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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.

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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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The mol­ecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted for clarity.
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fig1: The mol­ecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted for clarity.

Mentions: The structure of the title compound (1) is shown in Fig. 1 ▸. The terpyridine group of (1) assumes an all-transoid conformation and is essentially planar with angles between the mean planes of the central pyridine (N1, C1–C5, r.m.s deviation from the mean plane = 0.006 Å) and the two outer rings amounting to 3.87 (5)° (N4, C27–C31, r.m.s. deviation from the mean plane = 0.003 Å) and 1.98 (5)° (N2, C6–C10, r.m.s deviation from the mean plane = 0.006 Å), respectively. The pyrroline-N-oxyl unit commonly found for such nitroxyls is seen in the structure and its mean plane (N3, C19–C22, r.m.s deviation from the mean plane = 0.006 Å) subtends a dihedral angle of 88.44 (7)° to the mean plane of the central pyridine ring (for similar structural motifs, see Margraf et al., 2009 ▸ and Schuetz et al., 2010 ▸). The subunits are linked by a 4-ethinylene­phenyl­ene group. The mean plane of the phenyl­ene group (C11–C16, r.m.s deviation from the mean plane < 0.001 Å) is tilted with respect to both the central pyridine ring [dihedral angle of 51.36 (5)°] and the pyrroline-N-oxyl [dihedral angle of 37.62 (7)°]. The angles C18—C17—C14 [177.35 (19)°] and C17—C18—C19 [175.64 (18)°] are slightly lower than the 180° expected for a strictly linear shape of the mol­ecular backbone. Two short intra­molecular hydrogen–nitro­gen distances are observed between the two meta-protons of the central pyridine subunit and the nitro­gen atoms of the external pyridine rings (Table 1 ▸). Murguly et al. (1999 ▸) propose weak intra­molecular hydrogen bonds for these atoms. The intra­molecular separation between the terpyridine group and the nitroxyl amounts to 14.120 (2) Å (measured between O1 and N1).


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)

The mol­ecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted for clarity.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

fig1: The mol­ecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted for clarity.
Mentions: The structure of the title compound (1) is shown in Fig. 1 ▸. The terpyridine group of (1) assumes an all-transoid conformation and is essentially planar with angles between the mean planes of the central pyridine (N1, C1–C5, r.m.s deviation from the mean plane = 0.006 Å) and the two outer rings amounting to 3.87 (5)° (N4, C27–C31, r.m.s. deviation from the mean plane = 0.003 Å) and 1.98 (5)° (N2, C6–C10, r.m.s deviation from the mean plane = 0.006 Å), respectively. The pyrroline-N-oxyl unit commonly found for such nitroxyls is seen in the structure and its mean plane (N3, C19–C22, r.m.s deviation from the mean plane = 0.006 Å) subtends a dihedral angle of 88.44 (7)° to the mean plane of the central pyridine ring (for similar structural motifs, see Margraf et al., 2009 ▸ and Schuetz et al., 2010 ▸). The subunits are linked by a 4-ethinylene­phenyl­ene group. The mean plane of the phenyl­ene group (C11–C16, r.m.s deviation from the mean plane < 0.001 Å) is tilted with respect to both the central pyridine ring [dihedral angle of 51.36 (5)°] and the pyrroline-N-oxyl [dihedral angle of 37.62 (7)°]. The angles C18—C17—C14 [177.35 (19)°] and C17—C18—C19 [175.64 (18)°] are slightly lower than the 180° expected for a strictly linear shape of the mol­ecular backbone. Two short intra­molecular hydrogen–nitro­gen distances are observed between the two meta-protons of the central pyridine subunit and the nitro­gen atoms of the external pyridine rings (Table 1 ▸). Murguly et al. (1999 ▸) propose weak intra­molecular hydrogen bonds for these atoms. The intra­molecular separation between the terpyridine group and the nitroxyl amounts to 14.120 (2) Å (measured between O1 and N1).

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