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Guest inclusion in cyclic imides containing flexible tethers

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Abstract

Guest inclusion properties of two cyclic imides which have carboxylic acids connected through flexible tether, namely, 4-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-cyclohexanecarboxylic acid (1) and 4-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-ylmethyl)-cyclohexanecarboxylic acid (2) are studied. The crystals of host 1 containing one molecule of 1, the crystals of 4,4′-bipyridine (bpy) cocrystal of 1 containing one molecule of 1 and half molecule of bpy (1a), the crystals of 1,4-dioxane solvate of 1 containing two molecule of 1 and one and half molecule of 1,4-dioxane (1b) and the crystals of quinoline solvate of 1 containing one molecule of 1 and one molecule of quinoline (1c) in their crystallographic asymmetric units are investigated. Intermolecular hydrogen bonded two dimensional (2D) sheet structure of 1 and 3D channel network of 1b are comprised of cyclic R 22 (8) hydrogen bond motifs; whereas cleavage of dimeric carboxylic acid R 22 (8) motifs occurs in the structures of 1a and 1c in which 3D host–guest networks are comprised of discrete O–H···N and cyclic R 22 (7) interactions, respectively. Various types of weak interactions between the two symmetry nonequivalent host molecule are found to be responsible for the formation of channels (14 × 11 Å) filled by guest 1,4-dioxane molecules in the crystal lattice of 1b. Two different solvates of 2 containing one molecule of 2 with a water molecule (2a) and one molecule of 2 with a quinoline molecule (2b) in their crystallographic asymmetric units, respectively, are also crystallized in different space groups. The quinoline molecules are held with host molecules by discrete O–H···N and C–H···O interactions and reside inside the voids formed by 3D repeated hexameric assemblies of host molecules in the crystal lattice of 2b.

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Acknowledgments

The authors thank Department of Science and Technology, New Delhi (India) for financial support. One of the authors DS is thankful to Council of Scientific and Industrial Research, New Delhi (India) for senior research fellowship.

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  1. Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati, 781 039, Assam, India

    Devendra Singh & Jubaraj B. Baruah

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Correspondence to Jubaraj B. Baruah.

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10847_2012_196_MOESM1_ESM.doc

Supporting Information: The CIFs, tables of hydrogen bond parameters, and TGA curves are available as supporting information. (DOC 226 kb)

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Singh, D., Baruah, J.B. Guest inclusion in cyclic imides containing flexible tethers. J Incl Phenom Macrocycl Chem 76, 269–281 (2013). https://doi.org/10.1007/s10847-012-0196-7

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