(E)-2-Methyl-6-{[(5-methylpyridin-2-yl)imino]methyl}phenol

Abstract

In the title compound, C 14 H 14 N 2 O, the dihedral angle between the aromatic rings is 5.54 (9) . The conformation is reinforced by an intramolecular O-HÁ Á ÁN hydrogen bond, which closes an S(6) ring. The pyridine N atom and methyl group lie to opposite sides of the molecule. In the crystal, the molecules are linked into a zigzag chain propagating in [011] by weak C-HÁ Á ÁO hydrogen bonds. Structure descriptionAs part of our ongoing studies of phenolic Schiff-base compounds (Adam et al. (2015), we now describe the synthesis and structure of the title compound (Fig. 1), which features an intramolecular O-HÁ Á ÁN hydrogen bond (Table 1), which helps to establish nearcoplanarity of the aromatic rings [dihedral angle = 5.54 (9) ]. In the crystal, the molecules are linked by a C2-H2A-O1 hydrogen bond into a zigzag C(9) chain propagating in [011] (Table 1, Fig. 2). Adjacent molecules in the chain are related by c-glide symmetry. Synthesis and crystallizationThe synthesis scheme is shown in Fig. 3. 2-Hydroxy-3-methylbenzaldehyde (0.681 g, 5 mmol) was dissolved in 20 ml toluene and after adding 0.2 ml acetic acid, the mixture was refluxed for 30 min. Then, 5-methylpyridin-2-amine 0.541 g (5 mmol) solution in 20 ml toluene was added dropwise with stirring to the aldehyde solution. The resulting light-yellow solution was refluxed for 4 h with stirring. The solvent was allowed to evaporate. The crude product was washed with benzene and n-hexane. Orange blocks were obtained by slow evaporation of a solution in toluene; m.p.: 363-364 K; yield: 95%.