Received 20 December 2012
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(arene) interactions, near the short T-shaped limit, link molecules in the absence of strong acceptors.
Data collection: CrystalClear-SM Expert (Rigaku, 2009); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GG2107 ).
We are grateful to EPSRC for support.
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