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

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Authors
Novaković, Slađana B.
Bogdanović, Goran A.
Leovac, Vukadin M.
Rodić, Marko V.
Vojinović-Ješić, Ljiljana S.
Ivkovic, Sonja
Article
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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.
Source:
Acta Crystallographica. Section C: Crystal Structure Communications, 2013, 69, 761-+
Funding / projects:
  • Design, synthesis, characterization and assessment of practical applications of coordination and organometallic compounds (RS-172014)

DOI: 10.1107/S0108270113013929

ISSN: 0108-2701

PubMed: 23832038

WoS: 000321458200017

Scopus: 2-s2.0-84880179167
[ Google Scholar ]
1
1
URI
https://vinar.vin.bg.ac.rs/handle/123456789/5580
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  • WoS Import
Institution/Community
Vinča
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
Novaković SB, Bogdanović GA, Leovac VM, Rodić MV, Vojinović-Ješić LS, Ivkovic S. (E)-4-[(2-Carbamoylhydrazinylidene)methyl]-3-hydroxy-5-hydroxymethyl-2-methylpyridin-1-ium nitrate. in Acta Crystallographica. Section C: Crystal Structure Communications. 2013;69:761-+.
doi:10.1107/S0108270113013929 .
Novaković, Slađana B., Bogdanović, Goran A., Leovac, Vukadin M., Rodić, Marko V., Vojinović-Ješić, Ljiljana S., Ivkovic, Sonja, "(E)-4-[(2-Carbamoylhydrazinylidene)methyl]-3-hydroxy-5-hydroxymethyl-2-methylpyridin-1-ium nitrate" in Acta Crystallographica. Section C: Crystal Structure Communications, 69 (2013):761-+,
https://doi.org/10.1107/S0108270113013929 . .

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