Propyl 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 ring system. The crystal structure is stabilized by intermolecular C—H⋯π interactions between an H atom of the propyl methylene group closest to the carboxylate O atom and the benzene ring of a neighbouring molecule, and between an H atom of the outer propyl methylene group and the furan ring of a neighbouring molecule, respectively. Additionally, the crystal structure exhibits 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 ring system. The crystal structure is stabilized by intermolecular C-HÁ Á Á interactions between an H atom of the propyl methylene group closest to the carboxylate O atom and the benzene ring of a neighbouring molecule, and between an H atom of the outer propyl methylene group and the furan ring of a neighbouring molecule, respectively. Additionally, the crystal structure exhibits intermolecular C-HÁ Á ÁO hydrogen bonds.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2566).
The benzofuran unit is essentially planar, with a mean deviation of 0.012 (2) Å from the least-squares plane defined by the nine constituent atoms. The molecular packing ( Fig. 2) is stabilized by intermolecular C-H···π interactions within each stack of molecules; one between the hydrogen of 11-methylene group and the benzene ring of the benzofuran unit, with a C11-H11B···Cg1 i separation of 3.12 Å, and a second between the hydrogen of 12-methylene group and the furan ring of the benzofuran unit, with a C12-H12B···Cg2 i with a separation of 2.99 Å (Table 1 and Fig. 2; Cg1 and Cg2 are the centroids of the C2-C7 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively, symmetry code as in Fig. 2). In addition, intermolecular C-H···O hydrogen bonds in the structure are observed (Table 1).

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.