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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1449.
Published online 2008 July 9. doi:  10.1107/S1600536808020412
PMCID: PMC2962250

P,P-Diphenyl-N-(1,1,2,2-tetra­phenyl-1λ5-diphosphanyl­idene)phosphinous amide

Abstract

The title compound, C36H30NP3, a structural isomer of tris­(diphenyl­phosphino)amine, was unexpectedly isolated as the sole phospho­rus-containing product from the reaction of Mg[N(PPh2)2]2(THF)2 (THF is tetra­hydro­furan) with CO2. Its identity was confirmed by 31P NMR spectroscopy and single-crystal X-ray diffraction. The geometry at the two P(III) atoms is trigonal pyramidal, while the P(V) atom adopts a distorted tetrahedral geometry.

Related literature

For the original synthesis and spectroscopic characterization of the title compound, see: Nöth & Meinel (1967 [triangle]); Meinel & Nöth (1970 [triangle]). For the crystallographic characterization of the structural isomer N[P(C6H5)2]3, see: Ellermann et al. (1987 [triangle]). For related literature, see: Bruno et al. (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1449-scheme1.jpg

Experimental

Crystal data

  • C36H30NP3
  • M r = 569.52
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1449-efi1.jpg
  • a = 9.3026 (13) Å
  • b = 10.8167 (15) Å
  • c = 29.750 (4) Å
  • β = 98.589 (6)°
  • V = 2960.0 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.23 mm−1
  • T = 228 (2) K
  • 0.57 × 0.51 × 0.18 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.88, T max = 0.96
  • 76797 measured reflections
  • 11496 independent reflections
  • 9167 reflections with I > 2σ(I)
  • R int = 0.029

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.118
  • S = 1.05
  • 11496 reflections
  • 481 parameters
  • All H-atom parameters refined
  • Δρmax = 0.41 e Å−3
  • Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2003 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: DIAMOND (Brandenburg, 1999 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808020412/at2581sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020412/at2581Isup2.hkl

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

Acknowledgments

The authors thank Eileen Duesler (UNM) for the X-ray data collection. Funding was provided by the Natural Sciences and Engineering Research Council of Canada (NSERC PDF to DAD), the National Science Foundation (grant Nos. CHE-0213165 and CHE-0443580) and the Sandia LDRD Program (grant Nos. 105932 and 113486). Sandia is a multiprogram laboratory operated by Sandia Corporation, a Lockheed Martin Company, for the United States Department of Energy under contract No. DE-AC04-94AL85000.

supplementary crystallographic information

Comment

The molecular stucture of the title compound, (I), is shown in Fig. 1. It was originally prepared by Nöth and Meinel [Nöth & Meinel (1967); and Meinel & Nöth (1970)] but its crystal structure was not determined at that time. We report herein the isolation of (I) as an unexpected product of the reaction of carbon dioxide with Mg[N(PPh2)2]2(THF)2. This compound was characterized by 31P NMR spectroscopy and single-crystal X-ray diffraction. The P═N double bond measures 1.5690 (10) Å, very close to the average value of similar bonds in a Mogul (Bruno et al., 2004) search of the Cambridge structural database (mean P=N 1.573 Å). The P—N single bond of 1.6755 (11) Å is significantly shorter than those in the structural isomer N(PPh2)3 (Ellermann, et al. 1987) (mean P—N = 1.740 Å), which is not surprising when the different hybridization of nitrogen (sp2versus sp3) is considered. It is also, however, shorter than the average P—N(sp2) bond length of 1.706 Å. The geometry at each of the two P(III) atoms is trigonal pyramidal, due to the stereochemically active lone pair on each of these atoms. The P(V) atom adopts distorted tetrahedral geometry.

Experimental

Under an inert argon atmosphere, Mg[N(PPh2)2]2(THF)2 (0.67 g, 0.72 mmol) was dissolved in 40 ml anhydrous THF. The solution was exposed to 2 eq. of carbon dioxide at 10 psig. After 16 h, the solution was purged with argon. Colourless crystals of the title compound crystallized from the solution over the course of two weeks. 31P{1H} NMR (101.255 MHz, THF) δ 41.5 (d, 2JPP = 97 Hz, Ph2P-N), 17.8 (d of d, 2JPP = 97 Hz, 1JPP = 249 Hz, N=PPh2), -9.4 (d, 1JPP = 249 Hz, P-PPh2) p.p.m..

Refinement

H atoms were located from a difference Fourier map and refined isotropically.

Figures

Fig. 1.
View of the title compound showing full numbering scheme. Ellipsoids are shown at 50% probability and hydrogen atoms have been removed for clarity.

Crystal data

C36H30NP3F000 = 1192
Mr = 569.52Dx = 1.278 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9384 reflections
a = 9.3026 (13) Åθ = 2.3–33.2º
b = 10.8167 (15) ŵ = 0.23 mm1
c = 29.750 (4) ÅT = 228 (2) K
β = 98.589 (6)ºSquare, colourless
V = 2960.0 (7) Å30.58 × 0.51 × 0.18 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer11496 independent reflections
Radiation source: fine-focus sealed tube9167 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.029
T = 228(2) Kθmax = 33.5º
[var phi] and ω scansθmin = 2.4º
Absorption correction: multi-scan(SADABS; Bruker, 2001)h = −14→14
Tmin = 0.88, Tmax = 0.96k = −16→16
76797 measured reflectionsl = −45→45

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042All H-atom parameters refined
wR(F2) = 0.118  w = 1/[σ2(Fo2) + (0.0543P)2 + 1.05P] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
11496 reflectionsΔρmax = 0.41 e Å3
481 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
N10.89827 (12)0.55872 (10)0.13502 (4)0.0285 (2)
P10.83490 (3)0.52397 (3)0.080793 (10)0.02539 (7)
P20.98888 (3)0.67406 (3)0.154676 (10)0.02169 (6)
P30.88674 (3)0.85071 (3)0.171889 (11)0.02562 (7)
C10.92572 (12)0.37613 (11)0.07254 (4)0.0265 (2)
C20.94010 (18)0.34039 (15)0.02865 (5)0.0398 (3)
H20.915 (2)0.396 (2)0.0046 (7)0.052 (5)*
C30.9911 (2)0.22253 (18)0.02040 (7)0.0533 (4)
H30.998 (3)0.200 (2)−0.0104 (8)0.067 (7)*
C41.03047 (18)0.14200 (15)0.05566 (7)0.0494 (4)
H41.062 (2)0.061 (2)0.0493 (7)0.064 (6)*
C51.02013 (17)0.17767 (14)0.09955 (7)0.0433 (3)
H51.045 (2)0.120 (2)0.1238 (7)0.059 (6)*
C60.96912 (15)0.29430 (13)0.10817 (5)0.0344 (3)
H60.958 (2)0.3171 (19)0.1389 (7)0.053 (6)*
C110.65810 (12)0.45178 (11)0.08595 (4)0.0270 (2)
C120.60725 (15)0.43744 (13)0.12725 (5)0.0339 (3)
H120.661 (2)0.4670 (17)0.1541 (6)0.039 (5)*
C130.47230 (17)0.38278 (15)0.12874 (6)0.0444 (3)
H130.437 (2)0.380 (2)0.1578 (7)0.055 (6)*
C140.38678 (16)0.34312 (14)0.08938 (7)0.0468 (4)
H140.297 (2)0.306 (2)0.0912 (7)0.063 (6)*
C150.43625 (16)0.35656 (14)0.04816 (7)0.0439 (4)
H150.378 (2)0.332 (2)0.0199 (7)0.062 (6)*
C160.57122 (15)0.41024 (13)0.04646 (5)0.0349 (3)
H160.6072 (19)0.4179 (17)0.0181 (6)0.037 (4)*
C211.13511 (12)0.72160 (10)0.12433 (4)0.02325 (19)
C221.20846 (14)0.63055 (12)0.10377 (5)0.0318 (2)
H221.180 (2)0.5479 (18)0.1056 (6)0.045 (5)*
C231.32338 (15)0.66224 (14)0.08106 (5)0.0371 (3)
H231.372 (2)0.597 (2)0.0673 (7)0.057 (6)*
C241.36496 (15)0.78400 (14)0.07826 (5)0.0358 (3)
H241.448 (2)0.8079 (19)0.0628 (6)0.049 (5)*
C251.29177 (17)0.87515 (14)0.09808 (6)0.0420 (3)
H251.318 (2)0.957 (2)0.0961 (7)0.061 (6)*
C261.17755 (16)0.84426 (12)0.12116 (6)0.0371 (3)
H261.132 (2)0.909 (2)0.1355 (7)0.055 (6)*
C311.06971 (12)0.63888 (11)0.21231 (4)0.0256 (2)
C321.16599 (14)0.72246 (13)0.23711 (5)0.0326 (2)
H321.197 (2)0.7950 (18)0.2228 (6)0.042 (5)*
C331.21154 (17)0.70324 (17)0.28318 (5)0.0419 (3)
H331.277 (2)0.7602 (18)0.2992 (6)0.045 (5)*
C341.16275 (19)0.60144 (19)0.30440 (5)0.0488 (4)
H341.191 (2)0.587 (2)0.3358 (7)0.056 (6)*
C351.0706 (2)0.51676 (18)0.27995 (6)0.0491 (4)
H351.041 (2)0.449 (2)0.2946 (7)0.061 (6)*
C361.02326 (16)0.53572 (13)0.23390 (5)0.0362 (3)
H360.953 (2)0.4794 (18)0.2163 (6)0.047 (5)*
C410.77800 (13)0.90632 (11)0.11987 (4)0.0268 (2)
C420.78720 (15)0.86532 (13)0.07605 (5)0.0334 (3)
H420.842 (2)0.7942 (18)0.0716 (6)0.041 (5)*
C430.71842 (18)0.93088 (16)0.03862 (5)0.0420 (3)
H430.727 (2)0.9039 (19)0.0095 (7)0.052 (5)*
C440.64070 (18)1.03665 (16)0.04451 (6)0.0470 (4)
H440.597 (2)1.082 (2)0.0194 (7)0.058 (6)*
C450.6267 (2)1.07566 (16)0.08773 (7)0.0506 (4)
H450.578 (3)1.150 (2)0.0926 (8)0.070 (7)*
C460.69448 (17)1.01113 (14)0.12517 (6)0.0406 (3)
H460.684 (3)1.038 (2)0.1553 (8)0.069 (7)*
C510.75546 (14)0.78245 (12)0.20420 (4)0.0296 (2)
C520.78649 (17)0.79087 (16)0.25158 (5)0.0407 (3)
H520.878 (3)0.839 (2)0.2671 (8)0.067 (7)*
C530.6955 (2)0.73483 (19)0.27841 (6)0.0523 (4)
H530.719 (3)0.744 (2)0.3110 (8)0.073 (7)*
C540.5732 (2)0.67193 (19)0.25838 (7)0.0581 (5)
H540.512 (3)0.633 (2)0.2772 (8)0.071 (7)*
C550.5397 (2)0.66580 (18)0.21142 (7)0.0523 (4)
H550.460 (2)0.623 (2)0.1988 (7)0.058 (6)*
C560.63044 (15)0.72019 (14)0.18414 (5)0.0375 (3)
H560.608 (2)0.7168 (18)0.1505 (6)0.044 (5)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0314 (5)0.0258 (4)0.0285 (5)−0.0062 (4)0.0052 (4)−0.0046 (4)
P10.02921 (14)0.02131 (13)0.02575 (14)−0.00134 (10)0.00446 (11)0.00031 (10)
P20.02190 (12)0.01984 (12)0.02357 (13)0.00031 (9)0.00413 (9)−0.00128 (9)
P30.02697 (13)0.02346 (13)0.02645 (14)0.00363 (10)0.00405 (11)−0.00289 (10)
C10.0255 (5)0.0250 (5)0.0293 (5)−0.0026 (4)0.0054 (4)−0.0024 (4)
C20.0473 (8)0.0408 (7)0.0325 (7)0.0040 (6)0.0102 (6)−0.0065 (6)
C30.0592 (10)0.0503 (10)0.0526 (10)0.0056 (8)0.0156 (8)−0.0225 (8)
C40.0397 (7)0.0323 (7)0.0766 (12)0.0038 (6)0.0104 (8)−0.0161 (7)
C50.0372 (7)0.0297 (6)0.0628 (10)0.0048 (5)0.0063 (7)0.0041 (6)
C60.0359 (6)0.0307 (6)0.0374 (7)0.0035 (5)0.0083 (5)0.0025 (5)
C110.0249 (5)0.0220 (5)0.0331 (6)0.0018 (4)0.0009 (4)−0.0004 (4)
C120.0308 (6)0.0335 (6)0.0378 (7)−0.0013 (5)0.0066 (5)0.0010 (5)
C130.0349 (7)0.0404 (8)0.0605 (10)−0.0025 (6)0.0159 (7)0.0065 (7)
C140.0275 (6)0.0296 (6)0.0824 (13)−0.0023 (5)0.0047 (7)0.0017 (7)
C150.0327 (6)0.0313 (7)0.0621 (10)0.0017 (5)−0.0115 (6)−0.0075 (6)
C160.0333 (6)0.0302 (6)0.0383 (7)0.0035 (5)−0.0038 (5)−0.0041 (5)
C210.0229 (4)0.0222 (5)0.0249 (5)0.0011 (4)0.0042 (4)−0.0002 (4)
C220.0330 (6)0.0257 (5)0.0389 (7)0.0029 (4)0.0133 (5)−0.0014 (5)
C230.0362 (6)0.0369 (7)0.0418 (7)0.0059 (5)0.0179 (6)−0.0011 (5)
C240.0294 (6)0.0439 (7)0.0362 (7)0.0003 (5)0.0112 (5)0.0068 (5)
C250.0428 (7)0.0304 (6)0.0570 (9)−0.0060 (6)0.0216 (7)0.0032 (6)
C260.0395 (6)0.0231 (5)0.0533 (8)−0.0019 (5)0.0214 (6)−0.0032 (5)
C310.0246 (5)0.0256 (5)0.0265 (5)0.0029 (4)0.0035 (4)0.0013 (4)
C320.0288 (5)0.0358 (6)0.0319 (6)−0.0015 (5)0.0006 (5)−0.0008 (5)
C330.0358 (7)0.0542 (9)0.0329 (7)0.0022 (6)−0.0042 (5)−0.0036 (6)
C340.0501 (9)0.0644 (11)0.0297 (7)0.0090 (8)−0.0009 (6)0.0087 (7)
C350.0574 (9)0.0501 (9)0.0395 (8)0.0004 (8)0.0065 (7)0.0178 (7)
C360.0414 (7)0.0321 (6)0.0347 (7)−0.0024 (5)0.0043 (5)0.0063 (5)
C410.0270 (5)0.0227 (5)0.0306 (5)0.0023 (4)0.0044 (4)0.0014 (4)
C420.0363 (6)0.0321 (6)0.0314 (6)0.0050 (5)0.0039 (5)0.0009 (5)
C430.0453 (8)0.0467 (8)0.0322 (7)−0.0005 (6)−0.0002 (6)0.0070 (6)
C440.0443 (8)0.0412 (8)0.0506 (9)0.0016 (6)−0.0088 (7)0.0160 (7)
C450.0508 (9)0.0344 (7)0.0634 (11)0.0167 (7)−0.0021 (8)0.0064 (7)
C460.0440 (7)0.0319 (7)0.0451 (8)0.0143 (6)0.0045 (6)−0.0007 (6)
C510.0309 (5)0.0318 (6)0.0275 (5)0.0088 (4)0.0089 (4)0.0001 (4)
C520.0431 (7)0.0515 (9)0.0290 (6)0.0117 (6)0.0105 (6)0.0003 (6)
C530.0608 (10)0.0637 (11)0.0370 (8)0.0184 (9)0.0226 (7)0.0118 (7)
C540.0637 (11)0.0529 (10)0.0678 (12)0.0132 (8)0.0425 (10)0.0185 (9)
C550.0424 (8)0.0508 (9)0.0690 (12)−0.0034 (7)0.0252 (8)0.0009 (8)
C560.0329 (6)0.0409 (7)0.0408 (7)0.0017 (5)0.0118 (5)−0.0006 (6)

Geometric parameters (Å, °)

N1—P21.5690 (10)C24—H240.99 (2)
N1—P11.6755 (11)C25—C261.3892 (19)
P1—C11.8421 (12)C25—H250.92 (2)
P1—C111.8476 (12)C26—H260.95 (2)
P2—C311.8071 (12)C31—C361.3882 (18)
P2—C211.8156 (11)C31—C321.4023 (18)
P2—P32.2273 (5)C32—C331.388 (2)
P3—C511.8196 (13)C32—H320.958 (19)
P3—C411.8200 (13)C33—C341.379 (3)
C1—C21.3873 (18)C33—H330.94 (2)
C1—C61.3935 (19)C34—C351.385 (3)
C2—C31.395 (2)C34—H340.95 (2)
C2—H20.94 (2)C35—C361.390 (2)
C3—C41.371 (3)C35—H350.92 (2)
C3—H30.96 (2)C36—H360.99 (2)
C4—C51.379 (3)C41—C421.3917 (18)
C4—H40.95 (2)C41—C461.3965 (18)
C5—C61.385 (2)C42—C431.393 (2)
C5—H50.96 (2)C42—H420.943 (19)
C6—H60.97 (2)C43—C441.378 (2)
C11—C121.3895 (18)C43—H430.93 (2)
C11—C161.3972 (18)C44—C451.378 (3)
C12—C131.394 (2)C44—H440.93 (2)
C12—H120.933 (18)C45—C461.384 (2)
C13—C141.382 (3)C45—H450.95 (2)
C13—H130.97 (2)C46—H460.96 (2)
C14—C151.380 (3)C51—C561.398 (2)
C14—H140.93 (2)C51—C521.3991 (19)
C15—C161.391 (2)C52—C531.386 (2)
C15—H150.97 (2)C52—H521.04 (2)
C16—H160.957 (17)C53—C541.382 (3)
C21—C221.3909 (16)C53—H530.97 (2)
C21—C261.3915 (17)C54—C551.387 (3)
C22—C231.3901 (18)C54—H540.96 (2)
C22—H220.94 (2)C55—C561.386 (2)
C23—C241.379 (2)C55—H550.91 (2)
C23—H230.97 (2)C56—H560.990 (19)
C24—C251.379 (2)
P2—N1—P1129.01 (7)C24—C25—C26120.13 (13)
N1—P1—C1102.74 (6)C24—C25—H25120.2 (14)
N1—P1—C11101.80 (6)C26—C25—H25119.7 (14)
C1—P1—C1194.35 (5)C25—C26—C21120.58 (12)
N1—P2—C31108.08 (6)C25—C26—H26118.3 (13)
N1—P2—C21116.14 (5)C21—C26—H26121.1 (13)
C31—P2—C21107.15 (5)C36—C31—C32119.56 (12)
N1—P2—P3122.96 (4)C36—C31—P2119.62 (10)
C31—P2—P395.39 (4)C32—C31—P2120.40 (9)
C21—P2—P3104.38 (4)C33—C32—C31119.97 (13)
C51—P3—C41104.57 (6)C33—C32—H32119.6 (11)
C51—P3—P296.68 (4)C31—C32—H32120.4 (11)
C41—P3—P2106.86 (4)C34—C33—C32119.90 (15)
C2—C1—C6118.77 (13)C34—C33—H33121.4 (12)
C2—C1—P1118.55 (10)C32—C33—H33118.7 (12)
C6—C1—P1122.45 (10)C33—C34—C35120.53 (15)
C1—C2—C3120.23 (16)C33—C34—H34121.2 (13)
C1—C2—H2119.5 (13)C35—C34—H34118.3 (13)
C3—C2—H2120.2 (13)C34—C35—C36120.01 (15)
C4—C3—C2120.34 (16)C34—C35—H35119.2 (14)
C4—C3—H3121.6 (14)C36—C35—H35120.8 (14)
C2—C3—H3118.0 (15)C31—C36—C35120.00 (14)
C3—C4—C5119.92 (15)C31—C36—H36118.7 (11)
C3—C4—H4119.2 (13)C35—C36—H36121.3 (11)
C5—C4—H4120.9 (13)C42—C41—C46118.52 (12)
C4—C5—C6120.29 (16)C42—C41—P3125.94 (9)
C4—C5—H5119.1 (13)C46—C41—P3114.86 (10)
C6—C5—H5120.5 (13)C41—C42—C43120.11 (13)
C5—C6—C1120.40 (14)C41—C42—H42120.0 (11)
C5—C6—H6119.7 (12)C43—C42—H42119.8 (11)
C1—C6—H6119.8 (12)C44—C43—C42120.54 (15)
C12—C11—C16118.50 (12)C44—C43—H43119.9 (13)
C12—C11—P1123.05 (10)C42—C43—H43119.6 (13)
C16—C11—P1118.45 (10)C45—C44—C43119.81 (14)
C11—C12—C13120.16 (14)C45—C44—H44119.6 (13)
C11—C12—H12120.7 (11)C43—C44—H44120.6 (13)
C13—C12—H12119.1 (11)C44—C45—C46120.09 (15)
C14—C13—C12120.79 (16)C44—C45—H45121.3 (14)
C14—C13—H13121.1 (12)C46—C45—H45118.4 (14)
C12—C13—H13117.9 (13)C45—C46—C41120.86 (15)
C15—C14—C13119.60 (14)C45—C46—H46120.0 (14)
C15—C14—H14121.1 (13)C41—C46—H46119.1 (14)
C13—C14—H14119.3 (13)C56—C51—C52119.65 (13)
C14—C15—C16119.93 (15)C56—C51—P3123.44 (10)
C14—C15—H15121.8 (13)C52—C51—P3116.88 (11)
C16—C15—H15118.3 (13)C53—C52—C51119.98 (17)
C15—C16—C11121.02 (15)C53—C52—H52119.4 (12)
C15—C16—H16120.3 (11)C51—C52—H52120.6 (12)
C11—C16—H16118.6 (11)C54—C53—C52120.06 (16)
C22—C21—C26118.84 (11)C54—C53—H53122.1 (15)
C22—C21—P2118.12 (9)C52—C53—H53117.8 (15)
C26—C21—P2123.03 (9)C53—C54—C55120.31 (16)
C23—C22—C21120.17 (12)C53—C54—H54119.3 (14)
C23—C22—H22120.4 (12)C55—C54—H54120.4 (14)
C21—C22—H22119.4 (12)C56—C55—C54120.30 (18)
C24—C23—C22120.53 (12)C56—C55—H55120.5 (14)
C24—C23—H23121.4 (13)C54—C55—H55119.2 (14)
C22—C23—H23118.1 (13)C55—C56—C51119.66 (16)
C23—C24—C25119.74 (12)C55—C56—H56121.4 (11)
C23—C24—H24121.5 (12)C51—C56—H56118.9 (11)
C25—C24—H24118.7 (12)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2581).

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