Gomes, Ligia RebeloSouza, Marcus V. N. deDa Costa, Cristiane F.Wardell, James L.Low, John Nicolson2019-10-242019-10-242018Gomes, 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/S20569890180133612056-9890http://hdl.handle.net/10284/8175The 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.engCrystal structureHydrogen bondingSalicylaldoximeHirshfeld surface analysisjournal article10.1107/S2056989018013361