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Diallyl 5-[(4-hexyl­oxyphen­yl)imino­meth­yl]-m-phenyl­ene dicarbonate

The title mol­ecule, C(27)H(31)NO(7), an imine derivative bearing both carbonate and allyl functionalities, was synthesized in the hope of obtaining a mesogenic polymerizable material. The allyl­carbonate arms are fully disordered over two sets of sites, reflecting a large degree of rotational freed...

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Autores principales: Herrera-González, Ana María, López-Velázquez, Delia, Bernès, Sylvain
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2971017/
https://www.ncbi.nlm.nih.gov/pubmed/21578402
http://dx.doi.org/10.1107/S1600536809041142
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author Herrera-González, Ana María
López-Velázquez, Delia
Bernès, Sylvain
author_facet Herrera-González, Ana María
López-Velázquez, Delia
Bernès, Sylvain
author_sort Herrera-González, Ana María
collection PubMed
description The title mol­ecule, C(27)H(31)NO(7), an imine derivative bearing both carbonate and allyl functionalities, was synthesized in the hope of obtaining a mesogenic polymerizable material. The allyl­carbonate arms are fully disordered over two sets of sites, reflecting a large degree of rotational freedom about σ bonds [occupancies: 0.665 (9)/0.335 (9) for one substituent, 0.564 (9)/0.436 (9) for the other]. In contrast, the hexyl chain is ordered, and presents the common all-trans extended conformation. The benzene rings connected via the imine group make a dihedral angle of 9.64 (11)°. In the crystal, the Y-shaped mol­ecules are weakly associated into centrosymmetric dimers through pairs of C—H⋯O(hex­yl) contacts. The resulting layers of dimers, approximately parallel to (2[Image: see text]5), are closely packed in the crystal, allowing π⋯π inter­actions between benzene rings of neighboring layers: the separation between the centroid of the benzene ring substituted by allyl­carbonate and the centroid of the benzene ring bearing the hex­yloxy group in the adjacent layer is 3.895 (1) Å.
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spelling pubmed-29710172010-12-30 Diallyl 5-[(4-hexyl­oxyphen­yl)imino­meth­yl]-m-phenyl­ene dicarbonate Herrera-González, Ana María López-Velázquez, Delia Bernès, Sylvain Acta Crystallogr Sect E Struct Rep Online Organic Papers The title mol­ecule, C(27)H(31)NO(7), an imine derivative bearing both carbonate and allyl functionalities, was synthesized in the hope of obtaining a mesogenic polymerizable material. The allyl­carbonate arms are fully disordered over two sets of sites, reflecting a large degree of rotational freedom about σ bonds [occupancies: 0.665 (9)/0.335 (9) for one substituent, 0.564 (9)/0.436 (9) for the other]. In contrast, the hexyl chain is ordered, and presents the common all-trans extended conformation. The benzene rings connected via the imine group make a dihedral angle of 9.64 (11)°. In the crystal, the Y-shaped mol­ecules are weakly associated into centrosymmetric dimers through pairs of C—H⋯O(hex­yl) contacts. The resulting layers of dimers, approximately parallel to (2[Image: see text]5), are closely packed in the crystal, allowing π⋯π inter­actions between benzene rings of neighboring layers: the separation between the centroid of the benzene ring substituted by allyl­carbonate and the centroid of the benzene ring bearing the hex­yloxy group in the adjacent layer is 3.895 (1) Å. International Union of Crystallography 2009-10-23 /pmc/articles/PMC2971017/ /pubmed/21578402 http://dx.doi.org/10.1107/S1600536809041142 Text en © Herrera-González 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
Herrera-González, Ana María
López-Velázquez, Delia
Bernès, Sylvain
Diallyl 5-[(4-hexyl­oxyphen­yl)imino­meth­yl]-m-phenyl­ene dicarbonate
title Diallyl 5-[(4-hexyl­oxyphen­yl)imino­meth­yl]-m-phenyl­ene dicarbonate
title_full Diallyl 5-[(4-hexyl­oxyphen­yl)imino­meth­yl]-m-phenyl­ene dicarbonate
title_fullStr Diallyl 5-[(4-hexyl­oxyphen­yl)imino­meth­yl]-m-phenyl­ene dicarbonate
title_full_unstemmed Diallyl 5-[(4-hexyl­oxyphen­yl)imino­meth­yl]-m-phenyl­ene dicarbonate
title_short Diallyl 5-[(4-hexyl­oxyphen­yl)imino­meth­yl]-m-phenyl­ene dicarbonate
title_sort diallyl 5-[(4-hexyl­oxyphen­yl)imino­meth­yl]-m-phenyl­ene dicarbonate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2971017/
https://www.ncbi.nlm.nih.gov/pubmed/21578402
http://dx.doi.org/10.1107/S1600536809041142
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