5-Cyclohexyl-2-(4-fluorophenyl)-3-phenylsulfinyl-1-benzofuran

The asymmetric unit of the title compound, C26H23FO2S, contains two independent molecules (A and B), in both of which the cyclohexyl ring adopts a chair conformation. The benzofuran ring systems, the 4-fluorophenyl and phenyl rings are essentially planar, with r.m.s. deviations of 0.008 (1), 0.002 (1) and 0.003 (1) Å, respectively, for molecule A, and 0.016 (1), 0.004 (1) and 0.002 (1) Å, respectively, for molecule B. The dihedral angles between the benzofuran ring system and the pendant 4-fluorophenyl and phenyl rings are 12.3 (7) and 85.42 (4)°, respectively, for molecule A, and 39.67 (6) and 72.17 (4)°, respectively, for molecule B. In the crystal, molecules are linked by weak C—H⋯O and C—H⋯π interactions, 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. ( , 2012; Seo et al.  Table 1 Hydrogen-bond geometry (Å , ).

Comment
As a part of our continuing study of 2-(4-fluorophenyl)-3-phenylsulfinyl-1-benzofuran derivatives containing chloro (Choi et al., 2011), bromo (Seo et al., 2011), and iodo (Choi et al., 2012 groups in 5-position, we report here the crystal structure of the title compound which crystallizes with two independent molecules, A & B, in the asymmetric unit. In the title compound ( Fig. 1), the cyclohexyl ring of both molecules adopts a chair conformation. The benzofuran ring system is essentially planar, with a mean deviation of 0.008 (1) and 0.016 (1) Å, for A and B, respectively, from the leastsquares plane defined by the nine constituent atoms. The 4-fluorophenyl and phenyl rings are essentially planar, with mean deviations of 0.002 (1) and 0.003 (1) Å for molecule A, and 0.004 (1) and 0.002 (1) Å for molecule B, respectively, from the least-squares plane defined by the six constituent atoms. The dihedral angles formed by the benzofuran ring system and the pendant 4-fluorophenyl and phenyl rings are 12.31 (7) and 85.42 (4)° in molecule A, and 39.67 (6) and 72.17 (4)° in molecule B, respectively. In the crystal packing, molecules are connected by weak C-H···O hydrogen bonds ( Fig. 2 and Table 2) and C-H···π interactions ( Fig. 3 and Table 2, Cg1 and Cg2 are the centroids of the C41-C46 4-fluorophenyl ring and the C2-C7 benzene ring, respectively), resulting in a three-dimensional network.
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 63%, m.p. 403-404 K; R f = 0.78 (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 acetone 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. Uiso(H) = 1.2Ueq(C) for aryl, methine and methylene, and 1.5Ueq(C) for methyl H atoms The positions of methyl hydrogens were optimized rotationally.   The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.

5-Cyclohexyl-2-(4-fluorophenyl)-3-phenylsulfinyl-1-benzofuran
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.