2,4-Dichlorobenzyl 2-methoxybenzoate

In the title compound, C15H12Cl2O3, the aromatic rings make a dihedral angle of 10.78 (4)°. In the molecule, there is a short C—H⋯O contact. In the crystal, C—H⋯O contacts connect the molecules into C(7)C(8) chains along the b axis. The shortest intercentroid distance between two benzoic acid aromatic systems is 3.7416 (8) Å.

In the title compound, C 15 H 12 Cl 2 O 3 , the aromatic rings make a dihedral angle of 10.78 (4) . In the molecule, there is a short C-HÁ Á ÁO contact. In the crystal, C-HÁ Á ÁO contacts connect the molecules into C(7)C(8) chains along the b axis. The shortest intercentroid distance between two benzoic acid aromatic systems is 3.7416 (8) Å .

Related literature
For pharmacological properties of phenyl benzoates, see: Oxford et al. (2005); Ostergaard (1994). For graph-set analysis of hydrogen bonds, see: Bernstein et al. (1995); Etter et al.  Table 1 Hydrogen-bond geometry (Å , ). For decades, phenyl benzoate derivatives have found ample application in the identification of organic acids. 2,4-Dichlorobenzyl derivatives show pharmacological activity such as acting as mild antiseptics and showing the ability to kill bacteria and viruses associated with mouth and throat infections (Oxford et al., 2005;Ostergaard 1994). In continuation of our research focused on the crystal structures of medical compounds, the title compound was synthesized.
The molecule is essentially flat. The atom deviating most from the least-squares plane defined by all non-hydrogen atoms is the chlorine atom in para position to the benzyloxy moiety with a deviation of 0.237 (1) Å. The least-squares planes defined by the respective carbon atoms of the aromatic systems intersect at an angle of 10.78 (4) ° ( Fig. 1).
In the crystal, intermolecular C-H···O contacts whose range falls by more than 0.1 Å below the sum of van-der-Waals radii are observed. These are established between one of the hydrogen atoms of the methoxy group as well as one of the two hydrogen atoms in ortho position to the chlorine atom in para position to the benzyloxy group and chelate the ketonic oxygen atom of the ester moiety. In total, the molecules are connected to chains along the crystallographic b axis.
In terms of graph-set analysis (Etter et al., 1990;Bernstein et al., 1995), the descriptor for these contacts is C 1 1 (7)C 1 1 (8) on the unary level. Information about metrical parameters as well as the symmetry of those contacts has been summarized in Table 1. The shortest intercentroid distance between two aromatic systems was measured at 3.7416 (8) Å and is apparent between the benzoic acid moiety and its symmetry-generated equivalent (Fig. 2).
The packing of the title compound in the crystal structure is shown in Figure 3.

Refinement
Carbon-bound H atoms were placed in calculated positions (C-H 0.95 Å for aromatic carbon atoms and C-H 0.99 Å for methylene groups) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U eq (C).
The H atoms of the methyl groups were allowed to rotate with a fixed angle around the C-C bond to best fit the experimental electron density with U(H) set to 1.5U eq (C).