#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/40/2204050.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_2204050
loop_
_publ_author_name
'Genç, Sadık'
'Dege, Necmi'
'Çetin, Ahmet'
'Cansız,  Ahmet'
'Şekerci, Memet'
'Dinçer, Muharrem'
_publ_section_title
;
5-(2-Hydroxyphenyl)-4-(p-tolyl)-2,4-dihydro-1,2,4-triazole-3-thione
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica, Section E'
_journal_page_first              o1339
_journal_page_last               o1341
_journal_paper_doi               10.1107/S1600536804016551
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C15 H13 N3 O S'
_chemical_formula_moiety         'C15 H13 N3 O S'
_chemical_formula_sum            'C15 H13 N3 O S'
_chemical_formula_weight         283.34
_chemical_name_systematic
;
5-(2-Hydroxyphenyl)-4-(p-tolyl)-2,4-dihydro-1,2,4-triazole-3-thione
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.643(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.524(3)
_cell_length_b                   11.3288(18)
_cell_length_c                   9.2310(11)
_cell_measurement_reflns_used    10560
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.20
_cell_measurement_theta_min      1.59
_cell_volume                     2683.7(6)
_computing_cell_refinement       'X-AREA '
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'two-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1428
_diffrn_reflns_av_sigmaI/netI    0.0939
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9354
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.59
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.24
_exptl_absorpt_correction_T_max  0.9784
_exptl_absorpt_correction_T_min  0.9193
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       plate
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.257
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.599
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2636
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0540
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0749P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1338
_refine_ls_wR_factor_ref         0.1478
_reflns_number_gt                1775
_reflns_number_total             2636
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6236.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2204050
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_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
_atom_site_type_symbol
S1 0.01200(2) 0.69821(7) 0.02543(9) 0.0327(3) Uani d . 1 S
O1 0.15575(7) 0.41156(17) -0.3164(2) 0.0368(6) Uani d . 1 O
H1 0.1382 0.4075 -0.2551 0.055 Uiso calc R 1 H
N1 0.09264(7) 0.69074(19) -0.1113(3) 0.0261(6) Uani d . 1 N
N2 0.09765(8) 0.5010(2) -0.1596(3) 0.0319(6) Uani d . 1 N
N3 0.05803(8) 0.5225(2) -0.0939(3) 0.0324(6) Uani d . 1 N
H3 0.0377 0.4683 -0.0759 0.039 Uiso calc R 1 H
C1 0.17960(9) 0.5179(3) -0.3051(3) 0.0299(7) Uani d . 1 C
C2 0.22122(9) 0.5277(3) -0.3695(4) 0.0343(7) Uani d . 1 C
H2 0.2305 0.4634 -0.4199 0.041 Uiso calc R 1 H
C3 0.24902(9) 0.6307(3) -0.3601(4) 0.0362(8) Uani d . 1 C
H3A 0.2770 0.6357 -0.4035 0.043 Uiso calc R 1 H
C4 0.23540(9) 0.7272(3) -0.2859(4) 0.0368(8) Uani d . 1 C
H4 0.2546 0.7968 -0.2776 0.044 Uiso calc R 1 H
C5 0.19327(9) 0.7195(3) -0.2244(4) 0.0332(7) Uani d . 1 C
H5 0.1842 0.7851 -0.1760 0.040 Uiso calc R 1 H
C6 0.16385(9) 0.6166(3) -0.2325(3) 0.0267(6) Uani d . 1 C
C7 0.11891(9) 0.6040(2) -0.1687(3) 0.0266(6) Uani d . 1 C
C8 0.05382(9) 0.6361(2) -0.0602(3) 0.0269(7) Uani d . 1 C
C9 0.09922(9) 0.8174(2) -0.1062(3) 0.0250(6) Uani d . 1 C
C10 0.13459(9) 0.8698(3) 0.0140(3) 0.0295(7) Uani d . 1 C
H10 0.1548 0.8238 0.0904 0.035 Uiso calc R 1 H
C11 0.13906(10) 0.9907(3) 0.0177(3) 0.0316(7) Uani d . 1 C
H11 0.1633 1.0261 0.0963 0.038 Uiso calc R 1 H
C12 0.10809(9) 1.0616(3) -0.0934(3) 0.0291(7) Uani d . 1 C
C13 0.07306(10) 1.0065(3) -0.2112(4) 0.0330(7) Uani d . 1 C
H13 0.0523 1.0522 -0.2869 0.040 Uiso calc R 1 H
C14 0.06843(9) 0.8848(3) -0.2182(4) 0.0317(7) Uani d . 1 C
H14 0.0447 0.8490 -0.2977 0.038 Uiso calc R 1 H
C15 0.11145(10) 1.1944(3) -0.0873(4) 0.0387(8) Uani d . 1 C
H15A 0.1003 1.2224 -0.0023 0.058 Uiso calc R 1 H
H15B 0.0894 1.2269 -0.1772 0.058 Uiso calc R 1 H
H15C 0.1468 1.2184 -0.0785 0.058 Uiso calc R 1 H
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
_geom_angle_publ_flag
C1 O1 H1 109.5 ?
C8 N1 C7 107.6(2) ?
C8 N1 C9 121.8(2) yes
C7 N1 C9 130.5(2) ?
C7 N2 N3 105.2(2) ?
C8 N3 N2 113.3(2) ?
C8 N3 H3 123.3 ?
N2 N3 H3 123.3 ?
O1 C1 C2 116.5(3) ?
O1 C1 C6 123.4(2) yes
C2 C1 C6 120.1(3) ?
C3 C2 C1 121.0(3) ?
C3 C2 H2 119.5 ?
C1 C2 H2 119.5 ?
C2 C3 C4 120.0(3) ?
C2 C3 H3A 120.0 ?
C4 C3 H3A 120.0 ?
C5 C4 C3 119.5(3) ?
C5 C4 H4 120.2 ?
C3 C4 H4 120.2 ?
C4 C5 C6 122.2(3) ?
C4 C5 H5 118.9 ?
C6 C5 H5 118.9 ?
C5 C6 C1 117.1(2) ?
C5 C6 C7 124.2(3) ?
C1 C6 C7 118.7(2) ?
N2 C7 N1 110.0(2) ?
N2 C7 C6 121.4(2) yes
N1 C7 C6 128.6(2) ?
N3 C8 N1 103.8(2) ?
N3 C8 S1 128.4(2) yes
N1 C8 S1 127.9(2) ?
C14 C9 C10 121.0(3) ?
C14 C9 N1 118.9(2) ?
C10 C9 N1 120.1(2) ?
C11 C10 C9 118.8(3) ?
C11 C10 H10 120.6 ?
C9 C10 H10 120.6 ?
C10 C11 C12 121.7(3) ?
C10 C11 H11 119.2 ?
C12 C11 H11 119.2 ?
C13 C12 C11 118.0(3) ?
C13 C12 C15 120.0(3) ?
C11 C12 C15 122.0(3) yes
C14 C13 C12 121.2(3) ?
C14 C13 H13 119.4 ?
C12 C13 H13 119.4 ?
C9 C14 C13 119.3(3) ?
C9 C14 H14 120.3 ?
C13 C14 H14 120.3 ?
C12 C15 H15A 109.5 ?
C12 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C12 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C8 1.671(3) yes
O1 C1 1.353(3) yes
O1 H1 0.8200 ?
N1 C8 1.382(3) ?
N1 C7 1.385(3) ?
N1 C9 1.445(3) yes
N2 C7 1.308(3) ?
N2 N3 1.361(3) ?
N3 C8 1.335(4) ?
N3 H3 0.8600 ?
C1 C2 1.384(4) ?
C1 C6 1.420(4) ?
C2 C3 1.371(4) ?
C2 H2 0.9300 ?
C3 C4 1.387(4) ?
C3 H3A 0.9300 ?
C4 C5 1.378(4) ?
C4 H4 0.9300 ?
C5 C6 1.395(4) ?
C5 H5 0.9300 ?
C6 C7 1.464(4) yes
C9 C14 1.376(4) ?
C9 C10 1.392(4) ?
C10 C11 1.374(4) ?
C10 H10 0.9300 ?
C11 C12 1.396(4) ?
C11 H11 0.9300 ?
C12 C13 1.387(4) ?
C12 C15 1.507(4) yes
C13 C14 1.384(4) ?
C13 H13 0.9300 ?
C14 H14 0.9300 ?
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 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
N3 H3 S1 5_565 0.86 2.41 3.271(3) 174
C14 H14 S1 2_554 0.93 2.83 3.742(3) 168
O1 H1 N2 . 0.82 1.88 2.574(3) 142
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
C7 N2 N3 C8 -0.5(3) ?
O1 C1 C2 C3 -177.9(3) yes
C6 C1 C2 C3 2.3(4) ?
C1 C2 C3 C4 -0.3(4) ?
C2 C3 C4 C5 -1.2(4) ?
C3 C4 C5 C6 0.8(5) ?
C4 C5 C6 C1 1.1(4) ?
C4 C5 C6 C7 179.8(3) ?
O1 C1 C6 C5 177.6(3) yes
C2 C1 C6 C5 -2.6(4) ?
O1 C1 C6 C7 -1.2(4) yes
C2 C1 C6 C7 178.6(2) ?
N3 N2 C7 N1 -0.8(3) ?
N3 N2 C7 C6 179.3(2) ?
C8 N1 C7 N2 1.8(3) ?
C9 N1 C7 N2 -175.3(3) ?
C8 N1 C7 C6 -178.3(3) ?
C9 N1 C7 C6 4.6(5) ?
C5 C6 C7 N2 -169.5(3) ?
C1 C6 C7 N2 9.2(4) yes
C5 C6 C7 N1 10.6(4) ?
C1 C6 C7 N1 -170.7(3) yes
N2 N3 C8 N1 1.5(3) ?
N2 N3 C8 S1 -177.9(2) yes
C7 N1 C8 N3 -1.9(3) ?
C9 N1 C8 N3 175.5(2) ?
C7 N1 C8 S1 177.5(2) ?
C9 N1 C8 S1 -5.1(4) ?
C8 N1 C9 C14 -82.1(3) ?
C7 N1 C9 C14 94.6(3) ?
C8 N1 C9 C10 95.0(3) yes
C7 N1 C9 C10 -88.2(4) ?
C14 C9 C10 C11 -1.3(4) ?
N1 C9 C10 C11 -178.4(2) ?
C9 C10 C11 C12 1.8(4) ?
C10 C11 C12 C13 -1.5(4) ?
C10 C11 C12 C15 177.8(3) yes
C11 C12 C13 C14 0.6(4) ?
C15 C12 C13 C14 -178.7(3) yes
C10 C9 C14 C13 0.4(4) ?
N1 C9 C14 C13 177.6(3) ?
C12 C13 C14 C9 -0.1(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 17831512
