#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/96/2239611.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_2239611
loop_
_publ_author_name
'Sarojini, Balladka K.'
'Manjula, Padmanabha S.'
'Narayana, B.'
'Jasinski, Jerry P.'
_publ_section_title
;
 4-[(E)-(4-Hydroxybenzylidene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione
;
_journal_coeditor_code           SJ5405
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o733
_journal_page_last               o734
_journal_paper_doi               10.1107/S1600536814012215
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C10 H10 N4 O S'
_chemical_formula_moiety         'C10 H10 N4 O S'
_chemical_formula_sum            'C10 H10 N4 O S'
_chemical_formula_weight         234.28
_chemical_name_systematic
;
4-[(E)-(4-Hydroxybenzylidene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                84.104(8)
_cell_angle_beta                 77.719(8)
_cell_angle_gamma                73.358(9)
_cell_formula_units_Z            2
_cell_length_a                   5.7677(5)
_cell_length_b                   7.7233(8)
_cell_length_c                   12.7269(12)
_cell_measurement_reflns_used    1294
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      71.1260
_cell_measurement_theta_min      5.9780
_cell_volume                     530.22(9)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2012)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction        'CrysAlis RED (Agilent, 2012)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL2012 (Sheldrick, 2008)'
_computing_structure_solution
;
SUPERFLIP (Palatinus et al., 2012)
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.0416
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Agilent Eos Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3082
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.332
_diffrn_reflns_theta_min         3.558
_exptl_absorpt_coefficient_mu    2.592
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72306
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO and CrysAlis RED; Agilent, 2012)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_description       prism
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.398
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1987
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0630
_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
;
 w=1/[σ²(Fo²)+(0.0895P)²+0.0331P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1407
_refine_ls_wR_factor_ref         0.1511
_reflns_number_gt                1658
_reflns_number_total             1987
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5405sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        530.23(9)
_cod_database_code               2239611
_cod_database_fobs_code          2239611
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_occupancy
S S1 1.11567(12) 0.19885(9) 0.52135(5) 0.0379(3) Uani d 1
O O1 -0.1143(3) 0.9783(3) 0.86418(16) 0.0377(5) Uani d 1
H H1 -0.2048 1.0077 0.8180 0.057 Uiso calc 1
N N1 0.9248(4) 0.4001(3) 0.76560(17) 0.0283(5) Uani d 1
N N2 1.1501(4) 0.2819(3) 0.72431(16) 0.0256(4) Uani d 1
N N3 1.5264(4) 0.1215(3) 0.73740(18) 0.0307(5) Uani d 1
N N4 1.4752(4) 0.1066(3) 0.63900(17) 0.0300(5) Uani d 1
H H4 1.5835 0.0420 0.5881 0.036 Uiso calc 1
C C1 1.2477(4) 0.1981(3) 0.6267(2) 0.0265(5) Uani d 1
C C2 1.3255(4) 0.2280(3) 0.7878(2) 0.0287(5) Uani d 1
C C3 0.7774(5) 0.4764(3) 0.7032(2) 0.0318(6) Uani d 1
H H3 0.8179 0.4491 0.6293 0.038 Uiso calc 1
C C4 0.5459(4) 0.6061(3) 0.7454(2) 0.0276(5) Uani d 1
C C5 0.3644(5) 0.6680(4) 0.6829(2) 0.0322(6) Uani d 1
H H5 0.3944 0.6250 0.6126 0.039 Uiso calc 1
C C6 0.1427(5) 0.7901(3) 0.7209(2) 0.0316(6) Uani d 1
H H6 0.0210 0.8298 0.6773 0.038 Uiso calc 1
C C7 0.0976(4) 0.8550(3) 0.8236(2) 0.0289(5) Uani d 1
C C8 0.2773(5) 0.7967(3) 0.8869(2) 0.0327(6) Uani d 1
H H8 0.2482 0.8420 0.9566 0.039 Uiso calc 1
C C9 0.4976(5) 0.6732(3) 0.8483(2) 0.0324(6) Uani d 1
H H9 0.6186 0.6329 0.8923 0.039 Uiso calc 1
C C10 1.2826(5) 0.2836(4) 0.9004(2) 0.0384(6) Uani d 1
H H10A 1.1664 0.2240 0.9467 0.058 Uiso calc 1
H H10B 1.2139 0.4151 0.9029 0.058 Uiso calc 1
H H10C 1.4392 0.2481 0.9259 0.058 Uiso calc 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C7 O1 H1 109.5
C3 N1 N2 119.5(2)
N1 N2 C1 133.6(2)
C2 N2 N1 118.42(19)
C2 N2 C1 108.01(19)
C2 N3 N4 104.1(2)
N3 N4 H4 122.8
C1 N4 N3 114.5(2)
C1 N4 H4 122.8
N2 C1 S1 130.18(18)
N4 C1 S1 127.45(18)
N4 C1 N2 102.3(2)
N2 C2 C10 123.3(2)
N3 C2 N2 111.1(2)
N3 C2 C10 125.6(2)
N1 C3 H3 120.2
N1 C3 C4 119.6(2)
C4 C3 H3 120.2
C5 C4 C3 120.1(2)
C5 C4 C9 118.0(2)
C9 C4 C3 121.9(2)
C4 C5 H5 119.3
C6 C5 C4 121.4(2)
C6 C5 H5 119.3
C5 C6 H6 120.1
C5 C6 C7 119.7(2)
C7 C6 H6 120.1
O1 C7 C6 122.3(2)
O1 C7 C8 117.8(2)
C8 C7 C6 119.8(2)
C7 C8 H8 120.1
C9 C8 C7 119.9(2)
C9 C8 H8 120.1
C4 C9 H9 119.5
C8 C9 C4 121.1(2)
C8 C9 H9 119.5
C2 C10 H10A 109.5
C2 C10 H10B 109.5
C2 C10 H10C 109.5
H10A C10 H10B 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.675(2)
O1 H1 0.8400
O1 C7 1.354(3)
N1 N2 1.388(3)
N1 C3 1.267(3)
N2 C1 1.392(3)
N2 C2 1.374(3)
N3 N4 1.369(3)
N3 C2 1.295(3)
N4 H4 0.8800
N4 C1 1.334(3)
C2 C10 1.488(4)
C3 H3 0.9500
C3 C4 1.454(3)
C4 C5 1.396(4)
C4 C9 1.401(4)
C5 H5 0.9500
C5 C6 1.378(4)
C6 H6 0.9500
C6 C7 1.394(4)
C7 C8 1.393(4)
C8 H8 0.9500
C8 C9 1.379(3)
C9 H9 0.9500
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
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
O1 H1 N3 1_365 0.84 1.98 2.804(3) 165.1
N4 H4 S1 2_856 0.88 2.46 3.324(2) 166.1
C3 H3 S1 . 0.95 2.49 3.234(3) 134.9
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
O1 C7 C8 C9 -179.1(2)
N1 N2 C1 S1 -4.7(4)
N1 N2 C1 N4 178.3(2)
N1 N2 C2 N3 -178.6(2)
N1 N2 C2 C10 2.8(4)
N1 C3 C4 C5 -169.2(2)
N1 C3 C4 C9 11.1(4)
N2 N1 C3 C4 -177.4(2)
N3 N4 C1 S1 -175.24(19)
N3 N4 C1 N2 1.9(3)
N4 N3 C2 N2 -0.5(3)
N4 N3 C2 C10 178.1(3)
C1 N2 C2 N3 1.6(3)
C1 N2 C2 C10 -177.0(2)
C2 N2 C1 S1 175.0(2)
C2 N2 C1 N4 -2.0(3)
C2 N3 N4 C1 -0.9(3)
C3 N1 N2 C1 -12.7(4)
C3 N1 N2 C2 167.6(2)
C3 C4 C5 C6 179.6(2)
C3 C4 C9 C8 179.7(3)
C4 C5 C6 C7 0.5(4)
C5 C4 C9 C8 0.0(4)
C5 C6 C7 O1 178.4(3)
C5 C6 C7 C8 0.3(4)
C6 C7 C8 C9 -0.9(4)
C7 C8 C9 C4 0.7(4)
C9 C4 C5 C6 -0.6(4)
