#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/49/2014950.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_2014950
loop_
_publ_author_name
'Kazak, Canan'
'Yilmaz, Veysel T.'
'Servi, Suleyman'
'Koca, Murat'
'Heinemann, Frank W.'
_publ_section_title
;
 1,3-Dibenzoylimidazolidine-2-thione and
 1,3-dibenzoyl-3,4,5,6-tetrahydropyrimidine-2(1H)-thione
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o348
_journal_page_last               o350
_journal_paper_doi               10.1107/S0108270105009844
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C18 H16 N2 O2 S'
_chemical_formula_moiety         'C18 H16 N2 O2 S'
_chemical_formula_sum            'C18 H16 N2 O2 S'
_chemical_formula_weight         324.39
_chemical_name_systematic
;
1,3-Dibenzoyl-3,4,5,6-tetrahydropyrimidine-2(1H)-thione
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6803(6)
_cell_length_b                   21.9460(10)
_cell_length_c                   8.1845(9)
_cell_measurement_reflns_used    150
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      20.00
_cell_measurement_theta_min      6.00
_cell_volume                     1559.1(2)
_computing_cell_refinement       'EVALCCD (Bruker, 2002)'
_computing_data_collection       'COLLECT (Bruker, 2002)'
_computing_data_reduction        EVALCCD
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2002)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method
;
 φ and ω scans with 1.4° and 126 s per frame
;
_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  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            22525
_diffrn_reflns_theta_full        28.69
_diffrn_reflns_theta_max         28.69
_diffrn_reflns_theta_min         3.42
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.278
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         2051
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0382
_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)+(0.0438P)²+0.7208P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0951
_reflns_number_gt                1707
_reflns_number_total             2051
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tr1118.cif
_cod_data_source_block           II
_cod_database_code               2014950
_cod_database_fobs_code          2014950
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'
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 0.03972(5) 0.7500 0.05041(6) 0.01700(13) Uani d S 1 . . S
O1 0.18277(15) 0.61397(5) -0.15616(13) 0.0334(3) Uani d . 1 . . O
N1 0.30041(13) 0.69748(5) -0.04365(13) 0.0183(2) Uani d . 1 . . N
C1 0.27306(16) 0.63935(7) 0.26952(17) 0.0211(3) Uani d . 1 . . C
H1A 0.3281 0.6765 0.2588 0.025 Uiso calc R 1 . . H
C2 0.26144(18) 0.61116(8) 0.42084(18) 0.0302(4) Uani d . 1 . . C
H2A 0.3088 0.6291 0.5138 0.036 Uiso calc R 1 . . H
C3 0.1815(2) 0.55730(8) 0.4367(2) 0.0378(4) Uani d . 1 . . C
H3A 0.1729 0.5385 0.5408 0.045 Uiso calc R 1 . . H
C4 0.1137(2) 0.53055(8) 0.3019(2) 0.0398(5) Uani d . 1 . . C
H4A 0.0598 0.4931 0.3135 0.048 Uiso calc R 1 . . H
C5 0.12401(18) 0.55813(7) 0.1492(2) 0.0274(3) Uani d . 1 . . C
H5A 0.0771 0.5398 0.0566 0.033 Uiso calc R 1 . . H
C6 0.20375(15) 0.61295(6) 0.13345(16) 0.0177(3) Uani d . 1 . . C
C7 0.21906(16) 0.63974(6) -0.03214(16) 0.0192(3) Uani d . 1 . . C
C8 0.2246(2) 0.7500 -0.0151(2) 0.0157(4) Uani d S 1 . . C
C9 0.45417(16) 0.69417(7) -0.12014(19) 0.0257(3) Uani d . 1 . . C
H9A 0.4435 0.6920 -0.2404 0.031 Uiso calc R 1 . . H
H9B 0.5085 0.6571 -0.0825 0.031 Uiso calc R 1 . . H
C10 0.5456(2) 0.7500 -0.0738(3) 0.0266(5) Uani d S 1 . . C
H10A 0.6457 0.7500 -0.1317 0.032 Uiso calc SR 1 . . H
H10B 0.5659 0.7500 0.0452 0.032 Uiso calc SR 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0152(2) 0.0180(2) 0.0179(2) 0.000 0.00326(17) 0.000
O1 0.0498(7) 0.0282(6) 0.0221(6) 0.0020(5) -0.0116(5) -0.0064(4)
N1 0.0172(5) 0.0197(6) 0.0179(5) 0.0024(4) 0.0043(4) 0.0013(4)
C1 0.0194(6) 0.0248(7) 0.0191(6) 0.0018(5) -0.0006(5) 0.0012(5)
C2 0.0272(8) 0.0447(10) 0.0188(7) 0.0115(7) 0.0016(6) 0.0061(7)
C3 0.0376(9) 0.0412(10) 0.0345(9) 0.0170(8) 0.0159(7) 0.0198(8)
C4 0.0354(9) 0.0226(8) 0.0614(12) 0.0027(7) 0.0191(8) 0.0148(8)
C5 0.0239(7) 0.0187(7) 0.0398(9) 0.0006(6) 0.0026(6) -0.0020(6)
C6 0.0152(6) 0.0170(6) 0.0209(6) 0.0038(5) 0.0005(5) 0.0009(5)
C7 0.0210(6) 0.0168(6) 0.0197(6) 0.0043(5) -0.0035(5) -0.0017(5)
C8 0.0176(8) 0.0190(9) 0.0104(8) 0.000 0.0006(7) 0.000
C9 0.0190(7) 0.0310(8) 0.0271(7) 0.0061(6) 0.0066(6) -0.0019(6)
C10 0.0159(9) 0.0409(12) 0.0231(10) 0.000 0.0017(8) 0.000
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 C9 . . 115.08(11) yes
C8 N1 C7 . . 119.80(12) yes
C8 N1 C9 . . 123.87(12) yes
C2 C1 C6 . . 119.79(14) ?
C2 C1 H1A . . 120.1 ?
C6 C1 H1A . . 120.1 ?
C3 C2 C1 . . 120.21(16) ?
C3 C2 H2A . . 119.9 ?
C1 C2 H2A . . 119.9 ?
C2 C3 C4 . . 120.30(15) ?
C2 C3 H3A . . 119.8 ?
C4 C3 H3A . . 119.8 ?
C3 C4 C5 . . 120.32(15) ?
C3 C4 H4A . . 119.8 ?
C5 C4 H4A . . 119.8 ?
C4 C5 C6 . . 119.38(15) ?
C4 C5 H5A . . 120.3 ?
C6 C5 H5A . . 120.3 ?
C1 C6 C5 . . 119.98(13) ?
C1 C6 C7 . . 121.82(13) ?
C5 C6 C7 . . 118.11(13) ?
O1 C7 N1 . . 118.82(13) ?
O1 C7 C6 . . 124.10(13) ?
N1 C7 C6 . . 116.63(11) ?
N1 C8 N1 7_575 . 117.56(16) yes
N1 C8 S1 . . 121.21(8) yes
N1 C9 C10 . . 109.21(13) ?
N1 C9 H9A . . 109.8 ?
C10 C9 H9A . . 109.8 ?
N1 C9 H9B . . 109.8 ?
C10 C9 H9B . . 109.8 ?
H9A C9 H9B . . 108.3 ?
C9 C10 C9 . 7_575 108.66(17) ?
C9 C10 H10A . . 110.0 ?
C9 C10 H10A 7_575 . 110.0 ?
C9 C10 H10B . . 110.0 ?
C9 C10 H10B 7_575 . 110.0 ?
H10A C10 H10B . . 108.3 ?
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
N1 C7 . 1.4537(18) yes
N1 C8 . 1.3478(15) yes
N1 C9 . 1.4760(17) yes
O1 C7 . 1.2039(17) yes
S1 C8 . 1.6918(19) yes
C1 C2 . 1.388(2) ?
C1 C6 . 1.3920(19) ?
C1 H1A . 0.9500 ?
C2 C3 . 1.377(3) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.381(3) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.391(2) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.394(2) ?
C5 H5A . 0.9500 ?
C6 C7 . 1.4832(19) ?
C9 C10 . 1.5082(19) yes
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
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_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . -0.1(2) ?
C1 C2 C3 C4 . 0.7(2) ?
C2 C3 C4 C5 . -0.8(2) ?
C3 C4 C5 C6 . 0.2(2) ?
C2 C1 C6 C5 . -0.5(2) ?
C2 C1 C6 C7 . -177.07(13) ?
C4 C5 C6 C1 . 0.5(2) ?
C4 C5 C6 C7 . 177.16(13) ?
C8 N1 C7 O1 . 103.75(17) ?
C9 N1 C7 O1 . -63.95(17) ?
C8 N1 C7 C6 . -83.64(16) ?
C9 N1 C7 C6 . 108.66(13) ?
C1 C6 C7 O1 . 167.71(14) ?
C5 C6 C7 O1 . -8.9(2) ?
C1 C6 C7 N1 . -4.47(19) ?
C5 C6 C7 N1 . 178.89(12) ?
C7 N1 C8 N1 7_575 -173.28(10) yes
C9 N1 C8 N1 7_575 -6.7(2) yes
C7 N1 C8 S1 . 5.5(2) ?
C9 N1 C8 S1 . 172.02(11) yes
C8 N1 C9 C10 . 32.02(19) yes
C7 N1 C9 C10 . -160.84(12) ?
N1 C9 C10 C9 7_575 -54.9(2) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21133806
