Hydrogen-bonding landscape of the carbamoylcyanonitrosomethanide anion in the crystal structure of its ammonium salt
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 m...
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International Union of Crystallography
2021-11-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989021010239 |
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| author | Kostiantyn V. Domasevitch Ganna A. Senchyk Andrey B. Lysenko Eduard B. Rusanov |
| author_facet | Kostiantyn V. Domasevitch Ganna A. Senchyk Andrey B. Lysenko Eduard B. Rusanov |
| author_sort | Kostiantyn V. Domasevitch |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-10T23:13:31Z |
| format | Article |
| id | doaj.art-140ca9a30e37412c84616e04f5be0ff8 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-12-10T23:13:31Z |
| publishDate | 2021-11-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-140ca9a30e37412c84616e04f5be0ff82022-12-22T01:29:53ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902021-11-0177111103110810.1107/S2056989021010239hb7989Hydrogen-bonding landscape of the carbamoylcyanonitrosomethanide anion in the crystal structure of its ammonium saltKostiantyn V. Domasevitch0Ganna A. Senchyk1Andrey B. Lysenko2Eduard B. Rusanov3Inorganic Chemistry Department, National Taras Shevchenko University of Kyiv, Volodymyrska Str. 64/13, 01601 Kyiv, UkraineInorganic Chemistry Department, National Taras Shevchenko University of Kyiv, Volodymyrska Str. 64/13, 01601 Kyiv, UkraineInorganic Chemistry Department, National Taras Shevchenko University of Kyiv, Volodymyrska Str. 64/13, 01601 Kyiv, UkraineInstitute of Organic Chemistry, Murmanskaya Str. 4, Kyiv 253660, UkraineThe 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.http://scripts.iucr.org/cgi-bin/paper?S2056989021010239crystal structurecarbamoylcyanonitrosomethanidesupramolecular synthonhydrogen bonding |
| spellingShingle | Kostiantyn V. Domasevitch Ganna A. Senchyk Andrey B. Lysenko Eduard B. Rusanov Hydrogen-bonding landscape of the carbamoylcyanonitrosomethanide anion in the crystal structure of its ammonium salt Acta Crystallographica Section E: Crystallographic Communications crystal structure carbamoylcyanonitrosomethanide supramolecular synthon hydrogen bonding |
| 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 | crystal structure carbamoylcyanonitrosomethanide supramolecular synthon hydrogen bonding |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989021010239 |
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