Received 5 November 2012
In the 4-methoxyquinoline-2-carboxylate anion of the title salt, C5H8N3+·C11H8NO3-, the dihedral angle between the quinoline ring system and the carboxylate group is 16.54 (15)°. In the crystal, the cations and anions are linked via N-HO and N-HN hydrogen bonds, forming a centrosymmetric 2 + 2 aggregate with R22(9) and R42(8) ring motifs. These units are further connected via N-HO hydrogen bonds into a layer parallel to the bc plane. The crystal structure is also stabilized by weak C-HO hydrogen bonds and - interactions between pyridine rings [centroid-centroid distance = 3.5886 (8) Å] and between pyridine and benzene rings [centroid-centroid distance = 3.6328 (8) Å].
For background to the chemistry of substituted pyridines, see: Pozharski et al. (1997); Katritzky et al. (1996). For background to and the biological activity of quinoline derivatives, see: Morimoto et al. (1991); Markees et al. (1970). For a related structure, see: Hemamalini & Fun (2011). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For the 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: IS5215 ).
The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the research facilities and Fundamental Research Grant Scheme (FRGS) No. 203/PFIZIK/6711171 to conduct this work. KT thanks The Academy of Sciences for the Developing World and USM for a TWAS-USM fellowship.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Hemamalini, M. & Fun, H.-K. (2011). Acta Cryst. E67, o435-o436.
Katritzky, A. R., Rees, C. W. & Scriven, E. F. V. (1996). In Comprehensive Heterocyclic Chemistry II. Oxford: Pergamon Press.
Markees, D. G., Dewey, V. C. & Kidder, G. W. (1970). J. Med. Chem. 13, 324-326.
Morimoto, Y., Matsuda, F. & Shirahama, H. (1991). Synlett, 3, 202-203.
Pozharski, A. F., Soldatenkov, A. T. & Katritzky, A. R. (1997). In Heterocycles in Life and Society. New York: Wiley.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.