Polymorphism of 2,5-[(di­phenyl­phosphan­yl)meth­yl]-1,1,2,4,4,5-hexa­phenyl-1,4-diphospha-2,5-dibora­cyclo­hexa­ne

2,5-[(Di­phenyl­phosphan­yl)meth­yl]-1,1,2,4,4,5-hexa­phenyl-1,4-diphospha-2,5-dibora­cyclo­hexane shows polymorphism as two tetra­hydro­furan (THF) disolvates [C₆₄H₅₈B₂P₄·2C₄H₈O, (Ia) and (Ib)] and pseudo-polymorphism as its toluene mono­solvate [C₆₄H₅₈B₂P₄·C₇H₈, (Ic)]. In each of polymorphs (Ia) and (Ib), the diphosphadibora­cyclo­hexane mol­ecule is located on a centre of inversion. The THF mol­ecule of (Ib) is disordered over two sites, with a site-occupation factor of 0.612 (8) for the major-occupied site. Both structures crystallize in the same space group (P2₁/n), but they display a different crystal packing. For pseudo-polymorph (Ic), although the space group is P2₁/c, which is just a different setting of the P2₁/n space group of (Ia) and (Ib), the crystal packing is completely different. Although the crystal packing in these three structures is significantly different, their mol­ecular conformations are surprisingly the same.

S1. Introduction

Multidentate ligand systems have attracted considerable inter­est in recent decades. Prominent examples of this class of ligands are the (pyrazol-1-yl)borates (scorpionates) [R_nBpz_4-n]^- (R = H, alkyl, aryl; n = 2, 1, 0; pz = pyrazol-1-yl) (Trofimenko, 1993, 1999; Bieller et al., 2004, 2005, 2006; Zhang et al., 2004, 2007; Morawitz et al., 2008a,b). Scorpionates have found a wide range of chemical applications, from modelling the active site of metalloenzymes, through analytical chemistry and organic synthesis to catalysis and materials science (Adams & Cotton, 1988). One way to alter the donor/acceptor properties of scorpionate ligands over a wider range is to replace the pyrazolyl rings by phospho­rus-containing groups. Similar to parent scorpionates, these ligands provide a monoanionic tridentate face-capping coordination mode, but they differ from parent scorpionates with regard to the softness of their donor sets. Recently, we have reported on the syntheses of the hybrid scorpionates [ArBpz_x(CH₂SMe)_3-x]^- (Ar = Ph, C₆H₄SiMe₃), which were achieved by transamination of [ArB(CH₂SMe)Br]₂ and [ArB(CH₂SMe)₂]₂, respectively, with a mixture of pyrazole and alkali metal pyrazolide (Ruth et al., 2008). The starting materials for this approach, the heterocycles [ArB(CH₂SMe)Br]₂ and [ArB(CH₂SMe)₂]₂ (Ar = Ph, C₆H₄SiMe₃), were prepared from ArBBr₂ and one or two equivalents of Li[CH₂SMe]. Therefore, we asked ourselves the question if it is possible to synthesize the related phosphanyl­methyl-substituted scorpionates [PhBpz_x(CH₂PPh₂)_3-x]^- via the corresponding heterocycles [PhB(CH₂PPh₂)Cl]₂ and [PhB(CH₂PPh₂)₂]₂, respectively, from PhBCl₂ and Li[CH₂PPh₂].

Unfortunately, the reaction of PhBCl₂ with unsupported and tmeda-supported (tmeda is tetra­methyl­ethylenedi­amine) Li[CH₂PPh₂] gave, in all cases, a mixture of [PhB(CH₂PPh₂)][PhBCl₂]₂, [PhB(CH₂PPh₂)₂]₂ and Li[PhB(CH₂PPh₂)₃].

The addition compound [PhB(CH₂PPh₂)₂][PhBCl₂]₂ (Müller et al., 2014a) could be isolated from the solution of a 1:1 reaction of PhBCl₂ with unsupported Li[CH₂PPh₂] (Fink et al., 2014; Ruth et al., 2007). The heterocycle [PhB(CH₂PPh₂)₂]₂, (I), was obtained from the reaction of PhBCl₂ with tmeda-supported Li[CH₂PPh₂]. X-ray quality crystals of (I) were grown from THF [polymorphs (Ia) and (Ib) were obtained from THF, the first at 238 K and the second at room temperature), as well as from toluene [pseudo-polymorph (Ic)]. Treatment of PhBCl₂ with three equivalents of tmeda-supported Li(tmeda)[CH₂PPh₂] led to the replacement of all Cl substituents by (di­phenyl­phosphanyl)methyl groups and consequently to the addition of the third one. In this context, it should be noted that the scorpionate Li(tmeda)₂[PhB(CH₂PPh₂)₃] (III) (Steinborn et al., 1998) can be transformed into the heteroscorpionate Li(tmeda)[PhBpz₂(CH₂PPh₂)] (Müller et al., 2014b) by the reaction of Li(tmeda)₂[PhB(CH₂PPh₂)₃] with two equivalents of pyrazole.

S2. Experimental

S2.1. Synthesis and crystallization

For the synthesis of [PhB(CH₂PPh₂)₂]₂, (I), a solution of PhBCl₂ (0.10 mmol, 116 mg) in toluene (3 ml) was added to a cooled (195 K) mixture of a tmeda-supported Li(tmeda)[CH₂PPh₂] (0.22 mmol, 203 mg) in Et₂O (25 ml). The mixture was stirred for 1 h at 195 K and then warmed to room temperature. After removal of all volatiles in vacuo from the filtered reaction solution, the residue was extracted into THF (5 ml). Single crystals of (I) with two additional molecules of THF [i.e. (Ib)] were grown from this THF solution at 238 K (yield 40%). Remark: single crystals of a polymorph [i.e. (Ia)] were grown from a THF solution at room temperature. X-ray quality crystals of the toluene solvate [i.e. (Ic)] were obtained from toluene at room temperature.

S2.2. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. H atoms were refined using a riding model, with aromatic C—H = 0.95 Å, methyl C—H = 0.98 Å or methyl­ene C—H = 0.99 Å and with U_iso(H) = 1.5U_eq(C) for methyl groups or 1.2U_eq(C) otherwise. The methyl group of the toluene molecule in (Ic) was allowed to rotate but not to tip.

The THF solvent molecule in (Ib) is disordered over two sites, with a site-occupation factor of 0.612 (8) for the major occupied site. The displacement ellipsoids of the disordered atoms were restrained to an isotropic behaviour. The C—C and C—O distances, respectively, involving the disordered atoms were restrained to be equal.

The structure of (Ic) shows pseudosymmetry. PLATON (Spek, 2009) detects a pseudo-translation operation, i.e. a pseudo-I-centring. However, only 83% of the atoms comply with this pseudosymmetry element.

S3. Results and discussion

The asymmetric unit of polymorph (Ia) (Fig. 1) contains half a molecule of the title compound and one molecule of THF. The molecule is located on a centre of inversion (Fig. 1). The B atoms are almost ideally tetra­hedrally coordinated [103.74 (14)–114.13 (17)°]. For the P atoms, some minor distortion can be observed, especially for atom P2, where the lone pair significantly reduces the C—P—C angles [C21—P2—C31 = 99.30 (10)°, C21—P2—C2 = 102.60 (10)° and C31—P2—C2 = 102.14 (10)°]. The central six-membered B₂P₂C₂ ring adopts a chair conformation. The phenyl rings at the B atoms are in axial positions. The ring P atom, on the other hand, has one phenyl substituent in an axial the other in an equatorial position. The acyclic CH₂—P bonds are trans to the B—P bonds in the ring [P1—B1—C2—P2 = 176.41 (10)°].

In polymorph (Ib), the molecule (Fig. 2) is again located on a centre of inversion and there is one molecule of THF in the asymmetric unit. The B atoms are almost ideally tetra­hedrally coordinated [105.58 (13)–113.70 (16)°]. For the P atoms, some minor distortion can be observed, especially for atom P2, where the lone pair significantly reduces the C—P—C angles [C21—P2—C31 = 100.11 (9)°, C21—P2—C2 = 102.92 (9)° and C31—P2—C2 = 103.21 (9)°]. The central six-membered B₂P₂C₂ ring adopts a chair conformation. The phenyl rings at the B atoms are in axial positions. The acyclic CH₂—P bonds are trans to the B—P bonds in the ring [P1—B1—C2—P2 = 179.53 (9)°].

(Ib) is a polymorph of (Ia). Both structures crystallalize in the monoclinic crystal system with the same space group, i.e. P2₁/c. However, the cell parameters are rather different. Although, the a axis [12.5508 (6) Å for (Ia) and 12.3097 (6) Å for (Ib)] and the monoclinic angle [93.962 (4)° for (Ia) and 93.720 (4)° for (Ib)] are quite similar, the b [10.1916 (5) Å for (Ia) and 13.3629 (4) Å for (Ib)] and c [24.7009 (10) Å for (Ia) and 18.4243 (9) Å for (Ib)] axes differ significantly.

Furthermore, both polymorphs display a different crystal packing (Figs. 3 and 4). The central molecule in both packing diagrams is drawn in essentially the same orientation. The significant difference between the packing patterns of the two structures can be expressed by the dihedral angle between the planes of the two symmetry-equivalent B₂P₂C₂ heterocycles. Whereas the heterocycles are almost coplanar in (Ia) [18.78 (11)°], they are almost perpendicular in (Ib) [77.03 (4)°].

(Ic) (Fig. 5) is a pseudo-polymorph of (Ia) and (Ib). In the present case, there is one diphosphadibora­cyclo­hexane molecule together with one molecule of toluene in the asymmetric unit, both of which do not show any crystallographic symmetry. The B atoms are almost ideally tetra­hedrally coordinated [101.7 (2)–114.2 (3)° for B1 and 103.4 (3)–113.2 (3)° for B2]. For the P atoms, some minor distortion can be observed, especially for atoms P3 and P4, where the lone pair significantly reduces the C—P—C angles [C81—P3—C71 = 99.50 (17)°, C81—P3—C3 = 102.97 (17)° and C71—P3—C3 = 102.16 (17)°; C4—P4—C101 = 103.52 (17)°, C4—P4—C91 = 103.72 (17)° and C101—P4—C91 96.75 (16)°]. The central six-membered B₂P₂C₂ ring adopts a chair conformation. The phenyl rings at the B atoms are in an axial position of ring. The acyclic CH₂—P bonds are trans to the B—P bonds in the ring [P1—B1—C3—P3 = -176.54 (19)° and P2—B2—C4—P4 = 178.66 (18)°]. The space group of (Ic) is P2₁/c, which is just a different setting of the P2₁/n space group of (Ia) and (Ib). Nevertheless, apart from similar values for the b axis of (Ib) and (Ic) [13.3629 (4) and 13.4283 (6) Å, respectively], the cell parameters differ completely from those of (Ia) and (Ib).

In addition, the crystal packing (Fig. 6) is once again completely different, as in the previous two structures. The molecules inside of unit cell are in essentially the same orientation as in Figs. 3 and 5. The significant difference between the packing pattern between the two structures can again be expressed by the dihedral angle between the planes of the two symmetry-equivalent B₂P₂C₂ heterocycles, which is either 0° for inversion-related molecules or 37.39 (5)° for glide-plane- or screw-axis-related molecules.

In contrast to the different packing patterns in the three described structures, the molecular conformation of the molecule is essentially the same in all three structures. A least-squares fit (superimposing the central six-membered rings) of the three structures (Fig. 7) shows the striking similarities between the molecular conformations, which are essentially the same in all three cases.

Concluding, it can be said, that the title compound tends to form polymorphic crystal structures and it can be assumed that other (pseudo-)polymorphs might be found.

Related literature

For related literature, see: Adams & Cotton (1988); Bieller et al. (2004, 2005, 2006); Fink et al. (2014); Müller et al. (2014a, 2014b); Morawitz et al. (2008a, 2008b); Ruth et al. (2007, 2008); Spek (2009); Steinborn et al. (1998); Trofimenko (1993, 1999); Zhang et al. (2004, 2007).

Computing details

For all compounds, data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures

	Fig. 1. A perspective view of polymorph (Ia), with displacement ellipsoids drawn at the 50% probability level. H atoms and solvent molecules have been omitted for clarity. Atoms with the suffix `A' were generated using the symmetry operator (-x+1, -y+1, -z+1).
	Fig. 2. A perspective view of polymorph (Ib), with displacement ellipsoids drawn at the 50% probability level. H atoms and solvent molecules have been omitted for clarity. Atoms with the suffix `A' were generated using the symmetry operator (-x+1, -y+1, -z+1).
	Fig. 3. Packing diagram of polymorph (Ia), viewed on the ac plane. H atoms and solvent molecules have been omitted for clarity.
	Fig. 4. Packing diagram of polymorph (Ib). H atoms and solvent molecules have been omitted for clarity. The central molecule is in exactly the same orientation as the central molecule in Fig. 3.
	Fig. 5. Perspective view of pseudo-polymorph (Ic), with displacement ellipsoids drawn at the 50% probability level. H atoms and solvent molecules have been omitted for clarity.
	Fig. 6. Packing diagram of pseudo-polymorph(Ic). H atoms and solvent molecules have been omitted for clarity. The molecules drawn inside of the unit are in exactly the same orientation as the central molecule in Figs. 3 and 5.
	Fig. 7. Least-squares fit superimposing the central six-membered heterocycles of (Ia) (open bonds), (Ib) (dashed full bonds) and (Ic) (full bonds).

(Ia) 2,5-[(Diphenylphosphanyl)methyl]-1,1,2,4,4,5-hexaphenyl-1,4-diphospha-2,5-diboracyclohexane; tetrahydrofuran disolvate

Crystal data

C64H58B2P4·2C4H8O	F(000) = 1184
Mr = 1116.81	Dx = 1.177 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25506 reflections
a = 12.5508 (6) Å	θ = 3.5–25.8°
b = 10.1916 (5) Å	µ = 0.16 mm^−1
c = 24.7009 (10) Å	T = 173 K
β = 93.962 (4)°	Block, colourless
V = 3152.0 (3) Å^3	0.28 × 0.20 × 0.14 mm
Z = 2

Data collection

Stoe IPDS II two-circle diffractometer	5902 independent reflections
Radiation source: fine-focus sealed tube	4620 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.078
ω scans	θmax = 25.6°, θmin = 3.5°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −15→15
Tmin = 0.945, Tmax = 0.989	k = −12→12
39212 measured reflections	l = −30→29

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)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.122	w = 1/[σ^2(Fo^2) + (0.0619P)^2 + 1.5352P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
5902 reflections	Δρmax = 0.43 e Å^−3
362 parameters	Δρmin = −0.45 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0031 (7)

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.

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

	x	y	z	Uiso*/Ueq
C1	0.45419 (15)	0.3582 (2)	0.52603 (8)	0.0204 (4)
H1A	0.3907	0.3467	0.5004	0.024*
H1B	0.4581	0.2804	0.5501	0.024*
B1	0.43261 (18)	0.4881 (2)	0.56421 (9)	0.0204 (5)
P1	0.42835 (4)	0.64420 (5)	0.51348 (2)	0.01846 (14)
C2	0.53168 (16)	0.5225 (2)	0.60931 (8)	0.0223 (4)
H2A	0.5186	0.6092	0.6257	0.027*
H2B	0.5989	0.5285	0.5907	0.027*
P2	0.54756 (5)	0.39760 (6)	0.66400 (2)	0.02486 (15)
C11	0.31863 (16)	0.4772 (2)	0.59216 (8)	0.0215 (4)
C12	0.28156 (18)	0.5796 (2)	0.62408 (9)	0.0270 (5)
H12	0.3234	0.6569	0.6291	0.032*
C13	0.18473 (19)	0.5708 (3)	0.64874 (10)	0.0319 (5)
H13	0.1613	0.6421	0.6697	0.038*
C14	0.12265 (18)	0.4579 (3)	0.64263 (10)	0.0341 (6)
H14	0.0568	0.4518	0.6593	0.041*
C15	0.15781 (18)	0.3545 (3)	0.61201 (10)	0.0321 (5)
H15	0.1163	0.2768	0.6079	0.038*
C16	0.25435 (17)	0.3644 (2)	0.58715 (9)	0.0259 (5)
H16	0.2771	0.2926	0.5663	0.031*
C21	0.68023 (18)	0.4379 (2)	0.69721 (9)	0.0275 (5)
C22	0.7142 (2)	0.3623 (3)	0.74253 (11)	0.0452 (7)
H22	0.6675	0.2982	0.7557	0.054*
C23	0.8149 (2)	0.3791 (4)	0.76857 (12)	0.0535 (8)
H23	0.8355	0.3281	0.7998	0.064*
C24	0.8850 (2)	0.4690 (3)	0.74954 (12)	0.0486 (7)
H24	0.9542	0.4792	0.7672	0.058*
C25	0.8542 (2)	0.5444 (3)	0.70455 (11)	0.0407 (6)
H25	0.9022	0.6067	0.6913	0.049*
C26	0.75191 (19)	0.5289 (3)	0.67856 (10)	0.0343 (5)
H26	0.7313	0.5812	0.6478	0.041*
C31	0.46174 (18)	0.4644 (2)	0.71559 (9)	0.0284 (5)
C32	0.4739 (2)	0.5920 (3)	0.73588 (10)	0.0370 (6)
H32	0.5298	0.6459	0.7244	0.044*
C33	0.4048 (2)	0.6408 (3)	0.77277 (11)	0.0474 (7)
H33	0.4135	0.7278	0.7862	0.057*
C34	0.3229 (2)	0.5623 (4)	0.79006 (11)	0.0517 (8)
H34	0.2750	0.5963	0.8147	0.062*
C35	0.3115 (2)	0.4350 (3)	0.77129 (12)	0.0476 (7)
H35	0.2568	0.3807	0.7838	0.057*
C36	0.3802 (2)	0.3860 (3)	0.73396 (10)	0.0373 (6)
H36	0.3714	0.2987	0.7209	0.045*
C41	0.43105 (17)	0.8012 (2)	0.54989 (9)	0.0236 (4)
C42	0.52595 (19)	0.8489 (2)	0.57573 (9)	0.0294 (5)
H42	0.5911	0.8032	0.5723	0.035*
C43	0.5252 (2)	0.9639 (3)	0.60666 (10)	0.0382 (6)
H43	0.5898	0.9952	0.6244	0.046*
C44	0.4311 (3)	1.0327 (3)	0.61169 (11)	0.0423 (7)
H44	0.4312	1.1109	0.6326	0.051*
C45	0.3367 (2)	0.9865 (3)	0.58598 (11)	0.0415 (6)
H45	0.2722	1.0338	0.5892	0.050*
C46	0.33576 (19)	0.8718 (2)	0.55556 (10)	0.0323 (5)
H46	0.2705	0.8406	0.5385	0.039*
C51	0.31038 (16)	0.6642 (2)	0.46634 (8)	0.0224 (4)
C52	0.21687 (18)	0.5915 (2)	0.47087 (10)	0.0309 (5)
H52	0.2146	0.5243	0.4974	0.037*
C53	0.12689 (19)	0.6181 (3)	0.43616 (11)	0.0408 (6)
H53	0.0631	0.5693	0.4393	0.049*
C54	0.13038 (19)	0.7154 (3)	0.39706 (10)	0.0390 (6)
H54	0.0689	0.7330	0.3735	0.047*
C55	0.2226 (2)	0.7870 (3)	0.39212 (11)	0.0377 (6)
H55	0.2249	0.8529	0.3650	0.045*
C56	0.31216 (18)	0.7621 (2)	0.42696 (10)	0.0312 (5)
H56	0.3752	0.8123	0.4239	0.037*
O61	0.8383 (4)	0.8397 (6)	0.6055 (2)	0.163 (2)
C62	0.8358 (6)	0.7923 (10)	0.5562 (3)	0.165 (4)
H62A	0.7860	0.8442	0.5319	0.198*
H62B	0.8106	0.7002	0.5560	0.198*
C63	0.9395 (11)	0.7984 (16)	0.5381 (4)	0.269 (8)
H63A	0.9376	0.8391	0.5017	0.323*
H63B	0.9694	0.7089	0.5357	0.323*
C64	1.0056 (6)	0.8768 (15)	0.5769 (5)	0.226 (6)
H64A	1.0746	0.8330	0.5867	0.271*
H64B	1.0195	0.9650	0.5621	0.271*
C65	0.9418 (6)	0.8851 (7)	0.6227 (4)	0.148 (3)
H65A	0.9729	0.8300	0.6528	0.178*
H65B	0.9384	0.9769	0.6356	0.178*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0158 (9)	0.0246 (11)	0.0210 (10)	−0.0030 (8)	0.0029 (7)	0.0010 (8)
B1	0.0178 (11)	0.0248 (12)	0.0187 (11)	−0.0018 (9)	0.0031 (9)	0.0007 (9)
P1	0.0155 (2)	0.0208 (3)	0.0192 (3)	−0.0020 (2)	0.00175 (18)	−0.0006 (2)
C2	0.0211 (10)	0.0269 (11)	0.0192 (10)	−0.0009 (8)	0.0032 (8)	0.0004 (8)
P2	0.0280 (3)	0.0255 (3)	0.0209 (3)	−0.0032 (2)	0.0007 (2)	0.0008 (2)
C11	0.0180 (9)	0.0286 (11)	0.0179 (10)	−0.0008 (8)	0.0003 (8)	0.0036 (9)
C12	0.0256 (11)	0.0312 (12)	0.0246 (11)	−0.0005 (9)	0.0052 (9)	0.0010 (9)
C13	0.0292 (12)	0.0379 (14)	0.0295 (12)	0.0056 (10)	0.0089 (9)	−0.0009 (10)
C14	0.0198 (10)	0.0502 (15)	0.0332 (13)	−0.0008 (10)	0.0083 (9)	0.0054 (12)
C15	0.0236 (11)	0.0385 (13)	0.0345 (13)	−0.0085 (10)	0.0051 (9)	0.0033 (11)
C16	0.0227 (10)	0.0310 (12)	0.0241 (11)	−0.0024 (9)	0.0036 (8)	0.0012 (9)
C21	0.0290 (11)	0.0299 (12)	0.0231 (11)	0.0040 (9)	−0.0006 (9)	−0.0024 (9)
C22	0.0441 (15)	0.0530 (17)	0.0373 (15)	0.0009 (13)	−0.0055 (12)	0.0119 (13)
C23	0.0499 (17)	0.068 (2)	0.0400 (16)	0.0097 (15)	−0.0129 (13)	0.0103 (15)
C24	0.0327 (14)	0.069 (2)	0.0421 (16)	0.0107 (14)	−0.0108 (12)	−0.0114 (15)
C25	0.0295 (12)	0.0514 (16)	0.0406 (15)	−0.0038 (12)	−0.0009 (11)	−0.0107 (13)
C26	0.0298 (12)	0.0407 (14)	0.0319 (13)	0.0003 (10)	−0.0025 (10)	−0.0006 (11)
C31	0.0292 (11)	0.0362 (13)	0.0197 (11)	−0.0028 (10)	0.0001 (9)	0.0042 (9)
C32	0.0421 (14)	0.0415 (15)	0.0279 (12)	−0.0051 (11)	0.0059 (10)	−0.0039 (11)
C33	0.0570 (17)	0.0551 (18)	0.0309 (14)	0.0030 (14)	0.0090 (12)	−0.0085 (13)
C34	0.0481 (16)	0.081 (2)	0.0278 (13)	0.0125 (16)	0.0129 (12)	0.0047 (14)
C35	0.0379 (14)	0.069 (2)	0.0378 (15)	−0.0027 (14)	0.0116 (12)	0.0155 (14)
C36	0.0361 (13)	0.0449 (15)	0.0309 (13)	−0.0055 (11)	0.0032 (10)	0.0093 (11)
C41	0.0287 (11)	0.0209 (10)	0.0217 (10)	−0.0021 (9)	0.0057 (8)	0.0008 (9)
C42	0.0340 (12)	0.0284 (12)	0.0255 (11)	−0.0069 (10)	0.0013 (9)	0.0013 (10)
C43	0.0555 (16)	0.0305 (13)	0.0281 (13)	−0.0165 (12)	−0.0012 (11)	0.0009 (10)
C44	0.0724 (19)	0.0249 (13)	0.0306 (13)	−0.0051 (13)	0.0102 (13)	−0.0063 (11)
C45	0.0538 (16)	0.0304 (13)	0.0418 (15)	0.0069 (12)	0.0141 (13)	−0.0060 (11)
C46	0.0317 (12)	0.0297 (13)	0.0362 (13)	0.0004 (10)	0.0069 (10)	−0.0049 (10)
C51	0.0198 (10)	0.0263 (11)	0.0212 (10)	0.0015 (8)	0.0013 (8)	−0.0030 (9)
C52	0.0261 (11)	0.0353 (13)	0.0307 (12)	−0.0045 (10)	−0.0021 (9)	0.0035 (10)
C53	0.0213 (11)	0.0584 (18)	0.0419 (14)	−0.0077 (11)	−0.0035 (10)	0.0071 (13)
C54	0.0255 (12)	0.0552 (17)	0.0350 (14)	0.0049 (11)	−0.0070 (10)	0.0036 (12)
C55	0.0321 (13)	0.0436 (15)	0.0365 (14)	0.0042 (11)	−0.0031 (10)	0.0131 (12)
C56	0.0235 (11)	0.0339 (13)	0.0360 (13)	−0.0002 (9)	0.0003 (9)	0.0064 (11)
O61	0.132 (4)	0.221 (6)	0.137 (4)	−0.054 (4)	0.026 (3)	−0.051 (4)
C62	0.111 (5)	0.271 (10)	0.114 (5)	−0.045 (6)	0.022 (4)	−0.091 (6)
C63	0.223 (12)	0.43 (2)	0.161 (9)	−0.014 (13)	0.070 (9)	−0.149 (12)
C64	0.095 (5)	0.383 (18)	0.199 (10)	−0.041 (8)	0.011 (6)	0.129 (11)
C65	0.113 (5)	0.124 (5)	0.198 (8)	−0.002 (4)	−0.050 (5)	−0.057 (5)

Geometric parameters (Å, º)

C1—B1	1.658 (3)	C33—H33	0.9500
C1—P1^i	1.823 (2)	C34—C35	1.382 (5)
C1—H1A	0.9900	C34—H34	0.9500
C1—H1B	0.9900	C35—C36	1.397 (4)
B1—C11	1.635 (3)	C35—H35	0.9500
B1—C2	1.649 (3)	C36—H36	0.9500
B1—P1	2.023 (2)	C41—C42	1.399 (3)
P1—C1^i	1.823 (2)	C41—C46	1.411 (3)
P1—C51	1.831 (2)	C42—C43	1.399 (4)
P1—C41	1.835 (2)	C42—H42	0.9500
C2—P2	1.857 (2)	C43—C44	1.387 (4)
C2—H2A	0.9900	C43—H43	0.9500
C2—H2B	0.9900	C44—C45	1.387 (4)
P2—C21	1.851 (2)	C44—H44	0.9500
P2—C31	1.854 (2)	C45—C46	1.390 (4)
C11—C16	1.405 (3)	C45—H45	0.9500
C11—C12	1.406 (3)	C46—H46	0.9500
C12—C13	1.399 (3)	C51—C56	1.394 (3)
C12—H12	0.9500	C51—C52	1.399 (3)
C13—C14	1.392 (4)	C52—C53	1.396 (3)
C13—H13	0.9500	C52—H52	0.9500
C14—C15	1.387 (4)	C53—C54	1.388 (4)
C14—H14	0.9500	C53—H53	0.9500
C15—C16	1.399 (3)	C54—C55	1.381 (4)
C15—H15	0.9500	C54—H54	0.9500
C16—H16	0.9500	C55—C56	1.391 (3)
C21—C26	1.392 (4)	C55—H55	0.9500
C21—C22	1.401 (4)	C56—H56	0.9500
C22—C23	1.388 (4)	O61—C62	1.307 (7)
C22—H22	0.9500	O61—C65	1.416 (7)
C23—C24	1.376 (5)	C62—C63	1.406 (12)
C23—H23	0.9500	C62—H62A	0.9900
C24—C25	1.384 (4)	C62—H62B	0.9900
C24—H24	0.9500	C63—C64	1.461 (14)
C25—C26	1.404 (3)	C63—H63A	0.9900
C25—H25	0.9500	C63—H63B	0.9900
C26—H26	0.9500	C64—C65	1.434 (11)
C31—C36	1.399 (3)	C64—H64A	0.9900
C31—C32	1.399 (4)	C64—H64B	0.9900
C32—C33	1.393 (4)	C65—H65A	0.9900
C32—H32	0.9500	C65—H65B	0.9900
C33—C34	1.392 (4)
B1—C1—P1^i	119.01 (14)	C32—C33—H33	119.9
B1—C1—H1A	107.6	C35—C34—C33	119.9 (3)
P1^i—C1—H1A	107.6	C35—C34—H34	120.1
B1—C1—H1B	107.6	C33—C34—H34	120.1
P1^i—C1—H1B	107.6	C34—C35—C36	120.1 (3)
H1A—C1—H1B	107.0	C34—C35—H35	119.9
C11—B1—C2	111.74 (17)	C36—C35—H35	119.9
C11—B1—C1	111.59 (17)	C35—C36—C31	120.6 (3)
C2—B1—C1	114.13 (17)	C35—C36—H36	119.7
C11—B1—P1	109.19 (14)	C31—C36—H36	119.7
C2—B1—P1	103.74 (14)	C42—C41—C46	118.6 (2)
C1—B1—P1	105.88 (14)	C42—C41—P1	120.88 (17)
C1^i—P1—C51	108.03 (10)	C46—C41—P1	120.42 (17)
C1^i—P1—C41	106.62 (10)	C43—C42—C41	120.2 (2)
C51—P1—C41	101.61 (10)	C43—C42—H42	119.9
C1^i—P1—B1	109.46 (9)	C41—C42—H42	119.9
C51—P1—B1	117.84 (10)	C44—C43—C42	120.7 (2)
C41—P1—B1	112.53 (10)	C44—C43—H43	119.7
B1—C2—P2	112.55 (14)	C42—C43—H43	119.7
B1—C2—H2A	109.1	C43—C44—C45	119.6 (2)
P2—C2—H2A	109.1	C43—C44—H44	120.2
B1—C2—H2B	109.1	C45—C44—H44	120.2
P2—C2—H2B	109.1	C44—C45—C46	120.5 (3)
H2A—C2—H2B	107.8	C44—C45—H45	119.7
C21—P2—C31	99.30 (10)	C46—C45—H45	119.7
C21—P2—C2	102.60 (10)	C45—C46—C41	120.5 (2)
C31—P2—C2	102.14 (10)	C45—C46—H46	119.8
C16—C11—C12	116.51 (19)	C41—C46—H46	119.8
C16—C11—B1	122.17 (19)	C56—C51—C52	119.2 (2)
C12—C11—B1	121.29 (19)	C56—C51—P1	118.17 (16)
C13—C12—C11	121.8 (2)	C52—C51—P1	122.43 (17)
C13—C12—H12	119.1	C53—C52—C51	119.7 (2)
C11—C12—H12	119.1	C53—C52—H52	120.1
C14—C13—C12	120.1 (2)	C51—C52—H52	120.1
C14—C13—H13	119.9	C54—C53—C52	120.2 (2)
C12—C13—H13	119.9	C54—C53—H53	119.9
C15—C14—C13	119.4 (2)	C52—C53—H53	119.9
C15—C14—H14	120.3	C55—C54—C53	120.4 (2)
C13—C14—H14	120.3	C55—C54—H54	119.8
C14—C15—C16	120.2 (2)	C53—C54—H54	119.8
C14—C15—H15	119.9	C54—C55—C56	119.7 (2)
C16—C15—H15	119.9	C54—C55—H55	120.2
C15—C16—C11	122.0 (2)	C56—C55—H55	120.2
C15—C16—H16	119.0	C55—C56—C51	120.7 (2)
C11—C16—H16	119.0	C55—C56—H56	119.6
C26—C21—C22	117.6 (2)	C51—C56—H56	119.6
C26—C21—P2	125.69 (18)	C62—O61—C65	111.3 (6)
C22—C21—P2	116.54 (19)	O61—C62—C63	108.5 (7)
C23—C22—C21	121.3 (3)	O61—C62—H62A	110.0
C23—C22—H22	119.4	C63—C62—H62A	110.0
C21—C22—H22	119.4	O61—C62—H62B	110.0
C24—C23—C22	120.5 (3)	C63—C62—H62B	110.0
C24—C23—H23	119.8	H62A—C62—H62B	108.4
C22—C23—H23	119.8	C62—C63—C64	108.2 (7)
C23—C24—C25	119.6 (3)	C62—C63—H63A	110.1
C23—C24—H24	120.2	C64—C63—H63A	110.1
C25—C24—H24	120.2	C62—C63—H63B	110.1
C24—C25—C26	120.1 (3)	C64—C63—H63B	110.1
C24—C25—H25	120.0	H63A—C63—H63B	108.4
C26—C25—H25	120.0	C65—C64—C63	103.1 (7)
C21—C26—C25	121.0 (2)	C65—C64—H64A	111.1
C21—C26—H26	119.5	C63—C64—H64A	111.1
C25—C26—H26	119.5	C65—C64—H64B	111.1
C36—C31—C32	118.6 (2)	C63—C64—H64B	111.1
C36—C31—P2	119.1 (2)	H64A—C64—H64B	109.1
C32—C31—P2	122.23 (18)	O61—C65—C64	107.1 (7)
C33—C32—C31	120.6 (3)	O61—C65—H65A	110.3
C33—C32—H32	119.7	C64—C65—H65A	110.3
C31—C32—H32	119.7	O61—C65—H65B	110.3
C34—C33—C32	120.1 (3)	C64—C65—H65B	110.3
C34—C33—H33	119.9	H65A—C65—H65B	108.6
P1^i—C1—B1—C11	175.07 (14)	C2—P2—C31—C36	124.28 (19)
P1^i—C1—B1—C2	−57.1 (2)	C21—P2—C31—C32	51.1 (2)
P1^i—C1—B1—P1	56.38 (17)	C2—P2—C31—C32	−54.0 (2)
C11—B1—P1—C1^i	−170.82 (14)	C36—C31—C32—C33	−1.3 (4)
C2—B1—P1—C1^i	69.92 (15)	P2—C31—C32—C33	177.0 (2)
C1—B1—P1—C1^i	−50.56 (17)	C31—C32—C33—C34	0.3 (4)
C11—B1—P1—C51	−46.92 (18)	C32—C33—C34—C35	1.1 (4)
C2—B1—P1—C51	−166.18 (12)	C33—C34—C35—C36	−1.6 (4)
C1—B1—P1—C51	73.34 (15)	C34—C35—C36—C31	0.6 (4)
C11—B1—P1—C41	70.82 (16)	C32—C31—C36—C35	0.8 (4)
C2—B1—P1—C41	−48.44 (16)	P2—C31—C36—C35	−177.6 (2)
C1—B1—P1—C41	−168.91 (13)	C1^i—P1—C41—C42	−44.0 (2)
C11—B1—C2—P2	58.9 (2)	C51—P1—C41—C42	−156.97 (18)
C1—B1—C2—P2	−68.86 (19)	B1—P1—C41—C42	76.1 (2)
P1—B1—C2—P2	176.41 (10)	C1^i—P1—C41—C46	140.48 (18)
B1—C2—P2—C21	166.49 (14)	C51—P1—C41—C46	27.5 (2)
B1—C2—P2—C31	−90.96 (16)	B1—P1—C41—C46	−99.51 (19)
C2—B1—C11—C16	−123.9 (2)	C46—C41—C42—C43	0.3 (3)
C1—B1—C11—C16	5.3 (3)	P1—C41—C42—C43	−175.30 (17)
P1—B1—C11—C16	121.98 (19)	C41—C42—C43—C44	−0.7 (4)
C2—B1—C11—C12	54.1 (3)	C42—C43—C44—C45	0.3 (4)
C1—B1—C11—C12	−176.80 (18)	C43—C44—C45—C46	0.4 (4)
P1—B1—C11—C12	−60.1 (2)	C44—C45—C46—C41	−0.7 (4)
C16—C11—C12—C13	−1.2 (3)	C42—C41—C46—C45	0.3 (3)
B1—C11—C12—C13	−179.3 (2)	P1—C41—C46—C45	175.99 (19)
C11—C12—C13—C14	0.8 (4)	C1^i—P1—C51—C56	−47.9 (2)
C12—C13—C14—C15	0.1 (4)	C41—P1—C51—C56	64.09 (19)
C13—C14—C15—C16	−0.6 (4)	B1—P1—C51—C56	−172.48 (17)
C14—C15—C16—C11	0.1 (4)	C1^i—P1—C51—C52	136.62 (19)
C12—C11—C16—C15	0.7 (3)	C41—P1—C51—C52	−111.4 (2)
B1—C11—C16—C15	178.8 (2)	B1—P1—C51—C52	12.0 (2)
C31—P2—C21—C26	−112.6 (2)	C56—C51—C52—C53	−0.2 (4)
C2—P2—C21—C26	−7.9 (2)	P1—C51—C52—C53	175.3 (2)
C31—P2—C21—C22	72.9 (2)	C51—C52—C53—C54	0.5 (4)
C2—P2—C21—C22	177.6 (2)	C52—C53—C54—C55	−0.1 (4)
C26—C21—C22—C23	1.2 (4)	C53—C54—C55—C56	−0.7 (4)
P2—C21—C22—C23	176.2 (2)	C54—C55—C56—C51	1.0 (4)
C21—C22—C23—C24	−1.5 (5)	C52—C51—C56—C55	−0.5 (4)
C22—C23—C24—C25	0.9 (5)	P1—C51—C56—C55	−176.2 (2)
C23—C24—C25—C26	−0.1 (4)	C65—O61—C62—C63	2.3 (13)
C22—C21—C26—C25	−0.4 (4)	O61—C62—C63—C64	−10.4 (16)
P2—C21—C26—C25	−174.8 (2)	C62—C63—C64—C65	13.8 (16)
C24—C25—C26—C21	−0.2 (4)	C62—O61—C65—C64	6.7 (12)
C21—P2—C31—C36	−130.58 (19)	C63—C64—C65—O61	−12.2 (13)

Symmetry code: (i) −x+1, −y+1, −z+1.

(Ib) 2,5-[(Diphenylphosphanyl)methyl]-1,1,2,4,4,5-hexaphenyl-1,4-diphospha-2,5-diboracyclohexane tetrahydrofuran disolvate

Crystal data

C64H58B2P4·2C4H8O	F(000) = 1184
Mr = 1116.81	Dx = 1.226 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 41292 reflections
a = 12.3097 (6) Å	θ = 2.8–25.6°
b = 13.3629 (4) Å	µ = 0.17 mm^−1
c = 18.4243 (9) Å	T = 173 K
β = 93.720 (4)°	Block, colourless
V = 3024.3 (2) Å^3	0.36 × 0.22 × 0.21 mm
Z = 2

Data collection

Stoe IPDS II two-circle diffractometer	5652 independent reflections
Radiation source: fine-focus sealed tube	5027 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
ω scans	θmax = 25.6°, θmin = 3.1°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −14→14
Tmin = 0.941, Tmax = 0.965	k = −16→14
40239 measured reflections	l = −22→22

Refinement

Refinement on F^2	81 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.093	w = 1/[σ^2(Fo^2) + (0.0461P)^2 + 1.4685P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
5652 reflections	Δρmax = 0.32 e Å^−3
407 parameters	Δρmin = −0.26 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. 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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.58655 (11)	0.56292 (11)	0.44921 (7)	0.0200 (3)
H1A	0.5383	0.6195	0.4341	0.024*
H1B	0.6582	0.5766	0.4298	0.024*
B1	0.53662 (13)	0.46153 (12)	0.40738 (8)	0.0195 (3)
P1	0.39437 (3)	0.43308 (3)	0.45226 (2)	0.01833 (10)
C2	0.61218 (11)	0.36090 (11)	0.42210 (8)	0.0211 (3)
H2A	0.5745	0.3019	0.3998	0.025*
H2B	0.6236	0.3489	0.4751	0.025*
P2	0.74596 (3)	0.37834 (3)	0.38210 (2)	0.02165 (10)
C11	0.51448 (11)	0.48125 (11)	0.32027 (7)	0.0206 (3)
C12	0.46877 (12)	0.40667 (12)	0.27389 (8)	0.0249 (3)
H12	0.4489	0.3445	0.2942	0.030*
C13	0.45156 (13)	0.42096 (13)	0.19901 (8)	0.0306 (3)
H13	0.4192	0.3695	0.1693	0.037*
C14	0.48199 (13)	0.51072 (14)	0.16801 (8)	0.0328 (4)
H14	0.4704	0.5209	0.1171	0.039*
C15	0.52917 (14)	0.58519 (13)	0.21160 (9)	0.0313 (4)
H15	0.5514	0.6461	0.1905	0.038*
C16	0.54419 (12)	0.57079 (12)	0.28672 (8)	0.0256 (3)
H16	0.5755	0.6231	0.3160	0.031*
C21	0.83193 (12)	0.28152 (11)	0.42866 (8)	0.0229 (3)
C22	0.94501 (12)	0.29395 (12)	0.42785 (8)	0.0269 (3)
H22	0.9732	0.3486	0.4020	0.032*
C23	1.01661 (13)	0.22753 (13)	0.46424 (9)	0.0321 (4)
H23	1.0929	0.2373	0.4632	0.039*
C24	0.97697 (14)	0.14742 (14)	0.50194 (9)	0.0355 (4)
H24	1.0258	0.1024	0.5272	0.043*
C25	0.86501 (15)	0.13308 (14)	0.50269 (9)	0.0365 (4)
H25	0.8374	0.0776	0.5279	0.044*
C26	0.79324 (13)	0.19980 (13)	0.46659 (9)	0.0299 (3)
H26	0.7170	0.1896	0.4678	0.036*
C31	0.72433 (11)	0.32067 (12)	0.29068 (8)	0.0249 (3)
C32	0.70257 (15)	0.21931 (13)	0.27885 (9)	0.0360 (4)
H32	0.6977	0.1758	0.3193	0.043*
C33	0.68784 (17)	0.18112 (15)	0.20847 (10)	0.0452 (5)
H33	0.6730	0.1119	0.2012	0.054*
C34	0.69473 (15)	0.24376 (17)	0.14912 (10)	0.0441 (5)
H34	0.6850	0.2175	0.1012	0.053*
C35	0.71566 (15)	0.34406 (17)	0.15958 (9)	0.0440 (5)
H35	0.7197	0.3873	0.1189	0.053*
C36	0.73099 (14)	0.38241 (14)	0.23019 (9)	0.0344 (4)
H36	0.7462	0.4516	0.2370	0.041*
C41	0.34067 (11)	0.30822 (11)	0.42987 (8)	0.0223 (3)
C42	0.36930 (14)	0.22548 (12)	0.47309 (9)	0.0329 (4)
H42	0.4145	0.2342	0.5164	0.039*
C43	0.33226 (16)	0.13002 (13)	0.45345 (11)	0.0414 (4)
H43	0.3516	0.0744	0.4837	0.050*
C44	0.26745 (15)	0.11620 (14)	0.39006 (11)	0.0398 (4)
H44	0.2434	0.0510	0.3762	0.048*
C45	0.23769 (14)	0.19748 (14)	0.34689 (10)	0.0367 (4)
H45	0.1924	0.1880	0.3037	0.044*
C46	0.27369 (13)	0.29318 (13)	0.36629 (9)	0.0290 (3)
H46	0.2528	0.3486	0.3363	0.035*
C51	0.28054 (11)	0.51487 (11)	0.42355 (8)	0.0218 (3)
C52	0.29360 (13)	0.59554 (13)	0.37702 (9)	0.0294 (3)
H52	0.3633	0.6095	0.3601	0.035*
C53	0.20532 (14)	0.65593 (14)	0.35510 (10)	0.0362 (4)
H53	0.2155	0.7113	0.3239	0.043*
C54	0.10279 (13)	0.63586 (13)	0.37839 (9)	0.0330 (4)
H54	0.0427	0.6770	0.3630	0.040*
C55	0.08848 (13)	0.55529 (13)	0.42430 (9)	0.0317 (4)
H55	0.0181	0.5409	0.4400	0.038*
C56	0.17645 (12)	0.49547 (12)	0.44755 (8)	0.0272 (3)
H56	0.1662	0.4413	0.4798	0.033*
O61A_a	0.4761 (5)	0.9276 (4)	0.4052 (3)	0.0805 (16)	0.612 (8)
C62A_a	0.5271 (4)	0.9957 (4)	0.3594 (4)	0.0724 (17)	0.612 (8)
H62A_a	0.6072	0.9875	0.3639	0.087*	0.612 (8)
H62B_a	0.5090	1.0657	0.3716	0.087*	0.612 (8)
C63A_a	0.4820 (6)	0.9693 (7)	0.2835 (4)	0.097 (3)	0.612 (8)
H63A_a	0.4140	1.0069	0.2709	0.116*	0.612 (8)
H63B_a	0.5354	0.9855	0.2473	0.116*	0.612 (8)
C64A_a	0.4603 (11)	0.8601 (8)	0.2847 (5)	0.166 (4)	0.612 (8)
H64A_a	0.3921	0.8430	0.2559	0.199*	0.612 (8)
H64B_a	0.5213	0.8215	0.2660	0.199*	0.612 (8)
C65A_a	0.4509 (8)	0.8425 (6)	0.3612 (4)	0.103 (3)	0.612 (8)
H65A_a	0.3756	0.8210	0.3689	0.124*	0.612 (8)
H65B_a	0.5004	0.7872	0.3770	0.124*	0.612 (8)
O61B_b	0.3748 (10)	0.8645 (8)	0.3045 (5)	0.150 (4)	0.388 (8)
C62B_b	0.4259 (12)	0.9354 (8)	0.2661 (6)	0.114 (4)	0.388 (8)
H62C_b	0.3704	0.9766	0.2386	0.137*	0.388 (8)
H62D_b	0.4705	0.9019	0.2304	0.137*	0.388 (8)
C63B_b	0.4960 (11)	1.0009 (8)	0.3127 (7)	0.089 (4)	0.388 (8)
H63C_b	0.4615	1.0666	0.3205	0.107*	0.388 (8)
H63D_b	0.5680	1.0111	0.2928	0.107*	0.388 (8)
C64B_b	0.5042 (12)	0.9390 (12)	0.3810 (9)	0.102 (5)	0.388 (8)
H64C_b	0.5746	0.9030	0.3853	0.123*	0.388 (8)
H64D_b	0.4995	0.9825	0.4242	0.123*	0.388 (8)
C65B_b	0.4120 (8)	0.8660 (9)	0.3763 (5)	0.073 (3)	0.388 (8)
H65C_b	0.4374	0.7987	0.3923	0.088*	0.388 (8)
H65D_b	0.3537	0.8877	0.4074	0.088*	0.388 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0199 (7)	0.0220 (7)	0.0183 (7)	−0.0010 (5)	0.0018 (5)	0.0022 (5)
B1	0.0190 (7)	0.0214 (8)	0.0184 (7)	−0.0005 (6)	0.0031 (6)	0.0008 (6)
P1	0.01743 (18)	0.01992 (19)	0.01762 (18)	−0.00059 (13)	0.00094 (13)	0.00050 (13)
C2	0.0214 (7)	0.0231 (7)	0.0190 (7)	0.0003 (6)	0.0026 (5)	0.0016 (5)
P2	0.02077 (19)	0.0230 (2)	0.02136 (19)	0.00085 (14)	0.00262 (14)	0.00116 (14)
C11	0.0175 (7)	0.0254 (7)	0.0191 (7)	0.0025 (5)	0.0025 (5)	0.0013 (6)
C12	0.0241 (7)	0.0292 (8)	0.0213 (7)	−0.0013 (6)	0.0022 (6)	0.0010 (6)
C13	0.0309 (8)	0.0391 (9)	0.0213 (7)	−0.0025 (7)	−0.0021 (6)	−0.0027 (7)
C14	0.0353 (9)	0.0445 (10)	0.0182 (7)	0.0028 (7)	−0.0009 (6)	0.0049 (7)
C15	0.0349 (9)	0.0335 (9)	0.0254 (8)	0.0007 (7)	0.0021 (6)	0.0094 (7)
C16	0.0277 (8)	0.0268 (8)	0.0221 (7)	−0.0001 (6)	0.0006 (6)	0.0021 (6)
C21	0.0228 (7)	0.0262 (8)	0.0195 (7)	0.0027 (6)	0.0004 (5)	−0.0031 (6)
C22	0.0246 (7)	0.0324 (8)	0.0237 (7)	0.0011 (6)	0.0026 (6)	−0.0049 (6)
C23	0.0245 (8)	0.0442 (10)	0.0272 (8)	0.0072 (7)	−0.0011 (6)	−0.0076 (7)
C24	0.0358 (9)	0.0423 (10)	0.0276 (8)	0.0150 (8)	−0.0037 (7)	−0.0002 (7)
C25	0.0396 (9)	0.0367 (9)	0.0331 (9)	0.0058 (8)	0.0013 (7)	0.0095 (7)
C26	0.0264 (8)	0.0335 (9)	0.0299 (8)	0.0020 (7)	0.0013 (6)	0.0034 (7)
C31	0.0182 (7)	0.0334 (8)	0.0233 (7)	0.0048 (6)	0.0027 (5)	−0.0002 (6)
C32	0.0429 (10)	0.0343 (9)	0.0295 (9)	0.0063 (8)	−0.0060 (7)	−0.0019 (7)
C33	0.0499 (11)	0.0430 (11)	0.0408 (10)	0.0124 (9)	−0.0121 (8)	−0.0135 (8)
C34	0.0340 (9)	0.0709 (14)	0.0268 (9)	0.0141 (9)	−0.0033 (7)	−0.0136 (9)
C35	0.0367 (10)	0.0729 (14)	0.0227 (8)	0.0010 (9)	0.0050 (7)	0.0059 (9)
C36	0.0315 (9)	0.0457 (10)	0.0264 (8)	−0.0030 (7)	0.0053 (6)	0.0046 (7)
C41	0.0209 (7)	0.0231 (7)	0.0236 (7)	−0.0026 (6)	0.0053 (5)	−0.0022 (6)
C42	0.0381 (9)	0.0262 (8)	0.0337 (9)	−0.0017 (7)	−0.0027 (7)	−0.0007 (7)
C43	0.0509 (11)	0.0255 (9)	0.0475 (11)	−0.0032 (8)	0.0014 (9)	0.0012 (8)
C44	0.0396 (10)	0.0299 (9)	0.0505 (11)	−0.0095 (7)	0.0076 (8)	−0.0129 (8)
C45	0.0323 (9)	0.0429 (10)	0.0347 (9)	−0.0094 (8)	0.0012 (7)	−0.0124 (8)
C46	0.0270 (8)	0.0329 (9)	0.0271 (8)	−0.0053 (7)	0.0021 (6)	−0.0029 (6)
C51	0.0198 (7)	0.0248 (7)	0.0205 (7)	0.0018 (6)	−0.0011 (5)	−0.0029 (6)
C52	0.0246 (8)	0.0318 (8)	0.0321 (8)	0.0028 (6)	0.0040 (6)	0.0045 (7)
C53	0.0374 (9)	0.0366 (9)	0.0347 (9)	0.0087 (7)	0.0028 (7)	0.0095 (7)
C54	0.0272 (8)	0.0391 (9)	0.0320 (8)	0.0108 (7)	−0.0041 (6)	−0.0034 (7)
C55	0.0204 (7)	0.0388 (9)	0.0360 (9)	0.0024 (7)	0.0019 (6)	−0.0061 (7)
C56	0.0242 (7)	0.0298 (8)	0.0279 (8)	0.0003 (6)	0.0039 (6)	0.0006 (6)
O61A_a	0.111 (4)	0.062 (2)	0.066 (3)	0.015 (2)	−0.004 (2)	0.0068 (19)
C62A_a	0.063 (3)	0.060 (3)	0.096 (5)	0.017 (2)	0.024 (3)	0.003 (3)
C63A_a	0.065 (4)	0.156 (7)	0.069 (4)	0.000 (5)	−0.008 (3)	0.044 (5)
C64A_a	0.156 (7)	0.190 (8)	0.148 (7)	−0.064 (6)	−0.018 (6)	−0.040 (6)
C65A_a	0.116 (6)	0.102 (5)	0.090 (4)	−0.018 (5)	−0.009 (4)	0.014 (4)
O61B_b	0.167 (8)	0.164 (7)	0.115 (6)	−0.052 (6)	−0.019 (5)	0.022 (5)
C62B_b	0.157 (9)	0.087 (6)	0.095 (6)	−0.017 (6)	−0.020 (6)	−0.006 (5)
C63B_b	0.065 (6)	0.101 (6)	0.102 (8)	−0.008 (5)	0.014 (6)	−0.031 (6)
C64B_b	0.093 (7)	0.115 (9)	0.095 (9)	−0.001 (6)	−0.013 (6)	0.013 (7)
C65B_b	0.059 (5)	0.072 (6)	0.089 (6)	0.007 (4)	0.009 (4)	0.022 (5)

Geometric parameters (Å, º)

C1—B1	1.657 (2)	C41—C42	1.394 (2)
C1—P1^i	1.8163 (14)	C41—C46	1.403 (2)
C1—H1A	0.9900	C42—C43	1.395 (2)
C1—H1B	0.9900	C42—H42	0.9500
B1—C11	1.632 (2)	C43—C44	1.383 (3)
B1—C2	1.647 (2)	C43—H43	0.9500
B1—P1	2.0205 (16)	C44—C45	1.382 (3)
P1—C1^i	1.8163 (14)	C44—H44	0.9500
P1—C51	1.8280 (15)	C45—C46	1.392 (2)
P1—C41	1.8317 (15)	C45—H45	0.9500
C2—P2	1.8620 (14)	C46—H46	0.9500
C2—H2A	0.9900	C51—C52	1.393 (2)
C2—H2B	0.9900	C51—C56	1.406 (2)
P2—C21	1.8471 (15)	C52—C53	1.392 (2)
P2—C31	1.8557 (16)	C52—H52	0.9500
C11—C16	1.406 (2)	C53—C54	1.385 (2)
C11—C12	1.406 (2)	C53—H53	0.9500
C12—C13	1.395 (2)	C54—C55	1.387 (2)
C12—H12	0.9500	C54—H54	0.9500
C13—C14	1.390 (2)	C55—C56	1.391 (2)
C13—H13	0.9500	C55—H55	0.9500
C14—C15	1.383 (2)	C56—H56	0.9500
C14—H14	0.9500	O61A_a—C62A_a	1.417 (6)
C15—C16	1.398 (2)	O61A_a—C65A_a	1.419 (7)
C15—H15	0.9500	C62A_a—C63A_a	1.513 (6)
C16—H16	0.9500	C62A_a—H62A_a	0.9900
C21—C26	1.397 (2)	C62A_a—H62B_a	0.9900
C21—C22	1.403 (2)	C63A_a—C64A_a	1.485 (7)
C22—C23	1.392 (2)	C63A_a—H63A_a	0.9900
C22—H22	0.9500	C63A_a—H63B_a	0.9900
C23—C24	1.382 (3)	C64A_a—C65A_a	1.441 (7)
C23—H23	0.9500	C64A_a—H64A_a	0.9900
C24—C25	1.392 (3)	C64A_a—H64B_a	0.9900
C24—H24	0.9500	C65A_a—H65A_a	0.9900
C25—C26	1.393 (2)	C65A_a—H65B_a	0.9900
C25—H25	0.9500	O61B_b—C62B_b	1.361 (9)
C26—H26	0.9500	O61B_b—C65B_b	1.372 (9)
C31—C36	1.393 (2)	C62B_b—C63B_b	1.468 (8)
C31—C32	1.395 (2)	C62B_b—H62C_b	0.9900
C32—C33	1.395 (2)	C62B_b—H62D_b	0.9900
C32—H32	0.9500	C63B_b—C64B_b	1.505 (8)
C33—C34	1.384 (3)	C63B_b—H63C_b	0.9900
C33—H33	0.9500	C63B_b—H63D_b	0.9900
C34—C35	1.376 (3)	C64B_b—C65B_b	1.494 (8)
C34—H34	0.9500	C64B_b—H64C_b	0.9900
C35—C36	1.400 (2)	C64B_b—H64D_b	0.9900
C35—H35	0.9500	C65B_b—H65C_b	0.9900
C36—H36	0.9500	C65B_b—H65D_b	0.9900
B1—C1—P1^i	120.59 (10)	C41—C42—C43	120.72 (16)
B1—C1—H1A	107.2	C41—C42—H42	119.6
P1^i—C1—H1A	107.2	C43—C42—H42	119.6
B1—C1—H1B	107.2	C44—C43—C42	120.14 (17)
P1^i—C1—H1B	107.2	C44—C43—H43	119.9
H1A—C1—H1B	106.8	C42—C43—H43	119.9
C11—B1—C2	110.50 (11)	C45—C44—C43	119.86 (16)
C11—B1—C1	111.01 (11)	C45—C44—H44	120.1
C2—B1—C1	113.73 (12)	C43—C44—H44	120.1
C11—B1—P1	109.82 (10)	C44—C45—C46	120.40 (16)
C2—B1—P1	105.90 (9)	C44—C45—H45	119.8
C1—B1—P1	105.58 (9)	C46—C45—H45	119.8
C1^i—P1—C51	108.58 (7)	C45—C46—C41	120.41 (16)
C1^i—P1—C41	105.86 (7)	C45—C46—H46	119.8
C51—P1—C41	102.76 (7)	C41—C46—H46	119.8
C1^i—P1—B1	110.14 (6)	C52—C51—C56	118.68 (14)
C51—P1—B1	115.94 (7)	C52—C51—P1	121.59 (11)
C41—P1—B1	112.89 (7)	C56—C51—P1	119.72 (12)
B1—C2—P2	109.70 (9)	C53—C52—C51	120.54 (15)
B1—C2—H2A	109.7	C53—C52—H52	119.7
P2—C2—H2A	109.7	C51—C52—H52	119.7
B1—C2—H2B	109.7	C54—C53—C52	120.50 (16)
P2—C2—H2B	109.7	C54—C53—H53	119.8
H2A—C2—H2B	108.2	C52—C53—H53	119.8
C21—P2—C31	100.07 (7)	C53—C54—C55	119.56 (15)
C21—P2—C2	102.90 (7)	C53—C54—H54	120.2
C31—P2—C2	103.22 (7)	C55—C54—H54	120.2
C16—C11—C12	116.19 (13)	C54—C55—C56	120.44 (15)
C16—C11—B1	122.56 (13)	C54—C55—H55	119.8
C12—C11—B1	121.19 (13)	C56—C55—H55	119.8
C13—C12—C11	122.20 (15)	C55—C56—C51	120.27 (15)
C13—C12—H12	118.9	C55—C56—H56	119.9
C11—C12—H12	118.9	C51—C56—H56	119.9
C14—C13—C12	119.77 (15)	C62A_a—O61A_a—C65A_a	105.2 (5)
C14—C13—H13	120.1	O61A_a—C62A_a—C63A_a	104.5 (5)
C12—C13—H13	120.1	O61A_a—C62A_a—H62A_a	110.9
C15—C14—C13	119.76 (14)	C63A_a—C62A_a—H62A_a	110.9
C15—C14—H14	120.1	O61A_a—C62A_a—H62B_a	110.9
C13—C14—H14	120.1	C63A_a—C62A_a—H62B_a	110.9
C14—C15—C16	119.98 (15)	H62A_a—C62A_a—H62B_a	108.9
C14—C15—H15	120.0	C64A_a—C63A_a—C62A_a	105.7 (5)
C16—C15—H15	120.0	C64A_a—C63A_a—H63A_a	110.6
C15—C16—C11	122.07 (15)	C62A_a—C63A_a—H63A_a	110.6
C15—C16—H16	119.0	C64A_a—C63A_a—H63B_a	110.6
C11—C16—H16	119.0	C62A_a—C63A_a—H63B_a	110.6
C26—C21—C22	117.95 (14)	H63A_a—C63A_a—H63B_a	108.7
C26—C21—P2	125.19 (12)	C65A_a—C64A_a—C63A_a	101.6 (7)
C22—C21—P2	116.81 (12)	C65A_a—C64A_a—H64A_a	111.5
C23—C22—C21	121.13 (15)	C63A_a—C64A_a—H64A_a	111.5
C23—C22—H22	119.4	C65A_a—C64A_a—H64B_a	111.5
C21—C22—H22	119.4	C63A_a—C64A_a—H64B_a	111.5
C24—C23—C22	120.19 (15)	H64A_a—C64A_a—H64B_a	109.3
C24—C23—H23	119.9	O61A_a—C65A_a—C64A_a	113.6 (7)
C22—C23—H23	119.9	O61A_a—C65A_a—H65A_a	108.8
C23—C24—C25	119.57 (15)	C64A_a—C65A_a—H65A_a	108.8
C23—C24—H24	120.2	O61A_a—C65A_a—H65B_a	108.8
C25—C24—H24	120.2	C64A_a—C65A_a—H65B_a	108.8
C24—C25—C26	120.29 (16)	H65A_a—C65A_a—H65B_a	107.7
C24—C25—H25	119.9	C62B_b—O61B_b—C65B_b	110.8 (9)
C26—C25—H25	119.9	O61B_b—C62B_b—C63B_b	112.7 (9)
C25—C26—C21	120.86 (15)	O61B_b—C62B_b—H62C_b	109.1
C25—C26—H26	119.6	C63B_b—C62B_b—H62C_b	109.1
C21—C26—H26	119.6	O61B_b—C62B_b—H62D_b	109.1
C36—C31—C32	118.08 (15)	C63B_b—C62B_b—H62D_b	109.1
C36—C31—P2	117.89 (13)	H62C_b—C62B_b—H62D_b	107.8
C32—C31—P2	124.03 (12)	C62B_b—C63B_b—C64B_b	99.5 (10)
C33—C32—C31	120.84 (17)	C62B_b—C63B_b—H63C_b	111.9
C33—C32—H32	119.6	C64B_b—C63B_b—H63C_b	111.9
C31—C32—H32	119.6	C62B_b—C63B_b—H63D_b	111.9
C34—C33—C32	120.16 (19)	C64B_b—C63B_b—H63D_b	111.9
C34—C33—H33	119.9	H63C_b—C63B_b—H63D_b	109.6
C32—C33—H33	119.9	C65B_b—C64B_b—C63B_b	107.6 (10)
C35—C34—C33	119.94 (17)	C65B_b—C64B_b—H64C_b	110.2
C35—C34—H34	120.0	C63B_b—C64B_b—H64C_b	110.2
C33—C34—H34	120.0	C65B_b—C64B_b—H64D_b	110.2
C34—C35—C36	119.96 (18)	C63B_b—C64B_b—H64D_b	110.2
C34—C35—H35	120.0	H64C_b—C64B_b—H64D_b	108.5
C36—C35—H35	120.0	O61B_b—C65B_b—C64B_b	105.6 (9)
C31—C36—C35	121.03 (18)	O61B_b—C65B_b—H65C_b	110.6
C31—C36—H36	119.5	C64B_b—C65B_b—H65C_b	110.6
C35—C36—H36	119.5	O61B_b—C65B_b—H65D_b	110.6
C42—C41—C46	118.45 (14)	C64B_b—C65B_b—H65D_b	110.6
C42—C41—P1	121.30 (12)	H65C_b—C65B_b—H65D_b	108.7
C46—C41—P1	120.18 (12)
P1^i—C1—B1—C11	173.50 (9)	C33—C34—C35—C36	0.6 (3)
P1^i—C1—B1—C2	−61.14 (15)	C32—C31—C36—C35	0.4 (2)
P1^i—C1—B1—P1	54.54 (12)	P2—C31—C36—C35	179.96 (13)
C11—B1—C2—P2	60.67 (13)	C34—C35—C36—C31	−0.7 (3)
C1—B1—C2—P2	−64.96 (13)	C1^i—P1—C41—C42	−31.48 (14)
P1—B1—C2—P2	179.55 (7)	C51—P1—C41—C42	−145.30 (13)
B1—C2—P2—C21	162.08 (10)	B1—P1—C41—C42	89.07 (14)
B1—C2—P2—C31	−94.14 (10)	C1^i—P1—C41—C46	151.76 (12)
C2—B1—C11—C16	−122.00 (14)	C51—P1—C41—C46	37.94 (13)
C1—B1—C11—C16	5.15 (19)	B1—P1—C41—C46	−87.68 (13)
P1—B1—C11—C16	121.53 (13)	C46—C41—C42—C43	0.1 (2)
C2—B1—C11—C12	54.92 (17)	P1—C41—C42—C43	−176.73 (14)
C1—B1—C11—C12	−177.92 (12)	C41—C42—C43—C44	0.8 (3)
P1—B1—C11—C12	−61.54 (15)	C42—C43—C44—C45	−1.2 (3)
C16—C11—C12—C13	−1.3 (2)	C43—C44—C45—C46	0.8 (3)
B1—C11—C12—C13	−178.40 (14)	C44—C45—C46—C41	0.0 (3)
C11—C12—C13—C14	1.3 (2)	C42—C41—C46—C45	−0.5 (2)
C12—C13—C14—C15	0.0 (2)	P1—C41—C46—C45	176.35 (12)
C13—C14—C15—C16	−1.2 (2)	C1^i—P1—C51—C52	120.75 (13)
C14—C15—C16—C11	1.2 (2)	C41—P1—C51—C52	−127.43 (13)
C12—C11—C16—C15	0.1 (2)	B1—P1—C51—C52	−3.82 (15)
B1—C11—C16—C15	177.14 (14)	C1^i—P1—C51—C56	−60.50 (13)
C31—P2—C21—C26	−89.66 (14)	C41—P1—C51—C56	51.32 (13)
C2—P2—C21—C26	16.54 (15)	B1—P1—C51—C56	174.93 (11)
C31—P2—C21—C22	92.92 (12)	C56—C51—C52—C53	0.3 (2)
C2—P2—C21—C22	−160.88 (11)	P1—C51—C52—C53	179.08 (13)
C26—C21—C22—C23	−0.6 (2)	C51—C52—C53—C54	−0.9 (3)
P2—C21—C22—C23	177.04 (12)	C52—C53—C54—C55	0.4 (3)
C21—C22—C23—C24	0.1 (2)	C53—C54—C55—C56	0.7 (3)
C22—C23—C24—C25	0.6 (3)	C54—C55—C56—C51	−1.3 (2)
C23—C24—C25—C26	−0.9 (3)	C52—C51—C56—C55	0.8 (2)
C24—C25—C26—C21	0.5 (3)	P1—C51—C56—C55	−178.01 (12)
C22—C21—C26—C25	0.3 (2)	C65A_a—O61A_a—C62A_a—C63A_a	26.6 (8)
P2—C21—C26—C25	−177.14 (13)	O61A_a—C62A_a—C63A_a—C64A_a	−31.3 (9)
C21—P2—C31—C36	−137.62 (12)	C62A_a—C63A_a—C64A_a—C65A_a	22.3 (10)
C2—P2—C31—C36	116.44 (12)	C62A_a—O61A_a—C65A_a—C64A_a	−13.4 (10)
C21—P2—C31—C32	41.94 (15)	C63A_a—C64A_a—C65A_a—O61A_a	−6.3 (11)
C2—P2—C31—C32	−64.00 (15)	C65B_b—O61B_b—C62B_b—C63B_b	−6.8 (17)
C36—C31—C32—C33	−0.1 (2)	O61B_b—C62B_b—C63B_b—C64B_b	16.1 (16)
P2—C31—C32—C33	−179.61 (14)	C62B_b—C63B_b—C64B_b—C65B_b	−19.0 (16)
C31—C32—C33—C34	0.0 (3)	C62B_b—O61B_b—C65B_b—C64B_b	−6.2 (15)
C32—C33—C34—C35	−0.3 (3)	C63B_b—C64B_b—C65B_b—O61B_b	16.5 (16)

Symmetry code: (i) −x+1, −y+1, −z+1.

(Ic) 2,5-[(Diphenylphosphanyl)methyl]-1,1,2,4,4,5-hexaphenyl-1,4-diphospha-2,5-diboracyclohexane toluene monosolvate

Crystal data

C64H58B2P4·C7H8	F(000) = 2248
Mr = 1064.74	Dx = 1.209 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 15406 reflections
a = 22.8933 (18) Å	θ = 3.8–25.3°
b = 13.4283 (6) Å	µ = 0.17 mm^−1
c = 20.2287 (13) Å	T = 173 K
β = 109.813 (5)°	Block, colourless
V = 5850.5 (6) Å^3	0.18 × 0.17 × 0.15 mm
Z = 4

Data collection

Stoe IPDS II two-circle diffractometer	10969 independent reflections
Radiation source: fine-focus sealed tube	6016 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.081
ω scans	θmax = 25.7°, θmin = 3.4°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −27→27
Tmin = 0.952, Tmax = 0.983	k = −16→16
50113 measured reflections	l = −24→24

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.128	H-atom parameters constrained
S = 0.94	w = 1/[σ^2(Fo^2) + (0.039P)^2] where P = (Fo^2 + 2Fc^2)/3
10969 reflections	(Δ/σ)max < 0.001
695 parameters	Δρmax = 0.41 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

Experimental. ;

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.20960 (17)	0.7761 (2)	0.15536 (19)	0.0234 (8)
H1A	0.2220	0.8461	0.1523	0.028*
H1B	0.1853	0.7548	0.1070	0.028*
B1	0.16146 (19)	0.7758 (3)	0.2012 (2)	0.0224 (9)
P1	0.21366 (4)	0.81068 (6)	0.30159 (5)	0.0211 (2)
C2	0.28431 (16)	0.7372 (2)	0.32906 (19)	0.0216 (7)
H2A	0.3085	0.7566	0.3779	0.026*
H2B	0.2722	0.6666	0.3304	0.026*
B2	0.33225 (19)	0.7428 (3)	0.2822 (2)	0.0233 (9)
P2	0.28049 (4)	0.70182 (6)	0.18375 (5)	0.0211 (2)
C3	0.13489 (17)	0.6644 (2)	0.2111 (2)	0.0256 (8)
H3A	0.1093	0.6705	0.2417	0.031*
H3B	0.1706	0.6207	0.2355	0.031*
P3	0.08751 (5)	0.60361 (7)	0.12716 (5)	0.0262 (2)
C4	0.35378 (17)	0.8570 (2)	0.2720 (2)	0.0257 (8)
H4A	0.3165	0.8987	0.2503	0.031*
H4B	0.3782	0.8562	0.2399	0.031*
P4	0.40108 (5)	0.91200 (6)	0.35717 (5)	0.0256 (2)
C11	0.10665 (18)	0.8579 (3)	0.1707 (2)	0.0272 (8)
C12	0.10257 (19)	0.9202 (3)	0.1132 (2)	0.0324 (9)
H12	0.1323	0.9130	0.0903	0.039*
C13	0.0561 (2)	0.9925 (3)	0.0889 (3)	0.0466 (12)
H13	0.0557	1.0344	0.0509	0.056*
C14	0.0114 (2)	1.0036 (3)	0.1192 (3)	0.0528 (13)
H14	−0.0200	1.0528	0.1026	0.063*
C15	0.0128 (2)	0.9421 (3)	0.1742 (3)	0.0463 (11)
H15	−0.0182	0.9490	0.1956	0.056*
C16	0.05892 (18)	0.8698 (3)	0.1992 (2)	0.0345 (9)
H16	0.0580	0.8275	0.2365	0.041*
C21	0.39177 (17)	0.6679 (2)	0.3141 (2)	0.0261 (8)
C22	0.39923 (17)	0.6039 (3)	0.3708 (2)	0.0300 (9)
H22	0.3679	0.6023	0.3919	0.036*
C23	0.4511 (2)	0.5418 (3)	0.3978 (3)	0.0481 (12)
H23	0.4538	0.4976	0.4354	0.058*
C24	0.4988 (2)	0.5449 (3)	0.3696 (3)	0.0498 (12)
H24	0.5345	0.5041	0.3882	0.060*
C25	0.4932 (2)	0.6084 (3)	0.3143 (3)	0.0441 (11)
H25	0.5253	0.6107	0.2944	0.053*
C26	0.44138 (18)	0.6691 (3)	0.2870 (2)	0.0336 (9)
H26	0.4391	0.7126	0.2492	0.040*
C31	0.23447 (18)	0.9417 (2)	0.3232 (2)	0.0278 (8)
C32	0.2672 (2)	0.9670 (3)	0.3927 (2)	0.0385 (10)
H32	0.2808	0.9165	0.4274	0.046*
C33	0.2799 (2)	1.0667 (3)	0.4111 (3)	0.0527 (14)
H33	0.3019	1.0838	0.4586	0.063*
C34	0.2609 (2)	1.1408 (3)	0.3611 (4)	0.0594 (16)
H34	0.2699	1.2085	0.3743	0.071*
C35	0.2289 (2)	1.1168 (3)	0.2925 (3)	0.0528 (14)
H35	0.2160	1.1680	0.2581	0.063*
C36	0.2152 (2)	1.0164 (3)	0.2726 (3)	0.0352 (10)
H36	0.1931	0.9998	0.2250	0.042*
C41	0.17326 (17)	0.7831 (2)	0.36404 (19)	0.0247 (8)
C42	0.13529 (19)	0.8550 (3)	0.3786 (2)	0.0339 (9)
H42	0.1308	0.9183	0.3565	0.041*
C43	0.1038 (2)	0.8350 (3)	0.4253 (2)	0.0426 (11)
H43	0.0783	0.8849	0.4349	0.051*
C44	0.1094 (2)	0.7438 (3)	0.4576 (2)	0.0423 (11)
H44	0.0878	0.7307	0.4893	0.051*
C45	0.1466 (2)	0.6708 (3)	0.4441 (2)	0.0424 (11)
H45	0.1504	0.6077	0.4664	0.051*
C46	0.17873 (19)	0.6902 (3)	0.3975 (2)	0.0346 (9)
H46	0.2044	0.6401	0.3885	0.042*
C51	0.32078 (16)	0.7237 (2)	0.12081 (19)	0.0237 (8)
C52	0.3599 (2)	0.6493 (3)	0.1104 (2)	0.0364 (10)
H52	0.3639	0.5879	0.1349	0.044*
C53	0.3929 (2)	0.6639 (3)	0.0651 (3)	0.0448 (11)
H53	0.4190	0.6126	0.0587	0.054*
C54	0.3878 (2)	0.7528 (3)	0.0293 (2)	0.0446 (11)
H54	0.4105	0.7629	−0.0017	0.054*
C55	0.3496 (2)	0.8271 (3)	0.0389 (2)	0.0451 (11)
H55	0.3461	0.8881	0.0141	0.054*
C56	0.3163 (2)	0.8133 (3)	0.0844 (2)	0.0371 (10)
H56	0.2904	0.8652	0.0907	0.045*
C61	0.25851 (17)	0.5703 (2)	0.1674 (2)	0.0281 (8)
C62	0.2248 (2)	0.5403 (3)	0.0991 (2)	0.0365 (10)
H62	0.2127	0.5878	0.0620	0.044*
C63	0.2088 (2)	0.4402 (3)	0.0854 (3)	0.0498 (13)
H63	0.1859	0.4194	0.0389	0.060*
C64	0.2260 (2)	0.3714 (3)	0.1392 (3)	0.0527 (14)
H64	0.2148	0.3035	0.1295	0.063*
C65	0.2591 (2)	0.4001 (3)	0.2064 (3)	0.0465 (12)
H65	0.2706	0.3521	0.2431	0.056*
C66	0.2761 (2)	0.4994 (3)	0.2213 (2)	0.0349 (10)
H66	0.2995	0.5190	0.2679	0.042*
C71	0.08547 (18)	0.4719 (3)	0.1545 (2)	0.0286 (9)
C72	0.1045 (2)	0.4398 (3)	0.2244 (2)	0.0391 (10)
H72	0.1193	0.4871	0.2613	0.047*
C73	0.1020 (2)	0.3392 (3)	0.2408 (3)	0.0522 (13)
H73	0.1148	0.3186	0.2886	0.063*
C74	0.0807 (2)	0.2696 (3)	0.1875 (3)	0.0522 (13)
H74	0.0786	0.2012	0.1985	0.063*
C75	0.0629 (2)	0.2996 (3)	0.1190 (3)	0.0451 (11)
H75	0.0485	0.2515	0.0826	0.054*
C76	0.06535 (19)	0.4001 (3)	0.1016 (2)	0.0361 (10)
H76	0.0533	0.4195	0.0537	0.043*
C81	0.00757 (18)	0.6410 (2)	0.1179 (2)	0.0293 (9)
C82	−0.0208 (2)	0.7151 (3)	0.0690 (2)	0.0433 (10)
H82	0.0023	0.7457	0.0433	0.052*
C83	−0.0815 (2)	0.7454 (4)	0.0566 (3)	0.0538 (12)
H83	−0.0990	0.7971	0.0239	0.065*
C84	−0.1165 (2)	0.7004 (3)	0.0920 (3)	0.0487 (12)
H84	−0.1584	0.7195	0.0827	0.058*
C85	−0.0899 (2)	0.6279 (3)	0.1406 (3)	0.0545 (14)
H85	−0.1135	0.5973	0.1656	0.065*
C86	−0.0290 (2)	0.5989 (3)	0.1535 (3)	0.0477 (12)
H86	−0.0115	0.5487	0.1876	0.057*
C91	0.48233 (17)	0.8866 (2)	0.3622 (2)	0.0274 (8)
C92	0.52103 (19)	0.8391 (3)	0.4206 (2)	0.0386 (10)
H92	0.5048	0.8146	0.4549	0.046*
C93	0.5845 (2)	0.8260 (4)	0.4305 (3)	0.0557 (13)
H93	0.6111	0.7937	0.4715	0.067*
C94	0.6078 (2)	0.8606 (4)	0.3801 (3)	0.0551 (14)
H94	0.6505	0.8522	0.3863	0.066*
C95	0.5693 (2)	0.9069 (3)	0.3212 (3)	0.0493 (12)
H95	0.5853	0.9296	0.2863	0.059*
C96	0.50707 (19)	0.9209 (3)	0.3121 (2)	0.0380 (10)
H96	0.4810	0.9542	0.2714	0.046*
C101	0.40114 (18)	1.0472 (3)	0.3376 (2)	0.0288 (9)
C102	0.3749 (2)	1.0896 (3)	0.2710 (2)	0.0390 (10)
H102	0.3551	1.0483	0.2316	0.047*
C103	0.3777 (2)	1.1927 (3)	0.2619 (3)	0.0485 (12)
H103	0.3599	1.2211	0.2165	0.058*
C104	0.4065 (2)	1.2532 (3)	0.3192 (3)	0.0478 (12)
H104	0.4089	1.3230	0.3129	0.057*
C105	0.4314 (2)	1.2125 (3)	0.3851 (3)	0.0492 (12)
H105	0.4505	1.2542	0.4245	0.059*
C106	0.4286 (2)	1.1100 (3)	0.3940 (2)	0.0413 (11)
H106	0.4459	1.0825	0.4397	0.050*
C111	0.2579 (4)	0.4116 (4)	0.5242 (4)	0.0783 (19)
C112	0.2206 (4)	0.4227 (4)	0.4528 (4)	0.083 (2)
H112	0.1769	0.4305	0.4400	0.099*
C113	0.2501 (3)	0.4220 (4)	0.3988 (4)	0.078 (2)
H113	0.2261	0.4299	0.3506	0.094*
C114	0.3113 (4)	0.4101 (4)	0.4193 (4)	0.0790 (18)
H114	0.3312	0.4101	0.3850	0.095*
C115	0.3466 (4)	0.3977 (4)	0.4886 (4)	0.092 (2)
H115	0.3902	0.3884	0.5012	0.111*
C116	0.3194 (3)	0.3985 (4)	0.5412 (4)	0.0810 (19)
H116	0.3446	0.3897	0.5890	0.097*
C117	0.2305 (4)	0.4126 (4)	0.5796 (5)	0.114 (3)
H11A	0.2558	0.3720	0.6191	0.170*
H11B	0.1884	0.3854	0.5614	0.170*
H11C	0.2290	0.4812	0.5954	0.170*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0243 (19)	0.0240 (16)	0.025 (2)	0.0037 (14)	0.0118 (16)	−0.0025 (14)
B1	0.020 (2)	0.0242 (18)	0.023 (2)	−0.0029 (15)	0.0081 (17)	−0.0021 (16)
P1	0.0194 (5)	0.0210 (4)	0.0257 (5)	−0.0006 (3)	0.0115 (4)	−0.0030 (4)
C2	0.0179 (18)	0.0239 (16)	0.0235 (19)	−0.0018 (13)	0.0074 (15)	−0.0031 (14)
B2	0.019 (2)	0.031 (2)	0.023 (2)	0.0025 (16)	0.0108 (17)	−0.0006 (17)
P2	0.0198 (5)	0.0211 (4)	0.0248 (5)	−0.0004 (3)	0.0106 (4)	−0.0025 (4)
C3	0.0227 (19)	0.0267 (17)	0.029 (2)	−0.0012 (14)	0.0107 (16)	−0.0045 (15)
P3	0.0242 (5)	0.0278 (4)	0.0281 (6)	−0.0040 (4)	0.0109 (4)	−0.0041 (4)
C4	0.0202 (19)	0.0251 (17)	0.036 (2)	−0.0001 (14)	0.0152 (17)	−0.0012 (15)
P4	0.0233 (5)	0.0261 (4)	0.0300 (6)	−0.0040 (4)	0.0125 (4)	−0.0034 (4)
C11	0.0221 (19)	0.0300 (18)	0.031 (2)	0.0005 (14)	0.0108 (17)	−0.0057 (15)
C12	0.029 (2)	0.0370 (19)	0.030 (2)	0.0106 (16)	0.0089 (18)	0.0003 (17)
C13	0.044 (3)	0.040 (2)	0.048 (3)	0.014 (2)	0.007 (2)	0.009 (2)
C14	0.036 (3)	0.056 (3)	0.057 (3)	0.025 (2)	0.003 (2)	−0.001 (2)
C15	0.031 (2)	0.063 (3)	0.045 (3)	0.016 (2)	0.014 (2)	−0.009 (2)
C16	0.027 (2)	0.046 (2)	0.029 (2)	0.0051 (17)	0.0073 (18)	−0.0031 (17)
C21	0.025 (2)	0.0227 (16)	0.030 (2)	−0.0056 (14)	0.0078 (16)	−0.0084 (15)
C22	0.024 (2)	0.0363 (19)	0.030 (2)	0.0101 (16)	0.0093 (17)	0.0028 (17)
C23	0.048 (3)	0.049 (2)	0.039 (3)	0.014 (2)	0.004 (2)	0.005 (2)
C24	0.023 (2)	0.053 (3)	0.062 (3)	0.0158 (19)	0.000 (2)	−0.006 (2)
C25	0.027 (2)	0.050 (2)	0.056 (3)	0.0012 (18)	0.014 (2)	−0.020 (2)
C26	0.023 (2)	0.038 (2)	0.043 (2)	−0.0013 (16)	0.0150 (18)	−0.0096 (18)
C31	0.024 (2)	0.0253 (17)	0.037 (2)	−0.0047 (14)	0.0139 (18)	−0.0103 (16)
C32	0.029 (2)	0.040 (2)	0.046 (3)	−0.0061 (18)	0.012 (2)	−0.0150 (19)
C33	0.037 (3)	0.049 (3)	0.076 (4)	−0.015 (2)	0.024 (3)	−0.037 (3)
C34	0.044 (3)	0.029 (2)	0.116 (5)	−0.011 (2)	0.041 (3)	−0.030 (3)
C35	0.038 (3)	0.0234 (19)	0.105 (5)	0.0019 (18)	0.034 (3)	0.002 (2)
C36	0.030 (2)	0.0258 (18)	0.054 (3)	−0.0012 (16)	0.020 (2)	0.0013 (18)
C41	0.0198 (19)	0.0297 (17)	0.024 (2)	−0.0027 (14)	0.0068 (16)	−0.0053 (15)
C42	0.031 (2)	0.037 (2)	0.039 (2)	0.0021 (16)	0.019 (2)	−0.0021 (17)
C43	0.041 (3)	0.054 (2)	0.044 (3)	0.002 (2)	0.029 (2)	−0.010 (2)
C44	0.038 (3)	0.064 (3)	0.034 (3)	−0.006 (2)	0.024 (2)	0.001 (2)
C45	0.039 (3)	0.051 (2)	0.042 (3)	0.001 (2)	0.020 (2)	0.016 (2)
C46	0.032 (2)	0.037 (2)	0.043 (2)	0.0060 (17)	0.024 (2)	0.0066 (18)
C51	0.0177 (18)	0.0315 (17)	0.0246 (19)	0.0005 (14)	0.0104 (15)	−0.0007 (15)
C52	0.037 (2)	0.036 (2)	0.043 (3)	0.0046 (17)	0.022 (2)	0.0022 (18)
C53	0.037 (3)	0.058 (3)	0.052 (3)	0.013 (2)	0.030 (2)	0.000 (2)
C54	0.034 (3)	0.070 (3)	0.039 (3)	0.006 (2)	0.023 (2)	0.006 (2)
C55	0.053 (3)	0.048 (2)	0.045 (3)	0.007 (2)	0.030 (2)	0.015 (2)
C56	0.042 (3)	0.035 (2)	0.040 (2)	0.0068 (18)	0.021 (2)	0.0027 (18)
C61	0.0214 (19)	0.0262 (17)	0.039 (2)	−0.0008 (14)	0.0137 (18)	−0.0063 (16)
C62	0.029 (2)	0.040 (2)	0.038 (3)	0.0008 (17)	0.0087 (19)	−0.0092 (18)
C63	0.037 (3)	0.051 (3)	0.059 (3)	−0.012 (2)	0.012 (2)	−0.030 (2)
C64	0.041 (3)	0.027 (2)	0.095 (4)	−0.0052 (18)	0.029 (3)	−0.014 (2)
C65	0.042 (3)	0.0245 (18)	0.074 (4)	0.0036 (18)	0.021 (3)	0.002 (2)
C66	0.032 (2)	0.0275 (18)	0.046 (3)	−0.0010 (16)	0.015 (2)	−0.0013 (18)
C71	0.0212 (19)	0.0277 (17)	0.037 (2)	−0.0006 (15)	0.0095 (17)	−0.0013 (16)
C72	0.042 (3)	0.034 (2)	0.040 (3)	−0.0075 (18)	0.013 (2)	−0.0047 (18)
C73	0.061 (3)	0.041 (2)	0.048 (3)	−0.009 (2)	0.009 (2)	0.006 (2)
C74	0.050 (3)	0.029 (2)	0.072 (4)	−0.0055 (19)	0.013 (3)	0.006 (2)
C75	0.041 (3)	0.033 (2)	0.054 (3)	−0.0074 (19)	0.005 (2)	−0.011 (2)
C76	0.033 (2)	0.0337 (19)	0.038 (3)	−0.0049 (17)	0.0082 (19)	−0.0051 (18)
C81	0.026 (2)	0.0271 (17)	0.036 (2)	−0.0081 (15)	0.0120 (18)	−0.0100 (16)
C82	0.032 (2)	0.063 (3)	0.034 (2)	0.004 (2)	0.0098 (19)	0.006 (2)
C83	0.034 (3)	0.077 (3)	0.047 (3)	0.011 (2)	0.010 (2)	0.011 (2)
C84	0.028 (2)	0.052 (3)	0.063 (3)	−0.002 (2)	0.012 (2)	−0.018 (2)
C85	0.043 (3)	0.039 (2)	0.101 (4)	−0.005 (2)	0.049 (3)	−0.006 (2)
C86	0.049 (3)	0.033 (2)	0.075 (3)	−0.0004 (19)	0.038 (3)	0.002 (2)
C91	0.0239 (19)	0.0245 (16)	0.031 (2)	−0.0047 (14)	0.0064 (17)	−0.0063 (15)
C92	0.027 (2)	0.042 (2)	0.043 (3)	−0.0022 (17)	0.0078 (19)	−0.0095 (19)
C93	0.035 (3)	0.059 (3)	0.060 (3)	0.009 (2)	−0.001 (2)	−0.010 (2)
C94	0.021 (2)	0.063 (3)	0.080 (4)	0.000 (2)	0.015 (3)	−0.027 (3)
C95	0.040 (3)	0.050 (2)	0.068 (3)	−0.012 (2)	0.031 (3)	−0.021 (2)
C96	0.032 (2)	0.037 (2)	0.053 (3)	−0.0035 (17)	0.024 (2)	−0.0032 (19)
C101	0.027 (2)	0.0273 (17)	0.038 (2)	−0.0013 (15)	0.0198 (18)	−0.0068 (16)
C102	0.045 (3)	0.033 (2)	0.040 (3)	−0.0032 (18)	0.016 (2)	−0.0007 (18)
C103	0.066 (3)	0.032 (2)	0.051 (3)	−0.002 (2)	0.025 (2)	0.005 (2)
C104	0.057 (3)	0.0224 (18)	0.068 (3)	−0.0023 (19)	0.026 (3)	0.002 (2)
C105	0.055 (3)	0.034 (2)	0.057 (3)	−0.012 (2)	0.017 (3)	−0.012 (2)
C106	0.045 (3)	0.035 (2)	0.043 (3)	−0.0003 (19)	0.014 (2)	−0.0026 (19)
C111	0.100 (5)	0.033 (2)	0.102 (6)	−0.004 (3)	0.035 (5)	−0.004 (3)
C112	0.084 (5)	0.035 (3)	0.112 (6)	−0.007 (3)	0.011 (5)	−0.007 (3)
C113	0.065 (4)	0.048 (3)	0.102 (5)	0.001 (3)	0.003 (4)	−0.009 (3)
C114	0.103 (6)	0.045 (3)	0.086 (5)	−0.006 (3)	0.028 (4)	−0.003 (3)
C115	0.126 (7)	0.066 (4)	0.080 (5)	0.001 (4)	0.028 (5)	−0.002 (3)
C116	0.064 (4)	0.052 (3)	0.120 (6)	0.001 (3)	0.022 (4)	−0.008 (3)
C117	0.158 (8)	0.037 (3)	0.192 (9)	−0.015 (4)	0.119 (7)	−0.011 (4)

Geometric parameters (Å, º)

C1—B1	1.663 (5)	C53—H53	0.9500
C1—P2	1.824 (4)	C54—C55	1.383 (6)
C1—H1A	0.9900	C54—H54	0.9500
C1—H1B	0.9900	C55—C56	1.394 (6)
B1—C11	1.626 (5)	C55—H55	0.9500
B1—C3	1.654 (5)	C56—H56	0.9500
B1—P1	2.032 (4)	C61—C62	1.395 (6)
P1—C2	1.814 (4)	C61—C66	1.400 (6)
P1—C31	1.836 (3)	C62—C63	1.397 (6)
P1—C41	1.839 (4)	C62—H62	0.9500
C2—B2	1.677 (5)	C63—C64	1.379 (7)
C2—H2A	0.9900	C63—H63	0.9500
C2—H2B	0.9900	C64—C65	1.369 (7)
B2—C21	1.640 (5)	C64—H64	0.9500
B2—C4	1.645 (5)	C65—C66	1.393 (5)
B2—P2	2.018 (4)	C65—H65	0.9500
P2—C51	1.832 (4)	C66—H66	0.9500
P2—C61	1.836 (3)	C71—C76	1.397 (5)
C3—P3	1.865 (4)	C71—C72	1.400 (6)
C3—H3A	0.9900	C72—C73	1.397 (6)
C3—H3B	0.9900	C72—H72	0.9500
P3—C81	1.845 (4)	C73—C74	1.386 (7)
P3—C71	1.858 (4)	C73—H73	0.9500
C4—P4	1.850 (4)	C74—C75	1.365 (7)
C4—H4A	0.9900	C74—H74	0.9500
C4—H4B	0.9900	C75—C76	1.401 (6)
P4—C101	1.858 (4)	C75—H75	0.9500
P4—C91	1.859 (4)	C76—H76	0.9500
C11—C16	1.407 (5)	C81—C86	1.395 (6)
C11—C12	1.410 (6)	C81—C82	1.398 (6)
C12—C13	1.399 (5)	C82—C83	1.387 (6)
C12—H12	0.9500	C82—H82	0.9500
C13—C14	1.369 (7)	C83—C84	1.380 (7)
C13—H13	0.9500	C83—H83	0.9500
C14—C15	1.377 (7)	C84—C85	1.371 (7)
C14—H14	0.9500	C84—H84	0.9500
C15—C16	1.397 (6)	C85—C86	1.386 (6)
C15—H15	0.9500	C85—H85	0.9500
C16—H16	0.9500	C86—H86	0.9500
C21—C22	1.396 (5)	C91—C92	1.370 (6)
C21—C26	1.419 (5)	C91—C96	1.396 (5)
C22—C23	1.401 (6)	C92—C93	1.410 (6)
C22—H22	0.9500	C92—H92	0.9500
C23—C24	1.392 (7)	C93—C94	1.380 (8)
C23—H23	0.9500	C93—H93	0.9500
C24—C25	1.379 (7)	C94—C95	1.368 (7)
C24—H24	0.9500	C94—H94	0.9500
C25—C26	1.389 (6)	C95—C96	1.385 (6)
C25—H25	0.9500	C95—H95	0.9500
C26—H26	0.9500	C96—H96	0.9500
C31—C36	1.394 (6)	C101—C106	1.386 (6)
C31—C32	1.392 (6)	C101—C102	1.396 (6)
C32—C33	1.393 (6)	C102—C103	1.401 (6)
C32—H32	0.9500	C102—H102	0.9500
C33—C34	1.379 (8)	C103—C104	1.386 (7)
C33—H33	0.9500	C103—H103	0.9500
C34—C35	1.370 (8)	C104—C105	1.373 (7)
C34—H34	0.9500	C104—H104	0.9500
C35—C36	1.412 (6)	C105—C106	1.393 (6)
C35—H35	0.9500	C105—H105	0.9500
C36—H36	0.9500	C106—H106	0.9500
C41—C42	1.396 (5)	C111—C116	1.343 (9)
C41—C46	1.405 (5)	C111—C112	1.415 (9)
C42—C43	1.394 (6)	C111—C117	1.456 (10)
C42—H42	0.9500	C112—C113	1.465 (10)
C43—C44	1.374 (6)	C112—H112	0.9500
C43—H43	0.9500	C113—C114	1.331 (9)
C44—C45	1.384 (6)	C113—H113	0.9500
C44—H44	0.9500	C114—C115	1.370 (9)
C45—C46	1.403 (6)	C114—H114	0.9500
C45—H45	0.9500	C115—C116	1.403 (10)
C46—H46	0.9500	C115—H115	0.9500
C51—C56	1.397 (5)	C116—H116	0.9500
C51—C52	1.405 (5)	C117—H11A	0.9800
C52—C53	1.384 (6)	C117—H11B	0.9800
C52—H52	0.9500	C117—H11C	0.9800
C53—C54	1.381 (6)
B1—C1—P2	120.7 (2)	C53—C52—C51	121.1 (4)
B1—C1—H1A	107.2	C53—C52—H52	119.4
P2—C1—H1A	107.2	C51—C52—H52	119.4
B1—C1—H1B	107.2	C54—C53—C52	120.2 (4)
P2—C1—H1B	107.2	C54—C53—H53	119.9
H1A—C1—H1B	106.8	C52—C53—H53	119.9
C11—B1—C3	113.0 (3)	C53—C54—C55	119.7 (4)
C11—B1—C1	111.1 (3)	C53—C54—H54	120.2
C3—B1—C1	114.2 (3)	C55—C54—H54	120.2
C11—B1—P1	109.8 (2)	C54—C55—C56	120.7 (4)
C3—B1—P1	101.7 (2)	C54—C55—H55	119.6
C1—B1—P1	106.3 (2)	C56—C55—H55	119.6
C2—P1—C31	108.43 (17)	C55—C56—C51	120.2 (4)
C2—P1—C41	106.49 (17)	C55—C56—H56	119.9
C31—P1—C41	100.33 (17)	C51—C56—H56	119.9
C2—P1—B1	110.01 (17)	C62—C61—C66	119.5 (3)
C31—P1—B1	118.43 (17)	C62—C61—P2	118.8 (3)
C41—P1—B1	112.22 (17)	C66—C61—P2	121.7 (3)
B2—C2—P1	119.2 (2)	C61—C62—C63	119.6 (4)
B2—C2—H2A	107.5	C61—C62—H62	120.2
P1—C2—H2A	107.5	C63—C62—H62	120.2
B2—C2—H2B	107.5	C64—C63—C62	120.2 (4)
P1—C2—H2B	107.5	C64—C63—H63	119.9
H2A—C2—H2B	107.0	C62—C63—H63	119.9
C21—B2—C4	112.2 (3)	C65—C64—C63	120.7 (4)
C21—B2—C2	111.4 (3)	C65—C64—H64	119.7
C4—B2—C2	113.2 (3)	C63—C64—H64	119.7
C21—B2—P2	110.6 (2)	C64—C65—C66	120.2 (4)
C4—B2—P2	103.4 (3)	C64—C65—H65	119.9
C2—B2—P2	105.5 (2)	C66—C65—H65	119.9
C1—P2—C51	107.30 (16)	C65—C66—C61	119.8 (4)
C1—P2—C61	107.99 (17)	C65—C66—H66	120.1
C51—P2—C61	101.59 (17)	C61—C66—H66	120.1
C1—P2—B2	108.89 (16)	C76—C71—C72	118.0 (3)
C51—P2—B2	112.13 (17)	C76—C71—P3	117.7 (3)
C61—P2—B2	118.28 (18)	C72—C71—P3	124.3 (3)
B1—C3—P3	114.1 (3)	C73—C72—C71	121.0 (4)
B1—C3—H3A	108.7	C73—C72—H72	119.5
P3—C3—H3A	108.7	C71—C72—H72	119.5
B1—C3—H3B	108.7	C74—C73—C72	120.0 (4)
P3—C3—H3B	108.7	C74—C73—H73	120.0
H3A—C3—H3B	107.6	C72—C73—H73	120.0
C81—P3—C71	99.50 (17)	C75—C74—C73	119.8 (4)
C81—P3—C3	102.97 (17)	C75—C74—H74	120.1
C71—P3—C3	102.16 (17)	C73—C74—H74	120.1
B2—C4—P4	111.2 (3)	C74—C75—C76	121.0 (4)
B2—C4—H4A	109.4	C74—C75—H75	119.5
P4—C4—H4A	109.4	C76—C75—H75	119.5
B2—C4—H4B	109.4	C71—C76—C75	120.3 (4)
P4—C4—H4B	109.4	C71—C76—H76	119.9
H4A—C4—H4B	108.0	C75—C76—H76	119.9
C4—P4—C101	103.52 (17)	C86—C81—C82	116.0 (4)
C4—P4—C91	103.72 (17)	C86—C81—P3	125.8 (3)
C101—P4—C91	96.75 (16)	C82—C81—P3	118.2 (3)
C16—C11—C12	115.3 (3)	C83—C82—C81	122.2 (4)
C16—C11—B1	121.9 (3)	C83—C82—H82	118.9
C12—C11—B1	122.8 (3)	C81—C82—H82	118.9
C13—C12—C11	122.1 (4)	C84—C83—C82	120.0 (4)
C13—C12—H12	118.9	C84—C83—H83	120.0
C11—C12—H12	118.9	C82—C83—H83	120.0
C14—C13—C12	120.9 (4)	C85—C84—C83	119.2 (4)
C14—C13—H13	119.6	C85—C84—H84	120.4
C12—C13—H13	119.6	C83—C84—H84	120.4
C13—C14—C15	118.7 (4)	C84—C85—C86	120.5 (4)
C13—C14—H14	120.6	C84—C85—H85	119.7
C15—C14—H14	120.6	C86—C85—H85	119.7
C14—C15—C16	121.1 (4)	C85—C86—C81	122.0 (4)
C14—C15—H15	119.5	C85—C86—H86	119.0
C16—C15—H15	119.5	C81—C86—H86	119.0
C15—C16—C11	121.8 (4)	C92—C91—C96	118.4 (4)
C15—C16—H16	119.1	C92—C91—P4	118.4 (3)
C11—C16—H16	119.1	C96—C91—P4	123.0 (3)
C22—C21—C26	115.7 (3)	C91—C92—C93	121.1 (4)
C22—C21—B2	123.7 (3)	C91—C92—H92	119.5
C26—C21—B2	120.5 (3)	C93—C92—H92	119.5
C21—C22—C23	122.5 (4)	C94—C93—C92	119.3 (5)
C21—C22—H22	118.8	C94—C93—H93	120.3
C23—C22—H22	118.8	C92—C93—H93	120.3
C24—C23—C22	120.1 (4)	C95—C94—C93	120.0 (4)
C24—C23—H23	120.0	C95—C94—H94	120.0
C22—C23—H23	120.0	C93—C94—H94	120.0
C25—C24—C23	118.8 (4)	C94—C95—C96	120.5 (5)
C25—C24—H24	120.6	C94—C95—H95	119.8
C23—C24—H24	120.6	C96—C95—H95	119.8
C24—C25—C26	121.1 (4)	C95—C96—C91	120.7 (4)
C24—C25—H25	119.5	C95—C96—H96	119.6
C26—C25—H25	119.5	C91—C96—H96	119.6
C25—C26—C21	121.8 (4)	C106—C101—C102	118.2 (3)
C25—C26—H26	119.1	C106—C101—P4	116.9 (3)
C21—C26—H26	119.1	C102—C101—P4	124.9 (3)
C36—C31—C32	119.5 (3)	C101—C102—C103	120.3 (4)
C36—C31—P1	121.5 (3)	C101—C102—H102	119.8
C32—C31—P1	118.8 (3)	C103—C102—H102	119.8
C33—C32—C31	119.8 (4)	C104—C103—C102	120.0 (4)
C33—C32—H32	120.1	C104—C103—H103	120.0
C31—C32—H32	120.1	C102—C103—H103	120.0
C34—C33—C32	120.8 (5)	C105—C104—C103	120.1 (4)
C34—C33—H33	119.6	C105—C104—H104	120.0
C32—C33—H33	119.6	C103—C104—H104	120.0
C35—C34—C33	120.0 (4)	C104—C105—C106	119.8 (4)
C35—C34—H34	120.0	C104—C105—H105	120.1
C33—C34—H34	120.0	C106—C105—H105	120.1
C34—C35—C36	120.2 (5)	C101—C106—C105	121.5 (4)
C34—C35—H35	119.9	C101—C106—H106	119.2
C36—C35—H35	119.9	C105—C106—H106	119.2
C31—C36—C35	119.6 (4)	C116—C111—C112	119.5 (7)
C31—C36—H36	120.2	C116—C111—C117	119.4 (8)
C35—C36—H36	120.2	C112—C111—C117	121.0 (8)
C42—C41—C46	118.2 (3)	C111—C112—C113	119.3 (7)
C42—C41—P1	120.0 (3)	C111—C112—H112	120.4
C46—C41—P1	121.7 (3)	C113—C112—H112	120.4
C43—C42—C41	120.7 (4)	C114—C113—C112	118.2 (7)
C43—C42—H42	119.6	C114—C113—H113	120.9
C41—C42—H42	119.6	C112—C113—H113	120.9
C44—C43—C42	120.5 (4)	C113—C114—C115	121.8 (8)
C44—C43—H43	119.7	C113—C114—H114	119.1
C42—C43—H43	119.7	C115—C114—H114	119.1
C43—C44—C45	120.1 (4)	C114—C115—C116	121.1 (8)
C43—C44—H44	120.0	C114—C115—H115	119.5
C45—C44—H44	120.0	C116—C115—H115	119.5
C44—C45—C46	120.0 (4)	C111—C116—C115	120.2 (8)
C44—C45—H45	120.0	C111—C116—H116	119.9
C46—C45—H45	120.0	C115—C116—H116	119.9
C45—C46—C41	120.4 (4)	C111—C117—H11A	109.5
C45—C46—H46	119.8	C111—C117—H11B	109.5
C41—C46—H46	119.8	H11A—C117—H11B	109.5
C56—C51—C52	118.1 (3)	C111—C117—H11C	109.5
C56—C51—P2	122.7 (3)	H11A—C117—H11C	109.5
C52—C51—P2	119.1 (3)	H11B—C117—H11C	109.5
P2—C1—B1—C11	172.9 (2)	C41—C42—C43—C44	−0.3 (7)
P2—C1—B1—C3	−57.8 (4)	C42—C43—C44—C45	0.1 (7)
P2—C1—B1—P1	53.5 (3)	C43—C44—C45—C46	0.2 (7)
C11—B1—P1—C2	−167.3 (2)	C44—C45—C46—C41	−0.3 (7)
C3—B1—P1—C2	72.8 (3)	C42—C41—C46—C45	0.1 (6)
C1—B1—P1—C2	−47.0 (3)	P1—C41—C46—C45	−179.1 (3)
C11—B1—P1—C31	−41.8 (3)	C1—P2—C51—C56	29.9 (4)
C3—B1—P1—C31	−161.8 (2)	C61—P2—C51—C56	143.1 (3)
C1—B1—P1—C31	78.4 (3)	B2—P2—C51—C56	−89.6 (4)
C11—B1—P1—C41	74.3 (3)	C1—P2—C51—C52	−152.8 (3)
C3—B1—P1—C41	−45.6 (3)	C61—P2—C51—C52	−39.6 (3)
C1—B1—P1—C41	−165.4 (2)	B2—P2—C51—C52	87.7 (3)
C31—P1—C2—B2	−73.9 (3)	C56—C51—C52—C53	−0.4 (6)
C41—P1—C2—B2	178.9 (3)	P2—C51—C52—C53	−177.9 (4)
B1—P1—C2—B2	57.1 (3)	C51—C52—C53—C54	0.2 (7)
P1—C2—B2—C21	−177.9 (2)	C52—C53—C54—C55	−0.1 (7)
P1—C2—B2—C4	54.6 (4)	C53—C54—C55—C56	0.2 (7)
P1—C2—B2—P2	−57.8 (3)	C54—C55—C56—C51	−0.4 (7)
B1—C1—P2—C51	−179.1 (3)	C52—C51—C56—C55	0.5 (6)
B1—C1—P2—C61	72.0 (3)	P2—C51—C56—C55	177.9 (4)
B1—C1—P2—B2	−57.6 (3)	C1—P2—C61—C62	58.3 (4)
C21—B2—P2—C1	172.2 (2)	C51—P2—C61—C62	−54.4 (3)
C4—B2—P2—C1	−67.6 (3)	B2—P2—C61—C62	−177.6 (3)
C2—B2—P2—C1	51.6 (3)	C1—P2—C61—C66	−123.4 (3)
C21—B2—P2—C51	−69.2 (3)	C51—P2—C61—C66	123.9 (3)
C4—B2—P2—C51	51.0 (3)	B2—P2—C61—C66	0.8 (4)
C2—B2—P2—C51	170.2 (2)	C66—C61—C62—C63	0.3 (6)
C21—B2—P2—C61	48.5 (3)	P2—C61—C62—C63	178.7 (3)
C4—B2—P2—C61	168.7 (2)	C61—C62—C63—C64	0.3 (7)
C2—B2—P2—C61	−72.1 (3)	C62—C63—C64—C65	−0.3 (7)
C11—B1—C3—P3	65.8 (4)	C63—C64—C65—C66	−0.2 (7)
C1—B1—C3—P3	−62.5 (4)	C64—C65—C66—C61	0.7 (7)
P1—B1—C3—P3	−176.54 (19)	C62—C61—C66—C65	−0.8 (6)
B1—C3—P3—C81	−92.8 (3)	P2—C61—C66—C65	−179.1 (3)
B1—C3—P3—C71	164.4 (3)	C81—P3—C71—C76	88.4 (3)
C21—B2—C4—P4	−62.1 (3)	C3—P3—C71—C76	−166.1 (3)
C2—B2—C4—P4	65.0 (3)	C81—P3—C71—C72	−93.6 (4)
P2—B2—C4—P4	178.66 (18)	C3—P3—C71—C72	12.0 (4)
B2—C4—P4—C101	−164.8 (2)	C76—C71—C72—C73	−1.5 (7)
B2—C4—P4—C91	94.7 (3)	P3—C71—C72—C73	−179.5 (4)
C3—B1—C11—C16	48.0 (5)	C71—C72—C73—C74	0.3 (8)
C1—B1—C11—C16	177.9 (3)	C72—C73—C74—C75	0.6 (8)
P1—B1—C11—C16	−64.8 (4)	C73—C74—C75—C76	−0.3 (8)
C3—B1—C11—C12	−130.5 (4)	C72—C71—C76—C75	1.8 (6)
C1—B1—C11—C12	−0.5 (5)	P3—C71—C76—C75	180.0 (3)
P1—B1—C11—C12	116.8 (4)	C74—C75—C76—C71	−0.9 (7)
C16—C11—C12—C13	3.4 (6)	C71—P3—C81—C86	26.5 (4)
B1—C11—C12—C13	−178.1 (4)	C3—P3—C81—C86	−78.4 (4)
C11—C12—C13—C14	−1.8 (7)	C71—P3—C81—C82	−150.6 (3)
C12—C13—C14—C15	−0.1 (7)	C3—P3—C81—C82	104.5 (3)
C13—C14—C15—C16	0.3 (7)	C86—C81—C82—C83	0.2 (6)
C14—C15—C16—C11	1.5 (7)	P3—C81—C82—C83	177.6 (4)
C12—C11—C16—C15	−3.2 (6)	C81—C82—C83—C84	−1.6 (7)
B1—C11—C16—C15	178.3 (4)	C82—C83—C84—C85	1.9 (7)
C4—B2—C21—C22	131.3 (4)	C83—C84—C85—C86	−0.9 (7)
C2—B2—C21—C22	3.2 (5)	C84—C85—C86—C81	−0.4 (7)
P2—B2—C21—C22	−113.8 (3)	C82—C81—C86—C85	0.7 (6)
C4—B2—C21—C26	−45.0 (4)	P3—C81—C86—C85	−176.5 (4)
C2—B2—C21—C26	−173.1 (3)	C4—P4—C91—C92	−126.4 (3)
P2—B2—C21—C26	69.8 (4)	C101—P4—C91—C92	127.9 (3)
C26—C21—C22—C23	−2.4 (5)	C4—P4—C91—C96	59.0 (3)
B2—C21—C22—C23	−178.9 (4)	C101—P4—C91—C96	−46.8 (3)
C21—C22—C23—C24	2.3 (7)	C96—C91—C92—C93	0.8 (6)
C22—C23—C24—C25	−1.3 (7)	P4—C91—C92—C93	−174.1 (3)
C23—C24—C25—C26	0.5 (7)	C91—C92—C93—C94	−0.8 (6)
C24—C25—C26—C21	−0.8 (6)	C92—C93—C94—C95	−0.1 (7)
C22—C21—C26—C25	1.6 (5)	C93—C94—C95—C96	1.0 (7)
B2—C21—C26—C25	178.2 (4)	C94—C95—C96—C91	−1.1 (6)
C2—P1—C31—C36	126.3 (3)	C92—C91—C96—C95	0.1 (6)
C41—P1—C31—C36	−122.3 (3)	P4—C91—C96—C95	174.8 (3)
B1—P1—C31—C36	0.1 (4)	C4—P4—C101—C106	174.0 (3)
C2—P1—C31—C32	−57.4 (4)	C91—P4—C101—C106	−80.0 (3)
C41—P1—C31—C32	54.0 (3)	C4—P4—C101—C102	−4.9 (4)
B1—P1—C31—C32	176.4 (3)	C91—P4—C101—C102	101.0 (4)
C36—C31—C32—C33	0.6 (6)	C106—C101—C102—C103	1.3 (6)
P1—C31—C32—C33	−175.8 (3)	P4—C101—C102—C103	−179.8 (4)
C31—C32—C33—C34	−0.5 (7)	C101—C102—C103—C104	−0.2 (7)
C32—C33—C34—C35	0.1 (7)	C102—C103—C104—C105	−1.0 (8)
C33—C34—C35—C36	0.2 (7)	C103—C104—C105—C106	1.0 (8)
C32—C31—C36—C35	−0.3 (6)	C102—C101—C106—C105	−1.2 (7)
P1—C31—C36—C35	176.0 (3)	P4—C101—C106—C105	179.7 (4)
C34—C35—C36—C31	−0.1 (7)	C104—C105—C106—C101	0.1 (8)
C2—P1—C41—C42	150.7 (3)	C116—C111—C112—C113	−1.4 (8)
C31—P1—C41—C42	37.8 (3)	C117—C111—C112—C113	179.5 (4)
B1—P1—C41—C42	−88.9 (3)	C111—C112—C113—C114	0.5 (8)
C2—P1—C41—C46	−30.1 (4)	C112—C113—C114—C115	0.6 (8)
C31—P1—C41—C46	−143.0 (3)	C113—C114—C115—C116	−0.9 (9)
B1—P1—C41—C46	90.3 (3)	C112—C111—C116—C115	1.2 (8)
C46—C41—C42—C43	0.2 (6)	C117—C111—C116—C115	−179.7 (5)
P1—C41—C42—C43	179.4 (3)	C114—C115—C116—C111	0.0 (9)