(S)-2,2'-Bis­(di­cyclo­hexyl­phosphino­amino)-1,1'-bi­naphthyl

The the crystal structure of the title compound, C₄₄H₅₈N₂P₂, the molecule has a non-crystallographic twofold axis. The bond lengths and angles are within the expected ranges.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.068
• wR factor = 0.155
• Data-to-parameter ratio = 19.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_420  Alert C D-H Without Acceptor       N(1)   -   H(1A)             ?

PLAT_420  Alert C D-H Without Acceptor       N(2)   -   H(2A)             ?

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.55
         From the CIF: _reflns_number_total               4786
         Count of symmetry unique reflns         4815
         Completeness (_total/calc)             99.40%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present          yes
          WARNING: Large fraction of Friedel related reflns may
                   be needed to determine absolute structure


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 2 Alert Level C = Please check

---

Computing details

Data collection: SMART (Bruker, 1995); cell refinement: SMART; data reduction: SHELXTL-NT (Bruker, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-NT; software used to prepare material for publication: SHELXTL-NT.

(S)-2,2'-bis(dicyclohexylphosphinoamino)-1,1'-binaphthyl

Crystal data

C44H58N2P2	F(000) = 732
Mr = 676.89	Dx = 1.113 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 10.316 (3) Å	Cell parameters from 5501 reflections
b = 16.988 (5) Å	θ = 1–27.5°
c = 11.635 (3) Å	µ = 0.14 mm^−1
β = 97.971 (7)°	T = 294 K
V = 2019.4 (10) Å^3	Prism, colorless
Z = 2	0.30 × 0.28 × 0.26 mm

Data collection

Bruker CCD area-detector diffractometer	4786 independent reflections
Radiation source: fine-focus sealed tube	2931 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
φ and ω scans	θmax = 27.6°, θmin = 1.8°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	h = −11→13
Tmin = 0.960, Tmax = 0.965	k = −18→22
13673 measured reflections	l = −15→12

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.068	H-atom parameters constrained
wR(F^2) = 0.155	w = 1/[σ^2(Fo^2) + (0.05P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max < 0.001
8354 reflections	Δρmax = 0.42 e Å^−3
433 parameters	Δρmin = −0.30 e Å^−3
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (10)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
P1	0.21560 (10)	0.16590 (6)	0.30245 (8)	0.0585 (3)
P2	0.56995 (10)	−0.12912 (8)	0.20232 (9)	0.0668 (3)
N1	0.2423 (3)	0.06875 (17)	0.2831 (2)	0.0560 (8)
H1A	0.2920	0.0570	0.2321	0.067*
N2	0.4183 (3)	−0.0942 (2)	0.2207 (2)	0.0629 (9)
H2A	0.4069	−0.0807	0.2899	0.075*
C1	0.3126 (3)	−0.0856 (2)	0.1346 (3)	0.0504 (9)
C2	0.3318 (4)	−0.0839 (2)	0.0159 (3)	0.0638 (11)
H2B	0.4162	−0.0879	−0.0030	0.077*
C3	0.2298 (4)	−0.0765 (3)	−0.0701 (3)	0.0666 (11)
H3A	0.2455	−0.0755	−0.1469	0.080*
C4	0.0994 (4)	−0.0702 (2)	−0.0452 (3)	0.0548 (9)
C5	−0.0085 (4)	−0.0643 (2)	−0.1326 (3)	0.0688 (11)
H5A	0.0054	−0.0635	−0.2099	0.083*
C6	−0.1334 (4)	−0.0595 (3)	−0.1070 (3)	0.0714 (12)
H6A	−0.2035	−0.0553	−0.1662	0.086*
C7	−0.1548 (4)	−0.0611 (3)	0.0085 (3)	0.0692 (11)
H7A	−0.2400	−0.0592	0.0261	0.083*
C8	−0.0524 (4)	−0.0654 (2)	0.0966 (3)	0.0566 (9)
H8A	−0.0691	−0.0654	0.1732	0.068*
C9	0.0781 (3)	−0.0699 (2)	0.0736 (3)	0.0443 (8)
C10	0.1870 (3)	−0.0755 (2)	0.1628 (3)	0.0450 (8)
C11	0.1689 (3)	−0.0669 (2)	0.2888 (3)	0.0431 (8)
C12	0.1252 (3)	−0.1315 (2)	0.3519 (3)	0.0469 (8)
C13	0.1026 (4)	−0.2064 (2)	0.3040 (3)	0.0593 (10)
H13A	0.1192	−0.2153	0.2286	0.071*
C14	0.0566 (4)	−0.2673 (3)	0.3644 (4)	0.0727 (12)
H14A	0.0424	−0.3165	0.3301	0.087*
C15	0.0312 (4)	−0.2545 (3)	0.4789 (4)	0.0774 (13)
H15A	−0.0005	−0.2953	0.5204	0.093*
C16	0.0529 (4)	−0.1838 (3)	0.5275 (3)	0.0670 (11)
H16A	0.0349	−0.1764	0.6029	0.080*
C17	0.1018 (3)	−0.1199 (3)	0.4698 (3)	0.0541 (9)
C18	0.1280 (4)	−0.0451 (3)	0.5175 (3)	0.0648 (11)
H18A	0.1140	−0.0366	0.5938	0.078*
C19	0.1729 (4)	0.0156 (2)	0.4586 (3)	0.0575 (10)
H19A	0.1904	0.0639	0.4951	0.069*
C20	0.1934 (3)	0.0056 (2)	0.3400 (3)	0.0459 (8)
C21	0.1015 (4)	0.1917 (2)	0.1698 (3)	0.0625 (10)
H21A	0.0975	0.2493	0.1666	0.075*
C22	−0.0354 (4)	0.1633 (3)	0.1829 (4)	0.0822 (12)
H22A	−0.0613	0.1852	0.2533	0.099*
H22B	−0.0351	0.1064	0.1898	0.099*
C23	−0.1340 (5)	0.1878 (3)	0.0793 (5)	0.1027 (17)
H23A	−0.2189	0.1656	0.0875	0.123*
H23B	−0.1425	0.2447	0.0785	0.123*
C24	−0.0935 (5)	0.1607 (4)	−0.0353 (5)	0.1042 (18)
H24A	−0.0937	0.1036	−0.0384	0.125*
H24B	−0.1559	0.1799	−0.0992	0.125*
C25	0.0406 (5)	0.1910 (4)	−0.0472 (4)	0.1016 (18)
H25A	0.0387	0.2480	−0.0505	0.122*
H25B	0.0667	0.1717	−0.1191	0.122*
C26	0.1410 (4)	0.1644 (3)	0.0551 (3)	0.0784 (12)
H26A	0.1477	0.1075	0.0550	0.094*
H26B	0.2262	0.1859	0.0465	0.094*
C27	0.3726 (4)	0.2048 (2)	0.2703 (3)	0.0623 (10)
H27A	0.3986	0.1743	0.2057	0.075*
C28	0.3661 (4)	0.2912 (3)	0.2351 (4)	0.0800 (13)
H28A	0.3068	0.2967	0.1632	0.096*
H28B	0.3305	0.3213	0.2943	0.096*
C29	0.4976 (5)	0.3249 (3)	0.2188 (4)	0.0940 (15)
H29A	0.5278	0.2997	0.1526	0.113*
H29B	0.4878	0.3806	0.2019	0.113*
C30	0.5986 (5)	0.3139 (4)	0.3237 (5)	0.1082 (19)
H30A	0.5747	0.3448	0.3876	0.130*
H30B	0.6828	0.3325	0.3067	0.130*
C31	0.6087 (5)	0.2286 (4)	0.3577 (5)	0.1033 (17)
H31A	0.6686	0.2233	0.4293	0.124*
H31B	0.6445	0.1991	0.2980	0.124*
C32	0.4769 (4)	0.1939 (3)	0.3746 (4)	0.0802 (13)
H32A	0.4877	0.1381	0.3908	0.096*
H32B	0.4474	0.2185	0.4415	0.096*
C33	0.6714 (4)	−0.0829 (3)	0.3255 (3)	0.0703 (12)
H33A	0.7567	−0.1092	0.3326	0.084*
C34	0.6966 (4)	0.0039 (3)	0.2998 (4)	0.0790 (13)
H34A	0.7284	0.0080	0.2253	0.095*
H34B	0.6151	0.0329	0.2949	0.095*
C35	0.7964 (5)	0.0402 (3)	0.3933 (5)	0.1021 (17)
H35A	0.8073	0.0956	0.3763	0.123*
H35B	0.8803	0.0144	0.3936	0.123*
C36	0.7520 (6)	0.0317 (3)	0.5127 (5)	0.1027 (17)
H36A	0.8202	0.0516	0.5713	0.123*
H36B	0.6744	0.0636	0.5152	0.123*
C37	0.7223 (6)	−0.0513 (3)	0.5406 (4)	0.1048 (18)
H37A	0.6857	−0.0528	0.6130	0.126*
H37B	0.8028	−0.0816	0.5509	0.126*
C38	0.6253 (5)	−0.0890 (3)	0.4445 (4)	0.0888 (15)
H38A	0.6139	−0.1440	0.4630	0.107*
H38B	0.5410	−0.0632	0.4417	0.107*
C39	0.5611 (4)	−0.2328 (3)	0.2497 (4)	0.0779 (13)
H39A	0.5386	−0.2331	0.3288	0.093*
C40	0.6902 (5)	−0.2727 (4)	0.2514 (6)	0.1137 (19)
H40A	0.7541	−0.2471	0.3084	0.136*
H40B	0.7191	−0.2668	0.1761	0.136*
C41	0.6844 (6)	−0.3601 (4)	0.2806 (7)	0.134 (2)
H41A	0.7684	−0.3840	0.2738	0.161*
H41B	0.6688	−0.3658	0.3605	0.161*
C42	0.5785 (7)	−0.4035 (4)	0.2024 (6)	0.129 (2)
H42A	0.6014	−0.4058	0.1244	0.155*
H42B	0.5722	−0.4570	0.2301	0.155*
C43	0.4514 (7)	−0.3642 (4)	0.1999 (7)	0.138 (2)
H43A	0.4213	−0.3709	0.2746	0.165*
H43B	0.3883	−0.3894	0.1418	0.165*
C44	0.4564 (5)	−0.2768 (4)	0.1726 (6)	0.122 (2)
H44A	0.4711	−0.2705	0.0926	0.146*
H44B	0.3722	−0.2535	0.1802	0.146*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0654 (6)	0.0622 (7)	0.0493 (5)	0.0026 (6)	0.0133 (5)	−0.0038 (5)
P2	0.0518 (6)	0.0921 (9)	0.0584 (6)	0.0116 (6)	0.0150 (5)	0.0041 (6)
N1	0.0633 (18)	0.062 (2)	0.0463 (17)	0.0038 (16)	0.0200 (14)	−0.0010 (14)
N2	0.0530 (17)	0.094 (3)	0.0411 (17)	0.0132 (16)	0.0060 (14)	0.0032 (15)
C1	0.052 (2)	0.061 (2)	0.0383 (19)	0.0048 (18)	0.0072 (16)	−0.0006 (15)
C2	0.062 (2)	0.092 (3)	0.042 (2)	0.007 (2)	0.0206 (19)	−0.0004 (19)
C3	0.081 (3)	0.083 (3)	0.040 (2)	0.008 (2)	0.022 (2)	0.0017 (18)
C4	0.069 (2)	0.064 (2)	0.0316 (18)	−0.001 (2)	0.0073 (17)	−0.0004 (16)
C5	0.087 (3)	0.086 (3)	0.0302 (19)	−0.009 (3)	−0.003 (2)	−0.0031 (18)
C6	0.073 (3)	0.091 (4)	0.044 (2)	−0.007 (2)	−0.012 (2)	−0.002 (2)
C7	0.052 (2)	0.097 (3)	0.056 (2)	−0.008 (2)	−0.0002 (19)	−0.001 (2)
C8	0.057 (2)	0.070 (3)	0.041 (2)	0.002 (2)	0.0031 (17)	0.0037 (17)
C9	0.0466 (18)	0.052 (2)	0.0343 (17)	−0.0006 (17)	0.0046 (15)	−0.0049 (14)
C10	0.0506 (19)	0.052 (2)	0.0333 (17)	0.0055 (17)	0.0103 (15)	−0.0011 (14)
C11	0.0417 (17)	0.053 (2)	0.0355 (17)	0.0044 (16)	0.0072 (14)	0.0009 (14)
C12	0.0415 (17)	0.060 (2)	0.0384 (18)	0.0004 (18)	0.0018 (14)	0.0061 (16)
C13	0.070 (2)	0.063 (3)	0.045 (2)	−0.011 (2)	0.0083 (18)	0.0032 (17)
C14	0.080 (3)	0.075 (3)	0.061 (3)	−0.021 (2)	0.002 (2)	0.008 (2)
C15	0.084 (3)	0.089 (4)	0.060 (3)	−0.016 (3)	0.011 (2)	0.025 (2)
C16	0.074 (3)	0.082 (3)	0.046 (2)	−0.006 (2)	0.013 (2)	0.017 (2)
C17	0.052 (2)	0.075 (3)	0.0355 (18)	0.006 (2)	0.0071 (15)	0.0060 (18)
C18	0.073 (3)	0.088 (3)	0.034 (2)	0.003 (2)	0.0117 (18)	0.0008 (19)
C19	0.069 (2)	0.066 (3)	0.038 (2)	−0.002 (2)	0.0071 (18)	−0.0056 (16)
C20	0.0466 (19)	0.055 (2)	0.0362 (18)	0.0032 (17)	0.0056 (15)	0.0023 (15)
C21	0.064 (2)	0.061 (3)	0.062 (2)	−0.0026 (19)	0.008 (2)	0.0044 (18)
C22	0.068 (3)	0.096 (4)	0.082 (3)	−0.003 (3)	0.009 (2)	−0.006 (3)
C23	0.074 (3)	0.102 (5)	0.129 (5)	−0.007 (3)	0.002 (3)	0.006 (3)
C24	0.103 (4)	0.118 (5)	0.082 (4)	−0.031 (4)	−0.020 (3)	0.028 (3)
C25	0.089 (3)	0.142 (5)	0.067 (3)	−0.027 (3)	−0.014 (3)	0.033 (3)
C26	0.081 (3)	0.105 (4)	0.047 (2)	−0.003 (3)	0.004 (2)	0.009 (2)
C27	0.070 (2)	0.061 (3)	0.054 (2)	0.001 (2)	0.004 (2)	−0.0073 (18)
C28	0.091 (3)	0.078 (3)	0.071 (3)	−0.013 (3)	0.009 (2)	0.004 (2)
C29	0.096 (4)	0.095 (4)	0.090 (4)	−0.036 (3)	0.008 (3)	0.011 (3)
C30	0.082 (3)	0.126 (5)	0.113 (5)	−0.039 (3)	0.002 (3)	0.013 (4)
C31	0.077 (3)	0.120 (5)	0.106 (4)	−0.022 (3)	−0.010 (3)	0.016 (3)
C32	0.070 (3)	0.095 (4)	0.071 (3)	−0.006 (2)	−0.002 (2)	0.013 (2)
C33	0.049 (2)	0.099 (4)	0.062 (3)	0.001 (2)	0.0040 (19)	0.008 (2)
C34	0.067 (3)	0.096 (4)	0.077 (3)	−0.004 (3)	0.018 (2)	0.007 (3)
C35	0.085 (4)	0.104 (4)	0.114 (5)	−0.013 (3)	0.005 (3)	0.011 (3)
C36	0.107 (4)	0.100 (5)	0.092 (4)	−0.016 (3)	−0.015 (3)	−0.004 (3)
C37	0.118 (4)	0.121 (5)	0.067 (3)	−0.030 (4)	−0.018 (3)	0.012 (3)
C38	0.093 (3)	0.108 (4)	0.063 (3)	−0.021 (3)	0.002 (3)	0.009 (2)
C39	0.071 (3)	0.103 (4)	0.060 (3)	0.014 (3)	0.008 (2)	−0.012 (2)
C40	0.085 (4)	0.108 (5)	0.145 (5)	0.036 (3)	0.007 (3)	0.006 (4)
C41	0.118 (5)	0.117 (6)	0.165 (7)	0.044 (4)	0.012 (5)	0.019 (4)
C42	0.166 (6)	0.091 (5)	0.130 (5)	0.031 (5)	0.018 (5)	−0.009 (4)
C43	0.125 (5)	0.085 (5)	0.197 (8)	0.012 (4)	0.002 (5)	−0.003 (4)
C44	0.095 (4)	0.097 (5)	0.163 (6)	0.013 (4)	−0.018 (4)	−0.007 (4)

Geometric parameters (Å, º)

P1—N1	1.693 (3)	C25—C26	1.533 (6)
P1—C27	1.835 (4)	C25—H25A	0.9700
P1—C21	1.859 (4)	C25—H25B	0.9700
P2—N2	1.715 (3)	C26—H26A	0.9700
P2—C33	1.830 (4)	C26—H26B	0.9700
P2—C39	1.851 (5)	C27—C32	1.517 (5)
N1—C20	1.392 (4)	C27—C28	1.522 (6)
N1—H1A	0.8600	C27—H27A	0.9800
N2—C1	1.382 (4)	C28—C29	1.508 (6)
N2—H2A	0.8600	C28—H28A	0.9700
C1—C10	1.391 (4)	C28—H28B	0.9700
C1—C2	1.422 (4)	C29—C30	1.502 (7)
C2—C3	1.354 (5)	C29—H29A	0.9700
C2—H2B	0.9300	C29—H29B	0.9700
C3—C4	1.419 (5)	C30—C31	1.503 (7)
C3—H3A	0.9300	C30—H30A	0.9700
C4—C5	1.403 (5)	C30—H30B	0.9700
C4—C9	1.430 (4)	C31—C32	1.519 (6)
C5—C6	1.364 (5)	C31—H31A	0.9700
C5—H5A	0.9300	C31—H31B	0.9700
C6—C7	1.393 (5)	C32—H32A	0.9700
C6—H6A	0.9300	C32—H32B	0.9700
C7—C8	1.369 (5)	C33—C38	1.529 (5)
C7—H7A	0.9300	C33—C34	1.535 (6)
C8—C9	1.410 (5)	C33—H33A	0.9800
C8—H8A	0.9300	C34—C35	1.521 (6)
C9—C10	1.423 (4)	C34—H34A	0.9700
C10—C11	1.509 (4)	C34—H34B	0.9700
C11—C20	1.376 (5)	C35—C36	1.529 (7)
C11—C12	1.429 (5)	C35—H35A	0.9700
C12—C13	1.395 (5)	C35—H35B	0.9700
C12—C17	1.439 (4)	C36—C37	1.489 (6)
C13—C14	1.371 (5)	C36—H36A	0.9700
C13—H13A	0.9300	C36—H36B	0.9700
C14—C15	1.409 (6)	C37—C38	1.532 (6)
C14—H14A	0.9300	C37—H37A	0.9700
C15—C16	1.334 (6)	C37—H37B	0.9700
C15—H15A	0.9300	C38—H38A	0.9700
C16—C17	1.406 (5)	C38—H38B	0.9700
C16—H16A	0.9300	C39—C40	1.492 (6)
C17—C18	1.397 (5)	C39—C44	1.503 (7)
C18—C19	1.356 (5)	C39—H39A	0.9800
C18—H18A	0.9300	C40—C41	1.527 (9)
C19—C20	1.435 (4)	C40—H40A	0.9700
C19—H19A	0.9300	C40—H40B	0.9700
C21—C22	1.520 (5)	C41—C42	1.513 (8)
C21—C26	1.521 (6)	C41—H41A	0.9700
C21—H21A	0.9800	C41—H41B	0.9700
C22—C23	1.523 (6)	C42—C43	1.467 (8)
C22—H22A	0.9700	C42—H42A	0.9700
C22—H22B	0.9700	C42—H42B	0.9700
C23—C24	1.523 (7)	C43—C44	1.521 (8)
C23—H23A	0.9700	C43—H43A	0.9700
C23—H23B	0.9700	C43—H43B	0.9700
C24—C25	1.501 (6)	C44—H44A	0.9700
C24—H24A	0.9700	C44—H44B	0.9700
C24—H24B	0.9700
N1—P1—C27	99.15 (16)	C32—C27—C28	109.4 (3)
N1—P1—C21	102.46 (17)	C32—C27—P1	110.0 (3)
C27—P1—C21	102.78 (18)	C28—C27—P1	113.2 (3)
N2—P2—C33	100.76 (17)	C32—C27—H27A	108.1
N2—P2—C39	102.06 (18)	C28—C27—H27A	108.1
C33—P2—C39	102.8 (2)	P1—C27—H27A	108.1
C20—N1—P1	127.7 (2)	C29—C28—C27	113.1 (4)
C20—N1—H1A	116.1	C29—C28—H28A	109.0
P1—N1—H1A	116.1	C27—C28—H28A	109.0
C1—N2—P2	126.0 (2)	C29—C28—H28B	109.0
C1—N2—H2A	117.0	C27—C28—H28B	109.0
P2—N2—H2A	117.0	H28A—C28—H28B	107.8
N2—C1—C10	120.6 (3)	C30—C29—C28	112.7 (4)
N2—C1—C2	120.3 (3)	C30—C29—H29A	109.1
C10—C1—C2	119.1 (3)	C28—C29—H29A	109.1
C3—C2—C1	121.4 (3)	C30—C29—H29B	109.1
C3—C2—H2B	119.3	C28—C29—H29B	109.1
C1—C2—H2B	119.3	H29A—C29—H29B	107.8
C2—C3—C4	121.2 (3)	C29—C30—C31	110.4 (5)
C2—C3—H3A	119.4	C29—C30—H30A	109.6
C4—C3—H3A	119.4	C31—C30—H30A	109.6
C5—C4—C3	122.5 (3)	C29—C30—H30B	109.6
C5—C4—C9	119.2 (3)	C31—C30—H30B	109.6
C3—C4—C9	118.3 (3)	H30A—C30—H30B	108.1
C6—C5—C4	121.6 (3)	C30—C31—C32	112.1 (5)
C6—C5—H5A	119.2	C30—C31—H31A	109.2
C4—C5—H5A	119.2	C32—C31—H31A	109.2
C5—C6—C7	119.4 (3)	C30—C31—H31B	109.2
C5—C6—H6A	120.3	C32—C31—H31B	109.2
C7—C6—H6A	120.3	H31A—C31—H31B	107.9
C8—C7—C6	121.0 (4)	C27—C32—C31	113.5 (4)
C8—C7—H7A	119.5	C27—C32—H32A	108.9
C6—C7—H7A	119.5	C31—C32—H32A	108.9
C7—C8—C9	121.2 (3)	C27—C32—H32B	108.9
C7—C8—H8A	119.4	C31—C32—H32B	108.9
C9—C8—H8A	119.4	H32A—C32—H32B	107.7
C8—C9—C10	122.8 (3)	C38—C33—C34	108.9 (4)
C8—C9—C4	117.6 (3)	C38—C33—P2	117.7 (3)
C10—C9—C4	119.6 (3)	C34—C33—P2	110.7 (3)
C1—C10—C9	120.2 (3)	C38—C33—H33A	106.3
C1—C10—C11	119.0 (3)	C34—C33—H33A	106.3
C9—C10—C11	120.7 (3)	P2—C33—H33A	106.3
C20—C11—C12	121.1 (3)	C35—C34—C33	111.5 (4)
C20—C11—C10	117.9 (3)	C35—C34—H34A	109.3
C12—C11—C10	121.0 (3)	C33—C34—H34A	109.3
C13—C12—C11	122.9 (3)	C35—C34—H34B	109.3
C13—C12—C17	117.7 (3)	C33—C34—H34B	109.3
C11—C12—C17	119.4 (3)	H34A—C34—H34B	108.0
C14—C13—C12	122.2 (4)	C34—C35—C36	110.7 (4)
C14—C13—H13A	118.9	C34—C35—H35A	109.5
C12—C13—H13A	118.9	C36—C35—H35A	109.5
C13—C14—C15	119.4 (4)	C34—C35—H35B	109.5
C13—C14—H14A	120.3	C36—C35—H35B	109.5
C15—C14—H14A	120.3	H35A—C35—H35B	108.1
C16—C15—C14	119.8 (4)	C37—C36—C35	112.6 (5)
C16—C15—H15A	120.1	C37—C36—H36A	109.1
C14—C15—H15A	120.1	C35—C36—H36A	109.1
C15—C16—C17	122.9 (4)	C37—C36—H36B	109.1
C15—C16—H16A	118.5	C35—C36—H36B	109.1
C17—C16—H16A	118.5	H36A—C36—H36B	107.8
C18—C17—C16	125.1 (3)	C36—C37—C38	111.7 (4)
C18—C17—C12	117.1 (3)	C36—C37—H37A	109.3
C16—C17—C12	117.8 (4)	C38—C37—H37A	109.3
C19—C18—C17	123.5 (3)	C36—C37—H37B	109.3
C19—C18—H18A	118.3	C38—C37—H37B	109.3
C17—C18—H18A	118.3	H37A—C37—H37B	107.9
C18—C19—C20	120.1 (4)	C33—C38—C37	112.3 (4)
C18—C19—H19A	120.0	C33—C38—H38A	109.2
C20—C19—H19A	120.0	C37—C38—H38A	109.2
C11—C20—N1	122.7 (3)	C33—C38—H38B	109.2
C11—C20—C19	118.8 (3)	C37—C38—H38B	109.2
N1—C20—C19	118.5 (3)	H38A—C38—H38B	107.9
C22—C21—C26	110.9 (3)	C40—C39—C44	110.4 (4)
C22—C21—P1	109.4 (3)	C40—C39—P2	110.8 (4)
C26—C21—P1	116.2 (3)	C44—C39—P2	110.9 (4)
C22—C21—H21A	106.6	C40—C39—H39A	108.2
C26—C21—H21A	106.6	C44—C39—H39A	108.2
P1—C21—H21A	106.6	P2—C39—H39A	108.2
C21—C22—C23	111.2 (4)	C39—C40—C41	112.5 (5)
C21—C22—H22A	109.4	C39—C40—H40A	109.1
C23—C22—H22A	109.4	C41—C40—H40A	109.1
C21—C22—H22B	109.4	C39—C40—H40B	109.1
C23—C22—H22B	109.4	C41—C40—H40B	109.1
H22A—C22—H22B	108.0	H40A—C40—H40B	107.8
C24—C23—C22	112.1 (4)	C42—C41—C40	112.8 (6)
C24—C23—H23A	109.2	C42—C41—H41A	109.0
C22—C23—H23A	109.2	C40—C41—H41A	109.0
C24—C23—H23B	109.2	C42—C41—H41B	109.0
C22—C23—H23B	109.2	C40—C41—H41B	109.0
H23A—C23—H23B	107.9	H41A—C41—H41B	107.8
C25—C24—C23	110.2 (4)	C43—C42—C41	111.1 (6)
C25—C24—H24A	109.6	C43—C42—H42A	109.4
C23—C24—H24A	109.6	C41—C42—H42A	109.4
C25—C24—H24B	109.6	C43—C42—H42B	109.4
C23—C24—H24B	109.6	C41—C42—H42B	109.4
H24A—C24—H24B	108.1	H42A—C42—H42B	108.0
C24—C25—C26	111.1 (4)	C42—C43—C44	113.1 (6)
C24—C25—H25A	109.4	C42—C43—H43A	109.0
C26—C25—H25A	109.4	C44—C43—H43A	109.0
C24—C25—H25B	109.4	C42—C43—H43B	109.0
C26—C25—H25B	109.4	C44—C43—H43B	109.0
H25A—C25—H25B	108.0	H43A—C43—H43B	107.8
C21—C26—C25	111.0 (4)	C39—C44—C43	113.8 (5)
C21—C26—H26A	109.4	C39—C44—H44A	108.8
C25—C26—H26A	109.4	C43—C44—H44A	108.8
C21—C26—H26B	109.4	C39—C44—H44B	108.8
C25—C26—H26B	109.4	C43—C44—H44B	108.8
H26A—C26—H26B	108.0	H44A—C44—H44B	107.7
C27—P1—N1—C20	148.5 (3)	C12—C11—C20—C19	−0.6 (5)
C21—P1—N1—C20	−106.2 (3)	C10—C11—C20—C19	178.1 (3)
C33—P2—N2—C1	155.0 (3)	P1—N1—C20—C11	149.8 (3)
C39—P2—N2—C1	−99.2 (3)	P1—N1—C20—C19	−32.8 (4)
P2—N2—C1—C10	163.9 (3)	C18—C19—C20—C11	−1.1 (5)
P2—N2—C1—C2	−18.5 (5)	C18—C19—C20—N1	−178.6 (3)
N2—C1—C2—C3	179.2 (4)	N1—P1—C21—C22	77.7 (3)
C10—C1—C2—C3	−3.2 (6)	C27—P1—C21—C22	−179.8 (3)
C1—C2—C3—C4	−0.1 (6)	N1—P1—C21—C26	−48.9 (3)
C2—C3—C4—C5	−178.5 (4)	C27—P1—C21—C26	53.7 (4)
C2—C3—C4—C9	1.5 (6)	C26—C21—C22—C23	−54.1 (5)
C3—C4—C5—C6	178.9 (4)	P1—C21—C22—C23	176.4 (3)
C9—C4—C5—C6	−1.1 (6)	C21—C22—C23—C24	54.7 (6)
C4—C5—C6—C7	−0.4 (7)	C22—C23—C24—C25	−56.0 (6)
C5—C6—C7—C8	1.5 (6)	C23—C24—C25—C26	57.0 (7)
C6—C7—C8—C9	−1.2 (6)	C22—C21—C26—C25	55.5 (5)
C7—C8—C9—C10	−179.2 (3)	P1—C21—C26—C25	−178.7 (3)
C7—C8—C9—C4	−0.3 (6)	C24—C25—C26—C21	−57.5 (6)
C5—C4—C9—C8	1.4 (5)	N1—P1—C27—C32	−79.0 (3)
C3—C4—C9—C8	−178.6 (4)	C21—P1—C27—C32	175.9 (3)
C5—C4—C9—C10	−179.7 (3)	N1—P1—C27—C28	158.3 (3)
C3—C4—C9—C10	0.3 (5)	C21—P1—C27—C28	53.2 (3)
N2—C1—C10—C9	−177.4 (3)	C32—C27—C28—C29	52.0 (5)
C2—C1—C10—C9	5.0 (5)	P1—C27—C28—C29	175.0 (3)
N2—C1—C10—C11	5.4 (5)	C27—C28—C29—C30	−54.8 (6)
C2—C1—C10—C11	−172.2 (3)	C28—C29—C30—C31	54.4 (7)
C8—C9—C10—C1	175.3 (3)	C29—C30—C31—C32	−53.9 (6)
C4—C9—C10—C1	−3.6 (5)	C28—C27—C32—C31	−52.0 (5)
C8—C9—C10—C11	−7.6 (5)	P1—C27—C32—C31	−176.9 (4)
C4—C9—C10—C11	173.6 (3)	C30—C31—C32—C27	54.5 (6)
C1—C10—C11—C20	79.9 (4)	N2—P2—C33—C38	48.2 (4)
C9—C10—C11—C20	−97.3 (4)	C39—P2—C33—C38	−57.0 (4)
C1—C10—C11—C12	−101.4 (4)	N2—P2—C33—C34	−77.9 (3)
C9—C10—C11—C12	81.4 (4)	C39—P2—C33—C34	176.9 (3)
C20—C11—C12—C13	−178.3 (3)	C38—C33—C34—C35	57.4 (5)
C10—C11—C12—C13	3.0 (5)	P2—C33—C34—C35	−171.8 (3)
C20—C11—C12—C17	2.3 (5)	C33—C34—C35—C36	−56.7 (5)
C10—C11—C12—C17	−176.4 (3)	C34—C35—C36—C37	54.3 (6)
C11—C12—C13—C14	−177.9 (3)	C35—C36—C37—C38	−52.9 (7)
C17—C12—C13—C14	1.5 (5)	C34—C33—C38—C37	−55.7 (5)
C12—C13—C14—C15	−0.1 (6)	P2—C33—C38—C37	177.3 (4)
C13—C14—C15—C16	−0.5 (7)	C36—C37—C38—C33	54.4 (6)
C14—C15—C16—C17	−0.5 (7)	N2—P2—C39—C40	−174.4 (4)
C15—C16—C17—C18	−178.9 (4)	C33—P2—C39—C40	−70.3 (4)
C15—C16—C17—C12	2.0 (6)	N2—P2—C39—C44	62.6 (4)
C13—C12—C17—C18	178.4 (3)	C33—P2—C39—C44	166.7 (3)
C11—C12—C17—C18	−2.1 (5)	C44—C39—C40—C41	−52.1 (7)
C13—C12—C17—C16	−2.4 (5)	P2—C39—C40—C41	−175.4 (5)
C11—C12—C17—C16	177.0 (3)	C39—C40—C41—C42	53.7 (7)
C16—C17—C18—C19	−178.7 (4)	C40—C41—C42—C43	−52.5 (8)
C12—C17—C18—C19	0.4 (6)	C41—C42—C43—C44	51.6 (9)
C17—C18—C19—C20	1.3 (6)	C40—C39—C44—C43	51.7 (7)
C12—C11—C20—N1	176.7 (3)	P2—C39—C44—C43	175.0 (4)
C10—C11—C20—N1	−4.6 (5)	C42—C43—C44—C39	−52.7 (8)