5-Oxocyclooctanecarboxylic acid: Hydrogen-bonding pattern and conformational disorder in a medium-ring ε-keto acid

Roger A. Lalancette; Andrew P.J. Brunskill; Hugh W. Thompson

doi:10.1107/S0108270100009793

5-Oxocyclooctanecarboxylic acid: Hydrogen-bonding pattern and conformational disorder in a medium-ring ε-keto acid

Roger A. Lalancette, Andrew P.J. Brunskill, Hugh W. Thompson

Rutgers Newark, Chemistry

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

Abstract

Molecules of the title compound, C₉H₁₄O₃, adopt a chiral `boat-chair' conformation, in which the carboxyl group avoids potential cross-ring ketone interactions by an outward `equatorial' orientation. The asymmetric unit contains two such molecules, one conformationally fixed without disorder, (I), and the other, (I′), extensively disordered, both in the bond lengths and angles of the carboxyl and by a coupled `updown' conformational disordering [ratio of 60:40 (1)] of the remote ends of the boat-chair system. Each molecule in the asymmetric unit forms a centrosymmetric hydrogen-bonded carboxyl dimer with a second molecule of its own type. For (I), O···O = 2.658 (3) angstroms and O-H···O = 174°. For (I′), O···O = 2.653 (3) angstroms and O-H···O = 165°. A number of intermolecular C double bond O···H-C close contacts are found.

Original language	English (US)
Pages (from-to)	1260-1262
Number of pages	3
Journal	Acta Crystallographica, Section C: Crystal Structure Communications
Volume	56
Issue number	10
DOIs	https://doi.org/10.1107/S0108270100009793
State	Published - Oct 2000

All Science Journal Classification (ASJC) codes

General Biochemistry, Genetics and Molecular Biology

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title = "5-Oxocyclooctanecarboxylic acid: Hydrogen-bonding pattern and conformational disorder in a medium-ring ε-keto acid",

abstract = "Molecules of the title compound, C9H14O3, adopt a chiral `boat-chair' conformation, in which the carboxyl group avoids potential cross-ring ketone interactions by an outward `equatorial' orientation. The asymmetric unit contains two such molecules, one conformationally fixed without disorder, (I), and the other, (I′), extensively disordered, both in the bond lengths and angles of the carboxyl and by a coupled `updown' conformational disordering [ratio of 60:40 (1)] of the remote ends of the boat-chair system. Each molecule in the asymmetric unit forms a centrosymmetric hydrogen-bonded carboxyl dimer with a second molecule of its own type. For (I), O···O = 2.658 (3) angstroms and O-H···O = 174°. For (I′), O···O = 2.653 (3) angstroms and O-H···O = 165°. A number of intermolecular C double bond O···H-C close contacts are found.",

author = "Lalancette, {Roger A.} and Brunskill, {Andrew P.J.} and Thompson, {Hugh W.}",

year = "2000",

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T2 - Hydrogen-bonding pattern and conformational disorder in a medium-ring ε-keto acid

AU - Lalancette, Roger A.

AU - Brunskill, Andrew P.J.

AU - Thompson, Hugh W.

PY - 2000/10

Y1 - 2000/10

N2 - Molecules of the title compound, C9H14O3, adopt a chiral `boat-chair' conformation, in which the carboxyl group avoids potential cross-ring ketone interactions by an outward `equatorial' orientation. The asymmetric unit contains two such molecules, one conformationally fixed without disorder, (I), and the other, (I′), extensively disordered, both in the bond lengths and angles of the carboxyl and by a coupled `updown' conformational disordering [ratio of 60:40 (1)] of the remote ends of the boat-chair system. Each molecule in the asymmetric unit forms a centrosymmetric hydrogen-bonded carboxyl dimer with a second molecule of its own type. For (I), O···O = 2.658 (3) angstroms and O-H···O = 174°. For (I′), O···O = 2.653 (3) angstroms and O-H···O = 165°. A number of intermolecular C double bond O···H-C close contacts are found.

AB - Molecules of the title compound, C9H14O3, adopt a chiral `boat-chair' conformation, in which the carboxyl group avoids potential cross-ring ketone interactions by an outward `equatorial' orientation. The asymmetric unit contains two such molecules, one conformationally fixed without disorder, (I), and the other, (I′), extensively disordered, both in the bond lengths and angles of the carboxyl and by a coupled `updown' conformational disordering [ratio of 60:40 (1)] of the remote ends of the boat-chair system. Each molecule in the asymmetric unit forms a centrosymmetric hydrogen-bonded carboxyl dimer with a second molecule of its own type. For (I), O···O = 2.658 (3) angstroms and O-H···O = 174°. For (I′), O···O = 2.653 (3) angstroms and O-H···O = 165°. A number of intermolecular C double bond O···H-C close contacts are found.

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5-Oxocyclooctanecarboxylic acid: Hydrogen-bonding pattern and conformational disorder in a medium-ring ε-keto acid

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