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Crystal structure of 2-hy-droxy-imino-2-(pyridin-2-yl)-N'-[1-(pyridin-2-yl)ethyl-idene]acetohydrazide.

Plutenko MO, Lampeka RD, Haukka M, Nordlander E - Acta Crystallogr Sect E Struct Rep Online (2014)

Bottom Line: The oxime group is syn to the amide group, probably due to the formation of an intra-molecular N-H⋯N hydrogen bond that forms an S(6) ring motif.The latter are linked via C-H⋯O and C-H⋯N hydrogen bonds, forming sheets lying parallel to (502).The sheets are linked via π-π stacking inter-actions [inter-centroid distance = 3.7588 (9) Å], involving the pyridine rings of inversion-related mol-ecules, forming a three-dimensional structure.

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Affiliation: Department of Chemistry, National Taras Shevchenko University, Volodymyrska Street 64, 01601 Kyiv, Ukraine.

ABSTRACT
The mol-ecule of the title compound, C14H13N5O2, is approximately planar (r.m.s deviation for all non-H atoms = 0.093 Å), with the planes of the two pyridine rings inclined to one another by 5.51 (7)°. The oxime group is syn to the amide group, probably due to the formation of an intra-molecular N-H⋯N hydrogen bond that forms an S(6) ring motif. In the crystal, mol-ecules are linked by pairs of bifurcated O-H⋯(O,N) hydrogen bonds, forming inversion dimers. The latter are linked via C-H⋯O and C-H⋯N hydrogen bonds, forming sheets lying parallel to (502). The sheets are linked via π-π stacking inter-actions [inter-centroid distance = 3.7588 (9) Å], involving the pyridine rings of inversion-related mol-ecules, forming a three-dimensional structure.

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A view of the mol­ecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level. The intra­molecular N—H⋯N hydrogen bond is shown as a dashed line (see Table 1 ▶ for details).
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fig1: A view of the mol­ecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level. The intra­molecular N—H⋯N hydrogen bond is shown as a dashed line (see Table 1 ▶ for details).

Mentions: The mol­ecular structure of the title compound is illustrated in Fig. 1 ▶. The mol­ecule is approximately planar (r.m.s deviation for all non-H atoms = 0.093 Å) with the maximum deviations from the mean plane being 0.255 (1) Å for atom N1, and 0.198 (1) Å for atom O1. The two pyridine rings (N1/C1–C5) and N5/C10–C14) are inclined to one another by 5.51 (7)°. The N2—O1 [1.3691 (14) Å] and C6—N2 [1.2866 (17) Å] bond lengths of the oxime group have typical values (Fritsky et al., 1998 ▶). The pyridine N atom, N1, is situated in an anti position with respect to the azomethine group, in accordance with the structures of earlier synthesized ligands of this type (Plutenko et al., 2011 ▶, 2013 ▶).


Crystal structure of 2-hy-droxy-imino-2-(pyridin-2-yl)-N'-[1-(pyridin-2-yl)ethyl-idene]acetohydrazide.

Plutenko MO, Lampeka RD, Haukka M, Nordlander E - Acta Crystallogr Sect E Struct Rep Online (2014)

A view of the mol­ecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level. The intra­molecular N—H⋯N hydrogen bond is shown as a dashed line (see Table 1 ▶ for details).
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4257442&req=5

fig1: A view of the mol­ecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level. The intra­molecular N—H⋯N hydrogen bond is shown as a dashed line (see Table 1 ▶ for details).
Mentions: The mol­ecular structure of the title compound is illustrated in Fig. 1 ▶. The mol­ecule is approximately planar (r.m.s deviation for all non-H atoms = 0.093 Å) with the maximum deviations from the mean plane being 0.255 (1) Å for atom N1, and 0.198 (1) Å for atom O1. The two pyridine rings (N1/C1–C5) and N5/C10–C14) are inclined to one another by 5.51 (7)°. The N2—O1 [1.3691 (14) Å] and C6—N2 [1.2866 (17) Å] bond lengths of the oxime group have typical values (Fritsky et al., 1998 ▶). The pyridine N atom, N1, is situated in an anti position with respect to the azomethine group, in accordance with the structures of earlier synthesized ligands of this type (Plutenko et al., 2011 ▶, 2013 ▶).

Bottom Line: The oxime group is syn to the amide group, probably due to the formation of an intra-molecular N-H⋯N hydrogen bond that forms an S(6) ring motif.The latter are linked via C-H⋯O and C-H⋯N hydrogen bonds, forming sheets lying parallel to (502).The sheets are linked via π-π stacking inter-actions [inter-centroid distance = 3.7588 (9) Å], involving the pyridine rings of inversion-related mol-ecules, forming a three-dimensional structure.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, National Taras Shevchenko University, Volodymyrska Street 64, 01601 Kyiv, Ukraine.

ABSTRACT
The mol-ecule of the title compound, C14H13N5O2, is approximately planar (r.m.s deviation for all non-H atoms = 0.093 Å), with the planes of the two pyridine rings inclined to one another by 5.51 (7)°. The oxime group is syn to the amide group, probably due to the formation of an intra-molecular N-H⋯N hydrogen bond that forms an S(6) ring motif. In the crystal, mol-ecules are linked by pairs of bifurcated O-H⋯(O,N) hydrogen bonds, forming inversion dimers. The latter are linked via C-H⋯O and C-H⋯N hydrogen bonds, forming sheets lying parallel to (502). The sheets are linked via π-π stacking inter-actions [inter-centroid distance = 3.7588 (9) Å], involving the pyridine rings of inversion-related mol-ecules, forming a three-dimensional structure.

No MeSH data available.


Related in: MedlinePlus