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

Dickie, D.A.; Kemp, R.A.

doi:10.1107/S1600536808020412

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1449

doi:10.1107/S1600536808020412

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

Diane A. Dickie ^a and Richard A. Kemp ^a ^*‡

^aDepartment of Chemistry and Chemical Biology, MSC03 2060, 1 University of New Mexico, Albuquerque, NM 87131, USA
^*Correspondence e-mail: rakemp@unm.edu

(Received 23 June 2008; accepted 2 July 2008; online 9 July 2008)

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

Experimental

Crystal data

C₃₆H₃₀NP₃
M_r = 569.52
Monoclinic, P 2₁ /n
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 ) 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[F² > 2σ(F²)] = 0.042
wR(F²) = 0.118
S = 1.05
11496 reflections
481 parameters
All H-atom parameters refined
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.29 e Å⁻³

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

Supporting information

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

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

checkCIF report

Comment top

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 (sp² versus 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.

Related literature top

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

Experimental top

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, ²J_PP = 97 Hz, Ph₂P-N), 17.8 (d of d, ²J_PP = 97 Hz, ¹J_PP = 249 Hz, N=PPh₂), -9.4 (d, ¹J_PP = 249 Hz, P-PPh₂) p.p.m..

Computing details top

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

Figures top

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.

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

Crystal data top

C₃₆H₃₀NP₃	F(000) = 1192
M_r = 569.52	D_x = 1.278 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9384 reflections
a = 9.3026 (13) Å	θ = 2.3–33.2°
b = 10.8167 (15) Å	µ = 0.23 mm⁻¹
c = 29.750 (4) Å	T = 228 K
β = 98.589 (6)°	Square, colourless
V = 2960.0 (7) Å³	0.58 × 0.51 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	11496 independent reflections
Radiation source: fine-focus sealed tube	9167 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ϕ and ω scans	θ_max = 33.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −14→14
T_min = 0.88, T_max = 0.96	k = −16→16
76797 measured reflections	l = −45→45

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	All H-atom parameters refined
S = 1.06	w = 1/[σ²(F_o²) + (0.0543P)² + 1.05P] where P = (F_o² + 2F_c²)/3
11496 reflections	(Δ/σ)_max = 0.001
481 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₃₆H₃₀NP₃	V = 2960.0 (7) Å³
M_r = 569.52	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.3026 (13) Å	µ = 0.23 mm⁻¹
b = 10.8167 (15) Å	T = 228 K
c = 29.750 (4) Å	0.58 × 0.51 × 0.18 mm
β = 98.589 (6)°

Data collection top

Bruker SMART CCD area-detector diffractometer	11496 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	9167 reflections with I > 2σ(I)
T_min = 0.88, T_max = 0.96	R_int = 0.029
76797 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.118	All H-atom parameters refined
S = 1.06	Δρ_max = 0.41 e Å⁻³
11496 reflections	Δρ_min = −0.29 e Å⁻³
481 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
N1	0.89827 (12)	0.55872 (10)	0.13502 (4)	0.0285 (2)
P1	0.83490 (3)	0.52397 (3)	0.080793 (10)	0.02539 (7)
P2	0.98888 (3)	0.67406 (3)	0.154676 (10)	0.02169 (6)
P3	0.88674 (3)	0.85071 (3)	0.171889 (11)	0.02562 (7)
C1	0.92572 (12)	0.37613 (11)	0.07254 (4)	0.0265 (2)
C2	0.94010 (18)	0.34039 (15)	0.02865 (5)	0.0398 (3)
H2	0.915 (2)	0.396 (2)	0.0046 (7)	0.052 (5)*
C3	0.9911 (2)	0.22253 (18)	0.02040 (7)	0.0533 (4)
H3	0.998 (3)	0.200 (2)	−0.0104 (8)	0.067 (7)*
C4	1.03047 (18)	0.14200 (15)	0.05566 (7)	0.0494 (4)
H4	1.062 (2)	0.061 (2)	0.0493 (7)	0.064 (6)*
C5	1.02013 (17)	0.17767 (14)	0.09955 (7)	0.0433 (3)
H5	1.045 (2)	0.120 (2)	0.1238 (7)	0.059 (6)*
C6	0.96912 (15)	0.29430 (13)	0.10817 (5)	0.0344 (3)
H6	0.958 (2)	0.3171 (19)	0.1389 (7)	0.053 (6)*
C11	0.65810 (12)	0.45178 (11)	0.08595 (4)	0.0270 (2)
C12	0.60725 (15)	0.43744 (13)	0.12725 (5)	0.0339 (3)
H12	0.661 (2)	0.4670 (17)	0.1541 (6)	0.039 (5)*
C13	0.47230 (17)	0.38278 (15)	0.12874 (6)	0.0444 (3)
H13	0.437 (2)	0.380 (2)	0.1578 (7)	0.055 (6)*
C14	0.38678 (16)	0.34312 (14)	0.08938 (7)	0.0468 (4)
H14	0.297 (2)	0.306 (2)	0.0912 (7)	0.063 (6)*
C15	0.43625 (16)	0.35656 (14)	0.04816 (7)	0.0439 (4)
H15	0.378 (2)	0.332 (2)	0.0199 (7)	0.062 (6)*
C16	0.57122 (15)	0.41024 (13)	0.04646 (5)	0.0349 (3)
H16	0.6072 (19)	0.4179 (17)	0.0181 (6)	0.037 (4)*
C21	1.13511 (12)	0.72160 (10)	0.12433 (4)	0.02325 (19)
C22	1.20846 (14)	0.63055 (12)	0.10377 (5)	0.0318 (2)
H22	1.180 (2)	0.5479 (18)	0.1056 (6)	0.045 (5)*
C23	1.32338 (15)	0.66224 (14)	0.08106 (5)	0.0371 (3)
H23	1.372 (2)	0.597 (2)	0.0673 (7)	0.057 (6)*
C24	1.36496 (15)	0.78400 (14)	0.07826 (5)	0.0358 (3)
H24	1.448 (2)	0.8079 (19)	0.0628 (6)	0.049 (5)*
C25	1.29177 (17)	0.87515 (14)	0.09808 (6)	0.0420 (3)
H25	1.318 (2)	0.957 (2)	0.0961 (7)	0.061 (6)*
C26	1.17755 (16)	0.84426 (12)	0.12116 (6)	0.0371 (3)
H26	1.132 (2)	0.909 (2)	0.1355 (7)	0.055 (6)*
C31	1.06971 (12)	0.63888 (11)	0.21231 (4)	0.0256 (2)
C32	1.16599 (14)	0.72246 (13)	0.23711 (5)	0.0326 (2)
H32	1.197 (2)	0.7950 (18)	0.2228 (6)	0.042 (5)*
C33	1.21154 (17)	0.70324 (17)	0.28318 (5)	0.0419 (3)
H33	1.277 (2)	0.7602 (18)	0.2992 (6)	0.045 (5)*
C34	1.16275 (19)	0.60144 (19)	0.30440 (5)	0.0488 (4)
H34	1.191 (2)	0.587 (2)	0.3358 (7)	0.056 (6)*
C35	1.0706 (2)	0.51676 (18)	0.27995 (6)	0.0491 (4)
H35	1.041 (2)	0.449 (2)	0.2946 (7)	0.061 (6)*
C36	1.02326 (16)	0.53572 (13)	0.23390 (5)	0.0362 (3)
H36	0.953 (2)	0.4794 (18)	0.2163 (6)	0.047 (5)*
C41	0.77800 (13)	0.90632 (11)	0.11987 (4)	0.0268 (2)
C42	0.78720 (15)	0.86532 (13)	0.07605 (5)	0.0334 (3)
H42	0.842 (2)	0.7942 (18)	0.0716 (6)	0.041 (5)*
C43	0.71842 (18)	0.93088 (16)	0.03862 (5)	0.0420 (3)
H43	0.727 (2)	0.9039 (19)	0.0095 (7)	0.052 (5)*
C44	0.64070 (18)	1.03665 (16)	0.04451 (6)	0.0470 (4)
H44	0.597 (2)	1.082 (2)	0.0194 (7)	0.058 (6)*
C45	0.6267 (2)	1.07566 (16)	0.08773 (7)	0.0506 (4)
H45	0.578 (3)	1.150 (2)	0.0926 (8)	0.070 (7)*
C46	0.69448 (17)	1.01113 (14)	0.12517 (6)	0.0406 (3)
H46	0.684 (3)	1.038 (2)	0.1553 (8)	0.069 (7)*
C51	0.75546 (14)	0.78245 (12)	0.20420 (4)	0.0296 (2)
C52	0.78649 (17)	0.79087 (16)	0.25158 (5)	0.0407 (3)
H52	0.878 (3)	0.839 (2)	0.2671 (8)	0.067 (7)*
C53	0.6955 (2)	0.73483 (19)	0.27841 (6)	0.0523 (4)
H53	0.719 (3)	0.744 (2)	0.3110 (8)	0.073 (7)*
C54	0.5732 (2)	0.67193 (19)	0.25838 (7)	0.0581 (5)
H54	0.512 (3)	0.633 (2)	0.2772 (8)	0.071 (7)*
C55	0.5397 (2)	0.66580 (18)	0.21142 (7)	0.0523 (4)
H55	0.460 (2)	0.623 (2)	0.1988 (7)	0.058 (6)*
C56	0.63044 (15)	0.72019 (14)	0.18414 (5)	0.0375 (3)
H56	0.608 (2)	0.7168 (18)	0.1505 (6)	0.044 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0314 (5)	0.0258 (4)	0.0285 (5)	−0.0062 (4)	0.0052 (4)	−0.0046 (4)
P1	0.02921 (14)	0.02131 (13)	0.02575 (14)	−0.00134 (10)	0.00446 (11)	0.00031 (10)
P2	0.02190 (12)	0.01984 (12)	0.02357 (13)	0.00031 (9)	0.00413 (9)	−0.00128 (9)
P3	0.02697 (13)	0.02346 (13)	0.02645 (14)	0.00363 (10)	0.00405 (11)	−0.00289 (10)
C1	0.0255 (5)	0.0250 (5)	0.0293 (5)	−0.0026 (4)	0.0054 (4)	−0.0024 (4)
C2	0.0473 (8)	0.0408 (7)	0.0325 (7)	0.0040 (6)	0.0102 (6)	−0.0065 (6)
C3	0.0592 (10)	0.0503 (10)	0.0526 (10)	0.0056 (8)	0.0156 (8)	−0.0225 (8)
C4	0.0397 (7)	0.0323 (7)	0.0766 (12)	0.0038 (6)	0.0104 (8)	−0.0161 (7)
C5	0.0372 (7)	0.0297 (6)	0.0628 (10)	0.0048 (5)	0.0063 (7)	0.0041 (6)
C6	0.0359 (6)	0.0307 (6)	0.0374 (7)	0.0035 (5)	0.0083 (5)	0.0025 (5)
C11	0.0249 (5)	0.0220 (5)	0.0331 (6)	0.0018 (4)	0.0009 (4)	−0.0004 (4)
C12	0.0308 (6)	0.0335 (6)	0.0378 (7)	−0.0013 (5)	0.0066 (5)	0.0010 (5)
C13	0.0349 (7)	0.0404 (8)	0.0605 (10)	−0.0025 (6)	0.0159 (7)	0.0065 (7)
C14	0.0275 (6)	0.0296 (6)	0.0824 (13)	−0.0023 (5)	0.0047 (7)	0.0017 (7)
C15	0.0327 (6)	0.0313 (7)	0.0621 (10)	0.0017 (5)	−0.0115 (6)	−0.0075 (6)
C16	0.0333 (6)	0.0302 (6)	0.0383 (7)	0.0035 (5)	−0.0038 (5)	−0.0041 (5)
C21	0.0229 (4)	0.0222 (5)	0.0249 (5)	0.0011 (4)	0.0042 (4)	−0.0002 (4)
C22	0.0330 (6)	0.0257 (5)	0.0389 (7)	0.0029 (4)	0.0133 (5)	−0.0014 (5)
C23	0.0362 (6)	0.0369 (7)	0.0418 (7)	0.0059 (5)	0.0179 (6)	−0.0011 (5)
C24	0.0294 (6)	0.0439 (7)	0.0362 (7)	0.0003 (5)	0.0112 (5)	0.0068 (5)
C25	0.0428 (7)	0.0304 (6)	0.0570 (9)	−0.0060 (6)	0.0216 (7)	0.0032 (6)
C26	0.0395 (6)	0.0231 (5)	0.0533 (8)	−0.0019 (5)	0.0214 (6)	−0.0032 (5)
C31	0.0246 (5)	0.0256 (5)	0.0265 (5)	0.0029 (4)	0.0035 (4)	0.0013 (4)
C32	0.0288 (5)	0.0358 (6)	0.0319 (6)	−0.0015 (5)	0.0006 (5)	−0.0008 (5)
C33	0.0358 (7)	0.0542 (9)	0.0329 (7)	0.0022 (6)	−0.0042 (5)	−0.0036 (6)
C34	0.0501 (9)	0.0644 (11)	0.0297 (7)	0.0090 (8)	−0.0009 (6)	0.0087 (7)
C35	0.0574 (9)	0.0501 (9)	0.0395 (8)	0.0004 (8)	0.0065 (7)	0.0178 (7)
C36	0.0414 (7)	0.0321 (6)	0.0347 (7)	−0.0024 (5)	0.0043 (5)	0.0063 (5)
C41	0.0270 (5)	0.0227 (5)	0.0306 (5)	0.0023 (4)	0.0044 (4)	0.0014 (4)
C42	0.0363 (6)	0.0321 (6)	0.0314 (6)	0.0050 (5)	0.0039 (5)	0.0009 (5)
C43	0.0453 (8)	0.0467 (8)	0.0322 (7)	−0.0005 (6)	−0.0002 (6)	0.0070 (6)
C44	0.0443 (8)	0.0412 (8)	0.0506 (9)	0.0016 (6)	−0.0088 (7)	0.0160 (7)
C45	0.0508 (9)	0.0344 (7)	0.0634 (11)	0.0167 (7)	−0.0021 (8)	0.0064 (7)
C46	0.0440 (7)	0.0319 (7)	0.0451 (8)	0.0143 (6)	0.0045 (6)	−0.0007 (6)
C51	0.0309 (5)	0.0318 (6)	0.0275 (5)	0.0088 (4)	0.0089 (4)	0.0001 (4)
C52	0.0431 (7)	0.0515 (9)	0.0290 (6)	0.0117 (6)	0.0105 (6)	0.0003 (6)
C53	0.0608 (10)	0.0637 (11)	0.0370 (8)	0.0184 (9)	0.0226 (7)	0.0118 (7)
C54	0.0637 (11)	0.0529 (10)	0.0678 (12)	0.0132 (8)	0.0425 (10)	0.0185 (9)
C55	0.0424 (8)	0.0508 (9)	0.0690 (12)	−0.0034 (7)	0.0252 (8)	0.0009 (8)
C56	0.0329 (6)	0.0409 (7)	0.0408 (7)	0.0017 (5)	0.0118 (5)	−0.0006 (6)

Geometric parameters (Å, º) top

N1—P2	1.5690 (10)	C24—H24	0.99 (2)
N1—P1	1.6755 (11)	C25—C26	1.3892 (19)
P1—C1	1.8421 (12)	C25—H25	0.92 (2)
P1—C11	1.8476 (12)	C26—H26	0.95 (2)
P2—C31	1.8071 (12)	C31—C36	1.3882 (18)
P2—C21	1.8156 (11)	C31—C32	1.4023 (18)
P2—P3	2.2273 (5)	C32—C33	1.388 (2)
P3—C51	1.8196 (13)	C32—H32	0.958 (19)
P3—C41	1.8200 (13)	C33—C34	1.379 (3)
C1—C2	1.3873 (18)	C33—H33	0.94 (2)
C1—C6	1.3935 (19)	C34—C35	1.385 (3)
C2—C3	1.395 (2)	C34—H34	0.95 (2)
C2—H2	0.94 (2)	C35—C36	1.390 (2)
C3—C4	1.371 (3)	C35—H35	0.92 (2)
C3—H3	0.96 (2)	C36—H36	0.99 (2)
C4—C5	1.379 (3)	C41—C42	1.3917 (18)
C4—H4	0.95 (2)	C41—C46	1.3965 (18)
C5—C6	1.385 (2)	C42—C43	1.393 (2)
C5—H5	0.96 (2)	C42—H42	0.943 (19)
C6—H6	0.97 (2)	C43—C44	1.378 (2)
C11—C12	1.3895 (18)	C43—H43	0.93 (2)
C11—C16	1.3972 (18)	C44—C45	1.378 (3)
C12—C13	1.394 (2)	C44—H44	0.93 (2)
C12—H12	0.933 (18)	C45—C46	1.384 (2)
C13—C14	1.382 (3)	C45—H45	0.95 (2)
C13—H13	0.97 (2)	C46—H46	0.96 (2)
C14—C15	1.380 (3)	C51—C56	1.398 (2)
C14—H14	0.93 (2)	C51—C52	1.3991 (19)
C15—C16	1.391 (2)	C52—C53	1.386 (2)
C15—H15	0.97 (2)	C52—H52	1.04 (2)
C16—H16	0.957 (17)	C53—C54	1.382 (3)
C21—C22	1.3909 (16)	C53—H53	0.97 (2)
C21—C26	1.3915 (17)	C54—C55	1.387 (3)
C22—C23	1.3901 (18)	C54—H54	0.96 (2)
C22—H22	0.94 (2)	C55—C56	1.386 (2)
C23—C24	1.379 (2)	C55—H55	0.91 (2)
C23—H23	0.97 (2)	C56—H56	0.990 (19)
C24—C25	1.379 (2)

P2—N1—P1	129.01 (7)	C24—C25—C26	120.13 (13)
N1—P1—C1	102.74 (6)	C24—C25—H25	120.2 (14)
N1—P1—C11	101.80 (6)	C26—C25—H25	119.7 (14)
C1—P1—C11	94.35 (5)	C25—C26—C21	120.58 (12)
N1—P2—C31	108.08 (6)	C25—C26—H26	118.3 (13)
N1—P2—C21	116.14 (5)	C21—C26—H26	121.1 (13)
C31—P2—C21	107.15 (5)	C36—C31—C32	119.56 (12)
N1—P2—P3	122.96 (4)	C36—C31—P2	119.62 (10)
C31—P2—P3	95.39 (4)	C32—C31—P2	120.40 (9)
C21—P2—P3	104.38 (4)	C33—C32—C31	119.97 (13)
C51—P3—C41	104.57 (6)	C33—C32—H32	119.6 (11)
C51—P3—P2	96.68 (4)	C31—C32—H32	120.4 (11)
C41—P3—P2	106.86 (4)	C34—C33—C32	119.90 (15)
C2—C1—C6	118.77 (13)	C34—C33—H33	121.4 (12)
C2—C1—P1	118.55 (10)	C32—C33—H33	118.7 (12)
C6—C1—P1	122.45 (10)	C33—C34—C35	120.53 (15)
C1—C2—C3	120.23 (16)	C33—C34—H34	121.2 (13)
C1—C2—H2	119.5 (13)	C35—C34—H34	118.3 (13)
C3—C2—H2	120.2 (13)	C34—C35—C36	120.01 (15)
C4—C3—C2	120.34 (16)	C34—C35—H35	119.2 (14)
C4—C3—H3	121.6 (14)	C36—C35—H35	120.8 (14)
C2—C3—H3	118.0 (15)	C31—C36—C35	120.00 (14)
C3—C4—C5	119.92 (15)	C31—C36—H36	118.7 (11)
C3—C4—H4	119.2 (13)	C35—C36—H36	121.3 (11)
C5—C4—H4	120.9 (13)	C42—C41—C46	118.52 (12)
C4—C5—C6	120.29 (16)	C42—C41—P3	125.94 (9)
C4—C5—H5	119.1 (13)	C46—C41—P3	114.86 (10)
C6—C5—H5	120.5 (13)	C41—C42—C43	120.11 (13)
C5—C6—C1	120.40 (14)	C41—C42—H42	120.0 (11)
C5—C6—H6	119.7 (12)	C43—C42—H42	119.8 (11)
C1—C6—H6	119.8 (12)	C44—C43—C42	120.54 (15)
C12—C11—C16	118.50 (12)	C44—C43—H43	119.9 (13)
C12—C11—P1	123.05 (10)	C42—C43—H43	119.6 (13)
C16—C11—P1	118.45 (10)	C45—C44—C43	119.81 (14)
C11—C12—C13	120.16 (14)	C45—C44—H44	119.6 (13)
C11—C12—H12	120.7 (11)	C43—C44—H44	120.6 (13)
C13—C12—H12	119.1 (11)	C44—C45—C46	120.09 (15)
C14—C13—C12	120.79 (16)	C44—C45—H45	121.3 (14)
C14—C13—H13	121.1 (12)	C46—C45—H45	118.4 (14)
C12—C13—H13	117.9 (13)	C45—C46—C41	120.86 (15)
C15—C14—C13	119.60 (14)	C45—C46—H46	120.0 (14)
C15—C14—H14	121.1 (13)	C41—C46—H46	119.1 (14)
C13—C14—H14	119.3 (13)	C56—C51—C52	119.65 (13)
C14—C15—C16	119.93 (15)	C56—C51—P3	123.44 (10)
C14—C15—H15	121.8 (13)	C52—C51—P3	116.88 (11)
C16—C15—H15	118.3 (13)	C53—C52—C51	119.98 (17)
C15—C16—C11	121.02 (15)	C53—C52—H52	119.4 (12)
C15—C16—H16	120.3 (11)	C51—C52—H52	120.6 (12)
C11—C16—H16	118.6 (11)	C54—C53—C52	120.06 (16)
C22—C21—C26	118.84 (11)	C54—C53—H53	122.1 (15)
C22—C21—P2	118.12 (9)	C52—C53—H53	117.8 (15)
C26—C21—P2	123.03 (9)	C53—C54—C55	120.31 (16)
C23—C22—C21	120.17 (12)	C53—C54—H54	119.3 (14)
C23—C22—H22	120.4 (12)	C55—C54—H54	120.4 (14)
C21—C22—H22	119.4 (12)	C56—C55—C54	120.30 (18)
C24—C23—C22	120.53 (12)	C56—C55—H55	120.5 (14)
C24—C23—H23	121.4 (13)	C54—C55—H55	119.2 (14)
C22—C23—H23	118.1 (13)	C55—C56—C51	119.66 (16)
C23—C24—C25	119.74 (12)	C55—C56—H56	121.4 (11)
C23—C24—H24	121.5 (12)	C51—C56—H56	118.9 (11)
C25—C24—H24	118.7 (12)

Experimental details

Crystal data
Chemical formula	C₃₆H₃₀NP₃
M_r	569.52
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	228
a, b, c (Å)	9.3026 (13), 10.8167 (15), 29.750 (4)
β (°)	98.589 (6)
V (Å³)	2960.0 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.58 × 0.51 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.88, 0.96
No. of measured, independent and observed [I > 2σ(I)] reflections	76797, 11496, 9167
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.777

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.118, 1.06
No. of reflections	11496
No. of parameters	481
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.29

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), publCIF (Westrip, 2008).

Footnotes

‡Concurrent address: Advanced Materials Laboratory, Sandia National Laboratories, 1001 University Blvd SE, Albuquerque, NM 87106, USA.

Acknowledgements

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.

References

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