4-Methylphenyl 4-bromobenzoate

In the title compound, C14H11BrO2, an ester formed from the reaction of 4-methylphenol with 4-bromobenzoylchloride, the dihedral angle between the benzene rings is 54.43 (7)°, indicating a twist in the molecule. In the crystal, weak C—H⋯O interactions link the molecules into supramolecular layers in the bc plane, and these are connected along the a axis by Br⋯Br contacts [3.6328 (5) Å].

In the title compound, C 14 H 11 BrO 2 , an ester formed from the reaction of 4-methylphenol with 4-bromobenzoylchloride, the dihedral angle between the benzene rings is 54.43 (7) , indicating a twist in the molecule. In the crystal, weak C-HÁ Á ÁO interactions link the molecules into supramolecular layers in the bc plane, and these are connected along the a axis by BrÁ Á ÁBr contacts [3.6328 (5) Å ].

Structure Reports Online
The crystal packing is stabilized by C-H···O interactions (Nardelli, 1995); Table 1. These weak interactions link the molecules into supramolecular layers in the bc plane. The layers are connected by Br···Br interactions (Ritter, 2009).

Experimental
A solution containing equimolar quantities (3.4 mmol) of 4-bromobenzoyl chloride and 4-methylphenol in acetonitrile (60 ml) was gradually heated to reflux for 2 h and then allowed to cool. At room temperature, triethylamine was added to get a solid which was poured in cold water. The solid was recrystallized from its dichlorometane solution to yield colourless crystals; M.pt. 385 (1) K.

Refinement
The H-atoms were positioned geometrically [C-H = 0.93-0.96 Å, and with U iso (H) =1.2-1.5U eq (C). Fig. 1. Molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres 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.