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3-Oxocyclo-butane-carboxylic acid: hydrogen bonding in a small-ring ?-keto acid.

ABSTRACT: The title ketocarboxylic acid, C(5)H(6)O(3), is the smallest carboxy-cyclanone to have its crystal structure determined. It adopts a chiral conformation, by rotation of its carboxyl O atoms away from the plane of skeletal symmetry that passes through the carboxyl carbon and both atoms of the ketone carbonyl. The four-membered ring is non-planar, with a shallow fold of 14.3?(1)° along a line connecting the two ?-carbons of the ketone group. In the crystal, the molecules are linked by centrosymmetric hydrogen-bond pairing of ordered carboxylic acid groups [O?O = 2.6392?(12)?Å and O-H?O = 175.74?(15)°], yielding two different sets of dimers, related by by a 2(1) screw axis in c, in the cell. A C-H?O interaction is also present.

SUBMITTER: Efthimiopoulos G

PROVIDER: S-EPMC2968635 | biostudies-literature | 2009 Feb

REPOSITORIES: biostudies-literature

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3-Oxocyclo-butane-carboxylic acid: hydrogen bonding in a small-ring γ-keto acid.

Efthimiopoulos Georgia G Thompson Hugh W HW Lalancette Roger A RA

Acta crystallographica. Section E, Structure reports online 20090211 Pt 3

The title ketocarboxylic acid, C(5)H(6)O(3), is the smallest carboxy-cyclanone to have its crystal structure determined. It adopts a chiral conformation, by rotation of its carboxyl O atoms away from the plane of skeletal symmetry that passes through the carboxyl carbon and both atoms of the ketone carbonyl. The four-membered ring is non-planar, with a shallow fold of 14.3 (1)° along a line connecting the two α-carbons of the ketone group. In the crystal, the molecules are linked by centrosymmet ...[more]

PMID: 21582158

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