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Acta Crystallogr Sect E Struct Rep Online. 2008 April 1; 64(Pt 4): o711.
Published online 2008 March 14. doi:  10.1107/S1600536808006648
PMCID: PMC2960967

4,6-Bis(diphenyl­phosphino)phenoxazine (nixantphos)

Abstract

The title compound, C36H27NOP2, has been reported as a ligand on rhodium for the catalysis of hydro­formyl­ation reactions. The key feature of the compound is the intra­molecular 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 bis­ects the mol­ecule. 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 [triangle]); Claver & van Leeuwen (2000 [triangle]); Deprele & Montchamp (2004 [triangle]); van Leeuwen et al. (2002 [triangle]); Osiński et al. (2005 [triangle]); Petrassi et al. (2000 [triangle]); Ricken et al. (2006a [triangle],b [triangle],c [triangle]); Sandee et al. (1999 [triangle], 2001 [triangle]); Tolman (1977 [triangle]); van der Veen et al. (2000 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o711-scheme1.jpg

Experimental

Crystal data

  • C36H27NOP2
  • M r = 551.53
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o711-efi1.jpg
  • 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 [triangle]); cell refinement: SAINT-NT (Bruker, 2005 [triangle]); data reduction: SAINT-NT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 2003 [triangle]) and ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

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

Acknowledgments

We thank Dr Manuel Fernandez for the data collection, and SASOL, THRIP and the University of KwaZulu-Natal for financial support.

supplementary crystallographic information

Comment

The titled compound, (1) (Fig. 1), is a xanthene based diphenylphosphine ligand. The synthesis of the ligand has been reported in literature (van der Veen et al., 2000; Petrassi et al., 2000; Antonio et al., 1989), in addition it is commercially available and has been used extensively in synthesis and as a precursor for the synthesis of substituted bis(diphenylphoshino)phenoxazine ligands (Osiński et al., 2005; Ricken et al., 2006a,b). However, this is the first time that the crystal structure is being reported. This ligand and similar xantphos based ligands have been used on Rh as catalysts for the regioselective hydroformylation of 1-octene to octanal (Claver & van Leeuwen, 2000; van der Veen et al., 2000). Moreover, (1) has been successfully immobilized on silica (Sandee et al., 2001, 1999; van Leeuwen et al., 2002), polystyrene (Deprele & Montchamp, 2004), and dendritic supports (Ricken et al., 2006a).

The title compound (1) was prepared following literature procedures (Antonio et al., 1989; Petrassi et al., 2000) as part of our ongoing investigation of scorpionate-type ligands by the alkylation of the amine. The structural elucidation of this compound allows for the determination of important ligand factors such as the cone angle (Tolman, 1977), and the flexibility range of the natural bite angle (van der Veen et al., 2000). It is also useful for studies of the coordination chemistry and catalytic applications of xantphos-type ligands. For example, the intramolecular P···P distance of 4.255 Å for (1) is similar to values reported for nixantphos-type ligands functionalized at the nitrogen (Osiński, et al., 2005; Ricken et al., 2006a,c) indicating that a functionality at N has little influence on the bite angle of the ligand.

Experimental

The compound was synthesized via a three step procedure adapted from literature (Antonio et al., 1989; Petrassi et al., 2000; van der Veen et al., 2000). Yield: 70% of yellow crystals of (1), m.p. 457–459 K. Spectroscopic analysis: 1H NMR (600 MHz, CDCl3, δ, p.p.m): 5.16 (s, 1H; NH), 5.97 (d, 2H; J(H,H) = 6.4 Hz,), 6.34 (bd, 2H;J(H,H) = 7.3 Hz,), 6.58 (t, 2H J(H,H) = 7.7 Hz), 7.17–7.23 (bs, 20H). 13C NMR (600 MHz, CDCl3, δ, p.p.m): 113.7(CH), 123.7(CH), 125.8(CH), 128.1(CH), 128.2(CH), 128.3(C), 128.3 (C), 131.3(bs,CN), 133.9(CH), 134.0(C), 136.7 (C). 31P NMR (600 MHz, CDCl3, δ, p.p.m): -19.0 MS m/z (%): 552.1633 (M + H) calculated = 552.1648 for C36H27NOP2 Elemental Analysis: C, 78.01; H, 4.95; N, 2.47. Found: C, 77.61; H, 4.91; N,2.41. FTIR: cm-1 = 3408(w), (NH), 1565(s), 1452(s), 1398(s), 1286, CN,1256(m), 1206(m), 1090(m), 766(m), 739(m), (NH), 723(m), 690(s).

Refinement

All H atoms attached to C atoms were fixed geometrically and treated as riding with C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C). H atom attached to nitrogen was freely refined.

Figures

Fig. 1.
Molecular structure of the title complex with the atom labelling scheme. Ellipsoids are drawn at the 50% probability level.

Crystal data

C36H27NOP2Z = 2
Mr = 551.53F000 = 576
Triclinic, P1Dx = 1.334 Mg m3
Hall symbol: -P 1Melting point: 457(2) K
a = 10.4233 (3) ÅMo Kα radiation λ = 0.71073 Å
b = 10.9113 (3) ÅCell parameters from 3152 reflections
c = 12.9940 (4) Åθ = 2.2–25.5º
α = 104.055 (2)ºµ = 0.19 mm1
β = 102.555 (2)ºT = 173 (2) K
γ = 97.459 (2)ºTriangular, yellow
V = 1373.04 (7) Å30.40 × 0.18 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer3646 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.055
Monochromator: graphiteθmax = 26.0º
T = 173(2) Kθmin = 1.7º
[var phi] and ω scansh = −10→12
Absorption correction: nonek = −13→13
15968 measured reflectionsl = −16→16
5396 independent reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H 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 reflectionsΔρmax = 0.38 e Å3
365 parametersΔρmin = −0.29 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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 (Å2)

xyzUiso*/Ueq
C10.0632 (2)0.3597 (2)0.56267 (18)0.0339 (5)
C20.1275 (2)0.4755 (2)0.63818 (19)0.0391 (6)
H20.11110.49680.70890.047*
C30.2159 (2)0.5608 (2)0.61113 (19)0.0401 (6)
H30.25930.64070.66330.048*
C40.2414 (2)0.5308 (2)0.50922 (19)0.0347 (5)
H40.30290.59000.49210.042*
C50.1780 (2)0.41454 (19)0.43100 (17)0.0288 (5)
C60.0885 (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)
H9−0.2323−0.16120.29540.042*
C10−0.2214 (2)−0.0594 (2)0.4502 (2)0.0393 (6)
H10−0.2765−0.12500.46600.047*
C11−0.1690 (2)0.0565 (2)0.5287 (2)0.0395 (6)
H11−0.18970.07090.59780.047*
C12−0.0863 (2)0.1525 (2)0.50796 (19)0.0341 (5)
C210.3147 (2)0.50031 (19)0.28652 (17)0.0283 (5)
C220.2595 (2)0.6054 (2)0.2703 (2)0.0390 (6)
H220.16800.60490.26920.047*
C230.3343 (2)0.7100 (2)0.2558 (2)0.0415 (6)
H230.29500.78180.24700.050*
C240.4657 (2)0.7113 (2)0.25396 (19)0.0400 (6)
H240.51710.78290.24240.048*
C250.5217 (2)0.6081 (2)0.2690 (2)0.0423 (6)
H250.61260.60840.26790.051*
C260.4479 (2)0.5037 (2)0.28585 (19)0.0351 (5)
H260.48880.43350.29710.042*
C310.3144 (2)0.24846 (18)0.31367 (17)0.0280 (5)
C320.4063 (2)0.26320 (19)0.41242 (18)0.0329 (5)
H320.41260.33450.47340.040*
C330.4891 (2)0.1757 (2)0.4233 (2)0.0401 (6)
H330.55160.18670.49160.048*
C340.4812 (2)0.0733 (2)0.3362 (2)0.0450 (6)
H340.53830.01310.34400.054*
C350.3916 (3)0.0568 (2)0.2377 (2)0.0479 (7)
H350.3872−0.01420.17700.057*
C360.3075 (2)0.1434 (2)0.2262 (2)0.0385 (6)
H360.24450.13090.15790.046*
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)
H420.0234−0.23670.17380.055*
C43−0.1170 (3)−0.3900 (2)0.0759 (2)0.0570 (8)
H43−0.0627−0.45250.08310.068*
C44−0.2466 (3)−0.4270 (2)0.0113 (2)0.0568 (8)
H44−0.2820−0.5152−0.02630.068*
C45−0.3243 (3)−0.3372 (2)0.0015 (2)0.0567 (7)
H45−0.4137−0.3629−0.04320.068*
C46−0.2737 (2)−0.2084 (2)0.0563 (2)0.0465 (6)
H46−0.3288−0.14670.04880.056*
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)
H52−0.04390.14410.04550.055*
C53−0.2058 (3)0.2257 (3)0.0107 (2)0.0557 (7)
H53−0.17460.2680−0.03750.067*
C54−0.3276 (3)0.2372 (2)0.0307 (2)0.0525 (7)
H54−0.38190.2858−0.00520.063*
C55−0.3718 (3)0.1792 (2)0.1020 (2)0.0453 (6)
H55−0.45590.18870.11660.054*
C56−0.2939 (2)0.1070 (2)0.15255 (19)0.0386 (6)
H56−0.32490.06740.20250.046*
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)*
O10.02287 (15)0.21948 (13)0.37894 (12)0.0384 (4)
P10.20112 (5)0.36083 (5)0.29234 (5)0.03016 (16)
P2−0.06220 (6)−0.00273 (5)0.19630 (5)0.03407 (16)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0333 (13)0.0373 (13)0.0362 (14)0.0149 (10)0.0118 (11)0.0126 (10)
C20.0404 (14)0.0482 (14)0.0305 (14)0.0187 (11)0.0101 (11)0.0078 (11)
C30.0358 (13)0.0364 (13)0.0387 (15)0.0118 (11)0.0014 (11)−0.0018 (11)
C40.0260 (12)0.0330 (12)0.0406 (14)0.0056 (9)0.0035 (10)0.0066 (10)
C50.0252 (11)0.0298 (11)0.0323 (13)0.0114 (9)0.0042 (10)0.0100 (9)
C60.0275 (11)0.0285 (11)0.0325 (13)0.0092 (9)0.0058 (10)0.0057 (9)
C70.0253 (11)0.0354 (12)0.0376 (14)0.0088 (9)0.0108 (10)0.0177 (10)
C80.0231 (11)0.0348 (12)0.0363 (13)0.0068 (9)0.0041 (10)0.0142 (10)
C90.0246 (12)0.0394 (13)0.0404 (14)0.0024 (9)0.0038 (10)0.0161 (10)
C100.0285 (12)0.0452 (14)0.0503 (16)0.0036 (10)0.0099 (11)0.0267 (12)
C110.0325 (13)0.0562 (16)0.0419 (15)0.0157 (11)0.0179 (11)0.0251 (12)
C120.0312 (12)0.0396 (13)0.0378 (14)0.0139 (10)0.0113 (11)0.0167 (11)
C210.0295 (12)0.0278 (11)0.0261 (12)0.0030 (9)0.0050 (9)0.0077 (9)
C220.0348 (13)0.0386 (13)0.0498 (16)0.0118 (10)0.0137 (11)0.0188 (11)
C230.0503 (15)0.0314 (13)0.0462 (15)0.0139 (11)0.0113 (12)0.0151 (11)
C240.0403 (14)0.0307 (12)0.0446 (15)−0.0036 (10)0.0051 (11)0.0130 (11)
C250.0273 (12)0.0406 (14)0.0569 (17)0.0009 (10)0.0057 (11)0.0174 (12)
C260.0293 (12)0.0290 (12)0.0462 (15)0.0044 (9)0.0051 (11)0.0141 (10)
C310.0272 (11)0.0237 (11)0.0336 (13)0.0002 (8)0.0110 (10)0.0085 (9)
C320.0359 (13)0.0277 (11)0.0355 (14)0.0068 (9)0.0093 (11)0.0091 (9)
C330.0360 (13)0.0389 (13)0.0486 (16)0.0067 (10)0.0092 (12)0.0201 (12)
C340.0409 (14)0.0321 (13)0.0689 (19)0.0132 (11)0.0205 (14)0.0182 (12)
C350.0511 (16)0.0307 (13)0.0604 (19)0.0103 (11)0.0233 (14)0.0007 (12)
C360.0361 (13)0.0352 (13)0.0388 (14)0.0006 (10)0.0091 (11)0.0040 (10)
C410.0373 (13)0.0336 (12)0.0352 (14)0.0092 (10)0.0109 (11)0.0112 (10)
C420.0488 (15)0.0455 (15)0.0458 (16)0.0169 (12)0.0128 (13)0.0140 (12)
C430.080 (2)0.0410 (16)0.0562 (19)0.0263 (14)0.0215 (16)0.0142 (13)
C440.088 (2)0.0299 (14)0.0496 (18)0.0051 (14)0.0203 (16)0.0068 (12)
C450.0572 (17)0.0420 (15)0.0559 (18)0.0010 (13)0.0041 (14)0.0000 (13)
C460.0469 (15)0.0356 (14)0.0483 (16)0.0065 (11)0.0024 (13)0.0055 (11)
C510.0355 (13)0.0271 (11)0.0303 (13)−0.0020 (9)0.0055 (10)0.0062 (9)
C520.0444 (15)0.0511 (15)0.0436 (16)0.0021 (12)0.0138 (12)0.0174 (12)
C530.0628 (19)0.0604 (18)0.0529 (18)0.0077 (14)0.0145 (15)0.0351 (14)
C540.0589 (18)0.0488 (16)0.0542 (18)0.0128 (13)0.0074 (14)0.0275 (13)
C550.0464 (15)0.0447 (14)0.0494 (17)0.0136 (12)0.0121 (13)0.0192 (12)
C560.0408 (14)0.0406 (13)0.0399 (14)0.0094 (11)0.0126 (11)0.0189 (11)
N10.0534 (13)0.0434 (12)0.0354 (13)0.0145 (10)0.0226 (11)0.0132 (10)
O10.0460 (10)0.0326 (8)0.0359 (9)−0.0022 (7)0.0180 (8)0.0069 (7)
P10.0261 (3)0.0298 (3)0.0338 (3)0.0032 (2)0.0063 (3)0.0100 (2)
P20.0288 (3)0.0356 (3)0.0365 (4)0.0035 (2)0.0078 (3)0.0096 (3)

Geometric parameters (Å, °)

C1—C21.379 (3)C31—C361.386 (3)
C1—C61.386 (3)C31—P11.836 (2)
C1—N11.398 (3)C32—C331.379 (3)
C2—C31.384 (3)C32—H320.9500
C2—H20.9500C33—C341.363 (3)
C3—C41.377 (3)C33—H330.9500
C3—H30.9500C34—C351.366 (3)
C4—C51.394 (3)C34—H340.9500
C4—H40.9500C35—C361.383 (3)
C5—C61.381 (3)C35—H350.9500
C5—P11.833 (2)C36—H360.9500
C6—O11.392 (2)C41—C461.381 (3)
C7—C81.382 (3)C41—C421.387 (3)
C7—O11.386 (2)C41—P21.826 (2)
C7—C121.387 (3)C42—C431.377 (3)
C8—C91.400 (3)C42—H420.9500
C8—P21.825 (2)C43—C441.376 (4)
C9—C101.372 (3)C43—H430.9500
C9—H90.9500C44—C451.362 (3)
C10—C111.374 (3)C44—H440.9500
C10—H100.9500C45—C461.384 (3)
C11—C121.384 (3)C45—H450.9500
C11—H110.9500C46—H460.9500
C12—N11.403 (3)C51—C521.384 (3)
C21—C261.385 (3)C51—C561.388 (3)
C21—C221.388 (3)C51—P21.828 (2)
C21—P11.831 (2)C52—C531.380 (3)
C22—C231.372 (3)C52—H520.9500
C22—H220.9500C53—C541.365 (3)
C23—C241.374 (3)C53—H530.9500
C23—H230.9500C54—C551.366 (3)
C24—C251.369 (3)C54—H540.9500
C24—H240.9500C55—C561.377 (3)
C25—C261.380 (3)C55—H550.9500
C25—H250.9500C56—H560.9500
C26—H260.9500N1—H10.86 (3)
C31—C321.384 (3)
C2—C1—C6118.3 (2)C31—C32—H32119.6
C2—C1—N1122.0 (2)C34—C33—C32120.0 (2)
C6—C1—N1119.7 (2)C34—C33—H33120.0
C1—C2—C3120.1 (2)C32—C33—H33120.0
C1—C2—H2119.9C33—C34—C35120.3 (2)
C3—C2—H2119.9C33—C34—H34119.8
C4—C3—C2120.6 (2)C35—C34—H34119.8
C4—C3—H3119.7C34—C35—C36120.1 (2)
C2—C3—H3119.7C34—C35—H35120.0
C3—C4—C5120.7 (2)C36—C35—H35120.0
C3—C4—H4119.7C35—C36—C31120.5 (2)
C5—C4—H4119.7C35—C36—H36119.8
C6—C5—C4117.2 (2)C31—C36—H36119.8
C6—C5—P1116.86 (15)C46—C41—C42117.8 (2)
C4—C5—P1125.91 (18)C46—C41—P2125.83 (17)
C5—C6—C1123.1 (2)C42—C41—P2116.31 (18)
C5—C6—O1116.04 (19)C43—C42—C41121.4 (2)
C1—C6—O1120.89 (19)C43—C42—H42119.3
C8—C7—O1115.78 (19)C41—C42—H42119.3
C8—C7—C12122.8 (2)C44—C43—C42119.7 (2)
O1—C7—C12121.38 (19)C44—C43—H43120.2
C7—C8—C9117.3 (2)C42—C43—H43120.2
C7—C8—P2116.80 (16)C45—C44—C43120.0 (2)
C9—C8—P2125.87 (17)C45—C44—H44120.0
C10—C9—C8120.8 (2)C43—C44—H44120.0
C10—C9—H9119.6C44—C45—C46120.4 (3)
C8—C9—H9119.6C44—C45—H45119.8
C9—C10—C11120.5 (2)C46—C45—H45119.8
C9—C10—H10119.7C41—C46—C45120.8 (2)
C11—C10—H10119.7C41—C46—H46119.6
C10—C11—C12120.6 (2)C45—C46—H46119.6
C10—C11—H11119.7C52—C51—C56117.8 (2)
C12—C11—H11119.7C52—C51—P2118.61 (18)
C11—C12—C7118.0 (2)C56—C51—P2123.61 (18)
C11—C12—N1122.9 (2)C53—C52—C51120.9 (2)
C7—C12—N1119.1 (2)C53—C52—H52119.6
C26—C21—C22117.61 (19)C51—C52—H52119.6
C26—C21—P1124.86 (16)C54—C53—C52120.0 (2)
C22—C21—P1117.19 (16)C54—C53—H53120.0
C23—C22—C21121.4 (2)C52—C53—H53120.0
C23—C22—H22119.3C53—C54—C55120.4 (2)
C21—C22—H22119.3C53—C54—H54119.8
C22—C23—C24120.3 (2)C55—C54—H54119.8
C22—C23—H23119.8C54—C55—C56119.7 (2)
C24—C23—H23119.8C54—C55—H55120.1
C25—C24—C23119.1 (2)C56—C55—H55120.1
C25—C24—H24120.4C55—C56—C51121.2 (2)
C23—C24—H24120.4C55—C56—H56119.4
C24—C25—C26120.8 (2)C51—C56—H56119.4
C24—C25—H25119.6C1—N1—C12119.7 (2)
C26—C25—H25119.6C1—N1—H1115 (2)
C25—C26—C21120.7 (2)C12—N1—H1119.0 (19)
C25—C26—H26119.7C7—O1—C6118.82 (17)
C21—C26—H26119.7C21—P1—C5101.96 (10)
C32—C31—C36118.29 (19)C21—P1—C31102.20 (9)
C32—C31—P1123.48 (15)C5—P1—C3199.98 (9)
C36—C31—P1118.23 (17)C8—P2—C41100.81 (10)
C33—C32—C31120.8 (2)C8—P2—C5199.93 (10)
C33—C32—H32119.6C41—P2—C51103.02 (10)
C6—C1—C2—C3−0.8 (3)C41—C42—C43—C440.6 (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—C50.5 (3)C42—C41—C46—C450.4 (4)
C3—C4—C5—C60.7 (3)P2—C41—C46—C45178.5 (2)
C3—C4—C5—P1179.98 (16)C44—C45—C46—C410.0 (4)
C4—C5—C6—C1−2.0 (3)C56—C51—C52—C53−0.7 (3)
P1—C5—C6—C1178.60 (16)P2—C51—C52—C53−179.29 (19)
C4—C5—C6—O1177.72 (17)C51—C52—C53—C54−0.7 (4)
P1—C5—C6—O1−1.7 (2)C52—C53—C54—C551.6 (4)
C2—C1—C6—C52.1 (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—C551.3 (3)
N1—C1—C6—O10.6 (3)P2—C51—C56—C55179.79 (18)
O1—C7—C8—C9178.75 (17)C2—C1—N1—C12−177.0 (2)
C12—C7—C8—C9−0.3 (3)C6—C1—N1—C124.9 (3)
O1—C7—C8—P21.3 (2)C11—C12—N1—C1174.5 (2)
C12—C7—C8—P2−177.74 (16)C7—C12—N1—C1−5.5 (3)
C7—C8—C9—C100.1 (3)C8—C7—O1—C6−174.40 (17)
P2—C8—C9—C10177.27 (16)C12—C7—O1—C64.7 (3)
C8—C9—C10—C110.7 (3)C5—C6—O1—C7174.95 (17)
C9—C10—C11—C12−1.3 (3)C1—C6—O1—C7−5.3 (3)
C10—C11—C12—C71.0 (3)C26—C21—P1—C5109.83 (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—C316.7 (2)
O1—C7—C12—C11−179.27 (18)C22—C21—P1—C31179.77 (17)
C8—C7—C12—N1179.68 (19)C6—C5—P1—C21175.90 (15)
O1—C7—C12—N10.7 (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—C31101.45 (18)
C21—C22—C23—C241.9 (4)C32—C31—P1—C2173.74 (19)
C22—C23—C24—C25−1.3 (4)C36—C31—P1—C21−106.18 (18)
C23—C24—C25—C260.0 (4)C32—C31—P1—C5−30.94 (19)
C24—C25—C26—C210.8 (4)C36—C31—P1—C5149.14 (17)
C22—C21—C26—C25−0.3 (3)C7—C8—P2—C41176.03 (16)
P1—C21—C26—C25172.73 (18)C9—C8—P2—C41−1.1 (2)
C36—C31—C32—C330.1 (3)C7—C8—P2—C51−78.53 (17)
P1—C31—C32—C33−179.82 (17)C9—C8—P2—C51104.31 (19)
C31—C32—C33—C340.2 (3)C46—C41—P2—C887.2 (2)
C32—C33—C34—C350.1 (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—C310.9 (4)C42—C41—P2—C51162.34 (18)
C32—C31—C36—C35−0.7 (3)C52—C51—P2—C8151.05 (18)
P1—C31—C36—C35179.27 (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—C4176.2 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2322).

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