Crystal structure of abacavir hemisulfate: a nucleoside analog reverse transcriptase inhibitor

Jasinski, Jerry P. and Ray, Butcher J. and Yathirajan, H. S. and Mallesha, L. and Mohana, K. N. and Narayana, B. (2009) Crystal structure of abacavir hemisulfate: a nucleoside analog reverse transcriptase inhibitor. JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 39 (12). pp. 864-869. ISSN 1572-8854

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Official URL: http://doi.org/10.1007/s10870-009-9577-1

Abstract

The title compound, Abacavir hemisulfate Systematic name: {(1S,4R)-4-2-amino-6-(cyclopropylamino)- 9H-purin-9-yl]cyclopentene}-1-methanol hemisulfate, C14H19N6O+](2) SO42-, (I), crystallizes in the monoclinic space group C2 with unit cell parameters a = 18.7498(7), b = 8.3577(5), c = 13.2563(5), angstrom, beta = 130.575(3)degrees, Z = 2. In the asymmetric unit, the compound crystallizes with two C14H19N6O+ cations and one SO42- anion connected by strong intermolecular N-H center dot center dot center dot O hydrogen bond interactions between two of these C14H19N6O+ cations. Additional strong O-H center dot center dot center dot O hydrogen bond intermolecular interactions are observed between the C14H19N6O+ and SO42-, cation-anion, units, respectively. The C14H19N6O+](2) SO42- units link themselves into an infinite O-H center dot center dot center dot O-H center dot center dot center dot O-H one dimensional chain diagonally along the 101] plane of the unit cell. The dihedral angle between the mean planes of the 5-membered imidazole ring fused to the 6-membered pyrimidine ring is 2.6(8)degrees making it a nonplanar purin-9-yl ring. The dihedral angle between the mean planes of the imidazole and pyrimidine rings with those of the cyclopropane and cyclopentene rings are 63.3(7)degrees, 61.2(2)degrees and 63.2(2)degrees, 63.87 degrees, respectively. Intermolecular O-H center dot center dot center dot O and N-H center dot center dot center dot O hydrogen bond interactions influence the cyclopropane twist angle and therefore play a role in stabilizing crystal packing in the unit cell. The geometries of the C14H19N6O+, SO42-, cation-anion pair, were optimized means of density functional theory (DFT) molecular orbital theoretical calculation at the B3-LYP/6-311 + G(d,p) level and compared to the crystallographic results providing support for these observations.

Item Type: Article
Uncontrolled Keywords: Crystal structure; Hydrogen bonds; Hemisulfate; Nucleoside analog; Reverse transcriptase inhibitor; Density functional theory calculations, B3-LYP/6-311+G(d,p)
Subjects: C Chemical Science > Chemistry
Divisions: Department of > Chemistry
Depositing User: Shrirekha N
Date Deposited: 13 Aug 2019 05:35
Last Modified: 13 Aug 2019 05:35
URI: http://eprints.uni-mysore.ac.in/id/eprint/6306

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