(+)-3-Oxo-23,24-dinor-5α-cholan-22-oic acid: Hydrogen-bonding patterns in a steroidal keto acid and its monohydrate

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

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

The X-ray crystal structures of the title steroidal keto acid in both its anhydrous, C22H34O3, (I), and monohydrate, C22H34O3.H2O, (II), forms have been determined. Neither hydrogen-bonding pattern involves the ketone. Compound (I) forms infinite carboxyl-to-carboxyl hydrogen-bonding chains. This is the first observed case of a keto carboxylic acid forming such an acid-to-acid catemer. In (II), each carboxyl is hydrogen bonded to three water molecules and each water forms hydrogen bonds with carboxyl groups from three steroid molecules, creating a network of connected ten-membered hydrogen-bonding rings.

Original languageEnglish (US)
Pages (from-to)421-424
Number of pages4
JournalActa Crystallographica Section C: Crystal Structure Communications
Volume54
Issue number3
DOIs
StatePublished - Mar 15 1998

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Keto Acids
Hydrogen Bonding
Hydrogen bonds
Acids
Hydrogen
Water
Carboxylic Acids
Ketones
Molecules
Steroids
X-Rays
Crystal structure
X rays

All Science Journal Classification (ASJC) codes

  • Biochemistry, Genetics and Molecular Biology(all)

Cite this

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title = "(+)-3-Oxo-23,24-dinor-5α-cholan-22-oic acid: Hydrogen-bonding patterns in a steroidal keto acid and its monohydrate",
abstract = "The X-ray crystal structures of the title steroidal keto acid in both its anhydrous, C22H34O3, (I), and monohydrate, C22H34O3.H2O, (II), forms have been determined. Neither hydrogen-bonding pattern involves the ketone. Compound (I) forms infinite carboxyl-to-carboxyl hydrogen-bonding chains. This is the first observed case of a keto carboxylic acid forming such an acid-to-acid catemer. In (II), each carboxyl is hydrogen bonded to three water molecules and each water forms hydrogen bonds with carboxyl groups from three steroid molecules, creating a network of connected ten-membered hydrogen-bonding rings.",
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(+)-3-Oxo-23,24-dinor-5α-cholan-22-oic acid : Hydrogen-bonding patterns in a steroidal keto acid and its monohydrate. / Lalancette, Roger A.; Thompson, Hugh W.; Brunskill, Andrew P.J.

In: Acta Crystallographica Section C: Crystal Structure Communications, Vol. 54, No. 3, 15.03.1998, p. 421-424.

Research output: Contribution to journalArticle

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T1 - (+)-3-Oxo-23,24-dinor-5α-cholan-22-oic acid

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AU - Lalancette, Roger A.

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AU - Brunskill, Andrew P.J.

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AB - The X-ray crystal structures of the title steroidal keto acid in both its anhydrous, C22H34O3, (I), and monohydrate, C22H34O3.H2O, (II), forms have been determined. Neither hydrogen-bonding pattern involves the ketone. Compound (I) forms infinite carboxyl-to-carboxyl hydrogen-bonding chains. This is the first observed case of a keto carboxylic acid forming such an acid-to-acid catemer. In (II), each carboxyl is hydrogen bonded to three water molecules and each water forms hydrogen bonds with carboxyl groups from three steroid molecules, creating a network of connected ten-membered hydrogen-bonding rings.

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