Jasinski, Jerry P. and Butcher, Ray 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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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: | Users 19 not found. |
| Date Deposited: | 13 Aug 2019 05:35 |
| Last Modified: | 14 Jul 2022 11:18 |
| URI: | http://eprints.uni-mysore.ac.in/id/eprint/6306 |
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