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Acta Cryst. (2007). E63, o3359    [ doi:10.1107/S1600536807031479 ]

(R)-3,3'-Diphenyl-5,6,7,8,5',6',7',8'-octahydro-1,1'-binaphthyl-2,2'-diyl chlorophosphate

Y.-P. Li and S. W. Ng

Abstract top

The two fused ring systems in the 1,1'-bi-2-naphthol derivative title compound, C32H28ClO3P, are twisted by 61.1 (1)° about the linking C-C bond, thus conferring chirality on the molecule. In one of the fused ring systems, the four-atom aliphatic chain is disordered over two sites in a 0.5:0.5 ratio.

Comment top

3,3'-Diphenyl-5,6,7,8,5',6',7',8'-octahydro-[1,1']-binaphthalenyl-2,2'-phosphate is a highly enantioselective catalyst (Chen et al., 2006) as is starting reactant 3,3'-diphenyl-5,6,7,8,5',6',7',8'-octahydro-[1,1']-binaphthalenyl-2,2'-diol (McDougal & Schaus, 2003). The reaction of the diol with phosphorus oxychloride has yielded the title chlorophosphate, (I), (Fig. 1) which is also expected to exhibit such activity.

Related literature top

For a report on the enantioselective catalytic property of the related 3,3'-diphenyl-5,6,7,8,5',6',7',8'-octahydro-[1,1']-binaphthalenyl-2,2'-phosphate, see Chen et al. (2006). For a report on the synthesis of the 3,3'-diphenyl-5,6,7,8,5',6',7',8'-octahydro-[1,1']-binaphthalenyl-2,2'-diol reactant, see McDougal & Schaus (2003).

Experimental top

To a solution of (R)-3,3'-diphenyl-5,6,7,8,5',6',7',8'-octahydro-[1,1'] binaphthalenyl-2,2'-diol (2 mmol) in pyridine (5 ml) was added phosphorus oxychloride (4.0 mmol) at room temperature under nitrogen. The mixture was stirred at 343 K for 3 h. The solvent was then removed and the product purified by column chromatography on silica gel. Colorless blocks of (I) were obtained by recrystallization from ethanol.

Refinement top

The aliphatic portion of one of the two ten-membered fused rings is disordered over two sites. Its carbon-carbon distances were restrained to within 1.50±0.01 Å, and the Uij values were restrained to nearly isotropic behaviour. As the disorder refined to nearly 50:50, the ratio was fixed as 50:50.

The carbon-bound H-atoms were generated geometrically (C–H 0.93 – 0.97 Å), and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C,O).

The configuration in the studied crystal is the R-enantiomer.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006 or??2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures top
[Figure 1] Fig. 1. View of the molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level (H atoms as spheres of arbitrary radius). The disorder is not shown.
(R)-3,3'-Diphenyl-5,6,7,8,5',6',7',8'-octahydro-1,1'-binaphthyl- 2,2'-diyl chlorophosphate top
Crystal data top
C32H28ClO3PF(000) = 1104
Mr = 526.96Dx = 1.320 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac abCell parameters from 7841 reflections
a = 12.6642 (8) Åθ = 2.2–23.6°
b = 13.1613 (8) ŵ = 0.24 mm−1
c = 15.9097 (9) ÅT = 295 K
V = 2651.8 (3) Å3Block, colorless
Z = 40.32 × 0.17 × 0.07 mm
Data collection top
Bruker APEX CCD
diffractometer		4949 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
graphiteθmax = 27.5°, θmin = 2.2°
φ and ω scansh = −16→16
33491 measured reflectionsk = −17→16
6089 independent reflectionsl = −20→20
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)] = 0.037H-atom parameters constrained
wR(F2) = 0.099 w = 1/[σ2(Fo2) + (0.0547P)2 + 0.1321P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
6089 reflectionsΔρmax = 0.16 e Å−3
370 parametersΔρmin = −0.23 e Å−3
52 restraintsAbsolute structure: Flack (1983), 2674 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.02 (6)
Crystal data top
C32H28ClO3PV = 2651.8 (3) Å3
Mr = 526.96Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 12.6642 (8) ŵ = 0.24 mm−1
b = 13.1613 (8) ÅT = 295 K
c = 15.9097 (9) Å0.32 × 0.17 × 0.07 mm
Data collection top
Bruker APEX CCD
diffractometer		4949 reflections with I > 2σ(I)
33491 measured reflectionsRint = 0.032
6089 independent reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.099Δρmax = 0.16 e Å−3
S = 1.03Δρmin = −0.23 e Å−3
6089 reflectionsAbsolute structure: Flack (1983), 2674 Friedel pairs
370 parametersFlack parameter: 0.02 (6)
52 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.69670 (4)0.39625 (5)0.93762 (4)0.06273 (16)
P10.82905 (4)0.40064 (4)0.87055 (3)0.04711 (13)
O10.88918 (10)0.30781 (10)0.91181 (8)0.0459 (3)
O20.89086 (10)0.49825 (10)0.89966 (8)0.0464 (3)
O30.81117 (12)0.39828 (14)0.78038 (9)0.0666 (4)
C10.99403 (18)0.15174 (17)0.81908 (14)0.0541 (5)
C21.0106 (2)0.0517 (2)0.84163 (17)0.0743 (7)
H21.06030.03610.88270.089*
C30.9543 (3)−0.0251 (2)0.8038 (2)0.0937 (9)
H30.9651−0.09210.82050.112*
C40.8838 (3)−0.0043 (3)0.7430 (2)0.0931 (10)
H40.8458−0.05680.71810.112*
C50.8675 (3)0.0940 (3)0.71751 (18)0.0898 (9)
H50.81980.10780.67460.108*
C60.9218 (2)0.1723 (2)0.75553 (16)0.0727 (7)
H60.91000.23900.73860.087*
C71.05299 (14)0.37665 (14)0.96221 (11)0.0398 (4)
C81.00118 (14)0.30754 (15)0.91088 (11)0.0420 (4)
C91.05190 (15)0.23363 (15)0.86370 (12)0.0456 (4)
C101.16196 (16)0.23720 (16)0.86518 (13)0.0497 (5)
H101.19950.18780.83600.060*
C111.21748 (15)0.31100 (17)0.90821 (12)0.0477 (5)
C121.16399 (14)0.38174 (15)0.95733 (11)0.0445 (4)
C131.33695 (16)0.3147 (2)0.89788 (15)0.0648 (6)
H13A1.36550.24810.91080.078*
H13B1.35310.32920.83950.078*
C141.39153 (16)0.3922 (2)0.95210 (17)0.0703 (7)
H14A1.40260.36391.00770.084*
H14B1.46020.40750.92820.084*
C151.32899 (18)0.4890 (2)0.95974 (18)0.0704 (7)
H15A1.31850.51850.90450.085*
H15B1.36770.53760.99370.085*
C161.22350 (17)0.46740 (19)0.99976 (16)0.0612 (6)
H16A1.18070.52850.99780.073*
H16B1.23440.45011.05840.073*
C171.0695 (7)0.3533 (7)1.1426 (6)0.050 (2)0.50
H17A1.04310.28911.12140.059*0.50
H17B1.14250.36041.12510.059*0.50
C181.0632 (9)0.3543 (9)1.2377 (6)0.126 (5)0.50
H18A1.12870.38321.25830.152*0.50
H18B1.06140.28411.25620.152*0.50
C190.9729 (7)0.4097 (7)1.2819 (5)0.092 (2)0.50
H19A0.90660.37541.27070.111*0.50
H19B0.98460.40981.34220.111*0.50
C200.9683 (8)0.5169 (7)1.2499 (5)0.068 (3)0.50
H20A1.03530.55121.25850.081*0.50
H20B0.91320.55501.27820.081*0.50
C17'1.0817 (8)0.3751 (8)1.1556 (6)0.067 (3)0.50
H17C1.10620.32041.11970.081*0.50
H17D1.14250.41611.17060.081*0.50
C18'1.0346 (6)0.3299 (5)1.2351 (4)0.0596 (18)0.50
H18C0.96630.29891.22490.072*0.50
H18D1.08140.28081.26110.072*0.50
C19'1.0257 (6)0.4258 (5)1.2857 (4)0.078 (2)0.50
H19C1.01030.40921.34380.094*0.50
H19D1.09220.46231.28400.094*0.50
C20'0.9400 (7)0.4909 (8)1.2510 (5)0.068 (3)0.50
H20C0.94330.55681.27810.081*0.50
H20D0.87250.46061.26530.081*0.50
C210.99091 (14)0.44335 (15)1.01926 (12)0.0407 (4)
C220.91440 (14)0.50784 (14)0.98597 (12)0.0424 (4)
C230.85660 (15)0.57704 (15)1.03315 (14)0.0490 (5)
C240.87462 (17)0.57417 (18)1.11978 (15)0.0592 (6)
H240.83840.61951.15410.071*
C250.94419 (17)0.50649 (18)1.15635 (12)0.0585 (6)
C261.00400 (15)0.44054 (16)1.10670 (12)0.0484 (5)
C270.77742 (17)0.64701 (16)0.99610 (17)0.0581 (6)
C280.6822 (2)0.6646 (2)1.0379 (2)0.0778 (8)
H280.66870.63191.08860.093*
C290.6082 (2)0.7297 (3)1.0048 (3)0.1066 (12)
H290.54490.74051.03310.128*
C300.6273 (3)0.7787 (3)0.9303 (3)0.1088 (13)
H300.57630.82150.90760.131*
C310.7210 (3)0.7649 (2)0.8894 (2)0.0928 (10)
H310.73500.80020.83990.111*
C320.7958 (2)0.69762 (18)0.92191 (18)0.0714 (7)
H320.85870.68690.89310.086*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0366 (2)0.0759 (4)0.0756 (3)0.0012 (3)0.0016 (2)0.0015 (3)
P10.0374 (2)0.0571 (3)0.0468 (3)0.0049 (2)−0.0062 (2)−0.0003 (2)
O10.0359 (6)0.0487 (8)0.0532 (8)0.0021 (6)−0.0048 (6)−0.0029 (6)
O20.0410 (7)0.0504 (8)0.0476 (7)0.0046 (6)−0.0005 (5)0.0040 (6)
O30.0625 (9)0.0863 (11)0.0510 (8)0.0101 (9)−0.0140 (7)−0.0041 (8)
C10.0601 (12)0.0541 (13)0.0482 (12)0.0031 (10)0.0055 (10)−0.0119 (10)
C20.0904 (19)0.0542 (15)0.0783 (18)0.0092 (13)−0.0051 (14)−0.0167 (13)
C30.128 (3)0.0570 (16)0.096 (2)0.0008 (18)0.003 (2)−0.0223 (15)
C40.108 (2)0.082 (2)0.089 (2)−0.0242 (18)0.0082 (19)−0.0389 (17)
C50.099 (2)0.097 (2)0.0735 (17)−0.0095 (19)−0.0192 (15)−0.0266 (17)
C60.0865 (18)0.0690 (16)0.0626 (15)−0.0006 (14)−0.0148 (13)−0.0146 (12)
C70.0365 (8)0.0427 (10)0.0403 (9)0.0039 (7)−0.0010 (7)0.0008 (7)
C80.0359 (9)0.0480 (11)0.0421 (10)0.0041 (8)−0.0029 (7)−0.0002 (8)
C90.0485 (10)0.0461 (11)0.0423 (10)0.0068 (8)−0.0019 (9)−0.0021 (8)
C100.0509 (11)0.0513 (11)0.0470 (11)0.0162 (9)0.0059 (9)−0.0005 (9)
C110.0387 (9)0.0582 (12)0.0463 (10)0.0090 (9)0.0007 (8)0.0103 (9)
C120.0354 (8)0.0522 (11)0.0458 (10)0.0026 (8)−0.0010 (7)0.0024 (8)
C130.0395 (10)0.0830 (17)0.0720 (15)0.0167 (11)0.0080 (10)0.0097 (13)
C140.0356 (10)0.0850 (17)0.0901 (17)0.0012 (12)−0.0020 (10)0.0225 (15)
C150.0482 (12)0.0728 (16)0.0902 (18)−0.0076 (11)−0.0053 (12)0.0125 (13)
C160.0432 (11)0.0640 (14)0.0763 (14)−0.0081 (10)−0.0002 (10)−0.0099 (12)
C170.041 (3)0.065 (4)0.043 (4)0.001 (3)−0.008 (2)−0.003 (3)
C180.166 (9)0.137 (8)0.076 (5)0.039 (7)−0.013 (6)−0.010 (5)
C190.108 (5)0.121 (6)0.048 (3)−0.048 (5)−0.002 (4)0.003 (3)
C200.069 (5)0.089 (6)0.045 (3)−0.006 (4)0.006 (3)−0.016 (3)
C17'0.072 (5)0.085 (6)0.045 (4)0.011 (4)−0.012 (3)−0.001 (4)
C18'0.075 (3)0.058 (3)0.046 (3)−0.021 (3)−0.015 (3)0.014 (2)
C19'0.081 (4)0.099 (5)0.053 (3)−0.017 (4)−0.010 (3)−0.012 (3)
C20'0.071 (5)0.084 (6)0.048 (4)−0.010 (4)0.005 (3)−0.016 (3)
C210.0337 (8)0.0426 (10)0.0459 (10)−0.0023 (8)0.0018 (7)−0.0036 (8)
C220.0345 (8)0.0467 (11)0.0459 (10)−0.0032 (8)0.0018 (7)−0.0008 (8)
C230.0385 (9)0.0420 (11)0.0664 (13)0.0006 (8)0.0041 (9)−0.0078 (9)
C240.0507 (11)0.0632 (14)0.0636 (13)0.0060 (10)0.0095 (10)−0.0188 (11)
C250.0500 (11)0.0778 (16)0.0477 (12)0.0016 (11)0.0022 (9)−0.0139 (11)
C260.0415 (10)0.0582 (13)0.0456 (11)0.0005 (9)0.0002 (8)−0.0038 (9)
C270.0485 (11)0.0443 (11)0.0814 (16)0.0058 (9)−0.0034 (11)−0.0111 (11)
C280.0533 (13)0.0681 (16)0.112 (2)0.0156 (12)0.0060 (14)−0.0163 (14)
C290.0623 (17)0.091 (2)0.166 (4)0.0345 (17)−0.009 (2)−0.033 (2)
C300.083 (2)0.069 (2)0.175 (4)0.0355 (17)−0.043 (2)−0.025 (2)
C310.101 (2)0.0539 (16)0.123 (3)0.0139 (15)−0.030 (2)0.0059 (16)
C320.0642 (14)0.0524 (14)0.0977 (19)0.0071 (12)−0.0093 (13)0.0046 (13)
Geometric parameters (Å, °) top
Cl1—P11.9878 (7)C17—H17B0.9700
P1—O31.4526 (15)C18—C191.528 (8)
P1—O21.5741 (14)C18—H18A0.9700
P1—O11.5822 (14)C18—H18B0.9700
O1—C81.418 (2)C19—C201.501 (8)
O2—C221.411 (2)C19—H19A0.9700
C1—C21.381 (3)C19—H19B0.9700
C1—C61.390 (3)C20—C251.525 (7)
C1—C91.484 (3)C20—H20A0.9700
C2—C31.376 (4)C20—H20B0.9700
C2—H20.9300C17'—C18'1.520 (8)
C3—C41.346 (5)C17'—C261.522 (8)
C3—H30.9300C17'—H17C0.9700
C4—C51.371 (5)C17'—H17D0.9700
C4—H40.9300C18'—C19'1.502 (7)
C5—C61.379 (4)C18'—H18C0.9700
C5—H50.9300C18'—H18D0.9700
C6—H60.9300C19'—C20'1.489 (8)
C7—C81.387 (3)C19'—H19C0.9700
C7—C121.410 (2)C19'—H19D0.9700
C7—C211.487 (2)C20'—C251.521 (7)
C8—C91.386 (3)C20'—H20C0.9700
C9—C101.395 (3)C20'—H20D0.9700
C10—C111.381 (3)C21—C221.393 (3)
C10—H100.9300C21—C261.401 (3)
C11—C121.391 (3)C22—C231.389 (3)
C11—C131.523 (3)C23—C241.398 (3)
C12—C161.515 (3)C23—C271.484 (3)
C13—C141.505 (4)C24—C251.381 (3)
C13—H13A0.9700C24—H240.9300
C13—H13B0.9700C25—C261.397 (3)
C14—C151.505 (3)C27—C321.375 (4)
C14—H14A0.9700C27—C281.396 (3)
C14—H14B0.9700C28—C291.375 (4)
C15—C161.507 (3)C28—H280.9300
C15—H15A0.9700C29—C301.371 (5)
C15—H15B0.9700C29—H290.9300
C16—H16A0.9700C30—C311.367 (5)
C16—H16B0.9700C30—H300.9300
C17—C181.514 (8)C31—C321.396 (4)
C17—C261.528 (7)C31—H310.9300
C17—H17A0.9700C32—H320.9300
O3—P1—O2112.68 (9)C19—C18—H18B107.3
O3—P1—O1117.92 (9)H18A—C18—H18B106.9
O2—P1—O1105.59 (7)C20—C19—C18108.7 (8)
O3—P1—Cl1113.46 (7)C20—C19—H19A110.0
O2—P1—Cl1106.56 (6)C18—C19—H19A110.0
O1—P1—Cl199.24 (6)C20—C19—H19B110.0
C8—O1—P1118.61 (13)C18—C19—H19B110.0
C22—O2—P1117.68 (12)H19A—C19—H19B108.3
C2—C1—C6118.3 (2)C19—C20—C25104.8 (6)
C2—C1—C9119.5 (2)C19—C20—H20A110.8
C6—C1—C9122.1 (2)C25—C20—H20A110.8
C3—C2—C1120.5 (3)C19—C20—H20B110.8
C3—C2—H2119.7C25—C20—H20B110.8
C1—C2—H2119.7H20A—C20—H20B108.9
C4—C3—C2120.6 (3)C18'—C17'—C26113.1 (7)
C4—C3—H3119.7C18'—C17'—H17C109.0
C2—C3—H3119.7C26—C17'—H17C109.0
C3—C4—C5120.3 (3)C18'—C17'—H17D109.0
C3—C4—H4119.8C26—C17'—H17D109.0
C5—C4—H4119.8H17C—C17'—H17D107.8
C4—C5—C6120.1 (3)C19'—C18'—C17'98.4 (7)
C4—C5—H5120.0C19'—C18'—H18C112.1
C6—C5—H5120.0C17'—C18'—H18C112.1
C5—C6—C1120.1 (3)C19'—C18'—H18D112.1
C5—C6—H6120.0C17'—C18'—H18D112.1
C1—C6—H6120.0H18C—C18'—H18D109.7
C8—C7—C12118.06 (17)C20'—C19'—C18'109.8 (7)
C8—C7—C21119.75 (15)C20'—C19'—H19C109.7
C12—C7—C21122.19 (16)C18'—C19'—H19C109.7
C9—C8—C7124.03 (16)C20'—C19'—H19D109.7
C9—C8—O1118.08 (17)C18'—C19'—H19D109.7
C7—C8—O1117.72 (16)H19C—C19'—H19D108.2
C8—C9—C10115.48 (18)C19'—C20'—C25114.8 (7)
C8—C9—C1122.66 (17)C19'—C20'—H20C108.6
C10—C9—C1121.74 (18)C25—C20'—H20C108.6
C11—C10—C9122.75 (18)C19'—C20'—H20D108.6
C11—C10—H10118.6C25—C20'—H20D108.6
C9—C10—H10118.6H20C—C20'—H20D107.5
C10—C11—C12120.08 (17)C22—C21—C26118.42 (17)
C10—C11—C13118.4 (2)C22—C21—C7119.69 (16)
C12—C11—C13121.5 (2)C26—C21—C7121.84 (17)
C11—C12—C7118.99 (18)C23—C22—C21124.11 (18)
C11—C12—C16120.40 (17)C23—C22—O2118.26 (17)
C7—C12—C16120.46 (17)C21—C22—O2117.55 (16)
C14—C13—C11114.6 (2)C22—C23—C24115.42 (19)
C14—C13—H13A108.6C22—C23—C27123.27 (19)
C11—C13—H13A108.6C24—C23—C27121.26 (19)
C14—C13—H13B108.6C25—C24—C23122.48 (19)
C11—C13—H13B108.6C25—C24—H24118.8
H13A—C13—H13B107.6C23—C24—H24118.8
C15—C14—C13112.25 (19)C24—C25—C26120.55 (19)
C15—C14—H14A109.2C24—C25—C20'118.8 (4)
C13—C14—H14A109.2C26—C25—C20'119.7 (4)
C15—C14—H14B109.2C24—C25—C20118.7 (4)
C13—C14—H14B109.2C26—C25—C20119.9 (5)
H14A—C14—H14B107.9C25—C26—C21118.74 (18)
C14—C15—C16109.9 (2)C25—C26—C17'114.4 (4)
C14—C15—H15A109.7C21—C26—C17'126.8 (4)
C16—C15—H15A109.7C25—C26—C17123.4 (4)
C14—C15—H15B109.7C21—C26—C17117.1 (4)
C16—C15—H15B109.7C32—C27—C28118.3 (2)
H15A—C15—H15B108.2C32—C27—C23121.8 (2)
C15—C16—C12113.2 (2)C28—C27—C23119.8 (2)
C15—C16—H16A108.9C29—C28—C27120.7 (3)
C12—C16—H16A108.9C29—C28—H28119.7
C15—C16—H16B108.9C27—C28—H28119.7
C12—C16—H16B108.9C28—C29—C30120.3 (3)
H16A—C16—H16B107.8C28—C29—H29119.9
C18—C17—C26109.8 (7)C30—C29—H29119.9
C18—C17—H17A109.7C31—C30—C29120.2 (3)
C26—C17—H17A109.7C31—C30—H30119.9
C18—C17—H17B109.7C29—C30—H30119.9
C26—C17—H17B109.7C30—C31—C32119.8 (3)
H17A—C17—H17B108.2C30—C31—H31120.1
C17—C18—C19120.3 (9)C32—C31—H31120.1
C17—C18—H18A107.3C27—C32—C31120.7 (3)
C19—C18—H18A107.3C27—C32—H32119.6
C17—C18—H18B107.3C31—C32—H32119.6
O3—P1—O1—C884.18 (16)C12—C7—C21—C26−61.5 (3)
O2—P1—O1—C8−42.76 (15)C26—C21—C22—C236.4 (3)
Cl1—P1—O1—C8−152.95 (12)C7—C21—C22—C23−176.17 (17)
O3—P1—O2—C22−178.91 (13)C26—C21—C22—O2−170.31 (17)
O1—P1—O2—C22−48.85 (13)C7—C21—C22—O27.1 (2)
Cl1—P1—O2—C2256.04 (13)P1—O2—C22—C23−105.79 (17)
C6—C1—C2—C3−2.1 (4)P1—O2—C22—C2171.10 (18)
C9—C1—C2—C3177.0 (2)C21—C22—C23—C24−4.2 (3)
C1—C2—C3—C41.5 (5)O2—C22—C23—C24172.50 (17)
C2—C3—C4—C50.3 (5)C21—C22—C23—C27178.32 (19)
C3—C4—C5—C6−1.5 (5)O2—C22—C23—C27−5.0 (3)
C4—C5—C6—C10.8 (5)C22—C23—C24—C25−0.7 (3)
C2—C1—C6—C51.0 (4)C27—C23—C24—C25176.9 (2)
C9—C1—C6—C5−178.1 (2)C23—C24—C25—C263.2 (3)
C12—C7—C8—C99.3 (3)C23—C24—C25—C20'−165.5 (5)
C21—C7—C8—C9−171.49 (18)C23—C24—C25—C20173.0 (4)
C12—C7—C8—O1−175.67 (17)C19'—C20'—C25—C24−173.4 (5)
C21—C7—C8—O13.6 (3)C19'—C20'—C25—C2617.8 (9)
P1—O1—C8—C9−113.98 (17)C19'—C20'—C25—C20−78 (2)
P1—O1—C8—C770.7 (2)C19—C20—C25—C24140.2 (6)
C7—C8—C9—C10−5.0 (3)C19—C20—C25—C26−49.9 (8)
O1—C8—C9—C10179.97 (17)C19—C20—C25—C20'45 (2)
C7—C8—C9—C1171.05 (19)C24—C25—C26—C21−0.9 (3)
O1—C8—C9—C1−4.0 (3)C20'—C25—C26—C21167.7 (4)
C2—C1—C9—C8−117.0 (3)C20—C25—C26—C21−170.7 (4)
C6—C1—C9—C862.0 (3)C24—C25—C26—C17'176.5 (5)
C2—C1—C9—C1058.8 (3)C20'—C25—C26—C17'−14.9 (7)
C6—C1—C9—C10−122.2 (3)C20—C25—C26—C17'6.7 (7)
C8—C9—C10—C11−2.1 (3)C24—C25—C26—C17−170.4 (5)
C1—C9—C10—C11−178.14 (18)C20'—C25—C26—C17−1.8 (7)
C9—C10—C11—C124.5 (3)C20—C25—C26—C1719.9 (7)
C9—C10—C11—C13−173.4 (2)C22—C21—C26—C25−3.6 (3)
C10—C11—C12—C70.0 (3)C7—C21—C26—C25179.01 (18)
C13—C11—C12—C7177.81 (19)C22—C21—C26—C17'179.4 (6)
C10—C11—C12—C16−175.7 (2)C7—C21—C26—C17'2.0 (6)
C13—C11—C12—C162.2 (3)C22—C21—C26—C17166.5 (5)
C8—C7—C12—C11−6.5 (3)C7—C21—C26—C17−10.9 (5)
C21—C7—C12—C11174.34 (17)C18'—C17'—C26—C2544.0 (9)
C8—C7—C12—C16169.16 (19)C18'—C17'—C26—C21−138.8 (5)
C21—C7—C12—C16−10.0 (3)C18'—C17'—C26—C17−87 (3)
C10—C11—C13—C14−175.55 (19)C18—C17—C26—C25−2.9 (10)
C12—C11—C13—C146.6 (3)C18—C17—C26—C21−172.5 (6)
C11—C13—C14—C15−38.1 (3)C18—C17—C26—C17'53 (3)
C13—C14—C15—C1661.0 (3)C22—C23—C27—C32−42.4 (3)
C14—C15—C16—C12−51.5 (3)C24—C23—C27—C32140.2 (2)
C11—C12—C16—C1520.8 (3)C22—C23—C27—C28139.1 (2)
C7—C12—C16—C15−154.8 (2)C24—C23—C27—C28−38.3 (3)
C26—C17—C18—C1920.1 (14)C32—C27—C28—C291.0 (4)
C17—C18—C19—C20−53.2 (13)C23—C27—C28—C29179.6 (3)
C18—C19—C20—C2562.4 (9)C27—C28—C29—C30−0.3 (5)
C26—C17'—C18'—C19'−70.3 (8)C28—C29—C30—C31−1.4 (5)
C17'—C18'—C19'—C20'71.4 (8)C29—C30—C31—C322.4 (5)
C18'—C19'—C20'—C25−48.8 (10)C28—C27—C32—C310.0 (4)
C8—C7—C21—C22−58.1 (2)C23—C27—C32—C31−178.5 (2)
C12—C7—C21—C22121.1 (2)C30—C31—C32—C27−1.8 (4)
C8—C7—C21—C26119.3 (2)
Acknowledgements top

We thank China West Normal University (grant No. 05B024) and the University of Malaya for supporting this study.

references
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