The synthesis of phospho­rus heterocycles from tetra-tert-butyl­tetraphosphacubane

Tetra-tert-butyl­tetraphosphacubane, P₄C₄^tBu₄, reacts with water in the presence of `GaI' to yield two products, namely 4,6,7,8-tetra-tert-butyl-1,2,3-triphospha-5-phospho­niatetra­cyclo­[3.2.1.0^2,4.0^3,8]­oct-6-ene tetra­iodo­gallate(III), (C₂₀H₃₇P₄)[GaI₄], and tri­iodo(3,5,7,8-tetra-tert-butyl-1,2,4λ⁵,6-tetra­phos­pha­tetra­cyclo­[4.1.1.0^2,5.0^7,8]­octan-4-one)­gallium(III), [GaI₃(C₂₀H₃₈OP₄)], both of which have been structurally characterized. The X-ray crystal structure determination of the former compound shows it to be an ion-separated salt, while the latter compound is a neutral phosphinite complex of GaI₃.

S1. Comment

There is much interest in the reactivity of compounds derived from the cyclo-oligomerization of phosphaalkynes, RCP, especially the cyclotetramer of ^tBuCP (Hitchcock et al., 1995). This compound is of interest because a strong interaction between the P lone-pair electrons and the P–C σ^*antibonding orbitals considerably reduces the nucleophilicity of the P atoms (Wettling et al., 1989).

We have recently published a study on the reactivity of secondary phosphines towards "GaI". These reactions have yielded Ga—Ga bonded dimers with the coordination of one phosphine molecule per Ga^II centre (Baker et al., 2003). Therefore, we thought it worthwhile to investigate the reaction of "GaI" towards the relatively non-nucleophilic tetraphosphacubane, P₄C₄^tBu₄. No reaction occurred, but in the presence of trace water a rearrangement of the P₄C₄ skeleton occurred, yielding two products, both of which have been structurally characterized and are reported here.

The molecular structure of [C₂₀H₃₆P₄]⁺ [GaI₄]⁻, (I), is shown in Fig 1. The bond lengths and angles around the gallium centre of the anion are unremarkable. The tetraphosphabishomoprismane framework of the cation is comparable to the neutal analogue that forms a complex with two W(CO)₅ moeities, [(C₂₀H₃₆P₄){W(CO)₅}₂] (Hitchcock et al., 1995). The only major differences between these species are in the bond lengths around atom P4, which are slightly longer in (I). The bond angles around atom P4 are also greater in (I); the ΣCPC angle is 314.1° in (I) and 289° in [(C₂₀H₃₆P₄){W(CO)₅}₂]. In addition, the C═C bond length is 0.076 Å longer in (I) than in the tungsten complex. There is no specific, directional interaction between the cation and anion in (I).

The molecular structure of [C₂₀H₃₈GaI₃P₄O], (II), is shown in Fig 2. The 2,4-diphosphabicyclo[1.1.0]butane fragment is a rare structural motif and only three examples have been reported previously. The P—C and C—C bond lengths of the bicyclic framework are similar to those in previous examples (Jones et al., 2001; Niecke et al., 1999; Mack et al., 2002), and the P—O and Ga—O bond lengths of the phosphinite functionalty are also in keeping with previously reported examples of phosphinite-gallium adducts (Barron et al., 1996). The mechanisms of formation of (I) and (II) are unknown, but in both cases, the rearrangement of the tetraphosphacubane framework in the presence of water is mediated by "GaI", since no reaction occurs in its absence.

S2. Experimental

"GaI" was prepared by the ultrasonic activation of Ga (0.07 g, 0.99 mmol) and I₂ (0.24 g, 0.98 mmol) in toluene (10 ml) for 2 h. To the resulting green suspension, a solution of P₄C₄^tBu₄ (0.10 g, 0.25 mmol) in toluene (10 ml) was added. The reaction mixture was stirred for 30 min and a few drops of water were added. The suspension was then stirred overnight, after which the solvent was removed in vacuo. The residue was extraced with hexane, concentrated and stored at 243 K and yielded crystals of (I) in low yield (< 5%). Compound (II) was isolated (yield < 5%) by extraction of the residue with Et₂O, which was concentrated in vacuo. Storage at 243 K yielded suitable crystals.

S3. Refinement

In both compounds, methyl H atoms were placed in idealized positions [C—H = 0.96 Å] and refined as riding, with U_iso(H) values of 1.5U_eq(C). In (II), atom H4 attached to atom P4 was located from a difference Fourier map and refined isotropically, with the P—H distance restrained to 1.33 (2) Å. In (II), methine atom H1 was placed in an idealized position (C—H = 1.00 A) and refined as riding [U_iso(H) = 1.2 U_eq(C)], while atom H21 attached to atom P1 was treated in the same way as atom H4 in (I).

Computing details

For both compounds, data collection: COLLECT (Hooft, 2000); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The molecular structure of the cation of (I). Displacement ellipsoids are drawn at the 50% probability level and methyl H atoms have been omitted for clarity.
	Fig. 2. The molecular structure of (II). Displacement ellipsoids are drawn at the 50% probability level and methyl H atoms have been omitted for clarity.

(I) 4,6,7,8-tetra-tert-butyl-1,2,3-triphospha-5- phosphoniapentacyclo[3.2.1.0^2,4.0^3,8]oct-6-ene tetraiodogallate

Crystal data

(C20H37P4)[GaI4]	Z = 2
Mr = 978.70	F(000) = 920
Triclinic, P1	Dx = 2.001 Mg m^−3
a = 9.6290 (19) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.459 (3) Å	Cell parameters from 18935 reflections
c = 13.867 (3) Å	θ = 2.9–27.5°
α = 82.91 (3)°	µ = 4.85 mm^−1
β = 81.28 (3)°	T = 150 K
γ = 83.65 (3)°	Cut plate, yellow
V = 1624.6 (6) Å^3	0.15 × 0.15 × 0.07 mm

Data collection

Nonius KappaCCD diffractometer	7382 independent reflections
Radiation source: fine-focus sealed tube	5661 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.131
ϕ and ω scans to fill Ewald sphere	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	h = −12→12
Tmin = 0.471, Tmax = 0.712	k = −16→16
25682 measured reflections	l = −17→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.067P)^2 + 4.243P] where P = (Fo^2 + 2Fc^2)/3
7382 reflections	(Δ/σ)max = 0.001
277 parameters	Δρmax = 2.15 e Å^−3
1 restraint	Δρmin = −2.69 e Å^−3

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. Atom H4 attached to P4 was located from difference maps and its U(iso) set to 0.025, i.e. approximately 1.2 times that of P4. Its position refined satisfactorily using the DFIX command set at 1.33 Angstroms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	0.06047 (5)	0.85582 (4)	0.26162 (4)	0.03642 (14)
I2	0.32581 (6)	0.57923 (5)	0.20991 (6)	0.0664 (2)
I3	0.46260 (5)	0.88334 (5)	0.10629 (3)	0.04253 (16)
I4	0.42185 (5)	0.78986 (4)	0.40124 (3)	0.03937 (15)
Ga1	0.31709 (7)	0.77685 (6)	0.24522 (5)	0.02456 (17)
P1	0.07153 (18)	0.84752 (15)	0.57320 (12)	0.0280 (4)
P2	0.04906 (18)	0.68298 (16)	0.53638 (12)	0.0310 (4)
P3	0.22702 (16)	0.75207 (13)	0.66427 (11)	0.0226 (3)
P4	−0.02632 (16)	0.67533 (13)	0.73010 (11)	0.0205 (3)
C1	−0.0771 (6)	0.7636 (5)	0.6252 (4)	0.0220 (12)
C2	0.1318 (6)	0.6310 (5)	0.6555 (4)	0.0229 (12)
C3	0.1451 (7)	0.7832 (5)	0.7910 (4)	0.0221 (12)
C4	0.0230 (7)	0.7377 (5)	0.8288 (4)	0.0227 (12)
C5	−0.2302 (7)	0.8086 (6)	0.6138 (5)	0.0277 (14)
C6	−0.2347 (8)	0.8682 (7)	0.5109 (6)	0.0450 (19)
H6A	−0.3307	0.8924	0.5025	0.067*
H6B	−0.1956	0.8198	0.4628	0.067*
H6C	−0.1805	0.9297	0.5027	0.067*
C7	−0.3242 (7)	0.7149 (6)	0.6265 (6)	0.0345 (16)
H7A	−0.3235	0.6768	0.6911	0.052*
H7B	−0.2890	0.6658	0.5784	0.052*
H7C	−0.4190	0.7433	0.6182	0.052*
C8	−0.2828 (8)	0.8856 (7)	0.6898 (6)	0.044 (2)
H8A	−0.3757	0.9177	0.6802	0.067*
H8B	−0.2202	0.9417	0.6836	0.067*
H8C	−0.2861	0.8465	0.7542	0.067*
C9	0.2115 (7)	0.5172 (5)	0.6703 (5)	0.0313 (15)
C10	0.1171 (9)	0.4318 (7)	0.6586 (8)	0.056 (3)
H10A	0.1659	0.3609	0.6699	0.084*
H10B	0.0927	0.4422	0.5933	0.084*
H10C	0.0328	0.4380	0.7052	0.084*
C11	0.3435 (9)	0.5123 (7)	0.5934 (6)	0.047 (2)
H11A	0.4025	0.5668	0.6018	0.071*
H11B	0.3163	0.5254	0.5289	0.071*
H11C	0.3945	0.4419	0.6014	0.071*
C12	0.2548 (8)	0.4974 (6)	0.7718 (5)	0.0404 (17)
H12A	0.1722	0.5013	0.8201	0.061*
H12B	0.3146	0.5516	0.7795	0.061*
H12C	0.3051	0.4267	0.7802	0.061*
C13	0.2416 (7)	0.8565 (5)	0.8293 (5)	0.0272 (14)
C14	0.2933 (7)	0.9408 (6)	0.7443 (5)	0.0357 (16)
H14A	0.3536	0.9861	0.7667	0.054*
H14B	0.2137	0.9848	0.7221	0.054*
H14C	0.3450	0.9039	0.6913	0.054*
C15	0.3681 (7)	0.7807 (6)	0.8598 (6)	0.0372 (17)
H15A	0.4082	0.7388	0.8069	0.056*
H15B	0.3372	0.7327	0.9167	0.056*
H15C	0.4379	0.8231	0.8746	0.056*
C16	0.1758 (7)	0.9226 (6)	0.9143 (5)	0.0325 (15)
H16A	0.1429	0.8740	0.9704	0.049*
H16B	0.0979	0.9710	0.8947	0.049*
H16C	0.2454	0.9639	0.9310	0.049*
C17	−0.0675 (7)	0.7289 (6)	0.9314 (5)	0.0307 (15)
C18	−0.1839 (10)	0.6535 (7)	0.9350 (6)	0.046 (2)
H18A	−0.1425	0.5842	0.9161	0.069*
H18B	−0.2486	0.6849	0.8907	0.069*
H18C	−0.2335	0.6442	1.0006	0.069*
C19	−0.1423 (8)	0.8414 (7)	0.9559 (6)	0.0413 (18)
H19A	−0.2030	0.8689	0.9078	0.062*
H19B	−0.0728	0.8911	0.9554	0.062*
H19C	−0.1974	0.8336	1.0198	0.062*
C20	0.0272 (10)	0.6783 (7)	1.0085 (5)	0.045 (2)
H20A	−0.0279	0.6731	1.0724	0.068*
H20B	0.1023	0.7233	1.0079	0.068*
H20C	0.0664	0.6071	0.9934	0.068*
H4	−0.114 (6)	0.598 (4)	0.756 (4)	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0210 (2)	0.0424 (3)	0.0447 (3)	0.00242 (19)	−0.00730 (19)	−0.0019 (2)
I2	0.0357 (3)	0.0322 (3)	0.1383 (7)	−0.0013 (2)	−0.0245 (4)	−0.0235 (3)
I3	0.0358 (3)	0.0684 (4)	0.0254 (2)	−0.0226 (2)	−0.00118 (19)	−0.0007 (2)
I4	0.0297 (3)	0.0602 (3)	0.0272 (2)	0.0022 (2)	−0.00935 (19)	0.0003 (2)
Ga1	0.0176 (3)	0.0277 (4)	0.0287 (4)	−0.0029 (3)	−0.0049 (3)	−0.0014 (3)
P1	0.0191 (8)	0.0363 (9)	0.0293 (8)	−0.0060 (7)	−0.0070 (7)	0.0006 (7)
P2	0.0228 (9)	0.0468 (11)	0.0264 (8)	0.0010 (8)	−0.0067 (7)	−0.0158 (8)
P3	0.0144 (7)	0.0311 (9)	0.0238 (8)	−0.0012 (6)	−0.0031 (6)	−0.0088 (6)
P4	0.0143 (7)	0.0245 (8)	0.0240 (7)	−0.0010 (6)	−0.0034 (6)	−0.0076 (6)
C1	0.012 (3)	0.026 (3)	0.029 (3)	0.000 (2)	−0.004 (2)	−0.008 (2)
C2	0.017 (3)	0.029 (3)	0.024 (3)	0.001 (2)	−0.004 (2)	−0.009 (2)
C3	0.023 (3)	0.021 (3)	0.024 (3)	0.002 (2)	−0.008 (2)	−0.008 (2)
C4	0.023 (3)	0.023 (3)	0.023 (3)	0.001 (2)	−0.004 (2)	−0.007 (2)
C5	0.018 (3)	0.035 (4)	0.031 (3)	−0.001 (3)	−0.009 (3)	−0.002 (3)
C6	0.027 (4)	0.057 (5)	0.052 (5)	−0.003 (4)	−0.014 (3)	0.003 (4)
C7	0.017 (3)	0.037 (4)	0.051 (4)	−0.004 (3)	−0.009 (3)	−0.008 (3)
C8	0.029 (4)	0.046 (5)	0.063 (5)	0.009 (3)	−0.015 (4)	−0.024 (4)
C9	0.020 (3)	0.031 (4)	0.045 (4)	0.006 (3)	−0.006 (3)	−0.017 (3)
C10	0.035 (4)	0.034 (4)	0.107 (8)	−0.003 (4)	−0.012 (5)	−0.032 (5)
C11	0.045 (5)	0.047 (5)	0.047 (4)	0.018 (4)	0.001 (4)	−0.020 (4)
C12	0.038 (4)	0.036 (4)	0.044 (4)	0.012 (3)	−0.011 (3)	−0.002 (3)
C13	0.022 (3)	0.034 (4)	0.031 (3)	−0.002 (3)	−0.008 (3)	−0.018 (3)
C14	0.026 (4)	0.039 (4)	0.046 (4)	−0.002 (3)	−0.009 (3)	−0.021 (3)
C15	0.026 (4)	0.049 (4)	0.041 (4)	0.004 (3)	−0.013 (3)	−0.020 (3)
C16	0.023 (3)	0.038 (4)	0.041 (4)	0.002 (3)	−0.009 (3)	−0.020 (3)
C17	0.032 (4)	0.037 (4)	0.021 (3)	−0.001 (3)	0.001 (3)	−0.007 (3)
C18	0.056 (5)	0.046 (5)	0.037 (4)	−0.022 (4)	0.009 (4)	−0.011 (3)
C19	0.031 (4)	0.048 (5)	0.043 (4)	−0.002 (3)	0.010 (3)	−0.020 (4)
C20	0.061 (6)	0.049 (5)	0.022 (3)	0.001 (4)	−0.002 (3)	−0.004 (3)

Geometric parameters (Å, º)

I1—Ga1	2.5442 (11)	C9—C11	1.531 (10)
I2—Ga1	2.5590 (10)	C10—H10A	0.9600
I3—Ga1	2.5290 (12)	C10—H10B	0.9600
I4—Ga1	2.5513 (10)	C10—H10C	0.9600
P1—C1	1.869 (6)	C11—H11A	0.9600
P1—P2	2.214 (3)	C11—H11B	0.9600
P1—P3	2.249 (2)	C11—H11C	0.9600
P2—C1	1.893 (6)	C12—H12A	0.9600
P2—C2	1.950 (6)	C12—H12B	0.9600
P3—C2	1.875 (6)	C12—H12C	0.9600
P3—C3	1.882 (6)	C13—C15	1.535 (10)
P4—C2	1.781 (6)	C13—C16	1.539 (8)
P4—C4	1.801 (6)	C13—C14	1.540 (10)
P4—C1	1.807 (7)	C14—H14A	0.9600
P4—H4	1.33 (2)	C14—H14B	0.9600
C1—C5	1.542 (8)	C14—H14C	0.9600
C2—C9	1.542 (9)	C15—H15A	0.9600
C3—C4	1.366 (9)	C15—H15B	0.9600
C3—C13	1.561 (8)	C15—H15C	0.9600
C4—C17	1.550 (9)	C16—H16A	0.9600
C5—C8	1.507 (10)	C16—H16B	0.9600
C5—C6	1.529 (10)	C16—H16C	0.9600
C5—C7	1.533 (9)	C17—C18	1.531 (10)
C6—H6A	0.9600	C17—C20	1.542 (11)
C6—H6B	0.9600	C17—C19	1.555 (10)
C6—H6C	0.9600	C18—H18A	0.9600
C7—H7A	0.9600	C18—H18B	0.9600
C7—H7B	0.9600	C18—H18C	0.9600
C7—H7C	0.9600	C19—H19A	0.9600
C8—H8A	0.9600	C19—H19B	0.9600
C8—H8B	0.9600	C19—H19C	0.9600
C8—H8C	0.9600	C20—H20A	0.9600
C9—C10	1.511 (10)	C20—H20B	0.9600
C9—C12	1.512 (10)	C20—H20C	0.9600
I3—Ga1—I1	110.29 (4)	C11—C9—C2	108.2 (6)
I3—Ga1—I4	106.99 (3)	C9—C10—H10A	109.5
I1—Ga1—I4	110.60 (4)	C9—C10—H10B	109.5
I3—Ga1—I2	109.85 (4)	H10A—C10—H10B	109.5
I1—Ga1—I2	107.91 (4)	C9—C10—H10C	109.5
I4—Ga1—I2	111.21 (4)	H10A—C10—H10C	109.5
C1—P1—P2	54.46 (19)	H10B—C10—H10C	109.5
C1—P1—P3	94.8 (2)	C9—C11—H11A	109.5
P2—P1—P3	81.26 (9)	C9—C11—H11B	109.5
C1—P2—C2	81.5 (3)	H11A—C11—H11B	109.5
C1—P2—P1	53.5 (2)	C9—C11—H11C	109.5
C2—P2—P1	85.4 (2)	H11A—C11—H11C	109.5
C2—P3—C3	98.9 (3)	H11B—C11—H11C	109.5
C2—P3—P1	86.2 (2)	C9—C12—H12A	109.5
C3—P3—P1	100.8 (2)	C9—C12—H12B	109.5
C2—P4—C4	107.6 (3)	H12A—C12—H12B	109.5
C2—P4—C1	88.8 (3)	C9—C12—H12C	109.5
C4—P4—C1	117.7 (3)	H12A—C12—H12C	109.5
C2—P4—H4	113 (3)	H12B—C12—H12C	109.5
C4—P4—H4	116 (3)	C15—C13—C16	109.6 (5)
C1—P4—H4	110 (3)	C15—C13—C14	109.5 (6)
C5—C1—P4	124.4 (4)	C16—C13—C14	105.5 (6)
C5—C1—P1	119.8 (5)	C15—C13—C3	106.0 (5)
P4—C1—P1	108.4 (3)	C16—C13—C3	117.6 (5)
C5—C1—P2	126.6 (4)	C14—C13—C3	108.5 (5)
P4—C1—P2	92.2 (3)	C13—C14—H14A	109.5
P1—C1—P2	72.1 (2)	C13—C14—H14B	109.5
C9—C2—P4	124.3 (5)	H14A—C14—H14B	109.5
C9—C2—P3	118.2 (4)	C13—C14—H14C	109.5
P4—C2—P3	95.5 (3)	H14A—C14—H14C	109.5
C9—C2—P2	122.1 (4)	H14B—C14—H14C	109.5
P4—C2—P2	91.2 (3)	C13—C15—H15A	109.5
P3—C2—P2	98.9 (3)	C13—C15—H15B	109.5
C4—C3—C13	135.0 (5)	H15A—C15—H15B	109.5
C4—C3—P3	116.6 (4)	C13—C15—H15C	109.5
C13—C3—P3	108.3 (4)	H15A—C15—H15C	109.5
C3—C4—C17	134.0 (5)	H15B—C15—H15C	109.5
C3—C4—P4	105.7 (4)	C13—C16—H16A	109.5
C17—C4—P4	120.3 (5)	C13—C16—H16B	109.5
C8—C5—C6	110.0 (6)	H16A—C16—H16B	109.5
C8—C5—C7	110.1 (6)	C13—C16—H16C	109.5
C6—C5—C7	108.2 (6)	H16A—C16—H16C	109.5
C8—C5—C1	109.1 (5)	H16B—C16—H16C	109.5
C6—C5—C1	109.6 (5)	C18—C17—C20	107.1 (6)
C7—C5—C1	109.8 (5)	C18—C17—C4	110.8 (5)
C5—C6—H6A	109.5	C20—C17—C4	109.0 (6)
C5—C6—H6B	109.5	C18—C17—C19	106.7 (6)
H6A—C6—H6B	109.5	C20—C17—C19	112.0 (6)
C5—C6—H6C	109.5	C4—C17—C19	111.3 (6)
H6A—C6—H6C	109.5	C17—C18—H18A	109.5
H6B—C6—H6C	109.5	C17—C18—H18B	109.5
C5—C7—H7A	109.5	H18A—C18—H18B	109.5
C5—C7—H7B	109.5	C17—C18—H18C	109.5
H7A—C7—H7B	109.5	H18A—C18—H18C	109.5
C5—C7—H7C	109.5	H18B—C18—H18C	109.5
H7A—C7—H7C	109.5	C17—C19—H19A	109.5
H7B—C7—H7C	109.5	C17—C19—H19B	109.5
C5—C8—H8A	109.5	H19A—C19—H19B	109.5
C5—C8—H8B	109.5	C17—C19—H19C	109.5
H8A—C8—H8B	109.5	H19A—C19—H19C	109.5
C5—C8—H8C	109.5	H19B—C19—H19C	109.5
H8A—C8—H8C	109.5	C17—C20—H20A	109.5
H8B—C8—H8C	109.5	C17—C20—H20B	109.5
C10—C9—C12	109.2 (7)	H20A—C20—H20B	109.5
C10—C9—C11	110.4 (6)	C17—C20—H20C	109.5
C12—C9—C11	109.3 (6)	H20A—C20—H20C	109.5
C10—C9—C2	109.7 (6)	H20B—C20—H20C	109.5
C12—C9—C2	110.0 (5)
P3—P1—P2—C1	102.4 (2)	P1—P3—C3—C4	70.6 (5)
C1—P1—P2—C2	−82.9 (3)	C2—P3—C3—C13	161.5 (4)
P3—P1—P2—C2	19.49 (19)	P1—P3—C3—C13	−110.8 (4)
C1—P1—P3—C2	32.6 (3)	C13—C3—C4—C17	−7.4 (13)
P2—P1—P3—C2	−20.28 (19)	P3—C3—C4—C17	170.7 (6)
C1—P1—P3—C3	−65.7 (3)	C13—C3—C4—P4	174.6 (6)
P2—P1—P3—C3	−118.6 (2)	P3—C3—C4—P4	−7.3 (6)
C2—P4—C1—C5	158.2 (5)	C2—P4—C4—C3	31.7 (5)
C4—P4—C1—C5	−92.5 (5)	C1—P4—C4—C3	−66.5 (5)
C2—P4—C1—P1	−52.1 (3)	C2—P4—C4—C17	−146.7 (5)
C4—P4—C1—P1	57.2 (4)	C1—P4—C4—C17	115.1 (5)
C2—P4—C1—P2	19.7 (3)	P4—C1—C5—C8	66.6 (7)
C4—P4—C1—P2	129.1 (3)	P1—C1—C5—C8	−79.9 (7)
P2—P1—C1—C5	−122.4 (5)	P2—C1—C5—C8	−169.0 (5)
P3—P1—C1—C5	161.9 (4)	P4—C1—C5—C6	−173.0 (5)
P2—P1—C1—P4	86.3 (3)	P1—C1—C5—C6	40.5 (7)
P3—P1—C1—P4	10.6 (3)	P2—C1—C5—C6	−48.5 (8)
P3—P1—C1—P2	−75.67 (16)	P4—C1—C5—C7	−54.2 (7)
C2—P2—C1—C5	−155.2 (6)	P1—C1—C5—C7	159.3 (5)
P1—P2—C1—C5	114.2 (6)	P2—C1—C5—C7	70.2 (7)
C2—P2—C1—P4	−18.1 (3)	P4—C2—C9—C10	61.1 (8)
P1—P2—C1—P4	−108.7 (3)	P3—C2—C9—C10	−179.1 (6)
C2—P2—C1—P1	90.5 (2)	P2—C2—C9—C10	−56.1 (8)
C4—P4—C2—C9	91.0 (6)	P4—C2—C9—C12	−59.0 (7)
C1—P4—C2—C9	−150.3 (5)	P3—C2—C9—C12	60.8 (7)
C4—P4—C2—P3	−38.8 (3)	P2—C2—C9—C12	−176.3 (5)
C1—P4—C2—P3	79.9 (3)	P4—C2—C9—C11	−178.4 (5)
C4—P4—C2—P2	−137.8 (3)	P3—C2—C9—C11	−58.6 (7)
C1—P4—C2—P2	−19.1 (3)	P2—C2—C9—C11	64.3 (7)
C3—P3—C2—C9	−102.5 (5)	C4—C3—C13—C15	101.7 (8)
P1—P3—C2—C9	157.2 (5)	P3—C3—C13—C15	−76.5 (6)
C3—P3—C2—P4	31.5 (3)	C4—C3—C13—C16	−21.3 (11)
P1—P3—C2—P4	−68.9 (2)	P3—C3—C13—C16	160.5 (5)
C3—P3—C2—P2	123.5 (3)	C4—C3—C13—C14	−140.9 (7)
P1—P3—C2—P2	23.2 (2)	P3—C3—C13—C14	40.9 (6)
C1—P2—C2—C9	151.2 (6)	C3—C4—C17—C18	−171.7 (7)
P1—P2—C2—C9	−155.1 (5)	P4—C4—C17—C18	6.1 (8)
C1—P2—C2—P4	18.4 (3)	C3—C4—C17—C20	−54.1 (10)
P1—P2—C2—P4	72.1 (2)	P4—C4—C17—C20	123.7 (6)
C1—P2—C2—P3	−77.3 (3)	C3—C4—C17—C19	69.8 (10)
P1—P2—C2—P3	−23.6 (2)	P4—C4—C17—C19	−112.3 (6)
C2—P3—C3—C4	−17.1 (5)

(II) triiodo(3,5,7,8-tetra-tert-butyl-1,2,4λ⁵,6- tetraphosphatetracyclo[4.1.1.0^2,5.0^7,8]octan-4-one)gallium

Crystal data

[GaI3(C20H38OP4)]	F(000) = 1664
Mr = 868.80	Dx = 1.903 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.082 (2) Å	Cell parameters from 66215 reflections
b = 17.522 (4) Å	θ = 2.9–27.5°
c = 14.615 (3) Å	µ = 4.18 mm^−1
β = 101.47 (3)°	T = 150 K
V = 3032.2 (10) Å^3	Square prism, yellow
Z = 4	0.30 × 0.30 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer	6923 independent reflections
Radiation source: fine-focus sealed tube	6141 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.132
ϕ and ω scans to fill Ewald sphere	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	h = −15→15
Tmin = 0.302, Tmax = 0.658	k = −22→22
50118 measured reflections	l = −18→18

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.081	w = 1/[σ^2(Fo^2) + (0.01P)^2 + 7.857P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.002
6923 reflections	Δρmax = 1.12 e Å^−3
279 parameters	Δρmin = −1.48 e Å^−3
13 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00049 (10)

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. H(21) was located from difference maps, its distance from P(1) was fixed at 1.33 angstroms using the DFIX command. Its U(iso) was allowed to refine freely.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	0.39969 (2)	0.181500 (18)	0.98121 (2)	0.03477 (9)
I2	0.18517 (2)	0.160647 (17)	1.174780 (16)	0.03093 (9)
I3	0.07776 (3)	0.286179 (16)	0.923772 (19)	0.03541 (9)
Ga1	0.19902 (3)	0.18115 (2)	1.00780 (3)	0.01995 (10)
P1	0.14428 (7)	0.05323 (5)	0.85233 (6)	0.01767 (18)
P2	0.09661 (8)	−0.06783 (5)	0.75099 (6)	0.01818 (19)
P3	0.18704 (8)	−0.03818 (6)	0.63786 (6)	0.01996 (19)
P4	0.35355 (7)	−0.03525 (6)	0.81141 (6)	0.01871 (19)
O1	0.1368 (2)	0.09132 (15)	0.94456 (17)	0.0231 (5)
C1	0.0151 (3)	0.0187 (2)	0.7819 (2)	0.0180 (7)
H1	−0.0316	−0.0001	0.8266	0.022*
C2	0.2140 (3)	−0.0388 (2)	0.8517 (2)	0.0169 (7)
C3	0.3209 (3)	0.0075 (2)	0.6955 (2)	0.0203 (7)
C4	0.3224 (3)	−0.0800 (2)	0.6950 (2)	0.0198 (7)
C5	−0.0650 (3)	0.0674 (2)	0.7090 (2)	0.0219 (7)
C6	−0.1407 (4)	0.1146 (3)	0.7597 (3)	0.0384 (11)
H6A	−0.0938	0.1481	0.8053	0.058*
H6B	−0.1843	0.0803	0.7920	0.058*
H6C	−0.1924	0.1455	0.7142	0.058*
C7	−0.0021 (4)	0.1205 (3)	0.6549 (3)	0.0367 (10)
H7A	0.0430	0.1567	0.6980	0.055*
H7B	−0.0566	0.1486	0.6082	0.055*
H7C	0.0478	0.0905	0.6234	0.055*
C8	−0.1379 (4)	0.0118 (3)	0.6406 (3)	0.0358 (10)
H8A	−0.1945	0.0407	0.5967	0.054*
H8B	−0.1759	−0.0241	0.6755	0.054*
H8C	−0.0896	−0.0165	0.6059	0.054*
C9	0.2241 (3)	−0.0897 (2)	0.9418 (2)	0.0223 (8)
C10	0.1118 (3)	−0.0947 (3)	0.9740 (3)	0.0292 (9)
H10A	0.0549	−0.1178	0.9245	0.044*
H10B	0.0873	−0.0433	0.9877	0.044*
H10C	0.1209	−0.1262	1.0304	0.044*
C11	0.2592 (4)	−0.1702 (2)	0.9198 (3)	0.0321 (9)
H11A	0.2646	−0.2024	0.9754	0.048*
H11B	0.3327	−0.1684	0.9012	0.048*
H11C	0.2027	−0.1916	0.8688	0.048*
C12	0.3137 (3)	−0.0553 (3)	1.0219 (3)	0.0279 (8)
H12A	0.3181	−0.0863	1.0784	0.042*
H12B	0.2922	−0.0030	1.0344	0.042*
H12C	0.3875	−0.0549	1.0037	0.042*
C13	0.3834 (3)	0.0721 (2)	0.6566 (3)	0.0252 (8)
C14	0.5095 (5)	0.0663 (4)	0.6922 (5)	0.0667 (17)
H14A	0.5257	0.0666	0.7606	0.100*
H14B	0.5471	0.1098	0.6692	0.100*
H14C	0.5375	0.0187	0.6698	0.100*
C15	0.3401 (5)	0.1479 (3)	0.6869 (3)	0.0425 (11)
H15A	0.3543	0.1504	0.7552	0.064*
H15B	0.2588	0.1521	0.6621	0.064*
H15C	0.3794	0.1901	0.6629	0.064*
C16	0.3582 (5)	0.0716 (3)	0.5494 (3)	0.0486 (13)
H16A	0.3926	0.1165	0.5264	0.073*
H16B	0.2763	0.0727	0.5263	0.073*
H16C	0.3896	0.0252	0.5271	0.073*
C17	0.3846 (3)	−0.1458 (2)	0.6584 (3)	0.0273 (8)
C18	0.5085 (4)	−0.1476 (4)	0.7065 (4)	0.0572 (15)
H18A	0.5462	−0.1015	0.6903	0.086*
H18B	0.5447	−0.1927	0.6859	0.086*
H18C	0.5142	−0.1498	0.7743	0.086*
C19	0.3284 (6)	−0.2198 (3)	0.6802 (4)	0.0519 (14)
H19A	0.3393	−0.2263	0.7480	0.078*
H19B	0.3625	−0.2630	0.6533	0.078*
H19C	0.2475	−0.2177	0.6532	0.078*
C20	0.3734 (4)	−0.1403 (3)	0.5526 (3)	0.0375 (10)
H20A	0.2935	−0.1359	0.5229	0.056*
H20B	0.4054	−0.1863	0.5296	0.056*
H20C	0.4144	−0.0953	0.5373	0.056*
H21	0.192 (3)	0.097 (2)	0.796 (3)	0.033 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.02387 (14)	0.04394 (19)	0.03882 (16)	−0.00591 (11)	0.01181 (11)	−0.00404 (13)
I2	0.03157 (15)	0.04094 (18)	0.01973 (13)	−0.01160 (11)	0.00377 (10)	0.00137 (11)
I3	0.04414 (17)	0.02641 (16)	0.03408 (15)	0.00774 (12)	0.00391 (12)	0.00569 (11)
Ga1	0.0217 (2)	0.0192 (2)	0.01904 (19)	−0.00196 (15)	0.00436 (15)	−0.00208 (16)
P1	0.0173 (4)	0.0179 (4)	0.0177 (4)	0.0000 (3)	0.0032 (3)	−0.0011 (4)
P2	0.0186 (4)	0.0173 (5)	0.0177 (4)	−0.0013 (3)	0.0013 (3)	−0.0003 (3)
P3	0.0182 (4)	0.0246 (5)	0.0163 (4)	0.0020 (4)	0.0017 (3)	−0.0002 (4)
P4	0.0164 (4)	0.0209 (5)	0.0182 (4)	0.0010 (3)	0.0020 (3)	−0.0003 (4)
O1	0.0235 (13)	0.0224 (14)	0.0239 (12)	−0.0029 (11)	0.0059 (10)	−0.0065 (11)
C1	0.0207 (16)	0.0181 (18)	0.0145 (15)	−0.0010 (13)	0.0018 (13)	−0.0005 (13)
C2	0.0177 (16)	0.0168 (17)	0.0161 (15)	−0.0009 (13)	0.0030 (12)	0.0008 (13)
C3	0.0219 (17)	0.0184 (18)	0.0206 (16)	0.0015 (14)	0.0039 (13)	−0.0003 (14)
C4	0.0194 (17)	0.0191 (18)	0.0206 (16)	0.0002 (14)	0.0037 (13)	0.0001 (14)
C5	0.0203 (17)	0.0240 (19)	0.0197 (17)	0.0051 (14)	0.0004 (14)	0.0006 (15)
C6	0.031 (2)	0.051 (3)	0.031 (2)	0.018 (2)	0.0021 (17)	−0.002 (2)
C7	0.033 (2)	0.034 (2)	0.044 (2)	0.0078 (19)	0.0086 (19)	0.020 (2)
C8	0.039 (2)	0.035 (2)	0.027 (2)	−0.0019 (19)	−0.0095 (18)	0.0033 (18)
C9	0.0264 (18)	0.024 (2)	0.0158 (16)	0.0010 (15)	0.0023 (14)	0.0038 (15)
C10	0.029 (2)	0.037 (2)	0.0223 (18)	−0.0027 (17)	0.0058 (15)	0.0070 (17)
C11	0.042 (2)	0.024 (2)	0.028 (2)	0.0034 (18)	0.0019 (17)	0.0048 (17)
C12	0.029 (2)	0.033 (2)	0.0199 (17)	0.0025 (17)	0.0005 (15)	0.0011 (17)
C13	0.0242 (18)	0.024 (2)	0.0291 (19)	−0.0017 (15)	0.0091 (15)	0.0020 (16)
C14	0.038 (3)	0.068 (3)	0.091 (4)	−0.011 (2)	0.006 (2)	0.034 (3)
C15	0.065 (3)	0.026 (2)	0.044 (3)	−0.010 (2)	0.028 (2)	−0.003 (2)
C16	0.085 (4)	0.035 (3)	0.035 (2)	−0.011 (3)	0.035 (3)	−0.002 (2)
C17	0.0269 (19)	0.029 (2)	0.0252 (18)	0.0092 (16)	0.0047 (15)	−0.0043 (17)
C18	0.040 (2)	0.065 (3)	0.061 (3)	0.021 (2)	−0.003 (2)	−0.030 (3)
C19	0.089 (4)	0.024 (2)	0.051 (3)	0.013 (2)	0.034 (3)	0.002 (2)
C20	0.057 (3)	0.031 (2)	0.030 (2)	0.011 (2)	0.019 (2)	−0.0039 (19)

Geometric parameters (Å, º)

I1—Ga1	2.5305 (7)	C9—C11	1.526 (6)
I2—Ga1	2.5050 (7)	C9—C12	1.550 (5)
I3—Ga1	2.5152 (7)	C10—H10A	0.9800
Ga1—O1	1.903 (3)	C10—H10B	0.9800
P1—O1	1.523 (3)	C10—H10C	0.9800
P1—C1	1.795 (4)	C11—H11A	0.9800
P1—C2	1.819 (4)	C11—H11B	0.9800
P1—H21	1.33 (2)	C11—H11C	0.9800
P2—C2	1.899 (3)	C12—H12A	0.9800
P2—C1	1.911 (4)	C12—H12B	0.9800
P2—P3	2.2171 (14)	C12—H12C	0.9800
P3—C4	1.835 (4)	C13—C14	1.512 (7)
P3—C3	1.851 (4)	C13—C16	1.535 (6)
P4—C3	1.823 (4)	C13—C15	1.526 (6)
P4—C4	1.842 (4)	C14—H14A	0.9800
P4—C2	1.895 (4)	C14—H14B	0.9800
C1—C5	1.545 (5)	C14—H14C	0.9800
C1—H1	1.0000	C15—H15A	0.9800
C2—C9	1.575 (5)	C15—H15B	0.9800
C3—C13	1.531 (5)	C15—H15C	0.9800
C3—C4	1.534 (5)	C16—H16A	0.9800
C4—C17	1.530 (5)	C16—H16B	0.9800
C5—C7	1.520 (6)	C16—H16C	0.9800
C5—C6	1.529 (6)	C17—C19	1.526 (7)
C5—C8	1.541 (6)	C17—C20	1.529 (5)
C6—H6A	0.9800	C17—C18	1.522 (6)
C6—H6B	0.9800	C18—H18A	0.9800
C6—H6C	0.9800	C18—H18B	0.9800
C7—H7A	0.9800	C18—H18C	0.9800
C7—H7B	0.9800	C19—H19A	0.9800
C7—H7C	0.9800	C19—H19B	0.9800
C8—H8A	0.9800	C19—H19C	0.9800
C8—H8B	0.9800	C20—H20A	0.9800
C8—H8C	0.9800	C20—H20B	0.9800
C9—C10	1.525 (5)	C20—H20C	0.9800
O1—Ga1—I2	104.97 (8)	C10—C9—C12	108.7 (3)
O1—Ga1—I3	103.46 (8)	C11—C9—C12	109.7 (3)
I2—Ga1—I3	115.81 (2)	C10—C9—C2	111.4 (3)
O1—Ga1—I1	103.02 (8)	C11—C9—C2	109.0 (3)
I2—Ga1—I1	113.68 (3)	C12—C9—C2	109.8 (3)
I3—Ga1—I1	113.96 (2)	C9—C10—H10A	109.5
O1—P1—C1	117.21 (16)	C9—C10—H10B	109.5
O1—P1—C2	120.11 (15)	H10A—C10—H10B	109.5
C1—P1—C2	92.83 (16)	C9—C10—H10C	109.5
O1—P1—H21	114 (2)	H10A—C10—H10C	109.5
C1—P1—H21	105.7 (19)	H10B—C10—H10C	109.5
C2—P1—H21	104 (2)	C9—C11—H11A	109.5
C2—P2—C1	86.80 (15)	C9—C11—H11B	109.5
C2—P2—P3	96.46 (11)	H11A—C11—H11B	109.5
C1—P2—P3	110.13 (12)	C9—C11—H11C	109.5
C4—P3—C3	49.18 (16)	H11A—C11—H11C	109.5
C4—P3—P2	95.39 (12)	H11B—C11—H11C	109.5
C3—P3—P2	106.12 (12)	C9—C12—H12A	109.5
C3—P4—C4	49.47 (16)	C9—C12—H12B	109.5
C3—P4—C2	105.11 (16)	H12A—C12—H12B	109.5
C4—P4—C2	104.02 (16)	C9—C12—H12C	109.5
P1—O1—Ga1	134.87 (17)	H12A—C12—H12C	109.5
C5—C1—P1	124.3 (3)	H12B—C12—H12C	109.5
C5—C1—P2	123.8 (2)	C14—C13—C16	109.4 (4)
P1—C1—P2	88.42 (16)	C14—C13—C15	109.8 (4)
C5—C1—H1	106.0	C16—C13—C15	107.0 (4)
P1—C1—H1	106.0	C14—C13—C3	111.1 (4)
P2—C1—H1	106.0	C16—C13—C3	111.2 (3)
C9—C2—P1	117.2 (2)	C15—C13—C3	108.2 (3)
C9—C2—P2	114.7 (2)	C13—C14—H14A	109.5
P1—C2—P2	88.09 (15)	C13—C14—H14B	109.5
C9—C2—P4	110.6 (2)	H14A—C14—H14B	109.5
P1—C2—P4	114.46 (18)	C13—C14—H14C	109.5
P2—C2—P4	109.96 (17)	H14A—C14—H14C	109.5
C13—C3—C4	136.9 (3)	H14B—C14—H14C	109.5
C13—C3—P4	128.1 (3)	C13—C15—H15A	109.5
C4—C3—P4	65.94 (19)	C13—C15—H15B	109.5
C13—C3—P3	127.0 (3)	H15A—C15—H15B	109.5
C4—C3—P3	64.87 (19)	C13—C15—H15C	109.5
P4—C3—P3	104.66 (19)	H15A—C15—H15C	109.5
C17—C4—C3	139.7 (3)	H15B—C15—H15C	109.5
C17—C4—P3	126.6 (3)	C13—C16—H16A	109.5
C3—C4—P3	65.95 (19)	C13—C16—H16B	109.5
C17—C4—P4	128.3 (3)	H16A—C16—H16B	109.5
C3—C4—P4	64.59 (19)	C13—C16—H16C	109.5
P3—C4—P4	104.50 (18)	H16A—C16—H16C	109.5
C7—C5—C6	109.2 (4)	H16B—C16—H16C	109.5
C7—C5—C8	109.3 (3)	C19—C17—C20	108.1 (4)
C6—C5—C8	109.7 (4)	C19—C17—C4	107.4 (3)
C7—C5—C1	112.8 (3)	C20—C17—C4	110.9 (3)
C6—C5—C1	108.5 (3)	C19—C17—C18	108.8 (4)
C8—C5—C1	107.3 (3)	C20—C17—C18	110.4 (4)
C5—C6—H6A	109.5	C4—C17—C18	111.1 (3)
C5—C6—H6B	109.5	C17—C18—H18A	109.5
H6A—C6—H6B	109.5	C17—C18—H18B	109.5
C5—C6—H6C	109.5	H18A—C18—H18B	109.5
H6A—C6—H6C	109.5	C17—C18—H18C	109.5
H6B—C6—H6C	109.5	H18A—C18—H18C	109.5
C5—C7—H7A	109.5	H18B—C18—H18C	109.5
C5—C7—H7B	109.5	C17—C19—H19A	109.5
H7A—C7—H7B	109.5	C17—C19—H19B	109.5
C5—C7—H7C	109.5	H19A—C19—H19B	109.5
H7A—C7—H7C	109.5	C17—C19—H19C	109.5
H7B—C7—H7C	109.5	H19A—C19—H19C	109.5
C5—C8—H8A	109.5	H19B—C19—H19C	109.5
C5—C8—H8B	109.5	C17—C20—H20A	109.5
H8A—C8—H8B	109.5	C17—C20—H20B	109.5
C5—C8—H8C	109.5	H20A—C20—H20B	109.5
H8A—C8—H8C	109.5	C17—C20—H20C	109.5
H8B—C8—H8C	109.5	H20A—C20—H20C	109.5
C10—C9—C11	108.2 (3)	H20B—C20—H20C	109.5
C2—P2—P3—C4	43.55 (16)	C13—C3—C4—P3	−118.1 (4)
C1—P2—P3—C4	132.50 (16)	P4—C3—C4—P3	121.03 (16)
C2—P2—P3—C3	−5.44 (17)	C13—C3—C4—P4	120.8 (4)
C1—P2—P3—C3	83.51 (17)	P3—C3—C4—P4	−121.03 (16)
C1—P1—O1—Ga1	−135.4 (2)	C3—P3—C4—C17	−135.1 (4)
C2—P1—O1—Ga1	113.4 (2)	P2—P3—C4—C17	118.2 (3)
I2—Ga1—O1—P1	−160.3 (2)	P2—P3—C4—C3	−106.68 (18)
I3—Ga1—O1—P1	77.9 (2)	C3—P3—C4—P4	53.08 (19)
I1—Ga1—O1—P1	−41.0 (2)	P2—P3—C4—P4	−53.60 (16)
O1—P1—C1—C5	87.8 (3)	C3—P4—C4—C17	134.5 (4)
C2—P1—C1—C5	−146.0 (3)	C2—P4—C4—C17	−127.5 (3)
O1—P1—C1—P2	−141.31 (15)	C2—P4—C4—C3	98.1 (2)
C2—P1—C1—P2	−15.14 (15)	C3—P4—C4—P3	−53.9 (2)
C2—P2—C1—C5	145.8 (3)	C2—P4—C4—P3	44.1 (2)
P3—P2—C1—C5	50.1 (3)	P1—C1—C5—C7	38.7 (4)
C2—P2—C1—P1	14.50 (15)	P2—C1—C5—C7	−75.9 (4)
P3—P2—C1—P1	−81.22 (13)	P1—C1—C5—C6	−82.5 (4)
O1—P1—C2—C9	22.2 (3)	P2—C1—C5—C6	162.9 (3)
C1—P1—C2—C9	−101.7 (3)	P1—C1—C5—C8	159.1 (3)
O1—P1—C2—P2	139.15 (14)	P2—C1—C5—C8	44.5 (4)
C1—P1—C2—P2	15.24 (16)	P1—C2—C9—C10	47.7 (4)
O1—P1—C2—P4	−109.7 (2)	P2—C2—C9—C10	−53.6 (4)
C1—P1—C2—P4	126.35 (19)	P4—C2—C9—C10	−178.7 (3)
C1—P2—C2—C9	104.9 (3)	P1—C2—C9—C11	167.0 (3)
P3—P2—C2—C9	−145.2 (2)	P2—C2—C9—C11	65.8 (4)
C1—P2—C2—P1	−14.30 (15)	P4—C2—C9—C11	−59.3 (3)
P3—P2—C2—P1	95.61 (11)	P1—C2—C9—C12	−72.7 (3)
C1—P2—C2—P4	−129.69 (19)	P2—C2—C9—C12	−174.0 (3)
P3—P2—C2—P4	−19.78 (17)	P4—C2—C9—C12	60.9 (3)
C3—P4—C2—C9	168.3 (2)	C4—C3—C13—C14	−57.7 (6)
C4—P4—C2—C9	117.1 (2)	P4—C3—C13—C14	36.9 (5)
C3—P4—C2—P1	−56.7 (2)	P3—C3—C13—C14	−149.2 (4)
C4—P4—C2—P1	−107.9 (2)	C4—C3—C13—C16	64.5 (6)
C3—P4—C2—P2	40.6 (2)	P4—C3—C13—C16	159.0 (3)
C4—P4—C2—P2	−10.7 (2)	P3—C3—C13—C16	−27.1 (5)
C4—P4—C3—C13	−131.7 (4)	C4—C3—C13—C15	−178.3 (4)
C2—P4—C3—C13	132.6 (3)	P4—C3—C13—C15	−83.8 (4)
C2—P4—C3—C4	−95.7 (2)	P3—C3—C13—C15	90.2 (4)
C4—P4—C3—P3	53.31 (19)	C3—C4—C17—C19	−175.0 (4)
C2—P4—C3—P3	−42.4 (2)	P3—C4—C17—C19	−79.7 (4)
C4—P3—C3—C13	131.0 (4)	P4—C4—C17—C19	90.1 (4)
P2—P3—C3—C13	−145.9 (3)	C3—C4—C17—C20	−57.1 (6)
P2—P3—C3—C4	83.08 (18)	P3—C4—C17—C20	38.2 (5)
C4—P3—C3—P4	−53.98 (19)	P4—C4—C17—C20	−152.0 (3)
P2—P3—C3—P4	29.10 (19)	C3—C4—C17—C18	66.1 (6)
C13—C3—C4—C17	0.8 (8)	P3—C4—C17—C18	161.4 (4)
P4—C3—C4—C17	−120.0 (5)	P4—C4—C17—C18	−28.8 (5)
P3—C3—C4—C17	119.0 (5)