(Di-tert-butyl­phosphan­yl)bis­(diphenyl­phosphan­yl)phosphane

Wisniewska, A.; Baranowska, K.; Matern, E.; Pikies, J.

doi:10.1107/S1600536808019077

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1364

doi:10.1107/S1600536808019077

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(Di-tert-butylphosphanyl)bis(diphenylphosphanyl)phosphane

Aleksandra Wisniewska,^a Katarzyna Baranowska,^a ^* Eberhard Matern ^b and Jerzy Pikies ^a

^aDepartment of Inorganic Chemistry, Gdańsk University of Technology, 11/12 G. Narutowicz St. 80952-PL Gdańsk, Poland, and ^bInstitute for Inorganic Chemistry, University of Karlsruhe, 15 G. Engesserstrasse St., 76131 Karlsruhe, Germany
^*Correspondence e-mail: kasiab29@wp.pl

(Received 20 June 2008; accepted 24 June 2008; online 28 June 2008)

The title phosphane, C₃₂H₃₈P₄ or (Ph₂P)₂P(P^tBu₂), has a P atom that is linked to another three P atoms in a pyramidal configuration; the P—P distances in the range 2.2231 (7)–2.2446 (7) Å indicate that the P—P bonds are single bonds.

Related literature

For the synthesis of silylated triphosphanes, see: Kovacs et al. (1996 ). For other similar pyramidal isotetraphosphanes, see: Cowley et al. (1997 ); Fritz et al. (1987 ); Jones et al. (2002 ). For planar (^tBu₂P)₃P, see: Fritz et al. (1999 ). For evaluation of NMR data, see: Bruker (1999 ); Hägele et al. (1987 ).

Experimental

Crystal data

C₃₂H₃₈P₄
M_r = 546.5
Triclinic, $[P \overline 1]$
a = 10.0161 (6) Å
b = 11.9258 (7) Å
c = 12.9951 (7) Å
α = 104.831 (5)°
β = 100.201 (5)°
γ = 90.900 (5)°
V = 1473.79 (15) Å³
Z = 2
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 120 (2) K
0.32 × 0.15 × 0.13 mm

Data collection

Oxford Diffraction KM-4-CCD diffractometer
Absorption correction: none
10351 measured reflections
5474 independent reflections
4356 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.106
S = 1.07
5474 reflections
331 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808019077/ng2467sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808019077/ng2467Isup2.hkl

checkCIF report

Comment top

The reaction of Ph₂PCl with ^tBu₂P–P(SiMe₃)Li 1.5 THF in toluene at -30 °C (Kovacs et al. 1996) yielded unexpectedly (Ph₂P)₂P(P^tBu₂) (1) in the place of expected Ph₂P–P(SiMe₃)–P^tBu₂.

The molecular structure of (1) is shown in Fig.1. The geometry around P3 atom in (1) is pyramidal, the sum of angles around P3 is 310.26 degrees. The geometry around P1 atom indicates more pyramidal character (the sum of angles is 297.49 degrees) than around P3. The geometry around P4 atom is more planar (the sum of angles is 320.58 degrees) than around P3. The P–P distances (2.2327 Å - mean value) clearly indicate a single bond character of these bonds. The tendency of phosphane to planarity is more visible for compounds with big groups attached to the central P atom. This assumption is strongly supported by the planar geometry around the central P atom in (^tBu₂P)₃P. This planarity is accompanied by a significant shortening of the P–P distances (2.198 Å) (Fritz et al. 1987).

Related literature top

For the synthesis of silylated triphosphanes, see: Kovacs et al. (1996). For other similar pyramidal isotetraphosphanes, see: Cowley et al. (1997); Fritz et al. (1987); Jones et al. (2002). For planar (^tBu₂P)₃P, see: Fritz et al. (1999). For evaluation of NMR data, see: Bruker (1999); Hägele et al. (1987).

Experimental top

A solution of ^tBu₂P–P(SiMe₃)Li 1.5 THF (855 mg 3.42 mmol) in 20 ml toluene at -30 °C was dropped to a solution of Ph₂PCl (792 mg, 3.59 mmol) in 20 ml toluene. The resulting solution was stirred for 3 h at–30 °C and for 12 h at ambient temp. Then the solvent was removed under vacuum at 1 mTorr for 1 h, the residue dissolved in pentane (40 ml), filtered and concentrated to about 8 ml. After 6 days at -35 ^oC the solution yielded 688 mg of colourless crystals of (Ph₂P)₂P(P^tBu₂) (1).

³¹P{¹H} NMR of (Ph₂P1,2)₂P3(P4^tBu₂) (1) (Bruker Av400, C₆D₆, 298 K, external standard 85% H₃PO₄)(δ p.p.m.) 37.9 dt, P4; -19.5 dd*, P1, P2; -62.3 dt*, P3. ¹J(P3—P4) =–410.7 Hz, ¹J(P1—P3) = -253.3 Hz, ²J(P1—P4) = +33.9 Hz (*= multiplet of higher order).

Chemical shifts and coupling constants of (1) were optimized using Bruke software (Bruker 1999, Hägele et al. 1987).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. A view of the title molecule, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms have been omitted for clarity.
	Fig. 2. Crystal packing of the title compound, viewed approximately along the b axis.

(Di-tert--butylphosphanyl)bis(diphenylphosphanyl)phosphane top

Crystal data top

C₃₂H₃₈P₄	Z = 2
M_r = 546.5	F(000) = 580
Triclinic, P1	D_x = 1.232 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.0161 (6) Å	Cell parameters from 6775 reflections
b = 11.9258 (7) Å	θ = 2.4–32.4°
c = 12.9951 (7) Å	µ = 0.28 mm⁻¹
α = 104.831 (5)°	T = 120 K
β = 100.201 (5)°	Prism, colourless
γ = 90.900 (5)°	0.32 × 0.15 × 0.13 mm
V = 1473.79 (15) Å³

Data collection top

Oxford DiffractionKM-4-CCD diffractometer	4356 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 8.1883 pixels mm^-1	θ_max = 25.5°, θ_min = 2.4°
0.75° wide ω scans	h = −11→12
10351 measured reflections	k = −14→13
5474 independent reflections	l = −15→14

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0689P)²] where P = (F_o² + 2F_c²)/3
5474 reflections	(Δ/σ)_max < 0.001
331 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₃₂H₃₈P₄	γ = 90.900 (5)°
M_r = 546.5	V = 1473.79 (15) Å³
Triclinic, P1	Z = 2
a = 10.0161 (6) Å	Mo Kα radiation
b = 11.9258 (7) Å	µ = 0.28 mm⁻¹
c = 12.9951 (7) Å	T = 120 K
α = 104.831 (5)°	0.32 × 0.15 × 0.13 mm
β = 100.201 (5)°

Data collection top

Oxford DiffractionKM-4-CCD diffractometer	4356 reflections with I > 2σ(I)
10351 measured reflections	R_int = 0.023
5474 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.07	Δρ_max = 0.45 e Å⁻³
5474 reflections	Δρ_min = −0.30 e Å⁻³
331 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
C1	−0.05525 (19)	0.27686 (16)	0.36738 (15)	0.0197 (4)
C2	−0.10603 (19)	0.16151 (17)	0.33015 (16)	0.0223 (4)
H2	−0.0706	0.11	0.2741	0.027*
C3	−0.2075 (2)	0.12062 (18)	0.37356 (17)	0.0267 (5)
H3	−0.2412	0.0416	0.347	0.032*
C4	−0.2601 (2)	0.19420 (19)	0.45549 (17)	0.0299 (5)
H4	−0.3292	0.1659	0.4857	0.036*
C5	−0.2118 (2)	0.3082 (2)	0.49266 (18)	0.0354 (5)
H5	−0.2479	0.3592	0.5486	0.042*
C6	−0.1106 (2)	0.34949 (18)	0.44923 (17)	0.0288 (5)
H6	−0.0783	0.4288	0.4757	0.035*
C7	−0.03069 (19)	0.37273 (17)	0.19424 (16)	0.0222 (4)
C8	−0.0180 (2)	0.48242 (19)	0.17833 (18)	0.0325 (5)
H8	0.0439	0.5402	0.2289	0.039*
C9	−0.0951 (3)	0.5082 (2)	0.0890 (2)	0.0446 (7)
H9	−0.0871	0.5841	0.0792	0.054*
C10	−0.1834 (3)	0.4244 (2)	0.0143 (2)	0.0431 (6)
H10	−0.2353	0.4423	−0.0474	0.052*
C11	−0.1966 (2)	0.3146 (2)	0.02890 (18)	0.0368 (6)
H11	−0.2575	0.2569	−0.0227	0.044*
C12	−0.1212 (2)	0.28863 (19)	0.11857 (17)	0.0278 (5)
H12	−0.1309	0.2131	0.1288	0.033*
C13	0.24915 (19)	0.19694 (17)	0.47598 (16)	0.0214 (4)
C14	0.2700 (2)	0.31269 (17)	0.53800 (16)	0.0258 (5)
H14	0.3222	0.3667	0.5163	0.031*
C15	0.2149 (2)	0.34903 (18)	0.63082 (18)	0.0297 (5)
H15	0.2286	0.428	0.6719	0.036*
C16	0.1403 (2)	0.27079 (19)	0.66379 (17)	0.0313 (5)
H16	0.1035	0.2958	0.7278	0.038*
C17	0.1193 (2)	0.15651 (19)	0.60370 (18)	0.0313 (5)
H17	0.0675	0.103	0.6263	0.038*
C18	0.1735 (2)	0.11927 (18)	0.51040 (17)	0.0260 (5)
H18	0.1588	0.0402	0.4697	0.031*
C19	0.3207 (2)	−0.00176 (16)	0.32067 (15)	0.0206 (4)
C20	0.2027 (2)	−0.07357 (17)	0.27282 (16)	0.0253 (4)
H20	0.1186	−0.0399	0.2577	0.03*
C21	0.2071 (2)	−0.19302 (18)	0.24733 (17)	0.0291 (5)
H21	0.126	−0.2409	0.2153	0.035*
C22	0.3292 (2)	−0.24324 (19)	0.26830 (17)	0.0317 (5)
H22	0.3317	−0.3255	0.251	0.038*
C23	0.4468 (2)	−0.17404 (19)	0.31416 (18)	0.0334 (5)
H23	0.5308	−0.2084	0.3279	0.04*
C24	0.4427 (2)	−0.05407 (18)	0.34036 (16)	0.0269 (5)
H24	0.5242	−0.0068	0.3722	0.032*
C25	0.4464 (2)	0.34098 (17)	0.19073 (17)	0.0241 (4)
C26	0.4359 (2)	0.42053 (18)	0.30219 (18)	0.0300 (5)
H26A	0.5207	0.469	0.3328	0.045*
H26B	0.4204	0.3729	0.3508	0.045*
H26C	0.36	0.4703	0.2941	0.045*
C27	0.5567 (2)	0.25572 (19)	0.20422 (18)	0.0280 (5)
H27A	0.5694	0.2103	0.1327	0.042*
H27B	0.529	0.2032	0.2447	0.042*
H27C	0.6423	0.299	0.2439	0.042*
C28	0.4878 (2)	0.41895 (19)	0.1227 (2)	0.0334 (5)
H28A	0.4212	0.4777	0.1184	0.05*
H28B	0.4908	0.3714	0.0496	0.05*
H28C	0.5778	0.4575	0.1567	0.05*
C29	0.2723 (2)	0.14372 (18)	0.00756 (16)	0.0277 (5)
C30	0.3239 (2)	0.03535 (18)	0.04003 (18)	0.0333 (5)
H30A	0.267	0.014	0.087	0.05*
H30B	0.4181	0.0515	0.0791	0.05*
H30C	0.3196	−0.0289	−0.0251	0.05*
C31	0.3551 (2)	0.1739 (2)	−0.07156 (18)	0.0383 (6)
H31A	0.3423	0.1103	−0.138	0.058*
H31B	0.4516	0.1854	−0.0379	0.058*
H31C	0.3242	0.2455	−0.0893	0.058*
C32	0.1237 (2)	0.1177 (2)	−0.05120 (19)	0.0367 (5)
H32A	0.1174	0.0502	−0.1139	0.055*
H32B	0.091	0.1852	−0.0757	0.055*
H32C	0.0678	0.1009	−0.0015	0.055*
P1	0.07579 (5)	0.34576 (4)	0.31567 (4)	0.01952 (13)
P2	0.33268 (5)	0.15796 (4)	0.35823 (4)	0.02017 (14)
P3	0.17163 (5)	0.19161 (4)	0.22775 (4)	0.01832 (13)
P4	0.26732 (5)	0.27752 (4)	0.12351 (4)	0.02045 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0156 (9)	0.0236 (10)	0.0209 (10)	0.0015 (8)	0.0024 (8)	0.0079 (8)
C2	0.0207 (10)	0.0228 (10)	0.0249 (10)	0.0040 (8)	0.0074 (8)	0.0069 (8)
C3	0.0237 (11)	0.0252 (11)	0.0326 (12)	−0.0018 (9)	0.0030 (9)	0.0117 (9)
C4	0.0218 (11)	0.0421 (13)	0.0278 (11)	−0.0058 (10)	0.0057 (9)	0.0126 (10)
C5	0.0308 (12)	0.0417 (13)	0.0296 (12)	−0.0043 (10)	0.0124 (10)	−0.0021 (10)
C6	0.0249 (11)	0.0296 (12)	0.0279 (11)	−0.0054 (9)	0.0081 (9)	−0.0011 (9)
C7	0.0197 (10)	0.0263 (11)	0.0252 (11)	0.0094 (8)	0.0118 (8)	0.0093 (8)
C8	0.0415 (13)	0.0272 (12)	0.0341 (12)	0.0122 (10)	0.0153 (10)	0.0115 (10)
C9	0.0699 (19)	0.0379 (14)	0.0377 (14)	0.0269 (13)	0.0232 (14)	0.0204 (11)
C10	0.0430 (14)	0.0630 (17)	0.0331 (13)	0.0277 (13)	0.0118 (11)	0.0257 (13)
C11	0.0233 (11)	0.0606 (16)	0.0294 (12)	0.0093 (11)	0.0081 (10)	0.0145 (11)
C12	0.0197 (10)	0.0381 (12)	0.0294 (11)	0.0035 (9)	0.0071 (9)	0.0140 (9)
C13	0.0172 (9)	0.0241 (10)	0.0224 (10)	0.0036 (8)	0.0008 (8)	0.0068 (8)
C14	0.0235 (10)	0.0244 (11)	0.0268 (11)	−0.0003 (9)	−0.0014 (9)	0.0062 (9)
C15	0.0304 (11)	0.0241 (11)	0.0299 (11)	0.0056 (9)	0.0012 (9)	0.0013 (9)
C16	0.0343 (12)	0.0359 (13)	0.0251 (11)	0.0107 (10)	0.0097 (10)	0.0072 (9)
C17	0.0331 (12)	0.0313 (12)	0.0337 (12)	0.0045 (10)	0.0128 (10)	0.0115 (10)
C18	0.0285 (11)	0.0234 (10)	0.0255 (11)	0.0018 (9)	0.0046 (9)	0.0057 (8)
C19	0.0219 (10)	0.0215 (10)	0.0206 (10)	0.0048 (8)	0.0062 (8)	0.0080 (8)
C20	0.0234 (10)	0.0248 (11)	0.0294 (11)	0.0037 (8)	0.0063 (9)	0.0087 (9)
C21	0.0339 (12)	0.0244 (11)	0.0293 (11)	−0.0002 (9)	0.0068 (10)	0.0072 (9)
C22	0.0490 (14)	0.0218 (11)	0.0259 (11)	0.0116 (10)	0.0095 (10)	0.0070 (9)
C23	0.0366 (13)	0.0332 (12)	0.0315 (12)	0.0180 (10)	0.0062 (10)	0.0100 (10)
C24	0.0245 (11)	0.0298 (11)	0.0260 (11)	0.0054 (9)	0.0039 (9)	0.0070 (9)
C25	0.0176 (10)	0.0260 (11)	0.0313 (11)	0.0001 (8)	0.0060 (8)	0.0112 (9)
C26	0.0274 (11)	0.0248 (11)	0.0360 (12)	−0.0062 (9)	0.0071 (10)	0.0046 (9)
C27	0.0171 (10)	0.0351 (12)	0.0346 (12)	0.0035 (9)	0.0054 (9)	0.0138 (9)
C28	0.0248 (11)	0.0353 (13)	0.0473 (14)	0.0004 (9)	0.0126 (10)	0.0196 (11)
C29	0.0271 (11)	0.0330 (12)	0.0227 (11)	0.0047 (9)	0.0073 (9)	0.0048 (9)
C30	0.0362 (13)	0.0275 (11)	0.0338 (12)	0.0067 (10)	0.0133 (10)	−0.0010 (9)
C31	0.0382 (13)	0.0515 (15)	0.0263 (12)	0.0066 (11)	0.0125 (10)	0.0074 (10)
C32	0.0332 (12)	0.0413 (14)	0.0287 (12)	−0.0010 (11)	0.0000 (10)	0.0009 (10)
P1	0.0169 (3)	0.0182 (3)	0.0239 (3)	0.00124 (19)	0.0052 (2)	0.0054 (2)
P2	0.0165 (3)	0.0201 (3)	0.0244 (3)	0.0010 (2)	0.0029 (2)	0.0074 (2)
P3	0.0153 (2)	0.0183 (3)	0.0219 (3)	0.00182 (19)	0.0037 (2)	0.0060 (2)
P4	0.0165 (3)	0.0232 (3)	0.0239 (3)	0.0039 (2)	0.0057 (2)	0.0088 (2)

Geometric parameters (Å, º) top

C1—C2	1.391 (3)	C20—C21	1.381 (3)
C1—C6	1.393 (3)	C20—H20	0.95
C1—P1	1.847 (2)	C21—C22	1.385 (3)
C2—C3	1.385 (3)	C21—H21	0.95
C2—H2	0.95	C22—C23	1.376 (3)
C3—C4	1.384 (3)	C22—H22	0.95
C3—H3	0.95	C23—C24	1.386 (3)
C4—C5	1.369 (3)	C23—H23	0.95
C4—H4	0.95	C24—H24	0.95
C5—C6	1.385 (3)	C25—C27	1.530 (3)
C5—H5	0.95	C25—C26	1.537 (3)
C6—H6	0.95	C25—C28	1.535 (3)
C7—C8	1.383 (3)	C25—P4	1.902 (2)
C7—C12	1.395 (3)	C26—H26A	0.98
C7—P1	1.845 (2)	C26—H26B	0.98
C8—C9	1.382 (3)	C26—H26C	0.98
C8—H8	0.95	C27—H27A	0.98
C9—C10	1.376 (4)	C27—H27B	0.98
C9—H9	0.95	C27—H27C	0.98
C10—C11	1.378 (4)	C28—H28A	0.98
C10—H10	0.95	C28—H28B	0.98
C11—C12	1.380 (3)	C28—H28C	0.98
C11—H11	0.95	C29—C30	1.529 (3)
C12—H12	0.95	C29—C31	1.535 (3)
C13—C18	1.394 (3)	C29—C32	1.535 (3)
C13—C14	1.400 (3)	C29—P4	1.902 (2)
C13—P2	1.833 (2)	C30—H30A	0.98
C14—C15	1.387 (3)	C30—H30B	0.98
C14—H14	0.95	C30—H30C	0.98
C15—C16	1.382 (3)	C31—H31A	0.98
C15—H15	0.95	C31—H31B	0.98
C16—C17	1.378 (3)	C31—H31C	0.98
C16—H16	0.95	C32—H32A	0.98
C17—C18	1.388 (3)	C32—H32B	0.98
C17—H17	0.95	C32—H32C	0.98
C18—H18	0.95	P1—P3	2.2305 (7)
C19—C24	1.394 (3)	P2—P3	2.2446 (7)
C19—C20	1.397 (3)	P3—P4	2.2231 (7)
C19—P2	1.838 (2)

C2—C1—C6	117.64 (18)	C22—C23—C24	119.9 (2)
C2—C1—P1	126.30 (15)	C22—C23—H23	120
C6—C1—P1	116.03 (15)	C24—C23—H23	120
C3—C2—C1	120.96 (18)	C23—C24—C19	121.0 (2)
C3—C2—H2	119.5	C23—C24—H24	119.5
C1—C2—H2	119.5	C19—C24—H24	119.5
C2—C3—C4	120.36 (19)	C27—C25—C26	109.64 (17)
C2—C3—H3	119.8	C27—C25—C28	108.98 (17)
C4—C3—H3	119.8	C26—C25—C28	107.24 (17)
C5—C4—C3	119.4 (2)	C27—C25—P4	117.57 (14)
C5—C4—H4	120.3	C26—C25—P4	106.54 (13)
C3—C4—H4	120.3	C28—C25—P4	106.38 (14)
C4—C5—C6	120.4 (2)	C25—C26—H26A	109.5
C4—C5—H5	119.8	C25—C26—H26B	109.5
C6—C5—H5	119.8	H26A—C26—H26B	109.5
C5—C6—C1	121.2 (2)	C25—C26—H26C	109.5
C5—C6—H6	119.4	H26A—C26—H26C	109.5
C1—C6—H6	119.4	H26B—C26—H26C	109.5
C8—C7—C12	119.11 (19)	C25—C27—H27A	109.5
C8—C7—P1	117.40 (16)	C25—C27—H27B	109.5
C12—C7—P1	123.49 (15)	H27A—C27—H27B	109.5
C9—C8—C7	120.2 (2)	C25—C27—H27C	109.5
C9—C8—H8	119.9	H27A—C27—H27C	109.5
C7—C8—H8	119.9	H27B—C27—H27C	109.5
C10—C9—C8	120.3 (2)	C25—C28—H28A	109.5
C10—C9—H9	119.8	C25—C28—H28B	109.5
C8—C9—H9	119.8	H28A—C28—H28B	109.5
C9—C10—C11	120.1 (2)	C25—C28—H28C	109.5
C9—C10—H10	120	H28A—C28—H28C	109.5
C11—C10—H10	120	H28B—C28—H28C	109.5
C10—C11—C12	120.0 (2)	C30—C29—C31	110.04 (18)
C10—C11—H11	120	C30—C29—C32	108.77 (18)
C12—C11—H11	120	C31—C29—C32	107.76 (18)
C11—C12—C7	120.3 (2)	C30—C29—P4	115.98 (14)
C11—C12—H12	119.8	C31—C29—P4	109.73 (15)
C7—C12—H12	119.8	C32—C29—P4	104.12 (14)
C18—C13—C14	118.53 (19)	C29—C30—H30A	109.5
C18—C13—P2	124.94 (15)	C29—C30—H30B	109.5
C14—C13—P2	116.45 (15)	H30A—C30—H30B	109.5
C15—C14—C13	120.47 (19)	C29—C30—H30C	109.5
C15—C14—H14	119.8	H30A—C30—H30C	109.5
C13—C14—H14	119.8	H30B—C30—H30C	109.5
C16—C15—C14	120.2 (2)	C29—C31—H31A	109.5
C16—C15—H15	119.9	C29—C31—H31B	109.5
C14—C15—H15	119.9	H31A—C31—H31B	109.5
C17—C16—C15	120.0 (2)	C29—C31—H31C	109.5
C17—C16—H16	120	H31A—C31—H31C	109.5
C15—C16—H16	120	H31B—C31—H31C	109.5
C16—C17—C18	120.3 (2)	C29—C32—H32A	109.5
C16—C17—H17	119.8	C29—C32—H32B	109.5
C18—C17—H17	119.8	H32A—C32—H32B	109.5
C17—C18—C13	120.51 (19)	C29—C32—H32C	109.5
C17—C18—H18	119.7	H32A—C32—H32C	109.5
C13—C18—H18	119.7	H32B—C32—H32C	109.5
C24—C19—C20	118.16 (18)	C7—P1—C1	99.44 (9)
C24—C19—P2	115.67 (15)	C7—P1—P3	96.19 (6)
C20—C19—P2	126.16 (15)	C1—P1—P3	101.86 (6)
C21—C20—C19	120.70 (19)	C13—P2—C19	103.58 (9)
C21—C20—H20	119.7	C13—P2—P3	101.37 (6)
C19—C20—H20	119.7	C19—P2—P3	100.37 (6)
C20—C21—C22	120.2 (2)	P4—P3—P1	97.92 (3)
C20—C21—H21	119.9	P4—P3—P2	109.51 (3)
C22—C21—H21	119.9	P1—P3—P2	102.93 (3)
C23—C22—C21	119.98 (19)	C25—P4—C29	110.55 (9)
C23—C22—H22	120	C25—P4—P3	112.04 (7)
C21—C22—H22	120	C29—P4—P3	97.98 (7)

Experimental details

Crystal data
Chemical formula	C₃₂H₃₈P₄
M_r	546.5
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	10.0161 (6), 11.9258 (7), 12.9951 (7)
α, β, γ (°)	104.831 (5), 100.201 (5), 90.900 (5)
V (Å³)	1473.79 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.32 × 0.15 × 0.13

Data collection
Diffractometer	Oxford DiffractionKM-4-CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10351, 5474, 4356
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.106, 1.07
No. of reflections	5474
No. of parameters	331
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.30

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

References

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