Crystal and molecular structures of six differently with halogen substituted bis (benzylimido) perylene

The structures of bis (3,5-dichlorobenzylimido) perylene, bis (3-chlorobenz ylimido) perylene, bis (3-fluorobenzylimido) perylene, bis (3,5-difluoroben zylimido) perylene, bis (4-chlorobenzylimido) perylene, and bis (2,6-difluo rubenzylimido) perylene were solved by single crystal analysis. The compoun ds crystallize in Four different space groups, that is, in sequence of the compounds listed P (1) over bar, P (1) over bar, P2(1)/a, C2/c, Pbcn, P2(1) /n, respectively, although their chemical constitutions an very similar. Th e packing in different arrangements causes the twist of the benzene ring to differ with respect to the perylene ring and amounts to 111.4 degrees, 112 .3 degrees, 98.6 degrees, 105.1 degrees, 80.3 degrees, 72.0 degrees for the sequence of compounds listed, respectively. The first two compounds crysta llizing in space group P (1) over bar are isomorphous in structure and exhi bit the same dark blue color. The C-F bond distances lie between 1.36 and 1 .38 Angstrom, the C-Cl bond distances between 1.73 and 1.75 Angstrom. For a ll six structures investigated the planes of two adjacent perylene skeleton planes are 3.43 to 3.50 Angstrom apart and the tilt angles versus the shor test unit cell dimension lie between 20 and 45 degrees.