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

The structure of the title salt, ammonium carbamoyl­cyano­nitro­somethanide, NH(4) (+)·C(3)H(2)N(3)O(2) (−), 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...

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Detalles Bibliográficos
Autores principales: Domasevitch, Kostiantyn V., Senchyk, Ganna A., Lysenko, Andrey B., Rusanov, Eduard B.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8587992/
https://www.ncbi.nlm.nih.gov/pubmed/34868645
http://dx.doi.org/10.1107/S2056989021010239
Descripción
Sumario:The structure of the title salt, ammonium carbamoyl­cyano­nitro­somethanide, NH(4) (+)·C(3)H(2)N(3)O(2) (−), 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 [(NH(4))(O)(2)]. The most prominent bonds of the carbamoyl groups are mutual and they yield 2(1) 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 NH(4) (+)⋯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.