Synthesis, crystal structure and computational studies of new steroidal hemisuccinyl ester derivatives

Abstract

The synthesis and characterization of steroidal hemisuccinate esters derived from pregnanolone, pregnenolone, 3β,19-dihydroxy-androst-5-en-17-one and cholic acid are presented. A combined theoretical-experimental analysis of the conformation and self-assembly of the crystalline samples is carried out with support from single crystal X-ray diffraction experiments and DFT computations, featuring Cremer-Pople ring puckering and Quantum Theory of Atoms-in-Molecules (QTAIM) analyses, unveiling a proclivity of these molecules towards the formation of dimeric and trimeric supramolecular assemblies bound by means of classical and non-classical hydrogen bonding interactions, whose directionality and energetics are discussed in detail within reduced systems of the crystallographic structures.