Acta Cryst. (2009). E65, o490-o491  [ doi:10.1107/S1600536809001007 ]

(E)-2-[(2-Hydroxy-5-nitrophenyl)iminiomethyl]phenolate

Y. M. Hijji, B. Barare, R. J. Butcher and J. P. Jasinski

Abstract: In the title molecule, C₁₃H₁₀N₂O₄, the dihedral angle between the mean planes of the benzene and phenolate rings is 21.6 (4)°. The nitro O atoms are twisted slightly out of the plane of the ring to which the nitro group is attached [dihedral angle 8.4 (3)°]. The amine group forms an intramolecular hydrogen bond with both nearby O atoms. An extended delocalization throughout the entire molecule exists producing a zwitterionic effect in this region of the molecule. The shortened C-O bond [1.2997 (15) Å] in concert with the slightly longer C-OH bond [1.3310 (16) Å] provide evidence for this effect. The crystal packing is influenced by strong intermolecular O-HO hydrogen bonding. As a result, molecules are linked into an infinite zigzag chain running along the b axis. A MOPAC PM3 calculation provides support to these observations.

Online 11 February 2009

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