2,4-Dibenzoyl-1,3,5-triphenylcyclohexan-1-ol dichloromethane hemisolvate

✍ Scribed by Zhang, Jun-Hong ;He, Qing-Peng ;Wang, Yong ;Wang, Da-Qi

• Book ID: 104492411
• Publisher: International Union of Crystallography
• Year: 2007
• Tongue: English
• Weight: 535 KB
• Volume: 63
• Category: Article
• ISSN: 1600-5368
• DOI: 10.1107/s1600536807056322

✦ Synopsis

In this paper, we present the crystal structure of 2,4-Dibenzoyl-1,3,5-triphenyl-1-cyclohexanol (I) dichloromethane 2:1 solvate, which was synthesized through the condensation and Micheal addition of benzaldehyde with acetophenone under tetrabutyl ammonium bromide and solvent-free conditions.

In the crystal structure, the asymmetric unit contains two independent molecules of (I) (Fig. 1) with normal values of bond lengths and angles corresponding to the published ones (Luo et al., 2006;Huang et al., 2007), and one disordered dichloromethane solvent molecule. The hydroxyl groups in two independent molecules are involved in weak intramolecular hydrogen bonding (Table 1).

Experimental

Acetophenone (6.25 mmol), freshly distilled benzaldehyde (3.125 mmol), NaOH (6.25 mmol) and tetrabutyl ammonium bromide (1 mmol) were aggregated with a glass paddle in an open flask. The resulting mixture was washed with water several times to remove NaOH and was recrystallized from ethanol and CH 2 Cl 2 , affording the title compound as a crystalline solid. Elemental analysis: calculated for C 77 H 66 O 6 Cl 2 : C 79.85, H 5.74%; found: C 79.78, H 5.83%.

Refinement

C-bound H atoms were positioned geometrically and refined using a riding model with C-H = 0.93-0.98 Å and U iso (H) = U eq (C). The H atoms of hydroxyl were placed in idealized positions and constrained to ride on their parent atoms with O-H distances of 0.82%/A, and with U iso (H) = 1.2 U eq (O). The dichloromethane molecule was treated as disordered between two positions with the occupancies fixed to 0.6 and 0.4, respectively.