First molecular self-assembly of 1,4-diiodo-tetrafluoro-benzene and a ketone via (O/I) non-covalent halogen bonds

4,40-bis(dimethylamino)-benzophenone (1) is shown to self-assemble in the solid phase with 1,4-diiodo-tetrafluoro-benzene (TFDIB) to form the air stable compound 1 TFDIB. Single crystal X-ray analysis of this compound reveals a structure consisting of ribbon-like polymeric chains of alternating donor and acceptor molecules. The directing non-covalent halogen bond is characterised by a relatively long O/I distance of 3.097 A ° and an O/I–C angle of 163.298. These bond characteristics are due to the coordination of each carbonyl oxygen with two iodine atoms, resulting in a ‘zigzag’ geometry of the chains. Carbonyl derivatives can thus be considered as new tectons for the formation of hybrid perfluorocarbon–hydrocarbon crystalline materials. q 2004 Elsevier B.V. All rights reserved.