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Solvates of Two Ethyl 6-(2-(aryl)-4-oxothiazolidin-3-yl)-1-ethyl-4-oxo-1,4-dihydroquinoline-3-carboxylates

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Abstract

The crystal structures of solvates of ethyl 6-(2-(RC6H4)-4-oxothiazolidin-3-yl)-1-ethyl-4-oxo-1,4-dihydroquinoline-3-carboxylate derivatives, (1a; R = 3-Br) and (1b: R = H), namely [1a·(H2O)] and [(1b) 2·(H2O)2·(EtOH)], are reported. The solvate molecules in [(1b) 2·(H2O)2·(EtOH)] are disordered in contrast to the ordered hydrate molecule in [1a·(H2O)]. The disordered EtOH molecules merely solvate individual oxothiazolidine units, while the hydrate molecules in both compounds link the oxothiazolidine units into chains. Despite the differences involving the solvates, the supramolecular arrangements in the two solvated compounds are very similar, being made of O–H···O, C–H···O, C–H···π and π···π intermolecular interactions. It is noticeable that differently sited CH units in the RC6H4 rings are used in the C–H···π interactions. In each compound, the RC6H4 ring is near orthogonal to the very-near planar quinoline ring with angles between the best planes of 83.82(10)° and 88.52(3)°, for 1a and 1b, respectively. Compound (1) crystallizes in the triclinic space group P-1 with a = 10.7995(11) Å, b = 11.2612(11) Å, c = 11.3792(11) Å, α = 108.504(8)°, β = 116.317(8)°, γ = 92.846(7)°, and Z = 2. Compound (2) crystallizes in the triclinic space group P-1 with a = 10.8717(3) Å, b = 11.0038(3) Å, c = 11.2648(3) Å, α = 66.040(2)°, β = 86.422(2)°, γ = 67.052(1)°, and Z = 2.

Graphical Abstract

The supramolecular arrangements in the two solvated compounds are very similar, being made of O–H···O, C–H···O, C–H···π and π···π intermolecular interactions.

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Acknowledgments

The use of the National Crystallographic Service at Southampton and the valuable assistance of the staff there are gratefully acknowledged.

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Authors and Affiliations

  1. Departamento de Química Orgânica, Instituto de Química, Universidade Federal Fluminense, Outeiro de São João Batista, s/no, Centro, Niterói, Rio De Janeiro, 24020-141, Brazil

    Victor Facchinetti & Thatyana R. A. Vasconcelos

  2. Fundação Oswaldo Cruz, Instituto de Tecnologia em Fármacos - Farmanguinhos, Rua Sizenando Nabuco 100, Manguinhos, Rio De Janeiro, RJ, 21041-250, Brazil

    Victor Facchinetti, Claudia R. B. Gomes & Marcus V. N. de Souza

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

    Solange M. S. V. Wardell

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

    James L. Wardell

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  1. Victor Facchinetti
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  2. Claudia R. B. Gomes
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Correspondence to James L. Wardell.

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Facchinetti, V., Gomes, C.R.B., de Souza, M.V.N. et al. Solvates of Two Ethyl 6-(2-(aryl)-4-oxothiazolidin-3-yl)-1-ethyl-4-oxo-1,4-dihydroquinoline-3-carboxylates. J Chem Crystallogr 44, 471–479 (2014). https://doi.org/10.1007/s10870-014-0540-4

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  • DOI: https://doi.org/10.1007/s10870-014-0540-4

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