2-(4-Bromophenyl)-5,6-methylenedioxy-3-phenylsulfinyl-1-benzofuran benzene solvate

In the title compound, C21H13BrO4S·C6H6, the O atom and the phenyl group of the phenylsulfinyl substituent are located on opposite sides of the mean plane of the 5,6-methylenedioxybenzofuran fragment; the phenyl ring is almost perpendicular to this plane [83.66 (6)°]. The 4-bromophenyl ring is rotated slightly out of the 5,6-methylenedioxybenzofuran plane, making a dihedral angle of 2.9 (1)°. The crystal structure is stabilized by intermolecular C—H⋯O hydrogen bonds and intermolecular C—H⋯π interactions. The crystal structure also exhibits π–π interactions between the benzene ring and the 4-bromophenyl ring of an adjacent molecule [centroid–centroid distance = 3.586 (3) Å].

After being stirred at room temperature for 3 h, 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 colourless solid [yield 73%, m.p. 462-463 K; R f = 0.71 (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 benzene at room temperature.

Refinement
All H atoms were positioned geometrically and refined using a riding model, with C-H = 0.93 Å for the aryl and 0.97 Å for the methylene H atoms. U iso (H) = 1.2U eq (C) for the aryl and the methylene H atoms. The distances of C-C in the solvated benzene ring were restrained to 1.39 (1) Å using command DFIX.
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 cycles 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.