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Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o1153.
Published online 2009 April 30. doi:  10.1107/S1600536809015335
PMCID: PMC2977819

(S)-(−)-5,5′-Bis(diphenyl­phosphino)-4,4′-bi-1,3-benzodioxole

Abstract

In the chiral title compound, C38H28O4P2, the intra­molecular P(...)P separation is 3.671 (2) Å and the dihedral angle between the two benzene rings in the biphenyl unit is 77.9 (2)°.

Related literature

For background on asymmetric synthesis and catalysis using this type of chiral ligand, see: Horner et al. (1968 [triangle]); Aikawa et al. (2004 [triangle]). For the synthesis, see: Saito et al. (2001 [triangle]). For a related structure, see: Jones et al. (2003 [triangle]).

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Object name is e-65-o1153-scheme1.jpg

Experimental

Crystal data

  • C38H28O4P2
  • M r = 610.54
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1153-efi1.jpg
  • a = 10.4735 (10) Å
  • b = 15.8362 (15) Å
  • c = 18.7349 (17) Å
  • V = 3107.4 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.18 mm−1
  • T = 295 K
  • 0.22 × 0.20 × 0.17 mm

Data collection

  • Siemens SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Siemens, 1996 [triangle]) T min = 0.961, T max = 0.970
  • 16522 measured reflections
  • 5515 independent reflections
  • 4665 reflections with I > 2σ(I)
  • R int = 0.031

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.083
  • S = 1.03
  • 5515 reflections
  • 397 parameters
  • H-atom parameters constrained
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.16 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 2403 Friedel pairs
  • Flack parameter: 0.06 (8)

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809015335/hb2954sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015335/hb2954Isup2.hkl

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

supplementary crystallographic information

Comment

The ability to selectively form one enantiomer in preference to the other (asymmetric catalysis) is undoubtedly one of the major advances in modern drug design and synthesis. Since 1968, when a chiral phosphine was first utilized in asymmetric hydrogenation (Horner et al., 1968), much effort has been devoted to the design and synthesis of chiral phosphine ligands. The synthesis of the title compound has been reported in literature (Saito et al., 2001). However, this is the first time that the crystal structure is being reported. This ligand has been used on palladium for the catalysis of ketone-ene reactions (Aikawa et al., 2004). All bond lengths and angles in (I) are normal and are comparable to those in the related compound (S)-(–)-2,2'-Bis(diphenylphosphino) -1,1'-binaphthyl (Jones et al., 2003). The key feature of (I) is the intramolecular P···P distance of 3.671 (2) Å and the two benzene rings in the biphenyl moiety make a dihedral angle of 77.9 (2)°.

Experimental

The title compound was synthesized by the literature route of Saito et al. (2001). Colourless blocks of (I) were grown by slow evaporation of a solution of the compound in a acetone-ethanol (1:1 v/v) mixture.

Refinement

All the H atoms were initially located in a difference map, relocated in idealised positions (C—H = 0.93–0.97 Å) and refined as riding with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level. H atoms have been omitted for clarity.

Crystal data

C38H28O4P2F(000) = 1272
Mr = 610.54Dx = 1.305 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4758 reflections
a = 10.4735 (10) Åθ = 2.2–23.5°
b = 15.8362 (15) ŵ = 0.18 mm1
c = 18.7349 (17) ÅT = 295 K
V = 3107.4 (5) Å3Block, colourless
Z = 40.22 × 0.20 × 0.17 mm

Data collection

Siemens SMART CCD diffractometer5515 independent reflections
Radiation source: fine-focus sealed tube4665 reflections with I > 2σ(I)
graphiteRint = 0.031
ω scansθmax = 25.1°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Siemens, 1996)h = −12→8
Tmin = 0.961, Tmax = 0.970k = −18→18
16522 measured reflectionsl = −20→22

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.083w = 1/[σ2(Fo2) + (0.0405P)2 + 0.2496P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
5515 reflectionsΔρmax = 0.25 e Å3
397 parametersΔρmin = −0.16 e Å3
0 restraintsAbsolute structure: Flack (1983), 2403 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.06 (8)

Special details

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
P10.58912 (6)0.58094 (4)0.84832 (3)0.04188 (15)
P20.59298 (6)0.53283 (4)0.65667 (3)0.04263 (15)
O10.13104 (16)0.70954 (11)0.69648 (11)0.0662 (5)
O20.33097 (16)0.74812 (10)0.65651 (9)0.0569 (4)
O30.57161 (16)0.83894 (9)0.76483 (9)0.0518 (4)
O40.76116 (17)0.88509 (10)0.71511 (10)0.0597 (5)
C10.4390 (2)0.61654 (13)0.80753 (11)0.0355 (5)
C20.3188 (2)0.59414 (14)0.83092 (12)0.0432 (5)
H20.31170.55960.87090.052*
C30.2068 (2)0.62152 (15)0.79677 (14)0.0499 (6)
H30.12620.60480.81220.060*
C40.2228 (2)0.67396 (15)0.73985 (13)0.0461 (6)
C50.1990 (3)0.77173 (19)0.65656 (17)0.0694 (8)
H5A0.18850.82690.67830.083*
H5B0.16680.77420.60810.083*
C60.3422 (2)0.69712 (13)0.71610 (12)0.0402 (5)
C70.4530 (2)0.66937 (13)0.74655 (11)0.0359 (5)
C80.5330 (2)0.51007 (14)0.91959 (11)0.0406 (5)
C90.5239 (3)0.42500 (15)0.90265 (13)0.0541 (6)
H90.54460.40710.85680.065*
C100.4845 (3)0.36647 (17)0.95267 (16)0.0665 (8)
H100.47740.30980.94040.080*
C110.4561 (3)0.39259 (18)1.02055 (15)0.0652 (8)
H110.43000.35341.05450.078*
C120.4660 (2)0.47679 (18)1.03892 (13)0.0589 (7)
H120.44720.49421.08520.071*
C130.5039 (2)0.53493 (16)0.98843 (12)0.0478 (6)
H130.50990.59161.00080.057*
C140.6373 (2)0.67684 (15)0.89654 (12)0.0440 (6)
C150.5534 (3)0.73889 (16)0.91921 (13)0.0544 (7)
H150.46650.73250.91070.065*
C160.5973 (3)0.81080 (17)0.95458 (15)0.0649 (7)
H160.53950.85160.96990.078*
C170.7256 (3)0.82148 (19)0.96687 (16)0.0703 (8)
H170.75520.86910.99070.084*
C180.8092 (3)0.7612 (2)0.94363 (17)0.0736 (9)
H180.89620.76860.95140.088*
C190.7667 (3)0.68914 (17)0.90862 (14)0.0608 (7)
H190.82520.64890.89320.073*
C200.6520 (2)0.64110 (13)0.67129 (12)0.0419 (5)
C210.5790 (2)0.69450 (13)0.71579 (11)0.0360 (5)
C220.6264 (2)0.77484 (14)0.72645 (12)0.0400 (5)
C230.6690 (3)0.90246 (15)0.76970 (14)0.0581 (7)
H23A0.63230.95810.76280.070*
H23B0.70910.90080.81630.070*
C240.7386 (2)0.80219 (14)0.69604 (13)0.0463 (6)
C250.8098 (2)0.75234 (15)0.65207 (15)0.0568 (7)
H250.88470.77160.63090.068*
C260.7641 (2)0.67079 (15)0.64068 (14)0.0538 (6)
H260.81060.63470.61140.065*
C270.7379 (2)0.46870 (14)0.66098 (12)0.0443 (5)
C280.8398 (3)0.48831 (17)0.70534 (13)0.0580 (7)
H280.83930.53910.73030.070*
C290.9414 (3)0.4341 (2)0.71318 (14)0.0687 (8)
H291.00920.44910.74270.082*
C300.9438 (3)0.3586 (2)0.67796 (15)0.0732 (9)
H301.01250.32200.68380.088*
C310.8450 (3)0.33712 (17)0.63417 (16)0.0689 (8)
H310.84660.28590.60990.083*
C320.7425 (3)0.39115 (15)0.62571 (14)0.0580 (7)
H320.67540.37550.59600.070*
C330.5558 (2)0.53725 (14)0.56069 (12)0.0433 (5)
C340.4283 (2)0.55116 (16)0.54330 (14)0.0575 (7)
H340.36790.55600.57950.069*
C350.3904 (3)0.55778 (19)0.47284 (15)0.0703 (8)
H350.30530.56830.46190.084*
C360.4780 (3)0.54888 (18)0.41902 (14)0.0660 (8)
H360.45230.55300.37160.079*
C370.6031 (3)0.53395 (17)0.43509 (13)0.0596 (7)
H370.66210.52720.39840.072*
C380.6431 (2)0.52869 (16)0.50546 (12)0.0526 (6)
H380.72890.51940.51570.063*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
P10.0382 (3)0.0438 (3)0.0437 (3)0.0045 (3)0.0006 (3)0.0023 (3)
P20.0426 (3)0.0394 (3)0.0459 (3)−0.0018 (3)0.0061 (3)−0.0014 (3)
O10.0412 (10)0.0677 (12)0.0899 (14)0.0021 (9)−0.0192 (9)0.0103 (11)
O20.0532 (10)0.0582 (11)0.0592 (10)0.0064 (8)−0.0073 (9)0.0185 (9)
O30.0507 (10)0.0390 (9)0.0656 (11)−0.0013 (8)0.0148 (8)−0.0060 (8)
O40.0539 (11)0.0432 (10)0.0821 (12)−0.0109 (8)0.0146 (10)−0.0049 (9)
C10.0357 (12)0.0337 (11)0.0373 (11)0.0005 (9)0.0019 (9)−0.0017 (9)
C20.0429 (13)0.0415 (13)0.0450 (13)−0.0033 (10)0.0062 (11)0.0020 (11)
C30.0339 (13)0.0518 (15)0.0640 (16)−0.0072 (11)0.0047 (12)0.0000 (13)
C40.0353 (13)0.0432 (13)0.0599 (15)0.0029 (11)−0.0070 (11)−0.0050 (12)
C50.0551 (17)0.0711 (18)0.082 (2)0.0082 (14)−0.0180 (16)0.0153 (17)
C60.0420 (13)0.0360 (12)0.0427 (12)0.0032 (10)−0.0004 (11)−0.0010 (10)
C70.0352 (11)0.0319 (11)0.0406 (11)−0.0014 (10)0.0023 (10)−0.0035 (9)
C80.0400 (13)0.0379 (13)0.0438 (12)0.0033 (10)−0.0059 (10)0.0017 (10)
C90.0653 (17)0.0457 (14)0.0514 (14)0.0057 (13)−0.0047 (13)−0.0014 (12)
C100.087 (2)0.0408 (14)0.0721 (19)−0.0049 (14)−0.0048 (17)0.0085 (14)
C110.0703 (19)0.0642 (18)0.0612 (17)−0.0080 (14)−0.0057 (15)0.0241 (15)
C120.0607 (17)0.0720 (19)0.0439 (14)−0.0015 (14)−0.0014 (12)0.0045 (14)
C130.0515 (14)0.0477 (13)0.0442 (13)0.0031 (12)−0.0024 (11)−0.0005 (12)
C140.0413 (13)0.0462 (13)0.0444 (13)−0.0037 (11)−0.0049 (10)0.0084 (11)
C150.0477 (16)0.0526 (15)0.0631 (16)−0.0027 (12)−0.0066 (12)−0.0030 (13)
C160.0681 (19)0.0528 (15)0.0737 (18)−0.0040 (15)−0.0105 (16)−0.0095 (14)
C170.080 (2)0.0600 (17)0.0712 (19)−0.0237 (17)−0.0169 (17)−0.0010 (15)
C180.0518 (18)0.086 (2)0.083 (2)−0.0229 (18)−0.0204 (16)0.0056 (18)
C190.0469 (15)0.0660 (18)0.0694 (18)−0.0028 (13)−0.0099 (14)0.0054 (15)
C200.0418 (13)0.0382 (12)0.0459 (13)−0.0038 (10)0.0028 (11)0.0011 (10)
C210.0336 (11)0.0405 (12)0.0339 (11)0.0006 (10)0.0012 (10)0.0059 (9)
C220.0368 (13)0.0385 (12)0.0447 (13)0.0018 (10)0.0017 (10)0.0042 (11)
C230.0644 (17)0.0405 (14)0.0695 (17)−0.0057 (13)0.0094 (14)−0.0018 (13)
C240.0414 (13)0.0397 (13)0.0577 (15)−0.0038 (11)0.0036 (12)0.0022 (11)
C250.0441 (14)0.0530 (16)0.0734 (17)−0.0072 (12)0.0185 (14)−0.0015 (14)
C260.0488 (14)0.0477 (14)0.0648 (16)−0.0005 (12)0.0209 (13)−0.0060 (13)
C270.0494 (13)0.0410 (12)0.0427 (12)0.0027 (11)0.0052 (11)0.0049 (11)
C280.0612 (17)0.0672 (17)0.0457 (14)0.0074 (14)−0.0004 (13)−0.0052 (13)
C290.0667 (19)0.091 (2)0.0487 (15)0.0180 (17)−0.0089 (14)−0.0006 (15)
C300.074 (2)0.083 (2)0.0626 (18)0.0319 (17)0.0057 (16)0.0224 (16)
C310.085 (2)0.0463 (15)0.075 (2)0.0162 (15)0.0055 (17)0.0044 (14)
C320.0641 (17)0.0459 (15)0.0639 (16)0.0037 (13)−0.0066 (14)0.0035 (13)
C330.0415 (14)0.0377 (12)0.0507 (13)0.0012 (10)0.0002 (11)−0.0044 (11)
C340.0472 (15)0.0657 (17)0.0596 (15)0.0099 (13)0.0031 (13)−0.0031 (13)
C350.0551 (17)0.085 (2)0.0706 (19)0.0149 (15)−0.0136 (15)−0.0028 (15)
C360.079 (2)0.0689 (19)0.0498 (15)0.0104 (16)−0.0144 (15)0.0018 (13)
C370.0664 (19)0.0635 (16)0.0489 (14)0.0081 (16)0.0090 (13)0.0026 (13)
C380.0444 (14)0.0623 (15)0.0511 (14)0.0081 (13)0.0030 (11)0.0020 (13)

Geometric parameters (Å, °)

P1—C11.837 (2)C16—C171.374 (4)
P1—C141.838 (2)C16—H160.9300
P1—C81.841 (2)C17—C181.367 (4)
P2—C271.828 (2)C17—H170.9300
P2—C331.841 (2)C18—C191.390 (4)
P2—C201.843 (2)C18—H180.9300
O1—C41.379 (3)C19—H190.9300
O1—C51.427 (3)C20—C261.389 (3)
O2—C61.383 (3)C20—C211.412 (3)
O2—C51.432 (3)C21—C221.380 (3)
O3—C221.370 (3)C22—C241.375 (3)
O3—C231.435 (3)C23—H23A0.9700
O4—C241.381 (3)C23—H23B0.9700
O4—C231.433 (3)C24—C251.363 (3)
C1—C21.379 (3)C25—C261.394 (3)
C1—C71.424 (3)C25—H250.9300
C2—C31.405 (3)C26—H260.9300
C2—H20.9300C27—C281.388 (3)
C3—C41.362 (3)C27—C321.395 (3)
C3—H30.9300C28—C291.375 (4)
C4—C61.377 (3)C28—H280.9300
C5—H5A0.9700C29—C301.367 (4)
C5—H5B0.9700C29—H290.9300
C6—C71.366 (3)C30—C311.364 (4)
C7—C211.494 (3)C30—H300.9300
C8—C131.382 (3)C31—C321.382 (4)
C8—C91.387 (3)C31—H310.9300
C9—C101.381 (4)C32—H320.9300
C9—H90.9300C33—C381.388 (3)
C10—C111.370 (4)C33—C341.392 (3)
C10—H100.9300C34—C351.382 (4)
C11—C121.381 (4)C34—H340.9300
C11—H110.9300C35—C361.371 (4)
C12—C131.378 (3)C35—H350.9300
C12—H120.9300C36—C371.365 (4)
C13—H130.9300C36—H360.9300
C14—C151.385 (3)C37—C381.386 (3)
C14—C191.388 (3)C37—H370.9300
C15—C161.395 (3)C38—H380.9300
C15—H150.9300
C1—P1—C14100.70 (10)C17—C18—H18119.4
C1—P1—C8102.44 (10)C19—C18—H18119.4
C14—P1—C8103.58 (10)C14—C19—C18120.4 (3)
C27—P2—C33103.89 (10)C14—C19—H19119.8
C27—P2—C20103.41 (11)C18—C19—H19119.8
C33—P2—C20100.41 (10)C26—C20—C21119.9 (2)
C4—O1—C5104.07 (19)C26—C20—P2122.49 (18)
C6—O2—C5103.55 (19)C21—C20—P2117.62 (16)
C22—O3—C23104.76 (18)C22—C21—C20116.30 (19)
C24—O4—C23104.59 (18)C22—C21—C7120.49 (19)
C2—C1—C7120.04 (19)C20—C21—C7123.10 (19)
C2—C1—P1124.75 (16)O3—C22—C24109.99 (19)
C7—C1—P1115.19 (15)O3—C22—C21127.47 (19)
C1—C2—C3122.6 (2)C24—C22—C21122.5 (2)
C1—C2—H2118.7O4—C23—O3107.39 (18)
C3—C2—H2118.7O4—C23—H23A110.2
C4—C3—C2116.2 (2)O3—C23—H23A110.2
C4—C3—H3121.9O4—C23—H23B110.2
C2—C3—H3121.9O3—C23—H23B110.2
C3—C4—C6121.8 (2)H23A—C23—H23B108.5
C3—C4—O1128.6 (2)C25—C24—C22122.4 (2)
C6—C4—O1109.5 (2)C25—C24—O4127.8 (2)
O1—C5—O2107.6 (2)C22—C24—O4109.8 (2)
O1—C5—H5A110.2C24—C25—C26116.2 (2)
O2—C5—H5A110.2C24—C25—H25121.9
O1—C5—H5B110.2C26—C25—H25121.9
O2—C5—H5B110.2C20—C26—C25122.8 (2)
H5A—C5—H5B108.5C20—C26—H26118.6
C7—C6—C4123.4 (2)C25—C26—H26118.6
C7—C6—O2126.7 (2)C28—C27—C32117.0 (2)
C4—C6—O2109.8 (2)C28—C27—P2122.72 (18)
C6—C7—C1115.87 (19)C32—C27—P2119.78 (19)
C6—C7—C21120.25 (19)C29—C28—C27121.3 (2)
C1—C7—C21123.88 (18)C29—C28—H28119.3
C13—C8—C9118.3 (2)C27—C28—H28119.3
C13—C8—P1125.00 (17)C30—C29—C28120.6 (3)
C9—C8—P1116.62 (18)C30—C29—H29119.7
C10—C9—C8121.1 (2)C28—C29—H29119.7
C10—C9—H9119.4C31—C30—C29119.6 (3)
C8—C9—H9119.4C31—C30—H30120.2
C11—C10—C9119.5 (3)C29—C30—H30120.2
C11—C10—H10120.3C30—C31—C32120.3 (3)
C9—C10—H10120.3C30—C31—H31119.9
C10—C11—C12120.4 (2)C32—C31—H31119.9
C10—C11—H11119.8C31—C32—C27121.2 (3)
C12—C11—H11119.8C31—C32—H32119.4
C13—C12—C11119.7 (2)C27—C32—H32119.4
C13—C12—H12120.1C38—C33—C34118.3 (2)
C11—C12—H12120.1C38—C33—P2125.78 (18)
C12—C13—C8120.9 (2)C34—C33—P2115.96 (18)
C12—C13—H13119.6C35—C34—C33120.7 (2)
C8—C13—H13119.6C35—C34—H34119.6
C15—C14—C19118.0 (2)C33—C34—H34119.6
C15—C14—P1124.29 (18)C36—C35—C34120.2 (3)
C19—C14—P1117.7 (2)C36—C35—H35119.9
C14—C15—C16121.1 (3)C34—C35—H35119.9
C14—C15—H15119.5C37—C36—C35119.9 (3)
C16—C15—H15119.5C37—C36—H36120.1
C17—C16—C15120.1 (3)C35—C36—H36120.1
C17—C16—H16119.9C36—C37—C38120.7 (3)
C15—C16—H16119.9C36—C37—H37119.7
C18—C17—C16119.2 (3)C38—C37—H37119.7
C18—C17—H17120.4C37—C38—C33120.3 (2)
C16—C17—H17120.4C37—C38—H38119.9
C17—C18—C19121.2 (3)C33—C38—H38119.9
C14—P1—C1—C2−104.4 (2)C27—P2—C20—C21−138.78 (17)
C8—P1—C1—C22.2 (2)C33—P2—C20—C21114.08 (18)
C14—P1—C1—C777.10 (17)C26—C20—C21—C22−0.4 (3)
C8—P1—C1—C7−176.25 (15)P2—C20—C21—C22179.22 (16)
C7—C1—C2—C30.0 (3)C26—C20—C21—C7175.6 (2)
P1—C1—C2—C3−178.44 (18)P2—C20—C21—C7−4.7 (3)
C1—C2—C3—C4−1.8 (3)C6—C7—C21—C2275.5 (3)
C2—C3—C4—C61.5 (4)C1—C7—C21—C22−104.6 (2)
C2—C3—C4—O1179.4 (2)C6—C7—C21—C20−100.4 (3)
C5—O1—C4—C3168.0 (3)C1—C7—C21—C2079.5 (3)
C5—O1—C4—C6−14.0 (3)C23—O3—C22—C24−12.2 (3)
C4—O1—C5—O222.8 (3)C23—O3—C22—C21169.9 (2)
C6—O2—C5—O1−22.8 (3)C20—C21—C22—O3177.4 (2)
C3—C4—C6—C70.7 (4)C7—C21—C22—O31.2 (3)
O1—C4—C6—C7−177.6 (2)C20—C21—C22—C24−0.3 (3)
C3—C4—C6—O2178.0 (2)C7—C21—C22—C24−176.4 (2)
O1—C4—C6—O2−0.2 (3)C24—O4—C23—O3−17.8 (3)
C5—O2—C6—C7−168.5 (2)C22—O3—C23—O418.5 (3)
C5—O2—C6—C414.2 (3)O3—C22—C24—C25−176.8 (2)
C4—C6—C7—C1−2.5 (3)C21—C22—C24—C251.2 (4)
O2—C6—C7—C1−179.40 (19)O3—C22—C24—O41.1 (3)
C4—C6—C7—C21177.4 (2)C21—C22—C24—O4179.2 (2)
O2—C6—C7—C210.5 (3)C23—O4—C24—C25−171.8 (3)
C2—C1—C7—C62.1 (3)C23—O4—C24—C2210.4 (3)
P1—C1—C7—C6−179.30 (16)C22—C24—C25—C26−1.4 (4)
C2—C1—C7—C21−177.8 (2)O4—C24—C25—C26−178.9 (2)
P1—C1—C7—C210.8 (3)C21—C20—C26—C250.3 (4)
C1—P1—C8—C13−89.2 (2)P2—C20—C26—C25−179.4 (2)
C14—P1—C8—C1315.2 (2)C24—C25—C26—C200.6 (4)
C1—P1—C8—C993.1 (2)C33—P2—C27—C28138.3 (2)
C14—P1—C8—C9−162.46 (19)C20—P2—C27—C2833.8 (2)
C13—C8—C9—C101.2 (4)C33—P2—C27—C32−50.1 (2)
P1—C8—C9—C10179.0 (2)C20—P2—C27—C32−154.56 (19)
C8—C9—C10—C11−1.1 (4)C32—C27—C28—C291.0 (4)
C9—C10—C11—C120.3 (4)P2—C27—C28—C29172.9 (2)
C10—C11—C12—C130.5 (4)C27—C28—C29—C30−0.9 (4)
C11—C12—C13—C8−0.4 (4)C28—C29—C30—C310.6 (4)
C9—C8—C13—C12−0.4 (4)C29—C30—C31—C32−0.4 (4)
P1—C8—C13—C12−178.04 (19)C30—C31—C32—C270.5 (4)
C1—P1—C14—C1524.7 (2)C28—C27—C32—C31−0.8 (4)
C8—P1—C14—C15−81.1 (2)P2—C27—C32—C31−172.9 (2)
C1—P1—C14—C19−152.86 (19)C27—P2—C33—C38−25.8 (2)
C8—P1—C14—C19101.4 (2)C20—P2—C33—C3881.0 (2)
C19—C14—C15—C16−1.4 (4)C27—P2—C33—C34154.78 (19)
P1—C14—C15—C16−178.93 (19)C20—P2—C33—C34−98.5 (2)
C14—C15—C16—C170.7 (4)C38—C33—C34—C35−1.2 (4)
C15—C16—C17—C180.4 (4)P2—C33—C34—C35178.3 (2)
C16—C17—C18—C19−0.7 (5)C33—C34—C35—C361.4 (4)
C15—C14—C19—C181.1 (4)C34—C35—C36—C37−0.4 (5)
P1—C14—C19—C18178.8 (2)C35—C36—C37—C38−0.8 (5)
C17—C18—C19—C14−0.1 (4)C36—C37—C38—C331.0 (4)
C27—P2—C20—C2640.9 (2)C34—C33—C38—C370.0 (4)
C33—P2—C20—C26−66.3 (2)P2—C33—C38—C37−179.5 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2954).

References

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