Hydrogen-bonding landscape of the carbamoyl­cyano­nitro­somethanide anion in the crystal structure of its ammonium salt

ABSTRACT: The structure of the title salt, ammonium carbamoyl­cyano­nitro­somethanide, NH4+·C3H2N3O2−, features the co-existence of different hydrogen-bonding patterns, which are specific to each of the three functional groups (nitroso, carbamoyl and cyano) of the methanide anion. The relatively simple scheme of these inter­actions allows the delineation of the supra­molecular synthons, which may be applicable to crystal engineering of hydrogen-bonded solids containing polyfunctional methanide anions. The structure of the title salt, ammonium carbamoyl­cyano­nitro­somethanide, NH4+·C3H2N3O2−, features the co-existence of different hydrogen-bonding patterns, which are specific to each of the three functional groups (nitroso, carbamoyl and cyano) of the methanide anion. The nitroso O-atoms accept as many as three N—H⋯O bonds from the ammonium cations [N⋯O = 2.688 (3)–3.000 (3) Å] to form chains of fused rhombs [(NH4)(O)2]. The most prominent bonds of the carbamoyl groups are mutual and they yield 21 helices [N⋯O = 2.903 (2) Å], whereas the cyano N-atoms accept hydrogen bonds from sterically less accessible carbamoyl H-atoms [N⋯N = 3.004 (3) Å]. Two weaker NH4+⋯O=C bonds [N⋯O = 3.021 (2), 3.017 (2) Å] complete the hydrogen-bonded environment of the carbamoyl groups. A Hirshfeld surface analysis indicates that the most important inter­actions are overwhelmingly O⋯H/H⋯O and N⋯H/H⋯N, in total accounting for 64.1% of the contacts for the individual anions. The relatively simple scheme of these inter­actions allows the delineation of the supra­molecular synthons, which may be applicable to crystal engineering of hydrogen-bonded solids containing polyfunctional methanide anions.

SUBMITTER: Domasevitch K 

PROVIDER: S-EPMC8587992 | biostudies-literature |

REPOSITORIES: biostudies-literature