Received 26 April 2013
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-HO, rather than an O-HN, 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-HO hydrogen bonds involving the methanol molecule, which is located about a twofold rotation axis, and hence half-occupied, forming zigzag chains along . Molecules are also linked via C-H and - 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.
For azo compounds in the fields of dyes, pigments and advanced materials, see: Lee et al. (2004); Oueslati et al. (2004). For the synthesis of azo compounds, see: Wang et al. (2003). For the structures of related compounds, see: Jin et al. (2008); Xu et al. (2010).
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: PLATON (Spek, 2009); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2594 ).
The authors, particularly MB (PNR project), thank the MESRS (Algeria) for financial support. Thanks are also due to Professor 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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