9α-Chloro-16α-methyl-3,11-dioxoandrosta-1,4,6-triene-17β-carboxylic acid pinacolone solvate: catemeric hydrogen bonding and pinacolone solvation in a steroidal diketo acid derived from a commercial glucocorticoid
✍ Scribed by Azim, Irum ;Davison, Mark ;Dufort, Marisa DeVita ;Lalancette, Roger A. ;Thompson, Hugh W.
- Book ID
- 104490871
- Publisher
- International Union of Crystallography
- Year
- 2007
- Tongue
- English
- Weight
- 733 KB
- Volume
- 63
- Category
- Article
- ISSN
- 1600-5368
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✦ Synopsis
The title ketocarboxylic acid, synthesized from the antiinflammatory clocortolone pivalate, crystallizes as C 21 H 23 ClO 4 ÁC 6 H 12 O, with one molecule of steroid and one of 3,3-dimethylbutanone per asymmetric unit. The carboxyl group is highly ordered and the steroid molecules form translational carboxyl-to-ketone hydrogen-bonding catemers [OÁ Á ÁO = 2.682 (3) A ˚and O-HÁ Á ÁO = 158 ] that utilize the 3ketone group, with one chain proceeding in the [110] direction and the other in the [110] direction. One close intermolecular C-HÁ Á ÁO C contact is present, which involves the solvent O atom, but neither it nor the Cl atom nor the 11-ketone group play any role in the classical hydrogen bonding.
Related literature
For the A-ring geometry of a related steroid dienone, see: Thompson et al. (1999).