Tetramethylammonium (Z)-N′-cyanocarbamimidate

Abstract

In the structure of the tetramethyl ammonium salt of cyanourea, C4H12N+·C2H2N3O−, the N—C and O—C bond distances in the cyano and keto groups are in the normal range for such a moieties at 1.1641 (18) and 1.2550 (16) Å. However, the bonds about the central C and N atoms are much shorter than would be expected for single bonds and indicate that there is considerable electron delocalization in the anion as was also found in the silver salt. The NH2 group is coplanar with the central N2CO core, in contrast with the nitrile group where the dihedral angle between the N—C—N and N2CO planes is 36.5 (3)°. The packing of the cations and anions in the unit cell involves N—H...O hydrogen bonds between anions characterized by an R22(8) motif, as well as N—H...O hydrogen bonds between anions and C—H...O interactions between both cations and anions, forming an R33(14) pattern.

Keywords

• crystal structure
• cyanourea salt
• tetramethylammonium salt