Versatile inclusion behaviour of a dinitrocalix[4]arene having two ester pendants - Preparation and x-ray crystal structures of complexes

Tobias Gruber, Edwin Weber, Wilhelm Seichter, Petra Bombicz, Ingeborg Csöregh

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

An upper-rim dinitro-substituted calix[4]arene possessing two lower-rim ethyl ester pendant groups (1) has been shown to form solid inclusion compounds with acetone (1:1) (1a), DMF (1:1) (1b), DMSO (1:1) (1c) and n-BuOH (2:1) (1d). X-ray crystal structures of the four complexes 1a-d are reported and comparatively discussed, including isostructurality calculations. Although the solid-state conformation of the dinitrocalix[4]arene moiety, stabilized by two intramolecular O-H...O bonds, is maintained in the four inclusion compounds, and all four co-crystals have similar unit cell dimensions and identical space group symmetries, only three of them (1a-c) are homostructural. Depending on the nature of the guest molecule, either the upper or the lower rim site of the calixarene is involved in the complexation, demonstrating either cavitate- or clathrate-type of supramolecular interactions, respectively. Moreover, due to the different guest recognition modes, the calixarene host in 1d is rotated through a non-crystallographic virtual rotation of 180° within the unit cell, in relation to the host molecules in each of the other three homostructural compounds 1a-c, thus giving rise to supramolecular morphotropism - to our knowledge the first case ever described.

Original languageEnglish
Pages (from-to)537-547
Number of pages11
JournalSupramolecular Chemistry
Volume18
Issue number6
DOIs
Publication statusPublished - Sep 1 2006

Keywords

  • Calixarene host
  • Crystalline inclusion compounds
  • Isostructurality calculations
  • Morphotropism
  • Organic guests
  • Supramolecular interactions
  • X-ray crystal structures

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint Dive into the research topics of 'Versatile inclusion behaviour of a dinitrocalix[4]arene having two ester pendants - Preparation and x-ray crystal structures of complexes'. Together they form a unique fingerprint.

  • Cite this