Crystal and molecular structures of two triazole derivatives: 4-Cyclopropyl-4,5-dihydro-1H-1,2,3-triazole and Methyl 1-benzyl-1H-1,2,3-triazole-4-carboxylate
Document Type
Article
Publication Date
1-1-2010
Abstract
The molecule in 4-cyclopropyl-4,5-dihydro-1H-1,2,3-triazole (I) is disposed about a mirror plane with the triazole ring lying in the plane and being orthogonal to the cyclopropyl ring. Considerable delocalization of pi-electron density within the triazole ring is indicated by the pattern of bond distances in (I). The molecule of methyl 1-benzyl-1H-1,2,3-triazole-4-carboxylate (II) adopts a curved shape with the dihedral angle formed between the triazole and benzene rings being 63.23(8)A degrees. By contrast to (I), localization of pi-electron density within the triazole ring in (II) is indicated. Both (I), via N-H center dot center dot center dot N hydrogen bonding, and (II), via C-H center dot center dot center dot O and C-H center dot center dot center dot N interactions, associate in the solid state to form supramolecular chains. In (I), the chain is a zigzag with a flat topology, whereas in (II) the linear chain has a curved topology. Compound (I) crystallizes in the orthorhombic space group Pnma with a = 5.6470(2) angstrom, b = 7.3359(4) angstrom, c = 13.4404(7) angstrom, and Z = 4. Compound (II) crystallizes in the monoclinic space group P2(1)/c with a = 12.1314(5) angstrom, b = 5.5951(2) angstrom, c = 16.4339(7) angstrom, beta = 111.269(2)degrees, and Z = 4.
Keywords
Triazole, Hydrogen bonding, Conformation
Publication Title
Journal of Chemical Crystallography
Volume
40
Issue
12
Publisher
Kluwer (now part of Springer)
Publisher Location
233 SPRING ST, NEW YORK, NY 10013 USA