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

Liang-zhong Xu; Shan-qi Sun; Wei Guo; Qun-qun Su

doi:10.1107/S1600536809000579

. 2009 Jan 14;65(Pt 2):o302. doi: 10.1107/S1600536809000579

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

Liang-zhong Xu ^a,^*, Shan-qi Sun ^a, Wei Guo ^a, Qun-qun Su ^a

PMCID: PMC2968231 PMID: 21581911

Abstract

In the title compound, C₁₉H₂₂Cl₂O₃, the cyclohexane ring adopts a chair conformation. The furan ring plane forms dihedral angles of 81.88 (2) and 50.19 (3)°, respectively, with the benzene ring and the plane formed by the butyl C atoms. The crystal structure is stabilized by weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For the biological activity of related compounds, see: Thomas et al. (2003 ▶). For synthetic information, see: Raeppel et al. (1998 ▶); Sarcevic et al. (1973 ▶).

Experimental

Crystal data

C₁₉H₂₂Cl₂O₃
M _r = 369.27
Orthorhombic,
a = 15.177 (3) Å
b = 13.735 (3) Å
c = 17.497 (4) Å
V = 3647.4 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 113 (2) K
0.18 × 0.14 × 0.10 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.936, T _max = 0.964
23387 measured reflections
3217 independent reflections
2536 reflections with I > 2σ(I)
R _int = 0.090

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.131
S = 1.08
3217 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.35 e Å⁻³

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

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809000579/lh2747sup1.cif

e-65-0o302-sup1.cif^{(20.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000579/lh2747Isup2.hkl

e-65-0o302-Isup2.hkl^{(157.9KB, 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—H2B⋯O2ⁱ	0.97	2.54	3.316 (3)	137
C18—H18⋯O1ⁱⁱ	0.93	2.49	3.370 (3)	159

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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 (Thomas 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 (Thomas et al., 2003). The cyclohexane ring (C1—C6) adopts a chair conformation. The furan ring (O1/C1/C7/C12/C13) plane forms dihedral angles of 81.88 (2)° and 50.19 (3)° with the benzene ring (C14—C19) and the butyl group plane (C8—C11) respectively. In addition to van der Waals forces, the structure is stabilized by weak C—H···O 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 distill the toluene solvent. Then 1-bromobutane 1.51 g (11.0 mmol) and N,N-dimethylformamide(DMF) solvent (20 ml) were added while maintaining the temperature at 373K 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 removed on a water vacuum pump to obtain the oily product which was crystallized from methanol to afford the title compound 2.95 g (80% yield) (Raeppel et al., 1998; Sarcevic et al., 1973). Single crystals suitable for X-ray diffraction were obtained by recrystallization of the title compound from a mixture of acetone and methanol at room temperature.