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An unusual conformation of gabapentin (Gpn) in Pyr-Gpn-NH-NH-Pyr stabilized by weak interactions.

Research paper by Naiem Ahmad NA Wani, Vivek Kumar VK Gupta, Rajni R Kant, Subrayashastry S Aravinda, Rajkishor R Rai

Indexed on: 06 Aug '14Published on: 06 Aug '14Published in: Acta Crystallographica Section C



Abstract

The crystal structure of N-[(1-{2-oxo-2-[2-(pyrazin-2-ylcarbonyl)hydrazin-1-yl]ethyl}cyclohexyl)methyl]pyrazine-2-carboxamide monohydrate (Pyr-Gpn-NN-NH-Pyr·H2O), C19H23N7O3·H2O, reveals an unusual trans-gauche (tg(-)) conformation for the gabapentin (Gpn) residue around the C(γ)-C(β) (θ1) and C(β)-C(α) (θ2) bonds. The molecular conformation is stabilized by intramolecular N-H...N hydrogen bonds and weak C-H...O interactions. The packing of the molecules in the crystal lattice shows a network of strong N-H...O and O-H...O hydrogen bonds together with weak C-H...O and π-π inteactions.