4,5-Bis[bis­(diethyl­amino)phosphino]-9,9-dimethylxanthene

Adams, D.J.; Fawcett, J.; Hope, E.G.; Stuart, A.M.

doi:10.1107/S1600536805024797

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 61| Part 9| September 2005| Pages o2831-o2832

https://doi.org/10.1107/S1600536805024797

4,5-Bis[bis(diethylamino)phosphino]-9,9-dimethylxanthene

David J Adams,^a John Fawcett,^a Eric G. Hope ^a ^* and Alison M. Stuart ^a

^aDepartment of Chemistry, University of Leicester, Leicester LE1 7RH, England
^*Correspondence e-mail: egh1@leicester.ac.uk

(Received 24 June 2005; accepted 2 August 2005; online 6 August 2005)

The structure of the title compound, C₃₁H₅₂N₄OP₂, reveals a near-planar xanthene skeleton.

Comment

Xantphos, and related bidentate ligands with the xanthene backbone, have been shown to be remarkable ligands for the rhodium-catalysed hydroformylation of long-chain alkenes, giving exceptionally high selectivity to the industrially useful linear aldehyde (linear/branched ratio = 50:1) (Kranenburg et al., 1995 ). The title compound, (I), was prepared according to the literature procedure of Goertz et al. (2001 ) as an intermediate in work directed towards the synthesis of perfluoroalkylated derivatives of Xantphos (Adams et al., 2004 ). Crystals suitable for X-ray analysis were grown from hexane solution. The bond lengths and angles within the structure are unremarkable. The molecule has a pseudo-C2 axis of symmetry through O1 and C6, such that the lone pairs on phosphorus point either in front or behind an approximately planar xanthene skeleton.

Figure 1
The molecular structure of (I)

, showing the atom-labelling scheme and 50% probability displacement ellipsoids. H atoms have been omitted for clarity.

Experimental

The title compound was prepared according to the literature procedure of Goertz et al. (2001), Crystals suitable for X-ray analysis were grown from a hexane solution.

Crystal data

C₃₁H₅₂N₄OP₂
M_r = 558.71
Monoclinic, P 2₁ /c
a = 18.799 (1) Å
b = 11.4968 (6) Å
c = 15.2179 (8) Å
β = 100.880 (1)°
V = 3229.9 (3) Å³
Z = 4
D_x = 1.149 Mg m⁻³
Mo Kα radiation
Cell parameters from 6949 reflections
θ = 2.2–26.9°
μ = 0.16 mm⁻¹
T = 150 (2) K
Block, colourless
0.34 × 0.21 × 0.16 mm

Data collection

Bruker APEX CCD area-detector diffractometer
φ and ω scans
Absorption correction: multi-scan(SADABS; Sheldrick, 1996 )T_min = 0.93, T_max = 0.96
22958 measured reflections
5685 independent reflections
4653 reflections with I > 2σ(I)
R_int = 0.034
θ_max = 25.0°
h = −22 → 22
k = −13 → 13
l = −18 → 18

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.139
S = 1.06
5685 reflections
353 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0817P)² + 0.3182P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.002
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.35 e Å⁻³

All H atoms were included in calculated positions, riding on the bonded atom [C—H = 0.95 (CH), 0.98 (CH₃) and 0.99 Å (CH₂)], and with U_iso(H) values set at 1.5U_eq of the bonded C atom for methyl H atoms and at 1.2U_eq for all other H atoms.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1999 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536805024797/rn6058sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536805024797/rn6058Isup2.hkl

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.

4,5-Bis[bis(diethylamino)phosphino]-9,9-dimethylxanthene top

Crystal data top

C₃₁H₅₂N₄OP₂	F(000) = 1216
M_r = 558.71	D_x = 1.149 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 18.799 (1) Å	Cell parameters from 6949 reflections
b = 11.4968 (6) Å	θ = 2.2–26.9°
c = 15.2179 (8) Å	µ = 0.16 mm⁻¹
β = 100.880 (1)°	T = 150 K
V = 3229.9 (3) Å³	Block, colourless
Z = 4	0.34 × 0.21 × 0.16 mm

Data collection top

Bruker APEX CCD area-detector diffractometer	5685 independent reflections
Radiation source: fine-focus sealed tube	4653 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
φ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→22
T_min = 0.93, T_max = 0.96	k = −13→13
22958 measured reflections	l = −18→18

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0817P)² + 0.3182P] where P = (F_o² + 2F_c²)/3
5685 reflections	(Δ/σ)_max = 0.002
353 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Special details top

Experimental. absorption correction based on 11566 reflections (SADABS); R_int 0.042 before and 0.029 after correction.

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
P1	0.24064 (3)	0.79839 (4)	0.15134 (4)	0.03314 (17)
P2	0.34099 (3)	0.47707 (4)	0.26900 (4)	0.03378 (17)
O1	0.19529 (7)	0.58133 (11)	0.22875 (9)	0.0323 (3)
N1	0.25398 (9)	0.82334 (14)	0.26194 (12)	0.0335 (4)
N2	0.22386 (11)	0.92669 (15)	0.09521 (12)	0.0421 (5)
N3	0.32498 (9)	0.47476 (14)	0.15649 (12)	0.0341 (4)
N4	0.40281 (10)	0.37232 (15)	0.30858 (14)	0.0460 (5)
C1	0.14864 (10)	0.73710 (17)	0.13477 (13)	0.0299 (4)
C2	0.09075 (12)	0.78508 (19)	0.07518 (14)	0.0378 (5)
H2	0.0981	0.8535	0.0431	0.045*
C3	0.02307 (12)	0.7352 (2)	0.06197 (15)	0.0450 (6)
H3	−0.0154	0.7682	0.0199	0.054*
C4	0.01100 (12)	0.6380 (2)	0.10931 (15)	0.0431 (6)
H4	−0.0364	0.6061	0.1010	0.052*
C5	0.06652 (11)	0.58504 (18)	0.16925 (14)	0.0341 (5)
C6	0.05264 (12)	0.48505 (19)	0.22901 (17)	0.0436 (6)
C6'	0.02674 (16)	0.5366 (3)	0.3116 (2)	0.0691 (9)
H61	0.0167	0.4733	0.3506	0.104*
H62	−0.0175	0.5821	0.2918	0.104*
H63	0.0646	0.5872	0.3445	0.104*
C6"	−0.00587 (16)	0.4030 (3)	0.1799 (3)	0.0886 (11)
H64	0.0104	0.3692	0.1279	0.133*
H65	−0.0508	0.4467	0.1599	0.133*
H66	−0.0146	0.3406	0.2204	0.133*
C7	0.12274 (12)	0.41934 (17)	0.26105 (14)	0.0356 (5)
C8	0.12244 (14)	0.30780 (19)	0.29698 (17)	0.0491 (6)
H8	0.0776	0.2709	0.2989	0.059*
C9	0.18592 (16)	0.2506 (2)	0.32963 (18)	0.0571 (7)
H9	0.1847	0.1759	0.3559	0.069*
C10	0.25162 (14)	0.30120 (19)	0.32450 (16)	0.0464 (6)
H10	0.2952	0.2611	0.3483	0.056*
C11	0.25522 (11)	0.40994 (17)	0.28504 (13)	0.0331 (5)
C12	0.18949 (11)	0.46837 (16)	0.25811 (13)	0.0301 (5)
C13	0.13532 (10)	0.63374 (17)	0.17769 (13)	0.0292 (4)
C14	0.19883 (12)	0.85861 (18)	0.31332 (14)	0.0355 (5)
H14A	0.1507	0.8556	0.2735	0.043*
H14B	0.2080	0.9403	0.3327	0.043*
C15	0.19678 (14)	0.7844 (2)	0.39480 (15)	0.0494 (6)
H15A	0.1927	0.7023	0.3773	0.074*
H15B	0.1549	0.8065	0.4210	0.074*
H15C	0.2414	0.7963	0.4390	0.074*
C16	0.32828 (12)	0.8252 (2)	0.31135 (18)	0.0513 (6)
H16A	0.3602	0.7907	0.2735	0.062*
H16B	0.3315	0.7758	0.3653	0.062*
C17	0.35593 (16)	0.9459 (3)	0.3400 (2)	0.0730 (9)
H17A	0.3533	0.9954	0.2871	0.110*
H17B	0.4063	0.9408	0.3718	0.110*
H17C	0.3260	0.9796	0.3798	0.110*
C18	0.18840 (14)	1.02350 (18)	0.13247 (16)	0.0449 (6)
H18A	0.2254	1.0670	0.1749	0.054*
H18B	0.1531	0.9914	0.1668	0.054*
C19	0.14921 (17)	1.1079 (2)	0.06274 (19)	0.0656 (8)
H19A	0.1838	1.1414	0.0291	0.098*
H19B	0.1273	1.1702	0.0926	0.098*
H19C	0.1112	1.0664	0.0216	0.098*
C20	0.27251 (16)	0.9574 (2)	0.03463 (18)	0.0596 (7)
H20A	0.2441	0.9963	−0.0186	0.072*
H20B	0.2928	0.8850	0.0141	0.072*
C21	0.33337 (19)	1.0348 (3)	0.0748 (2)	0.0846 (10)
H21A	0.3140	1.1095	0.0906	0.127*
H21B	0.3652	1.0476	0.0316	0.127*
H21C	0.3610	0.9983	0.1288	0.127*
C22	0.28363 (13)	0.38731 (18)	0.09829 (15)	0.0408 (5)
H22A	0.2685	0.3252	0.1359	0.049*
H22B	0.3155	0.3516	0.0609	0.049*
C23	0.21694 (14)	0.4359 (2)	0.03769 (16)	0.0546 (7)
H23A	0.1860	0.4742	0.0740	0.082*
H23B	0.1901	0.3725	0.0034	0.082*
H23C	0.2317	0.4926	−0.0036	0.082*
C24	0.36406 (12)	0.55852 (19)	0.11121 (16)	0.0407 (5)
H24A	0.3758	0.6276	0.1501	0.049*
H24B	0.3319	0.5843	0.0554	0.049*
C25	0.43374 (14)	0.5114 (2)	0.0880 (2)	0.0588 (7)
H25A	0.4683	0.4941	0.1432	0.088*
H25B	0.4546	0.5695	0.0532	0.088*
H25C	0.4233	0.4401	0.0526	0.088*
C26	0.40659 (13)	0.2562 (2)	0.27059 (19)	0.0525 (7)
H26A	0.3605	0.2410	0.2286	0.063*
H26B	0.4105	0.1986	0.3196	0.063*
C27	0.46806 (16)	0.2363 (2)	0.2219 (2)	0.0665 (8)
H27A	0.4620	0.2868	0.1691	0.100*
H27B	0.4682	0.1548	0.2032	0.100*
H27C	0.5140	0.2544	0.2618	0.100*
C28	0.46724 (15)	0.4091 (2)	0.37006 (19)	0.0683 (9)
H28A	0.4594	0.4893	0.3900	0.082*
H28B	0.5080	0.4116	0.3373	0.082*
C29	0.4888 (3)	0.3344 (3)	0.4510 (2)	0.1249 (18)
H29A	0.4472	0.3240	0.4806	0.187*
H29B	0.5285	0.3717	0.4924	0.187*
H29C	0.5048	0.2583	0.4331	0.187*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0327 (3)	0.0226 (3)	0.0477 (4)	0.0019 (2)	0.0167 (3)	0.0019 (2)
P2	0.0341 (3)	0.0233 (3)	0.0428 (3)	0.0034 (2)	0.0045 (2)	−0.0032 (2)
O1	0.0293 (8)	0.0204 (7)	0.0463 (9)	−0.0018 (6)	0.0047 (6)	0.0051 (6)
N1	0.0250 (9)	0.0262 (9)	0.0489 (11)	0.0013 (7)	0.0062 (8)	0.0015 (8)
N2	0.0568 (12)	0.0292 (10)	0.0465 (11)	0.0027 (9)	0.0252 (9)	0.0080 (8)
N3	0.0348 (10)	0.0258 (9)	0.0436 (11)	−0.0028 (7)	0.0125 (8)	−0.0012 (7)
N4	0.0386 (11)	0.0278 (10)	0.0656 (13)	0.0065 (8)	−0.0051 (9)	−0.0067 (9)
C1	0.0307 (11)	0.0280 (10)	0.0331 (11)	0.0050 (8)	0.0114 (9)	−0.0011 (8)
C2	0.0434 (13)	0.0347 (12)	0.0358 (12)	0.0090 (10)	0.0087 (10)	0.0006 (9)
C3	0.0364 (13)	0.0523 (15)	0.0432 (13)	0.0134 (11)	−0.0007 (10)	−0.0033 (11)
C4	0.0260 (11)	0.0506 (14)	0.0525 (14)	0.0007 (10)	0.0070 (10)	−0.0117 (12)
C5	0.0289 (11)	0.0331 (11)	0.0418 (12)	−0.0006 (9)	0.0103 (9)	−0.0084 (9)
C6	0.0341 (12)	0.0368 (12)	0.0630 (16)	−0.0093 (10)	0.0174 (11)	−0.0005 (11)
C6'	0.0724 (19)	0.0618 (18)	0.090 (2)	0.0211 (15)	0.0569 (17)	0.0227 (15)
C6"	0.0591 (19)	0.0610 (19)	0.135 (3)	−0.0289 (16)	−0.0094 (19)	0.0131 (19)
C7	0.0428 (13)	0.0282 (11)	0.0401 (12)	−0.0048 (9)	0.0192 (10)	−0.0035 (9)
C8	0.0601 (16)	0.0325 (12)	0.0641 (16)	−0.0069 (11)	0.0362 (13)	0.0024 (11)
C9	0.080 (2)	0.0314 (13)	0.0695 (18)	0.0031 (13)	0.0380 (15)	0.0164 (12)
C10	0.0589 (16)	0.0330 (12)	0.0504 (14)	0.0099 (11)	0.0181 (12)	0.0119 (10)
C11	0.0433 (12)	0.0247 (10)	0.0328 (11)	0.0042 (9)	0.0113 (9)	−0.0006 (8)
C12	0.0416 (12)	0.0212 (10)	0.0297 (11)	−0.0012 (8)	0.0122 (9)	−0.0019 (8)
C13	0.0277 (11)	0.0273 (10)	0.0332 (11)	0.0032 (8)	0.0069 (8)	−0.0030 (8)
C14	0.0368 (12)	0.0313 (11)	0.0381 (12)	0.0019 (9)	0.0067 (9)	0.0003 (9)
C15	0.0621 (17)	0.0458 (14)	0.0399 (13)	−0.0022 (12)	0.0085 (12)	0.0050 (11)
C16	0.0311 (12)	0.0524 (15)	0.0677 (16)	−0.0042 (11)	0.0023 (11)	−0.0056 (13)
C17	0.0571 (18)	0.079 (2)	0.083 (2)	−0.0322 (16)	0.0133 (15)	−0.0303 (17)
C18	0.0589 (15)	0.0285 (12)	0.0488 (14)	0.0102 (10)	0.0141 (12)	0.0087 (10)
C19	0.088 (2)	0.0389 (14)	0.0653 (18)	0.0120 (14)	0.0036 (15)	0.0154 (13)
C20	0.082 (2)	0.0461 (14)	0.0577 (16)	−0.0171 (14)	0.0310 (15)	0.0000 (12)
C21	0.086 (2)	0.073 (2)	0.105 (3)	−0.0281 (18)	0.042 (2)	−0.0244 (19)
C22	0.0522 (14)	0.0318 (11)	0.0419 (13)	−0.0053 (10)	0.0183 (11)	−0.0057 (10)
C23	0.0701 (18)	0.0523 (15)	0.0380 (14)	−0.0116 (13)	0.0013 (12)	−0.0032 (11)
C24	0.0380 (12)	0.0297 (11)	0.0583 (15)	0.0004 (9)	0.0189 (11)	0.0027 (10)
C25	0.0481 (15)	0.0462 (14)	0.092 (2)	0.0016 (12)	0.0381 (15)	0.0040 (14)
C26	0.0425 (14)	0.0300 (12)	0.0789 (18)	0.0086 (10)	−0.0040 (12)	−0.0097 (12)
C27	0.072 (2)	0.0449 (15)	0.085 (2)	0.0168 (14)	0.0217 (16)	−0.0054 (14)
C28	0.0632 (18)	0.0544 (16)	0.0721 (19)	0.0192 (14)	−0.0260 (15)	−0.0176 (14)
C29	0.199 (5)	0.078 (2)	0.072 (2)	0.074 (3)	−0.039 (3)	−0.0197 (19)

Geometric parameters (Å, º) top

P1—N1	1.6789 (19)	C14—H14B	0.9900
P1—N2	1.7038 (18)	C15—H15A	0.9800
P1—C1	1.840 (2)	C15—H15B	0.9800
P2—N3	1.6816 (18)	C15—H15C	0.9800
P2—N4	1.7027 (18)	C16—C17	1.517 (4)
P2—C11	1.845 (2)	C16—H16A	0.9900
O1—C13	1.381 (2)	C16—H16B	0.9900
O1—C12	1.384 (2)	C17—H17A	0.9800
N1—C16	1.456 (3)	C17—H17B	0.9800
N1—C14	1.469 (3)	C17—H17C	0.9800
N2—C20	1.459 (3)	C18—C19	1.521 (3)
N2—C18	1.465 (3)	C18—H18A	0.9900
N3—C24	1.460 (3)	C18—H18B	0.9900
N3—C22	1.463 (3)	C19—H19A	0.9800
N4—C28	1.447 (3)	C19—H19B	0.9800
N4—C26	1.462 (3)	C19—H19C	0.9800
C1—C2	1.392 (3)	C20—C21	1.487 (4)
C1—C13	1.401 (3)	C20—H20A	0.9900
C2—C3	1.375 (3)	C20—H20B	0.9900
C2—H2	0.9500	C21—H21A	0.9800
C3—C4	1.371 (3)	C21—H21B	0.9800
C3—H3	0.9500	C21—H21C	0.9800
C4—C5	1.390 (3)	C22—C23	1.516 (3)
C4—H4	0.9500	C22—H22A	0.9900
C5—C13	1.393 (3)	C22—H22B	0.9900
C5—C6	1.519 (3)	C23—H23A	0.9800
C6—C7	1.517 (3)	C23—H23B	0.9800
C6—C6"	1.532 (3)	C23—H23C	0.9800
C6—C6'	1.549 (4)	C24—C25	1.520 (3)
C6'—H61	0.9800	C24—H24A	0.9900
C6'—H62	0.9800	C24—H24B	0.9900
C6'—H63	0.9800	C25—H25A	0.9800
C6"—H64	0.9800	C25—H25B	0.9800
C6"—H65	0.9800	C25—H25C	0.9800
C6"—H66	0.9800	C26—C27	1.503 (4)
C7—C12	1.384 (3)	C26—H26A	0.9900
C7—C8	1.394 (3)	C26—H26B	0.9900
C8—C9	1.371 (4)	C27—H27A	0.9800
C8—H8	0.9500	C27—H27B	0.9800
C9—C10	1.381 (4)	C27—H27C	0.9800
C9—H9	0.9500	C28—C29	1.494 (4)
C10—C11	1.394 (3)	C28—H28A	0.9900
C10—H10	0.9500	C28—H28B	0.9900
C11—C12	1.398 (3)	C29—H29A	0.9800
C14—C15	1.512 (3)	C29—H29B	0.9800
C14—H14A	0.9900	C29—H29C	0.9800

N1—P1—N2	109.46 (9)	N1—C16—C17	113.9 (2)
N1—P1—C1	99.29 (9)	N1—C16—H16A	108.8
N2—P1—C1	100.52 (9)	C17—C16—H16A	108.8
N3—P2—N4	109.15 (9)	N1—C16—H16B	108.8
N3—P2—C11	97.77 (9)	C17—C16—H16B	108.8
N4—P2—C11	102.27 (9)	H16A—C16—H16B	107.7
C13—O1—C12	119.03 (15)	C16—C17—H17A	109.5
C16—N1—C14	115.21 (18)	C16—C17—H17B	109.5
C16—N1—P1	117.86 (15)	H17A—C17—H17B	109.5
C14—N1—P1	126.45 (14)	C16—C17—H17C	109.5
C20—N2—C18	116.49 (18)	H17A—C17—H17C	109.5
C20—N2—P1	116.57 (16)	H17B—C17—H17C	109.5
C18—N2—P1	121.22 (14)	N2—C18—C19	114.2 (2)
C24—N3—C22	115.13 (17)	N2—C18—H18A	108.7
C24—N3—P2	117.43 (14)	C19—C18—H18A	108.7
C22—N3—P2	126.86 (14)	N2—C18—H18B	108.7
C28—N4—C26	115.18 (18)	C19—C18—H18B	108.7
C28—N4—P2	117.00 (15)	H18A—C18—H18B	107.6
C26—N4—P2	125.94 (16)	C18—C19—H19A	109.5
C2—C1—C13	116.95 (19)	C18—C19—H19B	109.5
C2—C1—P1	122.44 (16)	H19A—C19—H19B	109.5
C13—C1—P1	120.46 (15)	C18—C19—H19C	109.5
C3—C2—C1	121.2 (2)	H19A—C19—H19C	109.5
C3—C2—H2	119.4	H19B—C19—H19C	109.5
C1—C2—H2	119.4	N2—C20—C21	114.2 (2)
C4—C3—C2	120.2 (2)	N2—C20—H20A	108.7
C4—C3—H3	119.9	C21—C20—H20A	108.7
C2—C3—H3	119.9	N2—C20—H20B	108.7
C3—C4—C5	121.6 (2)	C21—C20—H20B	108.7
C3—C4—H4	119.2	H20A—C20—H20B	107.6
C5—C4—H4	119.2	C20—C21—H21A	109.5
C4—C5—C13	117.0 (2)	C20—C21—H21B	109.5
C4—C5—C6	122.15 (19)	H21A—C21—H21B	109.5
C13—C5—C6	120.70 (19)	C20—C21—H21C	109.5
C5—C6—C7	109.42 (17)	H21A—C21—H21C	109.5
C5—C6—C6"	111.2 (2)	H21B—C21—H21C	109.5
C7—C6—C6"	110.5 (2)	N3—C22—C23	113.50 (18)
C5—C6—C6'	108.16 (19)	N3—C22—H22A	108.9
C7—C6—C6'	108.5 (2)	C23—C22—H22A	108.9
C6"—C6—C6'	109.0 (2)	N3—C22—H22B	108.9
C6—C6'—H61	109.5	C23—C22—H22B	108.9
C6—C6'—H62	109.5	H22A—C22—H22B	107.7
H61—C6'—H62	109.5	C22—C23—H23A	109.5
C6—C6'—H63	109.5	C22—C23—H23B	109.5
H61—C6'—H63	109.5	H23A—C23—H23B	109.5
H62—C6'—H63	109.5	C22—C23—H23C	109.5
C6—C6"—H64	109.5	H23A—C23—H23C	109.5
C6—C6"—H65	109.5	H23B—C23—H23C	109.5
H64—C6"—H65	109.5	N3—C24—C25	114.03 (18)
C6—C6"—H66	109.5	N3—C24—H24A	108.7
H64—C6"—H66	109.5	C25—C24—H24A	108.7
H65—C6"—H66	109.5	N3—C24—H24B	108.7
C12—C7—C8	117.3 (2)	C25—C24—H24B	108.7
C12—C7—C6	121.64 (18)	H24A—C24—H24B	107.6
C8—C7—C6	121.09 (19)	C24—C25—H25A	109.5
C9—C8—C7	121.0 (2)	C24—C25—H25B	109.5
C9—C8—H8	119.5	H25A—C25—H25B	109.5
C7—C8—H8	119.5	C24—C25—H25C	109.5
C8—C9—C10	120.3 (2)	H25A—C25—H25C	109.5
C8—C9—H9	119.9	H25B—C25—H25C	109.5
C10—C9—H9	119.9	N4—C26—C27	115.7 (2)
C9—C10—C11	121.2 (2)	N4—C26—H26A	108.4
C9—C10—H10	119.4	C27—C26—H26A	108.4
C11—C10—H10	119.4	N4—C26—H26B	108.4
C10—C11—C12	116.43 (19)	C27—C26—H26B	108.4
C10—C11—P2	123.15 (17)	H26A—C26—H26B	107.4
C12—C11—P2	120.41 (15)	C26—C27—H27A	109.5
C7—C12—O1	121.31 (18)	C26—C27—H27B	109.5
C7—C12—C11	123.46 (18)	H27A—C27—H27B	109.5
O1—C12—C11	115.23 (17)	C26—C27—H27C	109.5
O1—C13—C5	121.45 (18)	H27A—C27—H27C	109.5
O1—C13—C1	115.70 (17)	H27B—C27—H27C	109.5
C5—C13—C1	122.85 (18)	N4—C28—C29	115.4 (3)
N1—C14—C15	114.25 (18)	N4—C28—H28A	108.4
N1—C14—H14A	108.7	C29—C28—H28A	108.4
C15—C14—H14A	108.7	N4—C28—H28B	108.4
N1—C14—H14B	108.7	C29—C28—H28B	108.4
C15—C14—H14B	108.7	H28A—C28—H28B	107.5
H14A—C14—H14B	107.6	C28—C29—H29A	109.5
C14—C15—H15A	109.5	C28—C29—H29B	109.5
C14—C15—H15B	109.5	H29A—C29—H29B	109.5
H15A—C15—H15B	109.5	C28—C29—H29C	109.5
C14—C15—H15C	109.5	H29A—C29—H29C	109.5
H15A—C15—H15C	109.5	H29B—C29—H29C	109.5
H15B—C15—H15C	109.5

N2—P1—N1—C16	−101.02 (17)	C9—C10—C11—C12	5.2 (3)
C1—P1—N1—C16	154.27 (16)	C9—C10—C11—P2	−175.46 (19)
N2—P1—N1—C14	70.55 (18)	N3—P2—C11—C10	113.93 (19)
C1—P1—N1—C14	−34.16 (17)	N4—P2—C11—C10	2.3 (2)
N1—P1—N2—C20	122.28 (17)	N3—P2—C11—C12	−66.72 (17)
C1—P1—N2—C20	−133.86 (18)	N4—P2—C11—C12	−178.34 (16)
N1—P1—N2—C18	−30.1 (2)	C8—C7—C12—O1	−175.96 (18)
C1—P1—N2—C18	73.8 (2)	C6—C7—C12—O1	2.4 (3)
N4—P2—N3—C24	−97.65 (16)	C8—C7—C12—C11	3.2 (3)
C11—P2—N3—C24	156.43 (15)	C6—C7—C12—C11	−178.5 (2)
N4—P2—N3—C22	73.12 (19)	C13—O1—C12—C7	−19.3 (3)
C11—P2—N3—C22	−32.80 (18)	C13—O1—C12—C11	161.51 (17)
N3—P2—N4—C28	124.9 (2)	C10—C11—C12—C7	−6.3 (3)
C11—P2—N4—C28	−132.3 (2)	P2—C11—C12—C7	174.29 (16)
N3—P2—N4—C26	−38.7 (2)	C10—C11—C12—O1	172.85 (18)
C11—P2—N4—C26	64.1 (2)	P2—C11—C12—O1	−6.5 (2)
N1—P1—C1—C2	122.63 (17)	C12—O1—C13—C5	12.3 (3)
N2—P1—C1—C2	10.69 (19)	C12—O1—C13—C1	−166.96 (16)
N1—P1—C1—C13	−62.09 (17)	C4—C5—C13—O1	−173.69 (18)
N2—P1—C1—C13	−174.03 (16)	C6—C5—C13—O1	11.3 (3)
C13—C1—C2—C3	2.4 (3)	C4—C5—C13—C1	5.5 (3)
P1—C1—C2—C3	177.83 (16)	C6—C5—C13—C1	−169.50 (19)
C1—C2—C3—C4	1.6 (3)	C2—C1—C13—O1	173.18 (17)
C2—C3—C4—C5	−2.2 (3)	P1—C1—C13—O1	−2.4 (2)
C3—C4—C5—C13	−1.3 (3)	C2—C1—C13—C5	−6.1 (3)
C3—C4—C5—C6	173.6 (2)	P1—C1—C13—C5	178.41 (15)
C4—C5—C6—C7	160.1 (2)	C16—N1—C14—C15	−59.4 (2)
C13—C5—C6—C7	−25.1 (3)	P1—N1—C14—C15	128.82 (18)
C4—C5—C6—C6"	37.7 (3)	C14—N1—C16—C17	−65.7 (3)
C13—C5—C6—C6"	−147.5 (2)	P1—N1—C16—C17	106.8 (2)
C4—C5—C6—C6'	−81.9 (3)	C20—N2—C18—C19	52.3 (3)
C13—C5—C6—C6'	92.9 (2)	P1—N2—C18—C19	−155.28 (19)
C5—C6—C7—C12	18.5 (3)	C18—N2—C20—C21	58.6 (3)
C6"—C6—C7—C12	141.4 (2)	P1—N2—C20—C21	−95.2 (3)
C6'—C6—C7—C12	−99.3 (2)	C24—N3—C22—C23	−71.2 (2)
C5—C6—C7—C8	−163.2 (2)	P2—N3—C22—C23	117.85 (19)
C6"—C6—C7—C8	−40.4 (3)	C22—N3—C24—C25	−77.7 (3)
C6'—C6—C7—C8	79.0 (3)	P2—N3—C24—C25	94.1 (2)
C12—C7—C8—C9	1.3 (3)	C28—N4—C26—C27	−56.6 (3)
C6—C7—C8—C9	−177.0 (2)	P2—N4—C26—C27	107.2 (2)
C7—C8—C9—C10	−2.4 (4)	C26—N4—C28—C29	−60.1 (4)
C8—C9—C10—C11	−1.1 (4)	P2—N4—C28—C29	134.5 (2)

Acknowledgements

The authors thank the EPSRC (DJA) and the Royal Society (AMS) for financial support.

References

Adams, D. J., Cole-Hamilton, D. J., Harding, D. A. J., Hope, E. G., Pogorzelec, P. & Stuart, A. M. (2004). Tetrahedron, 60, 4079–4085. Web of Science CrossRef CAS Google Scholar
Bruker (1997). SMART. Version 5.622. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (1999). SAINT. Version 6.02. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Goertz, W., Kamer, P. C. J., van Leeuwen, P. W. N. M. & Vogt, D. (2001). Chem. Eur. J. 7, 1614–1618. CrossRef PubMed CAS Google Scholar
Kranenburg, M., van der Burgt, Y. E. M., Kamer, P. C. J., van Leeuwen, P. W. N. M. (1995). Organometallics, 14, 3081–3089. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2000). SHELXTL. Version 6.10. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar

© International Union of Crystallography. Prior permission is not required to reproduce short quotations, tables and figures from this article, provided the original authors and source are cited. For more information, click here.