A polymorphic form of 4,4-dimethyl-8-methylene-3-azabicyclo[3.3.1]non-2-en- 2-yl 3-indolyl ketone, an indole alkaloid extracted from Aristotelia chilensis (maqui)

Autores
Paz, Cristian; Becerra, José; Silva, Mario; Freire Espeleta, Eleonora; Baggio, Ricardo Fortunato
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The title compound [systematic name: (4,4-dimethyl-8-methylene-3- azabicyclo[3.3.1]non-2-en-2-yl)(1H-indol-3-yl)methanone], C20H 22N2O, (II), was obtained from mother liquors extracted from Aristotelia chilensis (commonly known as maqui), a native Chilean tree. The compound is a polymorphic form of that obtained from the same source and reported by Watson, Nagl, Silva, Cespedes & Jakupovic [Acta Cryst. (1989), C45, 1322-1324], (Ia). The molecule consists of an indolyl ketone fragment and a nested three-ring system, with both groups linked by a C - C bridge. Comparison of both forms shows that they do not differ in their gross features but in the relative orientation of the two ring systems, due to different rotations around the bridge, as measured by the O=C - C=N torsion angle [130.0 (7)° in (Ia) and 161.6 (2)° in (II)]. The resulting slight conformational differences are reflected in a number of intramolecular contacts being observed in (II) but not in (Ia). Regarding intermolecular interactions, both forms share a similar N - H...O synthon but with differing hydrogen-bonding strength, leading in both cases to C(6) catemers with different chain motifs. There are marked differences between the two forms regarding colour and the (de)localization of a double bond, which allows speculation about the possible existence of different variants of this type of molecule.
Fil: Paz, Cristian. Universidad de Concepción; Chile
Fil: Becerra, José. Universidad de Concepción; Chile
Fil: Silva, Mario. Universidad de Concepción; Chile
Fil: Freire Espeleta, Eleonora. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Comisión Nacional de Energía Atómica. Centro Atómico Constituyentes; Argentina. Universidad Nacional de San Martín. Escuela de Ciencia y Tecnología; Argentina
Fil: Baggio, Ricardo Fortunato. Comisión Nacional de Energía Atómica. Centro Atómico Constituyentes; Argentina
Materia
ARISTOTELIA CHILENSIS
CRYSTAL STRUCTURE
INDOLE ALKALOIDS
MAQUI
POLYMORPHS
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:11336/88264
Acceder
id CONICETDig_2e870adde73de808289829111df4374a
oai_identifier_str oai:ri.conicet.gov.ar:11336/88264
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling A polymorphic form of 4,4-dimethyl-8-methylene-3-azabicyclo[3.3.1]non-2-en- 2-yl 3-indolyl ketone, an indole alkaloid extracted from Aristotelia chilensis (maqui)Paz, CristianBecerra, JoséSilva, MarioFreire Espeleta, EleonoraBaggio, Ricardo FortunatoARISTOTELIA CHILENSISCRYSTAL STRUCTUREINDOLE ALKALOIDSMAQUIPOLYMORPHShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The title compound [systematic name: (4,4-dimethyl-8-methylene-3- azabicyclo[3.3.1]non-2-en-2-yl)(1H-indol-3-yl)methanone], C20H 22N2O, (II), was obtained from mother liquors extracted from Aristotelia chilensis (commonly known as maqui), a native Chilean tree. The compound is a polymorphic form of that obtained from the same source and reported by Watson, Nagl, Silva, Cespedes & Jakupovic [Acta Cryst. (1989), C45, 1322-1324], (Ia). The molecule consists of an indolyl ketone fragment and a nested three-ring system, with both groups linked by a C - C bridge. Comparison of both forms shows that they do not differ in their gross features but in the relative orientation of the two ring systems, due to different rotations around the bridge, as measured by the O=C - C=N torsion angle [130.0 (7)° in (Ia) and 161.6 (2)° in (II)]. The resulting slight conformational differences are reflected in a number of intramolecular contacts being observed in (II) but not in (Ia). Regarding intermolecular interactions, both forms share a similar N - H...O synthon but with differing hydrogen-bonding strength, leading in both cases to C(6) catemers with different chain motifs. There are marked differences between the two forms regarding colour and the (de)localization of a double bond, which allows speculation about the possible existence of different variants of this type of molecule.Fil: Paz, Cristian. Universidad de Concepción; ChileFil: Becerra, José. Universidad de Concepción; ChileFil: Silva, Mario. Universidad de Concepción; ChileFil: Freire Espeleta, Eleonora. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Comisión Nacional de Energía Atómica. Centro Atómico Constituyentes; Argentina. Universidad Nacional de San Martín. Escuela de Ciencia y Tecnología; ArgentinaFil: Baggio, Ricardo Fortunato. Comisión Nacional de Energía Atómica. Centro Atómico Constituyentes; ArgentinaWiley Blackwell Publishing, Inc2013-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/88264Paz, Cristian; Becerra, José; Silva, Mario; Freire Espeleta, Eleonora; Baggio, Ricardo Fortunato; A polymorphic form of 4,4-dimethyl-8-methylene-3-azabicyclo[3.3.1]non-2-en- 2-yl 3-indolyl ketone, an indole alkaloid extracted from Aristotelia chilensis (maqui); Wiley Blackwell Publishing, Inc; Acta Crystallographica Section C-Crystal Structure Communications; 69; 12; 12-2013; 1509-15120108-2701CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1107/S0108270113025523info:eu-repo/semantics/altIdentifier/url/http://scripts.iucr.org/cgi-bin/paper?S0108270113025523info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:21:40Zoai:ri.conicet.gov.ar:11336/88264instacron: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 10:21:41.259CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv A polymorphic form of 4,4-dimethyl-8-methylene-3-azabicyclo[3.3.1]non-2-en- 2-yl 3-indolyl ketone, an indole alkaloid extracted from Aristotelia chilensis (maqui)
title A polymorphic form of 4,4-dimethyl-8-methylene-3-azabicyclo[3.3.1]non-2-en- 2-yl 3-indolyl ketone, an indole alkaloid extracted from Aristotelia chilensis (maqui)
spellingShingle A polymorphic form of 4,4-dimethyl-8-methylene-3-azabicyclo[3.3.1]non-2-en- 2-yl 3-indolyl ketone, an indole alkaloid extracted from Aristotelia chilensis (maqui)
Paz, Cristian
ARISTOTELIA CHILENSIS
CRYSTAL STRUCTURE
INDOLE ALKALOIDS
MAQUI
POLYMORPHS
title_short A polymorphic form of 4,4-dimethyl-8-methylene-3-azabicyclo[3.3.1]non-2-en- 2-yl 3-indolyl ketone, an indole alkaloid extracted from Aristotelia chilensis (maqui)
title_full A polymorphic form of 4,4-dimethyl-8-methylene-3-azabicyclo[3.3.1]non-2-en- 2-yl 3-indolyl ketone, an indole alkaloid extracted from Aristotelia chilensis (maqui)
title_fullStr A polymorphic form of 4,4-dimethyl-8-methylene-3-azabicyclo[3.3.1]non-2-en- 2-yl 3-indolyl ketone, an indole alkaloid extracted from Aristotelia chilensis (maqui)
title_full_unstemmed A polymorphic form of 4,4-dimethyl-8-methylene-3-azabicyclo[3.3.1]non-2-en- 2-yl 3-indolyl ketone, an indole alkaloid extracted from Aristotelia chilensis (maqui)
title_sort A polymorphic form of 4,4-dimethyl-8-methylene-3-azabicyclo[3.3.1]non-2-en- 2-yl 3-indolyl ketone, an indole alkaloid extracted from Aristotelia chilensis (maqui)
dc.creator.none.fl_str_mv Paz, Cristian
Becerra, José
Silva, Mario
Freire Espeleta, Eleonora
Baggio, Ricardo Fortunato
author Paz, Cristian
author_facet Paz, Cristian
Becerra, José
Silva, Mario
Freire Espeleta, Eleonora
Baggio, Ricardo Fortunato
author_role author
author2 Becerra, José
Silva, Mario
Freire Espeleta, Eleonora
Baggio, Ricardo Fortunato
author2_role author
author
author
author
dc.subject.none.fl_str_mv ARISTOTELIA CHILENSIS
CRYSTAL STRUCTURE
INDOLE ALKALOIDS
MAQUI
POLYMORPHS
topic ARISTOTELIA CHILENSIS
CRYSTAL STRUCTURE
INDOLE ALKALOIDS
MAQUI
POLYMORPHS
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The title compound [systematic name: (4,4-dimethyl-8-methylene-3- azabicyclo[3.3.1]non-2-en-2-yl)(1H-indol-3-yl)methanone], C20H 22N2O, (II), was obtained from mother liquors extracted from Aristotelia chilensis (commonly known as maqui), a native Chilean tree. The compound is a polymorphic form of that obtained from the same source and reported by Watson, Nagl, Silva, Cespedes & Jakupovic [Acta Cryst. (1989), C45, 1322-1324], (Ia). The molecule consists of an indolyl ketone fragment and a nested three-ring system, with both groups linked by a C - C bridge. Comparison of both forms shows that they do not differ in their gross features but in the relative orientation of the two ring systems, due to different rotations around the bridge, as measured by the O=C - C=N torsion angle [130.0 (7)° in (Ia) and 161.6 (2)° in (II)]. The resulting slight conformational differences are reflected in a number of intramolecular contacts being observed in (II) but not in (Ia). Regarding intermolecular interactions, both forms share a similar N - H...O synthon but with differing hydrogen-bonding strength, leading in both cases to C(6) catemers with different chain motifs. There are marked differences between the two forms regarding colour and the (de)localization of a double bond, which allows speculation about the possible existence of different variants of this type of molecule.
Fil: Paz, Cristian. Universidad de Concepción; Chile
Fil: Becerra, José. Universidad de Concepción; Chile
Fil: Silva, Mario. Universidad de Concepción; Chile
Fil: Freire Espeleta, Eleonora. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Comisión Nacional de Energía Atómica. Centro Atómico Constituyentes; Argentina. Universidad Nacional de San Martín. Escuela de Ciencia y Tecnología; Argentina
Fil: Baggio, Ricardo Fortunato. Comisión Nacional de Energía Atómica. Centro Atómico Constituyentes; Argentina
description The title compound [systematic name: (4,4-dimethyl-8-methylene-3- azabicyclo[3.3.1]non-2-en-2-yl)(1H-indol-3-yl)methanone], C20H 22N2O, (II), was obtained from mother liquors extracted from Aristotelia chilensis (commonly known as maqui), a native Chilean tree. The compound is a polymorphic form of that obtained from the same source and reported by Watson, Nagl, Silva, Cespedes & Jakupovic [Acta Cryst. (1989), C45, 1322-1324], (Ia). The molecule consists of an indolyl ketone fragment and a nested three-ring system, with both groups linked by a C - C bridge. Comparison of both forms shows that they do not differ in their gross features but in the relative orientation of the two ring systems, due to different rotations around the bridge, as measured by the O=C - C=N torsion angle [130.0 (7)° in (Ia) and 161.6 (2)° in (II)]. The resulting slight conformational differences are reflected in a number of intramolecular contacts being observed in (II) but not in (Ia). Regarding intermolecular interactions, both forms share a similar N - H...O synthon but with differing hydrogen-bonding strength, leading in both cases to C(6) catemers with different chain motifs. There are marked differences between the two forms regarding colour and the (de)localization of a double bond, which allows speculation about the possible existence of different variants of this type of molecule.
publishDate 2013
dc.date.none.fl_str_mv 2013-12
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/11336/88264
Paz, Cristian; Becerra, José; Silva, Mario; Freire Espeleta, Eleonora; Baggio, Ricardo Fortunato; A polymorphic form of 4,4-dimethyl-8-methylene-3-azabicyclo[3.3.1]non-2-en- 2-yl 3-indolyl ketone, an indole alkaloid extracted from Aristotelia chilensis (maqui); Wiley Blackwell Publishing, Inc; Acta Crystallographica Section C-Crystal Structure Communications; 69; 12; 12-2013; 1509-1512
0108-2701
CONICET Digital
CONICET
url http://hdl.handle.net/11336/88264
identifier_str_mv Paz, Cristian; Becerra, José; Silva, Mario; Freire Espeleta, Eleonora; Baggio, Ricardo Fortunato; A polymorphic form of 4,4-dimethyl-8-methylene-3-azabicyclo[3.3.1]non-2-en- 2-yl 3-indolyl ketone, an indole alkaloid extracted from Aristotelia chilensis (maqui); Wiley Blackwell Publishing, Inc; Acta Crystallographica Section C-Crystal Structure Communications; 69; 12; 12-2013; 1509-1512
0108-2701
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/S0108270113025523
info:eu-repo/semantics/altIdentifier/url/http://scripts.iucr.org/cgi-bin/paper?S0108270113025523
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 Wiley Blackwell Publishing, Inc
publisher.none.fl_str_mv Wiley Blackwell Publishing, Inc
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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score 13.070432

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