Received 19 January 2012
In the title compound, C15H15N5O4, a nitroformazan derivative, the formazan unit is essentially planar with an r.m.s. deviation of 0.0204 (6) Å and adopts a closed syn,s-cis configuration with an intramolecular N-HN hydrogen bond. The formazan plane makes dihedral angles of 4.32 (5) and 24.35 (5)° with the benzene rings. The dihedral angle between the formazan plane and the nitro group is 12.58 (8)°. In the crystal, C-HO interactions connect the molecules into an inversion dimer.
For synthetic background, see: Pelkis et al. (1957). For applications of formazans, see: Irving (1977). For related structures, see: Gilroy et al. (2008); Laing (1977); Mito et al. (1997); von Eschwege et al. (2011, 2012); von Eschwege & Swarts (2010).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5057 ).
Financial assistance from the University of the Free State is gratefully acknowledged. We also express our gratitude towards SASOL and the South African National Research Foundation (SA-NRF/THRIP) for financial support of this project. Part of this material is based on work supported by the SA-NRF/THRIP under grant No. GUN 2068915.
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Imapct GbR, Bonn, Germany.
Bruker (2004). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin. USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Eschwege, K. G. von, Conradie, J. & Kuhn, A. (2011). J. Phys. Chem. A, 115, 14637-14646.
Eschwege, K. G. von, Muller, F. & Hosten, E. C. (2012). Acta Cryst. E68, o199-o200.
Eschwege, K. G. von & Swarts, J. C. (2010). Polyhedron, 29, 1727-1733.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Gilroy, J. B., Otieno, P. O., Ferguson, M. J., McDonald, R. & Hicks, R. G. (2008). Inorg. Chem. 47, 1279-1286.
Irving, H. M. N. H. (1977). Dithizone. Analytical Sciences Monographs, No. 5. London: The Chemical Society.
Laing, M. (1977). J. Chem. Soc. Perkin Trans. 2, pp. 1248-1252.
Mito, M., Takeda, K., Mukai, K., Azuma, N., Gleiter, M. R., Krieger, C. & Neugebaue, F. A. (1997). J. Phys. Chem. B, 101, 9517-9524.
Pelkis, P. S., Dubenko, R. G. & Pupko, L. S. (1957). J. Org. Chem. USSR (Engl. Transl.), 27, 2190-2194.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.