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Abstract:

4′-Substituted derivatives of 2,2′:6′,2′′-terpyridine with N-containing heteroaromatic substituents, such as pyridyl groups, might be able to coordinate metal centres through the extra N-donor atom, in addition to the chelating terpyridine N atoms. The incorporation of these peripheral N-donor sites would also allow for the diversification of the types of noncovalent interactions present, such as hydrogen bonding and π-π stacking. The title compound, C24H16N4, consists of a 2,2′:6′,2′′-terpyridine nucleus (tpy), with a pendant isoquinoline group (isq) bound at the central pyridine (py) ring. The tpy nucleus deviates slightly from planarity, with interplanar angles between the lateral and central py rings in the range 2.24(7)-7.90(7)°, while the isq group is rotated significantly [by 46.57(6)°] out of this planar scheme, associated with a short Htpy⋯Hisq contact of 2.32Å. There are no strong noncovalent interactions in the structure, the main ones being of the π-π and C - H⋯π types, giving rise to columnar arrays along [001], further linked by C - H⋯N hydrogen bonds into a three-dimensional supramolecular structure. An Atoms In Molecules (AIM) analysis of the noncovalent interactions provided illuminating results, and while confirming the bonding character for all those interactions unquestionable from a geometrical point of view, it also provided answers for some cases where geometric parameters are not informative, in particular, the short Htpy⋯Hisq contact of 2.32Å to which AIM ascribed an attractive character. © 2016 International Union of Crystallography.

Registro:

Documento: Artículo
Título:Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine
Autor:Granifo, J.; Arévalo, B.; Gaviño, R.; Suárez, S.; Baggio, R.
Filiación:Departamento de Ciencias Químicas y Recursos Naturales, Facultad de Ingeniería y Ciencias, Universidad de la Frontera, Casilla 54-D, Temuco, Chile
Instituto de Química, Universidad Nacional Autónoma de México, Cd. Universitaria, Circuito Exterior Coyoacán, México, 04510, Mexico
Departamento de Química Inorgánica, Analítica y Química, Física/INQUIMAE-CONICET, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina
Gerencia de Investigación y Aplicaciones, Centro Atómico Constituyentes, Comisión Nacional de Energía Atómica, Buenos Aires, Argentina
Palabras clave:4′-substituted 2,2′:6′,2′′-terpyridine; AIM; atoms-in-molecules; attractive H⋯H interaction; Bader's theory; crystal structure; theoretical characterization; Atoms; Crystal structure; Hydrogen bonds; Ions; Molecules; Atoms in Molecules; Bader's theory; Bonding character; Columnar arrays; Non-covalent interaction; Supramolecular structure; Terpyridines; Title compounds; attractive H..H interaction; Crystal atomic structure
Año:2016
Volumen:72
Página de inicio:932
Página de fin:938
DOI: http://dx.doi.org/10.1107/S2053229616016533
Título revista:Acta Crystallographica Section C: Structural Chemistry
Título revista abreviado:Acta crystallogr., C Struct. Chem.
ISSN:20532296
CODEN:ACSCG
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_20532296_v72_n_p932_Granifo

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Citas:

---------- APA ----------
Granifo, J., Arévalo, B., Gaviño, R., Suárez, S. & Baggio, R. (2016) . Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine. Acta Crystallographica Section C: Structural Chemistry, 72, 932-938.
http://dx.doi.org/10.1107/S2053229616016533
---------- CHICAGO ----------
Granifo, J., Arévalo, B., Gaviño, R., Suárez, S., Baggio, R. "Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine" . Acta Crystallographica Section C: Structural Chemistry 72 (2016) : 932-938.
http://dx.doi.org/10.1107/S2053229616016533
---------- MLA ----------
Granifo, J., Arévalo, B., Gaviño, R., Suárez, S., Baggio, R. "Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine" . Acta Crystallographica Section C: Structural Chemistry, vol. 72, 2016, pp. 932-938.
http://dx.doi.org/10.1107/S2053229616016533
---------- VANCOUVER ----------
Granifo, J., Arévalo, B., Gaviño, R., Suárez, S., Baggio, R. Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine. Acta crystallogr., C Struct. Chem. 2016;72:932-938.
http://dx.doi.org/10.1107/S2053229616016533