data_2012628
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o242
_journal_page_last  o246
_publ_section_title
;
Two-component molecular crystals composed of chloronitrobenzoic acids and
4-aminopyridine
;
loop_
_publ_author_name
  'Sugiyama, Teruki'
  'Meng, Jiben'
  'Matsuura, Teruo'
_chemical_formula_moiety  'C5 H7 N2 + , C7 H3 Cl N O4 -'
_chemical_formula_sum  'C12 H10 Cl N3 O4'
_chemical_formula_iupac  'C5 H7 N2 + , C7 H3 Cl N O4 -'
_chemical_formula_weight  295.68
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'P 21/n'
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  12.624(4)
_cell_length_b  7.270(2)
_cell_length_c  14.023(5)
_cell_angle_alpha  90
_cell_angle_beta  96.329(5)
_cell_angle_gamma  90
_cell_volume  1279.1(7)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.535
_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 1.01449(4) 0.13515(8) 0.11788(4) 0.04517(18) Uani d . 1 . . Cl
  O1 0.83406(12) -0.1551(2) 0.05023(10) 0.0534(4) Uani d . 1 . . O
  O2 0.69773(11) 0.0320(2) 0.06848(10) 0.0510(4) Uani d . 1 . . O
  O3 0.67868(12) -0.0782(2) 0.43183(10) 0.0533(4) Uani d . 1 . . O
  O4 0.82083(13) -0.0220(3) 0.52749(10) 0.0719(6) Uani d . 1 . . O
  N1 0.54346(17) -0.1523(3) -0.39945(13) 0.0520(5) Uani d D 1 . . N
  H2 0.5928(17) -0.134(4) -0.4396(16) 0.081(9) Uiso d D 1 . . H
  H1 0.4803(12) -0.206(3) -0.4148(17) 0.073(8) Uiso d D 1 . . H
  N2 0.63461(15) -0.0477(3) -0.11447(12) 0.0472(5) Uani d D 1 . . N
  H3 0.656(2) -0.032(4) -0.0501(8) 0.080(8) Uiso d D 1 . . H
  C1 0.57376(16) -0.1142(3) -0.30697(14) 0.0382(5) Uani d . 1 . . C
  C2 0.50241(16) -0.1369(3) -0.23733(14) 0.0399(5) Uani d . 1 . . C
  H2A 0.4329 -0.1754 -0.2556 0.048 Uiso calc R 1 . . H
  N3 0.77181(14) -0.0301(3) 0.44713(12) 0.0454(5) Uani d . 1 . . N
  C3 0.53540(18) -0.1024(3) -0.14320(15) 0.0444(5) Uani d . 1 . . C
  H3A 0.4876 -0.1175 -0.0979 0.053 Uiso calc R 1 . . H
  C4 0.70447(18) -0.0222(3) -0.17941(16) 0.0542(6) Uani d . 1 . . C
  H4A 0.7733 0.0167 -0.1585 0.065 Uiso calc R 1 . . H
  C5 0.67689(17) -0.0517(3) -0.27428(16) 0.0499(6) Uani d . 1 . . C
  H5A 0.7261 -0.0307 -0.3178 0.060 Uiso calc R 1 . . H
  C6 0.78649(16) -0.0405(3) 0.09499(13) 0.0357(5) Uani d . 1 . . C
  C7 0.83698(14) 0.0160(3) 0.19436(13) 0.0317(4) Uani d . 1 . . C
  C8 0.78180(15) -0.0196(3) 0.27315(13) 0.0341(5) Uani d . 1 . . C
  H8A 0.7135 -0.0689 0.2641 0.041 Uiso calc R 1 . . H
  C9 0.82873(15) 0.0184(3) 0.36465(13) 0.0358(5) Uani d . 1 . . C
  C10 0.92851(17) 0.0979(3) 0.38164(14) 0.0417(5) Uani d . 1 . . C
  H10A 0.9578 0.1252 0.4438 0.050 Uiso calc R 1 . . H
  C11 0.98389(16) 0.1361(3) 0.30403(14) 0.0396(5) Uani d . 1 . . C
  H11A 1.0509 0.1907 0.3135 0.047 Uiso calc R 1 . . H
  C12 0.93874(15) 0.0925(3) 0.21184(13) 0.0340(5) Uani d . 1 . . 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 0.0388(3) 0.0564(4) 0.0414(3) -0.0021(2) 0.0093(2) 0.0090(3)
  O1 0.0503(9) 0.0663(11) 0.0421(8) 0.0106(8) -0.0013(7) -0.0153(8)
  O2 0.0401(9) 0.0727(11) 0.0374(8) 0.0110(8) -0.0084(7) -0.0068(7)
  O3 0.0469(10) 0.0672(11) 0.0476(9) -0.0109(8) 0.0135(8) 0.0003(8)
  O4 0.0607(11) 0.1253(17) 0.0285(9) -0.0042(11) -0.0002(8) 0.0081(9)
  N1 0.0528(13) 0.0674(14) 0.0354(10) -0.0090(11) 0.0027(9) -0.0064(9)
  N2 0.0458(12) 0.0585(12) 0.0349(10) 0.0080(9) -0.0056(9) -0.0021(9)
  C1 0.0407(12) 0.0374(11) 0.0353(11) 0.0036(9) -0.0003(9) -0.0005(9)
  C2 0.0350(11) 0.0421(12) 0.0417(12) -0.0053(9) -0.0003(9) -0.0022(10)
  N3 0.0472(12) 0.0552(12) 0.0344(10) 0.0022(9) 0.0063(9) 0.0017(8)
  C3 0.0455(13) 0.0485(13) 0.0393(12) 0.0012(10) 0.0057(10) 0.0010(10)
  C4 0.0329(12) 0.0730(17) 0.0545(15) 0.0020(12) -0.0055(11) -0.0093(12)
  C5 0.0375(12) 0.0682(16) 0.0448(13) -0.0004(11) 0.0080(10) -0.0043(11)
  C6 0.0338(11) 0.0428(12) 0.0302(10) -0.0045(10) 0.0021(9) 0.0032(9)
  C7 0.0322(10) 0.0331(11) 0.0291(10) 0.0043(8) -0.0001(8) 0.0020(8)
  C8 0.0294(10) 0.0377(11) 0.0347(10) 0.0004(9) 0.0012(8) 0.0005(9)
  C9 0.0365(11) 0.0410(12) 0.0300(10) 0.0013(9) 0.0035(9) 0.0013(9)
  C10 0.0439(12) 0.0484(13) 0.0311(10) -0.0026(10) -0.0034(9) -0.0033(9)
  C11 0.0333(11) 0.0413(12) 0.0424(11) -0.0070(9) -0.0031(9) 0.0009(10)
  C12 0.0321(11) 0.0350(11) 0.0346(10) 0.0023(8) 0.0021(9) 0.0053(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 C12 . 1.7390(19) no
  O1 C6 . 1.237(2) no
  O2 C6 . 1.257(2) no
  O3 N3 . 1.223(2) no
  O4 N3 . 1.226(2) no
  N1 C1 . 1.340(3) no
  N1 H2 . 0.894(10) no
  N1 H1 . 0.892(10) no
  N2 C3 . 1.334(3) no
  N2 C4 . 1.349(3) no
  N2 H3 . 0.920(10) no
  C1 C5 . 1.407(3) no
  C1 C2 . 1.409(3) no
  C2 C3 . 1.363(3) no
  C2 H2A . 0.9300 no
  N3 C9 . 1.470(3) no
  C3 H3A . 0.9300 no
  C4 C5 . 1.355(3) no
  C4 H4A . 0.9300 no
  C5 H5A . 0.9300 no
  C6 O2 1 1.257(2) no
  C6 C7 . 1.524(3) no
  C7 C8 . 1.394(3) no
  C7 C12 . 1.397(3) no
  C8 C9 . 1.381(3) no
  C8 H8A . 0.9300 no
  C9 C10 . 1.383(3) no
  C10 C11 . 1.385(3) no
  C10 H10A . 0.9300 no
  C11 C12 . 1.391(3) no
  C11 H11A . 0.9300 no