Analysis of C–H···O Intermolecular Interactions in 4-Androstene-3,17-dione

Abstract

4-Androstene-3,17-dione was synthesized for its crystallographic analysis and to investigate the role of intra- and intermolecular interactions in steroids. It crystallizes in the orthorhombic space group P212121 with unit cell parameters, a = 7.330(2) A, b = 13.095(11) A, c = 16.856(17) A, V = 1,618(5) A3 and Z = 4. The structure has been solved by direct methods using X-ray diffraction techniques and the refined final reliability index for the computed structure is 0.033 for 1,655 observed reflections. Two six-membered rings B and C exist in chair conformation while ring A occupies a sofa conformation. The five-membered ring D depicts envelope conformation. The C–H···O intermolecular hydrogen interaction results into a ring like configuration which makes the dimers. Androgen is the generic term for any natural or synthetic compound, usually a steroid hormone, that stimulates or controls the development and maintenance of masculine characteristics in vertebrates by binding to androgen receptors [1]. Androgens have been used in breast cancer when excision or radiotherapy have failed to control the progress of local recurrent disease. They are also used in case where the primary tumour is inoperable or is unsuited for, or resistant to, radiotherapy. Androgens are also believed to be responsible for linear bone growth in both males and females, probably in conjunction with somatotrophin [2]. In continuation to our work on the single crystal growth of X-ray diffraction quality crystals and crystallographic analysis of steroidal molecules, [3-7] synthesis and crystallographic study 4-androstene-3,17-dione is reported in this paper.