A competition between N---O and C---O through space interactions in the crystal structures of 3,3'-dinitro-2,2'-bipyridine N-oxides and N,N'-dioxides

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O'Leary, J and Wallis, JD ORCID: https://orcid.org/0000-0001-7259-8783, 2007. A competition between N---O and C---O through space interactions in the crystal structures of 3,3'-dinitro-2,2'-bipyridine N-oxides and N,N'-dioxides. CrystEngComm, 9 (10), pp. 941-950.

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Abstract

The crystal structures of a series of 3,3’-dinitro-2,2’-bipyridine N-oxides and N,N’-dioxides consistently show 1,5 interactions between nitro oxygen atoms and aromatic carbon atoms ((ON)O---C: 2.623(2)-2.839(2) Å) while there are also 1,6 interactions between N-oxide oxygen atoms and nitro nitrogen atoms in most cases (O---N(O2): 2.737(2)-2.874(3) Å). The O---C interactions appears to be a common feature in ortho-nitro-biphenyl systems, and there is some evidence that the effect is cooperative when there are ortho nitro groups on both rings. The O---N interactions are considerably longer than the corresponding 1,5 N---O interaction measured here in 8-nitroquinoline-1-oxide (O---N(O2): 2.5418(17) Å), which in turn is longer than the corresponding N---O interaction in the corresponding 8-diazonium-1-oxide analogue.

Item Type:	Journal article
Publication Title:	CrystEngComm
Creators:	O'Leary, J. and Wallis, J.D.
Publisher:	Royal Society of Chemistry
Date:	2007
Volume:	9
Number:	10
Divisions:	Schools > School of Science and Technology
Record created by:	EPrints Services
Date Added:	09 Oct 2015 10:20
Last Modified:	09 Jun 2017 13:26
URI:	https://irep.ntu.ac.uk/id/eprint/11379