2-Ethoxy-6-[(methylimino)methyl]phenol

In the title compound, C10H13NO2, synthesized by the reaction of 2-hydroxy-3-ethoxybenzaldehyde with methylamine, there is an an intramolecular O—H⋯N hydrogen bond involving the hydroxy substituent and the amino N atom. In the crystal, molecules form inversion dimers connected by pairs of C—H⋯O hydrogen bonds.

In the title compound, C 10 H 13 NO 2 , synthesized by the reaction of 2-hydroxy-3-ethoxybenzaldehyde with methylamine, there is an an intramolecular O-HÁ Á ÁN hydrogen bond involving the hydroxy substituent and the amino N atom. In the crystal, molecules form inversion dimers connected by pairs of C-HÁ Á ÁO hydrogen bonds.
In the crystal molecules are linked through weak intermolecular C-H···O hydrogen bond, to form dimers centered about an inversion center (Fig. 2).

Experimental
Compound 2-hydrogen-3-ethoxy-benzaldehyde (0.166 g, 1 mmol) was dissolved in ethanol (15 ml). To this solution was added a methylamine solution (0.5 ml) and the mixture was stirred and refluxed at 323 K for 2 h. After cooling to room temperature and filtration, the filtrate was left to stand at room temperature. Yellow block-like crystals, suitable for X-ray diffraction analysis, were obtained in a yield of 76 %. Analysis found (%): C 66.97, H 7.38, N 7.84; C 10 H 13 NO 2 requires (%): C 67.02, H 7.31, N 7.82.

Refinement
All the H-atoms were positioned geometrically and were treated as riding atoms: O-H 0.82 Å, C-H 0.93-0.97 Å, with U iso (H) = k × U eq (parent O or C-atom), where k = 1.2 for H-aromatic and = 1.5 for H-methyl and H-hydroxyl.

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating Rfactors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.