5-Bromo-2-methyl-3-(3-methylphenylsulfinyl)-1-benzofuran

In the title compound, C16H13BrO2S, the dihedral angle between the mean plane [r.m.s. deviation = 0.012 (1) Å] of the benzofuran ring system and the 3-methylphenyl ring is 84.83 (4)°. In the crystal, molecules are linked via pairs of Br⋯O [3.240 (1) Å] contacts, forming inversion dimers. These dimers are linked by C—H⋯π interactions, forming a three-dimensional network.


Related literature
For background information and the crystal structures of related compounds, see: Choi et al. (2010Choi et al. ( , 2012a. For a review of halogen bonding, see: Politzer et al. (2007).  Table 1 Hydrogen-bond geometry (Å , ).
Supporting information for this paper is available from the IUCr electronic archives (Reference: SU2700).
In the title molecule, Fig. 1, the benzofuran unit is essentially planar, with a mean deviation of 0.012 (1) Å from the mean plane defined by the nine constituent atoms. It is inclined to the 3-methylphenyl ring by 84.83 (4)°.

Experimental
3-Chloroperoxybenzoic acid (77%, 224 mg, 1.0 mmol) was added in small portions to a stirred solution of 5-bromo-2methyl-3-(3-methylphenylsulfanyl)-1-benzofuran (300 mg, 0.9 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 5h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane-ethyl acetate, 2:1 v/v) to afford the title compound as a colorless solid [Yield 78%, M.p. 413-414 K; R f = 0.49 (hexane-ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.

Refinement
All the H atoms were positioned geometrically and refined using a riding model: C-H = 0.95 Å for aryl and 0.99 Å for methyl H atoms with U iso (H) = 1.2U eq (C-aryl) and = 1.5U eq (C-methyl). The positions of the methyl hydrogens were optimized rotationally. program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).  The molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.   Table 1 for details; H atoms not involved in hydrogen-bonding have been omitted for clarity; symmetry codes : (i) -x + 1, -y + 1, -z + 2; (ii) x + 1, y, z; (iii) -x, -y + 1, -z + 1; (iv) x -1, y, z]. where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max = 0.001 Δρ max = 0.36 e Å −3 Δρ min = −0.54 e Å −3 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.