5-Iodo-7-methyl-3-methylsulfinyl-2-phenyl-1-benzofuran

The title compound, C16H13IO2S, was prepared by the oxidation of 5-iodo-7-methyl-3-methylsulfanyl-2-phenyl-1-benzofuran with 3-chloroperoxybenzoic acid. The phenyl ring makes a dihedral angle of 27.17 (9)° with the plane of the benzofuran fragment, with the O atom and the methyl group of the methylsulfinyl substituent lying on opposite sides of this plane. The crystal structure exhibits intermolecular C—H⋯I interactions, and an I⋯O halogen bond of 3.107 (2) Å with a nearly linear C—I⋯O angle of 173.73 (6)°.

The title compound, C 16 H 13 IO 2 S, was prepared by the oxidation of 5-iodo-7-methyl-3-methylsulfanyl-2-phenyl-1benzofuran with 3-chloroperoxybenzoic acid. The phenyl ring makes a dihedral angle of 27.17 (9) with the plane of the benzofuran fragment, with the O atom and the methyl group of the methylsulfinyl substituent lying on opposite sides of this plane. The crystal structure exhibits intermolecular C-HÁ Á ÁI interactions, and an IÁ Á ÁO halogen bond of 3.107 (2) Å with a nearly linear C-IÁ Á ÁO angle of 173.73 (6) .
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2118).
The benzofuran unit is essentially planar, with a mean deviation of 0.013 Å from the least-squares plane defined by the nine constituent atoms. The phenyl ring (C9-C14) makes a dihedral angle of 27.17 (9)° with the plane of the benzofuran fragment. The molecular packing ( Fig. 2) is stabilized by intermolecular C-H···I interactions (Table 1), and by an I···O halogen bond (Politzer et al., 2007) between the iodine atom and the oxygen of a neighbouring S═O unit, with an I···O2 i distance of 3.107 (2) Å (symmetry code as in Fig. 2).

Refinement
All H atoms were geometrically positioned and refined using a riding model, with C-H = 0.95 Å for aromatic H atoms, 0.98 Å for methyl H atoms, respectively, and with Uiso(H) = 1.2Ueq(C) for aromatic H atoms and 1.5Ueq(C) for methyl H atoms. The highest peak in the difference map is 0.98 Å from I and the largest hole is 0.92 Å from I.  5-Iodo-7-methyl-3-methylsulfinyl-2-phenyl-1-benzofuran

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.