5-(4-Bromophenyl)-2-methyl-3-methylsulfinyl-1-benzofuran

In the title compound, C16H13BrO2S, the O atom and the methyl group of the methylsulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. The 4-bromophenyl ring is rotated out of the benzofuran plane, making a dihedral angle of 39.23 (8)°. The crystal structure exhibits weak non-classical intermolecular C—H⋯O hydrogen bonds and two intermolecular C—H⋯π interactions.

In the title compound, C 16 H 13 BrO 2 S, the O atom and the methyl group of the methylsulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. The 4bromophenyl ring is rotated out of the benzofuran plane, making a dihedral angle of 39.23 (8) . The crystal structure exhibits weak non-classical intermolecular C-HÁ Á ÁO hydrogen bonds and two intermolecular C-HÁ Á Á interactions.
The benzofuran unit is essentially planar, with a mean deviation of 0.005 (2) Å from the least-squares plane defined by the nine constituent atoms. The 4-bromophenyl ring is rotated out of the benzofuran plane, with a dihedral angle of 39.23 (8)°. The molecular packing ( Fig. 2) is stabilized by weak non-classical intermolecular C-H···O hydrogen bonds; the first between the 4-bromophenyl H atom and the furan O atom, with C10-H10···O2 i , the second between the methyl H atom and the oxygen of the S═O unit, with C15-H15B···O1 ii , the third between the methyl H atom of the methylsulfinyl substituent and the furan O atom, with C16-H16A···O2 i , respectively (Table 1). The crystal packing (Fig. 3) is further stabilized by two intermolecular C-H···π interactions; the first between the 4-bromophenyl H atom and the furan ring of a neighbouring molecule, with C13-H13···Cg2 iii , the second between the methyl H atom of the methylsulfinyl substituent and the 4-bromophenyl ring of an adjacent molecule, with C16-H16B···Cg1 iv , respectively (Table 1; Cg1 and Cg2 are the centroids of the C9-C14 phenyl ring and the C1/C2/C7/O2/C8 furan ring, respectively).

Refinement
All H atoms were geometrically positioned and refined using a riding model, with C-H = 0.93 Å for the aryl and 0.96 Å for the methyl H atoms. U iso (H) = 1.2U eq (C) for the aryl and 1.5U eq (C) for the methyl H atoms.  Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius. [Symmetry codes: (iii) -x+1, y+1/2, -z+1/2; (iv) -x + 1, -y+1, -z+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.