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N-Carbethoxy-N′-[3-(4-methylphenyl)-1H-1,2,4-triazol-5-yl]thiourea
The title compound, [systematic name: ethyl ({[3-(4-methylphenyl)-1H-1,2,4-triazol-5-yl]amino}carbonothioyl)carbamate], C(13)H(16)N(5)O(2)S, exists in the 3-aryl-5-thioureido-1H-1,2,4-triazole tautomeric form. The molecular structure is stabilized by intramolecular hydrogen bonding (N—H⋯S=C betwe...
Autores principales: | , , , , |
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Formato: | Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2010
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2983713/ https://www.ncbi.nlm.nih.gov/pubmed/21580320 http://dx.doi.org/10.1107/S1600536810004289 |
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author | Dolzhenko, Anton V. Tan, Geok Kheng Koh, Lip Lin Dolzhenko, Anna V. Chui, Wai Keung |
author_facet | Dolzhenko, Anton V. Tan, Geok Kheng Koh, Lip Lin Dolzhenko, Anna V. Chui, Wai Keung |
author_sort | Dolzhenko, Anton V. |
collection | PubMed |
description | The title compound, [systematic name: ethyl ({[3-(4-methylphenyl)-1H-1,2,4-triazol-5-yl]amino}carbonothioyl)carbamate], C(13)H(16)N(5)O(2)S, exists in the 3-aryl-5-thioureido-1H-1,2,4-triazole tautomeric form. The molecular structure is stabilized by intramolecular hydrogen bonding (N—H⋯S=C between the endocyclic N-bound H atom and the thioureido S atom, and N—H⋯O=C within the ethoxycarbonylthiourea unit), both arranged in an S(6) graph-set motif. The mean planes of the phenyl and 1,2,4-triazole rings make a dihedral angle of 6.59 (10)°. In the crystal structure, the molecules form two types of centrosymmetric dimers connected by intermolecular hydrogen bonds; in the first, the N—NH triazole sides of two molecules are connected [R (2) (2)(6) graph-set motif] and the second is an N—H⋯S=C interaction between the imide H atoms and the thiocarbonyl S atoms [R (2) (2)(8) graph-set motif]. Together, they form a network parallel to the (111) plane. |
format | Text |
id | pubmed-2983713 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2010 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29837132010-12-30 N-Carbethoxy-N′-[3-(4-methylphenyl)-1H-1,2,4-triazol-5-yl]thiourea Dolzhenko, Anton V. Tan, Geok Kheng Koh, Lip Lin Dolzhenko, Anna V. Chui, Wai Keung Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, [systematic name: ethyl ({[3-(4-methylphenyl)-1H-1,2,4-triazol-5-yl]amino}carbonothioyl)carbamate], C(13)H(16)N(5)O(2)S, exists in the 3-aryl-5-thioureido-1H-1,2,4-triazole tautomeric form. The molecular structure is stabilized by intramolecular hydrogen bonding (N—H⋯S=C between the endocyclic N-bound H atom and the thioureido S atom, and N—H⋯O=C within the ethoxycarbonylthiourea unit), both arranged in an S(6) graph-set motif. The mean planes of the phenyl and 1,2,4-triazole rings make a dihedral angle of 6.59 (10)°. In the crystal structure, the molecules form two types of centrosymmetric dimers connected by intermolecular hydrogen bonds; in the first, the N—NH triazole sides of two molecules are connected [R (2) (2)(6) graph-set motif] and the second is an N—H⋯S=C interaction between the imide H atoms and the thiocarbonyl S atoms [R (2) (2)(8) graph-set motif]. Together, they form a network parallel to the (111) plane. International Union of Crystallography 2010-02-06 /pmc/articles/PMC2983713/ /pubmed/21580320 http://dx.doi.org/10.1107/S1600536810004289 Text en © Dolzhenko et al. 2010 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Organic Papers Dolzhenko, Anton V. Tan, Geok Kheng Koh, Lip Lin Dolzhenko, Anna V. Chui, Wai Keung N-Carbethoxy-N′-[3-(4-methylphenyl)-1H-1,2,4-triazol-5-yl]thiourea |
title |
N-Carbethoxy-N′-[3-(4-methylphenyl)-1H-1,2,4-triazol-5-yl]thiourea |
title_full |
N-Carbethoxy-N′-[3-(4-methylphenyl)-1H-1,2,4-triazol-5-yl]thiourea |
title_fullStr |
N-Carbethoxy-N′-[3-(4-methylphenyl)-1H-1,2,4-triazol-5-yl]thiourea |
title_full_unstemmed |
N-Carbethoxy-N′-[3-(4-methylphenyl)-1H-1,2,4-triazol-5-yl]thiourea |
title_short |
N-Carbethoxy-N′-[3-(4-methylphenyl)-1H-1,2,4-triazol-5-yl]thiourea |
title_sort | n-carbethoxy-n′-[3-(4-methylphenyl)-1h-1,2,4-triazol-5-yl]thiourea |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2983713/ https://www.ncbi.nlm.nih.gov/pubmed/21580320 http://dx.doi.org/10.1107/S1600536810004289 |
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