Mt. Ahmet et al., INFLUENCE OF CRYSTAL ENVIRONMENT ON MOLECULAR-CONFORMATION - P-BROMO-N-(P-DIMETHYLAMINOBENZYLIDENE)ANILINE, Acta crystallographica. Section C, Crystal structure communications, 50, 1994, pp. 1814-1818
p-Bromo-N-(p-dimethylaminobenzylidene) aniline, C15H15BrN2, (1), compr
ises two independent molecules with markedly different conformations.
Molecule A is essentially planar along its entire length (including th
e dimethylamino group) whereas molecule B deviates considerably from p
lanarity with an interplanar angle of 145.8 (3)degrees between the two
phenyl rings and the NMe(2) group twisted by 10 (2)degrees out of the
plane of the phenyl ring to which it is bound. While polymorphism and
crystal packing effects are well documented for benzylidene derivativ
es, this is an interesting example with two quite distinct conformatio
ns in the same crystal phase. The differences are accounted for in ter
ms of crystal-packing effects. The structure highlights the ability of
particular molecular arrangements to stabilize a less favourable mole
cular conformation.