Isopropyl 2-(5-iodo-7-methyl-3-methylsulfinyl-1-benzofuran-2-yl)acetate

In the title molecule, C15H17IO4S, the O atom and the methyl group of the methylsulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. In the crystal structure, intermolecular I⋯O [2.994 (3) Å] halogen bonding links the molecules into centrosymmetric dimers, which are further packed into ribbons along the c axis by intermolecular sulfinyl–sulfinyl interactions [S⋯O 3.128 (3) Å].

In the title molecule, C 15 H 17 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. In the crystal structure, intermolecular IÁ Á ÁO [2.994 (3) Å ] halogen bonding links the molecules into centrosymmetric dimers, which are further packed into ribbons along the c axis by intermolecular sulfinyl-sulfinyl interactions [SÁ Á ÁO 3.128 (3) Å ].
The benzofuran unit is essentially planar, with a mean deviation of 0.030 (3) Å from the least-squares plane defined by the nine constituent atoms. The molecular packing (  (Table 1). These dimers are further packed into ribbons along the c axis by sulfinyl-sulfinyl interactions (Table 1) interpreted as simliar to a type-II carbonyl-carbonyl interaction (Allen et al., 1998).
After being stirred for 3 h at room temperature, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuum.

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. Uiso(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq I 0.513353 (18)