Diethyl 2-[(3,5-dimethyl-1H-pyrazol-1-yl)(4-meth­oxy­phen­yl)meth­yl]propane­dioate

Meskini, I.; Daoudi, M.; Daran, J.-C.; Kerbal, A.; Zouihri, H.

doi:10.1107/S1600536810025572

Volume 66
Part 8
Page o1965
August 2010

Received 26 June 2010
Accepted 29 June 2010
Online 10 July 2010

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.056
wR = 0.154
Data-to-parameter ratio = 15.7
Details

Diethyl 2-[(3,5-dimethyl-1H-pyrazol-1-yl)(4-methoxyphenyl)methyl]propanedioate

Ihssan Meskini,^a Maria Daoudi,^a ^* Jean-Claude Daran,^b Abdelali Kerbal ^a and Hafid Zouihri ^c

^aLaboratoire de Chimie Organique, Faculté des Sciences Dhar el Mahraz, Université Sidi Mohammed Ben Abdellah, Fès, Morocco,^bLaboratoire de Chimie de Coordination, 205 Route de Narbonne, 31077 Toulouse Cedex, France, and ^cLaboratoires de Diffraction des Rayons X, Division UATRS, Centre National pour la Recherche Scientifique et Technique, Rabat, Morocco
Correspondence e-mail: daoudimaria@yahoo.fr

The title compound, C₂₀H₂₆N₂O₅, was prepared in good yield (76%) through condensation of diethyl (4-methoxybenzyl)propanedioate with 3,5-dimethyl-1H-pyrazole. The dihedral between the benzene and pyrazole rings is 83.96 (10)°. The crystal packing is stabilized by a C-HO interaction, which links the molecules into centrosymmetric dimers.

Related literature

For related compounds displaying biological activity, see: Dayam et al. (2007); Patil et al. (2007); Ramkumar et al. (2008); Sechi et al. (2009) & Zeng et al. (2008). For the synthetic procedure, see: Pommier & Neamati (2006).

Experimental

Crystal data

C₂₀H₂₆N₂O₅
M_r = 374.43
Monoclinic, P 2₁ /c
a = 11.9618 (3) Å
b = 7.9681 (2) Å
c = 21.1269 (6) Å
= 96.504 (1)°
V = 2000.70 (9) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 296 K
0.23 × 0.17 × 0.14 mm

Data collection

Bruker X8 APEXII CCD area-detector diffractometer
18616 measured reflections
3921 independent reflections
3177 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.056
wR(F²) = 0.154
S = 1.05
3921 reflections
249 parameters
H-atom parameters constrained
_max = 0.68 e Å^-3
_min = -0.45 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C12-H12O2ⁱ	0.93	2.51	3.358 (3)	152
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5280 ).

Acknowledgements

This work was supported by grants from Project PGR-UMP-BH-2005, the Centre National de Recherche Scientifique, CNRS (France), the Centre National pour la Recherche Scientifique et Technique, CNRST (Morocco), and the CURI (Morocco).

References

Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Dayam, R., Al-Mawsawi, L. Q. & Neamati, N. (2007). Bioorg. Med. Chem. Lett. 17, 6155-6159.
Patil, S., Kamath, S., Sanchez, T., Neamati, N., Schinazi, R. F. & Buolamwini, J. K. (2007). Bioorg. Med. Chem. 15, 1212-1228.
Pommier, Y. & Neamati, N. (2006). Bioorg. Med. Chem. 14, 3785-3792.
Ramkumar, K., Tambov, K. V., Gundla, R., Manaev, A. V., Yarovenko, V., Traven, V. F. & Neamati, N. (2008). Bioorg. Med. Chem. 16, 8988-8998.
Sechi, M., Carta, F., Sannia, L., Dallocchio, R., Dessì, A., Al-Safi, R. I. & Neamati, N. (2009). Antiviral Res. 81, 267-276.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.
Zeng, L. F., Zhang, H.-S. W., ang, Y. H., Sanchez, T., Zheng, Y. T., Neamati, N. & Long, Y. Q. (2008). Bioorg. Med. Chem. Lett. 18, 4521-4524.

organic compounds