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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.


A view along [04] of the O1—H1O⋯N1 hydrogen-bonded inversion dimer. The C12–C17 ring has been omitted for clarity.
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fig3: A view along [04] of the O1—H1O⋯N1 hydrogen-bonded inversion dimer. The C12–C17 ring has been omitted for clarity.

Mentions: The mol­ecular structure of the title compound is shown in Fig. 2 ▸. The O1—H1O bond is syn-periplanar with C1—C2 (Fig. 3 ▸), in contrast to the anti-periplanar hydroxyl conformation usually observed in carboxyl groups. This is a consequence of an O1—H1O⋯N1 hydrogen bond (Table 1 ▸; §3). The remaining structural features are typical. The atoms of the indole unit (N1/C4–C11) have an r.m.s. deviation of 0.010 (2) Å from the mean plane, with quaternary carbon C4 only 0.012 (2) Å out of plane. The O1/C1–C4/S2/C18 (O1–C18) chain adopts a staggered conformation whose plane of best fit is inclined by 87.97 (8)° to that of the indole unit. Phenyl ring C18–C23 is inclined by 79.39 (10)° to the mean plane of the O1–C18 chain. Phenyl ring C12–C17 ring is inclined by 71.91 (7)° to the mean plane of the indole unit (Fig. 2 ▸). The C12—S1 bond is syn-periplanar with bond N1=C11, supporting conjugation between atom S1 and the indole system.


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)

A view along [04] of the O1—H1O⋯N1 hydrogen-bonded inversion dimer. The C12–C17 ring has been omitted for clarity.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

fig3: A view along [04] of the O1—H1O⋯N1 hydrogen-bonded inversion dimer. The C12–C17 ring has been omitted for clarity.
Mentions: The mol­ecular structure of the title compound is shown in Fig. 2 ▸. The O1—H1O bond is syn-periplanar with C1—C2 (Fig. 3 ▸), in contrast to the anti-periplanar hydroxyl conformation usually observed in carboxyl groups. This is a consequence of an O1—H1O⋯N1 hydrogen bond (Table 1 ▸; §3). The remaining structural features are typical. The atoms of the indole unit (N1/C4–C11) have an r.m.s. deviation of 0.010 (2) Å from the mean plane, with quaternary carbon C4 only 0.012 (2) Å out of plane. The O1/C1–C4/S2/C18 (O1–C18) chain adopts a staggered conformation whose plane of best fit is inclined by 87.97 (8)° to that of the indole unit. Phenyl ring C18–C23 is inclined by 79.39 (10)° to the mean plane of the O1–C18 chain. Phenyl ring C12–C17 ring is inclined by 71.91 (7)° to the mean plane of the indole unit (Fig. 2 ▸). The C12—S1 bond is syn-periplanar with bond N1=C11, supporting conjugation between atom S1 and the indole system.

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.