Received 6 June 2013
In the 3-hydroxypicolinate anion of the title salt, C6H9N2+·C6H4NO3-, an intramolecular O-HO hydrogen bond with an S(6) graph-set motif is formed, so that the anion is essentially planar, with a dihedral angle of 9.55 (9)° between the pyridine ring and the carboxylate group. In the crystal, the cations and anions are linked via N-HO hydrogen bonds, forming a centrosymmetric 2 + 2 aggregate with R22(8) and R42(8) ring motifs. The crystal structure also features N-HN and weak C-H interactions.
For details of non-covalent interactions, see: Desiraju (2007); Aakeroy & Seddon (1993). For related structures, see: Nahringbauer & Kvick (1977); Robert et al. (2001); Thanigaimani et al. (2010, 2013). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5281 ).
The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the research facilities and USM Short Term Grant, No. 304/PFIZIK/6312078 to conduct this work. KT thanks The Academy of Sciences for the Developing World and USM for the TWAS-USM fellowship.
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