# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_3clsma3
_database_code_depnum_ccdc_archive 'CCDC 1062366'
_audit_update_record             
;
2015-04-29 deposited with the CCDC.
2015-10-07 downloaded from the CCDC.
;
#==================================================================
_audit_creation_date             2014-11-12
_audit_creation_method           
#==========================================================================

# SUBMISSION DETAILS
;
Olex2 1.2-beta
(compiled 2014.10.22 svn.r3046 for OlexSys, GUI svn.r4928)
;
_shelxl_version_number           2014-3
#==========================================================================
# CHEMICAL DATA
_chemical_name_common            ?
_chemical_name_systematic        
(3,5-bis(4-chlorophenyl)thiophen-2-yl)(4-chlorophenyl)methanone
_chemical_formula_moiety         'C23 H13 Cl3 O S'
_chemical_formula_sum            'C23 H13 Cl3 O S'
_chemical_formula_weight         443.74
_chemical_melting_point          438
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'

_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.
;
#==========================================================================

# CRYSTAL DATA 
_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                   7.5101(18)
_cell_length_b                   9.387(2)
_cell_length_c                   14.553(4)
_cell_angle_alpha                97.563(2)
_cell_angle_beta                 92.562(2)
_cell_angle_gamma                107.979(2)
_cell_volume                     963.4(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6130
_cell_measurement_temperature    110.15
_cell_measurement_theta_max      27.477
_cell_measurement_theta_min      2.517
_shelx_estimated_absorpt_T_max   0.832
_shelx_estimated_absorpt_T_min   0.728
_exptl_absorpt_coefficient_mu    0.596
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
#==========================================================================

# Experimental data 
;
SADABS-2014/3 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0910 before and 0.0417 after correction.
The Ratio of minimum to maximum transmission is 0.8580.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.32
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11148
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.536
_diffrn_reflns_theta_min         1.417
_diffrn_ambient_temperature      110.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3905
_reflns_number_total             4349
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4349
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0343
_refine_ls_restrained_S_all      1.034
_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)+(0.0383P)²+0.7457P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0878
#==========================================================================

# Refinement data 
_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:
 C3(H3), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14), C16(H16),
 C17(H17), C19(H19), C20(H20), C22(H22), C23(H23)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
#==========================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 
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 0.98152(7) 0.27986(6) 0.96261(3) 0.02715(12) Uani 1 1 d . . . . .
Cl2 Cl 0.51208(7) 0.72038(6) 1.02153(3) 0.02562(12) Uani 1 1 d . . . . .
Cl3 Cl 0.73372(6) 1.12266(5) 0.17300(3) 0.02158(11) Uani 1 1 d . . . . .
S1 S 0.78567(6) 0.59532(5) 0.46269(3) 0.01494(10) Uani 1 1 d . . . . .
O1 O 0.68988(18) 0.30414(14) 0.52928(8) 0.0202(3) Uani 1 1 d . . . . .
C1 C 0.7533(2) 0.56409(19) 0.57564(11) 0.0140(3) Uani 1 1 d . . . . .
C2 C 0.7317(2) 0.68948(18) 0.63035(11) 0.0135(3) Uani 1 1 d . . . . .
C3 C 0.7471(2) 0.81061(19) 0.57887(12) 0.0147(3) Uani 1 1 d . . . . .
H3 H 0.7385 0.9060 0.6055 0.018 Uiso 1 1 calc R . . . .
C4 C 0.7756(2) 0.77734(18) 0.48711(12) 0.0137(3) Uani 1 1 d . . . . .
C5 C 0.7427(2) 0.41055(18) 0.59309(11) 0.0140(3) Uani 1 1 d . . . . .
C6 C 0.8003(2) 0.38432(18) 0.68731(11) 0.0139(3) Uani 1 1 d . . . . .
C7 C 0.7099(2) 0.24488(19) 0.71492(12) 0.0158(3) Uani 1 1 d . . . . .
H7 H 0.6124 0.1709 0.6746 0.019 Uiso 1 1 calc R . . . .
C8 C 0.7618(3) 0.2138(2) 0.80094(12) 0.0178(3) Uani 1 1 d . . . . .
H8 H 0.6983 0.1203 0.8208 0.021 Uiso 1 1 calc R . . . .
C9 C 0.9080(3) 0.3218(2) 0.85734(12) 0.0178(3) Uani 1 1 d . . . . .
C10 C 0.9998(2) 0.4610(2) 0.83135(12) 0.0178(3) Uani 1 1 d . . . . .
H10 H 1.0992 0.5337 0.8713 0.021 Uiso 1 1 calc R . . . .
C11 C 0.9443(2) 0.49239(19) 0.74610(12) 0.0156(3) Uani 1 1 d . . . . .
H11 H 1.0046 0.5878 0.7278 0.019 Uiso 1 1 calc R . . . .
C12 C 0.6803(2) 0.69580(19) 0.72730(11) 0.0134(3) Uani 1 1 d . . . . .
C13 C 0.5458(2) 0.57355(19) 0.75544(12) 0.0150(3) Uani 1 1 d . . . . .
H13 H 0.4865 0.4850 0.7116 0.018 Uiso 1 1 calc R . . . .
C14 C 0.4974(2) 0.5793(2) 0.84618(12) 0.0163(3) Uani 1 1 d . . . . .
H14 H 0.4075 0.4947 0.8649 0.020 Uiso 1 1 calc R . . . .
C15 C 0.5816(2) 0.7096(2) 0.90921(12) 0.0167(3) Uani 1 1 d . . . . .
C16 C 0.7157(2) 0.8334(2) 0.88377(12) 0.0175(3) Uani 1 1 d . . . . .
H16 H 0.7738 0.9218 0.9279 0.021 Uiso 1 1 calc R . . . .
C17 C 0.7634(2) 0.82586(19) 0.79280(12) 0.0158(3) Uani 1 1 d . . . . .
H17 H 0.8542 0.9104 0.7746 0.019 Uiso 1 1 calc R . . . .
C18 C 0.7799(2) 0.86796(18) 0.41172(11) 0.0138(3) Uani 1 1 d . . . . .
C19 C 0.7413(2) 1.00604(19) 0.42723(12) 0.0166(3) Uani 1 1 d . . . . .
H19 H 0.7227 1.0453 0.4883 0.020 Uiso 1 1 calc R . . . .
C20 C 0.7301(2) 1.08599(19) 0.35462(12) 0.0169(3) Uani 1 1 d . . . . .
H20 H 0.7049 1.1796 0.3659 0.020 Uiso 1 1 calc R . . . .
C21 C 0.7560(2) 1.02784(19) 0.26553(12) 0.0152(3) Uani 1 1 d . . . . .
C22 C 0.7991(2) 0.89371(19) 0.24820(12) 0.0157(3) Uani 1 1 d . . . . .
H22 H 0.8194 0.8560 0.1871 0.019 Uiso 1 1 calc R . . . .
C23 C 0.8120(2) 0.81563(19) 0.32161(12) 0.0155(3) Uani 1 1 d . . . . .
H23 H 0.8434 0.7247 0.3103 0.019 Uiso 1 1 calc R . . . .

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

# MOLECULAR GEOMETRY 

_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 1.7392(18) . ?
Cl2 C15 1.7379(17) . ?
Cl3 C21 1.7380(17) . ?
S1 C1 1.7222(17) . ?
S1 C4 1.7246(17) . ?
O1 C5 1.223(2) . ?
C1 C2 1.388(2) . ?
C1 C5 1.475(2) . ?
C2 C3 1.421(2) . ?
C2 C12 1.478(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.372(2) . ?
C4 C18 1.470(2) . ?
C5 C6 1.493(2) . ?
C6 C7 1.396(2) . ?
C6 C11 1.393(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.388(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.385(3) . ?
C9 C10 1.387(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.388(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.397(2) . ?
C12 C17 1.400(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.384(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.383(3) . ?
C15 C16 1.388(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.385(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.405(2) . ?
C18 C23 1.397(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.388(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.385(2) . ?
C21 C22 1.389(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.389(2) . ?
C23 H23 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
C1 S1 C4 92.38(8) . . ?
C2 C1 S1 111.42(12) . . ?
C2 C1 C5 133.44(15) . . ?
C5 C1 S1 115.01(12) . . ?
C1 C2 C3 111.57(15) . . ?
C1 C2 C12 125.72(15) . . ?
C3 C2 C12 122.44(14) . . ?
C2 C3 H3 123.1 . . ?
C4 C3 C2 113.88(15) . . ?
C4 C3 H3 123.1 . . ?
C3 C4 S1 110.72(12) . . ?
C3 C4 C18 129.03(15) . . ?
C18 C4 S1 119.98(12) . . ?
O1 C5 C1 119.66(15) . . ?
O1 C5 C6 119.65(15) . . ?
C1 C5 C6 120.67(14) . . ?
C7 C6 C5 118.21(15) . . ?
C11 C6 C5 121.90(15) . . ?
C11 C6 C7 119.85(16) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.31(16) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 120.6 . . ?
C9 C8 C7 118.77(16) . . ?
C9 C8 H8 120.6 . . ?
C8 C9 Cl1 118.99(14) . . ?
C8 C9 C10 121.90(16) . . ?
C10 C9 Cl1 119.10(14) . . ?
C9 C10 H10 120.5 . . ?
C9 C10 C11 118.94(16) . . ?
C11 C10 H10 120.5 . . ?
C6 C11 H11 119.9 . . ?
C10 C11 C6 120.20(16) . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C2 120.98(15) . . ?
C13 C12 C17 118.40(15) . . ?
C17 C12 C2 120.62(15) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.07(16) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 120.4 . . ?
C15 C14 C13 119.14(16) . . ?
C15 C14 H14 120.4 . . ?
C14 C15 Cl2 119.13(14) . . ?
C14 C15 C16 121.41(16) . . ?
C16 C15 Cl2 119.43(13) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 C15 118.81(16) . . ?
C17 C16 H16 120.6 . . ?
C12 C17 H17 119.4 . . ?
C16 C17 C12 121.15(16) . . ?
C16 C17 H17 119.4 . . ?
C19 C18 C4 120.74(15) . . ?
C23 C18 C4 121.07(15) . . ?
C23 C18 C19 118.09(15) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 120.99(16) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 120.3 . . ?
C21 C20 C19 119.30(15) . . ?
C21 C20 H20 120.3 . . ?
C20 C21 Cl3 119.98(13) . . ?
C20 C21 C22 121.16(15) . . ?
C22 C21 Cl3 118.86(13) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 C21 118.97(15) . . ?
C23 C22 H22 120.5 . . ?
C18 C23 H23 119.3 . . ?
C22 C23 C18 121.42(15) . . ?
C22 C23 H23 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C9 C10 C11 178.17(13) . . . . ?
Cl2 C15 C16 C17 -177.03(13) . . . . ?
Cl3 C21 C22 C23 -178.31(13) . . . . ?
S1 C1 C2 C3 -1.52(18) . . . . ?
S1 C1 C2 C12 172.70(13) . . . . ?
S1 C1 C5 O1 -26.1(2) . . . . ?
S1 C1 C5 C6 152.39(13) . . . . ?
S1 C4 C18 C19 169.60(13) . . . . ?
S1 C4 C18 C23 -6.8(2) . . . . ?
O1 C5 C6 C7 -32.3(2) . . . . ?
O1 C5 C6 C11 145.58(17) . . . . ?
C1 S1 C4 C3 -0.35(13) . . . . ?
C1 S1 C4 C18 -174.95(14) . . . . ?
C1 C2 C3 C4 1.3(2) . . . . ?
C1 C2 C12 C13 -39.7(2) . . . . ?
C1 C2 C12 C17 141.35(17) . . . . ?
C1 C5 C6 C7 149.18(16) . . . . ?
C1 C5 C6 C11 -32.9(2) . . . . ?
C2 C1 C5 O1 149.47(19) . . . . ?
C2 C1 C5 C6 -32.0(3) . . . . ?
C2 C3 C4 S1 -0.46(19) . . . . ?
C2 C3 C4 C18 173.51(16) . . . . ?
C2 C12 C13 C14 -179.97(15) . . . . ?
C2 C12 C17 C16 179.67(15) . . . . ?
C3 C2 C12 C13 133.91(17) . . . . ?
C3 C2 C12 C17 -45.0(2) . . . . ?
C3 C4 C18 C19 -3.9(3) . . . . ?
C3 C4 C18 C23 179.66(17) . . . . ?
C4 S1 C1 C2 1.08(13) . . . . ?
C4 S1 C1 C5 177.63(13) . . . . ?
C4 C18 C19 C20 -174.69(15) . . . . ?
C4 C18 C23 C22 173.95(15) . . . . ?
C5 C1 C2 C3 -177.20(17) . . . . ?
C5 C1 C2 C12 -3.0(3) . . . . ?
C5 C6 C7 C8 178.42(15) . . . . ?
C5 C6 C11 C10 -176.93(15) . . . . ?
C6 C7 C8 C9 -1.8(2) . . . . ?
C7 C6 C11 C10 0.9(2) . . . . ?
C7 C8 C9 Cl1 -176.79(13) . . . . ?
C7 C8 C9 C10 1.8(3) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C9 C10 C11 C6 -1.0(2) . . . . ?
C11 C6 C7 C8 0.5(2) . . . . ?
C12 C2 C3 C4 -173.14(15) . . . . ?
C12 C13 C14 C15 1.2(2) . . . . ?
C13 C12 C17 C16 0.7(2) . . . . ?
C13 C14 C15 Cl2 176.74(12) . . . . ?
C13 C14 C15 C16 -1.2(3) . . . . ?
C14 C15 C16 C17 0.9(3) . . . . ?
C15 C16 C17 C12 -0.6(3) . . . . ?
C17 C12 C13 C14 -1.0(2) . . . . ?
C18 C19 C20 C21 0.5(3) . . . . ?
C19 C18 C23 C22 -2.6(2) . . . . ?
C19 C20 C21 Cl3 177.59(13) . . . . ?
C19 C20 C21 C22 -2.1(3) . . . . ?
C20 C21 C22 C23 1.4(3) . . . . ?
C21 C22 C23 C18 1.0(3) . . . . ?
C23 C18 C19 C20 1.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
# End of CIF  ============================================================
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
