(S(P),S(P))-(-)-(E)-1,2-Bis(methyl-phenyl-phosphino-yl)ethene.

The title compound, C(16)H(18)O(2)P(2), possesses two stereogenic P atoms and shows a distorted s-cis conformation of each O=P-C=C moiety. This has been suggested on the basis of the stereochemical result of 1,3-dipolar cyclo-additions with nitro-nes and is now confirmed by the present crystal structure analysis. There are two crystallographically independent molecules in the asymmetric unit.

Related literature

For optically active P-stereogenic 1,2-diphosphinoethanes and diphosphane dioxides, see: Crepy & Imamoto (2003a ▶,b ▶); Glueck (2008 ▶); Knowles (1983 ▶, 2002 ▶); Pietrusiewicz & Zablocka (1988 ▶); Demchuk et al. (2003 ▶); Vinokurov et al. (2006 ▶); Vinokurov, Garabatos-Perera et al. (2008 ▶) and Vinokurov, Pietrusiewicz et al. (2008 ▶). For the structures of (–)-(S P)-methyl­phenyl­phosphine oxide and (+)-(R P)-(tert-butyl­vinyl­phosphino­yl)benzene, see: Pietrusiewicz et al. (1991 ▶); Szmigielska et al. (2006 ▶). For the determination of the absolute configuration of the stereogenic centers for the title compound, see: Pietrusiewicz et al. (1984 ▶, 1991 ▶) and Vinokurov, Pietrusiewicz et al. (2008 ▶).

Experimental

Crystal data

C16H18O2P2

M = 304.24

Monoclinic,

a = 11.686 (5) Å

b = 5.5291 (15) Å

c = 24.132 (10) Å

β = 96.36 (5)°

V = 1549.7 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 297 K

0.35 × 0.29 × 0.18 mm

Data collection

Stoe IPDS diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.927, T max = 0.953

20851 measured reflections

6041 independent reflections

4640 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.097

S = 0.99

6041 reflections

361 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶), 2656 Friedel pairs

Flack parameter: 0.01 (9)

Data collection: IPDS (Stoe & Cie, 1999 ▶); cell refinement: IPDS; data reduction: IPDS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶) and WinGX (Farrugia, 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶) and publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809004632/jh2072sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809004632/jh2072Isup2.hkl

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

C16H18O2P2	F(000) = 640
Mr = 304.24	Dx = 1.304 Mg m−3
Monoclinic, P21	Melting point: 511 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 11.686 (5) Å	Cell parameters from 8000 reflections
b = 5.5291 (15) Å	θ = 2.3–25.4°
c = 24.132 (10) Å	µ = 0.28 mm−1
β = 96.36 (5)°	T = 297 K
V = 1549.7 (10) Å3	Plate, white
Z = 4	0.35 × 0.29 × 0.18 mm

Stoe IPDS diffractometer	6041 independent reflections
Radiation source: fine-focus sealed tube	4640 reflections with I > 2σ(I)
graphite	Rint = 0.067
psi scans	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (Blessing, 1995)	h = −14→14
Tmin = 0.927, Tmax = 0.953	k = −6→6
20851 measured reflections	l = −29→29

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)] = 0.041	H-atom parameters constrained
wR(F2) = 0.097	w = 1/[σ2(Fo2) + (0.0482P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.002
6041 reflections	Δρmax = 0.37 e Å−3
361 parameters	Δρmin = −0.19 e Å−3
1 restraint	Absolute structure: Flack (1983), 2656 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (9)

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	0.30457 (7)	0.21685 (14)	0.97574 (3)	0.0353 (2)
P2	0.39031 (6)	−0.02618 (15)	1.14954 (3)	0.0346 (2)
O1	0.3363 (2)	0.4760 (5)	0.98268 (10)	0.0538 (6)
O2	0.3896 (2)	−0.2919 (4)	1.14004 (10)	0.0470 (6)
C1A	0.3199 (3)	0.0452 (6)	1.03959 (12)	0.0390 (7)
H1A	0.3089	−0.1213	1.0382	0.047*
C2A	0.3466 (3)	0.1518 (6)	1.08850 (12)	0.0377 (7)
H2A	0.3427	0.3193	1.0913	0.045*
C3A	0.2989 (3)	0.0536 (6)	1.20236 (11)	0.0379 (7)
C4A	0.2921 (4)	−0.1114 (7)	1.24450 (15)	0.0600 (10)
H4A	0.3340	−0.2545	1.2446	0.072*
C5A	0.2234 (5)	−0.0671 (11)	1.28698 (17)	0.0792 (14)
H5A	0.2188	−0.1808	1.3150	0.095*
C6A	0.1639 (4)	0.1403 (10)	1.28732 (19)	0.0741 (13)
H6A	0.1185	0.1701	1.3159	0.089*
C7A	0.1693 (4)	0.3089 (9)	1.2460 (2)	0.0704 (12)
H7A	0.1271	0.4512	1.2464	0.085*
C8A	0.2380 (3)	0.2673 (8)	1.20324 (15)	0.0531 (8)
H8A	0.2427	0.3827	1.1755	0.064*
C9A	0.5286 (3)	0.0957 (8)	1.17267 (15)	0.0557 (10)
H9A1	0.5606	0.0118	1.2056	0.083*
H9A2	0.5212	0.2645	1.1809	0.083*
H9A3	0.5784	0.0765	1.1439	0.083*
C10A	0.1564 (3)	0.1880 (6)	0.94567 (12)	0.0355 (7)
C11A	0.1106 (3)	0.3729 (7)	0.91121 (15)	0.0525 (9)
H11A	0.1567	0.5032	0.9036	0.063*
C12A	−0.0027 (4)	0.3649 (8)	0.88820 (19)	0.0639 (11)
H12A	−0.0319	0.4875	0.8643	0.077*
C13A	−0.0721 (3)	0.1788 (9)	0.90020 (18)	0.0625 (11)
H13A	−0.1492	0.1782	0.8856	0.075*
C14A	−0.0288 (3)	−0.0100 (9)	0.93402 (17)	0.0644 (11)
H14A	−0.0760	−0.1382	0.9417	0.077*
C15A	0.0867 (3)	−0.0058 (7)	0.95651 (13)	0.0490 (8)
H15A	0.1169	−0.1329	0.9788	0.059*
C16A	0.3893 (3)	0.0436 (8)	0.93298 (14)	0.0508 (9)
H16A	0.3879	0.1190	0.8971	0.076*
H16B	0.3583	−0.1170	0.9286	0.076*
H16C	0.4672	0.0355	0.9503	0.076*
P3	0.69714 (6)	0.45422 (16)	0.52266 (3)	0.03485 (19)
P4	0.61341 (7)	0.25487 (16)	0.34535 (3)	0.0377 (2)
O3	0.6815 (2)	0.7189 (5)	0.51686 (10)	0.0521 (6)
O4	0.6118 (2)	−0.0103 (5)	0.35230 (10)	0.0528 (6)
C1B	0.6767 (2)	0.2977 (6)	0.45711 (12)	0.0363 (7)
H1B	0.6813	0.1298	0.4570	0.044*
C2B	0.6553 (2)	0.4128 (6)	0.40913 (11)	0.0361 (7)
H2B	0.6621	0.5803	0.4085	0.043*
C3B	0.7090 (3)	0.3418 (6)	0.29501 (12)	0.0395 (7)
C4B	0.7920 (3)	0.1795 (7)	0.28267 (15)	0.0518 (9)
H4B	0.8021	0.0365	0.3029	0.062*
C5B	0.8607 (3)	0.2254 (9)	0.24069 (18)	0.0677 (11)
H5B	0.9151	0.1122	0.2324	0.081*
C6B	0.8484 (4)	0.4391 (9)	0.21121 (17)	0.0662 (11)
H6B	0.8953	0.4718	0.1834	0.079*
C7B	0.7671 (4)	0.6022 (8)	0.22304 (18)	0.0679 (12)
H7B	0.7576	0.7451	0.2027	0.082*
C8B	0.6986 (4)	0.5562 (7)	0.26523 (16)	0.0584 (10)
H8B	0.6449	0.6709	0.2736	0.070*
C9B	0.4772 (3)	0.3870 (7)	0.32300 (15)	0.0547 (10)
H9B1	0.4460	0.3149	0.2884	0.082*
H9B2	0.4864	0.5578	0.3179	0.082*
H9B3	0.4256	0.3595	0.3507	0.082*
C10B	0.8407 (3)	0.3773 (6)	0.55361 (12)	0.0345 (7)
C11B	0.9281 (3)	0.5428 (8)	0.54766 (15)	0.0542 (9)
H11B	0.9113	0.6854	0.5280	0.065*
C12B	1.0393 (3)	0.4980 (9)	0.57053 (19)	0.0678 (12)
H12B	1.0971	0.6092	0.5658	0.081*
C13B	1.0648 (3)	0.2913 (9)	0.60005 (18)	0.0650 (12)
H13B	1.1397	0.2632	0.6160	0.078*
C14B	0.9795 (3)	0.1226 (9)	0.60642 (17)	0.0634 (11)
H14B	0.9971	−0.0187	0.6265	0.076*
C15B	0.8674 (3)	0.1661 (7)	0.58256 (16)	0.0508 (9)
H15B	0.8103	0.0520	0.5862	0.061*
C16B	0.5972 (3)	0.3059 (8)	0.56197 (14)	0.0520 (9)
H16D	0.6010	0.3767	0.5984	0.078*
H16E	0.6161	0.1371	0.5653	0.078*
H16F	0.5207	0.3239	0.5433	0.078*

	U11	U22	U33	U12	U13	U23
P1	0.0399 (4)	0.0320 (5)	0.0331 (4)	−0.0040 (3)	0.0008 (3)	0.0008 (3)
P2	0.0375 (4)	0.0341 (5)	0.0315 (4)	−0.0016 (4)	0.0000 (3)	0.0002 (3)
O1	0.0653 (15)	0.0310 (14)	0.0615 (14)	−0.0135 (12)	−0.0088 (12)	0.0025 (12)
O2	0.0612 (14)	0.0282 (13)	0.0521 (12)	0.0006 (11)	0.0089 (11)	−0.0009 (10)
C1A	0.0425 (17)	0.0376 (17)	0.0362 (15)	−0.0016 (14)	0.0015 (13)	0.0010 (13)
C2A	0.0434 (17)	0.0346 (17)	0.0349 (15)	0.0013 (13)	0.0036 (13)	0.0025 (12)
C3A	0.0377 (16)	0.0416 (17)	0.0331 (14)	−0.0029 (14)	−0.0024 (12)	−0.0020 (13)
C4A	0.080 (3)	0.054 (3)	0.0479 (19)	0.0009 (19)	0.0144 (19)	0.0109 (16)
C5A	0.112 (4)	0.083 (4)	0.048 (2)	−0.004 (3)	0.032 (2)	0.006 (2)
C6A	0.074 (3)	0.086 (3)	0.068 (3)	−0.015 (3)	0.034 (2)	−0.016 (2)
C7A	0.056 (2)	0.067 (3)	0.092 (3)	0.002 (2)	0.024 (2)	−0.014 (2)
C8A	0.052 (2)	0.046 (2)	0.062 (2)	0.0021 (17)	0.0120 (16)	0.0027 (17)
C9A	0.045 (2)	0.070 (3)	0.0511 (19)	−0.0026 (18)	−0.0025 (16)	0.0010 (19)
C10A	0.0431 (16)	0.0322 (18)	0.0312 (13)	0.0015 (13)	0.0032 (12)	−0.0009 (12)
C11A	0.054 (2)	0.046 (2)	0.057 (2)	0.0032 (16)	−0.0003 (17)	0.0054 (16)
C12A	0.058 (2)	0.059 (3)	0.070 (3)	0.014 (2)	−0.014 (2)	0.002 (2)
C13A	0.043 (2)	0.070 (3)	0.071 (2)	0.0076 (19)	−0.0055 (18)	−0.024 (2)
C14A	0.051 (2)	0.077 (3)	0.066 (2)	−0.015 (2)	0.0072 (18)	−0.007 (2)
C15A	0.0511 (18)	0.045 (2)	0.0483 (17)	−0.0064 (16)	−0.0042 (14)	0.0050 (16)
C16A	0.0446 (19)	0.059 (2)	0.0503 (18)	−0.0003 (16)	0.0116 (15)	0.0019 (17)
P3	0.0352 (4)	0.0359 (5)	0.0330 (4)	0.0013 (4)	0.0018 (3)	−0.0026 (4)
P4	0.0410 (4)	0.0376 (5)	0.0345 (4)	−0.0042 (4)	0.0039 (3)	−0.0058 (4)
O3	0.0566 (15)	0.0390 (15)	0.0578 (14)	0.0047 (12)	−0.0064 (11)	−0.0032 (12)
O4	0.0715 (16)	0.0363 (15)	0.0538 (13)	−0.0085 (12)	0.0205 (12)	−0.0051 (11)
C1B	0.0320 (15)	0.0399 (19)	0.0369 (15)	−0.0027 (13)	0.0025 (12)	−0.0022 (13)
C2B	0.0339 (15)	0.0399 (19)	0.0346 (14)	0.0015 (13)	0.0040 (12)	−0.0015 (13)
C3B	0.0430 (17)	0.0439 (18)	0.0303 (14)	−0.0042 (14)	−0.0020 (13)	−0.0005 (13)
C4B	0.0444 (18)	0.052 (2)	0.059 (2)	0.0056 (16)	0.0084 (16)	0.0110 (17)
C5B	0.053 (2)	0.077 (3)	0.077 (3)	0.008 (2)	0.024 (2)	0.000 (3)
C6B	0.072 (3)	0.072 (3)	0.059 (2)	−0.017 (3)	0.027 (2)	0.002 (2)
C7B	0.095 (3)	0.054 (3)	0.058 (2)	−0.002 (2)	0.022 (2)	0.012 (2)
C8B	0.079 (3)	0.042 (2)	0.058 (2)	0.0048 (19)	0.0219 (19)	0.0017 (18)
C9B	0.0432 (18)	0.065 (3)	0.0533 (19)	0.0008 (17)	−0.0058 (15)	−0.0185 (18)
C10B	0.0341 (15)	0.0381 (18)	0.0310 (14)	0.0000 (12)	0.0027 (12)	−0.0041 (12)
C11B	0.0449 (19)	0.056 (2)	0.062 (2)	−0.0049 (16)	0.0059 (16)	0.0030 (18)
C12B	0.0373 (19)	0.078 (3)	0.087 (3)	−0.013 (2)	0.0034 (18)	−0.011 (3)
C13B	0.041 (2)	0.079 (3)	0.071 (2)	0.015 (2)	−0.0086 (17)	−0.025 (2)
C14B	0.057 (2)	0.067 (3)	0.062 (2)	0.018 (2)	−0.0108 (18)	−0.002 (2)
C15B	0.0440 (19)	0.047 (2)	0.060 (2)	0.0004 (15)	0.0014 (16)	0.0042 (17)
C16B	0.0427 (18)	0.067 (3)	0.0485 (19)	−0.0010 (17)	0.0128 (15)	0.0009 (17)

P1—O1	1.485 (3)	P3—O3	1.480 (3)
P1—C16A	1.786 (4)	P3—C16B	1.784 (3)
P1—C1A	1.801 (3)	P3—C1B	1.796 (3)
P1—C10A	1.809 (3)	P3—C10B	1.810 (3)
P2—O2	1.487 (3)	P4—O4	1.476 (3)
P2—C9A	1.782 (4)	P4—C9B	1.780 (4)
P2—C2A	1.798 (3)	P4—C2B	1.790 (3)
P2—C3A	1.806 (3)	P4—C3B	1.804 (3)
C1A—C2A	1.325 (4)	C1B—C2B	1.321 (4)
C1A—H1A	0.9300	C1B—H1B	0.9300
C2A—H2A	0.9300	C2B—H2B	0.9300
C3A—C4A	1.375 (5)	C3B—C4B	1.378 (5)
C3A—C8A	1.381 (5)	C3B—C8B	1.385 (5)
C4A—C5A	1.392 (6)	C4B—C5B	1.384 (5)
C4A—H4A	0.9300	C4B—H4B	0.9300
C5A—C6A	1.341 (7)	C5B—C6B	1.378 (7)
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—C7A	1.372 (7)	C6B—C7B	1.363 (6)
C6A—H6A	0.9300	C6B—H6B	0.9300
C7A—C8A	1.394 (5)	C7B—C8B	1.387 (5)
C7A—H7A	0.9300	C7B—H7B	0.9300
C8A—H8A	0.9300	C8B—H8B	0.9300
C9A—H9A1	0.9600	C9B—H9B1	0.9600
C9A—H9A2	0.9600	C9B—H9B2	0.9600
C9A—H9A3	0.9600	C9B—H9B3	0.9600
C10A—C11A	1.387 (5)	C10B—C15B	1.379 (5)
C10A—C15A	1.388 (5)	C10B—C11B	1.391 (5)
C11A—C12A	1.378 (6)	C11B—C12B	1.377 (5)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.361 (6)	C12B—C13B	1.362 (7)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.386 (6)	C13B—C14B	1.386 (6)
C13A—H13A	0.9300	C13B—H13B	0.9300
C14A—C15A	1.397 (5)	C14B—C15B	1.392 (5)
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—H15A	0.9300	C15B—H15B	0.9300
C16A—H16A	0.9600	C16B—H16D	0.9600
C16A—H16B	0.9600	C16B—H16E	0.9600
C16A—H16C	0.9600	C16B—H16F	0.9600
O1—P1—C16A	115.80 (17)	O3—P3—C16B	115.05 (17)
O1—P1—C1A	114.32 (15)	O3—P3—C1B	112.97 (15)
C16A—P1—C1A	101.69 (17)	C16B—P3—C1B	102.46 (17)
O1—P1—C10A	110.28 (15)	O3—P3—C10B	111.77 (15)
C16A—P1—C10A	106.75 (16)	C16B—P3—C10B	107.71 (16)
C1A—P1—C10A	107.26 (15)	C1B—P3—C10B	106.10 (14)
O2—P2—C9A	114.30 (18)	O4—P4—C9B	114.84 (18)
O2—P2—C2A	114.73 (15)	O4—P4—C2B	113.11 (15)
C9A—P2—C2A	102.42 (17)	C9B—P4—C2B	102.15 (16)
O2—P2—C3A	110.87 (15)	O4—P4—C3B	110.94 (15)
C9A—P2—C3A	105.85 (17)	C9B—P4—C3B	106.63 (18)
C2A—P2—C3A	107.94 (14)	C2B—P4—C3B	108.58 (15)
C2A—C1A—P1	121.3 (3)	C2B—C1B—P3	122.3 (3)
C2A—C1A—H1A	119.4	C2B—C1B—H1B	118.9
P1—C1A—H1A	119.4	P3—C1B—H1B	118.9
C1A—C2A—P2	120.2 (3)	C1B—C2B—P4	121.8 (3)
C1A—C2A—H2A	119.9	C1B—C2B—H2B	119.1
P2—C2A—H2A	119.9	P4—C2B—H2B	119.1
C4A—C3A—C8A	118.9 (3)	C4B—C3B—C8B	117.9 (3)
C4A—C3A—P2	116.6 (3)	C4B—C3B—P4	118.4 (3)
C8A—C3A—P2	124.5 (2)	C8B—C3B—P4	123.5 (3)
C3A—C4A—C5A	120.9 (4)	C3B—C4B—C5B	121.2 (4)
C3A—C4A—H4A	119.6	C3B—C4B—H4B	119.4
C5A—C4A—H4A	119.6	C5B—C4B—H4B	119.4
C6A—C5A—C4A	119.8 (4)	C6B—C5B—C4B	120.0 (4)
C6A—C5A—H5A	120.1	C6B—C5B—H5B	120.0
C4A—C5A—H5A	120.1	C4B—C5B—H5B	120.0
C5A—C6A—C7A	120.7 (4)	C7B—C6B—C5B	119.6 (3)
C5A—C6A—H6A	119.7	C7B—C6B—H6B	120.2
C7A—C6A—H6A	119.7	C5B—C6B—H6B	120.2
C6A—C7A—C8A	120.2 (4)	C6B—C7B—C8B	120.3 (4)
C6A—C7A—H7A	119.9	C6B—C7B—H7B	119.8
C8A—C7A—H7A	119.9	C8B—C7B—H7B	119.8
C3A—C8A—C7A	119.5 (4)	C3B—C8B—C7B	120.9 (4)
C3A—C8A—H8A	120.3	C3B—C8B—H8B	119.5
C7A—C8A—H8A	120.3	C7B—C8B—H8B	119.5
P2—C9A—H9A1	109.5	P4—C9B—H9B1	109.5
P2—C9A—H9A2	109.5	P4—C9B—H9B2	109.5
H9A1—C9A—H9A2	109.5	H9B1—C9B—H9B2	109.5
P2—C9A—H9A3	109.5	P4—C9B—H9B3	109.5
H9A1—C9A—H9A3	109.5	H9B1—C9B—H9B3	109.5
H9A2—C9A—H9A3	109.5	H9B2—C9B—H9B3	109.5
C11A—C10A—C15A	119.1 (3)	C15B—C10B—C11B	118.8 (3)
C11A—C10A—P1	117.6 (3)	C15B—C10B—P3	123.8 (3)
C15A—C10A—P1	123.2 (2)	C11B—C10B—P3	117.4 (3)
C12A—C11A—C10A	120.5 (4)	C12B—C11B—C10B	120.8 (4)
C12A—C11A—H11A	119.8	C12B—C11B—H11B	119.6
C10A—C11A—H11A	119.8	C10B—C11B—H11B	119.6
C13A—C12A—C11A	120.5 (4)	C13B—C12B—C11B	120.2 (4)
C13A—C12A—H12A	119.8	C13B—C12B—H12B	119.9
C11A—C12A—H12A	119.8	C11B—C12B—H12B	119.9
C12A—C13A—C14A	120.5 (4)	C12B—C13B—C14B	120.3 (4)
C12A—C13A—H13A	119.8	C12B—C13B—H13B	119.8
C14A—C13A—H13A	119.8	C14B—C13B—H13B	119.8
C13A—C14A—C15A	119.4 (4)	C13B—C14B—C15B	119.5 (4)
C13A—C14A—H14A	120.3	C13B—C14B—H14B	120.2
C15A—C14A—H14A	120.3	C15B—C14B—H14B	120.2
C10A—C15A—C14A	120.0 (4)	C10B—C15B—C14B	120.4 (4)
C10A—C15A—H15A	120.0	C10B—C15B—H15B	119.8
C14A—C15A—H15A	120.0	C14B—C15B—H15B	119.8
P1—C16A—H16A	109.5	P3—C16B—H16D	109.5
P1—C16A—H16B	109.5	P3—C16B—H16E	109.5
H16A—C16A—H16B	109.5	H16D—C16B—H16E	109.5
P1—C16A—H16C	109.5	P3—C16B—H16F	109.5
H16A—C16A—H16C	109.5	H16D—C16B—H16F	109.5
H16B—C16A—H16C	109.5	H16E—C16B—H16F	109.5
C3A—P2—C2A—C1A	−125.9 (7)	O1—P1—C1A—C2A	6.21 (37)
P1—C1A—C2A—P2	−167.1 (5)	O2—P2—C2A—C1A	−1.83 (36)
C16A—P1—C1A—C2A	131.7 (2)	P1—C1A—C2A—P2	−167.15 (20)