2-Methoxyimino-2-{2-[(2-methylphenoxy)methyl]phenyl}ethanol

In the title compound, C17H19NO3, the dihedral angle between the benzene rings is 68.0 (1)°. The C—O—C—C torsion angle of the atoms joining these rings is 179.7 (2)°. The atoms of the methanol group were refined as disordered over two sets of sites with fixed occupancies of 0.86 and 0.14. The H atoms of the hydroxy group in the major component are disordered over a further two sets of sites with equal occupancies. This is a necessary arrangement to allow for hydrogen bonding without unrealistic H⋯H contacts. In the crystal, O—H⋯N and O—H⋯O hydrogen bonds connect molecules into chains along [001].

In the title compound, C 17 H 19 NO 3 , the dihedral angle between the benzene rings is 68.0 (1) . The C-O-C-C torsion angle of the atoms joining these rings is 179.7 (2) . The atoms of the methanol group were refined as disordered over two sets of sites with fixed occupancies of 0.86 and 0.14. The H atoms of the hydroxy group in the major component are disordered over a further two sets of sites with equal occupancies. This is a necessary arrangement to allow for hydrogen bonding without unrealistic HÁ Á ÁH contacts. In the crystal, O-HÁ Á ÁN and O-HÁ Á ÁO hydrogen bonds connect molecules into chains along [001].

Related literature
The title compound was derived from kresoxim-methyl. For the biological activity of kresoxim-methyl, see: Anke et al.   Table 1 Hydrogen-bond geometry (Å , ).  In (I) (Fig. 1), all bond lengths and angles are normal and correspond to those observed in the related structures (Chopra et al., 2004;Kant et al., 2012a,b). The dihedral angle between the two benzene rings is 68.0 (1)°. The C-O-C-C torsion angle of the atoms joining these rings is 179.7 (2) °. The atoms of the methanol group were refined as disordered over two sets of sites with fixed occupancies of 0.86 and 0.14. The H atoms of the hydroxy group in the major component are disordered over a further two sets of sites with equal occupancies. This is a necessary arrangement to allow for
Stirring and refluxing were maintained until the reaction was completed as monitored by TLC. After the end of the reaction, the reaction mixture was cooled to room temperature and quenched with a saturated solution of ammonium chloride (15 ml) for further period of 1.5 h. The product was separated by extraction with ethyl acetate (2x25 ml). The organic extracts were combined and dried over sodium sulfate and concentrated under low pressure to yield the final product. The synthesized compound was dissolved in methanol and subjected to slow evaporation to produce colourless crystals.

Refinement
All H atoms were positioned geometrically and were treated as riding on their parent atoms, with O-H distance of 0.84 Å and C-H distances of 0.93-0.97 Å and with U iso (H) = 1.2U eq (C) or 1.5U eq (methyl C,O). The disordered H atoms of the hydroxy group were placed in calculated positions which gave the most sensible hydrogen bonds. 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009).

Figure 1
The molecular structure of the title compound with ellipsoids drawn at the 40% probability level.  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 R-factors(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq Occ. (