(-)-Isosantonic acid: Alteration of the hydrogen-bonding mode by configurational inversion at a single centre in a γ,ε- diketocarboxylic acid

Autores
Zinczuk, Juan; Ruveda, Edmundo; Lalancette, Roger A.; Thompson, Hugh W.
Año de publicación
2006
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The title diketo acid, (1R,3aS,6aS,7R,9S)-(-)-α,3a,7-trimethyl-5,8- dioxo-1,4-ethanoperhydropentalene-1-acetic acid (C15H 20O4), is shown to aggregate in the crystal structure as acid-to-ketone hydrogen-bonding catemers, whose chains follow 21 screw axes from each carboxyl to a ketone in a neighbouring molecule [O⋯O = 2.7472(13) and O⋯H - O = 172.7(17)°]. Two parallel counterdirectional screw-related single-strand hydrogen-bonding chains pass through the cell in the a direction. Six intermolecular C - H⋯O=C close contacts are found. Comparisons are drawn with a diastereomer having the opposite configuration at the methylated chiral centre adjacent to the carboxyl group.
Fil: Zinczuk, Juan. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Ruveda, Edmundo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Lalancette, Roger A.. Rutgers University; Estados Unidos
Fil: Thompson, Hugh W.. Rutgers University; Estados Unidos
Materia
Single-crystal X-ray study
Mean (C–C) = 0.002 A
Data-to-parameter ratio = 9.2
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/133973
Acceder
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network_name_str CONICET Digital (CONICET)
spelling (-)-Isosantonic acid: Alteration of the hydrogen-bonding mode by configurational inversion at a single centre in a γ,ε- diketocarboxylic acidZinczuk, JuanRuveda, EdmundoLalancette, Roger A.Thompson, Hugh W.Single-crystal X-ray studyMean (C–C) = 0.002 AData-to-parameter ratio = 9.2https://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The title diketo acid, (1R,3aS,6aS,7R,9S)-(-)-α,3a,7-trimethyl-5,8- dioxo-1,4-ethanoperhydropentalene-1-acetic acid (C15H 20O4), is shown to aggregate in the crystal structure as acid-to-ketone hydrogen-bonding catemers, whose chains follow 21 screw axes from each carboxyl to a ketone in a neighbouring molecule [O⋯O = 2.7472(13) and O⋯H - O = 172.7(17)°]. Two parallel counterdirectional screw-related single-strand hydrogen-bonding chains pass through the cell in the a direction. Six intermolecular C - H⋯O=C close contacts are found. Comparisons are drawn with a diastereomer having the opposite configuration at the methylated chiral centre adjacent to the carboxyl group.Fil: Zinczuk, Juan. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Ruveda, Edmundo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Lalancette, Roger A.. Rutgers University; Estados UnidosFil: Thompson, Hugh W.. Rutgers University; Estados UnidosWiley Blackwell Publishing, Inc2006-06info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/133973Zinczuk, Juan; Ruveda, Edmundo; Lalancette, Roger A.; Thompson, Hugh W.; (-)-Isosantonic acid: Alteration of the hydrogen-bonding mode by configurational inversion at a single centre in a γ,ε- diketocarboxylic acid; Wiley Blackwell Publishing, Inc; Acta Crystallographica Section E; 62; 6; 6-2006; 1-41600-5368CONICET DigitalCONICETenginfo:eu-repo/semantics/reference/doi/https://doi.org/10.1107/S160053680601405X/lh2039sup1.cifinfo:eu-repo/semantics/reference/doi/https://doi.org/10.1107/S160053680601405X/lh2039Isup2.hklinfo:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/full/10.1107/S160053680601405X?sentby=iucrinfo:eu-repo/semantics/altIdentifier/doi/10.1107/S160053680601405Xinfo:eu-repo/semantics/altIdentifier/url/http://scripts.iucr.org/cgi-bin/paper?S160053680601405Xinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-11-05T09:51:37Zoai:ri.conicet.gov.ar:11336/133973instacron: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:34982025-11-05 09:51:38.092CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv (-)-Isosantonic acid: Alteration of the hydrogen-bonding mode by configurational inversion at a single centre in a γ,ε- diketocarboxylic acid
title (-)-Isosantonic acid: Alteration of the hydrogen-bonding mode by configurational inversion at a single centre in a γ,ε- diketocarboxylic acid
spellingShingle (-)-Isosantonic acid: Alteration of the hydrogen-bonding mode by configurational inversion at a single centre in a γ,ε- diketocarboxylic acid
Zinczuk, Juan
Single-crystal X-ray study
Mean (C–C) = 0.002 A
Data-to-parameter ratio = 9.2
title_short (-)-Isosantonic acid: Alteration of the hydrogen-bonding mode by configurational inversion at a single centre in a γ,ε- diketocarboxylic acid
title_full (-)-Isosantonic acid: Alteration of the hydrogen-bonding mode by configurational inversion at a single centre in a γ,ε- diketocarboxylic acid
title_fullStr (-)-Isosantonic acid: Alteration of the hydrogen-bonding mode by configurational inversion at a single centre in a γ,ε- diketocarboxylic acid
title_full_unstemmed (-)-Isosantonic acid: Alteration of the hydrogen-bonding mode by configurational inversion at a single centre in a γ,ε- diketocarboxylic acid
title_sort (-)-Isosantonic acid: Alteration of the hydrogen-bonding mode by configurational inversion at a single centre in a γ,ε- diketocarboxylic acid
dc.creator.none.fl_str_mv Zinczuk, Juan
Ruveda, Edmundo
Lalancette, Roger A.
Thompson, Hugh W.
author Zinczuk, Juan
author_facet Zinczuk, Juan
Ruveda, Edmundo
Lalancette, Roger A.
Thompson, Hugh W.
author_role author
author2 Ruveda, Edmundo
Lalancette, Roger A.
Thompson, Hugh W.
author2_role author
author
author
dc.subject.none.fl_str_mv Single-crystal X-ray study
Mean (C–C) = 0.002 A
Data-to-parameter ratio = 9.2
topic Single-crystal X-ray study
Mean (C–C) = 0.002 A
Data-to-parameter ratio = 9.2
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 diketo acid, (1R,3aS,6aS,7R,9S)-(-)-α,3a,7-trimethyl-5,8- dioxo-1,4-ethanoperhydropentalene-1-acetic acid (C15H 20O4), is shown to aggregate in the crystal structure as acid-to-ketone hydrogen-bonding catemers, whose chains follow 21 screw axes from each carboxyl to a ketone in a neighbouring molecule [O⋯O = 2.7472(13) and O⋯H - O = 172.7(17)°]. Two parallel counterdirectional screw-related single-strand hydrogen-bonding chains pass through the cell in the a direction. Six intermolecular C - H⋯O=C close contacts are found. Comparisons are drawn with a diastereomer having the opposite configuration at the methylated chiral centre adjacent to the carboxyl group.
Fil: Zinczuk, Juan. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Ruveda, Edmundo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Lalancette, Roger A.. Rutgers University; Estados Unidos
Fil: Thompson, Hugh W.. Rutgers University; Estados Unidos
description The title diketo acid, (1R,3aS,6aS,7R,9S)-(-)-α,3a,7-trimethyl-5,8- dioxo-1,4-ethanoperhydropentalene-1-acetic acid (C15H 20O4), is shown to aggregate in the crystal structure as acid-to-ketone hydrogen-bonding catemers, whose chains follow 21 screw axes from each carboxyl to a ketone in a neighbouring molecule [O⋯O = 2.7472(13) and O⋯H - O = 172.7(17)°]. Two parallel counterdirectional screw-related single-strand hydrogen-bonding chains pass through the cell in the a direction. Six intermolecular C - H⋯O=C close contacts are found. Comparisons are drawn with a diastereomer having the opposite configuration at the methylated chiral centre adjacent to the carboxyl group.
publishDate 2006
dc.date.none.fl_str_mv 2006-06
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/11336/133973
Zinczuk, Juan; Ruveda, Edmundo; Lalancette, Roger A.; Thompson, Hugh W.; (-)-Isosantonic acid: Alteration of the hydrogen-bonding mode by configurational inversion at a single centre in a γ,ε- diketocarboxylic acid; Wiley Blackwell Publishing, Inc; Acta Crystallographica Section E; 62; 6; 6-2006; 1-4
1600-5368
CONICET Digital
CONICET
url http://hdl.handle.net/11336/133973
identifier_str_mv Zinczuk, Juan; Ruveda, Edmundo; Lalancette, Roger A.; Thompson, Hugh W.; (-)-Isosantonic acid: Alteration of the hydrogen-bonding mode by configurational inversion at a single centre in a γ,ε- diketocarboxylic acid; Wiley Blackwell Publishing, Inc; Acta Crystallographica Section E; 62; 6; 6-2006; 1-4
1600-5368
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/reference/doi/https://doi.org/10.1107/S160053680601405X/lh2039sup1.cif
info:eu-repo/semantics/reference/doi/https://doi.org/10.1107/S160053680601405X/lh2039Isup2.hkl
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/full/10.1107/S160053680601405X?sentby=iucr
info:eu-repo/semantics/altIdentifier/doi/10.1107/S160053680601405X
info:eu-repo/semantics/altIdentifier/url/http://scripts.iucr.org/cgi-bin/paper?S160053680601405X
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by/2.5/ar/
dc.format.none.fl_str_mv application/pdf
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 13.084122

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