#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/07/2220711.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_2220711
loop_
_publ_author_name
'Binzet, Gün'
'Flörke, Ulrich'
'Külcü, Nevzat'
'Arslan, Hakan'
_publ_section_title
;
 3-Chloro-N-(diphenylcarbamothioyl)benzamide
;
_journal_coeditor_code           BQ2121
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o351
_journal_page_last               o352
_journal_paper_doi               10.1107/S1600536809001639
_journal_volume                  65
_journal_year                    2009
_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
;
3-Chloro-N-(diphenylcarbamothioyl)benzamide
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                72.565(10)
_cell_angle_beta                 70.495(10)
_cell_angle_gamma                71.303(10)
_cell_formula_units_Z            2
_cell_length_a                   8.196(5)
_cell_length_b                   10.357(6)
_cell_length_c                   11.699(6)
_cell_measurement_reflns_used    710
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.49
_cell_measurement_theta_min      2.96
_cell_volume                     865.8(9)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker SMART APEX'
_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  0.0802
_diffrn_reflns_av_sigmaI/netI    0.1041
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5401
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.13
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  430
_diffrn_standards_number         1420
_exptl_absorpt_coefficient_mu    0.351
_exptl_absorpt_correction_T_max  0.9657
_exptl_absorpt_correction_T_min  0.8467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.308
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3490
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.1078
_refine_ls_R_factor_gt           0.0614
_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)+(0.0629P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1460
_reflns_number_gt                2290
_reflns_number_total             3490
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bq2121.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 
;
_cod_database_code               2220711
_cod_database_fobs_code          2220711
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
Cl Cl1 0.51239(14) -0.17055(10) 0.41549(10) 0.0406(3) Uani d . 1 . .
S S1 0.36004(12) 0.69686(9) 0.05276(9) 0.0269(2) Uani d . 1 . .
O O1 0.2248(3) 0.3782(2) 0.3535(2) 0.0276(6) Uani d . 1 . .
N N1 0.2744(4) 0.4535(3) 0.1434(3) 0.0213(6) Uani d D 1 . .
H H1 0.364(3) 0.430(3) 0.078(2) 0.020(9) Uiso d D 1 . .
N N2 0.0613(3) 0.6406(3) 0.2112(3) 0.0210(6) Uani d . 1 . .
C C1 0.2248(4) 0.5945(3) 0.1413(3) 0.0210(7) Uani d . 1 . .
C C2 0.0059(4) 0.7766(4) 0.2405(3) 0.0226(7) Uani d . 1 . .
C C3 -0.0764(5) 0.8908(4) 0.1661(4) 0.0330(9) Uani d . 1 . .
H H3A -0.0918 0.8827 0.0917 0.040 Uiso calc R 1 . .
C C4 -0.1364(5) 1.0175(4) 0.2006(5) 0.0464(11) Uani d . 1 . .
H H4A -0.1930 1.0975 0.1494 0.056 Uiso calc R 1 . .
C C5 -0.1154(6) 1.0291(5) 0.3079(5) 0.0506(12) Uani d . 1 . .
H H5A -0.1565 1.1169 0.3309 0.061 Uiso calc R 1 . .
C C6 -0.0344(6) 0.9132(5) 0.3825(4) 0.0442(11) Uani d . 1 . .
H H6A -0.0227 0.9205 0.4582 0.053 Uiso calc R 1 . .
C C7 0.0294(5) 0.7869(4) 0.3478(3) 0.0322(9) Uani d . 1 . .
H H7A 0.0893 0.7075 0.3977 0.039 Uiso calc R 1 . .
C C8 -0.0738(4) 0.5643(3) 0.2509(3) 0.0205(7) Uani d . 1 . .
C C9 -0.1246(5) 0.5352(4) 0.1618(3) 0.0288(8) Uani d . 1 . .
H H9A -0.0697 0.5650 0.0763 0.035 Uiso calc R 1 . .
C C10 -0.2535(5) 0.4636(4) 0.1963(4) 0.0361(9) Uani d . 1 . .
H H10A -0.2869 0.4425 0.1349 0.043 Uiso calc R 1 . .
C C11 -0.3350(5) 0.4219(4) 0.3204(4) 0.0337(9) Uani d . 1 . .
H H11A -0.4245 0.3720 0.3447 0.040 Uiso calc R 1 . .
C C12 -0.2857(5) 0.4530(4) 0.4097(3) 0.0291(8) Uani d . 1 . .
H H12A -0.3416 0.4243 0.4952 0.035 Uiso calc R 1 . .
C C13 -0.1559(4) 0.5254(4) 0.3744(3) 0.0249(8) Uani d . 1 . .
H H13A -0.1235 0.5483 0.4353 0.030 Uiso calc R 1 . .
C C14 0.2666(4) 0.3508(4) 0.2519(3) 0.0220(7) Uani d . 1 . .
C C15 0.3130(4) 0.2074(3) 0.2337(3) 0.0213(7) Uani d . 1 . .
C C16 0.3799(4) 0.0992(3) 0.3218(3) 0.0235(8) Uani d . 1 . .
H H16A 0.3953 0.1180 0.3917 0.028 Uiso calc R 1 . .
C C17 0.4235(5) -0.0348(4) 0.3077(3) 0.0279(8) Uani d . 1 . .
C C18 0.3970(5) -0.0663(4) 0.2097(3) 0.0299(9) Uani d . 1 . .
H H18A 0.4264 -0.1604 0.2021 0.036 Uiso calc R 1 . .
C C19 0.3273(5) 0.0413(4) 0.1234(3) 0.0314(9) Uani d . 1 . .
H H19A 0.3074 0.0213 0.0557 0.038 Uiso calc R 1 . .
C C20 0.2864(5) 0.1766(4) 0.1339(3) 0.0266(8) Uani d . 1 . .
H H20A 0.2397 0.2501 0.0731 0.032 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C14 . . 123.6(3) ?
C1 N1 H1 . . 114(2) ?
C14 N1 H1 . . 115(2) ?
C1 N2 C8 . . 122.0(3) ?
C1 N2 C2 . . 121.4(3) ?
C8 N2 C2 . . 116.3(3) ?
N2 C1 N1 . . 115.3(3) ?
N2 C1 S1 . . 123.8(3) ?
N1 C1 S1 . . 120.9(3) ?
C3 C2 C7 . . 121.0(3) ?
C3 C2 N2 . . 120.6(3) ?
C7 C2 N2 . . 118.3(3) ?
C2 C3 C4 . . 119.0(4) ?
C2 C3 H3A . . 120.5 ?
C4 C3 H3A . . 120.5 ?
C5 C4 C3 . . 120.6(4) ?
C5 C4 H4A . . 119.7 ?
C3 C4 H4A . . 119.7 ?
C4 C5 C6 . . 119.8(4) ?
C4 C5 H5A . . 120.1 ?
C6 C5 H5A . . 120.1 ?
C7 C6 C5 . . 120.2(4) ?
C7 C6 H6A . . 119.9 ?
C5 C6 H6A . . 119.9 ?
C2 C7 C6 . . 119.3(4) ?
C2 C7 H7A . . 120.3 ?
C6 C7 H7A . . 120.3 ?
C13 C8 C9 . . 120.3(3) ?
C13 C8 N2 . . 120.9(3) ?
C9 C8 N2 . . 118.7(3) ?
C10 C9 C8 . . 120.2(3) ?
C10 C9 H9A . . 119.9 ?
C8 C9 H9A . . 119.9 ?
C9 C10 C11 . . 119.9(3) ?
C9 C10 H10A . . 120.0 ?
C11 C10 H10A . . 120.0 ?
C10 C11 C12 . . 119.8(3) ?
C10 C11 H11A . . 120.1 ?
C12 C11 H11A . . 120.1 ?
C13 C12 C11 . . 120.1(3) ?
C13 C12 H12A . . 120.0 ?
C11 C12 H12A . . 120.0 ?
C8 C13 C12 . . 119.7(3) ?
C8 C13 H13A . . 120.2 ?
C12 C13 H13A . . 120.2 ?
O1 C14 N1 . . 122.1(3) ?
O1 C14 C15 . . 123.2(3) ?
N1 C14 C15 . . 114.7(3) ?
C16 C15 C20 . . 119.1(3) ?
C16 C15 C14 . . 118.1(3) ?
C20 C15 C14 . . 122.7(3) ?
C17 C16 C15 . . 119.5(3) ?
C17 C16 H16A . . 120.3 ?
C15 C16 H16A . . 120.3 ?
C16 C17 C18 . . 121.8(3) ?
C16 C17 Cl1 . . 119.8(3) ?
C18 C17 Cl1 . . 118.4(3) ?
C19 C18 C17 . . 118.6(3) ?
C19 C18 H18A . . 120.7 ?
C17 C18 H18A . . 120.7 ?
C20 C19 C18 . . 120.7(3) ?
C20 C19 H19A . . 119.7 ?
C18 C19 H19A . . 119.7 ?
C19 C20 C15 . . 120.3(3) ?
C19 C20 H20A . . 119.9 ?
C15 C20 H20A . . 119.9 ?
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 C17 . 1.730(4) ?
S1 C1 . 1.659(3) ?
O1 C14 . 1.216(4) ?
N1 C1 . 1.380(4) ?
N1 C14 . 1.388(4) ?
N1 H1 . 0.894(10) ?
N2 C1 . 1.336(4) ?
N2 C8 . 1.437(4) ?
N2 C2 . 1.442(4) ?
C2 C3 . 1.369(5) ?
C2 C7 . 1.372(5) ?
C3 C4 . 1.378(5) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.367(6) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.375(6) ?
C5 H5A . 0.9500 ?
C6 C7 . 1.374(5) ?
C6 H6A . 0.9500 ?
C7 H7A . 0.9500 ?
C8 C13 . 1.370(5) ?
C8 C9 . 1.382(4) ?
C9 C10 . 1.366(5) ?
C9 H9A . 0.9500 ?
C10 C11 . 1.379(5) ?
C10 H10A . 0.9500 ?
C11 C12 . 1.387(5) ?
C11 H11A . 0.9500 ?
C12 C13 . 1.378(5) ?
C12 H12A . 0.9500 ?
C13 H13A . 0.9500 ?
C14 C15 . 1.473(5) ?
C15 C16 . 1.382(5) ?
C15 C20 . 1.395(4) ?
C16 C17 . 1.364(5) ?
C16 H16A . 0.9500 ?
C17 C18 . 1.380(5) ?
C18 C19 . 1.375(5) ?
C18 H18A . 0.9500 ?
C19 C20 . 1.367(5) ?
C19 H19A . 0.9500 ?
C20 H20A . 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_665 0.90(2) 2.48(3) 3.351(4) 162(2)
C13 H13A O1 2_566 0.95 2.59 3.434(5) 148
C18 H18A S1 1_545 0.95 2.87 3.609(5) 136
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
C8 N2 C1 N1 . . . . -20.3(4) ?
C2 N2 C1 N1 . . . . 166.0(3) ?
C8 N2 C1 S1 . . . . 157.6(2) ?
C2 N2 C1 S1 . . . . -16.2(4) ?
C14 N1 C1 N2 . . . . -53.3(4) ?
C14 N1 C1 S1 . . . . 128.9(3) ?
C1 N2 C2 C3 . . . . 91.3(4) ?
C8 N2 C2 C3 . . . . -82.8(4) ?
C1 N2 C2 C7 . . . . -92.0(4) ?
C8 N2 C2 C7 . . . . 93.9(4) ?
C7 C2 C3 C4 . . . . -0.2(5) ?
N2 C2 C3 C4 . . . . 176.4(3) ?
C2 C3 C4 C5 . . . . -0.4(6) ?
C3 C4 C5 C6 . . . . -0.4(6) ?
C4 C5 C6 C7 . . . . 1.8(6) ?
C3 C2 C7 C6 . . . . 1.5(5) ?
N2 C2 C7 C6 . . . . -175.1(3) ?
C5 C6 C7 C2 . . . . -2.3(6) ?
C1 N2 C8 C13 . . . . 123.8(4) ?
C2 N2 C8 C13 . . . . -62.2(4) ?
C1 N2 C8 C9 . . . . -58.6(4) ?
C2 N2 C8 C9 . . . . 115.4(4) ?
C13 C8 C9 C10 . . . . -2.0(5) ?
N2 C8 C9 C10 . . . . -179.6(3) ?
C8 C9 C10 C11 . . . . 0.9(6) ?
C9 C10 C11 C12 . . . . 0.1(6) ?
C10 C11 C12 C13 . . . . 0.0(6) ?
C9 C8 C13 C12 . . . . 2.1(5) ?
N2 C8 C13 C12 . . . . 179.6(3) ?
C11 C12 C13 C8 . . . . -1.1(5) ?
C1 N1 C14 O1 . . . . -4.4(5) ?
C1 N1 C14 C15 . . . . 175.7(3) ?
O1 C14 C15 C16 . . . . -26.1(5) ?
N1 C14 C15 C16 . . . . 153.8(3) ?
O1 C14 C15 C20 . . . . 151.6(3) ?
N1 C14 C15 C20 . . . . -28.4(4) ?
C20 C15 C16 C17 . . . . 2.0(5) ?
C14 C15 C16 C17 . . . . 179.8(3) ?
C15 C16 C17 C18 . . . . -2.3(5) ?
C15 C16 C17 Cl1 . . . . 178.4(2) ?
C16 C17 C18 C19 . . . . 1.1(5) ?
Cl1 C17 C18 C19 . . . . -179.7(3) ?
C17 C18 C19 C20 . . . . 0.5(5) ?
C18 C19 C20 C15 . . . . -0.8(5) ?
C16 C15 C20 C19 . . . . -0.5(5) ?
C14 C15 C20 C19 . . . . -178.2(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741595
