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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.

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.

SUBMITTER: Meyer A

PROVIDER: S-EPMC4518943 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Project description:The title compound, C44H35N4O3·2.5C6H6 (1), consists of a terpyridine and a N-oxylpyrroline-3-formate group separated by an aromatic spacer, viz. 4-(phenyl-ethyn-yl)-1,1'-biphenyl. It crystallized in the triclinic space group P-1 with two and a half benzene solvate mol-ecules (one benzene mol-ecule is located about an inversion center), while the di-chloro-methane solvate (2) of the same mol-ecule [Ackermann et al. (2015 ▸). Chem. Commun. 51, 5257-5260] crystallized in the tetra-gonal space group P42/n, with considerable disorder in the mol-ecule. In (1), the terpyridine (terpy) group assumes an all-trans conformation typical for terpyridines. It is essentially planar with the two outer pyridine rings (B and C) inclined to the central pyridine ring (A) by 8.70 (15) and 14.55 (14)°, respectively. The planes of the aromatic spacer (D, E and F) are nearly coplanar with dihedral angles D/E, D/F and E/F being 3.42 (15), 5.80 (15) and 4.00 (16)°, respectively. It is twisted with respect to the terpy group with, for example, dihedral angle A/D being 24.48 (14)°. The mean plane of the N-oxylpyrroline is almost normal to the biphenyl ring F, making a dihedral angle of 86.57 (16)°, and it is inclined to pyridine ring A by 72.61 (15)°. The intra-molecular separation between the O atom of the nitroxyl group and the N atom of the central pyridine ring of the terpyridine group is 25.044 (3) Å. In the crystal, mol-ecules are linked by pairs of C-H⋯O hydrogen bonds, forming inversion dimers. The dimers stack along the c axis forming columns. Within and between the columns, the spaces are occupied by benzene mol-ecules. The shortest oxygen-oxygen separation between nitroxyl groups is 4.004 (4) Å. The details of the title compound are compared with those of the di-chloro-methane solvate (2) and with the structure of a related mol-ecule, 4'-{4-[(2,2,5,5-tetra-methyl-N-oxyl-3-pyrrolin-3-yl)ethyn-yl]phen-yl}-2,2':6',2''-terpyridine (3), which has an ethynylphenyl spacer [Meyer et al. (2015). Acta Cryst. E71, 870-874].

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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.

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