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—H⋯N hydrogen bonding. Short intermolecular (C/N)—H⋯π(arene) interactions, near the short T-shaped limit, link molecules in the absence of strong acceptors.
Highlights
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 A ) 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
One of the N—H groups of one independent molecule is involved in classical N—HÁ Á ÁN hydrogen bonding
Cg1, Cg2 and Cg3 are the centroids of the C21–C25/C30, C25–C30 and C5– C10 rings, respectively
Summary
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 A ) 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. One of the N—H groups of one independent molecule is involved in classical N—HÁ Á ÁN hydrogen bonding. Related literature For general background to perimidines and their biological activity, see: Shaabani & Maleki (2008); Sauer et al (2006). See: Martinez-Belmonte et al (2010)
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