#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/43/2204306.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_2204306
loop_
_publ_author_name
'Dege, Necmi'
'Çetin, Ahmet'
'Cansız, Ahmet'
'Şekerci, Memet'
'Cavit, Kazaz'
'Dinçer, Muharrem'
'Büyükgüngör, Orhan'
_publ_section_title
;
 4-Benzyl-3-(2-hydroxyphenyl)-1H-1,2,4-triazole-5(4H)-thione
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1883
_journal_page_last               o1885
_journal_paper_doi               10.1107/S1600536804023682
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C15 H13 N3 O1 S1'
_chemical_formula_moiety         'C15 H13 N3 O1 S1'
_chemical_formula_structural     'C15 H13 N3 O1 S1'
_chemical_formula_sum            'C15 H13 N3 O S'
_chemical_formula_weight         283.34
_chemical_name_systematic
;
4-Benzyl-3-(2-hydroxyphenyl)-1H-1,2,4-triazole-5(4H)-thione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 104.655(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.7387(5)
_cell_length_b                   23.842(3)
_cell_length_c                   10.3045(9)
_cell_measurement_reflns_used    5446
_cell_measurement_temperature    296
_cell_measurement_theta_max      26.04
_cell_measurement_theta_min      1.71
_cell_volume                     1364.0(2)
_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      296
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS-2'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0776
_diffrn_reflns_av_sigmaI/netI    0.0701
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7312
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         1.71
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  0.9875
_exptl_absorpt_correction_T_min  0.8593
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.740
_exptl_crystal_size_mid          0.427
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.257
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.870
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2673
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.870
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0435
_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)+(0.0654P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1087
_reflns_number_gt                1737
_reflns_number_total             2673
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci6452.cif
_cod_data_source_block           III
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C15 H13 N3 O1 S1'
_cod_database_code               2204306
_cod_database_fobs_code          2204306
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 1.36193(10) -0.02084(2) 0.17678(6) 0.05650(18) Uani d . 1 S
O1 0.8270(4) 0.18499(8) -0.17450(19) 0.0874(6) Uani d . 1 O
H1 0.9308 0.1605 -0.1613 0.131 Uiso calc R 1 H
N1 1.0596(3) 0.06973(7) 0.14217(16) 0.0472(4) Uani d . 1 N
N2 1.1363(3) 0.11347(7) -0.03084(17) 0.0531(4) Uani d . 1 N
N3 1.2742(3) 0.06623(7) 0.00063(16) 0.0517(4) Uani d . 1 N
H3 1.3765 0.0556 -0.0426 0.062 Uiso calc R 1 H
C1 0.7406(4) 0.19044(9) -0.0643(3) 0.0653(6) Uani d . 1 C
C2 0.5610(5) 0.22983(11) -0.0708(3) 0.0823(8) Uani d . 1 C
H2 0.5036 0.2502 -0.1494 0.099 Uiso calc R 1 H
C3 0.4662(5) 0.23930(11) 0.0369(4) 0.0851(8) Uani d . 1 C
H3A 0.3450 0.2658 0.0305 0.102 Uiso calc R 1 H
C4 0.5492(5) 0.20992(11) 0.1536(3) 0.0757(7) Uani d . 1 C
H4 0.4867 0.2169 0.2269 0.091 Uiso calc R 1 H
C5 0.7257(4) 0.17008(10) 0.1616(2) 0.0657(6) Uani d . 1 C
H5 0.7812 0.1503 0.2411 0.079 Uiso calc R 1 H
C6 0.8244(4) 0.15849(8) 0.0527(2) 0.0531(5) Uani d . 1 C
C7 1.0053(4) 0.11520(8) 0.0561(2) 0.0482(5) Uani d . 1 C
C8 1.2340(3) 0.03832(8) 0.10510(19) 0.0466(5) Uani d . 1 C
C9 0.9526(4) 0.05143(9) 0.2495(2) 0.0540(5) Uani d . 1 C
H9A 0.9715 0.0111 0.2596 0.065 Uiso calc R 1 H
H9B 0.7813 0.0594 0.2232 0.065 Uiso calc R 1 H
C10 1.0586(3) 0.07848(8) 0.3829(2) 0.0494(5) Uani d . 1 C
C11 1.2717(4) 0.10784(10) 0.4115(2) 0.0621(6) Uani d . 1 C
H11 1.3554 0.1122 0.3458 0.075 Uiso calc R 1 H
C12 1.3628(4) 0.13096(12) 0.5378(2) 0.0725(7) Uani d . 1 C
H12 1.5071 0.1508 0.5562 0.087 Uiso calc R 1 H
C13 1.2414(5) 0.12471(11) 0.6350(2) 0.0699(7) Uani d . 1 C
H13 1.3022 0.1405 0.7193 0.084 Uiso calc R 1 H
C14 1.0306(5) 0.09525(10) 0.6082(2) 0.0691(7) Uani d . 1 C
H14 0.9488 0.0906 0.6748 0.083 Uiso calc R 1 H
C15 0.9384(4) 0.07232(9) 0.4828(2) 0.0618(6) Uani d . 1 C
H15 0.7941 0.0525 0.4652 0.074 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 yes
C8 N1 C7 108.02(15) ?
C8 N1 C9 121.40(16) yes
C7 N1 C9 130.44(16) yes
C7 N2 N3 105.19(16) ?
C8 N3 N2 113.21(15) ?
C8 N3 H3 123.4 ?
N2 N3 H3 123.4 ?
O1 C1 C2 116.8(2) yes
O1 C1 C6 123.3(2) yes
C2 C1 C6 119.9(2) ?
C3 C2 C1 121.0(3) ?
C3 C2 H2 119.5 ?
C1 C2 H2 119.5 ?
C4 C3 C2 120.3(2) ?
C4 C3 H3A 119.8 ?
C2 C3 H3A 119.8 ?
C3 C4 C5 119.6(3) ?
C3 C4 H4 120.2 ?
C5 C4 H4 120.2 ?
C4 C5 C6 121.8(2) ?
C4 C5 H5 119.1 ?
C6 C5 H5 119.1 ?
C1 C6 C5 117.3(2) ?
C1 C6 C7 119.48(19) yes
C5 C6 C7 123.2(2) yes
N2 C7 N1 109.79(17) ?
N2 C7 C6 122.33(18) yes
N1 C7 C6 127.83(17) ?
N3 C8 N1 103.79(17) ?
N3 C8 S1 129.07(15) yes
N1 C8 S1 127.13(15) yes
N1 C9 C10 114.47(16) yes
N1 C9 H9A 108.6 ?
C10 C9 H9A 108.6 ?
N1 C9 H9B 108.6 ?
C10 C9 H9B 108.6 ?
H9A C9 H9B 107.6 ?
C11 C10 C15 118.57(19) ?
C11 C10 C9 123.22(17) ?
C15 C10 C9 118.19(18) ?
C10 C11 C12 120.5(2) ?
C10 C11 H11 119.8 ?
C12 C11 H11 119.8 ?
C13 C12 C11 120.2(2) ?
C13 C12 H12 119.9 ?
C11 C12 H12 119.9 ?
C14 C13 C12 119.9(2) ?
C14 C13 H13 120.1 ?
C12 C13 H13 120.1 ?
C13 C14 C15 120.2(2) ?
C13 C14 H14 119.9 ?
C15 C14 H14 119.9 ?
C14 C15 C10 120.6(2) ?
C14 C15 H15 119.7 ?
C10 C15 H15 119.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C8 1.673(2) yes
O1 C1 1.355(3) yes
O1 H1 0.82 ?
N1 C8 1.379(2) yes
N1 C7 1.385(2) yes
N1 C9 1.461(2) yes
N2 C7 1.308(2) yes
N2 N3 1.368(2) yes
N3 C8 1.334(2) yes
N3 H3 0.86 ?
C1 C2 1.383(3) ?
C1 C6 1.404(3) ?
C2 C3 1.372(4) ?
C2 H2 0.93 ?
C3 C4 1.369(4) ?
C3 H3A 0.93 ?
C4 C5 1.376(3) ?
C4 H4 0.93 ?
C5 C6 1.407(3) ?
C5 H5 0.93 ?
C6 C7 1.458(3) yes
C9 C10 1.500(3) yes
C9 H9A 0.97 ?
C9 H9B 0.97 ?
C10 C11 1.375(3) ?
C10 C15 1.384(3) ?
C11 C12 1.388(3) ?
C11 H11 0.93 ?
C12 C13 1.366(3) ?
C12 H12 0.93 ?
C13 C14 1.365(4) ?
C13 H13 0.93 ?
C14 C15 1.380(3) ?
C14 H14 0.93 ?
C15 H15 0.93 ?
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 3_855 0.86 2.43 3.287(2) 175
O1 H1 N2 . 0.82 1.91 2.631(3) 146
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 -0.2(2) yes
O1 C1 C2 C3 -178.4(2) ?
C6 C1 C2 C3 1.5(4) ?
C1 C2 C3 C4 0.3(4) ?
C2 C3 C4 C5 -1.1(4) ?
C3 C4 C5 C6 0.0(4) ?
O1 C1 C6 C5 177.5(2) ?
C2 C1 C6 C5 -2.5(3) ?
O1 C1 C6 C7 -3.0(3) yes
C2 C1 C6 C7 177.0(2) ?
C4 C5 C6 C1 1.8(3) ?
C4 C5 C6 C7 -177.8(2) ?
N3 N2 C7 N1 0.2(2) ?
N3 N2 C7 C6 -177.20(17) ?
C8 N1 C7 N2 -0.2(2) ?
C9 N1 C7 N2 -175.77(18) ?
C8 N1 C7 C6 177.05(19) ?
C9 N1 C7 C6 1.4(3) yes
C1 C6 C7 N2 17.1(3) yes
C5 C6 C7 N2 -163.3(2) ?
C1 C6 C7 N1 -159.7(2) ?
C5 C6 C7 N1 19.8(3) yes
N2 N3 C8 N1 0.1(2) ?
N2 N3 C8 S1 -179.86(15) ?
C7 N1 C8 N3 0.0(2) ?
C9 N1 C8 N3 176.14(16) ?
C7 N1 C8 S1 179.98(15) ?
C9 N1 C8 S1 -3.9(3) yes
C8 N1 C9 C10 98.6(2) yes
C7 N1 C9 C10 -86.2(3) yes
N1 C9 C10 C11 -14.2(3) yes
N1 C9 C10 C15 167.40(18) ?
C15 C10 C11 C12 -0.3(3) ?
C9 C10 C11 C12 -178.7(2) ?
C10 C11 C12 C13 0.0(4) ?
C11 C12 C13 C14 0.5(4) ?
C12 C13 C14 C15 -0.7(4) ?
C13 C14 C15 C10 0.5(4) ?
C11 C10 C15 C14 0.1(3) ?
C9 C10 C15 C14 178.5(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 20122696
