The title compound, C9H13N4O3+center dot 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 angstrom). The molecules are linked into flat layers by N-H center dot center dot center dot O and C-H center dot center dot center dot O hydrogen bonds. O-H center dot center dot center dot O hydrogen bonds involving the hydroxymethyl group as a donor interconnect the layers into a three-dimensional structure.
TY - JOUR
AU - Novaković, Slađana B.
AU - Bogdanović, Goran A.
AU - Leovac, Vukadin M.
AU - Rodić, Marko V.
AU - Vojinović-Ješić, Ljiljana S.
AU - Ivkovic, Sonja
PY - 2013
UR - https://vinar.vin.bg.ac.rs/handle/123456789/5580
AB - The title compound, C9H13N4O3+center dot 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 angstrom). The molecules are linked into flat layers by N-H center dot center dot center dot O and C-H center dot center dot center dot O hydrogen bonds. O-H center dot center dot center dot O hydrogen bonds involving the hydroxymethyl group as a donor interconnect the layers into a three-dimensional structure.
T2 - Acta Crystallographica. Section C: Crystal Structure Communications
T1 - (E)-4-[(2-Carbamoylhydrazinylidene)methyl]-3-hydroxy-5-hydroxymethyl-2-methylpyridin-1-ium nitrate
VL - 69
SP - 761
EP - +
DO - 10.1107/S0108270113013929
ER -
@article{
author = "Novaković, Slađana B. and Bogdanović, Goran A. and Leovac, Vukadin M. and Rodić, Marko V. and Vojinović-Ješić, Ljiljana S. and Ivkovic, Sonja",
year = "2013",
abstract = "The title compound, C9H13N4O3+center dot 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 angstrom). The molecules are linked into flat layers by N-H center dot center dot center dot O and C-H center dot center dot center dot O hydrogen bonds. O-H center dot center dot center dot O hydrogen bonds involving the hydroxymethyl group as a donor interconnect the layers into a three-dimensional structure.",
journal = "Acta Crystallographica. Section C: Crystal Structure Communications",
title = "(E)-4-[(2-Carbamoylhydrazinylidene)methyl]-3-hydroxy-5-hydroxymethyl-2-methylpyridin-1-ium nitrate",
volume = "69",
pages = "761-+",
doi = "10.1107/S0108270113013929"
}
Novaković, S. B., Bogdanović, G. A., Leovac, V. M., Rodić, M. V., Vojinović-Ješić, L. S.,& Ivkovic, S.. (2013). (E)-4-[(2-Carbamoylhydrazinylidene)methyl]-3-hydroxy-5-hydroxymethyl-2-methylpyridin-1-ium nitrate. in Acta Crystallographica. Section C: Crystal Structure Communications, 69, 761-+.
https://doi.org/10.1107/S0108270113013929
