6-Chloro-4-(4-methylphenoxymethyl)-2H-chromen-2-one

In the title compound, C17H13ClO3, the coumarin and phenoxy moieties are essentially co-planar, making a dihedral angle of 1.99 (7)°. The phenoxy moiety is oriented antiperiplanar with respect to the coumarin ring as indicated by the C—C—O—C angle of −179.97 (16)°. In the crystal, the sheet-like packing is stabilized by intermolecular C—H⋯O and C—H⋯Cl hydrogen bonds.

In the title compound, C 17 H 13 ClO 3 , the coumarin and phenoxy moieties are essentially co-planar, making a dihedral angle of 1.99 (7) . The phenoxy moiety is oriented antiperiplanar with respect to the coumarin ring as indicated by the C-C-O-C angle of À179.97 (16) . In the crystal, the sheet-like packing is stabilized by intermolecular C-HÁ Á ÁO and C-HÁ Á ÁCl hydrogen bonds.

Comment
The first report on X-ray diffraction studies on 4-aryloxymethylcoumarins has revealed that in solid state the molecules exist as head-tail dimers as observed in the case of 7-methyl-4-tolyloxymethylcoumarin (Vasudevan et al., 1990). In the light of these observations a chloro substituted 4-aryloxymethylcoumarin has been subjected to X-ray diffraction studies. A significant bond deviation is observed at C5-C7 (1.449 (2) Å) due to the bridging of α-pyrone and benzene ring at C5 and the substituent present at C7. This is also reflected at C8-C9 and C7-C10 due to the presence of O2 at C9 and a phenoxy group at C10, respectively. Significant bond angle deviations are observed at C6-C5-C4 (117.91 (17)
Then, the resulting reaction mixture was poured to crushed ice. The separated solid was filtered and washed with 1:1 HCl (30 ml) and with water. Then product 6-chloro-4-[(4-methyl)phenoxymethyl]coumarin was recrystallized from ethyl acetate.

Refinement
Hydrogen atoms were positioned geometrically with C-H = 0.93-0.97 A° and included in the refinment in a riding-model approximation with U iso (H) = 1.2 U eq (C) or 1.5 U eq (C) for methyl C atoms. Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering.

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.