(E)-1,2-Bis(4-fluorophenyl)ethane-1,2-dione
The title compound, C14H8F2O2, 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, 1.5...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
| Published: |
International Union of Crystallography
2008-08-01
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| Series: | Acta Crystallographica Section E |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S1600536808023350 |
| _version_ | 1798026939990016000 |
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| author | Hoong-Kun Fun Reza Kia |
| author_facet | Hoong-Kun Fun Reza Kia |
| author_sort | Hoong-Kun Fun |
| collection | DOAJ |
| description | The title compound, C14H8F2O2, 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 Csp2—Csp2 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. |
| first_indexed | 2024-04-11T18:43:24Z |
| format | Article |
| id | doaj.art-c7538f25d08445fcbac3509be329f4c4 |
| institution | Directory Open Access Journal |
| issn | 1600-5368 |
| language | English |
| last_indexed | 2024-04-11T18:43:24Z |
| publishDate | 2008-08-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E |
| spelling | doaj.art-c7538f25d08445fcbac3509be329f4c42022-12-22T04:08:54ZengInternational Union of CrystallographyActa Crystallographica Section E1600-53682008-08-01648o1617o161810.1107/S1600536808023350(E)-1,2-Bis(4-fluorophenyl)ethane-1,2-dioneHoong-Kun FunReza KiaThe title compound, C14H8F2O2, 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 Csp2—Csp2 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.http://scripts.iucr.org/cgi-bin/paper?S1600536808023350 |
| spellingShingle | Hoong-Kun Fun Reza Kia (E)-1,2-Bis(4-fluorophenyl)ethane-1,2-dione Acta Crystallographica Section E |
| 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 |
| url | http://scripts.iucr.org/cgi-bin/paper?S1600536808023350 |
| work_keys_str_mv | AT hoongkunfun e12bis4fluorophenylethane12dione AT rezakia e12bis4fluorophenylethane12dione |