Crystal structure of 5-chloro-methyl-N-methyl-4-[(4-phenyl-1,2,3-triazol-1-yl)meth-yl]isoxazolidine-3-carboxamide.

Jihed Brahmi,Erwann Jeanneau,Moncef Msaddek,Sébastien Vidal,Kaïss Aouadi,Soumaya Nasri

doi:10.1107/s2056989016002784

Abstract

The title compound, C15H18ClN5O2, crystallizes with two independent mol-ecules (A and B) in the asymmetric unit. In both mol-ecules, the isoxazolidine rings have an envelope conformation with the O atoms at the flap positions. Each mol-ecule has three stereogenic centres with configurations 2(S), 3(S) and 4(R), confirmed by resonant scattering. Their conformations are significantly different, for example in mol-ecule A the phenyl ring is inclined to the triazole ring by 32.5 (2)°, while in mol-ecule B the corresponding dihedral angle is 10.7 (2)°. In the crystal, the A and B mol-ecules are linked via an N-H⋯O and a C-H⋯O hydrogen bond. These units are linked by C-H⋯O and C-H⋯N hydrogen bonds, forming slabs parallel to the ab plane. There are C-H⋯π inter-actions present within the slabs.

Highlights

The title compound, C15H18ClN5O2, crystallizes with two independent molecules (A and B) in the asymmetric unit
Each molecule has three stereogenic centres with configurations 2(S), 3(S) and 4(R), confirmed by resonant scattering. Their conformations are significantly different, for example in molecule A the phenyl ring is inclined to the triazole ring by
The 1,3-dipolar cycloaddition of nitrones to alkenes provides a straightforward route to isoxazolidines (Frederickson, 1997; Gothelf et al, 2002)

Summary

Chemical context

The 1,3-dipolar cycloaddition of nitrones to alkenes provides a straightforward route to isoxazolidines (Frederickson, 1997; Gothelf et al, 2002). Nitrone cycloadducts are attractive intermediates for the synthesis of several classes of natural products and biologically active compounds, such as unnatural aminoacids (Aouadi, et al, 2006) and alkaloids; for example (+)-febrifugine, ()-indolizidine 209B (Smith et al, 1988),. (+)-sedridine (Louis & Hootelé, 1995, 1997; Huisgen, 1984). We report on the synthesis, the molecular structure and the spectroscopic data of the title compound, (2)

Structural commentary

Supramolecular features

Synthesis and crystallization

Spectroscopic investigations