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

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 π-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)°. By contrast to (I), localization of π-electron density within the triazole ring in (II) is indicated. Both (I), via N–H···N hydrogen bonding, and (II), via C–H···O and C–H···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) Å, b = 7.3359(4) Å, c = 13.4404(7) Å, and Z = 4. Compound (II) crystallizes in the monoclinic space group P2₁/c with a = 12.1314(5) Å, b = 5.5951(2) Å, c = 16.4339(7) Å, β = 111.269(2)°, and Z = 4.

Graphical Abstract

Supramolecular chains mediated by N–H···N hydrogen bonding (illustrated) or C–H···O and C–H···N interactions are found in the title structures, respectively.