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The crystal structures of three 3-methyl-1H-1,2,4-triazole-5-thiones, including a second polymorph of 4-[(E)-(5-bromo-2-hydroxybenzylidene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione and a redetermination of 4-amino-3-methyl-1H-1,2,4-triazole-5(4H)-thione
The structures of three 3-methyl-1H-1,2,4-triazole-5-thione derivatives are reported. The structure of 4-amino-3-methyl-1H-1,2,4-triazole-5(4H)-thione, C(3)H(6)N(4)S, (I), has been redetermined with an improved model for the H atoms: the non-H atoms of (I) all lie on mirror planes in space group Pbc...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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International Union of Crystallography
2015
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4555427/ https://www.ncbi.nlm.nih.gov/pubmed/26396835 http://dx.doi.org/10.1107/S205698901501422X |
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author | Manjula, Padmanabha S. Sarojini, Balladka K. Yathirajan, Hemmige S. Akkurt, Mehmet Ersanlı, Cem Cüneyt Glidewell, Christopher |
author_facet | Manjula, Padmanabha S. Sarojini, Balladka K. Yathirajan, Hemmige S. Akkurt, Mehmet Ersanlı, Cem Cüneyt Glidewell, Christopher |
author_sort | Manjula, Padmanabha S. |
collection | PubMed |
description | The structures of three 3-methyl-1H-1,2,4-triazole-5-thione derivatives are reported. The structure of 4-amino-3-methyl-1H-1,2,4-triazole-5(4H)-thione, C(3)H(6)N(4)S, (I), has been redetermined with an improved model for the H atoms: the non-H atoms of (I) all lie on mirror planes in space group Pbcm, and the H atoms of the methyl group are disordered over two sets of reflection-related atomic sites having occupancy 0.5: two independent N—H⋯S hydrogen bonds link the molecules of compound (I) into complex sheets. The non-H atoms in the molecules of 4-[(E)-(3,4-dimethoxybenzylidene)amino]-3-methyl-1H-1,2,4-triazol-5(4H)-thione, C(12)H(14)N(4)O(2)S, (II), despite lying in general positions are close to planar, with a dihedral angle between the two rings of 6.31 (10)°: the molecules of compound (II) are linked by a three-centre N—H⋯(O)(2) hydrogen bond into a C(10)C(11)[R (1) (2)(5)] chain of rings. A second polymorph of 4-[(E)-(5-bromo-2-hydroxy-5-bromobenzylidene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione, C(10)H(9)BrN(4)OS, (III), has been identified; the non-H atoms are nearly co-planar with a dihedral angle between the two rings of 1.9 (4)°. There is an intramolecular O—H⋯N hydrogen bond and the molecules are linked by N—H⋯S hydrogen bonds, forming centrosymmetric R (2) (2)(8) dimers. Comparisons are made with some related structures. |
format | Online Article Text |
id | pubmed-4555427 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-45554272015-09-22 The crystal structures of three 3-methyl-1H-1,2,4-triazole-5-thiones, including a second polymorph of 4-[(E)-(5-bromo-2-hydroxybenzylidene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione and a redetermination of 4-amino-3-methyl-1H-1,2,4-triazole-5(4H)-thione Manjula, Padmanabha S. Sarojini, Balladka K. Yathirajan, Hemmige S. Akkurt, Mehmet Ersanlı, Cem Cüneyt Glidewell, Christopher Acta Crystallogr E Crystallogr Commun Research Communications The structures of three 3-methyl-1H-1,2,4-triazole-5-thione derivatives are reported. The structure of 4-amino-3-methyl-1H-1,2,4-triazole-5(4H)-thione, C(3)H(6)N(4)S, (I), has been redetermined with an improved model for the H atoms: the non-H atoms of (I) all lie on mirror planes in space group Pbcm, and the H atoms of the methyl group are disordered over two sets of reflection-related atomic sites having occupancy 0.5: two independent N—H⋯S hydrogen bonds link the molecules of compound (I) into complex sheets. The non-H atoms in the molecules of 4-[(E)-(3,4-dimethoxybenzylidene)amino]-3-methyl-1H-1,2,4-triazol-5(4H)-thione, C(12)H(14)N(4)O(2)S, (II), despite lying in general positions are close to planar, with a dihedral angle between the two rings of 6.31 (10)°: the molecules of compound (II) are linked by a three-centre N—H⋯(O)(2) hydrogen bond into a C(10)C(11)[R (1) (2)(5)] chain of rings. A second polymorph of 4-[(E)-(5-bromo-2-hydroxy-5-bromobenzylidene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione, C(10)H(9)BrN(4)OS, (III), has been identified; the non-H atoms are nearly co-planar with a dihedral angle between the two rings of 1.9 (4)°. There is an intramolecular O—H⋯N hydrogen bond and the molecules are linked by N—H⋯S hydrogen bonds, forming centrosymmetric R (2) (2)(8) dimers. Comparisons are made with some related structures. International Union of Crystallography 2015-08-06 /pmc/articles/PMC4555427/ /pubmed/26396835 http://dx.doi.org/10.1107/S205698901501422X Text en © Manjula et al. 2015 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/2.0/uk/ |
spellingShingle | Research Communications Manjula, Padmanabha S. Sarojini, Balladka K. Yathirajan, Hemmige S. Akkurt, Mehmet Ersanlı, Cem Cüneyt Glidewell, Christopher The crystal structures of three 3-methyl-1H-1,2,4-triazole-5-thiones, including a second polymorph of 4-[(E)-(5-bromo-2-hydroxybenzylidene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione and a redetermination of 4-amino-3-methyl-1H-1,2,4-triazole-5(4H)-thione |
title | The crystal structures of three 3-methyl-1H-1,2,4-triazole-5-thiones, including a second polymorph of 4-[(E)-(5-bromo-2-hydroxybenzylidene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione and a redetermination of 4-amino-3-methyl-1H-1,2,4-triazole-5(4H)-thione |
title_full | The crystal structures of three 3-methyl-1H-1,2,4-triazole-5-thiones, including a second polymorph of 4-[(E)-(5-bromo-2-hydroxybenzylidene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione and a redetermination of 4-amino-3-methyl-1H-1,2,4-triazole-5(4H)-thione |
title_fullStr | The crystal structures of three 3-methyl-1H-1,2,4-triazole-5-thiones, including a second polymorph of 4-[(E)-(5-bromo-2-hydroxybenzylidene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione and a redetermination of 4-amino-3-methyl-1H-1,2,4-triazole-5(4H)-thione |
title_full_unstemmed | The crystal structures of three 3-methyl-1H-1,2,4-triazole-5-thiones, including a second polymorph of 4-[(E)-(5-bromo-2-hydroxybenzylidene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione and a redetermination of 4-amino-3-methyl-1H-1,2,4-triazole-5(4H)-thione |
title_short | The crystal structures of three 3-methyl-1H-1,2,4-triazole-5-thiones, including a second polymorph of 4-[(E)-(5-bromo-2-hydroxybenzylidene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione and a redetermination of 4-amino-3-methyl-1H-1,2,4-triazole-5(4H)-thione |
title_sort | crystal structures of three 3-methyl-1h-1,2,4-triazole-5-thiones, including a second polymorph of 4-[(e)-(5-bromo-2-hydroxybenzylidene)amino]-3-methyl-1h-1,2,4-triazole-5(4h)-thione and a redetermination of 4-amino-3-methyl-1h-1,2,4-triazole-5(4h)-thione |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4555427/ https://www.ncbi.nlm.nih.gov/pubmed/26396835 http://dx.doi.org/10.1107/S205698901501422X |
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