#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/08/2220896.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_2220896
loop_
_publ_author_name
'Khawar Rauf, M.'
'Bolte, Michael'
'Badshah, Amin'
_publ_section_title
;
 1-(4-Chlorophenyl)-3-(2,4-dichlorobenzoyl)thiourea
;
_journal_coeditor_code           RK2121
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o260
_journal_paper_doi               10.1107/S160053680900004X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H9 Cl3 N2 O S'
_chemical_formula_moiety         'C14 H9 Cl3 N2 O S'
_chemical_formula_sum            'C14 H9 Cl3 N2 O S'
_chemical_formula_weight         359.65
_chemical_name_systematic
;
1-(4-Chlorophenyl)-3-(2,4-dichlorobenzoyl)thiourea
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                92.919(6)
_cell_angle_beta                 98.005(7)
_cell_angle_gamma                101.330(8)
_cell_formula_units_Z            2
_cell_length_a                   5.9674(6)
_cell_length_b                   9.6577(9)
_cell_length_c                   13.9585(13)
_cell_measurement_reflns_used    8758
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.1
_cell_measurement_theta_min      3.7
_cell_volume                     778.54(13)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2001)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Stoe IPDS II 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  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10758
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.09
_diffrn_reflns_theta_min         3.52
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.720
_exptl_absorpt_correction_T_max  0.7970
_exptl_absorpt_correction_T_min  0.7764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(MULABS; Spek, 2003; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.298
_refine_ls_extinction_coef       0.032(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3418
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0288
_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)+(0.0411P)²+0.3093P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0760
_refine_ls_wR_factor_ref         0.0778
_reflns_number_gt                3154
_reflns_number_total             3418
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rk2121.cif
_cod_data_source_block           I
_cod_database_code               2220896
_cod_database_fobs_code          2220896
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_disorder_assembly
_atom_site_disorder_group
S S1 0.67492(6) 0.98619(3) 0.38939(2) 0.02427(11) Uani d . 1 . .
Cl Cl1 1.21954(7) 0.58845(5) 0.63698(3) 0.03934(12) Uani d . 1 . .
Cl Cl2 1.28238(9) 0.84274(6) 0.99473(3) 0.05304(15) Uani d . 1 . .
Cl Cl3 -0.25621(7) 0.63336(6) 0.06553(3) 0.04618(14) Uani d . 1 . .
O O1 0.69489(18) 0.58953(10) 0.55419(8) 0.0271(2) Uani d . 1 . .
N N1 0.7744(2) 0.82647(12) 0.53113(8) 0.0217(2) Uani d . 1 . .
H H1 0.870(3) 0.901(2) 0.5518(14) 0.031(5) Uiso d . 1 . .
N N2 0.48353(19) 0.71427(12) 0.40789(8) 0.0214(2) Uani d . 1 . .
H H2 0.488(3) 0.644(2) 0.4369(15) 0.036(5) Uiso d . 1 . .
C C1 0.7879(2) 0.71114(13) 0.58426(10) 0.0198(2) Uani d . 1 . .
C C2 0.6359(2) 0.83297(13) 0.44250(9) 0.0194(2) Uani d . 1 . .
C C11 0.9208(2) 0.74977(13) 0.68462(10) 0.0211(3) Uani d . 1 . .
C C12 1.1140(2) 0.69336(14) 0.71709(11) 0.0253(3) Uani d . 1 . .
C C13 1.2283(3) 0.72390(16) 0.81191(11) 0.0319(3) Uani d . 1 . .
H H13 1.3614 0.6870 0.8331 0.038 Uiso calc R 1 . .
C C14 1.1437(3) 0.80951(17) 0.87478(11) 0.0332(3) Uani d . 1 . .
C C15 0.9539(3) 0.86812(18) 0.84524(12) 0.0357(3) Uani d . 1 . .
H H15 0.8995 0.9269 0.8895 0.043 Uiso calc R 1 . .
C C16 0.8441(3) 0.83931(16) 0.74932(11) 0.0294(3) Uani d . 1 . .
H H16 0.7162 0.8808 0.7277 0.035 Uiso calc R 1 . .
C C21 0.3125(2) 0.70259(13) 0.32315(9) 0.0202(3) Uani d . 1 . .
C C22 0.1340(2) 0.77684(15) 0.32197(11) 0.0266(3) Uani d . 1 . .
H H22 0.1311 0.8405 0.3757 0.032 Uiso calc R 1 . .
C C23 -0.0402(2) 0.75754(16) 0.24188(11) 0.0290(3) Uani d . 1 . .
H H23 -0.1616 0.8083 0.2401 0.035 Uiso calc R 1 . .
C C24 -0.0327(2) 0.66248(16) 0.16468(10) 0.0274(3) Uani d . 1 . .
C C25 0.1444(3) 0.58874(16) 0.16452(10) 0.0288(3) Uani d . 1 . .
H H25 0.1471 0.5253 0.1106 0.035 Uiso calc R 1 . .
C C26 0.3185(2) 0.60921(14) 0.24475(10) 0.0246(3) Uani d . 1 . .
H H26 0.4411 0.5594 0.2459 0.030 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C2 . . 128.79(11) ?
C1 N1 H1 . . 115.9(13) ?
C2 N1 H1 . . 115.1(13) ?
C2 N2 C21 . . 124.59(11) ?
C2 N2 H2 . . 117.6(14) ?
C21 N2 H2 . . 117.8(14) ?
O1 C1 N1 . . 123.60(12) ?
O1 C1 C11 . . 122.92(12) ?
N1 C1 C11 . . 113.44(11) ?
N2 C2 N1 . . 115.97(11) ?
N2 C2 S1 . . 125.98(10) ?
N1 C2 S1 . . 118.06(9) ?
C12 C11 C16 . . 118.82(13) ?
C12 C11 C1 . . 121.64(12) ?
C16 C11 C1 . . 119.48(12) ?
C13 C12 C11 . . 121.15(14) ?
C13 C12 Cl1 . . 119.15(11) ?
C11 C12 Cl1 . . 119.66(11) ?
C14 C13 C12 . . 118.49(14) ?
C14 C13 H13 . . 120.8 ?
C12 C13 H13 . . 120.8 ?
C15 C14 C13 . . 122.07(14) ?
C15 C14 Cl2 . . 119.67(13) ?
C13 C14 Cl2 . . 118.26(12) ?
C14 C15 C16 . . 118.83(15) ?
C14 C15 H15 . . 120.6 ?
C16 C15 H15 . . 120.6 ?
C15 C16 C11 . . 120.59(14) ?
C15 C16 H16 . . 119.7 ?
C11 C16 H16 . . 119.7 ?
C26 C21 C22 . . 120.47(12) ?
C26 C21 N2 . . 119.04(12) ?
C22 C21 N2 . . 120.35(12) ?
C23 C22 C21 . . 119.97(13) ?
C23 C22 H22 . . 120.0 ?
C21 C22 H22 . . 120.0 ?
C24 C23 C22 . . 118.73(13) ?
C24 C23 H23 . . 120.6 ?
C22 C23 H23 . . 120.6 ?
C25 C24 C23 . . 121.94(13) ?
C25 C24 Cl3 . . 119.11(11) ?
C23 C24 Cl3 . . 118.95(11) ?
C24 C25 C26 . . 118.95(13) ?
C24 C25 H25 . . 120.5 ?
C26 C25 H25 . . 120.5 ?
C21 C26 C25 . . 119.93(13) ?
C21 C26 H26 . . 120.0 ?
C25 C26 H26 . . 120.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C2 . 1.6786(13) ?
Cl1 C12 . 1.7336(15) ?
Cl2 C14 . 1.7454(16) ?
Cl3 C24 . 1.7529(14) ?
O1 C1 . 1.2217(16) ?
N1 C1 . 1.3784(16) ?
N1 C2 . 1.4003(17) ?
N1 H1 . 0.84(2) ?
N2 C2 . 1.3365(17) ?
N2 C21 . 1.4348(16) ?
N2 H2 . 0.81(2) ?
C1 C11 . 1.5004(18) ?
C11 C12 . 1.3993(19) ?
C11 C16 . 1.401(2) ?
C12 C13 . 1.391(2) ?
C13 C14 . 1.387(2) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.385(2) ?
C15 C16 . 1.395(2) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C21 C26 . 1.3912(19) ?
C21 C22 . 1.3947(19) ?
C22 C23 . 1.394(2) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.391(2) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.385(2) ?
C25 C26 . 1.395(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 2_776 0.84(2) 2.71(2) 3.4273(12) 144.3(16)
N2 H2 O1 . 0.81(2) 2.06(2) 2.7098(16) 136.4(19)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 O1 . . . . 9.0(2) ?
C2 N1 C1 C11 . . . . -168.72(12) ?
C21 N2 C2 N1 . . . . 174.17(12) ?
C21 N2 C2 S1 . . . . -6.02(19) ?
C1 N1 C2 N2 . . . . 5.5(2) ?
C1 N1 C2 S1 . . . . -174.29(11) ?
O1 C1 C11 C12 . . . . 59.43(18) ?
N1 C1 C11 C12 . . . . -122.82(13) ?
O1 C1 C11 C16 . . . . -117.54(15) ?
N1 C1 C11 C16 . . . . 60.22(16) ?
C16 C11 C12 C13 . . . . 0.5(2) ?
C1 C11 C12 C13 . . . . -176.50(12) ?
C16 C11 C12 Cl1 . . . . -177.26(11) ?
C1 C11 C12 Cl1 . . . . 5.75(17) ?
C11 C12 C13 C14 . . . . 1.4(2) ?
Cl1 C12 C13 C14 . . . . 179.14(11) ?
C12 C13 C14 C15 . . . . -1.8(2) ?
C12 C13 C14 Cl2 . . . . 177.96(11) ?
C13 C14 C15 C16 . . . . 0.3(2) ?
Cl2 C14 C15 C16 . . . . -179.43(12) ?
C14 C15 C16 C11 . . . . 1.6(2) ?
C12 C11 C16 C15 . . . . -2.0(2) ?
C1 C11 C16 C15 . . . . 175.05(13) ?
C2 N2 C21 C26 . . . . 118.68(15) ?
C2 N2 C21 C22 . . . . -65.50(18) ?
C26 C21 C22 C23 . . . . 0.1(2) ?
N2 C21 C22 C23 . . . . -175.68(13) ?
C21 C22 C23 C24 . . . . 0.7(2) ?
C22 C23 C24 C25 . . . . -1.1(2) ?
C22 C23 C24 Cl3 . . . . 177.91(11) ?
C23 C24 C25 C26 . . . . 0.8(2) ?
Cl3 C24 C25 C26 . . . . -178.21(11) ?
C22 C21 C26 C25 . . . . -0.4(2) ?
N2 C21 C26 C25 . . . . 175.42(12) ?
C24 C25 C26 C21 . . . . -0.1(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 856612
