4-Nitro­phenyl 1-naphthoate

Uzma Bibi; Humaira M Siddiqi; Zareen Akhter; Michael Bolte

doi:10.1107/S1600536810011736

. 2010 Apr 2;66(Pt 5):o1023. doi: 10.1107/S1600536810011736

4-Nitrophenyl 1-naphthoate

Uzma Bibi ^a, Humaira M Siddiqi ^a,^*, Zareen Akhter ^a, Michael Bolte ^b

PMCID: PMC2979124 PMID: 21579087

Abstract

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.

Related literature

For biological and synthetic background, see: Bezerra-Netto et al. (2006 ▶); Bibi et al. (2009 ▶); Kumarraja & Pitchumani (2004 ▶); Selvakumar et al. (2002 ▶); Tafesh & Weiguny (1996 ▶).

Experimental

Crystal data

C₁₇H₁₁NO₄
M _r = 293.27
Monoclinic,
a = 7.2049 (6) Å
b = 12.8175 (8) Å
c = 14.7838 (14) Å
β = 99.006 (7)°
V = 1348.44 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 173 K
0.25 × 0.21 × 0.21 mm

Data collection

Stoe IPDS-II two-circle diffractometer
10239 measured reflections
2508 independent reflections
1928 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.088
S = 0.96
2508 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810011736/tk2650sup1.cif

e-66-o1023-sup1.cif^{(18.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011736/tk2650Isup2.hkl

e-66-o1023-Isup2.hkl^{(123.2KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O2ⁱ	0.95	2.45	3.3728 (18)	164

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors are grateful to the University Research Fund 2008–09, Department of Chemistry, Quaid-I-Azam University, for support. The Institut für Anorganische Chemie, J.-W.-Goethe-Universität Frankfurt, is acknowledged for providing laboratory and analytical facilities.

supplementary crystallographic information

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% NaHCO₃ solution to remove unreacted acid and the extract was dried over anhydrous Na₂SO₄, 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)