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4,5-Diamino-3-[(E,E)-4-(4,5-diamino-4H-1,2,4-triazol-3-yl)buta-1,3-dienyl]-4H-1,2,4-triazol-1-ium chloride
The title compound, C(8)H(13)N(10) (+)·Cl(−), is the monochlorhydrate salt of an aromatic bis(diaminotriazole). The cation is centrosymmetric, lying about an inversion centre (C(i) symmetry) because the acidic H atom is disordered over two centrosymmetrically related ring N atoms, with equal mult...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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International Union of Crystallography
2013
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3770399/ https://www.ncbi.nlm.nih.gov/pubmed/24046684 http://dx.doi.org/10.1107/S1600536813016589 |
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author | Centore, Roberto Piccialli, Vincenzo |
author_facet | Centore, Roberto Piccialli, Vincenzo |
author_sort | Centore, Roberto |
collection | PubMed |
description | The title compound, C(8)H(13)N(10) (+)·Cl(−), is the monochlorhydrate salt of an aromatic bis(diaminotriazole). The cation is centrosymmetric, lying about an inversion centre (C(i) symmetry) because the acidic H atom is disordered over two centrosymmetrically related ring N atoms, with equal multiplicity. It is noteworthy that protonation occurs at an N atom of the ring, instead of at the C—NH(2) or N—NH(2) amino groups. The chloride anions are also in special positions, as they lie on binary axes, and so the crystallographically independent unit contains half of a formula unit. The N atom of the C—NH(2) group is sp (2)-hybridized and the amino group is coplanar with the triazole ring [dihedral angle = 5 (3)°], while the N atom of the N—NH(2) amino group is pyramidal. The C=C bonds are in E conformations and the cation is flat because the conformation of the carbon chain is fully extended. The chloride anions are hexacoordinated, in a distorted trigonal–prismatic geometry, and they are involved, as acceptors, in six hydrogen bonds. Chains of hydrogen-bonded cations, running along c and a + c, are generated by c-glide and C (2) rotation, respectively. This combination of N—H⋯Cl and N—H⋯N hydrogen bonds leads to the formation of a three-dimensional network. |
format | Online Article Text |
id | pubmed-3770399 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-37703992013-09-17 4,5-Diamino-3-[(E,E)-4-(4,5-diamino-4H-1,2,4-triazol-3-yl)buta-1,3-dienyl]-4H-1,2,4-triazol-1-ium chloride Centore, Roberto Piccialli, Vincenzo Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(8)H(13)N(10) (+)·Cl(−), is the monochlorhydrate salt of an aromatic bis(diaminotriazole). The cation is centrosymmetric, lying about an inversion centre (C(i) symmetry) because the acidic H atom is disordered over two centrosymmetrically related ring N atoms, with equal multiplicity. It is noteworthy that protonation occurs at an N atom of the ring, instead of at the C—NH(2) or N—NH(2) amino groups. The chloride anions are also in special positions, as they lie on binary axes, and so the crystallographically independent unit contains half of a formula unit. The N atom of the C—NH(2) group is sp (2)-hybridized and the amino group is coplanar with the triazole ring [dihedral angle = 5 (3)°], while the N atom of the N—NH(2) amino group is pyramidal. The C=C bonds are in E conformations and the cation is flat because the conformation of the carbon chain is fully extended. The chloride anions are hexacoordinated, in a distorted trigonal–prismatic geometry, and they are involved, as acceptors, in six hydrogen bonds. Chains of hydrogen-bonded cations, running along c and a + c, are generated by c-glide and C (2) rotation, respectively. This combination of N—H⋯Cl and N—H⋯N hydrogen bonds leads to the formation of a three-dimensional network. International Union of Crystallography 2013-06-22 /pmc/articles/PMC3770399/ /pubmed/24046684 http://dx.doi.org/10.1107/S1600536813016589 Text en © Centore and Piccialli 2013 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 Centore, Roberto Piccialli, Vincenzo 4,5-Diamino-3-[(E,E)-4-(4,5-diamino-4H-1,2,4-triazol-3-yl)buta-1,3-dienyl]-4H-1,2,4-triazol-1-ium chloride |
title | 4,5-Diamino-3-[(E,E)-4-(4,5-diamino-4H-1,2,4-triazol-3-yl)buta-1,3-dienyl]-4H-1,2,4-triazol-1-ium chloride |
title_full | 4,5-Diamino-3-[(E,E)-4-(4,5-diamino-4H-1,2,4-triazol-3-yl)buta-1,3-dienyl]-4H-1,2,4-triazol-1-ium chloride |
title_fullStr | 4,5-Diamino-3-[(E,E)-4-(4,5-diamino-4H-1,2,4-triazol-3-yl)buta-1,3-dienyl]-4H-1,2,4-triazol-1-ium chloride |
title_full_unstemmed | 4,5-Diamino-3-[(E,E)-4-(4,5-diamino-4H-1,2,4-triazol-3-yl)buta-1,3-dienyl]-4H-1,2,4-triazol-1-ium chloride |
title_short | 4,5-Diamino-3-[(E,E)-4-(4,5-diamino-4H-1,2,4-triazol-3-yl)buta-1,3-dienyl]-4H-1,2,4-triazol-1-ium chloride |
title_sort | 4,5-diamino-3-[(e,e)-4-(4,5-diamino-4h-1,2,4-triazol-3-yl)buta-1,3-dienyl]-4h-1,2,4-triazol-1-ium chloride |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3770399/ https://www.ncbi.nlm.nih.gov/pubmed/24046684 http://dx.doi.org/10.1107/S1600536813016589 |
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