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Structures of Protonated Bis(pyridine-2-yl) Ketone Arylhydrazone Derivatives: [(C5H4N)(C5H4NH)C=NNHC6H4Y]+[X]− (Y,X = 3-O2N,Cl: 4-Me,Cl:)

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Abstract

The crystal structures of two salts of protonated bis(pyridine-2-yl) ketone arylhydrazone derivatives, [(C5H4N)(C5H4NH)C=NNHC6H4Y]+[X]−, 2 (Y,X = 3-O2N,Cl), and the trihydrate of 3 (X,Y = 4-Me,Cl), are reported from data collected at 120 K. The cations in 2 and 3 exhibit different conformations, which have consequences in the type and number of intra- and intermolecular interactions exhibited. Three dimensional arrays are generated for both compounds by different combinations of intermolecular interactions. In 2, the cations are linked directly by π−π stacking interactions and by C−H···O hydrogen bonds, as well as by bridging chloride ions. The cations in [(3)·3H2O] are directly again linked by π−π stacking and also by C−H···π interactions, and indirectly via chloride ions and water molecules. Compound 2 crystallises in the monoclinic space group P21/c, with a = 14.4210(4) Å, b = 9.1543(3) Å, c = 12.3365(3) Å, β, 104.583(2)o and Z = 4. Compound 3 crystallises in the triclinic space group P-1, with a = 8.1352(2) Å, b = 10.0278(3) Å, c = 12.1482(4) Å, α = 106.4290(14)o, β = 92.8080(18)o, 90.3920(18)o, Z = 2.

Graphical Abstract

[Different three dimensional arrays are generated by different combinations of intermolecular interactions in [(C5H4N)(C5H4NH)C = NNHC6H4Y]+[X]−, 2 (Y,X = 3-O2N,Cl), and the trihydrate of 3 (X,Y = 4-Me, Cl.]

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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 and FAPEMIG for financial support.

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Authors and Affiliations

  1. Departamento de Quimica, ICEx, Universidade Federal de Minas Gerais, Belo Horizonte, MG, 31270-901, Brazil

    Geraldo M. de Lima

  2. 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

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

    James L. Wardell & R. Alan Howie

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

    Solange M. S. V. Wardell

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  1. Geraldo M. de Lima
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  2. James L. Wardell
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  3. R. Alan Howie
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  4. Solange M. S. V. Wardell
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Correspondence to James L. Wardell.

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de Lima, G.M., Wardell, J.L., Howie, R.A. et al. Structures of Protonated Bis(pyridine-2-yl) Ketone Arylhydrazone Derivatives: [(C5H4N)(C5H4NH)C=NNHC6H4Y]+[X]− (Y,X = 3-O2N,Cl: 4-Me,Cl:). J Chem Crystallogr 43, 36–43 (2013). https://doi.org/10.1007/s10870-012-0384-8

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  • DOI: https://doi.org/10.1007/s10870-012-0384-8

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