Substitutional disorder in the substituted nixantphos ligand C(39)H(32)Br(0.27)Cl(0.73)NOP(2).

The structure of 10-(3-bromo/chloro-prop-yl)-4,6-bis-(diphenyl-phosphino)-10H-phenoxazine, C(39)H(32)Br(0.27)Cl(0.73)NOP(2), shows chloro/bromo substitutional disorder in a 3:1 ratio. For application as a ligand in catalysis, the intra-molecular P⋯P distance of 4.263 (2) Å is relevant. The phenoxazine ring system is essentially planar.

Related literature

For related literature see: Osiński et al. (2005 ▶); Ricken et al. (2006a ▶,b ▶); (Marimuthu et al., 2008 ▶); Deprele & Montchamp (2004 ▶); Laungani et al. (2008 ▶); van Leeuwen et al. (2002 ▶); Norman et al. (2000 ▶); Ricken et al. (2006 ▶); Rotar et al. (2008 ▶); Sandee et al. (1999 ▶, 2001 ▶); Web et al. (2005 ▶).

Experimental

Crystal data

C39H32Br0.27Cl0.73n class="Gene">NOP2

M = 639.83

Triclinic,

a = 10.0539 (3) Å

b = 11.4469 (3) Å

c = 14.5299 (3) Å

α = 69.544 (1)°

β = 83.283 (2)°

γ = 81.453 (1)°

V = 1545.52 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.58 mm−1

T = 173 (2) K

0.42 × 0.19 × 0.17 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: integration (XPREP; Bruker, 2005 ▶) T min = 0.792, T max = 0.908

24195 measured reflections

7458 independent reflections

5180 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.097

S = 0.94

7458 reflections

401 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (n class="Chemical">Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 2003 ▶) and ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536808007848/pv2073sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808007848/pv2073Isup2.hkl

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

C39H32Br0.27Cl0.73NOP2	Z = 2
Mr = 639.83	F000 = 665.6
Triclinic, P1	Dx = 1.375 Mg m−3
Hall symbol: -P 1	Melting point: 493(2) K
a = 10.0539 (3) Å	Mo Kα radiation λ = 0.71073 Å
b = 11.4469 (3) Å	Cell parameters from 6264 reflections
c = 14.5299 (3) Å	θ = 2.5–28.2º
α = 69.544 (1)º	µ = 0.58 mm−1
β = 83.283 (2)º	T = 173 (2) K
γ = 81.453 (1)º	Prism, colourless
V = 1545.52 (7) Å3	0.42 × 0.19 × 0.17 mm

Bruker APEXII CCD area-detector diffractometer	7458 independent reflections
Radiation source: fine-focus sealed tube	5180 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.051
T = 173(2) K	θmax = 28.0º
φ and ω scans	θmin = 1.5º
Absorption correction: integration(XPREP; Bruker, 2005)	h = −13→12
Tmin = 0.792, Tmax = 0.908	k = −15→15
24195 measured reflections	l = −17→19

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) + (0.0499P)2] where P = (Fo2 + 2Fc2)/3
S = 0.94	(Δ/σ)max = 0.006
7458 reflections	Δρmax = 0.36 e Å−3
401 parameters	Δρmin = −0.28 e Å−3
2 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

Experimental. Spectroscopic analysis: 1H NMR (400 MHz,CDCl3, δ, p.p.m.) = 2.13(m, 2H; CH), 2.16(m, 2H; CH), 3.52(m, 2H; CH), 3.69(m, 2H; CH), 6.0(d, 2H; J(H,H) = 7.5 Hz,), 6.34(bd, 2H; J(H,H) = 7.5 Hz,), 6.65(t, 2H J(H,H) = 7.8 Hz), 7.18 – 7.21(bs, 20H); 13C NMR (400 MHz, CDCl3, δ, p.p.m.); = 27.5(ClCH2), 30.8(BrCH2), 41.8(NCH2), 42.6(NCH2), 42.6(NCH2), 111.6(CH), 123.7(CH), 125.5 (C), 128.1(CH), 132.8(CN), 133.8(C),136.8(C),147.0(CO) 31P NMR (600 MHz,CDCl3, δ, p.p.m.) = -19.0; FTIR: cm-1 = 1552(s), 1462(s), 1433(s), 1418(s), 1380(s), 1274(s CN), 1257(m),1206(m), 1092(m), 765(m), 747(m), 722(m), 697(s).516(s), 496(s), 433(s), 400(s); Calculated for C39H32Br0.27Cl0.73NOP2: C=72.03; H= 4.96; N= 2.15; Found C=71.55; H= 4.95; N= 2.26.

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	Occ. (<1)
C1	0.12106 (16)	0.58921 (15)	0.41860 (12)	0.0285 (4)
C2	0.06839 (17)	0.70497 (16)	0.42572 (13)	0.0337 (4)
H2	0.0852	0.7255	0.4809	0.040*
C3	−0.00868 (18)	0.79126 (17)	0.35303 (13)	0.0360 (4)
H3	−0.0466	0.8690	0.3601	0.043*
C4	−0.03072 (17)	0.76542 (16)	0.27087 (13)	0.0326 (4)
H4	−0.0819	0.8261	0.2210	0.039*
C5	0.02184 (16)	0.65037 (15)	0.26046 (12)	0.0275 (4)
C6	0.09436 (16)	0.56450 (15)	0.33551 (12)	0.0285 (4)
C7	0.22129 (16)	0.36362 (15)	0.39245 (11)	0.0278 (4)
C8	0.26881 (17)	0.25469 (15)	0.37271 (12)	0.0283 (4)
C9	0.35333 (18)	0.16430 (16)	0.43904 (12)	0.0349 (4)
H9	0.3863	0.0875	0.4285	0.042*
C10	0.38889 (19)	0.18641 (17)	0.51980 (13)	0.0376 (4)
H10	0.4471	0.1249	0.5642	0.045*
C11	0.34067 (17)	0.29726 (16)	0.53695 (12)	0.0322 (4)
H11	0.3677	0.3119	0.5921	0.039*
C12	0.25368 (16)	0.38670 (15)	0.47466 (12)	0.0284 (4)
C13	0.22292 (18)	0.52225 (17)	0.57888 (12)	0.0348 (4)
H13A	0.2434	0.4414	0.6323	0.042*
H13B	0.1411	0.5677	0.6012	0.042*
C14	0.33988 (17)	0.59931 (17)	0.56022 (12)	0.0348 (4)
H14A	0.4163	0.5629	0.5255	0.042*
H14B	0.3124	0.6860	0.5168	0.042*
C15	0.38590 (18)	0.60363 (13)	0.65430 (13)	0.0417 (5)
H15A	0.3061	0.6182	0.6975	0.050*
H15B	0.4399	0.6746	0.6385	0.050*
C21	−0.10597 (16)	0.74294 (16)	0.08074 (12)	0.0288 (4)
C22	−0.24546 (18)	0.75239 (18)	0.09281 (14)	0.0403 (4)
H22	−0.2878	0.6862	0.1412	0.048*
C23	−0.32390 (19)	0.8556 (2)	0.03611 (15)	0.0451 (5)
H23	−0.4193	0.8604	0.0467	0.054*
C24	−0.26619 (19)	0.95128 (18)	−0.03519 (13)	0.0409 (5)
H24	−0.3207	1.0222	−0.0746	0.049*
C25	−0.1281 (2)	0.9435 (2)	−0.04912 (14)	0.0481 (5)
H25	−0.0867	1.0091	−0.0988	0.058*
C26	−0.04918 (19)	0.84080 (18)	0.00873 (13)	0.0420 (5)
H26	0.0462	0.8374	−0.0012	0.050*
C31	0.15173 (17)	0.60609 (16)	0.08889 (12)	0.0327 (4)
C32	0.24948 (19)	0.6776 (2)	0.09138 (15)	0.0489 (5)
H32	0.2373	0.7233	0.1357	0.059*
C33	0.3658 (2)	0.6825 (2)	0.02890 (18)	0.0614 (6)
H33	0.4328	0.7318	0.0307	0.074*
C34	0.3846 (2)	0.6171 (2)	−0.03508 (16)	0.0588 (6)
H34	0.4641	0.6218	−0.0780	0.071*
C35	0.2896 (2)	0.5453 (2)	−0.03736 (16)	0.0567 (6)
H35	0.3026	0.4997	−0.0818	0.068*
C36	0.1751 (2)	0.53893 (18)	0.02441 (14)	0.0433 (5)
H36	0.1102	0.4873	0.0231	0.052*
C41	0.32148 (18)	0.09367 (15)	0.26043 (11)	0.0299 (4)
C42	0.45411 (19)	0.09954 (17)	0.22056 (13)	0.0374 (4)
H42	0.4897	0.1779	0.1972	0.045*
C43	0.53459 (19)	−0.00586 (19)	0.21437 (14)	0.0418 (5)
H43	0.6251	0.0000	0.1874	0.050*
C44	0.48400 (19)	−0.12036 (17)	0.24733 (13)	0.0380 (4)
H44	0.5392	−0.1932	0.2425	0.046*
C45	0.35297 (19)	−0.12821 (17)	0.28719 (12)	0.0370 (4)
H45	0.3178	−0.2068	0.3102	0.044*
C46	0.27231 (18)	−0.02186 (15)	0.29384 (12)	0.0318 (4)
H46	0.1822	−0.0282	0.3216	0.038*
C51	0.05273 (18)	0.19766 (15)	0.29170 (13)	0.0322 (4)
C52	−0.0264 (2)	0.21254 (18)	0.21515 (14)	0.0445 (5)
H52	0.0075	0.2503	0.1491	0.053*
C53	−0.1533 (2)	0.1735 (2)	0.23338 (17)	0.0534 (6)
H53	−0.2046	0.1821	0.1800	0.064*
C54	−0.2052 (2)	0.12224 (19)	0.32848 (17)	0.0494 (5)
H54	−0.2922	0.0946	0.3411	0.059*
C55	−0.13087 (19)	0.11098 (18)	0.40537 (15)	0.0423 (5)
H55	−0.1678	0.0782	0.4713	0.051*
C56	−0.00240 (18)	0.14728 (16)	0.38703 (13)	0.0347 (4)
H56	0.0488	0.1375	0.4407	0.042*
N1	0.19570 (15)	0.49747 (13)	0.49120 (10)	0.0332 (3)
O1	0.13571 (13)	0.44822 (11)	0.32597 (9)	0.0371 (3)
P1	−0.01140 (4)	0.60026 (4)	0.15924 (3)	0.02944 (12)
P2	0.22335 (5)	0.24299 (4)	0.25806 (3)	0.03152 (12)
Cl1	0.4842 (12)	0.4617 (8)	0.7179 (10)	0.0488 (6)	0.7338 (16)
Br1	0.4972 (14)	0.4545 (9)	0.7259 (12)	0.0488 (6)	0.2662 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0291 (9)	0.0290 (9)	0.0308 (9)	−0.0055 (7)	−0.0015 (7)	−0.0135 (7)
C2	0.0349 (10)	0.0347 (10)	0.0387 (10)	−0.0040 (8)	−0.0022 (8)	−0.0215 (8)
C3	0.0360 (10)	0.0317 (10)	0.0461 (11)	−0.0001 (8)	−0.0033 (8)	−0.0218 (8)
C4	0.0333 (9)	0.0284 (9)	0.0370 (9)	−0.0020 (8)	−0.0033 (7)	−0.0125 (8)
C5	0.0294 (9)	0.0250 (9)	0.0293 (8)	−0.0063 (7)	−0.0010 (7)	−0.0096 (7)
C6	0.0309 (9)	0.0251 (9)	0.0332 (9)	−0.0056 (7)	−0.0009 (7)	−0.0139 (7)
C7	0.0318 (9)	0.0251 (9)	0.0271 (8)	−0.0061 (7)	−0.0048 (7)	−0.0076 (7)
C8	0.0349 (9)	0.0243 (9)	0.0277 (8)	−0.0056 (7)	−0.0045 (7)	−0.0097 (7)
C9	0.0475 (11)	0.0240 (9)	0.0343 (9)	−0.0010 (8)	−0.0101 (8)	−0.0102 (7)
C10	0.0457 (11)	0.0325 (10)	0.0342 (10)	−0.0007 (8)	−0.0143 (8)	−0.0089 (8)
C11	0.0397 (10)	0.0321 (10)	0.0277 (9)	−0.0049 (8)	−0.0082 (7)	−0.0116 (7)
C12	0.0328 (9)	0.0281 (9)	0.0274 (8)	−0.0082 (7)	−0.0016 (7)	−0.0115 (7)
C13	0.0417 (10)	0.0361 (10)	0.0306 (9)	−0.0086 (8)	−0.0008 (8)	−0.0151 (8)
C14	0.0375 (10)	0.0350 (10)	0.0325 (9)	−0.0063 (8)	−0.0014 (8)	−0.0117 (8)
C15	0.0490 (12)	0.0382 (11)	0.0431 (11)	−0.0037 (9)	−0.0135 (9)	−0.0175 (9)
C21	0.0313 (9)	0.0306 (9)	0.0284 (9)	−0.0019 (7)	−0.0044 (7)	−0.0146 (7)
C22	0.0340 (10)	0.0389 (11)	0.0462 (11)	−0.0041 (9)	−0.0019 (8)	−0.0125 (9)
C23	0.0313 (10)	0.0525 (13)	0.0550 (12)	0.0018 (9)	−0.0081 (9)	−0.0236 (10)
C24	0.0470 (12)	0.0409 (11)	0.0354 (10)	0.0077 (9)	−0.0160 (9)	−0.0148 (9)
C25	0.0473 (12)	0.0459 (12)	0.0393 (11)	−0.0031 (10)	−0.0063 (9)	0.0004 (9)
C26	0.0334 (10)	0.0459 (12)	0.0394 (10)	−0.0040 (9)	−0.0043 (8)	−0.0050 (9)
C31	0.0317 (9)	0.0314 (10)	0.0314 (9)	0.0029 (8)	−0.0066 (7)	−0.0073 (8)
C32	0.0375 (11)	0.0573 (14)	0.0555 (13)	−0.0081 (10)	−0.0035 (9)	−0.0223 (11)
C33	0.0393 (12)	0.0654 (16)	0.0711 (16)	−0.0138 (11)	−0.0013 (11)	−0.0104 (13)
C34	0.0501 (14)	0.0506 (14)	0.0515 (13)	0.0140 (11)	0.0096 (10)	0.0004 (11)
C35	0.0631 (15)	0.0510 (14)	0.0477 (13)	0.0068 (12)	0.0093 (11)	−0.0159 (11)
C36	0.0486 (12)	0.0397 (11)	0.0410 (11)	0.0024 (9)	−0.0024 (9)	−0.0164 (9)
C41	0.0419 (10)	0.0256 (9)	0.0243 (8)	−0.0011 (8)	−0.0082 (7)	−0.0104 (7)
C42	0.0447 (11)	0.0349 (10)	0.0362 (10)	−0.0095 (9)	−0.0031 (8)	−0.0145 (8)
C43	0.0369 (10)	0.0507 (13)	0.0406 (11)	−0.0016 (9)	−0.0034 (8)	−0.0201 (9)
C44	0.0480 (11)	0.0346 (10)	0.0310 (9)	0.0104 (9)	−0.0113 (8)	−0.0140 (8)
C45	0.0548 (12)	0.0267 (9)	0.0287 (9)	−0.0029 (9)	−0.0051 (8)	−0.0082 (7)
C46	0.0409 (10)	0.0268 (9)	0.0278 (9)	−0.0024 (8)	−0.0019 (7)	−0.0100 (7)
C51	0.0421 (10)	0.0230 (9)	0.0366 (10)	0.0056 (8)	−0.0128 (8)	−0.0169 (7)
C52	0.0585 (13)	0.0376 (11)	0.0401 (11)	−0.0005 (10)	−0.0214 (9)	−0.0132 (9)
C53	0.0552 (13)	0.0475 (13)	0.0629 (14)	0.0005 (11)	−0.0333 (11)	−0.0189 (11)
C54	0.0403 (11)	0.0394 (12)	0.0740 (15)	0.0032 (9)	−0.0180 (11)	−0.0245 (11)
C55	0.0416 (11)	0.0380 (11)	0.0513 (12)	0.0013 (9)	−0.0038 (9)	−0.0222 (9)
C56	0.0386 (10)	0.0333 (10)	0.0382 (10)	0.0034 (8)	−0.0103 (8)	−0.0201 (8)
N1	0.0436 (9)	0.0305 (8)	0.0312 (8)	−0.0019 (7)	−0.0088 (7)	−0.0167 (6)
O1	0.0524 (8)	0.0265 (6)	0.0376 (7)	0.0075 (6)	−0.0200 (6)	−0.0169 (5)
P1	0.0326 (2)	0.0276 (2)	0.0302 (2)	−0.00380 (19)	−0.00480 (18)	−0.01137 (19)
P2	0.0463 (3)	0.0230 (2)	0.0269 (2)	−0.0012 (2)	−0.0079 (2)	−0.00993 (18)
Cl1	0.0433 (17)	0.0434 (7)	0.0459 (17)	−0.0032 (4)	−0.0128 (10)	0.0046 (7)
Br1	0.0433 (17)	0.0434 (7)	0.0459 (17)	−0.0032 (4)	−0.0128 (10)	0.0046 (7)

C1—C2	1.386 (2)	C24—C25	1.373 (3)
C1—C6	1.395 (2)	C24—H24	0.9500
C1—N1	1.398 (2)	C25—C26	1.380 (3)
C2—C3	1.388 (2)	C25—H25	0.9500
C2—H2	0.9500	C26—H26	0.9500
C3—C4	1.375 (2)	C31—C32	1.380 (3)
C3—H3	0.9500	C31—C36	1.386 (3)
C4—C5	1.396 (2)	C31—P1	1.8253 (18)
C4—H4	0.9500	C32—C33	1.389 (3)
C5—C6	1.382 (2)	C32—H32	0.9500
C5—P1	1.8345 (16)	C33—C34	1.365 (3)
C6—O1	1.3837 (19)	C33—H33	0.9500
C7—O1	1.3799 (19)	C34—C35	1.360 (3)
C7—C8	1.381 (2)	C34—H34	0.9500
C7—C12	1.393 (2)	C35—C36	1.368 (3)
C8—C9	1.398 (2)	C35—H35	0.9500
C8—P2	1.8313 (16)	C36—H36	0.9500
C9—C10	1.379 (2)	C41—C46	1.385 (2)
C9—H9	0.9500	C41—C42	1.392 (2)
C10—C11	1.385 (2)	C41—P2	1.8335 (17)
C10—H10	0.9500	C42—C43	1.374 (3)
C11—C12	1.380 (2)	C42—H42	0.9500
C11—H11	0.9500	C43—C44	1.381 (3)
C12—N1	1.402 (2)	C43—H43	0.9500
C13—N1	1.461 (2)	C44—C45	1.378 (3)
C13—C14	1.517 (2)	C44—H44	0.9500
C13—H13A	0.9900	C45—C46	1.385 (2)
C13—H13B	0.9900	C45—H45	0.9500
C14—C15	1.512 (2)	C46—H46	0.9500
C14—H14A	0.9900	C51—C56	1.384 (2)
C14—H14B	0.9900	C51—C52	1.390 (2)
C15—Cl1	1.7770 (18)	C51—P2	1.8281 (18)
C15—Br1	1.9266 (19)	C52—C53	1.380 (3)
C15—H15A	0.9900	C52—H52	0.9500
C15—H15B	0.9900	C53—C54	1.372 (3)
C21—C26	1.381 (2)	C53—H53	0.9500
C21—C22	1.386 (2)	C54—C55	1.374 (3)
C21—P1	1.8338 (17)	C54—H54	0.9500
C22—C23	1.375 (3)	C55—C56	1.383 (2)
C22—H22	0.9500	C55—H55	0.9500
C23—C24	1.365 (3)	C56—H56	0.9500
C23—H23	0.9500
C2—C1—C6	117.26 (15)	C24—C25—H25	119.8
C2—C1—N1	122.98 (15)	C26—C25—H25	119.8
C6—C1—N1	119.74 (15)	C25—C26—C21	121.39 (18)
C1—C2—C3	120.70 (16)	C25—C26—H26	119.3
C1—C2—H2	119.7	C21—C26—H26	119.3
C3—C2—H2	119.7	C32—C31—C36	118.05 (18)
C4—C3—C2	120.72 (17)	C32—C31—P1	124.77 (15)
C4—C3—H3	119.6	C36—C31—P1	117.08 (14)
C2—C3—H3	119.6	C31—C32—C33	119.9 (2)
C3—C4—C5	120.29 (17)	C31—C32—H32	120.1
C3—C4—H4	119.9	C33—C32—H32	120.1
C5—C4—H4	119.9	C34—C33—C32	120.7 (2)
C6—C5—C4	117.78 (15)	C34—C33—H33	119.7
C6—C5—P1	117.69 (12)	C32—C33—H33	119.7
C4—C5—P1	124.31 (13)	C35—C34—C33	119.9 (2)
C5—C6—O1	115.95 (14)	C35—C34—H34	120.0
C5—C6—C1	123.20 (15)	C33—C34—H34	120.0
O1—C6—C1	120.80 (15)	C34—C35—C36	119.9 (2)
O1—C7—C8	115.32 (14)	C34—C35—H35	120.0
O1—C7—C12	121.59 (15)	C36—C35—H35	120.0
C8—C7—C12	123.07 (15)	C35—C36—C31	121.5 (2)
C7—C8—C9	117.72 (15)	C35—C36—H36	119.2
C7—C8—P2	117.39 (12)	C31—C36—H36	119.2
C9—C8—P2	124.82 (13)	C46—C41—C42	118.10 (16)
C10—C9—C8	120.13 (16)	C46—C41—P2	125.35 (14)
C10—C9—H9	119.9	C42—C41—P2	116.47 (13)
C8—C9—H9	119.9	C43—C42—C41	121.27 (17)
C9—C10—C11	120.73 (17)	C43—C42—H42	119.4
C9—C10—H10	119.6	C41—C42—H42	119.4
C11—C10—H10	119.6	C42—C43—C44	120.04 (18)
C12—C11—C10	120.61 (15)	C42—C43—H43	120.0
C12—C11—H11	119.7	C44—C43—H43	120.0
C10—C11—H11	119.7	C45—C44—C43	119.59 (17)
C11—C12—C7	117.69 (16)	C45—C44—H44	120.2
C11—C12—N1	123.19 (14)	C43—C44—H44	120.2
C7—C12—N1	119.11 (15)	C44—C45—C46	120.22 (17)
N1—C13—C14	112.39 (14)	C44—C45—H45	119.9
N1—C13—H13A	109.1	C46—C45—H45	119.9
C14—C13—H13A	109.1	C41—C46—C45	120.78 (17)
N1—C13—H13B	109.1	C41—C46—H46	119.6
C14—C13—H13B	109.1	C45—C46—H46	119.6
H13A—C13—H13B	107.9	C56—C51—C52	117.67 (17)
C15—C14—C13	112.46 (15)	C56—C51—P2	125.18 (13)
C15—C14—H14A	109.1	C52—C51—P2	117.13 (14)
C13—C14—H14A	109.1	C53—C52—C51	121.25 (19)
C15—C14—H14B	109.1	C53—C52—H52	119.4
C13—C14—H14B	109.1	C51—C52—H52	119.4
H14A—C14—H14B	107.8	C54—C53—C52	120.04 (18)
C14—C15—Cl1	111.5 (5)	C54—C53—H53	120.0
C14—C15—Br1	114.0 (6)	C52—C53—H53	120.0
C14—C15—H15A	109.3	C53—C54—C55	119.73 (19)
Cl1—C15—H15A	109.3	C53—C54—H54	120.1
Br1—C15—H15A	109.2	C55—C54—H54	120.1
C14—C15—H15B	109.3	C54—C55—C56	120.16 (19)
Cl1—C15—H15B	109.3	C54—C55—H55	119.9
Br1—C15—H15B	106.8	C56—C55—H55	119.9
H15A—C15—H15B	108.0	C55—C56—C51	121.07 (17)
C26—C21—C22	117.21 (17)	C55—C56—H56	119.5
C26—C21—P1	125.12 (13)	C51—C56—H56	119.5
C22—C21—P1	117.65 (13)	C1—N1—C12	119.14 (13)
C23—C22—C21	121.32 (17)	C1—N1—C13	120.04 (14)
C23—C22—H22	119.3	C12—N1—C13	120.59 (14)
C21—C22—H22	119.3	C7—O1—C6	118.58 (12)
C24—C23—C22	120.74 (18)	C31—P1—C21	100.52 (7)
C24—C23—H23	119.6	C31—P1—C5	102.11 (8)
C22—C23—H23	119.6	C21—P1—C5	101.24 (7)
C23—C24—C25	118.97 (18)	C51—P2—C8	102.00 (8)
C23—C24—H24	120.5	C51—P2—C41	101.66 (8)
C25—C24—H24	120.5	C8—P2—C41	100.58 (7)
C24—C25—C26	120.35 (18)
C6—C1—C2—C3	0.6 (2)	C43—C44—C45—C46	0.2 (3)
N1—C1—C2—C3	−177.93 (15)	C42—C41—C46—C45	−0.3 (2)
C1—C2—C3—C4	−2.2 (3)	P2—C41—C46—C45	176.23 (13)
C2—C3—C4—C5	1.4 (3)	C44—C45—C46—C41	0.2 (3)
C3—C4—C5—C6	0.7 (2)	C56—C51—C52—C53	−2.7 (3)
C3—C4—C5—P1	175.10 (13)	P2—C51—C52—C53	175.83 (15)
C4—C5—C6—O1	175.16 (14)	C51—C52—C53—C54	1.9 (3)
P1—C5—C6—O1	0.4 (2)	C52—C53—C54—C55	0.6 (3)
C4—C5—C6—C1	−2.3 (2)	C53—C54—C55—C56	−2.2 (3)
P1—C5—C6—C1	−177.06 (13)	C54—C55—C56—C51	1.3 (3)
C2—C1—C6—C5	1.6 (2)	C52—C51—C56—C55	1.1 (3)
N1—C1—C6—C5	−179.76 (15)	P2—C51—C56—C55	−177.33 (14)
C2—C1—C6—O1	−175.72 (15)	C2—C1—N1—C12	−175.29 (15)
N1—C1—C6—O1	2.9 (2)	C6—C1—N1—C12	6.2 (2)
O1—C7—C8—C9	−178.47 (14)	C2—C1—N1—C13	−0.9 (2)
C12—C7—C8—C9	0.0 (2)	C6—C1—N1—C13	−179.40 (14)
O1—C7—C8—P2	4.6 (2)	C11—C12—N1—C1	172.78 (15)
C12—C7—C8—P2	−176.93 (12)	C7—C12—N1—C1	−8.2 (2)
C7—C8—C9—C10	−1.3 (2)	C11—C12—N1—C13	−1.6 (2)
P2—C8—C9—C10	175.33 (14)	C7—C12—N1—C13	177.40 (14)
C8—C9—C10—C11	0.7 (3)	C14—C13—N1—C1	−80.73 (19)
C9—C10—C11—C12	1.4 (3)	C14—C13—N1—C12	93.60 (19)
C10—C11—C12—C7	−2.7 (2)	C8—C7—O1—C6	−173.86 (14)
C10—C11—C12—N1	176.35 (16)	C12—C7—O1—C6	7.7 (2)
O1—C7—C12—C11	−179.65 (14)	C5—C6—O1—C7	172.70 (14)
C8—C7—C12—C11	2.0 (2)	C1—C6—O1—C7	−9.8 (2)
O1—C7—C12—N1	1.3 (2)	C32—C31—P1—C21	81.38 (17)
C8—C7—C12—N1	−177.05 (15)	C36—C31—P1—C21	−94.87 (15)
N1—C13—C14—C15	−168.77 (14)	C32—C31—P1—C5	−22.66 (18)
C13—C14—C15—Cl1	77.1 (5)	C36—C31—P1—C5	161.09 (14)
C13—C14—C15—Br1	78.6 (6)	C26—C21—P1—C31	−17.74 (17)
C26—C21—C22—C23	−0.7 (3)	C22—C21—P1—C31	160.68 (14)
P1—C21—C22—C23	−179.23 (15)	C26—C21—P1—C5	87.00 (16)
C21—C22—C23—C24	1.1 (3)	C22—C21—P1—C5	−94.58 (14)
C22—C23—C24—C25	−0.5 (3)	C6—C5—P1—C31	−76.01 (14)
C23—C24—C25—C26	−0.5 (3)	C4—C5—P1—C31	109.61 (15)
C24—C25—C26—C21	0.9 (3)	C6—C5—P1—C21	−179.49 (13)
C22—C21—C26—C25	−0.3 (3)	C4—C5—P1—C21	6.13 (16)
P1—C21—C26—C25	178.11 (15)	C56—C51—P2—C8	−18.19 (16)
C36—C31—C32—C33	1.3 (3)	C52—C51—P2—C8	163.35 (14)
P1—C31—C32—C33	−174.94 (16)	C56—C51—P2—C41	85.44 (16)
C31—C32—C33—C34	−0.1 (3)	C52—C51—P2—C41	−93.02 (14)
C32—C33—C34—C35	−0.6 (3)	C7—C8—P2—C51	−80.83 (14)
C33—C34—C35—C36	0.1 (3)	C9—C8—P2—C51	102.50 (15)
C34—C35—C36—C31	1.2 (3)	C7—C8—P2—C41	174.69 (13)
C32—C31—C36—C35	−1.8 (3)	C9—C8—P2—C41	−1.97 (16)
P1—C31—C36—C35	174.67 (16)	C46—C41—P2—C51	−7.91 (16)
C46—C41—C42—C43	−0.1 (3)	C42—C41—P2—C51	168.68 (13)
P2—C41—C42—C43	−176.90 (14)	C46—C41—P2—C8	96.84 (15)
C41—C42—C43—C44	0.5 (3)	C42—C41—P2—C8	−86.57 (14)
C42—C43—C44—C45	−0.6 (3)