4-Benz­yloxy-3-(2,4-dichloro­phen­yl)-1-oxaspiro­[4.5]dec-3-en-2-one

Liang-zhong Xu; Qun-qun Su; Jin Huang; Shan-qi Sun

doi:10.1107/S1600536809008356

. 2009 Mar 25;65(Pt 4):o845. doi: 10.1107/S1600536809008356

4-Benzyloxy-3-(2,4-dichlorophenyl)-1-oxaspiro[4.5]dec-3-en-2-one

Liang-zhong Xu ^a,^*, Qun-qun Su ^a, Jin Huang ^a, Shan-qi Sun ^a

PMCID: PMC2968969 PMID: 21582564

Abstract

In the title compound, C₂₂H₂₀Cl₂O₃, the cyclohexyl ring adopts a chair conformation. The furanyl ring plane makes dihedral angles of 70.10 (2) and 86.12 (3)° with the 2,4-dichlorophenyl ring and aromatic ring of the benzyl group, respectively. The crystal structure features weak intermolecular C—H⋯O and C—H⋯Cl hydrogen bonds.

Related literature

For similar compounds, see: Bretschneider et al. (2003 ▶). For the synthesis, see: Yu et al. (1994 ▶); Song et al. (2008 ▶).

Experimental

Crystal data

C₂₂H₂₀Cl₂O₃
M _r = 403.28
Triclinic,
a = 7.2624 (15) Å
b = 12.117 (2) Å
c = 12.679 (3) Å
α = 63.30 (2)°
β = 87.67 (3)°
γ = 73.32 (1)°
V = 949.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 113 K
0.18 × 0.16 × 0.10 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.938, T _max = 0.965
7095 measured reflections
3328 independent reflections
2376 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.078
S = 1.03
3328 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: CrystalClear (Rigaku, 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/S1600536809008356/ng2556sup1.cif

e-65-0o845-sup1.cif^{(21.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008356/ng2556Isup2.hkl

e-65-0o845-Isup2.hkl^{(163.2KB, 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
C2—H2A⋯O2ⁱ	0.97	2.54	3.477 (2)	162
C2—H2B⋯Cl1ⁱⁱ	0.97	2.69	3.5051 (19)	142

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

supplementary crystallographic information

Comment

The title compound (I) was prepared as part of a project in search for new compounds with biological activity (Bretschneider et al., 2003). We report here the crystal structure of (I).

In (I) (Fig. 1), all bond lengths and angles are normal and in a good agreement with those reported previously (Bretschneider et al., 2003). The cyclohexane ring (C1—C6) adopts a chair conformation. The furan ring (O1/C1/C7/C8/C9) plane forms dihedral angles of 71.10 (2)° and 86.12 (3)° with the benzene ring (C10—C15) and the benzyl plane (C16—C22) respectively. In addition to van der Waals forces, the structure is stabilized by weak C—H···O and C—H···Cl hydrogen bonds.

Experimental

3-(2,4-Dichlorophenyl)-2,4-dioxo-1-oxaspiro[4.5]decane 3.13 g (10.0 mmol), was suspended in a solution of sodium carbonate 0.54 g (5.1 mmol) in 20 ml of water in a flask equipped with stirrer, water separator and reflux condenser. Toluene (40 ml) was added after 0.5 h, the mixture was heated to dehydration to distil the toluene solvent. Then 1-(chloromethyl)benzene 1.39 g (11.0 mmol) and N,N-dimethylformamide(DMF) solvent (20 ml) were added while maintaining the temperature at 373 K for 4 h. Upon cooling at room temperature water (20 ml) was added. The mixture was extracted with CH₂Cl₂ (15 ml) and the organic layer was washed with water and dried over sodium sulfate. The excess CH₂Cl₂ was removedon a water vacuum pump to obtain the oily product. Crystallized from methanol to afford the title compound 2.95 g (80% yield) (Yu et al., 1994; Song et al., 2008). Single crystals suitable for X-ray diffraction were obtained by recrystallization from the mixture of acetone and methanol at room temperature.