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Methyl 3′-benzyl-4′-(2,4-dichlorophenyl)-1′-methyl-2-oxospiro[indoline-3,2′-pyrrolidine]-3′-carboxylate
In the title compound, C(27)H(24)Cl(2)N(2)O(3), the indole ring system is essentially planar, with a maximum deviation of 0.082 (2) Å for the carbonyl C atom. It makes a dihedral angle of 88.53 (6)° with the mean plane of the 4-methylpyrrolidine ring, which adopts an envelope conformation with the...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2014
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998484/ https://www.ncbi.nlm.nih.gov/pubmed/24765030 http://dx.doi.org/10.1107/S1600536814003523 |
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author | Karthikeyan, S. Narayanan, P. Sethusankar, K. Devaraj, Anthonisamy Bakthadoss, Manickam |
author_facet | Karthikeyan, S. Narayanan, P. Sethusankar, K. Devaraj, Anthonisamy Bakthadoss, Manickam |
author_sort | Karthikeyan, S. |
collection | PubMed |
description | In the title compound, C(27)H(24)Cl(2)N(2)O(3), the indole ring system is essentially planar, with a maximum deviation of 0.082 (2) Å for the carbonyl C atom. It makes a dihedral angle of 88.53 (6)° with the mean plane of the 4-methylpyrrolidine ring, which adopts an envelope conformation with the N atom at the flap position. The molecular structure is stabilized by intramolecular C—H⋯O hydrogen bonds, which generate S(6) and S(7) ring motifs, and an intramolecular π–π interaction involving the benzyl and dichloro-substituted benzene rings [centroid–centroid distance = 3.6291 (11) Å]. In the crystal, molecules are linked via N—H⋯O hydrogen bonds, forming C(7) chains running parallel to [10-1]. |
format | Online Article Text |
id | pubmed-3998484 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-39984842014-04-24 Methyl 3′-benzyl-4′-(2,4-dichlorophenyl)-1′-methyl-2-oxospiro[indoline-3,2′-pyrrolidine]-3′-carboxylate Karthikeyan, S. Narayanan, P. Sethusankar, K. Devaraj, Anthonisamy Bakthadoss, Manickam Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(27)H(24)Cl(2)N(2)O(3), the indole ring system is essentially planar, with a maximum deviation of 0.082 (2) Å for the carbonyl C atom. It makes a dihedral angle of 88.53 (6)° with the mean plane of the 4-methylpyrrolidine ring, which adopts an envelope conformation with the N atom at the flap position. The molecular structure is stabilized by intramolecular C—H⋯O hydrogen bonds, which generate S(6) and S(7) ring motifs, and an intramolecular π–π interaction involving the benzyl and dichloro-substituted benzene rings [centroid–centroid distance = 3.6291 (11) Å]. In the crystal, molecules are linked via N—H⋯O hydrogen bonds, forming C(7) chains running parallel to [10-1]. International Union of Crystallography 2014-02-22 /pmc/articles/PMC3998484/ /pubmed/24765030 http://dx.doi.org/10.1107/S1600536814003523 Text en © Karthikeyan et al. 2014 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 Karthikeyan, S. Narayanan, P. Sethusankar, K. Devaraj, Anthonisamy Bakthadoss, Manickam Methyl 3′-benzyl-4′-(2,4-dichlorophenyl)-1′-methyl-2-oxospiro[indoline-3,2′-pyrrolidine]-3′-carboxylate |
title | Methyl 3′-benzyl-4′-(2,4-dichlorophenyl)-1′-methyl-2-oxospiro[indoline-3,2′-pyrrolidine]-3′-carboxylate |
title_full | Methyl 3′-benzyl-4′-(2,4-dichlorophenyl)-1′-methyl-2-oxospiro[indoline-3,2′-pyrrolidine]-3′-carboxylate |
title_fullStr | Methyl 3′-benzyl-4′-(2,4-dichlorophenyl)-1′-methyl-2-oxospiro[indoline-3,2′-pyrrolidine]-3′-carboxylate |
title_full_unstemmed | Methyl 3′-benzyl-4′-(2,4-dichlorophenyl)-1′-methyl-2-oxospiro[indoline-3,2′-pyrrolidine]-3′-carboxylate |
title_short | Methyl 3′-benzyl-4′-(2,4-dichlorophenyl)-1′-methyl-2-oxospiro[indoline-3,2′-pyrrolidine]-3′-carboxylate |
title_sort | methyl 3′-benzyl-4′-(2,4-dichlorophenyl)-1′-methyl-2-oxospiro[indoline-3,2′-pyrrolidine]-3′-carboxylate |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998484/ https://www.ncbi.nlm.nih.gov/pubmed/24765030 http://dx.doi.org/10.1107/S1600536814003523 |
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