Isopropyl 2-(5-iodo-3-methylsulfinyl-1-benzofuran-2-yl)acetate

In the title compound, C14H15IO4S, the O atom and the methyl group of the methylsulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. The crystal structure is stabilized by C—H⋯π interactions between a methyl H atom and the benzene ring of an adjacent molecule, and by weak intermolecular C—H⋯O hydrogen bonds.

In the title compound, C 14 H 15 IO 4 S, the O atom and the methyl group of the methylsulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. The crystal structure is stabilized by C-HÁ Á Á interactions between a methyl H atom and the benzene ring of an adjacent molecule, and by weak intermolecular C-HÁ Á ÁO hydrogen bonds.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2107).
Here we report the crystal structure of the title compound, isopropyl 2-(5-iodo-3-methylsulfinyl-1-benzofuran-2-yl) acetate (Fig. 1). The benzofuran unit is essentially planar, with a mean deviation of 0.013 (2) Å from the least-squares plane defined by the nine constituent atoms. The molecular packing is stabilized by C-H···π interactions between a methyl H atom of isopropyl group and the benzene ring of the benzofuran unit, with a C13-H13C···Cg iii separation of 2.78 Å ( Fig. 2 and Table 1; Cg is the centroid of the C2-C7 benzene ring, symmetry code as in Fig. 2). Also weak intermolecular C-H···O hydrogen bonds in the structure were observed (Table 1

Refinement
All H atoms were geometrically positioned and refined using a riding model, with C-H = 0.93 Å for the aryl, 0.97 Å for the methylene, 0.98 Å for the methine, and 0.96 Å for the methyl H atoms. U iso (H) = 1.2Ueq(C) for the aryl, methine and methylene H atoms, and 1.5Ueq(C) for methyl H atoms.

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.