Sarah Maloney, Alexandra M Z Slawin, J. Derek Woollins*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)


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.

Original languageEnglish
JournalActa Crystallographica Section E: Structure Reports Online
Issue number2
Publication statusPublished - 1 Feb 2013


  • data-to-parameter ratio = 13.0
  • mean σ(C-C) = 0.004 Å
  • R factor = 0.056
  • single-crystal X-ray study
  • T = 93 K
  • wR factor = 0.133


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