Crystal structure of rac-3-[2,3-bis(phenylsulfanyl)-3H-indol-3-yl]propanoic acid

Wayland E Noland, Christopher D. Brown, Amanda M. Bisel, Andrew K. Schneerer, Kenneth J Tritch

Research output: Contribution to journalArticlepeer-review


The title compound, C23H19NO2S2, was obtained as an unexpected regioisomer from an attempted synthesis of an intermediate for a substituent-effect study on ergot alkaloids. This is the first report of a 1H-indole monothioating at the 2- and 3-positions to give a 3H-indole. In the crystal, the acid H atom is twisted roughly 180° from the typical carboxy conformation and forms centrosymmetric O - H⋯N hydrogen-bonded dimers with the indole N atom of an inversion-related molecule. Together with a weak C - H⋯O hydrogen bond involving the carbonyl O atom, chains are formed along [100].

Original languageEnglish (US)
Pages (from-to)1414-1417
Number of pages4
JournalActa Crystallographica Section E: Crystallographic Communications
StatePublished - 2015


  • 3H-indole
  • O - H⋯N hydrogen bond
  • Uhle's ketone
  • crystal structure
  • ergot
  • thioation


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