(-)-Isosantonic acid: Alteration of the hydrogen-bonding mode by configurational inversion at a single centre in a γ,ε- diketocarboxylic acid

Juan Zinczuk; Edmundo A. Ruveda; Roger A. Lalancette; Hugh W. Thompson

doi:10.1107/S160053680601405X

(-)-Isosantonic acid: Alteration of the hydrogen-bonding mode by configurational inversion at a single centre in a γ,ε- diketocarboxylic acid

Juan Zinczuk, Edmundo A. Ruveda, Roger A. Lalancette, Hugh W. Thompson

Rutgers Newark, Chemistry

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

Abstract

The title diketo acid, (1R,3aS,6aS,7R,9S)-(-)-α,3a,7-trimethyl-5,8- dioxo-1,4-ethanoperhydropentalene-1-acetic acid (C₁₅H ₂₀O₄), is shown to aggregate in the crystal structure as acid-to-ketone hydrogen-bonding catemers, whose chains follow 2₁ screw axes from each carboxyl to a ketone in a neighbouring molecule [O⋯O = 2.7472(13) and O⋯H - O = 172.7(17)°]. Two parallel counterdirectional screw-related single-strand hydrogen-bonding chains pass through the cell in the a direction. Six intermolecular C - H⋯O=C close contacts are found. Comparisons are drawn with a diastereomer having the opposite configuration at the methylated chiral centre adjacent to the carboxyl group.

Original language	English (US)
Pages (from-to)	o2120-o2122
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	62
Issue number	6
DOIs	https://doi.org/10.1107/S160053680601405X
State	Published - Jun 2006

All Science Journal Classification (ASJC) codes

Chemistry(all)
Materials Science(all)
Condensed Matter Physics

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title = "(-)-Isosantonic acid: Alteration of the hydrogen-bonding mode by configurational inversion at a single centre in a γ,ε- diketocarboxylic acid",

abstract = "The title diketo acid, (1R,3aS,6aS,7R,9S)-(-)-α,3a,7-trimethyl-5,8- dioxo-1,4-ethanoperhydropentalene-1-acetic acid (C15H 20O4), is shown to aggregate in the crystal structure as acid-to-ketone hydrogen-bonding catemers, whose chains follow 21 screw axes from each carboxyl to a ketone in a neighbouring molecule [O⋯O = 2.7472(13) and O⋯H - O = 172.7(17)°]. Two parallel counterdirectional screw-related single-strand hydrogen-bonding chains pass through the cell in the a direction. Six intermolecular C - H⋯O=C close contacts are found. Comparisons are drawn with a diastereomer having the opposite configuration at the methylated chiral centre adjacent to the carboxyl group.",

author = "Juan Zinczuk and Ruveda, {Edmundo A.} and Lalancette, {Roger A.} and Thompson, {Hugh W.}",

year = "2006",

month = jun,

doi = "10.1107/S160053680601405X",

language = "English (US)",

volume = "62",

pages = "o2120--o2122",

journal = "Acta Crystallographica Section E: Structure Reports Online",

issn = "1600-5368",

publisher = "International Union of Crystallography",

number = "6",

}

(-)-Isosantonic acid: Alteration of the hydrogen-bonding mode by configurational inversion at a single centre in a γ,ε- diketocarboxylic acid. / Zinczuk, Juan; Ruveda, Edmundo A.; Lalancette, Roger A. et al.
In: Acta Crystallographica Section E: Structure Reports Online, Vol. 62, No. 6, 06.2006, p. o2120-o2122.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - (-)-Isosantonic acid

T2 - Alteration of the hydrogen-bonding mode by configurational inversion at a single centre in a γ,ε- diketocarboxylic acid

AU - Zinczuk, Juan

AU - Ruveda, Edmundo A.

AU - Lalancette, Roger A.

AU - Thompson, Hugh W.

PY - 2006/6

Y1 - 2006/6

N2 - The title diketo acid, (1R,3aS,6aS,7R,9S)-(-)-α,3a,7-trimethyl-5,8- dioxo-1,4-ethanoperhydropentalene-1-acetic acid (C15H 20O4), is shown to aggregate in the crystal structure as acid-to-ketone hydrogen-bonding catemers, whose chains follow 21 screw axes from each carboxyl to a ketone in a neighbouring molecule [O⋯O = 2.7472(13) and O⋯H - O = 172.7(17)°]. Two parallel counterdirectional screw-related single-strand hydrogen-bonding chains pass through the cell in the a direction. Six intermolecular C - H⋯O=C close contacts are found. Comparisons are drawn with a diastereomer having the opposite configuration at the methylated chiral centre adjacent to the carboxyl group.

AB - The title diketo acid, (1R,3aS,6aS,7R,9S)-(-)-α,3a,7-trimethyl-5,8- dioxo-1,4-ethanoperhydropentalene-1-acetic acid (C15H 20O4), is shown to aggregate in the crystal structure as acid-to-ketone hydrogen-bonding catemers, whose chains follow 21 screw axes from each carboxyl to a ketone in a neighbouring molecule [O⋯O = 2.7472(13) and O⋯H - O = 172.7(17)°]. Two parallel counterdirectional screw-related single-strand hydrogen-bonding chains pass through the cell in the a direction. Six intermolecular C - H⋯O=C close contacts are found. Comparisons are drawn with a diastereomer having the opposite configuration at the methylated chiral centre adjacent to the carboxyl group.

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(-)-Isosantonic acid: Alteration of the hydrogen-bonding mode by configurational inversion at a single centre in a γ,ε- diketocarboxylic acid

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