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Acta Crystallogr C. 2013 Jul;69(Pt 7):761-4. doi: 10.1107/S0108270113013929. Epub 2013 Jun 8.

(E)-4-[(2-carbamoylhydrazinylidene)methyl]-3-hydroxy-5-hydroxymethyl-2-methylpyridin-1-ium nitrate.

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Vinča Institute of Nuclear Sciences, Laboratory of Theoretical Physics and Condensed Matter Physics, University of Belgrade, PO Box 522, 11001 Belgrade, Serbia.


The title compound, C9H13N4O3(+)·NO3(-), is the first structurally characterized Schiff base derived from semicarbazide and pyridoxal. Unusually for an unsubstituted semicarbazone, the compound adopts a syn conformation, in which the carbonyl O atom is in a cis disposition relative to the azomethine N atom. This arrangement is supported by a pair of hydrogen bonds between the organic cation and the nitrate anion. The cation is essentially planar, with only a hydroxymethyl O atom deviating significantly from the mean plane of the remaining atoms (r.m.s. deviation of the remaining non-H atoms = 0.01 Å). The molecules are linked into flat layers by N-H···O and C-H···O hydrogen bonds. O-H···O hydrogen bonds involving the hydroxymethyl group as a donor interconnect the layers into a three-dimensional structure.

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