(2S*,4aR*,8aS*)-6-Oxoperhydro-naphthalene-2-carboxylic acid

Dual hydrogen-bonding modes in a bicyclic -keto acid

Roger Lalancette, Hugh W. Thompson, Elizabeth M. Kikolski, Mark Davison

Research output: Contribution to journalArticle

Abstract

The title racemate, C11H16O3, displays two different hydrogen-bonding modes in the crystal structure. The chosen asymmetric unit consists of two mol-ecules of identical handedness that differ in the rotation of their carboxyl groups and are linked by an acid-to-ketone hydrogen bond [O⋯O = 2.7219 (17) Å and O - H⋯O = 174°]. The remaining carboxyl forms a centrosymmetric dimer with a second such unit [O⋯O = 2.6368 (15) Å and O - H⋯O = 174°], while the ketones at the extremities of this four-mol-ecule aggregate remain unengaged. Five inter-molecular C - H⋯O close contacts were found.

Original languageEnglish (US)
JournalActa Crystallographica Section E: Structure Reports Online
Volume63
Issue number4
DOIs
StatePublished - Mar 2 2007

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Keto Acids
Naphthalene
Carboxylic Acids
Ketones
Carboxylic acids
naphthalene
carboxylic acids
ketones
Hydrogen bonds
handedness
acids
Acids
carboxyl group
hydrogen
Dimers
Crystal structure
dimers
hydrogen bonds
crystal structure

All Science Journal Classification (ASJC) codes

  • Condensed Matter Physics
  • Structural Biology

Cite this

@article{6a86faf9ffa6490fbd15659acf1cdf00,
title = "(2S*,4aR*,8aS*)-6-Oxoperhydro-naphthalene-2-carboxylic acid: Dual hydrogen-bonding modes in a bicyclic -keto acid",
abstract = "The title racemate, C11H16O3, displays two different hydrogen-bonding modes in the crystal structure. The chosen asymmetric unit consists of two mol-ecules of identical handedness that differ in the rotation of their carboxyl groups and are linked by an acid-to-ketone hydrogen bond [O⋯O = 2.7219 (17) {\AA} and O - H⋯O = 174°]. The remaining carboxyl forms a centrosymmetric dimer with a second such unit [O⋯O = 2.6368 (15) {\AA} and O - H⋯O = 174°], while the ketones at the extremities of this four-mol-ecule aggregate remain unengaged. Five inter-molecular C - H⋯O close contacts were found.",
author = "Roger Lalancette and Thompson, {Hugh W.} and Kikolski, {Elizabeth M.} and Mark Davison",
year = "2007",
month = "3",
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doi = "https://doi.org/10.1107/S1600536807011609",
language = "English (US)",
volume = "63",
journal = "Acta Crystallographica Section E: Structure Reports Online",
issn = "1600-5368",
publisher = "International Union of Crystallography",
number = "4",

}

(2S*,4aR*,8aS*)-6-Oxoperhydro-naphthalene-2-carboxylic acid : Dual hydrogen-bonding modes in a bicyclic -keto acid. / Lalancette, Roger; Thompson, Hugh W.; Kikolski, Elizabeth M.; Davison, Mark.

In: Acta Crystallographica Section E: Structure Reports Online, Vol. 63, No. 4, 02.03.2007.

Research output: Contribution to journalArticle

TY - JOUR

T1 - (2S*,4aR*,8aS*)-6-Oxoperhydro-naphthalene-2-carboxylic acid

T2 - Dual hydrogen-bonding modes in a bicyclic -keto acid

AU - Lalancette, Roger

AU - Thompson, Hugh W.

AU - Kikolski, Elizabeth M.

AU - Davison, Mark

PY - 2007/3/2

Y1 - 2007/3/2

N2 - The title racemate, C11H16O3, displays two different hydrogen-bonding modes in the crystal structure. The chosen asymmetric unit consists of two mol-ecules of identical handedness that differ in the rotation of their carboxyl groups and are linked by an acid-to-ketone hydrogen bond [O⋯O = 2.7219 (17) Å and O - H⋯O = 174°]. The remaining carboxyl forms a centrosymmetric dimer with a second such unit [O⋯O = 2.6368 (15) Å and O - H⋯O = 174°], while the ketones at the extremities of this four-mol-ecule aggregate remain unengaged. Five inter-molecular C - H⋯O close contacts were found.

AB - The title racemate, C11H16O3, displays two different hydrogen-bonding modes in the crystal structure. The chosen asymmetric unit consists of two mol-ecules of identical handedness that differ in the rotation of their carboxyl groups and are linked by an acid-to-ketone hydrogen bond [O⋯O = 2.7219 (17) Å and O - H⋯O = 174°]. The remaining carboxyl forms a centrosymmetric dimer with a second such unit [O⋯O = 2.6368 (15) Å and O - H⋯O = 174°], while the ketones at the extremities of this four-mol-ecule aggregate remain unengaged. Five inter-molecular C - H⋯O close contacts were found.

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U2 - https://doi.org/10.1107/S1600536807011609

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