Acta Crystallographica Section E

Structure Reports Online

Volume 69, Part 8 (August 2013)

organic compounds

zs2267 scheme

Acta Cryst. (2013). E69, o1301-o1302    [ doi:10.1107/S1600536813019727 ]

N2-(4-Methoxysalicylidene)arginine hemihydrate

M. Sethuram, G. Bhargavi, M. Dhandapani, G. Amirthaganesan and M. NizamMohideen

Abstract: The title compound, C14H20N4O4·0.5H2O [systematic name: (2S)-5-{[amino(iminiumyl)methyl]amino}-2-{[(1Z)-4-methoxy-2-oxidobenzylidene]azaniumyl}pentanoate hemihydrate], has been synthesized by the reaction of L-arginine and 4-methoxysalicylaldehyde and crystallizes with two independent substituted L-arginine molecules and one water molecule of solvation in the asymmetric unit. Each molecule exists as a zwitterion and adopts a Z configuration about the central C=N. The molecular conformation is stabilized by strong intramolecular N-H...O hydrogen bonds that generate S(6) and S(10) ring motifs. Intermolecular N-H...O and O-H...O hydrogen bonds involving also the water molecule and weak intermolecular C-H...Owater interactions link the molecules into an infinite one-dimensional ribbon structure extending along the b axis. The known (2S) absolute configuration for L-arginine was invoked. Weak intermolecular C-H...[pi] interactions are also present.

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