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N-(9,11-Dimethoxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl)benzamide
The title schulzeine derivative, C(22)H(24)N(2)O(4), crystallizes with two crystallographically independent molecules of almost identical conformation in the asymmetric unit. The tricyclic core of schulzeine has a fused-three-ring system comprising the tetrahydroisoquinoline and δ-lactam moieties...
Autores principales: | , , , |
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2010
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3050218/ https://www.ncbi.nlm.nih.gov/pubmed/21522625 http://dx.doi.org/10.1107/S1600536810050737 |
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author | Fun, Hoong-Kun Kuntiyong, Punlop Tuntiwachwuttikul, Pittaya Chantrapromma, Suchada |
author_facet | Fun, Hoong-Kun Kuntiyong, Punlop Tuntiwachwuttikul, Pittaya Chantrapromma, Suchada |
author_sort | Fun, Hoong-Kun |
collection | PubMed |
description | The title schulzeine derivative, C(22)H(24)N(2)O(4), crystallizes with two crystallographically independent molecules of almost identical conformation in the asymmetric unit. The tricyclic core of schulzeine has a fused-three-ring system comprising the tetrahydroisoquinoline and δ-lactam moieties. In both molecules, the pyridine ring adopts a twisted-boat conformation, whereas the lactam ring is in a boat conformation. The two methoxy groups are slightly twisted from the attached benzene ring [C—O—C—C torsion angles = −21.3 (2) and −20.5 (2)° in molecule A, and −6.3 (2) and −16.2 (2)° in molecule B] and the benzamide moiety is in a (−)-synclinal conformation with respect to the lactam ring. In the crystal, molecules are linked into V-shaped dimers by intermolecular N—H⋯O hydrogen bonds and weak C—H⋯O interactions. These dimers are stacked into V-shaped columns along the a axis. Adjacent columns are further linked in an antiparallel manner. C—H⋯π interactions are also observed. |
format | Text |
id | pubmed-3050218 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2010 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-30502182011-04-26 N-(9,11-Dimethoxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl)benzamide Fun, Hoong-Kun Kuntiyong, Punlop Tuntiwachwuttikul, Pittaya Chantrapromma, Suchada Acta Crystallogr Sect E Struct Rep Online Organic Papers The title schulzeine derivative, C(22)H(24)N(2)O(4), crystallizes with two crystallographically independent molecules of almost identical conformation in the asymmetric unit. The tricyclic core of schulzeine has a fused-three-ring system comprising the tetrahydroisoquinoline and δ-lactam moieties. In both molecules, the pyridine ring adopts a twisted-boat conformation, whereas the lactam ring is in a boat conformation. The two methoxy groups are slightly twisted from the attached benzene ring [C—O—C—C torsion angles = −21.3 (2) and −20.5 (2)° in molecule A, and −6.3 (2) and −16.2 (2)° in molecule B] and the benzamide moiety is in a (−)-synclinal conformation with respect to the lactam ring. In the crystal, molecules are linked into V-shaped dimers by intermolecular N—H⋯O hydrogen bonds and weak C—H⋯O interactions. These dimers are stacked into V-shaped columns along the a axis. Adjacent columns are further linked in an antiparallel manner. C—H⋯π interactions are also observed. International Union of Crystallography 2010-12-11 /pmc/articles/PMC3050218/ /pubmed/21522625 http://dx.doi.org/10.1107/S1600536810050737 Text en © Fun et al. 2011 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 Fun, Hoong-Kun Kuntiyong, Punlop Tuntiwachwuttikul, Pittaya Chantrapromma, Suchada N-(9,11-Dimethoxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl)benzamide |
title |
N-(9,11-Dimethoxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl)benzamide |
title_full |
N-(9,11-Dimethoxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl)benzamide |
title_fullStr |
N-(9,11-Dimethoxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl)benzamide |
title_full_unstemmed |
N-(9,11-Dimethoxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl)benzamide |
title_short |
N-(9,11-Dimethoxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl)benzamide |
title_sort | n-(9,11-dimethoxy-4-oxo-2,3,4,6,7,11b-hexahydro-1h-pyrido[2,1-a]isoquinolin-3-yl)benzamide |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3050218/ https://www.ncbi.nlm.nih.gov/pubmed/21522625 http://dx.doi.org/10.1107/S1600536810050737 |
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