The solvates of 1,2-bis(bromomethyl)-3,4,5,6-tetraphenylbenzene

Solvates of 1,2-bis(bromomethyl)-3,4,5,6-tetraphenylbenzene (1) were obtained, and their crystal structures were determined by X-ray diffraction. Crystal structure analysis indicated the following chemical compositions of solvates: 1·benzene (2), 1·1/2 toluene (3), 1·1/2 chlorobenzene (4) and 1·1/4 ethyl acetate (5) were found by crystal structure analysis. 3 and 4 crystallize in orthorhombic space group Pccn, whereas 2 and 5 are monoclinic, space group P21/c. In a different crystalline environment the conformation of 1 differs significantly. Some similarities could be found in the structures of 3 and 4. In the structure of 5 two symmetrically independent molecules also adopt different conformations. The packing of the molecules is similar in all the structures, with open channels filled by disordered solvent molecules. DFT calculations performed for the isolated molecule of 1 revealed the highest preference for the anti arrangement of the bromomethyl groups which was also observed in the crystalline state. An attempt to explain the lack of reactivity of 1 towards formation of the propellane derivatives was made.