5-Cyclohexyl-3-(2-fluorophenylsulfonyl)-2-methyl-1-benzofuran

In the title compound, C21H21FO3S, the cyclohexyl ring adopts a chair conformation. The dihedral angle between the mean planes of the benzofuran ring system and the fluorophenyl ring is 87.61 (3)°. In the crystal, molecules related by inversion are linked into dimers via pairs of C—H⋯π interactions. These dimers are further linked by π–π interactions between the furan rings of neighbouring molecules [centroid–centroid distance = 3.407 (2) Å and between the 2-fluorophenyl rings of neighbouring molecules [centroid–centroid distance = 3.742 (2) Å], resulting in a three-dimensional supramolecular network.

In the title compound, C 21 H 21 FO 3 S, the cyclohexyl ring adopts a chair conformation. The dihedral angle between the mean planes of the benzofuran ring system and the fluorophenyl ring is 87.61 (3) . In the crystal, molecules related by inversion are linked into dimers via pairs of C-HÁ Á Á interactions. These dimers are further linked byinteractions between the furan rings of neighbouring molecules [centroid-centroid distance = 3.407 (2) Å and between the 2-fluorophenyl rings of neighbouring molecules [centroid-centroid distance = 3.742 (2) Å ], resulting in a three-dimensional supramolecular network.

Related literature
For background information and the crystal structures of related compounds, see: Choi et al. (2012Choi et al. ( , 2014 Table 1 Hydrogen-bond geometry (Å , ).
Supporting information for this paper is available from the IUCr electronic archives (Reference: ZS2290).

Comment
As a part of our ongoing study of 5-cyclohexyl-2-methyl-1-benzofuran derivatives containing 4-methylphenylsulfonyl (Choi et al., 2012) and 2-bromophenylsulfonyl (Choi et al., 2014) substituents in the 3-position, we report here on the crystal structure of the title compound.
In the title molecule ( Fig. 1), the benzofuran ring system is essentially planar, with a mean deviation of 0.020 (1) Å from the least-squares plane defined by the nine constituent atoms. The 2-fluorophenyl ring is essentially planar, with a mean deviation of 0.007 (1) Å from the least-squares plane defined by the six constituent atoms. The cyclohexyl ring has a chair conformation. The dihedral angle formed by the benzofuran ring system and the 2-fluorophenyl ring is 87.61 (3)°.
After being stirred at room temperature for 8h, 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 73%, m.p. 437-438 K; R f = 0.53 (benzene)]. 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 and methylene, and 1.5U eq (C) for methyl H atoms. The positions of methyl hydrogens were optimized using the SHELXL-97's command AFIX 137 (Sheldrick, 2008).  The molecular structure of the title molecule with the atom numbering scheme. The displacement ellipsoids are drawn at the 50% probability level. The hydrogen atoms are presented as small spheres of arbitrary radius.   where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max < 0.001 Δρ max = 0.38 e Å −3 Δρ min = −0.37 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.