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Planar versus non-planar: The important role of weak C—H⋯O hydrogen bonds in the crystal structure of 5-methyl­salicyl­aldehyde

The crystal structure of 5-methyl­salicyl­aldehyde (5-MSA; systematic name 2-hy­droxy-5-methyl­benzaldehyde), C(8)H(8)O(2), was discovered to be a textbook example of the drastic structural changes caused by just a few weak C—H⋯O inter­actions due to the additional methyl­ation of the aromatic ring...

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Autores principales: Baisch, Ulrich, Scicluna, Marie Christine, Näther, Christian, Vella-Zarb, Liana
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5290555/
https://www.ncbi.nlm.nih.gov/pubmed/28217332
http://dx.doi.org/10.1107/S2056989017000238
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author Baisch, Ulrich
Scicluna, Marie Christine
Näther, Christian
Vella-Zarb, Liana
author_facet Baisch, Ulrich
Scicluna, Marie Christine
Näther, Christian
Vella-Zarb, Liana
author_sort Baisch, Ulrich
collection PubMed
description The crystal structure of 5-methyl­salicyl­aldehyde (5-MSA; systematic name 2-hy­droxy-5-methyl­benzaldehyde), C(8)H(8)O(2), was discovered to be a textbook example of the drastic structural changes caused by just a few weak C—H⋯O inter­actions due to the additional methyl­ation of the aromatic ring compared to salicyl­aldehyde SA. This weak inter­molecular hydrogen bonding is observed between aromatic or methyl carbon donor atoms and hydroxyl or aldehyde acceptor oxygen atoms with d(D⋯A) = 3.4801 (18) and 3.499 (11) Å. The mol­ecule shows a distorted geometry of the aromatic ring with elongated bonds in the vicinity of substituted aldehyde and hydroxyl carbon atoms. The methyl hydrogen atoms are disordered over two sets of sites with occupancies of 0.69 (2) and 0.31 (2).
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spelling pubmed-52905552017-02-17 Planar versus non-planar: The important role of weak C—H⋯O hydrogen bonds in the crystal structure of 5-methyl­salicyl­aldehyde Baisch, Ulrich Scicluna, Marie Christine Näther, Christian Vella-Zarb, Liana Acta Crystallogr E Crystallogr Commun Research Communications The crystal structure of 5-methyl­salicyl­aldehyde (5-MSA; systematic name 2-hy­droxy-5-methyl­benzaldehyde), C(8)H(8)O(2), was discovered to be a textbook example of the drastic structural changes caused by just a few weak C—H⋯O inter­actions due to the additional methyl­ation of the aromatic ring compared to salicyl­aldehyde SA. This weak inter­molecular hydrogen bonding is observed between aromatic or methyl carbon donor atoms and hydroxyl or aldehyde acceptor oxygen atoms with d(D⋯A) = 3.4801 (18) and 3.499 (11) Å. The mol­ecule shows a distorted geometry of the aromatic ring with elongated bonds in the vicinity of substituted aldehyde and hydroxyl carbon atoms. The methyl hydrogen atoms are disordered over two sets of sites with occupancies of 0.69 (2) and 0.31 (2). International Union of Crystallography 2017-01-13 /pmc/articles/PMC5290555/ /pubmed/28217332 http://dx.doi.org/10.1107/S2056989017000238 Text en © Baisch et al. 2017 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
Baisch, Ulrich
Scicluna, Marie Christine
Näther, Christian
Vella-Zarb, Liana
Planar versus non-planar: The important role of weak C—H⋯O hydrogen bonds in the crystal structure of 5-methyl­salicyl­aldehyde
title Planar versus non-planar: The important role of weak C—H⋯O hydrogen bonds in the crystal structure of 5-methyl­salicyl­aldehyde
title_full Planar versus non-planar: The important role of weak C—H⋯O hydrogen bonds in the crystal structure of 5-methyl­salicyl­aldehyde
title_fullStr Planar versus non-planar: The important role of weak C—H⋯O hydrogen bonds in the crystal structure of 5-methyl­salicyl­aldehyde
title_full_unstemmed Planar versus non-planar: The important role of weak C—H⋯O hydrogen bonds in the crystal structure of 5-methyl­salicyl­aldehyde
title_short Planar versus non-planar: The important role of weak C—H⋯O hydrogen bonds in the crystal structure of 5-methyl­salicyl­aldehyde
title_sort planar versus non-planar: the important role of weak c—h⋯o hydrogen bonds in the crystal structure of 5-methyl­salicyl­aldehyde
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5290555/
https://www.ncbi.nlm.nih.gov/pubmed/28217332
http://dx.doi.org/10.1107/S2056989017000238
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