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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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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2008
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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. |
format | Text |
id | pubmed-2962135 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2008 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT funhoongkun e12bis4fluorophenylethane12dione AT kiareza e12bis4fluorophenylethane12dione |