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2,4-Bis(4-eth­oxy­phen­yl)-7-methyl-3-aza­bicyclo­[3.3.1]nonan-9-one

The mol­ecule of the title compound, C(25)H(31)NO(3), exists in a twin-chair conformation with an equatorial orientation of the 4-eth­oxy­phenyl groups, as observed for its ortho isomer [Parthiban, Ramkumar, Park & Jeong (2011b ▶), Acta Cryst. E67, o1475–o1476]. The methyl and 4-eth­oxy­phenyl g...

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Detalles Bibliográficos
Autores principales: Park, Dong Ho, Ramkumar, V., Parthiban, P.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3297850/
https://www.ncbi.nlm.nih.gov/pubmed/22412653
http://dx.doi.org/10.1107/S1600536812006563
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author Park, Dong Ho
Ramkumar, V.
Parthiban, P.
author_facet Park, Dong Ho
Ramkumar, V.
Parthiban, P.
author_sort Park, Dong Ho
collection PubMed
description The mol­ecule of the title compound, C(25)H(31)NO(3), exists in a twin-chair conformation with an equatorial orientation of the 4-eth­oxy­phenyl groups, as observed for its ortho isomer [Parthiban, Ramkumar, Park & Jeong (2011b ▶), Acta Cryst. E67, o1475–o1476]. The methyl and 4-eth­oxy­phenyl groups are also equatorially oriented on the bicycle, as in the ortho analogue. In particular, although the cyclo­hexa­none ring deviates from an ideal chair, the piperidone ring is closer to an ideal chair, whereas in the ortho isomer both rings are significantly puckered and deviate from ideal chairs. The 4-eth­oxy­phenyl groups on both sides of the secondary amine group are oriented at an angle of 26.11 (3)° with respect to each other, but the 2-eth­oxy­phenyl groups in the ortho isomer are oriented by less than half this [12.41 (4)°]. In contrast to the absence of any significant inter­actions in the crystal packing of the ortho isomer, the title compound features N—H⋯O inter­actions, linking the mol­ecules along the b axis.
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spelling pubmed-32978502012-03-12 2,4-Bis(4-eth­oxy­phen­yl)-7-methyl-3-aza­bicyclo­[3.3.1]nonan-9-one Park, Dong Ho Ramkumar, V. Parthiban, P. Acta Crystallogr Sect E Struct Rep Online Organic Papers The mol­ecule of the title compound, C(25)H(31)NO(3), exists in a twin-chair conformation with an equatorial orientation of the 4-eth­oxy­phenyl groups, as observed for its ortho isomer [Parthiban, Ramkumar, Park & Jeong (2011b ▶), Acta Cryst. E67, o1475–o1476]. The methyl and 4-eth­oxy­phenyl groups are also equatorially oriented on the bicycle, as in the ortho analogue. In particular, although the cyclo­hexa­none ring deviates from an ideal chair, the piperidone ring is closer to an ideal chair, whereas in the ortho isomer both rings are significantly puckered and deviate from ideal chairs. The 4-eth­oxy­phenyl groups on both sides of the secondary amine group are oriented at an angle of 26.11 (3)° with respect to each other, but the 2-eth­oxy­phenyl groups in the ortho isomer are oriented by less than half this [12.41 (4)°]. In contrast to the absence of any significant inter­actions in the crystal packing of the ortho isomer, the title compound features N—H⋯O inter­actions, linking the mol­ecules along the b axis. International Union of Crystallography 2012-02-17 /pmc/articles/PMC3297850/ /pubmed/22412653 http://dx.doi.org/10.1107/S1600536812006563 Text en © Park et al. 2012 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
Park, Dong Ho
Ramkumar, V.
Parthiban, P.
2,4-Bis(4-eth­oxy­phen­yl)-7-methyl-3-aza­bicyclo­[3.3.1]nonan-9-one
title 2,4-Bis(4-eth­oxy­phen­yl)-7-methyl-3-aza­bicyclo­[3.3.1]nonan-9-one
title_full 2,4-Bis(4-eth­oxy­phen­yl)-7-methyl-3-aza­bicyclo­[3.3.1]nonan-9-one
title_fullStr 2,4-Bis(4-eth­oxy­phen­yl)-7-methyl-3-aza­bicyclo­[3.3.1]nonan-9-one
title_full_unstemmed 2,4-Bis(4-eth­oxy­phen­yl)-7-methyl-3-aza­bicyclo­[3.3.1]nonan-9-one
title_short 2,4-Bis(4-eth­oxy­phen­yl)-7-methyl-3-aza­bicyclo­[3.3.1]nonan-9-one
title_sort 2,4-bis(4-eth­oxy­phen­yl)-7-methyl-3-aza­bicyclo­[3.3.1]nonan-9-one
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3297850/
https://www.ncbi.nlm.nih.gov/pubmed/22412653
http://dx.doi.org/10.1107/S1600536812006563
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