Acta Crystallographica Section C

Structural Chemistry

Volume 70, Part 2 (February 2014)

organic compounds

eg3145 scheme

Acta Cryst. (2014). C70, 202-206    [ doi:10.1107/S2053229613034232 ]

Photochemical dimerization of a fluorinated di­benzyl­ideneacetone in chloro­form solution

A. Schwarzer and E. Weber

Abstract: (1E,4E)-1,5-Bis(2,6-di­fluoro­phen­yl)penta-1,4-dien-3-one, C17H10F4O, (I), dimerizes under sunlight in chloro­form solution to form the corresponding cyclo­butane derivative, (2E,2'E)-1,1'-[2,4-bis­(2,6-di­fluoro­phen­yl)cyclo­butane-1,3-di­yl]bis­[3-(2,6-di­fluoro­phen­yl)prop-2-en-1-one], C34H20F8O2, (II). The crystal structure of (I) explains why no topochemical di­merization can occur in the solid state. In the solid, mol­ecules of dimer (II) show the `truxillic acid'-type arrangement of crystallographic centres of inversion, with half a mol­ecule per asymmetric unit and cell dimensions closely related to those of the monomer. Inter­molecular inter­actions in both solids are dominated by C-H...O and C-H...F contacts and also comprise inter­actions with aromatic systems (C-H...[pi] and [pi]-[pi]).

CCDC references: 742631 and 978150

Formula: C17H10F4O and C34H20F8O2

Keywords: crystal structure; photodimerization; di­benzyl­ideneacetone; cyclo­butane; fluorine interactions.

cmldisplay filedownload file

Chemical Markup Language (CML) file (5.1 kbytes)
[ doi:10.1107/S2053229613034232/eg3145Isup4.cml ]
Supplementary material

cmldisplay filedownload file

Chemical Markup Language (CML) file (10.3 kbytes)
[ doi:10.1107/S2053229613034232/eg3145IIsup5.cml ]
Supplementary material


To open or display or play some files, you may need to set your browser up to use the appropriate software. See the full list of file types for an explanation of the different file types and their related mime types and, where available links to sites from where the appropriate software may be obtained.

The download button will force most browsers to prompt for a file name to store the data on your hard disk.

Where possible, images are represented by thumbnails.

 bibliographic record in  format