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

• Main Authors: Jihed Brahmi, Soumaya Nasri, Kaïss Aouadi, Erwann Jeanneau, Sébastien Vidal, Moncef Msaddek
• Format: Article
• Language: English
• Published: International Union of Crystallography 2016-03-01
• Series: Acta Crystallographica Section E: Crystallographic Communications
• Subjects: crystal structure; 1,3-dipolar cycloaddition; isoxazolidine; hydrogen bonding
• Online Access: http://scripts.iucr.org/cgi-bin/paper?S2056989016002784

The title compound, C15H18ClN5O2, crystallizes with two independent molecules (A and B) in the asymmetric unit. In both molecules, the isoxazolidine rings have an envelope conformation with the O atoms at the flap positions. 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 32.5 (2)°, while in molecule B the corresponding dihedral angle is 10.7 (2)°. In the crystal, the A and B molecules 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 interactions present within the slabs.