Received 18 June 2013
There are two independent zwitterion molecules (A and B) in the asymmetric unit of the title compound, C17H11N3O, which belongs to the family of azo dyes. The dihedral angle between the benzene ring and the naphthalene ring system is 6.99 (6)° in molecule A and 4.38 (6)° in molecule B. The azo group adopts an E conformation with respect to the -N=N- bond and each of the independent molecules has an intramolecular N-HO hydrogen bond. In the crystal, molecules are linked by C-HO and C-HN hydrogen bonds, forming ribbons propagating along [-110]. The ribbons are linked via - interactions involving the benzene and naphthalene rings of inversion-related A and inversion-related B molecules, forming a three-dimensional structure. The most significant centroid-centroid distances vary from 3.6599 (6) to 3.7538 (9) Å.
For general background to azo compounds and their use in dyes, pigments and advanced materials, see: Lee et al. (2004); Oueslati et al. (2004). Many azo compounds have been synthesized by diazotization and diazo coupling reactions, see: Wang et al. (2003). For a related structure, see: Rãdulescu et al. (2006). For bond-length data, see: Allen et al. (1987).
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: SU2616 ).
We thank all researchers of the CHEMS Research Unit of the University of Constantine, Algeria, for the valuable assistance they have provided us throughout the realisation of this work. We also express our gratitude and thank Mr. L Ouahab, Director of Research at laboratory UMR LCSIM 6511, CNRS, Rennes I (France), for his valuable collaboration in the recording and interpretation of the XRD data.
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