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Photochemical dimerization of a fluorinated dibenzylideneacetone in chloroform solution
Author(s) -
Schwarzer Anke,
Weber Edwin
Publication year - 2014
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229613034232
Subject(s) - chloroform , chemistry , photochemistry , organic chemistry
(1 E ,4 E )‐1,5‐Bis(2,6‐difluorophenyl)penta‐1,4‐dien‐3‐one, C 17 H 10 F 4 O, (I), dimerizes under sunlight in chloroform solution to form the corresponding cyclobutane derivative, (2 E ,2′ E )‐1,1′‐[2,4‐bis(2,6‐difluorophenyl)cyclobutane‐1,3‐diyl]bis[3‐(2,6‐difluorophenyl)prop‐2‐en‐1‐one], C 34 H 20 F 8 O 2 , (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...π and π–π).