# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_3A25D_2_0m
_database_code_depnum_ccdc_archive 'CCDC 1952930'
loop_
_audit_author_name
_audit_author_address
'Ching Kheng Quah'
;Universiti Sains Malaysia
Malaysia
;
_audit_update_record             
;
2019-09-11 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;

#====================================================================  

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
(E)-3-(2,4-dichlorophenyl)-1-(2,5-dichlorothiophen-3-yl)prop-2-en-1-one
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H6 Cl4 O S'
_chemical_formula_sum            'C13 H6 Cl4 O S'
_chemical_formula_weight         352.04

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   3.9858(7)
_cell_length_b                   13.451(2)
_cell_length_c                   25.545(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1369.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296
_cell_measurement_reflns_used    1978
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      23.01
_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.341
_exptl_crystal_size_mid          0.229
_exptl_crystal_size_min          0.053
_exptl_absorpt_coefficient_mu    1.002
_shelx_estimated_absorpt_T_min   0.726
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6720
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7501
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.594
_diffrn_reflns_theta_max         26.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2968
_reflns_number_gt                2323
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.659
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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.
;

_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
SHELXTL (Sheldrick, 2008), Mercury (Macrae et al., 2008)
;
_computing_publication_material  
;
PLATON (Spek, 2009), publCIF (Westrip, 2010)
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0333P)²+0.0341P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 696 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2968
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.0836
_refine_ls_wR_factor_gt          0.0752
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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_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 -0.1744(3) 0.87634(8) 0.70261(4) 0.0581(3) Uani 1 1 d . . . . .
Cl2 Cl -0.3622(3) 0.63886(9) 0.51990(5) 0.0617(3) Uani 1 1 d . . . . .
Cl3 Cl 0.7235(3) 0.54852(8) 0.88761(5) 0.0663(4) Uani 1 1 d . . . . .
Cl4 Cl 0.8807(3) 0.90508(9) 0.97554(5) 0.0631(4) Uani 1 1 d . . . . .
S1 S -0.3322(3) 0.80056(8) 0.59886(4) 0.0484(3) Uani 1 1 d . . . . .
O1 O 0.1279(10) 0.5430(2) 0.71212(12) 0.0753(11) Uani 1 1 d . . . . .
C1 C -0.1674(10) 0.7780(3) 0.65981(15) 0.0422(9) Uani 1 1 d . . . . .
C2 C -0.2544(10) 0.6790(3) 0.58127(16) 0.0433(10) Uani 1 1 d . . . . .
C3 C -0.1139(9) 0.6257(3) 0.61959(15) 0.0423(10) Uani 1 1 d . . . . .
H3A H -0.057478 0.558918 0.616155 0.051 Uiso 1 1 calc R U . . .
C4 C -0.0592(9) 0.6817(3) 0.66646(16) 0.0394(10) Uani 1 1 d . . . . .
C5 C 0.0996(10) 0.6329(3) 0.71238(16) 0.0446(10) Uani 1 1 d . . . . .
C6 C 0.2228(10) 0.6934(3) 0.75591(16) 0.0515(11) Uani 1 1 d . . . . .
H6A H 0.189805 0.761692 0.753922 0.062 Uiso 1 1 calc R U . . .
C7 C 0.3753(11) 0.6590(3) 0.79731(16) 0.0486(11) Uani 1 1 d . . . . .
H7A H 0.405933 0.590579 0.799155 0.058 Uiso 1 1 calc R U . . .
C8 C 0.5027(9) 0.7180(3) 0.84106(16) 0.0402(10) Uani 1 1 d . . . . .
C9 C 0.6643(10) 0.6757(3) 0.88393(16) 0.0422(9) Uani 1 1 d . . . . .
C10 C 0.7818(10) 0.7322(3) 0.92507(16) 0.0461(10) Uani 1 1 d . . . . .
H10A H 0.889895 0.702282 0.953222 0.055 Uiso 1 1 calc R U . . .
C11 C 0.7369(10) 0.8331(3) 0.92383(17) 0.0448(10) Uani 1 1 d . . . . .
C12 C 0.5826(9) 0.8788(3) 0.88223(17) 0.0479(11) Uani 1 1 d . . . . .
H12A H 0.554721 0.947406 0.881776 0.057 Uiso 1 1 calc R U . . .
C13 C 0.4700(10) 0.8216(3) 0.84130(17) 0.0457(11) Uani 1 1 d . . . . .
H13A H 0.368844 0.852660 0.812864 0.055 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.716(4) . ?
Cl2 C2 1.713(4) . ?
Cl3 C9 1.730(4) . ?
Cl4 C11 1.735(4) . ?
S1 C1 1.717(4) . ?
S1 C2 1.723(4) . ?
O1 C5 1.214(5) . ?
C1 C4 1.375(5) . ?
C2 C3 1.337(5) . ?
C3 C4 1.431(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.486(5) . ?
C5 C6 1.462(5) . ?
C6 C7 1.304(5) . ?
C6 H6A 0.9300 . ?
C7 C8 1.461(6) . ?
C7 H7A 0.9300 . ?
C8 C9 1.392(5) . ?
C8 C13 1.400(6) . ?
C9 C10 1.379(5) . ?
C10 C11 1.369(6) . ?
C10 H10A 0.9300 . ?
C11 C12 1.373(6) . ?
C12 C13 1.373(6) . ?
C12 H12A 0.9300 . ?
C13 H13A 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
C1 S1 C2 90.01(19) . . ?
C4 C1 Cl1 130.7(3) . . ?
C4 C1 S1 113.5(3) . . ?
Cl1 C1 S1 115.8(2) . . ?
C3 C2 Cl2 127.3(3) . . ?
C3 C2 S1 113.2(3) . . ?
Cl2 C2 S1 119.5(2) . . ?
C2 C3 C4 113.2(4) . . ?
C2 C3 H3A 123.4 . . ?
C4 C3 H3A 123.4 . . ?
C1 C4 C3 110.2(4) . . ?
C1 C4 C5 130.3(4) . . ?
C3 C4 C5 119.5(4) . . ?
O1 C5 C6 121.8(4) . . ?
O1 C5 C4 118.4(4) . . ?
C6 C5 C4 119.9(4) . . ?
C7 C6 C5 125.2(4) . . ?
C7 C6 H6A 117.4 . . ?
C5 C6 H6A 117.4 . . ?
C6 C7 C8 126.2(4) . . ?
C6 C7 H7A 116.9 . . ?
C8 C7 H7A 116.9 . . ?
C9 C8 C13 116.5(4) . . ?
C9 C8 C7 122.7(4) . . ?
C13 C8 C7 120.7(4) . . ?
C10 C9 C8 122.1(4) . . ?
C10 C9 Cl3 117.2(3) . . ?
C8 C9 Cl3 120.7(3) . . ?
C11 C10 C9 119.0(4) . . ?
C11 C10 H10A 120.5 . . ?
C9 C10 H10A 120.5 . . ?
C10 C11 C12 121.3(4) . . ?
C10 C11 Cl4 119.5(3) . . ?
C12 C11 Cl4 119.2(3) . . ?
C11 C12 C13 119.0(4) . . ?
C11 C12 H12A 120.5 . . ?
C13 C12 H12A 120.5 . . ?
C12 C13 C8 122.0(4) . . ?
C12 C13 H13A 119.0 . . ?
C8 C13 H13A 119.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 S1 C1 C4 -0.3(3) . . . . ?
C2 S1 C1 Cl1 -178.5(3) . . . . ?
C1 S1 C2 C3 0.3(3) . . . . ?
C1 S1 C2 Cl2 179.5(3) . . . . ?
Cl2 C2 C3 C4 -179.4(3) . . . . ?
S1 C2 C3 C4 -0.2(5) . . . . ?
Cl1 C1 C4 C3 178.1(3) . . . . ?
S1 C1 C4 C3 0.2(4) . . . . ?
Cl1 C1 C4 C5 -2.8(7) . . . . ?
S1 C1 C4 C5 179.2(3) . . . . ?
C2 C3 C4 C1 0.0(5) . . . . ?
C2 C3 C4 C5 -179.2(3) . . . . ?
C1 C4 C5 O1 169.0(4) . . . . ?
C3 C4 C5 O1 -12.1(6) . . . . ?
C1 C4 C5 C6 -12.2(7) . . . . ?
C3 C4 C5 C6 166.7(4) . . . . ?
O1 C5 C6 C7 1.1(7) . . . . ?
C4 C5 C6 C7 -177.7(4) . . . . ?
C5 C6 C7 C8 179.5(4) . . . . ?
C6 C7 C8 C9 -179.8(4) . . . . ?
C6 C7 C8 C13 -0.5(7) . . . . ?
C13 C8 C9 C10 1.1(6) . . . . ?
C7 C8 C9 C10 -179.7(4) . . . . ?
C13 C8 C9 Cl3 -179.3(3) . . . . ?
C7 C8 C9 Cl3 0.0(5) . . . . ?
C8 C9 C10 C11 0.3(6) . . . . ?
Cl3 C9 C10 C11 -179.4(3) . . . . ?
C9 C10 C11 C12 -1.0(6) . . . . ?
C9 C10 C11 Cl4 179.5(3) . . . . ?
C10 C11 C12 C13 0.4(6) . . . . ?
Cl4 C11 C12 C13 179.8(3) . . . . ?
C11 C12 C13 C8 1.1(6) . . . . ?
C9 C8 C13 C12 -1.7(6) . . . . ?
C7 C8 C13 C12 179.0(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D    H    A    D - H    H...A    D...A      D - H...A    symm(A)
#
C6 H6A Cl1 0.9300 2.4900 3.227(4) 136.00 . yes

_refine_diff_density_max         0.217
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_mo_3A25D_4_0m
_database_code_depnum_ccdc_archive 'CCDC 1952931'
loop_
_audit_author_name
_audit_author_address
'Ching Kheng Quah'
;Universiti Sains Malaysia
Malaysia
;
_audit_update_record             
;
2019-09-11 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;

#====================================================================  

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
(E)-3-(2,6-dichlorophenyl)-1-(2,5-dichlorothiophen-3-yl)prop-2-en-1-one
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H6 Cl4 O S'
_chemical_formula_sum            'C13 H6 Cl4 O S'
_chemical_formula_weight         352.04

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   3.8532(7)
_cell_length_b                   14.632(3)
_cell_length_c                   24.278(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.236(3)
_cell_angle_gamma                90
_cell_volume                     1366.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296
_cell_measurement_reflns_used    3261
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      27.74

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.463
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.059
_exptl_absorpt_coefficient_mu    1.004
_shelx_estimated_absorpt_T_min   0.654
_shelx_estimated_absorpt_T_max   0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6895
_exptl_absorpt_correction_T_max  0.7768
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17830
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.626
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2962
_reflns_number_gt                2315
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
SHELXTL (Sheldrick, 2008), Mercury (Macrae et al., 2008)
;
_computing_publication_material  
;
PLATON (Spek, 2009), publCIF (Westrip, 2010)
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0381P)²+1.3236P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2962
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1154
_refine_ls_wR_factor_gt          0.1077
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_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_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 0.7218(3) 0.60276(6) 0.50032(4) 0.0557(3) Uani 1 1 d . . . . .
Cl2 Cl 0.2083(3) 0.94154(7) 0.57935(4) 0.0590(3) Uani 1 1 d . . . . .
Cl3 Cl 0.2708(3) 0.68005(7) 0.21100(4) 0.0617(3) Uani 1 1 d . . . . .
Cl4 Cl 0.8571(2) 0.47176(6) 0.37710(3) 0.0512(3) Uani 1 1 d . . . . .
S1 S 0.4704(3) 0.75277(6) 0.56755(3) 0.0493(2) Uani 1 1 d . . . . .
O1 O 0.6382(9) 0.82947(18) 0.37669(11) 0.0750(9) Uani 1 1 d . . . . .
C1 C 0.5584(8) 0.7111(2) 0.50386(13) 0.0374(7) Uani 1 1 d . . . . .
C2 C 0.3468(8) 0.8552(2) 0.53818(14) 0.0401(8) Uani 1 1 d . . . . .
C3 C 0.3770(9) 0.8577(2) 0.48319(14) 0.0423(8) Uani 1 1 d . . . . .
H3A H 0.324618 0.908580 0.461341 0.051 Uiso 1 1 calc R U . . .
C4 C 0.4994(8) 0.7725(2) 0.46224(12) 0.0366(7) Uani 1 1 d . . . . .
C5 C 0.5639(9) 0.7623(2) 0.40242(13) 0.0440(8) Uani 1 1 d . . . . .
C6 C 0.5195(9) 0.6717(2) 0.37649(13) 0.0433(8) Uani 1 1 d . . . . .
H6A H 0.434935 0.623457 0.396728 0.052 Uiso 1 1 calc R U . . .
C7 C 0.5989(9) 0.6581(2) 0.32449(13) 0.0451(8) Uani 1 1 d . . . . .
H7A H 0.692537 0.707485 0.306310 0.054 Uiso 1 1 calc R U . . .
C8 C 0.5533(8) 0.5729(2) 0.29296(12) 0.0374(7) Uani 1 1 d . . . . .
C9 C 0.4005(9) 0.5753(2) 0.23919(13) 0.0418(8) Uani 1 1 d . . . . .
C10 C 0.3407(9) 0.4986(3) 0.20770(14) 0.0496(9) Uani 1 1 d . . . . .
H10A H 0.234603 0.503114 0.172441 0.059 Uiso 1 1 calc R U . . .
C11 C 0.4392(10) 0.4151(3) 0.22878(15) 0.0530(10) Uani 1 1 d . . . . .
H11A H 0.398686 0.362596 0.207796 0.064 Uiso 1 1 calc R U . . .
C12 C 0.5979(9) 0.4085(2) 0.28092(15) 0.0473(8) Uani 1 1 d . . . . .
H12A H 0.669561 0.351972 0.294889 0.057 Uiso 1 1 calc R U . . .
C13 C 0.6494(8) 0.4864(2) 0.31218(13) 0.0383(7) 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 C1 1.710(3) . ?
Cl2 C2 1.714(3) . ?
Cl3 C9 1.741(3) . ?
Cl4 C13 1.740(3) . ?
S1 C1 1.714(3) . ?
S1 C2 1.716(3) . ?
O1 C5 1.207(4) . ?
C1 C4 1.362(4) . ?
C2 C3 1.347(4) . ?
C3 C4 1.436(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.495(4) . ?
C5 C6 1.473(5) . ?
C6 C7 1.331(4) . ?
C6 H6A 0.9300 . ?
C7 C8 1.468(5) . ?
C7 H7A 0.9300 . ?
C8 C13 1.392(4) . ?
C8 C9 1.402(4) . ?
C9 C10 1.370(5) . ?
C10 C11 1.369(5) . ?
C10 H10A 0.9300 . ?
C11 C12 1.378(5) . ?
C11 H11A 0.9300 . ?
C12 C13 1.378(5) . ?
C12 H12A 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
C1 S1 C2 90.03(16) . . ?
C4 C1 Cl1 128.4(3) . . ?
C4 C1 S1 113.7(2) . . ?
Cl1 C1 S1 117.88(19) . . ?
C3 C2 Cl2 127.3(3) . . ?
C3 C2 S1 113.4(3) . . ?
Cl2 C2 S1 119.3(2) . . ?
C2 C3 C4 112.1(3) . . ?
C2 C3 H3A 123.9 . . ?
C4 C3 H3A 123.9 . . ?
C1 C4 C3 110.8(3) . . ?
C1 C4 C5 128.7(3) . . ?
C3 C4 C5 120.4(3) . . ?
O1 C5 C6 122.4(3) . . ?
O1 C5 C4 118.6(3) . . ?
C6 C5 C4 118.9(3) . . ?
C7 C6 C5 120.9(3) . . ?
C7 C6 H6A 119.6 . . ?
C5 C6 H6A 119.6 . . ?
C6 C7 C8 126.5(3) . . ?
C6 C7 H7A 116.8 . . ?
C8 C7 H7A 116.8 . . ?
C13 C8 C9 115.1(3) . . ?
C13 C8 C7 125.1(3) . . ?
C9 C8 C7 119.8(3) . . ?
C10 C9 C8 123.2(3) . . ?
C10 C9 Cl3 117.8(3) . . ?
C8 C9 Cl3 118.9(3) . . ?
C11 C10 C9 119.2(3) . . ?
C11 C10 H10A 120.4 . . ?
C9 C10 H10A 120.4 . . ?
C10 C11 C12 120.3(3) . . ?
C10 C11 H11A 119.8 . . ?
C12 C11 H11A 119.8 . . ?
C11 C12 C13 119.4(3) . . ?
C11 C12 H12A 120.3 . . ?
C13 C12 H12A 120.3 . . ?
C12 C13 C8 122.7(3) . . ?
C12 C13 Cl4 116.2(3) . . ?
C8 C13 Cl4 121.1(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 S1 C1 C4 0.5(3) . . . . ?
C2 S1 C1 Cl1 177.9(2) . . . . ?
C1 S1 C2 C3 -1.0(3) . . . . ?
C1 S1 C2 Cl2 179.8(2) . . . . ?
Cl2 C2 C3 C4 -179.6(3) . . . . ?
S1 C2 C3 C4 1.2(4) . . . . ?
Cl1 C1 C4 C3 -177.0(3) . . . . ?
S1 C1 C4 C3 0.1(4) . . . . ?
Cl1 C1 C4 C5 -0.5(5) . . . . ?
S1 C1 C4 C5 176.5(3) . . . . ?
C2 C3 C4 C1 -0.8(4) . . . . ?
C2 C3 C4 C5 -177.6(3) . . . . ?
C1 C4 C5 O1 -149.0(4) . . . . ?
C3 C4 C5 O1 27.2(5) . . . . ?
C1 C4 C5 C6 33.7(5) . . . . ?
C3 C4 C5 C6 -150.2(3) . . . . ?
O1 C5 C6 C7 7.8(6) . . . . ?
C4 C5 C6 C7 -175.0(3) . . . . ?
C5 C6 C7 C8 -177.1(3) . . . . ?
C6 C7 C8 C13 -46.4(6) . . . . ?
C6 C7 C8 C9 133.2(4) . . . . ?
C13 C8 C9 C10 1.5(5) . . . . ?
C7 C8 C9 C10 -178.2(3) . . . . ?
C13 C8 C9 Cl3 -179.9(2) . . . . ?
C7 C8 C9 Cl3 0.4(4) . . . . ?
C8 C9 C10 C11 -1.2(5) . . . . ?
Cl3 C9 C10 C11 -179.9(3) . . . . ?
C9 C10 C11 C12 -0.3(6) . . . . ?
C10 C11 C12 C13 1.5(6) . . . . ?
C11 C12 C13 C8 -1.2(5) . . . . ?
C11 C12 C13 Cl4 -179.1(3) . . . . ?
C9 C8 C13 C12 -0.2(5) . . . . ?
C7 C8 C13 C12 179.4(3) . . . . ?
C9 C8 C13 Cl4 177.6(2) . . . . ?
C7 C8 C13 Cl4 -2.7(5) . . . . ?

_refine_diff_density_max         0.418
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.061

