data_2200006
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2005
_journal_volume  61
_journal_page_first  o3599
_journal_page_last  o3601
_publ_section_title
;
\(<i>Z</i>)-3-(2,6-Dichlorophenyl)-1-(pyridin-3-yl)-2-(1<i>H</i>-1,2,4-triazol-
\1-yl)prop- 2-en-1-one
;
loop_
_publ_author_name
  'Liu, Jian-Bing'
  'Dai, Hong'
  'Tao, Wei-Feng'
  'Jin, Zhong'
  'Fang, Jian-Xin'
_chemical_formula_moiety  'C16 H10 Cl2 N4 O'
_chemical_formula_sum  'C16 H10 Cl2 N4 O'
_chemical_formula_iupac  'C16 H10 Cl2 N4 O'
_chemical_formula_weight  345.18
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
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'
_cell_length_a  8.0749(14)
_cell_length_b  19.795(3)
_cell_length_c  10.1321(17)
_cell_angle_alpha  90.00
_cell_angle_beta  98.280(2)
_cell_angle_gamma  90.00
_cell_volume  1602.7(5)
_cell_formula_units_Z  4
_cell_measurement_temperature  294(2)
_exptl_crystal_density_diffrn  1.431
_diffrn_ambient_temperature  294(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 0.53194(6) 0.22862(2) -0.00434(5) 0.05926(17) Uani d . 1 . . Cl
  Cl2 0.26413(7) -0.01068(2) 0.10790(5) 0.06224(18) Uani d . 1 . . Cl
  O1 0.34217(17) 0.17995(8) 0.48814(13) 0.0645(4) Uani d . 1 . . O
  N1 0.17839(16) 0.13916(6) 0.24507(13) 0.0366(3) Uani d . 1 . . N
  N2 0.10677(19) 0.17336(8) 0.13496(16) 0.0528(4) Uani d . 1 . . N
  N3 -0.09093(19) 0.12797(8) 0.24402(17) 0.0532(4) Uani d . 1 . . N
  N4 0.77331(19) 0.02328(8) 0.50587(15) 0.0472(4) Uani d . 1 . . N
  C1 0.4274(2) 0.15470(8) -0.05478(17) 0.0394(4) Uani d . 1 . . C
  C2 0.3780(2) 0.14415(10) -0.18899(18) 0.0493(5) Uani d . 1 . . C
  H2 0.3994 0.1765 -0.2509 0.059 Uiso calc R 1 . . H
  C3 0.2969(2) 0.08540(10) -0.23022(18) 0.0535(5) Uani d . 1 . . C
  H3 0.2647 0.0776 -0.3208 0.064 Uiso calc R 1 . . H
  C4 0.2628(2) 0.03793(10) -0.13900(19) 0.0520(5) Uani d . 1 . . C
  H4 0.2083 -0.0020 -0.1674 0.062 Uiso calc R 1 . . H
  C5 0.3100(2) 0.05014(9) -0.00504(17) 0.0422(4) Uani d . 1 . . C
  C6 0.39462(19) 0.10862(8) 0.04147(15) 0.0355(4) Uani d . 1 . . C
  C7 0.4515(2) 0.12143(8) 0.18426(16) 0.0364(4) Uani d . 1 . . C
  H7 0.5665 0.1217 0.2118 0.044 Uiso calc R 1 . . H
  C8 0.3544(2) 0.13266(8) 0.27722(16) 0.0351(4) Uani d . 1 . . C
  C9 -0.0523(2) 0.16463(11) 0.1403(2) 0.0579(5) Uani d . 1 . . C
  H9 -0.1345 0.1826 0.0762 0.069 Uiso calc R 1 . . H
  C10 0.0572(2) 0.11358(9) 0.30755(19) 0.0454(4) Uani d . 1 . . C
  H10 0.0762 0.0887 0.3862 0.054 Uiso calc R 1 . . H
  C11 0.4217(2) 0.14637(8) 0.41929(16) 0.0401(4) Uani d . 1 . . C
  C12 0.5868(2) 0.11800(8) 0.47684(16) 0.0366(4) Uani d . 1 . . C
  C13 0.6351(2) 0.05341(8) 0.44660(16) 0.0398(4) Uani d . 1 . . C
  H13 0.5668 0.0296 0.3808 0.048 Uiso calc R 1 . . H
  C14 0.8701(2) 0.05943(10) 0.59702(19) 0.0501(5) Uani d . 1 . . C
  H14 0.9676 0.0394 0.6395 0.060 Uiso calc R 1 . . H
  C15 0.8360(2) 0.12404(10) 0.63258(19) 0.0532(5) Uani d . 1 . . C
  H15 0.9096 0.1473 0.6956 0.064 Uiso calc R 1 . . H
  C16 0.6896(2) 0.15388(9) 0.57269(18) 0.0476(4) Uani d . 1 . . C
  H16 0.6610 0.1973 0.5965 0.057 Uiso calc R 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 0.0578(3) 0.0467(3) 0.0701(3) -0.0132(2) -0.0014(2) 0.0085(2)
  Cl2 0.0746(4) 0.0493(3) 0.0644(3) -0.0157(2) 0.0152(3) 0.0077(2)
  O1 0.0566(9) 0.0838(10) 0.0508(8) 0.0319(8) 0.0000(6) -0.0192(7)
  N1 0.0306(7) 0.0379(7) 0.0410(8) 0.0041(6) 0.0045(6) 0.0051(6)
  N2 0.0374(9) 0.0614(10) 0.0585(10) 0.0082(7) 0.0031(7) 0.0252(8)
  N3 0.0357(9) 0.0566(10) 0.0678(11) -0.0036(7) 0.0095(8) 0.0026(8)
  N4 0.0412(9) 0.0476(9) 0.0509(9) 0.0090(7) 0.0002(7) 0.0032(7)
  C1 0.0315(9) 0.0426(9) 0.0439(10) 0.0005(7) 0.0046(7) 0.0033(7)
  C2 0.0468(11) 0.0601(12) 0.0410(10) 0.0032(9) 0.0066(8) 0.0117(8)
  C3 0.0531(12) 0.0686(13) 0.0371(10) 0.0011(10) 0.0011(8) -0.0043(9)
  C4 0.0489(12) 0.0532(11) 0.0515(12) -0.0049(9) -0.0008(9) -0.0107(9)
  C5 0.0384(10) 0.0428(10) 0.0457(10) -0.0013(7) 0.0068(8) 0.0018(8)
  C6 0.0280(9) 0.0414(9) 0.0370(9) 0.0029(7) 0.0048(7) 0.0012(7)
  C7 0.0306(9) 0.0394(9) 0.0384(9) 0.0010(7) 0.0020(7) 0.0021(7)
  C8 0.0325(9) 0.0336(8) 0.0385(9) 0.0037(7) 0.0024(7) 0.0038(7)
  C9 0.0337(11) 0.0688(13) 0.0687(13) 0.0080(9) -0.0008(9) 0.0164(11)
  C10 0.0428(11) 0.0449(10) 0.0502(11) -0.0001(8) 0.0125(8) 0.0051(8)
  C11 0.0398(10) 0.0401(9) 0.0405(9) 0.0077(8) 0.0058(8) 0.0009(7)
  C12 0.0350(9) 0.0413(9) 0.0338(9) 0.0027(7) 0.0061(7) 0.0017(7)
  C13 0.0376(10) 0.0424(10) 0.0387(9) 0.0025(7) 0.0033(7) 0.0011(7)
  C14 0.0365(10) 0.0596(12) 0.0520(11) 0.0061(9) -0.0011(8) 0.0100(9)
  C15 0.0439(11) 0.0595(12) 0.0523(11) -0.0077(9) -0.0064(9) -0.0042(9)
  C16 0.0479(11) 0.0440(10) 0.0495(10) 0.0017(8) 0.0022(9) -0.0059(8)
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 C1 . 1.7292(17) yes
  Cl2 C5 . 1.7373(17) yes
  O1 C11 . 1.212(2) yes
  N1 C10 . 1.339(2) yes
  N1 N2 . 1.3608(19) yes
  N1 C8 . 1.418(2) yes
  N2 C9 . 1.305(2) ?
  N3 C10 . 1.306(2) yes
  N3 C9 . 1.350(2) ?
  N4 C13 . 1.330(2) yes
  N4 C14 . 1.329(2) ?
  C1 C2 . 1.377(2) ?
  C1 C6 . 1.388(2) ?
  C2 C3 . 1.370(3) ?
  C2 H2 . 0.9300 ?
  C3 C4 . 1.374(3) ?
  C3 H3 . 0.9300 ?
  C4 C5 . 1.377(3) ?
  C4 H4 . 0.9300 ?
  C5 C6 . 1.392(2) yes
  C6 C7 . 1.475(2) yes
  C7 C8 . 1.328(2) yes
  C7 H7 . 0.9300 ?
  C8 C11 . 1.489(2) ?
  C9 H9 . 0.9300 yes
  C10 H10 . 0.9300 ?
  C11 C12 . 1.486(2) ?
  C12 C16 . 1.380(2) ?
  C12 C13 . 1.384(2) ?
  C13 H13 . 0.9300 ?
  C14 C15 . 1.367(3) ?
  C14 H14 . 0.9300 ?
  C15 C16 . 1.381(3) ?
  C15 H15 . 0.9300 ?
  C16 H16 . 0.9300 ?