Crystal structure of 3-(4-bromophenylsulfonyl)-2,5,6-trimethyl-1-benzofuran

In 3-(4-bromophenylsulfonyl)-2,5,6-trimethyl-1-benzofuran, molecules are linked into a chain along the b-axis direction by C—H⋯π hydrogen bonds and C—Br⋯π interactions.


Structural commentary
In the title molecule ( Fig. 1), the benzofuran unit (O1/C1-C8) is essentially planar, with a mean deviation of 0.015 (2) Å from the mean plane defined by the nine constituent atoms. The 4bromophenyl ring (C12-C17) is inclined to the benzofuran ring by 89.29 (6) . The title compound crystallized in the noncentrosymmetric space group Pc in spite of having no asymmetric C atoms.

Supramolecular features
In the crystal, molecules are linked into a chain along the baxis direction by C-HÁ Á Á hydrogen bonds ( Fig. 2
Cg1 is the centroid of the C2-C7 benzene ring.

Figure 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 shown as small spheres of arbitrary radius.

Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2. All H atoms were positioned geometrically and refined using a riding model, with C-H = 0.95 for aryl and 0.98 Å for methyl H atoms, and with U iso (H) = 1.2U eq (C) for aryl and 1.5U eq (C) for methyl H atoms. program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

3-(4-Bromophenylsulfonyl)-2,5,6-trimethyl-1-benzofuran
Crystal data   3H)). 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.