(Z)-Methyl 2-[(4-bromo-2-formylphenoxy)methyl]-3-o-tolylacrylate

In the title compound, C19H17BrO4, the dihedral angle between the two benzene rings is 82.1 (1)°. The molecular structure is stabilized by an intramolecular C—H⋯O hydrogen bond which generates an S(7) ring motif. The crystal packing is stabilized by intermolecular C—H⋯O hydrogen bonds and C—H⋯π interactions. Intermolecular C—H⋯O interactions are involved in the formation of centrosymmetric R 2 2(16) dimers, which are connected into supramolecular tapes running along the [100] direction.


Experimental
A solution of salicylaldehyde (3.7 mmol, 0.74g) and potassium carbonate (5.59 mmol, 0.77g) in acetonitrile as solvent (10ml) was stirred for 15 minutes at room temperature. To this solution, (Z-methyl 2-(bromomethyl)-3-o-tolylacrylate (3.7 mmol, 1g) was added dropwise. After the completion of the reaction as indicated by TLC, acetonitrile was evaporated. Ethylacetate (15ml) and water (15ml) were added to the crude mass and extracted. The organic layer was dried over anhydrous sodium sulfate. Removal of the solvent led to the crude product which was purified through pad of silica gel (100-200 mesh) using ethylacetate and hexanes (1:9) as solvents. The pure title compound was obtained as a colorless solid (1.32g, 91%). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a ethylacetate solution at room temperature.

Refinement
All H atoms were positioned geometrically, with C-H = 0.93 -0.96 Å and constrained to ride on their parent atom, with U iso (H)=1.5U eq for methyl and hydroxyl H atoms and 1.2U eq (C) for other 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 30% 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.