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

In the title compound, C15H17IO4S, 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 weak intermolecular C—H⋯π interactions between a methyl H atom of the methylsulfinyl group and the benzene ring of the benzofuran system, and by an I⋯O halogen bond of 3.173 (3) Å and a nearly linear C—I⋯O angle of 171.7 (1)°. In addition, the crystal structure exhibits weak intermolecular C—H⋯O hydrogen bonds. The O atom of the carbonyl group and the butyl chain are both disordered over two positions with site-occupancy factors from refinement of 0.55 (4) and 0.45 (4) (for the O atom), and 0.76 (2) and 0.24 (2) (for the butyl group).

In the title compound, 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. The crystal structure is stabilized by weak intermolecular C-HÁ Á Á interactions between a methyl H atom of the methylsulfinyl group and the benzene ring of the benzofuran system, and by an IÁ Á ÁO halogen bond of 3.173 (3) Å and a nearly linear C-IÁ Á ÁO angle of 171.7 (1) . In addition, the crystal structure exhibits weak intermolecular C-HÁ Á ÁO hydrogen bonds. The O atom of the carbonyl group and the butyl chain are both disordered over two positions with site-occupancy factors from refinement of 0.55 (4) and 0.45 (4) (for the O atom), and 0.76 (2) and 0.24 (2) (for the butyl group).
The benzofuran unit is essentially planar, with a mean deviation of 0.004 (3) Å from the least-squares plane defined by the nine constituent atoms. The oxygen atom of carbonyl group is disordered over two positions with site-occupancy factors of 0.55 (4) (for atom labelled A) and 0.45 (4) (for atom labelled B), and the butyl group over two positions with site-occupancy factors of 0.76 (2) (for atom labelled A) and 0.24 (2) (for atom labelled B), respectively, in Fig. 1. The molecular packing ( Fig. 2) is stabilized by intermolecular C-H···π interactions between a methyl H atom of the methylsulfinyl group and the benzene ring of the benzofuran unit, with a C15-H15B···Cg i separation of 2.97 Å (Table 1 and Fig. 2; Cg is the centroid of the C2-C7 benzene ring, symmetry code as in Fig. 2). The molecular packing is further stabilized 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···O4 iv distance of 3.173 (3) Å (symmetry code as in Fig. 2). In addition, weak intermolecular C-H···O hydrogen bonds in the structure are observed (Table 1 & Fig. 2).

Refinement
All H atoms were geometrically positioned and refined using a riding model, with C-H = 0.95 Å for the aryl, 0.99 Å for the methylene, and 0.98 Å for the methyl H atoms. Uiso(H) = 1.2Ueq(C) for the aryl and methylene H atoms, and 1.5Ueq(C) for methyl H atoms. The oxygen atom of carbonyl group and butyl group were found to be disordered over two positions and modelled with site-occupancy factors, from refinement of 0.55 (4) (O3A) and 0.45 (4) (O3B), and 0.76 (2) (C11A-C14A)) and 0.24 (2) (C11B-C14B), respectively. The displacement ellipsoids of part B were restrained using command ISOR (0.01), supplementary materials sup-2 both sets of O and C atoms were restrained using the command DELU and the distances of C-C were restrained to 1.480 (2) Å using command DFIX. The distances of C═O were restrained to 0.001 Å using command SADI. Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level. The oxygen atom of carbonyl group and butyl group are disordered over two positions with site-occupancy factors, from refinement of 0.55 (4) and 0.45 (4) (for the O atom), 0.76 (2) and 0.24 (2) (for the butyl group), respectively.

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.