7-Bromo-1-(4-fluorophenylsulfonyl)-2-methylnaphtho[2,1-b]furan

In the title compound, C19H12BrFO3S, the 4-fluorophenyl ring makes a dihedral angle of 80.32 (5)° with the mean plane of the naphthofuran fragment. In the crystal, molecules are linked by weak intermolecular C—H⋯O and C—H⋯π interactions. The crystal structure also exhibits aromatic π–π interactions between the central benzene rings of neighbouring molecules [centroid–centroid distance = 3.564 (3) Å].

In the title compound, C 19 H 12 BrFO 3 S, the 4-fluorophenyl ring makes a dihedral angle of 80.32 (5) with the mean plane of the naphthofuran fragment. In the crystal, molecules are linked by weak intermolecular C-HÁ Á ÁO and C-HÁ Á Á interactions. The crystal structure also exhibits aromaticinteractions between the central benzene rings of neighbouring molecules [centroid-centroid distance = 3.564 (3) Å ].
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2255). properties such as antibacterial, antitumor and anthelmintic activities (Einhorn et al., 1984, Hranjec et al., 2003, Mahadevan & Vaidya, 2003. As a part of our ongoing studies of the substituent effect on the solid state structures of 1-arylsulfonyl-7bromo-2-methylnaphtho[2,1-b]furan analogues (Choi et al., 2008a,b), we report herein on the crystal structure of the title compound.
In the title molecule ( Fig. 1), the naphthofuran moiety is essentially planar, with a mean deviation of 0.011 (2)Å from the least-squares plane defined by the thirteen constituent atoms. The dihedral angle formed by the mean plane of the naphthofuran system and the 4-fluorophenyl ring is 80.32 (5)°. The crystal packing (Fig. 2) is stabilized by weak intermolecular C-H···O hydrogen bonds; the first one between a benzene H atom and the oxygen of the O═S═O unit (Table 1; C5-H5···O2 i ), and the second one between the 4-fluorophenyl H atom and the oxygen of the O═S═O unit (Table 1; C18-H18···O2 ii ), and the third one between the 4-fluorophenyl H and the oxygen of the O═S═O unit (Table 1; C19-H19···O3 i ). The molecular packing (Fig. 3) is further stabilized by an intermolecular C-H···π interaction between a benzene H atom and the 4-fluorophenyl ring (Table 1; C10-H10···Cg1 iii , Cg1 is the centroid of the C14-C19 4-fluorophenyl ring). In addition, the crystal packing ( Fig. 3) exhibits an aromatic π-π interaction between the central benzene rings of neighbouring molecules.
Experimental 3-Chloroperoxybenzoic acid (77%) (404 mg, 1.8 mmol) was added in small portions to a stirred solution of 7-bromo-1-(4fluorophenylsulfanyl)-2-methylnaphtho[2,1-b]furan (348 mg, 0.9 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 10 h, 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, 4:1 v/v) to afford the title compound as a colourless solid [yield 73%, m.p. 485-486 K; R f = 0.52 (hexane-ethyl acetate, 4:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in acetone at room temperature.

Refinement
All H atoms were positioned geometrically and refined using a riding model, with C-H = 0.95Å for aryl and 0.98Å for methyl H atoms. U iso (H) = 1.2U eq (C) for aryl 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 50% probability level. H atoms are presented as a small spheres of arbitrary radius.