2-Methyl-3-phenylsulfinyl-1-benzofuran

The title compound, C15H12O2S, was prepared by the oxidation of 2-methyl-3-phenylsulfanyl-1-benzofuran with 3-chloroperoxybenzoic acid. The O atom and the phenyl group of the phenylsulfinyl substituent lie on opposite sides of the plane of the benzofuran system. The phenyl ring makes a dihedral angle of 78.76 (4)° with the benzofuran mean plane. The crystal structure is stabilized by π–π interactions between the furan and benzene rings of neighbouring molecules [centroid–centroid distance = 4.017 (3) Å]. In addition, the crystal structure exhibits intermolecular C—H⋯π and C—H⋯O interactions.

The title compound, C 15 H 12 O 2 S, was prepared by the oxidation of 2-methyl-3-phenylsulfanyl-1-benzofuran with 3chloroperoxybenzoic acid. The O atom and the phenyl group of the phenylsulfinyl substituent lie on opposite sides of the plane of the benzofuran system. The phenyl ring makes a dihedral angle of 78.76 (4) with the benzofuran mean plane. The crystal structure is stabilized byinteractions between the furan and benzene rings of neighbouring molecules [centroid-centroid distance = 4.017 (3) Å ]. In addition, the crystal structure exhibits intermolecular C-HÁ Á Á and C-HÁ Á ÁO interactions.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2156).
H. D. Choi, P. J. Seo, B. W. Son and U. Lee
The benzofuran unit is almost planar, with a mean deviation of 0.008 (1) ° from the least-squares plane defined by the nine constituent atoms. The phenyl ring (C9-C14) is almost perpendicular to the plane of the benzofuran ring system [78.76 (4)°] and is tilted slightly towards it. The crystal packing ( Fig. 2) is stabilized by aromatic π-π interactions between the furan and the benzene rings of neighbouring molecules. The Cg1···Cg2 iv distance is 4.017 (3) Å (Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2-C7 benzene ring, respectively, symmetry code as in Fig. 2). The crystal packing is further stabilized by C-H···π interactions between a phenyl H atom of the phenylsulfinyl substitutent and the benzene ring of the benzofuran unit, with a C12-H12···Cg2 iii separation of 3.20 Å ( Fig. 2 and Table 1; Cg2 is the centroid of the C2-C7 benzene ring, symmetry code as in Fig. 2). Additionally, intermolecular C-H···O interactions in the structure were observed ( Fig. 2 and Table 1; symmetry code as in Fig. 2).
Experimental 77% 3-Chloroperoxybenzoic acid (247 mg, 1.1 mmol) was added in small portions to a stirred solution of 2-methyl-3phenylsulfanyl-1-benzofuran (240 mg, 1.0 mmol) in dichloromethane (30 ml) at 273 K. After being stirred for 3 h at room temperature, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue was purified by column chromatography

Refinement
All H atoms were positioned geometrically and refined using a riding model, with C-H = 0.95 Å for aromatic H atoms and 0.98 Å for methyl H atoms, respectively, and with U iso (H) = 1.2Ueq(C) for aromatic and U iso (H) = 1.5Ueq(C) for methyl H atoms.
supplementary materials sup-2 Figures   Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level. Fig. 2. π-π, C-H···π and C-H···O interactions (dotted lines) in the title compound. Cg denotes the ring centroid. [Symmetry codes: (i) x, -y + 1/2, z + 1/2; (ii) x, -y + 3/2, z + 1/2; (iii)x, -y + 1, -z + 1; (iv) -x + 1, -y + 1, -z + 1; (v) x + 1, y, z.] 2-Methyl-3-phenylsulfinyl-1-benzofuran 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 > σ(F 2 ) is used only for calculating Rfactors(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.