data_2014293
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2004
_journal_volume  60
_journal_page_first  o665
_journal_page_last  o667
_publ_section_title
;
3,6-Bis(2-pyridyl)di-1,2,4-triazolo[3,4-a:4',3'-c]phthalazine
;
loop_
_publ_author_name
  'Chang, Wen-Fu'
  'Wen, Yuh-Sheng'
  'Liu, Ling-Kang'
_chemical_formula_moiety  'C20 H12 N8'
_chemical_formula_sum  'C20 H12 N8'
_chemical_formula_iupac  'C20 H12 N8'
_chemical_formula_weight  364.38
_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  8.1968(12)
_cell_length_b  12.390(2)
_cell_length_c  16.409(5)
_cell_angle_alpha  90.00
_cell_angle_beta  91.23(2)
_cell_angle_gamma  90.00
_cell_volume  1666.1(6)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.453
_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
  N1 0.01910(16) 0.84254(11) 0.58191(7) 0.0362(3) Uani d . 1 . . N
  N2 -0.01094(16) 0.85012(11) 0.66450(7) 0.0367(3) Uani d . 1 . . N
  N11 0.13455(18) 0.89263(13) 0.46880(8) 0.0496(4) Uani d . 1 . . N
  N12 0.03278(19) 0.80564(13) 0.45265(8) 0.0501(4) Uani d . 1 . . N
  N14 0.05590(19) 0.89496(13) 0.79008(9) 0.0512(4) Uani d . 1 . . N
  N15 -0.09433(19) 0.84524(13) 0.78929(8) 0.0503(4) Uani d . 1 . . N
  N22 -0.09507(18) 0.61730(13) 0.59863(8) 0.0467(4) Uani d . 1 . . N
  N32 -0.35555(17) 0.79389(12) 0.61635(8) 0.0448(4) Uani d . 1 . . N
  C3 0.1035(2) 0.89927(14) 0.71459(10) 0.0407(4) Uani d . 1 . . C
  C4 0.2364(2) 0.96101(13) 0.68143(10) 0.0393(4) Uani d . 1 . . C
  C5 0.3548(2) 1.00964(15) 0.73134(11) 0.0482(5) Uani d . 1 . . C
  H5 0.3570 0.9968 0.7872 0.058 Uiso calc R 1 . . H
  C6 0.4676(2) 1.07630(17) 0.69763(12) 0.0554(5) Uani d . 1 . . C
  H6 0.5477 1.1080 0.7307 0.066 Uiso calc R 1 . . H
  C7 0.4637(2) 1.09698(17) 0.61491(13) 0.0597(5) Uani d . 1 . . C
  H7 0.5396 1.1441 0.5931 0.072 Uiso calc R 1 . . H
  C8 0.3489(2) 1.04882(16) 0.56413(12) 0.0517(5) Uani d . 1 . . C
  H8 0.3475 1.0630 0.5085 0.062 Uiso calc R 1 . . H
  C9 0.2353(2) 0.97871(14) 0.59715(10) 0.0403(4) Uani d . 1 . . C
  C10 0.1275(2) 0.91271(14) 0.54713(10) 0.0399(4) Uani d . 1 . . C
  C13 -0.0324(2) 0.77310(14) 0.52089(9) 0.0393(4) Uani d . 1 . . C
  C16 -0.1377(2) 0.82081(14) 0.71403(9) 0.0394(4) Uani d . 1 . . C
  C21 -0.1209(2) 0.67138(14) 0.52889(9) 0.0391(4) Uani d . 1 . . C
  C23 -0.1693(2) 0.52197(17) 0.60461(11) 0.0545(5) Uani d . 1 . . C
  H23 -0.1544 0.4832 0.6527 0.065 Uiso calc R 1 . . H
  C24 -0.2666(2) 0.47728(17) 0.54405(12) 0.0568(5) Uani d . 1 . . C
  H24 -0.3150 0.4102 0.5512 0.068 Uiso calc R 1 . . H
  C25 -0.2906(2) 0.53393(17) 0.47285(11) 0.0546(5) Uani d . 1 . . C
  H25 -0.3562 0.5060 0.4310 0.066 Uiso calc R 1 . . H
  C26 -0.2159(2) 0.63285(16) 0.46458(10) 0.0473(5) Uani d . 1 . . C
  H26 -0.2291 0.6728 0.4169 0.057 Uiso calc R 1 . . H
  C31 -0.3006(2) 0.77931(13) 0.69284(10) 0.0392(4) Uani d . 1 . . C
  C33 -0.5062(2) 0.75735(17) 0.59940(12) 0.0532(5) Uani d . 1 . . C
  H33 -0.5466 0.7648 0.5463 0.064 Uiso calc R 1 . . H
  C34 -0.6051(2) 0.70944(16) 0.65571(13) 0.0545(5) Uani d . 1 . . C
  H34 -0.7087 0.6848 0.6409 0.065 Uiso calc R 1 . . H
  C35 -0.5465(2) 0.69901(17) 0.73456(13) 0.0575(5) Uani d . 1 . . C
  H35 -0.6114 0.6689 0.7744 0.069 Uiso calc R 1 . . H
  C36 -0.3919(2) 0.73348(16) 0.75362(11) 0.0505(5) Uani d . 1 . . C
  H36 -0.3492 0.7262 0.8063 0.061 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
  N1 0.0412(7) 0.0434(8) 0.0242(7) 0.0003(7) 0.0040(5) -0.0008(6)
  N2 0.0423(8) 0.0433(8) 0.0246(6) -0.0014(6) 0.0024(6) -0.0012(6)
  N11 0.0535(9) 0.0633(10) 0.0322(8) -0.0080(8) 0.0056(7) 0.0020(7)
  N12 0.0551(9) 0.0647(10) 0.0308(8) -0.0069(8) 0.0054(7) -0.0038(7)
  N14 0.0594(10) 0.0619(10) 0.0324(8) -0.0103(8) 0.0011(7) -0.0043(7)
  N15 0.0587(10) 0.0603(10) 0.0320(8) -0.0103(8) 0.0047(7) -0.0037(7)
  N22 0.0517(9) 0.0516(9) 0.0364(8) -0.0013(7) -0.0045(7) 0.0003(7)
  N32 0.0443(8) 0.0523(9) 0.0378(8) 0.0041(7) 0.0038(6) 0.0029(7)
  C3 0.0465(10) 0.0437(10) 0.0316(8) 0.0006(8) -0.0017(7) -0.0040(7)
  C4 0.0412(9) 0.0392(9) 0.0375(9) 0.0032(8) -0.0003(7) -0.0013(7)
  C5 0.0513(11) 0.0512(11) 0.0417(10) -0.0010(9) -0.0050(8) -0.0011(8)
  C6 0.0505(11) 0.0564(12) 0.0588(12) -0.0088(10) -0.0071(9) -0.0032(10)
  C7 0.0546(12) 0.0591(13) 0.0655(13) -0.0159(10) 0.0034(10) 0.0070(10)
  C8 0.0549(11) 0.0538(12) 0.0463(11) -0.0049(9) 0.0029(9) 0.0095(9)
  C9 0.0419(9) 0.0394(9) 0.0395(9) 0.0038(8) 0.0012(7) 0.0007(7)
  C10 0.0398(9) 0.0468(10) 0.0332(9) 0.0024(8) 0.0032(7) 0.0047(7)
  C13 0.0408(9) 0.0502(10) 0.0268(8) 0.0036(8) 0.0003(7) -0.0042(7)
  C16 0.0474(10) 0.0427(9) 0.0282(8) 0.0002(8) 0.0067(7) -0.0005(7)
  C21 0.0395(9) 0.0478(10) 0.0301(8) 0.0035(8) 0.0015(7) -0.0052(7)
  C23 0.0644(13) 0.0529(12) 0.0459(11) -0.0041(10) -0.0069(9) 0.0055(9)
  C24 0.0659(13) 0.0515(11) 0.0528(12) -0.0083(10) -0.0037(10) -0.0031(9)
  C25 0.0594(12) 0.0641(13) 0.0401(10) -0.0100(10) -0.0049(9) -0.0110(9)
  C26 0.0543(11) 0.0567(12) 0.0309(9) -0.0006(9) -0.0027(8) -0.0036(8)
  C31 0.0454(10) 0.0381(9) 0.0344(9) 0.0022(8) 0.0071(7) -0.0018(7)
  C33 0.0488(11) 0.0611(12) 0.0495(11) 0.0083(10) -0.0036(9) -0.0002(9)
  C34 0.0424(10) 0.0495(11) 0.0718(14) -0.0022(9) 0.0048(9) -0.0047(10)
  C35 0.0572(12) 0.0552(12) 0.0608(13) -0.0093(10) 0.0167(10) 0.0039(10)
  C36 0.0568(11) 0.0553(12) 0.0397(10) -0.0058(9) 0.0090(8) 0.0036(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
  N1 C10 . 1.376(2) Yes
  N1 C13 . 1.380(2) Yes
  N1 N2 . 1.3857(17) Yes
  N2 C3 . 1.376(2) Yes
  N2 C16 . 1.382(2) Yes
  N11 C10 . 1.312(2) Yes
  N11 N12 . 1.385(2) Yes
  N12 C13 . 1.314(2) Yes
  N14 C3 . 1.308(2) Yes
  N14 N15 . 1.377(2) Yes
  N15 C16 . 1.313(2) Yes
  N22 C23 . 1.333(2) Yes
  N22 C21 . 1.339(2) Yes
  N32 C31 . 1.337(2) Yes
  N32 C33 . 1.339(2) Yes
  C3 C4 . 1.446(2) Yes
  C4 C5 . 1.394(2) ?
  C4 C9 . 1.400(2) Yes
  C5 C6 . 1.366(3) ?
  C5 H5 . 0.9300 ?
  C6 C7 . 1.381(3) ?
  C6 H6 . 0.9300 ?
  C7 C8 . 1.379(3) ?
  C7 H7 . 0.9300 ?
  C8 C9 . 1.392(2) ?
  C8 H8 . 0.9300 ?
  C9 C10 . 1.446(2) Yes
  C13 C21 . 1.461(2) Yes
  C16 C31 . 1.465(2) Yes
  C21 C26 . 1.383(2) ?
  C23 C24 . 1.377(3) ?
  C23 H23 . 0.9300 ?
  C24 C25 . 1.374(3) ?
  C24 H24 . 0.9300 ?
  C25 C26 . 1.378(3) ?
  C25 H25 . 0.9300 ?
  C26 H26 . 0.9300 ?
  C31 C36 . 1.382(2) ?
  C33 C34 . 1.376(3) ?
  C33 H33 . 0.9300 ?
  C34 C35 . 1.376(3) ?
  C34 H34 . 0.9300 ?
  C35 C36 . 1.367(3) ?
  C35 H35 . 0.9300 ?
  C36 H36 . 0.9300 ?
  N22 N32 . 3.075(2) Yes