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Synthesis, crystal structure and Hirshfeld surface analysis of dimethyl 3-(3-bromophenyl)-6-methyl-7-oxo-3,5,6,7-tetrahydropyrazolo[1,2-a]pyrazole-1,2-dicarboxylate
The title compound, C(17)H(17)BrN(2)O(5), resulted from the 1,3-dipolar cycloaddition reaction between dimethyl acetylenedicarboxylate and (3-bromobenzylidene)-4-methyl-5-oxopyrazolidin-2-ium-1-ide in CHCl(3). The dihedral angle between the pyrazole rings (all atoms) is 32.91 (10)°; the oxo-py...
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/PMC8819431/ https://www.ncbi.nlm.nih.gov/pubmed/35145737 http://dx.doi.org/10.1107/S2056989021013621 |
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author | El Ajlaoui, Rahhal Hakmaoui, Yassine Rakib, El Mostapha Ketatni, El Mostafa Saadi, Mohamed El Ammari, Lahcen |
author_facet | El Ajlaoui, Rahhal Hakmaoui, Yassine Rakib, El Mostapha Ketatni, El Mostafa Saadi, Mohamed El Ammari, Lahcen |
author_sort | El Ajlaoui, Rahhal |
collection | PubMed |
description | The title compound, C(17)H(17)BrN(2)O(5), resulted from the 1,3-dipolar cycloaddition reaction between dimethyl acetylenedicarboxylate and (3-bromobenzylidene)-4-methyl-5-oxopyrazolidin-2-ium-1-ide in CHCl(3). The dihedral angle between the pyrazole rings (all atoms) is 32.91 (10)°; the oxo-pyrazole ring displays an envelope conformation whereas the other pyrazole ring adopts a twisted conformation. The bromophenyl ring subtends a dihedral angle of 88.95 (9)° with the mean plane of its attached pyrazole ring. In the crystal, the molecules are linked by C—H⋯O hydrogen bonds and aromatic π–π interactions with an inter-centroid distance of 3.8369 (10) Å. The Hirshfeld surface analysis and fingerprint plots reveal that the molecular packing is governed by H⋯H (37.1%), O⋯H/H⋯O (31.3%), Br⋯H/H⋯Br (13.5%) and C⋯H/H⋯C (10.6%) contacts. The energy framework indicates that dispersion energy is the major contributor to the molecular packing. |
format | Online Article Text |
id | pubmed-8819431 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-88194312022-02-09 Synthesis, crystal structure and Hirshfeld surface analysis of dimethyl 3-(3-bromophenyl)-6-methyl-7-oxo-3,5,6,7-tetrahydropyrazolo[1,2-a]pyrazole-1,2-dicarboxylate El Ajlaoui, Rahhal Hakmaoui, Yassine Rakib, El Mostapha Ketatni, El Mostafa Saadi, Mohamed El Ammari, Lahcen Acta Crystallogr E Crystallogr Commun Research Communications The title compound, C(17)H(17)BrN(2)O(5), resulted from the 1,3-dipolar cycloaddition reaction between dimethyl acetylenedicarboxylate and (3-bromobenzylidene)-4-methyl-5-oxopyrazolidin-2-ium-1-ide in CHCl(3). The dihedral angle between the pyrazole rings (all atoms) is 32.91 (10)°; the oxo-pyrazole ring displays an envelope conformation whereas the other pyrazole ring adopts a twisted conformation. The bromophenyl ring subtends a dihedral angle of 88.95 (9)° with the mean plane of its attached pyrazole ring. In the crystal, the molecules are linked by C—H⋯O hydrogen bonds and aromatic π–π interactions with an inter-centroid distance of 3.8369 (10) Å. The Hirshfeld surface analysis and fingerprint plots reveal that the molecular packing is governed by H⋯H (37.1%), O⋯H/H⋯O (31.3%), Br⋯H/H⋯Br (13.5%) and C⋯H/H⋯C (10.6%) contacts. The energy framework indicates that dispersion energy is the major contributor to the molecular packing. International Union of Crystallography 2022-01-07 /pmc/articles/PMC8819431/ /pubmed/35145737 http://dx.doi.org/10.1107/S2056989021013621 Text en © El Ajlaoui 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 El Ajlaoui, Rahhal Hakmaoui, Yassine Rakib, El Mostapha Ketatni, El Mostafa Saadi, Mohamed El Ammari, Lahcen Synthesis, crystal structure and Hirshfeld surface analysis of dimethyl 3-(3-bromophenyl)-6-methyl-7-oxo-3,5,6,7-tetrahydropyrazolo[1,2-a]pyrazole-1,2-dicarboxylate |
title | Synthesis, crystal structure and Hirshfeld surface analysis of dimethyl 3-(3-bromophenyl)-6-methyl-7-oxo-3,5,6,7-tetrahydropyrazolo[1,2-a]pyrazole-1,2-dicarboxylate |
title_full | Synthesis, crystal structure and Hirshfeld surface analysis of dimethyl 3-(3-bromophenyl)-6-methyl-7-oxo-3,5,6,7-tetrahydropyrazolo[1,2-a]pyrazole-1,2-dicarboxylate |
title_fullStr | Synthesis, crystal structure and Hirshfeld surface analysis of dimethyl 3-(3-bromophenyl)-6-methyl-7-oxo-3,5,6,7-tetrahydropyrazolo[1,2-a]pyrazole-1,2-dicarboxylate |
title_full_unstemmed | Synthesis, crystal structure and Hirshfeld surface analysis of dimethyl 3-(3-bromophenyl)-6-methyl-7-oxo-3,5,6,7-tetrahydropyrazolo[1,2-a]pyrazole-1,2-dicarboxylate |
title_short | Synthesis, crystal structure and Hirshfeld surface analysis of dimethyl 3-(3-bromophenyl)-6-methyl-7-oxo-3,5,6,7-tetrahydropyrazolo[1,2-a]pyrazole-1,2-dicarboxylate |
title_sort | synthesis, crystal structure and hirshfeld surface analysis of dimethyl 3-(3-bromophenyl)-6-methyl-7-oxo-3,5,6,7-tetrahydropyrazolo[1,2-a]pyrazole-1,2-dicarboxylate |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8819431/ https://www.ncbi.nlm.nih.gov/pubmed/35145737 http://dx.doi.org/10.1107/S2056989021013621 |
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