4,6-Bis(diphenyl­phosphan­yl)dibenzo[b,d]furan

Marimuthu, T.; Friedrich, H.B.; Bala, M.D.

doi:10.1107/S1600536811047787

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3319

https://doi.org/10.1107/S1600536811047787

Open

access

4,6-Bis(diphenylphosphanyl)dibenzo[b,d]furan

Thashree Marimuthu,^a Holger B. Friedrich ^a and Muhammad D. Bala ^a ^*

^aSchool of Chemistry, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban 4000, South Africa
^*Correspondence e-mail: bala@ukzn.ac.za

(Received 4 November 2011; accepted 10 November 2011; online 16 November 2011)

The asymmetric unit of the title compound, C₃₆H₂₆OP₂, comprises two molecules which have slightly different conformations of the phenyl ring substituents. In both molecules, the dibenzofuran unit is close to being planar, with dihedral angles of 3.20 (3) and 1.86 (2)° for the two molecules. Its planarity affects the intramolecular distances between P atoms, with P⋯P distances of 5.574 (2) and 5.485 (2) Å for the two molecules.

Related literature

For related syntheses, see: Kranenburg et al. (1995 ); Hillebrand et al. (1995 ). For related structures, see: Vogl et al. (1996 ); Marimuthu et al. (2008a ,b ). For structures containing the dibenzofuran unit, see: Dideberg et al. (1972 ); Banerjee (1973 ); Reppart et al., (1984 ).

Experimental

Crystal data

C₃₆H₂₆OP₂
M_r = 536.51
Triclinic, $[P \overline 1]$
a = 11.7463 (2) Å
b = 14.7238 (3) Å
c = 16.7140 (4) Å
α = 96.821 (2)°
β = 96.351 (5)°
γ = 95.240 (2)°
V = 2836.58 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 173 K
0.40 × 0.22 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer
28406 measured reflections
12364 independent reflections
8323 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.100
S = 0.90
12363 reflections
703 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT-Plus (Bruker, 2005); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811047787/kp2367sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811047787/kp2367Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811047787/kp2367Isup3.cml

checkCIF report

Comment top

The crystal structure of (I)comprises the two crystallographically independent conformers of the title compound (I)(Fig. 1). The dibenzofuran or aromatic ether backbone has been selectively functionalised with diphosphane donors. The diphosphane ligand has been used in Rh hydroformylation catalysis (Kranenburg et al., 1995). In a study towards the isolation of stable coordination complexes, the complex of Co with a ligand (I) was published (Vogl et al. 1996); herein we report a different conformation of the ligand to the reported one. The individual five and six membered rings of dibenzofuran moiety in (I) are planar, but not coplanar; dihedral angles of 1.32° & 1.88° (molecule A) and 1.52° & 0.42° (molecule B) are observed. The planarity of the dibenzofuran moiety has been a subject of interest reporting the dihedral angles of 1.12° (Dideberg et al., 1972), 1.1° (Banerjee, 1973) and 1.5° (Reppart et al., 1984). However, (Vogl et al. 1996) have reported a larger dihedral angle of 2.45° and 2.51° which is attributed to the difference in the disposition of the phenyl rings as compared to previous reports and the title compound.

In a chelating diphosphane compound, the magnitude of the intramolecular separation distances between P atoms has a big impact on the stability of its coordination compounds. In the title compound, the rigid backbone pushes the diphosphane pincers apart resulting in relatively large intramolecular separation distances between the P atoms of 5.574 (2) and 5.485 (2) for molecules A and B, respectively. This value is slightly smaller than the 5.741 (1) reported by (Vogl et al. 1996), but notably larger than in xantphos, [4.025 (2) (Kranenburg et al., 1995) and 4.046 Å (Hillebrand et al. 1995)] and nixantphos, 4.255 (2) Å (Marimuthu et al. 2008a).

Related literature top

For related syntheses, see: Kranenburg et al. (1995); Hillebrand et al. (1995). For related structures, see: Vogl et al. (1996); Marimuthu et al. (2008a,b). For structures containing the dibenzofuran unit, see: Dideberg et al. (1972); Banerjee (1973); Reppart et al., (1984).

Experimental top

The preparation of (I) was adapted from literature (Kranenburg et al., 1995). A solution of dibenzofuran (1.5 g, 8.9 mmol) in 60 mL of dry ether was cooled to 208 K, using a dry ice/acetone bath. Thereafter, tetramethylethylenediamine (3.8 mL, 25 mmol) was added and the solution stirred. Under a positive pressure of argon, nBuLi (15.6 mL, 25 mmol) was added dropwise and the reaction left to stir for a further 16 h. Thereafter, the stirred reaction mixture was cooled to 208 K and chlorodiphenylphosphane (4.6 mL, 25 mmol) in hexane (13 mL) added dropwise. Then, the reaction was left to stir overnight. A (1/1) mixture of dichloromethane (DCM)/water (25 mL) was added. After allowing sufficient time to stir, the organic layer was removed, and the aqueous layer extracted with DCM (2 x 15 mL). The combined organic fractions were dried over anhydrous MgSO₄, filtered, and the solvent evacuated to dryness. The resulting oil was washed with hexane and recrystalised from DCM/EtOH (1:1) to afford colourless crystals of (I) suitable for X-ray analysis. [yield: 3.4 g, 71%; m.p. 485 K]. Spectroscopic analysis: ¹H NMR (400 MHz, CDCl₃, δ, p.p.m.): 7.91 (dd, J = 7.7, 1.2 Hz, 2H), 7.44 – 7.09 (m, P(C₆H₅)₂ and H xanthene, 22H), 7.03 (td, J(H,H) = 7.4, J(P,H) 1.2 Hz, 2H); ¹³C NMR (101 MHz, CDCl₃, δ, p.p.m.): 157.9 (d, J(P,C) = 13.7 Hz, CO), 135.8 (d, J(P,C) = 10.7 Hz, phenyl C-ipso, PC), 133.8 (d, J(P,C) = 20.3 Hz, CH), 132.0 (d, J = 8.6 Hz, CH), 128.7 (s, CH), 128.3 (d, J (P,C) = 7.1 Hz, CH), 123.5 (bs, C), 123.1 (d, J(P,C) = 3.0 Hz, CH), 121.2 (d, J (P,C) = 19.5 Hz, C), 121.5 (CH); ³¹P NMR (243 MHz, CDCl₃ δ, p.p.m.): -16.9; IR (neat, ν_max, cm^-1): 3046 (w), 3006 (w), 1476 (m), 1433 (s), 1408 (s), 1387 (m), 1173 (s), 772 (m), 739 (s), 691 (s); HR—MS (ESI) (m/z): 537.1531 [M + H]⁺ calcd. for C₃₆H₂₇OP₂, 537.1532.

Structure description top

For related syntheses, see: Kranenburg et al. (1995); Hillebrand et al. (1995). For related structures, see: Vogl et al. (1996); Marimuthu et al. (2008a,b). For structures containing the dibenzofuran unit, see: Dideberg et al. (1972); Banerjee (1973); Reppart et al., (1984).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2005); data reduction: SAINT-Plus (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. ORTEP diagram of compound (I). Displacement ellipsoids are represented at the 50% probability level. Hydrogen atoms omitted for clarity.

4,6-Bis(diphenylphosphanyl)dibenzo[b,d]furan top

Crystal data top

C₃₆H₂₆OP₂	Z = 4
M_r = 536.51	F(000) = 1120
Triclinic, P1	D_x = 1.256 Mg m⁻³
Hall symbol: -P 1	Melting point: 485 K
a = 11.7463 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.7238 (3) Å	Cell parameters from 7048 reflections
c = 16.7140 (4) Å	θ = 2.3–26.9°
α = 96.821 (2)°	µ = 0.18 mm⁻¹
β = 96.351 (5)°	T = 173 K
γ = 95.240 (2)°	Prism, colourless
V = 2836.58 (10) Å³	0.40 × 0.22 × 0.18 mm

Data collection top

Bruker APEXII CCD diffractometer	8323 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.052
Graphite monochromator	θ_max = 27.0°, θ_min = 1.2°
φ and ω scans	h = −15→14
28406 measured reflections	k = −14→18
12364 independent reflections	l = −21→19

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H-atom parameters constrained
S = 0.90	w = 1/[σ²(F_o²) + (0.0468P)²] where P = (F_o² + 2F_c²)/3
12363 reflections	(Δ/σ)_max = 0.002
703 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₃₆H₂₆OP₂	γ = 95.240 (2)°
M_r = 536.51	V = 2836.58 (10) Å³
Triclinic, P1	Z = 4
a = 11.7463 (2) Å	Mo Kα radiation
b = 14.7238 (3) Å	µ = 0.18 mm⁻¹
c = 16.7140 (4) Å	T = 173 K
α = 96.821 (2)°	0.40 × 0.22 × 0.18 mm
β = 96.351 (5)°

Data collection top

Bruker APEXII CCD diffractometer	8323 reflections with I > 2σ(I)
28406 measured reflections	R_int = 0.052
12364 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 0.90	Δρ_max = 0.29 e Å⁻³
12363 reflections	Δρ_min = −0.30 e Å⁻³
703 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.

One reflection was an outlier.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1A	0.37941 (15)	0.82094 (11)	0.53677 (10)	0.0274 (4)
C2A	0.31908 (16)	0.88254 (12)	0.49585 (11)	0.0332 (4)
H2A	0.3066	0.8730	0.4382	0.040*
C3A	0.27640 (17)	0.95794 (12)	0.53724 (12)	0.0370 (5)
H3A	0.2357	0.9981	0.5071	0.044*
C4A	0.29204 (16)	0.97513 (12)	0.62065 (12)	0.0335 (4)
H4A	0.2625	1.0264	0.6482	0.040*
C5A	0.35234 (16)	0.91537 (11)	0.66360 (11)	0.0285 (4)
C6A	0.39397 (15)	0.84093 (11)	0.62080 (11)	0.0268 (4)
C7A	0.48344 (15)	0.79506 (11)	0.82089 (11)	0.0282 (4)
C8A	0.46446 (16)	0.84741 (12)	0.89246 (11)	0.0333 (4)
H8A	0.4901	0.8277	0.9429	0.040*
C9A	0.40934 (17)	0.92762 (13)	0.89305 (12)	0.0373 (5)
H9A	0.4002	0.9614	0.9436	0.045*
C10A	0.36791 (17)	0.95880 (12)	0.82206 (11)	0.0340 (5)
H10A	0.3293	1.0128	0.8228	0.041*
C11A	0.38466 (15)	0.90833 (11)	0.74890 (11)	0.0284 (4)
C12A	0.44181 (15)	0.82992 (11)	0.75056 (10)	0.0270 (4)
C21A	0.33887 (16)	0.62567 (11)	0.49008 (10)	0.0291 (4)
C22A	0.23537 (17)	0.63032 (13)	0.52293 (11)	0.0366 (5)
H22A	0.2125	0.6885	0.5417	0.044*
C23A	0.16524 (19)	0.55069 (14)	0.52854 (12)	0.0440 (5)
H23A	0.0955	0.5547	0.5520	0.053*
C24A	0.1962 (2)	0.46631 (13)	0.50037 (12)	0.0431 (5)
H24A	0.1477	0.4121	0.5041	0.052*
C25A	0.2978 (2)	0.45991 (13)	0.46652 (12)	0.0438 (5)
H25A	0.3189	0.4015	0.4463	0.053*
C26A	0.36865 (18)	0.53926 (12)	0.46226 (12)	0.0378 (5)
H26A	0.4391	0.5346	0.4399	0.045*
C31A	0.42922 (15)	0.74431 (11)	0.38134 (10)	0.0278 (4)
C32A	0.35837 (16)	0.68820 (12)	0.31898 (11)	0.0317 (4)
H32A	0.3069	0.6399	0.3316	0.038*
C33A	0.36212 (17)	0.70197 (13)	0.23882 (12)	0.0375 (5)
H33A	0.3141	0.6624	0.1970	0.045*
C34A	0.43455 (17)	0.77238 (13)	0.21902 (12)	0.0386 (5)
H34A	0.4369	0.7814	0.1639	0.046*
C35A	0.50414 (18)	0.83009 (13)	0.28039 (12)	0.0404 (5)
H35A	0.5533	0.8797	0.2674	0.048*
C36A	0.50225 (17)	0.81565 (12)	0.36026 (11)	0.0351 (5)
H36A	0.5514	0.8549	0.4017	0.042*
C41A	0.58347 (16)	0.67629 (11)	0.92241 (11)	0.0302 (4)
C42A	0.68812 (17)	0.71181 (12)	0.96745 (12)	0.0360 (5)
H42A	0.7459	0.7422	0.9416	0.043*
C43A	0.7095 (2)	0.70373 (14)	1.04910 (13)	0.0472 (6)
H43A	0.7812	0.7291	1.0789	0.057*
C44A	0.6276 (2)	0.65914 (14)	1.08731 (13)	0.0518 (6)
H44A	0.6424	0.6536	1.1435	0.062*
C45A	0.5234 (2)	0.62240 (14)	1.04374 (13)	0.0530 (6)
H45A	0.4668	0.5912	1.0699	0.064*
C46A	0.50146 (19)	0.63084 (13)	0.96218 (12)	0.0442 (5)
H46A	0.4295	0.6053	0.9328	0.053*
C51A	0.44897 (15)	0.60216 (11)	0.77260 (10)	0.0265 (4)
C52A	0.33230 (16)	0.61084 (12)	0.77160 (11)	0.0357 (5)
H52A	0.3082	0.6676	0.7932	0.043*
C53A	0.25030 (17)	0.53820 (12)	0.73967 (11)	0.0376 (5)
H53A	0.1707	0.5454	0.7392	0.045*
C54A	0.28428 (18)	0.45581 (13)	0.70864 (11)	0.0378 (5)
H54A	0.2282	0.4059	0.6867	0.045*
C55A	0.39956 (19)	0.44551 (13)	0.70934 (13)	0.0466 (6)
H55A	0.4230	0.3883	0.6884	0.056*
C56A	0.48183 (17)	0.51863 (13)	0.74064 (12)	0.0398 (5)
H56A	0.5613	0.5113	0.7401	0.048*
O1A	0.44942 (10)	0.78761 (7)	0.67250 (7)	0.0282 (3)
P1A	0.44520 (4)	0.72421 (3)	0.48805 (3)	0.02816 (12)
P2A	0.56344 (4)	0.69353 (3)	0.81530 (3)	0.02891 (12)
C1B	0.00064 (16)	0.29822 (12)	0.74027 (11)	0.0290 (4)
C2B	−0.01889 (16)	0.35240 (12)	0.67774 (11)	0.0338 (4)
H2B	0.0026	0.3324	0.6259	0.041*
C3B	−0.06894 (17)	0.43487 (12)	0.68878 (11)	0.0355 (5)
H3B	−0.0795	0.4697	0.6447	0.043*
C4B	−0.10324 (16)	0.46657 (12)	0.76244 (11)	0.0326 (4)
H4B	−0.1380	0.5223	0.7694	0.039*
C5B	−0.08556 (15)	0.41471 (11)	0.82632 (11)	0.0280 (4)
C6B	−0.03372 (15)	0.33400 (11)	0.81348 (10)	0.0269 (4)
C7B	−0.07776 (15)	0.32607 (11)	1.01918 (10)	0.0257 (4)
C8B	−0.12956 (16)	0.39021 (11)	1.06783 (11)	0.0307 (4)
H8B	−0.1366	0.3810	1.1225	0.037*
C9B	−0.17122 (17)	0.46730 (12)	1.03859 (12)	0.0354 (5)
H9B	−0.2063	0.5089	1.0737	0.043*
C10B	−0.16281 (16)	0.48458 (12)	0.96022 (11)	0.0335 (4)
H10B	−0.1914	0.5373	0.9410	0.040*
C11B	−0.11105 (16)	0.42244 (11)	0.90970 (11)	0.0277 (4)
C12B	−0.07107 (15)	0.34590 (11)	0.94068 (10)	0.0258 (4)
C21B	−0.04604 (17)	0.10425 (12)	0.73400 (10)	0.0297 (4)
C22B	−0.16215 (17)	0.11507 (13)	0.71759 (11)	0.0369 (5)
H22B	−0.1842	0.1739	0.7086	0.044*
C23B	−0.24634 (19)	0.04216 (13)	0.71404 (12)	0.0423 (5)
H23B	−0.3252	0.0509	0.7021	0.051*
C24B	−0.2155 (2)	−0.04334 (13)	0.72784 (12)	0.0450 (6)
H24B	−0.2730	−0.0936	0.7256	0.054*
C25B	−0.1012 (2)	−0.05521 (14)	0.74479 (13)	0.0513 (6)
H25B	−0.0797	−0.1140	0.7543	0.062*
C26B	−0.01721 (19)	0.01758 (13)	0.74821 (12)	0.0422 (5)
H26B	0.0615	0.0083	0.7605	0.051*
C31B	0.09720 (16)	0.17990 (12)	0.62744 (11)	0.0307 (4)
C32B	0.01672 (18)	0.13673 (13)	0.56366 (11)	0.0403 (5)
H32B	−0.0558	0.1104	0.5747	0.048*
C33B	0.04143 (19)	0.13184 (14)	0.48452 (12)	0.0455 (5)
H33B	−0.0141	0.1019	0.4416	0.055*
C34B	0.14588 (19)	0.17008 (13)	0.46724 (12)	0.0420 (5)
H34B	0.1620	0.1674	0.4126	0.050*
C35B	0.22697 (18)	0.21236 (13)	0.52976 (13)	0.0402 (5)
H35B	0.2993	0.2386	0.5182	0.048*
C36B	0.20306 (17)	0.21651 (12)	0.60921 (12)	0.0348 (5)
H36B	0.2599	0.2448	0.6520	0.042*
C41B	−0.01766 (15)	0.24706 (10)	1.16214 (10)	0.0247 (4)
C42B	0.08149 (16)	0.28867 (11)	1.21114 (11)	0.0301 (4)
H42B	0.1489	0.3044	1.1870	0.036*
C43B	0.08319 (17)	0.30748 (12)	1.29468 (11)	0.0343 (5)
H43B	0.1510	0.3368	1.3273	0.041*
C44B	−0.01381 (18)	0.28352 (12)	1.33004 (11)	0.0350 (5)
H44B	−0.0130	0.2966	1.3872	0.042*
C45B	−0.11229 (17)	0.24048 (12)	1.28261 (11)	0.0363 (5)
H45B	−0.1787	0.2233	1.3073	0.044*
C46B	−0.11418 (16)	0.22246 (12)	1.19921 (11)	0.0315 (4)
H46B	−0.1822	0.1930	1.1670	0.038*
C51B	−0.11728 (16)	0.13006 (11)	1.01669 (10)	0.0279 (4)
C52B	−0.20495 (17)	0.13010 (13)	0.95380 (11)	0.0387 (5)
H52B	−0.2184	0.1857	0.9325	0.046*
C53B	−0.27329 (19)	0.04889 (15)	0.92185 (12)	0.0477 (6)
H53B	−0.3328	0.0493	0.8785	0.057*
C54B	−0.25549 (19)	−0.03169 (14)	0.95239 (14)	0.0479 (6)
H54B	−0.3021	−0.0870	0.9300	0.058*
C55B	−0.16983 (19)	−0.03237 (13)	1.01565 (14)	0.0454 (6)
H55B	−0.1582	−0.0879	1.0376	0.055*
C56B	−0.10075 (17)	0.04794 (12)	1.04714 (12)	0.0361 (5)
H56B	−0.0411	0.0468	1.0902	0.043*
O1B	−0.02303 (10)	0.29065 (7)	0.88294 (7)	0.0272 (3)
P1B	0.07320 (4)	0.19318 (3)	0.73453 (3)	0.03273 (12)
P2B	−0.00896 (4)	0.22826 (3)	1.05283 (3)	0.02579 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1A	0.0267 (10)	0.0243 (9)	0.0301 (10)	−0.0013 (7)	0.0008 (8)	0.0037 (7)
C2A	0.0340 (11)	0.0309 (10)	0.0334 (11)	0.0027 (8)	−0.0024 (9)	0.0052 (8)
C3A	0.0363 (12)	0.0289 (10)	0.0453 (13)	0.0059 (8)	−0.0043 (9)	0.0089 (9)
C4A	0.0326 (11)	0.0233 (9)	0.0434 (12)	0.0034 (8)	0.0029 (9)	0.0017 (8)
C5A	0.0284 (10)	0.0216 (9)	0.0348 (11)	−0.0011 (7)	0.0040 (8)	0.0027 (7)
C6A	0.0253 (10)	0.0239 (9)	0.0309 (10)	−0.0003 (7)	0.0018 (8)	0.0059 (7)
C7A	0.0259 (10)	0.0286 (10)	0.0295 (10)	−0.0011 (7)	0.0046 (8)	0.0036 (8)
C8A	0.0326 (11)	0.0368 (11)	0.0298 (11)	0.0001 (8)	0.0044 (8)	0.0038 (8)
C9A	0.0419 (13)	0.0374 (11)	0.0309 (11)	0.0025 (9)	0.0088 (9)	−0.0047 (9)
C10A	0.0365 (12)	0.0269 (10)	0.0388 (12)	0.0027 (8)	0.0095 (9)	0.0007 (8)
C11A	0.0279 (10)	0.0232 (9)	0.0333 (10)	−0.0016 (7)	0.0055 (8)	0.0017 (7)
C12A	0.0275 (10)	0.0257 (9)	0.0267 (10)	−0.0006 (7)	0.0051 (8)	−0.0005 (7)
C21A	0.0320 (11)	0.0275 (10)	0.0269 (10)	0.0021 (8)	−0.0018 (8)	0.0057 (7)
C22A	0.0424 (13)	0.0325 (11)	0.0344 (11)	−0.0005 (9)	0.0085 (9)	0.0016 (8)
C23A	0.0474 (14)	0.0473 (13)	0.0355 (12)	−0.0084 (10)	0.0100 (10)	0.0036 (9)
C24A	0.0562 (15)	0.0332 (11)	0.0363 (12)	−0.0086 (10)	−0.0071 (10)	0.0116 (9)
C25A	0.0564 (15)	0.0279 (11)	0.0440 (13)	0.0066 (10)	−0.0086 (11)	0.0044 (9)
C26A	0.0389 (12)	0.0333 (11)	0.0412 (12)	0.0096 (9)	−0.0013 (9)	0.0063 (9)
C31A	0.0250 (10)	0.0304 (10)	0.0287 (10)	0.0052 (7)	0.0037 (8)	0.0047 (8)
C32A	0.0262 (10)	0.0353 (10)	0.0325 (11)	−0.0001 (8)	0.0026 (8)	0.0038 (8)
C33A	0.0339 (12)	0.0423 (12)	0.0336 (11)	0.0019 (9)	−0.0002 (9)	−0.0007 (9)
C34A	0.0399 (13)	0.0481 (12)	0.0310 (11)	0.0102 (9)	0.0074 (9)	0.0104 (9)
C35A	0.0405 (13)	0.0405 (12)	0.0408 (12)	−0.0022 (9)	0.0059 (10)	0.0125 (9)
C36A	0.0340 (12)	0.0347 (11)	0.0352 (11)	−0.0010 (8)	0.0013 (9)	0.0046 (8)
C41A	0.0312 (11)	0.0276 (10)	0.0310 (10)	0.0043 (8)	0.0004 (8)	0.0035 (8)
C42A	0.0332 (12)	0.0358 (11)	0.0376 (12)	0.0073 (8)	−0.0012 (9)	0.0013 (9)
C43A	0.0475 (14)	0.0491 (13)	0.0408 (13)	0.0166 (10)	−0.0117 (11)	−0.0041 (10)
C44A	0.0743 (18)	0.0514 (14)	0.0307 (12)	0.0215 (12)	−0.0020 (12)	0.0063 (10)
C45A	0.0734 (18)	0.0481 (13)	0.0387 (13)	−0.0017 (12)	0.0127 (12)	0.0111 (10)
C46A	0.0456 (14)	0.0480 (13)	0.0358 (12)	−0.0082 (10)	0.0007 (10)	0.0069 (9)
C51A	0.0274 (10)	0.0290 (9)	0.0229 (9)	0.0044 (8)	0.0016 (8)	0.0031 (7)
C52A	0.0309 (11)	0.0328 (10)	0.0407 (12)	0.0070 (8)	0.0023 (9)	−0.0068 (8)
C53A	0.0281 (11)	0.0396 (11)	0.0421 (12)	0.0028 (8)	0.0005 (9)	−0.0032 (9)
C54A	0.0367 (12)	0.0330 (11)	0.0398 (12)	−0.0010 (9)	−0.0004 (9)	−0.0024 (9)
C55A	0.0458 (14)	0.0311 (11)	0.0597 (15)	0.0070 (9)	0.0067 (11)	−0.0094 (10)
C56A	0.0300 (11)	0.0385 (11)	0.0508 (13)	0.0094 (9)	0.0068 (9)	−0.0013 (9)
O1A	0.0334 (7)	0.0257 (6)	0.0256 (7)	0.0053 (5)	0.0030 (5)	0.0028 (5)
P1A	0.0277 (3)	0.0285 (3)	0.0279 (3)	0.00275 (19)	0.0020 (2)	0.00360 (19)
P2A	0.0252 (3)	0.0323 (3)	0.0292 (3)	0.0020 (2)	0.0033 (2)	0.0044 (2)
C1B	0.0288 (10)	0.0293 (10)	0.0274 (10)	−0.0002 (8)	0.0008 (8)	0.0030 (7)
C2B	0.0347 (12)	0.0373 (11)	0.0280 (10)	−0.0010 (9)	0.0013 (8)	0.0052 (8)
C3B	0.0409 (12)	0.0313 (10)	0.0342 (11)	−0.0014 (9)	−0.0019 (9)	0.0144 (8)
C4B	0.0360 (12)	0.0228 (9)	0.0378 (11)	−0.0007 (8)	−0.0006 (9)	0.0070 (8)
C5B	0.0292 (10)	0.0219 (9)	0.0313 (10)	−0.0022 (7)	−0.0003 (8)	0.0041 (7)
C6B	0.0282 (10)	0.0258 (9)	0.0258 (10)	−0.0018 (7)	−0.0007 (8)	0.0066 (7)
C7B	0.0282 (10)	0.0208 (9)	0.0278 (10)	0.0007 (7)	0.0045 (8)	0.0021 (7)
C8B	0.0343 (11)	0.0276 (10)	0.0304 (10)	0.0038 (8)	0.0061 (8)	0.0024 (8)
C9B	0.0390 (12)	0.0287 (10)	0.0392 (12)	0.0084 (8)	0.0093 (9)	−0.0007 (8)
C10B	0.0369 (12)	0.0226 (9)	0.0403 (12)	0.0053 (8)	0.0007 (9)	0.0042 (8)
C11B	0.0299 (10)	0.0202 (9)	0.0317 (10)	−0.0013 (7)	0.0007 (8)	0.0038 (7)
C12B	0.0251 (10)	0.0213 (9)	0.0297 (10)	0.0011 (7)	0.0030 (8)	0.0002 (7)
C21B	0.0398 (12)	0.0309 (10)	0.0210 (9)	0.0118 (8)	0.0053 (8)	0.0061 (7)
C22B	0.0424 (13)	0.0302 (10)	0.0420 (12)	0.0123 (9)	0.0090 (10)	0.0113 (9)
C23B	0.0431 (13)	0.0413 (12)	0.0443 (13)	0.0068 (10)	0.0103 (10)	0.0067 (9)
C24B	0.0648 (17)	0.0334 (11)	0.0374 (12)	0.0007 (10)	0.0123 (11)	0.0048 (9)
C25B	0.0769 (19)	0.0294 (11)	0.0506 (14)	0.0166 (11)	0.0066 (13)	0.0112 (10)
C26B	0.0516 (14)	0.0396 (12)	0.0384 (12)	0.0216 (10)	0.0027 (10)	0.0074 (9)
C31B	0.0325 (11)	0.0307 (10)	0.0298 (10)	0.0086 (8)	0.0030 (8)	0.0038 (8)
C32B	0.0354 (12)	0.0540 (13)	0.0304 (11)	−0.0028 (10)	0.0040 (9)	0.0069 (9)
C33B	0.0507 (15)	0.0538 (13)	0.0306 (12)	0.0023 (11)	0.0021 (10)	0.0044 (9)
C34B	0.0535 (15)	0.0456 (12)	0.0343 (12)	0.0189 (10)	0.0169 (10)	0.0141 (9)
C35B	0.0363 (12)	0.0365 (11)	0.0542 (14)	0.0099 (9)	0.0176 (10)	0.0158 (10)
C36B	0.0340 (12)	0.0281 (10)	0.0427 (12)	0.0065 (8)	0.0036 (9)	0.0045 (8)
C41B	0.0297 (10)	0.0182 (8)	0.0269 (10)	0.0054 (7)	0.0034 (8)	0.0030 (7)
C42B	0.0334 (11)	0.0240 (9)	0.0322 (10)	−0.0024 (8)	0.0037 (8)	0.0053 (7)
C43B	0.0405 (12)	0.0261 (10)	0.0328 (11)	−0.0017 (8)	−0.0049 (9)	0.0025 (8)
C44B	0.0481 (13)	0.0315 (10)	0.0254 (10)	0.0087 (9)	0.0023 (9)	0.0027 (8)
C45B	0.0355 (12)	0.0401 (11)	0.0349 (11)	0.0065 (9)	0.0098 (9)	0.0048 (9)
C46B	0.0279 (11)	0.0344 (10)	0.0313 (11)	0.0025 (8)	0.0027 (8)	0.0025 (8)
C51B	0.0312 (11)	0.0264 (9)	0.0260 (10)	0.0012 (8)	0.0101 (8)	−0.0013 (7)
C52B	0.0429 (13)	0.0396 (11)	0.0317 (11)	−0.0064 (9)	0.0039 (9)	0.0053 (8)
C53B	0.0458 (14)	0.0568 (14)	0.0339 (12)	−0.0146 (11)	0.0044 (10)	−0.0056 (10)
C54B	0.0477 (14)	0.0359 (12)	0.0550 (15)	−0.0118 (10)	0.0212 (12)	−0.0163 (10)
C55B	0.0470 (14)	0.0234 (10)	0.0676 (16)	0.0029 (9)	0.0217 (12)	−0.0004 (10)
C56B	0.0372 (12)	0.0291 (10)	0.0429 (12)	0.0054 (8)	0.0111 (9)	0.0012 (8)
O1B	0.0333 (7)	0.0243 (6)	0.0245 (7)	0.0057 (5)	0.0038 (5)	0.0034 (5)
P1B	0.0339 (3)	0.0384 (3)	0.0262 (3)	0.0103 (2)	0.0005 (2)	0.0032 (2)
P2B	0.0272 (3)	0.0238 (2)	0.0267 (3)	0.00263 (19)	0.0049 (2)	0.00286 (18)

Geometric parameters (Å, º) top

C1A—C6A	1.388 (2)	C1B—C6B	1.390 (2)
C1A—C2A	1.396 (2)	C1B—C2B	1.400 (2)
C1A—P1A	1.8312 (18)	C1B—P1B	1.8306 (19)
C2A—C3A	1.399 (3)	C2B—C3B	1.398 (3)
C2A—H2A	0.9500	C2B—H2B	0.9500
C3A—C4A	1.376 (3)	C3B—C4B	1.380 (3)
C3A—H3A	0.9500	C3B—H3B	0.9500
C4A—C5A	1.394 (3)	C4B—C5B	1.393 (2)
C4A—H4A	0.9500	C4B—H4B	0.9500
C5A—C6A	1.393 (2)	C5B—C6B	1.389 (2)
C5A—C11A	1.453 (2)	C5B—C11B	1.451 (2)
C6A—O1A	1.385 (2)	C6B—O1B	1.3890 (19)
C7A—C8A	1.395 (2)	C7B—C12B	1.387 (2)
C7A—C12A	1.395 (2)	C7B—C8B	1.398 (2)
C7A—P2A	1.8355 (19)	C7B—P2B	1.8296 (18)
C8A—C9A	1.397 (3)	C8B—C9B	1.395 (2)
C8A—H8A	0.9500	C8B—H8B	0.9500
C9A—C10A	1.378 (3)	C9B—C10B	1.376 (3)
C9A—H9A	0.9500	C9B—H9B	0.9500
C10A—C11A	1.396 (2)	C10B—C11B	1.397 (2)
C10A—H10A	0.9500	C10B—H10B	0.9500
C11A—C12A	1.389 (2)	C11B—C12B	1.393 (2)
C12A—O1A	1.3933 (19)	C12B—O1B	1.3891 (19)
C21A—C26A	1.391 (2)	C21B—C22B	1.389 (3)
C21A—C22A	1.392 (3)	C21B—C26B	1.390 (2)
C21A—P1A	1.8320 (17)	C21B—P1B	1.8264 (19)
C22A—C23A	1.389 (2)	C22B—C23B	1.383 (3)
C22A—H22A	0.9500	C22B—H22B	0.9500
C23A—C24A	1.371 (3)	C23B—C24B	1.379 (3)
C23A—H23A	0.9500	C23B—H23B	0.9500
C24A—C25A	1.382 (3)	C24B—C25B	1.373 (3)
C24A—H24A	0.9500	C24B—H24B	0.9500
C25A—C26A	1.385 (3)	C25B—C26B	1.380 (3)
C25A—H25A	0.9500	C25B—H25B	0.9500
C26A—H26A	0.9500	C26B—H26B	0.9500
C31A—C32A	1.393 (2)	C31B—C36B	1.389 (3)
C31A—C36A	1.398 (2)	C31B—C32B	1.393 (2)
C31A—P1A	1.8344 (18)	C31B—P1B	1.8331 (18)
C32A—C33A	1.383 (2)	C32B—C33B	1.380 (3)
C32A—H32A	0.9500	C32B—H32B	0.9500
C33A—C34A	1.375 (3)	C33B—C34B	1.377 (3)
C33A—H33A	0.9500	C33B—H33B	0.9500
C34A—C35A	1.387 (3)	C34B—C35B	1.380 (3)
C34A—H34A	0.9500	C34B—H34B	0.9500
C35A—C36A	1.379 (3)	C35B—C36B	1.383 (3)
C35A—H35A	0.9500	C35B—H35B	0.9500
C36A—H36A	0.9500	C36B—H36B	0.9500
C41A—C42A	1.391 (2)	C41B—C46B	1.391 (2)
C41A—C46A	1.395 (3)	C41B—C42B	1.393 (2)
C41A—P2A	1.8305 (19)	C41B—P2B	1.8308 (17)
C42A—C43A	1.381 (3)	C42B—C43B	1.388 (2)
C42A—H42A	0.9500	C42B—H42B	0.9500
C43A—C44A	1.373 (3)	C43B—C44B	1.377 (3)
C43A—H43A	0.9500	C43B—H43B	0.9500
C44A—C45A	1.381 (3)	C44B—C45B	1.383 (3)
C44A—H44A	0.9500	C44B—H44B	0.9500
C45A—C46A	1.382 (3)	C45B—C46B	1.385 (2)
C45A—H45A	0.9500	C45B—H45B	0.9500
C46A—H46A	0.9500	C46B—H46B	0.9500
C51A—C56A	1.387 (2)	C51B—C56B	1.388 (2)
C51A—C52A	1.386 (2)	C51B—C52B	1.388 (3)
C51A—P2A	1.8321 (17)	C51B—P2B	1.8333 (17)
C52A—C53A	1.385 (2)	C52B—C53B	1.392 (2)
C52A—H52A	0.9500	C52B—H52B	0.9500
C53A—C54A	1.373 (3)	C53B—C54B	1.370 (3)
C53A—H53A	0.9500	C53B—H53B	0.9500
C54A—C55A	1.375 (3)	C54B—C55B	1.378 (3)
C54A—H54A	0.9500	C54B—H54B	0.9500
C55A—C56A	1.390 (3)	C55B—C56B	1.384 (2)
C55A—H55A	0.9500	C55B—H55B	0.9500
C56A—H56A	0.9500	C56B—H56B	0.9500

C6A—C1A—C2A	114.83 (16)	C6B—C1B—C2B	114.00 (17)
C6A—C1A—P1A	119.91 (14)	C6B—C1B—P1B	119.76 (14)
C2A—C1A—P1A	125.14 (14)	C2B—C1B—P1B	126.11 (14)
C1A—C2A—C3A	121.96 (18)	C3B—C2B—C1B	122.40 (17)
C1A—C2A—H2A	119.0	C3B—C2B—H2B	118.8
C3A—C2A—H2A	119.0	C1B—C2B—H2B	118.8
C4A—C3A—C2A	121.47 (18)	C4B—C3B—C2B	121.25 (17)
C4A—C3A—H3A	119.3	C4B—C3B—H3B	119.4
C2A—C3A—H3A	119.3	C2B—C3B—H3B	119.4
C3A—C4A—C5A	118.23 (17)	C3B—C4B—C5B	118.25 (18)
C3A—C4A—H4A	120.9	C3B—C4B—H4B	120.9
C5A—C4A—H4A	120.9	C5B—C4B—H4B	120.9
C6A—C5A—C4A	119.06 (17)	C6B—C5B—C4B	118.87 (17)
C6A—C5A—C11A	105.72 (16)	C6B—C5B—C11B	106.04 (15)
C4A—C5A—C11A	135.21 (17)	C4B—C5B—C11B	135.08 (17)
O1A—C6A—C1A	123.88 (16)	C5B—C6B—O1B	111.51 (15)
O1A—C6A—C5A	111.64 (15)	C5B—C6B—C1B	125.21 (17)
C1A—C6A—C5A	124.45 (17)	O1B—C6B—C1B	123.25 (16)
C8A—C7A—C12A	113.82 (17)	C12B—C7B—C8B	114.56 (16)
C8A—C7A—P2A	125.20 (15)	C12B—C7B—P2B	119.20 (13)
C12A—C7A—P2A	120.86 (13)	C8B—C7B—P2B	125.98 (14)
C7A—C8A—C9A	122.72 (18)	C9B—C8B—C7B	122.00 (17)
C7A—C8A—H8A	118.6	C9B—C8B—H8B	119.0
C9A—C8A—H8A	118.6	C7B—C8B—H8B	119.0
C10A—C9A—C8A	121.52 (17)	C10B—C9B—C8B	121.65 (17)
C10A—C9A—H9A	119.2	C10B—C9B—H9B	119.2
C8A—C9A—H9A	119.2	C8B—C9B—H9B	119.2
C9A—C10A—C11A	117.71 (18)	C9B—C10B—C11B	118.18 (17)
C9A—C10A—H10A	121.1	C9B—C10B—H10B	120.9
C11A—C10A—H10A	121.1	C11B—C10B—H10B	120.9
C12A—C11A—C10A	119.24 (17)	C12B—C11B—C10B	118.67 (17)
C12A—C11A—C5A	105.80 (15)	C12B—C11B—C5B	105.53 (15)
C10A—C11A—C5A	134.94 (18)	C10B—C11B—C5B	135.79 (17)
C11A—C12A—O1A	111.54 (15)	C7B—C12B—O1B	123.42 (15)
C11A—C12A—C7A	124.97 (16)	C7B—C12B—C11B	124.93 (16)
O1A—C12A—C7A	123.46 (16)	O1B—C12B—C11B	111.65 (15)
C26A—C21A—C22A	117.97 (17)	C22B—C21B—C26B	117.60 (18)
C26A—C21A—P1A	116.93 (15)	C22B—C21B—P1B	125.56 (14)
C22A—C21A—P1A	124.91 (14)	C26B—C21B—P1B	116.79 (15)
C23A—C22A—C21A	120.67 (18)	C23B—C22B—C21B	121.45 (18)
C23A—C22A—H22A	119.7	C23B—C22B—H22B	119.3
C21A—C22A—H22A	119.7	C21B—C22B—H22B	119.3
C24A—C23A—C22A	120.3 (2)	C24B—C23B—C22B	119.9 (2)
C24A—C23A—H23A	119.9	C24B—C23B—H23B	120.1
C22A—C23A—H23A	119.9	C22B—C23B—H23B	120.1
C23A—C24A—C25A	120.18 (18)	C25B—C24B—C23B	119.5 (2)
C23A—C24A—H24A	119.9	C25B—C24B—H24B	120.2
C25A—C24A—H24A	119.9	C23B—C24B—H24B	120.2
C24A—C25A—C26A	119.49 (19)	C24B—C25B—C26B	120.6 (2)
C24A—C25A—H25A	120.3	C24B—C25B—H25B	119.7
C26A—C25A—H25A	120.3	C26B—C25B—H25B	119.7
C25A—C26A—C21A	121.4 (2)	C25B—C26B—C21B	121.0 (2)
C25A—C26A—H26A	119.3	C25B—C26B—H26B	119.5
C21A—C26A—H26A	119.3	C21B—C26B—H26B	119.5
C32A—C31A—C36A	117.80 (16)	C36B—C31B—C32B	118.20 (18)
C32A—C31A—P1A	124.71 (13)	C36B—C31B—P1B	117.16 (14)
C36A—C31A—P1A	117.15 (13)	C32B—C31B—P1B	124.64 (15)
C33A—C32A—C31A	120.80 (16)	C33B—C32B—C31B	120.61 (19)
C33A—C32A—H32A	119.6	C33B—C32B—H32B	119.7
C31A—C32A—H32A	119.6	C31B—C32B—H32B	119.7
C34A—C33A—C32A	120.72 (17)	C34B—C33B—C32B	120.53 (19)
C34A—C33A—H33A	119.6	C34B—C33B—H33B	119.7
C32A—C33A—H33A	119.6	C32B—C33B—H33B	119.7
C33A—C34A—C35A	119.33 (18)	C33B—C34B—C35B	119.61 (19)
C33A—C34A—H34A	120.3	C33B—C34B—H34B	120.2
C35A—C34A—H34A	120.3	C35B—C34B—H34B	120.2
C36A—C35A—C34A	120.18 (17)	C34B—C35B—C36B	120.05 (19)
C36A—C35A—H35A	119.9	C34B—C35B—H35B	120.0
C34A—C35A—H35A	119.9	C36B—C35B—H35B	120.0
C35A—C36A—C31A	121.15 (17)	C35B—C36B—C31B	120.99 (18)
C35A—C36A—H36A	119.4	C35B—C36B—H36B	119.5
C31A—C36A—H36A	119.4	C31B—C36B—H36B	119.5
C42A—C41A—C46A	117.76 (18)	C46B—C41B—C42B	118.34 (16)
C42A—C41A—P2A	117.35 (14)	C46B—C41B—P2B	125.19 (13)
C46A—C41A—P2A	124.89 (14)	C42B—C41B—P2B	116.47 (13)
C43A—C42A—C41A	121.18 (19)	C43B—C42B—C41B	120.97 (17)
C43A—C42A—H42A	119.4	C43B—C42B—H42B	119.5
C41A—C42A—H42A	119.4	C41B—C42B—H42B	119.5
C44A—C43A—C42A	120.2 (2)	C44B—C43B—C42B	119.72 (17)
C44A—C43A—H43A	119.9	C44B—C43B—H43B	120.1
C42A—C43A—H43A	119.9	C42B—C43B—H43B	120.1
C43A—C44A—C45A	119.7 (2)	C43B—C44B—C45B	120.16 (17)
C43A—C44A—H44A	120.2	C43B—C44B—H44B	119.9
C45A—C44A—H44A	120.2	C45B—C44B—H44B	119.9
C44A—C45A—C46A	120.2 (2)	C44B—C45B—C46B	120.07 (18)
C44A—C45A—H45A	119.9	C44B—C45B—H45B	120.0
C46A—C45A—H45A	119.9	C46B—C45B—H45B	120.0
C45A—C46A—C41A	120.89 (19)	C45B—C46B—C41B	120.73 (17)
C45A—C46A—H46A	119.6	C45B—C46B—H46B	119.6
C41A—C46A—H46A	119.6	C41B—C46B—H46B	119.6
C56A—C51A—C52A	118.26 (16)	C56B—C51B—C52B	118.53 (17)
C56A—C51A—P2A	117.54 (14)	C56B—C51B—P2B	117.23 (15)
C52A—C51A—P2A	124.19 (13)	C52B—C51B—P2B	123.69 (14)
C53A—C52A—C51A	121.12 (17)	C51B—C52B—C53B	120.2 (2)
C53A—C52A—H52A	119.4	C51B—C52B—H52B	119.9
C51A—C52A—H52A	119.4	C53B—C52B—H52B	119.9
C54A—C53A—C52A	119.89 (19)	C54B—C53B—C52B	120.5 (2)
C54A—C53A—H53A	120.1	C54B—C53B—H53B	119.7
C52A—C53A—H53A	120.1	C52B—C53B—H53B	119.7
C53A—C54A—C55A	119.98 (17)	C53B—C54B—C55B	119.83 (18)
C53A—C54A—H54A	120.0	C53B—C54B—H54B	120.1
C55A—C54A—H54A	120.0	C55B—C54B—H54B	120.1
C54A—C55A—C56A	120.15 (18)	C54B—C55B—C56B	119.9 (2)
C54A—C55A—H55A	119.9	C54B—C55B—H55B	120.0
C56A—C55A—H55A	119.9	C56B—C55B—H55B	120.0
C51A—C56A—C55A	120.58 (19)	C55B—C56B—C51B	121.0 (2)
C51A—C56A—H56A	119.7	C55B—C56B—H56B	119.5
C55A—C56A—H56A	119.7	C51B—C56B—H56B	119.5
C6A—O1A—C12A	105.30 (13)	C12B—O1B—C6B	105.27 (13)
C1A—P1A—C21A	103.15 (8)	C21B—P1B—C1B	102.18 (8)
C1A—P1A—C31A	102.08 (8)	C21B—P1B—C31B	101.54 (8)
C21A—P1A—C31A	103.78 (8)	C1B—P1B—C31B	100.47 (8)
C41A—P2A—C51A	102.14 (8)	C7B—P2B—C41B	101.18 (8)
C41A—P2A—C7A	100.61 (8)	C7B—P2B—C51B	103.45 (8)
C51A—P2A—C7A	101.40 (8)	C41B—P2B—C51B	103.28 (8)

C6A—C1A—C2A—C3A	−0.4 (3)	C6B—C1B—C2B—C3B	−0.2 (3)
P1A—C1A—C2A—C3A	−176.48 (14)	P1B—C1B—C2B—C3B	−176.01 (14)
C1A—C2A—C3A—C4A	0.1 (3)	C1B—C2B—C3B—C4B	−0.9 (3)
C2A—C3A—C4A—C5A	0.2 (3)	C2B—C3B—C4B—C5B	0.7 (3)
C3A—C4A—C5A—C6A	−0.1 (3)	C3B—C4B—C5B—C6B	0.4 (3)
C3A—C4A—C5A—C11A	−178.70 (19)	C3B—C4B—C5B—C11B	−178.09 (19)
C2A—C1A—C6A—O1A	178.80 (15)	C4B—C5B—C6B—O1B	−179.74 (15)
P1A—C1A—C6A—O1A	−4.9 (2)	C11B—C5B—C6B—O1B	−0.82 (19)
C2A—C1A—C6A—C5A	0.5 (3)	C4B—C5B—C6B—C1B	−1.6 (3)
P1A—C1A—C6A—C5A	176.79 (13)	C11B—C5B—C6B—C1B	177.31 (16)
C4A—C5A—C6A—O1A	−178.72 (15)	C2B—C1B—C6B—C5B	1.4 (3)
C11A—C5A—C6A—O1A	0.23 (19)	P1B—C1B—C6B—C5B	177.55 (13)
C4A—C5A—C6A—C1A	−0.2 (3)	C2B—C1B—C6B—O1B	179.36 (15)
C11A—C5A—C6A—C1A	178.70 (16)	P1B—C1B—C6B—O1B	−4.5 (2)
C12A—C7A—C8A—C9A	−0.4 (3)	C12B—C7B—C8B—C9B	0.3 (2)
P2A—C7A—C8A—C9A	175.70 (14)	P2B—C7B—C8B—C9B	174.34 (14)
C7A—C8A—C9A—C10A	1.4 (3)	C7B—C8B—C9B—C10B	−0.4 (3)
C8A—C9A—C10A—C11A	−1.1 (3)	C8B—C9B—C10B—C11B	0.1 (3)
C9A—C10A—C11A—C12A	−0.1 (3)	C9B—C10B—C11B—C12B	0.3 (3)
C9A—C10A—C11A—C5A	177.58 (19)	C9B—C10B—C11B—C5B	−179.99 (19)
C6A—C5A—C11A—C12A	−0.64 (18)	C6B—C5B—C11B—C12B	0.66 (19)
C4A—C5A—C11A—C12A	178.05 (19)	C4B—C5B—C11B—C12B	179.32 (19)
C6A—C5A—C11A—C10A	−178.57 (19)	C6B—C5B—C11B—C10B	−179.04 (19)
C4A—C5A—C11A—C10A	0.1 (4)	C4B—C5B—C11B—C10B	−0.4 (4)
C10A—C11A—C12A—O1A	179.17 (15)	C8B—C7B—C12B—O1B	−179.80 (15)
C5A—C11A—C12A—O1A	0.86 (19)	P2B—C7B—C12B—O1B	5.8 (2)
C10A—C11A—C12A—C7A	1.3 (3)	C8B—C7B—C12B—C11B	0.1 (3)
C5A—C11A—C12A—C7A	−177.07 (16)	P2B—C7B—C12B—C11B	−174.35 (14)
C8A—C7A—C12A—C11A	−1.0 (3)	C10B—C11B—C12B—C7B	−0.4 (3)
P2A—C7A—C12A—C11A	−177.23 (13)	C5B—C11B—C12B—C7B	179.80 (16)
C8A—C7A—C12A—O1A	−178.66 (15)	C10B—C11B—C12B—O1B	179.47 (15)
P2A—C7A—C12A—O1A	5.1 (2)	C5B—C11B—C12B—O1B	−0.30 (19)
C26A—C21A—C22A—C23A	0.9 (3)	C26B—C21B—C22B—C23B	−1.1 (3)
P1A—C21A—C22A—C23A	−173.89 (15)	P1B—C21B—C22B—C23B	176.26 (15)
C21A—C22A—C23A—C24A	−1.2 (3)	C21B—C22B—C23B—C24B	0.7 (3)
C22A—C23A—C24A—C25A	0.3 (3)	C22B—C23B—C24B—C25B	−0.2 (3)
C23A—C24A—C25A—C26A	0.8 (3)	C23B—C24B—C25B—C26B	0.1 (3)
C24A—C25A—C26A—C21A	−1.1 (3)	C24B—C25B—C26B—C21B	−0.5 (3)
C22A—C21A—C26A—C25A	0.3 (3)	C22B—C21B—C26B—C25B	1.0 (3)
P1A—C21A—C26A—C25A	175.45 (15)	P1B—C21B—C26B—C25B	−176.59 (15)
C36A—C31A—C32A—C33A	1.1 (3)	C36B—C31B—C32B—C33B	−0.9 (3)
P1A—C31A—C32A—C33A	−171.98 (15)	P1B—C31B—C32B—C33B	178.46 (16)
C31A—C32A—C33A—C34A	−1.1 (3)	C31B—C32B—C33B—C34B	−0.4 (3)
C32A—C33A—C34A—C35A	−0.2 (3)	C32B—C33B—C34B—C35B	1.0 (3)
C33A—C34A—C35A—C36A	1.3 (3)	C33B—C34B—C35B—C36B	−0.2 (3)
C34A—C35A—C36A—C31A	−1.3 (3)	C34B—C35B—C36B—C31B	−1.1 (3)
C32A—C31A—C36A—C35A	0.0 (3)	C32B—C31B—C36B—C35B	1.6 (3)
P1A—C31A—C36A—C35A	173.67 (16)	P1B—C31B—C36B—C35B	−177.78 (14)
C46A—C41A—C42A—C43A	−1.0 (3)	C46B—C41B—C42B—C43B	−1.7 (3)
P2A—C41A—C42A—C43A	178.54 (15)	P2B—C41B—C42B—C43B	178.82 (14)
C41A—C42A—C43A—C44A	0.8 (3)	C41B—C42B—C43B—C44B	1.0 (3)
C42A—C43A—C44A—C45A	0.0 (3)	C42B—C43B—C44B—C45B	0.3 (3)
C43A—C44A—C45A—C46A	−0.4 (3)	C43B—C44B—C45B—C46B	−0.9 (3)
C44A—C45A—C46A—C41A	0.0 (3)	C44B—C45B—C46B—C41B	0.1 (3)
C42A—C41A—C46A—C45A	0.6 (3)	C42B—C41B—C46B—C45B	1.2 (3)
P2A—C41A—C46A—C45A	−178.90 (16)	P2B—C41B—C46B—C45B	−179.43 (14)
C56A—C51A—C52A—C53A	0.1 (3)	C56B—C51B—C52B—C53B	−0.8 (3)
P2A—C51A—C52A—C53A	−178.74 (14)	P2B—C51B—C52B—C53B	170.45 (15)
C51A—C52A—C53A—C54A	0.3 (3)	C51B—C52B—C53B—C54B	0.5 (3)
C52A—C53A—C54A—C55A	0.0 (3)	C52B—C53B—C54B—C55B	0.5 (3)
C53A—C54A—C55A—C56A	−0.7 (3)	C53B—C54B—C55B—C56B	−1.2 (3)
C52A—C51A—C56A—C55A	−0.7 (3)	C54B—C55B—C56B—C51B	0.9 (3)
P2A—C51A—C56A—C55A	178.18 (16)	C52B—C51B—C56B—C55B	0.1 (3)
C54A—C55A—C56A—C51A	1.0 (3)	P2B—C51B—C56B—C55B	−171.70 (14)
C1A—C6A—O1A—C12A	−178.20 (16)	C7B—C12B—O1B—C6B	179.72 (15)
C5A—C6A—O1A—C12A	0.28 (18)	C11B—C12B—O1B—C6B	−0.19 (18)
C11A—C12A—O1A—C6A	−0.72 (18)	C5B—C6B—O1B—C12B	0.64 (18)
C7A—C12A—O1A—C6A	177.24 (16)	C1B—C6B—O1B—C12B	−177.53 (16)
C6A—C1A—P1A—C21A	85.02 (15)	C22B—C21B—P1B—C1B	16.60 (18)
C2A—C1A—P1A—C21A	−99.11 (16)	C26B—C21B—P1B—C1B	−166.02 (14)
C6A—C1A—P1A—C31A	−167.50 (14)	C22B—C21B—P1B—C31B	−86.92 (17)
C2A—C1A—P1A—C31A	8.36 (17)	C26B—C21B—P1B—C31B	90.45 (15)
C26A—C21A—P1A—C1A	−175.24 (14)	C6B—C1B—P1B—C21B	75.77 (15)
C22A—C21A—P1A—C1A	−0.44 (18)	C2B—C1B—P1B—C21B	−108.63 (16)
C26A—C21A—P1A—C31A	78.58 (16)	C6B—C1B—P1B—C31B	−179.86 (14)
C22A—C21A—P1A—C31A	−106.62 (17)	C2B—C1B—P1B—C31B	−4.27 (18)
C32A—C31A—P1A—C1A	−112.56 (16)	C36B—C31B—P1B—C21B	−160.73 (15)
C36A—C31A—P1A—C1A	74.27 (16)	C32B—C31B—P1B—C21B	19.90 (19)
C32A—C31A—P1A—C21A	−5.57 (18)	C36B—C31B—P1B—C1B	94.39 (15)
C36A—C31A—P1A—C21A	−178.75 (14)	C32B—C31B—P1B—C1B	−84.98 (18)
C42A—C41A—P2A—C51A	158.45 (14)	C12B—C7B—P2B—C41B	169.08 (13)
C46A—C41A—P2A—C51A	−22.01 (19)	C8B—C7B—P2B—C41B	−4.67 (17)
C42A—C41A—P2A—C7A	−97.31 (15)	C12B—C7B—P2B—C51B	−84.18 (14)
C46A—C41A—P2A—C7A	82.23 (18)	C8B—C7B—P2B—C51B	102.07 (16)
C56A—C51A—P2A—C41A	−92.30 (16)	C46B—C41B—P2B—C7B	81.32 (16)
C52A—C51A—P2A—C41A	86.51 (17)	C42B—C41B—P2B—C7B	−99.27 (14)
C56A—C51A—P2A—C7A	164.08 (15)	C46B—C41B—P2B—C51B	−25.55 (17)
C52A—C51A—P2A—C7A	−17.11 (18)	C42B—C41B—P2B—C51B	153.86 (13)
C8A—C7A—P2A—C41A	8.64 (17)	C56B—C51B—P2B—C7B	−166.96 (14)
C12A—C7A—P2A—C41A	−175.55 (14)	C52B—C51B—P2B—C7B	21.73 (18)
C8A—C7A—P2A—C51A	113.48 (16)	C56B—C51B—P2B—C41B	−61.82 (16)
C12A—C7A—P2A—C51A	−70.72 (15)	C52B—C51B—P2B—C41B	126.87 (16)

Experimental details

Crystal data
Chemical formula	C₃₆H₂₆OP₂
M_r	536.51
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	11.7463 (2), 14.7238 (3), 16.7140 (4)
α, β, γ (°)	96.821 (2), 96.351 (5), 95.240 (2)
V (Å³)	2836.58 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.40 × 0.22 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	28406, 12364, 8323
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.100, 0.90
No. of reflections	12363
No. of parameters	703
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.30

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

We thank Dr Manuel Fernandes for the data collection and SASOL, THRIP and the University of KwaZulu-Natal for financial support.

References

Banerjee, A. (1973). Acta Cryst. B29, 2070–2074. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Bruker (2005). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dideberg, O., Dupont, L. & André, J. M. (1972). Acta Cryst. B28, 1002–1007. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Hillebrand, S., Bruckmann, J., Kruger, C. & Haenel, M. W. (1995). Tetrahedron Lett. 36, 75–78. CSD CrossRef CAS Web of Science Google Scholar
Kranenburg, M., Vanderburgt, Y. E. M., Kamer, P. C. J., van Leeuwen, P. W. N. M., Goubitz, K. & Fraanje, J. (1995). Organometallics, 14, 3081–3089. CrossRef CAS Web of Science Google Scholar
Marimuthu, T., Bala, M. D. & Friedrich, H. B. (2008a). Acta Cryst. E64, o711. Web of Science CSD CrossRef IUCr Journals Google Scholar
Marimuthu, T., Bala, M. D. & Friedrich, H. B. (2008b). Acta Cryst. E64, o772. Web of Science CSD CrossRef IUCr Journals Google Scholar
Reppart, W. J., Gallucci, J. C., Lundstedt, A. P. & Gerkin, R. E. (1984). Acta Cryst. C40, 1572–1576. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vogl, E. M., Bruckmann, J., Krüger, C. & Haenel, M. W. (1996). J. Organomet. Chem. 520, 249–252. CSD CrossRef CAS Web of Science Google Scholar