Received 5 June 2013
The title compound, C21H17N3O5·C3H7NO, exists in an E conformation with respect to the azomethine double bond of the hydrazide molecule. This molecule contains an intramolecular O-HN hydrogen bond, while an intermolecular N-HO hydrogen bond links the hydrazide to the formamide molecule of solvation. Nonclassical C-HO intermolecular hydrogen bonds build up a supramolecular architecture, together with two C-H interactions and a weak - interaction, with a centroid-centroid distance of 3.650 (13) Å.
For the biological and analytical applications of carbohydrazides, see: Vicini et al. (2002); Savini et al. (2002); Grande et al. (2007). For the synthesis of related compounds, see: Mathew & Kurup (2011); Despaigne et al. (2009). For related structures, see: Joseph et al. (2012).
Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2634 ).
BJ is grateful to the Council for Scientific and Industrial Research, New Delhi, India, for the award of a Senior Research Fellowship. MRPK is grateful to UGC, New Delhi, for a UGC-BSR one-time grant to Faculty. The authors are grateful to Dr Matthias Zeller, Department of Chemistry, Youngstown State University, for the support with data refinement. The authors are grateful to the Sophisticated Analytical Instruments Facility, Cochin University of Science and Technology, Kochi-22, India for the single-crystal X-ray diffraction measurements.
Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Despaigne, A. A. R., Silva, J. G. D., Carmo, A. C. M. D. & Piro, O. E. (2009). Inorg. Chim. Acta, 362, 2117-2122.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Grande, F., Aiello, F., Grazia, O. D., Brizzi, A., Garofalo, A. & Neamati, N. (2007). Bioorg. Med. Chem. 15, 288-294.
Joseph, B., Sithambaresan, M. & Kurup, M. R. P. (2012). Acta Cryst. E68, o1421-o1422.
Mathew, N. & Kurup, M. R. P. (2011). Spectrochim. Acta Part A, 78, 1424-1428.
Savini, L., Chiasserini, L., Gaeta, A. & Pellerano, C. (2002). Bioorg. Med. Chem. 10, 2193-2198.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Vicini, P., Zani, F., Cozzini, P. & Doytchinova, I. (2002). Eur. J. Med. Chem. 37, 553-564.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.