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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1472–o1473.
Published online 2008 July 12. doi:  10.1107/S160053680802117X
PMCID: PMC2962104

O-(tert-Butyl­dimethyl­silyl)tris­(O-4-methyl­phenyl­sulfon­yl)penta­erythritol

Abstract

In the title compound [systematic name: (tert-butyl­dimethyl­silyl)methane­triyl tris­(4-methyl­benzene­sulfonate)], C32H44O10S3Si, the central C atom and the SiIV center are in a tetra­hedral configuration. The inter­planar angles between pairs of the three benzene rings of the 4-methyl­phenyl­sulfonyl units are 41.15 (10), 18.11 (10) and 44.09 (10)°. C—H(...)π inter­actions are observed in the crystal structure. Mol­ecules are linked into screw chains along the b axis by weak C—H(...)O inter­actions. Weak intramolecular C—H(...)O hydrogen bonds are also present.

Related literature

For bond-length data, see: Allen et al. (1987 [triangle]). For background and applications of radioimmuno imaging, radioimmuno therapy and hypoxia markers, see, for example: Abdel-Jalil et al. (2006 [triangle]); Monge et al. (2001 [triangle]); Nagasawa et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1472-scheme1.jpg

Experimental

Crystal data

  • C32H44O10S3Si
  • M r = 712.94
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1472-efi1.jpg
  • a = 19.0551 (3) Å
  • b = 16.4726 (3) Å
  • c = 11.6751 (2) Å
  • β = 100.425 (1)°
  • V = 3604.17 (11) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.29 mm−1
  • T = 100.0 (1) K
  • 0.51 × 0.22 × 0.21 mm

Data collection

  • Bruker SMART APEX2 CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.865, T max = 0.941
  • 45850 measured reflections
  • 10507 independent reflections
  • 7229 reflections with I > 2σ(I)
  • R int = 0.061

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.128
  • S = 1.08
  • 10507 reflections
  • 423 parameters
  • H-atom parameters constrained
  • Δρmax = 0.57 e Å−3
  • Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 [triangle]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680802117X/at2586sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802117X/at2586Isup2.hkl

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

Acknowledgments

The authors gratefully acknowledge the financial assistance of Beijing Normal University. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

supplementary crystallographic information

Comment

Radio-immuno-imaging (RII) and radio-immuno-therapy (RIT) rely on the ability of a bifunctional molecule with a radioactive unit combined with a receptor-specific substrate such as 2-nitroimidazole unit which can act as a hypoxia marker (Abdel-Jalil et al., 2006; Monge et al., 2001; Nagasawa et al., 2006). This approach allows radiopharmaceuticals to be delivered specifically to malignant tissue while minimizing the risk of unspecific irradiation of sane tissue. As part of our research on the synthesis of new potential hypoxia markers, we report herein the synthesis and crystal structure of the O-(tert-Butyl- dimethylsilyl)-tris[O-(4-methylphenylsulfonyl)]-pentaerythritol (I)

In the title molecule (Fig. 1), the configurations of the SiV and central C atoms are tetrahedral. The interplanar angles between the three phenyl rings of the three 4-methylphenylsulfonyl group are 41.15 (10)°, 18.11 (10)° and 44.09 (10)° for A/B, A/C and B/C, respectively, where ring A is C3–C8, ring B is C11–C16 and ring C is C19–C24. Atoms O1, O7, C1, C2 and C18 lie on the same plane, with the most deviation of 0.011 (2) Å for atom C1. The dihedral angles between the O1/O7/C1/C2/C18 plane and the mean plane of phenyl rings A, B and C are 71.26 (12)°, 55.52 (12)° and 86.79 (13)°, respectively. The conformation of the three 4-methylphenylsulfonyl groups with respect to the pentaerythritol unit, (C1/C2/C10/C18/C26/O1/O4/O7/O10), can be indicated by the torsion angles S1–O1–C2–C1 = -172.71 (11)°, S2–O4–C10–C1 = -155.23 (12)° and S3–O7–C18–C1 = -168.07 (11)°.

The crystal packing of (I) in Fig. 2 shows that the molecules are linked into screw chains along the b axis by weak C17—H17C···O3 (symmetry code: 1 - x, 1/2 + y, 3/2 - z) and C25—H25B···O8 (symmetry code:-x, 1/2 + y, 3/2 - z) interactions (Table 1). The crystal is stabilized by weak C—H···O intra- and intermolecular interactions (Table 1) and further stabilized by C—H···π interactions (Table 1); Cg1 is the centroid of C19–C24 ring.

Experimental

The title compound was synthesized by disolving the 2,2-hydroxymethyl-2-(tert-butyldimethylsilyloxymethyl)-propan-1,3-diol (1.05 g, 4.0 mmol) in dry pyridine (40 ml) and tosyl chloride (3.05 g, 16.0 mmol) was then added. The reaction mixture was stirred for 24 h at room temperature, after which it was poured into ice-water (250 ml) and extracted with CH2Cl2 (250 ml). The organic layer was washed with water (250 ml), dried with MgSO4 and concentrated. The solid residue was purified by recrystalization with warm ethanol to afford the title compound as a white solid 2.27 g (yield: 80%). Colourless single crystals of the title compound suitable for x-ray structure determination were recrystallized from ethanol by slow evaporation of the solvent at room temperature [m.p. 371 K].

Refinement

All H atoms were placed in calculated positions, with C—H = 0.93 Å, Uiso = 1.2Ueq(C) for aromatic, C—H = 0.97 Å, Uiso = 1.2Ueq(C) for CH2 and C—H = 0.96 Å, Uiso = 1.5Ueq(C) for CH3 atoms. A rotating group model was used for the methyl groups.

Figures

Fig. 1.
The asymmetric unit of (I), showing 50% probability displacement ellipsoids and the atomic numbering.
Fig. 2.
The crystal packing of (I), viewed down the c axis, showing screw chains running along the b axis. Hydrogen bonds are shown as dashed lines.

Crystal data

C32H44O10S3SiF000 = 1512
Mr = 712.94Dx = 1.314 Mg m3
Monoclinic, P21/cMelting point: 371 K
Hall symbol: -P 2ybcMo Kα radiation λ = 0.71073 Å
a = 19.0551 (3) ÅCell parameters from 10507 reflections
b = 16.4726 (3) Åθ = 1.1–30.0º
c = 11.6751 (2) ŵ = 0.29 mm1
β = 100.4250 (10)ºT = 100.0 (1) K
V = 3604.17 (11) Å3Block, colourless
Z = 40.51 × 0.22 × 0.21 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer10507 independent reflections
Radiation source: fine-focus sealed tube7229 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.061
Detector resolution: 8.33 pixels mm-1θmax = 30.0º
T = 100.0(1) Kθmin = 1.1º
ω scansh = −26→26
Absorption correction: multi-scan(SADABS; Bruker, 2005)k = −20→23
Tmin = 0.865, Tmax = 0.941l = −16→16
45850 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.128  w = 1/[σ2(Fo2) + (0.0542P)2 + 0.5781P] where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
10507 reflectionsΔρmax = 0.57 e Å3
423 parametersΔρmin = −0.37 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

Experimental. The low-temparture data was collected with the Oxford Cryosystem Cobra low-temperature attachment.
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)

xyzUiso*/Ueq
S10.43907 (2)0.59668 (3)0.80628 (4)0.02743 (12)
S20.29545 (3)0.84432 (3)0.88867 (4)0.02536 (11)
S30.04614 (2)0.70517 (3)0.62782 (4)0.02418 (11)
Si10.15861 (3)0.41864 (3)0.71109 (5)0.02434 (12)
O10.35890 (7)0.60108 (8)0.82612 (11)0.0251 (3)
O20.45358 (7)0.66628 (9)0.74133 (12)0.0322 (3)
O30.47849 (7)0.58293 (10)0.92048 (12)0.0360 (4)
O40.25506 (7)0.77595 (7)0.80747 (11)0.0255 (3)
O50.24793 (8)0.87813 (9)0.95759 (12)0.0346 (3)
O60.36172 (8)0.81218 (9)0.94769 (13)0.0364 (4)
O70.11116 (6)0.66522 (8)0.71203 (11)0.0231 (3)
O8−0.01360 (7)0.68777 (9)0.68183 (13)0.0350 (3)
O90.04655 (7)0.67929 (8)0.51126 (12)0.0306 (3)
O100.22073 (7)0.48853 (7)0.75227 (11)0.0237 (3)
C10.23508 (9)0.63386 (10)0.77255 (15)0.0201 (3)
C20.30457 (9)0.62322 (11)0.72675 (15)0.0218 (4)
H2A0.29950.58090.66810.026*
H2B0.31740.67340.69220.026*
C30.44109 (10)0.50976 (12)0.72072 (17)0.0271 (4)
C40.42767 (10)0.51678 (13)0.60011 (17)0.0292 (4)
H4A0.41790.56720.56500.035*
C50.42907 (11)0.44783 (13)0.53309 (19)0.0323 (5)
H5A0.41940.45230.45240.039*
C60.44467 (10)0.37191 (13)0.5836 (2)0.0342 (5)
C70.45830 (11)0.36682 (14)0.7042 (2)0.0385 (5)
H7A0.46910.31660.73930.046*
C80.45632 (11)0.43424 (13)0.77347 (19)0.0345 (5)
H8A0.46500.42950.85420.041*
C90.44730 (13)0.29802 (14)0.5085 (2)0.0472 (6)
H9A0.46270.25200.55710.071*
H9B0.48020.30730.45660.071*
H9C0.40070.28770.46400.071*
C100.24235 (10)0.69985 (10)0.86520 (16)0.0226 (4)
H10A0.19910.70360.89770.027*
H10B0.28190.68790.92770.027*
C110.30845 (10)0.91365 (11)0.78179 (16)0.0241 (4)
C120.35159 (11)0.89374 (13)0.70172 (17)0.0297 (4)
H12A0.37320.84300.70380.036*
C130.36207 (11)0.95052 (13)0.61867 (18)0.0312 (4)
H13A0.39040.93730.56440.037*
C140.33077 (10)1.02698 (12)0.61554 (17)0.0296 (4)
C150.28933 (12)1.04578 (13)0.6978 (2)0.0366 (5)
H15A0.26901.09710.69750.044*
C160.27748 (12)0.98965 (12)0.78057 (19)0.0335 (5)
H16A0.24901.00290.83470.040*
C170.34224 (12)1.08795 (14)0.5246 (2)0.0377 (5)
H17A0.31331.13500.53010.057*
H17B0.32911.06430.44870.057*
H17C0.39161.10350.53720.057*
C180.17788 (9)0.65611 (11)0.66832 (15)0.0205 (4)
H18A0.19010.70650.63360.025*
H18B0.17340.61370.60980.025*
C190.06525 (10)0.80900 (11)0.63863 (17)0.0249 (4)
C200.06732 (12)0.85348 (12)0.53912 (18)0.0352 (5)
H20A0.06170.82820.46680.042*
C210.07791 (14)0.93662 (13)0.5490 (2)0.0439 (6)
H21A0.07900.96720.48230.053*
C220.08685 (12)0.97525 (13)0.6565 (2)0.0373 (5)
C230.08474 (12)0.92879 (13)0.75492 (19)0.0352 (5)
H23A0.09100.95370.82750.042*
C240.07355 (11)0.84620 (12)0.74651 (18)0.0308 (4)
H24A0.07160.81570.81290.037*
C250.09677 (14)1.06606 (13)0.6661 (2)0.0502 (7)
H25A0.12961.07880.73630.075*
H25B0.05171.09150.66800.075*
H25C0.11541.08570.60020.075*
C260.21518 (10)0.55424 (10)0.82791 (15)0.0216 (4)
H26A0.24690.54560.90170.026*
H26B0.16680.55780.84260.026*
C270.20588 (11)0.33913 (12)0.63907 (19)0.0321 (5)
C280.12636 (13)0.37836 (14)0.8409 (2)0.0406 (5)
H28D0.09470.41710.86630.061*
H28E0.16630.36890.90240.061*
H28F0.10130.32830.82110.061*
C290.08257 (12)0.46319 (13)0.6089 (2)0.0418 (6)
H29D0.06140.50580.64740.063*
H29E0.04760.42190.58390.063*
H29F0.09930.48500.54250.063*
C300.23327 (17)0.37496 (18)0.5347 (2)0.0607 (8)
H28A0.25740.33360.49880.091*
H28B0.26580.41850.56050.091*
H28C0.19380.39540.47930.091*
C310.26994 (13)0.30612 (15)0.7265 (3)0.0537 (7)
H29A0.29440.26590.68900.081*
H29B0.25330.28210.79150.081*
H29C0.30200.34980.75340.081*
C320.15490 (13)0.26888 (14)0.5985 (2)0.0460 (6)
H30A0.18030.22640.56710.069*
H30B0.11660.28780.53950.069*
H30C0.13580.24830.66340.069*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0203 (2)0.0361 (3)0.0249 (2)−0.00249 (19)0.00168 (19)0.0038 (2)
S20.0322 (3)0.0219 (2)0.0211 (2)−0.00499 (18)0.00224 (19)−0.00392 (18)
S30.0212 (2)0.0247 (2)0.0258 (2)0.00012 (17)0.00182 (18)0.00147 (18)
Si10.0269 (3)0.0195 (2)0.0257 (3)−0.0037 (2)0.0020 (2)0.0008 (2)
O10.0210 (6)0.0326 (7)0.0207 (6)0.0006 (5)0.0015 (5)0.0045 (6)
O20.0303 (7)0.0351 (8)0.0309 (7)−0.0093 (6)0.0048 (6)0.0038 (6)
O30.0250 (7)0.0525 (10)0.0276 (7)0.0001 (6)−0.0030 (6)0.0058 (7)
O40.0355 (7)0.0178 (6)0.0209 (6)−0.0054 (5)−0.0007 (6)−0.0012 (5)
O50.0491 (9)0.0306 (8)0.0275 (7)−0.0038 (7)0.0163 (7)−0.0046 (6)
O60.0366 (8)0.0333 (8)0.0342 (8)−0.0071 (6)−0.0071 (7)0.0011 (7)
O70.0206 (6)0.0270 (7)0.0217 (6)0.0029 (5)0.0040 (5)0.0027 (5)
O80.0236 (7)0.0365 (8)0.0461 (9)−0.0015 (6)0.0097 (6)0.0051 (7)
O90.0334 (8)0.0298 (7)0.0254 (7)0.0004 (6)−0.0032 (6)−0.0028 (6)
O100.0253 (7)0.0189 (6)0.0267 (7)−0.0022 (5)0.0041 (5)−0.0032 (5)
C10.0223 (9)0.0195 (8)0.0180 (8)−0.0011 (7)0.0019 (7)−0.0001 (7)
C20.0208 (9)0.0237 (9)0.0197 (9)−0.0002 (7)0.0003 (7)0.0028 (7)
C30.0203 (9)0.0332 (10)0.0280 (10)0.0024 (8)0.0052 (8)0.0054 (8)
C40.0251 (10)0.0319 (10)0.0311 (10)0.0017 (8)0.0064 (8)0.0065 (9)
C50.0285 (10)0.0345 (11)0.0348 (11)0.0018 (8)0.0079 (9)0.0015 (9)
C60.0219 (10)0.0341 (11)0.0476 (13)0.0011 (8)0.0087 (9)0.0018 (10)
C70.0315 (11)0.0320 (11)0.0523 (14)0.0056 (9)0.0080 (10)0.0128 (10)
C80.0285 (11)0.0398 (12)0.0342 (11)0.0030 (9)0.0034 (9)0.0123 (9)
C90.0420 (13)0.0352 (12)0.0650 (17)0.0000 (10)0.0111 (12)−0.0033 (12)
C100.0274 (9)0.0193 (8)0.0203 (9)−0.0030 (7)0.0023 (7)0.0020 (7)
C110.0259 (9)0.0223 (9)0.0237 (9)−0.0044 (7)0.0033 (8)−0.0037 (7)
C120.0295 (10)0.0291 (10)0.0305 (10)0.0031 (8)0.0057 (8)−0.0007 (8)
C130.0293 (10)0.0376 (11)0.0281 (10)0.0026 (9)0.0089 (8)0.0018 (9)
C140.0257 (10)0.0321 (10)0.0295 (10)−0.0073 (8)0.0007 (8)0.0009 (9)
C150.0427 (12)0.0224 (10)0.0469 (13)0.0005 (9)0.0139 (10)0.0020 (9)
C160.0431 (12)0.0240 (10)0.0377 (12)−0.0004 (9)0.0193 (10)−0.0032 (9)
C170.0345 (12)0.0372 (12)0.0402 (12)−0.0077 (9)0.0039 (10)0.0097 (10)
C180.0211 (9)0.0200 (8)0.0205 (8)0.0004 (7)0.0040 (7)0.0002 (7)
C190.0245 (9)0.0240 (9)0.0268 (10)0.0042 (7)0.0066 (8)0.0004 (8)
C200.0541 (14)0.0270 (10)0.0282 (11)0.0088 (9)0.0177 (10)0.0017 (8)
C210.0711 (17)0.0256 (11)0.0428 (13)0.0050 (11)0.0312 (13)0.0046 (10)
C220.0398 (12)0.0273 (11)0.0489 (13)0.0036 (9)0.0187 (11)−0.0034 (10)
C230.0397 (12)0.0329 (11)0.0330 (11)0.0020 (9)0.0066 (10)−0.0075 (9)
C240.0367 (11)0.0299 (10)0.0256 (10)0.0012 (8)0.0052 (9)−0.0002 (8)
C250.0618 (16)0.0251 (11)0.0679 (18)0.0025 (11)0.0229 (14)−0.0057 (11)
C260.0264 (9)0.0196 (8)0.0185 (8)−0.0022 (7)0.0029 (7)0.0001 (7)
C270.0335 (11)0.0269 (10)0.0354 (11)−0.0041 (8)0.0046 (9)−0.0093 (9)
C280.0474 (14)0.0353 (12)0.0417 (13)−0.0123 (10)0.0146 (11)0.0011 (10)
C290.0366 (12)0.0289 (11)0.0534 (14)−0.0051 (9)−0.0094 (11)0.0037 (10)
C300.081 (2)0.0573 (17)0.0529 (16)−0.0102 (15)0.0374 (15)−0.0153 (14)
C310.0426 (14)0.0424 (14)0.0708 (18)0.0112 (11)−0.0043 (13)−0.0224 (13)
C320.0474 (14)0.0300 (12)0.0576 (15)−0.0050 (10)0.0016 (12)−0.0173 (11)

Geometric parameters (Å, °)

S1—O31.4250 (14)C13—C141.391 (3)
S1—O21.4289 (14)C13—H13A0.9300
S1—O11.5875 (13)C14—C151.385 (3)
S1—C31.750 (2)C14—C171.505 (3)
S2—O61.4265 (15)C15—C161.385 (3)
S2—O51.4288 (14)C15—H15A0.9300
S2—O41.5797 (13)C16—H16A0.9300
S2—C111.7420 (19)C17—H17A0.9600
S3—O81.4266 (14)C17—H17B0.9600
S3—O91.4274 (14)C17—H17C0.9600
S3—O71.5791 (13)C18—H18A0.9700
S3—C191.7484 (19)C18—H18B0.9700
Si1—O101.6588 (13)C19—C201.380 (3)
Si1—C291.854 (2)C19—C241.384 (3)
Si1—C281.858 (2)C20—C211.386 (3)
Si1—C271.873 (2)C20—H20A0.9300
O1—C21.455 (2)C21—C221.390 (3)
O4—C101.464 (2)C21—H21A0.9300
O7—C181.461 (2)C22—C231.387 (3)
O10—C261.413 (2)C22—C251.509 (3)
C1—C101.522 (2)C23—C241.378 (3)
C1—C181.524 (2)C23—H23A0.9300
C1—C21.525 (2)C24—H24A0.9300
C1—C261.540 (2)C25—H25A0.9600
C2—H2A0.9700C25—H25B0.9600
C2—H2B0.9700C25—H25C0.9600
C3—C41.390 (3)C26—H26A0.9700
C3—C81.395 (3)C26—H26B0.9700
C4—C51.382 (3)C27—C301.528 (3)
C4—H4A0.9300C27—C321.530 (3)
C5—C61.392 (3)C27—C311.542 (3)
C5—H5A0.9300C28—H28D0.9600
C6—C71.388 (3)C28—H28E0.9600
C6—C91.506 (3)C28—H28F0.9600
C7—C81.378 (3)C29—H29D0.9600
C7—H7A0.9300C29—H29E0.9600
C8—H8A0.9300C29—H29F0.9600
C9—H9A0.9600C30—H28A0.9600
C9—H9B0.9600C30—H28B0.9600
C9—H9C0.9600C30—H28C0.9600
C10—H10A0.9700C31—H29A0.9600
C10—H10B0.9700C31—H29B0.9600
C11—C161.383 (3)C31—H29C0.9600
C11—C121.391 (3)C32—H30A0.9600
C12—C131.387 (3)C32—H30B0.9600
C12—H12A0.9300C32—H30C0.9600
O3—S1—O2120.27 (9)C14—C15—H15A119.3
O3—S1—O1103.23 (8)C16—C15—H15A119.3
O2—S1—O1108.94 (8)C11—C16—C15119.24 (19)
O3—S1—C3109.98 (9)C11—C16—H16A120.4
O2—S1—C3109.09 (9)C15—C16—H16A120.4
O1—S1—C3104.00 (8)C14—C17—H17A109.5
O6—S2—O5117.94 (9)C14—C17—H17B109.5
O6—S2—O4108.54 (8)H17A—C17—H17B109.5
O5—S2—O4109.04 (8)C14—C17—H17C109.5
O6—S2—C11111.17 (9)H17A—C17—H17C109.5
O5—S2—C11109.55 (9)H17B—C17—H17C109.5
O4—S2—C1198.89 (8)O7—C18—C1106.71 (14)
O8—S3—O9120.25 (9)O7—C18—H18A110.4
O8—S3—O7103.88 (8)C1—C18—H18A110.4
O9—S3—O7109.27 (8)O7—C18—H18B110.4
O8—S3—C19109.69 (9)C1—C18—H18B110.4
O9—S3—C19108.91 (9)H18A—C18—H18B108.6
O7—S3—C19103.48 (8)C20—C19—C24121.00 (19)
O10—Si1—C29110.21 (9)C20—C19—S3119.73 (15)
O10—Si1—C28109.60 (9)C24—C19—S3119.14 (15)
C29—Si1—C28109.34 (12)C19—C20—C21118.7 (2)
O10—Si1—C27103.86 (8)C19—C20—H20A120.6
C29—Si1—C27111.79 (11)C21—C20—H20A120.6
C28—Si1—C27111.93 (10)C20—C21—C22121.3 (2)
C2—O1—S1117.37 (11)C20—C21—H21A119.4
C10—O4—S2115.94 (11)C22—C21—H21A119.4
C18—O7—S3117.36 (11)C23—C22—C21118.6 (2)
C26—O10—Si1125.64 (11)C23—C22—C25120.5 (2)
C10—C1—C18110.83 (14)C21—C22—C25120.9 (2)
C10—C1—C2110.97 (15)C24—C23—C22120.9 (2)
C18—C1—C2106.77 (14)C24—C23—H23A119.6
C10—C1—C26107.92 (14)C22—C23—H23A119.6
C18—C1—C26110.20 (14)C23—C24—C19119.5 (2)
C2—C1—C26110.16 (14)C23—C24—H24A120.2
O1—C2—C1106.68 (13)C19—C24—H24A120.2
O1—C2—H2A110.4C22—C25—H25A109.5
C1—C2—H2A110.4C22—C25—H25B109.5
O1—C2—H2B110.4H25A—C25—H25B109.5
C1—C2—H2B110.4C22—C25—H25C109.5
H2A—C2—H2B108.6H25A—C25—H25C109.5
C4—C3—C8120.46 (19)H25B—C25—H25C109.5
C4—C3—S1119.42 (15)O10—C26—C1109.77 (14)
C8—C3—S1120.12 (16)O10—C26—H26A109.7
C5—C4—C3119.10 (19)C1—C26—H26A109.7
C5—C4—H4A120.5O10—C26—H26B109.7
C3—C4—H4A120.5C1—C26—H26B109.7
C4—C5—C6121.6 (2)H26A—C26—H26B108.2
C4—C5—H5A119.2C30—C27—C32109.5 (2)
C6—C5—H5A119.2C30—C27—C31108.7 (2)
C7—C6—C5118.1 (2)C32—C27—C31108.70 (19)
C7—C6—C9121.5 (2)C30—C27—Si1110.44 (16)
C5—C6—C9120.5 (2)C32—C27—Si1109.76 (15)
C8—C7—C6121.8 (2)C31—C27—Si1109.69 (15)
C8—C7—H7A119.1Si1—C28—H28D109.5
C6—C7—H7A119.1Si1—C28—H28E109.5
C7—C8—C3119.0 (2)H28D—C28—H28E109.5
C7—C8—H8A120.5Si1—C28—H28F109.5
C3—C8—H8A120.5H28D—C28—H28F109.5
C6—C9—H9A109.5H28E—C28—H28F109.5
C6—C9—H9B109.5Si1—C29—H29D109.5
H9A—C9—H9B109.5Si1—C29—H29E109.5
C6—C9—H9C109.5H29D—C29—H29E109.5
H9A—C9—H9C109.5Si1—C29—H29F109.5
H9B—C9—H9C109.5H29D—C29—H29F109.5
O4—C10—C1106.60 (14)H29E—C29—H29F109.5
O4—C10—H10A110.4C27—C30—H28A109.5
C1—C10—H10A110.4C27—C30—H28B109.5
O4—C10—H10B110.4H28A—C30—H28B109.5
C1—C10—H10B110.4C27—C30—H28C109.5
H10A—C10—H10B108.6H28A—C30—H28C109.5
C16—C11—C12120.62 (18)H28B—C30—H28C109.5
C16—C11—S2119.02 (15)C27—C31—H29A109.5
C12—C11—S2120.32 (15)C27—C31—H29B109.5
C13—C12—C11119.21 (19)H29A—C31—H29B109.5
C13—C12—H12A120.4C27—C31—H29C109.5
C11—C12—H12A120.4H29A—C31—H29C109.5
C12—C13—C14120.89 (19)H29B—C31—H29C109.5
C12—C13—H13A119.6C27—C32—H30A109.5
C14—C13—H13A119.6C27—C32—H30B109.5
C15—C14—C13118.68 (19)H30A—C32—H30B109.5
C15—C14—C17120.91 (19)C27—C32—H30C109.5
C13—C14—C17120.41 (19)H30A—C32—H30C109.5
C14—C15—C16121.34 (19)H30B—C32—H30C109.5
O3—S1—O1—C2173.78 (13)S2—C11—C12—C13−178.92 (15)
O2—S1—O1—C244.86 (14)C11—C12—C13—C140.8 (3)
C3—S1—O1—C2−71.37 (14)C12—C13—C14—C150.6 (3)
O6—S2—O4—C1056.27 (14)C12—C13—C14—C17−179.71 (19)
O5—S2—O4—C10−73.41 (14)C13—C14—C15—C16−1.4 (3)
C11—S2—O4—C10172.24 (13)C17—C14—C15—C16178.9 (2)
O8—S3—O7—C18166.39 (12)C12—C11—C16—C150.6 (3)
O9—S3—O7—C1836.88 (14)S2—C11—C16—C15178.17 (16)
C19—S3—O7—C18−79.02 (13)C14—C15—C16—C110.8 (3)
C29—Si1—O10—C2671.63 (16)S3—O7—C18—C1168.07 (11)
C28—Si1—O10—C26−48.75 (16)C10—C1—C18—O7−59.77 (18)
C27—Si1—O10—C26−168.49 (14)C2—C1—C18—O7179.26 (13)
S1—O1—C2—C1−172.71 (11)C26—C1—C18—O759.62 (17)
C10—C1—C2—O159.75 (18)O8—S3—C19—C20−124.09 (17)
C18—C1—C2—O1−179.37 (13)O9—S3—C19—C209.39 (19)
C26—C1—C2—O1−59.71 (18)O7—S3—C19—C20125.55 (17)
O3—S1—C3—C4−158.68 (15)O8—S3—C19—C2451.81 (18)
O2—S1—C3—C4−24.77 (18)O9—S3—C19—C24−174.70 (15)
O1—S1—C3—C491.34 (16)O7—S3—C19—C24−58.54 (17)
O3—S1—C3—C821.08 (19)C24—C19—C20—C210.0 (3)
O2—S1—C3—C8154.99 (15)S3—C19—C20—C21175.80 (18)
O1—S1—C3—C8−88.89 (17)C19—C20—C21—C220.4 (4)
C8—C3—C4—C50.5 (3)C20—C21—C22—C23−0.2 (4)
S1—C3—C4—C5−179.74 (15)C20—C21—C22—C25−178.7 (2)
C3—C4—C5—C6−1.0 (3)C21—C22—C23—C24−0.4 (3)
C4—C5—C6—C70.6 (3)C25—C22—C23—C24178.0 (2)
C4—C5—C6—C9−178.76 (19)C22—C23—C24—C190.9 (3)
C5—C6—C7—C80.3 (3)C20—C19—C24—C23−0.6 (3)
C9—C6—C7—C8179.7 (2)S3—C19—C24—C23−176.47 (16)
C6—C7—C8—C3−0.8 (3)Si1—O10—C26—C1−129.79 (13)
C4—C3—C8—C70.4 (3)C10—C1—C26—O10−169.26 (14)
S1—C3—C8—C7−179.36 (16)C18—C1—C26—O1069.59 (18)
S2—O4—C10—C1−155.23 (12)C2—C1—C26—O10−47.96 (19)
C18—C1—C10—O4−54.42 (18)O10—Si1—C27—C30−60.39 (18)
C2—C1—C10—O464.04 (18)C29—Si1—C27—C3058.41 (19)
C26—C1—C10—O4−175.17 (14)C28—Si1—C27—C30−178.54 (17)
O6—S2—C11—C16−128.23 (17)O10—Si1—C27—C32178.73 (15)
O5—S2—C11—C163.90 (19)C29—Si1—C27—C32−62.47 (19)
O4—S2—C11—C16117.85 (17)C28—Si1—C27—C3260.58 (19)
O6—S2—C11—C1249.36 (18)O10—Si1—C27—C3159.37 (17)
O5—S2—C11—C12−178.51 (15)C29—Si1—C27—C31178.17 (16)
O4—S2—C11—C12−64.57 (17)C28—Si1—C27—C31−58.78 (19)
C16—C11—C12—C13−1.4 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C2—H2A···O5i0.972.573.133 (2)117
C2—H2B···O20.972.562.902 (2)101
C4—H4A···O6i0.932.543.446 (3)166
C10—H10B···O10.972.502.856 (2)102
C10—H10B···O60.972.542.955 (2)106
C16—H16A···O50.932.512.896 (3)105
C17—H17C···O3ii0.962.463.361 (3)156
C18—H18A···O40.972.462.799 (2)100
C18—H18B···O5i0.972.473.056 (2)119
C20—H20A···O90.932.542.907 (2)104
C24—H24A···O9iii0.932.453.251 (2)144
C25—H25B···O8iv0.962.573.271 (3)131
C26—H26B···O70.972.452.851 (2)105
C29—H29E···O9v0.962.553.504 (3)172
C28—H28D···Cg1vi0.963.253.888 (3)125

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+1, y+1/2, −z+3/2; (iii) x, −y+3/2, z+1/2; (iv) −x, y+1/2, −z+3/2; (v) −x, −y+1, −z+1; (vi) −x, y−1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2586).

References

  • Abdel-Jalil, R. J. M., Übele, M., Ehrlichmann, W., Voelter, W. & Machulla, H. J. (2006). J. Radioanal. Nucl. Chem 267, 557–560.
  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19.
  • Bruker (2005). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Monge, S., Selambarom, J., Roque, J. P. & Pavia, A. (2001). Tetrahedron, 57, 9979–9987.
  • Nagasawa, H., Uto, Y., Kirk, K. L. & Hori, H. (2006). Biol. Pharm. Bull.29, 2335–2342. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.

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