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Crystal structure and Hirshfeld surface analysis of (RS)-3-hydroxy-2-{[(3aRS,6RS,7aRS)-2-(4-methylphenylsulfonyl)-2,3,3a,6,7,7a-hexahydro-3a,6-epoxy-1H-isoindol-6-yl]methyl}isoindolin-1-one
The title compound, C(24)H(24)N(2)O(5)S, crystallizes with two independent molecules (A and B) in the asymmetric unit. In the central ring systems of both molecules, the tetrahydrofuran rings adopt envelope conformations, the pyrrolidine rings adopt a twisted-envelope conformation and the six-me...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8061098/ https://www.ncbi.nlm.nih.gov/pubmed/33953948 http://dx.doi.org/10.1107/S2056989021001626 |
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author | Mertsalov, Dmitriy F. Nadirova, Maryana A. Sorokina, Elena A. Vinokurova, Marina A. Çelikesir, Sevim Türktekin Akkurt, Mehmet Kolesnik, Irina A. Bhattarai, Ajaya |
author_facet | Mertsalov, Dmitriy F. Nadirova, Maryana A. Sorokina, Elena A. Vinokurova, Marina A. Çelikesir, Sevim Türktekin Akkurt, Mehmet Kolesnik, Irina A. Bhattarai, Ajaya |
author_sort | Mertsalov, Dmitriy F. |
collection | PubMed |
description | The title compound, C(24)H(24)N(2)O(5)S, crystallizes with two independent molecules (A and B) in the asymmetric unit. In the central ring systems of both molecules, the tetrahydrofuran rings adopt envelope conformations, the pyrrolidine rings adopt a twisted-envelope conformation and the six-membered ring is in a boat conformation. In molecules A and B, the nine-membered groups attached to the central ring system are essentially planar (r.m.s. deviations of 0.002 and 0.003 Å, respectively). They form dihedral angles of 64.97 (9) and 56.06 (10)°, respectively, with the phenyl rings. In the crystal, strong intermolecular O—H⋯O hydrogen bonds and weak intermolecular C—H⋯O contacts link the molecules, forming a three-dimensional network. In addition weak π–π stacking interactions [centroid-to centroid distance = 3.7124 (13) Å] between the pyrrolidine rings of the nine-membered groups of A molecules are observed. Hirshfeld surface analysis and two-dimensional fingerprint plots were used to quantify the intermolecular interactions present in the crystal, indicating that the environments of the two molecules are very similar. The most important contributions for the crystal packing are from H⋯H (55.8% for molecule A and 53.5% for molecule B), O⋯H/H⋯O (24.5% for molecule A and 26.3% for molecule B) and C⋯H/H⋯C (12.6% for molecule A and 15.7% for molecule B) interactions. |
format | Online Article Text |
id | pubmed-8061098 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-80610982021-05-04 Crystal structure and Hirshfeld surface analysis of (RS)-3-hydroxy-2-{[(3aRS,6RS,7aRS)-2-(4-methylphenylsulfonyl)-2,3,3a,6,7,7a-hexahydro-3a,6-epoxy-1H-isoindol-6-yl]methyl}isoindolin-1-one Mertsalov, Dmitriy F. Nadirova, Maryana A. Sorokina, Elena A. Vinokurova, Marina A. Çelikesir, Sevim Türktekin Akkurt, Mehmet Kolesnik, Irina A. Bhattarai, Ajaya Acta Crystallogr E Crystallogr Commun Research Communications The title compound, C(24)H(24)N(2)O(5)S, crystallizes with two independent molecules (A and B) in the asymmetric unit. In the central ring systems of both molecules, the tetrahydrofuran rings adopt envelope conformations, the pyrrolidine rings adopt a twisted-envelope conformation and the six-membered ring is in a boat conformation. In molecules A and B, the nine-membered groups attached to the central ring system are essentially planar (r.m.s. deviations of 0.002 and 0.003 Å, respectively). They form dihedral angles of 64.97 (9) and 56.06 (10)°, respectively, with the phenyl rings. In the crystal, strong intermolecular O—H⋯O hydrogen bonds and weak intermolecular C—H⋯O contacts link the molecules, forming a three-dimensional network. In addition weak π–π stacking interactions [centroid-to centroid distance = 3.7124 (13) Å] between the pyrrolidine rings of the nine-membered groups of A molecules are observed. Hirshfeld surface analysis and two-dimensional fingerprint plots were used to quantify the intermolecular interactions present in the crystal, indicating that the environments of the two molecules are very similar. The most important contributions for the crystal packing are from H⋯H (55.8% for molecule A and 53.5% for molecule B), O⋯H/H⋯O (24.5% for molecule A and 26.3% for molecule B) and C⋯H/H⋯C (12.6% for molecule A and 15.7% for molecule B) interactions. International Union of Crystallography 2021-02-16 /pmc/articles/PMC8061098/ /pubmed/33953948 http://dx.doi.org/10.1107/S2056989021001626 Text en © Mertsalov et al. 2021 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 Mertsalov, Dmitriy F. Nadirova, Maryana A. Sorokina, Elena A. Vinokurova, Marina A. Çelikesir, Sevim Türktekin Akkurt, Mehmet Kolesnik, Irina A. Bhattarai, Ajaya Crystal structure and Hirshfeld surface analysis of (RS)-3-hydroxy-2-{[(3aRS,6RS,7aRS)-2-(4-methylphenylsulfonyl)-2,3,3a,6,7,7a-hexahydro-3a,6-epoxy-1H-isoindol-6-yl]methyl}isoindolin-1-one |
title | Crystal structure and Hirshfeld surface analysis of (RS)-3-hydroxy-2-{[(3aRS,6RS,7aRS)-2-(4-methylphenylsulfonyl)-2,3,3a,6,7,7a-hexahydro-3a,6-epoxy-1H-isoindol-6-yl]methyl}isoindolin-1-one |
title_full | Crystal structure and Hirshfeld surface analysis of (RS)-3-hydroxy-2-{[(3aRS,6RS,7aRS)-2-(4-methylphenylsulfonyl)-2,3,3a,6,7,7a-hexahydro-3a,6-epoxy-1H-isoindol-6-yl]methyl}isoindolin-1-one |
title_fullStr | Crystal structure and Hirshfeld surface analysis of (RS)-3-hydroxy-2-{[(3aRS,6RS,7aRS)-2-(4-methylphenylsulfonyl)-2,3,3a,6,7,7a-hexahydro-3a,6-epoxy-1H-isoindol-6-yl]methyl}isoindolin-1-one |
title_full_unstemmed | Crystal structure and Hirshfeld surface analysis of (RS)-3-hydroxy-2-{[(3aRS,6RS,7aRS)-2-(4-methylphenylsulfonyl)-2,3,3a,6,7,7a-hexahydro-3a,6-epoxy-1H-isoindol-6-yl]methyl}isoindolin-1-one |
title_short | Crystal structure and Hirshfeld surface analysis of (RS)-3-hydroxy-2-{[(3aRS,6RS,7aRS)-2-(4-methylphenylsulfonyl)-2,3,3a,6,7,7a-hexahydro-3a,6-epoxy-1H-isoindol-6-yl]methyl}isoindolin-1-one |
title_sort | crystal structure and hirshfeld surface analysis of (rs)-3-hydroxy-2-{[(3ars,6rs,7ars)-2-(4-methylphenylsulfonyl)-2,3,3a,6,7,7a-hexahydro-3a,6-epoxy-1h-isoindol-6-yl]methyl}isoindolin-1-one |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8061098/ https://www.ncbi.nlm.nih.gov/pubmed/33953948 http://dx.doi.org/10.1107/S2056989021001626 |
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