#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/03/2210357.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_2210357
loop_
_publ_author_name
'Wan, Rong'
'Wu, Feng'
'Han, Feng'
'Guan, Jian-Ling '
'Zhang, Jin-Jun'
'Wang, Jin-Tang'
_publ_section_title
2-(4-Fluorophenyl)-3-[5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-yl]thiazolidin-4-one
_journal_coeditor_code           OB2050
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3984
_journal_page_last               o3985
_journal_paper_doi               10.1107/S1600536806032636
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C18 H14 F N3 O2 S2'
_chemical_formula_moiety         'C18 H14 F N3 O2 S2'
_chemical_formula_sum            'C18 H14 F N3 O2 S2'
_chemical_formula_weight         387.44
_chemical_melting_point          .513E-305
_chemical_name_systematic
;
2-(4-Fluorophenyl)-3-[5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-yl]thiazolidin-
4-one
;
_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                90.00
_cell_angle_beta                 101.55(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.750(4)
_cell_length_b                   6.3720(13)
_cell_length_c                   31.761(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     3519.5(13)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Siemens, 1996)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0887
_diffrn_reflns_av_sigmaI/netI    0.0353
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            3562
_diffrn_reflns_theta_full        25.97
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         1.31
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.331
_exptl_absorpt_correction_T_max  0.9073
_exptl_absorpt_correction_T_min  0.8791
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.296
_refine_ls_extinction_coef       0.0034(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3449
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0528
_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)+(0.0642P)²+4.2621P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1458
_reflns_number_gt                2562
_reflns_number_total             3449
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob2050.cif
_cod_data_source_block           I
_cod_original_cell_volume        3519.5(12)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               2210357
_cod_database_fobs_code          2210357
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
S S1 0.90946(5) 0.58054(16) 0.67451(3) 0.0657(3) Uani d . 1
S S2 0.72967(4) 0.11650(11) 0.55477(2) 0.0421(2) Uani d . 1
F F 0.58643(14) 0.6857(5) 0.73877(8) 0.1073(10) Uani d . 1
O O1 0.86099(13) 0.0571(3) 0.61388(8) 0.0608(7) Uani d . 1
O O2 0.44110(12) -0.1486(3) 0.39128(7) 0.0508(6) Uani d . 1
N N1 0.80742(13) 0.3815(4) 0.61723(8) 0.0407(6) Uani d . 1
N N2 0.69904(15) 0.5014(4) 0.56896(9) 0.0477(6) Uani d . 1
N N3 0.64372(15) 0.4388(4) 0.53404(9) 0.0480(6) Uani d . 1
C C1 0.6419(2) 0.6637(8) 0.71515(12) 0.0679(11) Uani d . 1
C C2 0.6865(2) 0.4831(8) 0.72159(11) 0.0707(11) Uani d . 1
H H2B 0.6795 0.3826 0.7417 0.085 Uiso calc R 1
C C3 0.7417(2) 0.4588(6) 0.69693(11) 0.0575(9) Uani d . 1
H H3B 0.7729 0.3402 0.7007 0.069 Uiso calc R 1
C C4 0.75155(17) 0.6061(5) 0.66694(9) 0.0427(7) Uani d . 1
C C5 0.70540(19) 0.7841(5) 0.66169(11) 0.0538(8) Uani d . 1
H H5A 0.7117 0.8851 0.6415 0.065 Uiso calc R 1
C C6 0.6502(2) 0.8117(7) 0.68628(13) 0.0668(10) Uani d . 1
H H6A 0.6192 0.9307 0.6829 0.080 Uiso calc R 1
C C7 0.81308(17) 0.5820(5) 0.64034(10) 0.0446(7) Uani d . 1
H H7A 0.8091 0.6979 0.6197 0.054 Uiso calc R 1
C C8 0.92926(19) 0.3136(6) 0.66297(11) 0.0549(8) Uani d . 1
H H8A 0.9771 0.3053 0.6527 0.066 Uiso calc R 1
H H8B 0.9343 0.2293 0.6888 0.066 Uiso calc R 1
C C9 0.86426(17) 0.2327(5) 0.62928(10) 0.0456(7) Uani d . 1
C C10 0.74685(16) 0.3512(4) 0.58271(9) 0.0378(6) Uani d . 1
C C11 0.65188(17) 0.2433(4) 0.52302(10) 0.0399(7) Uani d . 1
C C12 0.60017(16) 0.1392(4) 0.48759(9) 0.0373(6) Uani d . 1
C C13 0.61607(18) -0.0597(5) 0.47280(10) 0.0444(7) Uani d . 1
H H13A 0.6620 -0.1258 0.4850 0.053 Uiso calc R 1
C C14 0.56529(17) -0.1594(5) 0.44058(10) 0.0446(7) Uani d . 1
H H14A 0.5774 -0.2904 0.4309 0.054 Uiso calc R 1
C C15 0.49628(17) -0.0643(4) 0.42269(9) 0.0391(7) Uani d . 1
C C16 0.47926(18) 0.1339(5) 0.43713(10) 0.0455(7) Uani d . 1
H H16A 0.4331 0.1989 0.4251 0.055 Uiso calc R 1
C C17 0.53033(18) 0.2328(5) 0.46893(10) 0.0442(7) Uani d . 1
H H17A 0.5183 0.3647 0.4783 0.053 Uiso calc R 1
C C18 0.4505(2) -0.3635(5) 0.37978(12) 0.0579(9) Uani d . 1
H H18A 0.4082 -0.4045 0.3575 0.087 Uiso calc R 1
H H18B 0.4519 -0.4513 0.4045 0.087 Uiso calc R 1
H H18C 0.4978 -0.3785 0.3697 0.087 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'
F F 0.0171 0.0103 '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
C8 S1 C7 94.71(15)
C10 S2 C11 86.19(14)
C15 O2 C18 117.4(2)
C9 N1 C10 122.1(3)
C9 N1 C7 119.1(3)
C10 N1 C7 118.8(2)
C10 N2 N3 111.6(2)
C11 N3 N2 112.9(3)
C6 C1 F 119.6(4)
C6 C1 C2 123.1(3)
F C1 C2 117.3(4)
C3 C2 C1 117.2(4)
C3 C2 H2B 121.4
C1 C2 H2B 121.4
C4 C3 C2 121.4(4)
C4 C3 H3B 119.3
C2 C3 H3B 119.3
C3 C4 C5 119.2(3)
C3 C4 C7 121.5(3)
C5 C4 C7 119.3(3)
C4 C5 C6 120.3(3)
C4 C5 H5A 119.9
C6 C5 H5A 119.9
C1 C6 C5 118.9(4)
C1 C6 H6A 120.6
C5 C6 H6A 120.6
N1 C7 C4 112.5(2)
N1 C7 S1 104.7(2)
C4 C7 S1 111.2(2)
N1 C7 H7A 109.5
C4 C7 H7A 109.5
S1 C7 H7A 109.5
C9 C8 S1 108.5(2)
C9 C8 H8A 110.0
S1 C8 H8A 110.0
C9 C8 H8B 110.0
S1 C8 H8B 110.0
H8A C8 H8B 108.4
O1 C9 N1 123.1(3)
O1 C9 C8 124.8(3)
N1 C9 C8 112.1(3)
N2 C10 N1 121.0(3)
N2 C10 S2 115.4(2)
N1 C10 S2 123.6(2)
N3 C11 C12 123.5(3)
N3 C11 S2 113.9(2)
C12 C11 S2 122.6(2)
C17 C12 C13 117.8(3)
C17 C12 C11 120.0(3)
C13 C12 C11 122.1(3)
C14 C13 C12 121.4(3)
C14 C13 H13A 119.3
C12 C13 H13A 119.3
C13 C14 C15 119.8(3)
C13 C14 H14A 120.1
C15 C14 H14A 120.1
O2 C15 C14 125.2(3)
O2 C15 C16 115.2(3)
C14 C15 C16 119.6(3)
C17 C16 C15 120.2(3)
C17 C16 H16A 119.9
C15 C16 H16A 119.9
C16 C17 C12 121.1(3)
C16 C17 H17A 119.4
C12 C17 H17A 119.4
O2 C18 H18A 109.5
O2 C18 H18B 109.5
H18A C18 H18B 109.5
O2 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C8 1.789(4)
S1 C7 1.833(3)
S2 C10 1.735(3)
S2 C11 1.737(3)
F C1 1.360(4)
O1 C9 1.218(4)
O2 C15 1.361(4)
O2 C18 1.436(4)
N1 C9 1.381(4)
N1 C10 1.387(4)
N1 C7 1.467(4)
N2 C10 1.295(4)
N2 N3 1.384(4)
N3 C11 1.310(4)
C1 C6 1.343(6)
C1 C2 1.389(6)
C2 C3 1.380(5)
C2 H2B 0.9300
C3 C4 1.373(4)
C3 H3B 0.9300
C4 C5 1.389(4)
C4 C7 1.516(4)
C5 C6 1.382(5)
C5 H5A 0.9300
C6 H6A 0.9300
C7 H7A 0.9800
C8 C9 1.499(5)
C8 H8A 0.9700
C8 H8B 0.9700
C11 C12 1.462(4)
C12 C17 1.396(4)
C12 C13 1.400(4)
C13 C14 1.376(4)
C13 H13A 0.9300
C14 C15 1.383(4)
C14 H14A 0.9300
C15 C16 1.397(4)
C16 C17 1.368(4)
C16 H16A 0.9300
C17 H17A 0.9300
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
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
C7 H7A O1 1_565 0.98 2.49 3.299(4) 140 yes
C13 H13A S2 . 0.93 2.77 3.163(3) 107 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
_geom_torsion_publ_flag
C10 N2 N3 C11 0.3(4) ?
C6 C1 C2 C3 0.4(6) ?
F C1 C2 C3 178.6(3) ?
C1 C2 C3 C4 -0.7(6) ?
C2 C3 C4 C5 0.6(5) ?
C2 C3 C4 C7 178.9(3) ?
C3 C4 C5 C6 -0.2(5) ?
C7 C4 C5 C6 -178.5(3) ?
F C1 C6 C5 -178.2(3) ?
C2 C1 C6 C5 0.0(6) ?
C4 C5 C6 C1 -0.1(5) ?
C9 N1 C7 C4 -111.6(3) ?
C10 N1 C7 C4 71.3(3) ?
C9 N1 C7 S1 9.3(3) yes
C10 N1 C7 S1 -167.9(2) ?
C3 C4 C7 N1 54.8(4) ?
C5 C4 C7 N1 -127.0(3) ?
C3 C4 C7 S1 -62.2(3) ?
C5 C4 C7 S1 116.0(3) ?
C8 S1 C7 N1 -8.0(2) yes
C8 S1 C7 C4 113.7(2) ?
C7 S1 C8 C9 5.5(2) yes
C10 N1 C9 O1 -8.4(5) ?
C7 N1 C9 O1 174.5(3) ?
C10 N1 C9 C8 171.4(3) ?
C7 N1 C9 C8 -5.7(4) yes
S1 C8 C9 O1 178.7(3) ?
S1 C8 C9 N1 -1.2(3) yes
N3 N2 C10 N1 179.3(2) ?
N3 N2 C10 S2 -0.2(3) ?
C9 N1 C10 N2 -172.2(3) ?
C7 N1 C10 N2 4.9(4) ?
C9 N1 C10 S2 7.2(4) ?
C7 N1 C10 S2 -175.7(2) ?
C11 S2 C10 N2 0.0(2) ?
C11 S2 C10 N1 -179.4(3) ?
N2 N3 C11 C12 179.1(3) ?
N2 N3 C11 S2 -0.3(3) ?
C10 S2 C11 N3 0.2(2) ?
C10 S2 C11 C12 -179.2(2) ?
N3 C11 C12 C17 -12.5(4) ?
S2 C11 C12 C17 166.9(2) ?
N3 C11 C12 C13 171.1(3) ?
S2 C11 C12 C13 -9.5(4) ?
C17 C12 C13 C14 0.8(4) ?
C11 C12 C13 C14 177.3(3) ?
C12 C13 C14 C15 -1.1(5) ?
C18 O2 C15 C14 8.7(4) ?
C18 O2 C15 C16 -171.1(3) ?
C13 C14 C15 O2 -178.9(3) ?
C13 C14 C15 C16 0.9(4) ?
O2 C15 C16 C17 179.4(3) ?
C14 C15 C16 C17 -0.4(4) ?
C15 C16 C17 C12 0.1(5) ?
C13 C12 C17 C16 -0.3(4) ?
C11 C12 C17 C16 -176.8(3) ?
