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. 2008 Feb 7;13(2):301-18.
doi: 10.3390/molecules13020301.

1,2-Diaryl(3-pyridyl)ethanone oximes. Intermolecular hydrogen bonding networks revealed by X-ray diffraction

Ermitas Alcalde  1 , Neus Mesquida, Carmen Alvarez-Rúa, Rosa Cuberes, Jordi Frigola, Santiago García-Granda
Affiliations

1,2-Diaryl(3-pyridyl)ethanone oximes. Intermolecular hydrogen bonding networks revealed by X-ray diffraction

Ermitas Alcalde et al. Molecules. .

Abstract

The synthesis of a set of 1-aryl-2-aryl(3-pyridyl)ethanones 1-5 and the corresponding ketoximes 6-9 is reported. Structural studies of oximes 6, 7 and 9 were performed in solution using (1)H-NMR and in the solid state by X-ray crystallography, providing evidence of H-bonding networks. The crystal packing was controlled by homomeric intermolecular oxime...oxime H-bond interactions for 6 and cooperative oxime...N(pyridyl) and CH/pi interactions for 7 and 9.

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Figures

Scheme 1
Scheme 1
Figure 1
Figure 1
Scheme 2
Scheme 2
Scheme 3
Scheme 3
Scheme 4
Scheme 4
Figure 2
Figure 2
Oximes 6, 7 and 9. Molecular structures and thermal ellipsoids (50% probability level). Intermolecular hydrogen bond oxime···oxime for 6 and oxime···N(py) for 7 and 9.
Figure 3
Figure 3
Crystal structure arrangements. Oxime 6: Zig-zag layers formed by isolated dimers (viewed down the crystallographic b axis). Oxime 9: Packing of dimers, viewed down the crystallographic b axis. Oxime 7: Infinite chains, viewed down the crystallographic a axis (left) and b axis (right).
Figure 4
Figure 4
C-H/π Hydrogen bonds. Oxime 7: (methyl)C-H···centroid(py) [2.66 Å, 164.86°]. Oxime 9: (py)C-Hα···centroid(aryl) [2.62 Å, 176.20°].
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