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Synthesis of 2-pyridone-fused 2,2 '-bipyridine derivatives. An unexpectedly complex solid state structure of 3,6-dimethyl-9H-4,5,9-triazaphenanthren-10-one

Jonsson, Stefan LU ; Solano, Carlos LU ; Wendt, Ola LU ; Siegel, Jay S and Wärnmark, Kenneth LU (2005) In Organic and Biomolecular Chemistry 3(6). p.996-1001
Abstract
2- Pyridone- fused 2,2'- bipyridine derivatives 1a and 1b were synthesised. X- Ray diffraction analysis of 1b revealed a highly complex solid state structure with a disordered molecule imbedded in a channel structure formed by a centrosymmetric lattice of hexagonally packed, hydrogen bonded columns. The columns are assembled from three symmetry independent molecules. Dimerisation of the self- complementary cis- amide hydrogen bond motif is overridden by the fulfilment of the proton coordination ability of the phenanthroline nitrogens in accordance with Etter's rules of hydrogen bond priorities.
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organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Organic and Biomolecular Chemistry
volume
3
issue
6
pages
996 - 1001
publisher
Royal Society of Chemistry
external identifiers
  • wos:000227454700008
  • pmid:15750641
  • scopus:16244378225
  • pmid:15750641
ISSN
1477-0539
DOI
10.1039/b417485b
language
English
LU publication?
yes
additional info
The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)
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ee72ba30-f204-4bf0-9d91-3935db3e1ea3 (old id 152421)
date added to LUP
2016-04-01 12:24:04
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2020-12-27 03:06:17
@article{ee72ba30-f204-4bf0-9d91-3935db3e1ea3,
  abstract     = {2- Pyridone- fused 2,2'- bipyridine derivatives 1a and 1b were synthesised. X- Ray diffraction analysis of 1b revealed a highly complex solid state structure with a disordered molecule imbedded in a channel structure formed by a centrosymmetric lattice of hexagonally packed, hydrogen bonded columns. The columns are assembled from three symmetry independent molecules. Dimerisation of the self- complementary cis- amide hydrogen bond motif is overridden by the fulfilment of the proton coordination ability of the phenanthroline nitrogens in accordance with Etter's rules of hydrogen bond priorities.},
  author       = {Jonsson, Stefan and Solano, Carlos and Wendt, Ola and Siegel, Jay S and Wärnmark, Kenneth},
  issn         = {1477-0539},
  language     = {eng},
  number       = {6},
  pages        = {996--1001},
  publisher    = {Royal Society of Chemistry},
  series       = {Organic and Biomolecular Chemistry},
  title        = {Synthesis of 2-pyridone-fused 2,2 '-bipyridine derivatives. An unexpectedly complex solid state structure of 3,6-dimethyl-9H-4,5,9-triazaphenanthren-10-one},
  url          = {http://dx.doi.org/10.1039/b417485b},
  doi          = {10.1039/b417485b},
  volume       = {3},
  year         = {2005},
}