A tungsten complex containing a highly delocalized metal-ligand system

Nucleophilic attack of (triphenyl­phospho­nio)cyclo­penta­di­en­ide on the dichloro­diazo­methane-tungsten complex trans-[BrW(dppe)₂(N₂CCl₂)]PF₆ [dppe is 1,2-bis(diphenyl­phos­phino)ethane] results in C-C bond formation and affords the title compound, trans-[W(C₂₄H₁₈ClN₂P)Br(C₂₆H₂₄P₂)₂]PF₆·0.6CH₂Cl₂. This complex, bis[1,2-bis(diphenyl­phosphino)­ethane]­bromido{chloro­[3-(triphenylphosphonio)­cyclo­penta­di­enyl­idene]­diazo­methane­diido}­tungsten hexa­fluoro­phos­phate dichloromethane 0.6-solvate, contains the previously unknown ligand chloro­[3-(triphenyl­phospho­nio)cyclo­penta­dienyl­idene]diazo­methane. Evidence from bond lengths and torsion angles indicates significant through-ligand delocalization of electron density from tungsten to the nominally cationic phosphorus(V) centre. This structural analysis clearly demonstrates that the tungsten-dinitro­gen unit is a powerful [pi]-electron donor with the ability to transfer electron density from the metal to a distant acceptor centre through an extended conjugated ligand system. As a consequence, complexes of this type could have potential applications as nonlinear optical materials and mol­ecular semiconductors.

S1. Comment

Transition metal complexes containing extended conjugated organic ligands have the potential to display a wide range of novel electronic, magnetic and optical properties (Chisholm & Macintosh, 2005; Ceccon et al., 2004; Schwab et al., 1999) and thus to provide a basis for the development of molecular materials and devices (Low, 2005; Chisholm, 2000). One of the challenges in synthesizing such complexes is to design ligands that provide an extended conjugation pathway between multiple metal or metal/metalloid centres. Examples of ligands so far investigated for this purpose include polyethynylenes (Zheng et al., 2004; Antonova et al., 2004), 1,4-phenylenediethynylene (Nguyen et al., 1999; Chawdhury et al., 1998) and 4-ethynylpyridine (Ronson et al., 2006; Zuo et al., 2002). The use of dinitrogen-derived ligands, containing, for example, diazenido(1-), M═N═N—R, or diazoalkane, M≡N—N═CR₂, moieties has been much less explored in this context, although we have recently shown that such complexes can have significant utility in the assembly of extended-chain polynuclear transition metal complexes (Colquhoun et al., 2007).

The cationic dichlorodiazomethane complex trans-[BrW(dppe)₂(N₂CCl₂]⁺, (I), is readily obtained from trans-W(dppe)₂(N₂)₂ via the hydrazido(2-) complex trans-[BrW(dppe)₂(NNH₂)]⁺, and undergoes facile replacement of one or both chloro-substituents by a wide range of nitrogen- and oxygen-based nucleophiles (Colquhoun, 1984). Here, we report the first example of such a reaction involving a carbon-centred nucleophile, (triphenylphosphonio)cyclopentadienide, which (probably for steric reasons) replaces just one of the two chloro-substituents at C to give trans-[BrW(dppe)₂{N₂C(Cl)(C₅H₃PPh₃)}]⁺, isolated as the title hexafluorophosphate salt, (II).

Two valence-bond structures, (a) and (b) (Fig. 1), may be drawn for the cation of (II), suggesting the possibility of extended delocalization of electron density between W and P via the π-system of the fully conjugated cyclopentadienylidene(chloro)diazomethane ligand. The structural features associated with such delocalization would be expected to include near-coplanarity of the entire metal–ligand framework from W to P, some degree of equalization of bond distances between the exocyclic and endocyclic C atoms involved in delocalization, and some degree of shortening of the P—C_{cyclopentadienylidene} bond relative to the adjacent P—C_phenyl bonds. To determine whether such geometric effects can in fact be observed, a single-crystal X-ray study of complex (II) was undertaken.

Compound (II) crystallizes with discrete cations and anions, in the form of a dichloromethane solvate. One of the phenyl rings of the triphenylphosphonium residue is rotationally disordered about the P5—C71 bond, but for clarity only one of the two orientations found is shown in Fig. 2. The metal–ligand system between atoms W1 and P5 exhibits a very high degree of coplanarity, with atoms W1 and N2 lying only 0.019 and 0.026 Å, respectively, out of the mean metal–ligand plane, and no other ligand atom being displaced from this plane by more than 0.01 Å (Fig. 3). Such coplanarity is certainly consistent with a degree of delocalization throughout the metal–ligand π-system, and an analysis of bond lengths tends to confirm this.

Thus, although the pattern of C—C bond lengths (Table 1) is, at first sight, compatible simply with canonical form (a), there are a number of features of the structure which also seem to require a significant contribution from form (b). For example, the endocyclic C2—C6 and exocyclic C1—C2 bond lengths differ by only 0.014 Å rather than showing the ca 0.18 Å difference expected between a single and a double C—C bond (Pauling, 1960). Moreover, the endocyclic double bond C5═C6, which could be involved in long-range delocalization, is indeed lengthened slightly relative to the `uninvolved' double bond C3—C4. Finally, the bond from P to the C₅ ring (P5—C5) is significantly shorter than the three adjacent P5—C bonds to phenyl (average 1.800 Å), once again consistent with a contribution from canonical form (b). The W—N bond length, at 1.775 (4) Å, is longer than that normally associated with a W≡N triple bond (Pyykko et al., 2005), whilst the N—N bond distance, at 1.312 (5) Å, represents a bond order of ca 1.5 (Allen et al., 1987). The W—N and N—N bond lengths thus also imply contributions to the structure from both canonical forms (a) and (b). The geometry at N1 is noticeably distorted from linear [W1—N1—N2 = 164.5 (3)°] as a result of steric repulsions between the chloro-substituent Cl1 and its adjacent diphosphine ligand.

The variations in bond lengths from those expected solely on the basis of canonical form (a), together with the coplanarity of the W1—N1—N2—C1(Cl1)—C₅H₃—P5 fragment and the torsion angles within the fragment, are thus fully compatible with delocalization of electron density throughout the metal–ligand π-system. Although the observed bond lengths do show some discrepancies from the bond orders suggested by Fig. 1 (notably the inequality of bonds C2—C3 and C3—C4), the overall pattern of bond lengths is clearly very much more consistent with the bond orders for this `averaged' model than for either canonical form alone.

This structural analysis clearly demonstrates that the tungsten(II)–dinitrogen unit is a powerful π-electron donor, with the ability to transfer electron density from the metal to a distant acceptor centre through an extended conjugated ligand system. As a consequence, complexes of this type could have potential application as non-linear optical materials and molecular semiconductors.

Related literature

For related literature, see: Allen et al. (1987); Antonova et al. (2004); Ceccon et al. (2004); Chawdhury et al. (1998); Chisholm (2000); Chisholm & Macintosh (2005); Colquhoun (1984); Colquhoun et al. (2007); Low (2005); Nguyen et al. (1999); Pauling (1960); Pyykko et al. (2005); Ronson et al. (2006); Schwab et al. (1999); Spek (2003); Zheng et al. (2004); Zuo et al. (2002).

S2. Experimental

(Triphenylphosphonio)cyclopentadienide (0.107 g, 0.329 mmol) and dry triethylamine (0.5 ml) were added, under nitrogen, to a stirred suspension of the dichlorodiazomethane complex, (I) (0.253 g. 0.192 mmol), in dichloromethane (20 ml). After 15 h, the deep yellow–brown solution was extracted with water (3 × 30 ml), dried over magnesium sulfate and evaporated to half-volume. Slow addition of diethyl ether (10 ml) resulted in formation of dark olive-green crystals of (II), which were filtered off, washed with diethyl ether and dried under vacuum (0.256 g, 83% yield). Analysis, found: C 54.62, H 4.35, N 1.73%; calculated for C₇₆H₆₆BrClF₆N₂P₆W.CH₂Cl₂: C 54.68, H 4.15, N 1.66%; ¹H NMR (CDCl₃, δ, p.p.m.): 7.06–7.38 (m, 40 H, PPh), 7.61–7.68 (m, 15 H), 6.49–6.54 (m, 2 H, Cp), 6.19–6.22 (m, 1 H, Cp), 2.88 (br d, 8 H, CH₂); ¹³C NMR (CDCl₃, δ, p.p.m.): 128.30, 129.01, 129.97, 130.17, 130.27, 130.91, 133.61, 133.95, 134.71, 134.46, 134.51, 134.88, 135.02, 135.37, 120.48, 120.95, 122.74, 124.79, 31.62 p.p.m.. Single crystals suitable for X-ray analysis were grown by vapour diffusion of diethyl ether into a solution of (II) in dichloromethane.

S3. Refinement

One of the phenyl rings attached to P5 was modelled as disordered over two positions. The C—C distances within each ring were restrained to 1.39 (1) Å. The occupancies of the two rings refined to 0.58 (3) (atoms C71–C76) and 0.42 (3) (atoms C720–C760). Not all the H atoms in the structure could be located in difference Fourier maps. H atoms were therefore positioned geometrically after each cycle of refinement, with C—H = 0.95 Å and U_iso(H) = 1.2U_eq(C). The crystal structure contains a solvent molecule of dichloromethane which was not sufficiently resolved in the electron density map to enable it to be modelled with disordered atoms. The residual electron density was therefore modelled using the SQUEEZE routine available in PLATON (Spek, 2003).

Computing details

Data collection: COLLECT (Nonius, 2001); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).

Figures

	Fig. 1. The potential delocalization of electron density in complex (II), as indicated by resonance between canonical forms (a) and (b). Form (a) represents a diazenido(1-) complex of W^II and form (b) a diazoalkane complex of W^IV.
	Fig. 2. The molecular structure of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity.
	Fig. 3. The structure of complex (II), showing the essential coplanarity of the extended diazoalkane ligand system. H atoms have been omitted for clarity.

Bis[1,2-(diphenylphosphino)ethane]bromido{chloro[3- (triphenylphosphonio)cyclopentadienylidene]diazomethanediido}tungsten(IV) hexafluorophosphate dichloromethane 0.6-solvate

Crystal data

C76H66BrClN2P5W·F6P·0.6(CH2Cl2)	F(000) = 3248
Mr = 1657.27	Dx = 1.431 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 16178 reflections
a = 18.2621 (10) Å	θ = 5–27°
b = 14.706 (1) Å	µ = 2.28 mm^−1
c = 28.934 (2) Å	T = 150 K
β = 98.236 (3)°	Plate, green
V = 7690.3 (9) Å^3	0.12 × 0.09 × 0.08 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	17372 independent reflections
Radiation source: fine-focus sealed tube	9841 reflections with I > 3σ(I)
Graphite monochromator	Rint = 0.027
ω scans	θmax = 27.5°, θmin = 5.1°
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	h = −23→23
Tmin = 0.79, Tmax = 0.84	k = 0→19
17372 measured reflections	l = 0→37

Refinement

Refinement on F	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.037	H-atom parameters not refined
S = 1.09	Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)] where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 Ai are: 0.292 0.504E-01 0.896E-01 Watkin, D. (1994). Acta Cryst. A50, 411–437.
9841 reflections	(Δ/σ)max = 0.003
875 parameters	Δρmax = 1.01 e Å^−3
24 restraints	Δρmin = −0.70 e Å^−3
0 constraints

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
W1	0.266376 (10)	0.448099 (12)	0.684906 (7)	0.0227
Br1	0.40946 (2)	0.43691 (3)	0.700747 (18)	0.0316
P1	0.27282 (7)	0.30408 (8)	0.63730 (5)	0.0285
P2	0.28076 (7)	0.32885 (8)	0.74751 (5)	0.0282
P3	0.27647 (7)	0.57382 (8)	0.62523 (5)	0.0269
P4	0.26774 (7)	0.58788 (8)	0.73508 (5)	0.0258
P5	−0.24945 (6)	0.43046 (9)	0.64000 (4)	0.0293
P6	0.33001 (11)	0.92489 (11)	0.58265 (6)	0.0529
F1	0.2764 (3)	0.9955 (3)	0.6030 (2)	0.0950
F2	0.2606 (3)	0.8642 (3)	0.5628 (2)	0.0975
F3	0.3213 (2)	0.9790 (3)	0.53475 (14)	0.0694
F4	0.3824 (3)	0.8549 (3)	0.56258 (16)	0.0869
F5	0.3976 (2)	0.9874 (3)	0.60252 (14)	0.0704
F6	0.3429 (3)	0.8695 (3)	0.63077 (16)	0.0951
N1	0.1683 (2)	0.4438 (3)	0.67720 (13)	0.0252
N2	0.0992 (2)	0.4197 (3)	0.67749 (16)	0.0326
Cl1	0.04964 (7)	0.57251 (8)	0.63429 (5)	0.0373
C1	0.0418 (3)	0.4654 (3)	0.66002 (17)	0.0283
C2	−0.0310 (2)	0.4312 (3)	0.66138 (18)	0.0305
C3	−0.0462 (3)	0.3451 (4)	0.6807 (2)	0.0422
C4	−0.1206 (3)	0.3341 (4)	0.6764 (2)	0.0409
C5	−0.1547 (3)	0.4135 (4)	0.65313 (18)	0.0308
C6	−0.0993 (3)	0.4726 (3)	0.64425 (17)	0.0287
C7	0.2877 (3)	0.2040 (3)	0.6771 (2)	0.0390
C8	0.3253 (3)	0.2295 (3)	0.7252 (2)	0.0354
C9	0.2707 (3)	0.6858 (3)	0.6534 (2)	0.0370
C10	0.2296 (3)	0.6805 (3)	0.69584 (18)	0.0305
C11	0.3419 (3)	0.2854 (3)	0.59836 (19)	0.0321
C12	0.3882 (3)	0.3547 (4)	0.5884 (2)	0.0393
C13	0.4411 (4)	0.3397 (4)	0.5587 (2)	0.0496
C14	0.4459 (4)	0.2557 (4)	0.5388 (2)	0.0480
C15	0.4005 (3)	0.1858 (4)	0.5482 (2)	0.0466
C16	0.3483 (3)	0.2004 (4)	0.5776 (2)	0.0375
C17	0.1856 (3)	0.2715 (4)	0.6013 (2)	0.0447
C18	0.1775 (4)	0.2697 (5)	0.5526 (3)	0.0669
C19	0.1106 (6)	0.2494 (7)	0.5262 (4)	0.1021
C20	0.0519 (6)	0.2319 (7)	0.5470 (5)	0.1186
C21	0.0556 (4)	0.2320 (6)	0.5960 (5)	0.1007
C22	0.1237 (3)	0.2526 (4)	0.6235 (3)	0.0611
C23	0.1943 (3)	0.2842 (4)	0.7625 (2)	0.0373
C24	0.1781 (3)	0.1911 (4)	0.7626 (2)	0.0445
C25	0.1107 (4)	0.1605 (5)	0.7752 (2)	0.0602
C26	0.0612 (4)	0.2215 (6)	0.7882 (3)	0.0717
C27	0.0766 (4)	0.3132 (6)	0.7887 (3)	0.0669
C28	0.1417 (3)	0.3450 (4)	0.7750 (2)	0.0492
C29	0.3367 (3)	0.3487 (3)	0.80452 (19)	0.0342
C30	0.3059 (3)	0.3910 (4)	0.8408 (2)	0.0441
C31	0.3496 (4)	0.4133 (5)	0.8820 (2)	0.0571
C32	0.4237 (4)	0.3930 (5)	0.8888 (3)	0.0603
C33	0.4550 (4)	0.3513 (4)	0.8543 (3)	0.0564
C34	0.4120 (3)	0.3281 (4)	0.8124 (2)	0.0435
C35	0.3611 (3)	0.5916 (3)	0.59904 (19)	0.0292
C36	0.3622 (3)	0.5796 (4)	0.5515 (2)	0.0382
C37	0.4274 (3)	0.5922 (5)	0.5326 (2)	0.0503
C38	0.4924 (3)	0.6135 (4)	0.5610 (3)	0.0516
C39	0.4917 (3)	0.6258 (4)	0.6081 (2)	0.0442
C40	0.4273 (3)	0.6142 (3)	0.6275 (2)	0.0368
C41	0.2035 (3)	0.5776 (3)	0.57491 (19)	0.0332
C42	0.1867 (3)	0.6586 (4)	0.5504 (2)	0.0494
C43	0.1322 (4)	0.6588 (5)	0.5112 (3)	0.0592
C44	0.0947 (3)	0.5826 (5)	0.4961 (2)	0.0542
C45	0.1120 (4)	0.5030 (5)	0.5199 (2)	0.0580
C46	0.1652 (3)	0.5007 (4)	0.5594 (2)	0.0461
C47	0.2064 (3)	0.5923 (3)	0.77964 (19)	0.0297
C48	0.2324 (3)	0.5974 (4)	0.82697 (19)	0.0350
C49	0.1827 (3)	0.5933 (4)	0.8594 (2)	0.0442
C50	0.1078 (3)	0.5852 (4)	0.8453 (2)	0.0466
C51	0.0817 (3)	0.5824 (4)	0.7985 (2)	0.0456
C52	0.1302 (3)	0.5851 (4)	0.7656 (2)	0.0372
C53	0.3561 (3)	0.6321 (3)	0.76398 (18)	0.0285
C54	0.3799 (3)	0.7212 (3)	0.75847 (19)	0.0334
C55	0.4463 (3)	0.7514 (4)	0.7815 (2)	0.0370
C56	0.4905 (3)	0.6951 (4)	0.8116 (2)	0.0375
C57	0.4686 (3)	0.6056 (4)	0.81764 (19)	0.0354
C58	0.4025 (3)	0.5749 (3)	0.79360 (18)	0.0297
C59	−0.2932 (2)	0.4477 (4)	0.69129 (17)	0.0326
C60	−0.2527 (3)	0.4344 (4)	0.73570 (18)	0.0345
C61	−0.2852 (3)	0.4507 (4)	0.77491 (19)	0.0454
C62	−0.3574 (3)	0.4814 (4)	0.7713 (2)	0.0438
C63	−0.3970 (3)	0.4964 (4)	0.7279 (2)	0.0480
C64	−0.3656 (3)	0.4792 (4)	0.6879 (2)	0.0443
C65	−0.2900 (3)	0.3330 (4)	0.60789 (18)	0.0351
C66	−0.2548 (3)	0.3010 (5)	0.5717 (2)	0.0472
C67	−0.2847 (4)	0.2276 (5)	0.5448 (2)	0.0536
C68	−0.3477 (4)	0.1863 (4)	0.5546 (2)	0.0519
C69	−0.3820 (3)	0.2168 (5)	0.5913 (2)	0.0479
C70	−0.3537 (3)	0.2910 (4)	0.61785 (18)	0.0385
C71	−0.2669 (3)	0.5309 (3)	0.60524 (16)	0.0324
C72	−0.2488 (14)	0.6162 (6)	0.6244 (5)	0.0612	0.58 (3)
C73	−0.2564 (16)	0.6959 (9)	0.5984 (3)	0.0726	0.58 (3)
C74	−0.2879 (4)	0.6886 (4)	0.5518 (2)	0.0552
C75	−0.3027 (13)	0.6068 (8)	0.5298 (5)	0.0643	0.58 (3)
C76	−0.2924 (13)	0.5303 (12)	0.5576 (3)	0.0520	0.58 (3)
C720	−0.2882 (12)	0.6100 (7)	0.6254 (6)	0.0387	0.42 (3)
C730	−0.3014 (12)	0.6867 (10)	0.5976 (4)	0.0421	0.42 (3)
C750	−0.2685 (16)	0.6061 (8)	0.5343 (6)	0.0475	0.42 (3)
C760	−0.2573 (16)	0.5251 (12)	0.5587 (4)	0.0423	0.42 (3)
H31	−0.0102	0.3027	0.6943	0.0511*
H41	−0.1458	0.2832	0.6869	0.0492*
H61	−0.1060	0.5303	0.6294	0.0345*
H71	0.2411	0.1775	0.6797	0.0480*
H72	0.3177	0.1610	0.6640	0.0480*
H81	0.3224	0.1797	0.7457	0.0431*
H82	0.3757	0.2433	0.7237	0.0431*
H91	0.3194	0.7076	0.6632	0.0456*
H92	0.2453	0.7269	0.6314	0.0456*
H101	0.2350	0.7366	0.7123	0.0366*
H102	0.1787	0.6693	0.6856	0.0366*
H121	0.3841	0.4131	0.6018	0.0489*
H131	0.4734	0.3873	0.5525	0.0627*
H141	0.4811	0.2457	0.5181	0.0597*
H151	0.4050	0.1276	0.5347	0.0575*
H161	0.3164	0.1522	0.5837	0.0454*
H181	0.2190	0.2827	0.5373	0.0776*
H191	0.1065	0.2478	0.4931	0.1157*
H201	0.0059	0.2189	0.5283	0.1342*
H211	0.0131	0.2186	0.6102	0.1203*
H221	0.1277	0.2537	0.6566	0.0736*
H241	0.2129	0.1484	0.7541	0.0534*
H251	0.0996	0.0974	0.7746	0.0718*
H261	0.0159	0.2006	0.7970	0.0877*
H271	0.0423	0.3550	0.7986	0.0826*
H281	0.1506	0.4086	0.7740	0.0600*
H301	0.2545	0.4042	0.8369	0.0536*
H311	0.3283	0.4431	0.9059	0.0684*
H321	0.4533	0.4081	0.9175	0.0691*
H331	0.5064	0.3379	0.8590	0.0652*
H341	0.4341	0.2979	0.7889	0.0514*
H361	0.3182	0.5628	0.5318	0.0465*
H371	0.4272	0.5860	0.4998	0.0617*
H381	0.5373	0.6196	0.5482	0.0643*
H391	0.5360	0.6425	0.6276	0.0532*
H401	0.4279	0.6216	0.6601	0.0447*
H421	0.2120	0.7132	0.5604	0.0586*
H431	0.1213	0.7140	0.4947	0.0696*
H441	0.0572	0.5842	0.4697	0.0639*
H451	0.0872	0.4485	0.5092	0.0679*
H461	0.1752	0.4451	0.5758	0.0545*
H481	0.2839	0.6037	0.8373	0.0421*
H491	0.2010	0.5961	0.8918	0.0536*
H501	0.0746	0.5816	0.8677	0.0583*
H511	0.0299	0.5785	0.7884	0.0559*
H521	0.1113	0.5820	0.7332	0.0450*
H541	0.3495	0.7615	0.7385	0.0411*
H551	0.4620	0.8118	0.7766	0.0454*
H561	0.5357	0.7171	0.8281	0.0460*
H571	0.4989	0.5661	0.8382	0.0424*
H581	0.3882	0.5135	0.7973	0.0363*
H601	−0.2029	0.4141	0.7387	0.0414*
H611	−0.2577	0.4407	0.8049	0.0554*
H621	−0.3794	0.4920	0.7986	0.0549*
H631	−0.4462	0.5187	0.7254	0.0594*
H641	−0.3937	0.4890	0.6580	0.0529*
H661	−0.2104	0.3289	0.5653	0.0576*
H671	−0.2612	0.2064	0.5196	0.0647*
H681	−0.3681	0.1365	0.5361	0.0608*
H691	−0.4251	0.1868	0.5984	0.0570*
H701	−0.3779	0.3127	0.6426	0.0463*
H721	−0.2305	0.6201	0.6568	0.0727*	0.58
H731	−0.2406	0.7529	0.6117	0.0872*	0.58
H741	−0.2998	0.7429	0.5345	0.0660*
H751	−0.3192	0.6030	0.4972	0.0734*	0.58
H761	−0.3036	0.4730	0.5432	0.0606*	0.58
H725	−0.2937	0.6118	0.6576	0.0477*	0.42
H735	−0.3203	0.7398	0.6105	0.0521*	0.42
H755	−0.2622	0.6048	0.5023	0.0541*	0.42
H765	−0.2441	0.4702	0.5447	0.0512*	0.42

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
W1	0.01851 (8)	0.01787 (8)	0.03285 (10)	−0.00011 (8)	0.00750 (6)	0.00461 (10)
Br1	0.0206 (2)	0.0284 (3)	0.0462 (3)	0.00102 (19)	0.00662 (19)	0.0059 (2)
P1	0.0244 (6)	0.0210 (6)	0.0411 (8)	0.0007 (5)	0.0079 (5)	0.0007 (5)
P2	0.0267 (6)	0.0217 (6)	0.0373 (7)	0.0007 (5)	0.0086 (5)	0.0101 (6)
P3	0.0262 (6)	0.0206 (6)	0.0355 (7)	0.0004 (4)	0.0092 (5)	0.0057 (5)
P4	0.0217 (6)	0.0207 (5)	0.0358 (7)	0.0001 (4)	0.0069 (5)	0.0016 (5)
P5	0.0199 (5)	0.0394 (8)	0.0282 (6)	−0.0009 (5)	0.0023 (5)	−0.0033 (6)
P6	0.0785 (12)	0.0372 (9)	0.0471 (10)	−0.0184 (8)	0.0231 (9)	−0.0080 (7)
F1	0.101 (4)	0.069 (3)	0.128 (4)	−0.022 (3)	0.061 (3)	−0.040 (3)
F2	0.101 (4)	0.072 (3)	0.124 (4)	−0.045 (3)	0.030 (3)	−0.035 (3)
F3	0.078 (3)	0.073 (3)	0.055 (2)	−0.008 (2)	0.000 (2)	0.007 (2)
F4	0.117 (4)	0.069 (3)	0.073 (3)	0.020 (3)	0.011 (3)	−0.014 (2)
F5	0.087 (3)	0.051 (2)	0.067 (3)	−0.022 (2)	−0.012 (2)	0.009 (2)
F6	0.174 (5)	0.050 (2)	0.065 (3)	−0.037 (3)	0.033 (3)	0.003 (2)
N1	0.0250 (18)	0.0191 (18)	0.033 (2)	−0.0009 (17)	0.0093 (15)	0.0024 (18)
N2	0.0166 (19)	0.030 (2)	0.051 (3)	0.0011 (16)	0.0054 (18)	0.0080 (19)
Cl1	0.0284 (6)	0.0316 (7)	0.0528 (8)	−0.0007 (5)	0.0090 (5)	0.0106 (6)
C1	0.027 (2)	0.025 (3)	0.034 (3)	0.0003 (18)	0.010 (2)	0.005 (2)
C2	0.020 (2)	0.033 (3)	0.039 (3)	0.0043 (19)	0.006 (2)	0.001 (2)
C3	0.028 (3)	0.028 (3)	0.072 (4)	0.000 (2)	0.011 (3)	0.014 (3)
C4	0.030 (3)	0.032 (3)	0.061 (4)	−0.004 (2)	0.007 (3)	0.012 (3)
C5	0.020 (2)	0.037 (3)	0.037 (3)	−0.0015 (19)	0.009 (2)	−0.002 (2)
C6	0.025 (2)	0.030 (3)	0.031 (3)	0.0024 (19)	0.005 (2)	−0.003 (2)
C7	0.047 (3)	0.021 (2)	0.052 (4)	−0.007 (2)	0.017 (3)	0.001 (2)
C8	0.038 (3)	0.022 (2)	0.047 (3)	0.000 (2)	0.011 (2)	0.012 (2)
C9	0.049 (3)	0.020 (2)	0.045 (3)	0.002 (2)	0.017 (3)	0.008 (2)
C10	0.028 (2)	0.025 (2)	0.039 (3)	0.0004 (19)	0.004 (2)	0.002 (2)
C11	0.031 (3)	0.028 (3)	0.040 (3)	0.007 (2)	0.011 (2)	0.005 (2)
C12	0.047 (3)	0.034 (3)	0.041 (3)	0.004 (2)	0.022 (3)	0.005 (2)
C13	0.055 (4)	0.040 (3)	0.061 (4)	0.002 (3)	0.036 (3)	0.012 (3)
C14	0.055 (4)	0.045 (3)	0.049 (4)	0.017 (3)	0.025 (3)	0.006 (3)
C15	0.056 (4)	0.037 (3)	0.051 (4)	0.013 (3)	0.021 (3)	−0.002 (3)
C16	0.036 (3)	0.031 (3)	0.047 (3)	0.002 (2)	0.009 (2)	0.001 (2)
C17	0.031 (3)	0.028 (3)	0.074 (5)	0.006 (2)	0.002 (3)	−0.016 (3)
C18	0.057 (4)	0.069 (5)	0.068 (5)	0.024 (4)	−0.014 (4)	−0.029 (4)
C19	0.066 (6)	0.106 (7)	0.117 (8)	0.035 (5)	−0.045 (6)	−0.059 (6)
C20	0.059 (6)	0.097 (7)	0.179 (12)	0.026 (5)	−0.052 (7)	−0.085 (8)
C21	0.037 (4)	0.057 (5)	0.206 (12)	−0.011 (3)	0.013 (6)	−0.048 (6)
C22	0.031 (3)	0.042 (3)	0.111 (6)	−0.004 (3)	0.012 (3)	−0.021 (4)
C23	0.031 (3)	0.035 (3)	0.045 (3)	−0.002 (2)	0.005 (2)	0.018 (3)
C24	0.049 (3)	0.043 (3)	0.041 (3)	−0.013 (3)	0.006 (3)	0.016 (3)
C25	0.063 (4)	0.059 (4)	0.057 (4)	−0.035 (4)	0.005 (3)	0.023 (3)
C26	0.042 (4)	0.094 (6)	0.083 (5)	−0.017 (4)	0.024 (4)	0.035 (5)
C27	0.040 (4)	0.085 (5)	0.082 (5)	0.004 (3)	0.028 (3)	0.034 (4)
C28	0.036 (3)	0.049 (4)	0.066 (4)	0.001 (3)	0.015 (3)	0.021 (3)
C29	0.036 (3)	0.026 (2)	0.039 (3)	0.001 (2)	0.002 (2)	0.018 (2)
C30	0.048 (3)	0.037 (3)	0.049 (4)	−0.011 (3)	0.013 (3)	0.004 (3)
C31	0.080 (5)	0.055 (4)	0.037 (4)	−0.014 (4)	0.008 (3)	0.000 (3)
C32	0.070 (5)	0.047 (4)	0.056 (4)	−0.017 (3)	−0.019 (4)	0.007 (3)
C33	0.054 (4)	0.041 (3)	0.068 (5)	0.003 (3)	−0.013 (3)	0.010 (3)
C34	0.044 (3)	0.033 (3)	0.051 (4)	0.008 (2)	0.000 (3)	0.017 (3)
C35	0.030 (3)	0.019 (2)	0.041 (3)	−0.0015 (19)	0.012 (2)	0.009 (2)
C36	0.032 (3)	0.042 (3)	0.042 (3)	−0.005 (2)	0.011 (2)	0.008 (2)
C37	0.043 (3)	0.065 (4)	0.047 (4)	−0.002 (3)	0.018 (3)	0.008 (3)
C38	0.037 (3)	0.051 (4)	0.072 (5)	−0.003 (3)	0.028 (3)	0.012 (3)
C39	0.029 (3)	0.037 (3)	0.067 (4)	−0.005 (2)	0.008 (3)	0.012 (3)
C40	0.040 (3)	0.026 (2)	0.046 (3)	−0.005 (2)	0.010 (2)	0.011 (2)
C41	0.028 (2)	0.033 (3)	0.041 (3)	0.005 (2)	0.013 (2)	0.011 (2)
C42	0.038 (3)	0.045 (3)	0.064 (4)	−0.003 (3)	0.001 (3)	0.018 (3)
C43	0.041 (3)	0.068 (5)	0.065 (5)	0.010 (3)	−0.004 (3)	0.030 (4)
C44	0.029 (3)	0.085 (5)	0.045 (4)	0.005 (3)	−0.004 (3)	0.014 (3)
C45	0.055 (4)	0.065 (5)	0.050 (4)	−0.011 (3)	−0.006 (3)	−0.005 (4)
C46	0.048 (3)	0.040 (3)	0.048 (4)	0.002 (3)	0.000 (3)	−0.002 (3)
C47	0.026 (2)	0.026 (2)	0.039 (3)	−0.001 (2)	0.011 (2)	−0.003 (2)
C48	0.028 (3)	0.035 (3)	0.043 (3)	0.003 (2)	0.006 (2)	0.003 (2)
C49	0.052 (4)	0.045 (3)	0.037 (3)	0.000 (3)	0.011 (3)	0.000 (3)
C50	0.042 (3)	0.050 (3)	0.054 (4)	0.003 (3)	0.027 (3)	0.005 (3)
C51	0.029 (3)	0.053 (4)	0.058 (4)	−0.001 (2)	0.016 (3)	−0.004 (3)
C52	0.029 (3)	0.043 (3)	0.040 (3)	−0.001 (2)	0.008 (2)	−0.002 (2)
C53	0.025 (2)	0.026 (2)	0.036 (3)	−0.0007 (19)	0.009 (2)	−0.002 (2)
C54	0.036 (3)	0.023 (2)	0.044 (3)	−0.002 (2)	0.015 (2)	0.001 (2)
C55	0.030 (3)	0.030 (3)	0.054 (4)	−0.008 (2)	0.015 (2)	−0.001 (3)
C56	0.023 (2)	0.040 (3)	0.052 (3)	−0.008 (2)	0.014 (2)	−0.013 (3)
C57	0.030 (3)	0.037 (3)	0.039 (3)	0.002 (2)	0.005 (2)	−0.007 (2)
C58	0.026 (2)	0.029 (3)	0.037 (3)	−0.0050 (18)	0.010 (2)	−0.001 (2)
C59	0.026 (2)	0.039 (3)	0.035 (3)	−0.005 (2)	0.0083 (19)	−0.006 (3)
C60	0.036 (3)	0.037 (3)	0.030 (3)	−0.006 (2)	0.005 (2)	0.000 (2)
C61	0.066 (4)	0.041 (3)	0.032 (3)	−0.009 (3)	0.015 (3)	−0.007 (3)
C62	0.053 (3)	0.038 (3)	0.046 (4)	−0.015 (3)	0.027 (3)	−0.017 (3)
C63	0.035 (3)	0.047 (3)	0.066 (4)	−0.012 (3)	0.023 (3)	−0.020 (3)
C64	0.020 (2)	0.060 (4)	0.052 (4)	−0.004 (2)	0.003 (2)	−0.013 (3)
C65	0.027 (3)	0.045 (3)	0.031 (3)	−0.002 (2)	−0.004 (2)	−0.008 (2)
C66	0.039 (3)	0.062 (4)	0.043 (3)	−0.012 (3)	0.014 (3)	−0.019 (3)
C67	0.055 (4)	0.063 (4)	0.043 (4)	−0.009 (3)	0.010 (3)	−0.017 (3)
C68	0.060 (4)	0.051 (4)	0.041 (4)	−0.013 (3)	−0.005 (3)	−0.011 (3)
C69	0.040 (3)	0.061 (4)	0.041 (3)	−0.018 (3)	0.001 (3)	−0.003 (3)
C70	0.034 (3)	0.055 (3)	0.028 (3)	−0.009 (2)	0.005 (2)	−0.006 (3)
C71	0.022 (2)	0.044 (3)	0.031 (3)	0.003 (2)	0.0021 (19)	−0.001 (2)
C72	0.104 (16)	0.045 (6)	0.033 (7)	0.037 (7)	0.003 (8)	−0.008 (5)
C73	0.14 (2)	0.045 (7)	0.038 (6)	0.042 (10)	0.013 (7)	0.002 (5)
C74	0.061 (4)	0.055 (4)	0.050 (4)	0.016 (3)	0.007 (3)	0.016 (3)
C75	0.064 (12)	0.079 (7)	0.041 (8)	−0.031 (8)	−0.024 (8)	0.017 (5)
C76	0.063 (11)	0.058 (8)	0.030 (5)	−0.026 (9)	−0.008 (5)	0.003 (5)
C720	0.037 (10)	0.037 (7)	0.045 (9)	0.004 (6)	0.016 (8)	0.002 (5)
C730	0.047 (11)	0.027 (7)	0.056 (8)	0.006 (7)	0.020 (8)	0.001 (6)
C750	0.066 (15)	0.048 (7)	0.021 (8)	−0.018 (8)	−0.018 (9)	−0.004 (6)
C760	0.048 (12)	0.033 (7)	0.047 (8)	−0.002 (9)	0.011 (8)	0.001 (6)

Geometric parameters (Å, º)

W1—Br1	2.5927 (5)	C33—C34	1.389 (9)
W1—P1	2.5383 (13)	C33—H331	0.950
W1—P2	2.5077 (12)	C34—H341	0.950
W1—P3	2.5543 (12)	C35—C36	1.390 (8)
W1—P4	2.5146 (13)	C35—C40	1.400 (7)
W1—N1	1.775 (4)	C36—C37	1.392 (8)
P1—C7	1.863 (6)	C36—H361	0.950
P1—C11	1.829 (5)	C37—C38	1.381 (9)
P1—C17	1.837 (6)	C37—H371	0.950
P2—C8	1.833 (5)	C38—C39	1.378 (9)
P2—C23	1.820 (5)	C38—H381	0.950
P2—C29	1.835 (6)	C39—C40	1.383 (7)
P3—C9	1.848 (5)	C39—H391	0.950
P3—C35	1.836 (5)	C40—H401	0.950
P3—C41	1.828 (6)	C41—C42	1.398 (8)
P4—C10	1.845 (5)	C41—C46	1.371 (8)
P4—C47	1.827 (5)	C42—C43	1.397 (9)
P4—C53	1.828 (5)	C42—H421	0.950
P5—C5	1.736 (5)	C43—C44	1.353 (10)
P5—C59	1.802 (5)	C43—H431	0.950
P5—C65	1.808 (5)	C44—C45	1.370 (10)
P5—C71	1.790 (5)	C44—H441	0.950
P6—F1	1.597 (5)	C45—C46	1.391 (9)
P6—F2	1.589 (5)	C45—H451	0.950
P6—F3	1.586 (4)	C46—H461	0.950
P6—F4	1.572 (5)	C47—C48	1.386 (8)
P6—F5	1.580 (4)	C47—C52	1.397 (7)
P6—F6	1.601 (5)	C48—C49	1.398 (8)
N1—N2	1.312 (5)	C48—H481	0.950
N2—C1	1.285 (6)	C49—C50	1.376 (9)
Cl1—C1	1.757 (5)	C49—H491	0.950
C1—C2	1.426 (6)	C50—C51	1.370 (9)
C2—C3	1.427 (7)	C50—H501	0.950
C2—C6	1.412 (6)	C51—C52	1.392 (8)
C3—C4	1.356 (7)	C51—H511	0.950
C3—H31	0.950	C52—H521	0.950
C4—C5	1.445 (7)	C53—C54	1.396 (7)
C4—H41	0.950	C53—C58	1.398 (7)
C5—C6	1.386 (7)	C54—C55	1.373 (7)
C6—H61	0.950	C54—H541	0.950
C7—C8	1.509 (8)	C55—C56	1.376 (8)
C7—H71	0.950	C55—H551	0.950
C7—H72	0.950	C56—C57	1.393 (8)
C8—H81	0.950	C56—H561	0.950
C8—H82	0.950	C57—C58	1.380 (7)
C9—C10	1.530 (7)	C57—H571	0.950
C9—H91	0.950	C58—H581	0.950
C9—H92	0.950	C59—C60	1.401 (7)
C10—H101	0.950	C59—C64	1.392 (7)
C10—H102	0.950	C60—C61	1.374 (7)
C11—C12	1.381 (7)	C60—H601	0.950
C11—C16	1.400 (7)	C61—C62	1.384 (9)
C12—C13	1.397 (7)	C61—H611	0.950
C12—H121	0.950	C62—C63	1.373 (9)
C13—C14	1.372 (9)	C62—H621	0.950
C13—H131	0.950	C63—C64	1.388 (8)
C14—C15	1.371 (9)	C63—H631	0.950
C14—H141	0.950	C64—H641	0.950
C15—C16	1.381 (8)	C65—C66	1.386 (8)
C15—H151	0.950	C65—C70	1.383 (7)
C16—H161	0.950	C66—C67	1.396 (8)
C17—C18	1.395 (10)	C66—H661	0.950
C17—C22	1.406 (9)	C67—C68	1.367 (9)
C18—C19	1.378 (11)	C67—H671	0.950
C18—H181	0.950	C68—C69	1.382 (9)
C19—C20	1.329 (17)	C68—H681	0.950
C19—H191	0.950	C69—C70	1.392 (8)
C20—C21	1.409 (17)	C69—H691	0.950
C20—H201	0.950	C70—H701	0.950
C21—C22	1.410 (11)	C71—C72	1.392 (9)
C21—H211	0.950	C71—C76	1.390 (8)
C22—H221	0.950	C71—C720	1.383 (9)
C23—C24	1.400 (8)	C71—C760	1.385 (9)
C23—C28	1.397 (8)	C72—C73	1.390 (9)
C24—C25	1.408 (8)	C72—H721	0.950
C24—H241	0.950	C73—C74	1.391 (9)
C25—C26	1.364 (11)	C73—H731	0.950
C25—H251	0.950	C74—C75	1.370 (9)
C26—C27	1.377 (11)	C74—H741	0.950
C26—H261	0.950	C74—C730	1.383 (9)
C27—C28	1.388 (8)	C74—C750	1.380 (9)
C27—H271	0.950	C74—H741	0.950
C28—H281	0.950	C75—C76	1.382 (9)
C29—C30	1.404 (8)	C75—H751	0.950
C29—C34	1.395 (8)	C76—H761	0.950
C30—C31	1.375 (9)	C720—C730	1.386 (9)
C30—H301	0.950	C720—H725	0.950
C31—C32	1.373 (10)	C730—H735	0.950
C31—H311	0.950	C750—C760	1.384 (9)
C32—C33	1.363 (10)	C750—H755	0.950
C32—H321	0.950	C760—H765	0.950
Br1—W1—P1	85.36 (3)	C29—C30—C31	120.6 (6)
Br1—W1—P2	80.17 (3)	C29—C30—H301	119.7
P1—W1—P2	78.48 (5)	C31—C30—H301	119.7
Br1—W1—P3	89.82 (3)	C30—C31—C32	120.7 (7)
P1—W1—P3	102.93 (4)	C30—C31—H311	119.7
P2—W1—P3	169.78 (4)	C32—C31—H311	119.7
Br1—W1—P4	91.34 (3)	C31—C32—C33	120.1 (6)
P1—W1—P4	176.33 (4)	C31—C32—H321	120.0
P2—W1—P4	99.40 (4)	C33—C32—H321	120.0
P3—W1—P4	78.63 (4)	C32—C33—C34	120.3 (6)
Br1—W1—N1	173.60 (12)	C32—C33—H331	119.9
P1—W1—N1	91.52 (13)	C34—C33—H331	119.9
P2—W1—N1	93.74 (13)	C29—C34—C33	120.8 (6)
P3—W1—N1	96.33 (13)	C29—C34—H341	119.6
P4—W1—N1	91.61 (13)	C33—C34—H341	119.6
W1—P1—C7	109.75 (18)	P3—C35—C36	121.5 (4)
W1—P1—C11	123.31 (17)	P3—C35—C40	119.9 (4)
C7—P1—C11	102.1 (2)	C36—C35—C40	118.5 (5)
W1—P1—C17	114.93 (17)	C35—C36—C37	120.5 (5)
C7—P1—C17	100.5 (3)	C35—C36—H361	119.8
C11—P1—C17	103.3 (3)	C37—C36—H361	119.8
W1—P2—C8	107.98 (17)	C36—C37—C38	120.4 (6)
W1—P2—C23	114.87 (17)	C36—C37—H371	119.8
C8—P2—C23	103.9 (2)	C38—C37—H371	119.8
W1—P2—C29	121.70 (16)	C37—C38—C39	119.4 (5)
C8—P2—C29	103.0 (2)	C37—C38—H381	120.3
C23—P2—C29	103.5 (3)	C39—C38—H381	120.3
W1—P3—C9	109.43 (17)	C38—C39—C40	120.9 (5)
W1—P3—C35	121.93 (16)	C38—C39—H391	119.5
C9—P3—C35	99.2 (2)	C40—C39—H391	119.5
W1—P3—C41	116.45 (16)	C35—C40—C39	120.3 (5)
C9—P3—C41	104.1 (2)	C35—C40—H401	119.9
C35—P3—C41	103.2 (2)	C39—C40—H401	119.9
W1—P4—C10	106.07 (17)	P3—C41—C42	120.8 (4)
W1—P4—C47	118.68 (16)	P3—C41—C46	121.0 (4)
C10—P4—C47	101.1 (2)	C42—C41—C46	118.2 (5)
W1—P4—C53	119.36 (16)	C41—C42—C43	119.5 (6)
C10—P4—C53	104.4 (2)	C41—C42—H421	120.3
C47—P4—C53	104.8 (2)	C43—C42—H421	120.3
C5—P5—C59	112.7 (2)	C42—C43—C44	122.0 (6)
C5—P5—C65	108.7 (2)	C42—C43—H431	119.0
C59—P5—C65	109.7 (2)	C44—C43—H431	119.0
C5—P5—C71	109.4 (2)	C43—C44—C45	118.4 (5)
C59—P5—C71	106.4 (2)	C43—C44—H441	120.8
C65—P5—C71	109.8 (2)	C45—C44—H441	120.8
F1—P6—F2	89.9 (3)	C44—C45—C46	121.1 (6)
F1—P6—F3	90.3 (3)	C44—C45—H451	119.4
F2—P6—F3	89.5 (3)	C46—C45—H451	119.4
F1—P6—F4	179.6 (3)	C45—C46—C41	120.8 (6)
F2—P6—F4	89.7 (3)	C45—C46—H461	119.6
F3—P6—F4	89.8 (3)	C41—C46—H461	119.6
F1—P6—F5	88.6 (3)	P4—C47—C48	122.8 (4)
F2—P6—F5	178.5 (3)	P4—C47—C52	118.5 (4)
F3—P6—F5	90.1 (2)	C48—C47—C52	118.6 (5)
F4—P6—F5	91.7 (3)	C47—C48—C49	119.9 (5)
F1—P6—F6	91.8 (3)	C47—C48—H481	120.1
F2—P6—F6	92.2 (3)	C49—C48—H481	120.1
F3—P6—F6	177.3 (3)	C48—C49—C50	121.2 (5)
F4—P6—F6	88.1 (3)	C48—C49—H491	119.4
F5—P6—F6	88.3 (2)	C50—C49—H491	119.4
W1—N1—N2	164.5 (3)	C49—C50—C51	119.1 (5)
N1—N2—C1	126.0 (4)	C49—C50—H501	120.4
Cl1—C1—N2	121.5 (4)	C51—C50—H501	120.4
Cl1—C1—C2	117.4 (4)	C50—C51—C52	120.7 (5)
N2—C1—C2	121.0 (4)	C50—C51—H511	119.6
C1—C2—C3	123.9 (4)	C52—C51—H511	119.6
C1—C2—C6	128.2 (5)	C47—C52—C51	120.5 (5)
C3—C2—C6	108.0 (4)	C47—C52—H521	119.8
C2—C3—C4	108.6 (5)	C51—C52—H521	119.8
C2—C3—H31	125.7	P4—C53—C54	123.4 (4)
C4—C3—H31	125.7	P4—C53—C58	118.9 (4)
C3—C4—C5	107.7 (4)	C54—C53—C58	117.7 (4)
C3—C4—H41	126.1	C53—C54—C55	121.1 (5)
C5—C4—H41	126.1	C53—C54—H541	119.5
C4—C5—P5	124.6 (4)	C55—C54—H541	119.5
C4—C5—C6	108.4 (4)	C54—C55—C56	120.6 (5)
P5—C5—C6	126.9 (4)	C54—C55—H551	119.7
C2—C6—C5	107.2 (4)	C56—C55—H551	119.7
C2—C6—H61	126.4	C55—C56—C57	119.7 (5)
C5—C6—H61	126.4	C55—C56—H561	120.1
P1—C7—C8	112.3 (3)	C57—C56—H561	120.1
P1—C7—H71	108.7	C56—C57—C58	119.5 (5)
C8—C7—H71	108.7	C56—C57—H571	120.3
P1—C7—H72	108.7	C58—C57—H571	120.3
C8—C7—H72	108.7	C53—C58—C57	121.4 (4)
H71—C7—H72	109.5	C53—C58—H581	119.3
C7—C8—P2	110.9 (4)	C57—C58—H581	119.3
C7—C8—H81	109.1	P5—C59—C60	119.8 (4)
P2—C8—H81	109.1	P5—C59—C64	121.2 (4)
C7—C8—H82	109.1	C60—C59—C64	118.9 (5)
P2—C8—H82	109.1	C59—C60—C61	120.0 (5)
H81—C8—H82	109.5	C59—C60—H601	120.0
P3—C9—C10	112.0 (3)	C61—C60—H601	120.0
P3—C9—H91	108.8	C60—C61—C62	120.9 (5)
C10—C9—H91	108.8	C60—C61—H611	119.6
P3—C9—H92	108.8	C62—C61—H611	119.6
C10—C9—H92	108.8	C61—C62—C63	119.6 (5)
H91—C9—H92	109.5	C61—C62—H621	120.2
C9—C10—P4	110.3 (3)	C63—C62—H621	120.2
C9—C10—H101	109.3	C62—C63—C64	120.5 (5)
P4—C10—H101	109.3	C62—C63—H631	119.8
C9—C10—H102	109.3	C64—C63—H631	119.8
P4—C10—H102	109.3	C59—C64—C63	120.2 (5)
H101—C10—H102	109.5	C59—C64—H641	119.9
P1—C11—C12	121.0 (4)	C63—C64—H641	119.9
P1—C11—C16	120.4 (4)	P5—C65—C66	117.2 (4)
C12—C11—C16	118.5 (5)	P5—C65—C70	122.8 (4)
C11—C12—C13	120.6 (5)	C66—C65—C70	120.0 (5)
C11—C12—H121	119.7	C65—C66—C67	119.8 (5)
C13—C12—H121	119.7	C65—C66—H661	120.1
C12—C13—C14	119.5 (5)	C67—C66—H661	120.1
C12—C13—H131	120.3	C66—C67—C68	120.1 (6)
C14—C13—H131	120.3	C66—C67—H671	119.9
C13—C14—C15	120.9 (5)	C68—C67—H671	119.9
C13—C14—H141	119.5	C67—C68—C69	120.1 (6)
C15—C14—H141	119.5	C67—C68—H681	119.9
C14—C15—C16	119.7 (5)	C69—C68—H681	119.9
C14—C15—H151	120.1	C68—C69—C70	120.4 (5)
C16—C15—H151	120.1	C68—C69—H691	119.8
C11—C16—C15	120.7 (5)	C70—C69—H691	119.8
C11—C16—H161	119.6	C69—C70—C65	119.5 (5)
C15—C16—H161	119.6	C69—C70—H701	120.3
P1—C17—C18	122.4 (5)	C65—C70—H701	120.3
P1—C17—C22	118.7 (5)	P5—C71—C72	120.5 (6)
C18—C17—C22	118.8 (6)	P5—C71—C76	124.0 (8)
C17—C18—H181	119.2	C72—C71—C76	115.3 (9)
C19—C18—H181	119.2	P5—C71—C720	119.7 (7)
C18—C19—C20	119.9 (10)	P5—C71—C760	117.3 (8)
C18—C19—H191	120.0	C720—C71—C760	123.0 (10)
C20—C19—H191	120.0	C71—C72—C73	123.0 (11)
C19—C20—C21	122.0 (8)	C71—C72—H721	118.5
C19—C20—H201	119.0	C73—C72—H721	118.5
C21—C20—H201	119.0	C72—C73—C74	117.1 (12)
C20—C21—C22	118.7 (9)	C72—C73—H731	121.4
C20—C21—H211	120.6	C74—C73—H731	121.4
C22—C21—H211	120.6	C73—C74—C75	123.0 (10)
C21—C22—C17	119.1 (8)	C73—C74—H741	118.5
C21—C22—H221	120.5	C75—C74—H741	118.5
C17—C22—H221	120.5	C730—C74—C750	115.1 (11)
P2—C23—C24	122.9 (4)	C730—C74—H741	117.6
P2—C23—C28	118.8 (4)	C750—C74—H741	126.6
C24—C23—C28	118.3 (5)	C74—C75—C76	116.2 (14)
C23—C24—C25	120.3 (6)	C74—C75—H751	121.9
C23—C24—H241	119.8	C76—C75—H751	121.9
C25—C24—H241	119.8	C71—C76—C75	124.8 (13)
C24—C25—C26	120.0 (6)	C71—C76—H761	117.6
C24—C25—H251	120.0	C75—C76—H761	117.6
C26—C25—H251	120.0	C71—C720—C730	118.4 (13)
C25—C26—C27	120.3 (6)	C71—C720—H725	120.8
C25—C26—H261	119.8	C730—C720—H725	120.8
C27—C26—H261	119.8	C720—C730—C74	122.2 (13)
C26—C27—C28	120.6 (7)	C720—C730—H735	118.9
C26—C27—H271	119.7	C74—C730—H735	118.9
C28—C27—H271	119.7	C74—C750—C760	126.6 (16)
C23—C28—C27	120.4 (6)	C74—C750—H755	116.7
C23—C28—H281	119.8	C760—C750—H755	116.7
C27—C28—H281	119.8	C71—C760—C750	114.3 (15)
P2—C29—C30	120.8 (4)	C71—C760—H765	122.8
P2—C29—C34	121.5 (4)	C750—C760—H765	122.8
C30—C29—C34	117.6 (5)
Br1—W1—N1—N2	1 (6)	C2—C6—C5—P5	179.3 (6)
W1—N1—N2—C1	180 (2)	N2—C1—C2—C3	−1.4 (11)
N1—N2—C1—Cl1	−2.4 (12)	C1—C2—C3—C4	179.9 (6)
N2—C1—C2—C6	179.5 (7)	C2—C3—C4—C5	1.1 (8)
C1—C2—C6—C5	179.5 (7)	C3—C4—C5—C6	−0.9 (6)