.0425
0 1 -8 0.1167
8 6 0 0.0506
0 -1 8 0.1360
-8 -6 0 0.0308

_exptl_crystal_size_max          0.257
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.08
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.5157 -2.6887 -7.8146 -0.1070 -0.0186 0.9941
-7.9082 5.8450 -0.0460 0.9810 0.1826 0.0655
2.5577 2.6586 7.8166 0.1019 0.0177 -0.9946
7.8759 -5.8717 -0.0410 -0.9817 -0.1827 -0.0544
-0.1862 0.5057 -8.4743 -0.0774 0.4107 0.9085
7.6508 6.0516 -0.0665 -0.1686 0.9083 -0.3829
0.1182 -0.5592 8.4716 0.0789 -0.4187 -0.9047
-7.6363 -6.0565 0.2788 0.1703 -0.9174 0.3596

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0861
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            72177
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.014
_diffrn_reflns_theta_min         4.275
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(7)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2774
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    5.00    --  -41.95 -38.00-180.00   99
  2  ω   -116.00 -17.00   1.00    5.00    --  -41.95 -38.00 -90.00   99
  3  ω    -32.00  66.00   1.00    5.00    --   41.95 -38.00  30.00   98
  4  ω      1.00  83.00   1.00    5.00    --   41.95 -99.00 150.00   82
  5  ω     23.00  98.00   1.00    5.00    --   41.95-125.00   0.00   75
  6  ω      1.00  83.00   1.00    5.00    --   41.95 -99.00   0.00   82
  7  ω     23.00  98.00   1.00    5.00    --   41.95-125.00  90.00   75
  8  ω     35.00 138.00   1.00   17.50    --  111.00 -31.00  -3.76  103
  9  ω     83.00 178.00   1.00   17.50    --  111.00  30.00 -60.00   95
 10  ω     38.00 141.00   1.00   17.50    --  111.00 -65.00-146.14  103
 11  ω     39.00 140.00   1.00   17.50    --  111.00 -61.00 -60.00  101
 12  ω     82.00 178.00   1.00   17.50    --  111.00  61.00 -60.00   96
 13  ω     36.00 143.00   1.00   17.50    --  111.00 -73.00 135.33  107
 14  ω     83.00 178.00   1.00   17.50    --  111.00  30.00   0.00   95
 15  ω    100.00 178.00   1.00   17.50    --  111.00 111.00-180.00   78
 16  ω     35.00 116.00   1.00   17.50    --  111.00-111.00  30.00   81
 17  ω     37.00 136.00   1.00   17.50    --  111.00 -39.00 -18.33   99
 18  ω     35.00 116.00   1.00   17.50    --  111.00-111.00 -90.00   81
 19  ω    100.00 178.00   1.00   17.50    --  111.00 111.00-150.00   78
 20  ω     35.00 116.00   1.00   17.50    --  111.00-111.00-120.00   81
 21  ω     85.00 178.00   1.00   17.50    --  111.00  45.00 -60.00   93
 22  ω     28.00 109.00   1.00   17.50    --  111.00 -94.00-150.00   81
 23  ω     31.00 111.00   1.00   17.50    --  111.00-100.00  95.00   80
 24  ω     35.00 116.00   1.00   17.50    --  111.00-111.00-180.00   81
 25  ω     58.00 178.00   1.00   17.50    --  111.00  15.00-180.00  120
 26  ω     38.00 137.00   1.00   17.50    --  111.00 -45.00 -60.00   99
 27  ω     35.00 116.00   1.00   17.50    --  111.00-111.00  90.00   81
 28  ω     28.00 109.00   1.00   17.50    --  111.00 -94.00 120.00   81
 29  ω     35.00 116.00   1.00   17.50    --  111.00-111.00 -30.00   81
 30  ω     35.00 116.00   1.00   17.50    --  111.00-111.00-150.00   81
 31  ω     38.00 137.00   1.00   17.50    --  111.00 -45.00  90.00   99
 32  ω     23.00 178.00   1.00   17.50    --  111.00   0.00 -90.00  155
 33  ω     83.00 178.00   1.00   17.50    --  111.00  30.00  60.00   95
 34  ω     35.00 139.00   1.00   17.50    --  111.00 -30.00 150.00  104
 35  ω     35.00 144.00   1.00   17.50    --  111.00 -77.00 -60.00  109
 36  ω     35.00 144.00   1.00   17.50    --  111.00 -77.00 150.00  109
 37  ω     35.00 116.00   1.00   17.50    --  111.00-111.00 150.00   81
 38  ω     38.00 137.00   1.00   17.50    --  111.00 -45.00 -90.00   99
 39  ω     29.00 164.00   1.00   17.50    --  111.00 -15.00  90.00  135
 40  ω     37.00 142.00   1.00   17.50    --  111.00 -72.00 102.51  105
 41  ω     28.00 109.00   1.00   17.50    --  111.00 -94.00 -90.00   81
 42  ω     32.00 109.00   1.00   17.50    --  111.00 -94.00   0.00   77
 43  ω    102.00 145.00   1.00   17.50    --  111.00 -85.00 -92.21   43
 44  ω     87.00 123.00   1.00   17.50    --  111.00  45.00 -90.00   36
 45  ω    141.00 171.00   1.00   17.50    --  111.00  45.00 -90.00   30
 46  ω    105.00 142.00   1.00   17.50    --  111.00 178.00-150.00   37
 47  ω     51.00 120.00   1.00   17.50    --  111.00 -48.00 134.98   69
 48  ω     34.00  93.00   1.00   17.50    --  111.00 -85.00 -92.21   59
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0747518000
_diffrn_orient_matrix_UB_12      0.0668136000
_diffrn_orient_matrix_UB_13      0.0147681000
_diffrn_orient_matrix_UB_21      0.0453587000
_diffrn_orient_matrix_UB_22      0.0922651000
_diffrn_orient_matrix_UB_23      -0.0439606000
_diffrn_orient_matrix_UB_31      -0.0285855000
_diffrn_orient_matrix_UB_32      -0.0283156000
_diffrn_orient_matrix_UB_33      -0.1082633000
_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                2777
_reflns_number_total             2779
_reflns_odcompleteness_completeness 99.90
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.153
_refine_diff_density_min         -0.683
_refine_diff_density_rms         0.126
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.237
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2779
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0615
_refine_ls_restrained_S_all      1.237
_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)+(0.0311P)²+15.7442P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1453
_refine_ls_wR_factor_ref         0.1454
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Fixed Sof: H14A(0.5) H14B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C6(H6), C12(H12)
;
_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
Cl1 Cl 0.51040(7) 0.76359(8) 0.60862(8) 0.0276(3) Uani 1 1 d . . . . .
S1 S 0.43029(6) 0.36895(8) 0.65515(8) 0.0241(3) Uani 1 1 d . . . . .
Cl3 Cl 0.20664(7) 0.65608(11) 0.70102(9) 0.0362(3) Uani 1 1 d . . . . .
Cl2 Cl 0.33389(8) 0.82559(10) 0.65202(10) 0.0394(3) Uani 1 1 d . . . . .
Cl4 Cl 0.50716(10) 0.09254(15) 0.63933(14) 0.0659(5) Uani 1 1 d . . . . .
N2 N 0.5416(2) 0.5471(3) 0.6135(2) 0.0164(7) Uani 1 1 d . . . . .
N1 N 0.5250(2) 0.3656(3) 0.6329(3) 0.0215(8) Uani 1 1 d . . . . .
C2 C 0.6528(2) 0.4367(3) 0.5937(3) 0.0174(8) Uani 1 1 d . . . . .
C1 C 0.5665(2) 0.4515(3) 0.6140(3) 0.0175(8) Uani 1 1 d . . . . .
C3 C 0.7016(3) 0.5207(3) 0.5769(3) 0.0202(9) Uani 1 1 d . . . . .
H3 H 0.679596 0.585697 0.576858 0.024 Uiso 1 1 calc R . . . .
C8 C 0.4630(2) 0.5694(3) 0.6342(3) 0.0187(8) Uani 1 1 d . . . . .
C13 C 0.4038(2) 0.4966(3) 0.6552(3) 0.0209(8) Uani 1 1 d . . . . .
C4 C 0.7826(3) 0.5084(4) 0.5601(3) 0.0238(9) Uani 1 1 d . . . . .
H4 H 0.814804 0.565072 0.549605 0.029 Uiso 1 1 calc R . . . .
C9 C 0.4396(3) 0.6722(3) 0.6345(3) 0.0217(9) Uani 1 1 d . . . . .
C5 C 0.8155(3) 0.4121(4) 0.5591(3) 0.0266(9) Uani 1 1 d . . . . .
H5 H 0.869760 0.403795 0.547170 0.032 Uiso 1 1 calc R . . . .
C7 C 0.6864(3) 0.3396(3) 0.5929(3) 0.0235(9) Uani 1 1 d . . . . .
H7 H 0.654427 0.282869 0.603930 0.028 Uiso 1 1 calc R . . . .
C6 C 0.7673(3) 0.3275(4) 0.5759(4) 0.0291(10) Uani 1 1 d . . . . .
H6 H 0.789519 0.262654 0.575599 0.035 Uiso 1 1 calc R . . . .
C11 C 0.3042(3) 0.6240(4) 0.6750(3) 0.0258(10) Uani 1 1 d . . . . .
C12 C 0.3252(3) 0.5235(4) 0.6761(3) 0.0248(9) Uani 1 1 d . . . . .
H12 H 0.287471 0.473635 0.690644 0.030 Uiso 1 1 calc R . . . .
C10 C 0.3611(3) 0.7001(4) 0.6547(3) 0.0273(10) Uani 1 1 d . . . . .
C14 C 0.500000 0.0189(6) 0.750000 0.064(3) Uani 1 2 d S T P . .
H14A H 0.453418 -0.024576 0.745025 0.077 Uiso 0.5 1 calc R . . . .
H14B H 0.546580 -0.024580 0.754974 0.077 Uiso 0.5 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 C9 1.722(5) . ?
S1 N1 1.615(4) . ?
S1 C13 1.735(5) . ?
Cl3 C11 1.723(4) . ?
Cl2 C10 1.711(5) . ?
Cl4 C14 1.742(5) . ?
N2 C1 1.324(5) . ?
N2 C8 1.376(5) . ?
N1 C1 1.347(5) . ?
C2 C1 1.485(6) . ?
C2 C3 1.390(6) . ?
C2 C7 1.395(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(6) . ?
C8 C13 1.405(6) . ?
C8 C9 1.407(6) . ?
C13 C12 1.392(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.380(6) . ?
C9 C10 1.391(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.391(7) . ?
C7 H7 0.9300 . ?
C7 C6 1.383(6) . ?
C6 H6 0.9300 . ?
C11 C12 1.367(7) . ?
C11 C10 1.408(7) . ?
C12 H12 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?

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
N1 S1 C13 106.1(2) . . ?
C1 N2 C8 120.2(4) . . ?
C1 N1 S1 121.2(3) . . ?
C3 C2 C1 119.9(4) . . ?
C3 C2 C7 119.1(4) . . ?
C7 C2 C1 121.0(4) . . ?
N2 C1 N1 129.2(4) . . ?
N2 C1 C2 115.5(4) . . ?
N1 C1 C2 115.3(4) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(4) . . ?
C4 C3 H3 119.7 . . ?
N2 C8 C13 124.8(4) . . ?
N2 C8 C9 118.2(4) . . ?
C13 C8 C9 117.0(4) . . ?
C8 C13 S1 118.4(3) . . ?
C12 C13 S1 119.2(3) . . ?
C12 C13 C8 122.4(4) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(4) . . ?
C5 C4 H4 120.0 . . ?
C8 C9 Cl1 118.4(3) . . ?
C10 C9 Cl1 120.4(3) . . ?
C10 C9 C8 121.2(4) . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.9(4) . . ?
C6 C5 H5 120.1 . . ?
C2 C7 H7 119.9 . . ?
C6 C7 C2 120.2(4) . . ?
C6 C7 H7 119.9 . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.2(4) . . ?
C7 C6 H6 119.9 . . ?
C12 C11 Cl3 118.7(4) . . ?
C12 C11 C10 120.8(4) . . ?
C10 C11 Cl3 120.5(4) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 C13 119.2(4) . . ?
C11 C12 H12 120.4 . . ?
C9 C10 Cl2 120.2(4) . . ?
C9 C10 C11 119.4(4) . . ?
C11 C10 Cl2 120.4(4) . . ?
Cl4 C14 Cl4 112.6(5) 3_656 . ?
Cl4 C14 H14A 109.1 . . ?
Cl4 C14 H14A 109.1 3_656 . ?
Cl4 C14 H14B 109.1 3_656 . ?
Cl4 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?


_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 1.406
_oxdiff_exptl_absorpt_empirical_full_min 0.781

# start Validation Reply Form
_vrf_PLAT340_serc114-r2-rf       
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00638 Ang.  
RESPONSE: This is ascribed to a consequence of partially disordered solvent.
;
# end Validation Reply Form
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
####################################################################### 
# 
# 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_serc118-r1-fm-non-equiv-rf1
_database_code_depnum_ccdc_archive 'CCDC 2101063'
loop_
_audit_author_name
_audit_author_address
'Andryj M Borys'
;University of Kent
United Kingdom
;
_audit_update_record             
;
2021-08-03 deposited with the CCDC.	2021-11-23 downloaded from the CCDC.
;
_audit_creation_date             2018-06-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C14 H8 Cl4 N2 S)'
_chemical_formula_sum            'C28 H16 Cl8 N4 S2'
_chemical_formula_weight         756.17
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C28 N4 S2 Cl8 H14'
_chemical_oxdiff_usercomment     ABS-295
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           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                   9.0246(3)
_cell_length_b                   13.7857(5)
_cell_length_c                   12.0756(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.513(3)
_cell_angle_gamma                90
_cell_volume                     1485.78(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    37692
_cell_measurement_temperature    100.0(6)
_cell_measurement_theta_max      75.7670
_cell_measurement_theta_min      3.6390
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.491
_exptl_absorpt_correction_T_max  0.722
_exptl_absorpt_correction_T_min  0.328
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark yellow'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 9 -1 0.0966
-3 -2 -6 0.0316
1 -8 2 0.1104
3 2 6 0.0453
5 1 -5 0.0271
-5 0 5 0.0135

_exptl_crystal_size_max          0.216
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.048
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.8737 8.6500 -1.4451 0.2117 -0.5070 0.8356
-3.1764 -2.0279 -5.6337 0.3262 -0.7879 -0.5223
1.1753 -8.3854 1.9807 -0.2417 0.5795 -0.7783
3.1737 2.0577 5.6294 -0.3255 0.7862 0.5252
4.9184 0.5528 -5.1710 -0.9221 -0.3828 0.0576
-4.8595 0.0125 5.3025 0.9236 0.3833 0.0089

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0805
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            54843
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.067
_diffrn_reflns_theta_min         3.701
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2774
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -1.00  25.00   1.00    5.00    --   38.00  95.00 -26.00   26
  2  ω      6.00  34.00   1.00    5.00    --   42.00  87.00-137.12   28
  3  ω   -114.00 -14.00   1.00    5.00    --  -42.08 -57.00-180.00  100
  4  ω   -116.00 -18.00   1.00    5.00    --  -42.08 -38.00  60.00   98
  5  ω    -67.00  32.00   1.00    5.00    --  -42.08  38.00-120.00   99
  6  ω   -116.00 -18.00   1.00    5.00    --  -42.08 -38.00 -90.00   98
  7  ω     23.00  98.00   1.00    5.00    --   42.08-125.00   0.00   75
  8  ω     23.00  98.00   1.00    5.00    --   42.08-125.00 150.00   75
  9  ω     16.00  45.00   1.00    5.00    --   50.00  82.00 123.54   29
 10  ω     17.00  46.00   1.00    5.00    --   50.00  80.00 -25.04   29
 11  ω     20.00  46.00   1.00    5.00    --   54.00  81.00-124.45   26
 12  ω     20.00  46.00   1.00    5.00    --   54.00  81.00  62.43   26
 13  ω     25.00 134.00   1.00    5.00    --   58.00  77.00  21.36  109
 14  ω     29.00 138.00   1.00    5.00    --   62.00  77.00 114.13  109
 15  ω     30.00 138.00   1.00    5.00    --   62.00  76.00 154.66  108
 16  ω     33.00 142.00   1.00    5.00    --   66.00  77.00-172.27  109
 17  ω     33.00 142.00   1.00    5.00    --   66.00  77.00 -44.94  109
 18  ω     38.00 146.00   1.00    5.00    --   70.00  76.00  34.91  108
 19  ω     38.00 146.00   1.00    5.00    --   70.00  76.00-137.16  108
 20  ω     38.00 146.00   1.00    5.00    --   70.00  76.00 -91.12  108
 21  ω     38.00 146.00   1.00    5.00    --   70.00  76.00 -15.51  108
 22  ω     78.00 178.00   1.00   20.00    --  111.00  77.00-180.00  100
 23  ω     82.00 178.00   1.00   20.00    --  111.00  61.00-150.00   96
 24  ω     78.00 178.00   1.00   20.00    --  111.00  77.00 -30.00  100
 25  ω     82.00 178.00   1.00   20.00    --  111.00  61.00  90.00   96
 26  ω     82.00 178.00   1.00   20.00    --  111.00  61.00 -30.00   96
 27  ω     82.00 178.00   1.00   20.00    --  111.00  61.00 -90.00   96
 28  ω     82.00 178.00   1.00   20.00    --  111.00  61.00-180.00   96
 29  ω     35.00 116.00   1.00   20.00    --  111.00-111.00 -90.00   81
 30  ω     78.00 178.00   1.00   20.00    --  111.00  77.00  90.00  100
 31  ω    100.00 178.00   1.00   20.00    --  111.00 111.00  30.00   78
 32  ω     35.00 116.00   1.00   20.00    --  111.00-111.00 120.00   81
 33  ω     78.00 178.00   1.00   20.00    --  111.00  77.00 -60.00  100
 34  ω     82.00 178.00   1.00   20.00    --  111.00  61.00  30.00   96
 35  ω     78.00 178.00   1.00   20.00    --  111.00  77.00   0.00  100
 36  ω     78.00 178.00   1.00   20.00    --  111.00  77.00-120.00  100
 37  ω     35.00 116.00   1.00   20.00    --  111.00-111.00   0.00   81
 38  ω     82.00 178.00   1.00   20.00    --  111.00  61.00 150.00   96
 39  ω     78.00 178.00   1.00   20.00    --  111.00  77.00-150.00  100
 40  ω     82.00 178.00   1.00   20.00    --  111.00  61.00  60.00   96
 41  ω     78.00 178.00   1.00   20.00    --  111.00  77.00  60.00  100
 42  ω     82.00 178.00   1.00   20.00    --  111.00  61.00 120.00   96
 43  ω     78.00 178.00   1.00   20.00    --  111.00  77.00 120.00  100
 44  ω     82.00 178.00   1.00   20.00    --  111.00  61.00   0.00   96
 45  ω     28.00 109.00   1.00   20.00    --  111.00 -94.00-180.00   81
 46  ω     78.00 178.00   1.00   20.00    --  111.00  77.00 150.00  100
 47  ω     35.00 116.00   1.00   20.00    --  111.00-111.00 -30.00   81
 48  ω     78.00 178.00   1.00   20.00    --  111.00  77.00  30.00  100
 49  ω     35.00 116.00   1.00   20.00    --  111.00-111.00  30.00   81
 50  ω     82.00 178.00   1.00   20.00    --  111.00  61.00 -60.00   96
 51  ω     38.00 137.00   1.00   20.00    --  111.00 -45.00  30.00   99
 52  ω     28.00 109.00   1.00   20.00    --  111.00 -94.00-150.00   81
 53  ω     35.00 144.00   1.00   20.00    --  111.00 -77.00  30.00  109
 54  ω     78.00 178.00   1.00   20.00    --  111.00  77.00 -90.00  100
 55  ω      7.00  35.00   1.00    5.00    --   42.00  86.00  79.66   28
 56  ω   -114.00 -14.00   1.00    5.00    --  -42.08 -57.00 120.00  100
 57  ω     11.00 116.00   1.00    5.00    --   42.08  70.00 142.30  105
 58  ω     16.00  45.00   1.00    5.00    --   50.00  82.00-163.20   29
 59  ω     21.00  49.00   1.00    5.00    --   54.00  78.00 -75.62   28
 60  ω     20.00  46.00   1.00    5.00    --   54.00  81.00 -55.32   26
 61  ω     20.00  46.00   1.00    5.00    --   54.00  81.00 104.84   26
 62  ω     25.00 134.00   1.00    5.00    --   58.00  77.00 -71.09  109
 63  ω     26.00 133.00   1.00    5.00    --   58.00  75.00   6.09  107
 64  ω     26.00 133.00   1.00    5.00    --   58.00  75.00 110.06  107
 65  ω     25.00 134.00   1.00    5.00    --   58.00  77.00-132.01  109
 66  ω     30.00 138.00   1.00    5.00    --   62.00  76.00-107.44  108
 67  ω     30.00 137.00   1.00    5.00    --   62.00  75.00  33.64  107
 68  ω     30.00 137.00   1.00    5.00    --   62.00  75.00-135.39  107
 69  ω     30.00 137.00   1.00    5.00    --   62.00  75.00  79.94  107
 70  ω     34.00 142.00   1.00    5.00    --   66.00  76.00 -67.40  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1599030000
_diffrn_orient_matrix_UB_12      0.0129340000
_diffrn_orient_matrix_UB_13      0.0276028000
_diffrn_orient_matrix_UB_21      0.0535925000
_diffrn_orient_matrix_UB_22      -0.0329002000
_diffrn_orient_matrix_UB_23      0.1214787000
_diffrn_orient_matrix_UB_31      0.0358979000
_diffrn_orient_matrix_UB_32      0.1059595000
_diffrn_orient_matrix_UB_33      0.0343349000
_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         0.878
_reflns_Friedel_fraction_full    0.964
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                5556
_reflns_number_total             5617
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.102
_refine_diff_density_min         -0.693
_refine_diff_density_rms         0.128
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.06(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         5617
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0766
_refine_ls_restrained_S_all      1.093
_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)+(0.1760P)²+0.9125P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2049
_refine_ls_wR_factor_ref         0.2058
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C27(H27), C7(H7), C5(H5), C19(H19), C21(H21), C18(H18), C4(H4),
 C20(H20), C6(H6)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C22(H22A,H22B,H22C)
;
_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
Cl3 Cl 0.7755(2) -0.02263(15) 0.98505(17) 0.0311(4) Uani 1 1 d . . . . .
S1 S 1.05732(19) 0.29669(13) 0.71939(14) 0.0243(4) Uani 1 1 d . . . . .
Cl4 Cl 1.0142(2) -0.07809(14) 0.83257(17) 0.0337(5) Uani 1 1 d . . . . .
Cl2 Cl 0.6901(2) 0.19556(15) 1.01086(19) 0.0361(5) Uani 1 1 d . . . . .
Cl8 Cl 0.6563(2) 0.29726(17) 0.58548(17) 0.0358(5) Uani 1 1 d . . . . .
Cl6 Cl 0.8387(2) 0.65634(17) 0.48551(17) 0.0343(5) Uani 1 1 d . . . . .
Cl1 Cl 1.2968(2) 0.30046(16) 0.81799(17) 0.0337(4) Uani 1 1 d . . . . .
Cl7 Cl 0.8636(2) 0.43066(17) 0.46551(15) 0.0342(5) Uani 1 1 d . . . . .
S2 S 0.4058(2) 0.61450(17) 0.74021(16) 0.0327(5) Uani 1 1 d . . . . .
Cl5 Cl 0.2023(2) 0.6139(2) 0.6107(2) 0.0451(6) Uani 1 1 d . . . . .
N2 N 0.8486(7) 0.3311(5) 0.8880(5) 0.0236(12) Uani 1 1 d . . . . .
N4 N 0.6171(7) 0.7242(6) 0.6173(6) 0.0289(14) Uani 1 1 d . . . . .
N1 N 0.9747(7) 0.3925(5) 0.7416(6) 0.0268(13) Uani 1 1 d . . . . .
C9 C 0.8841(8) 0.2371(6) 0.8685(6) 0.0237(14) Uani 1 1 d . . . . .
C23 C 0.6218(8) 0.6248(7) 0.6112(6) 0.0271(16) Uani 1 1 d . . . . .
C11 C 0.8560(9) 0.0657(7) 0.9141(6) 0.0268(16) Uani 1 1 d . . . . .
C13 C 1.0240(8) 0.1102(6) 0.7834(6) 0.0236(14) Uani 1 1 d . . . . .
H13 H 1.090943 0.093133 0.735064 0.028 Uiso 1 1 calc R . . . .
C14 C 0.9843(8) 0.2075(6) 0.7963(6) 0.0229(14) Uani 1 1 d . . . . .
N3 N 0.4549(8) 0.7222(7) 0.7579(6) 0.0348(16) Uani 1 1 d . . . . .
C27 C 0.5377(9) 0.4614(7) 0.6528(7) 0.0313(17) Uani 1 1 d . . . . .
H27 H 0.474210 0.421711 0.686726 0.038 Uiso 1 1 calc R . . . .
C2 C 0.8577(8) 0.5041(6) 0.8544(6) 0.0228(15) Uani 1 1 d . . . . .
C25 C 0.7358(8) 0.4819(7) 0.5395(6) 0.0282(16) Uani 1 1 d . . . . .
C1 C 0.8947(8) 0.4012(6) 0.8297(6) 0.0229(14) Uani 1 1 d . . . . .
C7 C 0.9445(9) 0.5770(6) 0.8138(7) 0.0275(16) Uani 1 1 d . . . . .
H7 H 1.017614 0.560011 0.770534 0.033 Uiso 1 1 calc R . . . .
C10 C 0.8171(8) 0.1621(6) 0.9255(6) 0.0239(14) Uani 1 1 d . . . . .
C16 C 0.5404(9) 0.8746(7) 0.6932(6) 0.0319(18) Uani 1 1 d . . . . .
C17 C 0.6382(9) 0.9351(7) 0.6410(7) 0.0327(18) Uani 1 1 d . . . . .
C5 C 0.8172(10) 0.6987(6) 0.9025(8) 0.0347(19) Uani 1 1 d . . . . .
H5 H 0.804355 0.763565 0.919989 0.042 Uiso 1 1 calc R . . . .
C19 C 0.5228(11) 1.0772(8) 0.7121(8) 0.038(2) Uani 1 1 d . . . . .
H19 H 0.516535 1.144245 0.717898 0.046 Uiso 1 1 calc R . . . .
C26 C 0.6411(9) 0.4221(7) 0.5936(6) 0.0286(16) Uani 1 1 d . . . . .
C12 C 0.9617(9) 0.0407(5) 0.8435(6) 0.0243(15) Uani 1 1 d . . . . .
C24 C 0.7256(9) 0.5811(7) 0.5485(6) 0.0296(17) Uani 1 1 d . . . . .
C21 C 0.4378(10) 0.9195(8) 0.7544(7) 0.0354(19) Uani 1 1 d . . . . .
H21 H 0.373921 0.880900 0.789282 0.043 Uiso 1 1 calc R . . . .
C3 C 0.7446(9) 0.5289(7) 0.9190(6) 0.0288(17) Uani 1 1 d . . . . .
C15 C 0.5406(8) 0.7679(7) 0.6861(6) 0.0284(17) Uani 1 1 d . . . . .
C28 C 0.5294(9) 0.5614(7) 0.6610(6) 0.0299(17) Uani 1 1 d . . . . .
C18 C 0.6254(10) 1.0355(8) 0.6516(8) 0.038(2) Uani 1 1 d . . . . .
H18 H 0.687551 1.075652 0.617011 0.045 Uiso 1 1 calc R . . . .
C4 C 0.7295(10) 0.6277(7) 0.9422(7) 0.0338(18) Uani 1 1 d . . . . .
H4 H 0.657801 0.646501 0.985886 0.041 Uiso 1 1 calc R . . . .
C20 C 0.4296(10) 1.0178(8) 0.7638(7) 0.038(2) Uani 1 1 d . . . . .
H20 H 0.361155 1.045232 0.805100 0.046 Uiso 1 1 calc R . . . .
C8 C 0.6366(10) 0.4589(7) 0.9583(7) 0.0323(17) Uani 1 1 d . . . . .
H8A H 0.591135 0.420250 0.896348 0.048 Uiso 1 1 calc GR . . . .
H8B H 0.560309 0.494159 0.988934 0.048 Uiso 1 1 calc GR . . . .
H8C H 0.689022 0.417468 1.014923 0.048 Uiso 1 1 calc GR . . . .
C6 C 0.9228(11) 0.6727(7) 0.8372(8) 0.0358(18) Uani 1 1 d . . . . .
H6 H 0.979875 0.720249 0.808802 0.043 Uiso 1 1 calc R . . . .
C22 C 0.7550(11) 0.8986(8) 0.5743(9) 0.041(2) Uani 1 1 d . . . . .
H22A H 0.816870 0.851387 0.617413 0.062 Uiso 1 1 calc GR . . . .
H22B H 0.815867 0.951901 0.556591 0.062 Uiso 1 1 calc GR . . . .
H22C H 0.706661 0.869383 0.506244 0.062 Uiso 1 1 calc GR . . . .


_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
Cl3 C11 1.712(8) . ?
S1 Cl1 2.308(2) . ?
S1 N1 1.560(7) . ?
S1 C14 1.729(8) . ?
Cl4 C12 1.715(8) . ?
Cl2 C10 1.714(8) . ?
Cl8 C26 1.730(9) . ?
Cl6 C24 1.711(9) . ?
Cl7 C25 1.713(8) . ?
S2 Cl5 2.229(3) . ?
S2 N3 1.556(9) . ?
S2 C28 1.735(9) . ?
N2 C9 1.364(11) . ?
N2 C1 1.300(11) . ?
N4 C23 1.373(13) . ?
N4 C15 1.303(11) . ?
N1 C1 1.376(10) . ?
C9 C14 1.407(11) . ?
C9 C10 1.425(11) . ?
C23 C24 1.423(11) . ?
C23 C28 1.404(12) . ?
C11 C10 1.386(12) . ?
C11 C12 1.413(11) . ?
C13 H13 0.9300 . ?
C13 C14 1.403(12) . ?
C13 C12 1.372(11) . ?
N3 C15 1.394(11) . ?
C27 H27 0.9300 . ?
C27 C26 1.368(12) . ?
C27 C28 1.385(14) . ?
C2 C1 1.498(11) . ?
C2 C7 1.406(11) . ?
C2 C3 1.415(11) . ?
C25 C26 1.415(12) . ?
C25 C24 1.375(14) . ?
C7 H7 0.9300 . ?
C7 C6 1.370(14) . ?
C16 C17 1.426(13) . ?
C16 C21 1.410(12) . ?
C16 C15 1.474(14) . ?
C17 C18 1.397(15) . ?
C17 C22 1.505(13) . ?
C5 H5 0.9300 . ?
C5 C4 1.388(15) . ?
C5 C6 1.371(14) . ?
C19 H19 0.9300 . ?
C19 C18 1.385(15) . ?
C19 C20 1.386(15) . ?
C21 H21 0.9300 . ?
C21 C20 1.363(15) . ?
C3 C4 1.402(14) . ?
C3 C8 1.498(13) . ?
C18 H18 0.9300 . ?
C4 H4 0.9300 . ?
C20 H20 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C6 H6 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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
N1 S1 Cl1 109.1(3) . . ?
N1 S1 C14 106.3(4) . . ?
C14 S1 Cl1 98.1(3) . . ?
N3 S2 Cl5 106.7(3) . . ?
N3 S2 C28 106.6(4) . . ?
C28 S2 Cl5 98.2(3) . . ?
C1 N2 C9 120.7(7) . . ?
C15 N4 C23 121.3(8) . . ?
C1 N1 S1 121.7(6) . . ?
N2 C9 C14 124.9(7) . . ?
N2 C9 C10 118.6(7) . . ?
C14 C9 C10 116.5(8) . . ?
N4 C23 C24 118.7(7) . . ?
N4 C23 C28 125.0(8) . . ?
C28 C23 C24 116.3(8) . . ?
C10 C11 Cl3 120.0(6) . . ?
C10 C11 C12 119.8(7) . . ?
C12 C11 Cl3 120.2(7) . . ?
C14 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?
C12 C13 C14 118.5(7) . . ?
C9 C14 S1 117.2(6) . . ?
C13 C14 S1 119.8(6) . . ?
C13 C14 C9 123.0(7) . . ?
C15 N3 S2 121.2(6) . . ?
C26 C27 H27 120.7 . . ?
C26 C27 C28 118.7(8) . . ?
C28 C27 H27 120.7 . . ?
C7 C2 C1 117.1(7) . . ?
C7 C2 C3 120.3(8) . . ?
C3 C2 C1 122.6(7) . . ?
C26 C25 Cl7 120.0(7) . . ?
C24 C25 Cl7 120.6(7) . . ?
C24 C25 C26 119.4(8) . . ?
N2 C1 N1 126.9(7) . . ?
N2 C1 C2 119.8(7) . . ?
N1 C1 C2 113.2(7) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 C2 120.8(8) . . ?
C6 C7 H7 119.6 . . ?
C9 C10 Cl2 117.7(6) . . ?
C11 C10 Cl2 121.3(6) . . ?
C11 C10 C9 121.0(7) . . ?
C17 C16 C15 123.5(8) . . ?
C21 C16 C17 118.2(9) . . ?
C21 C16 C15 118.3(8) . . ?
C16 C17 C22 124.7(9) . . ?
C18 C17 C16 118.3(9) . . ?
C18 C17 C22 117.0(9) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C6 C5 C4 119.7(8) . . ?
C18 C19 H19 120.3 . . ?
C18 C19 C20 119.4(10) . . ?
C20 C19 H19 120.3 . . ?
C27 C26 Cl8 119.3(7) . . ?
C27 C26 C25 121.0(9) . . ?
C25 C26 Cl8 119.7(7) . . ?
C11 C12 Cl4 119.9(6) . . ?
C13 C12 Cl4 119.1(6) . . ?
C13 C12 C11 121.0(7) . . ?
C23 C24 Cl6 117.6(7) . . ?
C25 C24 Cl6 121.1(7) . . ?
C25 C24 C23 121.4(8) . . ?
C16 C21 H21 119.1 . . ?
C20 C21 C16 121.8(9) . . ?
C20 C21 H21 119.1 . . ?
C2 C3 C8 125.2(8) . . ?
C4 C3 C2 116.3(8) . . ?
C4 C3 C8 118.4(8) . . ?
N4 C15 N3 125.6(9) . . ?
N4 C15 C16 120.2(8) . . ?
N3 C15 C16 114.1(8) . . ?
C23 C28 S2 116.4(7) . . ?
C27 C28 S2 120.4(7) . . ?
C27 C28 C23 123.2(8) . . ?
C17 C18 H18 119.0 . . ?
C19 C18 C17 122.0(10) . . ?
C19 C18 H18 119.0 . . ?
C5 C4 C3 122.6(8) . . ?
C5 C4 H4 118.7 . . ?
C3 C4 H4 118.7 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.3(9) . . ?
C21 C20 H20 119.8 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C6 C5 120.2(9) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?


_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 2.373
_oxdiff_exptl_absorpt_empirical_full_min 0.432

# start Validation Reply Form
_vrf_PLAT431_serc118-r1-fm-non-equiv-rf1 
;
PROBLEM: Short Inter HL..A Contact  Cl2      ..S2               3.44 Ang.  
RESPONSE: Weak intermolecular S...Cl contacts.
;
# end Validation Reply Form
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_serc086-r1-rf3
_database_code_depnum_ccdc_archive 'CCDC 2101067'
loop_
_audit_author_name
_audit_author_address
'Andryj M Borys'
;University of Kent
United Kingdom
;
_audit_update_record             
;
2021-08-03 deposited with the CCDC.	2021-11-23 downloaded from the CCDC.
;
_audit_creation_date             2018-06-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H12 Cl4 N2 S'
_chemical_formula_sum            'C16 H12 Cl4 N2 S'
_chemical_formula_weight         406.14
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H12 Cl4 N2 S1 '
_chemical_oxdiff_usercomment     'ABS-259 2,3-2-Me-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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_symmetry_space_group_name_H-M_alt 'P b c a'
_cell_length_a                   14.2979(4)
_cell_length_b                   14.0607(3)
_cell_length_c                   16.3174(4)
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_volume                     3280.41(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    39392
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.0870
_cell_measurement_theta_min      3.8700
_cell_oxdiff_angle_alpha         90.190(2)
_cell_oxdiff_angle_beta          90.074(2)
_cell_oxdiff_angle_gamma         89.788(3)
_cell_oxdiff_length_a            14.2814(5)
_cell_oxdiff_length_b            14.0999(4)
_cell_oxdiff_length_c            16.2910(4)
_cell_oxdiff_measurement_reflns_used 39480
_cell_oxdiff_volume              3280.41(17)
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.736
_exptl_absorpt_correction_T_max  0.404
_exptl_absorpt_correction_T_min  0.107
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orangish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
8 5 0 0.1888
7 -5 -4 0.0980
-7 -6 -1 0.1737
-6 6 4 0.0893
0 9 -3 0.1910
2 0 10 0.0796
-1 -9 1 0.2073
-2 0 -10 0.0871

_exptl_crystal_size_max          0.424
_exptl_crystal_size_mid          0.235
_exptl_crystal_size_min          0.177
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
7.6234 5.2343 0.0575 0.6867 -0.2405 0.6860
7.1910 -4.8568 -3.5635 0.8374 -0.2968 -0.4590
-6.9793 -6.0304 -0.5100 -0.6047 0.2113 -0.7679
-6.3102 5.8570 3.7162 -0.7657 0.2718 0.5829
0.4854 8.8605 -2.6228 0.1723 0.4817 0.8593
2.2519 -0.0650 10.2582 -0.3170 -0.9006 0.2973
-0.8175 -9.0597 1.2240 -0.1313 -0.3648 -0.9218
-2.3101 -0.4795 -10.2254 0.3104 0.8822 -0.3539

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            63211
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.270
_diffrn_reflns_theta_min         5.178
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2774
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -68.00  29.00   1.00    8.00    --  -41.51  57.00  90.00   97
  2  ω   -112.00 -15.00   1.00    8.00    --  -41.51 -57.00 -60.00   97
  3  ω   -114.00 -19.00   1.00    8.00    --  -41.51 -38.00  30.00   95
  4  ω    -64.00  31.00   1.00    8.00    --  -41.51  38.00-150.00   95
  5  ω     19.00 114.00   1.00    8.00    --   41.51  38.00 -90.00   95
  6  ω     23.00  97.00   1.00    8.00    --   41.51-125.00 120.00   74
  7  ω      1.00  81.00   1.00    8.00    --   41.51 -99.00 -60.00   80
  8  ω     30.00 109.00   1.00   20.00    --  111.00 -95.00 150.00   79
  9  ω     36.00 116.00   1.00   20.00    --  111.00-111.00  60.00   80
 10  ω     32.00 152.00   1.00   20.00    --  111.00 -17.00 -33.79  120
 11  ω     37.00 142.00   1.00   20.00    --  111.00 -77.00 -30.00  105
 12  ω     87.00 178.00   1.00   20.00    --  111.00  30.00-150.00   91
 13  ω     36.00 116.00   1.00   20.00    --  111.00-111.00 -60.00   80
 14  ω     87.00 178.00   1.00   20.00    --  111.00  30.00-180.00   91
 15  ω     36.00 116.00   1.00   20.00    --  111.00-111.00-120.00   80
 16  ω     57.00 151.00   1.00   20.00    --  111.00 178.00  60.00   94
 17  ω     36.00 116.00   1.00   20.00    --  111.00-111.00 120.00   80
 18  ω     36.00 116.00   1.00   20.00    --  111.00-111.00   0.00   80
 19  ω     37.00 142.00   1.00   20.00    --  111.00 -77.00-150.00  105
 20  ω     87.00 178.00   1.00   20.00    --  111.00  45.00-120.00   91
 21  ω     41.00 139.00   1.00   20.00    --  111.00 -61.00 -90.00   98
 22  ω     30.00 109.00   1.00   20.00    --  111.00 -95.00-180.00   79
 23  ω     50.00 120.00   1.00   20.00    --  111.00 -30.00-120.00   70
 24  ω     70.00 101.00   1.00   20.00    --  111.00 -95.00   0.00   31
 25  ω     70.00 112.00   1.00   20.00    --  111.00 -30.00   0.00   42
 26  ω    109.00 136.00   1.00   20.00    --  111.00  45.00 -60.00   27
 27  ω    107.00 175.00   1.00   20.00    --  111.00 111.00 -90.00   68
 28  ω     36.00  85.00   1.00   20.00    --  111.00 -30.00 150.00   49
 29  ω    153.00 178.00   1.00   20.00    --  111.00  15.00 -60.00   25
 30  ω     76.00 103.00   1.00   20.00    --  111.00 -95.00  60.00   27
 31  ω     83.00 122.00   1.00   20.00    --  111.00  15.00 -60.00   39
 32  ω     39.00 107.00   1.00   20.00    --  111.00 -95.00  30.00   68
 33  ω     54.00  81.00   1.00   20.00    --  111.00 -95.00 -60.00   27
 34  ω     33.00  85.00   1.00   20.00    --  111.00 -20.00 -42.64   52
 35  ω     84.00 131.00   1.00   20.00    --  111.00  61.00 -90.00   47
 36  ω     49.00  74.00   1.00   20.00    --  111.00-111.00-150.00   25
 37  ω     84.00 116.00   1.00   20.00    --  111.00-111.00-150.00   32
 38  ω     91.00 135.00   1.00   20.00    --  111.00 -45.00 -60.00   44
 39  ω    116.00 161.00   1.00   20.00    --  111.00  45.00  30.00   45
 40  ω     43.00 123.00   1.00   20.00    --  111.00 -45.00 -90.00   80
 41  ω     94.00 126.00   1.00   20.00    --  111.00 -61.00  90.00   32
 42  ω     45.00 114.00   1.00   20.00    --  111.00-111.00 150.00   69
 43  ω    101.00 148.00   1.00   20.00    --  111.00 111.00 -60.00   47
 44  ω     59.00  86.00   1.00   20.00    --  111.00 -77.00   0.00   27
 45  ω     91.00 118.00   1.00   20.00    --  111.00 -77.00   0.00   27
 46  ω     92.00 125.00   1.00   20.00    --  111.00 -77.00  90.00   33
 47  ω    108.00 141.00   1.00   20.00    --  111.00 -77.00 120.00   33
 48  ω     72.00  99.00   1.00   20.00    --  111.00  15.00 -90.00   27
 49  ω    142.00 167.00   1.00   20.00    --  111.00  15.00 -90.00   25
 50  ω    143.00 173.00   1.00   20.00    --  111.00 111.00-150.00   30
 51  ω     34.00  73.00   1.00   20.00    --  111.00 -95.00 120.00   39
 52  ω     89.00 116.00   1.00   20.00    --  111.00-111.00 -30.00   27
 53  ω     88.00 115.00   1.00   20.00    --  111.00-111.00  30.00   27
 54  ω     93.00 137.00   1.00   20.00    --  111.00 -58.00 -49.38   44
 55  ω    118.00 145.00   1.00   20.00    --  111.00  45.00  90.00   27
 56  ω    151.00 176.00   1.00   20.00    --  111.00  30.00  90.00   25
 57  ω     67.00 132.00   1.00   20.00    --  111.00 -40.00 131.86   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0908567000
_diffrn_orient_matrix_UB_12      -0.0005808000
_diffrn_orient_matrix_UB_13      -0.0508554000
_diffrn_orient_matrix_UB_21      -0.0550263000
_diffrn_orient_matrix_UB_22      0.0350278000
_diffrn_orient_matrix_UB_23      -0.0754912000
_diffrn_orient_matrix_UB_31      0.0187307000
_diffrn_orient_matrix_UB_32      0.1035064000
_diffrn_orient_matrix_UB_33      0.0255292000
_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                3176
_reflns_number_total             3183
_reflns_odcompleteness_completeness 99.91
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    ?
_refine_diff_density_max         0.997
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.108
_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)+(0.0369P)²+6.1544P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.0977
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
S1 S 0.59472(4) 0.44768(4) 0.61211(3) 0.02205(15) Uani 1 1 d . . . . .
Cl1 Cl 0.73630(5) 0.45442(4) 0.67464(4) 0.02939(16) Uani 1 1 d . . . . .
Cl4 Cl 0.61696(5) 0.08218(4) 0.52536(4) 0.03240(17) Uani 1 1 d . . . . .
Cl2 Cl 0.56852(5) 0.39080(5) 0.26017(4) 0.03649(18) Uani 1 1 d . . . . .
Cl3 Cl 0.53819(5) 0.10929(5) 0.32354(4) 0.03690(18) Uani 1 1 d . . . . .
N2 N 0.65253(14) 0.48730(14) 0.43850(12) 0.0203(4) Uani 1 1 d . . . . .
N1 N 0.58281(15) 0.54276(14) 0.56343(13) 0.0234(4) Uani 1 1 d . . . . .
C13 C 0.61251(18) 0.26664(17) 0.56003(15) 0.0231(5) Uani 1 1 d . . . . .
C14 C 0.62005(17) 0.36268(17) 0.53913(14) 0.0201(5) Uani 1 1 d . . . . .
C1 C 0.62365(17) 0.55420(17) 0.48810(15) 0.0208(5) Uani 1 1 d . . . . .
C10 C 0.65260(17) 0.32328(17) 0.39760(14) 0.0203(5) Uani 1 1 d . . . . .
C2 C 0.62579(17) 0.65431(17) 0.45904(16) 0.0225(5) Uani 1 1 d . . . . .
C12 C 0.62487(18) 0.20121(17) 0.49898(16) 0.0231(5) Uani 1 1 d . . . . .
C11 C 0.64300(18) 0.22725(17) 0.41685(15) 0.0235(5) Uani 1 1 d . . . . .
C7 C 0.63222(18) 0.73192(18) 0.51312(17) 0.0259(5) Uani 1 1 d . . . . .
C3 C 0.61591(18) 0.66991(19) 0.37494(17) 0.0259(5) Uani 1 1 d . . . . .
C15 C 0.67415(19) 0.35819(19) 0.31310(15) 0.0247(5) Uani 1 1 d . . . . .
C6 C 0.62539(19) 0.82315(19) 0.48015(19) 0.0310(6) Uani 1 1 d . . . . .
C5 C 0.6125(2) 0.8384(2) 0.3971(2) 0.0339(6) Uani 1 1 d . . . . .
C4 C 0.60872(19) 0.7614(2) 0.34397(18) 0.0311(6) Uani 1 1 d . . . . .
C8 C 0.6490(2) 0.7228(2) 0.60437(17) 0.0331(6) Uani 1 1 d . . . . .
H8A H 0.592096 0.703815 0.630940 0.050 Uiso 1 1 calc GR . . . .
H8B H 0.669068 0.783001 0.625918 0.050 Uiso 1 1 calc GR . . . .
H8C H 0.696506 0.675926 0.614128 0.050 Uiso 1 1 calc GR . . . .
C16 C 0.6525(2) 0.15020(19) 0.35360(16) 0.0294(6) Uani 1 1 d . . . . .
H16A H 0.688290 0.097660 0.376004 0.035 Uiso 1 1 calc R . . . .
H16B H 0.685605 0.174557 0.306138 0.035 Uiso 1 1 calc R . . . .
C9 C 0.64144(16) 0.39322(16) 0.45988(14) 0.0192(5) Uani 1 1 d . . . . .
H13 H 0.6014(18) 0.2445(19) 0.6237(16) 0.013(6) Uiso 1 1 d . . . . .
H5 H 0.608(2) 0.900(2) 0.3738(19) 0.028(8) Uiso 1 1 d . . . . .
H4 H 0.601(2) 0.769(2) 0.284(2) 0.036(9) Uiso 1 1 d . . . . .
H3 H 0.614(2) 0.619(2) 0.3378(19) 0.027(8) Uiso 1 1 d . . . . .
H15A H 0.707(2) 0.413(2) 0.3140(17) 0.020(7) Uiso 1 1 d . . . . .
H6 H 0.628(2) 0.872(2) 0.5156(19) 0.026(8) Uiso 1 1 d . . . . .
H15B H 0.707(2) 0.312(2) 0.2772(19) 0.030(8) Uiso 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
S1 Cl1 2.2689(9) . ?
S1 N1 1.564(2) . ?
S1 C14 1.726(2) . ?
Cl4 C12 1.732(2) . ?
Cl2 C15 1.799(3) . ?
Cl3 C16 1.801(3) . ?
N2 C1 1.308(3) . ?
N2 C9 1.377(3) . ?
N1 C1 1.370(3) . ?
C13 C14 1.397(3) . ?
C13 C12 1.367(4) . ?
C13 H13 1.10(3) . ?
C14 C9 1.397(3) . ?
C1 C2 1.486(3) . ?
C10 C11 1.393(3) . ?
C10 C15 1.496(3) . ?
C10 C9 1.423(3) . ?
C2 C7 1.406(4) . ?
C2 C3 1.397(4) . ?
C12 C11 1.413(4) . ?
C11 C16 1.503(3) . ?
C7 C6 1.394(4) . ?
C7 C8 1.514(4) . ?
C3 C4 1.386(4) . ?
C3 H3 0.94(3) . ?
C15 H15A 0.91(3) . ?
C15 H15B 1.00(3) . ?
C6 C5 1.383(4) . ?
C6 H6 0.90(3) . ?
C5 C4 1.388(4) . ?
C5 H5 0.95(3) . ?
C4 H4 1.00(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?

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
N1 S1 Cl1 106.84(9) . . ?
N1 S1 C14 105.33(11) . . ?
C14 S1 Cl1 98.74(8) . . ?
C1 N2 C9 119.8(2) . . ?
C1 N1 S1 120.63(17) . . ?
C14 C13 H13 121.2(14) . . ?
C12 C13 C14 117.6(2) . . ?
C12 C13 H13 121.2(14) . . ?
C13 C14 S1 119.01(18) . . ?
C9 C14 S1 118.16(18) . . ?
C9 C14 C13 122.7(2) . . ?
N2 C1 N1 127.2(2) . . ?
N2 C1 C2 118.5(2) . . ?
N1 C1 C2 114.0(2) . . ?
C11 C10 C15 123.1(2) . . ?
C11 C10 C9 119.8(2) . . ?
C9 C10 C15 117.0(2) . . ?
C7 C2 C1 122.4(2) . . ?
C3 C2 C1 117.4(2) . . ?
C3 C2 C7 120.1(2) . . ?
C13 C12 Cl4 117.4(2) . . ?
C13 C12 C11 122.7(2) . . ?
C11 C12 Cl4 119.87(19) . . ?
C10 C11 C12 118.9(2) . . ?
C10 C11 C16 122.3(2) . . ?
C12 C11 C16 118.8(2) . . ?
C2 C7 C8 124.2(2) . . ?
C6 C7 C2 117.8(3) . . ?
C6 C7 C8 117.9(2) . . ?
C2 C3 H3 121.1(19) . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 118.2(19) . . ?
Cl2 C15 H15A 103.3(18) . . ?
Cl2 C15 H15B 106.3(18) . . ?
C10 C15 Cl2 110.68(18) . . ?
C10 C15 H15A 111.9(17) . . ?
C10 C15 H15B 115.0(18) . . ?
H15A C15 H15B 109(3) . . ?
C7 C6 H6 117(2) . . ?
C5 C6 C7 122.0(3) . . ?
C5 C6 H6 121(2) . . ?
C6 C5 C4 119.8(3) . . ?
C6 C5 H5 122.8(19) . . ?
C4 C5 H5 117.4(19) . . ?
C3 C4 C5 119.5(3) . . ?
C3 C4 H4 118.2(19) . . ?
C5 C4 H4 122.3(19) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
Cl3 C16 H16A 109.8 . . ?
Cl3 C16 H16B 109.8 . . ?
C11 C16 Cl3 109.58(19) . . ?
C11 C16 H16A 109.8 . . ?
C11 C16 H16B 109.8 . . ?
H16A C16 H16B 108.2 . . ?
N2 C9 C14 123.7(2) . . ?
N2 C9 C10 118.0(2) . . ?
C14 C9 C10 118.3(2) . . ?


_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 1.580
_oxdiff_exptl_absorpt_empirical_full_min 0.638

# start Validation Reply Form
_vrf_PLAT094_serc086-r1-rf3      
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       2.10 Report
RESPONSE: Residual electron density is observed within close proximity of
methyl protons indicating very minor partial chlorination at these positions
that could not be explicity modelled.
;
_vrf_PLAT230_serc086-r1-rf3      
;
PROBLEM: Hirshfeld Test Diff for   Cl1      --S1        .        6.8 s.u.  
RESPONSE: Minor positional disorder in different directions for S1 and Cl1.
;
# end Validation Reply Form
_chemical_properties_physical    Moisture-sensitive
