#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/04/2220490.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_2220490
loop_
_publ_author_name
'Khawar Rauf, M.'
'Bolte, Michael'
'Badshah, Amin'
_publ_section_title
;
 1-(2,6-Dichlorobenzoyl)-3-(3,5-dichlorophenyl)thiourea
;
_journal_coeditor_code           FL2225
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o177
_journal_paper_doi               10.1107/S1600536808042736
_journal_volume                  65
_journal_year                    2009
_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_systematic
;
1-(2,6-Dichlorobenzoyl)-3-(3,5-dichlorophenyl)thiourea
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 97.250(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.7737(13)
_cell_length_b                   10.3744(6)
_cell_length_c                   10.6935(11)
_cell_measurement_reflns_used    13230
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.8
_cell_measurement_theta_min      3.8
_cell_volume                     1625.9(2)
_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 0.995
_diffrn_measured_fraction_theta_max 0.993
_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  0.0457
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12823
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         3.73
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.857
_exptl_absorpt_correction_T_max  0.8406
_exptl_absorpt_correction_T_min  0.7149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(MULABS; Spek, 2003; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.361
_refine_ls_extinction_coef       0.0246(15)
_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   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3724
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0317
_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)+(0.0525P)²+0.486P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0867
_reflns_number_gt                3306
_reflns_number_total             3724
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl2225.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2220490
_cod_database_fobs_code          2220490
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.35875(3) 0.16745(4) 0.09234(4) 0.02939(13) Uani d . 1 . .
Cl Cl2 0.39163(3) 0.58457(4) 0.39696(4) 0.02796(12) Uani d . 1 . .
Cl Cl3 0.93189(3) 0.14605(4) 0.52460(4) 0.03065(13) Uani d . 1 . .
Cl Cl4 0.97033(3) 0.59117(4) 0.27286(4) 0.02639(12) Uani d . 1 . .
C C1 0.46669(10) 0.35599(15) 0.26849(14) 0.0171(3) Uani d . 1 . .
O O1 0.50255(7) 0.29825(13) 0.36158(11) 0.0257(3) Uani d . 1 . .
N N1 0.51344(8) 0.40910(14) 0.17722(13) 0.0185(3) Uani d . 1 . .
H H1 0.4844(15) 0.443(2) 0.115(2) 0.028(5) Uiso d . 1 . .
S S1 0.64669(2) 0.48065(5) 0.04928(4) 0.02559(13) Uani d . 1 . .
C C2 0.60770(10) 0.41647(15) 0.17586(15) 0.0168(3) Uani d . 1 . .
N N2 0.65773(8) 0.36848(14) 0.27949(13) 0.0178(3) Uani d . 1 . .
H H2 0.6248(15) 0.327(2) 0.333(2) 0.033(6) Uiso d . 1 . .
C C11 0.36443(10) 0.37608(15) 0.24447(14) 0.0170(3) Uani d . 1 . .
C C12 0.30851(10) 0.29239(16) 0.16745(15) 0.0196(3) Uani d . 1 . .
C C13 0.21408(11) 0.30756(19) 0.14814(18) 0.0265(4) Uani d . 1 . .
H H13 0.1771 0.2506 0.0941 0.032 Uiso calc R 1 . .
C C14 0.17491(11) 0.40754(19) 0.2093(2) 0.0300(4) Uani d . 1 . .
H H14 0.1105 0.4177 0.1978 0.036 Uiso calc R 1 . .
C C15 0.22860(12) 0.49305(18) 0.28705(18) 0.0270(4) Uani d . 1 . .
H H15 0.2014 0.5610 0.3288 0.032 Uiso calc R 1 . .
C C16 0.32308(10) 0.47701(16) 0.30247(15) 0.0195(3) Uani d . 1 . .
C C21 0.75373(10) 0.37152(16) 0.31296(14) 0.0170(3) Uani d . 1 . .
C C22 0.79148(10) 0.27196(16) 0.39134(15) 0.0196(3) Uani d . 1 . .
H H22 0.7539 0.2054 0.4175 0.024 Uiso calc R 1 . .
C C23 0.88510(10) 0.27226(16) 0.43034(15) 0.0208(3) Uani d . 1 . .
C C24 0.94227(10) 0.36829(17) 0.39447(15) 0.0217(3) Uani d . 1 . .
H H24 1.0062 0.3666 0.4205 0.026 Uiso calc R 1 . .
C C25 0.90178(10) 0.46720(16) 0.31857(15) 0.0189(3) Uani d . 1 . .
C C26 0.80870(10) 0.47105(16) 0.27637(15) 0.0184(3) Uani d . 1 . .
H H26 0.7832 0.5394 0.2242 0.022 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
O1 C1 N1 . . 124.54(14) ?
O1 C1 C11 . . 121.70(13) ?
N1 C1 C11 . . 113.75(13) ?
C1 N1 C2 . . 128.18(14) ?
C1 N1 H1 . . 118.9(15) ?
C2 N1 H1 . . 112.9(15) ?
N2 C2 N1 . . 114.54(13) ?
N2 C2 S1 . . 127.07(11) ?
N1 C2 S1 . . 118.38(11) ?
C2 N2 C21 . . 128.79(13) ?
C2 N2 H2 . . 114.5(15) ?
C21 N2 H2 . . 116.7(15) ?
C12 C11 C16 . . 118.01(13) ?
C12 C11 C1 . . 121.24(14) ?
C16 C11 C1 . . 120.72(14) ?
C13 C12 C11 . . 121.66(15) ?
C13 C12 Cl1 . . 119.56(13) ?
C11 C12 Cl1 . . 118.78(11) ?
C14 C13 C12 . . 118.88(16) ?
C14 C13 H13 . . 120.6 ?
C12 C13 H13 . . 120.6 ?
C13 C14 C15 . . 121.08(15) ?
C13 C14 H14 . . 119.5 ?
C15 C14 H14 . . 119.5 ?
C14 C15 C16 . . 118.71(16) ?
C14 C15 H15 . . 120.6 ?
C16 C15 H15 . . 120.6 ?
C15 C16 C11 . . 121.63(15) ?
C15 C16 Cl2 . . 119.48(13) ?
C11 C16 Cl2 . . 118.89(12) ?
C26 C21 C22 . . 120.66(14) ?
C26 C21 N2 . . 122.87(14) ?
C22 C21 N2 . . 116.38(14) ?
C23 C22 C21 . . 118.86(15) ?
C23 C22 H22 . . 120.6 ?
C21 C22 H22 . . 120.6 ?
C24 C23 C22 . . 122.24(15) ?
C24 C23 Cl3 . . 119.19(12) ?
C22 C23 Cl3 . . 118.57(13) ?
C23 C24 C25 . . 117.16(14) ?
C23 C24 H24 . . 121.4 ?
C25 C24 H24 . . 121.4 ?
C26 C25 C24 . . 122.87(15) ?
C26 C25 Cl4 . . 118.19(13) ?
C24 C25 Cl4 . . 118.93(12) ?
C25 C26 C21 . . 118.19(14) ?
C25 C26 H26 . . 120.9 ?
C21 C26 H26 . . 120.9 ?
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
Cl1 C12 . 1.7397(17) ?
Cl2 C16 . 1.7417(17) ?
Cl3 C23 . 1.7414(17) ?
Cl4 C25 . 1.7445(16) ?
C1 O1 . 1.224(2) ?
C1 N1 . 1.3796(19) ?
C1 C11 . 1.5146(19) ?
N1 C2 . 1.3967(18) ?
N1 H1 . 0.82(2) ?
S1 C2 . 1.6745(16) ?
C2 N2 . 1.347(2) ?
N2 C21 . 1.4186(18) ?
N2 H2 . 0.91(2) ?
C11 C12 . 1.394(2) ?
C11 C16 . 1.396(2) ?
C12 C13 . 1.393(2) ?
C13 C14 . 1.390(3) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.393(3) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.395(2) ?
C15 H15 . 0.9500 ?
C21 C26 . 1.400(2) ?
C21 C22 . 1.401(2) ?
C22 C23 . 1.393(2) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.391(2) ?
C24 C25 . 1.395(2) ?
C24 H24 . 0.9500 ?
C25 C26 . 1.393(2) ?
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
N2 H2 O1 . 0.91(2) 1.89(2) 2.6581(17) 141(2)
N1 H1 S1 3_665 0.82(2) 2.57(2) 3.3653(14) 163(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 N1 C2 . . . . -4.9(3) ?
C11 C1 N1 C2 . . . . 174.63(15) ?
C1 N1 C2 N2 . . . . -2.2(2) ?
C1 N1 C2 S1 . . . . 177.27(14) ?
N1 C2 N2 C21 . . . . -173.75(15) ?
S1 C2 N2 C21 . . . . 6.9(3) ?
O1 C1 C11 C12 . . . . -95.3(2) ?
N1 C1 C11 C12 . . . . 85.17(19) ?
O1 C1 C11 C16 . . . . 82.6(2) ?
N1 C1 C11 C16 . . . . -96.94(18) ?
C16 C11 C12 C13 . . . . -0.1(2) ?
C1 C11 C12 C13 . . . . 177.83(15) ?
C16 C11 C12 Cl1 . . . . 179.03(12) ?
C1 C11 C12 Cl1 . . . . -3.0(2) ?
C11 C12 C13 C14 . . . . -1.1(3) ?
Cl1 C12 C13 C14 . . . . 179.72(14) ?
C12 C13 C14 C15 . . . . 1.1(3) ?
C13 C14 C15 C16 . . . . 0.2(3) ?
C14 C15 C16 C11 . . . . -1.5(3) ?
C14 C15 C16 Cl2 . . . . 178.83(14) ?
C12 C11 C16 C15 . . . . 1.5(2) ?
C1 C11 C16 C15 . . . . -176.47(15) ?
C12 C11 C16 Cl2 . . . . -178.89(12) ?
C1 C11 C16 Cl2 . . . . 3.2(2) ?
C2 N2 C21 C26 . . . . 30.3(3) ?
C2 N2 C21 C22 . . . . -152.93(16) ?
C26 C21 C22 C23 . . . . -1.2(2) ?
N2 C21 C22 C23 . . . . -178.08(14) ?
C21 C22 C23 C24 . . . . 0.2(2) ?
C21 C22 C23 Cl3 . . . . -178.45(12) ?
C22 C23 C24 C25 . . . . 1.1(2) ?
Cl3 C23 C24 C25 . . . . 179.77(12) ?
C23 C24 C25 C26 . . . . -1.5(2) ?
C23 C24 C25 Cl4 . . . . 179.11(12) ?
C24 C25 C26 C21 . . . . 0.5(2) ?
Cl4 C25 C26 C21 . . . . 179.94(12) ?
C22 C21 C26 C25 . . . . 0.9(2) ?
N2 C21 C26 C25 . . . . 177.49(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741437
