3-Oxo-5β-24-norcholanic acid: acid-to-acid hydrogen-bonding catemers employing the rareanticarboxyl conformation in the aggregation of a steroid keto acid

Abstract

The title ketocarboxylic acid [systematic name: (5R,8R,9S,10S,13R,14S,17R,20R)-3-oxo-24-norcholanic acid], C(23)H(36)O(3), forms acid-to-acid hydrogen-bonding chains [O...O = 2.620 (2) A and O-H...O = 163 (3) degrees ] in which all carboxyl groups adopt the rare anti conformation, while the ketone group does not participate in the hydrogen bonding. The occurrence and energetics of this conformation are discussed. One intermolecular C-H...O close contact exists, which plays a role in stabilizing the hydrogen-bonding arrangement.

A comprehensive classification and nomenclature of carboxyl–carboxyl(ate) supramolecular motifs and related catemers: implications for biomolecular systems

“…Note that the November 2006 CSD release contained less than 2/3 of the structures found in the November 2013 release. Thus, the present searches significantly extend those presented in earlier publications on smaller samples of structures (Kuduva et al, 1999;DeVita Dufort et al, 2007;Langkilde et al, 2008). Since carboxyl(ate) groups are involved in strong hydrogen bonds (Jeffrey, 1997;Steiner, 2001;Langkilde et al, 2008), a stringent hydrogen-bond cut-off criterion could be used (OÁ Á ÁO 2.8 Å ).…”

“…Interestingly, some of these dimers can form catemers (Fig. 1), defined as infinite one-dimensional patterns involving their carboxyl groups (Leiserowitz, 1976;Berkovitch-Yellin & Leiserowitz, 1982;Kuduva et al, 1999;Beyer & Price, 2000;Das et al, 2005;Das & Desiraju, 2006;DeVita Dufort et al, 2007;Rodríguez-Cuamatzi et al, 2007;Saravanakumar et al, 2009;Sanphui et al, 2013). A complete classification of catemer motifs is also currently missing.…”

Desvenlafaxine succinate monohydrate

“…the acid H atom points away from the carbonyl O atom). The occurrence and energetics of this conformation have been discussed by DeVita Dufort et al (2007).…”

(±)-2-Oxocyclopentaneacetic acid: catemeric hydrogen bonding in a γ-keto acid

“…The category of γ-keto acids is especially rich in H-bonding types, embracing internal H bonds and catemers of the screw, translation and glide types, as well as dimers and hydrated patterns. The intra-chain glide relationship found is considerably rarer than either screw or translational schemes generally, and is shared with three other γ-keto acids of our experience (Barcon et al, 1998(Barcon et al, , 2002DeVita Dufort et al, 2007). Fig.…”

“…Acid-to-ketone chains (catemers) constitute a sizable overall minority of cases, while acid-to-ketone dimers and intramolecular H-bonds are rarely observed. We have presented examples of many of these and have discussed factors that contribute to the choice of mode (Coté et al, 1996;Newman et al, 2002;Lalancette et al, 2006;DeVita Dufort et al, 2007).…”