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Crystal structure, hydrogen bonding and Hirshfeld surface analysis of 2-amino-4-methoxy-6-methylpyrimidinium 4-chlorobenzoate
In the crystal structure of the title salt, C(6)H(10)N(3)O(+)·C(7)H(4)ClO(2) (−), the dihedral angle between the pyrimidine ring of the 2-amino-4-methoxy-6-methylpyrimidine cation and the the benzene ring of the 2-chlorobenzoate anion is 2.2 (1)°. In the anion, the benzene ring forms a dihedral a...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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International Union of Crystallography
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5947481/ https://www.ncbi.nlm.nih.gov/pubmed/29850085 http://dx.doi.org/10.1107/S2056989018005583 |
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author | Jeevaraj, Muthaiah Sivajeyanthi, Palaniyappan Edison, Bellarmin Thanigaimani, Kaliyaperumal Balasubramani, Kasthuri |
author_facet | Jeevaraj, Muthaiah Sivajeyanthi, Palaniyappan Edison, Bellarmin Thanigaimani, Kaliyaperumal Balasubramani, Kasthuri |
author_sort | Jeevaraj, Muthaiah |
collection | PubMed |
description | In the crystal structure of the title salt, C(6)H(10)N(3)O(+)·C(7)H(4)ClO(2) (−), the dihedral angle between the pyrimidine ring of the 2-amino-4-methoxy-6-methylpyrimidine cation and the the benzene ring of the 2-chlorobenzoate anion is 2.2 (1)°. In the anion, the benzene ring forms a dihedral angle of 8.5 (2)° with the carboxyl group. The pyrimidine N atom of the cation is protonated and the methoxy substituent is essentially coplanar with the parent ring. The protonated N atom and the N atom of the 2-amino group are hydrogen bonded to the 4-chlorobenzoate anion through a pair of N—H⋯O(carboxyl) hydrogen bonds, forming an R (2) (2)(8) ring motif linked through a centrosymmetric R (2) (4)(8) ring motif, resulting in a pseudotetrameric DDAA array. These units are linked through intermolecular methoxy C—H⋯Cl hydrogen bonds into ribbon-like chains extending along the c-axis direction. The crystal structure also features π–π stacking interactions between the rings in the cation and anion [minimum ring centroid separation = 3.7707 (12) Å]. |
format | Online Article Text |
id | pubmed-5947481 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-59474812018-05-30 Crystal structure, hydrogen bonding and Hirshfeld surface analysis of 2-amino-4-methoxy-6-methylpyrimidinium 4-chlorobenzoate Jeevaraj, Muthaiah Sivajeyanthi, Palaniyappan Edison, Bellarmin Thanigaimani, Kaliyaperumal Balasubramani, Kasthuri Acta Crystallogr E Crystallogr Commun Research Communications In the crystal structure of the title salt, C(6)H(10)N(3)O(+)·C(7)H(4)ClO(2) (−), the dihedral angle between the pyrimidine ring of the 2-amino-4-methoxy-6-methylpyrimidine cation and the the benzene ring of the 2-chlorobenzoate anion is 2.2 (1)°. In the anion, the benzene ring forms a dihedral angle of 8.5 (2)° with the carboxyl group. The pyrimidine N atom of the cation is protonated and the methoxy substituent is essentially coplanar with the parent ring. The protonated N atom and the N atom of the 2-amino group are hydrogen bonded to the 4-chlorobenzoate anion through a pair of N—H⋯O(carboxyl) hydrogen bonds, forming an R (2) (2)(8) ring motif linked through a centrosymmetric R (2) (4)(8) ring motif, resulting in a pseudotetrameric DDAA array. These units are linked through intermolecular methoxy C—H⋯Cl hydrogen bonds into ribbon-like chains extending along the c-axis direction. The crystal structure also features π–π stacking interactions between the rings in the cation and anion [minimum ring centroid separation = 3.7707 (12) Å]. International Union of Crystallography 2018-04-12 /pmc/articles/PMC5947481/ /pubmed/29850085 http://dx.doi.org/10.1107/S2056989018005583 Text en © Jeevaraj 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 Jeevaraj, Muthaiah Sivajeyanthi, Palaniyappan Edison, Bellarmin Thanigaimani, Kaliyaperumal Balasubramani, Kasthuri Crystal structure, hydrogen bonding and Hirshfeld surface analysis of 2-amino-4-methoxy-6-methylpyrimidinium 4-chlorobenzoate |
title | Crystal structure, hydrogen bonding and Hirshfeld surface analysis of 2-amino-4-methoxy-6-methylpyrimidinium 4-chlorobenzoate |
title_full | Crystal structure, hydrogen bonding and Hirshfeld surface analysis of 2-amino-4-methoxy-6-methylpyrimidinium 4-chlorobenzoate |
title_fullStr | Crystal structure, hydrogen bonding and Hirshfeld surface analysis of 2-amino-4-methoxy-6-methylpyrimidinium 4-chlorobenzoate |
title_full_unstemmed | Crystal structure, hydrogen bonding and Hirshfeld surface analysis of 2-amino-4-methoxy-6-methylpyrimidinium 4-chlorobenzoate |
title_short | Crystal structure, hydrogen bonding and Hirshfeld surface analysis of 2-amino-4-methoxy-6-methylpyrimidinium 4-chlorobenzoate |
title_sort | crystal structure, hydrogen bonding and hirshfeld surface analysis of 2-amino-4-methoxy-6-methylpyrimidinium 4-chlorobenzoate |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5947481/ https://www.ncbi.nlm.nih.gov/pubmed/29850085 http://dx.doi.org/10.1107/S2056989018005583 |
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