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5-Amino-6-benzoyl-8-nitro-2,3-dihydro-1H-spiro[imidazo[1,2-a]pyridine-7,3′-indolin]-2′-one dimethyl sulfoxide monosolvate
In the title compound C(21)H(17)N(5)O(4)·C(2)H(6)OS, the central six-membered ring derived from 1,4-dihydropyridine adopts a distorted boat conformation with a small puckering amplitude of 0.127 (3) Å. The sums of bond angles around the pyridine N atom [358.7 (2)°] and the other imidazolidine N at...
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/PMC4011289/ https://www.ncbi.nlm.nih.gov/pubmed/24860398 http://dx.doi.org/10.1107/S1600536814008800 |
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author | Nagalakshmi, R. A. Suresh, J. Sivakumar, S. Kumar, R. Ranjith Lakshman, P. L. Nilantha |
author_facet | Nagalakshmi, R. A. Suresh, J. Sivakumar, S. Kumar, R. Ranjith Lakshman, P. L. Nilantha |
author_sort | Nagalakshmi, R. A. |
collection | PubMed |
description | In the title compound C(21)H(17)N(5)O(4)·C(2)H(6)OS, the central six-membered ring derived from 1,4-dihydropyridine adopts a distorted boat conformation with a small puckering amplitude of 0.127 (3) Å. The sums of bond angles around the pyridine N atom [358.7 (2)°] and the other imidazolidine N atom [60 (2)°] indicate that these atoms are in sp(2) hybridization, leading to an essentially planar imidazolidine ring. The last heterocycle, an oxindole moiety, is also nearly planar with an r.m.s. deviation of 0.0185 (1) Å. The amine NH(2) group forms an intramolecular hydrogen bond with the benzoyl group, giving a S(6) motif. In the crystal, N—H⋯O hydrogen bonds lead to the formation of chains along the c-axis direction. Within the chains there are further N—H⋯O and C—H⋯O hydrogen bonds enclosing R (2) (2)(14) ring motifs. The chains are linked via N—H⋯O and C—H⋯O hydrogen bonds involving the dimethyl sulfoxide solvent molecule which acts as both an acceptor and a donor.. |
format | Online Article Text |
id | pubmed-4011289 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-40112892014-05-23 5-Amino-6-benzoyl-8-nitro-2,3-dihydro-1H-spiro[imidazo[1,2-a]pyridine-7,3′-indolin]-2′-one dimethyl sulfoxide monosolvate Nagalakshmi, R. A. Suresh, J. Sivakumar, S. Kumar, R. Ranjith Lakshman, P. L. Nilantha Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound C(21)H(17)N(5)O(4)·C(2)H(6)OS, the central six-membered ring derived from 1,4-dihydropyridine adopts a distorted boat conformation with a small puckering amplitude of 0.127 (3) Å. The sums of bond angles around the pyridine N atom [358.7 (2)°] and the other imidazolidine N atom [60 (2)°] indicate that these atoms are in sp(2) hybridization, leading to an essentially planar imidazolidine ring. The last heterocycle, an oxindole moiety, is also nearly planar with an r.m.s. deviation of 0.0185 (1) Å. The amine NH(2) group forms an intramolecular hydrogen bond with the benzoyl group, giving a S(6) motif. In the crystal, N—H⋯O hydrogen bonds lead to the formation of chains along the c-axis direction. Within the chains there are further N—H⋯O and C—H⋯O hydrogen bonds enclosing R (2) (2)(14) ring motifs. The chains are linked via N—H⋯O and C—H⋯O hydrogen bonds involving the dimethyl sulfoxide solvent molecule which acts as both an acceptor and a donor.. International Union of Crystallography 2014-04-26 /pmc/articles/PMC4011289/ /pubmed/24860398 http://dx.doi.org/10.1107/S1600536814008800 Text en © Nagalakshmi 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 Nagalakshmi, R. A. Suresh, J. Sivakumar, S. Kumar, R. Ranjith Lakshman, P. L. Nilantha 5-Amino-6-benzoyl-8-nitro-2,3-dihydro-1H-spiro[imidazo[1,2-a]pyridine-7,3′-indolin]-2′-one dimethyl sulfoxide monosolvate |
title | 5-Amino-6-benzoyl-8-nitro-2,3-dihydro-1H-spiro[imidazo[1,2-a]pyridine-7,3′-indolin]-2′-one dimethyl sulfoxide monosolvate |
title_full | 5-Amino-6-benzoyl-8-nitro-2,3-dihydro-1H-spiro[imidazo[1,2-a]pyridine-7,3′-indolin]-2′-one dimethyl sulfoxide monosolvate |
title_fullStr | 5-Amino-6-benzoyl-8-nitro-2,3-dihydro-1H-spiro[imidazo[1,2-a]pyridine-7,3′-indolin]-2′-one dimethyl sulfoxide monosolvate |
title_full_unstemmed | 5-Amino-6-benzoyl-8-nitro-2,3-dihydro-1H-spiro[imidazo[1,2-a]pyridine-7,3′-indolin]-2′-one dimethyl sulfoxide monosolvate |
title_short | 5-Amino-6-benzoyl-8-nitro-2,3-dihydro-1H-spiro[imidazo[1,2-a]pyridine-7,3′-indolin]-2′-one dimethyl sulfoxide monosolvate |
title_sort | 5-amino-6-benzoyl-8-nitro-2,3-dihydro-1h-spiro[imidazo[1,2-a]pyridine-7,3′-indolin]-2′-one dimethyl sulfoxide monosolvate |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4011289/ https://www.ncbi.nlm.nih.gov/pubmed/24860398 http://dx.doi.org/10.1107/S1600536814008800 |
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