3-Cyclohexylsulfonyl-2-methyl-5-propyl-1-benzofuran

In the title compound, C18H24O3S, the cyclohexyl ring adopts a chair conformation. In the crystal, molecules are linked through weak intermolecular C—H⋯O hydrogen bonds and C—H⋯π interactions. In the propyl group, one C atom is disordered over two sites with site-occupancy factors of 0.546 (8) and 0.454 (8).

In the title compound, C 18 H 24 O 3 S, the cyclohexyl ring adopts a chair conformation. In the crystal, molecules are linked through weak intermolecular C-HÁ Á ÁO hydrogen bonds and C-HÁ Á Á interactions. In the propyl group, one C atom is disordered over two sites with site-occupancy factors of 0.546 (8) and 0.454 (8).   Table 1 Hydrogen-bond geometry (Å , ).
In the title molecule ( Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.008 (2) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring is in the chair form. In the propyl group, C10 atom is disordered over two positions with site occupancy factors, from refinement of 0.546 (8) (part A) and 0.454 (8) (part B). The molecular packing (Fig. 2) is stabilized by weak intermolecular C-H···O hydrogen bonds; the first one between a cyclohexyl H atom and the O atom of the sulfonyl group (Table 1; C13-H13···O3 i ), and the second one between a cyclohexyl H atom and the O atom of the sulfonyl group (Table 1; C18-H18A···O2 ii ). The crystal packing (Fig. 3) is further stabilized by intermolecular C-H···π interactions between a methyl H atom and the benzene ring (Table 1; Cg is the centroid of the C2-C7 benzene ring).

Experimental
77% 3-Chloroperoxybenzoic acid (560 mg, 2.5 mmol) was added in small portions to a stirred solution of 3-cyclohexylsulfanyl-2-methyl-5-propyl-1-benzofuran (346 mg, 1.2 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 8 h, 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 (hexane-ethyl acetate, 4:1 v/v) to afford the title compound as a colorless solid [yield 70%, m.p. 393-395 K; R f = 0.60 (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.

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, methylene and 1.5U eq (C) for methyl H atoms. The C10 atom of the propyl group is disordered over two positions with site occupancy factors, from refinement of 0.546 (8) (part A) and 0.454 (8) (part B). The C-C distance sets were restrained to 0.001 Å using command SADI, and displacement ellipsoids of C10A and C10B set were restrained to 0.01 using command ISOR, EADP and DELU.

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.