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(E)-1,2-Bis(4-fluoro-phen-yl)ethane-1,2-dione.

ABSTRACT: 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 inter-actions 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 ? system of the benzene rings. The dihedral angle between the aromatic rings is 64.74?(5)°. In the crystal structure, neighbouring mol-ecules are linked together by weak inter-molecular C-H?O (× 2) hydrogen bonds. In addition, the crystal structure is further stabilized by inter-molecular ?-? inter-actions with centroid-centroid distances in the range 3.6416?(6)-3.7150?(7)?Å.

SUBMITTER: Fun HK

PROVIDER: S-EPMC2962135 | biostudies-literature | 2008 Jul

REPOSITORIES: biostudies-literature

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(E)-1,2-Bis(4-fluoro-phen-yl)ethane-1,2-dione.

Fun Hoong-Kun HK Kia Reza R

Acta crystallographica. Section E, Structure reports online 20080731 Pt 8

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 inter-actions by increasing the di ...[more]

PMID: 21203308

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