Structure of a rearrangement product: 1-methyl-3-(5-amino-1-benzylimidazol-4-yl)-1,2,4-triazole, C13H14N6

Carol Afshar, Helen M. Berman, Patricia Sawzik, Leslie Lessinger, Benjamin B. Lim, Ramachandra S. Hosmane

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The title compound was prepared during the course of an attempt to synthesize 8-amino-3-benzyl-6-methylimidazo[4,5-e][1,2,4]triazepine. The crystals are monoclinic, space group P21/c, a=6.2375(5), b=9.1070(8), c=22.182(2) Å, β=91.797(7)°, Z=4. The structure was solved by direct methods and refined by least squares to R=0.063 on all 2142 measured reflections. The imidazol-4-yl-triazole system is planar, conjugated, and aromatic. One hydrogen atom of the exocyclic amino group is involved in a bifurcated hydrogen bond, of which one branch is an intramolecular attraction to a triazole ring nitrogen atom, while the other branch is intermolecular. The crystal is held together by two N-H⋯N hydrogen bonds between molecules related by translation along the a axis and by π-π stacking interactions of the imidazol-4-yl-triazole ring systems and the phenyl rings across centers of inversion.

Original languageEnglish (US)
Pages (from-to)533-543
Number of pages11
JournalJournal of Crystallographic and Spectroscopic Research
Issue number4
StatePublished - Aug 1987
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Structural Biology
  • Condensed Matter Physics
  • Spectroscopy


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