Received 15 May 2013
The title zwitterion,, C16H11ClN2O, is approximately planar, the dihedral angle between the benzene ring and naphthalene ring system is 1.55 (13)°; an intramolecular N-HO hydrogen bond stabilizes the planar conformation. In the crystal, - stacking between the benzene ring and the naphthalene ring system of adjacent molecules links the molecules into supramolecular chains running along the b axis, the centroid-centroid distance being 3.765 (2) Å.
For general background to the use of azo compounds as 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; for information, see: Wang et al. (2003). For a related structure, see: Elmali et al. (2001).
Data collection: KappaCCD Reference Manual (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; 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); software used to prepare material for publication: SHELXL97.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5708 ).
We are grateful to Mr L. Ouahab (University of Rennes, France) for his collaboration in the recording and interpretation of XRD data and express our gratitude for the valuable assistance he has provided throughout the realisation of this work.
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