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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...

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Autores principales: Fun, Hoong-Kun, Kuntiyong, Punlop, Tuntiwachwuttikul, Pittaya, Chantrapromma, Suchada
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
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.
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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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