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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].

SUBMITTER: Noland WE 

PROVIDER: S-EPMC4645081 | biostudies-other | 2015 Nov

REPOSITORIES: biostudies-other

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

Noland Wayland E WE   Brown Christopher D CD   Bisel Amanda M AM   Schneerer Andrew K AK   Tritch Kenneth J KJ  

Acta crystallographica. Section E, Crystallographic communications 20151031 Pt 11

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  ...[more]

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