Stereoelectronic interactions in the fragment N-C-CN from high-resolution X-ray diffraction data and quantum chemical computations

Analysis of the experimental electron density distribution function for the crystal and quantum chemical calculations revealed some distinctive features of stereoelectronic interactions (SI) in the fragment N-C-CN. The SI-induced changes in the atomic parameters were characterized in terms of the “Atoms in Molecules” theory. These interactions were compared with competitive SI in the fragment N-C-N. The crystal packing in organic cyanides is discussed. According to the data obtained, relatively weak SI in the fragment N-C-CN can be decisive for the molecular conformation in the crystal when there are no strong competitive interactions.