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Crystal structure of 4-(2-methoxyphenyl)piperazin-1-ium 3,5-dintrosalicylate
The title salt [systematic name: 4-(2-methoxyphenyl)piperazin-1-ium 2-carboxy-4,6-dinitrophenolate], C(11)H(17)N(2)O(+)·C(7)H(3)N(2)O(7) (−), exhibits secondary nitrogen atoms (N—H) in the 2-methoxyphenylpiperazine (2MeOPP) cation, which is protonated with a phenolic hydrogen atom of 3,5-dinitr...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9361365/ https://www.ncbi.nlm.nih.gov/pubmed/35974824 http://dx.doi.org/10.1107/S2056989022006831 |
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author | Subha, Veerappan Seethalakshmi, Thangaraj Balakrishnan, Thangavelu Percino, M. Judith Venkatesan, Perumal |
author_facet | Subha, Veerappan Seethalakshmi, Thangaraj Balakrishnan, Thangavelu Percino, M. Judith Venkatesan, Perumal |
author_sort | Subha, Veerappan |
collection | PubMed |
description | The title salt [systematic name: 4-(2-methoxyphenyl)piperazin-1-ium 2-carboxy-4,6-dinitrophenolate], C(11)H(17)N(2)O(+)·C(7)H(3)N(2)O(7) (−), exhibits secondary nitrogen atoms (N—H) in the 2-methoxyphenylpiperazine (2MeOPP) cation, which is protonated with a phenolic hydrogen atom of 3,5-dinitrosalicylic acid (DNSA). One of the oxygen atoms of the nitro group in the 3,5-dinitrosalicylate anion is disordered over two orientations with occupancy factors of 0.65 (7) and 0.35 (7) . The 2-methoxyphenylpiperazinium cation and 3,5-dinitrosalicylate anion are linked in the asymmetric unit by a bifurcated N—H⋯O hydrogen bond, which formed is between the H atom in the protonated piperazinium unit of the cation and the carboxylic acid group in the anion. The piperazine ring adopts a chair conformation. The crystal structure features N—H⋯O and C—H⋯O hydrogen bonds interactions, which lead to the formation of a sandwich-like arrangement. Hirshfeld surface analysis was used to determine the relative contributions of various intermolecular interactions, indicating that that H⋯O/O⋯H (38. 3%) and H⋯H (31. 8%) contacts are the major contributors. |
format | Online Article Text |
id | pubmed-9361365 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-93613652022-08-15 Crystal structure of 4-(2-methoxyphenyl)piperazin-1-ium 3,5-dintrosalicylate Subha, Veerappan Seethalakshmi, Thangaraj Balakrishnan, Thangavelu Percino, M. Judith Venkatesan, Perumal Acta Crystallogr E Crystallogr Commun Research Communications The title salt [systematic name: 4-(2-methoxyphenyl)piperazin-1-ium 2-carboxy-4,6-dinitrophenolate], C(11)H(17)N(2)O(+)·C(7)H(3)N(2)O(7) (−), exhibits secondary nitrogen atoms (N—H) in the 2-methoxyphenylpiperazine (2MeOPP) cation, which is protonated with a phenolic hydrogen atom of 3,5-dinitrosalicylic acid (DNSA). One of the oxygen atoms of the nitro group in the 3,5-dinitrosalicylate anion is disordered over two orientations with occupancy factors of 0.65 (7) and 0.35 (7) . The 2-methoxyphenylpiperazinium cation and 3,5-dinitrosalicylate anion are linked in the asymmetric unit by a bifurcated N—H⋯O hydrogen bond, which formed is between the H atom in the protonated piperazinium unit of the cation and the carboxylic acid group in the anion. The piperazine ring adopts a chair conformation. The crystal structure features N—H⋯O and C—H⋯O hydrogen bonds interactions, which lead to the formation of a sandwich-like arrangement. Hirshfeld surface analysis was used to determine the relative contributions of various intermolecular interactions, indicating that that H⋯O/O⋯H (38. 3%) and H⋯H (31. 8%) contacts are the major contributors. International Union of Crystallography 2022-07-12 /pmc/articles/PMC9361365/ /pubmed/35974824 http://dx.doi.org/10.1107/S2056989022006831 Text en © Subha et al. 2022 https://creativecommons.org/licenses/by/4.0/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. |
spellingShingle | Research Communications Subha, Veerappan Seethalakshmi, Thangaraj Balakrishnan, Thangavelu Percino, M. Judith Venkatesan, Perumal Crystal structure of 4-(2-methoxyphenyl)piperazin-1-ium 3,5-dintrosalicylate |
title | Crystal structure of 4-(2-methoxyphenyl)piperazin-1-ium 3,5-dintrosalicylate |
title_full | Crystal structure of 4-(2-methoxyphenyl)piperazin-1-ium 3,5-dintrosalicylate |
title_fullStr | Crystal structure of 4-(2-methoxyphenyl)piperazin-1-ium 3,5-dintrosalicylate |
title_full_unstemmed | Crystal structure of 4-(2-methoxyphenyl)piperazin-1-ium 3,5-dintrosalicylate |
title_short | Crystal structure of 4-(2-methoxyphenyl)piperazin-1-ium 3,5-dintrosalicylate |
title_sort | crystal structure of 4-(2-methoxyphenyl)piperazin-1-ium 3,5-dintrosalicylate |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9361365/ https://www.ncbi.nlm.nih.gov/pubmed/35974824 http://dx.doi.org/10.1107/S2056989022006831 |
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