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

Noland WE, Brown CD, Bisel AM, Schneerer AK, Tritch KJ - Acta Crystallogr E Crystallogr Commun (2015)

Bottom Line: 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.

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Affiliation: Department of Chemistry, University of Minnesota, Minneapolis, MN 55455-0431, USA.

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].

No MeSH data available.


The three 2-thio-3H-indoles found in the Cambridge Structural Database (CSD; Groom & Allen, 2014 ▸).
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fig5: The three 2-thio-3H-indoles found in the Cambridge Structural Database (CSD; Groom & Allen, 2014 ▸).

Mentions: A search was performed for variously substituted 3H-indoles in the Cambridge Structural Database (CSD, Version 5.36, update 3; Groom & Allen, 2014 ▸). No entries were found containing a 3-thio or 3-propanoic functionality. Three examples of 2-thio-3H-indoles were found. Spiro-fused cyclo­hexa­none (7) contains a 2-phenyl­thio group with similar geometry as is found in the title compound (Fig. 5 ▸; Feldman & Nuriye, 2009 ▸). The long chain in chloro­triester (8) is primarily staggered and normal to the indole unit, akin to the title compound (Novikov et al., 2003 ▸). The third example, (9), is a thia­zolium-4-oxide (Moody et al., 2003 ▸).


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

Noland WE, Brown CD, Bisel AM, Schneerer AK, Tritch KJ - Acta Crystallogr E Crystallogr Commun (2015)

The three 2-thio-3H-indoles found in the Cambridge Structural Database (CSD; Groom & Allen, 2014 ▸).
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4645081&req=5

fig5: The three 2-thio-3H-indoles found in the Cambridge Structural Database (CSD; Groom & Allen, 2014 ▸).
Mentions: A search was performed for variously substituted 3H-indoles in the Cambridge Structural Database (CSD, Version 5.36, update 3; Groom & Allen, 2014 ▸). No entries were found containing a 3-thio or 3-propanoic functionality. Three examples of 2-thio-3H-indoles were found. Spiro-fused cyclo­hexa­none (7) contains a 2-phenyl­thio group with similar geometry as is found in the title compound (Fig. 5 ▸; Feldman & Nuriye, 2009 ▸). The long chain in chloro­triester (8) is primarily staggered and normal to the indole unit, akin to the title compound (Novikov et al., 2003 ▸). The third example, (9), is a thia­zolium-4-oxide (Moody et al., 2003 ▸).

Bottom Line: 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.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, University of Minnesota, Minneapolis, MN 55455-0431, USA.

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].

No MeSH data available.