#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/88/2008807.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_2008807
loop_
_publ_author_name
'S. Shanmuga Sundara Raj'
'K. Puviarasan'
'D. Velmurugan'
'G. Jayanthi'
'Hoong-Kun Fun'
_publ_section_title
;
 N---H···S hydrogen bonding in
 N-benzoyl-N'-methyl-N'-phenylthiourea and
 N-benzoyl-N'-(3,4-dimethylphenyl)thiourea
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1318
_journal_page_last               1320
_journal_paper_doi               10.1107/S0108270199005788
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C15 H14 N2 O S'
_chemical_formula_weight         270.34
_chemical_name_systematic
;
N-Benzoyl-N'-methyl-N'-phenyl thiourea
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                91.1420(10)
_cell_angle_beta                 107.4370(10)
_cell_angle_gamma                113.0350(10)
_cell_formula_units_Z            2
_cell_length_a                   8.4551(2)
_cell_length_b                   8.9044(2)
_cell_length_c                   10.7293(3)
_cell_measurement_reflns_used    8192
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.01
_cell_volume                     700.50(3)
_computing_cell_refinement       'SAINT (Siemens, 1996b)'
_computing_data_collection       'SMART (Siemens, 1996a)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PARST (Nardelli, 1995)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_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  0.049
_diffrn_reflns_av_sigmaI/netI    0.0753
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5735
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.279
_refine_ls_extinction_coef       0.016(4)
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3325
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.925
_refine_ls_R_factor_all          0.069
_refine_ls_R_factor_gt           0.041
_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)+(0.0351P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.104
_reflns_number_gt                2219
_reflns_number_total             3325
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            na1414.cif
_cod_data_source_block           I
_cod_database_code               2008807
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
S1 0.08796(7) 0.88241(6) 0.16300(4) 0.05847(18) Uani d . 1 . . S
O1 -0.18736(17) 1.09165(15) 0.31387(11) 0.0555(3) Uani d . 1 . . O
N1 -0.02898(19) 1.11811(16) 0.17158(12) 0.0417(3) Uani d . 1 . . N
N2 0.18765(19) 1.11405(15) 0.36492(12) 0.0426(3) Uani d . 1 . . N
C1 -0.2754(2) 1.20662(17) 0.12122(14) 0.0413(4) Uani d . 1 . . C
C2 -0.4518(3) 1.1629(2) 0.11916(19) 0.0547(5) Uani d . 1 . . C
C3 -0.5638(3) 1.2214(3) 0.0323(2) 0.0723(7) Uani d . 1 . . C
C4 -0.4999(4) 1.3225(3) -0.0513(2) 0.0851(8) Uani d . 1 . . C
C5 -0.3235(5) 1.3702(3) -0.0481(2) 0.0878(8) Uani d . 1 . . C
C6 -0.2080(3) 1.3133(2) 0.03949(19) 0.0600(5) Uani d . 1 . . C
C7 -0.1625(2) 1.13462(18) 0.21242(14) 0.0401(3) Uani d . 1 . . C
C8 0.0846(2) 1.04516(18) 0.24039(14) 0.0411(4) Uani d . 1 . . C
C9 0.2078(2) 1.26935(18) 0.42559(15) 0.0429(4) Uani d . 1 . . C
C10 0.1792(3) 1.2794(2) 0.54485(16) 0.0526(4) Uani d . 1 . . C
C11 0.2001(3) 1.4289(3) 0.6031(2) 0.0652(5) Uani d . 1 . . C
C12 0.2470(3) 1.5664(3) 0.5417(2) 0.0718(6) Uani d . 1 . . C
C13 0.2772(3) 1.5555(2) 0.4241(2) 0.0684(6) Uani d . 1 . . C
C14 0.2614(3) 1.4086(2) 0.36611(17) 0.0527(4) Uani d . 1 . . C
C15 0.3026(3) 1.0372(3) 0.44303(19) 0.0535(5) Uani d . 1 . . C
H2 -0.496(3) 1.091(3) 0.169(2) 0.076(7) Uiso d . 1 . . H
H3 -0.681(4) 1.193(3) 0.031(2) 0.092(8) Uiso d . 1 . . H
H4 -0.578(3) 1.368(2) -0.110(2) 0.087(7) Uiso d . 1 . . H
H5 -0.279(4) 1.433(3) -0.100(3) 0.107(9) Uiso d . 1 . . H
H6 -0.088(3) 1.343(2) 0.0422(18) 0.056(5) Uiso d . 1 . . H
H10 0.143(3) 1.180(2) 0.5865(17) 0.061(5) Uiso d . 1 . . H
H11 0.182(3) 1.432(2) 0.689(2) 0.076(6) Uiso d . 1 . . H
H12 0.258(3) 1.667(2) 0.581(2) 0.075(6) Uiso d . 1 . . H
H13 0.310(3) 1.648(3) 0.382(2) 0.083(7) Uiso d . 1 . . H
H14 0.292(2) 1.403(2) 0.2911(17) 0.052(5) Uiso d . 1 . . H
H15A 0.231(3) 0.925(2) 0.4410(18) 0.064(6) Uiso d . 1 . . H
H15B 0.357(3) 1.095(2) 0.529(2) 0.061(5) Uiso d . 1 . . H
H15C 0.390(3) 1.046(2) 0.405(2) 0.077(7) Uiso d . 1 . . H
H1N1 -0.045(2) 1.1101(19) 0.0915(17) 0.046(5) Uiso d . 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'
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 123.49(13) y
C7 N1 H1N1 117.7(12) ?
C8 N1 H1N1 113.2(11) ?
C8 N2 C9 123.92(11) y
C8 N2 C15 118.87(14) ?
C9 N2 C15 116.94(13) ?
C2 C1 C6 120.07(16) ?
C2 C1 C7 118.24(15) ?
C6 C1 C7 121.69(16) ?
C1 C2 C3 120.2(2) ?
C1 C2 H2 119.6(14) ?
C3 C2 H2 120.0(14) ?
C4 C3 C2 120.0(2) ?
C4 C3 H3 119.8(14) ?
C2 C3 H3 120.3(14) ?
C3 C4 C5 120.46(19) ?
C3 C4 H4 120.0(14) ?
C5 C4 H4 119.4(14) ?
C4 C5 C6 120.4(2) ?
C4 C5 H5 122.8(18) ?
C6 C5 H5 116.7(18) ?
C1 C6 C5 118.8(2) ?
C1 C6 H6 119.4(10) ?
C5 C6 H6 121.7(11) ?
O1 C7 N1 122.38(13) ?
O1 C7 C1 122.57(16) y
N1 C7 C1 115.04(13) ?
N2 C8 N1 116.93(13) y
N2 C8 S1 123.66(10) ?
N1 C8 S1 119.39(11) ?
C10 C9 C14 120.35(16) ?
C10 C9 N2 119.73(14) ?
C14 C9 N2 119.89(15) ?
C9 C10 C11 119.50(17) ?
C9 C10 H10 119.5(11) ?
C11 C10 H10 121.0(11) ?
C12 C11 C10 120.2(2) ?
C12 C11 H11 122.7(11) ?
C10 C11 H11 117.0(11) ?
C13 C12 C11 119.77(19) ?
C13 C12 H12 120.4(13) ?
C11 C12 H12 119.9(13) ?
C12 C13 C14 120.8(2) ?
C12 C13 H13 120.2(13) ?
C14 C13 H13 118.9(14) ?
C13 C14 C9 119.23(19) ?
C13 C14 H14 121.3(10) ?
C9 C14 H14 119.4(10) ?
N2 C15 H15A 109.6(11) ?
N2 C15 H15B 107.4(10) ?
H15A C15 H15B 111.5(16) ?
N2 C15 H15C 107.9(12) ?
H15A C15 H15C 109.4(17) ?
H15B C15 H15C 110.9(19) ?
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 C8 . 1.670(2) y
O1 C7 . 1.2101(2) y
N1 C7 . 1.383(2) ?
N1 C8 . 1.404(2) y
N1 H1N1 . 0.83(2) ?
N2 C8 . 1.331(2) y
N2 C9 . 1.442(2) y
N2 C15 . 1.473(2) y
C1 C2 . 1.379(3) ?
C1 C6 . 1.380(2) ?
C1 C7 . 1.4910(18) ?
C2 C3 . 1.384(3) ?
C2 H2 . 0.88(2) ?
C3 C4 . 1.359(4) ?
C3 H3 . 0.92(3) ?
C4 C5 . 1.371(4) ?
C4 H4 . 0.98(2) ?
C5 C6 . 1.396(3) ?
C5 H5 . 0.86(3) ?
C6 H6 . 0.93(2) ?
C9 C10 . 1.379(2) ?
C9 C14 . 1.384(2) ?
C10 C11 . 1.383(3) ?
C10 H10 . 0.979(17) ?
C11 C12 . 1.378(3) ?
C11 H11 . 0.97(2) ?
C12 C13 . 1.369(3) ?
C12 H12 . 0.94(2) ?
C13 C14 . 1.377(3) ?
C13 H13 . 0.93(2) ?
C14 H14 . 0.921(18) ?
C15 H15A . 0.94(2) ?
C15 H15B . 0.94(2) ?
C15 H15C . 0.92(2) ?
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 H1N1 S1 2_575 0.83(2) 2.65(2) 3.4730(10) 174(2) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2300591
