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

Abstract

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.