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Crystal structure of 1,2-bis­[(2-tert-butyl­phen­yl)imino]­ethane

The whole molecule of the title compound, C(22)H(28)N(2), (I), is generated by inversion symmetry. The mol­ecule is rather similar to that of 2,3-bis­[(2-tert-butyl­phen­yl)imino]­butane, (II), a di­imine ligand comprising similar structural features [Ferreira et al. (2006 ▸). Acta Cryst. E62, o4282...

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Autores principales: Silvino, Alexandre C., Torres, Juliana M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4459346/
https://www.ncbi.nlm.nih.gov/pubmed/26090180
http://dx.doi.org/10.1107/S2056989015008610
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author Silvino, Alexandre C.
Torres, Juliana M.
author_facet Silvino, Alexandre C.
Torres, Juliana M.
author_sort Silvino, Alexandre C.
collection PubMed
description The whole molecule of the title compound, C(22)H(28)N(2), (I), is generated by inversion symmetry. The mol­ecule is rather similar to that of 2,3-bis­[(2-tert-butyl­phen­yl)imino]­butane, (II), a di­imine ligand comprising similar structural features [Ferreira et al. (2006 ▸). Acta Cryst. E62, o4282–o4284]. Both ligands crystallize with the –N=C(R)—C(R)=N– group around an inversion centre, in a trans configuration. Comparing the two structures, it may be noted that the independent planar groups in both mol­ecules [the central link, –N=C(R)—C(R)=N–, and the terminal aromatic ring] subtend an angle of 69.6 (1)° in (II) and 49.4 (2)° in (I). Ferreira and co-workers proposed that such angle deviation may be ascribed to the presence of two non-classical intra­molecular hydrogen bonds and steric factors. In fact, in (I), similar non-classical hydrogen bonds are observed, and the larger angular deviation in (II) may be assigned to the presence of methyl groups in the di­imino fragment, which can cause steric hindrance due to the presence of bulky tert-butyl substituents in the aromatic rings. The C=N bond lengths are similar in both compounds and agree with comonly accepted values.
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spelling pubmed-44593462015-06-18 Crystal structure of 1,2-bis­[(2-tert-butyl­phen­yl)imino]­ethane Silvino, Alexandre C. Torres, Juliana M. Acta Crystallogr E Crystallogr Commun Data Reports The whole molecule of the title compound, C(22)H(28)N(2), (I), is generated by inversion symmetry. The mol­ecule is rather similar to that of 2,3-bis­[(2-tert-butyl­phen­yl)imino]­butane, (II), a di­imine ligand comprising similar structural features [Ferreira et al. (2006 ▸). Acta Cryst. E62, o4282–o4284]. Both ligands crystallize with the –N=C(R)—C(R)=N– group around an inversion centre, in a trans configuration. Comparing the two structures, it may be noted that the independent planar groups in both mol­ecules [the central link, –N=C(R)—C(R)=N–, and the terminal aromatic ring] subtend an angle of 69.6 (1)° in (II) and 49.4 (2)° in (I). Ferreira and co-workers proposed that such angle deviation may be ascribed to the presence of two non-classical intra­molecular hydrogen bonds and steric factors. In fact, in (I), similar non-classical hydrogen bonds are observed, and the larger angular deviation in (II) may be assigned to the presence of methyl groups in the di­imino fragment, which can cause steric hindrance due to the presence of bulky tert-butyl substituents in the aromatic rings. The C=N bond lengths are similar in both compounds and agree with comonly accepted values. International Union of Crystallography 2015-05-09 /pmc/articles/PMC4459346/ /pubmed/26090180 http://dx.doi.org/10.1107/S2056989015008610 Text en © Silvino and Torres 2015 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 Data Reports
Silvino, Alexandre C.
Torres, Juliana M.
Crystal structure of 1,2-bis­[(2-tert-butyl­phen­yl)imino]­ethane
title Crystal structure of 1,2-bis­[(2-tert-butyl­phen­yl)imino]­ethane
title_full Crystal structure of 1,2-bis­[(2-tert-butyl­phen­yl)imino]­ethane
title_fullStr Crystal structure of 1,2-bis­[(2-tert-butyl­phen­yl)imino]­ethane
title_full_unstemmed Crystal structure of 1,2-bis­[(2-tert-butyl­phen­yl)imino]­ethane
title_short Crystal structure of 1,2-bis­[(2-tert-butyl­phen­yl)imino]­ethane
title_sort crystal structure of 1,2-bis­[(2-tert-butyl­phen­yl)imino]­ethane
topic Data Reports
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4459346/
https://www.ncbi.nlm.nih.gov/pubmed/26090180
http://dx.doi.org/10.1107/S2056989015008610
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