3-(4-Bromophenylsulfonyl)-5-chloro-2-methyl-1-benzofuran

In the title compound, C15H10BrClO3S, the 4-bromo-substituted benzene ring forms a dihedral angle of 72.55 (6)° with the mean plane [mean deviation = 0.008 (2) Å] of the benzofuran ring system. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds into chains along [001]. There are also π–π interactions between the furan and benzene rings of symmetry-related benzofuran systems [centroid–centroid distances = 3.549 (3) and 3.632 (3) Å].


Related literature
For background information and the crystal structures of related compounds, see: Choi et al. (2008Choi et al. ( , 2010 Table 1 Hydrogen-bond geometry (Å , ).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5482).

Experimental
3-Chloroperoxybenzoic acid (77%, 381 mg, 1.7 mmol) was added in small portions to a stirred solution of 3-(4-bromophenylsulfanyl)-5-chloro-2-methyl-1-benzofuran (318 mg, 0.8 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 8h, 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 (benzene) to afford the title compound as a colorless solid [yield 76%, m.p. 454-456 K; R f = 0.71 (benzene)]. 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 H atoms were positioned geometrically and refined using a riding model, with C-H = 0.95 Å for aryl and 0.98 Å for methyl H atoms. U iso (H) = 1.2U eq (C) for aryl and 1.5U eq (C) for methyl H atoms. The positions of methyl hydrogens were optimized rotationally.    A view of the π-π interactions (dotted lines) in the crystal packing of the title compound. All H atoms are omitted for clarity. [Symmetry codes: (iii) -x + 1,-y + 1,-z + 1; (iv) -x, -y + 1,-z + 1]. where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max = 0.001 Δρ max = 0.45 e Å −3 Δρ min = −0.43 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq