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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 5| May 2009| Page o1153

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

aShengjing Hospital of China Medical University, Shenyang 110004, People's Republic of China
*Correspondence e-mail: jianlingyan09@126.com

(Received 15 April 2009; accepted 24 April 2009; online 30 April 2009)

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[Horner, L., Siegel, H. & Buthe, H. (1968). Angew. Chem. Int. Ed. Engl. 7, 942-944.]); Aikawa et al. (2004[Aikawa, K., Kainuma, S., Hatano, M. & Mikami, K. (2004). Tetrahedron Lett. 45, 183-185.]). For the synthesis, see: Saito et al. (2001[Saito, T., Yokozawa, T., Ishizaki, T., Moroi, T., Sayo, N., Miura, T. & Kumobayashi, H. (2001). Adv. Synth. Catal 343, 264-267.]). For a related structure, see: Jones et al. (2003[Jones, M. D., Almeida Paz, F. A., Davies, J. E. & Johnson, B. F. G. (2003). Acta Cryst. E59, o535-o537.]).

[Scheme 1]

Experimental

Crystal data
  • C38H28O4P2

  • Mr = 610.54

  • Orthorhombic, P 21 21 21

  • 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[Siemens (1996). SMART, SAINT and SADABS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]) Tmin = 0.961, Tmax = 0.970

  • 16522 measured reflections

  • 5515 independent reflections

  • 4665 reflections with I > 2σ(I)

  • Rint = 0.031

Refinement
  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 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[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2403 Friedel pairs

  • Flack parameter: 0.06 (8)

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART, SAINT and SADABS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART, SAINT and SADABS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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)°.

Related literature top

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

Experimental top

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 top

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).

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level. H atoms have been omitted for clarity.
(S)-(-)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole top
Crystal data top
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 top
Siemens SMART CCD
diffractometer
5515 independent reflections
Radiation source: fine-focus sealed tube4665 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ω scansθmax = 25.1°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Siemens, 1996)
h = 128
Tmin = 0.961, Tmax = 0.970k = 1818
16522 measured reflectionsl = 2022
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)] = 0.034H-atom parameters constrained
wR(F2) = 0.083 w = 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 methodsAbsolute structure parameter: 0.06 (8)
Crystal data top
C38H28O4P2V = 3107.4 (5) Å3
Mr = 610.54Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 10.4735 (10) ŵ = 0.18 mm1
b = 15.8362 (15) ÅT = 295 K
c = 18.7349 (17) Å0.22 × 0.20 × 0.17 mm
Data collection top
Siemens SMART CCD
diffractometer
5515 independent reflections
Absorption correction: multi-scan
(SADABS; Siemens, 1996)
4665 reflections with I > 2σ(I)
Tmin = 0.961, Tmax = 0.970Rint = 0.031
16522 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.083Δρmax = 0.25 e Å3
S = 1.03Δρmin = 0.16 e Å3
5515 reflectionsAbsolute structure: Flack (1983), 2403 Friedel pairs
397 parametersAbsolute structure parameter: 0.06 (8)
0 restraints
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, º) top
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—C2104.4 (2)C27—P2—C20—C21138.78 (17)
C8—P1—C1—C22.2 (2)C33—P2—C20—C21114.08 (18)
C14—P1—C1—C777.10 (17)C26—C20—C21—C220.4 (3)
C8—P1—C1—C7176.25 (15)P2—C20—C21—C22179.22 (16)
C7—C1—C2—C30.0 (3)C26—C20—C21—C7175.6 (2)
P1—C1—C2—C3178.44 (18)P2—C20—C21—C74.7 (3)
C1—C2—C3—C41.8 (3)C6—C7—C21—C2275.5 (3)
C2—C3—C4—C61.5 (4)C1—C7—C21—C22104.6 (2)
C2—C3—C4—O1179.4 (2)C6—C7—C21—C20100.4 (3)
C5—O1—C4—C3168.0 (3)C1—C7—C21—C2079.5 (3)
C5—O1—C4—C614.0 (3)C23—O3—C22—C2412.2 (3)
C4—O1—C5—O222.8 (3)C23—O3—C22—C21169.9 (2)
C6—O2—C5—O122.8 (3)C20—C21—C22—O3177.4 (2)
C3—C4—C6—C70.7 (4)C7—C21—C22—O31.2 (3)
O1—C4—C6—C7177.6 (2)C20—C21—C22—C240.3 (3)
C3—C4—C6—O2178.0 (2)C7—C21—C22—C24176.4 (2)
O1—C4—C6—O20.2 (3)C24—O4—C23—O317.8 (3)
C5—O2—C6—C7168.5 (2)C22—O3—C23—O418.5 (3)
C5—O2—C6—C414.2 (3)O3—C22—C24—C25176.8 (2)
C4—C6—C7—C12.5 (3)C21—C22—C24—C251.2 (4)
O2—C6—C7—C1179.40 (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—C25171.8 (3)
C2—C1—C7—C62.1 (3)C23—O4—C24—C2210.4 (3)
P1—C1—C7—C6179.30 (16)C22—C24—C25—C261.4 (4)
C2—C1—C7—C21177.8 (2)O4—C24—C25—C26178.9 (2)
P1—C1—C7—C210.8 (3)C21—C20—C26—C250.3 (4)
C1—P1—C8—C1389.2 (2)P2—C20—C26—C25179.4 (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—C9162.46 (19)C20—P2—C27—C2833.8 (2)
C13—C8—C9—C101.2 (4)C33—P2—C27—C3250.1 (2)
P1—C8—C9—C10179.0 (2)C20—P2—C27—C32154.56 (19)
C8—C9—C10—C111.1 (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—C300.9 (4)
C11—C12—C13—C80.4 (4)C28—C29—C30—C310.6 (4)
C9—C8—C13—C120.4 (4)C29—C30—C31—C320.4 (4)
P1—C8—C13—C12178.04 (19)C30—C31—C32—C270.5 (4)
C1—P1—C14—C1524.7 (2)C28—C27—C32—C310.8 (4)
C8—P1—C14—C1581.1 (2)P2—C27—C32—C31172.9 (2)
C1—P1—C14—C19152.86 (19)C27—P2—C33—C3825.8 (2)
C8—P1—C14—C19101.4 (2)C20—P2—C33—C3881.0 (2)
C19—C14—C15—C161.4 (4)C27—P2—C33—C34154.78 (19)
P1—C14—C15—C16178.93 (19)C20—P2—C33—C3498.5 (2)
C14—C15—C16—C170.7 (4)C38—C33—C34—C351.2 (4)
C15—C16—C17—C180.4 (4)P2—C33—C34—C35178.3 (2)
C16—C17—C18—C190.7 (5)C33—C34—C35—C361.4 (4)
C15—C14—C19—C181.1 (4)C34—C35—C36—C370.4 (5)
P1—C14—C19—C18178.8 (2)C35—C36—C37—C380.8 (5)
C17—C18—C19—C140.1 (4)C36—C37—C38—C331.0 (4)
C27—P2—C20—C2640.9 (2)C34—C33—C38—C370.0 (4)
C33—P2—C20—C2666.3 (2)P2—C33—C38—C37179.5 (2)

Experimental details

Crystal data
Chemical formulaC38H28O4P2
Mr610.54
Crystal system, space groupOrthorhombic, P212121
Temperature (K)295
a, b, c (Å)10.4735 (10), 15.8362 (15), 18.7349 (17)
V3)3107.4 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.18
Crystal size (mm)0.22 × 0.20 × 0.17
Data collection
DiffractometerSiemens SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Siemens, 1996)
Tmin, Tmax0.961, 0.970
No. of measured, independent and
observed [I > 2σ(I)] reflections
16522, 5515, 4665
Rint0.031
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.083, 1.03
No. of reflections5515
No. of parameters397
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.25, 0.16
Absolute structureFlack (1983), 2403 Friedel pairs
Absolute structure parameter0.06 (8)

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

References

First citationAikawa, K., Kainuma, S., Hatano, M. & Mikami, K. (2004). Tetrahedron Lett. 45, 183–185.  Web of Science CSD CrossRef CAS Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationHorner, L., Siegel, H. & Buthe, H. (1968). Angew. Chem. Int. Ed. Engl. 7, 942–944.  CrossRef CAS Web of Science Google Scholar
First citationJones, M. D., Almeida Paz, F. A., Davies, J. E. & Johnson, B. F. G. (2003). Acta Cryst. E59, o535–o537.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSaito, T., Yokozawa, T., Ishizaki, T., Moroi, T., Sayo, N., Miura, T. & Kumobayashi, H. (2001). Adv. Synth. Catal 343, 264–267.  Web of Science CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSiemens (1996). SMART, SAINT and SADABS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar

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Volume 65| Part 5| May 2009| Page o1153
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