title: A structural study of (1RS,2SR,3RS,4SR,5RS)-2,4-dibenzoyl-1,3,5-triphenylcyclohexan-1-ol chloroform hemisolvate and (1RS,2SR,3RS,4SR,5RS)-2,4-dibenzoyl-1-phenyl-3,5-bis(2-methoxyphenyl)cyclohexan-1-ol.
abstract: (1RS,2SR,3RS,4SR,5RS)-2,4-Dibenzoyl-1,3,5-triphenylcyclohexan-1-ol or (4-hydroxy-2,4,6-triphenylcyclohexane-1,3-diyl)bis(phenylmethanone), C38H32O3, (1), is formed as a by-product in the NaOH-catalyzed synthesis of 1,3,5-triphenylpentane-1,5-dione from acetophenone and benzaldehyde. Single crystals of the chloroform hemisolvate, C38H32O3·0.5CHCl3, were grown from chloroform. The structure has triclinic (P1) symmetry. One diastereomer [as a pair of (1RS,2SR,3RS,4SR,5RS)-enantiomers] of (1) has been found in the crystal structure and confirmed by NMR studies. The dichoromethane hemisolvate has been reported previously [Zhang et al. (2007). Acta Cryst. E63, o4652]. (1RS,2SR,3RS,4SR,5RS)-2,4-Dibenzoyl-3,5-bis(2-methoxyphenyl)-1-phenylcyclohexan-1-ol or [4-hydroxy-2,6-bis(2-methoxyphenyl)-4-phenylcyclohexane-1,3-diyl]bis(phenylmethanone), C40H36O5, (2), is also formed as a by-product, under the same conditions, from acetophenone and 2-methoxybenzaldehyde. Crystals of (2) have been grown from chloroform. The structure has orthorhombic (Pca2₁) symmetry. A diastereomer of (2) possesses the same configuration as (1). In both structures, the cyclohexane ring adopts a chair conformation with all bulky groups (benzoyl, phenyl and 2-methoxyphenyl) in equatorial positions. The molecules of (1) and (2) both display one intramolecular O-H···O hydrogen bond.
authors.affiliation: A.V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, 29 Leninsky prospect, 119991 Moscow, Russian Federation.
authors.forename: Mikhail E
authors.initials: ME
authors.lastname: Minyaev
authors.affiliation: A.V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, 29 Leninsky prospect, 119991 Moscow, Russian Federation.
authors.forename: Dmitrii M
authors.initials: DM
authors.lastname: Roitershtein
authors.affiliation: A.V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, 29 Leninsky prospect, 119991 Moscow, Russian Federation.
authors.forename: Ilya E
authors.initials: IE
authors.lastname: Nifant'ev
authors.affiliation: A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova Str., 117813 Moscow, Russian Federation.
authors.forename: Ivan V
authors.initials: IV
authors.lastname: Ananyev
authors.affiliation: High school `Moomintroll', 1 Volokolamskoye shosse, Moscow, Russian Federation.
authors.forename: Tatyana V
authors.initials: TV
authors.lastname: Minyaeva
authors.affiliation: The Higher Chemical College of Russian Academy of Sciences, 9 Miusskaya square, 125047 Moscow, Russian Federation.
authors.forename: Timofey A
authors.initials: TA
authors.lastname: Mikhaylyev
keywords: NMR analysis; crystal structure; cyclohexanol; diastereomers; hydrogen bonding; triphenylcyclopentadiene synthesis