title: Crystal structure of rac-3-[2,3-bis-(phenyl-sulfan-yl)-3H-indol-3-yl]propanoic acid.
abstract: The title compound, C23H19NO2S2, was obtained as an unexpected regioisomer from an attempted synthesis of an inter-mediate for a substituent-effect study on ergot alkaloids. This is the first report of a 1H-indole mono-thio-ating 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 carb-oxy conformation and forms centrosymmetric O-H⋯N hydrogen-bonded dimers with the indole N atom of an inversion-related mol-ecule. Together with a weak C-H⋯O hydrogen bond involving the carbonyl O atom, chains are formed along [100].
authors.affiliation: Department of Chemistry, University of Minnesota, Minneapolis, MN 55455-0431, USA.
authors.forename: Wayland E
authors.initials: WE
authors.lastname: Noland
authors.affiliation: Department of Chemistry, University of Minnesota, Minneapolis, MN 55455-0431, USA.
authors.forename: Christopher D
authors.initials: CD
authors.lastname: Brown
authors.affiliation: Department of Chemistry, University of Minnesota, Minneapolis, MN 55455-0431, USA.
authors.forename: Amanda M
authors.initials: AM
authors.lastname: Bisel
authors.affiliation: Department of Chemistry, University of Minnesota, Minneapolis, MN 55455-0431, USA.
authors.forename: Andrew K
authors.initials: AK
authors.lastname: Schneerer
authors.affiliation: Department of Chemistry, University of Minnesota, Minneapolis, MN 55455-0431, USA.
authors.forename: Kenneth J
authors.initials: KJ
authors.lastname: Tritch
keywords: 3H-indole; O—H⋯N hydrogen bond; Uhle’s ketone; crystal structure; ergot; thio­ation