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4′-Methyl-1H-14′,19′-dioxa-4′-aza­spiro­[indole-3,5′-tetra­cyclo­[18.4.0.0(2,6).0(8,13)]tetra­cosa­ne]-1′(24′),8′,10′,12′,20′,22′-hexa­ene-2,7′(3H)-dione

In the title compound, C(29)H(28)N(2)O(4), the indoline ring system is essentially planar, with a maximum deviation of 0.027 (2) Å; the carbonyl O atom lies 0.102 (1) Å out of the least-squares plane of the indole ring. The pyrrolidine ring adopts a C-envelope conformation, with a C atom displaced b...

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Autores principales: Narayanan, Sibi, Srinivasan, Thothadri, Purushothaman, Santhanagopalan, Raghunathan, Raghavachary, Velmurugan, Devadasan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3588945/
https://www.ncbi.nlm.nih.gov/pubmed/23476181
http://dx.doi.org/10.1107/S1600536812046132
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author Narayanan, Sibi
Srinivasan, Thothadri
Purushothaman, Santhanagopalan
Raghunathan, Raghavachary
Velmurugan, Devadasan
author_facet Narayanan, Sibi
Srinivasan, Thothadri
Purushothaman, Santhanagopalan
Raghunathan, Raghavachary
Velmurugan, Devadasan
author_sort Narayanan, Sibi
collection PubMed
description In the title compound, C(29)H(28)N(2)O(4), the indoline ring system is essentially planar, with a maximum deviation of 0.027 (2) Å; the carbonyl O atom lies 0.102 (1) Å out of the least-squares plane of the indole ring. The pyrrolidine ring adopts a C-envelope conformation, with a C atom displaced by 0.643 (2) Å from the mean plane formed by the remaining ring atoms. The pyrrolidine ring makes a dihedral angle of 86.1 (8)° with the indoline ring system. In the crystal, N—H⋯O hydrogen bonds result in the formation of cyclic centrosymmetric dimers [R (2) (2)(8)]. C—H⋯π inter­actions also occur, leading to a chain along the b-axis direction. There is a rather weak π–π electron inter­action between the pyrrazole and benzene rings, with a centroid–centroid distance of 3.765 (1) Å.
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spelling pubmed-35889452013-03-08 4′-Methyl-1H-14′,19′-dioxa-4′-aza­spiro­[indole-3,5′-tetra­cyclo­[18.4.0.0(2,6).0(8,13)]tetra­cosa­ne]-1′(24′),8′,10′,12′,20′,22′-hexa­ene-2,7′(3H)-dione Narayanan, Sibi Srinivasan, Thothadri Purushothaman, Santhanagopalan Raghunathan, Raghavachary Velmurugan, Devadasan Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(29)H(28)N(2)O(4), the indoline ring system is essentially planar, with a maximum deviation of 0.027 (2) Å; the carbonyl O atom lies 0.102 (1) Å out of the least-squares plane of the indole ring. The pyrrolidine ring adopts a C-envelope conformation, with a C atom displaced by 0.643 (2) Å from the mean plane formed by the remaining ring atoms. The pyrrolidine ring makes a dihedral angle of 86.1 (8)° with the indoline ring system. In the crystal, N—H⋯O hydrogen bonds result in the formation of cyclic centrosymmetric dimers [R (2) (2)(8)]. C—H⋯π inter­actions also occur, leading to a chain along the b-axis direction. There is a rather weak π–π electron inter­action between the pyrrazole and benzene rings, with a centroid–centroid distance of 3.765 (1) Å. International Union of Crystallography 2012-11-14 /pmc/articles/PMC3588945/ /pubmed/23476181 http://dx.doi.org/10.1107/S1600536812046132 Text en © Narayanan 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
Narayanan, Sibi
Srinivasan, Thothadri
Purushothaman, Santhanagopalan
Raghunathan, Raghavachary
Velmurugan, Devadasan
4′-Methyl-1H-14′,19′-dioxa-4′-aza­spiro­[indole-3,5′-tetra­cyclo­[18.4.0.0(2,6).0(8,13)]tetra­cosa­ne]-1′(24′),8′,10′,12′,20′,22′-hexa­ene-2,7′(3H)-dione
title 4′-Methyl-1H-14′,19′-dioxa-4′-aza­spiro­[indole-3,5′-tetra­cyclo­[18.4.0.0(2,6).0(8,13)]tetra­cosa­ne]-1′(24′),8′,10′,12′,20′,22′-hexa­ene-2,7′(3H)-dione
title_full 4′-Methyl-1H-14′,19′-dioxa-4′-aza­spiro­[indole-3,5′-tetra­cyclo­[18.4.0.0(2,6).0(8,13)]tetra­cosa­ne]-1′(24′),8′,10′,12′,20′,22′-hexa­ene-2,7′(3H)-dione
title_fullStr 4′-Methyl-1H-14′,19′-dioxa-4′-aza­spiro­[indole-3,5′-tetra­cyclo­[18.4.0.0(2,6).0(8,13)]tetra­cosa­ne]-1′(24′),8′,10′,12′,20′,22′-hexa­ene-2,7′(3H)-dione
title_full_unstemmed 4′-Methyl-1H-14′,19′-dioxa-4′-aza­spiro­[indole-3,5′-tetra­cyclo­[18.4.0.0(2,6).0(8,13)]tetra­cosa­ne]-1′(24′),8′,10′,12′,20′,22′-hexa­ene-2,7′(3H)-dione
title_short 4′-Methyl-1H-14′,19′-dioxa-4′-aza­spiro­[indole-3,5′-tetra­cyclo­[18.4.0.0(2,6).0(8,13)]tetra­cosa­ne]-1′(24′),8′,10′,12′,20′,22′-hexa­ene-2,7′(3H)-dione
title_sort 4′-methyl-1h-14′,19′-dioxa-4′-aza­spiro­[indole-3,5′-tetra­cyclo­[18.4.0.0(2,6).0(8,13)]tetra­cosa­ne]-1′(24′),8′,10′,12′,20′,22′-hexa­ene-2,7′(3h)-dione
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3588945/
https://www.ncbi.nlm.nih.gov/pubmed/23476181
http://dx.doi.org/10.1107/S1600536812046132
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