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2-Bromo-3-phenyl-1-(3-phenyl­sydnon-4-yl)prop-2-en-1-one

The title sydnone derivative [systematic name: 2-bromo-1-(5-oxido-3-phenyl-1,2,3-oxadiazo­lium-4-yl)-3-phenyl­prop-2-en-1-one], C(17)H(11)BrN(2)O(3), exists in a Z configuration with respect to the acyclic C=C bond. An intra­molecular C—H⋯Br hydrogen bond generates a six-membered ring, producing an...

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Detalles Bibliográficos
Autores principales: Goh, Jia Hao, Fun, Hoong-Kun, Nithinchandra, Kalluraya, B.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2979081/
https://www.ncbi.nlm.nih.gov/pubmed/21579251
http://dx.doi.org/10.1107/S1600536810015205
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author Goh, Jia Hao
Fun, Hoong-Kun
Nithinchandra,
Kalluraya, B.
author_facet Goh, Jia Hao
Fun, Hoong-Kun
Nithinchandra,
Kalluraya, B.
author_sort Goh, Jia Hao
collection PubMed
description The title sydnone derivative [systematic name: 2-bromo-1-(5-oxido-3-phenyl-1,2,3-oxadiazo­lium-4-yl)-3-phenyl­prop-2-en-1-one], C(17)H(11)BrN(2)O(3), exists in a Z configuration with respect to the acyclic C=C bond. An intra­molecular C—H⋯Br hydrogen bond generates a six-membered ring, producing an S(6) ring motif. The 1,2,3-oxadiazole ring in the sydnone unit is essentially planar [maximum deviation = 0.011 (2) Å] and forms dihedral angles of 55.39 (13) and 57.12 (12)° with the two benzene rings. In the crystal structure, inter­molecular C—H⋯O hydrogen bonds link mol­ecules into two-mol­ecule-thick arrays parallel to the bc plane. The crystal structure also features a short inter­molecular N⋯C contacts [3.030 (3) Å] as well as C—H⋯π and π–π inter­actions [centroid–centroid distances = 3.3798 (11) and 3.2403 (12) Å].
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spelling pubmed-29790812010-12-30 2-Bromo-3-phenyl-1-(3-phenyl­sydnon-4-yl)prop-2-en-1-one Goh, Jia Hao Fun, Hoong-Kun Nithinchandra, Kalluraya, B. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title sydnone derivative [systematic name: 2-bromo-1-(5-oxido-3-phenyl-1,2,3-oxadiazo­lium-4-yl)-3-phenyl­prop-2-en-1-one], C(17)H(11)BrN(2)O(3), exists in a Z configuration with respect to the acyclic C=C bond. An intra­molecular C—H⋯Br hydrogen bond generates a six-membered ring, producing an S(6) ring motif. The 1,2,3-oxadiazole ring in the sydnone unit is essentially planar [maximum deviation = 0.011 (2) Å] and forms dihedral angles of 55.39 (13) and 57.12 (12)° with the two benzene rings. In the crystal structure, inter­molecular C—H⋯O hydrogen bonds link mol­ecules into two-mol­ecule-thick arrays parallel to the bc plane. The crystal structure also features a short inter­molecular N⋯C contacts [3.030 (3) Å] as well as C—H⋯π and π–π inter­actions [centroid–centroid distances = 3.3798 (11) and 3.2403 (12) Å]. International Union of Crystallography 2010-04-30 /pmc/articles/PMC2979081/ /pubmed/21579251 http://dx.doi.org/10.1107/S1600536810015205 Text en © Goh et al. 2010 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Goh, Jia Hao
Fun, Hoong-Kun
Nithinchandra,
Kalluraya, B.
2-Bromo-3-phenyl-1-(3-phenyl­sydnon-4-yl)prop-2-en-1-one
title 2-Bromo-3-phenyl-1-(3-phenyl­sydnon-4-yl)prop-2-en-1-one
title_full 2-Bromo-3-phenyl-1-(3-phenyl­sydnon-4-yl)prop-2-en-1-one
title_fullStr 2-Bromo-3-phenyl-1-(3-phenyl­sydnon-4-yl)prop-2-en-1-one
title_full_unstemmed 2-Bromo-3-phenyl-1-(3-phenyl­sydnon-4-yl)prop-2-en-1-one
title_short 2-Bromo-3-phenyl-1-(3-phenyl­sydnon-4-yl)prop-2-en-1-one
title_sort 2-bromo-3-phenyl-1-(3-phenyl­sydnon-4-yl)prop-2-en-1-one
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2979081/
https://www.ncbi.nlm.nih.gov/pubmed/21579251
http://dx.doi.org/10.1107/S1600536810015205
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AT kallurayab 2bromo3phenyl13phenylsydnon4ylprop2en1one