Received 3 July 2013
The title azo molecule, C16H9Br3N2O, adopts a trans conformation with respect to the azo N=N double bond. An intramolecular O-HN hydrogen bond forms an S(6) ring motif. The dihedral angle between the naphthalene ring system and the benzene ring is 33.80 (16)°. In the crystal, molecules are stacked in columns along the a axis by - interactions [centroid-centroid distances = 3.815 (3) and 3.990 (3) Å].
For applications of azo compounds, see: Gale et al. (1998). For the synthesis of similar compounds, see: Wang et al. (2003); Heinrich et al. (2007). For bond lengths and angles in related azo compounds, see: Deveci et al. (2005); El-Ghamry et al. (2008).
Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; 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: WinGX (Farrugia, 2012).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5290 ).
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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