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4-Bromo­acetyl-3-phenyl­sydnone

In the title compound (systematic name: 4-bromoacetyl-1,2,3-oxadiazol-3-ylium-5-olate), C(10)H(7)BrN(2)O(3), the 1,2,3-oxadiazole ring and bromo­acetyl group are essentially planar [maximum deviation = 0.010 (4) and 0.013 (3) Å respectively] and form dihedral angles of 59.31 (19) and 67.96 (11)°, re...

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Autores principales: Fun, Hoong-Kun, Chia, Tze Shyang, Nithinchandra, Kalluraya, Balakrishna, Shetty, Shobhitha
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3393916/
https://www.ncbi.nlm.nih.gov/pubmed/22798781
http://dx.doi.org/10.1107/S1600536812026049
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author Fun, Hoong-Kun
Chia, Tze Shyang
Nithinchandra,
Kalluraya, Balakrishna
Shetty, Shobhitha
author_facet Fun, Hoong-Kun
Chia, Tze Shyang
Nithinchandra,
Kalluraya, Balakrishna
Shetty, Shobhitha
author_sort Fun, Hoong-Kun
collection PubMed
description In the title compound (systematic name: 4-bromoacetyl-1,2,3-oxadiazol-3-ylium-5-olate), C(10)H(7)BrN(2)O(3), the 1,2,3-oxadiazole ring and bromo­acetyl group are essentially planar [maximum deviation = 0.010 (4) and 0.013 (3) Å respectively] and form dihedral angles of 59.31 (19) and 67.96 (11)°, respectively, with the phenyl ring. The 1,2,3-oxadiazole ring is twisted slightly from the mean plane of the bromo­acetyl group, forming a dihedral angle of 9.16 (24)°. In the crystal, mol­ecules are linked by pairs of weak C—H⋯O hydrogen bonds into inversion dimers with R (2) (2)(12) ring motifs. The dimers are further connected by weak C—H⋯O hydrogen bonds into an infinite tape parallel to the b axis. In addition, π–π stacking inter­actions [centroid–centroid distance = 3.6569 (19) Å] and short inter­molecular contacts [O⋯O = 2.827 (3) and C⋯C = 3.088 (5) Å] are observed.
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spelling pubmed-33939162012-07-13 4-Bromo­acetyl-3-phenyl­sydnone Fun, Hoong-Kun Chia, Tze Shyang Nithinchandra, Kalluraya, Balakrishna Shetty, Shobhitha Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound (systematic name: 4-bromoacetyl-1,2,3-oxadiazol-3-ylium-5-olate), C(10)H(7)BrN(2)O(3), the 1,2,3-oxadiazole ring and bromo­acetyl group are essentially planar [maximum deviation = 0.010 (4) and 0.013 (3) Å respectively] and form dihedral angles of 59.31 (19) and 67.96 (11)°, respectively, with the phenyl ring. The 1,2,3-oxadiazole ring is twisted slightly from the mean plane of the bromo­acetyl group, forming a dihedral angle of 9.16 (24)°. In the crystal, mol­ecules are linked by pairs of weak C—H⋯O hydrogen bonds into inversion dimers with R (2) (2)(12) ring motifs. The dimers are further connected by weak C—H⋯O hydrogen bonds into an infinite tape parallel to the b axis. In addition, π–π stacking inter­actions [centroid–centroid distance = 3.6569 (19) Å] and short inter­molecular contacts [O⋯O = 2.827 (3) and C⋯C = 3.088 (5) Å] are observed. International Union of Crystallography 2012-06-16 /pmc/articles/PMC3393916/ /pubmed/22798781 http://dx.doi.org/10.1107/S1600536812026049 Text en © Fun et al. 2012 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
Fun, Hoong-Kun
Chia, Tze Shyang
Nithinchandra,
Kalluraya, Balakrishna
Shetty, Shobhitha
4-Bromo­acetyl-3-phenyl­sydnone
title 4-Bromo­acetyl-3-phenyl­sydnone
title_full 4-Bromo­acetyl-3-phenyl­sydnone
title_fullStr 4-Bromo­acetyl-3-phenyl­sydnone
title_full_unstemmed 4-Bromo­acetyl-3-phenyl­sydnone
title_short 4-Bromo­acetyl-3-phenyl­sydnone
title_sort 4-bromo­acetyl-3-phenyl­sydnone
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3393916/
https://www.ncbi.nlm.nih.gov/pubmed/22798781
http://dx.doi.org/10.1107/S1600536812026049
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