#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/88/2228825.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_2228825
loop_
_publ_author_name
'Okuniewski, Andrzej'
'Chojnacki, Jaroslaw'
'Becker, Barbara'
_publ_section_title
;
 N,N'-Diphenylthiourea acetone monosolvate
;
_journal_coeditor_code           NG5077
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o55
_journal_paper_doi               10.1107/S1600536810050300
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C13 H12 N2 S, C3 H6 O'
_chemical_formula_moiety         'C13 H12 N2 S, C3 H6 O'
_chemical_formula_sum            'C16 H18 N2 O S'
_chemical_formula_weight         286.38
_chemical_melting_point          154.0(10)
_chemical_name_systematic
;
N,N'-Diphenylthiourea acetone monosolvate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.1797(6)
_cell_length_b                   10.0736(4)
_cell_length_c                   17.4700(7)
_cell_measurement_reflns_used    3367
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.6477
_cell_measurement_theta_min      2.3307
_cell_volume                     3023.4(2)
_computing_cell_refinement
;
CrysAlis PRO (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis PRO (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis PRO (Oxford Diffraction, 2009)
;
_computing_molecular_graphics
'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.1883
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Sapphire2'
_diffrn_measurement_method       'ω scans'
_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  0.0248
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7549
_diffrn_reflns_theta_full        27
_diffrn_reflns_theta_max         27
_diffrn_reflns_theta_min         2.62
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.819
_exptl_absorpt_correction_T_min  0.777
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.4609
_exptl_crystal_size_mid          0.4133
_exptl_crystal_size_min          0.266
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.207
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3245
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.939
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0540P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0924
_reflns_number_gt                2278
_reflns_number_total             3245
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng5077.cif
_cod_data_source_block           I
_cod_database_code               2228825
_cod_database_fobs_code          2228825
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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 1.00623(2) 0.60332(4) 0.60875(2) 0.02588(12) Uani d . 1 . .
N N1 0.90820(7) 0.42124(13) 0.56131(7) 0.0227(3) Uani d D 1 . .
H H1 0.9367(8) 0.4256(17) 0.5206(7) 0.033(5) Uiso d D 1 . .
N N2 0.89857(8) 0.47225(14) 0.68979(7) 0.0245(3) Uani d D 1 . .
H H2 0.8677(9) 0.4042(13) 0.6956(10) 0.040(5) Uiso d D 1 . .
C C1 0.93269(8) 0.49352(16) 0.62170(8) 0.0219(3) Uani d . 1 . .
C C11 0.84080(9) 0.34076(16) 0.55234(8) 0.0238(3) Uani d . 1 . .
C C12 0.84703(10) 0.23117(18) 0.50489(8) 0.0292(4) Uani d . 1 . .
H H12 0.8963 0.207 0.4846 0.035 Uiso calc R 1 . .
C C13 0.78192(11) 0.1567(2) 0.48687(10) 0.0389(5) Uani d . 1 . .
H H13 0.7864 0.0819 0.454 0.047 Uiso calc R 1 . .
C C14 0.71028(11) 0.1916(2) 0.51682(10) 0.0406(5) Uani d . 1 . .
H H14 0.6653 0.1414 0.5042 0.049 Uiso calc R 1 . .
C C15 0.70426(9) 0.2990(2) 0.56486(10) 0.0358(4) Uani d . 1 . .
H H15 0.655 0.3215 0.586 0.043 Uiso calc R 1 . .
C C16 0.76902(9) 0.37509(18) 0.58304(9) 0.0291(4) Uani d . 1 . .
H H16 0.7643 0.4496 0.616 0.035 Uiso calc R 1 . .
C C21 0.91899(8) 0.53867(17) 0.75969(8) 0.0238(4) Uani d . 1 . .
C C22 0.91081(9) 0.67464(17) 0.76642(9) 0.0285(4) Uani d . 1 . .
H H22 0.8934 0.7256 0.724 0.034 Uiso calc R 1 . .
C C23 0.92812(10) 0.73653(19) 0.83536(10) 0.0350(4) Uani d . 1 . .
H H23 0.9229 0.8301 0.84 0.042 Uiso calc R 1 . .
C C24 0.95281(10) 0.6625(2) 0.89701(9) 0.0376(5) Uani d . 1 . .
H H24 0.9645 0.7048 0.9442 0.045 Uiso calc R 1 . .
C C25 0.96061(11) 0.5259(2) 0.88998(9) 0.0371(5) Uani d . 1 . .
H H25 0.9775 0.4749 0.9326 0.045 Uiso calc R 1 . .
C C26 0.94387(9) 0.46364(19) 0.82118(8) 0.0305(4) Uani d . 1 . .
H H26 0.9495 0.3702 0.8164 0.037 Uiso calc R 1 . .
O O1 0.79841(7) 0.27541(12) 0.76020(7) 0.0398(3) Uani d . 1 . .
C C1A 0.80931(9) 0.15731(18) 0.76927(9) 0.0273(4) Uani d . 1 . .
C C2 0.85919(11) 0.0803(2) 0.71495(9) 0.0404(5) Uani d . 1 . .
H H2A 0.8556 0.1196 0.6638 0.061 Uiso calc R 1 . .
H H2B 0.8413 -0.012 0.7131 0.061 Uiso calc R 1 . .
H H2C 0.9134 0.0829 0.7324 0.061 Uiso calc R 1 . .
C C3 0.77585(10) 0.08360(18) 0.83558(9) 0.0328(4) Uani d . 1 . .
H H3A 0.7408 0.1422 0.8642 0.049 Uiso calc R 1 . .
H H3B 0.818 0.0538 0.8692 0.049 Uiso calc R 1 . .
H H3C 0.7467 0.0064 0.8169 0.049 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 0 '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 0.006 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 -5 22 0.1927
-20 -5 -10 0.1676
21 6 8 0.1483
1 14 -5 0.1847
-18 8 -10 0.2023
1 5 -23 0.2373
-1 -5 23 0.2221
5 13 9 0.1212
-5 -13 -9 0.1448
-12 9 15 0.1728
19 -8 -4 0.1439
-17 2 -18 0.1281
-7 -2 -23 0.1989
-3 -13 11 0.2382
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
C1 N1 C11 . . 130.37(13) ?
C1 N1 H1 . . 116.0(11) ?
C11 N1 H1 . . 113.6(11) ?
C1 N2 C21 . . 124.89(14) ?
C1 N2 H2 . . 119.5(12) ?
C21 N2 H2 . . 114.6(11) ?
N2 C1 N1 . . 118.05(14) ?
N2 C1 S1 . . 123.22(11) ?
N1 C1 S1 . . 118.71(11) ?
C12 C11 C16 . . 119.89(15) ?
C12 C11 N1 . . 117.23(14) ?
C16 C11 N1 . . 122.59(15) ?
C13 C12 C11 . . 120.40(16) ?
C13 C12 H12 . . 119.8 ?
C11 C12 H12 . . 119.8 ?
C14 C13 C12 . . 119.74(18) ?
C14 C13 H13 . . 120.1 ?
C12 C13 H13 . . 120.1 ?
C15 C14 C13 . . 119.91(17) ?
C15 C14 H14 . . 120 ?
C13 C14 H14 . . 120 ?
C14 C15 C16 . . 120.98(16) ?
C14 C15 H15 . . 119.5 ?
C16 C15 H15 . . 119.5 ?
C15 C16 C11 . . 119.07(17) ?
C15 C16 H16 . . 120.5 ?
C11 C16 H16 . . 120.5 ?
C26 C21 C22 . . 120.50(15) ?
C26 C21 N2 . . 118.82(15) ?
C22 C21 N2 . . 120.62(14) ?
C21 C22 C23 . . 119.81(16) ?
C21 C22 H22 . . 120.1 ?
C23 C22 H22 . . 120.1 ?
C24 C23 C22 . . 120.07(18) ?
C24 C23 H23 . . 120 ?
C22 C23 H23 . . 120 ?
C23 C24 C25 . . 119.85(16) ?
C23 C24 H24 . . 120.1 ?
C25 C24 H24 . . 120.1 ?
C26 C25 C24 . . 120.37(17) ?
C26 C25 H25 . . 119.8 ?
C24 C25 H25 . . 119.8 ?
C21 C26 C25 . . 119.40(17) ?
C21 C26 H26 . . 120.3 ?
C25 C26 H26 . . 120.3 ?
O1 C1A C3 . . 121.98(16) ?
O1 C1A C2 . . 120.89(16) ?
C3 C1A C2 . . 117.11(16) ?
C1A C2 H2A . . 109.5 ?
C1A C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
C1A C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
C1A C3 H3A . . 109.5 ?
C1A C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
C1A C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
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 C1 . 1.6943(16) ?
N1 C1 . 1.3492(18) ?
N1 C11 . 1.4221(19) ?
N1 H1 . 0.865(9) ?
N2 C1 . 1.3433(18) ?
N2 C21 . 1.4359(19) ?
N2 H2 . 0.873(9) ?
C11 C12 . 1.385(2) ?
C11 C16 . 1.389(2) ?
C12 C13 . 1.383(2) ?
C12 H12 . 0.95 ?
C13 C14 . 1.383(3) ?
C13 H13 . 0.95 ?
C14 C15 . 1.373(3) ?
C14 H14 . 0.95 ?
C15 C16 . 1.388(2) ?
C15 H15 . 0.95 ?
C16 H16 . 0.95 ?
C21 C26 . 1.381(2) ?
C21 C22 . 1.382(2) ?
C22 C23 . 1.388(2) ?
C22 H22 . 0.95 ?
C23 C24 . 1.377(3) ?
C23 H23 . 0.95 ?
C24 C25 . 1.387(3) ?
C24 H24 . 0.95 ?
C25 C26 . 1.386(2) ?
C25 H25 . 0.95 ?
C26 H26 . 0.95 ?
O1 C1A . 1.215(2) ?
C1A C3 . 1.491(2) ?
C1A C2 . 1.495(2) ?
C2 H2A . 0.98 ?
C2 H2B . 0.98 ?
C2 H2C . 0.98 ?
C3 H3A . 0.98 ?
C3 H3B . 0.98 ?
C3 H3C . 0.98 ?
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
N1 H1 S1 5_766 0.865(9) 2.480(13) 3.3240(13) 165.3(13)
N2 H2 O1 . 0.873(9) 2.091(14) 2.8993(18) 153.6(16)
C2 H2A Cg1 . 0.98 3.02 3.931(2) 155
C2 H2C Cg2 3_746 0.98 2.80 3.607(2) 140
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26231249
