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Highly Sheared Anti-Parallel Dipolar Carbonyl···Carbonyl Interaction in the Crystal Packing of Strapped Crown-3-Pyromellitimide
Ethan Nam Wei
Howe A,
Mohan
Bhadbhade B and
Pall
Thordarson A C
A
School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia.
B
Mark Wainwright Analytical Centre, The University of New South Wales, Sydney, NSW 2052, Australia.
C
Corresponding author. Email: p.thordarson@unsw.edu.au
Australian Journal of Chemistry
65(10)
1384-1389 http://dx.doi.org/10.1071/CH12085
Submitted: 8 February 2012 Accepted: 21 May 2012 Published:
28
June
2012
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Abstract
Non-covalent dipolar interactions between pairs of carbonyls have been demonstrated to play a significant role in the crystal packing and formation of supramolecular structural architecture of small organic molecules. Under high dilution, the strapped crown-3-pyromellitimide 4 and macrocyclic crown-6-bispyromellitimide 5 were synthesised in concert and demonstrated selective molecular recognition towards Na+ and K+, respectively. The molecular structure of strapped crown-3-pyromellitimide 4 was solved using X-ray crystallography and an unusual highly sheared anti-parallel dipolar carbonyl···carbonyl interaction was observed in the crystal packing. The intermolecular interaction has a torsion angle of 44.1°, and deviates from the three idealised motifs reported in literature. This finding further highlights the importance and versatility of dipolar carbonyl···carbonyl interaction in the crystal packing of organic molecules. 
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