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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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: | Users 19 not found. |
| 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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