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

doi:10.1107/S2056989015020241

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

Chemistry (Twin Cities)

Research output: Contribution to journal › Article

Abstract

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 language	English (US)
Pages (from-to)	1414-1417
Number of pages	4
Journal	Acta Crystallographica Section E: Crystallographic Communications
Volume	71
DOIs	https://doi.org/10.1107/S2056989015020241
State	Published - 2015

Keywords

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

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Noland, W. E., Brown, C. D., Bisel, A. M., Schneerer, A. K., & Tritch, K. J. (2015). Crystal structure of rac-3-[2,3-bis(phenylsulfanyl)-3H-indol-3-yl]propanoic acid. Acta Crystallographica Section E: Crystallographic Communications, 71, 1414-1417. https://doi.org/10.1107/S2056989015020241

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

abstract = "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].",

keywords = "3H-indole, O - H⋯N hydrogen bond, Uhle's ketone, crystal structure, ergot, thioation",

author = "Noland, {Wayland E} and Brown, {Christopher D.} and Bisel, {Amanda M.} and Schneerer, {Andrew K.} and Tritch, {Kenneth J}",

year = "2015",

doi = "10.1107/S2056989015020241",

language = "English (US)",

volume = "71",

pages = "1414--1417",

journal = "Acta Crystallographica Section E: Crystallographic Communications",

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publisher = "International Union of Crystallography",

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T1 - Crystal structure of rac-3-[2,3-bis(phenylsulfanyl)-3H-indol-3-yl]propanoic acid

AU - Noland, Wayland E

AU - Brown, Christopher D.

AU - Bisel, Amanda M.

AU - Schneerer, Andrew K.

AU - Tritch, Kenneth J

PY - 2015

Y1 - 2015

N2 - 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].

AB - 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].

KW - 3H-indole

KW - O - H⋯N hydrogen bond

KW - Uhle's ketone

KW - crystal structure

KW - ergot

KW - thioation

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