Methyl 2-(4-chlorobenzamido)benzoate

In the title compound, C15H12ClNO3, the central C—C(O)—N—C amide unit makes dihedral angles of 6.60 (2) and 3.42 (2)°, respectively, with the 4-chlorobenzene and anilino rings. The dihedral angle between the two benzene rings is 3.32 (3)°. Intramolecular N—H⋯O and C—H⋯O hydrogen bonds form S(6) rings and contribute to the planarity of this portion of the molecule. In the crystal, intermolecular C—H⋯O hydrogen bonds are observed, which link the molecules into [010] C(7) chains.

In the title compound, C 15 H 12 ClNO 3 , the central C-C(O)-N-C amide unit makes dihedral angles of 6.60 (2) and 3.42 (2) , respectively, with the 4-chlorobenzene and anilino rings. The dihedral angle between the two benzene rings is 3.32 (3) . Intramolecular N-HÁ Á ÁO and C-HÁ Á ÁO hydrogen bonds form S(6) rings and contribute to the planarity of this portion of the molecule. In the crystal, intermolecular C-HÁ Á ÁO hydrogen bonds are observed, which link the molecules into [010] C(7) chains.

Experimental
A solution of methyl anthranilate (390 µl, 3 mmol) in dichloromethane (15 ml) was treated dropwise with 4-chlorobenzoyl chloride (383 µl, 3 mmol) in the presence of triethanolamine (5 ml) as a catalyst. The resulting mixture was stirred for 1 h. On completion of reaction, precipitates formed, were filtered, dried and crystallized from methanol to yield colorless blocks of the title compound.

Refinement
All H-atoms were refined using riding model for hydrogen bonds with d(C-H) = 0.93Å (U iso =1.2U eq of the parent atom) for aromatic carbon atoms, d(N-H) = 0.86Å (U iso =1.2U eq of the parent atom) for imine nitrogen atom and d(C-H) = 0.96Å (U iso =1.5U eq of the parent atom) for methyl carbon atom. Fig. 1

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 > σ(F 2 ) is used only for calculating Rfactors(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.