Methyl 4-(3-chloropropoxy)-3-methoxybenzoate

In the title compound, C12H15ClO4, the molecules are linked by C—H⋯O interactions.

In the title compound, C 12 H 15 ClO 4 , the molecules are linked by C-HÁ Á ÁO interactions.
In the molecule of the title compound (Fig 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges.
Ring A (C4-C9) is, of course, planar. The intramolecular C-H···O hydrogen bond (Table 1) results in the formation of a five-membered ring B (O1/C1-C3/H1A), having envelope conformation with C2 atom displaced by -0.668 (3) Å from the plane of the other ring atoms.
In the crystal structure, intermolecular C-H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure.

S2. Experimental
For the preparation of the title compound, methyl 3-methoxy-4-hydroxybenzoate (55 mmol), 1-bromo-3-chloropropane (165 mmol) and potassium carbonate (275 mmol) were mixed with DMF (60 ml), and then the mixture was heated to reflux for 2 h. Reaction progress was monitored by TLC. After cooling and filtration, the title compound was obtained (yield; 93.7%, m.p. 384 K). Crystals suitable for X-ray analysis were obtained by slow evaporation of an ethyl acetate solution.

S3. Refinement
H atoms were positioned geometrically, with C-H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H, respectively, and constrained to ride on their parent atoms, with U iso (H) = xU eq (C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.  The molecular structure of the title molecule, with the atom-numbering scheme. Hydrogen bond is shown as dashed line. where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max < 0.001 Δρ max = 0.35 e Å −3 Δρ min = −0.29 e Å −3 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq