4,4′-(Cyclo­hexane-1,1-di­yl)diphenol methanol solvate

Jun Shuai; Ying Liu; Mo Liu; Dengke Liu

doi:10.1107/S1600536809000427

. 2009 Jan 10;65(Pt 2):o269. doi: 10.1107/S1600536809000427

4,4′-(Cyclohexane-1,1-diyl)diphenol methanol solvate

Jun Shuai ^a,^*, Ying Liu ^b, Mo Liu ^b, Dengke Liu ^b

PMCID: PMC2968192 PMID: 21581883

Abstract

The title compound, crystallized as a methanol solvate, C₁₈H₂₀O₂·CH₃OH, is an intermediate in the synthesis of the antilipidemic agent clinofibrate. Molecules are packed together with the methanol solvent molecule via two O—H⋯O hydrogen bonds. The third O—H⋯O hydrogen bond is between neighboring 4,4′-(cyclohexane-1,1-diyl)diphenol molecules. The dihedral angle between two benzene rings planes is 81.69 (6).

Related literature

For details of the anti-lipidemic agent clinofibrate, see: Nishizawa et al. (1993 ▶). For the synthesis of clinofibrate, see: Zimmerman et al. (1974 ▶). For a similar structure, see: Nassimbeni et al. (2007 ▶).

Experimental

Crystal data

C₁₈H₂₀O₂·CH₄O
M _r = 300.38
Triclinic,
a = 6.2245 (12) Å
b = 10.889 (2) Å
c = 12.712 (3) Å
α = 90.02 (3)°
β = 100.82 (3)°
γ = 90.03 (3)°
V = 846.3 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 113 (2) K
0.16 × 0.12 × 0.08 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T _min = 0.988, T _max = 0.994
8706 measured reflections
2946 independent reflections
2042 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.058
wR(F ²) = 0.182
S = 1.08
2946 reflections
203 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809000427/bq2114sup1.cif

e-65-0o269-sup1.cif^{(19.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000427/bq2114Isup2.hkl

e-65-0o269-Isup2.hkl^{(144.6KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.82	1.60	2.415 (2)	173
O2—H2⋯O3ⁱⁱ	0.82	2.08	2.860 (3)	159
O3—H3⋯O1ⁱⁱⁱ	0.82	1.96	2.767 (2)	166

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

The authors thank Mr Haibin Song, Nankai University, for the X-ray crystallographic determination, helpful discussions and theoretical analysis.

supplementary crystallographic information

Comment

Clinofibrate is an anti-lipidemic agent which is effective for the treatment of decreasing Blood lipid (Nishizawa et al., 1993). 4,4'-(cyclohexane-1,1-diyl)diphenol is an important intermediate in the synthesis of clinofibrate (Zimmerman et al., 1974). A similar structure, 4, 4'-(cyclohexane-1,1-diyl)diphenol±3-chlorophenol and 4, 4'-(cyclohexane-1,1-diyl)diphenol±4-chlorophenol (Nassimbeni et al., 2007), has been reported previously. Now we present the crystal structure of the title compound(I). The molecules of (I) are crystallized with the solvent molecule methanol (Fig. 1.). Adjacent molecules of (I) are linked via intermolecular O—H···O interactions between the O1—H1 and O2 from a neighboring molecule. The other two H bonds (O2—H2···O3 and O3—H3···O1) are formed between methanol and two neighboring (I) (Table 1.). Planar molecules are usually stabilized by π–π intermolecular interactions. However, (I) is not planar (the dihedral angle between two benzene rings planes is 81.69 (6)°), indicating an absence of π–π coupling.

Experimental

A mixture of cyclohexanone (196.g, 0.2 mol) and phenol (37,6 g, 0.4 mol) in hydrochloric acid (40 ml) and glacial acetic acid (20 ml) was heated at 328 K for 12 h. The mixture was stirred overnight at room temperature, and the resultant precipitates were collected by filtration. The filtrates were dissolved in acetone (200 ml); the solutions decolorize by active carbon, and concentrated under reduced pressure. The residue was washed by toluene (20 ml) to get white powder. The powder was dissolved in methanol and standing under 277 K, then the white crystals were generated slowly.