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Supramolecular interactions in 2,6-diamino-4-chloropyrimidin-1-ium 5-chlorosalicylate and bis(2,6-diamino-4-chloropyrimidin-1-ium) naphthalene-1,5-disulfonate
The crystals of two new salts, 2,6-diamino-4-chloropyrimidin-1-ium 5-chlorosalicylate, C(4)H(6)ClN(4) (+)·C(7)H(4)ClO(3) (−), (I), and bis(2,6-diamino-4-chloropyrimidin-1-ium) naphthalene-1,5-di-sulfonate, 2C(4)H(6)ClN(4) (+)·C(10)H(6)O(6)S(2) (2−), (II), have been synthesized and characterize...
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2018
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5956345/ https://www.ncbi.nlm.nih.gov/pubmed/29850062 http://dx.doi.org/10.1107/S2056989018001196 |
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author | Swinton Darious, Robert Thomas Muthiah, Packianathan Perdih, Franc |
author_facet | Swinton Darious, Robert Thomas Muthiah, Packianathan Perdih, Franc |
author_sort | Swinton Darious, Robert |
collection | PubMed |
description | The crystals of two new salts, 2,6-diamino-4-chloropyrimidin-1-ium 5-chlorosalicylate, C(4)H(6)ClN(4) (+)·C(7)H(4)ClO(3) (−), (I), and bis(2,6-diamino-4-chloropyrimidin-1-ium) naphthalene-1,5-di-sulfonate, 2C(4)H(6)ClN(4) (+)·C(10)H(6)O(6)S(2) (2−), (II), have been synthesized and characterized by single-crystal X-ray diffraction. In both compounds, the N atom of the pyrimidine group in between the amino substituents is protonated and the pyrimidinium cation forms a pair of N—H⋯O hydrogen bonds with the carboxylate/sulfonate ion, leading to a robust R (2) (2)(8) motif (supramolecular heterosynthon). In compound (I), a self-complementary base pairing involving the other pyrimidinium ring nitrogen atom and one of the amino groups via a pair of N—H⋯N hydrogen bonds [R (2) (2)(8) homosynthon] is also present. In compound (II), the crystallographic inversion centre coincides with the inversion centre of the naphthalene-1,5-disulfonate ion and all the sulfonate O atoms are hydrogen-bond acceptors, generating fused-ring motifs and a quadruple DDAA array. A halogen-bond (Cl⋯Cl) interaction is present in (I) with a distance and angle of 3.3505 (12) Å and 151.37 (10)°, respectively. In addition, a C—Cl⋯π interaction and a π–π interaction in (I) and a π–π interaction in (II) further stabilize these crystal structures. |
format | Online Article Text |
id | pubmed-5956345 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-59563452018-05-30 Supramolecular interactions in 2,6-diamino-4-chloropyrimidin-1-ium 5-chlorosalicylate and bis(2,6-diamino-4-chloropyrimidin-1-ium) naphthalene-1,5-disulfonate Swinton Darious, Robert Thomas Muthiah, Packianathan Perdih, Franc Acta Crystallogr E Crystallogr Commun Research Communications The crystals of two new salts, 2,6-diamino-4-chloropyrimidin-1-ium 5-chlorosalicylate, C(4)H(6)ClN(4) (+)·C(7)H(4)ClO(3) (−), (I), and bis(2,6-diamino-4-chloropyrimidin-1-ium) naphthalene-1,5-di-sulfonate, 2C(4)H(6)ClN(4) (+)·C(10)H(6)O(6)S(2) (2−), (II), have been synthesized and characterized by single-crystal X-ray diffraction. In both compounds, the N atom of the pyrimidine group in between the amino substituents is protonated and the pyrimidinium cation forms a pair of N—H⋯O hydrogen bonds with the carboxylate/sulfonate ion, leading to a robust R (2) (2)(8) motif (supramolecular heterosynthon). In compound (I), a self-complementary base pairing involving the other pyrimidinium ring nitrogen atom and one of the amino groups via a pair of N—H⋯N hydrogen bonds [R (2) (2)(8) homosynthon] is also present. In compound (II), the crystallographic inversion centre coincides with the inversion centre of the naphthalene-1,5-disulfonate ion and all the sulfonate O atoms are hydrogen-bond acceptors, generating fused-ring motifs and a quadruple DDAA array. A halogen-bond (Cl⋯Cl) interaction is present in (I) with a distance and angle of 3.3505 (12) Å and 151.37 (10)°, respectively. In addition, a C—Cl⋯π interaction and a π–π interaction in (I) and a π–π interaction in (II) further stabilize these crystal structures. International Union of Crystallography 2018-01-26 /pmc/articles/PMC5956345/ /pubmed/29850062 http://dx.doi.org/10.1107/S2056989018001196 Text en © Swinton Darious et al. 2018 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 Swinton Darious, Robert Thomas Muthiah, Packianathan Perdih, Franc Supramolecular interactions in 2,6-diamino-4-chloropyrimidin-1-ium 5-chlorosalicylate and bis(2,6-diamino-4-chloropyrimidin-1-ium) naphthalene-1,5-disulfonate |
title | Supramolecular interactions in 2,6-diamino-4-chloropyrimidin-1-ium 5-chlorosalicylate and bis(2,6-diamino-4-chloropyrimidin-1-ium) naphthalene-1,5-disulfonate |
title_full | Supramolecular interactions in 2,6-diamino-4-chloropyrimidin-1-ium 5-chlorosalicylate and bis(2,6-diamino-4-chloropyrimidin-1-ium) naphthalene-1,5-disulfonate |
title_fullStr | Supramolecular interactions in 2,6-diamino-4-chloropyrimidin-1-ium 5-chlorosalicylate and bis(2,6-diamino-4-chloropyrimidin-1-ium) naphthalene-1,5-disulfonate |
title_full_unstemmed | Supramolecular interactions in 2,6-diamino-4-chloropyrimidin-1-ium 5-chlorosalicylate and bis(2,6-diamino-4-chloropyrimidin-1-ium) naphthalene-1,5-disulfonate |
title_short | Supramolecular interactions in 2,6-diamino-4-chloropyrimidin-1-ium 5-chlorosalicylate and bis(2,6-diamino-4-chloropyrimidin-1-ium) naphthalene-1,5-disulfonate |
title_sort | supramolecular interactions in 2,6-diamino-4-chloropyrimidin-1-ium 5-chlorosalicylate and bis(2,6-diamino-4-chloropyrimidin-1-ium) naphthalene-1,5-disulfonate |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5956345/ https://www.ncbi.nlm.nih.gov/pubmed/29850062 http://dx.doi.org/10.1107/S2056989018001196 |
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