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5-Diethyl­amino-2-[(E)-(4-methyl-3-nitro­phenyl)­imino­meth­yl]phenol: a redetermination

The title compound, C(18)H(21)N(3)O(3), is a potential bidentate Schiff base ligand. The whole mol­ecule is disordered with a refined site-occupancy ratio of 0.567 (4):0.433 (4) and not just one ethyl group as reported previously [Sarojini et al. (2007 ▶). Acta Cryst. E63, o4782–o4782]. Using the wh...

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Detalles Bibliográficos
Autores principales: Fun, Hoong-Kun, Kia, Reza, Vijesh, A. M., Isloor, Arun M.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2968344/
https://www.ncbi.nlm.nih.gov/pubmed/21581950
http://dx.doi.org/10.1107/S1600536809001731
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author Fun, Hoong-Kun
Kia, Reza
Vijesh, A. M.
Isloor, Arun M.
author_facet Fun, Hoong-Kun
Kia, Reza
Vijesh, A. M.
Isloor, Arun M.
author_sort Fun, Hoong-Kun
collection PubMed
description The title compound, C(18)H(21)N(3)O(3), is a potential bidentate Schiff base ligand. The whole mol­ecule is disordered with a refined site-occupancy ratio of 0.567 (4):0.433 (4) and not just one ethyl group as reported previously [Sarojini et al. (2007 ▶). Acta Cryst. E63, o4782–o4782]. Using the whole mol­ecule disorder, R values are much smaller than those published. An intra­molecular O—H⋯N hydrogen bond generates a six-membered ring, producing an S(6) ring motif. The dihedral angle between the mean plane of the two benzene rings (major component) is 9.0 (5)°. The crystal structure shows short C⋯C [3.189 (15)–3.298 (12) Å] and C⋯O [2.983 (5)–3.149 (13) Å] contacts. Inter­molecular C—H⋯O inter­actions link neighbouring mol­ecules into dimers with R (2) (2)(18) motifs. In the crystal structure, these dimers are linked together by inter­molecular C—H⋯O inter­actions into one-dimensional extended chains along the b axis. The crystal structure is further stabilized by inter­molecular π–π stacking inter­actions [centroid–centroid distances = 3.458 (8)–3.691 (6) Å].
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spelling pubmed-29683442010-12-30 5-Diethyl­amino-2-[(E)-(4-methyl-3-nitro­phenyl)­imino­meth­yl]phenol: a redetermination Fun, Hoong-Kun Kia, Reza Vijesh, A. M. Isloor, Arun M. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(18)H(21)N(3)O(3), is a potential bidentate Schiff base ligand. The whole mol­ecule is disordered with a refined site-occupancy ratio of 0.567 (4):0.433 (4) and not just one ethyl group as reported previously [Sarojini et al. (2007 ▶). Acta Cryst. E63, o4782–o4782]. Using the whole mol­ecule disorder, R values are much smaller than those published. An intra­molecular O—H⋯N hydrogen bond generates a six-membered ring, producing an S(6) ring motif. The dihedral angle between the mean plane of the two benzene rings (major component) is 9.0 (5)°. The crystal structure shows short C⋯C [3.189 (15)–3.298 (12) Å] and C⋯O [2.983 (5)–3.149 (13) Å] contacts. Inter­molecular C—H⋯O inter­actions link neighbouring mol­ecules into dimers with R (2) (2)(18) motifs. In the crystal structure, these dimers are linked together by inter­molecular C—H⋯O inter­actions into one-dimensional extended chains along the b axis. The crystal structure is further stabilized by inter­molecular π–π stacking inter­actions [centroid–centroid distances = 3.458 (8)–3.691 (6) Å]. International Union of Crystallography 2009-01-17 /pmc/articles/PMC2968344/ /pubmed/21581950 http://dx.doi.org/10.1107/S1600536809001731 Text en © Fun et al. 2009 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
Kia, Reza
Vijesh, A. M.
Isloor, Arun M.
5-Diethyl­amino-2-[(E)-(4-methyl-3-nitro­phenyl)­imino­meth­yl]phenol: a redetermination
title 5-Diethyl­amino-2-[(E)-(4-methyl-3-nitro­phenyl)­imino­meth­yl]phenol: a redetermination
title_full 5-Diethyl­amino-2-[(E)-(4-methyl-3-nitro­phenyl)­imino­meth­yl]phenol: a redetermination
title_fullStr 5-Diethyl­amino-2-[(E)-(4-methyl-3-nitro­phenyl)­imino­meth­yl]phenol: a redetermination
title_full_unstemmed 5-Diethyl­amino-2-[(E)-(4-methyl-3-nitro­phenyl)­imino­meth­yl]phenol: a redetermination
title_short 5-Diethyl­amino-2-[(E)-(4-methyl-3-nitro­phenyl)­imino­meth­yl]phenol: a redetermination
title_sort 5-diethyl­amino-2-[(e)-(4-methyl-3-nitro­phenyl)­imino­meth­yl]phenol: a redetermination
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2968344/
https://www.ncbi.nlm.nih.gov/pubmed/21581950
http://dx.doi.org/10.1107/S1600536809001731
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