title: (E)-4-[(2-carbamoylhydrazinylidene)methyl]-3-hydroxy-5-hydroxymethyl-2-methylpyridin-1-ium nitrate.
abstract: 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.
authors.affiliation: Vinča Institute of Nuclear Sciences, Laboratory of Theoretical Physics and Condensed Matter Physics, University of Belgrade, PO Box 522, 11001 Belgrade, Serbia. snovak@vin.bg.ac.rs
authors.forename: Sladjana B
authors.initials: SB
authors.lastname: Novaković
authors.forename: Goran A
authors.initials: GA
authors.lastname: Bogdanović
authors.forename: Vukadin M
authors.initials: VM
authors.lastname: Leovac
authors.forename: Marko V
authors.initials: MV
authors.lastname: Rodić
authors.forename: Ljiljana S
authors.initials: LS
authors.lastname: Vojinović-Ješić
authors.forename: Sonja
authors.initials: S
authors.lastname: Ivković
mesh_terms: D018360:Crystallography, X-Ray; D006834:Hydrazines / Q000737:chemistry*; D006860:Hydrogen Bonding; D011726:Pyridinium Compounds / Q000737:chemistry*; D011730:Pyridoxal / Q000737:chemistry*; D012545:Schiff Bases / Q000138:chemical synthesis* / Q000737:chemistry; D012663:Semicarbazides / Q000737:chemistry*
chemical_list: C584208:(E)-4-((2-carbamoylhydrazinylidene)methyl)-3-hydroxy-5-hydroxymethyl-2-methylpyridin-1-ium nitrate; D006834:Hydrazines; D011726:Pyridinium Compounds; D012545:Schiff Bases; D012663:Semicarbazides; C010059:carbamylhydrazine; D011730:Pyridoxal