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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...

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Autores principales: Govindan, E., SakthiMurugesan, K., SubbiahPandi, A., Yuvaraj, P., Reddy, Boreddy S. R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
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].
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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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