2-Bromo-2-methyl-1-[4-(methylsulfanyl)phenyl]propan-1-one

In the title compound, C11H13BrOS, the thioether unit and the phenyl ring adopt an essentially planar conformation, with a maximum deviation of 0.063 Å. In the crystal, molecules are linked by C—H⋯O hydrogen bonds, extending in zigzag chains along the b axis. A weak intramolecular C—H⋯Br hydrogen bond is also observed, which forms an S(6) ring motif.

In the title compound, C 11 H 13 BrOS, the thioether unit and the phenyl ring adopt an essentially planar conformation, with a maximum deviation of 0.063 Å . In the crystal, molecules are linked by C-HÁ Á ÁO hydrogen bonds, extending in zigzag chains along the b axis. A weak intramolecular C-HÁ Á ÁBr hydrogen bond is also observed, which forms an S(6) ring motif.
The thioether moiety and phenyl ring adopt an essentially planar conformation with a maximum deviation of 0.063 Å ( Fig. 1). In the crystal, molecules are linked by C-H···O hydrogen bonds, extending as zigzag chains along the b axis ( Fig. 2). In addition, a weak intramolecular C-H···Br hydrogen bond is also observed, forming an S(6) ring motif. This H-bond geometry is listed in Table 1.

Experimental
To a mixture of dichloroethane (50 ml) and aluminium cloride (17.4 g, 130 mmol) was added isobutyryl chloride (13.8 g, 130 mmol) at 298 K. Thioanisole (10.8 g, 100 mmol) was added dropwise to the mixture. After completion, it was poured into diluted hydrochloric acid and the organic layer was extracted.
Then, bromine (10.4 g, 65 mmol) was added at 303 K. After completion, water was added, and the organic layer was washed by 5% sodium bicarbonate solution and concentrated to yield the title compound with a yield of 77.3%. The crude product was recrystallized by slow evaporation from ethanol to give the single crystals used for data collection.

Refinement
C-bound H atoms were positioned geometrically with C-H 0.95 Å and 0.98 Å for Csp 2 and methyl C, respectively, and were treated as riding on their parent atoms, with U iso (H)=1.2 U eq (C).

Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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.