5-Cyclohexyl-2-methyl-3-(4-methylphenylsulfonyl)-1-benzofuran

In the title compound, C22H24O3S, the cyclohexyl ring adopts a chair conformation. The 4-methylphenyl ring makes a dihedral angle of 80.95 (4)° with the mean plane [mean deviation = 0.011 (1) Å] of the benzofuran fragment. In the crystal, molecules are linked by weak C—H⋯O and C—H⋯π interactions.

In the title compound, C 22 H 24 O 3 S, the cyclohexyl ring adopts a chair conformation. The 4-methylphenyl ring makes a dihedral angle of 80.95 (4) with the mean plane [mean deviation = 0.011 (1) Å ] of the benzofuran fragment. In the crystal, molecules are linked by weak C-HÁ Á ÁO and C-HÁ Á Á interactions.

Related literature
For background information and the crystal structures of the related compounds, see: Choi et al. (2011Choi et al. ( , 2012 Table 1 Hydrogen-bond geometry (Å , ).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FB2242).
In the title molecule ( Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.011 (1) Å from the least-squares plane defined by the nine non-hydrogen constituent atoms. The cyclohexyl ring is in the chair conformation.

Experimental
77% 3-chloroperoxybenzoic acid -the product of Aldrich Chemical Co. -(381 mg, 1.7 mmol) was added in small portions to a stirred solution of 5-cyclohexyl-2-methyl-3-(4-methylphenylsulfanyl)-1-benzofuran (269 mg, 0.8 mmol) in dichloromethane (30 ml) at 273 K. After being stirred at room temperature for 8h, the mixture was washed with saturated solution of of NaHCO 3 and the organic layer was separated, dried over MgSO 4 , filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane-ethyl acetate, 4:1 v/v) to afford the title compound as a colorless solid [yield 72%, m.p. 437-438 K; R f = 0.48 (hexane-ethyl acetate, 4:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in benzene at room temperature. The average crystal size was approximatly 1.2 × 1.0 × 0.7 mm. (The measureed crystal was cut from the large one.) The crystals are colourless and soluble in polar solvents.

Refinement
All the hydrogens were discerned in the difference electron density maps. However, they were situated into the idealized positions and refined using a riding model, with C-H = 0.95, 1.0, 0.99 and 0.98 Å for aryl, methine, methylene and 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.
The positions of methyl hydrogens were optimized rotationally.  The title molecule with the atom numbering scheme. The displacement ellipsoids are drawn at the 50% probability level.

Computing details
H atoms are presented as small spheres of arbitrary radius.

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.