Analysis of intra- and intermolecular hydrogen bonding in androstane derivatives: A case study of steroids

Analysis of intra- and intermolecular hydrogen bonds for a series of sixty androstane derivatives has been made in the present paper. The CCDC survey sets out to collate existing diffraction data on androstane derivatives and its interpretation with special emphasis on intra- and intermolecular hydrogen bonds. X - H center dot center dot center dot A intra- and intermolecular hydrogen bonds in the identified molecules are described with the standard bond distance and angle cut-off criteria. D - theta and d - theta scatter plots for intra- and intermolecular interactions have been made for better understanding of packing interactions existing in this series of steroids. The frequency of occurrence of contacts like H(C) to O is compared with the frequency of occurrence of contacts like H(O) to O and it has been found that H(O) to O contacts are predominant over H(C) to O contacts. Solvent-solute/solute-solvent interactions have also been investigated to understand more complicated processes that occur for biomolecules in aqueous solutions.