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The crystal structure of 4'-{4-[(2,2,5,5-tetra-methyl-N-oxyl-3-pyrrolin-3-yl)ethyn-yl]phen-yl}-2,2':6',2''-terpyridine.

Meyer A, Wiecek J, Schnakenburg G, Schiemann O - Acta Crystallogr E Crystallogr Commun (2015)

Bottom Line: 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.Furthermore, edge-on C-H⋯π inter-actions between the phenyl-ene rings of neighbouring mol-ecules are observed along this direction.A two-dimensional C-H⋯O hydrogen-bonded network is formed within the (010) plane.

View Article: PubMed Central - HTML - PubMed

Affiliation: University of Bonn, Institute of Physical and Theoretical Chemistry, Wegelerstrasse 12, 53115 Bonn, Germany.

ABSTRACT
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 intra-molecular 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 mol-ecules are arranged in layers stacked along [001]. Slipped face-to-face π-π inter-actions 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 inter-actions between the phenyl-ene rings of neighbouring mol-ecules 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 mol-ecules is 5.412 (3) Å.

No MeSH data available.


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Closest distances between pyridine rings and edge-on C—H⋯π contact.
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fig5: Closest distances between pyridine rings and edge-on C—H⋯π contact.

Mentions: The packing within the crystal structure is shown in Figs. 2 ▸–4 ▸ ▸. The mol­ecules are stacked in layers along [001] (Fig. 2 ▸.) The oxygen atom of the nitroxyl group forms weak hydrogen bonds to the protons of the para-C—H group and the pyrroline C—H group of neighbouring mol­ecules (Table 1 ▸). These hydrogen bonds span a two-dimensional network within the (010) plane (Figs. 3 ▸ and 4 ▸). π–π inter­actions are observed along [001] between the terpyridine subunits of neighbouring mol­ecules (Figs. 3 ▸ and 5 ▸). These terpyridine subunits are arranged in a slipped face-to-face alignment (Janiak, 2000 ▸) with the shortest inter­molecular distances between the pyridine rings amounting to 3.700 (1) Å (measured from the centroid of N2, C6–C10 to the centroid of N4, C27–C31) and 3.781 (1) Å (centroid of N1, C1–C5 to the centroid of N4, C27–C31, see Fig. 5 ▸). Furthermore, the phenyl­ene rings of neighbouring mol­ecules show an edge-on C—H⋯π inter­action along the same axis (Table 1 ▸ and Fig. 5 ▸). The nitroxyl groups are arranged in an alternating manner pointing in opposite directions. The shortest oxygen–oxygen separation between neighbouring mol­ecules amounts to 5.412 (3) Å. The oxygen–oxygen distance is an important factor determining the strength of through space exchange inter­actions of nitroxyls (Rajca et al. 2006 ▸).


The crystal structure of 4'-{4-[(2,2,5,5-tetra-methyl-N-oxyl-3-pyrrolin-3-yl)ethyn-yl]phen-yl}-2,2':6',2''-terpyridine.

Meyer A, Wiecek J, Schnakenburg G, Schiemann O - Acta Crystallogr E Crystallogr Commun (2015)

Closest distances between pyridine rings and edge-on C—H⋯π contact.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4518943&req=5

fig5: Closest distances between pyridine rings and edge-on C—H⋯π contact.
Mentions: The packing within the crystal structure is shown in Figs. 2 ▸–4 ▸ ▸. The mol­ecules are stacked in layers along [001] (Fig. 2 ▸.) The oxygen atom of the nitroxyl group forms weak hydrogen bonds to the protons of the para-C—H group and the pyrroline C—H group of neighbouring mol­ecules (Table 1 ▸). These hydrogen bonds span a two-dimensional network within the (010) plane (Figs. 3 ▸ and 4 ▸). π–π inter­actions are observed along [001] between the terpyridine subunits of neighbouring mol­ecules (Figs. 3 ▸ and 5 ▸). These terpyridine subunits are arranged in a slipped face-to-face alignment (Janiak, 2000 ▸) with the shortest inter­molecular distances between the pyridine rings amounting to 3.700 (1) Å (measured from the centroid of N2, C6–C10 to the centroid of N4, C27–C31) and 3.781 (1) Å (centroid of N1, C1–C5 to the centroid of N4, C27–C31, see Fig. 5 ▸). Furthermore, the phenyl­ene rings of neighbouring mol­ecules show an edge-on C—H⋯π inter­action along the same axis (Table 1 ▸ and Fig. 5 ▸). The nitroxyl groups are arranged in an alternating manner pointing in opposite directions. The shortest oxygen–oxygen separation between neighbouring mol­ecules amounts to 5.412 (3) Å. The oxygen–oxygen distance is an important factor determining the strength of through space exchange inter­actions of nitroxyls (Rajca et al. 2006 ▸).

Bottom Line: 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.Furthermore, edge-on C-H⋯π inter-actions between the phenyl-ene rings of neighbouring mol-ecules are observed along this direction.A two-dimensional C-H⋯O hydrogen-bonded network is formed within the (010) plane.

View Article: PubMed Central - HTML - PubMed

Affiliation: University of Bonn, Institute of Physical and Theoretical Chemistry, Wegelerstrasse 12, 53115 Bonn, Germany.

ABSTRACT
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 intra-molecular 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 mol-ecules are arranged in layers stacked along [001]. Slipped face-to-face π-π inter-actions 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 inter-actions between the phenyl-ene rings of neighbouring mol-ecules 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 mol-ecules is 5.412 (3) Å.

No MeSH data available.


Related in: MedlinePlus