(IUCr) Crystallography Journals Online

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Acta Cryst. (2013). E69, o246
[ doi:10.1107/S1600536813000986 ]

2,2-Dimethyl-2,3-dihydro-1H-perimidine

S. Maloney, A. M. Z. Slawin and J. D. Woollins

Abstract: The title compound, C₁₃H₁₄N₂, was obtained from reaction of diaminonaphthalene with acetone. In both independent molecules in the asymmetric unit, the tricyclic perimidine consists of a planar (r.m.s. deviations = 0.0125 and 0.0181 Å) naphthalene ring system and an envelope conformation C₄N₂ ringwith the NCN group hinged with respect to the naphthalene backbone by 36.9 (2) and 41.3 (2)° in the two independent molecules. The methyl substituents are arranged approximately axial and equatorial on the apical C atom. In the crystal, one of the N-H groups of one independent molecule is involved in classical N-HN hydrogen bonding. Short intermolecular (C/N)-H [pi] (arene) interactions, near the short T-shaped limit, link molecules in the absence of strong acceptors.