Crystal structure of 3-oxo-4-aza-5-alpha-androstone-17 beta-tert-butyl carboxamide with an o center dot center dot center dot h-(c,n) acceptor four-center hydrogen bond

Jasinski, Jerry P. and Butcher, Ray J. and Mallesha, L. and Mohana, K. N. and Yathirajan, H. S. and Narayana, B. (2009) Crystal structure of 3-oxo-4-aza-5-alpha-androstone-17 beta-tert-butyl carboxamide with an o center dot center dot center dot h-(c,n) acceptor four-center hydrogen bond. Journal of Chemical Crystallography, 39 (6). pp. 458-465. ISSN 1572-8854

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Official URL: http://doi.org/10.1007/s10870-008-9503-y

Abstract

The title compound, C23H38N2O2, is the saturated form of a modified steroid derivative Finasteride, containing a delta-lactamide ring, fused to successive cyclohexane and cyclopentane rings which contain a tert-butylamide residue. It crystallizes in the monoclinic space group C2 with unit cell parameters a = 9.99450(10), b = 7.67870(10), c = 28.4954(3), angstrom, beta = 93.8706(10)degrees, Z = 4. Crystal packing effects are influenced by intermolecular hydrogen bond interactions dominated by an acceptor O center dot center dot center dot H-(C,N) four-center hydrogen bond interaction around the keto oxygen atom from the delta-lactamide ring in the asymmetric unit. Intramolecular three-center C-H center dot center dot center dot O hydrogen bonds around the tert-butylamide oxygen atom appear to have little effect on crystal packing. A comparison of the geometric parameters of the asymmetric unit (a 5 alpha isomer) is made and with a solvated analog compound (a 5 beta isomer) and some solvated Finasteride compounds which differ only in the unsaturation of the C1=C2 bond in the delta-lactamide ring. The dihedral angle between the mean planes of the fused delta-lactamide and cyclohexane rings is 2.5(8)degrees which differs significantly from the 74.8(8) and 76.1(9)degrees values observed in the solvated analog compound and with its geometry optimized (MOPAC) computed structure, respectively.

Item Type: Article
Uncontrolled Keywords: Androstone; Carboxamide; Finasteride; delta-Lactamide ring; Acceptor atom; Four-center hydrogen bond
Subjects: C Chemical Science > Chemistry
Divisions: Department of > Chemistry
Depositing User: Shrirekha N
Date Deposited: 26 Aug 2019 06:09
Last Modified: 26 Aug 2019 06:09
URI: http://eprints.uni-mysore.ac.in/id/eprint/7014

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