The crystal structure of 4′-{4-[(2,2,5,5-tetramethyl-N-oxyl-3-pyrrolin-3-yl)ethynyl]phenyl}-2,2′:6′,2″-terpyridine

Andreas Meyer, Jennifer Wiecek, Gregor Schnakenburg, Olav Schiemann

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

The terpyridine group of the title compound, C31H27N4O, assumes an alltransoid conformation and is essentially planar with the dihedral angles between the mean planes of the central pyridine and the two outer rings amounting to 3.87 (5) and 1.98 (5)°. The pyrroline-N-oxyl group commonly seen in such nitroxyls is found in the title structure and the mean plane of the pyrroline ring subtends a dihedral angle of 88.44 (7)° to the mean plane of the central pyridine ring. The intramolecular separation between the nitrogen atom of the central pyridine unit of the terpyridine group and the nitroxyl group is 14.120 (2) Å. In the crystal, the molecules are arranged in layers stacked along [001]. Slipped face-to-face π-π interactions between the pyridine rings are observed along this direction with the shortest centroid-centroid distances amounting to 3.700 (1) and 3.781 (1) Å. Furthermore, edge-on C-H⋯π interactions between the phenylene rings of neighbouring molecules are observed along this direction. A two-dimensional C-H⋯O hydrogen-bonded network is formed within the (010) plane. The shortest O⋯O separation between neighbouring molecules is 5.412 (3) Å.

Original languageEnglish
Pages (from-to)870-874
Number of pages5
JournalActa Crystallographica Section E: Crystallographic Communications
Volume71
Issue number7
DOIs
StatePublished - Jul 2015
Externally publishedYes

Keywords

  • C-H⋯O hydrogen bonding
  • C-H⋯π interactions
  • Crystal structure
  • Nitroxide
  • Nitroxyl
  • Terpyridine
  • π-π interactions

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