An unexpected tautomer: synthesis and crystal structure of N-[6-amino-4-(methylsulfanyl)-1,2-dihydro-1,3,5-triazin-2-ylidene]benzenesulfonamide
The title compound, C10H11N5O2S2, consists of an unexpected tautomer with a protonated nitrogen atom in the triazine ring and a formal exocyclic double bond C=N to the sulfonamide moiety. The ring angles at the unsubstituted nitrogen atoms are narrow, at 115.57 (12) and 115.19 (12)°, respectively, w...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2024-02-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989023011076 |
| _version_ | 1797323985008984064 |
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| author | Reham A. Mohamed-Ezzat Galal H. Elgemeie Peter G. Jones |
| author_facet | Reham A. Mohamed-Ezzat Galal H. Elgemeie Peter G. Jones |
| author_sort | Reham A. Mohamed-Ezzat |
| collection | DOAJ |
| description | The title compound, C10H11N5O2S2, consists of an unexpected tautomer with a protonated nitrogen atom in the triazine ring and a formal exocyclic double bond C=N to the sulfonamide moiety. The ring angles at the unsubstituted nitrogen atoms are narrow, at 115.57 (12) and 115.19 (12)°, respectively, whereas the angle at the carbon atom between these N atoms is very wide, 127.97 (13)°. The interplanar angle between the two rings is 79.56 (5)°. The molecules are linked by three classical hydrogen bonds, forming a ribbon structure. There are also unusual linkages involving three short contacts (< 3 Å) from a sulfonamide oxygen atom to the C—NH—C part of a triazine ring. |
| first_indexed | 2024-03-08T05:36:50Z |
| format | Article |
| id | doaj.art-6df59c65ba104e589181c63810892586 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-03-08T05:36:50Z |
| publishDate | 2024-02-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-6df59c65ba104e589181c638108925862024-02-05T17:27:26ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902024-02-0180212012410.1107/S2056989023011076yz2047An unexpected tautomer: synthesis and crystal structure of N-[6-amino-4-(methylsulfanyl)-1,2-dihydro-1,3,5-triazin-2-ylidene]benzenesulfonamideReham A. Mohamed-Ezzat0Galal H. Elgemeie1Peter G. Jones2Chemistry of Natural and Microbial Products Department, Pharmaceutical and Drug Industries Research Institute, National Research Centre, Cairo, EgyptChemistry Department, Faculty of Science, Helwan University, Cairo, EgyptInstitut für Anorganische und Analytische Chemie, Technische Universität Braunschweig, Hagenring 30, D-38106 Braunschweig, GermanyThe title compound, C10H11N5O2S2, consists of an unexpected tautomer with a protonated nitrogen atom in the triazine ring and a formal exocyclic double bond C=N to the sulfonamide moiety. The ring angles at the unsubstituted nitrogen atoms are narrow, at 115.57 (12) and 115.19 (12)°, respectively, whereas the angle at the carbon atom between these N atoms is very wide, 127.97 (13)°. The interplanar angle between the two rings is 79.56 (5)°. The molecules are linked by three classical hydrogen bonds, forming a ribbon structure. There are also unusual linkages involving three short contacts (< 3 Å) from a sulfonamide oxygen atom to the C—NH—C part of a triazine ring.http://scripts.iucr.org/cgi-bin/paper?S2056989023011076crystal structure1,3,5-triazinebenzenesulfonamidehydrogen bonds |
| spellingShingle | Reham A. Mohamed-Ezzat Galal H. Elgemeie Peter G. Jones An unexpected tautomer: synthesis and crystal structure of N-[6-amino-4-(methylsulfanyl)-1,2-dihydro-1,3,5-triazin-2-ylidene]benzenesulfonamide Acta Crystallographica Section E: Crystallographic Communications crystal structure 1,3,5-triazine benzenesulfonamide hydrogen bonds |
| title | An unexpected tautomer: synthesis and crystal structure of N-[6-amino-4-(methylsulfanyl)-1,2-dihydro-1,3,5-triazin-2-ylidene]benzenesulfonamide |
| title_full | An unexpected tautomer: synthesis and crystal structure of N-[6-amino-4-(methylsulfanyl)-1,2-dihydro-1,3,5-triazin-2-ylidene]benzenesulfonamide |
| title_fullStr | An unexpected tautomer: synthesis and crystal structure of N-[6-amino-4-(methylsulfanyl)-1,2-dihydro-1,3,5-triazin-2-ylidene]benzenesulfonamide |
| title_full_unstemmed | An unexpected tautomer: synthesis and crystal structure of N-[6-amino-4-(methylsulfanyl)-1,2-dihydro-1,3,5-triazin-2-ylidene]benzenesulfonamide |
| title_short | An unexpected tautomer: synthesis and crystal structure of N-[6-amino-4-(methylsulfanyl)-1,2-dihydro-1,3,5-triazin-2-ylidene]benzenesulfonamide |
| title_sort | unexpected tautomer synthesis and crystal structure of n 6 amino 4 methylsulfanyl 1 2 dihydro 1 3 5 triazin 2 ylidene benzenesulfonamide |
| topic | crystal structure 1,3,5-triazine benzenesulfonamide hydrogen bonds |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989023011076 |
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