#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/37/2223764.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_2223764
loop_
_publ_author_name
'Shahwar, Durre'
'Tahir, M. Nawaz'
'Raza, Muhammad Asam'
'Iqbal, Bushra'
'Naz, Sana'
_publ_section_title
;
 (5Z)-5-(2-Hydroxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one
 methanol hemisolvate
;
_journal_coeditor_code           HB5115
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2637
_journal_paper_doi               10.1107/S1600536809039555
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C10 H7 N O2 S2, 0.5C H4 O'
_chemical_formula_moiety         'C10 H7 N O2 S2, 0.5C H4 O'
_chemical_formula_sum            'C10.5 H9 N O2.5 S2'
_chemical_formula_weight         253.33
_chemical_name_systematic
;
(5Z)-5-(2-Hydroxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one methanol
hemisolvate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 108.724(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.4859(16)
_cell_length_b                   6.4422(4)
_cell_length_c                   18.4377(15)
_cell_measurement_reflns_used    2636
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.10
_cell_volume                     2304.5(3)
_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 7.50
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0518
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11803
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.10
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.448
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            'light red'
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'cut needle'
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.280
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2636
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0957
_refine_ls_R_factor_gt           0.0441
_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)+(0.0357P)²+1.2743P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0858
_refine_ls_wR_factor_ref         0.1006
_reflns_number_gt                1562
_reflns_number_total             2636
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5115.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C10.5 H9 N1 O2.5 S2'
_cod_database_code               2223764
_cod_database_fobs_code          2223764
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y,1/2-z
3 -x,-y,-z
4 x,-y,1/2+z
5 1/2+x,1/2+y,z
6 1/2-x,1/2+y,1/2-z
7 1/2-x,1/2-y,-z
8 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 0.15938(4) 0.58242(10) -0.00444(4) 0.0600(2) Uani . . 1.000
S S2 0.14589(4) 0.94002(13) -0.11023(5) 0.0802(3) Uani . . 1.000
O O1 0.06021(9) 0.1385(3) 0.18770(11) 0.0619(7) Uani . . 1.000
O O2 0.01091(8) 0.7729(2) 0.06117(9) 0.0516(6) Uani . . 1.000
N N1 0.06936(9) 0.8655(3) -0.02055(10) 0.0467(7) Uani . . 1.000
C C1 0.14189(11) 0.2372(3) 0.12922(12) 0.0389(7) Uani . . 1.000
C C2 0.12016(12) 0.0955(3) 0.17442(12) 0.0428(8) Uani . . 1.000
C C3 0.15870(12) -0.0790(4) 0.20299(13) 0.0485(8) Uani . . 1.000
C C4 0.21827(13) -0.1171(4) 0.18715(13) 0.0531(9) Uani . . 1.000
C C5 0.24140(13) 0.0198(4) 0.14359(14) 0.0566(9) Uani . . 1.000
C C6 0.20350(13) 0.1944(4) 0.11522(13) 0.0512(9) Uani . . 1.000
C C7 0.10043(11) 0.4192(3) 0.10120(12) 0.0422(8) Uani . . 1.000
C C8 0.10408(11) 0.5631(3) 0.05020(12) 0.0396(7) Uani . . 1.000
C C9 0.05620(11) 0.7391(3) 0.03308(12) 0.0405(8) Uani . . 1.000
C C10 0.12115(12) 0.8120(4) -0.04789(13) 0.0502(8) Uani . . 1.000
O O11 -0.0100(5) 0.8280(6) 0.2318(3) 0.066(3) Uani . . 0.500
C C11 0.014(2) 0.6235(11) 0.262(3) 0.112(14) Uani . . 0.500
H H1N 0.04538 0.97578 -0.03643 0.0561 Uiso . . 1.000
H H1O 0.04906 0.03909 0.20888 0.0743 Uiso . . 1.000
H H3 0.14403 -0.17151 0.23327 0.0582 Uiso . . 1.000
H H4 0.24344 -0.23670 0.20598 0.0637 Uiso . . 1.000
H H5 0.28232 -0.00571 0.13348 0.0680 Uiso . . 1.000
H H6 0.21932 0.28673 0.08585 0.0614 Uiso . . 1.000
H H7 0.06521 0.44009 0.12207 0.0507 Uiso . . 1.000
H H11 -0.035(3) 0.804(7) 0.1868(16) 0.0792 Uiso . . 0.500
H H11A -0.012(4) 0.500(7) 0.244(5) 0.1677 Uiso . . 0.500
H H11B 0.019(4) 0.608(13) 0.316(4) 0.1677 Uiso . . 0.500
H H11C 0.058(3) 0.572(11) 0.265(5) 0.1677 Uiso . . 0.500
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
C8 S1 C10 . . . 92.67(11) no
C2 O1 H1O . . . 109.00 no
C11 O11 H11 . . . 104(4) no
C9 N1 C10 . . . 118.3(2) no
C10 N1 H1N . . . 121.00 no
C9 N1 H1N . . . 121.00 no
C2 C1 C7 . . . 118.7(2) no
C2 C1 C6 . . . 117.4(2) no
C6 C1 C7 . . . 123.9(2) no
O1 C2 C3 . . . 122.6(2) no
O1 C2 C1 . . . 116.96(19) no
C1 C2 C3 . . . 120.4(2) no
C2 C3 C4 . . . 120.5(2) no
C3 C4 C5 . . . 120.6(2) no
C4 C5 C6 . . . 119.3(3) no
C1 C6 C5 . . . 121.8(2) no
C1 C7 C8 . . . 130.9(2) no
S1 C8 C9 . . . 109.51(15) no
C7 C8 C9 . . . 120.2(2) no
S1 C8 C7 . . . 130.34(18) no
N1 C9 C8 . . . 109.96(19) no
O2 C9 C8 . . . 126.50(19) no
O2 C9 N1 . . . 123.54(19) no
S1 C10 S2 . . . 124.08(16) no
S2 C10 N1 . . . 126.4(2) no
S1 C10 N1 . . . 109.52(17) no
C4 C3 H3 . . . 120.00 no
C2 C3 H3 . . . 120.00 no
C3 C4 H4 . . . 120.00 no
C5 C4 H4 . . . 120.00 no
C6 C5 H5 . . . 120.00 no
C4 C5 H5 . . . 120.00 no
C1 C6 H6 . . . 119.00 no
C5 C6 H6 . . . 119.00 no
C1 C7 H7 . . . 115.00 no
C8 C7 H7 . . . 115.00 no
O11 C11 H11A . . . 123(6) no
O11 C11 H11B . . . 113(6) no
O11 C11 H11C . . . 123(6) no
H11A C11 H11B . . . 98(8) no
H11A C11 H11C . . . 98(7) no
H11B C11 H11C . . . 97(8) 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 C8 . . 1.745(2) no
S1 C10 . . 1.744(3) no
S2 C10 . . 1.622(3) no
O1 C2 . . 1.356(3) no
O2 C9 . . 1.219(3) no
O1 H1O . . 0.8200 no
O11 C11 . . 1.45(2) no
O11 H11 . . 0.84(3) no
N1 C9 . . 1.373(3) no
N1 C10 . . 1.357(3) no
N1 H1N . . 0.8600 no
C1 C7 . . 1.443(3) no
C1 C2 . . 1.402(3) no
C1 C6 . . 1.395(4) no
C2 C3 . . 1.378(3) no
C3 C4 . . 1.365(4) no
C4 C5 . . 1.375(4) no
C5 C6 . . 1.372(4) no
C7 C8 . . 1.340(3) no
C8 C9 . . 1.466(3) no
C3 H3 . . 0.9300 no
C4 H4 . . 0.9300 no
C5 H5 . . 0.9300 no
C6 H6 . . 0.9300 no
C7 H7 . . 0.9300 no
C11 H11A . . 0.96(6) no
C11 H11B . . 0.97(9) no
C11 H11C . . 0.95(8) 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
N1 H1N O2 3_575 0.86 1.95 2.811(2) 173 yes
O1 H1O O11 1_545 0.82 1.95 2.735(7) 159 yes
O1 H1O O11 2_545 0.82 2.06 2.871(7) 169 yes
O11 H11 S2 3_575 0.84(3) 2.80(5) 3.317(8) 122(4) yes
C6 H6 S1 . 0.93 2.57 3.264(3) 132 yes
C4 H4 Cg2 6_545 0.93 2.81 3.599(3) 143 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
C10 S1 C8 C7 . . . . 179.8(2) no
C10 S1 C8 C9 . . . . 0.0(2) no
C8 S1 C10 S2 . . . . 179.12(17) no
C8 S1 C10 N1 . . . . 0.05(18) no
C10 N1 C9 O2 . . . . -179.9(2) no
C10 N1 C9 C8 . . . . 0.1(3) no
C9 N1 C10 S1 . . . . -0.1(3) no
C9 N1 C10 S2 . . . . -179.14(18) no
C6 C1 C2 O1 . . . . 180.0(2) no
C6 C1 C2 C3 . . . . -0.4(3) no
C7 C1 C2 O1 . . . . 1.1(3) no
C7 C1 C2 C3 . . . . -179.3(2) no
C2 C1 C6 C5 . . . . 0.7(3) no
C7 C1 C6 C5 . . . . 179.5(2) no
C2 C1 C7 C8 . . . . -170.5(2) no
C6 C1 C7 C8 . . . . 10.7(4) no
O1 C2 C3 C4 . . . . 179.1(2) no
C1 C2 C3 C4 . . . . -0.5(3) no
C2 C3 C4 C5 . . . . 1.2(4) no
C3 C4 C5 C6 . . . . -0.8(4) no
C4 C5 C6 C1 . . . . -0.1(4) no
C1 C7 C8 S1 . . . . 2.0(4) no
C1 C7 C8 C9 . . . . -178.2(2) no
S1 C8 C9 O2 . . . . 179.96(19) no
S1 C8 C9 N1 . . . . -0.1(2) no
C7 C8 C9 O2 . . . . 0.1(3) no
C7 C8 C9 N1 . . . . -179.90(19) no
