Crystal structure of (S)-5,7-diphenyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine

Ivy K. Price, Celine Rougeot, Jason E. Hein*, W. T A Harrison (Editor)

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)
7 Downloads (Pure)


The title compound, C16H13N5, was synthesized by coupling aminotetrazole with chalcone in the presence of an amine organocatalyst derived from chincona alkaloid. There are two molecules, A and B, in the asymmetric unit. In molecule A, the dihedral angles between the partly hydrogenated pyrimidine ring system (r.m.s. deviation = 0.056 Å) and the sp2- and sp3-bonded phenyl groups are 33.32 (11) and 86.53 (11)°, respectively. The equivalent data for molecule B are 0.049 Å, and 27.05 (10) and 85.27 (11)°, respectively. In the crystal, A+B dimers linked by pairs of N - H⋯N hydrogen bonds generate R 22(8) loops. The dimers are linked by aromatic π-π stacking interactions [shortest centroid-centroid separation = 3.5367 (15) Å], which results in a three-dimensional network.

Original languageEnglish
Pages (from-to)o220-o221
Number of pages2
JournalActa Crystallographica Section E: Structure Reports Online
Issue number4
Early online date4 Mar 2015
Publication statusPublished - 1 Apr 2015

Bibliographical note

The authors thank Christopher Daley, A. Rheingold and C. Moore (UCSD) for the data collection. Funding for this work was provided by the University of California, Merced and the National Science Foundation (CHE-1300686)


  • Crystal structure
  • Hydrogen bonding
  • Tetrazolo[1,5-a]pyrimidine
  • π-π stacking


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