data_2009045
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  1714
_journal_page_last  1717
_publ_section_title
;
1:2 Complexes of chloranilic acid with pyrimidine and pyrazine
;
loop_
_publ_author_name
  ' Ishida, Hiroyuki '
  ' Kashino, Setsuo '
_chemical_formula_moiety  '2C4 H4 N2, C6 H2 Cl2 O4'
_chemical_formula_sum  'C14 H10 Cl2 N4 O4'
_chemical_formula_weight  369.16
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/n'
loop_
_symmetry_equiv_pos_as_xyz
  '  +x,  +y,  +z'
  '1/2-x,1/2+y,1/2-z'
  '  -x,  -y,  -z'
  '1/2+x,1/2-y,1/2+z'
_cell_length_a  3.8283(7)
_cell_length_b  18.514(5)
_cell_length_c  10.795(3)
_cell_angle_alpha  90
_cell_angle_beta  94.48(2)
_cell_angle_gamma  90
_cell_volume  762.8(3)
_cell_formula_units_Z  2
_cell_measurement_temperature  296
_exptl_crystal_density_diffrn  1.607
_diffrn_ambient_temperature  296
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_calc_attached_atom
_atom_site_occupancy
  Cl  .7279(3)  .12075(6)  .67562(8)  .0356(3) Uani d ? 1.000
  O1 1.1169(7)  -.01280(10)
  .7450(2)  .0404(9) Uani d ? 1.000
  O2  .6310(7)  .1159(2)  .3998(2)  .0375(9) Uani d ? 1.000
  N1  .5514(8)  .1481(2)  .1658(3)  .0350(10)
  Uani d ? 1.000
  N2  .4787(9)  .1957(2)  -.0789(3)  .0420(10)
  Uani d ? 1.000
  C1 1.0580(10)
  -.0050(2)  .6331(3)  .0270(10)
  Uani d ? 1.000
  C2  .8720(10)
  .0557(2)  .5760(3)  .0260(10)
  Uani d ? 1.000
  C3  .8080(10)
  .0625(2)  .4512(3)  .0260(10)
  Uani d ? 1.000
  C4  .6610(10)
  .2131(3)  .1347(4)  .042(2) Uani d ? 1.000
  C5  .6240(10)
  .2360(2)  .0120(4)  .042(2) Uani d ? 1.000
  C6  .3680(10)
  .1304(3)  -.0452(4)  .0400(10)
  Uani d ? 1.000
  C7  .4070(10)
  .1063(3)  .0758(4)  .0400(10)
  Uani d ? 1.000
  H1  .610(10)
  .121(3)  .302(4)  .120(10)
  Uiso d ? 1.000
  H2  .774(8)  .243(2)  .197(3)  .030(10)
  Uiso d ? 1.000
  H3  .710(10)
  .282(2)  -.010(3)  .050(10)
  Uiso d ? 1.000
  H4  .257(9)  .105(2)  -.113(3)  .050(10)
  Uiso d ? 1.000
  H5  .307(9)  .064(2)  .103(3)  .030(10)
  Uiso d ? 1.000
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
  Cl  .0469(7)  .0345(6)  .0256(5)  .0036(7)  .0034(4)  -.0046(6)
  O1  .066(2)  .036(2)  .0190(10)
  .004(2)  .0000(10)
  .0020(10)
  O2  .057(2)  .029(2)  .0250(10)
  .014(2)  -.0030(10)
  -.0010(10)
  N1  .044(2)  .038(2)  .022(2)  .006(2)  -.003(2)  .002(2)
  N2  .058(3)  .042(2)  .027(2)  .003(2)  .001(2)  .003(2)
  C1  .030(2)  .029(2)  .021(2)  -.006(2)  .003(2)  -.001(2)
  C2  .030(2)  .026(2)  .021(2)  -.002(2)  .003(2)  -.003(2)
  C3  .029(2)  .028(2)  .022(2)  -.004(2)  .001(2)  -.002(2)
  C4  .046(3)  .041(3)  .037(3)  .006(2)  -.003(2)  -.008(2)
  C5  .054(3)  .034(3)  .039(3)  .010(3)  .008(2)  .007(2)
  C6  .044(3)  .047(3)  .027(2)  .003(3)  -.002(2)  -.008(3)
  C7  .044(3)  .040(3)  .036(3)  -.005(2)  .004(2)  .007(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  Cl C2 . . 1.733(4) yes
  O1 C1 . . 1.219(4) yes
  O2 C3 . . 1.298(5) yes
  O2 H1 . . 1.06(5) no
  C1 C2 . . 1.443(6) yes
  C1 C3 . 3_756 1.517(5) yes
  C2 C3 . . 1.356(5) yes
  N1 C4 . . 1.326(6) yes
  N1 C7 . . 1.329(5) yes
  N2 C5 . . 1.320(6) yes
  N2 C6 . . 1.340(6) yes
  C4 C5 . . 1.387(6) yes
  C4 H2 . .  .95(4) no
  C5 H3 . .  .96(4) no
  C6 C7 . . 1.378(6) yes
  C6 H4 . .  .94(4) no
  C7 H5 . .  .93(4) no