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(E)-1,2-Bis(4-fluoro­phen­yl)ethane-1,2-dione

The title compound, C(14)H(8)F(2)O(2), is a substituted benzil with an s-trans conformation of the dicarbonyl unit. This conformation is also shown by the O—C—C—O torsion angle of −110.65 (12)°. An unusual feature of the structure is the length, 1.536 (2) Å, of the central C—C bond connecting the ca...

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Autores principales: Fun, Hoong-Kun, Kia, Reza
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2008
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2962135/
https://www.ncbi.nlm.nih.gov/pubmed/21203308
http://dx.doi.org/10.1107/S1600536808023350
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author Fun, Hoong-Kun
Kia, Reza
author_facet Fun, Hoong-Kun
Kia, Reza
author_sort Fun, Hoong-Kun
collection PubMed
description The title compound, C(14)H(8)F(2)O(2), is a substituted benzil with an s-trans conformation of the dicarbonyl unit. This conformation is also shown by the O—C—C—O torsion angle of −110.65 (12)°. An unusual feature of the structure is the length, 1.536 (2) Å, of the central C—C bond connecting the carbonyl units, which is significantly longer than a normal Csp (2)—Csp (2) single bond. This is probably the result of decreasing the unfavourable vicinal dipole–dipole inter­actions by increasing the distance between the two electronegative O atoms [O⋯O = 3.1867 (12) Å] and allowing orbital overlap of the dione with the π system of the benzene rings. The dihedral angle between the aromatic rings is 64.74 (5)°. In the crystal structure, neighbouring mol­ecules are linked together by weak inter­molecular C—H⋯O (× 2) hydrogen bonds. In addition, the crystal structure is further stabilized by inter­molecular π–π inter­actions with centroid–centroid distances in the range 3.6416 (6)–3.7150 (7) Å.
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spelling pubmed-29621352010-12-30 (E)-1,2-Bis(4-fluoro­phen­yl)ethane-1,2-dione Fun, Hoong-Kun Kia, Reza Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(14)H(8)F(2)O(2), is a substituted benzil with an s-trans conformation of the dicarbonyl unit. This conformation is also shown by the O—C—C—O torsion angle of −110.65 (12)°. An unusual feature of the structure is the length, 1.536 (2) Å, of the central C—C bond connecting the carbonyl units, which is significantly longer than a normal Csp (2)—Csp (2) single bond. This is probably the result of decreasing the unfavourable vicinal dipole–dipole inter­actions by increasing the distance between the two electronegative O atoms [O⋯O = 3.1867 (12) Å] and allowing orbital overlap of the dione with the π system of the benzene rings. The dihedral angle between the aromatic rings is 64.74 (5)°. In the crystal structure, neighbouring mol­ecules are linked together by weak inter­molecular C—H⋯O (× 2) hydrogen bonds. In addition, the crystal structure is further stabilized by inter­molecular π–π inter­actions with centroid–centroid distances in the range 3.6416 (6)–3.7150 (7) Å. International Union of Crystallography 2008-07-31 /pmc/articles/PMC2962135/ /pubmed/21203308 http://dx.doi.org/10.1107/S1600536808023350 Text en © Fun and Kia 2008 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
Kia, Reza
(E)-1,2-Bis(4-fluoro­phen­yl)ethane-1,2-dione
title (E)-1,2-Bis(4-fluoro­phen­yl)ethane-1,2-dione
title_full (E)-1,2-Bis(4-fluoro­phen­yl)ethane-1,2-dione
title_fullStr (E)-1,2-Bis(4-fluoro­phen­yl)ethane-1,2-dione
title_full_unstemmed (E)-1,2-Bis(4-fluoro­phen­yl)ethane-1,2-dione
title_short (E)-1,2-Bis(4-fluoro­phen­yl)ethane-1,2-dione
title_sort (e)-1,2-bis(4-fluoro­phen­yl)ethane-1,2-dione
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2962135/
https://www.ncbi.nlm.nih.gov/pubmed/21203308
http://dx.doi.org/10.1107/S1600536808023350
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