(+)-(RR)-{μ-m-Phenyl­ene­di­methyl­enebis­[tert-butyl(phenyl)­phosphine]}bis­(borane)

The title compound, C₂₈H₄₂B₂P₂, (II), was synthesized with >95% enantiomeric excess, and the relative and absolute configuration was determined. Both P atoms have distorted tetrahedral geometry, and the average B—P—C angle and P—B distance are 112.7 (6)° and 1.910 (6) Å, respectively.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.035
• wR factor = 0.088
• Data-to-parameter ratio = 17.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



RADNW_01  Alert C The radiation wavelength lies outside the expected range
          for the supplied radiation type. Expected range 1.54175-1.54180
          Wavelength given =    1.54056

General Notes



RADNW_01  The radiation wavelength given implies that Cu Kalpha1 has
          been used. Please check that this is correct.
          Wavelength given =    1.54056

REFLT_03
         From the CIF: _diffrn_reflns_theta_max           69.84
         From the CIF: _reflns_number_total               5320
         Count of symmetry unique reflns         3046
         Completeness (_total/calc)            174.66%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured      2274
         Fraction of Friedel pairs measured     0.747
         Are heavy atom types Z>Si present          yes
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

S1. Comment

The importance of phosphine ligands in transition metal chemistry is remarkable. Among them optically active C₂-symmetric phosphine ligands proved to be instrumental in asymmetric catalysis (Yamanoi & Imamoto, 1999). Recently, P-chiral phosphines have emerged as a good chiral controller in transition metal-catalyzed reaction (Kolodiazhnyi, 1998). Transition metal complexes with phosphorus–carbon–phosphorus (PCP) tridentate or pincer ligands were studied extensively (Laurenti & Santelli, 1999). However, to our knowledge, no structure of a pincer ligand with P-chiral phosphines has been reported so far. Therefore, we wish to report the first crystallographic structure of a P-chiral PCP tridentate ligand as a bis-boron complex.

Fig. 1 clearly indicates the C₂-symmetry of (II). The two phosphorus substituents are on opposite sides of the aromatic ring. Both P atoms have adopted a distorted tetrahedral geometry. The average B—P—C angle and P—B distance are 112.7 (6)° and 1.910 (6) Å, respectively (Table 1).

S2. Experimental

According the literature procedure of Wolfe & Livinghouse (1998), the enantioselective alkylation of the phosphine–borane (I) with the lithium–sparteine complex afforded the desired C₂-symmetric diphosphine in 54% yield and 98.5% ee, contaminated with 5% of the meso diastereoisomer. Recrystallization from dichloromethane/ether afforded the enantio- and diastereomerically pure (>99%) bis(phosphine–borane) (II). Optical rotation of (II): [a]_D = +127.6 (c 2.78, CHCl₃).

S3. Refinement

The title compound, (II), is quite stable and can be stored for months on the bench, whitout any significant decomposition. It might be sensitive to the X-ray especially since it was a linear decay, which was corrected. H atoms were constrained to the parent site using a riding model; SHELXL96 defaults, C—H = 0.93–0.97 Å and B—H = 0.96 Å. The isotropic factors, U_iso, were adjusted to 150% of the value of the parent site for methyl and B—H H atoms and 120% for other H atoms.

Computing details

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: NRC-2 and NRC-2A (Ahmed et al., 1973); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL96 (Sheldrick, 1996); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXL96.

Figures

Fig. 1. ORTEP drawing of the title molecule. Ellipsoids correspond to 40% probability.

(I)

Crystal data

C28H42B2P2	Dx = 1.092 Mg m^−3
Mr = 462.18	Cu Kα radiation, λ = 1.54056 Å
Orthorhombic, P212121	Cell parameters from 25 reflections
a = 7.380 (6) Å	θ = 20.0–21.0°
b = 13.515 (6) Å	µ = 1.48 mm^−1
c = 28.189 (14) Å	T = 293 K
V = 2812 (3) Å^3	Block, colourless
Z = 4	0.83 × 0.22 × 0.14 mm
F(000) = 1000.0

Data collection

Nonius CAD-4 diffractometer	4737 reflections with I > 2σ(I)
Radiation source: normal-focus xray tube	Rint = 0.062
Graphite monochromator	θmax = 69.8°, θmin = 3.1°
ω scans	h = −8→8
Absorption correction: integration (ABSORP in NRCVAX; Gabe et al., 1989)	k = −16→16
Tmin = 0.539, Tmax = 0.830	l = −34→34
30802 measured reflections	5 standard reflections every 60 min
5320 independent reflections	intensity decay: 21.7%

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.035	w = 1/[σ^2(Fo^2) + (0.0491P)^2P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.088	(Δ/σ)max = 0.001
S = 0.98	Δρmax = 0.21 e Å^−3
5320 reflections	Δρmin = −0.22 e Å^−3
298 parameters	Extinction correction: SHELXL96, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0028 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 2274 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.004 (18)

Special details

Experimental. To a solution of (-)-sparteine (0.65 ml, 2.85 mmole) and t-butylphenylphosphine-borane (I) (453 mg, 2.52 mmole) in 15 ml of ether at -78°C was added n-butyllithium (2.00 M in hexanes, 1.30 ml, 2.52 mmole). The reaction was warmed to room temperature and stirred for 1 h, then cooled back to -78°C. The α,α'-dibromo-o-xylene (300 mg, 0.84 mmole) in THF (1.5 ml) was added drop wise. The resulting mixture was warmed to room temperature and stirred for 18 h. The reaction was quenched with 5% aqueous sulfuric acid (2 ml) and extracted with dichloromethane (3 x 10 ml). The combined organic phases were washed with water (5 ml) and brine (5 ml), then dried over MgSO₄. The solvent was removed under reduced pressure. The desired diphosphine-borane product (II) (194 mg, 0.45 mmole, 54%) was obtained as a white solid after flash chromatography on silica gel (50% DCM/Hexane). The enantiomeric excess was determined to be 98.5% (140:1) by chiral HPLC analysis (Chiracel OD, 1 ml/min, 20% 2-propanol/hexanes, tR 5.93 (major), 7.19 (meso) 8.06 (minor)). The compound (II) was recrystallized from DCM/Ether.

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. A final verification of possible voids was performed using the VOID routine of the PLATON program (Spek, 1995).

Refinement of F² against ALL reflections. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating R-factor_obs 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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.8903 (3)	0.47164 (17)	0.10781 (7)	0.0446 (5)
H1	0.8054	0.4254	0.0977	0.054*
C2	0.8552 (3)	0.52642 (16)	0.14833 (7)	0.0453 (5)
C3	0.9813 (4)	0.59595 (18)	0.16291 (7)	0.0574 (6)
H3	0.9602	0.6335	0.1900	0.069*
C4	1.1381 (4)	0.6092 (2)	0.13715 (8)	0.0646 (7)
H4	1.2224	0.6560	0.1470	0.077*
C5	1.1717 (4)	0.55390 (18)	0.09688 (7)	0.0563 (6)
H5	1.2780	0.5641	0.0798	0.068*
C6	1.0494 (3)	0.48394 (15)	0.08181 (7)	0.0431 (5)
C20	0.6796 (3)	0.51271 (18)	0.17506 (7)	0.0516 (5)
H20A	0.5830	0.5030	0.1522	0.062*
H20B	0.6536	0.5732	0.1923	0.062*
P20	0.67580 (7)	0.40987 (4)	0.216968 (17)	0.03970 (13)
B20	0.7582 (4)	0.2900 (2)	0.18879 (12)	0.0648 (8)
H20C	0.8852	0.2952	0.1819	0.097*
H20D	0.6926	0.2783	0.1599	0.097*
H20E	0.7382	0.2361	0.2103	0.097*
C21	0.8065 (3)	0.44666 (16)	0.26799 (7)	0.0421 (5)
C22	0.8822 (3)	0.3720 (2)	0.29513 (8)	0.0607 (7)
H22	0.8712	0.3067	0.2850	0.073*
C23	0.9728 (4)	0.3916 (3)	0.33640 (9)	0.0829 (10)
H23	1.0199	0.3399	0.3543	0.099*
C24	0.9937 (4)	0.4859 (3)	0.35108 (10)	0.0893 (11)
H24	1.0541	0.4989	0.3793	0.107*
C25	0.9261 (4)	0.5631 (3)	0.32451 (10)	0.0792 (10)
H25	0.9451	0.6281	0.3342	0.095*
C26	0.8287 (3)	0.54336 (19)	0.28293 (8)	0.0581 (6)
H26	0.7793	0.5951	0.2654	0.070*
C27	0.4377 (3)	0.4015 (2)	0.23797 (9)	0.0557 (6)
C28	0.3217 (4)	0.3616 (3)	0.19679 (11)	0.0863 (9)
H28A	0.1970	0.3589	0.2064	0.129*
H28B	0.3623	0.2965	0.1884	0.129*
H28C	0.3335	0.4047	0.1699	0.129*
C29	0.4320 (4)	0.3290 (2)	0.27968 (12)	0.0895 (10)
H29A	0.5013	0.3552	0.3056	0.134*
H29B	0.4824	0.2667	0.2700	0.134*
H29C	0.3087	0.3196	0.2896	0.134*
C30	0.3662 (4)	0.5016 (2)	0.25378 (10)	0.0746 (8)
H30A	0.2432	0.4947	0.2644	0.112*
H30B	0.3707	0.5471	0.2277	0.112*
H30C	0.4394	0.5262	0.2793	0.112*
C60	1.0864 (3)	0.42163 (17)	0.03827 (7)	0.0457 (5)
H60A	1.0468	0.3544	0.0445	0.055*
H60B	1.2161	0.4199	0.0328	0.055*
P60	0.97502 (7)	0.46565 (4)	−0.015697 (17)	0.03986 (13)
B60	0.7181 (4)	0.4778 (3)	−0.00786 (10)	0.0636 (8)
H60C	0.6921	0.5327	0.0126	0.095*
H60D	0.6709	0.4182	0.0059	0.095*
H60E	0.6625	0.4886	−0.0382	0.095*
C61	1.0838 (3)	0.58073 (16)	−0.03153 (7)	0.0442 (5)
C62	0.9838 (4)	0.65275 (19)	−0.05435 (9)	0.0648 (7)
H62	0.8602	0.6435	−0.0590	0.078*
C63	1.0662 (6)	0.7388 (2)	−0.07036 (11)	0.0852 (10)
H63	0.9976	0.7866	−0.0859	0.102*
C64	1.2485 (5)	0.7537 (2)	−0.06343 (11)	0.0820 (10)
H64	1.3034	0.8114	−0.0743	0.098*
C65	1.3482 (4)	0.6839 (2)	−0.04072 (9)	0.0665 (7)
H65	1.4714	0.6941	−0.0358	0.080*
C66	1.2683 (3)	0.59781 (18)	−0.02485 (7)	0.0499 (5)
H66	1.3384	0.5505	−0.0095	0.060*
C67	1.0402 (3)	0.37716 (16)	−0.06334 (7)	0.0447 (5)
C68	0.9210 (5)	0.2850 (2)	−0.05950 (10)	0.0796 (9)
H68A	0.9466	0.2413	−0.0855	0.119*
H68B	0.7957	0.3040	−0.0604	0.119*
H68C	0.9458	0.2517	−0.0301	0.119*
C69	1.0073 (4)	0.42745 (19)	−0.11134 (7)	0.0598 (6)
H69A	1.0900	0.4817	−0.1150	0.090*
H69B	0.8851	0.4516	−0.1126	0.090*
H69C	1.0262	0.3805	−0.1364	0.090*
C70	1.2385 (3)	0.34664 (19)	−0.05973 (8)	0.0558 (6)
H70A	1.2555	0.3062	−0.0321	0.084*
H70B	1.3130	0.4047	−0.0573	0.084*
H70C	1.2720	0.3098	−0.0875	0.084*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0473 (12)	0.0530 (12)	0.0335 (9)	−0.0033 (10)	−0.0008 (8)	0.0010 (9)
C2	0.0496 (12)	0.0528 (12)	0.0335 (9)	0.0067 (10)	0.0027 (9)	0.0050 (9)
C3	0.0726 (16)	0.0599 (13)	0.0396 (10)	−0.0098 (13)	0.0063 (11)	−0.0052 (10)
C4	0.0705 (17)	0.0733 (17)	0.0499 (13)	−0.0224 (14)	0.0036 (12)	−0.0090 (12)
C5	0.0556 (14)	0.0712 (15)	0.0422 (11)	−0.0162 (12)	0.0062 (10)	0.0015 (10)
C6	0.0487 (12)	0.0498 (12)	0.0308 (9)	0.0016 (10)	0.0007 (8)	0.0053 (8)
C20	0.0455 (12)	0.0690 (15)	0.0403 (10)	0.0114 (11)	0.0064 (10)	0.0006 (10)
P20	0.0344 (2)	0.0479 (3)	0.0368 (2)	−0.0008 (2)	0.0011 (2)	−0.0072 (2)
B20	0.0644 (19)	0.0558 (17)	0.0742 (19)	−0.0051 (14)	0.0074 (15)	−0.0204 (15)
C21	0.0358 (10)	0.0539 (12)	0.0366 (9)	−0.0056 (9)	0.0049 (8)	−0.0021 (9)
C22	0.0510 (14)	0.0798 (18)	0.0511 (13)	0.0015 (12)	−0.0030 (11)	0.0071 (12)
C23	0.0578 (17)	0.139 (3)	0.0515 (14)	−0.0001 (19)	−0.0118 (13)	0.0136 (17)
C24	0.0517 (17)	0.170 (4)	0.0460 (13)	−0.025 (2)	−0.0011 (12)	−0.0158 (19)
C25	0.0711 (19)	0.103 (2)	0.0631 (16)	−0.0409 (17)	0.0220 (14)	−0.0383 (16)
C26	0.0609 (14)	0.0655 (14)	0.0481 (11)	−0.0179 (13)	0.0124 (12)	−0.0150 (11)
C27	0.0352 (12)	0.0746 (16)	0.0574 (13)	−0.0025 (11)	0.0030 (10)	−0.0075 (12)
C28	0.0420 (15)	0.119 (3)	0.098 (2)	−0.0135 (16)	−0.0068 (16)	−0.021 (2)
C29	0.0547 (17)	0.108 (2)	0.106 (2)	−0.0055 (16)	0.0297 (17)	0.030 (2)
C30	0.0514 (16)	0.099 (2)	0.0735 (17)	0.0125 (14)	0.0160 (13)	−0.0121 (15)
C60	0.0483 (12)	0.0520 (12)	0.0366 (10)	0.0020 (10)	0.0043 (8)	0.0037 (9)
P60	0.0349 (3)	0.0499 (3)	0.0347 (2)	0.0011 (2)	0.0021 (2)	−0.0002 (2)
B60	0.0399 (15)	0.093 (2)	0.0583 (16)	0.0019 (14)	0.0024 (12)	−0.0090 (16)
C61	0.0489 (12)	0.0483 (12)	0.0356 (9)	0.0083 (10)	0.0030 (8)	−0.0008 (9)
C62	0.0614 (17)	0.0651 (15)	0.0680 (15)	0.0198 (14)	0.0039 (13)	0.0121 (12)
C63	0.116 (3)	0.0548 (16)	0.085 (2)	0.0280 (18)	0.023 (2)	0.0211 (15)
C64	0.117 (3)	0.0529 (16)	0.0760 (19)	−0.0072 (18)	0.039 (2)	0.0027 (14)
C65	0.074 (2)	0.0641 (16)	0.0614 (15)	−0.0187 (15)	0.0171 (14)	−0.0017 (13)
C66	0.0503 (13)	0.0546 (13)	0.0448 (12)	−0.0052 (11)	0.0044 (9)	0.0022 (10)
C67	0.0454 (12)	0.0503 (12)	0.0383 (10)	−0.0038 (10)	0.0043 (9)	−0.0018 (9)
C68	0.091 (2)	0.0737 (18)	0.0739 (18)	−0.0316 (17)	0.0249 (16)	−0.0222 (15)
C69	0.0649 (16)	0.0774 (16)	0.0370 (10)	0.0094 (14)	−0.0066 (11)	−0.0060 (10)
C70	0.0570 (15)	0.0654 (15)	0.0450 (12)	0.0158 (12)	0.0032 (10)	−0.0032 (11)

Geometric parameters (Å, º)

C1—C2	1.385 (3)	C29—H29A	0.9600
C1—C6	1.394 (3)	C29—H29B	0.9600
C1—H1	0.9300	C29—H29C	0.9600
C2—C3	1.385 (3)	C30—H30A	0.9600
C2—C20	1.510 (3)	C30—H30B	0.9600
C3—C4	1.378 (3)	C30—H30C	0.9600
C3—H3	0.9300	C60—P60	1.829 (2)
C4—C5	1.382 (3)	C60—H60A	0.9700
C4—H4	0.9300	C60—H60B	0.9700
C5—C6	1.375 (3)	P60—C61	1.806 (2)
C5—H5	0.9300	P60—C67	1.862 (2)
C6—C60	1.513 (3)	P60—B60	1.916 (3)
C20—P20	1.824 (2)	B60—H60C	0.9600
C20—H20A	0.9700	B60—H60D	0.9600
C20—H20B	0.9700	B60—H60E	0.9600
P20—C21	1.802 (2)	C61—C62	1.381 (3)
P20—C27	1.858 (3)	C61—C66	1.394 (3)
P20—B20	1.904 (3)	C62—C63	1.387 (4)
B20—H20C	0.9600	C62—H62	0.9300
B20—H20D	0.9600	C63—C64	1.375 (5)
B20—H20E	0.9600	C63—H63	0.9300
C21—C26	1.383 (3)	C64—C65	1.357 (4)
C21—C22	1.384 (3)	C64—H64	0.9300
C22—C23	1.368 (3)	C65—C66	1.379 (3)
C22—H22	0.9300	C65—H65	0.9300
C23—C24	1.349 (5)	C66—H66	0.9300
C23—H23	0.9300	C67—C70	1.524 (3)
C24—C25	1.378 (5)	C67—C68	1.529 (3)
C24—H24	0.9300	C67—C69	1.534 (3)
C25—C26	1.401 (3)	C68—H68A	0.9600
C25—H25	0.9300	C68—H68B	0.9600
C26—H26	0.9300	C68—H68C	0.9600
C27—C30	1.520 (4)	C69—H69A	0.9600
C27—C29	1.531 (4)	C69—H69B	0.9600
C27—C28	1.540 (3)	C69—H69C	0.9600
C28—H28A	0.9600	C70—H70A	0.9600
C28—H28B	0.9600	C70—H70B	0.9600
C28—H28C	0.9600	C70—H70C	0.9600
C2—C1—C6	121.8 (2)	C27—C29—H29C	109.5
C2—C1—H1	119.1	H29A—C29—H29C	109.5
C6—C1—H1	119.1	H29B—C29—H29C	109.5
C3—C2—C1	118.8 (2)	C27—C30—H30A	109.5
C3—C2—C20	120.8 (2)	C27—C30—H30B	109.5
C1—C2—C20	120.4 (2)	H30A—C30—H30B	109.5
C4—C3—C2	119.7 (2)	C27—C30—H30C	109.5
C4—C3—H3	120.1	H30A—C30—H30C	109.5
C2—C3—H3	120.1	H30B—C30—H30C	109.5
C3—C4—C5	120.9 (2)	C6—C60—P60	114.37 (15)
C3—C4—H4	119.6	C6—C60—H60A	108.7
C5—C4—H4	119.6	P60—C60—H60A	108.7
C6—C5—C4	120.5 (2)	C6—C60—H60B	108.7
C6—C5—H5	119.7	P60—C60—H60B	108.7
C4—C5—H5	119.7	H60A—C60—H60B	107.6
C5—C6—C1	118.2 (2)	C61—P60—C60	106.62 (11)
C5—C6—C60	121.0 (2)	C61—P60—C67	105.07 (10)
C1—C6—C60	120.8 (2)	C60—P60—C67	105.96 (10)
C2—C20—P20	115.46 (16)	C61—P60—B60	113.24 (13)
C2—C20—H20A	108.4	C60—P60—B60	112.13 (12)
P20—C20—H20A	108.4	C67—P60—B60	113.20 (12)
C2—C20—H20B	108.4	P60—B60—H60C	109.5
P20—C20—H20B	108.4	P60—B60—H60D	109.5
H20A—C20—H20B	107.5	H60C—B60—H60D	109.5
C21—P20—C20	107.36 (11)	P60—B60—H60E	109.5
C21—P20—C27	105.59 (11)	H60C—B60—H60E	109.5
C20—P20—C27	105.53 (11)	H60D—B60—H60E	109.5
C21—P20—B20	113.39 (13)	C62—C61—C66	117.9 (2)
C20—P20—B20	111.91 (13)	C62—C61—P60	119.0 (2)
C27—P20—B20	112.51 (13)	C66—C61—P60	122.92 (18)
P20—B20—H20C	109.5	C61—C62—C63	120.5 (3)
P20—B20—H20D	109.5	C61—C62—H62	119.7
H20C—B20—H20D	109.5	C63—C62—H62	119.7
P20—B20—H20E	109.5	C64—C63—C62	120.4 (3)
H20C—B20—H20E	109.5	C64—C63—H63	119.8
H20D—B20—H20E	109.5	C62—C63—H63	119.8
C26—C21—C22	118.2 (2)	C65—C64—C63	119.7 (3)
C26—C21—P20	124.57 (18)	C65—C64—H64	120.1
C22—C21—P20	117.13 (18)	C63—C64—H64	120.1
C23—C22—C21	121.7 (3)	C64—C65—C66	120.5 (3)
C23—C22—H22	119.1 (2)	C64—C65—H65	119.7
C21—C22—H22	119.1	C66—C65—H65	119.7
C24—C23—C22	120.0 (3)	C65—C66—C61	120.9 (2)
C24—C23—H23	120.0	C65—C66—H66	119.5
C22—C23—H23	120.0	C61—C66—H66	119.5
C23—C24—C25	120.5 (3)	C70—C67—C68	109.1 (2)
C23—C24—H24	119.8	C70—C67—C69	109.33 (19)
C25—C24—H24	119.8	C68—C67—C69	109.4 (2)
C24—C25—C26	119.8 (3)	C70—C67—P60	111.96 (16)
C24—C25—H25	120.1	C68—C67—P60	108.89 (16)
C26—C25—H25	120.1	C69—C67—P60	108.11 (15)
C21—C26—C25	119.7 (3)	C67—C68—H68A	109.5
C21—C26—H26	120.1	C67—C68—H68B	109.5
C25—C26—H26	120.1	H68A—C68—H68B	109.5
C30—C27—C29	109.6 (2)	C67—C68—H68C	109.5
C30—C27—C28	109.8 (2)	H68A—C68—H68C	109.5
C29—C27—C28	109.9 (2)	H68B—C68—H68C	109.5
C30—C27—P20	111.56 (18)	C67—C69—H69A	109.5
C29—C27—P20	108.05 (18)	C67—C69—H69B	109.5
C28—C27—P20	107.87 (18)	H69A—C69—H69B	109.5
C27—C28—H28A	109.5	C67—C69—H69C	109.5
C27—C28—H28B	109.5	H69A—C69—H69C	109.5
H28A—C28—H28B	109.5	H69B—C69—H69C	109.5
C27—C28—H28C	109.5	C67—C70—H70A	109.5
H28A—C28—H28C	109.5	C67—C70—H70B	109.5
H28B—C28—H28C	109.5	H70A—C70—H70B	109.5
C27—C29—H29A	109.5	C67—C70—H70C	109.5
C27—C29—H29B	109.5	H70A—C70—H70C	109.5
H29A—C29—H29B	109.5	H70B—C70—H70C	109.5
C6—C1—C2—C3	0.7 (3)	C20—P20—C27—C29	−170.04 (19)
C6—C1—C2—C20	178.69 (19)	B20—P20—C27—C29	67.7 (2)
C1—C2—C3—C4	−0.1 (3)	C21—P20—C27—C28	−175.3 (2)
C20—C2—C3—C4	−178.1 (2)	C20—P20—C27—C28	71.2 (2)
C2—C3—C4—C5	−0.1 (4)	B20—P20—C27—C28	−51.1 (2)
C3—C4—C5—C6	−0.3 (4)	C5—C6—C60—P60	−98.5 (2)
C4—C5—C6—C1	0.9 (3)	C1—C6—C60—P60	81.7 (2)
C4—C5—C6—C60	−178.9 (2)	C6—C60—P60—C61	68.73 (18)
C2—C1—C6—C5	−1.1 (3)	C6—C60—P60—C67	−179.69 (16)
C2—C1—C6—C60	178.67 (19)	C6—C60—P60—B60	−55.7 (2)
C3—C2—C20—P20	−98.5 (2)	C60—P60—C61—C62	−149.02 (18)
C1—C2—C20—P20	83.5 (2)	C67—P60—C61—C62	98.79 (19)
C2—C20—P20—C21	75.01 (19)	B60—P60—C61—C62	−25.2 (2)
C2—C20—P20—C27	−172.72 (17)	C60—P60—C61—C66	35.7 (2)
C2—C20—P20—B20	−50.0 (2)	C67—P60—C61—C66	−76.5 (2)
C20—P20—C21—C26	28.0 (2)	B60—P60—C61—C66	159.51 (18)
C27—P20—C21—C26	−84.3 (2)	C66—C61—C62—C63	0.6 (4)
B20—P20—C21—C26	152.1 (2)	P60—C61—C62—C63	−174.9 (2)
C20—P20—C21—C22	−155.19 (17)	C61—C62—C63—C64	−0.4 (4)
C27—P20—C21—C22	92.6 (2)	C62—C63—C64—C65	−0.1 (5)
B20—P20—C21—C22	−31.0 (2)	C63—C64—C65—C66	0.4 (4)
C26—C21—C22—C23	1.8 (3)	C64—C65—C66—C61	−0.3 (4)
P20—C21—C22—C23	−175.3 (2)	C62—C61—C66—C65	−0.2 (3)
C21—C22—C23—C24	−1.5 (4)	P60—C61—C66—C65	175.05 (17)
C22—C23—C24—C25	−0.7 (5)	C61—P60—C67—C70	72.15 (18)
C23—C24—C25—C26	2.5 (4)	C60—P60—C67—C70	−40.51 (19)
C22—C21—C26—C25	0.1 (3)	B60—P60—C67—C70	−163.80 (18)
P20—C21—C26—C25	176.87 (17)	C61—P60—C67—C68	−167.13 (19)
C24—C25—C26—C21	−2.2 (4)	C60—P60—C67—C68	80.2 (2)
C21—P20—C27—C30	64.0 (2)	B60—P60—C67—C68	−43.1 (2)
C20—P20—C27—C30	−49.5 (2)	C61—P60—C67—C69	−48.34 (19)
B20—P20—C27—C30	−171.8 (2)	C60—P60—C67—C69	−160.99 (16)
C21—P20—C27—C29	−56.5 (2)	B60—P60—C67—C69	75.7 (2)