7-Bromo-2-phenyl-1-(phenylsulfinyl)naphtho[2,1-b]furan benzene hemisolvate

The title compound, C24H15BrO2S·0.5C6H6, crystallizes as a benzene hemisolvate. The O atom and the phenyl group of the phenylsulfinyl substituent lie on opposite sides of the plane of the naphthofuran fragment, and the phenyl ring is almost perpendicular to the plane of the naphthofuran fragment [83.78 (8)°] and is tilted slightly towards it. The 2-phenyl ring is rotated out of the naphthofuran plane by a dihedral angle of 25.2 (1)°. The crystal structure is stabilized by aromatic π–π interactions between the central benzene ring and the furan ring of the neighbouring naphthofuran systems [centroid–centroid distance = 3.611 (3) Å], and by intermolecular C—H⋯π interactions between the benzene H atom of the phenylsulfinyl substituent and the 2-phenyl ring of an adjacent molecule. In addition, the crystal structure exhibits a weak non-classical intermolecular C—H⋯O hydrogen bond.

The title compound, C 24 H 15 BrO 2 SÁ0.5C 6 H 6 , crystallizes as a benzene hemisolvate. The O atom and the phenyl group of the phenylsulfinyl substituent lie on opposite sides of the plane of the naphthofuran fragment, and the phenyl ring is almost perpendicular to the plane of the naphthofuran fragment [83.78 (8) ] and is tilted slightly towards it. The 2-phenyl ring is rotated out of the naphthofuran plane by a dihedral angle of 25.2 (1) . The crystal structure is stabilized by aromaticinteractions between the central benzene ring and the furan ring of the neighbouring naphthofuran systems [centroidcentroid distance = 3.611 (3) Å ], and by intermolecular C-HÁ Á Á interactions between the benzene H atom of the phenylsulfinyl substituent and the 2-phenyl ring of an adjacent molecule. In addition, the crystal structure exhibits a weak non-classical intermolecular C-HÁ Á ÁO hydrogen bond.
The naphthofuran unit is essentially planar, with a mean deviation of 0.056 (2) Å from the least-squares plane defined by the thirteen constituent atoms. The dihedral angle in (I) formed by the plane of the naphthofuran ring and the plane of 2-phenyl ring is 25.2 (1)°, and the phenyl ring (C19-C24) with a dihedral angle of 83.78 (8)° is almost perpendicular and titlled slightly toward the naphthofuran moieity. The crystal packing (Fig. 2) is stabilized by aromatic π-π interactions between the central benzene ring and the furan ring from adjacent molecules. The Cg2···Cg3 iv distance is 3.611 (3) Å (Cg2 and Cg3 are the centroides of the C1/C2/C11/O1/C12 furan ring and the C2/C3/C8/C9/C10/C11 benzene ring, respectively, symmetry code as in Fig. 2). The molecular packing is further stabilized by intermolecular C-H···π interactions between the benzene H atom of the phenylsulfinyl substituent and the 2-phenyl ring of an adjacent molecule (Table 1 and Fig. 2).
Additionally, a weak non-calssical intermolecular C-H···O hydrogen bond in the structure was observed ( Fig. 2 and Table   1; symmetry code as in Fig. 2).
Experimental 3-chloroperoxybenzoic acid (77%, 217 mg, 0.88 mmol) was added in small portions to a stirred solution of 7-bromo-2phenyl-1-(phenylsulfanyl)naphtho[2,1-b]furan (345 mg, 0.8 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 4h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was purified by column chromatography (hexane-ethyl acetate, 2:1 v/v) to afford the title compound as a colorless solid [yield 78%, m.p. 448-449 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 for aromatic H atoms and with Uiso(H) = 1.2Ueq(C) for aromatic H atoms. The distances of C-C in the solvated benzene ring were restrained to 1.40 (1) Å using command DFIX.

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 Br 1.02842 (5)