2-(3-Fluorophenyl)-3-methylsulfanyl-5-phenyl-1-benzofuran

In the title compound, C21H15FOS, the dihedral angles between the mean plane of the benzofuran fragment and the pendant 3-fluorophenyl and phenyl rings are 1.76 (5) and 32.29 (5)°, respectively. In the crystal, molecules are linked by a slipped π–π interaction between the furan and benzene rings of neighbouring molecules [centroid–centroid distance = 3.665 (2) Å, interplanar distance = 3.391 (2) Å and slippage = 1.390 (2) Å].

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FF2033).

Comment
Recently, many compounds having a benzofuran moiety have drawn much attention due to their valuable pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2009, Galal et al., 2009, Khan et al., 2005. These benzofuran derivatives occur in a wide range of natural products (Akgul & Anil, 2003;Soekamto et al., 2003). As a part of our ongoing study of benzofuranderivatives containing either 2-(4-fluorophenyl) (Choi et al., 2009) or 2-(4-chlorophenyl) (Choi et al., 2010) substituents, 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 0.007 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angles between the mean plane of the benzofuran fragment and the 4-fluorophenyl and phenyl rings are 1.76 (5)° and 32.29 (5)°, respectively. The crystal packing ( Fig. 2) is stabilized by a slipped π-π interaction between the furan and benzene rings of adjacent molecules, with a Cg1···Cg2 i distance of 3.665 (2) Å and an interplanar distance of 3.391 (2) Å resulting in a slippage of 1.390 (2) Å (Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2-C7 benzene ring, respectively).

Experimental
Zinc chloride (273 mg, 2.0 mmol) was added to a stirred solution of 4-phenylphenol (340 mg, 2.0 mmol) and 2-chloro-2methylsulfanyl-3'-fluoroacetophenone (437 mg, 2.0 mmol) in dichloromethane (30 mL) at room temperature, and stirring was continued at the same temperature for 1h. The reaction was quenched by the addition of water and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane-benzene, 5:2 v/v) to afford the title compound as a colorless solid [yield 54%, m.p. 357-358 K; R f = 0.61 (hexane-benzene, 5:2 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in acetone 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. 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.