Publication
Different classical hydrogen-bonding patterns in three salicylaldoxime derivatives, 2-HO-4-XC6H3C=NOH (X = Me, OH and MeO)
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Advisor(s)
Abstract(s)
The crystal structures of three salicyaldoxime compounds, namely 2-hy-droxy-4-methyl-benzaldehyde oxime, C8H9NO2, 1, 2,4-di-hydroxy-benzaldehyde oxime, C7H7NO3, 2, and 2-hy-droxy-4-meth-oxy-benzaldehyde oxime, C8H9NO3, 3, are discussed. In each compound, the hydroxyl groups are essentially coplanar with their attached phenyl group. The inter-planar angles between the C=N-O moieties of the oxime unit and their attached phenyl rings are 0.08 (9), 1.08 (15) and 6.65 (15)° in 1, 2 and 3, respectively. In all three mol-ecules, the 2-hy-droxy group forms an intra-molecular O-H⋯N(oxime) hydrogen bond. In compound (1), inter-molecular O-H(oxime)⋯O(hydrox-yl) hydrogen bonds generate R22(14) dimers, related by inversion centres. In compound 2, inter-molecular O-H(oxime)⋯O(4-hy-droxy) hydrogen bonds generate C9 chains along the b-axis direction, while O-H(4-hydrox-yl)⋯O(2-hydrox-yl) inter-actions form zigzag C6 spiral chains along the c-axis direction, generated by a screw axis at 1, y, 1/4: the combination of the two chains provides a bimolecular sheet running parallel to the b axis, which lies between 0-1/2 c and 1/2-1 c. In compound 3, similar C9 chains, along the b-axis direction are generated by O-H(oxime)⋯O(4-meth-oxy) hydrogen bonds. Further weaker, C-H⋯π (in 1), π-π (in 2) and both C-H⋯π and π-π inter-actions (in 3) further cement the three-dimensional structures. Hirshfeld surface and fingerprint analyses are discussed.
Description
Keywords
Crystal structure Hydrogen bonding Salicylaldoxime Hirshfeld surface analysis
Citation
Gomes, L. R., de Souza, M., Da Costa, C. F., Wardell, J. L., & Low, J. N. (2018). Different classical hydrogen-bonding patterns in three salicylaldoxime derivatives, 2-HO-4-XC6H3C=NOH (X = Me, OH and MeO). Acta crystallographica. Section E, Crystallographic communications, 74(Pt 10), 1480–1485. doi:10.1107/S2056989018013361
Publisher
International Union of Crystallography