3-Benzyl-5-methyl-1,2-benzoxazole 2-oxide

In the title compound, C15H13NO2, the isoxazole unit and the attached benzene ring are almost coplanar, making a dihedral angle of 1.42 (8)°. The benzyl ring is inclined to the isoxazole ring by 74.19 (8)° and is in a +sc conformation with respect to the benzisoxazole unit. In the crystal, C—H⋯O hydrogen bonds link the molecules, forming zigzag chains propagating along the b axis. There are also π–π interactions present involving the isoxazole and benzyl rings [centroid–centroid distance = 3.5209 (10) Å], and C—H⋯π interactions involving the benzene ring of the benzoisoxazole unit and the methylene bridging group.

In the title compound, C 15 H 13 NO 2 , the isoxazole unit and the attached benzene ring are almost coplanar, making a dihedral angle of 1.42 (8) . The benzyl ring is inclined to the isoxazole ring by 74.19 (8) and is in a +sc conformation with respect to the benzisoxazole unit. In the crystal, C-HÁ Á ÁO hydrogen bonds link the molecules, forming zigzag chains propagating along the b axis. There are alsointeractions present involving the isoxazole and benzyl rings [centroid-centroid distance = 3.5209 (10) Å ], and C-HÁ Á Á interactions involving the benzene ring of the benzoisoxazole unit and the methylene bridging group.
Benzoxazole derivatives show antiepileptic, antispasmodic and antifungal properties (Jian et al., 2007). 3-substituted 1,2benzisoxazole derivatives are emerging as potential antipsychotic compounds, antiseizure agents and are also used to block the repetitive firing of voltage-sensitive sodium channels and so reduce voltage-sensitive T-type calcium currents (Veera Reddy et al., 2011).
The bond lengths and angles in the title compound are in good agreement with the expected values and are comparable with the corresponding values reported for 5-chloro-3-methyl-1,2-benzisoxazole-2-oxide (Ghari & Viterbo, 1982).
In the crystal, molecules are linked via C-H···O hydrogen bonds leading to the formation of zigzag chains propagating along the a axis direction (Tabel 1 and Fig. 2). Molecules are also linked via C-H···π (Table 1) and π···π interactions.

Experimental
The compound was synthesized by the published method (Veera Reddy et al., 2011)

Refinement
All the H atoms were positioned geometrically and treated as riding atoms: C-H = 0.93, 0.96 and 0.97 Å for CH, CH 3 and CH 2 H atoms, respectively, with U iso (H) = k × U eq (C), where k = 1.5 for CH 3 H atoms and = 1.2 for other H atoms.

Computing details
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).    Table 1 for details; H atoms not involved in these interactions have been omitted for clarity). Special details Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles 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.