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(E)-3-Methyl-4-[(2-oxidoquinolin-1-ium-3-yl)methyleneamino]-1H-1,2,4-triazole-5(4H)-thione N,N-dimethylformamide solvate
The title 1,2,4-triazole compound, C(13)H(11)N(5)OS·C(3)H(7)NO, crystallizes as a 1:1 dimethylformamide (DMF) solvate. The main molecule exists in a trans configuration with respect to the acyclic C=N bond. An intramolecular C—H⋯S hydrogen bond generates an S(6) ring motif. In the synthesis, a pr...
Autores principales: | , , , |
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2009
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2972175/ https://www.ncbi.nlm.nih.gov/pubmed/21578940 http://dx.doi.org/10.1107/S1600536809050090 |
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author | Goh, Jia Hao Fun, Hoong-Kun Adhikari, Adithya Kalluraya, B. |
author_facet | Goh, Jia Hao Fun, Hoong-Kun Adhikari, Adithya Kalluraya, B. |
author_sort | Goh, Jia Hao |
collection | PubMed |
description | The title 1,2,4-triazole compound, C(13)H(11)N(5)OS·C(3)H(7)NO, crystallizes as a 1:1 dimethylformamide (DMF) solvate. The main molecule exists in a trans configuration with respect to the acyclic C=N bond. An intramolecular C—H⋯S hydrogen bond generates an S(6) ring motif. In the synthesis, a proton is transferred from the O atom of a hydroxy group to the quinoline group N atom. The essentially planar triazole ring and quinoline ring system [maximum deviations of 0.001 (2) and 0.013 (2) Å, respectively] form a dihedral angle of 5.86 (9)°. In the crystal structure, molecules of (E)-4-[(2-hydroxy-3-quinolyl)methyleneamino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione are linked into R (2) (2)(8) centrosymmteric dimers via N—H⋯O hydrogen bonds. These dimers are further linked into an extended three-dimensional structure by the DMF solvent molecules via intermolecular N—H⋯O and C—H⋯O hydrogen bonds. The crystal structure is consolidated by two different intermolecular π–π interactions [centroid–centroid distances = 3.6593 (12) and 3.6892 (12) Å]. |
format | Text |
id | pubmed-2972175 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2009 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29721752010-12-30 (E)-3-Methyl-4-[(2-oxidoquinolin-1-ium-3-yl)methyleneamino]-1H-1,2,4-triazole-5(4H)-thione N,N-dimethylformamide solvate Goh, Jia Hao Fun, Hoong-Kun Adhikari, Adithya Kalluraya, B. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title 1,2,4-triazole compound, C(13)H(11)N(5)OS·C(3)H(7)NO, crystallizes as a 1:1 dimethylformamide (DMF) solvate. The main molecule exists in a trans configuration with respect to the acyclic C=N bond. An intramolecular C—H⋯S hydrogen bond generates an S(6) ring motif. In the synthesis, a proton is transferred from the O atom of a hydroxy group to the quinoline group N atom. The essentially planar triazole ring and quinoline ring system [maximum deviations of 0.001 (2) and 0.013 (2) Å, respectively] form a dihedral angle of 5.86 (9)°. In the crystal structure, molecules of (E)-4-[(2-hydroxy-3-quinolyl)methyleneamino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione are linked into R (2) (2)(8) centrosymmteric dimers via N—H⋯O hydrogen bonds. These dimers are further linked into an extended three-dimensional structure by the DMF solvent molecules via intermolecular N—H⋯O and C—H⋯O hydrogen bonds. The crystal structure is consolidated by two different intermolecular π–π interactions [centroid–centroid distances = 3.6593 (12) and 3.6892 (12) Å]. International Union of Crystallography 2009-11-28 /pmc/articles/PMC2972175/ /pubmed/21578940 http://dx.doi.org/10.1107/S1600536809050090 Text en © Goh et al. 2009 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 Goh, Jia Hao Fun, Hoong-Kun Adhikari, Adithya Kalluraya, B. (E)-3-Methyl-4-[(2-oxidoquinolin-1-ium-3-yl)methyleneamino]-1H-1,2,4-triazole-5(4H)-thione N,N-dimethylformamide solvate |
title | (E)-3-Methyl-4-[(2-oxidoquinolin-1-ium-3-yl)methyleneamino]-1H-1,2,4-triazole-5(4H)-thione N,N-dimethylformamide solvate |
title_full | (E)-3-Methyl-4-[(2-oxidoquinolin-1-ium-3-yl)methyleneamino]-1H-1,2,4-triazole-5(4H)-thione N,N-dimethylformamide solvate |
title_fullStr | (E)-3-Methyl-4-[(2-oxidoquinolin-1-ium-3-yl)methyleneamino]-1H-1,2,4-triazole-5(4H)-thione N,N-dimethylformamide solvate |
title_full_unstemmed | (E)-3-Methyl-4-[(2-oxidoquinolin-1-ium-3-yl)methyleneamino]-1H-1,2,4-triazole-5(4H)-thione N,N-dimethylformamide solvate |
title_short | (E)-3-Methyl-4-[(2-oxidoquinolin-1-ium-3-yl)methyleneamino]-1H-1,2,4-triazole-5(4H)-thione N,N-dimethylformamide solvate |
title_sort | (e)-3-methyl-4-[(2-oxidoquinolin-1-ium-3-yl)methyleneamino]-1h-1,2,4-triazole-5(4h)-thione n,n-dimethylformamide solvate |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2972175/ https://www.ncbi.nlm.nih.gov/pubmed/21578940 http://dx.doi.org/10.1107/S1600536809050090 |
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