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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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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
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author Domasevitch, Kostiantyn V.
Senchyk, Ganna A.
Lysenko, Andrey B.
Rusanov, Eduard B.
author_facet Domasevitch, Kostiantyn V.
Senchyk, Ganna A.
Lysenko, Andrey B.
Rusanov, Eduard B.
author_sort Domasevitch, Kostiantyn V.
collection PubMed
description 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.
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spelling pubmed-85879922021-12-02 Hydrogen-bonding landscape of the carbamoyl­cyano­nitro­somethanide anion in the crystal structure of its ammonium salt Domasevitch, Kostiantyn V. Senchyk, Ganna A. Lysenko, Andrey B. Rusanov, Eduard B. Acta Crystallogr E Crystallogr Commun Research Communications 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. International Union of Crystallography 2021-10-13 /pmc/articles/PMC8587992/ /pubmed/34868645 http://dx.doi.org/10.1107/S2056989021010239 Text en © Domasevitch et al. 2021 https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Research Communications
Domasevitch, Kostiantyn V.
Senchyk, Ganna A.
Lysenko, Andrey B.
Rusanov, Eduard B.
Hydrogen-bonding landscape of the carbamoyl­cyano­nitro­somethanide anion in the crystal structure of its ammonium salt
title Hydrogen-bonding landscape of the carbamoyl­cyano­nitro­somethanide anion in the crystal structure of its ammonium salt
title_full Hydrogen-bonding landscape of the carbamoyl­cyano­nitro­somethanide anion in the crystal structure of its ammonium salt
title_fullStr Hydrogen-bonding landscape of the carbamoyl­cyano­nitro­somethanide anion in the crystal structure of its ammonium salt
title_full_unstemmed Hydrogen-bonding landscape of the carbamoyl­cyano­nitro­somethanide anion in the crystal structure of its ammonium salt
title_short Hydrogen-bonding landscape of the carbamoyl­cyano­nitro­somethanide anion in the crystal structure of its ammonium salt
title_sort hydrogen-bonding landscape of the carbamoyl­cyano­nitro­somethanide anion in the crystal structure of its ammonium salt
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8587992/
https://www.ncbi.nlm.nih.gov/pubmed/34868645
http://dx.doi.org/10.1107/S2056989021010239
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