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Acta Cryst. (2013). E69, o867-o868
[ doi:10.1107/S1600536813012245 ]

1-(4-Hydroxyphenyl)-2-(2-oxidonaphthalen-1-yl)diazen-1-ium methanol hemisolvate

M. A. Benaouida, S. Chetioui and S. E. Bouaoud

Abstract: In the title compound, C16H12N2O2·0.5CH3OH, the H atom of the -OH group has been transfered to the N atom in the azo group, forming a zwitterion. Hence, there is an intramolecular N-H...O, rather than an O-H...N, hydrogen bond in the molecule. The molecule is almost planar, the dihedral angle between the benzene ring and the mean plane of the naphthalene ring system being 4.51 (6)°. In the crystal, molecules are linked to and bridged by O-H...O hydrogen bonds involving the methanol molecule, which is located about a twofold rotation axis, and hence half-occupied, forming zigzag chains along [001]. Molecules are also linked via C-H...[pi] and [pi]-[pi] interactions, the latter involving adjacent benzene and naphthalene rings and having a centroid-centroid distance of 3.6616 (13) Å, forming a three-dimensional network.

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