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Breaking Down the Interdigitated Dimeric Structure of Calix[4]arenediphosphonic Acid: the Structures of the Complexes with Piroxicam and 9-Aminoacridine

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Abstract

The solid-state structures of the complexes of calix[4]arenediphosphonic acid with piroxicam and 9-aminoacridine are described, in both cases, the classical interdigitated dimer formed by calix[4]arenediphosphonic acid is no longer present. For the 9-aminoacridine complex, a π–π stacked dimer of 9-aminoacridine is surrounded by calix[4]arenediphosphonic acid molecules with dimethyl sulfoxide included in the calix arene cavity. In the case of the piroxicam complex the piroxicam molecule forms a true inclusion complex and the pyridinium ring projects out to hydrogen bond to an opposing calix[4]arenediphosphonic acid, thus spanning the bilayer.

Graphical Abstract

The structures of the complexes of calix[4]arenediphosphonic acid with piroxicam and 9-aminoacridine show a breakdown in the classical interdigated calix-arene dimer with formation of trus inclusion complexes and exo-complexation.

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Authors and Affiliations

  1. Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland

    Aleksander Shkurenko & Kinga Suwinska

  2. LMI, Université Lyon 1 CNRS UMR 5615, 43 bvd 11 Novembre, 69622, Villeurbanne, France

    Hassim Seriouna, Karim Kedim, Jean-Baptiste Gervès & Anthony W. Coleman

  3. Faculty of Biology and Environmental Sciences, Cardinal Stefan Wyszynski University, K. Woycickiego 1/3, 01-938, Warsaw, Poland

    Kinga Suwinska

Authors
  1. Aleksander Shkurenko
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  2. Hassim Seriouna
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  3. Karim Kedim
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  4. Jean-Baptiste Gervès
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  5. Kinga Suwinska
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  6. Anthony W. Coleman
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Corresponding authors

Correspondence to Kinga Suwinska or Anthony W. Coleman.

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Shkurenko, A., Seriouna, H., Kedim, K. et al. Breaking Down the Interdigitated Dimeric Structure of Calix[4]arenediphosphonic Acid: the Structures of the Complexes with Piroxicam and 9-Aminoacridine. J Chem Crystallogr 44, 380–385 (2014). https://doi.org/10.1007/s10870-014-0526-2

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  • DOI: https://doi.org/10.1007/s10870-014-0526-2

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