Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine

Autores
Granifo, Juan; Arévalo, Beatriz; Gaviño, Rubén; Suarez, Sebastian; Baggio, Ricardo Fortunato
Año de publicación
2016
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
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.
Fil: Granifo, Juan. Universidad de La Frontera; Chile
Fil: Arévalo, Beatriz. Universidad de La Frontera; Chile
Fil: Gaviño, Rubén. Universidad Nacional Autónoma de México; México
Fil: Suarez, Sebastian. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina. Comisión Nacional de Energía Atómica. Centro Atómico Constituyentes; Argentina
Fil: Baggio, Ricardo Fortunato. Comisión Nacional de Energía Atómica. Centro Atómico Constituyentes; Argentina
Materia
4′-SUBSTITUTED 2,2′:6′,2′′-TERPYRIDINE
AIM
ATOMS-IN-MOLECULES
ATTRACTIVE H⋯H INTERACTION
BADER'S THEORY
CRYSTAL STRUCTURE
THEORETICAL CHARACTERIZATION
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/117864

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oai_identifier_str oai:ri.conicet.gov.ar:11336/117864
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridineGranifo, JuanArévalo, BeatrizGaviño, RubénSuarez, SebastianBaggio, Ricardo Fortunato4′-SUBSTITUTED 2,2′:6′,2′′-TERPYRIDINEAIMATOMS-IN-MOLECULESATTRACTIVE H⋯H INTERACTIONBADER'S THEORYCRYSTAL STRUCTURETHEORETICAL CHARACTERIZATIONhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/14′-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.Fil: Granifo, Juan. Universidad de La Frontera; ChileFil: Arévalo, Beatriz. Universidad de La Frontera; ChileFil: Gaviño, Rubén. Universidad Nacional Autónoma de México; MéxicoFil: Suarez, Sebastian. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina. Comisión Nacional de Energía Atómica. Centro Atómico Constituyentes; ArgentinaFil: Baggio, Ricardo Fortunato. Comisión Nacional de Energía Atómica. Centro Atómico Constituyentes; ArgentinaInternational Union of Crystallography2016-10info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/117864Granifo, Juan; Arévalo, Beatriz; Gaviño, Rubén; Suarez, Sebastian; Baggio, Ricardo Fortunato; Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine; International Union of Crystallography; Acta Crystallographica Section C: Structural Chemistry; 72; 10-2016; 932-9382053-2296CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1107/S2053229616016533info:eu-repo/semantics/altIdentifier/url/http://scripts.iucr.org/cgi-bin/paper?S2053229616016533info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:25:54Zoai:ri.conicet.gov.ar:11336/117864instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 10:25:54.659CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine
title Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine
spellingShingle Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine
Granifo, Juan
4′-SUBSTITUTED 2,2′:6′,2′′-TERPYRIDINE
AIM
ATOMS-IN-MOLECULES
ATTRACTIVE H⋯H INTERACTION
BADER'S THEORY
CRYSTAL STRUCTURE
THEORETICAL CHARACTERIZATION
title_short Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine
title_full Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine
title_fullStr Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine
title_full_unstemmed Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine
title_sort Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine
dc.creator.none.fl_str_mv Granifo, Juan
Arévalo, Beatriz
Gaviño, Rubén
Suarez, Sebastian
Baggio, Ricardo Fortunato
author Granifo, Juan
author_facet Granifo, Juan
Arévalo, Beatriz
Gaviño, Rubén
Suarez, Sebastian
Baggio, Ricardo Fortunato
author_role author
author2 Arévalo, Beatriz
Gaviño, Rubén
Suarez, Sebastian
Baggio, Ricardo Fortunato
author2_role author
author
author
author
dc.subject.none.fl_str_mv 4′-SUBSTITUTED 2,2′:6′,2′′-TERPYRIDINE
AIM
ATOMS-IN-MOLECULES
ATTRACTIVE H⋯H INTERACTION
BADER'S THEORY
CRYSTAL STRUCTURE
THEORETICAL CHARACTERIZATION
topic 4′-SUBSTITUTED 2,2′:6′,2′′-TERPYRIDINE
AIM
ATOMS-IN-MOLECULES
ATTRACTIVE H⋯H INTERACTION
BADER'S THEORY
CRYSTAL STRUCTURE
THEORETICAL CHARACTERIZATION
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv 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.
Fil: Granifo, Juan. Universidad de La Frontera; Chile
Fil: Arévalo, Beatriz. Universidad de La Frontera; Chile
Fil: Gaviño, Rubén. Universidad Nacional Autónoma de México; México
Fil: Suarez, Sebastian. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina. Comisión Nacional de Energía Atómica. Centro Atómico Constituyentes; Argentina
Fil: Baggio, Ricardo Fortunato. Comisión Nacional de Energía Atómica. Centro Atómico Constituyentes; Argentina
description 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.
publishDate 2016
dc.date.none.fl_str_mv 2016-10
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/117864
Granifo, Juan; Arévalo, Beatriz; Gaviño, Rubén; Suarez, Sebastian; Baggio, Ricardo Fortunato; Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine; International Union of Crystallography; Acta Crystallographica Section C: Structural Chemistry; 72; 10-2016; 932-938
2053-2296
CONICET Digital
CONICET
url http://hdl.handle.net/11336/117864
identifier_str_mv Granifo, Juan; Arévalo, Beatriz; Gaviño, Rubén; Suarez, Sebastian; Baggio, Ricardo Fortunato; Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine; International Union of Crystallography; Acta Crystallographica Section C: Structural Chemistry; 72; 10-2016; 932-938
2053-2296
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1107/S2053229616016533
info:eu-repo/semantics/altIdentifier/url/http://scripts.iucr.org/cgi-bin/paper?S2053229616016533
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv International Union of Crystallography
publisher.none.fl_str_mv International Union of Crystallography
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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