1-(1-Benzofuran-2-yl)ethanone O-(4-chlorobenzyl)oxime

In the title compound, C17H14ClNO2, the p-chlorobenzyloxy residue assumes an E conformation with respect to the benzofuran system. The carbo- and heterocyclic systems make a dihedral angle of 47.99 (4)°. In the crystal, there are no significant intermolecular interactions present.

In the title compound, C 17 H 14 ClNO 2 , the p-chlorobenzyloxy residue assumes an E conformation with respect to the benzofuran system. The carbo-and heterocyclic systems make a dihedral angle of 47.99 (4) . In the crystal, there are no significant intermolecular interactions present.  supplementary materials Acta Cryst. (2012). E68, o3178 [doi:10.1107/S1600536812042675]

Comment
The study of free oximes and their ethers have become of much interest in recent years on account of their diverse biological activities. Antienteroviral, antifungal, antibacterial, antineoplastic, anticonvulsant and antimicrobial activities (Chern et al., 2004;Emami et al., 2004;Demirayak et al., 2002;Bhandari et al., 2009;Jindal et al., 2003;Karakurt et al., 2001) are a few among many other activities.
The crystal structure investigation of the title compound was undertaken in order to obtain information about the spatial structure of the molecule.
The molecular structure of the title compound and the atom-labelling scheme is illustrated in Fig. 1.
The nine-membered benzofuran system is almost planar with an r.m.s. deviation of 0.0122 Å. The p-chlorobenzyloxy moiety is in E configuration with respect to the C2 atom of the benzofuran system. This arrangement is confirmed by the torsional angle C2-C10-N12-O13 of 179.91 (17)°. Simultaneously, the torsion angle C10-N12-O13-C14, 173.34 (18)°, reveals an antiperiplanar conformation for atoms C10 and C14. Furthermore, the dihedral angle made by the mean planes of the above mentioned systems amounts to 47.99 (4)°.
The main factor that determines the crystal packing are normal van der Waals interactions.

Refinement
All H atoms were set to idealized positions and were refined with the riding model approximation: C methyl -H = 0.96 Å, C methylene -H = 0.97 Å, C(sp 2 )-H = 0.93 Å; U iso (H) = 1.2U eq (C) or 1.5U eq (C) for methyl H. The methyl group was refined as rigid group which was allowed to rotate.  The molecular structure of the title compound showing the atomic labelling scheme. Non-H atoms are drawn as 30% probability displacement ellipsoids; H atoms are shown as small spheres of arbitrary radius.

Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 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.