4,6-Bis(diphenyl-phosphino)phenoxazine (nixantphos).

The title compound, C(36)H(27)NOP(2), has been reported as a ligand on rhodium for the catalysis of hydro-formyl-ation reactions. The key feature of the compound is the intra-molecular P⋯P distance of 4.255 (2) Å. The bond angles at the P atoms range from 99.93 (10) to 103.02 (10)°. The phenoxazine ring system is essentially planar and a non-crystallographic mirror plane through the N⋯O vector bis-ects the mol-ecule. The C-O bond lengths range from 1.388 (2) to 1.392 (2) Å and the C-N bond lengths range from 1.398 (3) to 1.403 (3) Å.

Related literature

For related literature, see: Antonio et al. (1989 ▶); Claver & van Leeuwen (2000 ▶); Deprele & Montchamp (2004 ▶); n class="Disease">van Leeuwen et al. (2002 ▶); Osiński et al. (2005 ▶); Petrassi et al. (2000 ▶); Ricken et al. (2006a ▶,b ▶,c ▶); Sandee et al. (1999 ▶, 2001 ▶); Tolman (1977 ▶); van der Veen et al. (2000 ▶).

Experimental

Crystal data

C36H27NOP2

M = 551.53

Triclinic,

a = 10.4233 (3) Å

b = 10.9113 (3) Å

c = 12.9940 (4) Å

α = 104.055 (2)°

β = 102.555 (2)°

γ = 97.459 (2)°

V = 1373.04 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.19 mm−1

T = 173 (2) K

0.40 × 0.18 × 0.12 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: none

15968 measured reflections

5396 independent reflections

3646 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.105

S = 0.95

5396 reflections

365 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.29 e Å−3

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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808006648/dn2322sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808006648/dn2322Isup2.hkl

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

C36H27NOP2	Z = 2
Mr = 551.53	F000 = 576
Triclinic, P1	Dx = 1.334 Mg m−3
Hall symbol: -P 1	Melting point: 457(2) K
a = 10.4233 (3) Å	Mo Kα radiation λ = 0.71073 Å
b = 10.9113 (3) Å	Cell parameters from 3152 reflections
c = 12.9940 (4) Å	θ = 2.2–25.5º
α = 104.055 (2)º	µ = 0.19 mm−1
β = 102.555 (2)º	T = 173 (2) K
γ = 97.459 (2)º	Triangular, yellow
V = 1373.04 (7) Å3	0.40 × 0.18 × 0.12 mm

Bruker SMART CCD area-detector diffractometer	3646 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.055
Monochromator: graphite	θmax = 26.0º
T = 173(2) K	θmin = 1.7º
φ and ω scans	h = −10→12
Absorption correction: none	k = −13→13
15968 measured reflections	l = −16→16
5396 independent reflections

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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.048P)2] where P = (Fo2 + 2Fc2)/3
S = 0.95	(Δ/σ)max = 0.001
5396 reflections	Δρmax = 0.38 e Å−3
365 parameters	Δρmin = −0.29 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
C1	0.0632 (2)	0.3597 (2)	0.56267 (18)	0.0339 (5)
C2	0.1275 (2)	0.4755 (2)	0.63818 (19)	0.0391 (6)
H2	0.1111	0.4968	0.7089	0.047*
C3	0.2159 (2)	0.5608 (2)	0.61113 (19)	0.0401 (6)
H3	0.2593	0.6407	0.6633	0.048*
C4	0.2414 (2)	0.5308 (2)	0.50922 (19)	0.0347 (5)
H4	0.3029	0.5900	0.4921	0.042*
C5	0.1780 (2)	0.41454 (19)	0.43100 (17)	0.0288 (5)
C6	0.0885 (2)	0.33272 (19)	0.45990 (18)	0.0300 (5)
C7	−0.0601 (2)	0.1287 (2)	0.40544 (18)	0.0307 (5)
C8	−0.1125 (2)	0.0139 (2)	0.32431 (18)	0.0311 (5)
C9	−0.1946 (2)	−0.0809 (2)	0.34914 (19)	0.0350 (5)
H9	−0.2323	−0.1612	0.2954	0.042*
C10	−0.2214 (2)	−0.0594 (2)	0.4502 (2)	0.0393 (6)
H10	−0.2765	−0.1250	0.4660	0.047*
C11	−0.1690 (2)	0.0565 (2)	0.5287 (2)	0.0395 (6)
H11	−0.1897	0.0709	0.5978	0.047*
C12	−0.0863 (2)	0.1525 (2)	0.50796 (19)	0.0341 (5)
C21	0.3147 (2)	0.50031 (19)	0.28652 (17)	0.0283 (5)
C22	0.2595 (2)	0.6054 (2)	0.2703 (2)	0.0390 (6)
H22	0.1680	0.6049	0.2692	0.047*
C23	0.3343 (2)	0.7100 (2)	0.2558 (2)	0.0415 (6)
H23	0.2950	0.7818	0.2470	0.050*
C24	0.4657 (2)	0.7113 (2)	0.25396 (19)	0.0400 (6)
H24	0.5171	0.7829	0.2424	0.048*
C25	0.5217 (2)	0.6081 (2)	0.2690 (2)	0.0423 (6)
H25	0.6126	0.6084	0.2679	0.051*
C26	0.4479 (2)	0.5037 (2)	0.28585 (19)	0.0351 (5)
H26	0.4888	0.4335	0.2971	0.042*
C31	0.3144 (2)	0.24846 (18)	0.31367 (17)	0.0280 (5)
C32	0.4063 (2)	0.26320 (19)	0.41242 (18)	0.0329 (5)
H32	0.4126	0.3345	0.4734	0.040*
C33	0.4891 (2)	0.1757 (2)	0.4233 (2)	0.0401 (6)
H33	0.5516	0.1867	0.4916	0.048*
C34	0.4812 (2)	0.0733 (2)	0.3362 (2)	0.0450 (6)
H34	0.5383	0.0131	0.3440	0.054*
C35	0.3916 (3)	0.0568 (2)	0.2377 (2)	0.0479 (7)
H35	0.3872	−0.0142	0.1770	0.057*
C36	0.3075 (2)	0.1434 (2)	0.2262 (2)	0.0385 (6)
H36	0.2445	0.1309	0.1579	0.046*
C41	−0.1440 (2)	−0.1688 (2)	0.12171 (18)	0.0346 (5)
C42	−0.0664 (3)	−0.2619 (2)	0.1300 (2)	0.0457 (6)
H42	0.0234	−0.2367	0.1738	0.055*
C43	−0.1170 (3)	−0.3900 (2)	0.0759 (2)	0.0570 (8)
H43	−0.0627	−0.4525	0.0831	0.068*
C44	−0.2466 (3)	−0.4270 (2)	0.0113 (2)	0.0568 (8)
H44	−0.2820	−0.5152	−0.0263	0.068*
C45	−0.3243 (3)	−0.3372 (2)	0.0015 (2)	0.0567 (7)
H45	−0.4137	−0.3629	−0.0432	0.068*
C46	−0.2737 (2)	−0.2084 (2)	0.0563 (2)	0.0465 (6)
H46	−0.3288	−0.1467	0.0488	0.056*
C51	−0.1711 (2)	0.09115 (19)	0.13194 (18)	0.0325 (5)
C52	−0.1280 (2)	0.1525 (2)	0.0605 (2)	0.0459 (6)
H52	−0.0439	0.1441	0.0455	0.055*
C53	−0.2058 (3)	0.2257 (3)	0.0107 (2)	0.0557 (7)
H53	−0.1746	0.2680	−0.0375	0.067*
C54	−0.3276 (3)	0.2372 (2)	0.0307 (2)	0.0525 (7)
H54	−0.3819	0.2858	−0.0052	0.063*
C55	−0.3718 (3)	0.1792 (2)	0.1020 (2)	0.0453 (6)
H55	−0.4559	0.1887	0.1166	0.054*
C56	−0.2939 (2)	0.1070 (2)	0.15255 (19)	0.0386 (6)
H56	−0.3249	0.0674	0.2025	0.046*
N1	−0.0284 (2)	0.27159 (19)	0.58580 (18)	0.0414 (5)
H1	−0.018 (3)	0.277 (3)	0.655 (2)	0.079 (11)*
O1	0.02287 (15)	0.21948 (13)	0.37894 (12)	0.0384 (4)
P1	0.20112 (5)	0.36083 (5)	0.29234 (5)	0.03016 (16)
P2	−0.06220 (6)	−0.00273 (5)	0.19630 (5)	0.03407 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0333 (13)	0.0373 (13)	0.0362 (14)	0.0149 (10)	0.0118 (11)	0.0126 (10)
C2	0.0404 (14)	0.0482 (14)	0.0305 (14)	0.0187 (11)	0.0101 (11)	0.0078 (11)
C3	0.0358 (13)	0.0364 (13)	0.0387 (15)	0.0118 (11)	0.0014 (11)	−0.0018 (11)
C4	0.0260 (12)	0.0330 (12)	0.0406 (14)	0.0056 (9)	0.0035 (10)	0.0066 (10)
C5	0.0252 (11)	0.0298 (11)	0.0323 (13)	0.0114 (9)	0.0042 (10)	0.0100 (9)
C6	0.0275 (11)	0.0285 (11)	0.0325 (13)	0.0092 (9)	0.0058 (10)	0.0057 (9)
C7	0.0253 (11)	0.0354 (12)	0.0376 (14)	0.0088 (9)	0.0108 (10)	0.0177 (10)
C8	0.0231 (11)	0.0348 (12)	0.0363 (13)	0.0068 (9)	0.0041 (10)	0.0142 (10)
C9	0.0246 (12)	0.0394 (13)	0.0404 (14)	0.0024 (9)	0.0038 (10)	0.0161 (10)
C10	0.0285 (12)	0.0452 (14)	0.0503 (16)	0.0036 (10)	0.0099 (11)	0.0267 (12)
C11	0.0325 (13)	0.0562 (16)	0.0419 (15)	0.0157 (11)	0.0179 (11)	0.0251 (12)
C12	0.0312 (12)	0.0396 (13)	0.0378 (14)	0.0139 (10)	0.0113 (11)	0.0167 (11)
C21	0.0295 (12)	0.0278 (11)	0.0261 (12)	0.0030 (9)	0.0050 (9)	0.0077 (9)
C22	0.0348 (13)	0.0386 (13)	0.0498 (16)	0.0118 (10)	0.0137 (11)	0.0188 (11)
C23	0.0503 (15)	0.0314 (13)	0.0462 (15)	0.0139 (11)	0.0113 (12)	0.0151 (11)
C24	0.0403 (14)	0.0307 (12)	0.0446 (15)	−0.0036 (10)	0.0051 (11)	0.0130 (11)
C25	0.0273 (12)	0.0406 (14)	0.0569 (17)	0.0009 (10)	0.0057 (11)	0.0174 (12)
C26	0.0293 (12)	0.0290 (12)	0.0462 (15)	0.0044 (9)	0.0051 (11)	0.0141 (10)
C31	0.0272 (11)	0.0237 (11)	0.0336 (13)	0.0002 (8)	0.0110 (10)	0.0085 (9)
C32	0.0359 (13)	0.0277 (11)	0.0355 (14)	0.0068 (9)	0.0093 (11)	0.0091 (9)
C33	0.0360 (13)	0.0389 (13)	0.0486 (16)	0.0067 (10)	0.0092 (12)	0.0201 (12)
C34	0.0409 (14)	0.0321 (13)	0.0689 (19)	0.0132 (11)	0.0205 (14)	0.0182 (12)
C35	0.0511 (16)	0.0307 (13)	0.0604 (19)	0.0103 (11)	0.0233 (14)	0.0007 (12)
C36	0.0361 (13)	0.0352 (13)	0.0388 (14)	0.0006 (10)	0.0091 (11)	0.0040 (10)
C41	0.0373 (13)	0.0336 (12)	0.0352 (14)	0.0092 (10)	0.0109 (11)	0.0112 (10)
C42	0.0488 (15)	0.0455 (15)	0.0458 (16)	0.0169 (12)	0.0128 (13)	0.0140 (12)
C43	0.080 (2)	0.0410 (16)	0.0562 (19)	0.0263 (14)	0.0215 (16)	0.0142 (13)
C44	0.088 (2)	0.0299 (14)	0.0496 (18)	0.0051 (14)	0.0203 (16)	0.0068 (12)
C45	0.0572 (17)	0.0420 (15)	0.0559 (18)	0.0010 (13)	0.0041 (14)	0.0000 (13)
C46	0.0469 (15)	0.0356 (14)	0.0483 (16)	0.0065 (11)	0.0024 (13)	0.0055 (11)
C51	0.0355 (13)	0.0271 (11)	0.0303 (13)	−0.0020 (9)	0.0055 (10)	0.0062 (9)
C52	0.0444 (15)	0.0511 (15)	0.0436 (16)	0.0021 (12)	0.0138 (12)	0.0174 (12)
C53	0.0628 (19)	0.0604 (18)	0.0529 (18)	0.0077 (14)	0.0145 (15)	0.0351 (14)
C54	0.0589 (18)	0.0488 (16)	0.0542 (18)	0.0128 (13)	0.0074 (14)	0.0275 (13)
C55	0.0464 (15)	0.0447 (14)	0.0494 (17)	0.0136 (12)	0.0121 (13)	0.0192 (12)
C56	0.0408 (14)	0.0406 (13)	0.0399 (14)	0.0094 (11)	0.0126 (11)	0.0189 (11)
N1	0.0534 (13)	0.0434 (12)	0.0354 (13)	0.0145 (10)	0.0226 (11)	0.0132 (10)
O1	0.0460 (10)	0.0326 (8)	0.0359 (9)	−0.0022 (7)	0.0180 (8)	0.0069 (7)
P1	0.0261 (3)	0.0298 (3)	0.0338 (3)	0.0032 (2)	0.0063 (3)	0.0100 (2)
P2	0.0288 (3)	0.0356 (3)	0.0365 (4)	0.0035 (2)	0.0078 (3)	0.0096 (3)

C1—C2	1.379 (3)	C31—C36	1.386 (3)
C1—C6	1.386 (3)	C31—P1	1.836 (2)
C1—N1	1.398 (3)	C32—C33	1.379 (3)
C2—C3	1.384 (3)	C32—H32	0.9500
C2—H2	0.9500	C33—C34	1.363 (3)
C3—C4	1.377 (3)	C33—H33	0.9500
C3—H3	0.9500	C34—C35	1.366 (3)
C4—C5	1.394 (3)	C34—H34	0.9500
C4—H4	0.9500	C35—C36	1.383 (3)
C5—C6	1.381 (3)	C35—H35	0.9500
C5—P1	1.833 (2)	C36—H36	0.9500
C6—O1	1.392 (2)	C41—C46	1.381 (3)
C7—C8	1.382 (3)	C41—C42	1.387 (3)
C7—O1	1.386 (2)	C41—P2	1.826 (2)
C7—C12	1.387 (3)	C42—C43	1.377 (3)
C8—C9	1.400 (3)	C42—H42	0.9500
C8—P2	1.825 (2)	C43—C44	1.376 (4)
C9—C10	1.372 (3)	C43—H43	0.9500
C9—H9	0.9500	C44—C45	1.362 (3)
C10—C11	1.374 (3)	C44—H44	0.9500
C10—H10	0.9500	C45—C46	1.384 (3)
C11—C12	1.384 (3)	C45—H45	0.9500
C11—H11	0.9500	C46—H46	0.9500
C12—N1	1.403 (3)	C51—C52	1.384 (3)
C21—C26	1.385 (3)	C51—C56	1.388 (3)
C21—C22	1.388 (3)	C51—P2	1.828 (2)
C21—P1	1.831 (2)	C52—C53	1.380 (3)
C22—C23	1.372 (3)	C52—H52	0.9500
C22—H22	0.9500	C53—C54	1.365 (3)
C23—C24	1.374 (3)	C53—H53	0.9500
C23—H23	0.9500	C54—C55	1.366 (3)
C24—C25	1.369 (3)	C54—H54	0.9500
C24—H24	0.9500	C55—C56	1.377 (3)
C25—C26	1.380 (3)	C55—H55	0.9500
C25—H25	0.9500	C56—H56	0.9500
C26—H26	0.9500	N1—H1	0.86 (3)
C31—C32	1.384 (3)
C2—C1—C6	118.3 (2)	C31—C32—H32	119.6
C2—C1—N1	122.0 (2)	C34—C33—C32	120.0 (2)
C6—C1—N1	119.7 (2)	C34—C33—H33	120.0
C1—C2—C3	120.1 (2)	C32—C33—H33	120.0
C1—C2—H2	119.9	C33—C34—C35	120.3 (2)
C3—C2—H2	119.9	C33—C34—H34	119.8
C4—C3—C2	120.6 (2)	C35—C34—H34	119.8
C4—C3—H3	119.7	C34—C35—C36	120.1 (2)
C2—C3—H3	119.7	C34—C35—H35	120.0
C3—C4—C5	120.7 (2)	C36—C35—H35	120.0
C3—C4—H4	119.7	C35—C36—C31	120.5 (2)
C5—C4—H4	119.7	C35—C36—H36	119.8
C6—C5—C4	117.2 (2)	C31—C36—H36	119.8
C6—C5—P1	116.86 (15)	C46—C41—C42	117.8 (2)
C4—C5—P1	125.91 (18)	C46—C41—P2	125.83 (17)
C5—C6—C1	123.1 (2)	C42—C41—P2	116.31 (18)
C5—C6—O1	116.04 (19)	C43—C42—C41	121.4 (2)
C1—C6—O1	120.89 (19)	C43—C42—H42	119.3
C8—C7—O1	115.78 (19)	C41—C42—H42	119.3
C8—C7—C12	122.8 (2)	C44—C43—C42	119.7 (2)
O1—C7—C12	121.38 (19)	C44—C43—H43	120.2
C7—C8—C9	117.3 (2)	C42—C43—H43	120.2
C7—C8—P2	116.80 (16)	C45—C44—C43	120.0 (2)
C9—C8—P2	125.87 (17)	C45—C44—H44	120.0
C10—C9—C8	120.8 (2)	C43—C44—H44	120.0
C10—C9—H9	119.6	C44—C45—C46	120.4 (3)
C8—C9—H9	119.6	C44—C45—H45	119.8
C9—C10—C11	120.5 (2)	C46—C45—H45	119.8
C9—C10—H10	119.7	C41—C46—C45	120.8 (2)
C11—C10—H10	119.7	C41—C46—H46	119.6
C10—C11—C12	120.6 (2)	C45—C46—H46	119.6
C10—C11—H11	119.7	C52—C51—C56	117.8 (2)
C12—C11—H11	119.7	C52—C51—P2	118.61 (18)
C11—C12—C7	118.0 (2)	C56—C51—P2	123.61 (18)
C11—C12—N1	122.9 (2)	C53—C52—C51	120.9 (2)
C7—C12—N1	119.1 (2)	C53—C52—H52	119.6
C26—C21—C22	117.61 (19)	C51—C52—H52	119.6
C26—C21—P1	124.86 (16)	C54—C53—C52	120.0 (2)
C22—C21—P1	117.19 (16)	C54—C53—H53	120.0
C23—C22—C21	121.4 (2)	C52—C53—H53	120.0
C23—C22—H22	119.3	C53—C54—C55	120.4 (2)
C21—C22—H22	119.3	C53—C54—H54	119.8
C22—C23—C24	120.3 (2)	C55—C54—H54	119.8
C22—C23—H23	119.8	C54—C55—C56	119.7 (2)
C24—C23—H23	119.8	C54—C55—H55	120.1
C25—C24—C23	119.1 (2)	C56—C55—H55	120.1
C25—C24—H24	120.4	C55—C56—C51	121.2 (2)
C23—C24—H24	120.4	C55—C56—H56	119.4
C24—C25—C26	120.8 (2)	C51—C56—H56	119.4
C24—C25—H25	119.6	C1—N1—C12	119.7 (2)
C26—C25—H25	119.6	C1—N1—H1	115 (2)
C25—C26—C21	120.7 (2)	C12—N1—H1	119.0 (19)
C25—C26—H26	119.7	C7—O1—C6	118.82 (17)
C21—C26—H26	119.7	C21—P1—C5	101.96 (10)
C32—C31—C36	118.29 (19)	C21—P1—C31	102.20 (9)
C32—C31—P1	123.48 (15)	C5—P1—C31	99.98 (9)
C36—C31—P1	118.23 (17)	C8—P2—C41	100.81 (10)
C33—C32—C31	120.8 (2)	C8—P2—C51	99.93 (10)
C33—C32—H32	119.6	C41—P2—C51	103.02 (10)
C6—C1—C2—C3	−0.8 (3)	C41—C42—C43—C44	0.6 (4)
N1—C1—C2—C3	−178.9 (2)	C42—C43—C44—C45	−0.2 (4)
C1—C2—C3—C4	−0.5 (3)	C43—C44—C45—C46	−0.1 (4)
C2—C3—C4—C5	0.5 (3)	C42—C41—C46—C45	0.4 (4)
C3—C4—C5—C6	0.7 (3)	P2—C41—C46—C45	178.5 (2)
C3—C4—C5—P1	179.98 (16)	C44—C45—C46—C41	0.0 (4)
C4—C5—C6—C1	−2.0 (3)	C56—C51—C52—C53	−0.7 (3)
P1—C5—C6—C1	178.60 (16)	P2—C51—C52—C53	−179.29 (19)
C4—C5—C6—O1	177.72 (17)	C51—C52—C53—C54	−0.7 (4)
P1—C5—C6—O1	−1.7 (2)	C52—C53—C54—C55	1.6 (4)
C2—C1—C6—C5	2.1 (3)	C53—C54—C55—C56	−1.0 (4)
N1—C1—C6—C5	−179.71 (19)	C54—C55—C56—C51	−0.4 (4)
C2—C1—C6—O1	−177.62 (18)	C52—C51—C56—C55	1.3 (3)
N1—C1—C6—O1	0.6 (3)	P2—C51—C56—C55	179.79 (18)
O1—C7—C8—C9	178.75 (17)	C2—C1—N1—C12	−177.0 (2)
C12—C7—C8—C9	−0.3 (3)	C6—C1—N1—C12	4.9 (3)
O1—C7—C8—P2	1.3 (2)	C11—C12—N1—C1	174.5 (2)
C12—C7—C8—P2	−177.74 (16)	C7—C12—N1—C1	−5.5 (3)
C7—C8—C9—C10	0.1 (3)	C8—C7—O1—C6	−174.40 (17)
P2—C8—C9—C10	177.27 (16)	C12—C7—O1—C6	4.7 (3)
C8—C9—C10—C11	0.7 (3)	C5—C6—O1—C7	174.95 (17)
C9—C10—C11—C12	−1.3 (3)	C1—C6—O1—C7	−5.3 (3)
C10—C11—C12—C7	1.0 (3)	C26—C21—P1—C5	109.83 (19)
C10—C11—C12—N1	−178.9 (2)	C22—C21—P1—C5	−77.11 (18)
C8—C7—C12—C11	−0.2 (3)	C26—C21—P1—C31	6.7 (2)
O1—C7—C12—C11	−179.27 (18)	C22—C21—P1—C31	179.77 (17)
C8—C7—C12—N1	179.68 (19)	C6—C5—P1—C21	175.90 (15)
O1—C7—C12—N1	0.7 (3)	C4—C5—P1—C21	−3.4 (2)
C26—C21—C22—C23	−1.0 (3)	C6—C5—P1—C31	−79.23 (17)
P1—C21—C22—C23	−174.60 (19)	C4—C5—P1—C31	101.45 (18)
C21—C22—C23—C24	1.9 (4)	C32—C31—P1—C21	73.74 (19)
C22—C23—C24—C25	−1.3 (4)	C36—C31—P1—C21	−106.18 (18)
C23—C24—C25—C26	0.0 (4)	C32—C31—P1—C5	−30.94 (19)
C24—C25—C26—C21	0.8 (4)	C36—C31—P1—C5	149.14 (17)
C22—C21—C26—C25	−0.3 (3)	C7—C8—P2—C41	176.03 (16)
P1—C21—C26—C25	172.73 (18)	C9—C8—P2—C41	−1.1 (2)
C36—C31—C32—C33	0.1 (3)	C7—C8—P2—C51	−78.53 (17)
P1—C31—C32—C33	−179.82 (17)	C9—C8—P2—C51	104.31 (19)
C31—C32—C33—C34	0.2 (3)	C46—C41—P2—C8	87.2 (2)
C32—C33—C34—C35	0.1 (4)	C42—C41—P2—C8	−94.69 (19)
C33—C34—C35—C36	−0.6 (4)	C46—C41—P2—C51	−15.8 (2)
C34—C35—C36—C31	0.9 (4)	C42—C41—P2—C51	162.34 (18)
C32—C31—C36—C35	−0.7 (3)	C52—C51—P2—C8	151.05 (18)
P1—C31—C36—C35	179.27 (18)	C56—C51—P2—C8	−27.4 (2)
C46—C41—C42—C43	−0.7 (4)	C52—C51—P2—C41	−105.31 (19)
P2—C41—C42—C43	−179.0 (2)	C56—C51—P2—C41	76.2 (2)