[1,4-Phenyl-enebis(methyl-ene)]bis-(tri-phenyl-phospho-nium) bis-(tetra-fluoro-borate).

The crystal structure of the title salt, C(44)H(38)P(2) (2+)2BF(4) (-), consists of discrete dications inter-laced with the BF(4) (-) counter-ions. In each cation, both phospho-nium groups lie on the same side of the plane of the central benzene ring. The tetra-fluoro-borate anions are involved in intensive thermal motion, thus some B-F bond lengths [range 1.329 (6) to 1.391 (6) Å] deviate significantly from their standard values.

Related literature

For a related synthetic strategy, see: Ganesan & Alias (2008 ▶). For salts containing the triphenyl­phospho­nium cation, see: Kariuki et al. (2009 ▶). For applications of phospho­nium salts as ionic liquids, see: Cieniecka-Roslonkiewicz et al. (2005 ▶). For a similar mono-phospho­nium compound, see: Hafiz (2008 ▶).

Experimental

Crystal data

C44H38P2 2+·2BF4 −

M = 802.30

Monoclinic,

a = 21.8874 (5) Å

b = 14.4610 (3) Å

c = 15.2818 (3) Å

β = 123.898 (1)°

V = 4014.78 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 173 K

0.52 × 0.22 × 0.13 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

25162 measured reflections

4853 independent reflections

3786 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.113

S = 1.10

4853 reflections

506 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT-Plus (Bruker, 2009 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811048975/yk2028sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048975/yk2028Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811048975/yk2028Isup3.cml

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

C44H38P22+·2BF4−	F(000) = 1656
Mr = 802.30	Dx = 1.327 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 5943 reflections
a = 21.8874 (5) Å	θ = 2.7–24.0°
b = 14.4610 (3) Å	µ = 0.18 mm−1
c = 15.2818 (3) Å	T = 173 K
β = 123.898 (1)°	Needle, colourless
V = 4014.78 (15) Å3	0.52 × 0.22 × 0.13 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	3786 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.058
graphite	θmax = 28.0°, θmin = 1.8°
φ and ω scans	h = −28→28
25162 measured reflections	k = −19→18
4853 independent reflections	l = −20→20

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0571P)2] where P = (Fo2 + 2Fc2)/3
4853 reflections	(Δ/σ)max = 0.032
506 parameters	Δρmax = 0.43 e Å−3
2 restraints	Δρmin = −0.33 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C1	0.29567 (19)	0.8761 (2)	0.3995 (3)	0.0254 (7)
C2	0.35338 (19)	0.8962 (2)	0.3896 (3)	0.0278 (7)
H2	0.4001	0.9118	0.4507	0.033*
C3	0.34422 (19)	0.8942 (2)	0.2920 (3)	0.0290 (7)
H3	0.3845	0.9085	0.2868	0.035*
C4	0.2764 (2)	0.8712 (2)	0.2019 (3)	0.0271 (8)
C5	0.2178 (2)	0.8531 (3)	0.2112 (3)	0.0328 (8)
H5	0.1707	0.8393	0.1498	0.039*
C6	0.22707 (19)	0.8549 (3)	0.3082 (3)	0.0314 (8)
H6	0.1866	0.8416	0.3131	0.038*
C7	0.3067 (2)	0.8733 (2)	0.5052 (3)	0.0291 (8)
H7A	0.2626	0.8990	0.4992	0.035*
H7B	0.3493	0.9128	0.5548	0.035*
C8	0.2650 (2)	0.8716 (2)	0.0939 (3)	0.0303 (8)
H8A	0.3084	0.9013	0.1014	0.036*
H8B	0.2218	0.9110	0.0463	0.036*
C11	0.2368 (2)	0.6952 (2)	0.4900 (3)	0.0318 (8)
C12	0.2281 (2)	0.6090 (3)	0.4461 (4)	0.0579 (13)
H12	0.2684	0.5795	0.4500	0.069*
C13	0.1602 (3)	0.5654 (3)	0.3962 (4)	0.0693 (16)
H13	0.1535	0.5072	0.3632	0.083*
C14	0.1027 (3)	0.6053 (3)	0.3939 (4)	0.0546 (12)
H14	0.0574	0.5732	0.3638	0.066*
C15	0.1109 (3)	0.6928 (3)	0.4358 (4)	0.0609 (13)
H15	0.0705	0.7222	0.4314	0.073*
C16	0.1782 (2)	0.7373 (3)	0.4840 (4)	0.0545 (12)
H16	0.1840	0.7972	0.5132	0.065*
C21	0.3574 (2)	0.7610 (3)	0.6955 (3)	0.0334 (9)
C22	0.3793 (3)	0.8412 (3)	0.7521 (3)	0.0498 (11)
H22	0.3768	0.8978	0.7187	0.060*
C23	0.4056 (3)	0.8405 (4)	0.8588 (3)	0.0586 (13)
H23	0.4201	0.8967	0.8975	0.070*
C24	0.4103 (3)	0.7607 (4)	0.9069 (3)	0.0543 (12)
H24	0.4260	0.7608	0.9788	0.065*
C25	0.3925 (4)	0.6795 (4)	0.8526 (4)	0.093 (2)
H25	0.3998	0.6229	0.8888	0.112*
C26	0.3641 (4)	0.6779 (4)	0.7460 (4)	0.0770 (18)
H26	0.3494	0.6213	0.7080	0.092*
C31	0.3883 (2)	0.6991 (2)	0.5404 (3)	0.0309 (8)
C32	0.4589 (2)	0.6802 (3)	0.6277 (3)	0.0391 (9)
H32	0.4727	0.6970	0.6965	0.047*
C33	0.5089 (2)	0.6361 (3)	0.6123 (4)	0.0492 (11)
H33	0.5568	0.6215	0.6714	0.059*
C34	0.4900 (3)	0.6137 (3)	0.5133 (4)	0.0516 (12)
H34	0.5248	0.5844	0.5040	0.062*
C35	0.4212 (3)	0.6332 (3)	0.4280 (4)	0.0510 (11)
H35	0.4086	0.6173	0.3595	0.061*
C36	0.3697 (2)	0.6759 (3)	0.4396 (3)	0.0400 (9)
H36	0.3220	0.6894	0.3795	0.048*
C41	0.3354 (2)	0.6988 (2)	0.0830 (3)	0.0287 (8)
C42	0.4020 (2)	0.7307 (3)	0.1686 (3)	0.0385 (9)
H42	0.4043	0.7878	0.2011	0.046*
C43	0.4653 (2)	0.6789 (3)	0.2064 (3)	0.0521 (12)
H43	0.5108	0.7006	0.2655	0.062*
C44	0.4634 (2)	0.5968 (3)	0.1599 (3)	0.0438 (10)
H44	0.5071	0.5617	0.1872	0.053*
C45	0.3975 (2)	0.5654 (3)	0.0733 (3)	0.0483 (11)
H45	0.3958	0.5089	0.0402	0.058*
C46	0.3340 (2)	0.6168 (3)	0.0349 (3)	0.0452 (10)
H46	0.2889	0.5956	−0.0253	0.054*
C51	0.21135 (19)	0.7844 (2)	−0.1065 (3)	0.0257 (7)
C52	0.2345 (2)	0.8608 (3)	−0.1341 (3)	0.0384 (9)
H52	0.2723	0.8992	−0.0809	0.046*
C53	0.2026 (2)	0.8817 (3)	−0.2394 (3)	0.0453 (10)
H53	0.2182	0.9349	−0.2584	0.054*
C54	0.1484 (2)	0.8259 (3)	−0.3166 (3)	0.0447 (10)
H54	0.1257	0.8417	−0.3887	0.054*
C55	0.1271 (2)	0.7475 (3)	−0.2899 (3)	0.0482 (11)
H55	0.0912	0.7077	−0.3436	0.058*
C56	0.1577 (2)	0.7263 (3)	−0.1851 (3)	0.0368 (8)
H56	0.1425	0.6724	−0.1666	0.044*
C61	0.1912 (2)	0.6890 (3)	0.0463 (3)	0.0327 (8)
C62	0.1165 (2)	0.7106 (3)	−0.0065 (3)	0.0401 (9)
H62	0.0967	0.7608	−0.0548	0.048*
C63	0.0715 (3)	0.6593 (4)	0.0112 (4)	0.0577 (13)
H63	0.0205	0.6734	−0.0256	0.069*
C64	0.1005 (3)	0.5871 (4)	0.0827 (5)	0.0771 (18)
H64	0.0693	0.5519	0.0950	0.093*
C65	0.1740 (3)	0.5657 (4)	0.1361 (5)	0.0755 (16)
H65	0.1934	0.5161	0.1852	0.091*
C66	0.2201 (3)	0.6165 (3)	0.1186 (4)	0.0533 (11)
H66	0.2710	0.6019	0.1558	0.064*
B1	0.1000 (3)	0.9769 (3)	0.4235 (4)	0.0422 (11)
B2	0.4719 (2)	1.0386 (3)	0.6578 (3)	0.0331 (10)
F1	0.16257 (17)	0.95422 (19)	0.5214 (2)	0.0692 (8)
F2	0.1130 (2)	0.9491 (3)	0.3495 (3)	0.0983 (12)
F3	0.0411 (2)	0.9335 (3)	0.4089 (4)	0.1183 (16)
F4	0.09095 (14)	1.07117 (18)	0.4166 (2)	0.0594 (7)
F5	0.40535 (15)	1.0708 (2)	0.5748 (2)	0.0770 (10)
F6	0.4802 (3)	1.0623 (3)	0.7481 (3)	0.144 (2)
F7	0.5246 (3)	1.0771 (3)	0.6519 (5)	0.143 (2)
F8	0.47676 (13)	0.94392 (17)	0.6507 (2)	0.0544 (7)
P1	0.32289 (5)	0.75698 (6)	0.55775 (6)	0.0273 (2)
P2	0.25107 (5)	0.76029 (6)	0.03033 (6)	0.0247 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0266 (18)	0.0248 (17)	0.0266 (18)	0.0027 (14)	0.0160 (16)	0.0003 (13)
C2	0.0271 (17)	0.0296 (17)	0.0226 (17)	−0.0056 (14)	0.0113 (14)	−0.0037 (14)
C3	0.0296 (18)	0.0264 (17)	0.036 (2)	−0.0058 (14)	0.0215 (16)	−0.0030 (14)
C4	0.033 (2)	0.0223 (17)	0.0261 (18)	0.0062 (14)	0.0167 (16)	0.0025 (13)
C5	0.0236 (17)	0.045 (2)	0.0272 (18)	0.0038 (16)	0.0126 (15)	−0.0030 (16)
C6	0.0271 (18)	0.036 (2)	0.0316 (19)	0.0000 (15)	0.0166 (16)	−0.0050 (16)
C7	0.0310 (19)	0.0296 (19)	0.0286 (19)	−0.0041 (15)	0.0178 (16)	−0.0046 (14)
C8	0.037 (2)	0.0280 (19)	0.0283 (19)	0.0034 (15)	0.0193 (17)	0.0001 (15)
C11	0.033 (2)	0.0305 (19)	0.0281 (19)	−0.0064 (16)	0.0143 (17)	−0.0025 (15)
C12	0.038 (2)	0.038 (2)	0.080 (3)	−0.0002 (19)	0.022 (2)	−0.016 (2)
C13	0.057 (3)	0.044 (3)	0.090 (4)	−0.015 (2)	0.031 (3)	−0.029 (3)
C14	0.041 (2)	0.056 (3)	0.056 (3)	−0.020 (2)	0.021 (2)	−0.012 (2)
C15	0.048 (3)	0.064 (3)	0.081 (4)	−0.017 (2)	0.042 (3)	−0.015 (3)
C16	0.051 (3)	0.053 (3)	0.078 (3)	−0.018 (2)	0.048 (3)	−0.029 (2)
C21	0.041 (2)	0.039 (2)	0.0264 (19)	−0.0021 (17)	0.0219 (17)	−0.0015 (15)
C22	0.072 (3)	0.047 (2)	0.031 (2)	−0.007 (2)	0.029 (2)	−0.0030 (18)
C23	0.074 (3)	0.066 (3)	0.034 (2)	−0.010 (3)	0.029 (2)	−0.013 (2)
C24	0.054 (3)	0.085 (4)	0.025 (2)	0.006 (2)	0.023 (2)	0.003 (2)
C25	0.171 (7)	0.071 (4)	0.054 (3)	0.014 (4)	0.073 (4)	0.020 (3)
C26	0.142 (5)	0.048 (3)	0.054 (3)	−0.007 (3)	0.062 (4)	0.002 (2)
C31	0.036 (2)	0.0264 (18)	0.032 (2)	0.0013 (15)	0.0197 (17)	0.0016 (15)
C32	0.037 (2)	0.046 (2)	0.040 (2)	−0.0042 (18)	0.0249 (19)	−0.0035 (18)
C33	0.033 (2)	0.048 (3)	0.069 (3)	0.0001 (18)	0.030 (2)	0.003 (2)
C34	0.061 (3)	0.044 (2)	0.078 (3)	0.003 (2)	0.056 (3)	0.002 (2)
C35	0.083 (3)	0.039 (2)	0.055 (3)	0.006 (2)	0.053 (3)	0.002 (2)
C36	0.055 (2)	0.0337 (19)	0.035 (2)	0.0070 (18)	0.0278 (19)	0.0019 (15)
C41	0.033 (2)	0.0256 (17)	0.0287 (19)	0.0011 (15)	0.0183 (17)	0.0024 (14)
C42	0.033 (2)	0.038 (2)	0.034 (2)	0.0044 (16)	0.0113 (17)	−0.0027 (16)
C43	0.031 (2)	0.061 (3)	0.039 (2)	0.0088 (19)	0.0042 (19)	−0.006 (2)
C44	0.033 (2)	0.046 (2)	0.047 (2)	0.0119 (19)	0.0190 (19)	0.0058 (19)
C45	0.042 (2)	0.036 (2)	0.057 (3)	0.0065 (18)	0.022 (2)	−0.0081 (19)
C46	0.036 (2)	0.038 (2)	0.053 (3)	−0.0011 (17)	0.0190 (19)	−0.0121 (18)
C51	0.0268 (18)	0.0290 (17)	0.0237 (17)	0.0011 (14)	0.0156 (15)	0.0022 (14)
C52	0.050 (2)	0.041 (2)	0.0285 (19)	−0.0148 (18)	0.0248 (19)	−0.0074 (16)
C53	0.062 (3)	0.045 (2)	0.037 (2)	−0.009 (2)	0.033 (2)	0.0044 (17)
C54	0.047 (2)	0.059 (3)	0.029 (2)	0.001 (2)	0.0222 (19)	0.0041 (19)
C55	0.053 (3)	0.053 (3)	0.026 (2)	−0.014 (2)	0.0148 (19)	−0.0028 (17)
C56	0.040 (2)	0.038 (2)	0.0288 (19)	−0.0120 (17)	0.0168 (17)	−0.0035 (15)
C61	0.043 (2)	0.032 (2)	0.032 (2)	−0.0051 (17)	0.0267 (18)	−0.0015 (16)
C62	0.038 (2)	0.043 (2)	0.044 (2)	−0.0062 (18)	0.0258 (19)	−0.0022 (18)
C63	0.054 (3)	0.063 (3)	0.073 (3)	−0.019 (2)	0.045 (3)	−0.019 (3)
C64	0.093 (4)	0.074 (4)	0.106 (5)	−0.028 (3)	0.081 (4)	−0.002 (3)
C65	0.091 (4)	0.073 (4)	0.091 (4)	−0.001 (3)	0.069 (4)	0.030 (3)
C66	0.064 (3)	0.050 (3)	0.061 (3)	0.004 (2)	0.044 (2)	0.017 (2)
B1	0.045 (3)	0.045 (3)	0.045 (3)	−0.007 (2)	0.030 (2)	−0.012 (2)
B2	0.027 (2)	0.037 (2)	0.034 (2)	0.0011 (18)	0.0156 (19)	−0.0049 (18)
F1	0.089 (2)	0.0490 (15)	0.0475 (15)	−0.0135 (15)	0.0243 (15)	0.0046 (12)
F2	0.134 (3)	0.115 (3)	0.078 (2)	0.057 (2)	0.079 (2)	0.0109 (19)
F3	0.066 (2)	0.099 (3)	0.182 (4)	−0.042 (2)	0.064 (3)	−0.028 (3)
F4	0.0533 (16)	0.0487 (15)	0.0649 (18)	0.0071 (12)	0.0260 (14)	−0.0031 (13)
F5	0.0611 (18)	0.0594 (18)	0.065 (2)	0.0157 (15)	0.0068 (15)	−0.0042 (14)
F6	0.225 (5)	0.139 (3)	0.054 (2)	0.128 (4)	0.070 (3)	0.030 (2)
F7	0.121 (3)	0.063 (2)	0.311 (7)	−0.022 (2)	0.162 (4)	−0.015 (3)
F8	0.0449 (14)	0.0435 (13)	0.0596 (16)	0.0008 (11)	0.0197 (12)	−0.0028 (12)
P1	0.0313 (5)	0.0290 (5)	0.0239 (5)	−0.0035 (4)	0.0168 (4)	−0.0032 (4)
P2	0.0248 (4)	0.0276 (4)	0.0226 (4)	0.0006 (4)	0.0137 (4)	0.0012 (4)

C1—C2	1.384 (5)	C34—C35	1.362 (7)
C1—C6	1.399 (5)	C34—H34	0.9500
C1—C7	1.495 (5)	C35—C36	1.381 (6)
C2—C3	1.391 (5)	C35—H35	0.9500
C2—H2	0.9500	C36—H36	0.9500
C3—C4	1.390 (5)	C41—C42	1.386 (5)
C3—H3	0.9500	C41—C46	1.387 (5)
C4—C5	1.392 (5)	C41—P2	1.785 (4)
C4—C8	1.525 (5)	C42—C43	1.387 (5)
C5—C6	1.380 (5)	C42—H42	0.9500
C5—H5	0.9500	C43—C44	1.372 (6)
C6—H6	0.9500	C43—H43	0.9500
C7—P1	1.812 (4)	C44—C45	1.381 (6)
C7—H7A	0.9900	C44—H44	0.9500
C7—H7B	0.9900	C45—C46	1.386 (6)
C8—P2	1.817 (4)	C45—H45	0.9500
C8—H8A	0.9900	C46—H46	0.9500
C8—H8B	0.9900	C51—C52	1.377 (5)
C11—C16	1.376 (6)	C51—C56	1.398 (5)
C11—C12	1.378 (6)	C51—P2	1.795 (3)
C11—P1	1.800 (4)	C52—C53	1.384 (5)
C12—C13	1.387 (6)	C52—H52	0.9500
C12—H12	0.9500	C53—C54	1.374 (6)
C13—C14	1.367 (7)	C53—H53	0.9500
C13—H13	0.9500	C54—C55	1.371 (6)
C14—C15	1.382 (7)	C54—H54	0.9500
C14—H14	0.9500	C55—C56	1.383 (5)
C15—C16	1.385 (6)	C55—H55	0.9500
C15—H15	0.9500	C56—H56	0.9500
C16—H16	0.9500	C61—C66	1.393 (6)
C21—C22	1.363 (6)	C61—C62	1.398 (5)
C21—C26	1.391 (6)	C61—P2	1.788 (4)
C21—P1	1.797 (4)	C62—C63	1.376 (6)
C22—C23	1.395 (6)	C62—H62	0.9500
C22—H22	0.9500	C63—C64	1.383 (8)
C23—C24	1.340 (7)	C63—H63	0.9500
C23—H23	0.9500	C64—C65	1.372 (8)
C24—C25	1.364 (8)	C64—H64	0.9500
C24—H24	0.9500	C65—C66	1.389 (6)
C25—C26	1.383 (7)	C65—H65	0.9500
C25—H25	0.9500	C66—H66	0.9500
C26—H26	0.9500	B1—F3	1.336 (6)
C31—C32	1.393 (5)	B1—F2	1.371 (6)
C31—C36	1.398 (5)	B1—F4	1.374 (6)
C31—P1	1.801 (4)	B1—F1	1.391 (6)
C32—C33	1.397 (6)	B2—F7	1.329 (6)
C32—H32	0.9500	B2—F6	1.331 (6)
C33—C34	1.365 (7)	B2—F5	1.373 (5)
C33—H33	0.9500	B2—F8	1.383 (5)
C2—C1—C6	118.3 (3)	C35—C36—C31	119.5 (4)
C2—C1—C7	121.0 (3)	C35—C36—H36	120.2
C6—C1—C7	120.6 (3)	C31—C36—H36	120.2
C1—C2—C3	121.2 (3)	C42—C41—C46	119.0 (3)
C1—C2—H2	119.4	C42—C41—P2	122.6 (3)
C3—C2—H2	119.4	C46—C41—P2	118.4 (3)
C2—C3—C4	120.2 (3)	C41—C42—C43	119.6 (4)
C2—C3—H3	119.9	C41—C42—H42	120.2
C4—C3—H3	119.9	C43—C42—H42	120.2
C5—C4—C3	118.7 (3)	C44—C43—C42	121.1 (4)
C5—C4—C8	120.5 (3)	C44—C43—H43	119.5
C3—C4—C8	120.7 (3)	C42—C43—H43	119.5
C6—C5—C4	120.9 (3)	C43—C44—C45	119.7 (4)
C6—C5—H5	119.5	C43—C44—H44	120.1
C4—C5—H5	119.5	C45—C44—H44	120.1
C5—C6—C1	120.6 (3)	C44—C45—C46	119.5 (4)
C5—C6—H6	119.7	C44—C45—H45	120.2
C1—C6—H6	119.7	C46—C45—H45	120.2
C1—C7—P1	112.2 (2)	C45—C46—C41	121.0 (4)
C1—C7—H7A	109.2	C45—C46—H46	119.5
P1—C7—H7A	109.2	C41—C46—H46	119.5
C1—C7—H7B	109.2	C52—C51—C56	119.7 (3)
P1—C7—H7B	109.2	C52—C51—P2	119.4 (3)
H7A—C7—H7B	107.9	C56—C51—P2	120.9 (3)
C4—C8—P2	116.9 (2)	C51—C52—C53	119.9 (4)
C4—C8—H8A	108.1	C51—C52—H52	120.1
P2—C8—H8A	108.1	C53—C52—H52	120.1
C4—C8—H8B	108.1	C54—C53—C52	120.3 (4)
P2—C8—H8B	108.1	C54—C53—H53	119.9
H8A—C8—H8B	107.3	C52—C53—H53	119.9
C16—C11—C12	119.8 (4)	C55—C54—C53	120.3 (4)
C16—C11—P1	117.1 (3)	C55—C54—H54	119.9
C12—C11—P1	123.0 (3)	C53—C54—H54	119.9
C11—C12—C13	119.5 (4)	C54—C55—C56	120.2 (4)
C11—C12—H12	120.2	C54—C55—H55	119.9
C13—C12—H12	120.2	C56—C55—H55	119.9
C14—C13—C12	120.8 (4)	C55—C56—C51	119.6 (3)
C14—C13—H13	119.6	C55—C56—H56	120.2
C12—C13—H13	119.6	C51—C56—H56	120.2
C13—C14—C15	119.5 (4)	C66—C61—C62	119.6 (4)
C13—C14—H14	120.2	C66—C61—P2	120.0 (3)
C15—C14—H14	120.2	C62—C61—P2	120.2 (3)
C16—C15—C14	119.9 (5)	C63—C62—C61	120.1 (4)
C16—C15—H15	120.1	C63—C62—H62	120.0
C14—C15—H15	120.1	C61—C62—H62	120.0
C11—C16—C15	120.3 (4)	C62—C63—C64	120.0 (5)
C11—C16—H16	119.8	C62—C63—H63	120.0
C15—C16—H16	119.8	C64—C63—H63	120.0
C22—C21—C26	119.4 (4)	C65—C64—C63	120.6 (5)
C22—C21—P1	122.7 (3)	C65—C64—H64	119.7
C26—C21—P1	117.8 (3)	C63—C64—H64	119.7
C21—C22—C23	120.4 (4)	C64—C65—C66	120.2 (5)
C21—C22—H22	119.8	C64—C65—H65	119.9
C23—C22—H22	119.8	C66—C65—H65	119.9
C24—C23—C22	120.2 (5)	C65—C66—C61	119.6 (5)
C24—C23—H23	119.9	C65—C66—H66	120.2
C22—C23—H23	119.9	C61—C66—H66	120.2
C23—C24—C25	119.9 (4)	F3—B1—F2	110.4 (4)
C23—C24—H24	120.0	F3—B1—F4	111.6 (4)
C25—C24—H24	120.0	F2—B1—F4	108.3 (4)
C24—C25—C26	121.3 (5)	F3—B1—F1	110.4 (5)
C24—C25—H25	119.4	F2—B1—F1	106.6 (4)
C26—C25—H25	119.4	F4—B1—F1	109.3 (4)
C25—C26—C21	118.6 (5)	F7—B2—F6	109.9 (5)
C25—C26—H26	120.7	F7—B2—F5	108.0 (4)
C21—C26—H26	120.7	F6—B2—F5	109.4 (4)
C32—C31—C36	119.6 (3)	F7—B2—F8	107.5 (4)
C32—C31—P1	119.9 (3)	F6—B2—F8	111.4 (4)
C36—C31—P1	120.5 (3)	F5—B2—F8	110.6 (3)
C33—C32—C31	118.9 (4)	C21—P1—C11	108.16 (18)
C33—C32—H32	120.5	C21—P1—C31	109.73 (18)
C31—C32—H32	120.5	C11—P1—C31	110.33 (18)
C34—C33—C32	120.9 (4)	C21—P1—C7	109.83 (18)
C34—C33—H33	119.6	C11—P1—C7	108.83 (18)
C32—C33—H33	119.6	C31—P1—C7	109.92 (17)
C35—C34—C33	120.1 (4)	C41—P2—C61	107.66 (17)
C35—C34—H34	119.9	C41—P2—C51	109.23 (16)
C33—C34—H34	119.9	C61—P2—C51	110.82 (17)
C34—C35—C36	121.0 (4)	C41—P2—C8	112.16 (17)
C34—C35—H35	119.5	C61—P2—C8	110.80 (18)
C36—C35—H35	119.5	C51—P2—C8	106.19 (16)
C6—C1—C2—C3	−1.0 (5)	C52—C51—C56—C55	−1.7 (6)
C7—C1—C2—C3	176.6 (3)	P2—C51—C56—C55	178.8 (3)
C1—C2—C3—C4	−0.3 (5)	C66—C61—C62—C63	−1.4 (6)
C2—C3—C4—C5	1.8 (5)	P2—C61—C62—C63	−175.7 (3)
C2—C3—C4—C8	178.1 (3)	C61—C62—C63—C64	1.0 (7)
C3—C4—C5—C6	−2.0 (5)	C62—C63—C64—C65	−0.2 (8)
C8—C4—C5—C6	−178.3 (3)	C63—C64—C65—C66	−0.2 (9)
C4—C5—C6—C1	0.7 (6)	C64—C65—C66—C61	−0.2 (8)
C2—C1—C6—C5	0.8 (5)	C62—C61—C66—C65	1.0 (7)
C7—C1—C6—C5	−176.9 (3)	P2—C61—C66—C65	175.3 (4)
C2—C1—C7—P1	−96.2 (4)	C22—C21—P1—C11	−129.0 (4)
C6—C1—C7—P1	81.5 (4)	C26—C21—P1—C11	53.3 (5)
C5—C4—C8—P2	−72.5 (4)	C22—C21—P1—C31	110.6 (4)
C3—C4—C8—P2	111.3 (3)	C26—C21—P1—C31	−67.1 (4)
C16—C11—C12—C13	0.0 (7)	C22—C21—P1—C7	−10.3 (4)
P1—C11—C12—C13	179.2 (4)	C26—C21—P1—C7	171.9 (4)
C11—C12—C13—C14	−2.8 (8)	C16—C11—P1—C21	68.4 (4)
C12—C13—C14—C15	4.3 (8)	C12—C11—P1—C21	−110.8 (4)
C13—C14—C15—C16	−3.1 (8)	C16—C11—P1—C31	−171.6 (3)
C12—C11—C16—C15	1.1 (7)	C12—C11—P1—C31	9.2 (4)
P1—C11—C16—C15	−178.1 (4)	C16—C11—P1—C7	−50.9 (4)
C14—C15—C16—C11	0.4 (8)	C12—C11—P1—C7	129.9 (4)
C26—C21—C22—C23	−2.5 (7)	C32—C31—P1—C21	−11.2 (4)
P1—C21—C22—C23	179.8 (4)	C36—C31—P1—C21	171.1 (3)
C21—C22—C23—C24	0.9 (8)	C32—C31—P1—C11	−130.3 (3)
C22—C23—C24—C25	2.9 (8)	C36—C31—P1—C11	52.0 (3)
C23—C24—C25—C26	−5.1 (10)	C32—C31—P1—C7	109.7 (3)
C24—C25—C26—C21	3.4 (10)	C36—C31—P1—C7	−68.0 (3)
C22—C21—C26—C25	0.4 (9)	C1—C7—P1—C21	166.1 (3)
P1—C21—C26—C25	178.2 (5)	C1—C7—P1—C11	−75.6 (3)
C36—C31—C32—C33	−1.6 (5)	C1—C7—P1—C31	45.3 (3)
P1—C31—C32—C33	−179.3 (3)	C42—C41—P2—C61	−117.1 (3)
C31—C32—C33—C34	1.5 (6)	C46—C41—P2—C61	64.2 (3)
C32—C33—C34—C35	−0.8 (7)	C42—C41—P2—C51	122.5 (3)
C33—C34—C35—C36	0.1 (7)	C46—C41—P2—C51	−56.2 (3)
C34—C35—C36—C31	−0.2 (6)	C42—C41—P2—C8	5.1 (4)
C32—C31—C36—C35	1.0 (6)	C46—C41—P2—C8	−173.7 (3)
P1—C31—C36—C35	178.7 (3)	C66—C61—P2—C41	18.8 (4)
C46—C41—C42—C43	−2.1 (6)	C62—C61—P2—C41	−166.9 (3)
P2—C41—C42—C43	179.2 (3)	C66—C61—P2—C51	138.2 (3)
C41—C42—C43—C44	0.6 (7)	C62—C61—P2—C51	−47.5 (4)
C42—C43—C44—C45	0.7 (7)	C66—C61—P2—C8	−104.2 (4)
C43—C44—C45—C46	−0.6 (7)	C62—C61—P2—C8	70.1 (4)
C44—C45—C46—C41	−0.8 (7)	C52—C51—P2—C41	−83.8 (3)
C42—C41—C46—C45	2.2 (6)	C56—C51—P2—C41	95.7 (3)
P2—C41—C46—C45	−179.0 (4)	C52—C51—P2—C61	157.7 (3)
C56—C51—C52—C53	2.5 (6)	C56—C51—P2—C61	−22.8 (4)
P2—C51—C52—C53	−177.9 (3)	C52—C51—P2—C8	37.3 (4)
C51—C52—C53—C54	−0.7 (7)	C56—C51—P2—C8	−143.2 (3)
C52—C53—C54—C55	−2.0 (7)	C4—C8—P2—C41	−78.5 (3)
C53—C54—C55—C56	2.8 (7)	C4—C8—P2—C61	41.8 (3)
C54—C55—C56—C51	−0.9 (7)	C4—C8—P2—C51	162.2 (3)