#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:09:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201973 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/20/2202079.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_2202079
loop_
_publ_author_name
'Arslan, Hakan'
'Flörke, Ulrich'
'Külcü, Nevzat'
_publ_section_title
;
 N'-(4-Chlorobenzoyl)-N,N-diphenylthiourea
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o641
_journal_page_last               o642
_journal_paper_doi               10.1107/S1600536803007992
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C20 H15 Cl N2 O S'
_chemical_formula_moiety         'C20 H15 Cl N2 O S'
_chemical_formula_sum            'C20 H15 Cl N2 O S'
_chemical_formula_weight         366.85
_chemical_name_systematic
;
N'-(4-Chlorobenzoyl)-N,N-diphenylthiourea
;
_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           SHELXL-97
_cell_angle_alpha                88.140(10)
_cell_angle_beta                 79.12(2)
_cell_angle_gamma                89.540(10)
_cell_formula_units_Z            2
_cell_length_a                   6.811(2)
_cell_length_b                   9.9500(10)
_cell_length_c                   13.442(2)
_cell_measurement_reflns_used    26
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.644
_cell_measurement_theta_min      7.464
_cell_volume                     894.1(3)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        'SHELXTL (Bruker, 1998)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker P4'
_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  0.0164
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5122
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.05
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 397
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.340
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_correction_T_min  0.811
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.247
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4095
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0411
_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)+(0.0433P)²+0.3889P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1216
_reflns_number_gt                2774
_reflns_number_total             4095
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            na6220.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               2202079
_cod_database_fobs_code          2202079
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_type_symbol
Cl1 0.67643(11) 0.47923(8) 0.88792(5) 0.0729(3) Uani d . 1 . . Cl
S1 0.25792(10) 1.13391(6) 0.47986(4) 0.04738(18) Uani d . 1 . . S
O1 0.0084(2) 0.89838(16) 0.73884(13) 0.0501(4) Uani d . 1 . . O
N1 0.2933(3) 0.98879(17) 0.64473(13) 0.0396(4) Uani d . 1 . . N
H1A 0.4201 0.9775 0.6261 0.047 Uiso calc R 1 . . H
N2 0.0871(3) 1.17658(17) 0.67074(12) 0.0390(4) Uani d . 1 . . N
C1 0.5091(3) 0.8203(2) 0.76573(16) 0.0426(5) Uani d . 1 . . C
H1B 0.5658 0.9035 0.7444 0.051 Uiso calc R 1 . . H
C2 0.6187(4) 0.7239(3) 0.80842(17) 0.0492(6) Uani d . 1 . . C
H2A 0.7488 0.7421 0.8159 0.059 Uiso calc R 1 . . H
C3 0.5335(4) 0.6012(2) 0.83954(16) 0.0466(5) Uani d . 1 . . C
C4 0.3408(4) 0.5725(2) 0.83064(18) 0.0506(6) Uani d . 1 . . C
H4A 0.2846 0.4894 0.8527 0.061 Uiso calc R 1 . . H
C5 0.2315(4) 0.6689(2) 0.78835(17) 0.0446(5) Uani d . 1 . . C
H5A 0.1007 0.6506 0.7823 0.054 Uiso calc R 1 . . H
C6 0.3154(3) 0.79303(19) 0.75479(15) 0.0362(4) Uani d . 1 . . C
C7 0.1890(3) 0.8953(2) 0.71348(15) 0.0381(5) Uani d . 1 . . C
C8 0.2062(3) 1.09956(19) 0.60398(15) 0.0371(5) Uani d . 1 . . C
C9 0.0873(4) 1.1734(2) 0.77834(15) 0.0418(5) Uani d . 1 . . C
C10 -0.0919(4) 1.1638(3) 0.84553(17) 0.0538(6) Uani d . 1 . . C
H10A -0.2108 1.1550 0.8218 0.065 Uiso calc R 1 . . H
C11 -0.0941(5) 1.1672(3) 0.94835(19) 0.0685(8) Uani d . 1 . . C
H11A -0.2151 1.1621 0.9939 0.082 Uiso calc R 1 . . H
C12 0.0813(6) 1.1782(3) 0.9839(2) 0.0734(9) Uani d . 1 . . C
H12A 0.0795 1.1780 1.0532 0.088 Uiso calc R 1 . . H
C13 0.2573(5) 1.1895(3) 0.9170(2) 0.0700(8) Uani d . 1 . . C
H13A 0.3756 1.1981 0.9412 0.084 Uiso calc R 1 . . H
C14 0.2638(4) 1.1884(2) 0.81301(18) 0.0529(6) Uani d . 1 . . C
H14A 0.3847 1.1975 0.7677 0.063 Uiso calc R 1 . . H
C15 -0.0397(3) 1.2783(2) 0.63622(14) 0.0373(5) Uani d . 1 . . C
C16 -0.2060(4) 1.2421(2) 0.60088(19) 0.0523(6) Uani d . 1 . . C
H16A -0.2337 1.1519 0.5937 0.063 Uiso calc R 1 . . H
C17 -0.3338(4) 1.3421(3) 0.5757(2) 0.0651(7) Uani d . 1 . . C
H17A -0.4482 1.3188 0.5520 0.078 Uiso calc R 1 . . H
C18 -0.2913(4) 1.4752(3) 0.5858(2) 0.0611(7) Uani d . 1 . . C
H18A -0.3779 1.5416 0.5697 0.073 Uiso calc R 1 . . H
C19 -0.1227(4) 1.5100(2) 0.61939(18) 0.0539(6) Uani d . 1 . . C
H19A -0.0934 1.6004 0.6248 0.065 Uiso calc R 1 . . H
C20 0.0053(4) 1.4121(2) 0.64556(16) 0.0449(5) Uani d . 1 . . C
H20A 0.1199 1.4359 0.6691 0.054 Uiso calc R 1 . . H
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 C8 124.4(2) y
C7 N1 H1A 117.8 ?
C8 N1 H1A 117.8 ?
C8 N2 C9 123.9(2) ?
C8 N2 C15 120.6(2) ?
C9 N2 C15 115.2(2) ?
C6 C1 C2 120.2(2) ?
C6 C1 H1B 119.9 ?
C2 C1 H1B 119.9 ?
C3 C2 C1 119.4(2) ?
C3 C2 H2A 120.3 ?
C1 C2 H2A 120.3 ?
C4 C3 C2 121.5(2) ?
C4 C3 Cl1 119.8(2) ?
C2 C3 Cl1 118.8(2) ?
C3 C4 C5 119.0(2) ?
C3 C4 H4A 120.5 ?
C5 C4 H4A 120.5 ?
C4 C5 C6 120.6(2) ?
C4 C5 H5A 119.7 ?
C6 C5 H5A 119.7 ?
C1 C6 C5 119.3(2) ?
C1 C6 C7 122.1(2) ?
C5 C6 C7 118.5(2) ?
O1 C7 N1 122.3(2) y
O1 C7 C6 122.7(2) y
N1 C7 C6 115.0(2) y
N2 C8 N1 116.1(2) y
N2 C8 S1 123.6(2) y
N1 C8 S1 120.3(2) y
C10 C9 C14 120.5(2) ?
C10 C9 N2 119.1(2) ?
C14 C9 N2 120.3(2) ?
C9 C10 C11 119.6(3) ?
C9 C10 H10A 120.2 ?
C11 C10 H10A 120.2 ?
C12 C11 C10 120.5(3) ?
C12 C11 H11A 119.8 ?
C10 C11 H11A 119.8 ?
C13 C12 C11 119.6(3) ?
C13 C12 H12A 120.2 ?
C11 C12 H12A 120.2 ?
C12 C13 C14 121.2(3) ?
C12 C13 H13A 119.4 ?
C14 C13 H13A 119.4 ?
C9 C14 C13 118.7(3) ?
C9 C14 H14A 120.7 ?
C13 C14 H14A 120.7 ?
C16 C15 C20 121.1(2) ?
C16 C15 N2 120.3(2) ?
C20 C15 N2 118.5(2) ?
C15 C16 C17 119.0(2) ?
C15 C16 H16A 120.5 ?
C17 C16 H16A 120.5 ?
C18 C17 C16 120.2(3) ?
C18 C17 H17A 119.9 ?
C16 C17 H17A 119.9 ?
C19 C18 C17 120.2(2) ?
C19 C18 H18A 119.9 ?
C17 C18 H18A 119.9 ?
C18 C19 C20 120.5(2) ?
C18 C19 H19A 119.8 ?
C20 C19 H19A 119.8 ?
C19 C20 C15 118.9(2) ?
C19 C20 H20A 120.5 ?
C15 C20 H20A 120.5 ?
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 C3 . 1.735(2) y
S1 C8 . 1.664(2) y
O1 C7 . 1.213(3) y
N1 C7 . 1.389(3) y
N1 C8 . 1.393(2) y
N1 H1A . 0.8600 ?
N2 C8 . 1.346(3) y
N2 C9 . 1.446(3) ?
N2 C15 . 1.447(2) ?
C1 C6 . 1.385(3) ?
C1 C2 . 1.386(3) ?
C1 H1B . 0.9300 ?
C2 C3 . 1.375(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.374(3) ?
C4 C5 . 1.382(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.390(3) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.489(3) ?
C9 C10 . 1.377(3) ?
C9 C14 . 1.380(3) ?
C10 C11 . 1.381(3) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.374(4) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.359(5) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.391(3) ?
C13 H13A . 0.9300 ?
C14 H14A . 0.9300 ?
C15 C16 . 1.364(3) ?
C15 C20 . 1.384(3) ?
C16 C17 . 1.391(3) ?
C16 H16A . 0.9300 ?
C17 C18 . 1.374(4) ?
C17 H17A . 0.9300 ?
C18 C19 . 1.362(4) ?
C18 H18A . 0.9300 ?
C19 C20 . 1.383(3) ?
C19 H19A . 0.9300 ?
C20 H20A . 0.9300 ?
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 0.1(3)
C1 C2 C3 C4 -1.0(4)
C1 C2 C3 Cl1 177.3(2)
C2 C3 C4 C5 0.7(4)
Cl1 C3 C4 C5 -177.5(2)
C3 C4 C5 C6 0.3(4)
C2 C1 C6 C5 0.9(3)
C2 C1 C6 C7 177.3(2)
C4 C5 C6 C1 -1.1(3)
C4 C5 C6 C7 -177.7(2)
C8 N1 C7 O1 4.9(3)
C8 N1 C7 C6 -174.1(2)
C1 C6 C7 O1 -149.4(2)
C5 C6 C7 O1 27.0(3)
C1 C6 C7 N1 29.6(3)
C5 C6 C7 N1 -153.9(2)
C9 N2 C8 N1 17.2(3)
C15 N2 C8 N1 -168.3(2)
C9 N2 C8 S1 -160.5(2)
C15 N2 C8 S1 14.0(3)
C7 N1 C8 N2 49.8(3)
C7 N1 C8 S1 -132.4(2)
C8 N2 C9 C10 -131.6(2)
C15 N2 C9 C10 53.6(3)
C8 N2 C9 C14 52.5(3)
C15 N2 C9 C14 -122.3(2)
C14 C9 C10 C11 -0.9(4)
N2 C9 C10 C11 -176.9(2)
C9 C10 C11 C12 -0.9(4)
C10 C11 C12 C13 1.8(5)
C11 C12 C13 C14 -0.8(5)
C10 C9 C14 C13 1.9(4)
N2 C9 C14 C13 177.8(2)
C12 C13 C14 C9 -1.0(4)
C8 N2 C15 C16 73.0(3)
C9 N2 C15 C16 -112.1(2)
C8 N2 C15 C20 -110.8(2)
C9 N2 C15 C20 64.2(3)
C20 C15 C16 C17 -1.2(4)
N2 C15 C16 C17 175.0(2)
C15 C16 C17 C18 0.4(4)
C16 C17 C18 C19 0.8(4)
C17 C18 C19 C20 -1.3(4)
C18 C19 C20 C15 0.6(3)
C16 C15 C20 C19 0.7(3)
N2 C15 C20 C19 -175.5(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21131777
