2,4-Bis(4-chlorobenzoyl)-1-(4-chlorophenyl)-3,5-di-2-thienylcyclohexanol methanol hemisolvate

Xiao-Fang Wang,Xian-Qiang Huang

doi:10.1107/s1600536808008428

Abstract

The title compound, C34H25Cl3O3S2·0.5CH3OH, was synthesized by the reaction of thiophene-2-carbaldehyde with acetophenone and NaOH under solvent-free conditions, using tetrabutylammonium bromide as a phase-transfer catalyst. The central six-membered ring adopts a chair conformation with the bulky thiophene, 4-chlorophenyl and 4-chlorobenzoyl substituents in equatorial positions. The hydroxyl group is in an axial position and forms an intramolecular O—H⋯O hydrogen bond to the carbonyl group of an adjacent 4-chlorobenzoyl substituent. The methanol solvent molecules are disordered equally over two positions within one-dimensional channels, with site occupancy factors of 0.25.

Highlights

The title compound, C34H25Cl3O3S2Á0.5CH3OH, was synthesized by the reaction of thiophene-2-carbaldehyde with acetophenone and NaOH under solvent-free conditions, using tetrabutylammonium bromide as a phase-transfer catalyst
The hydroxyl group is in an axial position and forms an intramolecular O—HÁ Á ÁO hydrogen bond to the carbonyl group of an adjacent 4chlorobenzoyl substituent
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BI2281)

Summary

Structure Reports Online

Key indicators: single-crystal X-ray study; T = 298 K; mean (C–C) = 0.012 A; disorder in solvent or counterion; R factor = 0.081; wR factor = 0.290; data-toparameter ratio = 10.8. The title compound, C34H25Cl3O3S2Á0.5CH3OH, was synthesized by the reaction of thiophene-2-carbaldehyde with acetophenone and NaOH under solvent-free conditions, using tetrabutylammonium bromide as a phase-transfer catalyst. The central six-membered ring adopts a chair conformation with the bulky thiophene, 4-chlorophenyl and 4-chlorobenzoyl substituents in equatorial positions. The hydroxyl group is in an axial position and forms an intramolecular O—HÁ Á ÁO hydrogen bond to the carbonyl group of an adjacent 4chlorobenzoyl substituent. The methanol solvent molecules are disordered over two positions within onedimensional channels, with site occupancy factors of 0.25. Related literature For related structures, see: Luo & Shan (2006); Huang & Wang (2007)

Bruker SMART CCD diffractometer

HÁ Á ÁA

Special details