2-(3-Fluorophenyl)-5-iodo-7-methyl-3-methylsulfinyl-1-benzofuran

In the title compound, C16H12FIO2S, the 3-fluorophenyl ring makes a dihedral angle of 34.93 (7)° with the mean plane [r.m.s. deviation = 0.019 (1) Å] of the benzofuran fragment. In the crystal, molecules are linked via pairs of I⋯O contacts [3.088 (2) Å] into inversion dimers. These dimers are connected by weak C—H⋯O hydrogen bonds.


Related literature
For background information and the crystal structures of related compounds, see: Choi et al. (2008Choi et al. ( , 2010. For a review of halogen bonding, see: Politzer et al. (2007).  Table 1 Hydrogen-bond geometry (Å , ).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5901).

Experimental
3-Chloroperoxybenzoic acid (77%, 202 mg, 0.9 mmol) was added in small portions to a stirred solution of 2-(3-fluorophenyl)-5-iodo-7-methyl-3-methylsulfanyl-1-benzofuran (326 mg, 0.8 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 70%, m.p. 459-460 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 ethyl acetate at room temperature.

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. U iso (H) was set to 1.2U eq (C) for aryl and 1.5U eq (C) for methyl H atoms. The positions of methyl hydrogens were optimized rotationally. program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).  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 2
A view of the C-H···O and I···O interactions (dotted lines) in the crystal structure of the title compound. H atoms nonparticipating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) -x + 2, -y + 1, -z + 2; (ii) x -1, y, z; where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max = 0.002 Δρ max = 0.45 e Å −3 Δρ min = −0.55 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.