4-Nitrophenyl 1-naphthoate

In the title compound, C17H11NO4, the dihedral angle between the two benzene rings is 8.66 (3)°. The nitro group is twisted by 4.51 (9)° out of the plane of the aromatic ring to which it is attached. The presence of intermolecular C—H⋯O contacts in the crystal structure leads to the formation of chains along the c axis.

In the title compound, C 17 H 11 NO 4 , the dihedral angle between the two benzene rings is 8.66 (3) . The nitro group is twisted by 4.51 (9) out of the plane of the aromatic ring to which it is attached. The presence of intermolecular C-HÁ Á ÁO contacts in the crystal structure leads to the formation of chains along the c axis.   Table 1 Hydrogen-bond geometry (Å , ).

Comment
The ability of non-steroidal anti-inflammatory drugs (NSAID's) to modulate the pain, inflammation and fever make them attractive drugs (Bezerra-Netto et al., 2006). Aromatic esters containing a nitro-substituted phenyl ring form a medicinally important class of NSAID's. These can be used as starting materials for the preparation of several analgesic and anti-inflammatory drugs, and some of them are potential intermediates in natural product syntheses (Selvakumar et al., 2002). Nitro compounds can be reduced to give amines which are important synthons for preparing a large number of technologically important materials (Kumarraja et al., 2004;Tafesh et al., 1996). In continuation of studies on related compounds (Bibi et al., 2009), the title compound is reported herein.
A perspective view of the title compound is shown in Fig. 1. The dihedral angle formed between the two aromatic ring systems is 8.66 (3)°. The nitro group is twisted by only 4.51 (9)° out of the plane of the aromatic ring to which it is attached.
The crystal structure is stabilized by C-H···O contacts, Table 1.
Experimental 1-Naphthoic acid (1.5 g, 1 mol) was taken in a 100 ml two neck round bottom flask and warmed on a water bath to 323 K. An excess of dry thionyl chloride was added slowly with stirring. Drops (2-3) of DMF were added and the mixture was refluxed for about 50-60 minutes at 343 K. After the completion of the reaction, excess thionyl chloride was removed by repeated evaporations at reduced pressure. 4-Nitrophenol (1.5 g, 0.0065 mol) was dissolved in dry dichloromethane containing triethyl amine at room temperature. The acid chloride was added drop-wise with constant stirring at room temperature for half an hour. The reaction mixture was heated gently for 30 minutes under anhydrous condition and then the solution was poured with constant stirring into cold water (20 ml ). Excess triethyl amine was destroyed by adding the cold dilute HCl solution.
The reaction was monitored by TLC using ethyl acetate:n-hexane (1:1). 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). Washing was done with 5% NaHCO 3 solution to remove unreacted acid and the extract was dried over anhydrous Na 2 SO 4 , filtered, and concentrated on a rotary evaporator. The ester soon solidified and was filtered. The title compound was recrystallized from n-hexane (Yield 36.5 %, m.pt. 385-393 K) Refinement H atoms were found in a difference map, but they were refined with fixed individual isotropic displacement parameters [U iso (H) = 1.2U eq (C)] using a riding model, with C-H = 0.95 Å.

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.