5-Chloro-3-ethylsulfinyl-2-(4-iodophenyl)-1-benzofuran

In the title compound, C16H12ClIO2S, the 4-iodophenyl ring is rotated out of the benzofuran plane by 9.4 (1)°. In the crystal structure, intermolecular C—H⋯π interactions and short intermolecular I⋯O contacts [3.142 (2) Å] are observed.

Cg is the centroid of the C2-C7 phenyl ring.
Experimental 3-chloroperoxybenzoic acid (77%) (202 mg, 0.9 mmol) was added in small portions to a stirred solution of 5-chloro-3-ethylsulfanyl-2-(4-iodophenyl)-1-benzofuran (373 mg, 0.9 mmol) in dichloromethane (30 mL) at 273 K. The mixture was stirred for 5 h at room temperature, 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 76%, m.p. 439-440 K; R f = 0.56 (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. Fig. 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 a small spheres of arbitrary radius.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq I 0.020729 (12)