Isoamyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate

In the title compound, C16H19BrO4S, 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 exhibits aromatic π–π interactions between the benzene rings of adjacent molecules [centroid–centroid distance = 3.643 (2) Å] and nonclassical C—H⋯O hydrogen bonds.

In the title compound, C 16 H 19 BrO 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 exhibits aromaticinteractions between the benzene rings of adjacent molecules [centroid-centroid distance = 3.643 (2) Å ] and nonclassical C-HÁ Á ÁO hydrogen bonds.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2569).
The benzofuran unit is essentially planar, with a mean deviation of 0.015 (1) Å from the least-squares plane defined by the nine constituent atoms. The crystal packing (Fig. 2) is stabilized by aromatic π···π interactions between the benzene rings from the adjacent molecules. The Cg···Cg ii distance of 3.643 (2) Å (Cg is the centroid of C2-C7 benzene ring. symmetry code as in Fig. 2). The molecular packing is further stabilized by four different types of non-calssical C-H···O hydrogen bonds; the first between a benzene H atom and the S=O unit, the second between a benzene H atom and the C═O unit, the third between an H atom of the methylene group bonded to the carboxylate C atom and the S═O unit, the fourth between an H atom of the methylene group bonded to the carboxylate C atom and the furan O atom, respectively (Table 1 and Fig. 2; symmetry code as in Fig. 2).

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 Br 0.09369 (2)