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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...

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Autores principales: Mertsalov, Dmitriy F., Nadirova, Maryana A., Sorokina, Elena A., Vinokurova, Marina A., Çelikesir, Sevim Türktekin, Akkurt, Mehmet, Kolesnik, Irina A., Bhattarai, Ajaya
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2021
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.
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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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