#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/75/2217542.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_2217542
loop_
_publ_author_name
'Sun, Hong-Shun'
'Xu, Ye-Ming'
'He, Wei'
'Tang, Shi-Gui'
'Guo, Cheng'
_publ_section_title
;
 (Z)-5-(4-Fluorobenzylidene)-1,3-thiazolidine-2,4-dione
;
_journal_coeditor_code           HK2407
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o524
_journal_page_last               o524
_journal_paper_doi               10.1107/S1600536807068316
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C10 H6 F N O2 S'
_chemical_formula_moiety         'C10 H6 F N O2 S'
_chemical_formula_sum            'C10 H6 F N O2 S'
_chemical_formula_weight         223.22
_chemical_name_systematic
;
(Z)-5-(4-Fluorobenzylidene)-1,3-thiazolidine-2,4-dione
;
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_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            16
_cell_length_a                   26.519(5)
_cell_length_b                   36.509(7)
_cell_length_c                   3.8490(8)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_cell_volume                     3726.5(13)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_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 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Enraf--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  0.0422
_diffrn_reflns_av_sigmaI/netI    0.0918
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            2087
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.90
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.338
_exptl_absorpt_correction_T_max  0.9670
_exptl_absorpt_correction_T_min  0.9054
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorles
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.658
_refine_ls_abs_structure_details 'Flack (1983), no Friedel pairs'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1059
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0531
_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)+(0.05P)²+3P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1207
_reflns_number_gt                790
_reflns_number_total             1059
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2407.cif
_cod_data_source_block           I
_cod_original_cell_volume        3726.6(13)
_cod_database_code               2217542
_cod_database_fobs_code          2217542
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,z
1/4-x,1/4+y,1/4+z
3/4+x,3/4-y,1/4+z
x,1/2+y,1/2+z
-x,1/2-y,1/2+z
1/4-x,3/4+y,3/4+z
3/4+x,1/4-y,3/4+z
1/2+x,y,1/2+z
1/2-x,-y,1/2+z
3/4-x,1/4+y,3/4+z
1/4+x,3/4-y,3/4+z
1/2+x,1/2+y,z
1/2-x,1/2-y,z
3/4-x,3/4+y,1/4+z
1/4+x,1/4-y,1/4+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
S S 0.08943(4) -0.00189(3) -0.0089(5) 0.0379(3) Uani d . 1
F F -0.06109(11) 0.13395(8) 0.6207(12) 0.0681(12) Uani d . 1
O O1 0.13745(13) -0.05739(9) -0.3062(14) 0.0619(12) Uani d . 1
O O2 0.21942(10) 0.03754(8) 0.2142(14) 0.0493(10) Uani d . 1
N N 0.18501(14) -0.01228(9) -0.0627(14) 0.0425(11) Uani d . 1
H H0A 0.2136 -0.0219 -0.1150 0.051 Uiso calc R 1
C C1 -0.01787(17) 0.11646(12) 0.5430(15) 0.0416(12) Uani d . 1
C C2 0.02675(18) 0.13443(12) 0.5921(16) 0.0484(15) Uani d . 1
H H2A 0.0273 0.1584 0.6744 0.058 Uiso calc R 1
C C3 0.07078(19) 0.11621(11) 0.5166(17) 0.0444(13) Uani d . 1
H H3A 0.1015 0.1278 0.5559 0.053 Uiso calc R 1
C C4 0.07035(16) 0.08082(10) 0.3826(13) 0.0346(11) Uani d . 1
C C5 0.02378(16) 0.06382(12) 0.3314(15) 0.0400(12) Uani d . 1
H H5A 0.0225 0.0402 0.2421 0.048 Uiso calc R 1
C C6 -0.02016(15) 0.08195(12) 0.4125(16) 0.0452(14) Uani d . 1
H H6A -0.0512 0.0707 0.3782 0.054 Uiso calc R 1
C C7 0.11827(16) 0.06366(11) 0.3095(14) 0.0352(10) Uani d . 1
H H7A 0.1462 0.0772 0.3782 0.042 Uiso calc R 1
C C8 0.12929(15) 0.03151(11) 0.1597(14) 0.0317(10) Uani d . 1
C C9 0.18224(17) 0.02026(11) 0.1107(15) 0.0370(12) Uani d . 1
C C10 0.14053(17) -0.02927(12) -0.1510(17) 0.0450(13) Uani d . 1
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
S 0.0303(5) 0.0391(5) 0.0444(6) -0.0005(4) 0.0015(7) -0.0028(6)
F 0.0400(16) 0.0705(18) 0.094(3) 0.0212(14) 0.003(2) -0.024(2)
O1 0.058(2) 0.0465(17) 0.081(3) 0.0105(16) 0.000(3) -0.026(2)
O2 0.0267(16) 0.0444(16) 0.077(3) 0.0002(12) -0.0039(19) 0.001(2)
N 0.0295(18) 0.0403(18) 0.058(3) 0.0068(15) 0.001(2) 0.001(2)
C1 0.033(2) 0.051(2) 0.041(3) 0.012(2) 0.003(2) -0.009(3)
C2 0.047(3) 0.042(2) 0.056(4) 0.012(2) -0.009(3) -0.018(3)
C3 0.047(3) 0.036(2) 0.050(3) -0.0028(19) -0.002(3) -0.007(3)
C4 0.031(2) 0.036(2) 0.036(3) 0.0030(17) -0.002(2) -0.002(2)
C5 0.035(2) 0.038(2) 0.047(3) 0.0012(17) -0.001(2) -0.006(2)
C6 0.0209(18) 0.056(3) 0.058(4) -0.0019(18) 0.007(2) -0.018(3)
C7 0.030(2) 0.042(2) 0.033(3) -0.0057(17) 0.000(2) 0.008(2)
C8 0.024(2) 0.040(2) 0.031(3) 0.0007(16) -0.003(2) 0.009(2)
C9 0.032(2) 0.037(2) 0.042(3) 0.0039(18) -0.001(2) 0.011(2)
C10 0.038(2) 0.042(2) 0.055(4) 0.0065(19) -0.002(3) 0.002(3)
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 S C10 92.6(2)
C9 N C10 117.9(4)
C9 N H0A 121.1
C10 N H0A 121.1
F C1 C6 119.0(4)
F C1 C2 118.6(4)
C6 C1 C2 122.4(4)
C1 C2 C3 118.3(4)
C1 C2 H2A 120.9
C3 C2 H2A 120.9
C2 C3 C4 121.4(4)
C2 C3 H3A 119.3
C4 C3 H3A 119.3
C3 C4 C5 118.2(4)
C3 C4 C7 117.9(4)
C5 C4 C7 123.9(4)
C6 C5 C4 120.2(4)
C6 C5 H5A 119.9
C4 C5 H5A 119.9
C1 C6 C5 119.5(4)
C1 C6 H6A 120.3
C5 C6 H6A 120.3
C8 C7 C4 131.0(4)
C8 C7 H7A 114.5
C4 C7 H7A 114.5
C7 C8 C9 120.4(4)
C7 C8 S 129.9(3)
C9 C8 S 109.6(3)
O2 C9 N 124.0(4)
O2 C9 C8 125.1(4)
N C9 C8 110.9(4)
O1 C10 N 124.9(4)
O1 C10 S 126.1(4)
N C10 S 109.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S C8 1.739(4)
S C10 1.770(5)
F C1 1.346(5)
O1 C10 1.191(6)
O2 C9 1.237(5)
N C9 1.364(6)
N C10 1.375(6)
N H0A 0.8600
C1 C6 1.358(6)
C1 C2 1.366(7)
C2 C3 1.375(6)
C2 H2A 0.9300
C3 C4 1.391(6)
C3 H3A 0.9300
C4 C5 1.396(6)
C4 C7 1.445(6)
C5 C6 1.376(6)
C5 H5A 0.9300
C6 H6A 0.9300
C7 C8 1.340(6)
C7 H7A 0.9300
C8 C9 1.475(6)
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
N H0A O2 10_554 0.86 1.98 2.830(5) 171.00
C5 H5A S . 0.93 2.54 3.241(5) 133.00
C7 H7A O2 . 0.93 2.50 2.870(5) 104.00
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
F C1 C2 C3 179.1(5)
C6 C1 C2 C3 -2.2(9)
C1 C2 C3 C4 2.1(9)
C2 C3 C4 C5 -1.0(8)
C2 C3 C4 C7 179.8(5)
C3 C4 C5 C6 0.0(8)
C7 C4 C5 C6 179.1(5)
F C1 C6 C5 179.8(5)
C2 C1 C6 C5 1.2(9)
C4 C5 C6 C1 -0.1(9)
C3 C4 C7 C8 -174.7(5)
C5 C4 C7 C8 6.3(9)
C4 C7 C8 C9 179.3(5)
C4 C7 C8 S 0.6(9)
C10 S C8 C7 177.2(5)
C10 S C8 C9 -1.5(4)
C10 N C9 O2 177.5(5)
C10 N C9 C8 -1.9(6)
C7 C8 C9 O2 3.9(8)
S C8 C9 O2 -177.2(4)
C7 C8 C9 N -176.7(4)
S C8 C9 N 2.2(5)
C9 N C10 O1 178.9(6)
C9 N C10 S 0.7(6)
C8 S C10 O1 -177.6(6)
C8 S C10 N 0.6(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1041377
