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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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Detalles Bibliográficos
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
Descripción
Sumario: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).