3-Ethylsulfinyl-2-(3-fluorophenyl)-5-phenyl-1-benzofuran

In the title compound, C22H17FO2S, the dihedral angles between the mean plane [r.m.s. deviation = 0.005 (1) Å] of the benzofuran ring system and the pendant 3-fluorophenyl and phenyl rings are 23.92 (5) and 32.44 (5)°, respectively. In the crystal, molecules are linked by two weak C—H⋯O(sulfinyl) hydrogen bonds and a C—H⋯π interaction, forming a sheet, which lies in the ab plane. A π–π interaction between the benzene and furan rings of neighbouring molecules [centroid–centroid distance = 3.976 (2) Å] links the molecules into inversion dimers and connects adjacent sheets, resulting in a three-dimensional network.

In the title compound, C 22 H 17 FO 2 S, the dihedral angles between the mean plane [r.m.s. deviation = 0.005 (1) Å ] of the benzofuran ring system and the pendant 3-fluorophenyl and phenyl rings are 23.92 (5) and 32.44 (5) , respectively. In the crystal, molecules are linked by two weak C-HÁ Á ÁO(sulfinyl) hydrogen bonds and a C-HÁ Á Á interaction, forming a sheet, which lies in the ab plane. Ainteraction between the benzene and furan rings of neighbouring molecules [centroidcentroid distance = 3.976 (2) Å ] links the molecules into inversion dimers and connects adjacent sheets, resulting in a three-dimensional network.

Related literature
For background information and the crystal structures of related compounds, see: Choi et al. (2006Choi et al. ( , 2010 Table 1 Hydrogen-bond geometry (Å , ).
Experimental 3-Chloroperoxybenzoic acid (77%, 202 mg, 0.9 mmol) was added in small portions to a stirred solution of 3-ethylsulfanyl-2-(3-fluorophenyl)-5-phenyl-1-benzofuran (278 mg, 0.8 mmol) in dichloromethane (30 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 colorless solid [yield 62%, m.p. 445-446 K; Rf = 0.51 (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.

Figure 1
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.

Figure 3
A view of the π-π interactions (dotted lines) in the crystal structure of the title compound. All H atoms were omitted for clarity. [Symmetry codes: (v) -x + 1, -y, -z + 1.] where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max < 0.001 Δρ max = 0.85 e Å −3 Δρ min = −0.41 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.