Received 25 November 2009
The molecule of the title compound, C12H10N4O4, displays an E configuration about the C=N bond. The dihedral angle between the benzene and isoxazole rings is 1.36 (5)° and the molecular conformation is stabilized by the an intramolecular C-HN hydrogen bond. In the crystal structure, centrosymmetrically related molecules are connected by pairs of N-HO hydrogen bonds into dimers, which are further linked into a three-dimensional network by intermolecular C-HO hydrogen bonds and by stacking interactions involving adjacent benzene and isoxazole rings, with a centroid-centroid separation of 3.861 (3) Å.
For the biological activity and coordination ability of hydrazone compounds, see: Khattab (2005); Reiter et al. (1985). For the properties of isoxazole derivatives, see: Stevens & Albizati (1984). For examples of crystal structures of hydrazone compounds, see: Fun et al. (2008); Wei et al. (2009); Khaledi et al. (2008). For reference bond-length data, see: Allen et al. (1987).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2400 ).
The author acknowledges financial support by the Zhejiang Provincial Natural Science Foundation of China (No. Y406049).
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-S19.
Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Fun, H.-K., Patil, P. S., Rao, J. N., Kalluraya, B. & Chantrapromma, S. (2008). Acta Cryst. E64, o1707.
Khaledi, H., Mohd Ali, H. & Ng, S. W. (2008). Acta Cryst. E64, o2481.
Khattab, S. N. (2005). Molecules, 10, 1218-1228.
Reiter, J., Somoral, T. & Dvortsak, P. (1985). Heterocycl. Chem. 22, 385-394.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Stevens, R. V. & Albizati, K. F. (1984). Tetrahedron Lett. 25, 4587-4591.
Wei, Y.-J., Wang, F.-W. & Zhu, Q.-Y. (2009). Acta Cryst. E65, o688.