2-[4-(Methylsulfonyl)phenyl]acetonitrile

In the title compound, C9H9NO2S, the benzene ring and the acetonitrile group are approximately coplanar, with a C—C—C—C torsion angle of 1.1 (3)° between them. In the crystal, molecules are linked via intermolecular C—H⋯O hydrogen bonds into layers parallel to (001).


Comment
Compounds bearing the 4-methylsulfonylphenyl moiety are found to possess diverse biological properties. They are found to be highly potent and specific COX-2 inhibitors (Orjales et al., 2008;Zarghi et al., 2008;Shah et al., 2010). Recent studies have shown that selective COX-2 inhibitors can induce apoptosis in colon, stomach, prostate, and breast cancer cell lines (Arico et al., 2002;Davies et al., 2002;Sawaoka et al., 1998;Liu et al., 2000). Selective COX-2 inhibitors offer potential treatment for the prophylactic prevention of inflammatory neurodegerative disorders such as Alzheimer's disease (Pasinetti, 2001). They are also found to be anti-inflammatory agents (Norman et al., 1995). The crystal structure of a methylsulfonylphenyl derivative has been reported (Charlier et al., 2004).
Experimental 4-Methylthiophenylacetonitrile (0.1 mol) was taken in 3 mL of acetic anhydride and cooled to 5°C. To the reaction mixture sodium tungstate (0.02 mol) was added followed by 30% hydrogen peroxide (0.2 mol) in 1.2 mL of acetic acid and water mixture (in 2:1 ratio). The temperature of the reaction mixture was slowly brought to room temperature. The completion of reaction was monitored by TLC. The solid precipitate was filtered and washed with water until the pH became neutral. The product was dried at 65 °C for 10-12 h. The product was then recrystallized in methanol (m. p.: 120-124 °C).

Refinement
All H atoms were positioned geometrically and refined using a riding model with C-H = 0.93-0.97 Å and U iso (H) = 1.2 or 1.5 U eq (C). The highest residual electron density peak is located at 0.88 Å from C3 and the deepest hole is located at 0.74 Å from S1. A rotating-group model was applied for the methyl group.

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 > 2sigma(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.