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A structural study of (1 RS ,2 SR ,3 RS ,4 SR ,5 RS )‐2,4‐dibenzoyl‐1,3,5‐triphenylcyclohexan‐1‐ol chloroform hemisolvate and (1 RS ,2 SR ,3 RS ,4 SR ,5 RS )‐2,4‐dibenzoyl‐1‐phenyl‐3,5‐bis(2‐methoxyphenyl)cyclohexan‐1‐ol
Author(s) -
Minyaev Mikhail E.,
Roitershtein Dmitrii M.,
Nifant'ev Ilya E.,
Ananyev Ivan V.,
Minyaeva Tatyana V.,
Mikhaylyev Timofey A.
Publication year - 2015
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229615009857
Subject(s) - chemistry , stereochemistry , intramolecular force , diastereomer , triclinic crystal system , acetophenone , crystal structure , crystallography , organic chemistry , catalysis
(1 RS ,2 SR ,3 RS ,4 SR ,5 RS )‐2,4‐Dibenzoyl‐1,3,5‐triphenylcyclohexan‐1‐ol or (4‐hydroxy‐2,4,6‐triphenylcyclohexane‐1,3‐diyl)bis(phenylmethanone), C 38 H 32 O 3 , (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 38 H 32 O 3 ·0.5CHCl 3 , were grown from chloroform. The structure has triclinic ( P ) symmetry. One diastereomer [as a pair of (1 RS ,2 SR ,3 RS ,4 SR ,5 RS )‐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. E 63 , o4652]. (1 RS ,2 SR ,3 RS ,4 SR ,5 RS )‐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 40 H 36 O 5 , (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 ( Pca 2 1 ) 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.