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Synthesis and crystal structures of 5,5′-(propane-2,2-diyl)bis(2-hydroxybenzaldehyde) and 5,5′-(propane-2,2-diyl)bis(2-hydroxyisophthalaldehyde)
The title compounds 5,5′-(propane-2,2-diyl)bis(2-hydroxybenzaldehyde), C(17)H(16)O(4), (1), and 5,5′-(propane-2,2-diyl)bis(2-hydroxyisophthalaldehyde), C(19)H(16)O(6), (2), crystallize with one molecule in the asymmetric unit. In molecule (1), a >C(CH(3))(2) group bridges two nearly pla...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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International Union of Crystallography
2018
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6281094/ https://www.ncbi.nlm.nih.gov/pubmed/30574391 http://dx.doi.org/10.1107/S2056989018016316 |
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author | Sausa, Rosario C. Lastovickova, Dominika N. La Scala, John J. |
author_facet | Sausa, Rosario C. Lastovickova, Dominika N. La Scala, John J. |
author_sort | Sausa, Rosario C. |
collection | PubMed |
description | The title compounds 5,5′-(propane-2,2-diyl)bis(2-hydroxybenzaldehyde), C(17)H(16)O(4), (1), and 5,5′-(propane-2,2-diyl)bis(2-hydroxyisophthalaldehyde), C(19)H(16)O(6), (2), crystallize with one molecule in the asymmetric unit. In molecule (1), a >C(CH(3))(2) group bridges two nearly planar salicylaldehyde groups [r.m.s deviations = 0.010 (1) and 0.025 (2) Å], each comprising a planar phenyl ring bonded with a hydroxyl and an aldehyde group. Similarly, compound (2) has the same bridging group, but it connects two nearly planar appendants [r.m.s deviations = 0.034 (1) and 0.035 (1) Å], each comprising a phenyl ring bonded with a hydroxyl and two aldehyde groups. Molecule (1) exhibits a bridge angle of 109.5 (2)° with the salicylaldehyde planes subtending a dihedral angle of 88.4 (1)°. In contrast, molecule (2) presents a bridge angle of 108.9 (2)° with its appendants subtending a dihedral angle of 79.6 (3)°. Both molecules exhibit two intramolecular O—H⋯O hydrogen bonds involving the phenolic H atoms and carboxyl O-atom acceptors. In the crystal of (2), O—H⋯O hydrogen bonds between one of the hydroxyl H atoms and a carboxyl O atom from a symmetry-related molecule form a chain along [10[Image: see text]]. In addition, (2) exhibits a strong visible luminescence when excited with ultraviolet radiation. |
format | Online Article Text |
id | pubmed-6281094 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-62810942018-12-20 Synthesis and crystal structures of 5,5′-(propane-2,2-diyl)bis(2-hydroxybenzaldehyde) and 5,5′-(propane-2,2-diyl)bis(2-hydroxyisophthalaldehyde) Sausa, Rosario C. Lastovickova, Dominika N. La Scala, John J. Acta Crystallogr E Crystallogr Commun Research Communications The title compounds 5,5′-(propane-2,2-diyl)bis(2-hydroxybenzaldehyde), C(17)H(16)O(4), (1), and 5,5′-(propane-2,2-diyl)bis(2-hydroxyisophthalaldehyde), C(19)H(16)O(6), (2), crystallize with one molecule in the asymmetric unit. In molecule (1), a >C(CH(3))(2) group bridges two nearly planar salicylaldehyde groups [r.m.s deviations = 0.010 (1) and 0.025 (2) Å], each comprising a planar phenyl ring bonded with a hydroxyl and an aldehyde group. Similarly, compound (2) has the same bridging group, but it connects two nearly planar appendants [r.m.s deviations = 0.034 (1) and 0.035 (1) Å], each comprising a phenyl ring bonded with a hydroxyl and two aldehyde groups. Molecule (1) exhibits a bridge angle of 109.5 (2)° with the salicylaldehyde planes subtending a dihedral angle of 88.4 (1)°. In contrast, molecule (2) presents a bridge angle of 108.9 (2)° with its appendants subtending a dihedral angle of 79.6 (3)°. Both molecules exhibit two intramolecular O—H⋯O hydrogen bonds involving the phenolic H atoms and carboxyl O-atom acceptors. In the crystal of (2), O—H⋯O hydrogen bonds between one of the hydroxyl H atoms and a carboxyl O atom from a symmetry-related molecule form a chain along [10[Image: see text]]. In addition, (2) exhibits a strong visible luminescence when excited with ultraviolet radiation. International Union of Crystallography 2018-11-22 /pmc/articles/PMC6281094/ /pubmed/30574391 http://dx.doi.org/10.1107/S2056989018016316 Text en © Sausa et al. 2018 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/2.0/uk/ |
spellingShingle | Research Communications Sausa, Rosario C. Lastovickova, Dominika N. La Scala, John J. Synthesis and crystal structures of 5,5′-(propane-2,2-diyl)bis(2-hydroxybenzaldehyde) and 5,5′-(propane-2,2-diyl)bis(2-hydroxyisophthalaldehyde) |
title | Synthesis and crystal structures of 5,5′-(propane-2,2-diyl)bis(2-hydroxybenzaldehyde) and 5,5′-(propane-2,2-diyl)bis(2-hydroxyisophthalaldehyde) |
title_full | Synthesis and crystal structures of 5,5′-(propane-2,2-diyl)bis(2-hydroxybenzaldehyde) and 5,5′-(propane-2,2-diyl)bis(2-hydroxyisophthalaldehyde) |
title_fullStr | Synthesis and crystal structures of 5,5′-(propane-2,2-diyl)bis(2-hydroxybenzaldehyde) and 5,5′-(propane-2,2-diyl)bis(2-hydroxyisophthalaldehyde) |
title_full_unstemmed | Synthesis and crystal structures of 5,5′-(propane-2,2-diyl)bis(2-hydroxybenzaldehyde) and 5,5′-(propane-2,2-diyl)bis(2-hydroxyisophthalaldehyde) |
title_short | Synthesis and crystal structures of 5,5′-(propane-2,2-diyl)bis(2-hydroxybenzaldehyde) and 5,5′-(propane-2,2-diyl)bis(2-hydroxyisophthalaldehyde) |
title_sort | synthesis and crystal structures of 5,5′-(propane-2,2-diyl)bis(2-hydroxybenzaldehyde) and 5,5′-(propane-2,2-diyl)bis(2-hydroxyisophthalaldehyde) |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6281094/ https://www.ncbi.nlm.nih.gov/pubmed/30574391 http://dx.doi.org/10.1107/S2056989018016316 |
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