6-{5-Amino-3-tert-butyl-4-[(E)-(3-methyl-1,2,4-thiadiazol-5-yl)diazenyl]-1H-pyrazol-1-yl}-1,3,5-triazine-2,4(1H,3H)-dione–1-methylpyrrolidin-2-one–water (1/1/1)
In the title compound, C13H16N10O2S·C5H9NO·H2O, the entire 1-methylpyrrolidin-2-one (NMP) molecule is disordered over two sites with occupancies of 0.488 (5) and 0.512 (5). The six-membered triazine ring and the two five-membered pyrazole and thi...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2010-04-01
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| Series: | Acta Crystallographica Section E |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S1600536810010871 |
| _version_ | 1818907621038489600 |
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| author | Hiroki Shibata Jin Mizuguchi |
| author_facet | Hiroki Shibata Jin Mizuguchi |
| author_sort | Hiroki Shibata |
| collection | DOAJ |
| description | In the title compound, C13H16N10O2S·C5H9NO·H2O, the entire 1-methylpyrrolidin-2-one (NMP) molecule is disordered over two sites with occupancies of 0.488 (5) and 0.512 (5). The six-membered triazine ring and the two five-membered pyrazole and thiadiazole rings, together with the diazene (–N=N–) linkage are almost coplanar (r.m.s. deviation for the non-H atoms = 0.0256 Å) with methyl groups from the tert-butyl substituent on the pyrazole ring located above and below the plane. Three intramolecular N—H...N hydrogen bonds contribute to the planarity of the system. The O atom of the NMP molecule is hydrogen bonded to an O—H group of water. In turn, the water molecule is hydrogen bonded to the mono-azo skeleton through intermolecular N—H...O and O—H...N hydrogen bonds. At both ends of the long molecular axis of the main molecule there are intermolecular N—H...N hydrogen bonds, arranged in a head-to-tail fashion, between the N—H group of the triazine ring of one molecule and the N atom of the thiadiazole ring of a neighboring molecule. These form a polymeric chain along [110] or [1overline10]. The main molecules are stacked alternately along the b axis, which effectively cancels their dipole moments. In addition, pairs of alternate molecules are dimerized via intermolecular hydrogen bonds involving the solvent molecules. |
| first_indexed | 2024-12-19T21:58:02Z |
| format | Article |
| id | doaj.art-b847e5f3a93141a498e7ef2d469a2420 |
| institution | Directory Open Access Journal |
| issn | 1600-5368 |
| language | English |
| last_indexed | 2024-12-19T21:58:02Z |
| publishDate | 2010-04-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E |
| spelling | doaj.art-b847e5f3a93141a498e7ef2d469a24202022-12-21T20:04:14ZengInternational Union of CrystallographyActa Crystallographica Section E1600-53682010-04-01664o944o94510.1107/S16005368100108716-{5-Amino-3-tert-butyl-4-[(E)-(3-methyl-1,2,4-thiadiazol-5-yl)diazenyl]-1H-pyrazol-1-yl}-1,3,5-triazine-2,4(1H,3H)-dione–1-methylpyrrolidin-2-one–water (1/1/1)Hiroki ShibataJin MizuguchiIn the title compound, C13H16N10O2S·C5H9NO·H2O, the entire 1-methylpyrrolidin-2-one (NMP) molecule is disordered over two sites with occupancies of 0.488 (5) and 0.512 (5). The six-membered triazine ring and the two five-membered pyrazole and thiadiazole rings, together with the diazene (–N=N–) linkage are almost coplanar (r.m.s. deviation for the non-H atoms = 0.0256 Å) with methyl groups from the tert-butyl substituent on the pyrazole ring located above and below the plane. Three intramolecular N—H...N hydrogen bonds contribute to the planarity of the system. The O atom of the NMP molecule is hydrogen bonded to an O—H group of water. In turn, the water molecule is hydrogen bonded to the mono-azo skeleton through intermolecular N—H...O and O—H...N hydrogen bonds. At both ends of the long molecular axis of the main molecule there are intermolecular N—H...N hydrogen bonds, arranged in a head-to-tail fashion, between the N—H group of the triazine ring of one molecule and the N atom of the thiadiazole ring of a neighboring molecule. These form a polymeric chain along [110] or [1overline10]. The main molecules are stacked alternately along the b axis, which effectively cancels their dipole moments. In addition, pairs of alternate molecules are dimerized via intermolecular hydrogen bonds involving the solvent molecules.http://scripts.iucr.org/cgi-bin/paper?S1600536810010871 |
| spellingShingle | Hiroki Shibata Jin Mizuguchi 6-{5-Amino-3-tert-butyl-4-[(E)-(3-methyl-1,2,4-thiadiazol-5-yl)diazenyl]-1H-pyrazol-1-yl}-1,3,5-triazine-2,4(1H,3H)-dione–1-methylpyrrolidin-2-one–water (1/1/1) Acta Crystallographica Section E |
| title | 6-{5-Amino-3-tert-butyl-4-[(E)-(3-methyl-1,2,4-thiadiazol-5-yl)diazenyl]-1H-pyrazol-1-yl}-1,3,5-triazine-2,4(1H,3H)-dione–1-methylpyrrolidin-2-one–water (1/1/1) |
| title_full | 6-{5-Amino-3-tert-butyl-4-[(E)-(3-methyl-1,2,4-thiadiazol-5-yl)diazenyl]-1H-pyrazol-1-yl}-1,3,5-triazine-2,4(1H,3H)-dione–1-methylpyrrolidin-2-one–water (1/1/1) |
| title_fullStr | 6-{5-Amino-3-tert-butyl-4-[(E)-(3-methyl-1,2,4-thiadiazol-5-yl)diazenyl]-1H-pyrazol-1-yl}-1,3,5-triazine-2,4(1H,3H)-dione–1-methylpyrrolidin-2-one–water (1/1/1) |
| title_full_unstemmed | 6-{5-Amino-3-tert-butyl-4-[(E)-(3-methyl-1,2,4-thiadiazol-5-yl)diazenyl]-1H-pyrazol-1-yl}-1,3,5-triazine-2,4(1H,3H)-dione–1-methylpyrrolidin-2-one–water (1/1/1) |
| title_short | 6-{5-Amino-3-tert-butyl-4-[(E)-(3-methyl-1,2,4-thiadiazol-5-yl)diazenyl]-1H-pyrazol-1-yl}-1,3,5-triazine-2,4(1H,3H)-dione–1-methylpyrrolidin-2-one–water (1/1/1) |
| title_sort | 6 5 amino 3 tert butyl 4 e 3 methyl 1 2 4 thiadiazol 5 yl diazenyl 1h pyrazol 1 yl 1 3 5 triazine 2 4 1h 3h dione amp 8211 1 methylpyrrolidin 2 one amp 8211 water 1 1 1 |
| url | http://scripts.iucr.org/cgi-bin/paper?S1600536810010871 |
| work_keys_str_mv | AT hirokishibata 65amino3tertbutyl4e3methyl124thiadiazol5yldiazenyl1hpyrazol1yl135triazine241h3hdioneamp82111methylpyrrolidin2oneamp8211water111 AT jinmizuguchi 65amino3tertbutyl4e3methyl124thiadiazol5yldiazenyl1hpyrazol1yl135triazine241h3hdioneamp82111methylpyrrolidin2oneamp8211water111 |