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

• Published in: Acta crystallographica. Section C, Crystal structure communications Vol. 69; no. 7; pp. 761 - 764
• Main Authors: Novaković, Sladjana B., Bogdanović, Goran A., Leovac, Vukadin M., Rodić, Marko V., Vojinović-Ješić, Ljiljana S., Ivković, Sonja
• Format: Journal Article
• Language: English
• Published: 5 Abbey Square, Chester, Cheshire CH1 2HU, England International Union of Crystallography 01.07.2013; Wiley Subscription Services, Inc
• Subjects: Crystal structure; Crystallography; Crystallography, X-Ray; Hydrazines - chemistry; Hydrogen Bonding; Hydrogen bonds; Molecular chemistry; Pyridinium Compounds - chemistry; Pyridoxal - chemistry; Schiff Bases - chemical synthesis; Schiff Bases - chemistry; Semicarbazides - chemistry
• ISSN: 0108-2701; 1600-5759
• DOI: 10.1107/S0108270113013929

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.