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Crystal structure of 1,2-bis(3,5-difluorophenyl)ethane-1,2-dione

ABSTRACT: The title compound crystallizes with half of a molecule per asymmetric unit and exhibits bond lengths and angles typical of α-diketones. A network of C—H⋯F contacts and π–π stacking interactions is observed within the structure. The title compound, C14H6F4O2, crystallizes with half of a molecule per asymmetric unit and exhibits bond lengths and angles typical of α-diketones. A network of C—H⋯F contacts and π–π stacking interactions is observed within the structure.

SUBMITTER: Brown L

PROVIDER: S-EPMC8382065 | biostudies-literature |

REPOSITORIES: biostudies-literature

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

Project 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 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.

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

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Project description:The mol-ecule of the title compound, C(18)H(12)N(2)O(4), is situated on a crystallographic centre of symmetry. The mol-ecule has a zigzag structure, with two parallel symmetry-related indoline-2,3-dione fragments linked by an ethyl-ene group at each N atom. In the crystal, the mol-ecules stack in columns along the b axis. There are two such columns in the structure. The mol-ecules within each column are parallel; however, the mol-ecules in the two columns differ in the respective orientation of the indoline-2,3-dione fragments. In one column, they are approximately parallel to (112), while in the other they are approximately parallel to (12). The inter-planar angle between the indoline-2,3-dione fragments in the two columns is 80.83?(3)°. The mol-ecules within each column are related by mutual displacement of their centres of symmetry, that is (0, ±1/2, ±1/2). The packing between the mol-ecules is provided by weak inter-actions only, viz. C-H?O hydrogen bonds and ?-? [centroid-centroid distance = 3.8745?(8)?Å] and C=O?? inter-actions.

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