Relationship between the structure and luminescent properties for two crystal modifications of N-butyl-2-cyano-3-[4-(dimethylamino)phenyl]-2-propenamide

Two crystal modifications ( 1o and 1y ) of N -butyl-2-cyano-3-[4-(dimethylamino)phenyl]-2-propenamide, which differ in the color of crystals and the color of luminescence, have been studied by X-ray diffraction and spectral-luminescence methods. The corresponding bond lengths and bond angles in the molecules of two crystal modifications are virtually identical. In both crystal structures, there are two systems of weak intermolecular interactions: π-stacking interactions and -CN…H-N hydrogen bonds involving nitrile and NH groups. In the crystal structures, two hydrogen bonds connect pairs of molecules into centrosymmetric dimers. The N…H distances are 2.21 and 2.41 Å in 1o and 1y , respectively. The interplanar distances in the π-stacked systems of 1o and 1y are 3.33 and 3.41 Å, respectively. Both types of weak interactions are stronger in 1o than in 1y , which accounts for a larger shift of absorption and luminescence bands for the former compound.