organic compounds
Ethyl 5-(ethoxycarbonyl)-3-(4-methoxyphenyl)-1H-pyrazole-1-acetate
aSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China, and bShandong University of Traditional Chinese Medicine, Jinan 250355, People's Republic of China
*Correspondence e-mail: bxzhao@hotmail.com
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
|
Refinement
|
Data collection: APEX2 (Bruker, 2005); cell 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).
Supporting information
https://doi.org/10.1107/S1600536807057297/fj2063sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807057297/fj2063Isup2.hkl
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.
All H atoms were placed in geometrically calculated positions and refined using a riding model with C—H = 0.97 Å (for CH2 groups) and 0.96 Å (for CH3 groups), their isotropic displacement parameters were set to 1.2 times (1.5times for CH3 groups) the equivalent displacement parameter of their parent atoms.
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
of ethyl 3-(4-chlorophenyl)-5-(ethoxycarbonyl)-1H-pyrazole-1-acetate (Dong et al., 2007). We report here the 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)o and 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 of the title compound, (I).
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).
Data collection: APEX2 (Bruker, 2005); cell
APEX2 (Bruker, 2005); data reduction: APEX2 (Bruker, 2005); 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).Fig. 1. The structure of the title molecule showing displacement ellipsoids drawn at the 50% probability level. | |
Fig. 2. Packing view of (I), shown down the a axis. |
C17H20N2O5 | Z = 2 |
Mr = 332.35 | F(000) = 352 |
Triclinic, P1 | Dx = 1.290 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.4267 (1) Å | Cell parameters from 3567 reflections |
b = 11.0511 (2) Å | θ = 3.0–24.5° |
c = 11.7139 (2) Å | µ = 0.10 mm−1 |
α = 106.721 (1)° | T = 296 K |
β = 97.898 (1)° | Prism, colourless |
γ = 106.796 (1)° | 0.45 × 0.39 × 0.28 mm |
V = 855.59 (3) Å3 |
Bruker APEXII CCD area-detector diffractometer | 3806 independent reflections |
Radiation source: fine-focus sealed tube | 2376 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
φ and ω scans | θmax = 27.5°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −9→9 |
Tmin = 0.846, Tmax = 0.974 | k = −14→14 |
13041 measured reflections | l = −15→13 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.166 | w = 1/[σ2(Fo2) + (0.0775P)2 + 0.1127P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
3806 reflections | Δρmax = 0.32 e Å−3 |
221 parameters | Δρmin = −0.16 e Å−3 |
3 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.016 (4) |
C17H20N2O5 | γ = 106.796 (1)° |
Mr = 332.35 | V = 855.59 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.4267 (1) Å | Mo Kα radiation |
b = 11.0511 (2) Å | µ = 0.10 mm−1 |
c = 11.7139 (2) Å | T = 296 K |
α = 106.721 (1)° | 0.45 × 0.39 × 0.28 mm |
β = 97.898 (1)° |
Bruker APEXII CCD area-detector diffractometer | 3806 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 2376 reflections with I > 2σ(I) |
Tmin = 0.846, Tmax = 0.974 | Rint = 0.023 |
13041 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 3 restraints |
wR(F2) = 0.166 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.32 e Å−3 |
3806 reflections | Δρmin = −0.16 e Å−3 |
221 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | −0.7281 (3) | 0.0919 (3) | 0.9802 (3) | 0.1071 (8) | |
H1A | −0.7815 | 0.0997 | 0.9043 | 0.161* | |
H1B | −0.8148 | 0.0990 | 1.0334 | 0.161* | |
H1C | −0.7110 | 0.0062 | 0.9639 | 0.161* | |
C2 | −0.4043 (3) | 0.2015 (2) | 0.9716 (2) | 0.0792 (5) | |
C3 | −0.2328 (3) | 0.3033 (2) | 1.0311 (2) | 0.0871 (6) | |
H3 | −0.2183 | 0.3626 | 1.1091 | 0.104* | |
C4 | −0.0829 (3) | 0.3176 (2) | 0.9754 (2) | 0.0815 (6) | |
H4 | 0.0339 | 0.3872 | 1.0170 | 0.098* | |
C5 | −0.0974 (3) | 0.23132 (17) | 0.85765 (17) | 0.0676 (5) | |
C6 | −0.2716 (3) | 0.1283 (2) | 0.7993 (2) | 0.0783 (6) | |
H6 | −0.2865 | 0.0685 | 0.7214 | 0.094* | |
C7 | −0.4285 (3) | 0.1127 (2) | 0.8567 (2) | 0.0823 (6) | |
H7 | −0.5462 | 0.0432 | 0.8171 | 0.099* | |
C8 | 0.0682 (3) | 0.25088 (16) | 0.80054 (16) | 0.0645 (5) | |
C9 | 0.0946 (3) | 0.17110 (17) | 0.69185 (17) | 0.0674 (5) | |
H9 | 0.0062 | 0.0898 | 0.6365 | 0.081* | |
C10 | 0.2765 (3) | 0.23673 (16) | 0.68338 (16) | 0.0640 (5) | |
C11 | 0.5351 (3) | 0.46068 (18) | 0.81994 (17) | 0.0722 (5) | |
H11A | 0.6397 | 0.4248 | 0.8165 | 0.087* | |
H11B | 0.5551 | 0.5187 | 0.9038 | 0.087* | |
C12 | 0.5401 (3) | 0.54247 (18) | 0.73607 (18) | 0.0744 (5) | |
C13 | 0.7510 (4) | 0.7109 (3) | 0.6817 (3) | 0.1111 (9) | |
H13A | 0.6755 | 0.7696 | 0.6977 | 0.133* | |
H13B | 0.7114 | 0.6574 | 0.5949 | 0.133* | |
C14 | 0.9606 (5) | 0.7918 (3) | 0.7167 (3) | 0.1405 (13) | |
H14A | 0.9996 | 0.8409 | 0.8034 | 0.211* | |
H14B | 0.9843 | 0.8539 | 0.6730 | 0.211* | |
H14C | 1.0335 | 0.7330 | 0.6963 | 0.211* | |
C15 | 0.3773 (3) | 0.19420 (18) | 0.58813 (18) | 0.0714 (5) | |
C16 | 0.6729 (3) | 0.2462 (3) | 0.5236 (2) | 0.0952 (7) | |
H16A | 0.6079 | 0.2275 | 0.4395 | 0.114* | |
H16B | 0.7006 | 0.1670 | 0.5287 | 0.114* | |
C17 | 0.8560 (4) | 0.3647 (3) | 0.5629 (3) | 0.1128 (9) | |
H17A | 0.8293 | 0.4383 | 0.5452 | 0.169* | |
H17B | 0.9483 | 0.3412 | 0.5193 | 0.169* | |
H17C | 0.9080 | 0.3909 | 0.6496 | 0.169* | |
N1 | 0.2268 (2) | 0.36044 (14) | 0.85650 (14) | 0.0697 (4) | |
N2 | 0.3521 (2) | 0.35071 (14) | 0.78541 (14) | 0.0664 (4) | |
O1 | −0.5490 (2) | 0.19486 (17) | 1.03670 (16) | 0.1040 (5) | |
O2 | 0.4038 (2) | 0.53626 (15) | 0.66541 (16) | 0.1015 (5) | |
O3 | 0.7201 (2) | 0.62366 (14) | 0.75458 (13) | 0.0866 (5) | |
O4 | 0.3061 (2) | 0.08992 (16) | 0.50282 (15) | 0.1068 (6) | |
O5 | 0.55182 (19) | 0.28057 (13) | 0.60626 (13) | 0.0793 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0884 (16) | 0.0961 (16) | 0.127 (2) | 0.0173 (13) | 0.0019 (14) | 0.0497 (15) |
C2 | 0.0858 (13) | 0.0741 (12) | 0.0800 (12) | 0.0337 (11) | 0.0114 (10) | 0.0275 (9) |
C3 | 0.0879 (15) | 0.0757 (13) | 0.0808 (14) | 0.0253 (11) | 0.0101 (12) | 0.0105 (10) |
C4 | 0.0789 (13) | 0.0690 (12) | 0.0812 (14) | 0.0205 (10) | 0.0088 (11) | 0.0137 (10) |
C5 | 0.0714 (11) | 0.0561 (9) | 0.0686 (11) | 0.0195 (8) | 0.0012 (9) | 0.0217 (8) |
C6 | 0.0816 (13) | 0.0689 (11) | 0.0720 (12) | 0.0169 (10) | 0.0042 (10) | 0.0220 (9) |
C7 | 0.0760 (12) | 0.0665 (11) | 0.0860 (13) | 0.0112 (9) | −0.0028 (10) | 0.0234 (9) |
C8 | 0.0682 (11) | 0.0522 (9) | 0.0622 (10) | 0.0151 (8) | −0.0010 (8) | 0.0176 (8) |
C9 | 0.0697 (11) | 0.0500 (9) | 0.0656 (11) | 0.0123 (8) | −0.0031 (9) | 0.0129 (8) |
C10 | 0.0688 (11) | 0.0497 (8) | 0.0575 (10) | 0.0127 (8) | −0.0034 (8) | 0.0119 (7) |
C11 | 0.0730 (11) | 0.0625 (10) | 0.0548 (10) | 0.0035 (8) | −0.0051 (8) | 0.0118 (8) |
C12 | 0.0791 (12) | 0.0573 (10) | 0.0655 (11) | 0.0093 (9) | −0.0017 (10) | 0.0136 (8) |
C13 | 0.129 (2) | 0.0820 (15) | 0.1059 (19) | 0.0067 (14) | 0.0078 (16) | 0.0480 (14) |
C14 | 0.146 (3) | 0.106 (2) | 0.127 (2) | −0.0186 (19) | 0.021 (2) | 0.0466 (18) |
C15 | 0.0744 (12) | 0.0624 (10) | 0.0650 (11) | 0.0193 (9) | 0.0023 (9) | 0.0152 (9) |
C16 | 0.0941 (16) | 0.1076 (17) | 0.0903 (16) | 0.0433 (14) | 0.0266 (13) | 0.0332 (13) |
C17 | 0.0953 (17) | 0.1129 (19) | 0.150 (3) | 0.0370 (15) | 0.0466 (17) | 0.0653 (19) |
N1 | 0.0757 (10) | 0.0590 (8) | 0.0591 (9) | 0.0129 (7) | 0.0038 (8) | 0.0144 (7) |
N2 | 0.0691 (9) | 0.0556 (8) | 0.0563 (8) | 0.0093 (7) | −0.0014 (7) | 0.0127 (6) |
O1 | 0.0940 (11) | 0.0954 (11) | 0.1023 (12) | 0.0215 (9) | 0.0206 (9) | 0.0175 (9) |
O2 | 0.0943 (10) | 0.0906 (10) | 0.1036 (12) | 0.0156 (8) | −0.0142 (9) | 0.0441 (9) |
O3 | 0.0868 (9) | 0.0727 (8) | 0.0778 (9) | 0.0016 (7) | 0.0001 (7) | 0.0287 (7) |
O4 | 0.0975 (11) | 0.0835 (10) | 0.0917 (11) | 0.0104 (8) | 0.0154 (9) | −0.0146 (8) |
O5 | 0.0756 (8) | 0.0742 (8) | 0.0753 (9) | 0.0172 (7) | 0.0137 (7) | 0.0178 (7) |
C1—O1 | 1.397 (3) | C11—C12 | 1.512 (3) |
C1—H1A | 0.9600 | C11—H11A | 0.9700 |
C1—H1B | 0.9600 | C11—H11B | 0.9700 |
C1—H1C | 0.9600 | C12—O2 | 1.188 (2) |
C2—C3 | 1.360 (3) | C12—O3 | 1.325 (2) |
C2—C7 | 1.370 (3) | C13—O3 | 1.452 (3) |
C2—O1 | 1.398 (3) | C13—C14 | 1.483 (4) |
C3—C4 | 1.359 (3) | C13—H13A | 0.9700 |
C3—H3 | 0.9300 | C13—H13B | 0.9700 |
C4—C5 | 1.402 (3) | C14—H14A | 0.9600 |
C4—H4 | 0.9300 | C14—H14B | 0.9600 |
C5—C6 | 1.377 (2) | C14—H14C | 0.9600 |
C5—C8 | 1.470 (3) | C15—O4 | 1.203 (2) |
C6—C7 | 1.417 (3) | C15—O5 | 1.315 (2) |
C6—H6 | 0.9300 | C16—O5 | 1.455 (3) |
C7—H7 | 0.9300 | C16—C17 | 1.492 (3) |
C8—N1 | 1.338 (2) | C16—H16A | 0.9700 |
C8—C9 | 1.400 (3) | C16—H16B | 0.9700 |
C9—C10 | 1.369 (3) | C17—H17A | 0.9600 |
C9—H9 | 0.9300 | C17—H17B | 0.9600 |
C10—N2 | 1.368 (2) | C17—H17C | 0.9600 |
C10—C15 | 1.469 (3) | N1—N2 | 1.338 (2) |
C11—N2 | 1.449 (2) | ||
O1—C1—H1A | 109.5 | H11A—C11—H11B | 108.0 |
O1—C1—H1B | 109.5 | O2—C12—O3 | 125.12 (19) |
H1A—C1—H1B | 109.5 | O2—C12—C11 | 125.49 (19) |
O1—C1—H1C | 109.5 | O3—C12—C11 | 109.39 (16) |
H1A—C1—H1C | 109.5 | O3—C13—C14 | 107.6 (2) |
H1B—C1—H1C | 109.5 | O3—C13—H13A | 110.2 |
C3—C2—C7 | 121.2 (2) | C14—C13—H13A | 110.2 |
C3—C2—O1 | 115.1 (2) | O3—C13—H13B | 110.2 |
C7—C2—O1 | 123.7 (2) | C14—C13—H13B | 110.2 |
C4—C3—C2 | 119.4 (2) | H13A—C13—H13B | 108.5 |
C4—C3—H3 | 120.3 | C13—C14—H14A | 109.5 |
C2—C3—H3 | 120.3 | C13—C14—H14B | 109.5 |
C3—C4—C5 | 122.6 (2) | H14A—C14—H14B | 109.5 |
C3—C4—H4 | 118.7 | C13—C14—H14C | 109.5 |
C5—C4—H4 | 118.7 | H14A—C14—H14C | 109.5 |
C6—C5—C4 | 117.2 (2) | H14B—C14—H14C | 109.5 |
C6—C5—C8 | 122.06 (18) | O4—C15—O5 | 123.9 (2) |
C4—C5—C8 | 120.78 (17) | O4—C15—C10 | 122.73 (19) |
C5—C6—C7 | 120.6 (2) | O5—C15—C10 | 113.38 (15) |
C5—C6—H6 | 119.7 | O5—C16—C17 | 106.8 (2) |
C7—C6—H6 | 119.7 | O5—C16—H16A | 110.4 |
C2—C7—C6 | 119.0 (2) | C17—C16—H16A | 110.4 |
C2—C7—H7 | 120.5 | O5—C16—H16B | 110.4 |
C6—C7—H7 | 120.5 | C17—C16—H16B | 110.4 |
N1—C8—C9 | 110.03 (17) | H16A—C16—H16B | 108.6 |
N1—C8—C5 | 119.14 (17) | C16—C17—H17A | 109.5 |
C9—C8—C5 | 130.83 (16) | C16—C17—H17B | 109.5 |
C10—C9—C8 | 106.19 (15) | H17A—C17—H17B | 109.5 |
C10—C9—H9 | 126.9 | C16—C17—H17C | 109.5 |
C8—C9—H9 | 126.9 | H17A—C17—H17C | 109.5 |
N2—C10—C9 | 106.01 (17) | H17B—C17—H17C | 109.5 |
N2—C10—C15 | 125.70 (17) | C8—N1—N2 | 105.97 (15) |
C9—C10—C15 | 128.25 (16) | N1—N2—C10 | 111.79 (15) |
N2—C11—C12 | 111.51 (14) | N1—N2—C11 | 118.33 (14) |
N2—C11—H11A | 109.3 | C10—N2—C11 | 129.73 (18) |
C12—C11—H11A | 109.3 | C1—O1—C2 | 117.6 (2) |
N2—C11—H11B | 109.3 | C12—O3—C13 | 116.71 (17) |
C12—C11—H11B | 109.3 | C15—O5—C16 | 118.99 (16) |
C7—C2—C3—C4 | 0.2 (3) | C9—C10—C15—O4 | −0.7 (3) |
O1—C2—C3—C4 | 179.65 (19) | N2—C10—C15—O5 | −2.6 (3) |
C2—C3—C4—C5 | 0.3 (3) | C9—C10—C15—O5 | 179.77 (16) |
C3—C4—C5—C6 | −0.7 (3) | C9—C8—N1—N2 | −0.21 (18) |
C3—C4—C5—C8 | 179.64 (18) | C5—C8—N1—N2 | 179.32 (14) |
C4—C5—C6—C7 | 0.6 (3) | C8—N1—N2—C10 | 0.48 (19) |
C8—C5—C6—C7 | −179.75 (16) | C8—N1—N2—C11 | 176.47 (14) |
C3—C2—C7—C6 | −0.3 (3) | C9—C10—N2—N1 | −0.56 (19) |
O1—C2—C7—C6 | −179.68 (18) | C15—C10—N2—N1 | −178.58 (15) |
C5—C6—C7—C2 | −0.1 (3) | C9—C10—N2—C11 | −175.96 (16) |
C6—C5—C8—N1 | 173.34 (16) | C15—C10—N2—C11 | 6.0 (3) |
C4—C5—C8—N1 | −7.0 (2) | C12—C11—N2—N1 | −106.75 (19) |
C6—C5—C8—C9 | −7.2 (3) | C12—C11—N2—C10 | 68.4 (2) |
C4—C5—C8—C9 | 172.38 (18) | C3—C2—O1—C1 | −179.77 (19) |
N1—C8—C9—C10 | −0.12 (19) | C7—C2—O1—C1 | −0.4 (3) |
C5—C8—C9—C10 | −179.58 (16) | O2—C12—O3—C13 | −0.3 (3) |
C8—C9—C10—N2 | 0.40 (18) | C11—C12—O3—C13 | −179.51 (19) |
C8—C9—C10—C15 | 178.35 (16) | C14—C13—O3—C12 | −179.8 (2) |
N2—C11—C12—O2 | 13.2 (3) | O4—C15—O5—C16 | −4.0 (3) |
N2—C11—C12—O3 | −167.54 (16) | C10—C15—O5—C16 | 175.57 (16) |
N2—C10—C15—O4 | 176.88 (19) | C17—C16—O5—C15 | 177.34 (17) |
Experimental details
Crystal data | |
Chemical formula | C17H20N2O5 |
Mr | 332.35 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 7.4267 (1), 11.0511 (2), 11.7139 (2) |
α, β, γ (°) | 106.721 (1), 97.898 (1), 106.796 (1) |
V (Å3) | 855.59 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.45 × 0.39 × 0.28 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.846, 0.974 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13041, 3806, 2376 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.166, 1.06 |
No. of reflections | 3806 |
No. of parameters | 221 |
No. of restraints | 3 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.32, −0.16 |
Computer programs: APEX2 (Bruker, 2005), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), WinGX (Farrugia, 1999).
X—H···Cg | X—H | H···Cg | X···Cg | X—H···Cg |
C1—H1A···Cg1i | 0.96 | 2.89 | 3.731 (3) | 147 |
Symmetry code: (i) 1+x,y,z. |
Acknowledgements
This study was supported by the Natural Science Foundation of Shandong Province (grant No. Y2005B12).
References
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Brough, P. A., Barril, X. & Beswick, M. (2005). Bioorg. Med. Chem. Lett. 15, 5197–5201. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (1997). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2005). APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cheng, H., Lundy DeMello, K. M., Li, J. & Sakya, S. M. (2006). Bioorg. Med. Chem. Lett. 16, 2076–2080. Web of Science CrossRef PubMed CAS Google Scholar
Dong, W.-L., Dong, W.-L., Xia, Y., Ge, Y.-Q. & Zhao, B.-X. (2007). Acta Cryst. E63, o4468. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Sehon, C., McClure, K., Hack, M., Morton, M., Gomez, L. & Li, L. (2006). Bioorg. Med. Chem. Lett. 15, 1677–1680. Google Scholar
Sheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany. Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wei, F., Zhao, B. X., Huang, B., Zhang, L., Sun, C. H., Dong, W. L., Shin, D. S. & Miao, J. Y. (2006). Bioorg. Med. Chem. Lett. 16, 6342–6347. Web of Science CrossRef PubMed CAS Google Scholar
Xia, Y., Dong, Z. W., Zhao, B. X., Ge, X., Meng, N., Shin, D. S. & Miao, J. Y. (2007). Bioorg. Med. Chem. 15, 6893–6899. Web of Science CrossRef PubMed CAS Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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)o and 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).