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Open Access Crystal structure of 2,4-di-tert-butyl-6-(hydroxymethyl)phenol

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The title compound, C15H24O2, is an example of a phenol-based pendant-arm precursor. In the molecule, the phenol hydroxy group participates in an intramolecular O—H...O hydrogen bond with the pendant alcohol group, forming an S(6) ring. This ring adopts a half-chair conformation. In the crystal, O—H...O hydrogen bonds connect molecules related by the 31 screw axes, forming chains along the c axis. The C—C—O angles for the hydroxy groups are different as a result of the type of hybridization for the C atoms that are involved in these angles. The C—C—O angle for the phenol hydroxy group is 119.21 (13)°, while the angle within the pendant alcohol is 111.99 (13)°. The bond length involving the phenolic oxygen is 1.3820 (19) Å, which contrasts with that of the alcoholic oxygen which is 1.447 (2) Å. The former is conjugated with the aromatic ring and so leads to the observed shorter bond length.
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Document Type: Research Article

Affiliations: 1: School of Science and the Environment, Division of Chemistry and Environmental Science, Manchester Metropolitan University, John Dalton Building, Chester St, Manchester, M1 5GD, England 2: School of Science and Technology, Nottingham Trent University, Nottingham, NG11 8NS, England

Publication date: January 1, 2016

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