Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 3| March 2012| Page o900
doi:10.1107/S1600536812008069

1D-1-O-tert-Butyl­di­phenyl­silyl-2,3,6-O-tris­­(meth­­oxy­methyl­ene)-myo-inositol 4,5-bis­­(di­benzyl­phosphate)

Regan J. Andersona and Graeme J. Gainsforda*

aIndustrial Research Limited, PO Box 31-310, Lower Hutt, New Zealand
*Correspondence e-mail: g.gainsford@irl.cri.nz

(Received 14 December 2011; accepted 22 February 2012; online 29 February 2012)

The title compound [systematic name: tetra­benzyl (1R,2R,3S,4R,5R,6S)-4-(tert-butyl­diphenyl­sil­yloxy)-3,5,6-tris­(meth­oxy­meth­oxy)cyclo­hexane-1,2-diyl bis­phosphate], C56H68O15P2Si, was isolated as an inter­mediate in the preparation of a phosphatidylinositol phosphate for biological studies. In the crystal, the mol­ecules are connected via one methyl­ene C—H⋯π and two weak phen­yl–ether C—H⋯O inter­actions. One benz­yloxy group is disordered over two overlapping positions with an occupancy ratio of 0.649 (7):0.351 (7).

Related literature

For background material on the synthesis, see: Kubiak & Bruzik (2003[Kubiak, R. J. & Bruzik, K. S. (2003). J. Org. Chem. 68, 960-968.]). For structurally similar compounds, see: Bello et al. (2007[Bello, D., Aslam, T., Bultynck, G., Slawin, A. M. Z., Roderick, H. L., Bootman, M. D. & Conway, S. J. (2007). J. Org. Chem. 72, 5647-5650.]); Sato et al. (2008[Sato, K.-I., Akai, S., Shoji, H., Sugita, N., Yoshida, S., Nagai, Y., Suzuki, K., Nakamura, Y., Kaijihara, Y., Funabashi, M. & Yoshimura, Y. (2008). J. Org. Chem. 73, 1234-1242.]). For the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data

  • C56H68O15P2Si

  • Mr = 1071.13

  • Orthorhombic, P 21 21 2

  • a = 10.4052 (7) Å

  • b = 53.019 (3) Å

  • c = 10.0786 (6) Å

  • V = 5560.1 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.17 mm−1

  • T = 118 K

  • 0.50 × 0.42 × 0.05 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan [SADABS (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS . Bruker AXS Inc., Madison, Wisconsin, USA.]); Blessing (1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.])] Tmin = 0.600, Tmax = 0.745

  • 68347 measured reflections

  • 8042 independent reflections

  • 7297 reflections with I > 2σ(I)

  • Rint = 0.081
Refinement

  • R[F2 > 2σ(F2)] = 0.071

  • wR(F2) = 0.181

  • S = 1.04

  • 8042 reflections

  • 655 parameters

  • 16 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.38 e Å−3

  • Δρmin = −0.43 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2324 Friedel pairs

  • Flack parameter: 0.12 (15)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8–C13 ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C19—H19⋯O13i 0.95 2.50 3.342 (9) 148
C32A—H32A⋯O10ii 0.95 2.30 3.243 (11) 173
C14—H14B⋯Cg1iii 0.99 2.86 3.832 (7) 168
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]; (ii) -x+1, -y+1, z; (iii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS . Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS . Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and SADABS (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS . Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812008069/gk2443sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812008069/gk2443Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812008069/gk2443Isup3.cml

checkCIF report


Comment top

As part of a program to synthesize phosphatidylinositol phosphates for biological studies, the synthesis of phosphatidylinositol 4,5-bisphosphate was undertaken following a literature procedure (Kubiak & Bruzik, 2003). Crystals of an intermediate, the title compound (I), C56H68O15P2Si, were obtained from a hot EtOAc/petroleum ether (1:4) solution, after chromatographic purification.

The asymmetric unit of (I) contains one independent molecule of the title compound (Fig. 1). The absolute configuration of the molecule was indicated at low significance by anomalous dispersion effects and it confirmed the expected configuration.

One benzyloxy substituent (C28—C34) on atom P2 was disordered; only the major final model is shown in Figure 1. There is a wide variation in O–C (methylene) bond lengths (1.425 (7)–1.482 (7)) in the benzoyloxy chains but the average, and all other dimensions are consistent with previous reports of related compounds [CSD (Allen, 2002) codes TIXDUA (Sato et al., 2008) and MIHYOS (Bello et al., 2007)]. Crystal stabilization is provided by weak non-classical phenyl C–H···O and C–H···π interactions (Table 2, Cg1 is the centroid of ring C8–C13) building head to tail chains along the b axis. The key motifs (Bernstein et al., 1995) are C(14) and R22(28), the latter shown in Figure 2 involving the H32A···O10 interactions.

Related literature top

For background material on the synthesis, see: Kubiak & Bruzik (2003). For structurally similar compounds, see: Bello et al. (2007); Sato et al. (2008). For the Cambridge Structural Database, see: Allen (2002). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

The title compound was prepared as described for compound 66 in Kubiak & Bruzik (2003). Crystals were obtained from a hot EtOAc/petroleum ether (1:4) solution after purification and isolation (mp: 368–369K). [α]20D = +7.3 (c 2.0 g 100 mL-1, CHCl3); 31P NMR (202 MHz, CDCl3) δ -1.4, -1.1; HRMS(ESI) calcd for C56H68NaO15P2Si [M+Na] 1093.3700, found 1093.3712

Refinement top

Refinement of the final model gave conventional R (R1) of 12% with many data having Fo >> Fc. This was consistent with overlap of data given the (unexpectedly large) length of the c axis, and the initial difficulty in defining the unit cell for data processing. It was not possible to recollect data using more suitable diffractometer settings or radiation wavelength. Data with I(obs) > x*I(calc) and with I(obs)-I(calc) > x*Sigma(Iobs) were removed from the dataset, progessively from x 2.0 to x=1.3. Using the remaining 8053 data from an x value of 1.45 gave a "worst agreement" table which indicated that most of the overlapped data had been removed: the 1977 reflections removed gave an R1 of 0.36. In refinement, 10 further reflections measured at low theta angle with I(obs) << I(calc) were removed as outliers.

The phenyl ring atoms C29—C34 (Figure 1) were disordered over two orientations dictated by the two-site disorder of C28. The two corresponding phenyl ring atom sets were located and refined with a total occupancy of 1.0 with each having a group and individual C–C distance constraint (AFIX 6 & DFIX) of 1.39 Å. All carbon atoms were given a common isotropic Uisod value and hydrogen atoms were added at expected positions with fixed U values of 1.5*Uisod. The C–H distances for the two C28 sites were refined with a C—H restraint of 0.99 (3) Å. Final group occupancies were 0.649 (7):0.351 (7) and the common carbon U was 0.0510 (11) Å2. All other carbon-bound H atoms were constrained to their expected geometries [C—H 0.95,0.98, 0.99 Å]. All methyl H atoms were free to rotate (HFIX 137). All methyl & disordered H/other H atoms were refined with Uiso 1.5/1.2 times the Ueq of their parent atom. All other non-hydrogen atoms were refined with anisotropic thermal parameters.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005) and SADABS (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. Asymmetric unit contents of the title compound; only the major conformer for benzyl atoms C28—C34 is shown (see text). H-atoms have been removed for clarity. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Packing diagram of (I) viewed down the c axis with hydrogen bonds shown as dashed lines (Macrae et al., 2008). H atoms not involved in intermolecular contacts (Table 1) are excluded. Symmetry operations: (i) 1/2 + x, 1/2 - y, 1 - z (ii) 1 - x, 1 - y, z.
tetrabenzyl (1R,2R,3S,4R,5R,6S)-4-(tert- butyldiphenylsilyloxy)-3,5,6-tris(methoxymethoxy)cyclohexane-1,2-diyl bisphosphate top
Crystal data top
C56H68O15P2SiF(000) = 2272
Mr = 1071.13Dx = 1.280 Mg m−3
Orthorhombic, P21212Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2abCell parameters from 9935 reflections
a = 10.4052 (7) Åθ = 2.3–24.9°
b = 53.019 (3) ŵ = 0.17 mm−1
c = 10.0786 (6) ÅT = 118 K
V = 5560.1 (6) Å3Triangular, colourless
Z = 40.50 × 0.42 × 0.05 mm
Data collection top
Bruker APEXII CCD
diffractometer		8042 independent reflections
Radiation source: fine-focus sealed tube7297 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.081
Detector resolution: 8.333 pixels mm-1θmax = 25.3°, θmin = 2.5°
ϕ and ω scansh = −12→12
Absorption correction: multi-scan
[SADABS (Bruker, 2005); Blessing (1995)]		k = −63→62
Tmin = 0.600, Tmax = 0.745l = −11→12
68347 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.071H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.181 w = 1/[σ2(Fo2) + (0.1107P)2 + 10.0351P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.007
8042 reflectionsΔρmax = 0.38 e Å−3
655 parametersΔρmin = −0.43 e Å−3
16 restraintsAbsolute structure: Flack (1983), 2324 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.12 (15)
Crystal data top
C56H68O15P2SiV = 5560.1 (6) Å3
Mr = 1071.13Z = 4
Orthorhombic, P21212Mo Kα radiation
a = 10.4052 (7) ŵ = 0.17 mm−1
b = 53.019 (3) ÅT = 118 K
c = 10.0786 (6) Å0.50 × 0.42 × 0.05 mm
Data collection top
Bruker APEXII CCD
diffractometer		8042 independent reflections
Absorption correction: multi-scan
[SADABS (Bruker, 2005); Blessing (1995)]		7297 reflections with I > 2σ(I)
Tmin = 0.600, Tmax = 0.745Rint = 0.081
68347 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.071H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.181 w = 1/[σ2(Fo2) + (0.1107P)2 + 10.0351P]
where P = (Fo2 + 2Fc2)/3
S = 1.04Δρmax = 0.38 e Å−3
8042 reflectionsΔρmin = −0.43 e Å−3
655 parametersAbsolute structure: Flack (1983), 2324 Friedel pairs
16 restraintsAbsolute structure parameter: 0.12 (15)
Special details top

Experimental. 1H NMR (500?MHz, CDCl3) δ 1.11 (s, 9H), 2.96 (s, 3H), 3.19 (dd, J = 2.1, 10.0?Hz, 1H), 3.25 (s, 3H), 3.28 (t, J = 2.1?Hz, 1H), 3.38 (s, 3H), 3.86 (dd, J = 2.0, 9.7?Hz, 1H), 4.04 (d, J = 7.0?Hz, 1H), 4.19 (t, J = 9.6?Hz, 1H), 4.27–4.34 (m, 2H), 4.52 (d, J = 6.4?Hz, 1H), 4.58 (d, J = 6.4?Hz, 1H), 4.75–4.82 (m, 2H), 4.92 (dd, J = 6.5, 11.8?Hz, 1H), 4.97–5.11 (m, 7H), 5.14 (dd, J = 7.4, 11.9?Hz, 1H), 7.20–7.31 (m, 20H), 7.36–7.45 (m, 6H), 7.69–7.70 (m, 2H), 7.76–7.78 (m, 2H); 13C NMR (126?MHz, CDCl3) δ 19.2, 27.3, 55.6, 55.7, 57.0, 69.1 (d, J = 4.4?Hz), 69.3 (d, J = 4.4?Hz), 69.4 (d, J = 5.4?Hz), 69.5 (d, J = 5.2?Hz), 73.8, 74.2, 75.6, 75.9, 77.9, 78.6, 96.0, 97.4, 98.8, 127.80, 127.84, 127.9, 128.0, 128.1, 128.2, 128.3, 128.4, 130.0, 130.1, 132.6, 134.0, 135.9, 136.1, 136.26, 136.30, 136.4;

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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*/UeqOcc. (<1)
P10.51021 (15)0.30563 (3)0.81745 (14)0.0248 (3)
P20.68940 (14)0.37535 (3)0.89914 (14)0.0218 (3)
Si10.22969 (15)0.42782 (3)0.40560 (16)0.0236 (3)
O10.5361 (4)0.32847 (7)0.7182 (4)0.0238 (8)
O20.4477 (4)0.31308 (7)0.9399 (4)0.0300 (9)
O30.4419 (5)0.28550 (7)0.7295 (4)0.0340 (10)
O40.6450 (4)0.29329 (7)0.8285 (4)0.0263 (9)
O50.5440 (3)0.37372 (7)0.8640 (3)0.0220 (8)
O60.7822 (3)0.36617 (7)0.8036 (4)0.0270 (8)
O70.7058 (4)0.40374 (8)0.9378 (4)0.0362 (10)
O80.6963 (4)0.36004 (7)1.0325 (4)0.0271 (9)
O90.4538 (4)0.41785 (7)0.7376 (4)0.0237 (8)
O100.3178 (4)0.44486 (7)0.8584 (5)0.0381 (11)
O110.2570 (4)0.41287 (7)0.5474 (4)0.0227 (8)
O120.1881 (4)0.36476 (7)0.6405 (4)0.0262 (8)
O130.0361 (4)0.33465 (8)0.5734 (4)0.0357 (10)
O140.3313 (4)0.32276 (7)0.5353 (4)0.0226 (8)
O150.3933 (6)0.31597 (8)0.3167 (5)0.0481 (13)
C10.4384 (5)0.34754 (9)0.7015 (5)0.0206 (11)
H10.36660.34470.76570.025*
C20.5002 (5)0.37315 (10)0.7267 (5)0.0197 (10)
H20.57370.37600.66460.024*
C30.3976 (5)0.39422 (9)0.7101 (5)0.0203 (11)
H30.32430.39110.77220.024*
C40.3498 (5)0.39319 (10)0.5663 (5)0.0220 (11)
H40.42340.39540.50350.026*
C50.2870 (5)0.36739 (10)0.5453 (5)0.0209 (11)
H50.24950.36650.45410.025*
C60.3886 (5)0.34639 (9)0.5621 (6)0.0223 (11)
H60.46100.34930.49870.027*
C70.7482 (6)0.30298 (11)0.9161 (7)0.0331 (13)
H7A0.71430.30541.00700.040*
H7B0.77880.31950.88280.040*
C80.8564 (5)0.28471 (10)0.9188 (5)0.0215 (11)
C90.8509 (6)0.26185 (10)0.8541 (6)0.0288 (13)
H90.77640.25730.80530.035*
C100.9577 (6)0.24519 (11)0.8609 (6)0.0318 (14)
H100.95510.22940.81680.038*
C111.0667 (7)0.25229 (14)0.9332 (6)0.0375 (15)
H111.13810.24120.93810.045*
C121.0715 (6)0.27491 (14)0.9963 (7)0.0364 (15)
H121.14670.27981.04320.044*
C130.9633 (6)0.29117 (11)0.9915 (6)0.0292 (13)
H130.96470.30671.03880.035*
C140.3399 (6)0.27005 (12)0.7774 (6)0.0347 (14)
H14A0.26280.28050.79360.042*
H14B0.36540.26220.86240.042*
C150.3096 (7)0.25028 (12)0.6794 (6)0.0352 (14)
C160.2071 (7)0.25236 (12)0.5926 (7)0.0437 (16)
H160.15030.26630.59900.052*
C170.1871 (7)0.23391 (14)0.4957 (7)0.0407 (16)
H170.11860.23570.43400.049*
C180.2662 (8)0.21320 (13)0.4893 (6)0.0450 (18)
H180.25100.20060.42420.054*
C190.3641 (9)0.21062 (13)0.5739 (7)0.050 (2)
H190.41650.19600.56920.060*
C200.3909 (7)0.22900 (12)0.6690 (7)0.0392 (15)
H200.46300.22720.72610.047*
C210.5946 (6)0.36118 (14)1.1330 (6)0.0356 (15)
H21A0.52680.37301.10380.043*
H21B0.55520.34431.14340.043*
C220.6467 (6)0.36949 (11)1.2602 (6)0.0329 (14)*
C230.6542 (6)0.39494 (12)1.2917 (6)0.0306 (13)
H230.62060.40711.23160.037*
C240.7104 (6)0.40299 (13)1.4099 (7)0.0382 (14)
H240.71490.42041.43090.046*
C250.7593 (6)0.38516 (13)1.4959 (6)0.0340 (14)
H250.79900.39051.57600.041*
C260.7520 (6)0.35983 (13)1.4681 (7)0.0368 (15)
H260.78360.34791.53040.044*
C270.6984 (6)0.35154 (12)1.3492 (6)0.0329 (14)
H270.69660.33411.32820.039*
C350.4252 (6)0.42804 (12)0.8605 (7)0.0353 (15)
H35A0.50140.43730.89380.042*
H35B0.40690.41410.92330.042*
C360.1951 (7)0.43296 (13)0.8674 (7)0.0409 (16)
H36A0.18740.42020.79760.061*
H36B0.12740.44560.85630.061*
H36C0.18620.42490.95440.061*
C370.3809 (6)0.44399 (10)0.3504 (6)0.0283 (13)
C380.4702 (6)0.45191 (12)0.4419 (6)0.0343 (14)
H380.45850.44780.53280.041*
C390.5775 (7)0.46586 (13)0.4043 (8)0.0456 (17)
H390.63810.47100.46930.055*
C400.5963 (7)0.47231 (14)0.2713 (7)0.0449 (17)
H400.67050.48150.24480.054*
C410.5031 (9)0.46498 (12)0.1769 (8)0.054 (2)
H410.51220.46960.08630.064*
C420.4002 (8)0.45125 (12)0.2175 (6)0.0393 (16)
H420.33840.44630.15330.047*
C430.1779 (6)0.40495 (11)0.2738 (5)0.0254 (12)
C440.2746 (6)0.39225 (11)0.1977 (6)0.0305 (13)
H440.36290.39590.21180.037*
C450.2382 (7)0.37443 (12)0.1024 (7)0.0429 (16)
H450.30240.36640.05020.052*
C460.1120 (6)0.36830 (13)0.0831 (7)0.0369 (14)
H460.08950.35610.01790.044*
C470.0168 (7)0.37972 (14)0.1580 (8)0.0475 (18)
H47−0.07090.37530.14540.057*
C480.0506 (6)0.39768 (12)0.2512 (6)0.0346 (14)
H48−0.01550.40540.30200.042*
C490.1022 (7)0.45170 (11)0.4550 (7)0.0361 (15)
C500.1681 (7)0.47292 (12)0.5370 (7)0.0394 (15)
H50A0.10290.48480.56900.059*
H50B0.22990.48190.48080.059*
H50C0.21310.46550.61290.059*
C51−0.0050 (7)0.44043 (13)0.5350 (8)0.0434 (17)
H51A−0.06940.45340.55410.065*
H51B0.02940.43380.61860.065*
H51C−0.04500.42670.48470.065*
C520.0453 (9)0.46379 (14)0.3285 (8)0.058 (2)
H52A0.11520.46970.27140.086*
H52B−0.00950.47810.35330.086*
H52C−0.00600.45120.28060.086*
C530.0641 (6)0.36038 (11)0.5964 (7)0.0362 (15)
H53A0.05040.36990.51310.043*
H53B0.00300.36700.66310.043*
C540.0393 (9)0.32090 (13)0.6974 (8)0.055 (2)
H54A0.12870.31790.72320.083*
H54B−0.00510.30470.68650.083*
H54C−0.00370.33080.76650.083*
C550.4009 (7)0.30731 (12)0.4478 (6)0.0356 (15)
H55A0.49200.30690.47580.043*
H55B0.36680.28990.45250.043*
C560.2721 (8)0.31194 (13)0.2592 (7)0.060 (2)
H56A0.24080.29510.28350.089*
H56B0.27920.31310.16240.089*
H56C0.21170.32470.29140.089*
C28A0.8291 (8)0.41653 (17)0.9201 (10)0.0511 (10)*0.649 (7)
H28A0.89950.40500.89410.077*0.649 (7)
H28B0.83100.41881.01760.077*0.649 (7)
C30A0.7303 (12)0.4523 (2)0.7929 (11)0.0511 (10)*0.649 (7)
H30A0.70420.44090.72550.077*0.649 (7)
C31A0.7039 (12)0.47780 (19)0.7838 (12)0.0511 (10)*0.649 (7)
H31A0.65310.48350.71150.077*0.649 (7)
C32A0.7474 (12)0.4954 (2)0.8739 (11)0.0511 (10)*0.649 (7)
H32A0.72920.51280.86170.077*0.649 (7)
C33A0.8183 (13)0.48738 (19)0.9826 (12)0.0511 (10)*0.649 (7)
H33A0.84900.49901.04710.077*0.649 (7)
C34A0.8425 (11)0.46165 (17)0.9935 (10)0.0511 (10)*0.649 (7)
H34A0.89330.45591.06580.077*0.649 (7)
C29A0.7966 (11)0.44406 (17)0.9048 (10)0.0511 (10)*0.649 (7)
C28B0.773 (2)0.4201 (4)0.834 (2)0.0511 (10)*0.351 (7)
H28C0.862 (10)0.413 (4)0.83 (3)0.077*0.351 (7)
H28D0.701 (17)0.418 (5)0.77 (2)0.077*0.351 (7)
C30B0.715 (2)0.4629 (3)0.811 (2)0.0511 (10)*0.351 (7)
H30B0.67210.45680.73450.077*0.351 (7)
C31B0.700 (2)0.4885 (3)0.843 (2)0.0511 (10)*0.351 (7)
H31B0.64610.50000.79640.077*0.351 (7)
C32B0.776 (2)0.4946 (4)0.952 (2)0.0511 (10)*0.351 (7)
H32B0.77510.51190.97610.077*0.351 (7)
C33B0.851 (2)0.4793 (3)1.032 (2)0.0511 (10)*0.351 (7)
H33B0.89220.48531.10970.077*0.351 (7)
C34B0.864 (2)0.4544 (3)0.989 (2)0.0511 (10)*0.351 (7)
H34B0.92300.44341.03070.077*0.351 (7)
C29B0.788 (3)0.4460 (4)0.884 (2)0.0511 (10)*0.351 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0329 (8)0.0219 (6)0.0197 (7)0.0017 (6)−0.0025 (6)0.0005 (6)
P20.0250 (7)0.0244 (7)0.0161 (6)−0.0008 (5)−0.0038 (6)0.0005 (5)
Si10.0236 (7)0.0250 (7)0.0223 (7)0.0031 (6)−0.0054 (6)0.0032 (6)
O10.029 (2)0.0209 (18)0.0217 (19)0.0122 (16)0.0082 (17)0.0038 (15)
O20.041 (2)0.031 (2)0.0181 (19)0.0073 (18)0.0021 (17)−0.0038 (16)
O30.052 (3)0.0198 (19)0.030 (2)−0.0074 (18)0.000 (2)−0.0065 (17)
O40.026 (2)0.0252 (19)0.028 (2)0.0110 (15)0.0055 (17)0.0037 (16)
O50.0150 (18)0.033 (2)0.0177 (18)0.0020 (16)−0.0040 (14)−0.0053 (15)
O60.0120 (18)0.039 (2)0.030 (2)0.0025 (15)−0.0044 (16)−0.0010 (17)
O70.038 (3)0.030 (2)0.040 (3)−0.0069 (19)−0.001 (2)−0.0041 (18)
O80.0147 (19)0.037 (2)0.030 (2)0.0088 (16)0.0029 (17)0.0048 (17)
O90.027 (2)0.0217 (18)0.0223 (19)−0.0024 (15)0.0008 (16)−0.0016 (15)
O100.032 (2)0.025 (2)0.057 (3)0.0063 (18)0.008 (2)−0.0066 (19)
O110.0223 (19)0.027 (2)0.0189 (18)0.0041 (16)−0.0114 (16)0.0016 (15)
O120.0164 (18)0.033 (2)0.029 (2)0.0001 (16)−0.0016 (16)0.0069 (16)
O130.032 (2)0.037 (2)0.038 (3)0.0005 (19)0.012 (2)−0.0053 (19)
O140.021 (2)0.0236 (18)0.0230 (19)−0.0028 (15)−0.0038 (16)−0.0062 (15)
O150.086 (4)0.032 (2)0.026 (2)−0.013 (2)−0.012 (3)−0.0082 (19)
C10.023 (3)0.021 (3)0.017 (3)0.003 (2)−0.005 (2)0.004 (2)
C20.014 (2)0.031 (3)0.014 (2)0.004 (2)0.000 (2)0.003 (2)
C30.021 (3)0.022 (2)0.018 (3)0.001 (2)−0.002 (2)0.000 (2)
C40.019 (3)0.022 (3)0.025 (3)0.000 (2)0.004 (2)0.003 (2)
C50.014 (2)0.027 (3)0.022 (3)0.003 (2)0.004 (2)0.005 (2)
C60.024 (3)0.014 (2)0.028 (3)0.004 (2)0.001 (2)0.001 (2)
C70.035 (3)0.026 (3)0.039 (3)−0.007 (2)−0.002 (3)−0.003 (3)
C80.017 (2)0.027 (3)0.021 (3)−0.001 (2)−0.002 (2)0.003 (2)
C90.028 (3)0.024 (3)0.034 (3)−0.001 (2)0.001 (2)−0.001 (2)
C100.023 (3)0.036 (3)0.036 (3)0.007 (2)0.011 (2)0.002 (3)
C110.038 (4)0.054 (4)0.021 (3)0.008 (3)−0.005 (3)0.014 (3)
C120.013 (3)0.061 (4)0.035 (3)−0.001 (3)−0.002 (2)0.015 (3)
C130.027 (3)0.035 (3)0.026 (3)−0.003 (2)−0.003 (2)−0.001 (2)
C140.038 (4)0.043 (3)0.023 (3)−0.017 (3)−0.006 (3)−0.003 (3)
C150.039 (4)0.037 (3)0.030 (3)−0.014 (3)−0.001 (3)−0.005 (3)
C160.050 (4)0.033 (3)0.048 (4)−0.006 (3)0.010 (4)−0.008 (3)
C170.038 (4)0.059 (4)0.026 (3)−0.006 (3)−0.002 (3)−0.003 (3)
C180.070 (5)0.041 (4)0.024 (3)−0.018 (3)−0.017 (3)−0.011 (3)
C190.082 (6)0.031 (3)0.036 (4)−0.008 (4)0.009 (4)−0.001 (3)
C200.046 (4)0.037 (3)0.034 (4)0.000 (3)−0.007 (3)0.005 (3)
C210.022 (3)0.064 (4)0.020 (3)−0.007 (3)0.011 (2)0.000 (3)
C230.025 (3)0.048 (3)0.019 (3)0.003 (3)−0.008 (2)0.004 (3)
C240.034 (3)0.047 (4)0.033 (3)0.000 (3)0.000 (3)−0.010 (3)
C250.023 (3)0.059 (4)0.021 (3)−0.005 (3)−0.011 (2)0.001 (3)
C260.022 (3)0.053 (4)0.036 (4)0.003 (3)0.001 (3)0.005 (3)
C270.029 (3)0.043 (3)0.027 (3)−0.004 (3)0.013 (3)0.005 (3)
C350.030 (3)0.030 (3)0.045 (4)0.004 (3)−0.018 (3)−0.020 (3)
C360.043 (4)0.043 (4)0.037 (4)−0.001 (3)0.001 (3)−0.005 (3)
C370.025 (3)0.027 (3)0.033 (3)−0.002 (2)−0.004 (3)0.011 (2)
C380.038 (4)0.035 (3)0.030 (3)0.006 (3)−0.007 (3)−0.008 (3)
C390.037 (4)0.044 (4)0.056 (5)−0.015 (3)−0.010 (4)0.000 (3)
C400.043 (4)0.047 (4)0.045 (4)−0.018 (3)0.004 (3)−0.001 (3)
C410.086 (6)0.035 (3)0.040 (4)−0.005 (4)0.023 (4)0.004 (3)
C420.065 (5)0.030 (3)0.022 (3)−0.006 (3)−0.008 (3)−0.002 (2)
C430.025 (3)0.035 (3)0.016 (3)−0.005 (2)−0.011 (2)0.004 (2)
C440.035 (3)0.031 (3)0.025 (3)0.000 (2)−0.002 (3)−0.002 (2)
C450.049 (4)0.033 (3)0.047 (4)0.002 (3)−0.012 (3)−0.014 (3)
C460.033 (3)0.045 (4)0.033 (3)−0.007 (3)0.000 (3)−0.006 (3)
C470.031 (4)0.055 (4)0.056 (5)−0.005 (3)−0.009 (3)−0.012 (3)
C480.027 (3)0.051 (4)0.026 (3)−0.012 (3)0.008 (3)−0.003 (3)
C490.039 (4)0.027 (3)0.042 (4)0.011 (3)−0.016 (3)−0.003 (3)
C500.041 (4)0.039 (3)0.039 (4)0.002 (3)0.001 (3)−0.007 (3)
C510.027 (3)0.046 (4)0.056 (4)0.002 (3)0.013 (3)−0.012 (3)
C520.083 (6)0.045 (4)0.045 (4)0.032 (4)−0.006 (4)0.006 (3)
C530.028 (3)0.031 (3)0.049 (4)0.004 (2)−0.015 (3)0.014 (3)
C540.075 (6)0.028 (3)0.063 (5)−0.013 (3)0.011 (5)0.020 (3)
C550.060 (4)0.026 (3)0.021 (3)0.011 (3)0.004 (3)−0.003 (2)
C560.095 (7)0.046 (4)0.037 (4)0.006 (4)−0.036 (4)−0.016 (3)
Geometric parameters (Å, º) top
P1—O21.450 (4)C25—H250.9500
P1—O41.552 (4)C26—C271.393 (9)
P1—O31.559 (4)C26—H260.9500
P1—O11.593 (4)C27—H270.9500
P2—O61.448 (4)C35—H35A0.9900
P2—O51.556 (4)C35—H35B0.9900
P2—O71.564 (4)C36—H36A0.9800
P2—O81.571 (4)C36—H36B0.9800
Si1—O111.659 (4)C36—H36C0.9800
Si1—C371.876 (6)C37—C381.375 (9)
Si1—C431.878 (6)C37—C421.407 (9)
Si1—C491.900 (7)C38—C391.391 (10)
O1—C11.445 (6)C38—H380.9500
O3—C141.425 (7)C39—C401.397 (11)
O4—C71.482 (7)C39—H390.9500
O5—C21.458 (6)C40—C411.413 (11)
O7—C28A1.461 (10)C40—H400.9500
O7—C28B1.53 (2)C41—C421.357 (11)
O8—C211.467 (7)C41—H410.9500
O9—C351.384 (7)C42—H420.9500
O9—C31.410 (6)C43—C481.399 (8)
O10—C361.427 (8)C43—C441.433 (9)
O10—C351.430 (7)C44—C451.399 (9)
O11—C41.434 (6)C44—H440.9500
O12—C531.384 (7)C45—C461.367 (10)
O12—C51.415 (6)C45—H450.9500
O13—C531.414 (7)C46—C471.385 (10)
O13—C541.448 (9)C46—H460.9500
O14—C551.404 (7)C47—C481.383 (9)
O14—C61.414 (6)C47—H470.9500
O15—C551.401 (8)C48—H480.9500
O15—C561.405 (9)C49—C511.501 (10)
C1—C61.498 (7)C49—C521.544 (10)
C1—C21.524 (7)C49—C501.556 (9)
C1—H11.0000C50—H50A0.9800
C2—C31.554 (7)C50—H50B0.9800
C2—H21.0000C50—H50C0.9800
C3—C41.533 (7)C51—H51A0.9800
C3—H31.0000C51—H51B0.9800
C4—C51.531 (7)C51—H51C0.9800
C4—H41.0000C52—H52A0.9800
C5—C61.545 (7)C52—H52B0.9800
C5—H51.0000C52—H52C0.9800
C6—H61.0000C53—H53A0.9900
C7—C81.486 (8)C53—H53B0.9900
C7—H7A0.9900C54—H54A0.9800
C7—H7B0.9900C54—H54B0.9800
C8—C131.375 (8)C54—H54C0.9800
C8—C91.378 (8)C55—H55A0.9900
C9—C101.421 (8)C55—H55B0.9900
C9—H90.9500C56—H56A0.9800
C10—C111.399 (9)C56—H56B0.9800
C10—H100.9500C56—H56C0.9800
C11—C121.359 (10)C28A—C29A1.506 (13)
C11—H110.9500C28A—H28A0.9899
C12—C131.419 (9)C28A—H28B0.9900
C12—H120.9500C30A—C31A1.381 (9)
C13—H130.9500C30A—C29A1.393 (9)
C14—C151.474 (8)C30A—H30A0.9500
C14—H14A0.9900C31A—C32A1.379 (9)
C14—H14B0.9900C31A—H31A0.9500
C15—C161.384 (10)C32A—C33A1.388 (9)
C15—C201.414 (10)C32A—H32A0.9500
C16—C171.398 (9)C33A—C34A1.392 (9)
C16—H160.9500C33A—H33A0.9500
C17—C181.374 (11)C34A—C29A1.3771
C17—H170.9500C34A—H34A0.9500
C18—C191.336 (11)C28B—C29B1.47 (3)
C18—H180.9500C28B—H28C0.99 (3)
C19—C201.395 (9)C28B—H28D0.99 (3)
C19—H190.9500C30B—C29B1.391 (10)
C20—H200.9500C30B—C31B1.401 (10)
C21—C221.460 (9)C30B—H30B0.9500
C21—H21A0.9900C31B—C32B1.393 (10)
C21—H21B0.9900C31B—H31B0.9500
C22—C231.388 (9)C32B—C33B1.387 (10)
C22—C271.415 (9)C32B—H32B0.9500
C23—C241.395 (9)C33B—C34B1.392 (10)
C23—H230.9500C33B—H33B0.9500
C24—C251.380 (9)C34B—C29B1.389 (10)
C24—H240.9500C34B—H34B0.9500
C25—C261.374 (10)
O2—P1—O4117.3 (2)O9—C35—H35A108.9
O2—P1—O3117.8 (3)O10—C35—H35A108.9
O4—P1—O399.4 (2)O9—C35—H35B108.9
O2—P1—O1113.8 (2)O10—C35—H35B108.9
O4—P1—O1102.3 (2)H35A—C35—H35B107.7
O3—P1—O1103.9 (2)O10—C36—H36A109.5
O6—P2—O5118.6 (2)O10—C36—H36B109.5
O6—P2—O7114.6 (2)H36A—C36—H36B109.5
O5—P2—O7102.5 (2)O10—C36—H36C109.5
O6—P2—O8111.4 (2)H36A—C36—H36C109.5
O5—P2—O8102.1 (2)H36B—C36—H36C109.5
O7—P2—O8106.2 (2)C38—C37—C42117.3 (6)
O11—Si1—C37109.3 (2)C38—C37—Si1120.5 (5)
O11—Si1—C43110.5 (2)C42—C37—Si1121.8 (5)
C37—Si1—C43109.0 (3)C37—C38—C39121.4 (6)
O11—Si1—C49102.3 (3)C37—C38—H38119.3
C37—Si1—C49111.0 (3)C39—C38—H38119.3
C43—Si1—C49114.5 (3)C38—C39—C40120.3 (7)
C1—O1—P1119.1 (3)C38—C39—H39119.9
C14—O3—P1122.7 (4)C40—C39—H39119.9
C7—O4—P1123.5 (4)C39—C40—C41118.8 (6)
C2—O5—P2121.4 (3)C39—C40—H40120.6
C28A—O7—P2120.8 (4)C41—C40—H40120.6
C28B—O7—P2115.3 (9)C42—C41—C40119.0 (7)
C21—O8—P2122.5 (4)C42—C41—H41120.5
C35—O9—C3115.7 (5)C40—C41—H41120.5
C36—O10—C35115.0 (5)C41—C42—C37123.1 (7)
C4—O11—Si1125.3 (3)C41—C42—H42118.5
C53—O12—C5118.5 (5)C37—C42—H42118.5
C53—O13—C54109.8 (5)C48—C43—C44116.6 (5)
C55—O14—C6114.8 (5)C48—C43—Si1124.4 (5)
C55—O15—C56113.0 (6)C44—C43—Si1118.8 (4)
O1—C1—C6108.9 (4)C45—C44—C43119.7 (6)
O1—C1—C2107.9 (4)C45—C44—H44120.2
C6—C1—C2109.8 (4)C43—C44—H44120.2
O1—C1—H1110.1C46—C45—C44121.2 (7)
C6—C1—H1110.1C46—C45—H45119.4
C2—C1—H1110.1C44—C45—H45119.4
O5—C2—C1108.0 (4)C45—C46—C47120.4 (6)
O5—C2—C3107.6 (4)C45—C46—H46119.8
C1—C2—C3109.4 (4)C47—C46—H46119.8
O5—C2—H2110.6C48—C47—C46119.3 (6)
C1—C2—H2110.6C48—C47—H47120.4
C3—C2—H2110.6C46—C47—H47120.4
O9—C3—C4110.6 (4)C47—C48—C43122.8 (6)
O9—C3—C2109.5 (4)C47—C48—H48118.6
C4—C3—C2107.4 (4)C43—C48—H48118.6
O9—C3—H3109.8C51—C49—C52108.9 (6)
C4—C3—H3109.8C51—C49—C50109.3 (6)
C2—C3—H3109.8C52—C49—C50107.9 (6)
O11—C4—C5110.1 (4)C51—C49—Si1113.2 (4)
O11—C4—C3108.5 (4)C52—C49—Si1109.2 (5)
C5—C4—C3107.5 (4)C50—C49—Si1108.2 (5)
O11—C4—H4110.2C49—C50—H50A109.5
C5—C4—H4110.2C49—C50—H50B109.5
C3—C4—H4110.2H50A—C50—H50B109.5
O12—C5—C4107.8 (4)C49—C50—H50C109.5
O12—C5—C6110.7 (4)H50A—C50—H50C109.5
C4—C5—C6109.7 (4)H50B—C50—H50C109.5
O12—C5—H5109.6C49—C51—H51A109.5
C4—C5—H5109.6C49—C51—H51B109.5
C6—C5—H5109.6H51A—C51—H51B109.5
O14—C6—C1111.2 (4)C49—C51—H51C109.5
O14—C6—C5109.2 (4)H51A—C51—H51C109.5
C1—C6—C5108.1 (4)H51B—C51—H51C109.5
O14—C6—H6109.5C49—C52—H52A109.5
C1—C6—H6109.5C49—C52—H52B109.5
C5—C6—H6109.5H52A—C52—H52B109.5
O4—C7—C8109.5 (4)C49—C52—H52C109.5
O4—C7—H7A109.8H52A—C52—H52C109.5
C8—C7—H7A109.8H52B—C52—H52C109.5
O4—C7—H7B109.8O12—C53—O13114.0 (5)
C8—C7—H7B109.8O12—C53—H53A108.8
H7A—C7—H7B108.2O13—C53—H53A108.8
C13—C8—C9120.3 (5)O12—C53—H53B108.8
C13—C8—C7117.5 (5)O13—C53—H53B108.8
C9—C8—C7122.2 (5)H53A—C53—H53B107.6
C8—C9—C10119.4 (6)O13—C54—H54A109.5
C8—C9—H9120.3O13—C54—H54B109.5
C10—C9—H9120.3H54A—C54—H54B109.5
C11—C10—C9119.5 (6)O13—C54—H54C109.5
C11—C10—H10120.3H54A—C54—H54C109.5
C9—C10—H10120.3H54B—C54—H54C109.5
C12—C11—C10120.7 (6)O15—C55—O14111.8 (5)
C12—C11—H11119.6O15—C55—H55A109.3
C10—C11—H11119.6O14—C55—H55A109.3
C11—C12—C13119.4 (6)O15—C55—H55B109.3
C11—C12—H12120.3O14—C55—H55B109.3
C13—C12—H12120.3H55A—C55—H55B107.9
C8—C13—C12120.6 (6)O15—C56—H56A109.5
C8—C13—H13119.7O15—C56—H56B109.5
C12—C13—H13119.7H56A—C56—H56B109.5
O3—C14—C15110.0 (5)O15—C56—H56C109.5
O3—C14—H14A109.7H56A—C56—H56C109.5
C15—C14—H14A109.7H56B—C56—H56C109.5
O3—C14—H14B109.7O7—C28A—C29A105.4 (7)
C15—C14—H14B109.7O7—C28A—H28A113.3
H14A—C14—H14B108.2O7—C28A—H28B87.3
C16—C15—C20118.5 (6)O7—C28A—H28C109 (10)
C16—C15—C14122.1 (6)C31A—C30A—C29A117.4 (10)
C20—C15—C14119.3 (6)C31A—C30A—H30A121.3
C15—C16—C17120.1 (7)C29A—C30A—H30A121.3
C15—C16—H16120.0C32A—C31A—C30A123.6 (11)
C17—C16—H16120.0C32A—C31A—H31A118.2
C18—C17—C16120.2 (7)C30A—C31A—H31A118.2
C18—C17—H17119.9C31A—C32A—C33A119.1 (11)
C16—C17—H17119.9C31A—C32A—H32A120.5
C19—C18—C17120.6 (6)C33A—C32A—H32A120.5
C19—C18—H18119.7C32A—C33A—C34A117.4 (10)
C17—C18—H18119.7C32A—C33A—H33A121.3
C18—C19—C20121.3 (7)C34A—C33A—H33A121.3
C18—C19—H19119.4C29A—C34A—C33A123.4 (7)
C20—C19—H19119.4C29A—C34A—H34A118.3
C19—C20—C15119.3 (7)C33A—C34A—H34A118.3
C19—C20—H20120.4C34A—C29A—C30A119.0 (7)
C15—C20—H20120.4C34A—C29A—C28A120.8 (5)
C22—C21—O8110.6 (5)C30A—C29A—C28A119.9 (9)
C22—C21—H21A109.5C29B—C28B—O7110.0 (19)
O8—C21—H21A109.5C29B—C28B—H28C106 (10)
C22—C21—H21B109.5O7—C28B—H28C106 (10)
O8—C21—H21B109.5C29B—C28B—H28D115 (10)
H21A—C21—H21B108.1O7—C28B—H28D90 (10)
C23—C22—C27119.2 (6)H28C—C28B—H28D129
C23—C22—C21121.0 (6)C29B—C30B—C31B124 (2)
C27—C22—C21119.7 (6)C29B—C30B—H30B117.8
C22—C23—C24121.1 (6)C31B—C30B—H30B117.8
C22—C23—H23119.4C32B—C31B—C30B109.9 (19)
C24—C23—H23119.4C32B—C31B—H31B125.0
C25—C24—C23118.8 (6)C30B—C31B—H31B125.0
C25—C24—H24120.6C33B—C32B—C31B130 (2)
C23—C24—H24120.6C33B—C32B—H32B114.9
C26—C25—C24121.4 (6)C31B—C32B—H32B114.9
C26—C25—H25119.3C32B—C33B—C34B115 (2)
C24—C25—H25119.3C32B—C33B—H33B122.4
C25—C26—C27120.4 (6)C34B—C33B—H33B122.4
C25—C26—H26119.8C29B—C34B—C33B119 (2)
C27—C26—H26119.8C29B—C34B—H34B120.3
C26—C27—C22119.0 (6)C33B—C34B—H34B120.3
C26—C27—H27120.5C34B—C29B—C30B120 (2)
C22—C27—H27120.5C34B—C29B—C28B128.5 (19)
O9—C35—O10113.5 (5)C30B—C29B—C28B111.3 (18)
O2—P1—O1—C1−41.0 (4)C16—C15—C20—C19−1.3 (10)
O4—P1—O1—C1−168.6 (4)C14—C15—C20—C19−178.3 (6)
O3—P1—O1—C188.3 (4)P2—O8—C21—C22−122.4 (5)
O2—P1—O3—C14−15.3 (6)O8—C21—C22—C2388.3 (7)
O4—P1—O3—C14112.5 (5)O8—C21—C22—C27−87.3 (7)
O1—P1—O3—C14−142.2 (5)C27—C22—C23—C24−0.8 (9)
O2—P1—O4—C7−44.4 (5)C21—C22—C23—C24−176.4 (6)
O3—P1—O4—C7−172.5 (4)C22—C23—C24—C250.3 (10)
O1—P1—O4—C780.9 (4)C23—C24—C25—C26−1.0 (10)
O6—P2—O5—C2−25.0 (5)C24—C25—C26—C272.3 (10)
O7—P2—O5—C2102.3 (4)C25—C26—C27—C22−2.7 (9)
O8—P2—O5—C2−147.8 (4)C23—C22—C27—C262.0 (9)
O6—P2—O7—C28A−22.2 (6)C21—C22—C27—C26177.7 (5)
O5—P2—O7—C28A−152.0 (6)C3—O9—C35—O10−93.8 (6)
O8—P2—O7—C28A101.2 (6)C36—O10—C35—O983.7 (7)
O6—P2—O7—C28B24.7 (11)O11—Si1—C37—C38−28.4 (6)
O5—P2—O7—C28B−105.1 (11)C43—Si1—C37—C38−149.3 (5)
O8—P2—O7—C28B148.1 (11)C49—Si1—C37—C3883.7 (5)
O6—P2—O8—C21−165.0 (4)O11—Si1—C37—C42159.5 (5)
O5—P2—O8—C21−37.5 (5)C43—Si1—C37—C4238.7 (6)
O7—P2—O8—C2169.6 (5)C49—Si1—C37—C42−88.4 (6)
C37—Si1—O11—C4−60.1 (4)C42—C37—C38—C39−1.9 (10)
C43—Si1—O11—C459.8 (5)Si1—C37—C38—C39−174.3 (5)
C49—Si1—O11—C4−177.9 (4)C37—C38—C39—C400.4 (11)
P1—O1—C1—C6−114.4 (4)C38—C39—C40—C411.7 (11)
P1—O1—C1—C2126.5 (4)C39—C40—C41—C42−2.0 (11)
P2—O5—C2—C1114.5 (4)C40—C41—C42—C370.4 (11)
P2—O5—C2—C3−127.5 (4)C38—C37—C42—C411.5 (10)
O1—C1—C2—O5−62.9 (5)Si1—C37—C42—C41173.8 (6)
C6—C1—C2—O5178.5 (4)O11—Si1—C43—C4888.0 (5)
O1—C1—C2—C3−179.8 (4)C37—Si1—C43—C48−151.9 (5)
C6—C1—C2—C361.6 (6)C49—Si1—C43—C48−26.8 (6)
C35—O9—C3—C4139.1 (5)O11—Si1—C43—C44−86.4 (5)
C35—O9—C3—C2−102.8 (5)C37—Si1—C43—C4433.7 (5)
O5—C2—C3—O961.0 (5)C49—Si1—C43—C44158.8 (5)
C1—C2—C3—O9178.1 (4)C48—C43—C44—C452.8 (9)
O5—C2—C3—C4−178.9 (4)Si1—C43—C44—C45177.6 (5)
C1—C2—C3—C4−61.8 (5)C43—C44—C45—C46−2.0 (10)
Si1—O11—C4—C5−92.7 (5)C44—C45—C46—C470.1 (11)
Si1—O11—C4—C3149.9 (4)C45—C46—C47—C480.9 (11)
O9—C3—C4—O11−59.3 (5)C46—C47—C48—C430.0 (11)
C2—C3—C4—O11−178.7 (4)C44—C43—C48—C47−1.8 (10)
O9—C3—C4—C5−178.4 (4)Si1—C43—C48—C47−176.3 (5)
C2—C3—C4—C562.2 (5)O11—Si1—C49—C51−47.2 (5)
C53—O12—C5—C4122.3 (5)C37—Si1—C49—C51−163.7 (5)
C53—O12—C5—C6−117.8 (5)C43—Si1—C49—C5172.3 (5)
O11—C4—C5—O12−61.0 (5)O11—Si1—C49—C52−168.7 (5)
C3—C4—C5—O1257.1 (5)C37—Si1—C49—C5274.8 (6)
O11—C4—C5—C6178.5 (4)C43—Si1—C49—C52−49.2 (6)
C3—C4—C5—C6−63.4 (5)O11—Si1—C49—C5074.1 (5)
C55—O14—C6—C1−109.5 (5)C37—Si1—C49—C50−42.4 (5)
C55—O14—C6—C5131.4 (5)C43—Si1—C49—C50−166.4 (4)
O1—C1—C6—O1461.7 (6)C5—O12—C53—O1385.6 (6)
C2—C1—C6—O14179.6 (4)C54—O13—C53—O1265.8 (8)
O1—C1—C6—C5−178.5 (4)C56—O15—C55—O14−72.3 (7)
C2—C1—C6—C5−60.5 (6)C6—O14—C55—O15−73.3 (7)
O12—C5—C6—O1464.5 (6)C28B—O7—C28A—C29A60.1 (15)
C4—C5—C6—O14−176.7 (4)P2—O7—C28A—C29A154.4 (5)
O12—C5—C6—C1−56.6 (6)C29A—C30A—C31A—C32A5 (2)
C4—C5—C6—C162.2 (5)C30A—C31A—C32A—C33A−2 (2)
P1—O4—C7—C8171.3 (4)C31A—C32A—C33A—C34A0.6 (19)
O4—C7—C8—C13177.5 (5)C32A—C33A—C34A—C29A−2.1 (16)
O4—C7—C8—C9−3.9 (8)C33A—C34A—C29A—C30A4.8 (9)
C13—C8—C9—C10−1.2 (9)C33A—C34A—C29A—C28A178.4 (15)
C7—C8—C9—C10−179.8 (5)C31A—C30A—C29A—C34A−5.9 (15)
C8—C9—C10—C11−0.1 (9)C31A—C30A—C29A—C28A−179.6 (11)
C9—C10—C11—C12−0.2 (9)O7—C28A—C29A—C34A119.2 (4)
C10—C11—C12—C131.7 (9)O7—C28A—C29A—C30A−67.3 (13)
C9—C8—C13—C122.7 (9)C28A—O7—C28B—C29B−68.7 (17)
C7—C8—C13—C12−178.6 (5)P2—O7—C28B—C29B−177.4 (13)
C11—C12—C13—C8−2.9 (9)C29B—C30B—C31B—C32B4 (4)
P1—O3—C14—C15−170.9 (4)C30B—C31B—C32B—C33B−4 (4)
O3—C14—C15—C16−99.6 (7)C31B—C32B—C33B—C34B7 (4)
O3—C14—C15—C2077.4 (7)C32B—C33B—C34B—C29B−9 (3)
C20—C15—C16—C17−1.2 (10)C33B—C34B—C29B—C30B9 (4)
C14—C15—C16—C17175.8 (6)C33B—C34B—C29B—C28B−172 (3)
C15—C16—C17—C182.4 (10)C31B—C30B—C29B—C34B−7 (4)
C16—C17—C18—C19−1.1 (11)C31B—C30B—C29B—C28B174 (2)
C17—C18—C19—C20−1.4 (12)O7—C28B—C29B—C34B67 (3)
C18—C19—C20—C152.6 (11)O7—C28B—C29B—C30B−114 (2)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C8–C13 ring.
D—H···AD—HH···AD···AD—H···A
C19—H19···O13i0.952.503.342 (9)148
C32A—H32A···O10ii0.952.303.243 (11)173
C14—H14B···Cg1iii0.992.863.832 (7)168
Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) −x+1, −y+1, z; (iii) x−1/2, −y+1/2, −z+2.

Experimental details

Crystal data
Chemical formulaC56H68O15P2Si
Mr1071.13
Crystal system, space groupOrthorhombic, P21212
Temperature (K)118
a, b, c (Å)10.4052 (7), 53.019 (3), 10.0786 (6)
V (Å3)5560.1 (6)
Z4
Radiation typeMo Kα
µ (mm−1)0.17
Crystal size (mm)0.50 × 0.42 × 0.05
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
[SADABS (Bruker, 2005); Blessing (1995)]
Tmin, Tmax0.600, 0.745
No. of measured, independent and
observed [I > 2σ(I)] reflections		68347, 8042, 7297
Rint0.081
(sin θ/λ)max (Å−1)0.601
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.071, 0.181, 1.04
No. of reflections8042
No. of parameters655
No. of restraints16
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
w = 1/[σ2(Fo2) + (0.1107P)2 + 10.0351P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å−3)0.38, −0.43
Absolute structureFlack (1983), 2324 Friedel pairs
Absolute structure parameter0.12 (15)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005) and SADABS (Bruker, 2005), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C8–C13 ring.
D—H···AD—HH···AD···AD—H···A
C19—H19···O13i0.952.503.342 (9)148
C32A—H32A···O10ii0.952.303.243 (11)173
C14—H14B···Cg1iii0.992.863.832 (7)168
Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) −x+1, −y+1, z; (iii) x−1/2, −y+1/2, −z+2.
 

Acknowledgements

This work was supported by a New Zealand Foundation for Research Science and Technology grant (contract No. IRLX0502). We thank Drs J. Wikaira and C. Fitchett of the University of Canterbury for their assistance.

References

First citationAllen, F. H. (2002). Acta Cryst. B58, 380–388.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationBello, D., Aslam, T., Bultynck, G., Slawin, A. M. Z., Roderick, H. L., Bootman, M. D. & Conway, S. J. (2007). J. Org. Chem. 72, 5647–5650.  Web of Science CSD CrossRef PubMed CAS Google Scholar
 First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
 First citationBlessing, R. H. (1995). Acta Cryst. A51, 33–38.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationBruker (2005). APEX2, SAINT and SADABS . Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationKubiak, R. J. & Bruzik, K. S. (2003). J. Org. Chem. 68, 960–968.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationMacrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSato, K.-I., Akai, S., Shoji, H., Sugita, N., Yoshida, S., Nagai, Y., Suzuki, K., Nakamura, Y., Kaijihara, Y., Funabashi, M. & Yoshimura, Y. (2008). J. Org. Chem. 73, 1234–1242.  Web of Science CSD CrossRef PubMed CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals 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.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 3| March 2012| Page o900
doi:10.1107/S1600536812008069
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS