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rac-Ethyl 2-hy­droxy-2,7,7-trimethyl-4-(4-nitro­phen­yl)-5-oxo-3,4,5,6,7,8-hexa­hydro-2H-chromene-3-carboxyl­ate

The title mol­ecule, C(21)H(25)NO(7), has four stereogenic centres and crystallized as a racemate. It consists of enanti­omeric pairs with the relative configuration rac-(1R*,2S*,3R*). The cyclo­hexenone ring adopts an envelope conformation; the dimethyl-substituted C atom lies 0.640 (1) Å out of th...

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Autores principales: Maharramov, Abel M., Ismiev, Arif I., Rashidov, Bahruz A., Askerov, Rizvan K., Potekhin, Konstantin A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3588292/
https://www.ncbi.nlm.nih.gov/pubmed/23476478
http://dx.doi.org/10.1107/S1600536812050581
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author Maharramov, Abel M.
Ismiev, Arif I.
Rashidov, Bahruz A.
Askerov, Rizvan K.
Potekhin, Konstantin A.
author_facet Maharramov, Abel M.
Ismiev, Arif I.
Rashidov, Bahruz A.
Askerov, Rizvan K.
Potekhin, Konstantin A.
author_sort Maharramov, Abel M.
collection PubMed
description The title mol­ecule, C(21)H(25)NO(7), has four stereogenic centres and crystallized as a racemate. It consists of enanti­omeric pairs with the relative configuration rac-(1R*,2S*,3R*). The cyclo­hexenone ring adopts an envelope conformation; the dimethyl-substituted C atom lies 0.640 (1) Å out of the mean plane formed by the rest of the ring atoms (r.m.s. deviation = 0.016 Å). The oxacyclo­hexene ring adopts a half-chair conformation, the hy­droxy- and carboxyl-substituted C atoms lying −0.336 (1) and 0.419 (1) Å, respectively, out of the mean plane formed by the rest of the ring atoms (r.m.s. deviation = 0.002 Å). In the crystal, O—H⋯O hydrogen bonds link the mol­ecules into a chain along the c-axis direction.
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spelling pubmed-35882922013-03-08 rac-Ethyl 2-hy­droxy-2,7,7-trimethyl-4-(4-nitro­phen­yl)-5-oxo-3,4,5,6,7,8-hexa­hydro-2H-chromene-3-carboxyl­ate Maharramov, Abel M. Ismiev, Arif I. Rashidov, Bahruz A. Askerov, Rizvan K. Potekhin, Konstantin A. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title mol­ecule, C(21)H(25)NO(7), has four stereogenic centres and crystallized as a racemate. It consists of enanti­omeric pairs with the relative configuration rac-(1R*,2S*,3R*). The cyclo­hexenone ring adopts an envelope conformation; the dimethyl-substituted C atom lies 0.640 (1) Å out of the mean plane formed by the rest of the ring atoms (r.m.s. deviation = 0.016 Å). The oxacyclo­hexene ring adopts a half-chair conformation, the hy­droxy- and carboxyl-substituted C atoms lying −0.336 (1) and 0.419 (1) Å, respectively, out of the mean plane formed by the rest of the ring atoms (r.m.s. deviation = 0.002 Å). In the crystal, O—H⋯O hydrogen bonds link the mol­ecules into a chain along the c-axis direction. International Union of Crystallography 2012-12-15 /pmc/articles/PMC3588292/ /pubmed/23476478 http://dx.doi.org/10.1107/S1600536812050581 Text en © Maharramov et al. 2013 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
Maharramov, Abel M.
Ismiev, Arif I.
Rashidov, Bahruz A.
Askerov, Rizvan K.
Potekhin, Konstantin A.
rac-Ethyl 2-hy­droxy-2,7,7-trimethyl-4-(4-nitro­phen­yl)-5-oxo-3,4,5,6,7,8-hexa­hydro-2H-chromene-3-carboxyl­ate
title rac-Ethyl 2-hy­droxy-2,7,7-trimethyl-4-(4-nitro­phen­yl)-5-oxo-3,4,5,6,7,8-hexa­hydro-2H-chromene-3-carboxyl­ate
title_full rac-Ethyl 2-hy­droxy-2,7,7-trimethyl-4-(4-nitro­phen­yl)-5-oxo-3,4,5,6,7,8-hexa­hydro-2H-chromene-3-carboxyl­ate
title_fullStr rac-Ethyl 2-hy­droxy-2,7,7-trimethyl-4-(4-nitro­phen­yl)-5-oxo-3,4,5,6,7,8-hexa­hydro-2H-chromene-3-carboxyl­ate
title_full_unstemmed rac-Ethyl 2-hy­droxy-2,7,7-trimethyl-4-(4-nitro­phen­yl)-5-oxo-3,4,5,6,7,8-hexa­hydro-2H-chromene-3-carboxyl­ate
title_short rac-Ethyl 2-hy­droxy-2,7,7-trimethyl-4-(4-nitro­phen­yl)-5-oxo-3,4,5,6,7,8-hexa­hydro-2H-chromene-3-carboxyl­ate
title_sort rac-ethyl 2-hy­droxy-2,7,7-trimethyl-4-(4-nitro­phen­yl)-5-oxo-3,4,5,6,7,8-hexa­hydro-2h-chromene-3-carboxyl­ate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3588292/
https://www.ncbi.nlm.nih.gov/pubmed/23476478
http://dx.doi.org/10.1107/S1600536812050581
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