# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_bd60m
_database_code_depnum_ccdc_archive 'CCDC 1524476'
_audit_update_record             
;
2016-12-26 deposited with the CCDC.
2017-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'4-(4-chlorophenyl)-2-(5-(4-chlorophenyl)-1H-pyrazol-1-yl) thiazole'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H11 Cl2 N3 S'
_chemical_formula_sum            'C18 H11 Cl2 N3 S'
_chemical_formula_weight         372.26

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'

_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'

_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'
'-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                   7.3400(7)
_cell_length_b                   18.9644(18)
_cell_length_c                   23.232(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3233.9(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5645
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      27.32

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_F_000             1520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.270
_exptl_absorpt_coefficient_mu    0.535
_shelx_estimated_absorpt_T_min   0.839
_shelx_estimated_absorpt_T_max   0.869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.834
_exptl_absorpt_correction_T_max  0.865
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   
'Sheldrick,G.M.,(2003),University of gottingen,Germany'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31269
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.148
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3164
_reflns_number_gt                3057
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0317P)²+3.7395P] 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         3164
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0591
_refine_ls_wR_factor_ref         0.1253
_refine_ls_wR_factor_gt          0.1245
_refine_ls_goodness_of_fit_ref   1.337
_refine_ls_restrained_S_all      1.337
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8579(4) 0.22799(15) 0.59085(12) 0.0356(6) Uani 1 1 d . . . . .
C2 C 0.9537(4) 0.28533(16) 0.61082(12) 0.0403(7) Uani 1 1 d . . . . .
H2 H 1.0283 0.2813 0.6430 0.048 Uiso 1 1 calc R U . . .
C3 C 0.9373(4) 0.34910(16) 0.58225(12) 0.0388(7) Uani 1 1 d . . . . .
H3 H 1.0008 0.3883 0.5956 0.047 Uiso 1 1 calc R U . . .
C4 C 0.8273(4) 0.35531(14) 0.53384(11) 0.0317(6) Uani 1 1 d . . . . .
C5 C 0.7329(4) 0.29607(15) 0.51461(11) 0.0332(6) Uani 1 1 d . . . . .
H5 H 0.6595 0.2994 0.4821 0.040 Uiso 1 1 calc R U . . .
C6 C 0.7469(4) 0.23273(15) 0.54309(12) 0.0356(6) Uani 1 1 d . . . . .
H6 H 0.6824 0.1935 0.5303 0.043 Uiso 1 1 calc R U . . .
C7 C 0.7956(4) 0.42583(15) 0.50940(11) 0.0338(6) Uani 1 1 d . . . . .
C8 C 0.7578(5) 0.48652(16) 0.53871(13) 0.0443(7) Uani 1 1 d . . . . .
H8 H 0.7556 0.4924 0.5784 0.053 Uiso 1 1 calc R U . . .
C9 C 0.7231(5) 0.53789(16) 0.49726(15) 0.0495(8) Uani 1 1 d . . . . .
H9 H 0.6919 0.5842 0.5058 0.059 Uiso 1 1 calc R U . . .
C10 C 0.8303(4) 0.40755(15) 0.40157(11) 0.0339(6) Uani 1 1 d . . . . .
C11 C 0.8971(5) 0.37881(17) 0.30395(13) 0.0501(8) Uani 1 1 d . . . . .
H11 H 0.9181 0.3752 0.2646 0.060 Uiso 1 1 calc R U . . .
C12 C 0.9146(4) 0.32474(15) 0.34159(11) 0.0345(6) Uani 1 1 d . . . . .
C13 C 0.9723(4) 0.25241(15) 0.32850(11) 0.0323(6) Uani 1 1 d . . . . .
C14 C 1.0706(4) 0.23627(17) 0.27888(12) 0.0404(7) Uani 1 1 d . . . . .
H14 H 1.0969 0.2718 0.2526 0.048 Uiso 1 1 calc R U . . .
C15 C 1.1295(4) 0.16856(17) 0.26809(12) 0.0426(7) Uani 1 1 d . . . . .
H15 H 1.1956 0.1584 0.2349 0.051 Uiso 1 1 calc R U . . .
C16 C 1.0893(4) 0.11617(16) 0.30709(12) 0.0392(7) Uani 1 1 d . . . . .
C17 C 0.9900(4) 0.12970(16) 0.35625(12) 0.0386(7) Uani 1 1 d . . . . .
H17 H 0.9621 0.0936 0.3819 0.046 Uiso 1 1 calc R U . . .
C18 C 0.9330(4) 0.19780(15) 0.36658(11) 0.0357(6) Uani 1 1 d . . . . .
H18 H 0.8667 0.2075 0.3998 0.043 Uiso 1 1 calc R U . . .
Cl1 Cl 0.87887(12) 0.14753(4) 0.62683(4) 0.0523(2) Uani 1 1 d . . . . .
Cl2 Cl 1.17373(16) 0.03129(5) 0.29588(4) 0.0654(3) Uani 1 1 d . . . . .
N1 N 0.7396(4) 0.51337(13) 0.44485(11) 0.0449(6) Uani 1 1 d . . . . .
N2 N 0.7832(3) 0.44383(12) 0.45195(10) 0.0358(5) Uani 1 1 d . . . . .
N3 N 0.8741(3) 0.34224(12) 0.39824(9) 0.0330(5) Uani 1 1 d . . . . .
S1 S 0.83118(15) 0.45501(4) 0.33806(3) 0.0543(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
C1 C2 1.376(4) . ?
C1 C6 1.379(4) . ?
C1 Cl1 1.747(3) . ?
C2 C3 1.385(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(4) . ?
C4 C7 1.471(4) . ?
C5 C6 1.375(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.366(4) . ?
C7 N2 1.381(3) . ?
C8 C9 1.393(4) . ?
C8 H8 0.9300 . ?
C9 N1 1.309(4) . ?
C9 H9 0.9300 . ?
C10 N3 1.282(4) . ?
C10 N2 1.401(4) . ?
C10 S1 1.728(3) . ?
C11 C12 1.354(4) . ?
C11 S1 1.718(3) . ?
C11 H11 0.9300 . ?
C12 N3 1.389(3) . ?
C12 C13 1.467(4) . ?
C13 C18 1.392(4) . ?
C13 C14 1.394(4) . ?
C14 C15 1.378(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.379(4) . ?
C16 Cl2 1.745(3) . ?
C17 C18 1.379(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
N1 N2 1.367(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.4(3) . . ?
C2 C1 Cl1 119.0(2) . . ?
C6 C1 Cl1 119.6(2) . . ?
C1 C2 C3 119.0(3) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 120.8(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 118.7(3) . . ?
C3 C4 C7 118.8(2) . . ?
C5 C4 C7 122.0(2) . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 119.2(3) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C8 C7 N2 105.1(2) . . ?
C8 C7 C4 127.3(3) . . ?
N2 C7 C4 127.5(2) . . ?
C7 C8 C9 106.4(3) . . ?
C7 C8 H8 126.8 . . ?
C9 C8 H8 126.8 . . ?
N1 C9 C8 112.2(3) . . ?
N1 C9 H9 123.9 . . ?
C8 C9 H9 123.9 . . ?
N3 C10 N2 125.9(2) . . ?
N3 C10 S1 116.8(2) . . ?
N2 C10 S1 117.3(2) . . ?
C12 C11 S1 111.5(2) . . ?
C12 C11 H11 124.3 . . ?
S1 C11 H11 124.3 . . ?
C11 C12 N3 114.2(3) . . ?
C11 C12 C13 127.0(3) . . ?
N3 C12 C13 118.8(2) . . ?
C18 C13 C14 118.0(3) . . ?
C18 C13 C12 120.3(2) . . ?
C14 C13 C12 121.7(3) . . ?
C15 C14 C13 121.2(3) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C16 C15 C14 119.0(3) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C15 C16 C17 121.6(3) . . ?
C15 C16 Cl2 119.4(2) . . ?
C17 C16 Cl2 118.9(2) . . ?
C16 C17 C18 118.6(3) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
C17 C18 C13 121.6(3) . . ?
C17 C18 H18 119.2 . . ?
C13 C18 H18 119.2 . . ?
C9 N1 N2 104.6(2) . . ?
N1 N2 C7 111.8(2) . . ?
N1 N2 C10 115.5(2) . . ?
C7 N2 C10 132.1(2) . . ?
C10 N3 C12 110.0(2) . . ?
C11 S1 C10 87.52(14) . . ?

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
C6 C1 C2 C3 0.2(4) . . . . ?
Cl1 C1 C2 C3 179.9(2) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C2 C3 C4 C7 172.2(3) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C7 C4 C5 C6 -171.3(3) . . . . ?
C4 C5 C6 C1 -0.8(4) . . . . ?
C2 C1 C6 C5 0.5(4) . . . . ?
Cl1 C1 C6 C5 -179.2(2) . . . . ?
C3 C4 C7 C8 -43.5(4) . . . . ?
C5 C4 C7 C8 128.2(3) . . . . ?
C3 C4 C7 N2 142.1(3) . . . . ?
C5 C4 C7 N2 -46.2(4) . . . . ?
N2 C7 C8 C9 0.4(4) . . . . ?
C4 C7 C8 C9 -174.9(3) . . . . ?
C7 C8 C9 N1 -1.0(4) . . . . ?
S1 C11 C12 N3 0.7(4) . . . . ?
S1 C11 C12 C13 -178.5(2) . . . . ?
C11 C12 C13 C18 -160.7(3) . . . . ?
N3 C12 C13 C18 20.1(4) . . . . ?
C11 C12 C13 C14 20.8(5) . . . . ?
N3 C12 C13 C14 -158.4(3) . . . . ?
C18 C13 C14 C15 -0.9(4) . . . . ?
C12 C13 C14 C15 177.7(3) . . . . ?
C13 C14 C15 C16 0.3(5) . . . . ?
C14 C15 C16 C17 0.7(5) . . . . ?
C14 C15 C16 Cl2 -176.5(2) . . . . ?
C15 C16 C17 C18 -1.1(5) . . . . ?
Cl2 C16 C17 C18 176.2(2) . . . . ?
C16 C17 C18 C13 0.5(4) . . . . ?
C14 C13 C18 C17 0.5(4) . . . . ?
C12 C13 C18 C17 -178.1(3) . . . . ?
C8 C9 N1 N2 1.0(4) . . . . ?
C9 N1 N2 C7 -0.7(4) . . . . ?
C9 N1 N2 C10 -172.4(3) . . . . ?
C8 C7 N2 N1 0.2(3) . . . . ?
C4 C7 N2 N1 175.5(3) . . . . ?
C8 C7 N2 C10 170.1(3) . . . . ?
C4 C7 N2 C10 -14.6(5) . . . . ?
N3 C10 N2 N1 -179.4(3) . . . . ?
S1 C10 N2 N1 1.1(3) . . . . ?
N3 C10 N2 C7 11.0(5) . . . . ?
S1 C10 N2 C7 -168.5(3) . . . . ?
N2 C10 N3 C12 -179.2(3) . . . . ?
S1 C10 N3 C12 0.3(3) . . . . ?
C11 C12 N3 C10 -0.7(4) . . . . ?
C13 C12 N3 C10 178.6(3) . . . . ?
C12 C11 S1 C10 -0.4(3) . . . . ?
N3 C10 S1 C11 0.0(3) . . . . ?
N2 C10 S1 C11 179.6(3) . . . . ?

_refine_diff_density_max         0.313
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.056

