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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...
Autores principales: | , , , |
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2010
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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]. |
format | Text |
id | pubmed-2979081 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2010 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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