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2-Methyl-4-(naphthalen-2-yl)-3a-nitro-3,3a,4,9b-tetra­hydro-2H-spiro­[chromeno[3,4-c]pyrrole-1,3′-indolin]-2′-one

In the title compound, C(29)H(23)N(3)O(4), the 2-methylpyrrolidine ring adopts a twist conformation on the N—C bond involving the spiro C atom, while the hydropyran ring adopts an envelope conformation with the methine C atom bonded to the O atom as the flap. The mean plane of the indoline-2-one rin...

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Autores principales: Devi, Seenivasan Karthiga, Srinivasan, Thothadri, Rao, Jonnalagadda Naga Siva, Raghunathan, Raghavachary, Velmurugan, Devadasan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3772478/
https://www.ncbi.nlm.nih.gov/pubmed/24046621
http://dx.doi.org/10.1107/S160053681301533X
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author Devi, Seenivasan Karthiga
Srinivasan, Thothadri
Rao, Jonnalagadda Naga Siva
Raghunathan, Raghavachary
Velmurugan, Devadasan
author_facet Devi, Seenivasan Karthiga
Srinivasan, Thothadri
Rao, Jonnalagadda Naga Siva
Raghunathan, Raghavachary
Velmurugan, Devadasan
author_sort Devi, Seenivasan Karthiga
collection PubMed
description In the title compound, C(29)H(23)N(3)O(4), the 2-methylpyrrolidine ring adopts a twist conformation on the N—C bond involving the spiro C atom, while the hydropyran ring adopts an envelope conformation with the methine C atom bonded to the O atom as the flap. The mean plane of the indoline-2-one ring system is almost perpendicular to the mean plane of the pyrrolidine ring, making a dihedral angle of 89.73 (8)°. The latter ring makes dihedral angles of 47.80 (8) with the naphthalene ring system and 32.38 (8)° with the hydropyran ring mean plane. There is an intra­molecular C-H⋯O hydrogen bond involving the indoline-2-one O atom. In the crystal, adjacent mol­ecules are linked via N—H⋯O hydrogen bonds, forming chains propagating along [100]. The chains are linked via weak C—H⋯O hydrogen bonds, forming two-dimensional networks, lying parallel to (101), and consolidated by C—H⋯π inter­actions.
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spelling pubmed-37724782013-09-17 2-Methyl-4-(naphthalen-2-yl)-3a-nitro-3,3a,4,9b-tetra­hydro-2H-spiro­[chromeno[3,4-c]pyrrole-1,3′-indolin]-2′-one Devi, Seenivasan Karthiga Srinivasan, Thothadri Rao, Jonnalagadda Naga Siva Raghunathan, Raghavachary Velmurugan, Devadasan Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(29)H(23)N(3)O(4), the 2-methylpyrrolidine ring adopts a twist conformation on the N—C bond involving the spiro C atom, while the hydropyran ring adopts an envelope conformation with the methine C atom bonded to the O atom as the flap. The mean plane of the indoline-2-one ring system is almost perpendicular to the mean plane of the pyrrolidine ring, making a dihedral angle of 89.73 (8)°. The latter ring makes dihedral angles of 47.80 (8) with the naphthalene ring system and 32.38 (8)° with the hydropyran ring mean plane. There is an intra­molecular C-H⋯O hydrogen bond involving the indoline-2-one O atom. In the crystal, adjacent mol­ecules are linked via N—H⋯O hydrogen bonds, forming chains propagating along [100]. The chains are linked via weak C—H⋯O hydrogen bonds, forming two-dimensional networks, lying parallel to (101), and consolidated by C—H⋯π inter­actions. International Union of Crystallography 2013-06-08 /pmc/articles/PMC3772478/ /pubmed/24046621 http://dx.doi.org/10.1107/S160053681301533X Text en © Devi et al. 2013 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
Devi, Seenivasan Karthiga
Srinivasan, Thothadri
Rao, Jonnalagadda Naga Siva
Raghunathan, Raghavachary
Velmurugan, Devadasan
2-Methyl-4-(naphthalen-2-yl)-3a-nitro-3,3a,4,9b-tetra­hydro-2H-spiro­[chromeno[3,4-c]pyrrole-1,3′-indolin]-2′-one
title 2-Methyl-4-(naphthalen-2-yl)-3a-nitro-3,3a,4,9b-tetra­hydro-2H-spiro­[chromeno[3,4-c]pyrrole-1,3′-indolin]-2′-one
title_full 2-Methyl-4-(naphthalen-2-yl)-3a-nitro-3,3a,4,9b-tetra­hydro-2H-spiro­[chromeno[3,4-c]pyrrole-1,3′-indolin]-2′-one
title_fullStr 2-Methyl-4-(naphthalen-2-yl)-3a-nitro-3,3a,4,9b-tetra­hydro-2H-spiro­[chromeno[3,4-c]pyrrole-1,3′-indolin]-2′-one
title_full_unstemmed 2-Methyl-4-(naphthalen-2-yl)-3a-nitro-3,3a,4,9b-tetra­hydro-2H-spiro­[chromeno[3,4-c]pyrrole-1,3′-indolin]-2′-one
title_short 2-Methyl-4-(naphthalen-2-yl)-3a-nitro-3,3a,4,9b-tetra­hydro-2H-spiro­[chromeno[3,4-c]pyrrole-1,3′-indolin]-2′-one
title_sort 2-methyl-4-(naphthalen-2-yl)-3a-nitro-3,3a,4,9b-tetra­hydro-2h-spiro­[chromeno[3,4-c]pyrrole-1,3′-indolin]-2′-one
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3772478/
https://www.ncbi.nlm.nih.gov/pubmed/24046621
http://dx.doi.org/10.1107/S160053681301533X
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