(E)-4-[(2-Carbamoylhydrazinylidene)methyl]-3-hydroxy-5-hydroxymethyl-2-methylpyridin-1-ium nitrate
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Novaković, Slađana B.
Bogdanović, Goran A.

Leovac, Vukadin M.

Rodić, Marko V.

Vojinović-Ješić, Ljiljana S.

Ivkovic, Sonja
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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.
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Acta Crystallographica. Section C: Crystal Structure Communications, 2013, 69, 761-+Funding / projects:
DOI: 10.1107/S0108270113013929
ISSN: 0108-2701
PubMed: 23832038
WoS: 000321458200017
Scopus: 2-s2.0-84880179167
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VinčaTY - 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 . .