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Acta Cryst. (2013). E69, o1175-o1176  [ doi:10.1107/S1600536813017261 ]

(E)-1-[2-(2-Cyanophenyl)diazen-2-ium-1-yl]naphthalen-2-olate

H. Bougueria, M. A. Benaouida, S. Bouacida and A. el kader Bouchoul

Abstract: 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-H...O hydrogen bond. In the crystal, molecules are linked by C-H...O and C-H...N hydrogen bonds, forming ribbons propagating along [-110]. The ribbons are linked via [pi]-[pi] 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.


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