Received 6 August 2013
aDepartment of Chemistry and Research Centre, PRNSS College, Mattanur 670 702, Kannur, Kerala, India,bDepartment of Chemistry, Faculty of Science, Eastern University, Sri Lanka, Chenkalady, Sri Lanka, and cDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India
Correspondence e-mail: email@example.com
The title compound, C15H12N4O, adopts an E conformation with respect to the azomethine bond and crystallizes in its hydrazinylidene tautomeric form. The dihedral angle between the ring systems is 15.98 (7)°. The phenol O-H group forms an intramolecular O-HN hydrogen bond. In the crystal, pairs of N-HN and C-HO hydrogen bonds link neighbouring molecules into centrosymmetric dimers. These dimers are interconnected by means of three types of - stacking interactions. One, with a centroid-centroid distance of 3.577 (1) Å [interplanar separation = 3.4673 (6) Å], connects adjacent molecules into centrosymmetric dimers. The other two interactions, on the outward facing sides of the dimers, are between phenol rings of neighboring molecules [centroid-centroid separation = 3.7907 (13) Å and interplanar separation = 3.5071 (8) Å], and between phthalazin units [centroid-centroid separation = 3.6001 (12) Å and interplanar separation = 3.4891 (7) Å]. In combination, the - interactions lead to the formation of infinite layers with molecules stacked along [0-11]. These layers are, in turn, connected with neighbouring layers through the N-HN and C-HO hydrogen bonds, yielding a three-dimensional supramolecular architecture.
For biological properties of phthalazine and its derivatives, see: Awadallah et al. (2012); Minami et al. (1985); Zhang et al. (2010); Bian et al. (2013). For applications of 1-phthalazinyl hydrazones in optoelectronics, see: Caruso et al. (2005). For the synthesis of related compounds, see: El-Sherif et al. (2012). For related structures and background references, see: Shafiq et al. (2013).
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 for Windows (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: ZL2563 ).
MKP is thankful to the University Grants Commission, Bangalore, India, for the award of a Teacher Fellowship. MRPK is thankful to the UGC, New Delhi, for a UGC-BSR one-time grant to Faculty. The authors are grateful to the Sophisticated Analytical Instruments Facility, Cochin University of Science and Technology, Kochi-22, India, for the diffraction measurements.
Awadallah, F. M., El-Eraky, W. I. & Saleh, D. O. (2012). Eur. J. Med. Chem. 52, 14-21.
Bian, M., Deng, X.-Q., Gong, G.-H., Wei, C.-X. & Quan, Z.-S. (2013). J. Enzyme Inhib. Med. Chem. 28, 792-800.
Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2004). SADABS, APEX2, XPREP and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Caruso, U., Centore, R., Panunzi, B., Roviello, A. & Tuzi, A. (2005). Eur. J. Inorg. Chem. 25, 2747-2753.
El-Sherif, A. A., Shoukry, M. M. & Abd-Elgawad, M. M. A. (2012). Spectrochim. Acta Part A, 98, 307-321.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Minami, M., Togashi, H., Sano, M., Saito, I., Morii, K., Nomura, A., Yoshioka, M. & Saito, H. (1985). Hokkaido Igaku Zasshi, 60, 856-864.
Shafiq, M., Tahir, M. N., Harrison, W. T. A., Bukhari, I. H. & Khan, I. U. (2013). Acta Cryst. E69, o164.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.
Zhang, S., Zhao, Y., Liu, Y., Chen, D., Lan, W., Zhao, Q., Dong, C., Xia, L. & Gong, P. (2010). Eur. J. Med. Chem. 45, 3504-3510.