The crystal structure of 4′-{4-[(2,2,5,5-tetramethyl-N-oxyl-3-pyrrolin-3-yl)ethynyl]phenyl}-2,2′:6′,2′′-terpyridine
The terpyridine group of the title compound, C31H27N4O, assumes an all-transoid 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 suc...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2015-07-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989015012086 |
| _version_ | 1819290954115317760 |
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| author | Andreas Meyer Jennifer Wiecek Gregor Schnakenburg Olav Schiemann |
| author_facet | Andreas Meyer Jennifer Wiecek Gregor Schnakenburg Olav Schiemann |
| author_sort | Andreas Meyer |
| collection | DOAJ |
| description | The terpyridine group of the title compound, C31H27N4O, assumes an all-transoid 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. |
| first_indexed | 2024-12-24T03:30:56Z |
| format | Article |
| id | doaj.art-15be93787f1346a99a48653979a060b5 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-12-24T03:30:56Z |
| publishDate | 2015-07-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-15be93787f1346a99a48653979a060b52022-12-21T17:17:12ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902015-07-0171787087410.1107/S2056989015012086lh5769The crystal structure of 4′-{4-[(2,2,5,5-tetramethyl-N-oxyl-3-pyrrolin-3-yl)ethynyl]phenyl}-2,2′:6′,2′′-terpyridineAndreas Meyer0Jennifer Wiecek1Gregor Schnakenburg2Olav Schiemann3University of Bonn, Institute of Physical and Theoretical Chemistry, Wegelerstrasse 12, 53115 Bonn, GermanyUniversity of Bonn, Institute of Physical and Theoretical Chemistry, Wegelerstrasse 12, 53115 Bonn, GermanyUniversity of Bonn, Institute of Inorganic Chemistry, Gerhard-Domagk-Strasse 1, 53121 Bonn, GermanyUniversity of Bonn, Institute of Physical and Theoretical Chemistry, Wegelerstrasse 12, 53115 Bonn, GermanyThe terpyridine group of the title compound, C31H27N4O, assumes an all-transoid 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.http://scripts.iucr.org/cgi-bin/paper?S2056989015012086crystal structureterpyridinenitroxidenitroxylC—H...π interactionsπ–π interactionsC—H...O hydrogen bonding |
| spellingShingle | Andreas Meyer Jennifer Wiecek Gregor Schnakenburg Olav Schiemann The crystal structure of 4′-{4-[(2,2,5,5-tetramethyl-N-oxyl-3-pyrrolin-3-yl)ethynyl]phenyl}-2,2′:6′,2′′-terpyridine Acta Crystallographica Section E: Crystallographic Communications crystal structure terpyridine nitroxide nitroxyl C—H...π interactions π–π interactions C—H...O hydrogen bonding |
| title | The crystal structure of 4′-{4-[(2,2,5,5-tetramethyl-N-oxyl-3-pyrrolin-3-yl)ethynyl]phenyl}-2,2′:6′,2′′-terpyridine |
| title_full | The crystal structure of 4′-{4-[(2,2,5,5-tetramethyl-N-oxyl-3-pyrrolin-3-yl)ethynyl]phenyl}-2,2′:6′,2′′-terpyridine |
| title_fullStr | The crystal structure of 4′-{4-[(2,2,5,5-tetramethyl-N-oxyl-3-pyrrolin-3-yl)ethynyl]phenyl}-2,2′:6′,2′′-terpyridine |
| title_full_unstemmed | The crystal structure of 4′-{4-[(2,2,5,5-tetramethyl-N-oxyl-3-pyrrolin-3-yl)ethynyl]phenyl}-2,2′:6′,2′′-terpyridine |
| title_short | The crystal structure of 4′-{4-[(2,2,5,5-tetramethyl-N-oxyl-3-pyrrolin-3-yl)ethynyl]phenyl}-2,2′:6′,2′′-terpyridine |
| title_sort | crystal structure of 4 4 2 2 5 5 tetramethyl n oxyl 3 pyrrolin 3 yl ethynyl phenyl 2 2 6 2 terpyridine |
| topic | crystal structure terpyridine nitroxide nitroxyl C—H...π interactions π–π interactions C—H...O hydrogen bonding |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989015012086 |
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