2-(4-Bromophenyl)-5-fluoro-3-phenylsulfinyl-1-benzofuran

In the title compound, C20H12BrFO2S, the O atom and the phenyl group of the phenylsulfinyl substituent lie on opposite sides of the plane through the benzofuran fragment; the phenyl ring is nearly perpendicular to this plane [dihedral angle = 86.98 (6)°]. The 4-bromophenyl ring is rotated slightly out of the benzofuran plane, making a dihedral angle of 1.56 (8)°. The crystal structure features aromatic π–π interactions between the furan and phenyl rings of neighbouring molecules [centroid–centroid distance = 3.506 (3) Å], and an intermolecular C—H⋯π interaction. The crystal structure also exhibits a short intermolecular S⋯S contact [3.2635 (8) Å].

In the title compound, C 20 H 12 BrFO 2 S, the O atom and the phenyl group of the phenylsulfinyl substituent lie on opposite sides of the plane through the benzofuran fragment; the phenyl ring is nearly perpendicular to this plane [dihedral angle = 86.98 (6) ]. The 4-bromophenyl ring is rotated slightly out of the benzofuran plane, making a dihedral angle of 1.56 (8) . The crystal structure features aromaticinteractions between the furan and phenyl rings of neighbouring molecules [centroid-centroid distance = 3.506 (3) Å ], and an intermolecular C-HÁ Á Á interaction. The crystal structure also exhibits a short intermolecular SÁ Á ÁS contact [3.2635 (8) Å ].
Cg3 is the centroid of the C15-C20 phenyl ring.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2256). properties such as antifungal, antitumor and antiviral, antimicrobial activities (Aslam et al., 2006, Galal et al., 2009, Khan et al., 2005. These compounds occur widely in nature (Akgul & Anil, 2003;Soekamto et al., 2003). As a part of our continuing studies of the substituent effect on the solid state structures of 5-halo-2-phenyl-3-phenylsulfinyl-1-benzofuran analogues (Choi et al., 2009a,b,c), we report the crystal structure of the title compound (Fig. 1).
The benzofuran unit is essentially planar, with a mean deviation of 0.063 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the benzofuran plane and the phenyl ring is 86.98 (6)°, and the 4-bromophenyl ring with 1.56 (8)° lies toward the benzofuran plane. The crystal packing (Fig. 2) is stabilized by aromatic π-π interactions between the furan and benzene rings of the adjacent molecules, with a Cg1···Cg2 ii distance of 3.506 (3) Å (Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2-C7 benzene ring, respectively). The molecular packing ( Fig. 2) is further stabilized by an intermolecular C-H···π interaction between the benzene H atom and the phenyl ring of a neighbouring molecule, with a C5-H5···Cg3 i (Table 1; Cg3 is the centroid of the C15-C20 phenyl ring). The crystal structure also exhibits a short intermolecular S···S contact (Munshi & Guru Row, 2004), with a S···S iv distance of 3.2635 (8) Å Experimental 77% 3-chloroperoxybenzoic acid (247 mg, 1.1 mmol) was added in small portions to a stirred solution of 2-(4-bromophenyl)-5-fluoro-3-phenylsulfanyl-1-benzofuran (439 mg, 0.8 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 6h, 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 68%, m.p. 465-466 K; Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in benzene at room temperature.

Refinement
All H atoms were positioned geometrically and refined using a riding model, with C-H = 0.93 Å and U iso (H) = 1.2U eq (C).
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 a 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.