7-Bromo-1-methylsulfinyl-2-phenylnaphtho[2,1-b]furan

In the title compound, C19H13BrO2S, the O atom and the methyl group of the methylsulfinyl substituent lie on opposite sides of the plane of the naphthofuran unit. The phenyl ring is rotated out of the naphthofuran plane, making a dihedral angle of 42.2 (1)°. The crystal structure is stabilized by two intermolecular C—H⋯π interactions, and by non-classical intermolecular C—H⋯O and C—H⋯Br hydrogen bonds.

In the title compound, C 19 H 13 BrO 2 S, the O atom and the methyl group of the methylsulfinyl substituent lie on opposite sides of the plane of the naphthofuran unit. The phenyl ring is rotated out of the naphthofuran plane, making a dihedral angle of 42.2 (1) . The crystal structure is stabilized by two intermolecular C-HÁ Á Á interactions, and by non-classical intermolecular C-HÁ Á ÁO and C-HÁ Á ÁBr hydrogen bonds.
The naphthofuran unit is essentially planar, with a mean deviation of 0.045 (3)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 42.2 (1)°. The molecular packing ( Fig. 2) is stabilized by two intermolecular C-H···π interactions; the first between an H atom of the 2-phenyl ring and the central benzene ring of the naphthofuran fragment (C14-H14···Cg1 i ), the second between the methyl H atom of the methylsulfinyl substituent and the phenyl ring (C19-H19B···Cg2 ii ), respectively (Table 1 and Fig. 2; Cg1 and Cg2 are the centroids of the C2/C3/C8/C9/C10/C11 benzene and C13-C18 benzene rings).

Experimental
The 77% 3-chloroperoxybenzoic acid (157 mg, 0.7 mmol) was added in small portions to a stirred solution of 7-bromo-1methylsulfanyl-2-phenylnaphtho[2,1-b]furan (258 mg, 0.7 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, 1 : 2 v/v) to afford the title compound as a colorless solid [yield 78%, m.p. 503-504 K; R f = 0.72 (hexane-ethyl acetate, 1 : 2 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in dichloromethane at room temperature.

Refinement
All H atoms were geometrically positioned and refined using a riding model, with C-H = 0.93 Å for the aryl and 0.96 Å for the methyl H atoms. U iso (H) = 1.2U eq (C) for the aryl H atoms and 1.5U eq (C) for methyl 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 30% probability level. H atoms are presented as a small spheres of arbitrary radius.

Special details
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The 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 > 2σ(F 2 ) is used only for calculating Rfactors(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 1.04085 (7)