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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o426.
Published online 2010 January 23. doi:  10.1107/S1600536810002400
PMCID: PMC2979752

3,9-Bis(2-chloro­phen­yl)-2,4,8,10-tetra­oxaspiro­[5.5]undeca­ne

Abstract

The complete mol­ecule of the title compound, C19H18Cl2O4, is generated by a crystallographic twofold axis that passes through the spiro C atom. The 1,3-dioxane ring adopts a chair conformation and the phenyl substituent occupies an equatorial site.

Related literature

For the crystal structure of 3,9-diphenyl-2,4,8,10-tetra­oxaspiro­[5.5]undecane, see: Wang et al. (2006 [triangle]).

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Object name is e-66-0o426-scheme1.jpg

Experimental

Crystal data

  • C19H18Cl2O4
  • M r = 381.23
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o426-efi1.jpg
  • a = 10.7116 (5) Å
  • b = 9.4693 (5) Å
  • c = 17.7080 (9) Å
  • β = 106.745 (1)°
  • V = 1719.98 (15) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.40 mm−1
  • T = 173 K
  • 0.46 × 0.42 × 0.22 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.838, T max = 0.917
  • 6932 measured reflections
  • 1883 independent reflections
  • 1707 reflections with I > 2σ(I)
  • R int = 0.015

Refinement

  • R[F 2 > 2σ(F 2)] = 0.032
  • wR(F 2) = 0.092
  • S = 1.00
  • 1883 reflections
  • 114 parameters
  • H-atom parameters constrained
  • Δρmax = 0.30 e Å−3
  • Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 2003 [triangle]); cell refinement: SAINT (Bruker, 2003 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810002400/bt5174sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002400/bt5174Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank the Key Subject Construction Project of Hunan Province (No. 2006–180), the Key Scientific Research Project of Hunan Provincial Education Department (No. 08 A023, 05 C736), The NSF of Hunan Province (09 J J3028) and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

Pentaerythritol (2 g, 0.014 mol), 2-chlorobenzaldehyde(4.6 g, 0.033 mol), toluene (12 ml) and a catalytic amount (0.2 g) of p-toluenesulfonic acid were heated for 4 hours. The mixture was cooled and then filtered. The organic phase was washed with water and 5% sodium bicarbonate (20 ml). The solvent was evaporated and the product recrystallized from ethyl acetate to afford colourless crystals (yield 70%); m.p. 418.5–419 K.

Refinement

H-atoms were placed in calculated positions (C—H 0.95–0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C).

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot of C19H18Cl2O4 at the 70% probability level; hydrogen atoms are shown as spheres of arbitrary radius.

Crystal data

C19H18Cl2O4F(000) = 792
Mr = 381.23Dx = 1.472 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 5105 reflections
a = 10.7116 (5) Åθ = 2.4–27.1°
b = 9.4693 (5) ŵ = 0.40 mm1
c = 17.7080 (9) ÅT = 173 K
β = 106.745 (1)°Block, yellow
V = 1719.98 (15) Å30.46 × 0.42 × 0.22 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer1883 independent reflections
Radiation source: fine-focus sealed tube1707 reflections with I > 2σ(I)
graphiteRint = 0.015
ω scansθmax = 27.1°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −13→13
Tmin = 0.838, Tmax = 0.917k = −12→11
6932 measured reflectionsl = −22→22

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0542P)2 + 1.3419P] where P = (Fo2 + 2Fc2)/3
1883 reflections(Δ/σ)max = 0.001
114 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = −0.25 e Å3

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

xyzUiso*/Ueq
Cl1−0.05287 (3)0.53900 (4)0.14620 (2)0.04156 (14)
O10.30941 (9)0.51739 (10)0.13408 (5)0.0283 (2)
O20.31431 (8)0.34130 (10)0.22630 (5)0.0298 (2)
C1−0.00068 (12)0.40843 (14)0.09327 (7)0.0261 (3)
C2−0.09394 (12)0.34711 (16)0.03040 (8)0.0329 (3)
H2−0.18150.37990.01600.040*
C3−0.05826 (13)0.23835 (18)−0.01081 (8)0.0381 (3)
H3−0.12140.1960−0.05390.046*
C40.07000 (15)0.19038 (18)0.01047 (9)0.0398 (3)
H40.09410.1134−0.01680.048*
C50.16221 (13)0.25578 (16)0.07170 (8)0.0342 (3)
H50.25010.22420.08520.041*
C60.12931 (12)0.36636 (14)0.11379 (7)0.0259 (3)
C70.23515 (12)0.44177 (14)0.17524 (8)0.0265 (3)
H70.19600.50840.20590.032*
C80.40974 (12)0.59806 (14)0.18815 (8)0.0303 (3)
H8A0.36920.66900.21480.036*
H8B0.46140.64910.15860.036*
C90.50000.50311 (19)0.25000.0240 (3)
C100.41483 (12)0.41154 (15)0.28641 (7)0.0291 (3)
H10A0.46990.34020.32160.035*
H10B0.37430.47150.31870.035*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0294 (2)0.0446 (2)0.0492 (2)0.01101 (14)0.00891 (16)−0.00178 (15)
O10.0231 (4)0.0307 (5)0.0247 (4)−0.0053 (4)−0.0034 (4)0.0058 (4)
O20.0220 (4)0.0323 (5)0.0290 (5)−0.0030 (4)−0.0024 (4)0.0091 (4)
C10.0204 (6)0.0298 (6)0.0271 (6)0.0012 (5)0.0051 (5)0.0078 (5)
C20.0182 (6)0.0495 (8)0.0282 (6)−0.0041 (5)0.0022 (5)0.0102 (6)
C30.0283 (7)0.0560 (9)0.0275 (6)−0.0157 (6)0.0042 (5)−0.0035 (6)
C40.0353 (7)0.0459 (9)0.0389 (8)−0.0068 (6)0.0120 (6)−0.0098 (6)
C50.0223 (6)0.0391 (7)0.0390 (7)0.0011 (5)0.0055 (5)−0.0028 (6)
C60.0194 (6)0.0293 (6)0.0262 (6)−0.0012 (5)0.0024 (5)0.0052 (5)
C70.0191 (6)0.0295 (6)0.0278 (6)0.0013 (5)0.0016 (5)0.0039 (5)
C80.0258 (6)0.0259 (6)0.0304 (6)−0.0036 (5)−0.0057 (5)0.0046 (5)
C90.0208 (8)0.0257 (8)0.0214 (8)0.000−0.0004 (6)0.000
C100.0224 (6)0.0376 (7)0.0232 (6)−0.0006 (5)0.0000 (5)0.0051 (5)

Geometric parameters (Å, °)

Cl1—C11.7384 (14)C5—C61.388 (2)
O1—C71.4181 (15)C5—H50.9500
O1—C81.4361 (15)C6—C71.5062 (17)
O2—C71.4141 (15)C7—H71.0000
O2—C101.4402 (15)C8—C91.5272 (16)
C1—C21.3906 (18)C8—H8A0.9900
C1—C61.3921 (17)C8—H8B0.9900
C2—C31.378 (2)C9—C8i1.5272 (16)
C2—H20.9500C9—C101.5293 (16)
C3—C41.392 (2)C9—C10i1.5293 (16)
C3—H30.9500C10—H10A0.9900
C4—C51.385 (2)C10—H10B0.9900
C4—H40.9500
C7—O1—C8110.41 (9)O1—C7—C6106.55 (10)
C7—O2—C10110.16 (10)O2—C7—H7110.2
C2—C1—C6121.55 (13)O1—C7—H7110.2
C2—C1—Cl1117.40 (10)C6—C7—H7110.2
C6—C1—Cl1121.04 (10)O1—C8—C9111.25 (10)
C3—C2—C1119.41 (12)O1—C8—H8A109.4
C3—C2—H2120.3C9—C8—H8A109.4
C1—C2—H2120.3O1—C8—H8B109.4
C2—C3—C4120.21 (13)C9—C8—H8B109.4
C2—C3—H3119.9H8A—C8—H8B108.0
C4—C3—H3119.9C8i—C9—C8107.86 (14)
C5—C4—C3119.45 (14)C8i—C9—C10111.27 (7)
C5—C4—H4120.3C8—C9—C10107.75 (7)
C3—C4—H4120.3C8i—C9—C10i107.75 (7)
C6—C5—C4121.57 (12)C8—C9—C10i111.27 (7)
C6—C5—H5119.2C10—C9—C10i110.92 (16)
C4—C5—H5119.2O2—C10—C9111.10 (9)
C5—C6—C1117.72 (12)O2—C10—H10A109.4
C5—C6—C7119.39 (11)C9—C10—H10A109.4
C1—C6—C7122.75 (12)O2—C10—H10B109.4
O2—C7—O1110.28 (9)C9—C10—H10B109.4
O2—C7—C6109.32 (10)H10A—C10—H10B108.0
C6—C1—C2—C32.55 (19)C8—O1—C7—C6177.43 (10)
Cl1—C1—C2—C3−176.83 (11)C5—C6—C7—O2−50.34 (15)
C1—C2—C3—C40.1 (2)C1—C6—C7—O2133.95 (12)
C2—C3—C4—C5−2.1 (2)C5—C6—C7—O168.83 (15)
C3—C4—C5—C61.5 (2)C1—C6—C7—O1−106.88 (13)
C4—C5—C6—C11.0 (2)C7—O1—C8—C958.27 (13)
C4—C5—C6—C7−174.90 (13)O1—C8—C9—C8i−171.63 (13)
C2—C1—C6—C5−3.07 (19)O1—C8—C9—C10−51.41 (14)
Cl1—C1—C6—C5176.29 (10)O1—C8—C9—C10i70.39 (14)
C2—C1—C6—C7172.71 (12)C7—O2—C10—C9−58.74 (14)
Cl1—C1—C6—C7−7.93 (17)C8i—C9—C10—O2169.66 (10)
C10—O2—C7—O164.19 (13)C8—C9—C10—O251.61 (14)
C10—O2—C7—C6−178.97 (10)C10i—C9—C10—O2−70.41 (9)
C8—O1—C7—O2−64.03 (13)

Symmetry codes: (i) −x+1, y, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5174).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2003). SAINT and SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wang, J.-K., Yan, D.-Y., Liu, L.-J., Liu, S. & Wang, J.-T. (2006). Acta Cryst. E62, o3062–o3063.
  • Westrip, S. P. (2010). publCIF In preparation.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography