(E)-2-({2-[(E)-(Hydroxyimino)methyl]phenoxy}methyl)-3-o-tolylacrylonitrile

In the title compound, C18H16N2O2, the dihedral angle between the mean planes through the two benzene rings is 56.8 (6)°. The enoate group assumes an extended conformation. The hydroxyethanimine group is essentially coplanar with the benzene ring, the largest deviation from the mean plane being 0.047 (1) Å for the hydroxyimino O atom. In the crystal, the molecules are linked into cyclic centrosymmetric dimers with R 2 2(6) motifs via O—H⋯N hydrogen bonds.

In the title compound, C 18 H 16 N 2 O 2 , the dihedral angle between the mean planes through the two benzene rings is 56.8 (6) . The enoate group assumes an extended conformation. The hydroxyethanimine group is essentially coplanar with the benzene ring, the largest deviation from the mean plane being 0.047 (1) Å for the hydroxyimino O atom. In the crystal, the molecules are linked into cyclic centrosymmetric dimers with R 2 2 (6) motifs via O-HÁ Á ÁN hydrogen bonds.

Related literature
For the use of 2-cyanoacrylates and oximes as agrochemicals, see: Zhang et al. (2009). For the use of oximes as chelating ligands in coordination and analytical chemistry, see: Chaudhuri et al. (2003). For a related structure, see: Govindan et al.  Table 1 Hydrogen-bond geometry (Å , ).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009   Recently, 2-cyanoacrylates have been extensively used as agrochemicals because of their unique mechanism of action and good environmental profiles (Zhang et al., 2009). Oximes are a classical type of chelating ligands which are widely used in coordination and analytical chemistry (Chaudhuri, 2003). Against this background, and in order to obtain detailed information on molecular conformations in the solid state, an X-ray study of the title compound was carried out.
X-Ray analysis confirms the molecular structure and atom connectivity as illustrated in Fig. 1. The bond lengths and angles in (Fig. 1) agree with those observed in other tolylacrylonitile derivatives (Govindan et al., 2011). The whole molecule is not planar as the dihedral angle between the two phenyl rings is 56.8 (6)°, The oxime group having the C=N forming an E configuration. The hydroxyethanimine group is essentially coplanar with the benzene ring, the largest deviation from the mean plane of the hydroxyethanimine [C=N-OH] group is 0.047 (1) Å. for the O1 atom.

Experimental
To a stirred solution of (E)-2-((2-formylphenoxy)methyl)-3-o-tolylacrylonitrile (4 mmol) in 10 ml of EtOH/H 2 O mixture (1:1) was added NH 2 OH.HCl (6 mmol) in the presence of 50% NaOH at room temperature. Then the reaction mixture was allowed to stir at room temperature for 1.5 h. After completion of the reaction, solvent was removed and the crude mass was diluted with water (15 ml) and extracted with ethyl acetate (3 x 15 ml). The combined organic layer was washed with brine (2 x 10 ml) and dried over anhydrous Na 2 SO 4 and then evaporated under reduced pressure to obtain (2E)-2-((2-((Hydroxyimino)methyl) phenoxy)methyl)-3-o-tolylacrylonitrile as a colourless solid.

Refinement
All H atoms were fixed geometrically and allowed to ride on their parent C atoms, with C-H distances fixed in the range 0.93-0.97 Å with U iso (H) = 1.5U eq (C) for methyl H 1.2U eq (C) for other H atoms.
supplementary materials sup-2 Figures Fig. 1. View of the title molecule with the atom labelling scheme. The displacement ellipsoids are drawn at the 30% probability level while the H atoms are shown as small spheres of arbitrary radii.   (14)