5-Chloro-3-cyclohexylsulfonyl-2-methyl-1-benzofuran

In the title compound, C15H17ClO3S, the cyclohexyl ring adopts a chair conformation. In the crystal, molecules are linked through weak intermolecular C—H⋯O and C—H⋯π interactions.

In the title compound, C 15 H 17 ClO 3 S, the cyclohexyl ring adopts a chair conformation. In the crystal, molecules are linked through weak intermolecular C-HÁ Á ÁO and C-HÁ Á Á interactions.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2340).

Comment
Many compounds containing a benzofuran ring exhibit interesting pharmacological properties such as antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2006;Galal et al., 2009;Khan et al., 2005). These compounds occur in a wide range of natural products (Akgul & Anil, 2003;Soekamto et al., 2003). As a part of our ongoing study of the substituent effect on the solid state structures of 3-arylsulfonyl-5-chloro-2-methyl-1-benzofuran analogues (Choi et al., 2008(Choi et al., , 2010, we report herein the crystal structure of the title compound. In the title molecule ( Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.009 (1) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring is in the chair form. The molecular packing ( Fig. 2) is stabilized by weak intermolecular C-H···O hydrogen bonds; the first one between a benzene H atom and the O atom of the sulfonyl unit (Table 1: C6-H6···O3 i ), and the second one between a cyclohexyl H atom and the O atom of the sulfonyl unit (Table 1: C10-H10···O2 ii ). The crystal packing (Fig. 2) is further stabilized by intermolecular C-H···π interactions between a methyl H atoms and the benzene rings (Table 1: C9-H9C···Cg iii , 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-cyclohexylsulfanyl-2-methyl-1-benzofuran (389 mg, 1.1 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 5 h, 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, 4:1 v/v) to afford the title compound as a colorless solid [yield 73%, m.p. 440-441 K; 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, 1.00 Å for methine, 0.99 Å for methylene and 0.98 Å for methyl H atoms, respectively. U iso (H) = 1.2U eq (C) for aryl, methine and methylene, and 1.5U eq (C) for methyl H atoms.

Hydrogen-bond geometry (Å, °)
Cg is the centroid of the benzene ring.