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4-Cyclopropyl-1-(1-methyl-4-nitro-1H-imidazol-5-yl)-1H-1,2,3-triazole and Ethyl 1-(1-methyl-4-nitro-1H-imidazol-5-yl)-1H-1,2,3-triazole-4-carboxylate

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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 Abstract

The 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.

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Acknowledgments

JLW gratefully acknowledges FAPERJ and CNPq, Brazil for support. The NCS X-ray Crystallography Service, based at the University of Southampton, UK, is thanked for the collection of the X-ray data.

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Authors and Affiliations

  1. Fundação Oswaldo Cruz, Instituto de Tecnologia em Fármacos, Departamento de Síntese de Fármacos, Manguinhos, Rio De Janeiro, RJ, 21041-250, Brazil

    Núbia Boechat, Alcione S. Carvalho, Bruna M. C. S. Quaresma & James L. Wardell

  2. Universidade Federal do Rio de Janeiro, Instituto de Ciências Biomédicas, Programa de Pós-graduação em Farmacologia e Química Medicinal, Av. Carlos Chagas, 373-bl.K, 2º andar, sala 35-Prédio do Centro de Ciências da Saúde, Cidade Universitária, Ilha do Fundão, Rio De Janeiro, RJ, 21941-902, Brazil

    Bruna M. C. S. Quaresma

  3. Department of Chemistry, University of Aberdeen, Aberdeen, AB24 3UE, Scotland, UK

    James L. Wardell

  4. CHEMSOL, 1 Harcourt Road, Aberdeen, AB15 5NY, Scotland, UK

    Solange M. S. V. Wardell

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  1. Núbia Boechat
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  2. Alcione S. Carvalho
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  3. Bruna M. C. S. Quaresma
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Correspondence to James L. Wardell.

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Boechat, N., Carvalho, A.S., Quaresma, B.M.C.S. et al. 4-Cyclopropyl-1-(1-methyl-4-nitro-1H-imidazol-5-yl)-1H-1,2,3-triazole and Ethyl 1-(1-methyl-4-nitro-1H-imidazol-5-yl)-1H-1,2,3-triazole-4-carboxylate. J Chem Crystallogr 46, 296–302 (2016). https://doi.org/10.1007/s10870-016-0659-6

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