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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...

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Autores principales: El Ajlaoui, Rahhal, Hakmaoui, Yassine, Rakib, El Mostapha, Ketatni, El Mostafa, Saadi, Mohamed, El Ammari, Lahcen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2022
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.
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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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