2-Phenyl-1-(phenylsulfinyl)naphtho[2,1-b]furan

In the title compound, C24H16O2S, the O atom and the phenyl group of the phenylsulfinyl substituent lie on opposite sides of the plane of the naphthofuran fragment; the phenyl ring is almost perpendicular to this plane [82.34 (5)°]. The 2-phenyl ring is rotated out of the naphthofuran plane making a dihedral angle of 48.21 (6)°. The crystal structure shows π–π interactions between the central benzene rings of adjacent molecules [centroid–centroid distance = 3.516 (3) Å], as well as non-classical C—H⋯O hydrogen bonds.

In the title compound, C 24 H 16 O 2 S, the O atom and the phenyl group of the phenylsulfinyl substituent lie on opposite sides of the plane of the naphthofuran fragment; the phenyl ring is almost perpendicular to this plane [82.34 (5) ]. The 2-phenyl ring is rotated out of the naphthofuran plane making a dihedral angle of 48.21 (6) . The crystal structure showsinteractions between the central benzene rings of adjacent molecules [centroid-centroid distance = 3.516 (3) Å ], as well as non-classical C-HÁ Á ÁO hydrogen bonds.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2587).
The naphthofuran unit is essentially planar, with a mean deviation of 0.015 (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 48.21 (6)°, and the phenyl ring (C19-C24) with 82.34 (5)° lies toward the naphthofuran plane. The crystal packing ( Fig. 2) is stabilized by aromatic π-π interactions between the central benzene rings from the adjacent molecules.
The Cg···Cg iii distance is 3.516 (3) Å (Cg is the centroide of the C2/C3/C8/C9/C10/C11 benzene ring, symmetry code as in Fig. 2). The molecular packing is further stabilized by weak non-classical intermolecular C-H···O hydrogen bonds, the first between an aromatic H atom of the naphthofuran fragment and the S═O unit, the second between an aromatic H atom of 2-phenyl ring and the S═O unit, respectively (Table 1 and Fig. 2; symmetry code as in Fig. 2).

Experimental
The 77% 3-chloroperoxybenzoic acid (77%, 247 mg, 1.1 mmol) was added in small portions to a stirred solution of 2phenyl-1-(phenylsulfanyl)naphtho[2,1-b]furan (352 mg, 1.0 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 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 81%, m.p. 462-463 K; R f = 0.54 (hexane-ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title χompound in benzene at room temperature.

Refinement
All H atoms were positioned geometrically and refined using a riding model, with C-H = 0.95 Å for aromatic H atoms and with Uiso(H) = 1.2Ueq (C) for aromatic H atoms.
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.