2-Chloro-8-methyl-3-[(pyrimidin-4-yloxy)methyl]quinoline

In the title compound, C15H12ClN3O, the quinoline ring system is essentially planar, with a maximum deviation of 0.017 (1) Å. The crystal packing is stabilized by π–π stacking interactions between the quinoline rings of adjacent molecule, with a centroid–centroid distance of 3.5913 (8) Å. A weak C—H⋯π contact is also observed between molecules.

In the title compound, C 15 H 12 ClN 3 O, the quinoline ring system is essentially planar, with a maximum deviation of 0.017 (1) Å . The crystal packing is stabilized bystacking interactions between the quinoline rings of adjacent molecule, with a centroid-centroid distance of 3.5913 (8) Å . A weak C-HÁ Á Á contact is also observed between molecules.
In the title molecule, there is a weak intramolecular C-H···O interaction, generating an S(5) graph-set motif (Bernstein et al., 1995) (Table 1). The crystal packing is stabilized by π-π stacking interactions between the benzene rings of the quinoline ring system of the molecules related by the symmetry operator (1-x, 1-y, -z) [centroid-to-centroid distance = 3.5913 (8) Å].
In addition, a weak C-H···π contact is also observed between molecules (Table 1). The packing diagram viewing down the b-axis is shown in Fig. 2.

Experimental
To a mixed well solution of 4(3H)-pyrimidone (96 mg, 1 mmol, in 5 ml DMSO), NaH (25 mg, 1 mmol) and 2-chloro-3-(chloromethyl)-8-methylquinoline (225 mg, 1 mmol) were added and the resulting mixture was refluxed for 1 h. Completion of the reaction was monitored by TLC. After the completion of the reaction, cooled and removed the excess of solvent under reduced pressure. Crushed ice was mixed with the residue. White solid was formed, filtered and dried, purified by column chromatography using hexane and ethylacetate as the eluant. The low polar compound was subjected into crystallization by solvent evaporation from a solution of the compound in chloroform.

Refinement
All H atoms were placed in geometrically idealised positions and constrained to ride on their parent atoms (C-H = 0.93, 0.96 and 0.97 Å) and U iso (H) values were taken to be equal to 1.2 U eq (C) for aromatic and methylene H atoms and 1.5U eq (C) for methyl H atoms.
supplementary materials sup-2 Figures Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

Special details
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and tor-

sion angles
Refinement. Refinement on F 2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted Rfactors wR and all goodnesses 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 observed criterion of F 2 > σ(F 2 ) is used only for calculating -R-factor-obs 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.