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2-[(4-Chloro­phen­yl)selan­yl]-3,4-di­hydro-2H-benzo[h]chromene-5,6-dione: crystal structure and Hirshfeld analysis

The title organoselenium compound, C(19)H(13)ClO(3)Se {systematic name: 2-[(4-chloro­phen­yl)selan­yl]-2H,3H,4H,5H,6H-naphtho­[1,2-b]pyran-5,6-dione}, has the substituted 2-pyranyl ring in a half-chair conformation with the methyl­ene-C atom bound to the methine-C atom being the flap atom. The dihed...

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Autores principales: Zukerman-Schpector, Julio, Prado, Karinne E., Name, Luccas L., Cella, Rodrigo, Jotani, Mukesh M., Tiekink, Edward R. T.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5458324/
https://www.ncbi.nlm.nih.gov/pubmed/28638659
http://dx.doi.org/10.1107/S2056989017007605
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author Zukerman-Schpector, Julio
Prado, Karinne E.
Name, Luccas L.
Cella, Rodrigo
Jotani, Mukesh M.
Tiekink, Edward R. T.
author_facet Zukerman-Schpector, Julio
Prado, Karinne E.
Name, Luccas L.
Cella, Rodrigo
Jotani, Mukesh M.
Tiekink, Edward R. T.
author_sort Zukerman-Schpector, Julio
collection PubMed
description The title organoselenium compound, C(19)H(13)ClO(3)Se {systematic name: 2-[(4-chloro­phen­yl)selan­yl]-2H,3H,4H,5H,6H-naphtho­[1,2-b]pyran-5,6-dione}, has the substituted 2-pyranyl ring in a half-chair conformation with the methyl­ene-C atom bound to the methine-C atom being the flap atom. The dihedral angle between the two aromatic regions of the mol­ecule is 9.96 (9)° and indicates a step-like conformation. An intra­molecular Se⋯O inter­action of 2.8122 (13) Å is noted. In the crystal, π–π contacts between naphthyl rings [inter-centroid distance = 3.7213 (12) Å] and between naphthyl and chloro­benzene rings [inter-centroid distance = 3.7715 (13) Å], along with C—Cl⋯π(chloro­benzene) contacts, lead to supra­molecular layers parallel to the ab plane, which are connected into a three-dimensional architecture via methyl­ene-C—H⋯O(carbon­yl) inter­actions. The contributions of these and other weak contacts to the Hirshfeld surface is described.
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spelling pubmed-54583242017-06-21 2-[(4-Chloro­phen­yl)selan­yl]-3,4-di­hydro-2H-benzo[h]chromene-5,6-dione: crystal structure and Hirshfeld analysis Zukerman-Schpector, Julio Prado, Karinne E. Name, Luccas L. Cella, Rodrigo Jotani, Mukesh M. Tiekink, Edward R. T. Acta Crystallogr E Crystallogr Commun Research Communications The title organoselenium compound, C(19)H(13)ClO(3)Se {systematic name: 2-[(4-chloro­phen­yl)selan­yl]-2H,3H,4H,5H,6H-naphtho­[1,2-b]pyran-5,6-dione}, has the substituted 2-pyranyl ring in a half-chair conformation with the methyl­ene-C atom bound to the methine-C atom being the flap atom. The dihedral angle between the two aromatic regions of the mol­ecule is 9.96 (9)° and indicates a step-like conformation. An intra­molecular Se⋯O inter­action of 2.8122 (13) Å is noted. In the crystal, π–π contacts between naphthyl rings [inter-centroid distance = 3.7213 (12) Å] and between naphthyl and chloro­benzene rings [inter-centroid distance = 3.7715 (13) Å], along with C—Cl⋯π(chloro­benzene) contacts, lead to supra­molecular layers parallel to the ab plane, which are connected into a three-dimensional architecture via methyl­ene-C—H⋯O(carbon­yl) inter­actions. The contributions of these and other weak contacts to the Hirshfeld surface is described. International Union of Crystallography 2017-05-31 /pmc/articles/PMC5458324/ /pubmed/28638659 http://dx.doi.org/10.1107/S2056989017007605 Text en © Zukerman-Schpector et al. 2017 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/2.0/uk/
spellingShingle Research Communications
Zukerman-Schpector, Julio
Prado, Karinne E.
Name, Luccas L.
Cella, Rodrigo
Jotani, Mukesh M.
Tiekink, Edward R. T.
2-[(4-Chloro­phen­yl)selan­yl]-3,4-di­hydro-2H-benzo[h]chromene-5,6-dione: crystal structure and Hirshfeld analysis
title 2-[(4-Chloro­phen­yl)selan­yl]-3,4-di­hydro-2H-benzo[h]chromene-5,6-dione: crystal structure and Hirshfeld analysis
title_full 2-[(4-Chloro­phen­yl)selan­yl]-3,4-di­hydro-2H-benzo[h]chromene-5,6-dione: crystal structure and Hirshfeld analysis
title_fullStr 2-[(4-Chloro­phen­yl)selan­yl]-3,4-di­hydro-2H-benzo[h]chromene-5,6-dione: crystal structure and Hirshfeld analysis
title_full_unstemmed 2-[(4-Chloro­phen­yl)selan­yl]-3,4-di­hydro-2H-benzo[h]chromene-5,6-dione: crystal structure and Hirshfeld analysis
title_short 2-[(4-Chloro­phen­yl)selan­yl]-3,4-di­hydro-2H-benzo[h]chromene-5,6-dione: crystal structure and Hirshfeld analysis
title_sort 2-[(4-chloro­phen­yl)selan­yl]-3,4-di­hydro-2h-benzo[h]chromene-5,6-dione: crystal structure and hirshfeld analysis
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5458324/
https://www.ncbi.nlm.nih.gov/pubmed/28638659
http://dx.doi.org/10.1107/S2056989017007605
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