Ethyl 5-(ethoxy­carbon­yl)-3-(4-methoxy­phen­yl)-1H-pyrazole-1-acetate

Wen-Liang Dong; Yan-Qing Ge; Bao-Xiang Zhao

doi:10.1107/S1600536807057297

. 2007 Dec 6;64(Pt 1):o64. doi: 10.1107/S1600536807057297

Ethyl 5-(ethoxycarbonyl)-3-(4-methoxyphenyl)-1H-pyrazole-1-acetate

Wen-Liang Dong ^a,^b, Yan-Qing Ge ^a, Bao-Xiang Zhao ^a,^*

PMCID: PMC2915022 PMID: 21200941

Abstract

In the title compound, C₁₇H₂₀N₂O₅, all bond lengths and angles show normal values. The dihedral angle between the pyrazole ring and the benzene ring is 6.98 (11)°. The molecules are linked by intermolecular C—H⋯π interactions.

Related literature

For related literature, see: Allen et al. (1987 ▶); Brough et al. (2005 ▶); Cheng et al. (2006 ▶); Dong et al. (2007 ▶); Sehon et al. (2006 ▶); Wei et al. (2006 ▶); Xia et al. (2007 ▶).

Experimental

Crystal data

C₁₇H₂₀N₂O₅
M _r = 332.35
Triclinic,
a = 7.4267 (1) Å
b = 11.0511 (2) Å
c = 11.7139 (2) Å
α = 106.721 (1)°
β = 97.898 (1)°
γ = 106.796 (1)°
V = 855.59 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 (2) K
0.45 × 0.39 × 0.28 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.846, T _max = 0.974
13041 measured reflections
3806 independent reflections
2376 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.166
S = 1.06
3806 reflections
221 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807057297/fj2063sup1.cif

e-64-00o64-sup1.cif^{(19KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807057297/fj2063Isup2.hkl

e-64-00o64-Isup2.hkl^{(186.6KB, hkl)}

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

Table 1. X—H⋯π-ring interactions calculated by PLATON (Spek, 2003 ▶). Cg ⁱ is a centroid of the pyrazole ring N1/N2/C8/C9/C10.

X—H⋯Cg	X—H	H⋯Cg	X⋯Cg	X—H⋯Cg
C1—H1A⋯Cg1ⁱ	0.96	2.89	3.731 (3)	147

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Symmetry code: (i) Inline graphic . Cg1 is the centroid of the the pyrazole ring.

Acknowledgments

This study was supported by the Natural Science Foundation of Shandong Province (grant No. Y2005B12).

supplementary crystallographic information

Comment

The pyrazole unit is one of the core structures in a number of natural products. Many pyrazole derivatives are known to exhibit a wide range of biological properties such as antagonists (Sehon et al., 2006), anti-inflammatory (Cheng et al., 2006), inhibitors of the Hsp90 (Brough et al., 2005), antitumor (Wei et al., 2006; Xia et al., 2007). In our previous paper, we reported the crystal structure of ethyl 3-(4-chlorophenyl)-5-(ethoxycarbonyl)-1H-pyrazole-1-acetate (Dong et al., 2007). We report here the crystal structure of the title compound, (I).

In compound (I) (Fig. 1), all bond lengths and angles are normal (Allen et al., 1987). The dihedral angles between the rings of the pyrazole and the benzene ring is 6.98 (11)^o. The two ethyl carboxylate groups are inclined to the attached pyrazole ring by 2.16 (9)^oand 75.95 (11)^o, respectively. The molecules are linked into a network parallel by C—H···π interactions (Table 1) involving the pyrazole ring (centroid Cg1). We report here the crystal structure of the title compound, (I).

Experimental

A mixture of ethyl 3-(4-methoxyphenyl)-1H-pyrazole-5-carboxylate (0.01 mol), ethyl chloroacetate (0.015 mol) and potassium carbonate (0.02 mol) in acetonitrile (50 ml) was heated to reflux for 15 h. The solvent was removed under reduced pressure, and the residue was dissolved in the mixture of water (50 ml) and ethyl acetate (50 ml). After separated, the water phase was extracted with ethyl acetate (25 ml), and then the organic phase was combined, dried over anhydrous magnesium sulfate and filtered. The solvent was removed under reduced pressure. The solid product was recrystallized from ethyl acetate (yield 55%). Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of a solution of the solid in ethyl acetate at room temperature for 6 d.