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3′-[Hydroxy(4-oxo-4H-chromen-3-yl)methyl]-2-oxospiro[indoline-3,2′-pyrrolidine]-3′-carbonitrile
In the title compound, C(23)H(19)N(3)O(4), the pyran ring adopts a half-chair conformation, while the pyrrolidine (with a C atom as the flap atom) and the five-membered ring in the indoline (with a C atom as the flap atom) ring system adopt slight envelope conformations. The pyrrolidine ring makes d...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2011
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3254481/ https://www.ncbi.nlm.nih.gov/pubmed/22259423 http://dx.doi.org/10.1107/S1600536811053098 |
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author | Govindan, E. SakthiMurugesan, K. SubbiahPandi, A. Yuvaraj, P. Reddy, Boreddy S. R. |
author_facet | Govindan, E. SakthiMurugesan, K. SubbiahPandi, A. Yuvaraj, P. Reddy, Boreddy S. R. |
author_sort | Govindan, E. |
collection | PubMed |
description | In the title compound, C(23)H(19)N(3)O(4), the pyran ring adopts a half-chair conformation, while the pyrrolidine (with a C atom as the flap atom) and the five-membered ring in the indoline (with a C atom as the flap atom) ring system adopt slight envelope conformations. The pyrrolidine ring makes dihedral angles of 83.3 (1) and 60.4 (1)° with the mean plane through all non-H atoms of the indoline and chromene ring systems, respectively. In the crystal, molecules are connected by two unique N—H⋯O and O—H⋯O hydrogen-bonding interactions, which form centrosymmetric patterns described by graph-set motifs R (2) (2)(18) and R (2) (2)(14). These two motifs combine to form a hydrogen-bonded chain which propagates in the a-axis direction. The crystal structure is also stablized by C—H⋯O interactions and by aromatic π–π stacking interactions between the pyran and benzene rings of neighbouring molecules [centroid–centroid distance = 3.755 (1) Å and slippage = 1.371 (2) Å]. |
format | Online Article Text |
id | pubmed-3254481 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2011 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-32544812012-01-18 3′-[Hydroxy(4-oxo-4H-chromen-3-yl)methyl]-2-oxospiro[indoline-3,2′-pyrrolidine]-3′-carbonitrile Govindan, E. SakthiMurugesan, K. SubbiahPandi, A. Yuvaraj, P. Reddy, Boreddy S. R. Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(23)H(19)N(3)O(4), the pyran ring adopts a half-chair conformation, while the pyrrolidine (with a C atom as the flap atom) and the five-membered ring in the indoline (with a C atom as the flap atom) ring system adopt slight envelope conformations. The pyrrolidine ring makes dihedral angles of 83.3 (1) and 60.4 (1)° with the mean plane through all non-H atoms of the indoline and chromene ring systems, respectively. In the crystal, molecules are connected by two unique N—H⋯O and O—H⋯O hydrogen-bonding interactions, which form centrosymmetric patterns described by graph-set motifs R (2) (2)(18) and R (2) (2)(14). These two motifs combine to form a hydrogen-bonded chain which propagates in the a-axis direction. The crystal structure is also stablized by C—H⋯O interactions and by aromatic π–π stacking interactions between the pyran and benzene rings of neighbouring molecules [centroid–centroid distance = 3.755 (1) Å and slippage = 1.371 (2) Å]. International Union of Crystallography 2011-12-17 /pmc/articles/PMC3254481/ /pubmed/22259423 http://dx.doi.org/10.1107/S1600536811053098 Text en © Govindan et al. 2012 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Organic Papers Govindan, E. SakthiMurugesan, K. SubbiahPandi, A. Yuvaraj, P. Reddy, Boreddy S. R. 3′-[Hydroxy(4-oxo-4H-chromen-3-yl)methyl]-2-oxospiro[indoline-3,2′-pyrrolidine]-3′-carbonitrile |
title | 3′-[Hydroxy(4-oxo-4H-chromen-3-yl)methyl]-2-oxospiro[indoline-3,2′-pyrrolidine]-3′-carbonitrile |
title_full | 3′-[Hydroxy(4-oxo-4H-chromen-3-yl)methyl]-2-oxospiro[indoline-3,2′-pyrrolidine]-3′-carbonitrile |
title_fullStr | 3′-[Hydroxy(4-oxo-4H-chromen-3-yl)methyl]-2-oxospiro[indoline-3,2′-pyrrolidine]-3′-carbonitrile |
title_full_unstemmed | 3′-[Hydroxy(4-oxo-4H-chromen-3-yl)methyl]-2-oxospiro[indoline-3,2′-pyrrolidine]-3′-carbonitrile |
title_short | 3′-[Hydroxy(4-oxo-4H-chromen-3-yl)methyl]-2-oxospiro[indoline-3,2′-pyrrolidine]-3′-carbonitrile |
title_sort | 3′-[hydroxy(4-oxo-4h-chromen-3-yl)methyl]-2-oxospiro[indoline-3,2′-pyrrolidine]-3′-carbonitrile |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3254481/ https://www.ncbi.nlm.nih.gov/pubmed/22259423 http://dx.doi.org/10.1107/S1600536811053098 |
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