5-Cyclohexyl-3-ethylsulfinyl-2-(3-fluorophenyl)-1-benzofuran

In the title compound, C22H23FO2S, the cyclohexyl ring adopts a chair conformation. The dihedral angle between the mean plane [r.m.s. deviation = 0.013 (2) Å] of the benzofuran ring system and the mean plane [r.m.s. deviation = 0.009 (2) Å] of the 3-fluorophenyl ring is 24.80 (4)°. In the crystal, molecules are connected by C—H⋯O hydrogen bonds, forming chains along [10-1]. These chains are linked via C—H⋯F hydrogen bonds, forming a three-dimensional structure. There are also interplanar interactions present involving the furan ring of the benzofuran ring system and the 3-fluorophenyl ring [centroid–centroid distance = 3.728 (2) Å].

In the title compound, C 22 H 23 FO 2 S, the cyclohexyl ring adopts a chair conformation. The dihedral angle between the mean plane [r.m.s. deviation = 0.013 (2) Å ] of the benzofuran ring system and the mean plane [r.m.s. deviation = 0.009 (2) Å ] of the 3-fluorophenyl ring is 24.80 (4) . In the crystal, molecules are connected by C-HÁ Á ÁO hydrogen bonds, forming chains along [101]. These chains are linked via C-HÁ Á ÁF hydrogen bonds, forming a three-dimensional structure. There are also interplanar interactions present involving the furan ring of the benzofuran ring system and the 3-fluorophenyl ring [centroidcentroid distance = 3.728 (2) Å ].

Related literature
For background information and the crystal structures of related compounds, see: Choi et al. (2011Choi et al. ( , 2012 Table 1 Hydrogen-bond geometry (Å , ).
supplementary materials . E69, o1462 [doi:10.1107/S1600536813023180] The title compound crystallizes in the non-centrosymmetric space group C c in spite of having no asymmetric C atoms.

5-Cyclohexyl
In the title molecule, Fig. 1, the cyclohexyl ring adopts a chair conformation. The benzofuran ring system is essentially planar, with a mean deviation of 0.013 (2) Å from the mean plane defined by the nine non-H atoms. The 3-fluorophenyl ring is essentially planar, with a mean deviation of 0.009 (2) Å from the mean plane defined by the six non-H atoms. The dihedral angle formed by the benzofuran ring system and the 3-fluorophenyl ring is 24.80 (4)°.
In the crystal structure, molecules are connected by weak C-H···O hydrogen bonds (Table 1), forming chains along the [10-1] direction.

Experimental
3-Chloroperoxybenzoic acid (77%, 202 mg, 0.9 mmol) was added in small portions to a stirred solution of 5-cyclohexyl-3-ethylsulfanyl-2-(3-fluorophenyl)-1-benzofuran (283 mg, 0.8 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 5h, 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 colourless solid [yield 70%, m.p. 417-418 K; R f = 0.68 (hexane-ethyl acetate, 2:1 v/v)]. Colourless block-like crystals, suitable for X-ray diffraction analysis, were prepared by slow evaporation of a solution of the title compound in acetone at room temperature.

Figure 1
The molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.  where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max = 0.001 Δρ max = 0.17 e Å −3 Δρ min = −0.22 e Å −3 Absolute structure: Flack (1983), 1045 (51%) Friedel pairs Absolute structure parameter: 0.05 (7) 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.