{[(N-Methyl-p-toluidino)­di­phenyl­phospho­ranyl­idene]­methyl}(N-methyl-p-toluidino)­di­phenyl­phospho­nium iodide

The cationic part of the homodifunctional amino­phospho­ranyl ligand, C₄₁H₄₁N₂P₂⁺·I^-, shows interesting features associated with the N-P-C-P-N skeleton. The P-C(H) bond distances [1.696 (3) and 1.697 (3) Å] possess partial double-bond characteristics. The nature of the P-C(H) and P-N bonds suggests that the positive charge is only distributed around the P-C-P atoms. The structure has near twofold symmetry through the central methyl­ide-C atom.

S1. Comment

The amino-[(R₂P-NXR')CR"] and iminophosphoranyl ligands [(R₂P=NR')CXR"] are essentially tautomeric forms, their basicity and reactivity altered by changing the groups at either phosphorus (R = Me, Ph), nitrogen (X = H, Me; R' = H, Me, Ph, C₆H₄Y-4 where Y = Me, NO₂) or methylide carbon (R" = H, Me, SiMe₃). The iminophosphoranyl ligands and their mono-anions, are known to coordinate in various forms to electron rich metals such as Rh^I, Ir^I, Pd^II and Pt^II. They donate one, two or four electrons to the metal centre, ligating via nitrogen and methylide carbon atoms, producing chelating, ylid and terdentate species (Avis et al., 1995; Imhoff et al., 1991, 1995).

The title compound, (I), was unexpectedly synthesized in the reaction of [Rh(CH{PPh₂=N-p-tolyl}₂)(COD)] with MeI, involving formation of [Rh(COD)I]₂ and the transfer of Me groups to nitrogen. The formation of the discrete cation-anion pair, shown in Figure 1, is distinct from a similar reaction of [Rh(CH{PPh₂=N-p-tolyl}₂)(COD)] with HCl (Imhoff et al., 1995) which resulted in protonation at one N and the methanide C. The cationic ligand (I) consists of two (N-methyl-N-p-tolylamino)diphenylphosphoranyl units attached via the phosphorus to a common methylide moiety. The P—N bond distances [1.656 (3) and 1.657 (3) Å] are typical of those found in aminophosphonium groups of metal complexes (Avis, et al., 1995, 1997; Imhoff, et al., 1989, 1993), but are significantly longer than those found in iminophosphoranyl ligands such as (Ph₂P=NC₆H₄Me-4)₂CH₂ (Imhoff, et al., 1990) and (Ph₂P=NC₆H₄Me-4)₂CHMe (Avis et al., 1996). The P—N bond characteristics in these imino species were attributed to a p π (N) − d π (P) interaction. The nitrogen atoms in (I) are also sp² hybridized but planar (nitrogen bond angles given in Table 1), producing little or no overlap between the nitrogen lone pair and the phosphorus d orbital. Both phosphorus atoms exhibit distorted tetrahedral geometries, with angles ranging from 103.96 (14)–114.01 (14)° around P1, and 103.84 (14)–114.40 (15)° for P2. \sch

The N—C and P—C(Ph) bond distances are in good agreement with values observed in related systems. The P—C(H) distances of 1.696 (3) and 1.697 (3) Å are comparable to those found in the [Ph₃P=CH-PPh₃]⁺ cation (Carroll & Titus, 1977), Na[PhCHPPh₂CHPPh₂] (Schmidbaur et al., 1980) and (MeSi)₂CPh₂-CHPPh₂CH(MeSi)₂ (Appel et al., 1984). These values lie between those expected for single and double P—C bonds, resulting in partial double-bond characteristics. The molecule possesses non-crystallographic C₂-symmetry, considering the equivalence of bond lengths and bond angles around the N—P—C—P—N core. The puckering of the P—C—P component leads to a distorted trigonal geometry at C1, P1—C1—P2 = 133.0 (4)°, and reduces the overall symmetry to C₁. The widening of this angle from the ideal 120° is possibly caused by steric repulsions between adjacent phenyl groups on the phosphorus atoms.

Only the P—C(H)—P distances have non-integral bond orders so presumably the charge is localized within the P—C—P component, as depicted by the mesomeric structure in the chemical scheme. Further delocalization, over the whole N—P—C—P—N skeleton, is precluded because of the non-planar arrangement of the atoms. The diffuse nature of the positive charge, and possibly steric hindrance, isolates the iodide anion from the cation. The shortest contacts between the iodide and adjacent aminophosphoranyl molecules involves interactions with methyl or phenyl H atoms: I1···H14Cⁱ [3.15 Å], I1···H37ⁱⁱ [3.20 Å] and I1···H10 of 3.22 Å, [Symmetry codes: (i) 1 − x, −1/2 + y, 1/2 − z, (ii) 1 − x, 1/2 + y, 1/2 − z].

S2. Experimental

Compound (I) was obtained in the reaction of [Rh(CH{PPh₂=N-p-tolyl}₂)(COD)] with about 10 equivalents of MeI in benzene (Imhoff et al., 1995). Brown crystals suitable for X-ray diffraction were grown by slow diffusion of hexane into a room temperature solution of the compound in (1:1) benzene-dichloromethane.

S3. Refinement

X-ray data were collected with a sufficiently large collimator tube to ensure a homogeneous X-ray beam at the crystal by use of a Zr β-filter rather than the graphite monochromator (Alexander & Smith, 1962).

All hydrogen atoms, with the exception of H1 on C1, were constrained and allowed to ride on their carbon atoms with U_iso(H) = 1.2U_eq(C) or U_iso(H) = 1.5U_eq(methyl). Methyl-H atoms were refined as rigid groups which allow for rotation around the C—C bonds, whilst maintaining a tetrahedral geometry at the C atom. H1 was located from a difference Fourier map and its coordinates allowed to refine with the isotropic displacement parameter constrained to U_iso(H) = 1.2U_eq(C1); the C1—H1 bond length refined to 0.98 (3) Å.

Computing details

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: SET4 (de Boer & Duisenberg, 1984); data reduction: HELENA (Spek, 1997); program(s) used to solve structure: DIRDIF (Beurskens, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: PLATON.

Figures

Fig. 1. Plot of (I) with 30% probability displacement ellipsoids. H atoms have been omitted for clarity.

(I)

Crystal data

C41H41N2P2^+·I^−	F(000) = 1536
Mr = 750.60	Dx = 1.385 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 13.3126 (5) Å	θ = 14.0–18.0°
b = 14.3251 (5) Å	µ = 1.01 mm^−1
c = 18.9767 (7) Å	T = 295 K
β = 95.819 (3)°	Block, brown
V = 3600.3 (2) Å^3	0.40 × 0.30 × 0.13 mm
Z = 4

Data collection

Enraf Nonius CAD-4F diffractometer	5992 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.000
Graphite monochromator	θmax = 28.0°, θmin = 1.5°
ω/2θ scans	h = −17→17
Absorption correction: ψ scan (North et al., 1968)	k = −18→0
Tmin = 0.788, Tmax = 0.877	l = 0→24
8582 measured reflections	3 standard reflections every 60 min
8582 independent reflections	intensity decay: 1.0%

Refinement

Refinement on F^2	Primary atom site location: heavy-atom method
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0489P)^2 + 3.4354P] where P = (Fo^2 + 2Fc^2)/3
8582 reflections	(Δ/σ)max = 0.003
423 parameters	Δρmax = 1.35 e Å^−3
0 restraints	Δρmin = −0.97 e Å^−3

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	0.70774 (5)	0.22908 (5)	0.20870 (4)	0.03127 (16)
P2	0.75940 (6)	0.01665 (5)	0.21083 (4)	0.03257 (17)
N1	0.80742 (19)	0.29886 (17)	0.21373 (14)	0.0379 (6)
N2	0.66219 (19)	−0.05518 (18)	0.21320 (14)	0.0409 (6)
C1	0.7284 (2)	0.1223 (2)	0.17440 (16)	0.0338 (6)
H1	0.723 (2)	0.125 (2)	0.1224 (17)	0.037 (9)*
C2	0.6057 (2)	0.2817 (2)	0.15102 (15)	0.0357 (6)
C3	0.6031 (3)	0.3760 (2)	0.13516 (18)	0.0472 (8)
H3	0.6548	0.4148	0.1544	0.057*
C4	0.5243 (3)	0.4130 (3)	0.0910 (2)	0.0573 (10)
H4	0.5228	0.4767	0.0814	0.069*
C5	0.4478 (3)	0.3565 (3)	0.06124 (19)	0.0547 (9)
H5	0.3952	0.3817	0.0312	0.066*
C6	0.4496 (2)	0.2628 (3)	0.07619 (19)	0.0527 (9)
H6	0.3982	0.2244	0.0560	0.063*
C7	0.5276 (2)	0.2251 (2)	0.12108 (17)	0.0438 (7)
H7	0.5278	0.1616	0.1313	0.053*
C8	0.6730 (2)	0.2260 (2)	0.29823 (16)	0.0370 (6)
C9	0.5745 (2)	0.2077 (2)	0.31212 (19)	0.0468 (8)
H9	0.5240	0.2004	0.2750	0.056*
C10	0.5518 (3)	0.2004 (3)	0.3817 (2)	0.0610 (10)
H10	0.4862	0.1868	0.3911	0.073*
C11	0.6258 (3)	0.2131 (3)	0.4366 (2)	0.0651 (11)
H11	0.6099	0.2089	0.4831	0.078*
C12	0.7230 (3)	0.2319 (3)	0.42324 (19)	0.0572 (9)
H12	0.7728	0.2405	0.4607	0.069*
C13	0.7473 (3)	0.2379 (3)	0.35474 (18)	0.0473 (8)
H13	0.8135	0.2500	0.3460	0.057*
C14	0.8098 (3)	0.3909 (2)	0.2490 (2)	0.0502 (8)
H14A	0.8680	0.3945	0.2832	0.075*
H14B	0.7498	0.3988	0.2724	0.075*
H14C	0.8134	0.4392	0.2143	0.075*
C15	0.8963 (2)	0.2792 (2)	0.17885 (16)	0.0363 (6)
C16	0.9005 (3)	0.2991 (2)	0.10848 (18)	0.0465 (8)
H16	0.8435	0.3218	0.0815	0.056*
C17	0.9891 (3)	0.2855 (3)	0.0775 (2)	0.0547 (9)
H17	0.9905	0.2979	0.0295	0.066*
C18	1.0759 (3)	0.2539 (3)	0.1168 (2)	0.0531 (9)
C19	1.0706 (2)	0.2334 (3)	0.1875 (2)	0.0526 (9)
H19	1.1274	0.2103	0.2145	0.063*
C20	0.9822 (2)	0.2467 (2)	0.21863 (18)	0.0462 (8)
H20	0.9804	0.2338	0.2665	0.055*
C21	1.1731 (3)	0.2429 (4)	0.0831 (3)	0.0810 (14)
H21A	1.2263	0.2253	0.1186	0.121*
H21B	1.1900	0.3009	0.0619	0.121*
H21C	1.1649	0.1953	0.0473	0.121*
C22	0.6704 (3)	−0.1469 (2)	0.2488 (2)	0.0503 (8)
H22A	0.6196	−0.1519	0.2811	0.076*
H22B	0.7360	−0.1530	0.2744	0.076*
H22C	0.6609	−0.1956	0.2139	0.076*
C23	0.5665 (2)	−0.0399 (2)	0.17224 (18)	0.0410 (7)
C24	0.5508 (3)	−0.0704 (3)	0.1033 (2)	0.0578 (10)
H24	0.6035	−0.0977	0.0821	0.069*
C25	0.4572 (4)	−0.0607 (3)	0.0655 (3)	0.0753 (13)
H25	0.4477	−0.0822	0.0191	0.090*
C26	0.3786 (3)	−0.0205 (3)	0.0946 (3)	0.0736 (13)
C27	0.3935 (3)	0.0104 (3)	0.1639 (3)	0.0727 (14)
H27	0.3407	0.0386	0.1844	0.087*
C28	0.4882 (3)	−0.0005 (3)	0.2035 (2)	0.0540 (9)
H28	0.4975	0.0187	0.2505	0.065*
C29	0.2744 (4)	−0.0103 (4)	0.0527 (4)	0.121 (3)
H29A	0.2238	−0.0042	0.0850	0.182*
H29B	0.2605	−0.0645	0.0236	0.182*
H29C	0.2738	0.0442	0.0232	0.182*
C30	0.8141 (2)	0.0214 (2)	0.30156 (16)	0.0370 (6)
C31	0.7527 (2)	0.0092 (2)	0.35614 (17)	0.0445 (8)
H31	0.6841	−0.0022	0.3453	0.053*
C32	0.7924 (3)	0.0138 (3)	0.42560 (19)	0.0535 (9)
H32	0.7512	0.0047	0.4618	0.064*
C33	0.8939 (3)	0.0320 (3)	0.4415 (2)	0.0604 (10)
H33	0.9208	0.0354	0.4886	0.072*
C34	0.9558 (3)	0.0453 (3)	0.3885 (2)	0.0619 (10)
H34	1.0239	0.0589	0.3997	0.074*
C35	0.9164 (3)	0.0382 (3)	0.31857 (19)	0.0488 (8)
H35	0.9586	0.0446	0.2827	0.059*
C36	0.8512 (2)	−0.0341 (2)	0.15745 (16)	0.0370 (6)
C37	0.8521 (3)	−0.1285 (2)	0.14133 (19)	0.0479 (8)
H37	0.8040	−0.1680	0.1575	0.057*
C38	0.9246 (3)	−0.1641 (3)	0.1012 (2)	0.0552 (9)
H38	0.9245	−0.2274	0.0904	0.066*
C39	0.9959 (3)	−0.1072 (3)	0.0773 (2)	0.0552 (9)
H39	1.0448	−0.1318	0.0510	0.066*
C40	0.9954 (3)	−0.0128 (3)	0.0924 (2)	0.0536 (9)
H40	1.0437	0.0261	0.0758	0.064*
C41	0.9233 (2)	0.0238 (2)	0.13203 (18)	0.0456 (8)
H41	0.9230	0.0875	0.1418	0.055*
I1	0.25447 (2)	0.118402 (18)	0.374177 (18)	0.06976 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0296 (3)	0.0310 (4)	0.0334 (4)	−0.0001 (3)	0.0038 (3)	0.0016 (3)
P2	0.0316 (4)	0.0300 (4)	0.0361 (4)	−0.0014 (3)	0.0031 (3)	0.0027 (3)
N1	0.0360 (13)	0.0341 (13)	0.0443 (15)	−0.0055 (10)	0.0079 (11)	−0.0045 (11)
N2	0.0391 (14)	0.0345 (13)	0.0479 (16)	−0.0073 (11)	−0.0013 (12)	0.0083 (12)
C1	0.0397 (15)	0.0308 (14)	0.0312 (15)	−0.0012 (12)	0.0045 (12)	0.0012 (12)
C2	0.0330 (15)	0.0385 (16)	0.0357 (16)	0.0046 (12)	0.0042 (12)	0.0035 (13)
C3	0.053 (2)	0.0397 (17)	0.0476 (19)	0.0025 (15)	−0.0005 (15)	0.0005 (15)
C4	0.073 (3)	0.0448 (19)	0.054 (2)	0.0216 (18)	0.0020 (19)	0.0064 (17)
C5	0.046 (2)	0.073 (3)	0.044 (2)	0.0239 (18)	0.0006 (15)	0.0064 (18)
C6	0.0337 (17)	0.076 (3)	0.048 (2)	0.0008 (17)	0.0028 (14)	0.0008 (19)
C7	0.0369 (16)	0.0465 (18)	0.0476 (19)	−0.0034 (14)	0.0019 (14)	0.0062 (15)
C8	0.0412 (16)	0.0355 (15)	0.0354 (16)	0.0041 (13)	0.0097 (12)	0.0029 (13)
C9	0.0400 (17)	0.0498 (19)	0.052 (2)	0.0025 (14)	0.0130 (15)	0.0007 (16)
C10	0.056 (2)	0.063 (2)	0.070 (3)	0.0041 (18)	0.034 (2)	0.005 (2)
C11	0.085 (3)	0.071 (3)	0.043 (2)	0.011 (2)	0.025 (2)	0.0062 (19)
C12	0.070 (2)	0.061 (2)	0.041 (2)	0.010 (2)	0.0061 (17)	0.0005 (17)
C13	0.0478 (19)	0.052 (2)	0.0423 (19)	0.0054 (15)	0.0054 (15)	0.0017 (15)
C14	0.054 (2)	0.0400 (18)	0.057 (2)	−0.0055 (15)	0.0044 (16)	−0.0102 (16)
C15	0.0354 (15)	0.0340 (15)	0.0398 (17)	−0.0073 (12)	0.0054 (12)	−0.0020 (13)
C16	0.0474 (19)	0.0497 (19)	0.0426 (19)	0.0013 (15)	0.0056 (15)	0.0033 (15)
C17	0.063 (2)	0.059 (2)	0.045 (2)	−0.0047 (18)	0.0218 (17)	0.0001 (17)
C18	0.0428 (19)	0.048 (2)	0.071 (3)	−0.0139 (15)	0.0190 (18)	−0.0149 (18)
C19	0.0336 (17)	0.057 (2)	0.066 (2)	−0.0023 (15)	−0.0033 (15)	−0.0047 (19)
C20	0.0419 (17)	0.051 (2)	0.0444 (19)	−0.0077 (15)	−0.0015 (14)	0.0031 (15)
C21	0.054 (2)	0.084 (3)	0.110 (4)	−0.012 (2)	0.037 (2)	−0.028 (3)
C22	0.054 (2)	0.0398 (17)	0.057 (2)	−0.0089 (15)	0.0052 (17)	0.0140 (16)
C23	0.0357 (16)	0.0365 (16)	0.0507 (19)	−0.0097 (13)	0.0035 (14)	0.0059 (14)
C24	0.049 (2)	0.067 (2)	0.057 (2)	−0.0077 (18)	0.0013 (17)	−0.0022 (19)
C25	0.070 (3)	0.079 (3)	0.071 (3)	−0.018 (2)	−0.020 (2)	0.008 (2)
C26	0.048 (2)	0.060 (3)	0.107 (4)	−0.016 (2)	−0.019 (2)	0.024 (3)
C27	0.040 (2)	0.050 (2)	0.131 (4)	−0.0030 (17)	0.023 (2)	0.020 (3)
C28	0.0472 (19)	0.047 (2)	0.070 (2)	−0.0072 (16)	0.0164 (17)	0.0025 (18)
C29	0.064 (3)	0.095 (4)	0.191 (7)	−0.015 (3)	−0.053 (4)	0.048 (4)
C30	0.0391 (16)	0.0339 (15)	0.0372 (16)	0.0002 (12)	−0.0006 (12)	0.0040 (13)
C31	0.0447 (18)	0.0458 (18)	0.0427 (19)	−0.0016 (14)	0.0027 (14)	0.0048 (14)
C32	0.065 (2)	0.054 (2)	0.0416 (19)	0.0023 (18)	0.0067 (17)	0.0080 (16)
C33	0.074 (3)	0.062 (2)	0.042 (2)	0.006 (2)	−0.0112 (18)	0.0049 (18)
C34	0.045 (2)	0.071 (3)	0.065 (3)	−0.0003 (18)	−0.0173 (18)	0.006 (2)
C35	0.0400 (17)	0.054 (2)	0.051 (2)	−0.0003 (15)	−0.0028 (15)	0.0069 (16)
C36	0.0390 (16)	0.0356 (15)	0.0363 (16)	0.0009 (12)	0.0034 (12)	0.0003 (13)
C37	0.058 (2)	0.0364 (17)	0.050 (2)	−0.0002 (15)	0.0091 (16)	0.0016 (15)
C38	0.074 (3)	0.0399 (19)	0.053 (2)	0.0108 (18)	0.0135 (19)	−0.0061 (16)
C39	0.055 (2)	0.064 (2)	0.049 (2)	0.0109 (18)	0.0169 (17)	−0.0051 (18)
C40	0.0468 (19)	0.059 (2)	0.058 (2)	−0.0022 (17)	0.0166 (16)	−0.0003 (18)
C41	0.0446 (18)	0.0398 (17)	0.054 (2)	−0.0013 (14)	0.0121 (15)	−0.0017 (15)
I1	0.06647 (18)	0.04617 (15)	0.0939 (2)	0.00539 (12)	−0.00543 (15)	−0.00224 (14)

Geometric parameters (Å, º)

P1—N1	1.656 (3)	C21—H21A	0.9600
P1—C1	1.696 (3)	C21—H21B	0.9600
P1—C8	1.806 (3)	C21—H21C	0.9600
P1—C2	1.820 (3)	C22—H22A	0.9600
P2—N2	1.658 (3)	C22—H22B	0.9600
P2—C1	1.697 (3)	C22—H22C	0.9600
P2—C30	1.801 (3)	C23—C28	1.372 (5)
P2—C36	1.816 (3)	C23—C24	1.375 (5)
N1—C15	1.441 (4)	C24—C25	1.380 (6)
N1—C14	1.477 (4)	C24—H24	0.9300
N2—C23	1.440 (4)	C25—C26	1.360 (7)
N2—C22	1.477 (4)	C25—H25	0.9300
C1—H1	0.98 (3)	C26—C27	1.381 (7)
C2—C3	1.384 (4)	C26—C29	1.534 (6)
C2—C7	1.393 (4)	C27—C28	1.410 (6)
C3—C4	1.380 (5)	C27—H27	0.9300
C3—H3	0.9300	C28—H28	0.9300
C4—C5	1.377 (6)	C29—H29A	0.9600
C4—H4	0.9300	C29—H29B	0.9600
C5—C6	1.371 (5)	C29—H29C	0.9600
C5—H5	0.9300	C30—C35	1.389 (4)
C6—C7	1.384 (5)	C30—C31	1.394 (4)
C6—H6	0.9300	C31—C32	1.371 (5)
C7—H7	0.9300	C31—H31	0.9300
C8—C9	1.387 (4)	C32—C33	1.379 (5)
C8—C13	1.394 (4)	C32—H32	0.9300
C9—C10	1.388 (5)	C33—C34	1.377 (6)
C9—H9	0.9300	C33—H33	0.9300
C10—C11	1.371 (6)	C34—C35	1.380 (5)
C10—H10	0.9300	C34—H34	0.9300
C11—C12	1.370 (6)	C35—H35	0.9300
C11—H11	0.9300	C36—C37	1.387 (4)
C12—C13	1.374 (5)	C36—C41	1.392 (4)
C12—H12	0.9300	C37—C38	1.385 (5)
C13—H13	0.9300	C37—H37	0.9300
C14—H14A	0.9600	C38—C39	1.363 (5)
C14—H14B	0.9600	C38—H38	0.9300
C14—H14C	0.9600	C39—C40	1.382 (5)
C15—C16	1.372 (4)	C39—H39	0.9300
C15—C20	1.384 (4)	C40—C41	1.382 (5)
C16—C17	1.384 (5)	C40—H40	0.9300
C16—H16	0.9300	C41—H41	0.9300
C17—C18	1.387 (5)	P1—P2	3.1192 (11)
C17—H17	0.9300	P1—N2	4.119 (3)
C18—C19	1.382 (5)	P2—N1	4.092 (3)
C18—C21	1.509 (5)	N1—C1	2.812 (4)
C19—C20	1.383 (5)	N1—N2	5.427 (3)
C19—H19	0.9300	N2—C1	2.813 (4)
C20—H20	0.9300
N1—P1—C1	113.99 (14)	C19—C20—C15	120.3 (3)
N1—P1—C8	103.94 (14)	C19—C20—H20	119.9
C1—P1—C8	113.95 (14)	C15—C20—H20	119.9
N1—P1—C2	109.26 (14)	C18—C21—H21A	109.5
C1—P1—C2	106.43 (14)	C18—C21—H21B	109.5
C8—P1—C2	109.20 (14)	H21A—C21—H21B	109.5
N2—P2—C1	113.96 (14)	C18—C21—H21C	109.5
N2—P2—C30	103.81 (14)	H21A—C21—H21C	109.5
C1—P2—C30	114.43 (14)	H21B—C21—H21C	109.5
N2—P2—C36	109.75 (14)	N2—C22—H22A	109.5
C1—P2—C36	106.21 (15)	N2—C22—H22B	109.5
C30—P2—C36	108.60 (14)	H22A—C22—H22B	109.5
C15—N1—C14	113.7 (2)	N2—C22—H22C	109.5
C15—N1—P1	123.1 (2)	H22A—C22—H22C	109.5
C14—N1—P1	123.0 (2)	H22B—C22—H22C	109.5
C23—N2—C22	113.7 (2)	C28—C23—C24	119.6 (3)
C23—N2—P2	122.8 (2)	C28—C23—N2	119.9 (3)
C22—N2—P2	122.9 (2)	C24—C23—N2	120.4 (3)
P1—C1—P2	133.64 (19)	C23—C24—C25	120.3 (4)
C3—C2—C7	118.6 (3)	C23—C24—H24	119.9
C3—C2—P1	122.4 (2)	C25—C24—H24	119.9
C7—C2—P1	119.0 (2)	C26—C25—C24	121.5 (5)
C4—C3—C2	120.5 (3)	C26—C25—H25	119.2
C4—C3—H3	119.7	C24—C25—H25	119.2
C2—C3—H3	119.7	C25—C26—C27	118.7 (4)
C5—C4—C3	120.6 (3)	C25—C26—C29	121.5 (6)
C5—C4—H4	119.7	C27—C26—C29	119.9 (5)
C3—C4—H4	119.7	C26—C27—C28	120.4 (4)
C6—C5—C4	119.6 (3)	C26—C27—H27	119.8
C6—C5—H5	120.2	C28—C27—H27	119.8
C4—C5—H5	120.2	C23—C28—C27	119.5 (4)
C5—C6—C7	120.4 (4)	C23—C28—H28	120.3
C5—C6—H6	119.8	C27—C28—H28	120.3
C7—C6—H6	119.8	C26—C29—H29A	109.5
C6—C7—C2	120.4 (3)	C26—C29—H29B	109.5
C6—C7—H7	119.8	H29A—C29—H29B	109.5
C2—C7—H7	119.8	C26—C29—H29C	109.5
C9—C8—C13	119.2 (3)	H29A—C29—H29C	109.5
C9—C8—P1	121.4 (3)	H29B—C29—H29C	109.5
C13—C8—P1	119.4 (2)	C35—C30—C31	119.0 (3)
C8—C9—C10	119.7 (3)	C35—C30—P2	121.4 (3)
C8—C9—H9	120.1	C31—C30—P2	119.6 (2)
C10—C9—H9	120.1	C32—C31—C30	120.7 (3)
C11—C10—C9	120.2 (4)	C32—C31—H31	119.7
C11—C10—H10	119.9	C30—C31—H31	119.7
C9—C10—H10	119.9	C31—C32—C33	119.5 (3)
C12—C11—C10	120.4 (4)	C31—C32—H32	120.2
C12—C11—H11	119.8	C33—C32—H32	120.2
C10—C11—H11	119.8	C34—C33—C32	120.8 (3)
C11—C12—C13	120.3 (4)	C34—C33—H33	119.6
C11—C12—H12	119.9	C32—C33—H33	119.6
C13—C12—H12	119.9	C33—C34—C35	119.6 (4)
C12—C13—C8	120.2 (3)	C33—C34—H34	120.2
C12—C13—H13	119.9	C35—C34—H34	120.2
C8—C13—H13	119.9	C34—C35—C30	120.3 (3)
N1—C14—H14A	109.5	C34—C35—H35	119.8
N1—C14—H14B	109.5	C30—C35—H35	119.8
H14A—C14—H14B	109.5	C37—C36—C41	118.9 (3)
N1—C14—H14C	109.5	C37—C36—P2	122.4 (2)
H14A—C14—H14C	109.5	C41—C36—P2	118.8 (2)
H14B—C14—H14C	109.5	C38—C37—C36	120.2 (3)
C16—C15—C20	119.2 (3)	C38—C37—H37	119.9
C16—C15—N1	121.5 (3)	C36—C37—H37	119.9
C20—C15—N1	119.1 (3)	C39—C38—C37	120.6 (3)
C15—C16—C17	120.3 (3)	C39—C38—H38	119.7
C15—C16—H16	119.8	C37—C38—H38	119.7
C17—C16—H16	119.8	C38—C39—C40	119.9 (3)
C16—C17—C18	121.1 (3)	C38—C39—H39	120.1
C16—C17—H17	119.4	C40—C39—H39	120.1
C18—C17—H17	119.4	C39—C40—C41	120.2 (3)
C19—C18—C17	118.0 (3)	C39—C40—H40	119.9
C19—C18—C21	121.3 (4)	C41—C40—H40	119.9
C17—C18—C21	120.7 (4)	C40—C41—C36	120.2 (3)
C18—C19—C20	121.0 (3)	C40—C41—H41	119.9
C18—C19—H19	119.5	C36—C41—H41	119.9
C20—C19—H19	119.5
C1—P1—N1—C15	12.6 (3)	N1—C15—C16—C17	175.5 (3)
C8—P1—N1—C15	137.2 (2)	C15—C16—C17—C18	−1.5 (6)
C2—P1—N1—C15	−106.3 (3)	C16—C17—C18—C19	2.0 (6)
C1—P1—N1—C14	−173.1 (3)	C16—C17—C18—C21	−177.7 (4)
C8—P1—N1—C14	−48.4 (3)	C17—C18—C19—C20	−1.9 (5)
C2—P1—N1—C14	68.0 (3)	C21—C18—C19—C20	177.8 (4)
C1—P2—N2—C23	15.4 (3)	C18—C19—C20—C15	1.4 (5)
C30—P2—N2—C23	140.6 (3)	C16—C15—C20—C19	−0.9 (5)
C36—P2—N2—C23	−103.5 (3)	N1—C15—C20—C19	−175.5 (3)
C1—P2—N2—C22	−174.0 (3)	C22—N2—C23—C28	89.4 (4)
C30—P2—N2—C22	−48.8 (3)	P2—N2—C23—C28	−99.2 (3)
C36—P2—N2—C22	67.1 (3)	C22—N2—C23—C24	−86.0 (4)
N1—P1—C1—P2	96.4 (3)	P2—N2—C23—C24	85.4 (4)
C8—P1—C1—P2	−22.7 (3)	C28—C23—C24—C25	0.7 (6)
C2—P1—C1—P2	−143.1 (2)	N2—C23—C24—C25	176.1 (3)
N2—P2—C1—P1	99.8 (3)	C23—C24—C25—C26	0.5 (7)
C30—P2—C1—P1	−19.5 (3)	C24—C25—C26—C27	−0.5 (7)
C36—P2—C1—P1	−139.3 (2)	C24—C25—C26—C29	−179.6 (4)
N1—P1—C2—C3	−19.6 (3)	C25—C26—C27—C28	−0.6 (6)
C1—P1—C2—C3	−143.1 (3)	C29—C26—C27—C28	178.5 (4)
C8—P1—C2—C3	93.5 (3)	C24—C23—C28—C27	−1.8 (5)
N1—P1—C2—C7	159.9 (2)	N2—C23—C28—C27	−177.3 (3)
C1—P1—C2—C7	36.4 (3)	C26—C27—C28—C23	1.8 (6)
C8—P1—C2—C7	−87.1 (3)	N2—P2—C30—C35	151.2 (3)
C7—C2—C3—C4	0.5 (5)	C1—P2—C30—C35	−83.9 (3)
P1—C2—C3—C4	179.9 (3)	C36—P2—C30—C35	34.5 (3)
C2—C3—C4—C5	−1.0 (6)	N2—P2—C30—C31	−29.5 (3)
C3—C4—C5—C6	0.6 (6)	C1—P2—C30—C31	95.3 (3)
C4—C5—C6—C7	0.2 (6)	C36—P2—C30—C31	−146.2 (3)
C5—C6—C7—C2	−0.7 (5)	C35—C30—C31—C32	0.2 (5)
C3—C2—C7—C6	0.4 (5)	P2—C30—C31—C32	−179.1 (3)
P1—C2—C7—C6	−179.1 (3)	C30—C31—C32—C33	0.9 (5)
N1—P1—C8—C9	153.9 (3)	C31—C32—C33—C34	−0.3 (6)
C1—P1—C8—C9	−81.4 (3)	C32—C33—C34—C35	−1.4 (6)
C2—P1—C8—C9	37.4 (3)	C33—C34—C35—C30	2.5 (6)
N1—P1—C8—C13	−29.1 (3)	C31—C30—C35—C34	−1.9 (5)
C1—P1—C8—C13	95.5 (3)	P2—C30—C35—C34	177.4 (3)
C2—P1—C8—C13	−145.7 (3)	N2—P2—C36—C37	−18.2 (3)
C13—C8—C9—C10	−0.8 (5)	C1—P2—C36—C37	−141.8 (3)
P1—C8—C9—C10	176.2 (3)	C30—P2—C36—C37	94.7 (3)
C8—C9—C10—C11	1.4 (6)	N2—P2—C36—C41	162.1 (2)
C9—C10—C11—C12	−0.9 (6)	C1—P2—C36—C41	38.4 (3)
C10—C11—C12—C13	−0.1 (6)	C30—P2—C36—C41	−85.1 (3)
C11—C12—C13—C8	0.7 (6)	C41—C36—C37—C38	0.6 (5)
C9—C8—C13—C12	−0.2 (5)	P2—C36—C37—C38	−179.1 (3)
P1—C8—C13—C12	−177.2 (3)	C36—C37—C38—C39	0.3 (6)
C14—N1—C15—C16	−93.3 (4)	C37—C38—C39—C40	−0.9 (6)
P1—N1—C15—C16	81.6 (4)	C38—C39—C40—C41	0.5 (6)
C14—N1—C15—C20	81.3 (4)	C39—C40—C41—C36	0.4 (6)
P1—N1—C15—C20	−103.9 (3)	C37—C36—C41—C40	−1.0 (5)
C20—C15—C16—C17	0.9 (5)	P2—C36—C41—C40	178.8 (3)