Crystal structure of 2-(3-fluorophenyl)-5-iodo-3-methylsulfinyl-1-benzofuran

In the title compound, C15H10FIO2S, the dihedral angle between the planes of the benzofuran ring system [r.m.s. deviation = 0.015 (2) Å] and the 3-fluorophenyl ring is 29.63 (7)°. In the crystal, molecules are linked into inversion dimers along the b-axis direction by two different pairs of C—H⋯O hydrogen bonds and I⋯O [3.228 (1) Å] contacts.

After being stirred at room temperature for 8h, the mixture was washed with saturated sodium bicarbonate solution (2 X 10 ml) 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, 1:2 v/v) to afford the title compound as a colorless solid [yield 73% (263 mg); m.p. 453-454 K; R f = 0.55 (hexane-ethyl acetate, 1:2 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound (26 mg) in ethyl acetate (25 ml) at room temperature.

S3. Refinement
All H atoms were positioned geometrically and refined using a riding model, with C-H = 0.95 Å for aryl, and 0.98 Å for methyl H atoms, respectively. U iso (H) = 1.2U eq (C) for aryl 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).

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.  (iii) -x + 1, -y + 2, -z + 2.] 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 I1 0.171392 (16