3-(4-Fluorophenylsulfinyl)-5-iodo-2-methyl-1-benzofuran

In the title compound, C15H10FIO2S, the O atom and the 4-fluorophenyl group of the 4-fluorophenylsulfinyl substituent are located on opposite sides of the plane through the benzofuran fragment; the 4-fluorophenyl ring is nearly perpendicular to this plane, making a dihedral angle of 83.37 (7)°. The crystal structure is stabilized by weak intermolecular C—H⋯O hydrogen bonds and an I⋯O interaction [I⋯O = 3.255 (2) Å]. The crystal structure also exhibits intermolecular C—F⋯π interactions [3.068 (2) Å], and aromatic π–π interactions between the furan and benzene rings of neighbouring benzofuran fragments [centroid–centroid distance = 3.636 (2) Å].

In the title compound, C 15 H 10 FIO 2 S, the O atom and the 4fluorophenyl group of the 4-fluorophenylsulfinyl substituent are located on opposite sides of the plane through the benzofuran fragment; the 4-fluorophenyl ring is nearly perpendicular to this plane, making a dihedral angle of 83.37 (7) . The crystal structure is stabilized by weak intermolecular C-HÁ Á ÁO hydrogen bonds and an IÁ Á ÁO interaction [IÁ Á ÁO = 3.255 (2) Å ]. The crystal structure also exhibits intermolecular C-FÁ Á Á interactions [3.068 (2) Å ], and aromaticinteractions between the furan and benzene rings of neighbouring benzofuran fragments [centroidcentroid distance = 3.636 (2) Å ].
The benzofuran unit is essentially planar, with a mean deviation of 0.008 (2) Å from the least-squares plane defined by the nine constituent atoms. The 4-fluorophenyl ring is almost perpendicular to the plane of the benzofuran fragment [83.37 (7)°] and is tilted slightly towards it. The crystal packing ( Fig. 2) is stabilized by weak intermolecular C-H···O hydrogen bonds; the first one between the benzene H atom and the furan O atom with a C5-H5···O1 i , and the second one between the methyl H atom and the oxygen of the S═O unit, with a C9-H9C···O2 ii , respectively (Table 1). The molecular packing ( Fig. 2) is also stabilized by an I···O halogen bonding between the iodine and the oxygen of the S═O unit (Politzer et al., 2007). The crystal packing (Fig. 3) also exhibits intermolecular C-F···π interactions between the fluorine and the benzene ring of an adjacent benzofuran system, with a C13-F···Cg2 vii distance of 3.068 (2) Å (Cg2 is the centroid of the C2-C7 benzene ring), and aromatic π-π interactions between the furan and the benzene rings of the adjacent benzofuran systems, with a Cg1···Cg2 viii distance of 3.636 (2) Å (Cg1 is the centroid of the C1/C2/C7/O1/C8 furan ring).
Experimental 77% 3-Chloroperoxybenzoic acid (166 mg, 1.0 mmol) was added in small portions to a stirred solution of 3-(4-fluorophenylsulfanyl)-5-iodo-2-methyl-1-benzofuran (346 mg, 0.9 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 3h, 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, 1:1 v/v) to afford the title compound as a colorless solid [yield 77%, m.p. 428-429 K; R f = 0.64 (hexane-ethyl acetate, 1:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in benzene at room temperature.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq I 0.774810 (15)