Acta Crystallographica Section E

Structure Reports Online

Volume 69, Part 6 (June 2013)

organic compounds

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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