#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/06/2220692.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_2220692
loop_
_publ_author_name
'Binzet, Gün'
'Flörke, Ulrich'
'Külcü, Nevzat'
'Arslan, Hakan'
_publ_section_title
;
 N-(Diphenylcarbamothioyl)-3-methylbenzamide
;
_journal_coeditor_code           AT2712
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o378
_journal_page_last               o379
_journal_paper_doi               10.1107/S1600536809002554
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C21 H18 N2 O S'
_chemical_formula_moiety         'C21 H18 N2 O S'
_chemical_formula_sum            'C21 H18 N2 O S'
_chemical_formula_weight         346.43
_chemical_name_systematic
;
N-(Diphenylcarbamothioyl)-3-methylbenzamide
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.6928(12)
_cell_length_b                   16.7647(17)
_cell_length_c                   19.865(2)
_cell_measurement_reflns_used    801
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.90
_cell_measurement_theta_min      2.49
_cell_volume                     3561.0(6)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0984
_diffrn_reflns_av_sigmaI/netI    0.0696
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            29957
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         2.05
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  430
_diffrn_standards_number         2203
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_correction_T_min  0.9253
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.377
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4241
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.947
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0471
_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)+(0.0429P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.1012
_reflns_number_gt                2955
_reflns_number_total             4241
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2712.cif
_cod_data_source_block           I
_cod_database_code               2220692
_cod_database_fobs_code          2220692
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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 0.49155(4) 0.96594(3) 0.60687(2) 0.02357(13) Uani d . 1 . .
O O1 0.83581(11) 0.88560(8) 0.53805(6) 0.0282(3) Uani d . 1 . .
N N1 0.63123(14) 0.90441(8) 0.50788(7) 0.0194(3) Uani d D 1 . .
H H1 0.5892(15) 0.9383(8) 0.4811(7) 0.029(5) Uiso d D 1 . .
N N2 0.61147(13) 0.82693(8) 0.60385(7) 0.0198(3) Uani d . 1 . .
C C1 0.75893(17) 0.89869(10) 0.49441(8) 0.0204(4) Uani d . 1 . .
C C2 0.79282(16) 0.91117(10) 0.42236(8) 0.0201(4) Uani d . 1 . .
C C3 0.90683(17) 0.94747(10) 0.40766(9) 0.0226(4) Uani d . 1 . .
H H3A 0.9603 0.9633 0.4434 0.027 Uiso calc R 1 . .
C C4 0.94370(18) 0.96101(10) 0.34132(9) 0.0252(4) Uani d . 1 . .
C C5 1.0663(2) 1.00079(12) 0.32634(10) 0.0360(5) Uani d . 1 . .
H H5A 1.1349 0.9638 0.3362 0.054 Uiso calc R 1 . .
H H5B 1.0750 1.0486 0.3543 0.054 Uiso calc R 1 . .
H H5C 1.0692 1.0159 0.2787 0.054 Uiso calc R 1 . .
C C6 0.86364(18) 0.93615(11) 0.29006(9) 0.0283(4) Uani d . 1 . .
H H6A 0.8863 0.9456 0.2445 0.034 Uiso calc R 1 . .
C C7 0.75192(18) 0.89805(11) 0.30421(8) 0.0280(4) Uani d . 1 . .
H H7A 0.7001 0.8801 0.2685 0.034 Uiso calc R 1 . .
C C8 0.71531(17) 0.88605(10) 0.37039(9) 0.0237(4) Uani d . 1 . .
H H8A 0.6378 0.8608 0.3801 0.028 Uiso calc R 1 . .
C C9 0.58249(16) 0.89564(10) 0.57267(8) 0.0190(4) Uani d . 1 . .
C C10 0.65779(16) 0.75696(10) 0.56929(8) 0.0200(4) Uani d . 1 . .
C C11 0.58848(18) 0.72236(10) 0.51815(8) 0.0241(4) Uani d . 1 . .
H H11A 0.5118 0.7455 0.5040 0.029 Uiso calc R 1 . .
C C12 0.63308(19) 0.65307(10) 0.48777(9) 0.0307(5) Uani d . 1 . .
H H12A 0.5872 0.6291 0.4522 0.037 Uiso calc R 1 . .
C C13 0.7437(2) 0.61921(11) 0.50926(10) 0.0346(5) Uani d . 1 . .
H H13A 0.7741 0.5723 0.4881 0.042 Uiso calc R 1 . .
C C14 0.81025(19) 0.65320(11) 0.56141(11) 0.0360(5) Uani d . 1 . .
H H14A 0.8852 0.6289 0.5768 0.043 Uiso calc R 1 . .
C C15 0.76792(18) 0.72271(11) 0.59126(9) 0.0287(4) Uani d . 1 . .
H H15A 0.8143 0.7467 0.6267 0.034 Uiso calc R 1 . .
C C16 0.59063(16) 0.81692(10) 0.67524(8) 0.0191(4) Uani d . 1 . .
C C17 0.50108(18) 0.76351(11) 0.69656(9) 0.0285(4) Uani d . 1 . .
H H17A 0.4504 0.7359 0.6649 0.034 Uiso calc R 1 . .
C C18 0.4862(2) 0.75071(12) 0.76492(9) 0.0371(5) Uani d . 1 . .
H H18A 0.4246 0.7143 0.7803 0.045 Uiso calc R 1 . .
C C19 0.5600(2) 0.79033(11) 0.81074(9) 0.0342(5) Uani d . 1 . .
H H19A 0.5486 0.7814 0.8576 0.041 Uiso calc R 1 . .
C C20 0.65082(19) 0.84305(12) 0.78887(9) 0.0317(5) Uani d . 1 . .
H H20A 0.7026 0.8697 0.8206 0.038 Uiso calc R 1 . .
C C21 0.66613(18) 0.85692(11) 0.72048(9) 0.0258(4) Uani d . 1 . .
H H21A 0.7277 0.8934 0.7050 0.031 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'
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 C9 . . 122.34(14) ?
C1 N1 H1 . . 114.8(12) ?
C9 N1 H1 . . 115.1(12) ?
C9 N2 C16 . . 121.07(14) ?
C9 N2 C10 . . 123.73(14) ?
C16 N2 C10 . . 115.11(13) ?
O1 C1 N1 . . 122.56(16) ?
O1 C1 C2 . . 123.08(16) ?
N1 C1 C2 . . 114.35(15) ?
C8 C2 C3 . . 119.91(16) ?
C8 C2 C1 . . 121.72(16) ?
C3 C2 C1 . . 118.36(16) ?
C2 C3 C4 . . 121.10(17) ?
C2 C3 H3A . . 119.5 ?
C4 C3 H3A . . 119.5 ?
C6 C4 C3 . . 117.92(17) ?
C6 C4 C5 . . 121.64(17) ?
C3 C4 C5 . . 120.44(17) ?
C4 C5 H5A . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C4 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C7 C6 C4 . . 121.31(17) ?
C7 C6 H6A . . 119.3 ?
C4 C6 H6A . . 119.3 ?
C6 C7 C8 . . 120.24(17) ?
C6 C7 H7A . . 119.9 ?
C8 C7 H7A . . 119.9 ?
C7 C8 C2 . . 119.48(17) ?
C7 C8 H8A . . 120.3 ?
C2 C8 H8A . . 120.3 ?
N2 C9 N1 . . 115.40(15) ?
N2 C9 S1 . . 123.43(13) ?
N1 C9 S1 . . 121.15(12) ?
C15 C10 C11 . . 120.93(16) ?
C15 C10 N2 . . 118.63(15) ?
C11 C10 N2 . . 120.30(15) ?
C10 C11 C12 . . 118.94(18) ?
C10 C11 H11A . . 120.5 ?
C12 C11 H11A . . 120.5 ?
C13 C12 C11 . . 120.17(18) ?
C13 C12 H12A . . 119.9 ?
C11 C12 H12A . . 119.9 ?
C12 C13 C14 . . 120.30(18) ?
C12 C13 H13A . . 119.9 ?
C14 C13 H13A . . 119.9 ?
C13 C14 C15 . . 120.05(19) ?
C13 C14 H14A . . 120.0 ?
C15 C14 H14A . . 120.0 ?
C10 C15 C14 . . 119.59(18) ?
C10 C15 H15A . . 120.2 ?
C14 C15 H15A . . 120.2 ?
C17 C16 C21 . . 121.43(16) ?
C17 C16 N2 . . 118.97(15) ?
C21 C16 N2 . . 119.46(16) ?
C16 C17 C18 . . 118.82(18) ?
C16 C17 H17A . . 120.6 ?
C18 C17 H17A . . 120.6 ?
C19 C18 C17 . . 120.57(18) ?
C19 C18 H18A . . 119.7 ?
C17 C18 H18A . . 119.7 ?
C18 C19 C20 . . 120.24(17) ?
C18 C19 H19A . . 119.9 ?
C20 C19 H19A . . 119.9 ?
C19 C20 C21 . . 119.82(18) ?
C19 C20 H20A . . 120.1 ?
C21 C20 H20A . . 120.1 ?
C16 C21 C20 . . 119.11(18) ?
C16 C21 H21A . . 120.4 ?
C20 C21 H21A . . 120.4 ?
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 C9 . 1.6721(17) ?
O1 C1 . 1.215(2) ?
N1 C1 . 1.395(2) ?
N1 C9 . 1.396(2) ?
N1 H1 . 0.899(14) ?
N2 C9 . 1.344(2) ?
N2 C16 . 1.445(2) ?
N2 C10 . 1.447(2) ?
C1 C2 . 1.491(2) ?
C2 C8 . 1.389(2) ?
C2 C3 . 1.393(2) ?
C3 C4 . 1.394(2) ?
C3 H3A . 0.9500 ?
C4 C6 . 1.394(3) ?
C4 C5 . 1.501(3) ?
C5 H5A . 0.9800 ?
C5 H5B . 0.9800 ?
C5 H5C . 0.9800 ?
C6 C7 . 1.383(3) ?
C6 H6A . 0.9500 ?
C7 C8 . 1.386(2) ?
C7 H7A . 0.9500 ?
C8 H8A . 0.9500 ?
C10 C15 . 1.381(2) ?
C10 C11 . 1.385(2) ?
C11 C12 . 1.393(2) ?
C11 H11A . 0.9500 ?
C12 C13 . 1.379(3) ?
C12 H12A . 0.9500 ?
C13 C14 . 1.380(3) ?
C13 H13A . 0.9500 ?
C14 C15 . 1.384(3) ?
C14 H14A . 0.9500 ?
C15 H15A . 0.9500 ?
C16 C17 . 1.378(2) ?
C16 C21 . 1.382(2) ?
C17 C18 . 1.384(2) ?
C17 H17A . 0.9500 ?
C18 C19 . 1.375(3) ?
C18 H18A . 0.9500 ?
C19 C20 . 1.383(3) ?
C19 H19A . 0.9500 ?
C20 C21 . 1.388(2) ?
C20 H20A . 0.9500 ?
C21 H21A . 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 5_676 0.899(14) 2.525(14) 3.4123(15) 169.3(13)
C5 H5B O1 5_776 0.98 2.59 3.461(2) 148
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
C9 N1 C1 O1 . . . . 0.1(2) ?
C9 N1 C1 C2 . . . . -179.01(15) ?
O1 C1 C2 C8 . . . . 146.21(18) ?
N1 C1 C2 C8 . . . . -34.7(2) ?
O1 C1 C2 C3 . . . . -32.3(2) ?
N1 C1 C2 C3 . . . . 146.80(15) ?
C8 C2 C3 C4 . . . . 1.6(3) ?
C1 C2 C3 C4 . . . . -179.81(15) ?
C2 C3 C4 C6 . . . . -0.8(3) ?
C2 C3 C4 C5 . . . . 179.50(16) ?
C3 C4 C6 C7 . . . . -1.0(3) ?
C5 C4 C6 C7 . . . . 178.66(17) ?
C4 C6 C7 C8 . . . . 2.1(3) ?
C6 C7 C8 C2 . . . . -1.2(3) ?
C3 C2 C8 C7 . . . . -0.6(3) ?
C1 C2 C8 C7 . . . . -179.09(16) ?
C16 N2 C9 N1 . . . . 166.64(14) ?
C10 N2 C9 N1 . . . . -17.1(2) ?
C16 N2 C9 S1 . . . . -14.9(2) ?
C10 N2 C9 S1 . . . . 161.33(13) ?
C1 N1 C9 N2 . . . . -56.1(2) ?
C1 N1 C9 S1 . . . . 125.41(15) ?
C9 N2 C10 C15 . . . . 126.34(18) ?
C16 N2 C10 C15 . . . . -57.2(2) ?
C9 N2 C10 C11 . . . . -57.8(2) ?
C16 N2 C10 C11 . . . . 118.63(17) ?
C15 C10 C11 C12 . . . . -1.6(3) ?
N2 C10 C11 C12 . . . . -177.31(15) ?
C10 C11 C12 C13 . . . . 0.9(3) ?
C11 C12 C13 C14 . . . . 0.7(3) ?
C12 C13 C14 C15 . . . . -1.7(3) ?
C11 C10 C15 C14 . . . . 0.6(3) ?
N2 C10 C15 C14 . . . . 176.38(16) ?
C13 C14 C15 C10 . . . . 1.1(3) ?
C9 N2 C16 C17 . . . . 112.65(19) ?
C10 N2 C16 C17 . . . . -63.9(2) ?
C9 N2 C16 C21 . . . . -71.6(2) ?
C10 N2 C16 C21 . . . . 111.85(18) ?
C21 C16 C17 C18 . . . . 0.7(3) ?
N2 C16 C17 C18 . . . . 176.37(16) ?
C16 C17 C18 C19 . . . . -0.3(3) ?
C17 C18 C19 C20 . . . . -0.5(3) ?
C18 C19 C20 C21 . . . . 1.0(3) ?
C17 C16 C21 C20 . . . . -0.2(3) ?
N2 C16 C21 C20 . . . . -175.88(16) ?
C19 C20 C21 C16 . . . . -0.6(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741631
