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ISSN: 2056-9890
Volume 68| Part 5| May 2012| Page o1531

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

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[Bretschneider, T., Benet-Buchholz, J., Fischer, R. & Nauen, R. (2003). Chimia, 57, 697-701.]). For the synthesis, see: Lu et al. (2008[Lu, Y., Tao, J. Z. & Zhang, Z. R. (2008). Chem. Intermed. 10, 25-28.]).

[Scheme 1]

Experimental

Crystal data
  • C19H18Cl2O4

  • Mr = 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[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.922, Tmax = 0.950

  • 17672 measured reflections

  • 4371 independent reflections

  • 3362 reflections with I > 2σ(I)

  • Rint = 0.034

Refinement
  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 0.092

  • S = 1.03

  • 4371 reflections

  • 227 parameters

  • H-atom parameters constrained

  • Δρmax = 0.55 e Å−3

  • Δρmin = −0.36 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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.

Refinement top

H atoms were placed in calculated positions, with C—H = 0.95 - 0.99 Å, and included in the final cycles of refinement using a riding model, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C) for methyl C atoms.

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
[Figure 1] 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
C19H18Cl2O4F(000) = 792
Mr = 381.23Dx = 1.381 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6104 reflections
a = 10.759 (1) Åθ = 1.4–28.1°
b = 11.8778 (11) ŵ = 0.37 mm1
c = 15.0130 (15) ÅT = 113 K
β = 107.047 (4)°Prism, colorless
V = 1834.3 (3) Å30.22 × 0.20 × 0.14 mm
Z = 4
Data collection top
Rigaku Saturn CCD
diffractometer
4371 independent reflections
Radiation source: rotating anode3362 reflections with I > 2σ(I)
Multilayer monochromatorRint = 0.034
Detector resolution: 14.63 pixels mm-1θmax = 27.9°, θmin = 2.1°
ω and ϕ scansh = 1314
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
k = 1415
Tmin = 0.922, Tmax = 0.950l = 1919
17672 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0557P)2]
where P = (Fo2 + 2Fc2)/3
4371 reflections(Δ/σ)max = 0.002
227 parametersΔρmax = 0.55 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
C19H18Cl2O4V = 1834.3 (3) Å3
Mr = 381.23Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.759 (1) ŵ = 0.37 mm1
b = 11.8778 (11) ÅT = 113 K
c = 15.0130 (15) Å0.22 × 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)
Tmin = 0.922, Tmax = 0.950Rint = 0.034
17672 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.092H-atom parameters constrained
S = 1.03Δρmax = 0.55 e Å3
4371 reflectionsΔρmin = 0.36 e Å3
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
xyzUiso*/Ueq
Cl10.51046 (3)0.62323 (3)1.13695 (2)0.02998 (11)
Cl20.37184 (4)0.19570 (3)1.04198 (3)0.03410 (12)
O10.00843 (9)0.29580 (7)1.08091 (6)0.0212 (2)
O20.07870 (8)0.18353 (7)0.95872 (6)0.01666 (19)
O30.10997 (9)0.21926 (8)0.80025 (7)0.0243 (2)
O40.10974 (10)0.40685 (8)0.77325 (7)0.0279 (2)
C10.00933 (12)0.26065 (10)1.00566 (9)0.0162 (3)
C20.09833 (12)0.28979 (10)0.95101 (9)0.0174 (3)
C30.05816 (13)0.23083 (10)0.87256 (9)0.0182 (3)
C40.06139 (12)0.16271 (10)0.86751 (8)0.0159 (3)
C50.18169 (13)0.20806 (10)0.79466 (9)0.0202 (3)
H5A0.19450.28810.80820.024*
H5B0.16820.20400.73230.024*
C60.30301 (13)0.14107 (11)0.79411 (10)0.0234 (3)
H6A0.32150.15090.85450.028*
H6B0.37850.17000.74430.028*
C70.28405 (14)0.01632 (11)0.77779 (10)0.0252 (3)
H7A0.36270.02600.77940.030*
H7B0.27200.00600.71540.030*
C80.16622 (14)0.02997 (11)0.85182 (10)0.0239 (3)
H8A0.15340.10990.83790.029*
H8B0.18260.02680.91330.029*
C90.04271 (13)0.03628 (10)0.85624 (9)0.0194 (3)
H9A0.01830.02300.79840.023*
H9B0.02930.00890.90940.023*
C100.20514 (12)0.37111 (10)0.98884 (9)0.0176 (3)
C110.17792 (13)0.48609 (11)0.98462 (9)0.0213 (3)
H110.09320.51140.95140.026*
C120.27197 (13)0.56429 (11)1.02792 (9)0.0223 (3)
H120.25230.64241.02410.027*
C130.39456 (13)0.52694 (11)1.07668 (9)0.0211 (3)
C140.42685 (13)0.41434 (11)1.08054 (10)0.0225 (3)
H140.51230.38981.11270.027*
C150.33101 (13)0.33740 (11)1.03600 (9)0.0205 (3)
C160.14479 (13)0.31519 (11)0.75941 (9)0.0208 (3)
C170.22568 (13)0.28559 (12)0.69809 (9)0.0243 (3)
C180.28787 (15)0.18689 (13)0.70703 (12)0.0344 (4)
H18A0.28060.13460.75310.041*
H18B0.33940.16900.66730.041*
C190.23706 (16)0.37669 (14)0.63240 (11)0.0375 (4)
H19A0.29590.35230.59720.056*
H19B0.27160.44490.66770.056*
H19C0.15110.39260.58920.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.02639 (19)0.0348 (2)0.02668 (19)0.01427 (15)0.00461 (15)0.00520 (14)
Cl20.02374 (19)0.02107 (19)0.0554 (3)0.00275 (13)0.00842 (18)0.00714 (15)
O10.0225 (5)0.0261 (5)0.0155 (5)0.0015 (4)0.0066 (4)0.0027 (4)
O20.0173 (4)0.0202 (4)0.0135 (4)0.0023 (3)0.0061 (4)0.0013 (3)
O30.0303 (5)0.0248 (5)0.0243 (5)0.0074 (4)0.0182 (4)0.0054 (4)
O40.0303 (6)0.0293 (5)0.0268 (5)0.0020 (4)0.0127 (5)0.0018 (4)
C10.0153 (6)0.0157 (6)0.0174 (6)0.0022 (5)0.0043 (5)0.0021 (5)
C20.0163 (6)0.0183 (6)0.0184 (6)0.0002 (5)0.0064 (5)0.0008 (5)
C30.0198 (6)0.0181 (6)0.0193 (6)0.0007 (5)0.0100 (5)0.0001 (5)
C40.0184 (6)0.0180 (6)0.0131 (6)0.0013 (5)0.0073 (5)0.0007 (5)
C50.0244 (7)0.0189 (6)0.0162 (6)0.0027 (5)0.0041 (5)0.0018 (5)
C60.0173 (6)0.0295 (7)0.0205 (7)0.0027 (5)0.0010 (5)0.0002 (5)
C70.0225 (7)0.0275 (7)0.0236 (7)0.0063 (6)0.0036 (6)0.0028 (6)
C80.0260 (7)0.0177 (6)0.0268 (7)0.0038 (5)0.0061 (6)0.0008 (5)
C90.0197 (6)0.0177 (6)0.0208 (7)0.0011 (5)0.0060 (5)0.0013 (5)
C100.0169 (6)0.0216 (6)0.0153 (6)0.0021 (5)0.0064 (5)0.0009 (5)
C110.0185 (6)0.0227 (7)0.0218 (7)0.0004 (5)0.0047 (5)0.0011 (5)
C120.0243 (7)0.0199 (7)0.0237 (7)0.0025 (5)0.0085 (6)0.0032 (5)
C130.0204 (6)0.0261 (7)0.0172 (6)0.0087 (5)0.0061 (5)0.0030 (5)
C140.0156 (6)0.0283 (7)0.0228 (7)0.0028 (5)0.0044 (5)0.0045 (5)
C150.0205 (7)0.0204 (6)0.0220 (7)0.0001 (5)0.0087 (6)0.0039 (5)
C160.0171 (6)0.0276 (7)0.0178 (6)0.0063 (5)0.0051 (5)0.0015 (5)
C170.0203 (7)0.0358 (8)0.0185 (7)0.0114 (6)0.0082 (6)0.0080 (6)
C180.0284 (8)0.0465 (9)0.0350 (9)0.0084 (7)0.0195 (7)0.0147 (7)
C190.0334 (9)0.0564 (10)0.0272 (8)0.0130 (8)0.0160 (7)0.0021 (7)
Geometric parameters (Å, º) top
Cl1—C131.7378 (13)C8—C91.5291 (18)
Cl2—C151.7351 (13)C8—H8A0.9900
O1—C11.2071 (15)C8—H8B0.9900
O2—C11.3570 (15)C9—H9A0.9900
O2—C41.4562 (14)C9—H9B0.9900
O3—C31.3649 (15)C10—C151.3904 (18)
O3—C161.3962 (16)C10—C111.3943 (19)
O4—C161.1902 (16)C11—C121.3870 (18)
C1—C21.4734 (17)C11—H110.9500
C2—C31.3289 (18)C12—C131.3807 (19)
C2—C101.4810 (17)C12—H120.9500
C3—C41.5025 (17)C13—C141.3789 (19)
C4—C51.5270 (18)C14—C151.3933 (19)
C4—C91.5310 (17)C14—H140.9500
C5—C61.5265 (18)C16—C171.4827 (18)
C5—H5A0.9900C17—C181.337 (2)
C5—H5B0.9900C17—C191.493 (2)
C6—C71.5253 (19)C18—H18A0.9500
C6—H6A0.9900C18—H18B0.9500
C6—H6B0.9900C19—H19A0.9800
C7—C81.523 (2)C19—H19B0.9800
C7—H7A0.9900C19—H19C0.9800
C7—H7B0.9900
C1—O2—C4109.93 (9)H8A—C8—H8B107.9
C3—O3—C16119.46 (10)C8—C9—C4111.66 (10)
O1—C1—O2121.58 (11)C8—C9—H9A109.3
O1—C1—C2128.67 (12)C4—C9—H9A109.3
O2—C1—C2109.75 (10)C8—C9—H9B109.3
C3—C2—C1105.91 (11)C4—C9—H9B109.3
C3—C2—C10134.25 (12)H9A—C9—H9B108.0
C1—C2—C10119.83 (11)C15—C10—C11117.74 (12)
C2—C3—O3130.95 (12)C15—C10—C2122.54 (11)
C2—C3—C4112.32 (11)C11—C10—C2119.49 (12)
O3—C3—C4116.67 (11)C12—C11—C10121.34 (13)
O2—C4—C3101.81 (10)C12—C11—H11119.3
O2—C4—C5107.36 (10)C10—C11—H11119.3
C3—C4—C5112.30 (10)C13—C12—C11119.05 (12)
O2—C4—C9109.13 (10)C13—C12—H12120.5
C3—C4—C9113.30 (10)C11—C12—H12120.5
C5—C4—C9112.21 (10)C14—C13—C12121.58 (12)
C6—C5—C4111.34 (10)C14—C13—Cl1118.88 (11)
C6—C5—H5A109.4C12—C13—Cl1119.52 (10)
C4—C5—H5A109.4C13—C14—C15118.31 (13)
C6—C5—H5B109.4C13—C14—H14120.8
C4—C5—H5B109.4C15—C14—H14120.8
H5A—C5—H5B108.0C10—C15—C14121.92 (12)
C7—C6—C5110.66 (11)C10—C15—Cl2119.98 (10)
C7—C6—H6A109.5C14—C15—Cl2118.09 (10)
C5—C6—H6A109.5O4—C16—O3122.02 (12)
C7—C6—H6B109.5O4—C16—C17126.80 (12)
C5—C6—H6B109.5O3—C16—C17111.16 (11)
H6A—C6—H6B108.1C18—C17—C16120.88 (13)
C8—C7—C6110.82 (11)C18—C17—C19124.49 (13)
C8—C7—H7A109.5C16—C17—C19114.52 (13)
C6—C7—H7A109.5C17—C18—H18A120.0
C8—C7—H7B109.5C17—C18—H18B120.0
C6—C7—H7B109.5H18A—C18—H18B120.0
H7A—C7—H7B108.1C17—C19—H19A109.5
C7—C8—C9111.89 (11)C17—C19—H19B109.5
C7—C8—H8A109.2H19A—C19—H19B109.5
C9—C8—H8A109.2C17—C19—H19C109.5
C7—C8—H8B109.2H19A—C19—H19C109.5
C9—C8—H8B109.2H19B—C19—H19C109.5
C4—O2—C1—O1175.71 (11)C7—C8—C9—C452.98 (15)
C4—O2—C1—C24.42 (13)O2—C4—C9—C867.09 (14)
O1—C1—C2—C3178.77 (13)C3—C4—C9—C8179.75 (11)
O2—C1—C2—C31.38 (14)C5—C4—C9—C851.77 (14)
O1—C1—C2—C101.1 (2)C3—C2—C10—C1584.2 (2)
O2—C1—C2—C10178.79 (10)C1—C2—C10—C1595.97 (15)
C1—C2—C3—O3174.75 (13)C3—C2—C10—C11101.37 (18)
C10—C2—C3—O35.4 (3)C1—C2—C10—C1178.41 (16)
C1—C2—C3—C42.16 (15)C15—C10—C11—C121.63 (19)
C10—C2—C3—C4177.64 (13)C2—C10—C11—C12173.02 (12)
C16—O3—C3—C250.0 (2)C10—C11—C12—C130.5 (2)
C16—O3—C3—C4133.19 (12)C11—C12—C13—C142.3 (2)
C1—O2—C4—C35.30 (12)C11—C12—C13—Cl1176.24 (10)
C1—O2—C4—C5112.83 (10)C12—C13—C14—C151.9 (2)
C1—O2—C4—C9125.32 (10)Cl1—C13—C14—C15176.66 (10)
C2—C3—C4—O24.59 (14)C11—C10—C15—C142.05 (19)
O3—C3—C4—O2172.81 (10)C2—C10—C15—C14172.42 (12)
C2—C3—C4—C5109.94 (13)C11—C10—C15—Cl2178.86 (10)
O3—C3—C4—C572.66 (14)C2—C10—C15—Cl26.66 (18)
C2—C3—C4—C9121.62 (12)C13—C14—C15—C100.34 (19)
O3—C3—C4—C955.77 (15)C13—C14—C15—Cl2179.44 (10)
O2—C4—C5—C666.13 (13)C3—O3—C16—O414.1 (2)
C3—C4—C5—C6177.23 (10)C3—O3—C16—C17166.98 (11)
C9—C4—C5—C653.77 (14)O4—C16—C17—C18161.57 (15)
C4—C5—C6—C756.48 (15)O3—C16—C17—C1819.56 (18)
C5—C6—C7—C857.59 (15)O4—C16—C17—C1914.7 (2)
C6—C7—C8—C956.08 (15)O3—C16—C17—C19164.16 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11···O1i0.952.523.2470 (17)133
C18—H18B···O1ii0.952.563.4486 (17)156
Symmetry codes: (i) x, y+1, z+2; (ii) x+1/2, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC19H18Cl2O4
Mr381.23
Crystal system, space groupMonoclinic, P21/n
Temperature (K)113
a, b, c (Å)10.759 (1), 11.8778 (11), 15.0130 (15)
β (°) 107.047 (4)
V3)1834.3 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.37
Crystal size (mm)0.22 × 0.20 × 0.14
Data collection
DiffractometerRigaku Saturn CCD
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.922, 0.950
No. of measured, independent and
observed [I > 2σ(I)] reflections
17672, 4371, 3362
Rint0.034
(sin θ/λ)max1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.092, 1.03
No. of reflections4371
No. of parameters227
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
C11—H11···O1i0.952.523.2470 (17)133.1
C18—H18B···O1ii0.952.563.4486 (17)156.1
Symmetry codes: (i) x, y+1, z+2; (ii) x+1/2, y+1/2, z1/2.
 

References

First citationBretschneider, T., Benet-Buchholz, J., Fischer, R. & Nauen, R. (2003). Chimia, 57, 697–701.  Web of Science CrossRef CAS Google Scholar
First citationLu, Y., Tao, J. Z. & Zhang, Z. R. (2008). Chem. Intermed. 10, 25–28.  Google Scholar
First citationRigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, 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
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