Received 8 July 2013
The title zwitterion, C17H14N2O2, crystallizes with two independent molecules in the asymmetric unit, both of which are approximately planar, the dihedral angles between the benzene ring and the naphthalene ring system being 4.39 (12)° in one molecule and 5.83 (12)° in the other, and show an E conformation with respect to the azo double bond. An intramolecular N-HO hydrogen bond in each molecule helps to establish their near planar conformation. In the crystal, molecules are linked through O-HO hydrogen bonds into infinite chains running along the a-axis direction. In addition, the chains are stacked along the b axis via - interactions between the benzene and the naphthalene rings of adjacent molecules, the centroid-centroid distances being 3.722 (3) and 3.823 (4) Å.
For general background to the use of azo compounds as dyes, pigments and advanced materials, see: Lee et al. (2004). For details of azo pigments, see: Herbst & Hunger (2004). For related structures of hydrazone derivatives, see: Olivieri et al. (1989); Oakes (2002). For bond-length data, see: Yazici et al. (2010); Karadayi et al. (2006). Many azo compounds have been synthesized by diazotization and diazo coupling reactions, see: Wang et al. (2003).
Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LR2112 ).
We thank all researchers of the CHEMS Research Unit, University of Constantine, Algeria, for their valuable assistance. Thanks are due to the MESRS (Ministère de l'Enseignement Supérieur et de la Recherche Scientifique -Algérie) for financial support. We also express our gratitude to Professor L. Ouahab, Director of Research at the Laboratory UMR LCSIM 6511, CNRS, Rennes I (France), for recording the diffraction data and help with the structure determination.
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