#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/04/2210448.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_2210448
loop_
_publ_author_name
'Sabino, Jose R.'
'Silvio Cunha'
'Rodrigo M. Bastos'
'Vencato, Ivo'
_publ_section_title
;
 N-(Benzylaminothiocarbonyl)benzamide
;
_journal_coeditor_code           XU2109
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3918
_journal_page_last               o3920
_journal_paper_doi               10.1107/S1600536806031928
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C15 H14 N2 O S'
_chemical_formula_moiety         'C15 H14 N2 O S'
_chemical_formula_sum            'C15 H14 N2 O S'
_chemical_formula_weight         270.35
_chemical_melting_point          .397E-305
_chemical_name_systematic
;
N-(Benzylaminothiocarbonyl)benzamide
;
_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'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 124.40(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   30.560(7)
_cell_length_b                   6.112(2)
_cell_length_c                   17.364(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      46.6
_cell_measurement_theta_min      14.8
_cell_volume                     2676.1(14)
_computing_cell_refinement       CAD-4-PC
_computing_data_collection       'CAD-4-PC (Enraf--Nonius, 1993)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       'non-profiled ω/2θ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2569
_diffrn_reflns_theta_full        67.9
_diffrn_reflns_theta_max         67.9
_diffrn_reflns_theta_min         3.5
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    2.086
_exptl_absorpt_correction_T_max  0.7300
_exptl_absorpt_correction_T_min  0.5182
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.59
_refine_diff_density_min         -0.38
_refine_ls_extinction_coef       0.0045(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2439
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.151
_refine_ls_R_factor_gt           0.052
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1204P)²+2.5013P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.199
_reflns_number_gt                2125
_reflns_number_total             2439
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2109.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2210448
_cod_database_fobs_code          2210448
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
N N1 0.08960(9) 0.9770(4) 0.05564(16) 0.0494(6) Uani d . 1
H H1 0.0752 1.0836 0.0167 0.059 Uiso calc R 1
C C2 0.06464(10) 0.7880(5) 0.03078(17) 0.0420(6) Uani d . 1
N N3 0.01820(8) 0.7737(4) -0.05851(15) 0.0477(6) Uani d . 1
H H3 0.0012 0.6519 -0.0725 0.057 Uiso calc R 1
C C4 -0.00367(11) 0.9316(5) -0.12683(19) 0.0473(7) Uani d . 1
S S5 0.08431(3) 0.56316(12) 0.09774(5) 0.0559(3) Uani d . 1
O O6 0.01307(9) 1.1177(4) -0.11381(15) 0.0632(6) Uani d . 1
C C7 -0.04922(10) 0.8561(5) -0.22074(18) 0.0472(7) Uani d . 1
C C8 -0.05384(12) 0.6455(6) -0.2528(2) 0.0548(7) Uani d . 1
H H8 -0.0301 0.5386 -0.2129 0.066 Uiso calc R 1
C C9 -0.09361(15) 0.5921(7) -0.3441(2) 0.0706(10) Uani d . 1
H H9 -0.0959 0.4513 -0.3664 0.085 Uiso calc R 1
C C10 -0.12985(14) 0.7500(7) -0.4017(2) 0.0729(10) Uani d . 1
H H10 -0.1566 0.7153 -0.4631 0.088 Uiso calc R 1
C C11 -0.12686(15) 0.9558(8) -0.3694(2) 0.0757(11) Uani d . 1
H H11 -0.1523 1.059 -0.4082 0.091 Uiso calc R 1
C C12 -0.08610(12) 1.0132(6) -0.2791(2) 0.0588(8) Uani d . 1
H H12 -0.0835 1.1554 -0.2578 0.071 Uiso calc R 1
C C13 0.13974(10) 1.0191(5) 0.14400(18) 0.0484(7) Uani d . 1
H H13A 0.1471 0.9004 0.1868 0.058 Uiso calc R 1
H H13B 0.1367 1.1528 0.1708 0.058 Uiso calc R 1
C C14 0.18548(10) 1.0409(5) 0.13401(17) 0.0447(6) Uani d . 1
C C15 0.22077(11) 0.8693(6) 0.1590(2) 0.0558(7) Uani d . 1
H H15 0.2159 0.7383 0.1805 0.067 Uiso calc R 1
C C16 0.26362(13) 0.8943(7) 0.1518(2) 0.0696(10) Uani d . 1
H H16 0.2873 0.7794 0.1682 0.083 Uiso calc R 1
C C17 0.27098(13) 1.0864(7) 0.1208(2) 0.0708(10) Uani d . 1
H H17 0.2998 1.1018 0.1164 0.085 Uiso calc R 1
C C18 0.23634(13) 1.2574(6) 0.0959(2) 0.0638(9) Uani d . 1
H H18 0.2416 1.3878 0.0746 0.077 Uiso calc R 1
C C19 0.19353(12) 1.2345(5) 0.1026(2) 0.0522(7) Uani d . 1
H H19 0.17 1.3502 0.0858 0.063 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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-3 1 5
-15 -1 2
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
C2 N1 C13 124.9(2) yes
C2 N1 H1 117.6 ?
C13 N1 H1 117.6 ?
N1 C2 N3 117.2(2) yes
N1 C2 S5 125.3(2) yes
N3 C2 S5 117.5(2) yes
C4 N3 C2 127.6(2) yes
C4 N3 H3 116.2 ?
C2 N3 H3 116.2 ?
O6 C4 N3 123.3(3) yes
O6 C4 C7 121.7(3) ?
N3 C4 C7 115.0(2) ?
C8 C7 C12 119.7(3) ?
C8 C7 C4 123.2(3) ?
C12 C7 C4 116.9(3) ?
C7 C8 C9 120.4(3) ?
C7 C8 H8 119.8 ?
C9 C8 H8 119.8 ?
C10 C9 C8 119.3(4) ?
C10 C9 H9 120.3 ?
C8 C9 H9 120.3 ?
C11 C10 C9 120.6(3) ?
C11 C10 H10 119.7 ?
C9 C10 H10 119.7 ?
C10 C11 C12 120.5(4) ?
C10 C11 H11 119.7 ?
C12 C11 H11 119.7 ?
C7 C12 C11 119.3(4) ?
C7 C12 H12 120.3 ?
C11 C12 H12 120.3 ?
N1 C13 C14 112.8(2) ?
N1 C13 H13A 109 ?
C14 C13 H13A 109 ?
N1 C13 H13B 109 ?
C14 C13 H13B 109 ?
H13A C13 H13B 107.8 ?
C19 C14 C15 119.4(3) ?
C19 C14 C13 120.3(3) ?
C15 C14 C13 120.3(3) ?
C14 C15 C16 119.5(3) ?
C14 C15 H15 120.2 ?
C16 C15 H15 120.2 ?
C17 C16 C15 120.3(3) ?
C17 C16 H16 119.9 ?
C15 C16 H16 119.9 ?
C16 C17 C18 120.7(3) ?
C16 C17 H17 119.7 ?
C18 C17 H17 119.7 ?
C17 C18 C19 119.6(3) ?
C17 C18 H18 120.2 ?
C19 C18 H18 120.2 ?
C14 C19 C18 120.5(3) ?
C14 C19 H19 119.8 ?
C18 C19 H19 119.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 1.316(4) yes
N1 C13 1.453(3) yes
N1 H1 0.86 ?
C2 N3 1.393(3) yes
C2 S5 1.677(3) yes
N3 C4 1.375(4) yes
N3 H3 0.86 ?
C4 O6 1.215(4) yes
C4 C7 1.498(4) yes
C7 C8 1.377(5) ?
C7 C12 1.388(4) ?
C8 C9 1.386(5) ?
C8 H8 0.93 ?
C9 C10 1.381(6) ?
C9 H9 0.93 ?
C10 C11 1.359(6) ?
C10 H10 0.93 ?
C11 C12 1.388(5) ?
C11 H11 0.93 ?
C12 H12 0.93 ?
C13 C14 1.509(4) ?
C13 H13A 0.97 ?
C13 H13B 0.97 ?
C14 C19 1.382(4) ?
C14 C15 1.386(4) ?
C15 C16 1.393(5) ?
C15 H15 0.93 ?
C16 C17 1.362(6) ?
C16 H16 0.93 ?
C17 C18 1.372(5) ?
C17 H17 0.93 ?
C18 C19 1.385(4) ?
C18 H18 0.93 ?
C19 H19 0.93 ?
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
_geom_hbond_publ_flag
N1 H1 O6 . 0.86 1.98 2.663(3) 136 yes
N3 H3 S5 5_565 0.86 2.73 3.479(2) 146 yes
C13 H13A S5 . 0.97 2.64 3.121(3) 111 yes
C13 H13B S5 1_565 0.97 2.86 3.610(3) 135 yes
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
C13 N1 C2 N3 -176.9(2) ?
C13 N1 C2 S5 2.9(4) yes
N1 C2 N3 C4 3.8(4) yes
S5 C2 N3 C4 -176.0(2) yes
C2 N3 C4 O6 -7.4(4) ?
C2 N3 C4 C7 170.8(2) ?
O6 C4 C7 C8 147.2(3) ?
N3 C4 C7 C8 -31.0(4) yes
O6 C4 C7 C12 -28.4(4) yes
N3 C4 C7 C12 153.3(2) ?
C12 C7 C8 C9 3.0(4) ?
C4 C7 C8 C9 -172.6(3) ?
C7 C8 C9 C10 -2.5(5) ?
C8 C9 C10 C11 -0.2(6) ?
C9 C10 C11 C12 2.5(6) ?
C8 C7 C12 C11 -0.7(4) ?
C4 C7 C12 C11 175.1(3) ?
C10 C11 C12 C7 -2.0(5) ?
C2 N1 C13 C14 107.0(3) yes
N1 C13 C14 C19 79.6(3) ?
N1 C13 C14 C15 -102.4(3) ?
C19 C14 C15 C16 -0.2(4) ?
C13 C14 C15 C16 -178.2(3) ?
C14 C15 C16 C17 0.3(5) ?
C15 C16 C17 C18 -0.3(6) ?
C16 C17 C18 C19 0.2(5) ?
C15 C14 C19 C18 0.1(4) ?
C13 C14 C19 C18 178.1(3) ?
C17 C18 C19 C14 -0.1(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 610909
