4-Nitrophenyl 2-methylbenzoate

The title compound, C14H11NO4, crystallizes with two molecules in the asymmetric unit. The major conformational difference between these two molecules is the dihedral angle between the aromatic rings, namely 36.99 (5) and 55.04 (5)°. The nitro groups are coplanar with the phenyl rings to which they are attached, the O—N—C—C torsion angles being −1.9 (3) and 1.0 (3)° in the two molecules.

The title compound, C 14 H 11 NO 4 , crystallizes with two molecules in the asymmetric unit. The major conformational difference between these two molecules is the dihedral angle between the aromatic rings, namely 36.99 (5) and 55.04 (5) . The nitro groups are coplanar with the phenyl rings to which they are attached, the O-N-C-C torsion angles being À1.9 (3) and 1.0 (3) in the two molecules.
ence between the two molecules is the dihedral angle between the aromatic rings, namely 36.99 (5)° and 55.04 (5)°.
Experimental 2-Toluic acid (1.5 g, 1 mol) in a 100 ml two neck round bottom flask was gradually warmed on a water bath to 323 K. Dry thionyl chloride was added in excess slowly with stirring along with 2-3 drops of DMF as catalyst. The mixture was refluxed for about 50-60 minutes at 343 K. The excess of thionyl chloride was removed by repeated evaporation at reduced pressure.
In a separate flask, 4-nitrophenol (1.5 g, 0.0065 mol) was dissolved in dry dichloromethane to which triethyl amine was added at room temperature to get transparent solution. The acid chloride was added into it drop wise with constant stirring at room temperature for 30 minutes under anhydrous condition and then poured into 20 ml of cold water. Excess of triethyl amine was removed by adding cold dilute HCl solution. The reaction was monitored by TLC using ethyl acetate: n-hexane (1:2). After the completion of reaction the oily product was allowed to settle down and the supernatant liquid was decanted.
The product was stirred well with distilled water and extracted with ethyl acetate (3 x 40 ml), washed with 5% NaHCO 3 solution and dried over anhydrous Na 2 SO 4 . After filtration the solution was concentrated to obtain the title compound which was recrystallized from n-hexane (Yield: 37 %; m.p. 336-344 K).

Refinement
H atoms were positioned geometrically and refined using a riding model with with C-H distances 0.95 and 0.98 Å for aromatic and methyl H-atoms, respectively, and displacement parameters, U iso = 1.2 and 1.5 times U eq of aromatic and methyl C-atoms, respectively. The methyl groups were allowed to rotate but not to tip. Due to the absence of anomalous scatterers, the absolute structure could not be determined which was set arbitrarily and Friedel pairs (1929) were merged.  Fig. 1. Molecular structure of the independent molecule of the title compound with displacement parameters drawn at the 50% probability level. Fig. 2. Molecular structure of the other independent molecule of the title compound with displacement parameters drawn at the 50% probability level.  (7) 0.0458 (9) −0.0024 (6) −0.0051 (7) 0.0052 (7) O2 0.0326 (9) 0.0235 (7) 0.0490 (10) −0.0024 (7) −0.0090 (7) −0.0003 (7)