organic compounds
(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
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 et al. (1968); Aikawa et al. (2004). For the synthesis, see: Saito et al. (2001). For a related structure, see: Jones et al. (2003).
and catalysis using this type of chiral ligand, see: HornerExperimental
Crystal data
|
Data collection: SMART (Siemens, 1996); cell SAINT (Siemens, 1996); data reduction: SAINT; 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.
Supporting information
10.1107/S1600536809015335/hb2954sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809015335/hb2954Isup2.hkl
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.
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).
Data collection: SMART (Siemens, 1996); cell
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).Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level. H atoms have been omitted for clarity. |
C38H28O4P2 | F(000) = 1272 |
Mr = 610.54 | Dx = 1.305 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 4758 reflections |
a = 10.4735 (10) Å | θ = 2.2–23.5° |
b = 15.8362 (15) Å | µ = 0.18 mm−1 |
c = 18.7349 (17) Å | T = 295 K |
V = 3107.4 (5) Å3 | Block, colourless |
Z = 4 | 0.22 × 0.20 × 0.17 mm |
Siemens SMART CCD diffractometer | 5515 independent reflections |
Radiation source: fine-focus sealed tube | 4665 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
ω scans | θmax = 25.1°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Siemens, 1996) | h = −12→8 |
Tmin = 0.961, Tmax = 0.970 | k = −18→18 |
16522 measured reflections | l = −20→22 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H-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 reflections | Δρmax = 0.25 e Å−3 |
397 parameters | Δρmin = −0.16 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 2403 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.06 (8) |
C38H28O4P2 | V = 3107.4 (5) Å3 |
Mr = 610.54 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 10.4735 (10) Å | µ = 0.18 mm−1 |
b = 15.8362 (15) Å | T = 295 K |
c = 18.7349 (17) Å | 0.22 × 0.20 × 0.17 mm |
Siemens SMART CCD diffractometer | 5515 independent reflections |
Absorption correction: multi-scan (SADABS; Siemens, 1996) | 4665 reflections with I > 2σ(I) |
Tmin = 0.961, Tmax = 0.970 | Rint = 0.031 |
16522 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.083 | Δρmax = 0.25 e Å−3 |
S = 1.03 | Δρmin = −0.16 e Å−3 |
5515 reflections | Absolute structure: Flack (1983), 2403 Friedel pairs |
397 parameters | Absolute structure parameter: 0.06 (8) |
0 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
P1 | 0.58912 (6) | 0.58094 (4) | 0.84832 (3) | 0.04188 (15) | |
P2 | 0.59298 (6) | 0.53283 (4) | 0.65667 (3) | 0.04263 (15) | |
O1 | 0.13104 (16) | 0.70954 (11) | 0.69648 (11) | 0.0662 (5) | |
O2 | 0.33097 (16) | 0.74812 (10) | 0.65651 (9) | 0.0569 (4) | |
O3 | 0.57161 (16) | 0.83894 (9) | 0.76483 (9) | 0.0518 (4) | |
O4 | 0.76116 (17) | 0.88509 (10) | 0.71511 (10) | 0.0597 (5) | |
C1 | 0.4390 (2) | 0.61654 (13) | 0.80753 (11) | 0.0355 (5) | |
C2 | 0.3188 (2) | 0.59414 (14) | 0.83092 (12) | 0.0432 (5) | |
H2 | 0.3117 | 0.5596 | 0.8709 | 0.052* | |
C3 | 0.2068 (2) | 0.62152 (15) | 0.79677 (14) | 0.0499 (6) | |
H3 | 0.1262 | 0.6048 | 0.8122 | 0.060* | |
C4 | 0.2228 (2) | 0.67396 (15) | 0.73985 (13) | 0.0461 (6) | |
C5 | 0.1990 (3) | 0.77173 (19) | 0.65656 (17) | 0.0694 (8) | |
H5A | 0.1885 | 0.8269 | 0.6783 | 0.083* | |
H5B | 0.1668 | 0.7742 | 0.6081 | 0.083* | |
C6 | 0.3422 (2) | 0.69712 (13) | 0.71610 (12) | 0.0402 (5) | |
C7 | 0.4530 (2) | 0.66937 (13) | 0.74655 (11) | 0.0359 (5) | |
C8 | 0.5330 (2) | 0.51007 (14) | 0.91959 (11) | 0.0406 (5) | |
C9 | 0.5239 (3) | 0.42500 (15) | 0.90265 (13) | 0.0541 (6) | |
H9 | 0.5446 | 0.4071 | 0.8568 | 0.065* | |
C10 | 0.4845 (3) | 0.36647 (17) | 0.95267 (16) | 0.0665 (8) | |
H10 | 0.4774 | 0.3098 | 0.9404 | 0.080* | |
C11 | 0.4561 (3) | 0.39259 (18) | 1.02055 (15) | 0.0652 (8) | |
H11 | 0.4300 | 0.3534 | 1.0545 | 0.078* | |
C12 | 0.4660 (2) | 0.47679 (18) | 1.03892 (13) | 0.0589 (7) | |
H12 | 0.4472 | 0.4942 | 1.0852 | 0.071* | |
C13 | 0.5039 (2) | 0.53493 (16) | 0.98843 (12) | 0.0478 (6) | |
H13 | 0.5099 | 0.5916 | 1.0008 | 0.057* | |
C14 | 0.6373 (2) | 0.67684 (15) | 0.89654 (12) | 0.0440 (6) | |
C15 | 0.5534 (3) | 0.73889 (16) | 0.91921 (13) | 0.0544 (7) | |
H15 | 0.4665 | 0.7325 | 0.9107 | 0.065* | |
C16 | 0.5973 (3) | 0.81080 (17) | 0.95458 (15) | 0.0649 (7) | |
H16 | 0.5395 | 0.8516 | 0.9699 | 0.078* | |
C17 | 0.7256 (3) | 0.82148 (19) | 0.96687 (16) | 0.0703 (8) | |
H17 | 0.7552 | 0.8691 | 0.9907 | 0.084* | |
C18 | 0.8092 (3) | 0.7612 (2) | 0.94363 (17) | 0.0736 (9) | |
H18 | 0.8962 | 0.7686 | 0.9514 | 0.088* | |
C19 | 0.7667 (3) | 0.68914 (17) | 0.90862 (14) | 0.0608 (7) | |
H19 | 0.8252 | 0.6489 | 0.8932 | 0.073* | |
C20 | 0.6520 (2) | 0.64110 (13) | 0.67129 (12) | 0.0419 (5) | |
C21 | 0.5790 (2) | 0.69450 (13) | 0.71579 (11) | 0.0360 (5) | |
C22 | 0.6264 (2) | 0.77484 (14) | 0.72645 (12) | 0.0400 (5) | |
C23 | 0.6690 (3) | 0.90246 (15) | 0.76970 (14) | 0.0581 (7) | |
H23A | 0.6323 | 0.9581 | 0.7628 | 0.070* | |
H23B | 0.7091 | 0.9008 | 0.8163 | 0.070* | |
C24 | 0.7386 (2) | 0.80219 (14) | 0.69604 (13) | 0.0463 (6) | |
C25 | 0.8098 (2) | 0.75234 (15) | 0.65207 (15) | 0.0568 (7) | |
H25 | 0.8847 | 0.7716 | 0.6309 | 0.068* | |
C26 | 0.7641 (2) | 0.67079 (15) | 0.64068 (14) | 0.0538 (6) | |
H26 | 0.8106 | 0.6347 | 0.6114 | 0.065* | |
C27 | 0.7379 (2) | 0.46870 (14) | 0.66098 (12) | 0.0443 (5) | |
C28 | 0.8398 (3) | 0.48831 (17) | 0.70534 (13) | 0.0580 (7) | |
H28 | 0.8393 | 0.5391 | 0.7303 | 0.070* | |
C29 | 0.9414 (3) | 0.4341 (2) | 0.71318 (14) | 0.0687 (8) | |
H29 | 1.0092 | 0.4491 | 0.7427 | 0.082* | |
C30 | 0.9438 (3) | 0.3586 (2) | 0.67796 (15) | 0.0732 (9) | |
H30 | 1.0125 | 0.3220 | 0.6838 | 0.088* | |
C31 | 0.8450 (3) | 0.33712 (17) | 0.63417 (16) | 0.0689 (8) | |
H31 | 0.8466 | 0.2859 | 0.6099 | 0.083* | |
C32 | 0.7425 (3) | 0.39115 (15) | 0.62571 (14) | 0.0580 (7) | |
H32 | 0.6754 | 0.3755 | 0.5960 | 0.070* | |
C33 | 0.5558 (2) | 0.53725 (14) | 0.56069 (12) | 0.0433 (5) | |
C34 | 0.4283 (2) | 0.55116 (16) | 0.54330 (14) | 0.0575 (7) | |
H34 | 0.3679 | 0.5560 | 0.5795 | 0.069* | |
C35 | 0.3904 (3) | 0.55778 (19) | 0.47284 (15) | 0.0703 (8) | |
H35 | 0.3053 | 0.5683 | 0.4619 | 0.084* | |
C36 | 0.4780 (3) | 0.54888 (18) | 0.41902 (14) | 0.0660 (8) | |
H36 | 0.4523 | 0.5530 | 0.3716 | 0.079* | |
C37 | 0.6031 (3) | 0.53395 (17) | 0.43509 (13) | 0.0596 (7) | |
H37 | 0.6621 | 0.5272 | 0.3984 | 0.072* | |
C38 | 0.6431 (2) | 0.52869 (16) | 0.50546 (12) | 0.0526 (6) | |
H38 | 0.7289 | 0.5194 | 0.5157 | 0.063* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0382 (3) | 0.0438 (3) | 0.0437 (3) | 0.0045 (3) | 0.0006 (3) | 0.0023 (3) |
P2 | 0.0426 (3) | 0.0394 (3) | 0.0459 (3) | −0.0018 (3) | 0.0061 (3) | −0.0014 (3) |
O1 | 0.0412 (10) | 0.0677 (12) | 0.0899 (14) | 0.0021 (9) | −0.0192 (9) | 0.0103 (11) |
O2 | 0.0532 (10) | 0.0582 (11) | 0.0592 (10) | 0.0064 (8) | −0.0073 (9) | 0.0185 (9) |
O3 | 0.0507 (10) | 0.0390 (9) | 0.0656 (11) | −0.0013 (8) | 0.0148 (8) | −0.0060 (8) |
O4 | 0.0539 (11) | 0.0432 (10) | 0.0821 (12) | −0.0109 (8) | 0.0146 (10) | −0.0049 (9) |
C1 | 0.0357 (12) | 0.0337 (11) | 0.0373 (11) | 0.0005 (9) | 0.0019 (9) | −0.0017 (9) |
C2 | 0.0429 (13) | 0.0415 (13) | 0.0450 (13) | −0.0033 (10) | 0.0062 (11) | 0.0020 (11) |
C3 | 0.0339 (13) | 0.0518 (15) | 0.0640 (16) | −0.0072 (11) | 0.0047 (12) | 0.0000 (13) |
C4 | 0.0353 (13) | 0.0432 (13) | 0.0599 (15) | 0.0029 (11) | −0.0070 (11) | −0.0050 (12) |
C5 | 0.0551 (17) | 0.0711 (18) | 0.082 (2) | 0.0082 (14) | −0.0180 (16) | 0.0153 (17) |
C6 | 0.0420 (13) | 0.0360 (12) | 0.0427 (12) | 0.0032 (10) | −0.0004 (11) | −0.0010 (10) |
C7 | 0.0352 (11) | 0.0319 (11) | 0.0406 (11) | −0.0014 (10) | 0.0023 (10) | −0.0035 (9) |
C8 | 0.0400 (13) | 0.0379 (13) | 0.0438 (12) | 0.0033 (10) | −0.0059 (10) | 0.0017 (10) |
C9 | 0.0653 (17) | 0.0457 (14) | 0.0514 (14) | 0.0057 (13) | −0.0047 (13) | −0.0014 (12) |
C10 | 0.087 (2) | 0.0408 (14) | 0.0721 (19) | −0.0049 (14) | −0.0048 (17) | 0.0085 (14) |
C11 | 0.0703 (19) | 0.0642 (18) | 0.0612 (17) | −0.0080 (14) | −0.0057 (15) | 0.0241 (15) |
C12 | 0.0607 (17) | 0.0720 (19) | 0.0439 (14) | −0.0015 (14) | −0.0014 (12) | 0.0045 (14) |
C13 | 0.0515 (14) | 0.0477 (13) | 0.0442 (13) | 0.0031 (12) | −0.0024 (11) | −0.0005 (12) |
C14 | 0.0413 (13) | 0.0462 (13) | 0.0444 (13) | −0.0037 (11) | −0.0049 (10) | 0.0084 (11) |
C15 | 0.0477 (16) | 0.0526 (15) | 0.0631 (16) | −0.0027 (12) | −0.0066 (12) | −0.0030 (13) |
C16 | 0.0681 (19) | 0.0528 (15) | 0.0737 (18) | −0.0040 (15) | −0.0105 (16) | −0.0095 (14) |
C17 | 0.080 (2) | 0.0600 (17) | 0.0712 (19) | −0.0237 (17) | −0.0169 (17) | −0.0010 (15) |
C18 | 0.0518 (18) | 0.086 (2) | 0.083 (2) | −0.0229 (18) | −0.0204 (16) | 0.0056 (18) |
C19 | 0.0469 (15) | 0.0660 (18) | 0.0694 (18) | −0.0028 (13) | −0.0099 (14) | 0.0054 (15) |
C20 | 0.0418 (13) | 0.0382 (12) | 0.0459 (13) | −0.0038 (10) | 0.0028 (11) | 0.0011 (10) |
C21 | 0.0336 (11) | 0.0405 (12) | 0.0339 (11) | 0.0006 (10) | 0.0012 (10) | 0.0059 (9) |
C22 | 0.0368 (13) | 0.0385 (12) | 0.0447 (13) | 0.0018 (10) | 0.0017 (10) | 0.0042 (11) |
C23 | 0.0644 (17) | 0.0405 (14) | 0.0695 (17) | −0.0057 (13) | 0.0094 (14) | −0.0018 (13) |
C24 | 0.0414 (13) | 0.0397 (13) | 0.0577 (15) | −0.0038 (11) | 0.0036 (12) | 0.0022 (11) |
C25 | 0.0441 (14) | 0.0530 (16) | 0.0734 (17) | −0.0072 (12) | 0.0185 (14) | −0.0015 (14) |
C26 | 0.0488 (14) | 0.0477 (14) | 0.0648 (16) | −0.0005 (12) | 0.0209 (13) | −0.0060 (13) |
C27 | 0.0494 (13) | 0.0410 (12) | 0.0427 (12) | 0.0027 (11) | 0.0052 (11) | 0.0049 (11) |
C28 | 0.0612 (17) | 0.0672 (17) | 0.0457 (14) | 0.0074 (14) | −0.0004 (13) | −0.0052 (13) |
C29 | 0.0667 (19) | 0.091 (2) | 0.0487 (15) | 0.0180 (17) | −0.0089 (14) | −0.0006 (15) |
C30 | 0.074 (2) | 0.083 (2) | 0.0626 (18) | 0.0319 (17) | 0.0057 (16) | 0.0224 (16) |
C31 | 0.085 (2) | 0.0463 (15) | 0.075 (2) | 0.0162 (15) | 0.0055 (17) | 0.0044 (14) |
C32 | 0.0641 (17) | 0.0459 (15) | 0.0639 (16) | 0.0037 (13) | −0.0066 (14) | 0.0035 (13) |
C33 | 0.0415 (14) | 0.0377 (12) | 0.0507 (13) | 0.0012 (10) | 0.0002 (11) | −0.0044 (11) |
C34 | 0.0472 (15) | 0.0657 (17) | 0.0596 (15) | 0.0099 (13) | 0.0031 (13) | −0.0031 (13) |
C35 | 0.0551 (17) | 0.085 (2) | 0.0706 (19) | 0.0149 (15) | −0.0136 (15) | −0.0028 (15) |
C36 | 0.079 (2) | 0.0689 (19) | 0.0498 (15) | 0.0104 (16) | −0.0144 (15) | 0.0018 (13) |
C37 | 0.0664 (19) | 0.0635 (16) | 0.0489 (14) | 0.0081 (16) | 0.0090 (13) | 0.0026 (13) |
C38 | 0.0444 (14) | 0.0623 (15) | 0.0511 (14) | 0.0081 (13) | 0.0030 (11) | 0.0020 (13) |
P1—C1 | 1.837 (2) | C16—C17 | 1.374 (4) |
P1—C14 | 1.838 (2) | C16—H16 | 0.9300 |
P1—C8 | 1.841 (2) | C17—C18 | 1.367 (4) |
P2—C27 | 1.828 (2) | C17—H17 | 0.9300 |
P2—C33 | 1.841 (2) | C18—C19 | 1.390 (4) |
P2—C20 | 1.843 (2) | C18—H18 | 0.9300 |
O1—C4 | 1.379 (3) | C19—H19 | 0.9300 |
O1—C5 | 1.427 (3) | C20—C26 | 1.389 (3) |
O2—C6 | 1.383 (3) | C20—C21 | 1.412 (3) |
O2—C5 | 1.432 (3) | C21—C22 | 1.380 (3) |
O3—C22 | 1.370 (3) | C22—C24 | 1.375 (3) |
O3—C23 | 1.435 (3) | C23—H23A | 0.9700 |
O4—C24 | 1.381 (3) | C23—H23B | 0.9700 |
O4—C23 | 1.433 (3) | C24—C25 | 1.363 (3) |
C1—C2 | 1.379 (3) | C25—C26 | 1.394 (3) |
C1—C7 | 1.424 (3) | C25—H25 | 0.9300 |
C2—C3 | 1.405 (3) | C26—H26 | 0.9300 |
C2—H2 | 0.9300 | C27—C28 | 1.388 (3) |
C3—C4 | 1.362 (3) | C27—C32 | 1.395 (3) |
C3—H3 | 0.9300 | C28—C29 | 1.375 (4) |
C4—C6 | 1.377 (3) | C28—H28 | 0.9300 |
C5—H5A | 0.9700 | C29—C30 | 1.367 (4) |
C5—H5B | 0.9700 | C29—H29 | 0.9300 |
C6—C7 | 1.366 (3) | C30—C31 | 1.364 (4) |
C7—C21 | 1.494 (3) | C30—H30 | 0.9300 |
C8—C13 | 1.382 (3) | C31—C32 | 1.382 (4) |
C8—C9 | 1.387 (3) | C31—H31 | 0.9300 |
C9—C10 | 1.381 (4) | C32—H32 | 0.9300 |
C9—H9 | 0.9300 | C33—C38 | 1.388 (3) |
C10—C11 | 1.370 (4) | C33—C34 | 1.392 (3) |
C10—H10 | 0.9300 | C34—C35 | 1.382 (4) |
C11—C12 | 1.381 (4) | C34—H34 | 0.9300 |
C11—H11 | 0.9300 | C35—C36 | 1.371 (4) |
C12—C13 | 1.378 (3) | C35—H35 | 0.9300 |
C12—H12 | 0.9300 | C36—C37 | 1.365 (4) |
C13—H13 | 0.9300 | C36—H36 | 0.9300 |
C14—C15 | 1.385 (3) | C37—C38 | 1.386 (3) |
C14—C19 | 1.388 (3) | C37—H37 | 0.9300 |
C15—C16 | 1.395 (3) | C38—H38 | 0.9300 |
C15—H15 | 0.9300 | ||
C1—P1—C14 | 100.70 (10) | C17—C18—H18 | 119.4 |
C1—P1—C8 | 102.44 (10) | C19—C18—H18 | 119.4 |
C14—P1—C8 | 103.58 (10) | C14—C19—C18 | 120.4 (3) |
C27—P2—C33 | 103.89 (10) | C14—C19—H19 | 119.8 |
C27—P2—C20 | 103.41 (11) | C18—C19—H19 | 119.8 |
C33—P2—C20 | 100.41 (10) | C26—C20—C21 | 119.9 (2) |
C4—O1—C5 | 104.07 (19) | C26—C20—P2 | 122.49 (18) |
C6—O2—C5 | 103.55 (19) | C21—C20—P2 | 117.62 (16) |
C22—O3—C23 | 104.76 (18) | C22—C21—C20 | 116.30 (19) |
C24—O4—C23 | 104.59 (18) | C22—C21—C7 | 120.49 (19) |
C2—C1—C7 | 120.04 (19) | C20—C21—C7 | 123.10 (19) |
C2—C1—P1 | 124.75 (16) | O3—C22—C24 | 109.99 (19) |
C7—C1—P1 | 115.19 (15) | O3—C22—C21 | 127.47 (19) |
C1—C2—C3 | 122.6 (2) | C24—C22—C21 | 122.5 (2) |
C1—C2—H2 | 118.7 | O4—C23—O3 | 107.39 (18) |
C3—C2—H2 | 118.7 | O4—C23—H23A | 110.2 |
C4—C3—C2 | 116.2 (2) | O3—C23—H23A | 110.2 |
C4—C3—H3 | 121.9 | O4—C23—H23B | 110.2 |
C2—C3—H3 | 121.9 | O3—C23—H23B | 110.2 |
C3—C4—C6 | 121.8 (2) | H23A—C23—H23B | 108.5 |
C3—C4—O1 | 128.6 (2) | C25—C24—C22 | 122.4 (2) |
C6—C4—O1 | 109.5 (2) | C25—C24—O4 | 127.8 (2) |
O1—C5—O2 | 107.6 (2) | C22—C24—O4 | 109.8 (2) |
O1—C5—H5A | 110.2 | C24—C25—C26 | 116.2 (2) |
O2—C5—H5A | 110.2 | C24—C25—H25 | 121.9 |
O1—C5—H5B | 110.2 | C26—C25—H25 | 121.9 |
O2—C5—H5B | 110.2 | C20—C26—C25 | 122.8 (2) |
H5A—C5—H5B | 108.5 | C20—C26—H26 | 118.6 |
C7—C6—C4 | 123.4 (2) | C25—C26—H26 | 118.6 |
C7—C6—O2 | 126.7 (2) | C28—C27—C32 | 117.0 (2) |
C4—C6—O2 | 109.8 (2) | C28—C27—P2 | 122.72 (18) |
C6—C7—C1 | 115.87 (19) | C32—C27—P2 | 119.78 (19) |
C6—C7—C21 | 120.25 (19) | C29—C28—C27 | 121.3 (2) |
C1—C7—C21 | 123.88 (18) | C29—C28—H28 | 119.3 |
C13—C8—C9 | 118.3 (2) | C27—C28—H28 | 119.3 |
C13—C8—P1 | 125.00 (17) | C30—C29—C28 | 120.6 (3) |
C9—C8—P1 | 116.62 (18) | C30—C29—H29 | 119.7 |
C10—C9—C8 | 121.1 (2) | C28—C29—H29 | 119.7 |
C10—C9—H9 | 119.4 | C31—C30—C29 | 119.6 (3) |
C8—C9—H9 | 119.4 | C31—C30—H30 | 120.2 |
C11—C10—C9 | 119.5 (3) | C29—C30—H30 | 120.2 |
C11—C10—H10 | 120.3 | C30—C31—C32 | 120.3 (3) |
C9—C10—H10 | 120.3 | C30—C31—H31 | 119.9 |
C10—C11—C12 | 120.4 (2) | C32—C31—H31 | 119.9 |
C10—C11—H11 | 119.8 | C31—C32—C27 | 121.2 (3) |
C12—C11—H11 | 119.8 | C31—C32—H32 | 119.4 |
C13—C12—C11 | 119.7 (2) | C27—C32—H32 | 119.4 |
C13—C12—H12 | 120.1 | C38—C33—C34 | 118.3 (2) |
C11—C12—H12 | 120.1 | C38—C33—P2 | 125.78 (18) |
C12—C13—C8 | 120.9 (2) | C34—C33—P2 | 115.96 (18) |
C12—C13—H13 | 119.6 | C35—C34—C33 | 120.7 (2) |
C8—C13—H13 | 119.6 | C35—C34—H34 | 119.6 |
C15—C14—C19 | 118.0 (2) | C33—C34—H34 | 119.6 |
C15—C14—P1 | 124.29 (18) | C36—C35—C34 | 120.2 (3) |
C19—C14—P1 | 117.7 (2) | C36—C35—H35 | 119.9 |
C14—C15—C16 | 121.1 (3) | C34—C35—H35 | 119.9 |
C14—C15—H15 | 119.5 | C37—C36—C35 | 119.9 (3) |
C16—C15—H15 | 119.5 | C37—C36—H36 | 120.1 |
C17—C16—C15 | 120.1 (3) | C35—C36—H36 | 120.1 |
C17—C16—H16 | 119.9 | C36—C37—C38 | 120.7 (3) |
C15—C16—H16 | 119.9 | C36—C37—H37 | 119.7 |
C18—C17—C16 | 119.2 (3) | C38—C37—H37 | 119.7 |
C18—C17—H17 | 120.4 | C37—C38—C33 | 120.3 (2) |
C16—C17—H17 | 120.4 | C37—C38—H38 | 119.9 |
C17—C18—C19 | 121.2 (3) | C33—C38—H38 | 119.9 |
C14—P1—C1—C2 | −104.4 (2) | C27—P2—C20—C21 | −138.78 (17) |
C8—P1—C1—C2 | 2.2 (2) | C33—P2—C20—C21 | 114.08 (18) |
C14—P1—C1—C7 | 77.10 (17) | C26—C20—C21—C22 | −0.4 (3) |
C8—P1—C1—C7 | −176.25 (15) | P2—C20—C21—C22 | 179.22 (16) |
C7—C1—C2—C3 | 0.0 (3) | C26—C20—C21—C7 | 175.6 (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—C22 | 75.5 (3) |
C2—C3—C4—C6 | 1.5 (4) | C1—C7—C21—C22 | −104.6 (2) |
C2—C3—C4—O1 | 179.4 (2) | C6—C7—C21—C20 | −100.4 (3) |
C5—O1—C4—C3 | 168.0 (3) | C1—C7—C21—C20 | 79.5 (3) |
C5—O1—C4—C6 | −14.0 (3) | C23—O3—C22—C24 | −12.2 (3) |
C4—O1—C5—O2 | 22.8 (3) | C23—O3—C22—C21 | 169.9 (2) |
C6—O2—C5—O1 | −22.8 (3) | C20—C21—C22—O3 | 177.4 (2) |
C3—C4—C6—C7 | 0.7 (4) | C7—C21—C22—O3 | 1.2 (3) |
O1—C4—C6—C7 | −177.6 (2) | C20—C21—C22—C24 | −0.3 (3) |
C3—C4—C6—O2 | 178.0 (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—O4 | 18.5 (3) |
C5—O2—C6—C4 | 14.2 (3) | O3—C22—C24—C25 | −176.8 (2) |
C4—C6—C7—C1 | −2.5 (3) | C21—C22—C24—C25 | 1.2 (4) |
O2—C6—C7—C1 | −179.40 (19) | O3—C22—C24—O4 | 1.1 (3) |
C4—C6—C7—C21 | 177.4 (2) | C21—C22—C24—O4 | 179.2 (2) |
O2—C6—C7—C21 | 0.5 (3) | C23—O4—C24—C25 | −171.8 (3) |
C2—C1—C7—C6 | 2.1 (3) | C23—O4—C24—C22 | 10.4 (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—C21 | 0.8 (3) | C21—C20—C26—C25 | 0.3 (4) |
C1—P1—C8—C13 | −89.2 (2) | P2—C20—C26—C25 | −179.4 (2) |
C14—P1—C8—C13 | 15.2 (2) | C24—C25—C26—C20 | 0.6 (4) |
C1—P1—C8—C9 | 93.1 (2) | C33—P2—C27—C28 | 138.3 (2) |
C14—P1—C8—C9 | −162.46 (19) | C20—P2—C27—C28 | 33.8 (2) |
C13—C8—C9—C10 | 1.2 (4) | C33—P2—C27—C32 | −50.1 (2) |
P1—C8—C9—C10 | 179.0 (2) | C20—P2—C27—C32 | −154.56 (19) |
C8—C9—C10—C11 | −1.1 (4) | C32—C27—C28—C29 | 1.0 (4) |
C9—C10—C11—C12 | 0.3 (4) | P2—C27—C28—C29 | 172.9 (2) |
C10—C11—C12—C13 | 0.5 (4) | C27—C28—C29—C30 | −0.9 (4) |
C11—C12—C13—C8 | −0.4 (4) | C28—C29—C30—C31 | 0.6 (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—C27 | 0.5 (4) |
C1—P1—C14—C15 | 24.7 (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—C19 | 101.4 (2) | C20—P2—C33—C38 | 81.0 (2) |
C19—C14—C15—C16 | −1.4 (4) | C27—P2—C33—C34 | 154.78 (19) |
P1—C14—C15—C16 | −178.93 (19) | C20—P2—C33—C34 | −98.5 (2) |
C14—C15—C16—C17 | 0.7 (4) | C38—C33—C34—C35 | −1.2 (4) |
C15—C16—C17—C18 | 0.4 (4) | P2—C33—C34—C35 | 178.3 (2) |
C16—C17—C18—C19 | −0.7 (5) | C33—C34—C35—C36 | 1.4 (4) |
C15—C14—C19—C18 | 1.1 (4) | C34—C35—C36—C37 | −0.4 (5) |
P1—C14—C19—C18 | 178.8 (2) | C35—C36—C37—C38 | −0.8 (5) |
C17—C18—C19—C14 | −0.1 (4) | C36—C37—C38—C33 | 1.0 (4) |
C27—P2—C20—C26 | 40.9 (2) | C34—C33—C38—C37 | 0.0 (4) |
C33—P2—C20—C26 | −66.3 (2) | P2—C33—C38—C37 | −179.5 (2) |
Experimental details
Crystal data | |
Chemical formula | C38H28O4P2 |
Mr | 610.54 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 295 |
a, b, c (Å) | 10.4735 (10), 15.8362 (15), 18.7349 (17) |
V (Å3) | 3107.4 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.18 |
Crystal size (mm) | 0.22 × 0.20 × 0.17 |
Data collection | |
Diffractometer | Siemens SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Siemens, 1996) |
Tmin, Tmax | 0.961, 0.970 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16522, 5515, 4665 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.083, 1.03 |
No. of reflections | 5515 |
No. of parameters | 397 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.25, −0.16 |
Absolute structure | Flack (1983), 2403 Friedel pairs |
Absolute structure parameter | 0.06 (8) |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
References
Aikawa, K., Kainuma, S., Hatano, M. & Mikami, K. (2004). Tetrahedron Lett. 45, 183–185. Web of Science CSD CrossRef CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Horner, L., Siegel, H. & Buthe, H. (1968). Angew. Chem. Int. Ed. Engl. 7, 942–944. CrossRef CAS Web of Science Google Scholar
Jones, 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
Saito, 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
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART, SAINT and SADABS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. 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.
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)°.