#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/38/2223812.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_2223812
loop_
_publ_author_name
'Shahwar, Durre'
'Tahir, M. Nawaz'
'Raza, Muhammad Asam'
'Iqbal, Bushra'
_publ_section_title
;
 (5Z)-5-(2-Hydroxybenzylidene)-3-phenyl-2-thioxo-1,3-thiazolidin-4-one
;
_journal_coeditor_code           HB5180
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2903
_journal_paper_doi               10.1107/S1600536809044286
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H11 N O2 S2'
_chemical_formula_moiety         'C16 H11 N O2 S2'
_chemical_formula_sum            'C16 H11 N O2 S2'
_chemical_formula_weight         313.40
_chemical_name_systematic
;
(5Z)-5-(2-Hydroxybenzylidene)-3-phenyl-2-thioxo-1,3-thiazolidin-4-one
;
_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
_cell_angle_beta                 95.131(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6553(7)
_cell_length_b                   7.3424(4)
_cell_length_c                   16.8256(10)
_cell_measurement_reflns_used    3481
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.03
_cell_measurement_theta_min      2.04
_cell_volume                     1434.13(14)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 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      296(2)
_diffrn_detector_area_resol_mean 7.40
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_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  0.0484
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15580
_diffrn_reflns_theta_full        28.03
_diffrn_reflns_theta_max         28.03
_diffrn_reflns_theta_min         2.04
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.374
_exptl_absorpt_correction_T_max  0.937
_exptl_absorpt_correction_T_min  0.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            'orange yellow'
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prisms
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.268
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3481
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0375P)²+0.3260P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.1016
_reflns_number_gt                2194
_reflns_number_total             3481
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5180.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2223812
_cod_database_fobs_code          2223812
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
S S1 0.16936(5) 0.50419(7) 0.48587(3) 0.0463(2) Uani . . 1.000
S S2 0.12725(6) 0.16709(8) 0.57270(4) 0.0591(2) Uani . . 1.000
O O1 0.45774(15) 0.5967(2) 0.60654(9) 0.0572(6) Uani . . 1.000
O O2 0.40155(14) 1.1358(2) 0.44795(9) 0.0515(6) Uani . . 1.000
N N1 0.30920(15) 0.3922(2) 0.60195(9) 0.0376(6) Uani . . 1.000
C C1 0.35642(18) 0.2866(3) 0.66982(12) 0.0370(7) Uani . . 1.000
C C2 0.3410(2) 0.3461(3) 0.74551(12) 0.0432(7) Uani . . 1.000
C C3 0.3835(2) 0.2416(3) 0.81002(12) 0.0477(8) Uani . . 1.000
C C4 0.4398(2) 0.0815(3) 0.79786(14) 0.0497(8) Uani . . 1.000
C C5 0.4550(2) 0.0235(3) 0.72188(14) 0.0524(9) Uani . . 1.000
C C6 0.4139(2) 0.1273(3) 0.65678(13) 0.0466(8) Uani . . 1.000
C C7 0.20684(19) 0.3439(3) 0.55947(12) 0.0399(7) Uani . . 1.000
C C8 0.29274(19) 0.6347(3) 0.51013(11) 0.0385(7) Uani . . 1.000
C C9 0.3643(2) 0.5470(3) 0.57636(12) 0.0401(7) Uani . . 1.000
C C10 0.32304(19) 0.7938(3) 0.47846(12) 0.0418(7) Uani . . 1.000
C C11 0.26629(19) 0.9014(3) 0.41462(11) 0.0379(7) Uani . . 1.000
C C12 0.31041(19) 1.0743(3) 0.39934(12) 0.0389(7) Uani . . 1.000
C C13 0.2611(2) 1.1796(3) 0.33719(13) 0.0494(8) Uani . . 1.000
C C14 0.1673(2) 1.1153(3) 0.28976(13) 0.0540(9) Uani . . 1.000
C C15 0.1207(2) 0.9486(3) 0.30463(13) 0.0533(9) Uani . . 1.000
C C16 0.1702(2) 0.8438(3) 0.36550(13) 0.0478(8) Uani . . 1.000
H H2 0.30268 0.45483 0.75331 0.0518 Uiso . . 1.000
H H2A 0.43058 1.22336 0.42710 0.0772 Uiso . . 1.000
H H3 0.37382 0.28003 0.86166 0.0572 Uiso . . 1.000
H H4 0.46807 0.01166 0.84139 0.0596 Uiso . . 1.000
H H5 0.49284 -0.08572 0.71418 0.0629 Uiso . . 1.000
H H6 0.42501 0.08995 0.60520 0.0559 Uiso . . 1.000
H H10 0.39181 0.84263 0.50141 0.0502 Uiso . . 1.000
H H13 0.29121 1.29390 0.32743 0.0593 Uiso . . 1.000
H H14 0.13538 1.18544 0.24737 0.0648 Uiso . . 1.000
H H15 0.05592 0.90715 0.27356 0.0640 Uiso . . 1.000
H H16 0.13881 0.72999 0.37452 0.0574 Uiso . . 1.000
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 S1 C8 . . . 93.20(10) no
C12 O2 H2A . . . 109.00 no
C1 N1 C9 . . . 121.85(17) no
C7 N1 C9 . . . 116.78(17) no
C1 N1 C7 . . . 121.37(16) no
N1 C1 C6 . . . 119.07(18) no
C2 C1 C6 . . . 121.6(2) no
N1 C1 C2 . . . 119.28(19) no
C1 C2 C3 . . . 118.9(2) no
C2 C3 C4 . . . 120.1(2) no
C3 C4 C5 . . . 120.5(2) no
C4 C5 C6 . . . 120.1(2) no
C1 C6 C5 . . . 118.8(2) no
S1 C7 S2 . . . 122.00(13) no
S1 C7 N1 . . . 110.23(15) no
S2 C7 N1 . . . 127.77(16) no
S1 C8 C9 . . . 109.54(15) no
S1 C8 C10 . . . 128.64(17) no
C9 C8 C10 . . . 121.8(2) no
O1 C9 C8 . . . 127.4(2) no
N1 C9 C8 . . . 110.11(18) no
O1 C9 N1 . . . 122.45(19) no
C8 C10 C11 . . . 130.6(2) no
C10 C11 C16 . . . 124.3(2) no
C12 C11 C16 . . . 116.97(19) no
C10 C11 C12 . . . 118.71(19) no
O2 C12 C13 . . . 121.3(2) no
C11 C12 C13 . . . 120.7(2) no
O2 C12 C11 . . . 118.06(18) no
C12 C13 C14 . . . 120.1(2) no
C13 C14 C15 . . . 120.5(2) no
C14 C15 C16 . . . 119.5(2) no
C11 C16 C15 . . . 122.4(2) no
C1 C2 H2 . . . 121.00 no
C3 C2 H2 . . . 121.00 no
C2 C3 H3 . . . 120.00 no
C4 C3 H3 . . . 120.00 no
C3 C4 H4 . . . 120.00 no
C5 C4 H4 . . . 120.00 no
C4 C5 H5 . . . 120.00 no
C6 C5 H5 . . . 120.00 no
C1 C6 H6 . . . 121.00 no
C5 C6 H6 . . . 121.00 no
C8 C10 H10 . . . 115.00 no
C11 C10 H10 . . . 115.00 no
C12 C13 H13 . . . 120.00 no
C14 C13 H13 . . . 120.00 no
C13 C14 H14 . . . 120.00 no
C15 C14 H14 . . . 120.00 no
C14 C15 H15 . . . 120.00 no
C16 C15 H15 . . . 120.00 no
C11 C16 H16 . . . 119.00 no
C15 C16 H16 . . . 119.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C7 . . 1.736(2) no
S1 C8 . . 1.746(2) no
S2 C7 . . 1.623(2) no
O1 C9 . . 1.216(3) no
O2 C12 . . 1.359(3) no
O2 H2A . . 0.8200 no
N1 C7 . . 1.381(3) no
N1 C9 . . 1.393(3) no
N1 C1 . . 1.448(3) no
C1 C6 . . 1.375(3) no
C1 C2 . . 1.373(3) no
C2 C3 . . 1.384(3) no
C3 C4 . . 1.371(3) no
C4 C5 . . 1.374(3) no
C5 C6 . . 1.384(3) no
C8 C9 . . 1.479(3) no
C8 C10 . . 1.344(3) no
C10 C11 . . 1.445(3) no
C11 C16 . . 1.397(3) no
C11 C12 . . 1.402(3) no
C12 C13 . . 1.384(3) no
C13 C14 . . 1.378(3) no
C14 C15 . . 1.371(3) no
C15 C16 . . 1.367(3) no
C2 H2 . . 0.9300 no
C3 H3 . . 0.9300 no
C4 H4 . . 0.9300 no
C5 H5 . . 0.9300 no
C6 H6 . . 0.9300 no
C10 H10 . . 0.9300 no
C13 H13 . . 0.9300 no
C14 H14 . . 0.9300 no
C15 H15 . . 0.9300 no
C16 H16 . . 0.9300 no
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
C16 H16 S1 . 0.93 2.50 3.213(2) 133 yes
O2 H2A O1 3_676 0.82 1.97 2.767(2) 163 yes
C10 H10 O2 3_676 0.93 2.49 3.375(3) 160 yes
C2 H2 CgB 2_556 0.93 2.91 3.774(2) 155 yes
C14 H14 CgB 4_464 0.93 2.91 3.515(2) 124 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
C8 S1 C7 S2 . . . . -179.12(15) no
C8 S1 C7 N1 . . . . 1.29(16) no
C7 S1 C8 C9 . . . . 0.95(16) no
C7 S1 C8 C10 . . . . -177.2(2) no
C7 N1 C1 C2 . . . . -99.9(2) no
C7 N1 C1 C6 . . . . 78.9(3) no
C9 N1 C1 C2 . . . . 80.0(3) no
C9 N1 C1 C6 . . . . -101.2(2) no
C1 N1 C7 S1 . . . . 176.46(14) no
C1 N1 C7 S2 . . . . -3.1(3) no
C9 N1 C7 S1 . . . . -3.5(2) no
C9 N1 C7 S2 . . . . 176.98(17) no
C1 N1 C9 O1 . . . . 4.1(3) no
C1 N1 C9 C8 . . . . -175.75(17) no
C7 N1 C9 O1 . . . . -176.0(2) no
C7 N1 C9 C8 . . . . 4.2(2) no
N1 C1 C2 C3 . . . . 178.1(2) no
C6 C1 C2 C3 . . . . -0.7(3) no
N1 C1 C6 C5 . . . . -177.6(2) no
C2 C1 C6 C5 . . . . 1.3(3) no
C1 C2 C3 C4 . . . . -0.1(3) no
C2 C3 C4 C5 . . . . 0.2(4) no
C3 C4 C5 C6 . . . . 0.3(4) no
C4 C5 C6 C1 . . . . -1.1(3) no
S1 C8 C9 O1 . . . . 177.26(19) no
S1 C8 C9 N1 . . . . -2.9(2) no
C10 C8 C9 O1 . . . . -4.5(4) no
C10 C8 C9 N1 . . . . 175.33(19) no
S1 C8 C10 C11 . . . . -1.9(4) no
C9 C8 C10 C11 . . . . -179.8(2) no
C8 C10 C11 C12 . . . . 172.8(2) no
C8 C10 C11 C16 . . . . -8.2(4) no
C10 C11 C12 O2 . . . . -3.0(3) no
C10 C11 C12 C13 . . . . 177.9(2) no
C16 C11 C12 O2 . . . . 177.90(19) no
C16 C11 C12 C13 . . . . -1.2(3) no
C10 C11 C16 C15 . . . . -178.6(2) no
C12 C11 C16 C15 . . . . 0.5(3) no
O2 C12 C13 C14 . . . . -178.7(2) no
C11 C12 C13 C14 . . . . 0.3(3) no
C12 C13 C14 C15 . . . . 1.3(3) no
C13 C14 C15 C16 . . . . -2.0(3) no
C14 C15 C16 C11 . . . . 1.1(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1310881
