N. Boechat, A. S. Carvalho, Bruna Maria Cs Quaresma
Jul 18, 2016
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Journal
Journal of Chemical Crystallography
Abstract
The crystal structures of 4-cyclopropyl-1-(1-methyl-4-nitro-1H-imidazol-5-yl)-1H-1,2,3-triazole, 1, and ethyl 1-(1-methyl-4-nitro-1H-imidazol-5-yl)-1H-1,2,3-triazole-4-carboxylate, 2, are reported. The two molecules are non-planar as indicated by the dihedral angles between the heteroaryl rings of 53.94 (7)° in 1 and 70.68 (12)° in 2. Considerable delocalization of π -electron density within the triazole ring is indicated by the pattern of bond distances in 1. By contrast to 1, localization of π -electron density within the triazole ring in 2 is apparent. In both molecules, the nitro group takes part in N–O···π(imidazole) interactions. Compound 1 crystallizes in the orthorhombic space group P212121 with a = 7.8053(3) Å, b = 8.5264(3) Å, c = 15.7343(11) Å and Z = 4. Compound 2 crystallizes in the monoclinic space group, P21/c with a = 5.2740(4) Å, b = 8.9695(5) Å, c = 26.0080(18) Å, β = 92.622(2)° and Z = 4.Graphical AbstractThe bond lengths indicate more bond fixation in the triazole rings of ethyl 1-(1-methyl-4-nitro-1H-imidazol-5-yl)-1H-1,2,3-triazole-4-carboxylate and more delocalization in 4-cyclopropyl-1-(1-methyl-4-nitro-1H-imidazol-5-yl)-1H-1,2,3-triazole.