#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/69/2236910.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2236910
loop_
_publ_author_name
'Selvakumaran, N.'
'Sheeba, M. Mary'
'Karvembu, R.'
'Ng, Seik Weng'
'Tiekink, Edward R. T.'
_publ_section_title
;
 1-Benzoyl-3-(4-chlorophenyl)thiourea dichloromethane hemisolvate
;
_journal_coeditor_code           HG5268
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3313
_journal_paper_doi               10.1107/S1600536812045588
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C14 H11 Cl N2 O S, 0.5C H2 Cl2'
_chemical_formula_moiety         'C14 H11 Cl N2 O S, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C14.5 H12 Cl2 N2 O S'
_chemical_formula_weight         333.23
_chemical_name_systematic
;
1-Benzoyl-3-(4-chlorophenyl)thiourea dichloromethane hemisolvate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 117.690(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.0800(4)
_cell_length_b                   16.0136(2)
_cell_length_c                   10.3752(2)
_cell_measurement_reflns_used    3963
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.2207
_cell_measurement_theta_min      3.7116
_cell_volume                     2954.10(12)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2012)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2012)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg,
2006) and
Qmol (Gans & Shalloway, 2001)
;
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type
'Agilent SuperNova Dual diffractometer with an Atlas detector'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0127
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5766
_diffrn_reflns_theta_full        74.39
_diffrn_reflns_theta_max         74.39
_diffrn_reflns_theta_min         3.71
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.257
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.629
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2937
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0310
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0515P)²+3.8195P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0897
_reflns_number_gt                2802
_reflns_number_total             2937
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg5268.cif
_cod_data_source_block           I
_cod_original_cell_volume        2954.10(9)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C14.5 H12 Cl2 N2 O1 S1'
_cod_database_code               2236910
_cod_database_fobs_code          2236910
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Cl Cl1 0.64817(3) 0.24103(3) 1.38168(4) 0.02772(13) Uani d . 1 1
Cl Cl2 0.06334(3) 0.49157(3) 0.21781(6) 0.04144(16) Uani d . 1 1
S S1 0.34276(2) 0.21105(2) 0.68579(4) 0.01812(12) Uani d . 1 1
O O1 0.40404(6) 0.47474(7) 0.61554(12) 0.0182(2) Uani d . 1 1
N N2 0.43155(7) 0.34562(8) 0.78527(14) 0.0141(3) Uani d . 1 1
N N1 0.33686(7) 0.35253(8) 0.54885(14) 0.0139(3) Uani d . 1 1
C C1 0.30153(8) 0.46811(10) 0.37713(17) 0.0142(3) Uani d . 1 1
C C2 0.26545(9) 0.41884(10) 0.25243(17) 0.0161(3) Uani d . 1 1
H H2 0.2727 0.3601 0.2585 0.019 Uiso calc R 1 1
C C3 0.21909(9) 0.45587(11) 0.11989(18) 0.0196(3) Uani d . 1 1
H H3 0.1946 0.4224 0.0350 0.024 Uiso calc R 1 1
C C4 0.20837(9) 0.54186(11) 0.11089(18) 0.0210(3) Uani d . 1 1
H H4 0.1760 0.5669 0.0201 0.025 Uiso calc R 1 1
C C5 0.24478(9) 0.59118(11) 0.23394(19) 0.0199(3) Uani d . 1 1
H H5 0.2374 0.6499 0.2271 0.024 Uiso calc R 1 1
C C6 0.29191(9) 0.55510(10) 0.36699(18) 0.0166(3) Uani d . 1 1
H H6 0.3176 0.5891 0.4509 0.020 Uiso calc R 1 1
C C7 0.35206(8) 0.43302(10) 0.52309(17) 0.0143(3) Uani d . 1 1
C C8 0.37385(8) 0.30647(10) 0.67746(17) 0.0135(3) Uani d . 1 1
C C9 0.48080(8) 0.31534(10) 0.92652(17) 0.0136(3) Uani d . 1 1
C C10 0.50405(8) 0.37306(10) 1.03984(17) 0.0151(3) Uani d . 1 1
H H10 0.4840 0.4280 1.0210 0.018 Uiso calc R 1 1
C C12 0.55623(9) 0.35074(10) 1.17967(17) 0.0166(3) Uani d . 1 1
H H12 0.5727 0.3901 1.2568 0.020 Uiso calc R 1 1
C C13 0.58394(9) 0.26988(11) 1.20494(18) 0.0172(3) Uani d . 1 1
C C14 0.56186(9) 0.21168(10) 1.09322(18) 0.0179(3) Uani d . 1 1
H H14 0.5820 0.1567 1.1126 0.021 Uiso calc R 1 1
C C15 0.51002(9) 0.23468(10) 0.95287(17) 0.0156(3) Uani d . 1 1
H H15 0.4946 0.1956 0.8754 0.019 Uiso calc R 1 1
C C16 0.0000 0.5521(2) 0.2500 0.090(2) Uani d S 1 2
H H16A -0.0286 0.5885 0.1647 0.108 Uiso calc PR 0.50 1
H H16B 0.0286 0.5885 0.3353 0.108 Uiso calc PR 0.50 1
H H1n 0.2952(13) 0.3301(14) 0.485(2) 0.026(6) Uiso d . 1 1
H H2n 0.4380(12) 0.3990(15) 0.767(2) 0.029(6) Uiso d . 1 1
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'
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C8 N2 C9 . . 128.44(14)
C8 N2 H2n . . 115.0(14)
C9 N2 H2n . . 116.4(14)
C7 N1 C8 . . 127.64(13)
C7 N1 H1n . . 117.6(15)
C8 N1 H1n . . 113.8(15)
C2 C1 C6 . . 119.81(15)
C2 C1 C7 . . 123.01(14)
C6 C1 C7 . . 117.16(14)
C3 C2 C1 . . 119.86(15)
C3 C2 H2 . . 120.1
C1 C2 H2 . . 120.1
C2 C3 C4 . . 120.15(15)
C2 C3 H3 . . 119.9
C4 C3 H3 . . 119.9
C5 C4 C3 . . 120.25(15)
C5 C4 H4 . . 119.9
C3 C4 H4 . . 119.9
C4 C5 C6 . . 120.24(15)
C4 C5 H5 . . 119.9
C6 C5 H5 . . 119.9
C5 C6 C1 . . 119.67(15)
C5 C6 H6 . . 120.2
C1 C6 H6 . . 120.2
O1 C7 N1 . . 122.58(14)
O1 C7 C1 . . 121.13(14)
N1 C7 C1 . . 116.29(13)
N2 C8 N1 . . 114.91(13)
N2 C8 S1 . . 125.93(12)
N1 C8 S1 . . 119.15(11)
C15 C9 C10 . . 120.27(14)
C15 C9 N2 . . 123.21(14)
C10 C9 N2 . . 116.34(14)
C12 C10 C9 . . 120.40(15)
C12 C10 H10 . . 119.8
C9 C10 H10 . . 119.8
C10 C12 C13 . . 118.77(15)
C10 C12 H12 . . 120.6
C13 C12 H12 . . 120.6
C12 C13 C14 . . 121.64(15)
C12 C13 Cl1 . . 118.83(13)
C14 C13 Cl1 . . 119.53(13)
C13 C14 C15 . . 119.32(15)
C13 C14 H14 . . 120.3
C15 C14 H14 . . 120.3
C14 C15 C9 . . 119.59(15)
C14 C15 H15 . . 120.2
C9 C15 H15 . . 120.2
Cl2 C16 Cl2 . 2 112.8(2)
Cl2 C16 H16A . . 109.0
Cl2 C16 H16A 2 . 109.0
Cl2 C16 H16B . . 109.0
Cl2 C16 H16B 2 . 109.0
H16A C16 H16B . . 107.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cl1 C13 . 1.7439(16)
Cl2 C16 . 1.750(2)
S1 C8 . 1.6679(16)
O1 C7 . 1.2350(19)
N2 C8 . 1.335(2)
N2 C9 . 1.419(2)
N2 H2n . 0.90(2)
N1 C7 . 1.379(2)
N1 C8 . 1.398(2)
N1 H1n . 0.87(2)
C1 C2 . 1.396(2)
C1 C6 . 1.403(2)
C1 C7 . 1.487(2)
C2 C3 . 1.385(2)
C2 H2 . 0.9500
C3 C4 . 1.390(2)
C3 H3 . 0.9500
C4 C5 . 1.386(3)
C4 H4 . 0.9500
C5 C6 . 1.386(2)
C5 H5 . 0.9500
C6 H6 . 0.9500
C9 C15 . 1.392(2)
C9 C10 . 1.395(2)
C10 C12 . 1.385(2)
C10 H10 . 0.9500
C12 C13 . 1.385(2)
C12 H12 . 0.9500
C13 C14 . 1.390(2)
C14 C15 . 1.390(2)
C14 H14 . 0.9500
C15 H15 . 0.9500
C16 Cl2 2 1.750(2)
C16 H16A . 0.9900
C16 H16B . 0.9900
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H2n O1 . 0.90(2) 1.85(2) 2.6034(17) 140.6(18)
N1 H1n S1 7_556 0.87(2) 2.59(2) 3.4368(15) 167(2)
C12 H12 O1 5_667 0.95 2.47 3.3743(19) 160
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
C6 C1 C2 C3 -1.4(2)
C7 C1 C2 C3 179.99(14)
C1 C2 C3 C4 -0.1(2)
C2 C3 C4 C5 0.9(2)
C3 C4 C5 C6 -0.3(2)
C4 C5 C6 C1 -1.2(2)
C2 C1 C6 C5 2.0(2)
C7 C1 C6 C5 -179.27(14)
C8 N1 C7 O1 1.6(2)
C8 N1 C7 C1 -177.64(14)
C2 C1 C7 O1 151.52(15)
C6 C1 C7 O1 -27.2(2)
C2 C1 C7 N1 -29.2(2)
C6 C1 C7 N1 152.07(14)
C9 N2 C8 N1 -178.51(14)
C9 N2 C8 S1 2.8(2)
C7 N1 C8 N2 -1.7(2)
C7 N1 C8 S1 177.10(12)
C8 N2 C9 C15 41.7(2)
C8 N2 C9 C10 -143.19(16)
C15 C9 C10 C12 -0.2(2)
N2 C9 C10 C12 -175.41(13)
C9 C10 C12 C13 -0.9(2)
C10 C12 C13 C14 1.4(2)
C10 C12 C13 Cl1 -178.67(12)
C12 C13 C14 C15 -0.8(2)
Cl1 C13 C14 C15 179.28(12)
C13 C14 C15 C9 -0.3(2)
C10 C9 C15 C14 0.8(2)
N2 C9 C15 C14 175.69(14)
