#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/03/2210302.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_2210302
loop_
_publ_author_name
'Zhang, Bin'
'Su, Bi-Quan'
'Xian, Liang'
_publ_section_title
;
 N-Benzoyl-N'-(2-methylphenyl)thiourea
;
_journal_coeditor_code           JH2028
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4024
_journal_page_last               o4026
_journal_paper_doi               10.1107/S1600536806032740
_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         270.34
_chemical_name_systematic
;
N-Benzoyl-N'-(2-methylphenyl)thiourea
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.216(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.6441(10)
_cell_length_b                   25.165(4)
_cell_length_c                   9.6851(17)
_cell_measurement_reflns_used    2356
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.65
_cell_measurement_theta_min      2.65
_cell_volume                     1375.6(4)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            7656
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.167
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2792
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0387
_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)+(0.0498P)²+0.1902P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.1091
_reflns_number_gt                1816
_reflns_number_total             2792
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jh2028.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2210302
_cod_database_fobs_code          2210302
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
S S1 0.64767(12) 0.44364(2) 0.63254(6) 0.0676(2) Uani d . 1
N N1 0.7095(3) 0.35643(6) 0.47815(17) 0.0486(4) Uani d . 1
H H1 0.657(4) 0.3397(8) 0.406(2) 0.059(6) Uiso d . 1
N N2 0.4401(3) 0.41790(6) 0.39893(16) 0.0483(4) Uani d . 1
H H2 0.388(4) 0.4499(8) 0.409(2) 0.053(6) Uiso d . 1
O O1 0.4452(3) 0.34613(5) 0.25749(15) 0.0696(5) Uani d . 1
C C1 0.6042(3) 0.40303(7) 0.49881(18) 0.0456(5) Uani d . 1
C C2 0.8678(3) 0.32847(7) 0.56687(18) 0.0460(5) Uani d . 1
C C3 0.8358(3) 0.27361(8) 0.57925(19) 0.0486(5) Uani d . 1
C C4 0.9884(4) 0.24641(9) 0.6661(2) 0.0675(6) Uani d . 1
H H4 0.9690 0.2100 0.6775 0.081 Uiso calc R 1
C C5 1.1671(5) 0.27173(12) 0.7357(2) 0.0791(8) Uani d . 1
H H5 1.2652 0.2526 0.7949 0.095 Uiso calc R 1
C C6 1.2022(4) 0.32515(12) 0.7187(2) 0.0747(7) Uani d . 1
H H6 1.3264 0.3421 0.7643 0.090 Uiso calc R 1
C C7 1.0531(4) 0.35382(9) 0.6338(2) 0.0592(6) Uani d . 1
H H7 1.0769 0.3901 0.6215 0.071 Uiso calc R 1
C C8 0.6458(4) 0.24438(8) 0.5012(2) 0.0626(6) Uani d . 1
H H8A 0.6338 0.2087 0.5358 0.094 Uiso calc R 1
H H8B 0.6851 0.2435 0.4049 0.094 Uiso calc R 1
H H8C 0.4970 0.2623 0.5131 0.094 Uiso calc R 1
C C9 0.3601(4) 0.38939(7) 0.28725(19) 0.0488(5) Uani d . 1
C C10 0.1637(3) 0.41274(7) 0.20478(19) 0.0468(5) Uani d . 1
C C11 0.0082(4) 0.45052(7) 0.2554(2) 0.0543(5) Uani d . 1
H H11 0.0268 0.4635 0.3447 0.065 Uiso calc R 1
C C12 -0.1745(4) 0.46888(9) 0.1731(2) 0.0645(6) Uani d . 1
H H12 -0.2772 0.4947 0.2068 0.077 Uiso calc R 1
C C13 -0.2056(4) 0.44941(9) 0.0421(3) 0.0697(6) Uani d . 1
H H13 -0.3302 0.4617 -0.0123 0.084 Uiso calc R 1
C C14 -0.0532(4) 0.41187(9) -0.0087(2) 0.0712(7) Uani d . 1
H H14 -0.0742 0.3987 -0.0976 0.085 Uiso calc R 1
C C15 0.1302(4) 0.39367(8) 0.0717(2) 0.0611(6) Uani d . 1
H H15 0.2333 0.3683 0.0366 0.073 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
C1 N1 C2 128.67(17)
C1 N1 H1 113.3(14)
C2 N1 H1 117.4(13)
C9 N2 C1 128.66(17)
C9 N2 H2 117.9(13)
C1 N2 H2 113.4(13)
N1 C1 N2 115.47(16)
N1 C1 S1 126.36(15)
N2 C1 S1 118.16(14)
C7 C2 C3 120.86(18)
C7 C2 N1 121.75(18)
C3 C2 N1 117.33(17)
C4 C3 C2 117.43(19)
C4 C3 C8 120.35(19)
C2 C3 C8 122.21(17)
C5 C4 C3 121.7(2)
C5 C4 H4 119.2
C3 C4 H4 119.2
C4 C5 C6 120.3(2)
C4 C5 H5 119.9
C6 C5 H5 119.9
C5 C6 C7 119.8(2)
C5 C6 H6 120.1
C7 C6 H6 120.1
C6 C7 C2 119.8(2)
C6 C7 H7 120.1
C2 C7 H7 120.1
C3 C8 H8A 109.5
C3 C8 H8B 109.5
H8A C8 H8B 109.5
C3 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
O1 C9 N2 121.47(18)
O1 C9 C10 121.17(17)
N2 C9 C10 117.36(16)
C11 C10 C15 118.79(19)
C11 C10 C9 123.66(17)
C15 C10 C9 117.49(18)
C12 C11 C10 119.9(2)
C12 C11 H11 120.0
C10 C11 H11 120.0
C13 C12 C11 120.5(2)
C13 C12 H12 119.8
C11 C12 H12 119.8
C14 C13 C12 120.0(2)
C14 C13 H13 120.0
C12 C13 H13 120.0
C13 C14 C15 120.0(2)
C13 C14 H14 120.0
C15 C14 H14 120.0
C14 C15 C10 120.8(2)
C14 C15 H15 119.6
C10 C15 H15 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.6671(18)
N1 C1 1.330(2)
N1 C2 1.424(2)
N1 H1 0.87(2)
N2 C9 1.373(2)
N2 C1 1.388(2)
N2 H2 0.86(2)
O1 C9 1.225(2)
C2 C7 1.384(3)
C2 C3 1.397(3)
C3 C4 1.383(3)
C3 C8 1.502(3)
C4 C5 1.369(3)
C4 H4 0.9300
C5 C6 1.369(4)
C5 H5 0.9300
C6 C7 1.378(3)
C6 H6 0.9300
C7 H7 0.9300
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 C10 1.485(3)
C10 C11 1.385(3)
C10 C15 1.388(3)
C11 C12 1.380(3)
C11 H11 0.9300
C12 C13 1.371(3)
C12 H12 0.9300
C13 C14 1.370(3)
C13 H13 0.9300
C14 C15 1.372(3)
C14 H14 0.9300
C15 H15 0.9300
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
N2 H2 S1 3_666 0.86(2) 2.72(2) 3.5326(18) 157.9(17)
N1 H1 O1 . 0.87(2) 1.87(2) 2.614(2) 142.4(19)
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
C2 N1 C1 N2 -173.91(18)
C2 N1 C1 S1 4.9(3)
C9 N2 C1 N1 5.0(3)
C9 N2 C1 S1 -173.91(16)
C1 N1 C2 C7 -45.1(3)
C1 N1 C2 C3 137.7(2)
C7 C2 C3 C4 3.2(3)
N1 C2 C3 C4 -179.58(18)
C7 C2 C3 C8 -176.17(19)
N1 C2 C3 C8 1.0(3)
C2 C3 C4 C5 -1.2(3)
C8 C3 C4 C5 178.2(2)
C3 C4 C5 C6 -1.3(4)
C4 C5 C6 C7 1.7(4)
C5 C6 C7 C2 0.4(3)
C3 C2 C7 C6 -2.9(3)
N1 C2 C7 C6 -179.96(19)
C1 N2 C9 O1 -5.6(3)
C1 N2 C9 C10 173.57(18)
O1 C9 C10 C11 157.1(2)
N2 C9 C10 C11 -22.0(3)
O1 C9 C10 C15 -20.1(3)
N2 C9 C10 C15 160.73(18)
C15 C10 C11 C12 -0.7(3)
C9 C10 C11 C12 -177.87(19)
C10 C11 C12 C13 1.0(3)
C11 C12 C13 C14 -0.7(4)
C12 C13 C14 C15 0.1(4)
C13 C14 C15 C10 0.2(4)
C11 C10 C15 C14 0.1(3)
C9 C10 C15 C14 177.5(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 604163
