#------------------------------------------------------------------------------
#$Date: 2011-09-28 15:24:46 +0100 (Wed, 28 Sep 2011) $
#$Revision: 26848 $
#$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/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2008321
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1999
_journal_volume 55
_journal_page_first  581
_journal_page_last  582
_publ_section_title
;
3-(2-Chlorophenyl)-4-phenyl-1,2,4-triazole-5-thione
;
loop_
_publ_author_name
  'Kumaran,D.'
  'Ponnuswamy,M.N.'
  'Jayanthi,G.'
  'Ramakrishnan, V.T.'
  'Chinnakali, K.'
  'Fun, H.-K.'
_chemical_formula_sum  'C14 H10 Cl N3 S'
_chemical_formula_weight  287.76
_chemical_melting_point  241
_symmetry_cell_setting  triclinic
_symmetry_space_group_name_H-M  'P -1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  6.9693(2)
_cell_length_b  9.5268(3)
_cell_length_c  11.1032(4)
_cell_angle_alpha  97.5950(10)
_cell_angle_beta  104.2951(5)
_cell_angle_gamma  95.327(2)
_cell_volume  702.04(4)
_cell_formula_units_Z  2
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.361
_diffrn_ambient_temperature  293(2)
_refine_ls_R_factor_obs  0.0478
_refine_ls_wR_factor_obs  0.1126
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_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_
_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) ?
_cod_database_code 2008321