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

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ISSN: 2056-9890

Isoprop­yl 2,5-anhydro-3,4-di-O-tert-butyl­di­phenyl­sil­yl-L-ribonate

aChemical Crystallography, Chemical Research Laboratory, University of Oxford, Oxford OX1 3TA, England, bDivision of Organic Synthesis, National Chemical Laboratory, Pune 411 008, India, cBiological Chemistry, Division of Biomedical Sciences, Imperial College, London SW7 2AZ, England, and dDepartment of Organic Chemistry, Chemical Research Laboratory, Mansfield Road, Oxford OX1 3TA, England
*Correspondence e-mail: david.watkin@chem.ox.ac.uk

(Received 15 July 2005; accepted 25 July 2005; online 27 July 2005)

Determination of the crystal structure of the title compound, C40H50O5Si2, firmly established its relative configuration and hence that of some related tetra­hydro­furan carboxyl­ates. The material crystallizes with Z′ = 2. Except for the chiral centres, the two independent mol­ecules are related by a pseudo-centre of symmetry.

Comment

The reaction of methanol with lactones containing 2-O-trifluoro­methane­sulfonates (trifluoro­methane­sulfonates) in the presence of either acid (Wheatley et al., 1993[Wheatley, J. R., Bichard, C. J. F., Mantell, S. J., Son, J. C., Hughes, D. J., Fleet, G. W. J. & Brown, D. (1993). J. Chem. Soc. Chem. Commun. pp. 1065-1067.]) or base (Choi et al., 1992[Choi, S. S., Myerscough, P. M., Fairbanks, A. J., Skead, B. M., Bichard, C. J. F., Mantell, S. J., Fleet, G. W. J., Saunders, J. & Brown, D. (1992). J. Chem. Soc. Chem. Commun. pp. 1605-1607.]) provides a general synthesis of meth­yl tetra­hydro­furan-2-carboxyl­ates. Such materials have been exploited in the preparation of sugar amino acids (SAAs) for use as peptidomimetics (Chakraborty et al., 2004[Chakraborty, T. K., Srinivasi, P., Tapadar, S. & Mohan, B. K. (2004). J. Chem. Sci. 116, 187-207.]; Grotenberg et al., 2004[Grotenberg, G. M., Timmerj, M. S. M., Llamas-Saiz, A. L., Verdoes, M., van der Marel, G. A., van Raaij, M. J., Overkleeft, H. S. & Overhand, M. (2004). J. Am. Chem. Soc. 126, 3444-3446.]; Smith et al., 2003[Smith, M. D., Claridge, T. D. W., Sansom, M. P. & Fleet, G. W. J. (2003). Org. Biomol. Chem. 1, 3647-3655.]). Many THF SAA scaffolds are predisposed to form secondary structures in short oligomers (Claridge et al., 2005[Claridge, T. D. W., Long, D. D., Baker, C. M., Odell, B., Grant, G. H., Edwards, A. A., Tranter, G. E., Fleet., G. W. J. & Smith, M. D. (2005). J. Org. Chem. 70, 2082-2090.]; Long et al., 1999[Long, D. D., Hungerford, N. L., Smith, M. D., Brittain, D. E. A., Marquess, D. G., Claridge, T. D. W. & Fleet, G. W. J. (1999). Tetrahedron Lett. 40, 2195-2198.], 2002[Long, D. D., Smith M. D., Martin, A., Wheatley, J. R., Watkin, D. G., Muller, M. & Fleet, G. W. J. (2002). J. Chem. Soc. Perkin Trans. 1, pp. 1982-1998.]; Hungerford et al., 2000[Hungerford, N. L., Claridge, T. D. W., Watterson, M. P., Aplin, R. T., Moreno, A. & Fleet, G. W. J. (2000). J. Chem. Soc. Perkin Trans. 1, pp. 3666-3679.]). There are only limited reports of γ-peptides based on cyclic templates (Curran et al., 1996[Curran, T. P., Chandler, N. M., Kennedy, R. J. & Keaney, M. T. (1996). Tetrahedron Lett. 37, 1933-1936.]; Crisma et al., 2001[Crisma, M., Moretto, A., Toniolo, C., Kaczmarek, K. & Zabrocki, J. (2001). Macromolecules, 14, 5048-5052.]). In a programme directed towards the synthesis of γ-THF SAAs, it was found that reaction of the δ-lactone trifluoro­methane­sulfonate (1) (Stewart et al., 2002[Stewart, A. J., Evans, R. M., Weymouth-Wilson, A. C., Cowley, A. R., Watkin, D. J. & Fleet, G. W. J. (2002). Tetrahedron Asymmetry, 13, 2667-2672.]) with methanol in the presence of sodium carbonate gave a mixture of the THF carboxyl­ates (2) and (3). In order to ensure the correct assignment of the stereochemistry at C-2 in the epimers, (3) was converted to the crystalline disil­yl ether (4), the structure of which is reported in this paper (Fig. 1[link]).

[Scheme 1]

The structure of (4) contains two mol­ecules in the asymmetric unit (Z′ = 2). Except for the 1,4-anhydro­ribonate units (which are chiral and therefore cannot be related by an improper operator), the mol­ecules are related by a pseudo-centre of symmetry at ([{1\over 2}],[{1\over 5}],[{3\over 4}]). The absolute configuration of the material was known unambiguously from the synthesis; the Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]) parameter is in agreement with this assignment.

The structure consists of mol­ecular layers (Fig. 2[link]) lying parallel to the bc plane, and characterized by a hydro­philic and a hydro­phobic surface. The hydro­phobic surface of one layer faces the equivalent surface of the adjacent layer (Fig. 3[link]).

[Figure 1]
Figure 1
The structure of one mol­ecule of the title compound with displacement ellipsoids drawn at the 50% probability level. All H atoms, except for H31, H41, H61 and H71, have been omitted for clarity. The H atoms are drawn with an arbitary radius.
[Figure 2]
Figure 2
The crystal structure projected on to the bc plane.
[Figure 3]
Figure 3
The crystal structure projected along the b axis, showing two hydro­phobic faces opposing each other. By symmetry, pairs of hydro­philic faces also oppose each other.

Experimental

Epimer (3) was converted to the corresponding disil­yl ether by standard procedures (Sanjayan et al., 2003[Sanjayan, G. J., Stewart, A. J., Hachisu, S., Gonzalez, R., Watterson., M. P. & Fleet, G. W. J. (2003). Tetrahedron Lett. 44, 5847-5852.]) and was crystallized from eth­yl acetate–hexa­ne (1:4).

Crystal data
  • C40H50O5Si2

  • Mr = 667.01

  • Monoclinic, P 21

  • a = 17.2952 (2) Å

  • b = 10.7468 (2) Å

  • c = 20.4914 (4) Å

  • β = 100.7864 (5)°

  • V = 3741.40 (11) Å3

  • Z = 4

  • Dx = 1.184 Mg m−3

  • Mo Kα radiation

  • Cell parameters from 8312 reflections

  • θ = 5–30°

  • μ = 0.14 mm−1

  • T = 190 K

  • Prism, colourless

  • 0.40 × 0.20 × 0.20 mm

Data collection
  • Nonius KappaCCD diffractometer

  • ω scans

  • Absorption correction: multi-scan(DENZO/SCALEPACK; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.])Tmin = 0.70, Tmax = 0.97

  • 27685 measured reflections

  • 17372 independent reflections

  • 17372 reflections with I > −3σ(I)

  • Rint = 0.027

  • θmax = 30.0°

  • h = −24 → 24

  • k = −15 → 15

  • l = −28 → 28

Refinement
  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 0.096

  • S = 0.97

  • 17372 reflections

  • 848 parameters

  • H-atom parameters constrained

  • w = 1/[σ2(F2) + (0.02P)2 + 2.21P] where P = [max(Fo2,0) + 2Fc2]/3

  • (Δ/σ)max = 0.003

  • Δρmax = 0.70 e Å−3

  • Δρmin = −0.47 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 17372 Friedel pairs

  • Flack parameter: 0.05 (7)

The H atoms were all located in a difference map, but those attached to C atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularize their geometry (C—H = 0.93–98 Å) and displace­ment parameters [Uiso(H) = 1.2–1.5Ueq(parent atom)], after which they were refined with riding constraints. The pseudo-centre of inversion did not lead to any refinement problems.

Data collection: COLLECT (Nonius, 2001[Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO/SCALEPACK; data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003[Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.]); molecular graphics: CAMERON (Watkin et al., 1996[Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England.]); software used to prepare material for publication: CRYSTALS.

Supporting information


Comment top

The reaction of methanol with lactones containing 2-O-trifluoromethanesulfonates (trifluoromethanesulfonates) in the presence of either acid (Wheatley et al., 1993) or base (Choi et al., 1992) provides a general synthesis of methyl tetrahydrofuran-2-carboxylates. Such materials have been exploited in the preparation of sugar amino acids (SAAs) for use as peptidomimetics (Chakraborty et al., 2004; Grotenberg et al., 2004; Smith et al., 2003). Many THF SAA scaffolds are predisposed to form secondary structures in short oligomers (Claridge et al., 2005; Long et al., 1999, 2002; Hungerford et al., 2000). There are only limited reports of γ-peptides based on cyclic templates (Curran et al., 1996; Crisma et al., 2001). In a program directed towards the synthesis of γ-THF SAAs, it was found that reaction of the δ-lactone trifluoromethanesulfonate (1) (Stewart et al., 2002) with methanol in the presence of sodium carbonate gave a mixture of the THF carboxylates (2) and (3). In order to ensure the correct assignment of the stereochemistry at C-2 in the epimers, (3) was converted to the crystalline disilyl ether (4), the structure of which is reported in this paper (Fig. 1).

The structure of (4) contains two molecules in the asymmetric unit (Z' = 2). Except for the 1,4-anhydroribonate units (which are chiral and therefore cannot be related by an improper operator), the molecules are related by a pseudo-centre of symmetry at (1/2,1/5,3/4). The absolute configuration of the material was known unambiguously from the synthesis; the Flack (1983) parameter is in agreement with this assignment.

The structure consists of molecular layers (Fig. 2) lying parallel to the bc plane, and characterized by a hydrophilic and a hydrophobic surface. The hydrophobic surface of one layer faces the equivalent surface of the adjacent layer (Fig. 3).

Experimental top

Epimer (3) was converted to the corresponding disilyl ether by standard procedures (Sanjayan et al., 2003) and was crystallized from ethyl acetate–hexane (1:4).

Refinement top

The H atoms were all located in a difference map, but those attached to C atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularize their geometry (C—H = 0.93–98 Å) and displacement parameters [Uiso(H) = 1.2–1.5Ueq(parent atom)], after which they were refined with riding constraints to their adjacent non-H atom. The pseudo-centre of inversion did not lead to any refinement problems.

Computing details top

Data collection: COLLECT (Nonius, 2001); cell refinement: DENZO/SCALEPACK; data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS.

Figures top
[Figure 1] Fig. 1. The structure of one molecule of the title compound with displacement ellipsoids drawn at the 50% probability level. All H atoms, except for H31, H41, H61 and H71, have been omitted for clarity. The H atoms are drawn with an arbitary radius.
[Figure 2] Fig. 2. The crystal structure projected on to the bc plane.
[Figure 3] Fig. 3. The crystal structure projected along the b axis, showing two hydrophobic faces opposing each other. By symmetry, pairs of hydrophilic faces also oppose each other.
Isopropyl 2,5-anhydro-3,4-di-O-tert-butyldiphenylsilyl-L-ribonate top
Crystal data top
C40H50O5Si2F(000) = 1432
Mr = 667.01Dx = 1.184 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 17.2952 (2) ÅCell parameters from 8312 reflections
b = 10.7468 (2) Åθ = 5–30°
c = 20.4914 (4) ŵ = 0.14 mm1
β = 100.7864 (5)°T = 190 K
V = 3741.40 (11) Å3Prism, colourless
Z = 40.40 × 0.20 × 0.20 mm
Data collection top
Nonius KappaCCD
diffractometer
17372 reflections with I > 3σ(I)
Graphite monochromatorRint = 0.027
ω scansθmax = 30.0°, θmin = 5.1°
Absorption correction: multi-scan
(DENZO/SCALEPACK; Otwinowski & Minor, 1997)
h = 2424
Tmin = 0.70, Tmax = 0.97k = 1515
27685 measured reflectionsl = 2828
17372 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.050 w = 1/[σ2(F2) + (0.02P)2 + 2.21P]
where P = [max(Fo2,0) + 2Fc2]/3
wR(F2) = 0.096(Δ/σ)max = 0.003
S = 0.97Δρmax = 0.70 e Å3
17372 reflectionsΔρmin = 0.47 e Å3
848 parametersAbsolute structure: Flack (1983), 17372 Friedel pairs
370 restraintsAbsolute structure parameter: 0.05 (7)
Primary atom site location: structure-invariant direct methods
Crystal data top
C40H50O5Si2V = 3741.40 (11) Å3
Mr = 667.01Z = 4
Monoclinic, P21Mo Kα radiation
a = 17.2952 (2) ŵ = 0.14 mm1
b = 10.7468 (2) ÅT = 190 K
c = 20.4914 (4) Å0.40 × 0.20 × 0.20 mm
β = 100.7864 (5)°
Data collection top
Nonius KappaCCD
diffractometer
17372 independent reflections
Absorption correction: multi-scan
(DENZO/SCALEPACK; Otwinowski & Minor, 1997)
17372 reflections with I > 3σ(I)
Tmin = 0.70, Tmax = 0.97Rint = 0.027
27685 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.096Δρmax = 0.70 e Å3
S = 0.97Δρmin = 0.47 e Å3
17372 reflectionsAbsolute structure: Flack (1983), 17372 Friedel pairs
848 parametersAbsolute structure parameter: 0.05 (7)
370 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Si1010.27529 (3)0.30044 (6)0.61323 (3)0.0217
O1020.22809 (7)0.31163 (14)0.53577 (7)0.0246
C1030.16486 (10)0.23538 (18)0.50601 (11)0.0217
C1040.10903 (11)0.3046 (2)0.45241 (11)0.0282
O1050.06189 (8)0.20842 (15)0.41694 (9)0.0345
C1060.10724 (10)0.0968 (2)0.42112 (11)0.0256
C1070.18749 (10)0.12338 (18)0.46664 (10)0.0200
O1080.24611 (7)0.16056 (13)0.43144 (8)0.0238
Si1090.28559 (3)0.09829 (6)0.37194 (3)0.0200
C1100.33216 (10)0.05648 (19)0.39734 (11)0.0243
C1110.34049 (12)0.1010 (2)0.46209 (13)0.0336
C1120.37400 (13)0.2174 (2)0.47959 (14)0.0422
C1130.40042 (13)0.2900 (2)0.43265 (16)0.0409
C1140.39413 (12)0.2468 (2)0.36844 (14)0.0372
C1150.35986 (11)0.1320 (2)0.35080 (13)0.0306
C1160.20935 (10)0.06992 (19)0.29509 (11)0.0249
C1170.17521 (14)0.1650 (2)0.25346 (14)0.0449
C1180.11585 (17)0.1416 (3)0.19988 (16)0.0666
C1190.08840 (14)0.0229 (3)0.18565 (15)0.0565
C1200.12005 (12)0.0733 (3)0.22609 (13)0.0408
C1210.17941 (11)0.0500 (2)0.27999 (12)0.0307
C1220.36373 (11)0.2169 (2)0.36274 (12)0.0264
C1230.42608 (13)0.2113 (3)0.42695 (14)0.0388
C1240.32958 (14)0.3495 (2)0.35564 (15)0.0405
C1250.29827 (17)0.5551 (2)0.62102 (18)0.0505
C1480.40210 (14)0.1865 (2)0.30316 (14)0.0395
C1260.06575 (10)0.00860 (19)0.45023 (11)0.0280
O1270.09712 (9)0.11542 (14)0.43647 (9)0.0392
C1280.07317 (14)0.2296 (2)0.46593 (14)0.0414
C1290.1227 (2)0.2470 (5)0.5320 (3)0.1084
C1300.0765 (4)0.3287 (3)0.4166 (3)0.1335
O1310.01441 (10)0.00282 (16)0.48086 (11)0.0526
C1320.34696 (12)0.4345 (2)0.62344 (13)0.0310
C1330.39454 (14)0.4398 (2)0.56774 (14)0.0414
C1340.40334 (15)0.4268 (3)0.69109 (14)0.0448
C1360.20439 (11)0.31981 (19)0.67144 (11)0.0254
C1370.22535 (12)0.2833 (2)0.73774 (12)0.0314
C1380.17757 (14)0.3079 (2)0.78365 (13)0.0383
C1390.10643 (14)0.3670 (2)0.76361 (15)0.0452
C1400.08355 (14)0.4029 (2)0.69816 (15)0.0460
C1410.13198 (13)0.3803 (2)0.65244 (14)0.0376
C1420.32126 (11)0.1427 (2)0.62873 (11)0.0255
C1430.39989 (12)0.1172 (2)0.62551 (13)0.0377
C1440.43137 (13)0.0014 (2)0.63734 (13)0.0429
C1450.38510 (14)0.0979 (2)0.65155 (12)0.0380
C1460.30716 (13)0.0770 (2)0.65378 (11)0.0338
C1470.27602 (12)0.0428 (2)0.64295 (11)0.0299
H10310.13760.20560.53940.0312*
H10410.13970.34800.42330.0397*
H10420.07720.36440.46920.0400*
H10610.11400.07220.37640.0355*
H10710.20380.05060.49530.0263*
H11110.32330.05240.49460.0475*
H11210.37880.24700.52420.0598*
H11310.42350.36740.44460.0570*
H11410.41380.29590.33650.0521*
H11510.35460.10550.30620.0426*
H11710.19320.24710.26140.0590*
H11810.09530.20780.17370.0872*
H11910.04860.00780.14910.0747*
H12010.09980.15620.21700.0566*
H12110.20180.11900.30790.0417*
H12310.46680.27280.42520.0672*
H12320.45090.13180.43150.0664*
H12330.40150.22630.46480.0678*
H12410.37110.40930.35730.0727*
H12420.29420.35720.31280.0727*
H12430.30040.36500.39180.0728*
H12810.01730.21700.47200.0623*
H12910.10300.31420.55580.1845*
H12920.17430.27260.52260.1841*
H12930.12770.17140.55730.1853*
H13010.04460.39840.42470.2656*
H13020.06020.29530.37300.2656*
H13030.13070.35250.42230.2660*
H13310.42730.51420.57140.0744*
H13320.35940.44340.52490.0753*
H13330.42800.36670.56890.0745*
H13410.43760.49880.69590.0794*
H13420.43720.35210.69530.0795*
H13430.37270.42900.72740.0797*
H13710.27400.24200.75100.0450*
H13810.19450.28360.82900.0550*
H13910.07100.38000.79380.0669*
H14010.03520.44320.68440.0655*
H14110.11580.40780.60750.0532*
H14310.43360.18280.61460.0538*
H14410.48390.01770.63230.0626*
H14510.40550.17840.65980.0529*
H14610.27590.14580.66260.0479*
H14710.22350.05610.64820.0414*
H12510.33410.62450.62410.0922*
H12520.26210.56060.57900.0916*
H12530.26940.55750.65730.0914*
H14810.44590.24680.29910.0723*
H14820.36380.18720.26230.0736*
H14830.42500.10350.30830.0731*
Si10.72364 (3)0.30675 (6)1.12684 (3)0.0204
O20.75835 (7)0.24766 (14)1.06464 (8)0.0260
C30.82073 (11)0.26353 (19)1.03004 (12)0.0255
C40.90180 (11)0.2759 (2)1.07447 (12)0.0309
O50.92895 (9)0.15133 (16)1.09127 (10)0.0419
C60.87482 (11)0.06489 (19)1.05594 (11)0.0262
C70.83186 (10)0.13924 (18)0.99583 (10)0.0215
O80.76326 (7)0.07700 (13)0.96519 (7)0.0229
Si90.71442 (3)0.09575 (6)0.88852 (3)0.0208
C100.66986 (11)0.25538 (19)0.87472 (11)0.0236
C110.59149 (12)0.2803 (2)0.87726 (12)0.0348
C120.56001 (13)0.3987 (2)0.86442 (13)0.0414
C130.60653 (14)0.4952 (2)0.84966 (12)0.0371
C140.68474 (14)0.4740 (2)0.84830 (12)0.0360
C150.71607 (12)0.3554 (2)0.86050 (12)0.0302
C160.78341 (10)0.07544 (18)0.82865 (11)0.0245
C170.85308 (12)0.0067 (2)0.84432 (13)0.0321
C180.90013 (13)0.0147 (2)0.79708 (15)0.0405
C190.87767 (14)0.0310 (2)0.73354 (14)0.0420
C200.80865 (14)0.0981 (2)0.71612 (13)0.0404
C210.76297 (12)0.1211 (2)0.76376 (12)0.0309
C220.64055 (12)0.0354 (2)0.87710 (12)0.0280
C230.59349 (14)0.0406 (2)0.93337 (14)0.0399
C240.68739 (15)0.1577 (2)0.87864 (16)0.0434
C250.58456 (13)0.0253 (3)0.81001 (13)0.0399
C260.91929 (10)0.04672 (19)1.03593 (10)0.0269
O270.88236 (9)0.15138 (14)1.04527 (11)0.0452
C280.91735 (14)0.2698 (2)1.02870 (15)0.0426
C290.9674 (3)0.3147 (4)1.0886 (2)0.1224
C300.8509 (2)0.3547 (4)1.0019 (3)0.1365
O310.97855 (9)0.04067 (15)1.01401 (10)0.0422
C320.64550 (11)0.18924 (19)1.13738 (12)0.0259
C330.58200 (13)0.1943 (2)1.07413 (15)0.0386
C340.60892 (14)0.2200 (2)1.19755 (14)0.0396
C350.67821 (13)0.0551 (2)1.14394 (15)0.0393
C360.80372 (10)0.33135 (19)1.20143 (11)0.0252
C370.83211 (12)0.4511 (2)1.21847 (12)0.0311
C380.89514 (12)0.4715 (2)1.27029 (13)0.0395
C390.93142 (14)0.3739 (3)1.30614 (14)0.0527
C400.90507 (16)0.2544 (3)1.29044 (16)0.0646
C410.84217 (14)0.2334 (2)1.23836 (14)0.0454
C420.67599 (10)0.46124 (19)1.10335 (11)0.0232
C430.64981 (11)0.5375 (2)1.15032 (12)0.0281
C440.61324 (11)0.6509 (2)1.13260 (13)0.0327
C450.60239 (13)0.6909 (2)1.06750 (16)0.0395
C460.62701 (13)0.6172 (2)1.02008 (14)0.0409
C470.66296 (12)0.5029 (2)1.03770 (12)0.0317
H310.80990.33300.99810.0353*
H410.90030.32251.11460.0440*
H420.93680.31861.05040.0445*
H610.83800.03191.08280.0346*
H710.87000.14990.96470.0290*
H1110.55780.21290.88840.0487*
H1210.50550.41160.86560.0588*
H1310.58520.57460.84130.0519*
H1410.71810.53750.83820.0517*
H1510.76950.34250.85900.0445*
H1710.86840.02660.88700.0456*
H1810.94720.06150.80810.0594*
H1910.90910.01500.70220.0637*
H2010.79330.13030.67300.0597*
H2110.71730.16930.75230.0443*
H2310.56130.11580.92580.0723*
H2320.62710.04840.97710.0717*
H2330.55900.02930.93270.0716*
H2410.65030.22730.87420.0764*
H2420.72510.16680.92090.0763*
H2430.71620.15890.84130.0773*
H2510.55110.09920.80460.0684*
H2520.55080.04900.80860.0689*
H2530.61400.02200.77250.0685*
H2810.94270.25550.99170.0645*
H2911.00730.36921.07650.2047*
H2920.92750.36281.10930.2041*
H2930.98890.24871.11790.2057*
H3010.87000.44031.00340.2369*
H3020.80630.34421.02430.2373*
H3030.83420.33220.95560.2374*
H3310.54200.13501.07550.0679*
H3320.55730.27521.06790.0661*
H3330.60270.17471.03440.0669*
H3410.56670.16041.19910.0727*
H3420.64780.21121.23780.0729*
H3430.58840.30411.19400.0739*
H3510.63510.00391.14490.0688*
H3520.71690.04471.18360.0700*
H3530.70190.03741.10680.0699*
H3710.81030.51831.19290.0431*
H3810.91090.55411.28140.0550*
H3910.97460.38891.34150.0705*
H4010.92750.18711.31450.0831*
H4110.82610.15231.22780.0598*
H4310.65780.51321.19550.0393*
H4410.59500.70151.16510.0455*
H4510.57730.76841.05540.0549*
H4610.61970.64450.97610.0578*
H4710.67910.45221.00500.0437*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Si1010.0227 (2)0.0186 (2)0.0240 (3)0.0011 (2)0.0046 (2)0.0021 (2)
O1020.0272 (6)0.0222 (6)0.0241 (8)0.0041 (6)0.0043 (5)0.0013 (6)
C1030.0180 (7)0.0240 (9)0.0234 (10)0.0005 (7)0.0048 (7)0.0006 (8)
C1040.0231 (8)0.0260 (9)0.0356 (11)0.0059 (8)0.0058 (8)0.0042 (9)
O1050.0216 (6)0.0347 (8)0.0424 (10)0.0025 (6)0.0060 (6)0.0043 (7)
C1060.0196 (7)0.0302 (10)0.0266 (10)0.0019 (8)0.0033 (7)0.0003 (9)
C1070.0174 (7)0.0207 (9)0.0215 (10)0.0000 (6)0.0025 (7)0.0000 (7)
O1080.0199 (6)0.0256 (7)0.0271 (8)0.0031 (5)0.0075 (5)0.0054 (6)
Si1090.0177 (2)0.0211 (2)0.0209 (3)0.00225 (19)0.00274 (18)0.0004 (2)
C1100.0197 (8)0.0244 (10)0.0269 (11)0.0029 (7)0.0007 (7)0.0015 (9)
C1110.0326 (10)0.0343 (12)0.0329 (14)0.0103 (9)0.0039 (9)0.0029 (11)
C1120.0461 (13)0.0406 (14)0.0383 (16)0.0147 (11)0.0038 (11)0.0136 (12)
C1130.0386 (12)0.0270 (11)0.0535 (19)0.0131 (9)0.0010 (11)0.0052 (12)
C1140.0324 (10)0.0308 (11)0.0453 (16)0.0091 (9)0.0011 (10)0.0100 (11)
C1150.0299 (9)0.0302 (11)0.0304 (13)0.0042 (8)0.0025 (9)0.0029 (10)
C1160.0217 (8)0.0289 (10)0.0235 (10)0.0038 (7)0.0030 (7)0.0028 (8)
C1170.0456 (13)0.0344 (13)0.0459 (16)0.0044 (10)0.0142 (12)0.0026 (12)
C1180.0658 (18)0.0546 (18)0.061 (2)0.0127 (15)0.0352 (16)0.0082 (16)
C1190.0435 (14)0.0607 (18)0.0529 (19)0.0042 (13)0.0232 (12)0.0104 (15)
C1200.0292 (10)0.0434 (13)0.0457 (16)0.0021 (9)0.0034 (10)0.0142 (12)
C1210.0265 (9)0.0321 (11)0.0313 (12)0.0020 (8)0.0001 (8)0.0038 (10)
C1220.0220 (8)0.0268 (10)0.0310 (12)0.0033 (7)0.0061 (8)0.0004 (9)
C1230.0277 (10)0.0477 (14)0.0381 (15)0.0084 (10)0.0012 (10)0.0011 (12)
C1240.0392 (12)0.0282 (11)0.0554 (18)0.0043 (9)0.0125 (11)0.0037 (12)
C1250.0608 (16)0.0212 (11)0.072 (2)0.0071 (11)0.0183 (15)0.0060 (13)
C1480.0374 (11)0.0452 (14)0.0410 (15)0.0054 (10)0.0200 (10)0.0018 (12)
C1260.0194 (8)0.0313 (10)0.0335 (11)0.0057 (7)0.0054 (7)0.0069 (8)
O1270.0443 (8)0.0288 (7)0.0525 (11)0.0037 (6)0.0299 (8)0.0047 (7)
C1280.0444 (12)0.0323 (11)0.0546 (16)0.0044 (9)0.0272 (11)0.0014 (11)
C1290.079 (3)0.126 (4)0.107 (4)0.025 (3)0.016 (2)0.060 (3)
C1300.274 (7)0.0324 (16)0.135 (5)0.037 (3)0.141 (5)0.023 (2)
O1310.0464 (9)0.0373 (9)0.0866 (16)0.0035 (7)0.0446 (10)0.0030 (9)
C1320.0327 (10)0.0257 (10)0.0347 (13)0.0081 (8)0.0069 (9)0.0047 (10)
C1330.0458 (13)0.0367 (13)0.0440 (15)0.0163 (11)0.0148 (11)0.0034 (12)
C1340.0431 (13)0.0474 (15)0.0423 (16)0.0168 (11)0.0040 (11)0.0145 (13)
C1360.0283 (8)0.0235 (9)0.0251 (10)0.0022 (7)0.0064 (7)0.0036 (9)
C1370.0333 (10)0.0305 (11)0.0304 (12)0.0004 (8)0.0058 (9)0.0008 (9)
C1380.0475 (12)0.0409 (13)0.0282 (12)0.0055 (11)0.0117 (10)0.0013 (11)
C1390.0468 (13)0.0491 (15)0.0458 (16)0.0011 (12)0.0248 (12)0.0097 (13)
C1400.0370 (12)0.0566 (16)0.0461 (16)0.0141 (11)0.0122 (11)0.0031 (13)
C1410.0367 (11)0.0416 (13)0.0347 (14)0.0114 (10)0.0071 (9)0.0004 (11)
C1420.0245 (8)0.0242 (9)0.0276 (11)0.0015 (7)0.0041 (8)0.0020 (9)
C1430.0261 (9)0.0299 (12)0.0578 (17)0.0006 (8)0.0099 (10)0.0015 (12)
C1440.0286 (10)0.0372 (13)0.063 (2)0.0115 (10)0.0090 (11)0.0029 (13)
C1450.0452 (12)0.0266 (11)0.0403 (16)0.0090 (9)0.0034 (11)0.0025 (11)
C1460.0416 (11)0.0248 (10)0.0356 (14)0.0010 (9)0.0089 (10)0.0029 (10)
C1470.0273 (9)0.0278 (11)0.0347 (13)0.0004 (8)0.0061 (9)0.0016 (10)
Si10.0194 (2)0.0204 (2)0.0210 (3)0.00287 (19)0.00248 (19)0.0002 (2)
O20.0214 (6)0.0279 (7)0.0300 (9)0.0009 (5)0.0079 (6)0.0052 (6)
C30.0227 (8)0.0230 (9)0.0321 (12)0.0005 (7)0.0087 (8)0.0007 (9)
C40.0224 (8)0.0337 (11)0.0373 (13)0.0061 (8)0.0075 (8)0.0129 (9)
O50.0340 (8)0.0385 (9)0.0450 (11)0.0072 (7)0.0137 (7)0.0127 (8)
C60.0234 (8)0.0279 (10)0.0259 (10)0.0053 (7)0.0008 (7)0.0031 (8)
C70.0214 (8)0.0228 (9)0.0211 (10)0.0007 (7)0.0061 (7)0.0005 (8)
O80.0219 (6)0.0235 (7)0.0228 (7)0.0017 (5)0.0027 (5)0.0005 (6)
Si90.0202 (2)0.0204 (2)0.0215 (3)0.0002 (2)0.00308 (19)0.0002 (2)
C100.0236 (8)0.0208 (9)0.0256 (11)0.0006 (7)0.0025 (8)0.0027 (8)
C110.0267 (9)0.0274 (11)0.0508 (16)0.0009 (8)0.0088 (9)0.0024 (11)
C120.0306 (10)0.0328 (12)0.0609 (19)0.0066 (9)0.0088 (11)0.0019 (12)
C130.0464 (12)0.0245 (11)0.0393 (15)0.0109 (9)0.0050 (11)0.0033 (10)
C140.0456 (12)0.0233 (10)0.0401 (15)0.0032 (9)0.0107 (11)0.0056 (10)
C150.0300 (9)0.0261 (10)0.0354 (13)0.0024 (8)0.0085 (9)0.0026 (10)
C160.0241 (8)0.0229 (9)0.0269 (11)0.0011 (7)0.0057 (7)0.0012 (8)
C170.0330 (10)0.0345 (11)0.0290 (12)0.0060 (9)0.0065 (9)0.0034 (10)
C180.0314 (11)0.0421 (13)0.0510 (16)0.0080 (9)0.0157 (10)0.0065 (12)
C190.0472 (13)0.0433 (14)0.0424 (15)0.0038 (11)0.0261 (11)0.0056 (12)
C200.0535 (13)0.0423 (13)0.0295 (13)0.0007 (12)0.0183 (10)0.0041 (11)
C210.0319 (9)0.0330 (11)0.0290 (12)0.0005 (8)0.0085 (8)0.0011 (10)
C220.0269 (9)0.0235 (9)0.0324 (12)0.0052 (8)0.0028 (8)0.0024 (9)
C230.0401 (11)0.0398 (13)0.0420 (15)0.0148 (10)0.0139 (10)0.0014 (12)
C240.0445 (12)0.0227 (11)0.0623 (19)0.0024 (9)0.0081 (12)0.0037 (12)
C250.0350 (11)0.0483 (15)0.0332 (14)0.0107 (10)0.0019 (10)0.0076 (12)
C260.0224 (8)0.0296 (9)0.0275 (10)0.0059 (7)0.0012 (7)0.0008 (8)
O270.0384 (8)0.0267 (7)0.0776 (14)0.0054 (6)0.0291 (8)0.0011 (8)
C280.0402 (12)0.0272 (10)0.0661 (18)0.0077 (9)0.0249 (12)0.0032 (11)
C290.185 (5)0.091 (3)0.074 (3)0.101 (3)0.020 (3)0.020 (2)
C300.079 (3)0.063 (2)0.246 (8)0.021 (2)0.027 (3)0.054 (4)
O310.0328 (7)0.0343 (8)0.0643 (12)0.0025 (6)0.0219 (8)0.0004 (8)
C320.0229 (8)0.0265 (10)0.0290 (12)0.0013 (7)0.0068 (8)0.0008 (9)
C330.0279 (10)0.0429 (13)0.0421 (16)0.0065 (9)0.0006 (10)0.0009 (12)
C340.0413 (12)0.0411 (13)0.0411 (15)0.0054 (10)0.0198 (11)0.0008 (12)
C350.0352 (11)0.0235 (10)0.0599 (19)0.0005 (9)0.0105 (11)0.0038 (12)
C360.0218 (8)0.0286 (10)0.0240 (10)0.0035 (7)0.0014 (7)0.0008 (8)
C370.0262 (9)0.0303 (11)0.0351 (13)0.0026 (8)0.0012 (9)0.0003 (10)
C380.0304 (10)0.0424 (13)0.0409 (14)0.0078 (9)0.0054 (10)0.0061 (12)
C390.0389 (12)0.0598 (17)0.0489 (18)0.0090 (12)0.0194 (12)0.0073 (14)
C400.0575 (17)0.0462 (16)0.072 (2)0.0009 (13)0.0351 (16)0.0166 (16)
C410.0458 (13)0.0309 (12)0.0504 (17)0.0013 (10)0.0142 (12)0.0076 (12)
C420.0202 (8)0.0228 (9)0.0254 (11)0.0024 (7)0.0008 (7)0.0002 (9)
C430.0276 (9)0.0299 (11)0.0247 (11)0.0066 (8)0.0006 (8)0.0021 (9)
C440.0295 (10)0.0291 (11)0.0375 (14)0.0068 (8)0.0013 (9)0.0073 (10)
C450.0363 (11)0.0297 (12)0.0494 (18)0.0111 (9)0.0000 (11)0.0063 (12)
C460.0480 (13)0.0401 (14)0.0337 (14)0.0122 (11)0.0055 (11)0.0122 (12)
C470.0342 (10)0.0355 (12)0.0244 (12)0.0065 (9)0.0032 (9)0.0016 (10)
Geometric parameters (Å, º) top
Si101—O1021.6478 (16)Si1—O21.6354 (15)
Si101—C1321.887 (2)Si1—C321.891 (2)
Si101—C1361.876 (2)Si1—C361.879 (2)
Si101—C1421.874 (2)Si1—C421.876 (2)
O102—C1031.411 (2)O2—C31.408 (2)
C103—C1041.515 (3)C3—C41.528 (3)
C103—C1071.540 (3)C3—C71.537 (3)
C103—H10310.956C3—H310.988
C104—O1051.428 (3)C4—O51.439 (3)
C104—H10410.986C4—H410.968
C104—H10420.952C4—H420.966
O105—C1061.427 (2)O5—C61.418 (2)
C106—C1071.547 (3)C6—C71.538 (3)
C106—C1261.522 (3)C6—C261.522 (3)
C106—H10610.981C6—H610.983
C107—O1081.408 (2)C7—O81.404 (2)
C107—H10710.986C7—H711.005
O108—Si1091.6469 (15)O8—Si91.6512 (16)
Si109—C1101.879 (2)Si9—C101.880 (2)
Si109—C1161.880 (2)Si9—C161.877 (2)
Si109—C1221.893 (2)Si9—C221.887 (2)
C110—C1111.392 (3)C10—C111.392 (3)
C110—C1151.403 (3)C10—C151.402 (3)
C111—C1121.397 (3)C11—C121.390 (3)
C111—H11110.937C11—H1110.983
C112—C1131.381 (4)C12—C131.380 (3)
C112—H11210.956C12—H1210.957
C113—C1141.380 (4)C13—C141.377 (3)
C113—H11310.935C13—H1310.932
C114—C1151.386 (3)C14—C151.390 (3)
C114—H11410.953C14—H1410.941
C115—H11510.946C15—H1510.940
C116—C1171.390 (3)C16—C171.398 (3)
C116—C1211.402 (3)C16—C211.399 (3)
C117—C1181.379 (4)C17—C181.395 (3)
C117—H11710.939C17—H1710.935
C118—C1191.374 (5)C18—C191.378 (4)
C118—H11810.921C18—H1810.947
C119—C1201.373 (4)C19—C201.383 (4)
C119—H11910.931C19—H1910.932
C120—C1211.383 (3)C20—C211.388 (3)
C120—H12010.963C20—H2010.939
C121—H12110.971C21—H2110.937
C122—C1231.538 (3)C22—C231.532 (3)
C122—C1241.538 (3)C22—C241.542 (3)
C122—C1481.530 (3)C22—C251.530 (3)
C123—H12310.971C23—H2310.977
C123—H12320.953C23—H2320.976
C123—H12330.965C23—H2330.957
C124—H12410.960C24—H2410.978
C124—H12420.975C24—H2420.987
C124—H12430.986C24—H2430.988
C125—C1321.541 (3)C25—H2510.976
C125—H12510.964C25—H2520.986
C125—H12520.967C25—H2530.999
C125—H12530.969C26—O271.325 (2)
C148—H14811.011C26—O311.195 (2)
C148—H14820.967O27—C281.475 (3)
C148—H14830.974C28—C291.446 (5)
C126—O1271.323 (2)C28—C301.491 (5)
C126—O1311.186 (2)C28—H2810.956
O127—C1281.461 (3)C29—H2910.972
C128—C1291.473 (5)C29—H2921.016
C128—C1301.477 (4)C29—H2930.959
C128—H12811.006C30—H3010.977
C129—H12910.969C30—H3020.975
C129—H12920.987C30—H3030.968
C129—H12930.959C32—C331.535 (3)
C130—H13010.962C32—C341.524 (3)
C130—H13020.954C32—C351.545 (3)
C130—H13030.958C33—H3310.945
C132—C1331.528 (3)C33—H3320.966
C132—C1341.541 (4)C33—H3330.971
C133—H13310.975C34—H3410.977
C133—H13320.970C34—H3420.967
C133—H13330.973C34—H3430.968
C134—H13410.969C35—H3510.982
C134—H13420.988C35—H3520.957
C134—H13430.991C35—H3530.949
C136—C1371.395 (3)C36—C371.399 (3)
C136—C1411.400 (3)C36—C411.391 (3)
C137—C1381.389 (3)C37—C381.389 (3)
C137—H13710.945C37—H3710.930
C138—C1391.377 (4)C38—C391.364 (4)
C138—H13810.957C38—H3810.944
C139—C1401.380 (4)C39—C401.381 (4)
C139—H13910.958C39—H3910.952
C140—C1411.390 (3)C40—C411.392 (4)
C140—H14010.938C40—H4010.919
C141—H14110.957C41—H4110.927
C142—C1431.401 (3)C42—C431.402 (3)
C142—C1471.391 (3)C42—C471.396 (3)
C143—C1441.389 (3)C43—C441.390 (3)
C143—H14310.967C43—H4310.946
C144—C1451.374 (4)C44—C451.381 (4)
C144—H14410.949C44—H4410.958
C145—C1461.376 (3)C45—C461.381 (4)
C145—H14510.938C45—H4510.951
C146—C1471.397 (3)C46—C471.394 (3)
C146—H14610.952C46—H4610.933
C147—H14710.945C47—H4710.945
O102—Si101—C132104.35 (10)O2—Si1—C32101.78 (9)
O102—Si101—C136109.85 (8)O2—Si1—C36111.48 (8)
C132—Si101—C136109.81 (10)C32—Si1—C36115.76 (10)
O102—Si101—C142110.31 (9)O2—Si1—C42110.57 (9)
C132—Si101—C142115.03 (10)C32—Si1—C42109.35 (8)
C136—Si101—C142107.44 (9)C36—Si1—C42107.80 (9)
Si101—O102—C103125.33 (13)Si1—O2—C3140.64 (14)
O102—C103—C104111.43 (16)O2—C3—C4114.49 (19)
O102—C103—C107115.35 (14)O2—C3—C7107.31 (15)
C104—C103—C107101.20 (17)C4—C3—C799.66 (16)
O102—C103—H1031109.4O2—C3—H31111.0
C104—C103—H1031110.5C4—C3—H31111.7
C107—C103—H1031108.7C7—C3—H31112.2
C103—C104—O105103.81 (16)C3—C4—O5106.50 (16)
C103—C104—H1041109.2C3—C4—H41112.6
O105—C104—H1041110.8O5—C4—H41109.7
C103—C104—H1042113.8C3—C4—H42109.2
O105—C104—H1042111.0O5—C4—H42110.9
H1041—C104—H1042108.2H41—C4—H42107.9
C104—O105—C106108.85 (14)C4—O5—C6109.43 (15)
O105—C106—C107107.59 (16)O5—C6—C7104.03 (16)
O105—C106—C126110.81 (15)O5—C6—C26109.59 (15)
C107—C106—C126109.67 (17)C7—C6—C26112.73 (17)
O105—C106—H1061109.3O5—C6—H61112.7
C107—C106—H1061111.3C7—C6—H61111.7
C126—C106—H1061108.2C26—C6—H61106.2
C103—C107—C10699.95 (14)C6—C7—C399.74 (17)
C103—C107—O108108.95 (15)C6—C7—O8110.60 (16)
C106—C107—O108113.22 (17)C3—C7—O8116.78 (15)
C103—C107—H1071112.3C6—C7—H71106.9
C106—C107—H1071109.7C3—C7—H71110.0
O108—C107—H1071112.2O8—C7—H71111.8
C107—O108—Si109134.60 (13)C7—O8—Si9127.34 (13)
O108—Si109—C110111.73 (9)O8—Si9—C10112.14 (9)
O108—Si109—C116111.29 (8)O8—Si9—C16109.46 (8)
C110—Si109—C116106.60 (9)C10—Si9—C16107.49 (9)
O108—Si109—C122101.69 (9)O8—Si9—C22103.93 (9)
C110—Si109—C122110.29 (9)C10—Si9—C22114.44 (9)
C116—Si109—C122115.33 (10)C16—Si9—C22109.30 (10)
Si109—C110—C111122.06 (16)Si9—C10—C11122.98 (15)
Si109—C110—C115120.48 (17)Si9—C10—C15119.79 (14)
C111—C110—C115117.5 (2)C11—C10—C15117.22 (19)
C110—C111—C112121.1 (2)C10—C11—C12121.2 (2)
C110—C111—H1111119.7C10—C11—H111119.4
C112—C111—H1111119.2C12—C11—H111119.4
C111—C112—C113120.2 (3)C11—C12—C13120.4 (2)
C111—C112—H1121120.0C11—C12—H121118.7
C113—C112—H1121119.8C13—C12—H121120.9
C112—C113—C114119.8 (2)C12—C13—C14119.7 (2)
C112—C113—H1131120.1C12—C13—H131120.1
C114—C113—H1131120.2C14—C13—H131120.2
C113—C114—C115120.1 (2)C13—C14—C15120.0 (2)
C113—C114—H1141119.6C13—C14—H141122.0
C115—C114—H1141120.3C15—C14—H141118.0
C110—C115—C114121.4 (2)C10—C15—C14121.49 (19)
C110—C115—H1151119.9C10—C15—H151119.7
C114—C115—H1151118.7C14—C15—H151118.8
Si109—C116—C117123.05 (17)Si9—C16—C17122.49 (17)
Si109—C116—C121120.41 (16)Si9—C16—C21120.12 (14)
C117—C116—C121116.3 (2)C17—C16—C21117.18 (19)
C116—C117—C118121.5 (3)C16—C17—C18121.1 (2)
C116—C117—H1171119.7C16—C17—H171119.9
C118—C117—H1171118.8C18—C17—H171119.0
C117—C118—C119121.0 (3)C17—C18—C19119.9 (2)
C117—C118—H1181118.1C17—C18—H181120.5
C119—C118—H1181120.9C19—C18—H181119.5
C118—C119—C120119.2 (2)C18—C19—C20120.4 (2)
C118—C119—H1191120.4C18—C19—H191119.2
C120—C119—H1191120.3C20—C19—H191120.3
C119—C120—C121119.9 (2)C19—C20—C21119.3 (2)
C119—C120—H1201119.4C19—C20—H201120.9
C121—C120—H1201120.7C21—C20—H201119.8
C116—C121—C120122.1 (2)C16—C21—C20122.0 (2)
C116—C121—H1211118.8C16—C21—H211118.9
C120—C121—H1211119.1C20—C21—H211119.1
Si109—C122—C123106.72 (16)Si9—C22—C23112.14 (16)
Si109—C122—C124111.37 (13)Si9—C22—C24107.06 (14)
C123—C122—C124108.2 (2)C23—C22—C24107.7 (2)
Si109—C122—C148111.10 (16)Si9—C22—C25111.02 (16)
C123—C122—C148109.55 (19)C23—C22—C25110.05 (18)
C124—C122—C148109.8 (2)C24—C22—C25108.7 (2)
C122—C123—H1231109.8C22—C23—H231106.2
C122—C123—H1232110.4C22—C23—H232112.6
H1231—C123—H1232107.3H231—C23—H232107.3
C122—C123—H1233109.7C22—C23—H233112.2
H1231—C123—H1233110.4H231—C23—H233108.1
H1232—C123—H1233109.3H232—C23—H233110.1
C122—C124—H1241110.2C22—C24—H241108.5
C122—C124—H1242109.2C22—C24—H242111.1
H1241—C124—H1242108.3H241—C24—H242108.7
C122—C124—H1243109.1C22—C24—H243109.5
H1241—C124—H1243110.2H241—C24—H243109.6
H1242—C124—H1243109.8H242—C24—H243109.4
C132—C125—H1251107.9C22—C25—H251107.8
C132—C125—H1252109.8C22—C25—H252110.8
H1251—C125—H1252108.2H251—C25—H252108.7
C132—C125—H1253110.7C22—C25—H253111.5
H1251—C125—H1253110.2H251—C25—H253108.5
H1252—C125—H1253109.9H252—C25—H253109.4
C122—C148—H1481111.8C6—C26—O27110.39 (16)
C122—C148—H1482111.1C6—C26—O31124.78 (19)
H1481—C148—H1482109.1O27—C26—O31124.82 (19)
C122—C148—H1483109.8C26—O27—C28117.98 (16)
H1481—C148—H1483107.4O27—C28—C29107.4 (3)
H1482—C148—H1483107.5O27—C28—C30107.0 (2)
C106—C126—O127108.69 (16)C29—C28—C30114.0 (4)
C106—C126—O131125.83 (19)O27—C28—H281108.2
O127—C126—O131125.5 (2)C29—C28—H281115.8
C126—O127—C128118.79 (16)C30—C28—H281104.1
O127—C128—C129109.0 (2)C28—C29—H291109.0
O127—C128—C130105.8 (2)C28—C29—H292100.3
C129—C128—C130116.6 (4)H291—C29—H292111.7
O127—C128—H1281107.0C28—C29—H293112.7
C129—C128—H1281108.1H291—C29—H293113.3
C130—C128—H1281110.0H292—C29—H293109.2
C128—C129—H1291110.9C28—C30—H301109.3
C128—C129—H1292104.4C28—C30—H302112.3
H1291—C129—H1292107.8H301—C30—H302112.8
C128—C129—H1293111.6C28—C30—H303106.0
H1291—C129—H1293111.4H301—C30—H303107.7
H1292—C129—H1293110.4H302—C30—H303108.4
C128—C130—H1301110.2Si1—C32—C33107.06 (16)
C128—C130—H1302109.1Si1—C32—C34111.17 (16)
H1301—C130—H1302112.1C33—C32—C34109.61 (19)
C128—C130—H1303105.7Si1—C32—C35112.03 (13)
H1301—C130—H1303110.5C33—C32—C35107.4 (2)
H1302—C130—H1303109.0C34—C32—C35109.4 (2)
C125—C132—Si101107.16 (15)C32—C33—H331111.3
C125—C132—C133108.2 (2)C32—C33—H332111.8
Si101—C132—C133112.32 (16)H331—C33—H332107.7
C125—C132—C134108.9 (2)C32—C33—H333112.5
Si101—C132—C134110.53 (17)H331—C33—H333105.3
C133—C132—C134109.60 (19)H332—C33—H333107.9
C132—C133—H1331111.0C32—C34—H341108.1
C132—C133—H1332110.1C32—C34—H342109.9
H1331—C133—H1332107.1H341—C34—H342108.3
C132—C133—H1333110.7C32—C34—H343110.1
H1331—C133—H1333109.0H341—C34—H343110.4
H1332—C133—H1333108.9H342—C34—H343110.1
C132—C134—H1341108.7C32—C35—H351109.7
C132—C134—H1342112.8C32—C35—H352111.7
H1341—C134—H1342107.4H351—C35—H352108.7
C132—C134—H1343109.6C32—C35—H353108.9
H1341—C134—H1343108.0H351—C35—H353109.3
H1342—C134—H1343110.2H352—C35—H353108.6
Si101—C136—C137120.42 (15)Si1—C36—C37120.23 (16)
Si101—C136—C141122.15 (17)Si1—C36—C41122.72 (17)
C137—C136—C141117.20 (19)C37—C36—C41116.8 (2)
C136—C137—C138121.8 (2)C36—C37—C38121.6 (2)
C136—C137—H1371117.9C36—C37—H371119.1
C138—C137—H1371120.3C38—C37—H371119.1
C137—C138—C139119.8 (2)C37—C38—C39120.4 (2)
C137—C138—H1381119.6C37—C38—H381118.8
C139—C138—H1381120.6C39—C38—H381120.7
C138—C139—C140119.7 (2)C38—C39—C40119.4 (2)
C138—C139—H1391121.2C38—C39—H391119.7
C140—C139—H1391119.0C40—C39—H391120.8
C139—C140—C141120.4 (2)C39—C40—C41120.4 (3)
C139—C140—H1401119.9C39—C40—H401121.3
C141—C140—H1401119.6C41—C40—H401118.3
C136—C141—C140121.0 (2)C40—C41—C36121.3 (2)
C136—C141—H1411119.8C40—C41—H411119.2
C140—C141—H1411119.2C36—C41—H411119.4
Si101—C142—C143123.59 (17)Si1—C42—C43121.59 (17)
Si101—C142—C147119.75 (14)Si1—C42—C47121.01 (16)
C143—C142—C147116.6 (2)C43—C42—C47117.36 (19)
C142—C143—C144121.5 (2)C42—C43—C44121.5 (2)
C142—C143—H1431120.1C42—C43—H431120.2
C144—C143—H1431118.4C44—C43—H431118.2
C143—C144—C145120.3 (2)C43—C44—C45119.9 (2)
C143—C144—H1441120.2C43—C44—H441120.6
C145—C144—H1441119.3C45—C44—H441119.5
C144—C145—C146119.8 (2)C44—C45—C46119.8 (2)
C144—C145—H1451121.3C44—C45—H451119.9
C146—C145—H1451118.9C46—C45—H451120.3
C145—C146—C147119.7 (2)C45—C46—C47120.3 (2)
C145—C146—H1461118.3C45—C46—H461119.7
C147—C146—H1461122.0C47—C46—H461120.0
C146—C147—C142121.95 (19)C42—C47—C46121.1 (2)
C146—C147—H1471118.1C42—C47—H471118.8
C142—C147—H1471119.8C46—C47—H471120.1

Experimental details

Crystal data
Chemical formulaC40H50O5Si2
Mr667.01
Crystal system, space groupMonoclinic, P21
Temperature (K)190
a, b, c (Å)17.2952 (2), 10.7468 (2), 20.4914 (4)
β (°) 100.7864 (5)
V3)3741.40 (11)
Z4
Radiation typeMo Kα
µ (mm1)0.14
Crystal size (mm)0.40 × 0.20 × 0.20
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(DENZO/SCALEPACK; Otwinowski & Minor, 1997)
Tmin, Tmax0.70, 0.97
No. of measured, independent and
observed [I > 3σ(I)] reflections
27685, 17372, 17372
Rint0.027
(sin θ/λ)max1)0.704
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.096, 0.97
No. of reflections17372
No. of parameters848
No. of restraints370
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.70, 0.47
Absolute structureFlack (1983), 17372 Friedel pairs
Absolute structure parameter0.05 (7)

Computer programs: COLLECT (Nonius, 2001), DENZO/SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), CRYSTALS (Betteridge et al., 2003), CAMERON (Watkin et al., 1996), CRYSTALS.

 

Acknowledgements

Financial support (to AAE) from the EPSRC and (to GJS) from DST, New Delhi, for a BOYSCAST Fellowship, is gratefully acknowledged.

References

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