#------------------------------------------------------------------------------
#$Date: 2011-09-17 22:27:16 +0200 (Sat, 17 Sep 2011) $
#$Revision: 26029 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008188.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_2008188
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1999
_journal_volume 55
_publ_section_title
;
3,4-Bis(2-chlorophenyl)-1,2,4-1H-triazole-5(4H)-thione
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
loop_
_publ_author_name
  'Kandasamy Chinnakali'
  'Hoong-Kun Fun'
  'Annamalai Senthilvelan'
  'Vayalakkavoor T. Ramakrishnan'
_chemical_formula_sum  'C14 H9 Cl2 N3 S'
_chemical_formula_iupac  'C14 H9 Cl2 N3 S'
_chemical_formula_weight  322.20
_symmetry_cell_setting  monoclinic
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, 1/2-y, z+1/2'
_cell_length_a  7.03770(10)
_cell_length_b  25.6325(2)
_cell_length_c  8.77690(10)
_cell_angle_alpha  90.00
_cell_angle_beta  108.7310(10)
_cell_angle_gamma  90.00
_cell_volume  1499.44(3)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.427
_diffrn_ambient_temperature  293(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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
  Cl1 0.03522(16) 0.62467(5) 0.02054(14) 0.0835(4) Uani d . 1 . . Cl
  S1 0.15511(17) 0.48371(4) 0.31030(13) 0.0677(4) Uani d . 1 . . S
  N1 0.2960(4) 0.58400(11) 0.3351(3) 0.0464(7) Uani d . 1 . . N
  N2 0.1927(5) 0.61835(13) 0.5255(4) 0.0681(10) Uani d . 1 . . N
  N3 0.1363(5) 0.56682(12) 0.4974(3) 0.0594(8) Uani d . 1 . . N
  H3A 0.0690 0.5506 0.5490 0.071 Uiso calc R 1 . . H
  C1 0.1957(5) 0.54426(14) 0.3828(4) 0.0478(8) Uani d . 1 . . C
  C2 0.2904(6) 0.62752(15) 0.4246(4) 0.0568(10) Uani d D 1 . . C
  C3 0.3782(5) 0.58031(13) 0.2048(4) 0.0447(8) Uani d . 1 . . C
  C4 0.2702(5) 0.59841(14) 0.0546(4) 0.0511(9) Uani d . 1 . . C
  C5 0.3475(7) 0.59464(17) -0.0718(4) 0.0685(12) Uani d . 1 . . C
  H5A 0.2747 0.6069 -0.1736 0.082 Uiso calc R 1 A . H
  C6 0.5340(8) 0.5724(2) -0.0443(6) 0.0832(15) Uani d . 1 . . C
  H6A 0.5868 0.5696 -0.1284 0.100 Uiso calc R 1 . . H
  C7 0.6401(7) 0.5549(2) 0.1026(7) 0.0822(14) Uani d . 1 . . C
  H7A 0.7665 0.5405 0.1188 0.099 Uiso calc R 1 A . H
  C8 0.5650(6) 0.55768(17) 0.2310(5) 0.0643(10) Uani d . 1 . . C
  H8A 0.6381 0.5447 0.3317 0.077 Uiso calc R 1 . . H
  Cl2A 0.7182(3) 0.64647(10) 0.5802(4) 0.1049(8) Uani d PDU 0.62 A 1 Cl
  C9A 0.3573(11) 0.6821(3) 0.4017(13) 0.0462(17) Uani d PDU 0.62 A 1 C
  C10A 0.2301(15) 0.7214(3) 0.3154(11) 0.069(2) Uani d PDU 0.62 A 1 C
  H10A 0.0931 0.7151 0.2725 0.083 Uiso calc PR 0.62 A 1 H
  C11A 0.3059(17) 0.7699(3) 0.2931(10) 0.089(2) Uani d PDU 0.62 A 1 C
  H11A 0.2203 0.7959 0.2358 0.106 Uiso calc PR 0.62 A 1 H
  C12A 0.5011(17) 0.7788(4) 0.3542(15) 0.096(3) Uani d PDU 0.62 A 1 C
  H12A 0.5506 0.8111 0.3366 0.116 Uiso calc PR 0.62 A 1 H
  C13A 0.6327(15) 0.7423(4) 0.442(2) 0.089(3) Uani d PDU 0.62 A 1 C
  H13A 0.7688 0.7497 0.4859 0.107 Uiso calc PR 0.62 A 1 H
  C14A 0.5568(13) 0.6939(3) 0.4634(11) 0.070(2) Uani d PDU 0.62 A 1 C
  Cl2B 0.0831(7) 0.72391(17) 0.3320(6) 0.1209(15) Uani d PDU 0.38 A 2 Cl
  C9B 0.4341(17) 0.6701(4) 0.422(2) 0.056(3) Uani d PDU 0.38 A 2 C
  C10B 0.6413(19) 0.6683(6) 0.4667(14) 0.071(3) Uani d PDU 0.38 A 2 C
  H10B 0.7072 0.6368 0.4996 0.085 Uiso calc PR 0.38 A 2 H
  C11B 0.751(2) 0.7124(6) 0.4634(19) 0.102(4) Uani d PDU 0.38 A 2 C
  H11B 0.8900 0.7101 0.4893 0.122 Uiso calc PR 0.38 A 2 H
  C12B 0.660(3) 0.7580(8) 0.423(6) 0.137(10) Uani d PDU 0.38 A 2 C
  H12B 0.7360 0.7879 0.4249 0.164 Uiso calc PR 0.38 A 2 H
  C13B 0.456(3) 0.7613(7) 0.380(3) 0.123(7) Uani d PDU 0.38 A 2 C
  H13B 0.3911 0.7931 0.3488 0.148 Uiso calc PR 0.38 A 2 H
  C14B 0.345(2) 0.7160(6) 0.382(2) 0.086(5) Uani d PDU 0.38 A 2 C
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 0.0681(7) 0.1035(10) 0.0761(7) 0.0109(6) 0.0190(6) 0.0119(6)
  S1 0.0996(8) 0.0520(6) 0.0789(7) -0.0152(5) 0.0669(6) -0.0075(5)
  N1 0.0579(16) 0.0506(17) 0.0390(14) -0.0099(13) 0.0274(12) 0.0002(12)
  N2 0.105(3) 0.062(2) 0.0575(19) -0.0217(18) 0.0533(18) -0.0093(15)
  N3 0.085(2) 0.056(2) 0.0535(17) -0.0175(16) 0.0451(16) -0.0061(14)
  C1 0.0584(19) 0.054(2) 0.0391(16) -0.0053(16) 0.0268(15) 0.0061(15)
  C2 0.081(2) 0.057(2) 0.0404(17) -0.0173(19) 0.0307(17) -0.0037(16)
  C3 0.0504(18) 0.052(2) 0.0400(17) -0.0128(15) 0.0256(15) -0.0010(14)
  C4 0.058(2) 0.055(2) 0.0472(19) -0.0122(17) 0.0260(16) -0.0035(16)
  C5 0.095(3) 0.075(3) 0.046(2) -0.026(2) 0.037(2) -0.0025(19)
  C6 0.099(3) 0.095(4) 0.084(3) -0.028(3) 0.070(3) -0.018(3)
  C7 0.069(3) 0.087(3) 0.113(4) -0.004(2) 0.061(3) -0.005(3)
  C8 0.057(2) 0.069(3) 0.077(3) -0.0026(19) 0.034(2) 0.005(2)
  Cl2A 0.0715(12) 0.0887(17) 0.135(2) 0.0121(11) 0.0061(13) -0.0095(15)
  C9A 0.062(4) 0.038(4) 0.052(4) -0.001(3) 0.037(4) -0.002(3)
  C10A 0.093(5) 0.039(4) 0.085(7) 0.011(4) 0.041(5) 0.006(3)
  C11A 0.137(6) 0.044(4) 0.081(5) 0.009(5) 0.029(5) 0.020(4)
  C12A 0.139(7) 0.054(6) 0.121(8) -0.018(5) 0.077(7) 0.000(5)
  C13A 0.085(6) 0.063(6) 0.132(9) -0.022(4) 0.054(6) -0.024(6)
  C14A 0.070(4) 0.044(4) 0.103(6) -0.002(3) 0.036(4) -0.011(4)
  Cl2B 0.113(3) 0.091(3) 0.152(4) 0.038(2) 0.032(3) 0.003(3)
  C9B 0.072(7) 0.046(6) 0.066(9) -0.006(5) 0.046(9) -0.020(6)
  C10B 0.076(7) 0.075(8) 0.057(7) -0.026(6) 0.014(7) 0.003(7)
  C11B 0.096(9) 0.097(10) 0.130(12) -0.042(7) 0.060(9) -0.038(9)
  C12B 0.161(12) 0.073(10) 0.19(3) -0.051(11) 0.08(2) -0.017(16)
  C13B 0.164(11) 0.053(9) 0.17(2) -0.010(9) 0.083(18) 0.017(11)
  C14B 0.104(8) 0.061(8) 0.114(15) 0.004(7) 0.064(11) 0.008(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 C4 . 1.720(4) yes
  S1 C1 . 1.667(4) yes
  N1 C2 . 1.372(4) yes
  N1 C1 . 1.379(4) yes
  N1 C3 . 1.442(4) yes
  N2 C2 . 1.306(4) yes
  N2 N3 . 1.378(4) yes
  N3 C1 . 1.338(4) yes
  N3 H3A . 0.8600 ?
  C2 C9B . 1.492(9) yes
  C2 C9A . 1.510(7) yes
  C3 C4 . 1.373(5) ?
  C3 C8 . 1.386(5) ?
  C4 C5 . 1.388(5) ?
  C5 C6 . 1.379(7) ?
  C5 H5A . 0.9300 ?
  C6 C7 . 1.343(7) ?
  C6 H6A . 0.9300 ?
  C7 C8 . 1.392(6) ?
  C7 H7A . 0.9300 ?
  C8 H8A . 0.9300 ?
  Cl2A C14A . 1.752(9) yes
  C9A C14A . 1.367(10) ?
  C9A C10A . 1.398(10) ?
  C10A C11A . 1.391(10) ?
  C10A H10A . 0.9300 ?
  C11A C12A . 1.324(14) ?
  C11A H11A . 0.9300 ?
  C12A C13A . 1.367(12) ?
  C12A H12A . 0.9300 ?
  C13A C14A . 1.387(12) ?
  C13A H13A . 0.9300 ?
  Cl2B C14B . 1.762(14) ?
  C9B C14B . 1.328(14) ?
  C9B C10B . 1.384(14) ?
  C10B C11B . 1.375(14) ?
  C10B H10B . 0.9300 ?
  C11B C12B . 1.326(19) ?
  C11B H11B . 0.9300 ?
  C12B C13B . 1.370(16) ?
  C12B H12B . 0.9300 ?
  C13B C14B . 1.404(17) ?
  C13B H13B . 0.9300 ?
_cod_database_code 2008188