#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/82/2228287.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228287
loop_
_publ_author_name
'Woei Hung, Wong'
'Kassim, Mohammad B.'
_publ_section_title
;
 1-Benzoyl-3-[4-(3-benzoylthioureido)phenyl]thiourea
;
_journal_coeditor_code           DN2618
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3182
_journal_paper_doi               10.1107/S160053681004599X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C22 H18 N4 O2 S2'
_chemical_formula_moiety         'C22 H18 N4 O2 S2'
_chemical_formula_sum            'C22 H18 N4 O2 S2'
_chemical_formula_weight         434.52
_chemical_melting_point          511
_chemical_name_systematic
;
1-Benzoyl-3-[4-(3-benzoylthioureido)phenyl]thiourea
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 101.146(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.513(4)
_cell_length_b                   4.5279(16)
_cell_length_c                   20.209(7)
_cell_measurement_reflns_used    1244
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.49
_cell_measurement_theta_min      1.89
_cell_volume                     1033.6(6)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia,
1997) and
PLATON (Spek, 2009)
;
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
;
Bruker SMART APEX CCD area-detector
;
_diffrn_measurement_method       'ω scan'
_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  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0463
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6173
_diffrn_reflns_theta_full        26.49
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.226
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2142
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0625
_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)+(0.0839P)²+0.1163P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1580
_refine_ls_wR_factor_ref         0.1710
_reflns_number_gt                1529
_reflns_number_total             2142
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2618.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2228287
_cod_database_fobs_code          2228287
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.16597(7) 0.6404(2) 1.04023(4) 0.0663(4) Uani d . 1 . .
O O1 0.25185(19) 0.2798(6) 0.84661(10) 0.0637(7) Uani d . 1 . .
N N1 0.14062(19) 0.3425(5) 0.92651(10) 0.0425(6) Uani d . 1 . .
H H1A 0.0767 0.2852 0.9388 0.051 Uiso calc R 1 . .
N N2 0.30760(19) 0.6294(5) 0.94925(11) 0.0432(6) Uani d . 1 . .
H H2A 0.3149 0.5546 0.9112 0.052 Uiso calc R 1 . .
C C1 0.0805(3) -0.0367(8) 0.76267(15) 0.0643(10) Uani d . 1 . .
H H1 0.1454 0.0344 0.7464 0.077 Uiso calc R 1 . .
C C2 -0.0026(4) -0.2077(10) 0.72171(17) 0.0836(13) Uani d . 1 . .
H H2 0.0062 -0.2506 0.6779 0.100 Uiso calc R 1 . .
C C3 -0.0988(3) -0.3159(8) 0.74552(18) 0.0709(11) Uani d . 1 . .
H H3 -0.1557 -0.4286 0.7176 0.085 Uiso calc R 1 . .
C C4 -0.1102(3) -0.2566(8) 0.81058(16) 0.0563(8) Uani d . 1 . .
H H4 -0.1742 -0.3323 0.8270 0.068 Uiso calc R 1 . .
C C5 -0.0271(3) -0.0849(7) 0.85172(14) 0.0465(7) Uani d . 1 . .
H H5 -0.0352 -0.0467 0.8958 0.056 Uiso calc R 1 . .
C C6 0.0684(2) 0.0310(6) 0.82792(13) 0.0422(7) Uani d . 1 . .
C C7 0.1604(2) 0.2252(7) 0.86697(13) 0.0425(7) Uani d . 1 . .
C C8 0.2103(2) 0.5429(6) 0.97010(13) 0.0407(7) Uani d . 1 . .
C C9 0.4014(2) 0.8203(6) 0.97749(12) 0.0386(7) Uani d . 1 . .
C C10 0.4932(2) 0.8417(7) 0.94239(13) 0.0478(8) Uani d . 1 . .
H H10 0.4887 0.7333 0.9029 0.057 Uiso calc R 1 . .
C C11 0.4091(2) 0.9828(7) 1.03623(13) 0.0472(8) Uani d . 1 . .
H H11 0.3490 0.9734 1.0610 0.057 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
C7 N1 C8 . . 128.9(2) ?
C7 N1 H1A . . 115.5 ?
C8 N1 H1A . . 115.5 ?
C8 N2 C9 . . 132.6(2) ?
C8 N2 H2A . . 113.7 ?
C9 N2 H2A . . 113.7 ?
C2 C1 C6 . . 120.8(3) ?
C2 C1 H1 . . 119.6 ?
C6 C1 H1 . . 119.6 ?
C1 C2 C3 . . 120.1(3) ?
C1 C2 H2 . . 120.0 ?
C3 C2 H2 . . 120.0 ?
C4 C3 C2 . . 119.7(3) ?
C4 C3 H3 . . 120.1 ?
C2 C3 H3 . . 120.1 ?
C3 C4 C5 . . 120.2(3) ?
C3 C4 H4 . . 119.9 ?
C5 C4 H4 . . 119.9 ?
C4 C5 C6 . . 120.6(3) ?
C4 C5 H5 . . 119.7 ?
C6 C5 H5 . . 119.7 ?
C5 C6 C1 . . 118.6(3) ?
C5 C6 C7 . . 125.0(2) ?
C1 C6 C7 . . 116.5(3) ?
O1 C7 N1 . . 120.9(3) ?
O1 C7 C6 . . 120.8(2) ?
N1 C7 C6 . . 118.3(2) ?
N2 C8 N1 . . 113.9(2) ?
N2 C8 S1 . . 127.6(2) ?
N1 C8 S1 . . 118.45(19) ?
C11 C9 C10 . . 118.2(2) ?
C11 C9 N2 . . 126.0(2) ?
C10 C9 N2 . . 115.8(2) ?
C11 C10 C9 3_677 . 122.5(3) ?
C11 C10 H10 3_677 . 118.8 ?
C9 C10 H10 . . 118.8 ?
C10 C11 C9 3_677 . 119.3(2) ?
C10 C11 H11 3_677 . 120.4 ?
C9 C11 H11 . . 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 C8 . 1.656(3) ?
O1 C7 . 1.227(3) ?
N1 C7 . 1.374(3) ?
N1 C8 . 1.403(3) ?
N1 H1A . 0.8600 ?
N2 C8 . 1.330(3) ?
N2 C9 . 1.415(3) ?
N2 H2A . 0.8600 ?
C1 C2 . 1.376(5) ?
C1 C6 . 1.386(4) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.381(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.373(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.380(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.386(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.481(4) ?
C9 C11 . 1.385(4) ?
C9 C10 . 1.385(4) ?
C10 C11 3_677 1.376(4) ?
C10 H10 . 0.9300 ?
C11 C10 3_677 1.376(4) ?
C11 H11 . 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_D
_geom_hbond_site_symmetry_H
_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
N2 H2A O1 . . 1_555 0.86 1.85 2.590(3) 144 yes
C11 H11 S1 . . 1_555 0.93 2.56 3.215(3) 128 yes
C5 H5 S1 . . 3_567 0.93 2.84 3.567(3) 136 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -0.4(7) ?
C1 C2 C3 C4 . . . . -1.2(7) ?
C2 C3 C4 C5 . . . . 1.2(6) ?
C3 C4 C5 C6 . . . . 0.4(5) ?
C4 C5 C6 C1 . . . . -1.9(5) ?
C4 C5 C6 C7 . . . . 177.9(3) ?
C2 C1 C6 C5 . . . . 2.0(5) ?
C2 C1 C6 C7 . . . . -177.9(3) ?
C8 N1 C7 O1 . . . . 3.9(5) ?
C8 N1 C7 C6 . . . . -176.1(3) ?
C5 C6 C7 O1 . . . . 168.1(3) ?
C1 C6 C7 O1 . . . . -12.0(5) ?
C5 C6 C7 N1 . . . . -11.9(4) ?
C1 C6 C7 N1 . . . . 168.0(3) ?
C9 N2 C8 N1 . . . . -178.7(3) ?
C9 N2 C8 S1 . . . . 0.3(5) ?
C7 N1 C8 N2 . . . . 0.7(4) ?
C7 N1 C8 S1 . . . . -178.4(2) ?
C8 N2 C9 C11 . . . . -3.8(5) ?
C8 N2 C9 C10 . . . . 175.8(3) ?
C11 C9 C10 C11 . . . 3_677 0.0(5) ?
N2 C9 C10 C11 . . . 3_677 -179.6(3) ?
C10 C9 C11 C10 . . . 3_677 0.0(5) ?
N2 C9 C11 C10 . . . 3_677 179.6(3) ?
