Crystal structure of a second polymorph of gabapentin hydrochloride hemihydrate with a three-center bifurcated hydrogen bond

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 a second polymorph of gabapentin hydrochloride hemihydrate with a three-center bifurcated hydrogen bond. Journal of chemical crystallography, 39 (11). pp. 777-780. ISSN 1572-8854

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Official URL: http://doi.org/10.1007/s10870-009-9569-1

Abstract

Gabapentin hydrochloride hemihydrate, a derivative of Gabapentin or 1-(aminomethyl) cyclohexaneacetic acid; Gpn, C6H17NO2], is a salt of C9H18NO2 (+) Cl- 0.5 H2O, which crystallizes in the monoclinic space group I 2/a with unit cell parameters a = 13.2467(3), b = 6.5552(2), c = 26.0094(8)angstrom, beta = 96.561(3)degrees, Z = 8. The crystal structure and bonding network is compared to its isostructural and previously reported polymorphic derivative, Gpn hydrochloride hemihydrate C9H17NO2 HCl 1/2 H2O]. Both of these derivatives exhibit extensive inter and intra molecular hydrogen bonding networks between the NH3 (+) group and neighboring Cl-, water and carboxyl oxygen atoms as well as similar interactions between the chloride anion and nearby water and carboxyl oxygen atoms. A unique and relatively rare three-center hydrogen bond configuration (with a bifurcated chlorine Cl-center dot center dot center dot H-(N,O) and Cl-center dot center dot center dot H-O acceptor hydrogen bonds) as well as N-H center dot center dot center dot O donor hydrogen bonds can be seen linking the molecules into chains along the 1 0 1] plane of the unit cell.

Item Type: Article
Uncontrolled Keywords: Crystal structure; Hydrogen bonds; Derivative; Salt; Hemihydrate; Gabapentin; Three-center bond; Bifurcated; MOPAC; PM3
Subjects: C Chemical Science > Chemistry
Divisions: Department of > Chemistry
Depositing User: Shrirekha N
Date Deposited: 14 Aug 2019 07:56
Last Modified: 14 Aug 2019 07:57
URI: http://eprints.uni-mysore.ac.in/id/eprint/6371

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