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(S)-Methyl 2-{(S)-2-[bis­(4-meth­oxy­phen­yl)methyl­idene­amino]-3-hy­droxy­propanamido}-3-methyl­butano­ate

The title compound, C(24)H(30)N(2)O(6), a Schiff base, adopts an extended conformation in which the meth­oxy groups are essentially coplanar with the aromatic ring to which they are bonded (mean planes fitted through the non-H atoms of each methoxyphenyl group have r.m.s. deviations of 0.078 and 0.0...

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Detalles Bibliográficos
Autores principales: Keyari, Charles M., Polt, Robin, Nichol, Gary S.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3050411/
https://www.ncbi.nlm.nih.gov/pubmed/21522640
http://dx.doi.org/10.1107/S1600536810049032
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author Keyari, Charles M.
Polt, Robin
Nichol, Gary S.
author_facet Keyari, Charles M.
Polt, Robin
Nichol, Gary S.
author_sort Keyari, Charles M.
collection PubMed
description The title compound, C(24)H(30)N(2)O(6), a Schiff base, adopts an extended conformation in which the meth­oxy groups are essentially coplanar with the aromatic ring to which they are bonded (mean planes fitted through the non-H atoms of each methoxyphenyl group have r.m.s. deviations of 0.078 and 0.044 Å) and the angle between mean planes fitted through the aromatic rings is 87.57 (10)°. An intra­molecular N—H⋯N hydrogen bond keeps the imine and amide groups essentially coplanar. A mean plane fitted through these groups has an r.m.s. deviation of 0.0545 Å. Additional O—H⋯O hydrogen bonding parallel with the a axis links the mol­ecules into a hydrogen-bonded chain in the crystal. C—H⋯O and C—H⋯π inter­actions are found within the crystal packing. The compound has been assigned the S,S configuration on the basis of the chemical synthesis, which used pure homotopic l-amino acids, and we have no reason to believe that the compound has epimerized.
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spelling pubmed-30504112011-04-26 (S)-Methyl 2-{(S)-2-[bis­(4-meth­oxy­phen­yl)methyl­idene­amino]-3-hy­droxy­propanamido}-3-methyl­butano­ate Keyari, Charles M. Polt, Robin Nichol, Gary S. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(24)H(30)N(2)O(6), a Schiff base, adopts an extended conformation in which the meth­oxy groups are essentially coplanar with the aromatic ring to which they are bonded (mean planes fitted through the non-H atoms of each methoxyphenyl group have r.m.s. deviations of 0.078 and 0.044 Å) and the angle between mean planes fitted through the aromatic rings is 87.57 (10)°. An intra­molecular N—H⋯N hydrogen bond keeps the imine and amide groups essentially coplanar. A mean plane fitted through these groups has an r.m.s. deviation of 0.0545 Å. Additional O—H⋯O hydrogen bonding parallel with the a axis links the mol­ecules into a hydrogen-bonded chain in the crystal. C—H⋯O and C—H⋯π inter­actions are found within the crystal packing. The compound has been assigned the S,S configuration on the basis of the chemical synthesis, which used pure homotopic l-amino acids, and we have no reason to believe that the compound has epimerized. International Union of Crystallography 2010-12-04 /pmc/articles/PMC3050411/ /pubmed/21522640 http://dx.doi.org/10.1107/S1600536810049032 Text en © Keyari 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
Keyari, Charles M.
Polt, Robin
Nichol, Gary S.
(S)-Methyl 2-{(S)-2-[bis­(4-meth­oxy­phen­yl)methyl­idene­amino]-3-hy­droxy­propanamido}-3-methyl­butano­ate
title (S)-Methyl 2-{(S)-2-[bis­(4-meth­oxy­phen­yl)methyl­idene­amino]-3-hy­droxy­propanamido}-3-methyl­butano­ate
title_full (S)-Methyl 2-{(S)-2-[bis­(4-meth­oxy­phen­yl)methyl­idene­amino]-3-hy­droxy­propanamido}-3-methyl­butano­ate
title_fullStr (S)-Methyl 2-{(S)-2-[bis­(4-meth­oxy­phen­yl)methyl­idene­amino]-3-hy­droxy­propanamido}-3-methyl­butano­ate
title_full_unstemmed (S)-Methyl 2-{(S)-2-[bis­(4-meth­oxy­phen­yl)methyl­idene­amino]-3-hy­droxy­propanamido}-3-methyl­butano­ate
title_short (S)-Methyl 2-{(S)-2-[bis­(4-meth­oxy­phen­yl)methyl­idene­amino]-3-hy­droxy­propanamido}-3-methyl­butano­ate
title_sort (s)-methyl 2-{(s)-2-[bis­(4-meth­oxy­phen­yl)methyl­idene­amino]-3-hy­droxy­propanamido}-3-methyl­butano­ate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3050411/
https://www.ncbi.nlm.nih.gov/pubmed/21522640
http://dx.doi.org/10.1107/S1600536810049032
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