Antioxidative succinobucol–sterol conjugates: Crystal structures and pseudosymmetry in the crystals

An extensive study to attach succinobucol to sterols has provided conjugates which comprise two pharmaceutically important compounds into one entity where the components are expected to have a synergistic effect. The motivation to design these novel conjugates was the need to broaden the armamentarium of current agents used in the treatment of atherosclerotic diseases and type 2 diabetes. In desire for detailed information of these compounds in solid state, which also have an influence to their physiological activity, systematic crystallization experiments were performed and as a result, X-ray quality single crystals were obtained from four succinobucol–sterol conjugates. All of these compounds crystallized in space group P1 with two or four molecules in an asymmetric unit and the crystallographically independent molecules were found to be related by pseudosymmetry (i.e. by pseudoinversion in 1–3 and by pseudoinversion plus pseudotranslation in 4).

► Solid state structures of antioxidative sterol-succinobucol conjugates were studied.
► Interesting pseudosymmetry was found in the crystals.
► Isostructurality between some crystals were found.
► Pseudosymmetry leads to pseudo achiral crystals of chiral steroid derivative.