#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/05/2210581.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_2210581
loop_
_publ_author_name
'Khawar Rauf, M.'
'Badshah, Amin'
'Bolte, Michael'
_publ_section_title
;
 1-(2,4-Dichlorobenzoyl)-3-(3,4-dichlorophenyl)thiourea
;
_journal_coeditor_code           EZ2029
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4296
_journal_page_last               o4298
_journal_paper_doi               10.1107/S160053680603474X
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C14 H8 Cl4 N2 O S'
_chemical_formula_moiety         'C14 H8 Cl4 N2 O S'
_chemical_formula_sum            'C14 H8 Cl4 N2 O S'
_chemical_formula_weight         394.08
_chemical_name_common
1-(2,4-Dichlorobenzoyl)-3-(3,4-dichlorophenyl)thiourea
_chemical_name_systematic
;
1-(2,4-Dichlorobenzoyl)-3-(3,4-dichlorophenyl)thiourea
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.697(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.7287(11)
_cell_length_b                   9.2935(6)
_cell_length_c                   14.6300(15)
_cell_measurement_reflns_used    10746
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.7
_cell_measurement_theta_min      3.6
_cell_volume                     1608.0(3)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        X-AREA
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 1991)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Stoe IPDSII two-circle'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_av_sigmaI/netI    0.025
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10362
_diffrn_reflns_theta_full        25.6
_diffrn_reflns_theta_max         25.6
_diffrn_reflns_theta_min         3.6
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.866
_exptl_absorpt_correction_T_max  0.794
_exptl_absorpt_correction_T_min  0.707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(MULABS; Spek, 2003; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.37
_refine_ls_extinction_coef       0.0082(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2984
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.032
_refine_ls_R_factor_gt           0.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0379P)²+0.8376P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.069
_refine_ls_wR_factor_ref         0.071
_reflns_number_gt                2703
_reflns_number_total             2984
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ez2029.cif
_cod_data_source_block           I
_cod_original_cell_volume        1608.0(2)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2210581
_cod_database_fobs_code          2210581
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'
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
S S1 0.67564(3) 0.41198(4) 0.57312(3) 0.01751(12) Uani d . 1
Cl Cl1 0.48068(4) 0.81872(5) 0.29436(4) 0.03308(14) Uani d . 1
Cl Cl2 0.05644(4) 0.67716(6) 0.06373(4) 0.04495(17) Uani d . 1
Cl Cl3 1.12591(4) 0.40752(5) 0.72486(3) 0.03158(14) Uani d . 1
Cl Cl4 1.22243(3) 0.19052(6) 0.60743(4) 0.03204(14) Uani d . 1
C C1 0.53897(13) 0.49869(18) 0.28664(12) 0.0175(3) Uani d . 1
O O1 0.60245(10) 0.47027(16) 0.24341(9) 0.0297(3) Uani d . 1
N N1 0.56809(11) 0.48696(16) 0.38697(10) 0.0170(3) Uani d . 1
H H1 0.5202(18) 0.502(2) 0.4088(17) 0.029(6) Uiso d . 1
C C2 0.66861(13) 0.43466(17) 0.45698(12) 0.0150(3) Uani d . 1
N N2 0.75004(12) 0.40355(16) 0.42214(11) 0.0201(3) Uani d . 1
H H2 0.7320(17) 0.415(2) 0.3645(18) 0.020(5) Uiso d . 1
C C11 0.41848(13) 0.54509(18) 0.23138(11) 0.0163(3) Uani d . 1
C C12 0.38381(13) 0.68752(18) 0.23090(12) 0.0176(3) Uani d . 1
C C13 0.27285(14) 0.72927(19) 0.17857(12) 0.0215(4) Uani d . 1
H H13 0.2501 0.8267 0.1785 0.026 Uiso calc R 1
C C14 0.19605(14) 0.6247(2) 0.12645(13) 0.0237(4) Uani d . 1
C C15 0.22781(14) 0.4827(2) 0.12274(14) 0.0263(4) Uani d . 1
H H15 0.1743 0.4134 0.0852 0.032 Uiso calc R 1
C C16 0.33996(14) 0.44369(19) 0.17528(13) 0.0227(4) Uani d . 1
H H16 0.3632 0.3471 0.1729 0.027 Uiso calc R 1
C C21 0.86052(13) 0.34701(19) 0.47421(12) 0.0180(3) Uani d . 1
C C22 0.92976(13) 0.39681(18) 0.56701(12) 0.0184(3) Uani d . 1
H H22 0.9021 0.4651 0.6009 0.022 Uiso calc R 1
C C23 1.04035(13) 0.34474(18) 0.60935(12) 0.0191(3) Uani d . 1
C C24 1.08203(13) 0.24635(19) 0.55924(13) 0.0209(4) Uani d . 1
C C25 1.01149(15) 0.1951(2) 0.46766(14) 0.0256(4) Uani d . 1
H H25 1.0389 0.1256 0.4343 0.031 Uiso calc R 1
C C26 0.90106(14) 0.2453(2) 0.42487(13) 0.0236(4) Uani d . 1
H H26 0.8532 0.2105 0.3622 0.028 Uiso calc R 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Cl Cl 0.1484 0.1585 '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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O1 C1 N1 124.30(15) ?
O1 C1 C11 121.27(15) ?
N1 C1 C11 114.40(13) ?
C1 N1 C2 128.35(14) y
C1 N1 H1 117.8(16) ?
C2 N1 H1 113.4(16) ?
N2 C2 N1 114.97(14) y
N2 C2 S1 126.55(12) ?
N1 C2 S1 118.45(11) ?
C2 N2 C21 128.43(15) ?
C2 N2 H2 114.4(15) ?
C21 N2 H2 117.1(15) ?
C12 C11 C16 118.73(14) ?
C12 C11 C1 122.09(15) ?
C16 C11 C1 119.12(15) ?
C13 C12 C11 121.53(15) ?
C13 C12 Cl1 118.30(13) ?
C11 C12 Cl1 120.16(12) ?
C14 C13 C12 118.21(16) ?
C14 C13 H13 120.9 ?
C12 C13 H13 120.9 ?
C15 C14 C13 122.06(16) ?
C15 C14 Cl2 120.07(14) ?
C13 C14 Cl2 117.87(14) ?
C14 C15 C16 118.62(16) ?
C14 C15 H15 120.7 ?
C16 C15 H15 120.7 ?
C15 C16 C11 120.78(16) ?
C15 C16 H16 119.6 ?
C11 C16 H16 119.6 ?
C22 C21 C26 120.34(14) ?
C22 C21 N2 122.65(15) ?
C26 C21 N2 116.84(15) ?
C21 C22 C23 119.10(15) ?
C21 C22 H22 120.5 ?
C23 C22 H22 120.5 ?
C24 C23 C22 120.72(15) ?
C24 C23 Cl3 120.53(12) ?
C22 C23 Cl3 118.74(13) ?
C25 C24 C23 119.68(15) ?
C25 C24 Cl4 119.21(13) ?
C23 C24 Cl4 121.07(13) ?
C26 C25 C24 120.21(16) ?
C26 C25 H25 119.9 ?
C24 C25 H25 119.9 ?
C25 C26 C21 119.91(16) ?
C25 C26 H26 120.0 ?
C21 C26 H26 120.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C2 1.6815(16) y
Cl1 C12 1.7385(16) ?
Cl2 C14 1.7412(17) ?
Cl3 C23 1.7383(17) ?
Cl4 C24 1.7403(16) ?
C1 O1 1.225(2) y
C1 N1 1.379(2) y
C1 C11 1.508(2) ?
N1 C2 1.398(2) y
N1 H1 0.80(2) ?
C2 N2 1.345(2) y
N2 C21 1.429(2) ?
N2 H2 0.79(2) ?
C11 C12 1.395(2) ?
C11 C16 1.398(2) ?
C12 C13 1.390(2) ?
C13 C14 1.389(3) ?
C13 H13 0.9500 ?
C14 C15 1.387(3) ?
C15 C16 1.396(2) ?
C15 H15 0.9500 ?
C16 H16 0.9500 ?
C21 C22 1.396(2) ?
C21 C26 1.399(2) ?
C22 C23 1.398(2) ?
C22 H22 0.9500 ?
C23 C24 1.394(2) ?
C24 C25 1.392(3) ?
C25 C26 1.391(2) ?
C25 H25 0.9500 ?
C26 H26 0.9500 ?
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
N1 H1 S1 3_666 0.80(2) 2.72(2) 3.4910(14) 162(2)
N2 H2 O1 . 0.79(2) 1.99(2) 2.6681(19) 143(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
O1 C1 N1 C2 -4.0(3)
C11 C1 N1 C2 173.73(15)
C1 N1 C2 N2 6.1(2)
C1 N1 C2 S1 -172.09(14)
N1 C2 N2 C21 -179.06(16)
S1 C2 N2 C21 -1.0(3)
O1 C1 C11 C12 -105.6(2)
N1 C1 C11 C12 76.6(2)
O1 C1 C11 C16 71.6(2)
N1 C1 C11 C16 -106.29(18)
C16 C11 C12 C13 2.0(2)
C1 C11 C12 C13 179.10(15)
C16 C11 C12 Cl1 -176.54(13)
C1 C11 C12 Cl1 0.6(2)
C11 C12 C13 C14 0.3(2)
Cl1 C12 C13 C14 178.84(14)
C12 C13 C14 C15 -2.2(3)
C12 C13 C14 Cl2 178.37(13)
C13 C14 C15 C16 1.7(3)
Cl2 C14 C15 C16 -178.87(15)
C14 C15 C16 C11 0.7(3)
C12 C11 C16 C15 -2.5(3)
C1 C11 C16 C15 -179.69(16)
C2 N2 C21 C22 -43.7(3)
C2 N2 C21 C26 141.01(18)
C26 C21 C22 C23 0.7(2)
N2 C21 C22 C23 -174.50(15)
C21 C22 C23 C24 1.1(2)
C21 C22 C23 Cl3 179.95(13)
C22 C23 C24 C25 -2.5(3)
Cl3 C23 C24 C25 178.69(14)
C22 C23 C24 Cl4 175.44(13)
Cl3 C23 C24 Cl4 -3.4(2)
C23 C24 C25 C26 2.1(3)
Cl4 C24 C25 C26 -175.87(14)
C24 C25 C26 C21 -0.3(3)
C22 C21 C26 C25 -1.1(3)
N2 C21 C26 C25 174.39(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 875098
