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

Kong, F.; Wang, Q.; Xu, L.

doi:10.1107/S1600536812016340

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1531

doi:10.1107/S1600536812016340

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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 and Liang-zhong Xu ^a

^aCollege of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China
^*Correspondence e-mail: farykong@163.com

(Received 3 April 2012; accepted 15 April 2012; online 25 April 2012)

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, P 2₁ /n
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[F² > 2σ(F²)] = 0.035
wR(F²) = 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

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
Symmetry codes: (i) -x, -y+1, -z+2; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812016340/lh5451sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812016340/lh5451Isup3.cml

checkCIF report

Comment top

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.

Related literature top

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 top

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.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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 (Sheldrick, 2008).

Figures top

Fig. 1. View of the title compound with displacement ellipsoids drawn at the 40% probability level.

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

Crystal data top

C₁₉H₁₈Cl₂O₄	F(000) = 792
M_r = 381.23	D_x = 1.381 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6104 reflections
a = 10.759 (1) Å	θ = 1.4–28.1°
b = 11.8778 (11) Å	µ = 0.37 mm⁻¹
c = 15.0130 (15) Å	T = 113 K
β = 107.047 (4)°	Prism, colorless
V = 1834.3 (3) Å³	0.22 × 0.20 × 0.14 mm
Z = 4

Data collection top

Rigaku Saturn CCD diffractometer	4371 independent reflections
Radiation source: rotating anode	3362 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.034
Detector resolution: 14.63 pixels mm^-1	θ_max = 27.9°, θ_min = 2.1°
ω and ϕ scans	h = −13→14
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −14→15
T_min = 0.922, T_max = 0.950	l = −19→19
17672 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0557P)²] where P = (F_o² + 2F_c²)/3
4371 reflections	(Δ/σ)_max = 0.002
227 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₉H₁₈Cl₂O₄	V = 1834.3 (3) Å³
M_r = 381.23	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.759 (1) Å	µ = 0.37 mm⁻¹
b = 11.8778 (11) Å	T = 113 K
c = 15.0130 (15) Å	0.22 × 0.20 × 0.14 mm
β = 107.047 (4)°

Data collection top

Rigaku Saturn CCD diffractometer	4371 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	3362 reflections with I > 2σ(I)
T_min = 0.922, T_max = 0.950	R_int = 0.034
17672 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.03	Δρ_max = 0.55 e Å⁻³
4371 reflections	Δρ_min = −0.36 e Å⁻³
227 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.51046 (3)	0.62323 (3)	1.13695 (2)	0.02998 (11)
Cl2	0.37184 (4)	0.19570 (3)	1.04198 (3)	0.03410 (12)
O1	0.00843 (9)	0.29580 (7)	1.08091 (6)	0.0212 (2)
O2	−0.07870 (8)	0.18353 (7)	0.95872 (6)	0.01666 (19)
O3	0.10997 (9)	0.21926 (8)	0.80025 (7)	0.0243 (2)
O4	0.10974 (10)	0.40685 (8)	0.77325 (7)	0.0279 (2)
C1	0.00933 (12)	0.26065 (10)	1.00566 (9)	0.0162 (3)
C2	0.09833 (12)	0.28979 (10)	0.95101 (9)	0.0174 (3)
C3	0.05816 (13)	0.23083 (10)	0.87256 (9)	0.0182 (3)
C4	−0.06139 (12)	0.16271 (10)	0.86751 (8)	0.0159 (3)
C5	−0.18169 (13)	0.20806 (10)	0.79466 (9)	0.0202 (3)
H5A	−0.1945	0.2881	0.8082	0.024*
H5B	−0.1682	0.2040	0.7323	0.024*
C6	−0.30301 (13)	0.14107 (11)	0.79411 (10)	0.0234 (3)
H6A	−0.3215	0.1509	0.8545	0.028*
H6B	−0.3785	0.1700	0.7443	0.028*
C7	−0.28405 (14)	0.01632 (11)	0.77779 (10)	0.0252 (3)
H7A	−0.3627	−0.0260	0.7794	0.030*
H7B	−0.2720	0.0060	0.7154	0.030*
C8	−0.16622 (14)	−0.02997 (11)	0.85182 (10)	0.0239 (3)
H8A	−0.1534	−0.1099	0.8379	0.029*
H8B	−0.1826	−0.0268	0.9133	0.029*
C9	−0.04271 (13)	0.03628 (10)	0.85624 (9)	0.0194 (3)
H9A	−0.0183	0.0230	0.7984	0.023*
H9B	0.0293	0.0089	0.9094	0.023*
C10	0.20514 (12)	0.37111 (10)	0.98884 (9)	0.0176 (3)
C11	0.17792 (13)	0.48609 (11)	0.98462 (9)	0.0213 (3)
H11	0.0932	0.5114	0.9514	0.026*
C12	0.27197 (13)	0.56429 (11)	1.02792 (9)	0.0223 (3)
H12	0.2523	0.6424	1.0241	0.027*
C13	0.39456 (13)	0.52694 (11)	1.07668 (9)	0.0211 (3)
C14	0.42685 (13)	0.41434 (11)	1.08054 (10)	0.0225 (3)
H14	0.5123	0.3898	1.1127	0.027*
C15	0.33101 (13)	0.33740 (11)	1.03600 (9)	0.0205 (3)
C16	0.14479 (13)	0.31519 (11)	0.75941 (9)	0.0208 (3)
C17	0.22568 (13)	0.28559 (12)	0.69809 (9)	0.0243 (3)
C18	0.28787 (15)	0.18689 (13)	0.70703 (12)	0.0344 (4)
H18A	0.2806	0.1346	0.7531	0.041*
H18B	0.3394	0.1690	0.6673	0.041*
C19	0.23706 (16)	0.37669 (14)	0.63240 (11)	0.0375 (4)
H19A	0.2959	0.3523	0.5972	0.056*
H19B	0.2716	0.4449	0.6677	0.056*
H19C	0.1511	0.3926	0.5892	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.02639 (19)	0.0348 (2)	0.02668 (19)	−0.01427 (15)	0.00461 (15)	−0.00520 (14)
Cl2	0.02374 (19)	0.02107 (19)	0.0554 (3)	0.00275 (13)	0.00842 (18)	0.00714 (15)
O1	0.0225 (5)	0.0261 (5)	0.0155 (5)	−0.0015 (4)	0.0066 (4)	−0.0027 (4)
O2	0.0173 (4)	0.0202 (4)	0.0135 (4)	−0.0023 (3)	0.0061 (4)	−0.0013 (3)
O3	0.0303 (5)	0.0248 (5)	0.0243 (5)	−0.0074 (4)	0.0182 (4)	−0.0054 (4)
O4	0.0303 (6)	0.0293 (5)	0.0268 (5)	0.0020 (4)	0.0127 (5)	0.0018 (4)
C1	0.0153 (6)	0.0157 (6)	0.0174 (6)	0.0022 (5)	0.0043 (5)	0.0021 (5)
C2	0.0163 (6)	0.0183 (6)	0.0184 (6)	0.0002 (5)	0.0064 (5)	0.0008 (5)
C3	0.0198 (6)	0.0181 (6)	0.0193 (6)	−0.0007 (5)	0.0100 (5)	−0.0001 (5)
C4	0.0184 (6)	0.0180 (6)	0.0131 (6)	−0.0013 (5)	0.0073 (5)	−0.0007 (5)
C5	0.0244 (7)	0.0189 (6)	0.0162 (6)	0.0027 (5)	0.0041 (5)	0.0018 (5)
C6	0.0173 (6)	0.0295 (7)	0.0205 (7)	0.0027 (5)	0.0010 (5)	0.0002 (5)
C7	0.0225 (7)	0.0275 (7)	0.0236 (7)	−0.0063 (6)	0.0036 (6)	−0.0028 (6)
C8	0.0260 (7)	0.0177 (6)	0.0268 (7)	−0.0038 (5)	0.0061 (6)	−0.0008 (5)
C9	0.0197 (6)	0.0177 (6)	0.0208 (7)	0.0011 (5)	0.0060 (5)	−0.0013 (5)
C10	0.0169 (6)	0.0216 (6)	0.0153 (6)	−0.0021 (5)	0.0064 (5)	−0.0009 (5)
C11	0.0185 (6)	0.0227 (7)	0.0218 (7)	−0.0004 (5)	0.0047 (5)	−0.0011 (5)
C12	0.0243 (7)	0.0199 (7)	0.0237 (7)	−0.0025 (5)	0.0085 (6)	−0.0032 (5)
C13	0.0204 (6)	0.0261 (7)	0.0172 (6)	−0.0087 (5)	0.0061 (5)	−0.0030 (5)
C14	0.0156 (6)	0.0283 (7)	0.0228 (7)	−0.0028 (5)	0.0044 (5)	0.0045 (5)
C15	0.0205 (7)	0.0204 (6)	0.0220 (7)	−0.0001 (5)	0.0087 (6)	0.0039 (5)
C16	0.0171 (6)	0.0276 (7)	0.0178 (6)	−0.0063 (5)	0.0051 (5)	−0.0015 (5)
C17	0.0203 (7)	0.0358 (8)	0.0185 (7)	−0.0114 (6)	0.0082 (6)	−0.0080 (6)
C18	0.0284 (8)	0.0465 (9)	0.0350 (9)	−0.0084 (7)	0.0195 (7)	−0.0147 (7)
C19	0.0334 (9)	0.0564 (10)	0.0272 (8)	−0.0130 (8)	0.0160 (7)	−0.0021 (7)

Geometric parameters (Å, º) top

Cl1—C13	1.7378 (13)	C8—C9	1.5291 (18)
Cl2—C15	1.7351 (13)	C8—H8A	0.9900
O1—C1	1.2071 (15)	C8—H8B	0.9900
O2—C1	1.3570 (15)	C9—H9A	0.9900
O2—C4	1.4562 (14)	C9—H9B	0.9900
O3—C3	1.3649 (15)	C10—C15	1.3904 (18)
O3—C16	1.3962 (16)	C10—C11	1.3943 (19)
O4—C16	1.1902 (16)	C11—C12	1.3870 (18)
C1—C2	1.4734 (17)	C11—H11	0.9500
C2—C3	1.3289 (18)	C12—C13	1.3807 (19)
C2—C10	1.4810 (17)	C12—H12	0.9500
C3—C4	1.5025 (17)	C13—C14	1.3789 (19)
C4—C5	1.5270 (18)	C14—C15	1.3933 (19)
C4—C9	1.5310 (17)	C14—H14	0.9500
C5—C6	1.5265 (18)	C16—C17	1.4827 (18)
C5—H5A	0.9900	C17—C18	1.337 (2)
C5—H5B	0.9900	C17—C19	1.493 (2)
C6—C7	1.5253 (19)	C18—H18A	0.9500
C6—H6A	0.9900	C18—H18B	0.9500
C6—H6B	0.9900	C19—H19A	0.9800
C7—C8	1.523 (2)	C19—H19B	0.9800
C7—H7A	0.9900	C19—H19C	0.9800
C7—H7B	0.9900

C1—O2—C4	109.93 (9)	H8A—C8—H8B	107.9
C3—O3—C16	119.46 (10)	C8—C9—C4	111.66 (10)
O1—C1—O2	121.58 (11)	C8—C9—H9A	109.3
O1—C1—C2	128.67 (12)	C4—C9—H9A	109.3
O2—C1—C2	109.75 (10)	C8—C9—H9B	109.3
C3—C2—C1	105.91 (11)	C4—C9—H9B	109.3
C3—C2—C10	134.25 (12)	H9A—C9—H9B	108.0
C1—C2—C10	119.83 (11)	C15—C10—C11	117.74 (12)
C2—C3—O3	130.95 (12)	C15—C10—C2	122.54 (11)
C2—C3—C4	112.32 (11)	C11—C10—C2	119.49 (12)
O3—C3—C4	116.67 (11)	C12—C11—C10	121.34 (13)
O2—C4—C3	101.81 (10)	C12—C11—H11	119.3
O2—C4—C5	107.36 (10)	C10—C11—H11	119.3
C3—C4—C5	112.30 (10)	C13—C12—C11	119.05 (12)
O2—C4—C9	109.13 (10)	C13—C12—H12	120.5
C3—C4—C9	113.30 (10)	C11—C12—H12	120.5
C5—C4—C9	112.21 (10)	C14—C13—C12	121.58 (12)
C6—C5—C4	111.34 (10)	C14—C13—Cl1	118.88 (11)
C6—C5—H5A	109.4	C12—C13—Cl1	119.52 (10)
C4—C5—H5A	109.4	C13—C14—C15	118.31 (13)
C6—C5—H5B	109.4	C13—C14—H14	120.8
C4—C5—H5B	109.4	C15—C14—H14	120.8
H5A—C5—H5B	108.0	C10—C15—C14	121.92 (12)
C7—C6—C5	110.66 (11)	C10—C15—Cl2	119.98 (10)
C7—C6—H6A	109.5	C14—C15—Cl2	118.09 (10)
C5—C6—H6A	109.5	O4—C16—O3	122.02 (12)
C7—C6—H6B	109.5	O4—C16—C17	126.80 (12)
C5—C6—H6B	109.5	O3—C16—C17	111.16 (11)
H6A—C6—H6B	108.1	C18—C17—C16	120.88 (13)
C8—C7—C6	110.82 (11)	C18—C17—C19	124.49 (13)
C8—C7—H7A	109.5	C16—C17—C19	114.52 (13)
C6—C7—H7A	109.5	C17—C18—H18A	120.0
C8—C7—H7B	109.5	C17—C18—H18B	120.0
C6—C7—H7B	109.5	H18A—C18—H18B	120.0
H7A—C7—H7B	108.1	C17—C19—H19A	109.5
C7—C8—C9	111.89 (11)	C17—C19—H19B	109.5
C7—C8—H8A	109.2	H19A—C19—H19B	109.5
C9—C8—H8A	109.2	C17—C19—H19C	109.5
C7—C8—H8B	109.2	H19A—C19—H19C	109.5
C9—C8—H8B	109.2	H19B—C19—H19C	109.5

C4—O2—C1—O1	175.71 (11)	C7—C8—C9—C4	52.98 (15)
C4—O2—C1—C2	−4.42 (13)	O2—C4—C9—C8	67.09 (14)
O1—C1—C2—C3	−178.77 (13)	C3—C4—C9—C8	179.75 (11)
O2—C1—C2—C3	1.38 (14)	C5—C4—C9—C8	−51.77 (14)
O1—C1—C2—C10	1.1 (2)	C3—C2—C10—C15	−84.2 (2)
O2—C1—C2—C10	−178.79 (10)	C1—C2—C10—C15	95.97 (15)
C1—C2—C3—O3	−174.75 (13)	C3—C2—C10—C11	101.37 (18)
C10—C2—C3—O3	5.4 (3)	C1—C2—C10—C11	−78.41 (16)
C1—C2—C3—C4	2.16 (15)	C15—C10—C11—C12	−1.63 (19)
C10—C2—C3—C4	−177.64 (13)	C2—C10—C11—C12	173.02 (12)
C16—O3—C3—C2	−50.0 (2)	C10—C11—C12—C13	−0.5 (2)
C16—O3—C3—C4	133.19 (12)	C11—C12—C13—C14	2.3 (2)
C1—O2—C4—C3	5.30 (12)	C11—C12—C13—Cl1	−176.24 (10)
C1—O2—C4—C5	−112.83 (10)	C12—C13—C14—C15	−1.9 (2)
C1—O2—C4—C9	125.32 (10)	Cl1—C13—C14—C15	176.66 (10)
C2—C3—C4—O2	−4.59 (14)	C11—C10—C15—C14	2.05 (19)
O3—C3—C4—O2	172.81 (10)	C2—C10—C15—C14	−172.42 (12)
C2—C3—C4—C5	109.94 (13)	C11—C10—C15—Cl2	−178.86 (10)
O3—C3—C4—C5	−72.66 (14)	C2—C10—C15—Cl2	6.66 (18)
C2—C3—C4—C9	−121.62 (12)	C13—C14—C15—C10	−0.34 (19)
O3—C3—C4—C9	55.77 (15)	C13—C14—C15—Cl2	−179.44 (10)
O2—C4—C5—C6	−66.13 (13)	C3—O3—C16—O4	−14.1 (2)
C3—C4—C5—C6	−177.23 (10)	C3—O3—C16—C17	166.98 (11)
C9—C4—C5—C6	53.77 (14)	O4—C16—C17—C18	161.57 (15)
C4—C5—C6—C7	−56.48 (15)	O3—C16—C17—C18	−19.56 (18)
C5—C6—C7—C8	57.59 (15)	O4—C16—C17—C19	−14.7 (2)
C6—C7—C8—C9	−56.08 (15)	O3—C16—C17—C19	164.16 (12)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x, −y+1, −z+2; (ii) x+1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈Cl₂O₄
M_r	381.23
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	113
a, b, c (Å)	10.759 (1), 11.8778 (11), 15.0130 (15)
β (°)	107.047 (4)
V (Å³)	1834.3 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.22 × 0.20 × 0.14

Data collection
Diffractometer	Rigaku Saturn CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.922, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	17672, 4371, 3362
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.092, 1.03
No. of reflections	4371
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.36

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1ⁱ	0.95	2.52	3.2470 (17)	133.1
C18—H18B···O1ⁱⁱ	0.95	2.56	3.4486 (17)	156.1

Symmetry codes: (i) −x, −y+1, −z+2; (ii) x+1/2, −y+1/2, z−1/2.

References

Bretschneider, T., Benet-Buchholz, J., Fischer, R. & Nauen, R. (2003). Chimia, 57, 697–701. Web of Science CrossRef CAS Google Scholar
Lu, Y., Tao, J. Z. & Zhang, Z. R. (2008). Chem. Intermed. 10, 25–28. Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 5| May 2012| Page o1531

doi:10.1107/S1600536812016340

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

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