#------------------------------------------------------------------------------
#$Date: 2009-11-18 14:56:34 +0000 (Wed, 18 Nov 2009) $
#$Revision: 858 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202116.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2202116
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o420
_journal_page_last  o422
_publ_section_title
;
3-Hydroxypyridinium 2,5-dihydroxybenzoate
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
loop_
_publ_author_name
  'Takeo Fukunaga'
  'Setsuo Kashino'
  'Hiroyuki Ishida'
_chemical_formula_moiety  'C5 H6 N O 1+, C7 H5 O4 1-'
_chemical_formula_sum            'C12 H11 N O5'
_[local]_cod_chemical_formula_sum_orig 'C12 H11 N O5 '
_chemical_formula_iupac  'C5 H6 N O 1+, C7 H5 O4 1-'
_chemical_formula_weight  249.22
_symmetry_cell_setting  monoclinic
loop_
_symmetry_equiv_pos_as_xyz
  '  +x,  +y,  +z'
  '  -x,1/2+y,1/2-z'
  '  -x,  -y,  -z'
  '  +x,1/2-y,1/2+z'
_cell_length_a  7.659(2)
_cell_length_b  7.1731(17)
_cell_length_c  20.468(4)
_cell_angle_alpha  90
_cell_angle_beta  95.454(18)
_cell_angle_gamma  90
_cell_volume  1119.4(5)
_cell_formula_units_Z  4
_cell_measurement_temperature  298
_exptl_crystal_density_diffrn  1.479
_diffrn_ambient_temperature  298
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_refinement_flags
_atom_site_occupancy
  O1 0.4951(3) 1.1583(2) 0.61801(10) 0.0619(5) Uani d ? . 1.000
  O2 0.2621(2) 0.1928(2) 0.52261(8) 0.0585(5) Uani d ? . 1.000
  O3 0.2599(2) 0.4962(2) 0.50114(7) 0.0513(5) Uani d ? . 1.000
  O4 0.0893(2) 0.6228(2) 0.39858(9) 0.0546(5) Uani d ? . 1.000
  O5 -0.1000(2) -0.0975(2) 0.33037(8) 0.0549(5) Uani d ? . 1.000
  N1 0.4441(2) 0.6629(3) 0.60081(9) 0.0387(5) Uani d ? . 1.000
  C2 0.4276(3) 0.8440(3) 0.58707(10) 0.0388(5) Uani d ? . 1.000
  C3 0.5064(3) 0.9755(3) 0.62988(10) 0.0404(5) Uani d ? . 1.000
  C4 0.6014(3) 0.9113(3) 0.68671(11) 0.0435(6) Uani d ? . 1.000
  C5 0.6149(3) 0.7233(3) 0.69940(11) 0.0443(6) Uani d ? . 1.000
  C6 0.5358(3) 0.5985(3) 0.65547(11) 0.0431(6) Uani d ? . 1.000
  C7 0.0973(2) 0.2951(3) 0.42658(9) 0.0322(5) Uani d ? . 1.000
  C8 0.0433(3) 0.4427(3) 0.38454(10) 0.0358(5) Uani d ? . 1.000
  C9 -0.0555(3) 0.4051(3) 0.32527(10) 0.0404(5) Uani d ? . 1.000
  C10 -0.1008(3) 0.2249(3) 0.30804(10) 0.0398(5) Uani d ? . 1.000
  C11 -0.0497(3) 0.0777(3) 0.35006(10) 0.0371(5) Uani d ? . 1.000
  C12 0.0484(3) 0.1147(3) 0.40892(10) 0.0354(5) Uani d ? . 1.000
  C13 0.2143(3) 0.3294(3) 0.48844(9) 0.0371(5) Uani d ? . 1.000
  H1 0.381(3) 0.577(4) 0.5691(13) 0.053(7) Uiso d ? . 1.000
  H2 0.358(3) 0.881(3) 0.5457(11) 0.039(6) Uiso d ? . 1.000
  H3 0.412(4) 1.184(4) 0.5847(15) 0.072(8) Uiso d ? . 1.000
  H4 0.660(3) 0.999(4) 0.7144(13) 0.054(7) Uiso d ? . 1.000
  H5 0.685(3) 0.676(4) 0.7393(13) 0.057(7) Uiso d ? . 1.000
  H6 0.543(3) 0.472(4) 0.6596(12) 0.055(7) Uiso d ? . 1.000
  H7 0.152(4) 0.619(4) 0.4392(15) 0.072(8) Uiso d ? . 1.000
  H8 -0.094(4) 0.505(5) 0.2961(14) 0.070(8) Uiso d ? . 1.000
  H9 -0.173(3) 0.198(3) 0.2656(11) 0.040(6) Uiso d ? . 1.000
  H10 -0.044(4) -0.171(4) 0.3587(15) 0.067(8) Uiso d ? . 1.000
  H11 0.085(3) 0.017(3) 0.4374(11) 0.038(5) 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
  O1 0.0763(12) 0.0317(9) 0.0698(12) -0.0054(8) -0.0349(10) 0.0013(8)
  O2 0.0811(12) 0.0392(9) 0.0483(9) -0.0009(8) -0.0300(8) 0.0067(7)
  O3 0.0667(11) 0.0344(9) 0.0480(9) -0.0033(7) -0.0198(8) -0.0060(7)
  O4 0.0710(11) 0.0253(8) 0.0608(11) -0.0023(7) -0.0286(9) 0.0020(7)
  O5 0.0788(12) 0.0304(8) 0.0492(10) -0.0051(8) -0.0267(8) -0.0025(7)
  N1 0.0436(10) 0.0324(9) 0.0381(9) -0.0006(7) -0.0064(7) -0.0054(7)
  C2 0.0443(11) 0.0341(11) 0.0353(10) -0.0007(9) -0.0106(9) -0.0010(8)
  C3 0.0417(11) 0.0324(10) 0.0444(11) -0.0018(8) -0.0091(9) -0.0025(9)
  C4 0.0447(12) 0.0414(12) 0.0407(11) 0.0002(9) -0.0153(9) -0.0084(9)
  C5 0.0475(12) 0.0458(12) 0.0368(11) 0.0057(10) -0.0099(9) -0.0007(9)
  C6 0.0484(12) 0.0338(11) 0.0453(12) 0.0042(9) -0.0050(9) -0.0003(9)
  C7 0.0376(10) 0.0273(9) 0.0305(9) 0.0022(7) -0.0035(8) 0.0000(7)
  C8 0.0396(10) 0.0249(10) 0.0407(11) 0.0015(8) -0.0078(8) 0.0004(8)
  C9 0.0455(11) 0.0329(10) 0.0398(11) 0.0025(9) -0.0117(9) 0.0066(9)
  C10 0.0423(11) 0.0377(11) 0.0365(10) -0.0004(9) -0.0116(8) 0.0020(9)
  C11 0.0432(11) 0.0282(9) 0.0379(10) 0.0011(8) -0.0061(8) -0.0028(8)
  C12 0.0424(11) 0.0279(10) 0.0341(10) 0.0010(8) -0.0053(8) 0.0028(8)
  C13 0.0437(11) 0.0328(10) 0.0326(10) 0.0024(8) -0.0073(8) -0.0032(8)
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
  O1 C3 . . 1.334(3) yes
  O1 H3 . . 0.90(3) no
  O2 C13 . . 1.239(3) yes
  O3 C13 . . 1.267(3) yes
  O4 C8 . . 1.363(3) yes
  O4 H7 . . 0.92(3) no
  O5 C11 . . 1.364(3) yes
  O5 H10 . . 0.87(4) no
  N1 C2 . . 1.332(3) yes
  N1 C6 . . 1.345(3) yes
  N1 H1 . . 0.99(3) no
  C2 C3 . . 1.387(3) yes
  C2 H2 . . 0.99(2) no
  C3 C4 . . 1.391(3) yes
  C4 C5 . . 1.375(3) yes
  C4 H4 . . 0.93(3) no
  C5 C6 . . 1.369(3) yes
  C5 H5 . . 0.99(3) no
  C6 H6 . . 0.91(3) no
  C7 C8 . . 1.402(3) yes
  C7 C12 . . 1.386(3) yes
  C7 C13 . . 1.500(3) yes
  C8 C9 . . 1.393(3) yes
  C9 C10 . . 1.376(3) yes
  C9 H8 . . 0.96(3) no
  C10 C11 . . 1.394(3) yes
  C10 H9 . . 1.00(2) no
  C11 C12 . . 1.383(3) yes
  C12 H11 . . 0.94(2) no