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Redetermination of 6,6′-dimeth­oxy-2,2′-[hexane-1,6-diylbis(nitrilo­dimethyl­idyne)]diphenol

The title compound, C(22)H(28)N(2)O(4), contains two independent centrosymmetric mol­ecules (A and B). In the previous structure determination [Xia et al. (2007 ▶). Acta Cryst. E63, o259] both A and B were modelled as neutral mol­ecules with the H atoms of the the O—H groups included in calculated p...

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Autores principales: Tabatabaee, M., Fotuhiardakani, M. R., Lough, Alan J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3151875/
https://www.ncbi.nlm.nih.gov/pubmed/21836990
http://dx.doi.org/10.1107/S1600536811020599
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author Tabatabaee, M.
Fotuhiardakani, M. R.
Lough, Alan J.
author_facet Tabatabaee, M.
Fotuhiardakani, M. R.
Lough, Alan J.
author_sort Tabatabaee, M.
collection PubMed
description The title compound, C(22)H(28)N(2)O(4), contains two independent centrosymmetric mol­ecules (A and B). In the previous structure determination [Xia et al. (2007 ▶). Acta Cryst. E63, o259] both A and B were modelled as neutral mol­ecules with the H atoms of the the O—H groups included in calculated positions. In this redetermination, the transferrable H atoms were located in difference maps and freely refined, indicating that one mol­ecule (A) crystallizes in the neutral (nonzwitterionic) form and the other in the zwitterionic form, namely 6,6′-dimeth­oxy-2,2′-[hexane-1,6-diylbis(nitrilo­dimethyl­idyne)]­di­phenol–6,6′-dimeth­oxy-2,2′-[hexane-1,6-diylbis(nitrilio­di­methyl­idyne)]diphenolate (1/1). This finding is supported by significant differences in the C—O(H) (A) and C—O(−) (B) bond lengths. In the crystal, the zwitterionic mol­ecules (B) are involved in inter­molecular N—H⋯O hydrogen bonds forming one-dimensional chains along [001]. Each independent mol­ecule forms an intra­molecular O—H⋯N (A) or N—H⋯O (B) hydrogen bond. In mol­ecule B, one of the –CH(2)– groups is disordered over two sets of sites with refined occupancies of 0.659 (8) and 0.341 (8).
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spelling pubmed-31518752011-08-11 Redetermination of 6,6′-dimeth­oxy-2,2′-[hexane-1,6-diylbis(nitrilo­dimethyl­idyne)]diphenol Tabatabaee, M. Fotuhiardakani, M. R. Lough, Alan J. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(22)H(28)N(2)O(4), contains two independent centrosymmetric mol­ecules (A and B). In the previous structure determination [Xia et al. (2007 ▶). Acta Cryst. E63, o259] both A and B were modelled as neutral mol­ecules with the H atoms of the the O—H groups included in calculated positions. In this redetermination, the transferrable H atoms were located in difference maps and freely refined, indicating that one mol­ecule (A) crystallizes in the neutral (nonzwitterionic) form and the other in the zwitterionic form, namely 6,6′-dimeth­oxy-2,2′-[hexane-1,6-diylbis(nitrilo­dimethyl­idyne)]­di­phenol–6,6′-dimeth­oxy-2,2′-[hexane-1,6-diylbis(nitrilio­di­methyl­idyne)]diphenolate (1/1). This finding is supported by significant differences in the C—O(H) (A) and C—O(−) (B) bond lengths. In the crystal, the zwitterionic mol­ecules (B) are involved in inter­molecular N—H⋯O hydrogen bonds forming one-dimensional chains along [001]. Each independent mol­ecule forms an intra­molecular O—H⋯N (A) or N—H⋯O (B) hydrogen bond. In mol­ecule B, one of the –CH(2)– groups is disordered over two sets of sites with refined occupancies of 0.659 (8) and 0.341 (8). International Union of Crystallography 2011-06-04 /pmc/articles/PMC3151875/ /pubmed/21836990 http://dx.doi.org/10.1107/S1600536811020599 Text en © Tabatabaee 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
Tabatabaee, M.
Fotuhiardakani, M. R.
Lough, Alan J.
Redetermination of 6,6′-dimeth­oxy-2,2′-[hexane-1,6-diylbis(nitrilo­dimethyl­idyne)]diphenol
title Redetermination of 6,6′-dimeth­oxy-2,2′-[hexane-1,6-diylbis(nitrilo­dimethyl­idyne)]diphenol
title_full Redetermination of 6,6′-dimeth­oxy-2,2′-[hexane-1,6-diylbis(nitrilo­dimethyl­idyne)]diphenol
title_fullStr Redetermination of 6,6′-dimeth­oxy-2,2′-[hexane-1,6-diylbis(nitrilo­dimethyl­idyne)]diphenol
title_full_unstemmed Redetermination of 6,6′-dimeth­oxy-2,2′-[hexane-1,6-diylbis(nitrilo­dimethyl­idyne)]diphenol
title_short Redetermination of 6,6′-dimeth­oxy-2,2′-[hexane-1,6-diylbis(nitrilo­dimethyl­idyne)]diphenol
title_sort redetermination of 6,6′-dimeth­oxy-2,2′-[hexane-1,6-diylbis(nitrilo­dimethyl­idyne)]diphenol
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3151875/
https://www.ncbi.nlm.nih.gov/pubmed/21836990
http://dx.doi.org/10.1107/S1600536811020599
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