#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/72/2217264.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_2217264
loop_
_publ_author_name
'Wan, Rong'
'Yin, Li-he'
'Han, Feng'
'Wang, Bin'
'Wang, Jin-tang'
_publ_section_title
2-(2,4-Dichlorophenyl)-3-[5-(3,5-dimethylphenyl)-1,3,4-thiadiazol-2-yl]thiazolidin-4-one
_journal_coeditor_code           RN2029
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o260
_journal_page_last               o260
_journal_paper_doi               10.1107/S1600536807066068
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C19 H15 Cl2 N3 O S2'
_chemical_formula_moiety         'C19 H15 Cl2 N3 O S2'
_chemical_formula_sum            'C19 H15 Cl2 N3 O S2'
_chemical_formula_weight         436.36
_chemical_melting_point          .476E-305
_chemical_name_systematic
;
2-(2,4-Dichlorophenyl)-3-[5-(3,5-dimethylphenyl)-1,3,4-thiadiazol-2-
yl]thiazolidin-4-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                80.60(3)
_cell_angle_beta                 80.82(3)
_cell_angle_gamma                63.92(3)
_cell_formula_units_Z            2
_cell_length_a                   8.1760(16)
_cell_length_b                   9.1650(18)
_cell_length_c                   14.483(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      10
_cell_volume                     956.9(4)
_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, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0442
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4042
_diffrn_reflns_theta_full        25.98
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         1.43
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.572
_exptl_absorpt_correction_T_max  0.8941
_exptl_absorpt_correction_T_min  0.8034
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.450
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3761
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0552
_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+2.5P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1653
_reflns_number_gt                2824
_reflns_number_total             3761
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rn2029.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2217264
_cod_database_fobs_code          2217264
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Cl Cl1 0.6127(2) 0.7754(2) -0.14356(11) 0.0843(5) Uani d . 1
Cl Cl2 1.25961(17) 0.62298(16) -0.02409(9) 0.0667(4) Uani d . 1
S S1 1.13265(18) 0.90179(17) 0.12924(9) 0.0626(4) Uani d . 1
S S2 0.80372(16) 0.67126(13) 0.42066(7) 0.0469(3) Uani d . 1
O O 0.7989(6) 0.9660(4) 0.3520(3) 0.0818(12) Uani d . 1
N N1 0.9137(5) 0.4033(4) 0.3485(2) 0.0522(9) Uani d . 1
N N2 0.9641(5) 0.5066(4) 0.2796(2) 0.0523(9) Uani d . 1
N N3 0.9527(5) 0.7697(4) 0.2528(2) 0.0487(8) Uani d . 1
C C1 0.7096(8) -0.0041(6) 0.5859(4) 0.0672(13) Uani d . 1
H H1B 0.6622 -0.0377 0.6465 0.101 Uiso calc R 1
H H1C 0.8348 -0.0796 0.5727 0.101 Uiso calc R 1
H H1D 0.6386 -0.0023 0.5386 0.101 Uiso calc R 1
C C2 0.6989(6) 0.1640(6) 0.5861(3) 0.0514(11) Uani d . 1
C C3 0.7698(6) 0.2378(5) 0.5073(3) 0.0469(10) Uani d . 1
H H3A 0.8261 0.1815 0.4547 0.056 Uiso calc R 1
C C4 0.7565(6) 0.3936(5) 0.5074(3) 0.0439(9) Uani d . 1
C C5 0.6693(6) 0.4783(6) 0.5844(3) 0.0496(10) Uani d . 1
H H5A 0.6602 0.5831 0.5842 0.059 Uiso calc R 1
C C6 0.5944(6) 0.4091(6) 0.6629(3) 0.0486(10) Uani d . 1
C C7 0.6134(6) 0.2527(6) 0.6616(3) 0.0527(11) Uani d . 1
H H7A 0.5664 0.2048 0.7140 0.063 Uiso calc R 1
C C8 0.4899(7) 0.5073(7) 0.7442(3) 0.0698(14) Uani d . 1
H H8A 0.4485 0.4418 0.7920 0.105 Uiso calc R 1
H H8B 0.3863 0.6025 0.7226 0.105 Uiso calc R 1
H H8C 0.5683 0.5402 0.7698 0.105 Uiso calc R 1
C C9 0.8307(5) 0.4717(5) 0.4236(3) 0.0409(9) Uani d . 1
C C10 0.9149(6) 0.6481(5) 0.3094(3) 0.0443(9) Uani d . 1
C C11 1.0540(6) 0.7385(5) 0.1604(3) 0.0480(10) Uani d . 1
H H11A 1.1602 0.6323 0.1651 0.058 Uiso calc R 1
C C12 0.9563(9) 1.0308(7) 0.2078(4) 0.0745(16) Uani d . 1
H H12A 1.0026 1.0901 0.2380 0.089 Uiso calc R 1
H H12B 0.8546 1.1093 0.1738 0.089 Uiso calc R 1
C C13 0.8942(7) 0.9217(6) 0.2809(3) 0.0576(12) Uani d . 1
C C14 0.9401(6) 0.7419(5) 0.0871(3) 0.0431(9) Uani d . 1
C C15 0.7515(6) 0.7987(5) 0.1026(3) 0.0500(10) Uani d . 1
H H15A 0.6923 0.8314 0.1610 0.060 Uiso calc R 1
C C16 0.6505(6) 0.8074(6) 0.0324(3) 0.0532(11) Uani d . 1
H H16A 0.5239 0.8462 0.0431 0.064 Uiso calc R 1
C C17 0.7404(7) 0.7576(5) -0.0542(3) 0.0538(11) Uani d . 1
C C18 0.9264(6) 0.6968(5) -0.0713(3) 0.0505(10) Uani d . 1
H H18A 0.9855 0.6604 -0.1290 0.061 Uiso calc R 1
C C19 1.0239(6) 0.6911(5) -0.0003(3) 0.0461(10) Uani d . 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C12 S1 C11 92.2(2)
C10 S2 C9 86.20(19)
C9 N1 N2 112.7(3)
C10 N2 N1 110.8(3)
C13 N3 C10 121.6(4)
C13 N3 C11 118.1(3)
C10 N3 C11 120.2(3)
C2 C1 H1B 109.5
C2 C1 H1C 109.5
H1B C1 H1C 109.5
C2 C1 H1D 109.5
H1B C1 H1D 109.5
H1C C1 H1D 109.5
C7 C2 C3 117.9(4)
C7 C2 C1 121.2(4)
C3 C2 C1 120.9(4)
C4 C3 C2 120.5(4)
C4 C3 H3A 119.8
C2 C3 H3A 119.8
C5 C4 C3 119.7(4)
C5 C4 C9 120.0(4)
C3 C4 C9 120.3(4)
C4 C5 C6 121.0(4)
C4 C5 H5A 119.5
C6 C5 H5A 119.5
C7 C6 C5 117.9(4)
C7 C6 C8 121.8(4)
C5 C6 C8 120.2(4)
C6 C7 C2 123.0(4)
C6 C7 H7A 118.5
C2 C7 H7A 118.5
C6 C8 H8A 109.5
C6 C8 H8B 109.5
H8A C8 H8B 109.5
C6 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
N1 C9 C4 124.8(4)
N1 C9 S2 114.6(3)
C4 C9 S2 120.6(3)
N2 C10 N3 120.8(4)
N2 C10 S2 115.7(3)
N3 C10 S2 123.5(3)
N3 C11 C14 113.4(3)
N3 C11 S1 104.4(3)
C14 C11 S1 110.7(3)
N3 C11 H11A 109.4
C14 C11 H11A 109.4
S1 C11 H11A 109.4
C13 C12 S1 107.3(4)
C13 C12 H12A 110.3
S1 C12 H12A 110.3
C13 C12 H12B 110.3
S1 C12 H12B 110.3
H12A C12 H12B 108.5
O C13 N3 124.4(4)
O C13 C12 124.1(4)
N3 C13 C12 111.5(4)
C15 C14 C19 117.8(4)
C15 C14 C11 122.4(4)
C19 C14 C11 119.7(4)
C16 C15 C14 120.9(4)
C16 C15 H15A 119.6
C14 C15 H15A 119.6
C15 C16 C17 119.0(4)
C15 C16 H16A 120.5
C17 C16 H16A 120.5
C18 C17 C16 121.8(4)
C18 C17 Cl1 119.2(4)
C16 C17 Cl1 119.0(4)
C17 C18 C19 118.0(4)
C17 C18 H18A 121.0
C19 C18 H18A 121.0
C18 C19 C14 122.4(4)
C18 C19 Cl2 117.9(3)
C14 C19 Cl2 119.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C17 1.734(5)
Cl2 C19 1.739(4)
S1 C12 1.786(6)
S1 C11 1.841(4)
S2 C10 1.716(4)
S2 C9 1.738(4)
O C13 1.198(6)
N1 C9 1.285(5)
N1 N2 1.401(5)
N2 C10 1.303(5)
N3 C13 1.368(6)
N3 C10 1.391(5)
N3 C11 1.458(5)
C1 C2 1.504(6)
C1 H1B 0.9600
C1 H1C 0.9600
C1 H1D 0.9600
C2 C7 1.376(6)
C2 C3 1.406(6)
C3 C4 1.383(6)
C3 H3A 0.9300
C4 C5 1.378(6)
C4 C9 1.488(5)
C5 C6 1.398(6)
C5 H5A 0.9300
C6 C7 1.375(6)
C6 C8 1.509(6)
C7 H7A 0.9300
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C11 C14 1.507(6)
C11 H11A 0.9800
C12 C13 1.518(6)
C12 H12A 0.9700
C12 H12B 0.9700
C14 C15 1.386(6)
C14 C19 1.388(6)
C15 C16 1.380(6)
C15 H15A 0.9300
C16 C17 1.385(6)
C16 H16A 0.9300
C17 C18 1.365(6)
C18 C19 1.378(6)
C18 H18A 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C15 H15A N3 0.93 2.49 2.842(6) 102 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
C9 N1 N2 C10 0.5(5)
C7 C2 C3 C4 1.3(6)
C1 C2 C3 C4 178.9(4)
C2 C3 C4 C5 -1.5(6)
C2 C3 C4 C9 -179.6(4)
C3 C4 C5 C6 0.2(6)
C9 C4 C5 C6 178.4(4)
C4 C5 C6 C7 1.2(6)
C4 C5 C6 C8 -176.4(4)
C5 C6 C7 C2 -1.4(7)
C8 C6 C7 C2 176.2(4)
C3 C2 C7 C6 0.2(7)
C1 C2 C7 C6 -177.4(4)
N2 N1 C9 C4 178.1(4)
N2 N1 C9 S2 -0.3(5)
C5 C4 C9 N1 -179.9(4)
C3 C4 C9 N1 -1.8(6)
C5 C4 C9 S2 -1.6(5)
C3 C4 C9 S2 176.5(3)
C10 S2 C9 N1 0.0(3)
C10 S2 C9 C4 -178.5(3)
N1 N2 C10 N3 179.3(4)
N1 N2 C10 S2 -0.5(5)
C13 N3 C10 N2 176.7(4)
C11 N3 C10 N2 -2.2(6)
C13 N3 C10 S2 -3.5(6)
C11 N3 C10 S2 177.7(3)
C9 S2 C10 N2 0.3(3)
C9 S2 C10 N3 -179.6(4)
C13 N3 C11 C14 -102.2(4)
C10 N3 C11 C14 76.7(5)
C13 N3 C11 S1 18.4(5)
C10 N3 C11 S1 -162.7(3)
C12 S1 C11 N3 -22.7(3)
C12 S1 C11 C14 99.6(3)
C11 S1 C12 C13 22.1(4)
C10 N3 C13 O -4.5(8)
C11 N3 C13 O 174.4(5)
C10 N3 C13 C12 178.8(4)
C11 N3 C13 C12 -2.4(6)
S1 C12 C13 O 167.6(5)
S1 C12 C13 N3 -15.6(6)
N3 C11 C14 C15 11.2(6)
S1 C11 C14 C15 -105.7(4)
N3 C11 C14 C19 -170.7(3)
S1 C11 C14 C19 72.4(4)
C19 C14 C15 C16 -1.3(6)
C11 C14 C15 C16 176.9(4)
C14 C15 C16 C17 0.3(7)
C15 C16 C17 C18 1.4(7)
C15 C16 C17 Cl1 -177.7(3)
C16 C17 C18 C19 -2.1(6)
Cl1 C17 C18 C19 177.1(3)
C17 C18 C19 C14 1.1(6)
C17 C18 C19 Cl2 -176.9(3)
C15 C14 C19 C18 0.6(6)
C11 C14 C19 C18 -177.6(4)
C15 C14 C19 Cl2 178.6(3)
C11 C14 C19 Cl2 0.4(5)
