3-(2,4-Dichloro­phen­yl)-2-oxo-1-oxaspiro­[4.5]dec-3-en-4-yl 2-methyl­prop-2-enoate

Fan-rui Kong; Qiang Wang; Liang-zhong Xu

doi:10.1107/S1600536812016340

. 2012 Apr 25;68(Pt 5):o1531. doi: 10.1107/S1600536812016340

3-(2,4-Dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-yl 2-methylprop-2-enoate

Fan-rui Kong ^a,^*, Qiang Wang ^a, Liang-zhong Xu ^a

PMCID: PMC3344633 PMID: 22590395

Abstract

In the title molecule, C₁₉H₁₈Cl₂O₄, the cyclohexane ring adopts a chair conformation. The furan ring is essentially planar and forms a dihedral angle of 82.1 (1)° with the benzene ring. In the crystal, weak C—H⋯O interactions are present.

Related literature

For the potential biological activity of the title compound and the crystal structures of related compounds, see: Bretschneider et al. (2003 ▶). For the synthesis, see: Lu et al. (2008 ▶).

Experimental

Crystal data

C₁₉H₁₈Cl₂O₄
M _r = 381.23
Monoclinic,
a = 10.759 (1) Å
b = 11.8778 (11) Å
c = 15.0130 (15) Å
β = 107.047 (4)°
V = 1834.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 113 K
0.22 × 0.20 × 0.14 mm

Data collection

Rigaku Saturn CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.922, T _max = 0.950
17672 measured reflections
4371 independent reflections
3362 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.092
S = 1.03
4371 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.36 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 datablock(s) I, global. DOI: 10.1107/S1600536812016340/lh5451sup1.cif

e-68-o1531-sup1.cif^{(20.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016340/lh5451Isup2.hkl

e-68-o1531-Isup2.hkl^{(214.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812016340/lh5451Isup3.cml

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
C11—H11⋯O1ⁱ	0.95	2.52	3.2470 (17)	133
C18—H18B⋯O1ⁱⁱ	0.95	2.56	3.4486 (17)	156

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

supplementary crystallographic information

Comment

The title compound (I) was synthesized as a new compound with potential biological activity (Bretschneider et al., 2003). We report herein its crystal structure.

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 (C4—C9) adopts a chair conformation. The furan ring (O2/C1-C4) plane forms a dihedral angle of 82.1 (1)° with the benzene ring (C10—C15). In the crystal, weak intermolecular C—H···O hydrogen bonds are present.

Experimental

The synthesis followed the prodedure of Lu et al. (2008). In a flask equipped with stirrer and reflux condenser, 3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-ene-4-ol 3.13 g (10.0 mmol), and triethylamine 5 ml was mixed in dichloromethane (30 ml), at 273-278K. The mixture was stirred, then methacryloyl chloride 1.25g (12.0 mmol) for was added dropwise for 1h, then the mixtures was left at room temperature for 3 h. The mixture was then washed with 1% HCl (60 ml) and water (60 ml), and the organic layer was dried over sodium sulfate. Excess dichloromethane was removed on a water vacuum pump to obtain an oily colorless product. The product was crystallized from methanol to afford the title compound 3.39 g (89% yield). Single crystals suitable for X-ray measurements were obtained from a solution of the title compound in acetone and methanol at room temperature.