3,3,5,5-Tetra­methyl-3,5-disila-4,10-dioxatetra­cyclo­[5.5.1.02,6.08,12]tridecane-9,11-dione

Sheng, P.-P.; Zhang, J.-Y.; Zhang, L.

doi:10.1107/S1600536809009222

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o788

doi:10.1107/S1600536809009222

Open

access

3,3,5,5-Tetramethyl-3,5-disila-4,10-dioxatetracyclo[5.5.1.0^2,6.0^8,12]tridecane-9,11-dione

Peng-Peng Sheng,^a Jun-Ying Zhang ^a ^* and Lin Zhang ^a

^aLaboratory of Adhesives and in-situ Polymerization Technology, Beijing University of Chemical Technology, Beijing 100029, People's Republic of China and Research Center of Laser Fusion, China Academy of Engineering Physics, Mianyang 621900, Sichuan, People's Republic of China
^*Correspondence e-mail: zjybuct@gmail.com

(Received 25 February 2009; accepted 12 March 2009; online 19 March 2009)

The title compound, C₁₃H₂₀O₄Si₂, is a siloxane-functionalized norbornane anhydride. Both five-membered heterocyclic rings of the molecule have a planar structure, whereas the two five-membered aliphatic rings assume envelope conformations. Weak intermolecular C—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For the synthesis and curing properties with the epoxy resin of silylnorbornane anhydrides, see: Eddy et al. (1990 ); Ryang (1983 ). For the preparation of the title complex by reacting 1,1,3,3-tetramethyldisiloxane and 5-norbornene-2,3-dicarboxylic acid anhydride in the presence of a platinum catalyst, see: Buese (1986 ); Eddy & Hallgren (1985 ); Ryang (1983); Swint & Buese (1991 ). In this reaction, the unsaturated anhydride was hydrosilylated with silicon hydride, see: Eddy & Hallgren (1987 ); Lewis & Uriarte (1990 ); Lewis (1990 ); Onopchenko & Sabourin (1987 ).

Experimental

Crystal data

C₁₃H₂₀O₄Si₂
M_r = 296.47
Monoclinic, P 2₁ /n
a = 8.0475 (16) Å
b = 12.047 (2) Å
c = 15.361 (3) Å
β = 95.84 (3)°
V = 1481.5 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 173 K
0.77 × 0.55 × 0.40 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.833, T_max = 0.908
6539 measured reflections
3398 independent reflections
2921 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.102
S = 1.15
3398 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O3ⁱ	0.98	2.56	3.432 (2)	149
C12—H12C⋯O3ⁱⁱ	0.98	2.57	3.443 (2)	149
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x-1, y, z.

Data collection: RAPID-AUTO (Rigaku, 2001 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809009222/xu2490sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809009222/xu2490Isup2.hkl

checkCIF report

Comment top

Recently, we are interested in the synthesis and curing properties with epoxy resin of silylnorbornane anhydrides. The cured products show improved thermal and physical properties as compared to conventional curing agents (Eddy et al., 1990; Ryang, 1983). The title complex was provided by reacting 1,1,3,3-tetramethyldisiloxane and 5-norbornene-2,3-dicarboxylic acid anhydride in the presence of a platinum catalyst (Buese, 1986; Eddy & Hallgren, 1985; Ryang, 1983; Swint & Buese,1991). In this reaction, the unsaturated anhydride was hydrosilylated with silicon hydride (Eddy & Hallgren, 1987; Lewis & Uriarte, 1990; Lewis, 1990; Onopchenko & Sabourin, 1987).

In the title compound, the two Si atoms in tetramethyldisiloxane are linked into a ring by carbon-silicon linkages by two C atoms (Fig. 1). Both five-membered heterocyclic rings of the molecule have planar structure, whereas two five-membered aliphatic rings assume the envelope conformation. The weak intermolecular C—H···O hydrogen bonding presents in the crystal structure (Table 1).

Related literature top

For general background, see: Buese (1986); Eddy & Hallgren (1985; 1987); Eddy et al. (1990); Ryang (1983); Swint & Buese (1991); Lewis & Uriarte (1990); Lewis (1990); Onopchenko & Sabourin (1987).

Experimental top

Synthetic reaction was performed in refluxing toluene under hermetic condition. Toluene was dried over appropriate drying agent and distilled prior to use. There was added 10 drops platinum catalyst to a mixture while it was being stirred of 36.08 g (0.22 mole) of 5-norbornene-2,3- dicarboxylic acid anhydride, 13.4 g (0.1 mole) of 1,1,3,3-tetramethyldisiloxane and 150 ml of toluene. The resulting mixture was heated to 70°C for 8 h and then 100°C overnight. After cooling, filtration, removal of the solvent under vacuum and addition of dry diethyl ether resulted in the precipitation of white powder. Colourless crystals of the title compound suitable for X-ray structure analysis were obtained by crystallization in appropriate solvent.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2001); cell refinement: RAPID-AUTO (Rigaku, 2001); data reduction: RAPID-AUTO (Rigaku, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound at 50% probability level.

3,3,5,5-Tetramethyl-3,5-disila-4,10- dioxatetracyclo[5.5.1.0^2,6.0^8,12]tridecane-9,11-dione top

Crystal data top

C₁₃H₂₀O₄Si₂	F(000) = 632
M_r = 296.47	D_x = 1.329 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 687 reflections
a = 8.0475 (16) Å	θ = 2.2–27.5°
b = 12.047 (2) Å	µ = 0.25 mm⁻¹
c = 15.361 (3) Å	T = 173 K
β = 95.84 (3)°	Block, colourless
V = 1481.5 (5) Å³	0.77 × 0.55 × 0.40 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID IP area-detector diffractometer	3398 independent reflections
Radiation source: rotating anode	2921 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
ω scans at fixed χ = 45°	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
T_min = 0.833, T_max = 0.908	k = −15→15
6539 measured reflections	l = −19→19

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.15	w = 1/[σ²(F_o²) + (0.0539P)²] where P = (F_o² + 2F_c²)/3
3398 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₃H₂₀O₄Si₂	V = 1481.5 (5) Å³
M_r = 296.47	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.0475 (16) Å	µ = 0.25 mm⁻¹
b = 12.047 (2) Å	T = 173 K
c = 15.361 (3) Å	0.77 × 0.55 × 0.40 mm
β = 95.84 (3)°

Data collection top

Rigaku R-AXIS RAPID IP area-detector diffractometer	3398 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2921 reflections with I > 2σ(I)
T_min = 0.833, T_max = 0.908	R_int = 0.016
6539 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.15	Δρ_max = 0.27 e Å⁻³
3398 reflections	Δρ_min = −0.37 e Å⁻³
172 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
Si1	0.16741 (6)	0.26208 (4)	0.90062 (3)	0.02159 (13)
Si2	−0.13909 (6)	0.22004 (4)	0.97218 (3)	0.01986 (13)
O1	0.1060 (2)	0.08686 (13)	1.26700 (10)	0.0447 (4)
O2	0.34875 (17)	0.10991 (11)	1.21113 (8)	0.0295 (3)
O3	0.57506 (18)	0.17797 (12)	1.15730 (9)	0.0371 (4)
O4	−0.03918 (16)	0.25012 (11)	0.88621 (8)	0.0268 (3)
C1	0.1966 (3)	0.14869 (17)	1.23476 (11)	0.0295 (4)
C2	0.4400 (2)	0.19586 (15)	1.17782 (11)	0.0264 (4)
C3	0.3389 (2)	0.30054 (14)	1.17335 (11)	0.0239 (4)
H3A	0.3993	0.3615	1.2076	0.029*
C4	0.2776 (2)	0.33916 (14)	1.07905 (11)	0.0216 (4)
H4A	0.3590	0.3866	1.0509	0.026*
C5	0.1164 (2)	0.39877 (14)	1.09749 (11)	0.0239 (4)
H5A	0.0507	0.4253	1.0435	0.029*
H5B	0.1368	0.4605	1.1397	0.029*
C6	0.0379 (2)	0.29693 (14)	1.13743 (11)	0.0222 (4)
H6A	−0.0747	0.3105	1.1575	0.027*
C7	0.1770 (2)	0.26977 (15)	1.21202 (11)	0.0254 (4)
H7A	0.1630	0.3151	1.2653	0.031*
C8	0.2102 (2)	0.23867 (14)	1.02310 (10)	0.0196 (3)
H8A	0.2885	0.1746	1.0341	0.024*
C9	0.0397 (2)	0.21144 (13)	1.06256 (10)	0.0191 (3)
H9A	0.0451	0.1348	1.0876	0.023*
C10	0.2621 (3)	0.15072 (18)	0.83835 (13)	0.0359 (5)
H10A	0.2381	0.1647	0.7755	0.054*
H10B	0.2149	0.0788	0.8528	0.054*
H10C	0.3832	0.1498	0.8539	0.054*
C11	0.2318 (2)	0.40101 (16)	0.86415 (12)	0.0299 (4)
H11A	0.2057	0.4074	0.8006	0.045*
H11B	0.3523	0.4105	0.8793	0.045*
H11C	0.1716	0.4585	0.8933	0.045*
C12	−0.2961 (2)	0.32903 (15)	0.98616 (12)	0.0278 (4)
H12A	−0.3828	0.3271	0.9365	0.042*
H12B	−0.2418	0.4019	0.9888	0.042*
H12C	−0.3470	0.3158	1.0405	0.042*
C13	−0.2450 (3)	0.08331 (15)	0.95812 (14)	0.0348 (5)
H13A	−0.3371	0.0884	0.9114	0.052*
H13B	−0.2890	0.0621	1.0129	0.052*
H13C	−0.1647	0.0273	0.9427	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Si1	0.0194 (2)	0.0322 (3)	0.0130 (2)	0.0056 (2)	0.00060 (17)	−0.00032 (18)
Si2	0.0180 (2)	0.0239 (2)	0.0170 (2)	0.00166 (18)	−0.00122 (17)	−0.00031 (17)
O1	0.0419 (9)	0.0574 (10)	0.0347 (8)	−0.0030 (7)	0.0025 (7)	0.0191 (7)
O2	0.0328 (8)	0.0327 (7)	0.0219 (6)	0.0063 (6)	−0.0031 (5)	0.0023 (5)
O3	0.0284 (8)	0.0543 (9)	0.0280 (7)	0.0140 (7)	0.0002 (6)	0.0065 (6)
O4	0.0209 (7)	0.0447 (8)	0.0142 (6)	0.0031 (6)	−0.0012 (5)	0.0008 (5)
C1	0.0314 (10)	0.0421 (11)	0.0141 (8)	0.0028 (8)	−0.0025 (7)	0.0031 (7)
C2	0.0281 (10)	0.0355 (10)	0.0139 (8)	0.0037 (8)	−0.0066 (7)	0.0004 (7)
C3	0.0238 (9)	0.0289 (9)	0.0175 (8)	0.0026 (7)	−0.0046 (7)	−0.0023 (7)
C4	0.0210 (9)	0.0251 (8)	0.0177 (8)	0.0024 (7)	−0.0022 (7)	0.0000 (6)
C5	0.0257 (9)	0.0243 (9)	0.0206 (8)	0.0051 (7)	−0.0033 (7)	−0.0031 (6)
C6	0.0212 (9)	0.0300 (9)	0.0150 (8)	0.0063 (7)	0.0004 (6)	−0.0022 (6)
C7	0.0278 (10)	0.0351 (10)	0.0128 (8)	0.0045 (8)	−0.0009 (7)	−0.0035 (7)
C8	0.0180 (8)	0.0258 (8)	0.0146 (7)	0.0066 (7)	−0.0004 (6)	−0.0011 (6)
C9	0.0212 (8)	0.0220 (8)	0.0139 (8)	0.0042 (6)	0.0005 (6)	−0.0009 (6)
C10	0.0392 (12)	0.0486 (12)	0.0206 (9)	0.0149 (10)	0.0056 (8)	−0.0044 (8)
C11	0.0270 (10)	0.0403 (11)	0.0218 (9)	0.0021 (8)	0.0003 (7)	0.0042 (7)
C12	0.0215 (9)	0.0322 (9)	0.0294 (10)	0.0058 (7)	0.0018 (7)	0.0022 (7)
C13	0.0357 (11)	0.0292 (10)	0.0373 (11)	−0.0018 (8)	−0.0078 (9)	−0.0021 (8)

Geometric parameters (Å, º) top

Si1—O4	1.6609 (14)	C5—H5A	0.9900
Si1—C11	1.856 (2)	C5—H5B	0.9900
Si1—C10	1.856 (2)	C6—C9	1.545 (2)
Si1—C8	1.8988 (17)	C6—C7	1.553 (2)
Si2—O4	1.6547 (14)	C6—H6A	1.0000
Si2—C12	1.8501 (18)	C7—H7A	1.0000
Si2—C13	1.8570 (19)	C8—C9	1.589 (2)
Si2—C9	1.8977 (18)	C8—H8A	1.0000
O1—C1	1.185 (2)	C9—H9A	1.0000
O2—C1	1.393 (2)	C10—H10A	0.9800
O2—C2	1.396 (2)	C10—H10B	0.9800
O3—C2	1.182 (2)	C10—H10C	0.9800
C1—C7	1.505 (3)	C11—H11A	0.9800
C2—C3	1.499 (3)	C11—H11B	0.9800
C3—C7	1.531 (3)	C11—H11C	0.9800
C3—C4	1.553 (2)	C12—H12A	0.9800
C3—H3A	1.0000	C12—H12B	0.9800
C4—C5	1.535 (2)	C12—H12C	0.9800
C4—C8	1.551 (2)	C13—H13A	0.9800
C4—H4A	1.0000	C13—H13B	0.9800
C5—C6	1.536 (2)	C13—H13C	0.9800

O4—Si1—C11	110.16 (8)	C7—C6—H6A	114.5
O4—Si1—C10	109.06 (9)	C1—C7—C3	104.57 (15)
C11—Si1—C10	110.76 (10)	C1—C7—C6	115.23 (15)
O4—Si1—C8	101.37 (8)	C3—C7—C6	103.91 (14)
C11—Si1—C8	113.90 (8)	C1—C7—H7A	110.9
C10—Si1—C8	111.15 (8)	C3—C7—H7A	110.9
O4—Si2—C12	109.29 (8)	C6—C7—H7A	110.9
O4—Si2—C13	110.85 (9)	C4—C8—C9	102.53 (13)
C12—Si2—C13	109.41 (10)	C4—C8—Si1	116.81 (12)
O4—Si2—C9	101.65 (7)	C9—C8—Si1	109.40 (11)
C12—Si2—C9	115.46 (8)	C4—C8—H8A	109.3
C13—Si2—C9	109.96 (8)	C9—C8—H8A	109.3
C1—O2—C2	110.85 (15)	Si1—C8—H8A	109.3
Si2—O4—Si1	118.28 (8)	C6—C9—C8	102.71 (13)
O1—C1—O2	119.50 (18)	C6—C9—Si2	116.39 (12)
O1—C1—C7	130.70 (19)	C8—C9—Si2	109.22 (11)
O2—C1—C7	109.81 (16)	C6—C9—H9A	109.4
O3—C2—O2	119.65 (17)	C8—C9—H9A	109.4
O3—C2—C3	130.63 (19)	Si2—C9—H9A	109.4
O2—C2—C3	109.71 (16)	Si1—C10—H10A	109.5
C2—C3—C7	104.96 (15)	Si1—C10—H10B	109.5
C2—C3—C4	114.45 (14)	H10A—C10—H10B	109.5
C7—C3—C4	103.46 (14)	Si1—C10—H10C	109.5
C2—C3—H3A	111.2	H10A—C10—H10C	109.5
C7—C3—H3A	111.2	H10B—C10—H10C	109.5
C4—C3—H3A	111.2	Si1—C11—H11A	109.5
C5—C4—C8	102.28 (14)	Si1—C11—H11B	109.5
C5—C4—C3	99.31 (14)	H11A—C11—H11B	109.5
C8—C4—C3	110.06 (14)	Si1—C11—H11C	109.5
C5—C4—H4A	114.5	H11A—C11—H11C	109.5
C8—C4—H4A	114.5	H11B—C11—H11C	109.5
C3—C4—H4A	114.5	Si2—C12—H12A	109.5
C4—C5—C6	95.15 (13)	Si2—C12—H12B	109.5
C4—C5—H5A	112.7	H12A—C12—H12B	109.5
C6—C5—H5A	112.7	Si2—C12—H12C	109.5
C4—C5—H5B	112.7	H12A—C12—H12C	109.5
C6—C5—H5B	112.7	H12B—C12—H12C	109.5
H5A—C5—H5B	110.2	Si2—C13—H13A	109.5
C5—C6—C9	101.53 (13)	Si2—C13—H13B	109.5
C5—C6—C7	99.69 (14)	H13A—C13—H13B	109.5
C9—C6—C7	110.38 (14)	Si2—C13—H13C	109.5
C5—C6—H6A	114.5	H13A—C13—H13C	109.5
C9—C6—H6A	114.5	H13B—C13—H13C	109.5

C12—Si2—O4—Si1	123.01 (10)	C4—C3—C7—C6	−1.66 (17)
C13—Si2—O4—Si1	−116.32 (10)	C5—C6—C7—C1	−148.19 (15)
C9—Si2—O4—Si1	0.51 (10)	C9—C6—C7—C1	−41.9 (2)
C11—Si1—O4—Si2	−122.87 (10)	C5—C6—C7—C3	−34.41 (16)
C10—Si1—O4—Si2	115.37 (10)	C9—C6—C7—C3	71.83 (17)
C8—Si1—O4—Si2	−1.94 (10)	C5—C4—C8—C9	−33.12 (15)
C2—O2—C1—O1	−177.51 (17)	C3—C4—C8—C9	71.70 (16)
C2—O2—C1—C7	2.98 (19)	C5—C4—C8—Si1	86.45 (15)
C1—O2—C2—O3	177.48 (16)	C3—C4—C8—Si1	−168.72 (12)
C1—O2—C2—C3	−3.49 (19)	O4—Si1—C8—C4	−113.01 (13)
O3—C2—C3—C7	−178.57 (19)	C11—Si1—C8—C4	5.26 (15)
O2—C2—C3—C7	2.54 (18)	C10—Si1—C8—C4	131.21 (14)
O3—C2—C3—C4	68.7 (3)	O4—Si1—C8—C9	2.82 (12)
O2—C2—C3—C4	−110.17 (17)	C11—Si1—C8—C9	121.09 (12)
C2—C3—C4—C5	150.76 (16)	C10—Si1—C8—C9	−112.96 (12)
C7—C3—C4—C5	37.17 (16)	C5—C6—C9—C8	36.63 (15)
C2—C3—C4—C8	43.9 (2)	C7—C6—C9—C8	−68.39 (17)
C7—C3—C4—C8	−69.65 (17)	C5—C6—C9—Si2	−82.62 (15)
C8—C4—C5—C6	55.13 (15)	C7—C6—C9—Si2	172.36 (12)
C3—C4—C5—C6	−57.91 (15)	C4—C8—C9—C6	−2.16 (15)
C4—C5—C6—C9	−56.45 (15)	Si1—C8—C9—C6	−126.78 (11)
C4—C5—C6—C7	56.84 (14)	C4—C8—C9—Si2	121.97 (11)
O1—C1—C7—C3	179.3 (2)	Si1—C8—C9—Si2	−2.65 (13)
O2—C1—C7—C3	−1.26 (18)	O4—Si2—C9—C6	117.15 (13)
O1—C1—C7—C6	−67.3 (3)	C12—Si2—C9—C6	−1.00 (16)
O2—C1—C7—C6	112.13 (17)	C13—Si2—C9—C6	−125.37 (14)
C2—C3—C7—C1	−0.75 (17)	O4—Si2—C9—C8	1.49 (12)
C4—C3—C7—C1	119.55 (15)	C12—Si2—C9—C8	−116.66 (12)
C2—C3—C7—C6	−121.95 (14)	C13—Si2—C9—C8	118.97 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O3ⁱ	0.98	2.56	3.432 (2)	149
C12—H12C···O3ⁱⁱ	0.98	2.57	3.443 (2)	149

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

Experimental details

Crystal data
Chemical formula	C₁₃H₂₀O₄Si₂
M_r	296.47
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	8.0475 (16), 12.047 (2), 15.361 (3)
β (°)	95.84 (3)
V (Å³)	1481.5 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.77 × 0.55 × 0.40

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP area-detector diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.833, 0.908
No. of measured, independent and observed [I > 2σ(I)] reflections	6539, 3398, 2921
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.102, 1.15
No. of reflections	3398
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.37

Computer programs: RAPID-AUTO (Rigaku, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O3ⁱ	0.98	2.56	3.432 (2)	149
C12—H12C···O3ⁱⁱ	0.98	2.57	3.443 (2)	149

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

Acknowledgements

The work was supported financially by the 863 Project of China.

References

Buese, M. A. (1986). US Patent No. 4 598 135. Google Scholar
Eddy, V. J. & Hallgren, J. E. (1985). US Patent No. 4 542 226. Google Scholar
Eddy, V. J. & Hallgren, J. E. (1987). J. Org. Chem. 52, 1903–1906. CrossRef CAS Web of Science Google Scholar
Eddy, V. J., Hallgren, J. E. & Colborn, R. E. (1990). J. Polym. Sci. Part A Polym. Chem. 28, 2417–2426. CrossRef CAS Web of Science Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Lewis, L. N. (1990). J. Am. Chem. Soc. 112, 5998–6004. CrossRef CAS Web of Science Google Scholar
Lewis, L. N. & Uriarte, R. J. (1990). Organometallics, 9, 621–625. CrossRef CAS Web of Science Google Scholar
Onopchenko, A. & Sabourin, E. T. (1987). J. Org. Chem. 52, 4118–4121. CrossRef CAS Web of Science Google Scholar
Rigaku (2001). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Ryang, H.-S. (1983). US Patent No. 4 381 396. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Swint, S. A. & Buese, M. A. (1991). J. Organomet. Chem. 402, 145–153. CrossRef CAS Web of Science Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o788

doi:10.1107/S1600536809009222

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

3,3,5,5-Tetra­methyl-3,5-disila-4,10-dioxa­tetra­cyclo­[5.5.1.02,6.08,12]tri­decane-9,11-dione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3,3,5,5-Tetramethyl-3,5-disila-4,10-dioxatetracyclo[5.5.1.0^2,6.0^8,12]tridecane-9,11-dione