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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...

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Autores principales: Manjula, Padmanabha S., Sarojini, Balladka K., Yathirajan, Hemmige S., Akkurt, Mehmet, Ersanlı, Cem Cüneyt, Glidewell, Christopher
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2015
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.
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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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