data_2011939
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2001
_journal_volume  57
_journal_page_first  627
_journal_page_last  631
_publ_section_title
;
Hydrogen-bonded complexes of 2-pyridone with centrosymmetric and
noncentrosymmetric dicarboxylic acids
;
loop_
_publ_author_name
  'Kashino, Setsuo'
  'Fukunaga, Takeo'
  'Izutsu, Hironobu'
  'Miyashita, Shiho'
_chemical_formula_moiety  'C5 H5 N O , C4 H6 O6 , H2 O'
_chemical_formula_sum  'C9 H13 N O8'
_chemical_formula_structural  'C5 H5 N O , C4 H6 O6 , H2 O'
_chemical_formula_weight  263.20
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P 21 21 21'
loop_
_symmetry_equiv_pos_as_xyz
  '  +x,  +y,  +z'
  '1/2-x,  -y,1/2+z'
  '1/2+x,1/2-y,  -z'
  '  -x,1/2+y,1/2-z'
_cell_length_a  8.528(5)
_cell_length_b  20.668(8)
_cell_length_c  6.5438(15)
_cell_angle_alpha  90
_cell_angle_beta  90
_cell_angle_gamma  90
_cell_volume  1153.4(7)
_cell_formula_units_Z  4
_cell_measurement_temperature  295
_exptl_crystal_density_diffrn  1.516
_diffrn_ambient_temperature  295
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  .49399(12)  .43810(5)  .25423(17)  .0541(3) Uani d ? . 1.000
  O2  .31341(10)  .53184(5)  .21738(18)  .0558(3) Uani d ? . 1.000
  O3  .51062(10)  .60285(4)  .19044(15)  .0467(3) Uani d ? . 1.000
  O4  .31260(12)  .70141(5)  .13139(18)  .0496(3) Uani d ? . 1.000
  O5  .25390(12)  .66734(5)  .53540(15)  .0458(3) Uani d ? . 1.000
  O6  -.09014(13)  .66162(5)  .22679(19)  .0556(4) Uani d ? . 1.000
  O7  -.01411(11)  .73370(4)  .46179(16)  .0540(3) Uani d ? . 1.000
  O8  -.34509(12)  .73051(6)  .1702(2)  .0470(3) Uani d ? . 1.000
  N1  .72157(13)  .49451(6)  .2167(2)  .0423(4) Uani d ? . 1.000
  C2  .64150(17)  .43759(7)  .2387(2)  .0431(4) Uani d ? . 1.000
  C3  .73498(19)  .38140(7)  .2403(3)  .0488(5) Uani d ? . 1.000
  C4  .89252(18)  .38451(8)  .2219(3)  .0548(6) Uani d ? . 1.000
  C5  .96815(19)  .44382(9)  .2021(3)  .0518(5) Uani d ? . 1.000
  C6  .88088(19)  .49770(8)  .1992(3)  .0490(5) Uani d ? . 1.000
  C7  .37157(17)  .58980(7)  .1943(2)  .0409(4) Uani d ? . 1.000
  C8  .24346(17)  .64044(6)  .1745(2)  .0375(4) Uani d ? . 1.000
  C9  .15579(16)  .64452(7)  .3785(2)  .0369(4) Uani d ? . 1.000
  C10  .00891(16)  .68594(7)  .3606(2)  .0406(4) Uani d ? . 1.000
  H1  .6595(14)  .5334(6)  .211(2)  .059(5) Uiso d ? . 1.000
  H2  .6820(14)  .3442(5)  .2578(19)  .041(4) Uiso d ? . 1.000
  H3  .9538(16)  .3431(6)  .227(2)  .070(5) Uiso d ? . 1.000
  H4 1.0811(15)  .4476(6)  .178(2)  .062(5) Uiso d ? . 1.000
  H5  .9227(12)  .5395(5)  .1839(19)  .033(4) Uiso d ? . 1.000
  H6  .1714(12)  .6266(5)  .0702(17)  .027(4) Uiso d ? . 1.000
  H7  .1185(11)  .6012(4)  .4129(15)  .015(3) Uiso d ? . 1.000
  H8  .2600(17)  .7179(7)  .045(3)  .077(7) Uiso d ? . 1.000
  H9  .318(2)  .7022(8)  .491(3)  .145(9) Uiso d ? . 1.000
  H10  .4094(19)  .4904(8)  .246(3)  .101(6) Uiso d ? . 1.000
  H11  -.1720(17)  .6843(7)  .219(3)  .073(6) Uiso d ? . 1.000
  H12  -.427(2)  .7064(10)  .156(4)  .146(10) Uiso d ? . 1.000
  H13  -.3645(19)  .7532(7)  .266(2)  .074(7) 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  .0408(6)  .0429(6)  .0786(8)  .0001(5)  -.0053(6)  -.0040(6)
  O2  .0380(5)  .0405(5)  .0889(8)  -.0019(5)  .0013(6)  -.0001(6)
  O3  .0329(5)  .0459(6)  .0611(7)  .0000(5)  .0045(6)  -.0007(6)
  O4  .0455(6)  .0484(6)  .0549(8)  -.0049(5)  -.0052(6)  .0161(6)
  O5  .0402(6)  .0524(6)  .0449(6)  -.0019(6)  -.0059(6)  -.0039(6)
  O6  .0415(6)  .0569(7)  .0685(8)  .0114(6)  -.0137(7)  -.0156(7)
  O7  .0478(6)  .0416(6)  .0726(8)  .0073(5)  -.0033(6)  -.0165(6)
  O8  .0369(6)  .0577(7)  .0464(7)  -.0031(6)  .0040(6)  -.0055(6)
  N1  .0451(8)  .0398(7)  .0419(8)  .0001(6)  -.0015(7)  -.0043(7)
  C2  .0485(9)  .0408(8)  .0400(9)  -.0027(8)  -.0031(8)  -.0066(8)
  C3  .0556(10)  .0349(8)  .0560(11)  -.0006(8)  -.0042(10)  -.0054(8)
  C4  .0541(10)  .0549(11)  .0552(12)  .0102(9)  -.0008(10)  -.0073(10)
  C5  .0432(10)  .0602(11)  .0521(11)  .0012(9)  .0038(9)  -.0028(10)
  C6  .0542(10)  .0519(10)  .0408(10)  -.0121(9)  .0020(9)  .0009(9)
  C7  .0425(8)  .0455(9)  .0347(9)  .0005(7)  .0022(8)  -.0010(8)
  C8  .0349(7)  .0386(8)  .0391(9)  -.0038(7)  -.0040(8)  .0028(7)
  C9  .0324(8)  .0320(7)  .0464(10)  -.0044(7)  .0008(8)  .0012(7)
  C10  .0350(8)  .0398(8)  .0471(10)  -.0031(7)  .0038(9)  .0039(7)
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 C2 . . 1.262(2) yes
  N1 C2 . . 1.368(2) yes
  N1 C6 . . 1.365(3) yes
  N1 H1 . .  .962(16) no
  C2 C3 . . 1.409(3) yes
  C3 C4 . . 1.350(3) yes
  C3 H2 . .  .900(15) no
  C4 C5 . . 1.391(3) yes
  C4 H3 . . 1.003(17) no
  C5 C6 . . 1.340(3) yes
  C5 H4 . .  .979(16) no
  C6 H5 . .  .941(14) no
  O2 C7 . . 1.305(2) no
  O2 H10 . . 1.20(2) no
  O3 C7 . . 1.216(2) no
  O4 C8 . . 1.419(2) no
  O4 H8 . .  .80(2) no
  O5 C9 . . 1.406(2) no
  O5 H9 . .  .95(2) no
  O6 C10 . . 1.316(2) no
  O6 H11 . .  .842(19) no
  O7 C10 . . 1.205(2) no
  C7 C8 . . 1.518(3) no
  C8 C9 . . 1.532(3) no
  C8 H6 . .  .962(15) no
  C9 C10 . . 1.522(3) no
  C9 H7 . .  .976(12) no
  O8 H12 . .  .86(3) no
  O8 H13 . .  .798(19) no