(IUCr) Crystallography Journals Online

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Acta Cryst. (2002). E58, o317-o320 [ doi:10.1107/S1600536802003057 ]

N-(3-Chlorophenyl)-2-hydroxy-1-naphthaldimine at 200 K

G. Pavlovic, J. M. Sosa, D. Vikic-Topic and I. Leban

Abstract: The title compound, C₁₇H₁₂ClNO, (I), exists as the enol-imino tautomer [Csp²-O 1.333 (2) Å] in the solid state at 200 K, while NMR spectroscopy reveals the ketoamino form in dimethyl sulfoxide solution. The orientation of the Csp²-O (for the OH tautomer) and the Csp²=O bond (for the NH tautomer) towards the N-3-chlorophenyl substituent shows that both tautomers are E isomers with respect to the imino N=C bond. The solid-state OH tautomer is benzenoid, forming the very short resonance-assisted O-HN intramolecular hydrogen bond [NO 2.537 (2) Å]. The molecules are assembled using only van der Waals contacts. The packing of the molecules within the unit cell implies [pi] - [pi] interactions of adjacent naphthalene and phenyl rings, respectively. The energetically more favourable non-planar geometry [the dihedral angle between the naphthalene and 3-chlorophenyl rings is 17.2 (1)°] is in accordance with the absence of intermolecular hydrogen bonding that could compensate the formation of a less energetically favourable planar molecule.

Online 22 February 2002