#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/86/2208664.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_2208664
loop_
_publ_author_name
'Rauf, M. Khawar'
'Badshah, Amin'
'Flörke, Ulrich'
'Saeed, Aamer'
_publ_section_title
;
 1-Benzoyl-3-(3,4-dichlorophenyl)thiourea
;
_journal_coeditor_code           LH2018
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1380
_journal_page_last               o1381
_journal_paper_doi               10.1107/S1600536806008336
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C14 H10 Cl2 N2 O S'
_chemical_formula_moiety         'C14 H10 Cl2 N2 O S'
_chemical_formula_sum            'C14 H10 Cl2 N2 O S'
_chemical_formula_weight         325.20
_chemical_name_common            1-Benzoyl-3-(3,4-dichlorophenyl)thiourea
_chemical_name_systematic
;
1-Benzoyl-3-(3,4-dichlorophenyl)thiourea
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.326(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.070(2)
_cell_length_b                   3.8928(4)
_cell_length_c                   28.137(3)
_cell_measurement_reflns_used    3197
_cell_measurement_temperature    120.0(10)
_cell_measurement_theta_max      27.95
_cell_measurement_theta_min      2.90
_cell_volume                     2741.3(5)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2002)'
_diffrn_ambient_temperature      120.0(10)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            11673
_diffrn_reflns_theta_full        28.07
_diffrn_reflns_theta_max         28.07
_diffrn_reflns_theta_min         1.45
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.621
_exptl_absorpt_correction_T_max  0.9816
_exptl_absorpt_correction_T_min  0.7633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.240
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3320
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0479P)²+2.0546P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0967
_reflns_number_gt                2845
_reflns_number_total             3320
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2018.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      'C 2/c'
_cod_database_code               2208664
_cod_database_fobs_code          2208664
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
Cl Cl1 0.131153(19) 0.77466(14) 0.207743(17) 0.02684(14) Uani d . 1
Cl Cl2 0.245001(18) 1.11187(13) 0.197975(17) 0.02482(13) Uani d . 1
S S1 0.036317(17) 0.27044(12) 0.055105(16) 0.01846(12) Uani d . 1
O O1 0.16030(5) 0.3097(4) -0.05548(5) 0.0287(4) Uani d . 1
N N1 0.13156(6) 0.4968(4) 0.02837(5) 0.0179(3) Uani d . 1
H H1A 0.1516 0.5140 0.0038 0.022 Uiso calc R 1
N N2 0.07732(6) 0.2223(4) -0.02852(5) 0.0172(3) Uani d . 1
H H2B 0.0453 0.1425 -0.0369 0.021 Uiso calc R 1
C C1 0.15474(7) 0.6402(5) 0.07055(6) 0.0166(4) Uani d . 1
C C2 0.13238(7) 0.6377(5) 0.11461(6) 0.0172(4) Uani d . 1
H H2A 0.0983 0.5375 0.1180 0.021 Uiso calc R 1
C C3 0.16034(7) 0.7828(5) 0.15351(7) 0.0177(4) Uani d . 1
C C4 0.21010(7) 0.9316(5) 0.14943(6) 0.0179(4) Uani d . 1
C C5 0.23212(7) 0.9372(5) 0.10543(7) 0.0197(4) Uani d . 1
H H5A 0.2660 1.0403 0.1021 0.024 Uiso calc R 1
C C6 0.20483(7) 0.7931(5) 0.06653(7) 0.0196(4) Uani d . 1
H H6A 0.2202 0.7975 0.0365 0.024 Uiso calc R 1
C C7 0.08462(7) 0.3388(5) 0.01841(6) 0.0155(4) Uani d . 1
C C8 0.11363(7) 0.2162(5) -0.06332(7) 0.0186(4) Uani d . 1
C C9 0.09422(7) 0.0860(5) -0.11079(6) 0.0168(4) Uani d . 1
C C10 0.13174(7) -0.0570(5) -0.13970(7) 0.0207(4) Uani d . 1
H H10A 0.1682 -0.0707 -0.1286 0.025 Uiso calc R 1
C C11 0.11608(8) -0.1785(5) -0.18444(7) 0.0232(4) Uani d . 1
H H11A 0.1416 -0.2781 -0.2039 0.028 Uiso calc R 1
C C12 0.06281(8) -0.1549(5) -0.20093(7) 0.0236(4) Uani d . 1
H H12A 0.0520 -0.2402 -0.2316 0.028 Uiso calc R 1
C C13 0.02560(8) -0.0076(5) -0.17277(7) 0.0230(4) Uani d . 1
H H13A -0.0107 0.0093 -0.1843 0.028 Uiso calc R 1
C C14 0.04111(7) 0.1153(5) -0.12785(7) 0.0192(4) Uani d . 1
H H14A 0.0156 0.2193 -0.1087 0.023 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'
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'
Cl Cl 0.1484 0.1585 '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
C7 N1 C1 132.23(15) y
C7 N1 H1A 113.9 ?
C1 N1 H1A 113.9 ?
C8 N2 C7 128.49(15) y
C8 N2 H2B 115.8 ?
C7 N2 H2B 115.8 ?
C2 C1 C6 119.01(17) ?
C2 C1 N1 125.57(16) ?
C6 C1 N1 115.42(16) ?
C3 C2 C1 119.35(16) ?
C3 C2 H2A 120.3 ?
C1 C2 H2A 120.3 ?
C2 C3 C4 121.43(17) ?
C2 C3 Cl1 117.96(14) ?
C4 C3 Cl1 120.62(15) ?
C5 C4 C3 119.20(17) ?
C5 C4 Cl2 119.39(14) ?
C3 C4 Cl2 121.41(14) ?
C6 C5 C4 119.95(17) ?
C6 C5 H5A 120.0 ?
C4 C5 H5A 120.0 ?
C5 C6 C1 121.06(17) ?
C5 C6 H6A 119.5 ?
C1 C6 H6A 119.5 ?
N1 C7 N2 114.26(15) y
N1 C7 S1 127.33(14) ?
N2 C7 S1 118.42(13) ?
O1 C8 N2 121.86(17) ?
O1 C8 C9 121.34(16) ?
N2 C8 C9 116.79(16) y
C14 C9 C10 119.68(17) ?
C14 C9 C8 122.60(16) ?
C10 C9 C8 117.66(16) ?
C11 C10 C9 120.20(17) ?
C11 C10 H10A 119.9 ?
C9 C10 H10A 119.9 ?
C10 C11 C12 119.88(18) ?
C10 C11 H11A 120.1 ?
C12 C11 H11A 120.1 ?
C13 C12 C11 120.18(18) ?
C13 C12 H12A 119.9 ?
C11 C12 H12A 119.9 ?
C12 C13 C14 120.19(18) ?
C12 C13 H13A 119.9 ?
C14 C13 H13A 119.9 ?
C13 C14 C9 119.84(17) ?
C13 C14 H14A 120.1 ?
C9 C14 H14A 120.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C3 1.7304(19) y
Cl2 C4 1.7277(18) y
S1 C7 1.6579(17) y
O1 C8 1.233(2) y
N1 C7 1.343(2) y
N1 C1 1.406(2) y
N1 H1A 0.8800 ?
N2 C8 1.375(2) y
N2 C7 1.398(2) y
N2 H2B 0.8800 ?
C1 C2 1.390(2) ?
C1 C6 1.400(2) ?
C2 C3 1.385(3) ?
C2 H2A 0.9500 ?
C3 C4 1.386(3) ?
C4 C5 1.385(3) ?
C5 C6 1.376(3) ?
C5 H5A 0.9500 ?
C6 H6A 0.9500 ?
C8 C9 1.484(3) ?
C9 C14 1.394(3) ?
C9 C10 1.395(2) ?
C10 C11 1.380(3) ?
C10 H10A 0.9500 ?
C11 C12 1.391(3) ?
C11 H11A 0.9500 ?
C12 C13 1.383(3) ?
C12 H12A 0.9500 ?
C13 C14 1.386(3) ?
C13 H13A 0.9500 ?
C14 H14A 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 H1A O1 . 0.88 1.87 2.610(2) 140
N2 H2B S1 5 0.88 2.63 3.4798(16) 163
C5 H5A O1 7_565 0.95 2.40 3.265(2) 152
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_publ_flag
C7 N1 C1 C2 2.2(3) ?
C7 N1 C1 C6 -178.47(19) y
C6 C1 C2 C3 -0.7(3) ?
N1 C1 C2 C3 178.61(17) ?
C1 C2 C3 C4 0.2(3) ?
C1 C2 C3 Cl1 179.98(14) ?
C2 C3 C4 C5 0.4(3) ?
Cl1 C3 C4 C5 -179.33(15) ?
C2 C3 C4 Cl2 -179.88(14) ?
Cl1 C3 C4 Cl2 0.4(2) ?
C3 C4 C5 C6 -0.6(3) ?
Cl2 C4 C5 C6 179.71(15) ?
C4 C5 C6 C1 0.1(3) ?
C2 C1 C6 C5 0.5(3) ?
N1 C1 C6 C5 -178.84(17) ?
C1 N1 C7 N2 -178.10(18) ?
C1 N1 C7 S1 1.8(3) ?
C8 N2 C7 N1 7.7(3) ?
C8 N2 C7 S1 -172.20(16) ?
C7 N2 C8 O1 2.6(3) ?
C7 N2 C8 C9 -178.36(17) ?
O1 C8 C9 C14 -152.0(2) ?
N2 C8 C9 C14 29.0(3) ?
O1 C8 C9 C10 25.2(3) ?
N2 C8 C9 C10 -153.84(18) y
C14 C9 C10 C11 -2.0(3) ?
C8 C9 C10 C11 -179.23(18) ?
C9 C10 C11 C12 0.7(3) ?
C10 C11 C12 C13 0.5(3) ?
C11 C12 C13 C14 -0.4(3) ?
C12 C13 C14 C9 -0.9(3) ?
C10 C9 C14 C13 2.1(3) ?
C8 C9 C14 C13 179.17(18) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 604164
