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4-Oxocyclo-hexa-neacetic acid: catemeric hydrogen bonding and spontaneous resolution of a single conformational enanti-omer in an achiral ∊-keto acid.

ABSTRACT: The asymmetric unit of the title compound, C(8)H(12)O(3), consists of a single conformational enanti-omer, which aggregates in the catemeric acid-to-ketone hydrogen-bonding mode [O⋯O = 2.682 (4) Å and O-H⋯O = 172 (6)°]. Four hydrogen-bonding chains of translationally related mol-ecules pass through the cell orthogonal to the 4(3) screw axis along c, alternating in the 110 and the 10 direction, with alignment with respect to this axis of + + - -. Successive chains are rotated by 90° around the c axis. One C-H⋯O=C close contact, involving the carboxyl group, exists.

SUBMITTER: Barcon A

PROVIDER: S-EPMC2983244 | biostudies-literature | 2010 Sep

REPOSITORIES: biostudies-literature

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4-Oxocyclo-hexa-neacetic acid: catemeric hydrogen bonding and spontaneous resolution of a single conformational enanti-omer in an achiral ∊-keto acid.

Barcon Alan A Brunskill Andrew P J AP Lalancette Roger A RA Thompson Hugh W HW

Acta crystallographica. Section E, Structure reports online 20100918 Pt 10

The asymmetric unit of the title compound, C(8)H(12)O(3), consists of a single conformational enanti-omer, which aggregates in the catemeric acid-to-ketone hydrogen-bonding mode [O⋯O = 2.682 (4) Å and O-H⋯O = 172 (6)°]. Four hydrogen-bonding chains of translationally related mol-ecules pass through the cell orthogonal to the 4(3) screw axis along c, alternating in the 110 and the 10 direction, with alignment with respect to this axis of + + - -. Successive chains are rotated by 90° around the c ...[more]

PMID: 21587559

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