3-(2,3,5,6,7,8-Hexahydro-1H-cyclo­penta­[b]quinolin-9-yl)-1,5-bis­(4-methoxy­phen­yl)biuret

Ipidacrine (2,3,5,6,7,8-hexa­hydro-1H-cyclo­penta­[b]quinolin-9-amine) was reacted with 4-methoxy­phenyl isocyanate to give the title compound, C(28)H(30)N(4)O(4). An intra­molecular N—H⋯O hydrogen bond results in an essentially planar [r.m.s. deviation from the mean plane is 0.126 (1) Å] conformati...

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Detalles Bibliográficos
Autores principales: Sakurai, Kaori, Noguchi, Keiichi, Nishibe, Koichiro
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2983504/
https://www.ncbi.nlm.nih.gov/pubmed/21580406
http://dx.doi.org/10.1107/S1600536810006057
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author Sakurai, Kaori
Noguchi, Keiichi
Nishibe, Koichiro
author_facet Sakurai, Kaori
Noguchi, Keiichi
Nishibe, Koichiro
author_sort Sakurai, Kaori
collection PubMed
description Ipidacrine (2,3,5,6,7,8-hexa­hydro-1H-cyclo­penta­[b]quinolin-9-amine) was reacted with 4-methoxy­phenyl isocyanate to give the title compound, C(28)H(30)N(4)O(4). An intra­molecular N—H⋯O hydrogen bond results in an essentially planar [r.m.s. deviation from the mean plane is 0.126 (1) Å] conformation for the biuret unit. The central ring of the quinoline unit is twisted by 78.2 (1)° with respect to the biuret mean plane, whereas the two 4-methoxy­benzene rings are twisted out of this plane by 24.3 (1)° and 48.5 (1)°, resulting in an overall propeller-like structure. An inter­molecular N—H⋯N hydrogen bond between the biuret NH atom and the quinoline ring nitro­gen defines the crystal packing.
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spelling pubmed-29835042010-12-30 3-(2,3,5,6,7,8-Hexahydro-1H-cyclo­penta­[b]quinolin-9-yl)-1,5-bis­(4-methoxy­phen­yl)biuret Sakurai, Kaori Noguchi, Keiichi Nishibe, Koichiro Acta Crystallogr Sect E Struct Rep Online Organic Papers Ipidacrine (2,3,5,6,7,8-hexa­hydro-1H-cyclo­penta­[b]quinolin-9-amine) was reacted with 4-methoxy­phenyl isocyanate to give the title compound, C(28)H(30)N(4)O(4). An intra­molecular N—H⋯O hydrogen bond results in an essentially planar [r.m.s. deviation from the mean plane is 0.126 (1) Å] conformation for the biuret unit. The central ring of the quinoline unit is twisted by 78.2 (1)° with respect to the biuret mean plane, whereas the two 4-methoxy­benzene rings are twisted out of this plane by 24.3 (1)° and 48.5 (1)°, resulting in an overall propeller-like structure. An inter­molecular N—H⋯N hydrogen bond between the biuret NH atom and the quinoline ring nitro­gen defines the crystal packing. International Union of Crystallography 2010-02-20 /pmc/articles/PMC2983504/ /pubmed/21580406 http://dx.doi.org/10.1107/S1600536810006057 Text en © Sakurai et al. 2010 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
Sakurai, Kaori
Noguchi, Keiichi
Nishibe, Koichiro
3-(2,3,5,6,7,8-Hexahydro-1H-cyclo­penta­[b]quinolin-9-yl)-1,5-bis­(4-methoxy­phen­yl)biuret
title 3-(2,3,5,6,7,8-Hexahydro-1H-cyclo­penta­[b]quinolin-9-yl)-1,5-bis­(4-methoxy­phen­yl)biuret
title_full 3-(2,3,5,6,7,8-Hexahydro-1H-cyclo­penta­[b]quinolin-9-yl)-1,5-bis­(4-methoxy­phen­yl)biuret
title_fullStr 3-(2,3,5,6,7,8-Hexahydro-1H-cyclo­penta­[b]quinolin-9-yl)-1,5-bis­(4-methoxy­phen­yl)biuret
title_full_unstemmed 3-(2,3,5,6,7,8-Hexahydro-1H-cyclo­penta­[b]quinolin-9-yl)-1,5-bis­(4-methoxy­phen­yl)biuret
title_short 3-(2,3,5,6,7,8-Hexahydro-1H-cyclo­penta­[b]quinolin-9-yl)-1,5-bis­(4-methoxy­phen­yl)biuret
title_sort 3-(2,3,5,6,7,8-hexahydro-1h-cyclo­penta­[b]quinolin-9-yl)-1,5-bis­(4-methoxy­phen­yl)biuret
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2983504/
https://www.ncbi.nlm.nih.gov/pubmed/21580406
http://dx.doi.org/10.1107/S1600536810006057
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AT nishibekoichiro 3235678hexahydro1hcyclopentabquinolin9yl15bis4methoxyphenylbiuret

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