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

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