data_2012630
_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  'C 2/c'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y, -z+1/2'
  'x+1/2, y+1/2, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y, z-1/2'
  '-x+1/2, -y+1/2, -z'
  'x+1/2, -y+1/2, z-1/2'
_cell_length_a  25.608(19)
_cell_length_b  8.475(6)
_cell_length_c  12.433(10)
_cell_angle_alpha  90
_cell_angle_beta  103.749(14)
_cell_angle_gamma  90
_cell_volume  2621(3)
_cell_formula_units_Z  8
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.499
_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 0.46273(3) 0.19463(9) 1.09806(7) 0.0691(3) Uani d . 1 . . Cl
  O1 0.67956(8) 0.5915(2) 1.03009(16) 0.0627(6) Uani d . 1 . . O
  O2 0.64006(7) 0.5301(2) 0.85667(16) 0.0623(6) Uani d . 1 . . O
  O3 0.64154(9) 0.1909(3) 0.86890(18) 0.0766(7) Uani d . 1 . . O
  O4 0.56335(9) 0.2125(3) 0.76201(18) 0.0929(9) Uani d . 1 . . O
  N1 0.67789(10) 0.7470(3) 0.73599(19) 0.0543(6) Uani d . 1 . . N
  H1 0.6714(13) 0.672(4) 0.785(3) 0.087(11) Uiso d . 1 . . H
  N2 0.71828(11) 1.0873(3) 0.5373(2) 0.0553(7) Uani d . 1 . . N
  H22 0.7050(12) 1.173(3) 0.530(2) 0.052(9) Uiso d . 1 . . H
  H21 0.7497(13) 1.077(3) 0.510(2) 0.076(10) Uiso d . 1 . . H
  N3 0.59496(10) 0.2314(3) 0.84955(19) 0.0499(6) Uani d . 1 . . N
  C1 0.72010(12) 0.7263(3) 0.6911(2) 0.0545(7) Uani d . 1 . . C
  H1A 0.7399 0.6334 0.7052 0.065 Uiso calc R 1 . . H
  C2 0.73461(10) 0.8376(3) 0.6258(2) 0.0475(7) Uani d . 1 . . C
  H2A 0.7645 0.8213 0.5970 0.057 Uiso calc R 1 . . H
  C3 0.70500(9) 0.9766(3) 0.6015(2) 0.0405(6) Uani d . 1 . . C
  C4 0.66046(10) 0.9934(3) 0.6484(2) 0.0500(7) Uani d . 1 . . C
  H4A 0.6391 1.0832 0.6341 0.060 Uiso calc R 1 . . H
  C5 0.64896(11) 0.8785(4) 0.7142(2) 0.0574(8) Uani d . 1 . . C
  H5A 0.6197 0.8918 0.7456 0.069 Uiso calc R 1 . . H
  C6 0.51680(10) 0.2849(3) 1.0603(2) 0.0440(6) Uani d . 1 . . C
  C7 0.54252(10) 0.4093(3) 1.1214(2) 0.0472(7) Uani d . 1 . . C
  H7A 0.5318 0.4439 1.1838 0.057 Uiso calc R 1 . . H
  C8 0.58457(10) 0.4825(3) 1.0888(2) 0.0437(6) Uani d . 1 . . C
  H8A 0.6016 0.5677 1.1297 0.052 Uiso calc R 1 . . H
  C9 0.60195(9) 0.4326(3) 0.99716(18) 0.0361(6) Uani d . 1 . . C
  C10 0.57535(9) 0.3041(3) 0.94051(19) 0.0377(6) Uani d . 1 . . C
  C11 0.53250(10) 0.2298(3) 0.9689(2) 0.0435(6) Uani d . 1 . . C
  H11A 0.5149 0.1456 0.9276 0.052 Uiso calc R 1 . . H
  C12 0.64452(10) 0.5254(3) 0.9582(2) 0.0430(6) 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 0.0676(5) 0.0614(5) 0.0935(7) -0.0098(4) 0.0490(4) 0.0062(4)
  O1 0.0603(13) 0.0647(12) 0.0681(13) -0.0248(10) 0.0255(10) -0.0151(11)
  O2 0.0682(13) 0.0773(13) 0.0494(12) -0.0148(11) 0.0299(9) 0.0101(10)
  O3 0.0678(15) 0.0954(17) 0.0710(15) 0.0281(12) 0.0255(11) -0.0145(12)
  O4 0.0675(15) 0.162(3) 0.0502(13) -0.0161(15) 0.0163(11) -0.0370(15)
  N1 0.0667(16) 0.0543(14) 0.0447(14) -0.0130(13) 0.0190(12) 0.0040(12)
  N2 0.0563(16) 0.0445(14) 0.0714(17) 0.0042(12) 0.0278(13) 0.0142(12)
  N3 0.0552(15) 0.0565(14) 0.0418(13) -0.0058(12) 0.0191(11) -0.0076(11)
  C1 0.0603(18) 0.0512(16) 0.0517(17) 0.0056(14) 0.0125(14) 0.0093(14)
  C2 0.0431(14) 0.0503(15) 0.0520(16) 0.0047(12) 0.0173(12) 0.0057(13)
  C3 0.0396(14) 0.0402(13) 0.0424(14) -0.0045(11) 0.0114(11) -0.0023(11)
  C4 0.0448(15) 0.0465(15) 0.0631(18) 0.0012(12) 0.0213(13) -0.0025(13)
  C5 0.0530(17) 0.0678(19) 0.0595(18) -0.0126(15) 0.0298(14) -0.0105(16)
  C6 0.0434(15) 0.0423(14) 0.0524(16) 0.0027(11) 0.0233(12) 0.0105(12)
  C7 0.0568(16) 0.0485(15) 0.0445(15) 0.0041(13) 0.0284(12) 0.0013(12)
  C8 0.0533(16) 0.0408(14) 0.0399(14) -0.0009(12) 0.0170(11) -0.0030(11)
  C9 0.0371(13) 0.0379(13) 0.0354(13) 0.0026(11) 0.0126(10) 0.0046(11)
  C10 0.0421(14) 0.0397(13) 0.0339(13) 0.0047(11) 0.0142(10) 0.0031(11)
  C11 0.0435(15) 0.0392(14) 0.0489(15) -0.0020(11) 0.0129(11) 0.0013(11)
  C12 0.0462(15) 0.0370(13) 0.0523(16) 0.0021(12) 0.0247(13) 0.0040(13)
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 C6 . 1.742(3) no
  O1 C12 . 1.240(3) no
  O2 C12 . 1.241(3) no
  O3 N3 . 1.209(3) no
  O4 N3 . 1.203(3) no
  N1 C5 . 1.330(4) no
  N1 C1 . 1.340(4) no
  N1 H1 . 0.93(3) no
  N2 C3 . 1.327(3) no
  N2 H22 . 0.80(3) no
  N2 H21 . 0.95(3) no
  N3 C10 . 1.477(3) no
  C1 C2 . 1.353(4) no
  C1 H1A . 0.9300 no
  C2 C3 . 1.394(4) no
  C2 H2A . 0.9300 no
  C3 C4 . 1.406(3) no
  C4 C5 . 1.349(4) no
  C4 H4A . 0.9300 no
  C5 H5A . 0.9300 no
  C6 C7 . 1.372(4) no
  C6 C11 . 1.374(3) no
  C7 C8 . 1.384(3) no
  C7 H7A . 0.9300 no
  C8 C9 . 1.385(3) no
  C8 H8A . 0.9300 no
  C9 C10 . 1.384(3) no
  C9 C12 . 1.514(3) no
  C10 C11 . 1.382(3) no
  C11 H11A . 0.9300 no