“…In most of the 25 guanidines retrieved from the Cambridge Crystallographic Data File, there are no significant differences between the three C-N distances; in crystals, the C-N bonds are widely delocalized. E.g., in (DJdicyanodiamide ( = (DJcyanoguanidine)[32], the values of the three C-N distances are 1.328, 1.329, and 1.330(2) A. The guanidine moiety has a planar geometry in most of these examples.Due to restricted rotation about their C-N bonds, eight different conformations may theoretically be adopted by N',N"-disubstituted N-cyanoguanidines (see D-K, R' # R2, Scheme 2).…”