Ethyl 4-nitro­phenyl­acetate

Ji Li; Jun Liu; Hui-Qing Peng

doi:10.1107/S1600536807066184

. 2008 Jan 16;64(Pt 2):o443. doi: 10.1107/S1600536807066184

Ethyl 4-nitrophenylacetate

Ji Li ^a, Jun Liu ^a, Hui-Qing Peng ^a,^*

PMCID: PMC2960243 PMID: 21201470

Abstract

In the asymmetric unit of the title compound, C₁₀H₁₁NO₄, there are two crystallographically independent molecules, which are connected via a C—H⋯O hydrogen bond. The crystal structure is stabilized by this hydrogen bond together with an N—O⋯π contact [O⋯Cg 3.297 (5) Å; Cg is the centroid of one of the benzene rings].

Related literature

For related literature, see: Brown et al. (2006 ▶); Shokat et al. (1991 ▶); Sagamihara (1988 ▶).

Experimental

Crystal data

C₁₀H₁₁NO₄
M _r = 209.20
Orthorhombic,
a = 15.9132 (13) Å
b = 5.2298 (4) Å
c = 24.878 (2) Å
V = 2070.4 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 292 (2) K
0.40 × 0.04 × 0.02 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T _min = 0.959, T _max = 0.998
13522 measured reflections
2318 independent reflections
1422 reflections with I > 2σ(I)
R _int = 0.065

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.122
S = 1.01
2318 reflections
273 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 2001 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807066184/is2259sup1.cif

e-64-0o443-sup1.cif^{(20.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807066184/is2259Isup2.hkl

e-64-0o443-Isup2.hkl^{(113.9KB, 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
C6—H6⋯O5	0.93	2.47	3.186 (6)	134

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Acknowledgments

The authors acknowledge the teachers of the College of Chemistry of Central China Normal University.

supplementary crystallographic information

Comment

Ethyl 4-nitrophenylacetate, (I), has been widely used as an intermediator of the anti-rheumatoid drugs (Kevan et al., 1991; Sagamihara, 1988). The similar compound, cyclodecyl 4-nitrophenylacetate, has been reported by Brown et al. (2006). Here we present the molecular structure of (I), as shown in Fig. 1. In the asymmetric unit of (I), there is a dimer via a C—H···O interaction (Table 1). The angles involving the acetate groups in the dimer are 126.7 (4), 124.0 (4), 126.1 (4) and 123.1 (4)°, and the average distances of C=O and C—O are 1.202 (5) and 2.792 (5) Å, respectively. The C—N bond lengths on the benzene ring range from 1.202 (5) to 1.219 (4) Å. The benzene ring planes of the two independent molecules are nearly directional parallel with the dihedral angle of 19.2 (2)°, but no significant π-π interaction. The molecular packing diagram of (I) is stabilized by N1—O2···π contact [O2···Cgⁱ 3.297 (5) Å, N1—O2···Cgⁱ 156.3 (3)°; Cg is the centroid of the benzene C11—C16 ring; symmetry code: (i) 1/2 + x, 1 - y, z] together with hydrogen bond, as shown in Fig. 2.

Experimental

Ethyl 4-nitrophenylacetate was obtained from the Jiachen Chemical Company Inc, ShangHai. The crystals were grown by vapour diffusion of 95% ethanol.