5-Chloro-3-(4-fluorophenylsulfonyl)-2-methyl-1-benzofuran

In the title compound, C15H10ClFO3S, the 4-fluorophenyl ring makes a dihedral angle of 75.83 (5)° with the plane of the benzofuran fragment. In the crystal, weak intermolecular C—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers, which are further linked via an aromatic π–π interaction between the benzene rings of adjacent molecules [centroid–centroid distance = 3.510 (2) Å].

In the title compound, C 15 H 10 ClFO 3 S, the 4-fluorophenyl ring makes a dihedral angle of 75.83 (5) with the plane of the benzofuran fragment. In the crystal, weak intermolecular C-HÁ Á ÁO hydrogen bonds link the molecules into centrosymmetric dimers, which are further linked via an aromaticinteraction between the benzene rings of adjacent molecules [centroid-centroid distance = 3.510 (2) Å ].
The benzofuran unit is essentially planar, with a mean deviation of 0.013 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the benzofuran plane and the 4-fluorophenyl ring is 75.83 (5)°.
The crystal packing ( Fig. 2) is stabilized by weak intermolecular C-H···O hydrogen bonds between the 4-fluorophenyl H atom and the oxygen of the O═S═O unit, with C11-H11···O3 i ( Table 1). The packing is further stabilized by an aromatic π-π interaction between the benzene rings of neighbouring molecules, with a Cg···Cg ii distance of 3.510 (2) Å (Cg is the centroid of the C2-C7 benzene ring).

Experimental
77% 3-chloroperoxybenzoic acid (515 mg, 2.3 mmol) was added in small portions to a stirred solution of 5-chloro-3-(4fluorophenylsulfanyl)-2-methyl-1-benzofuran (339 mg, 1.1 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 10h, 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 colourless solid [yield 78%, m.p. 452-453 K; R f = 0.54 (benzene)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in chloroform at room temperature.

Refinement
All H atoms were clearly located from Fourier difference maps and refined at idealized positions using a riding model, with C-H = 0.93 Å for aryl and 0.96 Å for methyl H atoms. U iso (H) = 1.2U eq (C) for aryl and 1.5U eq (C) for methyl H atoms.
supplementary materials sup-2 Figures 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.

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.