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. Issue 6 (26th May 2015)

• Record Type: Journal Article
• Authors: Minyaev, Mikhail E.; Roitershtein, Dmitrii M.; Nifant'ev, Ilya E.; Ananyev, Ivan V.; Minyaeva, Tatyana V.; Mikhaylyev, Timofey A.
• Is Part Of: Acta crystallographica. Volume 71:Issue 6(2015:Jun.)
• Page Start: 491
• Page End: 498
• Publication Date: 2015-05-26
• Subjects: Crystallography -- Periodicals; Crystals -- Periodicals; 548.3
• DOI: 10.1107/S2053229615009857
• Languages: English
• ISSNs: 2053-2296

Abstract

<abstract abstract-type="main" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p>(1<italic>RS</italic>, 2<italic>SR</italic>, 3<italic>RS</italic>, 4<italic>SR</italic>, 5<italic>RS</italic>)‐2, 4‐Dibenzoyl‐1, 3, 5‐triphenylcyclohexan‐1‐ol or (4‐hydroxy‐2, 4, 6‐triphenylcyclohexane‐1, 3‐diyl)bis(phenylmethanone), C<sub>38</sub>H<sub>32</sub>O<sub>3</sub>, (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, C<sub>38</sub>H<sub>32</sub>O<sub>3</sub>·0.5CHCl<sub>3</sub>, were grown from chloroform. The structure has triclinic (<italic>P</italic><inline-graphic xlink:href="ark:/27927/pgj14nhz3p5" mimetype="image" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" />) symmetry. One diastereomer [as a pair of (1<italic>RS</italic>, 2<italic>SR</italic>, 3<italic>RS</italic>, 4<italic>SR</italic>, 5<italic>RS</italic>)‐enantiomers] of (1) has been found in the crystal structure and confirmed by NMR studies. The dichoromethane hemisolvate has been reported previously [Zhang <italic>et al.</italic> (2007). <italic>Acta Cryst.</italic> E<bold>63</bold>, o4652]. (1<italic>RS</italic>, 2<italic>SR</italic>, 3<italic>RS</italic>, 4<italic>SR</italic>, 5<italic>RS</italic>)‐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), C<sub>40</sub>H<sub>36</sub>O<sub>5</sub>, (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 (<italic>Pca</italic>2<sub>1</sub>) 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.</p> </abstract>