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Structures of two N-{2-([(5-amino-1,3,4-thiadiazol-2-yl)difluoromethyl]-4-halophenyl}acetamides

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Abstract

The compounds, N-{2-[(5-amino-1,3,4-thiadiazol-2-yl)difluoromethyl]-4-chlorophenyl}acetamide (1: X = Cl) and N-{2([(5-amino-1,3,4-thiadiazol-2-yl)difluoromethyl]-4-bromo-phenyl}acetamide (1: X = Br), are isostructural. The molecules are near ‘‘V’’ shaped with the angles between the two aromatic planes ca. 84° in each case. The various intermolecular interactions, namely N–H···O, N–H···N, N–H···F, and C–H···N hydrogen bonds and C–H···π, C–Cl···π and C–O···π interactions, generate 3-D arrays. Compound (1: X = Cl) crystallizes in the monoclinic space group P21/c with a = 16.9032(7) Å, 10.2193(4) Å, c = 7.5227(4) Å, β = 100.179(3)° and Z = 4. Compound (1: X = Br) crystallizes in the monoclinic space group P21/c with a = 17.2119(4) Å, 10.2167(2) Å, c = 7.5677(2) Å, β = 100.326(2)° and Z = 4.

Graphical Abstract

Generation of 3-D arrays via N–H···O, N–H···N, N–H···F, and C–H···N hydrogen bonds and C–H···π, C–Cl···π and C–O···π intermolecular interactions.

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Acknowledgments

The use of the EPSRC X-ray crystallographic service at Southampton and the valuable assistance of the staff there are gratefully acknowledged. JLW thanks CAPES for financial support.

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Authors and Affiliations

  1. Fundação Oswaldo Cruz, Far-Manguinhos, Avenida Brasil, Rio de Janeiro, RJ, 21041-250, Brazil

    Núbia Boechat, Mônica M. Bastos & Lindalva C. Maciel

  2. Instituto de Química, Universidade Federal do Rio de Janeiro, Ilha do Fundão, Rio de Janeiro, RJ, 21941-590, Brazil

    Mônica M. Bastos & Warner B. Kover

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

    Solange M. S. V. Wardell

  4. Centro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Av. Brasil 4365, Rio de Janeiro, RJ, 21040-900, Brazil

    James L. Wardell

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  1. Núbia Boechat
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  2. Mônica M. Bastos
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  3. Lindalva C. Maciel
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  5. Solange M. S. V. Wardell
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  6. James L. Wardell
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Correspondence to James L. Wardell.

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Boechat, N., Bastos, M.M., Maciel, L.C. et al. Structures of two N-{2-([(5-amino-1,3,4-thiadiazol-2-yl)difluoromethyl]-4-halophenyl}acetamides. J Chem Crystallogr 41, 874–879 (2011). https://doi.org/10.1007/s10870-011-0016-8

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  • DOI: https://doi.org/10.1007/s10870-011-0016-8

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