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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...

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Autores principales: Jeevaraj, Muthaiah, Sivajeyanthi, Palaniyappan, Edison, Bellarmin, Thanigaimani, Kaliyaperumal, Balasubramani, Kasthuri
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2018
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].
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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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