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Vol. 25 No. 2 (2013): Vol 25 Issue 2

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Synthesis and Structural Characterization of N-2,3-Dimethyl-5-oxo-1-phenyl-1H-pyrazol-4-yl-7-oxa-bicyclo[2,2,1]hept-5-ene-2,3-dicarboximide

https://doi.org/10.14233/ajchem.2013.12174
Zu-Pei Liang
Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, P.R. China
Jian Li
Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, P.R. China

Corresponding Author(s) : Zu-Pei Liang

lzpwfu@163.com

Asian Journal of Chemistry, Vol. 25 No. 2 (2013): Vol 25 Issue 2

Abstract

Present compound N-2,3-dimethyl-5-oxo-1-phenyl-1H-pyrazol-4-yl-exo-7-oxabicyclo[ 2,2,1]hept-5-ene-2,3-dicarboximide (C19H17N3O4, Mr = 351.36) was synthesized and characterized by elemental analysis, 1H NMR spectra, IR spectra and single crystal X-ray diffraction. The crystal belongs to orthorhombic, space group P212121, with a = 6.4582(8), b = 15.8179(14), c = 16.2269(15) Å, b = 90º, V = 1657.7(3) Å3, Z = 4, Dc = 1.408 g/cm3, l = 0.71073 Å, μ(MoKa) = 0.101 mm-1, F(000) = 736. The final refinement gave R = 0.0326, wR(F2) = 0.0723 for 1,702 observed reflections with I > 2s(I). The structure of the title compound comprises a racemic mixture of chiral molecules containing four stereogenic centres. X-Ray diffraction analysis reveals that the cyclohexane ring tends towards a boat conformation. The dihedral angle between the dihydropyrazole ring and the pyrrolidine ring and the aromatic ring is 82.0(1) and 57.3(1)º, respectively. The crystal structure is stabilized by N-H···O, C-H···O, C-H···N and N-H···N hydrogen bonds.

Keywords

N-2,3-Dimethyl-5-oxo-1-phenyl-1H-pyrazol-4-yl-exo-7-oxa-bicyclo[2,2,1]hept5-ene-2,3-dicarboximide Synthesis Structural characterization
Liang, Z.-P., & Li, J. (2012). Synthesis and Structural Characterization of N-2,3-Dimethyl-5-oxo-1-phenyl-1H-pyrazol-4-yl-7-oxa-bicyclo[2,2,1]hept-5-ene-2,3-dicarboximide. Asian Journal of Chemistry, 25(2), 685–687. https://doi.org/10.14233/ajchem.2013.12174
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