2-(4-Chlorophenyl)-3-ethylsulfinyl-5-fluoro-1-benzofuran

In the title compound, C16H12ClFO2S, the 4-chlorophenyl ring is rotated out of the benzofuran plane, as indicated by the dihedral angle of 19.79 (8)°. The crystal structure exhibits weak intermolecular C—H⋯O hydrogen bonds and C—H⋯π interactions.

In the title compound, C 16 H 12 ClFO 2 S, the 4-chlorophenyl ring is rotated out of the benzofuran plane, as indicated by the dihedral angle of 19.79 (8) . The crystal structure exhibits weak intermolecular C-HÁ Á ÁO hydrogen bonds and C-HÁ Á Á interactions.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2275).
The benzofuran unit is essentially planar, with a mean deviation of 0.012 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the benzofuran plane and the 4-fluorophenyl ring is 19.79 (8)°. The crystal packing ( Fig. 2) is stabilized by two different C-H···O hydrogen bonds; the first between the benzene H atom and the oxygen of the S═O unit, with a C6-H6···O2 i , and the second between the 4-chlorophenyl H atom and the oxygen of the S═O unit, with a C11-H11···O2 ii , respectively (Table 1). The crystal packing (Fig. 2) is further stabilized by a C-H···π interaction between the methylene H atom and the 4-chlorophenyl ring, with a C15-H15A···Cg ii (Table 1; Cg is the centroid of the C9-C14 4-chlorophenyl ring).

Experimental
77% 3-Chloroperoxybenzoic acid (291 mg, 1.3 mmol) was added in small portions to a stirred solution of 2-(4chlorophenyl)-3-ethylsulfanyl-5-fluoro-1-benzofuran (368 mg, 1.2 mmol) in dichloromethane (30 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, 1:1 v/v) to afford the title compound as a colorless solid [yield 79%, m.p. 405-406 K; R f = 0.64 (hexane-ethyl acetate, 1:1 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 = 0.93 Å for aryl, 0.97 Å for methylene, and 0.96 Å for methyl H atoms. U iso (H) = 1.2U eq (C) for aryl and methylene H atoms, and 1.5U eq (C) for methyl H atoms.