3-(3-Bromophenylsulfinyl)-5-cyclohexyl-2-methyl-1-benzofuran

In the title compound, C21H21BrO2S, the cyclohexyl ring adopts a chair conformation. The dihedral angle between the mean plane [r.m.s. deviation = 0.178 (2) Å] of the benzofuran ring system and the mean plane of the 3-bromophenyl ring is 86.52 (6)°. In the crystal, molecules are linked by weak C—H⋯O and C—H⋯π hydrogen bonds, and by a slipped π–π interaction between the furan rings of neighbouring molecules [centroid–centroid distance = 3.518 (3) Å, interplanar distance = 3.471 (3) Å and slippage = 0.573 (3) Å], resulting in a three-dimensional network.


Related literature
For background information and the crystal structures of related compounds, see: Choi et al. (2011Choi et al. ( , 2012a Table 1 Hydrogen-bond geometry (Å , ).
Supporting information for this paper is available from the IUCr electronic archives (Reference: GK2602).
In the title molecule ( Fig. 1), the cyclohexyl ring has a chair conformation. The benzofuran ring system is essentially planar, with a mean deviation of 0.178 (2) Å from the least-squares plane defined by the nine constituent atoms. The 3bromophenyl ring is essentially planar, with a mean deviation of 0.005 (2) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring system and the 3-bromophenyl ring is 86.52 (6)°.

Experimental
3-Chloroperoxybenzoic acid (77%, 224 mg, 1.0 mmol) was added in small portions to a stirred solution of 3-(3-bromophenylsulfanyl)-5-cyclohexyl-2-methyl-1-benzofuran(361 mg, 0.9 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 4h, 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, 2:1 v/v) to afford the title compound as a colorless solid [yield 71%, m.p. 415-416 K; R f = 0.47 (hexane-ethyl acetate, 2:1 v/v)]. 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. The positions of methyl hydrogens were optimized rotationally. 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, 2012) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).   x, -y + 1/2, z -1/2; (iii) -x + 1, -y + 1, -z + 1; (iv) -x + 1, y + 1/2, -z + 1/2; (v) x, -y + 1/2, z + 1/2.] where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max = 0.001 Δρ max = 0.33 e Å −3 Δρ min = −0.35 e Å −3 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq