#------------------------------------------------------------------------------
#$Date: 2015-01-23 12:30:19 +0000 (Fri, 23 Jan 2015) $
#$Revision: 130086 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/83/2008321.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_2008321
loop_
_publ_author_name
Kumaran,D.
Ponnuswamy,M.N.
Jayanthi,G.
'Ramakrishnan, V.T.'
'Chinnakali, K.'
'Fun, H.-K.'
_publ_section_title
;
 3-(2-Chlorophenyl)-4-phenyl-1,2,4-triazole-5-thione
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              581
_journal_page_last               582
_journal_paper_doi               10.1107/S0108270198013808
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C14 H10 Cl N3 S'
_chemical_formula_weight         287.76
_chemical_melting_point          241
_chemical_name_systematic
;
4-Phenyl 5-(2-chlorophenyl) 1,2,4-triazole-3-thione
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL
_cell_angle_alpha                97.5950(10)
_cell_angle_beta                 104.2951(5)
_cell_angle_gamma                95.327(2)
_cell_formula_units_Z            2
_cell_length_a                   6.9693(2)
_cell_length_b                   9.5268(3)
_cell_length_c                   11.1032(4)
_cell_measurement_reflns_used    2783
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33.2
_cell_measurement_theta_min      2.66
_cell_volume                     702.04(4)
_computing_cell_refinement       'SAINT (Siemens, 1996b)'
_computing_data_collection       'SMART (Siemens, 1996a)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ZORTEP (Zsolnai, 1997)'
_computing_publication_material  'PARST (Nardelli, 1983, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device
;
Siemens SMART CCD area detector diffractometer
;
_diffrn_measurement_method       '\w scans'
_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  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4631
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.66
_exptl_absorpt_coefficient_mu    0.409
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_correction_T_min  0.834
_exptl_absorpt_correction_type   'empirical (SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_description       Column
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.429
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.043
_refine_ls_goodness_of_fit_obs   1.054
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3133
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_restrained_S_obs      1.054
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_obs          0.0478
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0532P)^2^+0.3068P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1288
_refine_ls_wR_factor_obs         0.1126
_reflns_number_observed          2390
_reflns_number_total             3133
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    bm1285.cif
_[local]_cod_data_source_block   np10
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               2008321
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Cl1 0.0857(6) 0.0980(6) 0.0538(4) -0.0221(5) 0.0106(4) -0.0086(4)
S1 0.0546(3) 0.0411(3) 0.0540(3) 0.0146(2) 0.0297(3) 0.0088(2)
N1 0.0657(13) 0.0360(9) 0.0622(12) 0.0123(9) 0.0351(10) 0.0095(8)
N2 0.0642(12) 0.0351(9) 0.0599(11) 0.0176(9) 0.0355(10) 0.0073(8)
C3 0.0388(11) 0.0369(10) 0.0418(10) 0.0084(8) 0.0151(8) -0.0001(8)
N4 0.0403(9) 0.0310(8) 0.0405(8) 0.0083(7) 0.0175(7) 0.0025(7)
C5 0.0443(11) 0.0333(10) 0.0446(11) 0.0052(8) 0.0167(9) 0.0047(8)
C6 0.0504(12) 0.0395(11) 0.0431(11) 0.0105(9) 0.0192(9) 0.0105(9)
C7 0.0559(15) 0.067(2) 0.0571(14) 0.0013(13) 0.0231(12) 0.0112(13)
C8 0.056(2) 0.112(3) 0.080(2) 0.005(2) 0.031(2) 0.031(2)
C9 0.078(2) 0.126(3) 0.065(2) 0.028(2) 0.043(2) 0.022(2)
C10 0.095(2) 0.097(2) 0.0471(15) 0.025(2) 0.0344(15) 0.004(2)
C11 0.0615(15) 0.0585(14) 0.0430(12) 0.0111(12) 0.0175(11) 0.0064(11)
C12 0.0464(11) 0.0304(9) 0.0332(9) 0.0090(8) 0.0160(8) 0.0023(7)
C13 0.0517(13) 0.0392(11) 0.0458(12) 0.0001(10) 0.0170(10) 0.0000(9)
C14 0.082(2) 0.0328(11) 0.0485(13) -0.0040(11) 0.0266(12) 0.0004(9)
C15 0.093(2) 0.0392(12) 0.0501(13) 0.0253(12) 0.0353(13) 0.0107(10)
C16 0.066(2) 0.0527(14) 0.0504(13) 0.0277(12) 0.0248(12) 0.0143(11)
C17 0.0455(12) 0.0415(11) 0.0440(11) 0.0099(9) 0.0177(9) 0.0073(9)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
Cl1 0.16094(13) 0.16525(10) -0.47723(7) 0.0847(3) Uani d . 1 . Cl
S1 0.05926(9) 0.26959(6) 0.00810(6) 0.0465(2) Uani d . 1 . S
N1 0.2733(3) 0.5049(2) -0.2032(2) 0.0508(5) Uani d . 1 . N
N2 0.1729(3) 0.4780(2) -0.1145(2) 0.0489(5) Uani d . 1 . N
C3 0.1665(3) 0.3438(2) -0.0923(2) 0.0387(5) Uani d . 1 . C
N4 0.2719(2) 0.2809(2) -0.1701(2) 0.0361(4) Uani d . 1 . N
C5 0.3324(3) 0.3838(2) -0.2349(2) 0.0400(5) Uani d . 1 . C
C6 0.4565(3) 0.3631(2) -0.3243(2) 0.0424(5) Uani d . 1 . C
C7 0.6382(4) 0.4481(3) -0.2995(3) 0.0588(7) Uani d . 1 . C
C8 0.7569(5) 0.4358(4) -0.3830(3) 0.0791(9) Uani d . 1 . C
C9 0.6949(5) 0.3367(4) -0.4908(3) 0.0837(10) Uani d . 1 . C
C10 0.5159(6) 0.2507(4) -0.5173(3) 0.0769(9) Uani d . 1 . C
C11 0.3950(4) 0.2657(3) -0.4355(2) 0.0536(6) Uani d . 1 . C
C12 0.3248(3) 0.1381(2) -0.1726(2) 0.0357(4) Uani d . 1 . C
C13 0.1772(4) 0.0221(2) -0.2043(2) 0.0459(5) Uani d . 1 . C
C14 0.2341(5) -0.1137(2) -0.2046(2) 0.0541(6) Uani d . 1 . C
C15 0.4333(5) -0.1316(3) -0.1736(2) 0.0563(6) Uani d . 1 . C
C16 0.5781(4) -0.0155(3) -0.1439(2) 0.0527(6) Uani d . 1 . C
C17 0.5246(3) 0.1212(2) -0.1421(2) 0.0423(5) Uani d . 1 . C
H2 0.111(5) 0.538(3) -0.088(3) 0.071(9) Uiso d . 1 . H
H7 0.687(4) 0.519(3) -0.227(2) 0.050(7) Uiso d . 1 . H
H8 0.874(5) 0.496(4) -0.362(3) 0.089(11) Uiso d . 1 . H
H9 0.779(5) 0.321(4) -0.557(3) 0.100(11) Uiso d . 1 . H
H10 0.479(5) 0.180(4) -0.587(3) 0.093(11) Uiso d . 1 . H
H13 0.031(4) 0.042(3) -0.229(2) 0.058(7) Uiso d . 1 . H
H14 0.139(4) -0.192(3) -0.227(3) 0.065(8) Uiso d . 1 . H
H15 0.470(4) -0.224(3) -0.175(3) 0.072(9) Uiso d . 1 . H
H16 0.714(5) -0.029(4) -0.115(3) 0.086(10) Uiso d . 1 . H
H17 0.618(4) 0.201(3) -0.121(2) 0.046(7) Uiso d . 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'
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
_geom_angle_publ_flag
C5 N1 N2 103.8(2) y
C3 N2 N1 114.0(2) y
C3 N2 H2 125.(2) ?
N1 N2 H2 120.(2) ?
N2 C3 N4 103.4(2) y
N2 C3 S1 128.3(2) y
N4 C3 S1 128.3(2) y
C3 N4 C5 107.5(2) y
C3 N4 C12 125.4(2) y
C5 N4 C12 126.8(2) y
N1 C5 N4 111.3(2) y
N1 C5 C6 123.3(2) y
N4 C5 C6 125.4(2) y
C7 C6 C11 118.3(2) ?
C7 C6 C5 118.9(2) ?
C11 C6 C5 122.7(2) ?
C6 C7 C8 120.9(3) ?
C6 C7 H7 122.7(15) ?
C8 C7 H7 116.4(15) ?
C9 C8 C7 119.7(3) ?
C9 C8 H8 124.(2) ?
C7 C8 H8 117.(2) ?
C10 C9 C8 120.5(3) ?
C10 C9 H9 116.0(19) ?
C8 C9 H9 123.4(19) ?
C9 C10 C11 119.7(3) ?
C9 C10 H10 120.(2) ?
C11 C10 H10 120.(2) ?
C10 C11 C6 120.8(3) ?
C10 C11 Cl1 118.7(2) ?
C6 C11 Cl1 120.4(2) ?
C17 C12 C13 121.6(2) ?
C17 C12 N4 118.4(2) ?
C13 C12 N4 120.1(2) ?
C12 C13 C14 118.4(2) ?
C12 C13 H13 117.4(14) ?
C14 C13 H13 124.1(14) ?
C15 C14 C13 120.5(2) ?
C15 C14 H14 119.6(19) ?
C13 C14 H14 119.9(19) ?
C16 C15 C14 120.4(2) ?
C16 C15 H15 119.8(18) ?
C14 C15 H15 119.7(18) ?
C15 C16 C17 120.1(2) ?
C15 C16 H16 119.(2) ?
C17 C16 H16 120.(2) ?
C12 C17 C16 119.1(2) ?
C12 C17 H17 119.1(15) ?
C16 C17 H17 121.8(16) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C11 . 1.735(3) y
S1 C3 . 1.680(2) y
N1 C5 . 1.295(3) y
N1 N2 . 1.378(3) y
N2 C3 . 1.333(3) y
N2 H2 . 0.81(3) ?
C3 N4 . 1.379(3) y
N4 C5 . 1.384(3) y
N4 C12 . 1.441(2) y
C5 C6 . 1.475(3) y
C6 C7 . 1.383(3) ?
C6 C11 . 1.390(3) ?
C7 C8 . 1.387(4) ?
C7 H7 . 0.95(2) ?
C8 C9 . 1.372(5) ?
C8 H8 . 0.91(3) ?
C9 C10 . 1.371(5) ?
C9 H9 . 1.05(4) ?
C10 C11 . 1.386(4) ?
C10 H10 . 0.92(4) ?
C12 C17 . 1.379(3) ?
C12 C13 . 1.382(3) ?
C13 C14 . 1.388(3) ?
C13 H13 . 1.03(3) ?
C14 C15 . 1.378(4) ?
C14 H14 . 0.91(3) ?
C15 C16 . 1.371(4) ?
C15 H15 . 0.94(3) ?
C16 C17 . 1.387(3) ?
C16 H16 . 0.95(3) ?
C17 H17 . 0.92(2) ?
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
C5 N1 N2 C3 -0.8(3) y
N1 N2 C3 N4 0.9(3) y
N1 N2 C3 S1 180.0(2) y
N2 C3 N4 C5 -0.6(2) y
S1 C3 N4 C5 -179.7(2) y
N2 C3 N4 C12 173.8(2) y
S1 C3 N4 C12 -5.3(3) y
N2 N1 C5 N4 0.4(3) y
N2 N1 C5 C6 -176.9(2) y
C3 N4 C5 N1 0.1(2) y
C12 N4 C5 N1 -174.1(2) y
C3 N4 C5 C6 177.3(2) y
C12 N4 C5 C6 3.0(3) y
N1 C5 C6 C7 56.8(3) ?
N4 C5 C6 C7 -120.1(2) ?
N1 C5 C6 C11 -120.4(3) ?
N4 C5 C6 C11 62.8(3) ?
C11 C6 C7 C8 -0.5(4) ?
C5 C6 C7 C8 -177.8(3) ?
C6 C7 C8 C9 -0.9(5) ?
C7 C8 C9 C10 0.6(6) ?
C8 C9 C10 C11 1.1(6) ?
C9 C10 C11 C6 -2.6(5) ?
C9 C10 C11 Cl1 175.1(3) ?
C7 C6 C11 C10 2.3(4) ?
C5 C6 C11 C10 179.4(3) ?
C7 C6 C11 Cl1 -175.4(2) ?
C5 C6 C11 Cl1 1.8(3) ?
C3 N4 C12 C17 -117.7(2) ?
C5 N4 C12 C17 55.6(3) ?
C3 N4 C12 C13 61.8(3) ?
C5 N4 C12 C13 -124.9(2) ?
C17 C12 C13 C14 0.1(3) ?
N4 C12 C13 C14 -179.4(2) ?
C12 C13 C14 C15 0.2(3) ?
C13 C14 C15 C16 -1.0(4) ?
C14 C15 C16 C17 1.5(4) ?
C13 C12 C17 C16 0.3(3) ?
N4 C12 C17 C16 179.9(2) ?
C15 C16 C17 C12 -1.2(3) ?