5-Cyclohexyl-3-cyclohexylsulfonyl-2-methyl-1-benzofuran

In the title compound, C21H28O3S, the benzofuran unit is essentially planar, with a mean deviation of 0.016 (1) Å from the least-squares plane defined by the nine constituent atoms. Both cyclohexane rings adopt chair conformations.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NK2090). antitumor and antiviral, and antimicrobial activities (Aslam et al., 2006, Galal et al., 2009, Khan et al., 2005. These compounds occur in a wide range of natural products (Akgul & Anil, 2003;Soekamto et al., 2003). As a part of our ongoing study of the substituent effect on the solid state structures of 2-aryl-5-cyclohexyl-3-methylsufinyl-1-benzofuran analogues (Choi et al., 2011a, b), we report herein on the crystal structure of the title compound.
In the title molecule ( Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.016 (1) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexane rings in each are in the chair form.
The molecular packing is stabilized by weak intermolecular C-H···π interactions between a cyclohexyl H atom in the 5-position and the furan ring (Table 1).

Experimental
77% 3-chloroperoxybenzoic acid (448 mg, 2.0 mmol) was added in small portions to a stirred solution of 5-cyclohexyl-3cyclohexylsulfanyl-2-methyl-1-benzofuran (295 mg, 0.9 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 6h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (benzene) to afford the title compound as a colorless solid [yield 79%, m.p. 378-379 K; R f = 0.65 (benzene)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.

Refinement
All H atoms were positioned geometrically and refined using a riding model, with C-H = 0.95 Å for aryl, 1.00 Å for methine, 0.99 Å for methylene and 0.98 Å for methyl H atoms, respectively. U iso (H) = 1.2U eq (C) for aryl, methine and methylene, and 1.5U eq (C) for methyl H atoms.

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 supplementary materials sup-3 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.