Bis(1,3-diphen­ylpropane-1,3-dionato-κ2O,O′){hydro­tris[3-(2-pyrid­yl)pyrazol-1-yl]borato}praseodymium(III): another member of an unpredicta­ble series

Davies, G.M.; Adams, H.; Ward, M.D.

doi:10.1107/S0108270105007791

metal-organic compounds

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 61| Part 5| May 2005| Pages m221-m223

doi:10.1107/S0108270105007791

Bis(1,3-diphenylpropane-1,3-dionato-κ²O,O′){hydrotris[3-(2-pyridyl)pyrazol-1-yl]borato}praseodymium(III): another member of an unpredictable series

Graham M. Davies,^a Harry Adams ^a and Michael D. Ward ^a ^*

^aDepartment of Chemistry, University of Sheffield, Sheffield S3 7HF, England
^*Correspondence e-mail: m.d.ward@sheffield.ac.uk

(Received 8 March 2005; accepted 11 March 2005; online 2 April 2005)

Reaction of praseodymium(III) chloride with stoichometric quantities of dibenzoylmethane (Hdbm) and hydrotris[3-(2-pyridyl)pyrazol-1-yl]borate (Tp^2py) affords the title complex, [Pr(C₂₄H₁₉BN₉)(C₁₅H₁₁O₄)₂]. The lanthanide ion in this ternary complex exhibits an N₆O₄ ten-coordinate geometry arising from the five bidentate arms found on the anionic ligands. The structure is entirely different from those found in other lanthanide complexes with the same ligand set.

Comment

Since their introduction, poly(pyrazolyl)borate ligands [for a review, see Trofimenko (1993 )] have proved extremely popular for the coordination chemistry of lanthanide(III) ions (Marques et al., 2002 ). This is largely for two reasons: firstly, their multiple denticity, hard donor set and single negative charge are ideally attractive to the hard lanthanide(III) cations; secondly, the ease with which substituents can be added at the 3- and 5-positions of the pyrazolyl rings allows fine-tuning of the size of the ligand cavity. We have been interested in both the structural and photophysical properties of such complexes (Amoroso et al., 1994 ; Bardwell et al., 1997 ; Jones et al., 1997 ; Armaroli et al., 1999 ; Reeves et al., 1999 ; Beeby et al., 2002 ), particularly with the ligand hydrotris[3-(2-pyridyl)pyrazol-1-yl]borate (Tp^2py), in which the pyrazolyl rings are functionalized with 2-pyridyl substituents, creating a hexadentate podand-type ligand.

We have used dbm (Hdbm is dibenzoylmethane) as a co-ligand in order to exclude solvent molecules from the coordination sphere of the metal ion, which is essential for optimization of the photophysical properties of lanthanide(III) complexes (Beeby et al., 1999 ), and have recently structurally characterized two types of mixed-ligand Tp^2py/dbm complex with lanthanide(III) ions. In eight-coordinate [Ln(Tp^2py)(dbm)₂] (Ln is Eu or Tb), one of the three bidentate arms of Tp^2py is pendant, such that this ligand is only tetradentate and the metal centre has an N₄O₄ coordination sphere (Ward et al., 1999 ; Davies et al., 2004 ). In contrast, [Nd(Tp^2py)₂][Nd(dbm)₄] contains 12-coordinate [Nd(Tp^2py)₂]⁺ cations and eight-coordinate [Nd(dbm)₄]⁻ anions, the former with an icosahedral N₁₂ coordination and the latter with unusual O₈ cubic geometry (Davies et al., 2004). In this paper, we report a new structural type in this series, the title compound, [Pr(Tp^2py)(dbm)₂], (I), which is ten-coordinate, with the Pr^III ion in an N₆O₄ environment with all three chelating arms of Tp^2py attached to the metal centre.

Complex (I) (Fig. 1) was prepared by the reaction of praseodymium(III) chloride hydrate with KTp^2py and Hdbm (1:1:2 molar ratio) in aqueous methanol with a few drops of triethylamine added. By comparison with the analogous Eu^III and Tb^III structures, the original concept of the ligand design is achieved in this case, with all three arms of the Tp^2py molecule chelating to the Pr^III ion. The larger ionic radius of Pr^III allows the two dbm units to coordinate without displacing one of the arms of the scorpionate, in contrast with the behaviour shown by the smaller ions Eu^III and Tb^III. This places the metal ion in a ten-coordinate N₆O₄ coordination environment, with all five chelating units (three pyrazolyl-pyridine units and two dbm ligands) being approximately parallel to one another.

Many ten-donor coordination spheres exist among Pr^III complexes, although only two previous examples of N₆O₄ environments have been reported to date (Jones et al., 1997; Tamboura et al., 2004 ). The Pr—N and Pr—O bond lengths are unremarkable, with averages of 2.652, 2.738, and 2.469 Å for the Pr—N_pz, Pr—N_py and Pr—O bonds (pz is pyrazolyl and py is pyridyl), respectively, all of which are understandably longer than those of the Eu^III and Tb^III analogues.

The coordination geometry of (I) does not obviously match any of the `ideal' arrangments of ten-coordination (Kepert, 1987 ). The best way of looking at the coordination geometry is down the N122—Pr1 bond (Fig. 2). The other two pyrazole N atoms, N102 and N142, form a pentagon with pyridyl atom N131 and atoms O55 and O21 from the dbm units. The average edge length and angle for this pentagon are 2.818 Å and 107.6°, respectively, using O55; if O55′ is used instead, these values become 2.871 Å and 106.9°, respectively. These five atoms display an average deviation from their mean plane of 0.095 (if O55 is used) or 0.180 Å (if O55′ is used). The pentagon is capped by atom N122, while on the other side of the pentagon resides a distorted square described by atoms O25, N151, N111 and O51. This `square' has an average edge of 2.983 Å and an average angle of 89.5° at its corners, but is rather irregular, with the corner angles varying from 75.50 to 102.31°. The mean deviation from the plane of these four atoms is 0.135 Å.

In conclusion, the contrast of this structure with those of the Eu^III, Tb^III and Nd^III analogues with the same stoichiometry is remarkable. The difference between this Pr^III structure and the eight-coordinate complexes with Tb^III and Eu^III can be rationalized on the basis of the larger ionic radius of Pr^III. The contrast with the structure of [Nd(Tp^2py)₂][Nd(dbm)₄] is less easy to explain. It is possible that there is an equilibrium mixture of structural types in solution which is perturbed in one direction or another by crystallization. We examined several crystals of (I) and found them all to have the same unit cell.

Figure 1
A view of (I)

, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level and H atoms have been omitted for clarity.

Figure 2
The coordination geometry about the Pr^III ion in (I)

. Only the major component of the disorder is shown.

Experimental

KTp^2py was prepared according to the published method of Amoroso et al. (1994). KTp^2py (202 mg, 0.42 mmol) in MeOH (5 ml) was added to a solution of PrCl₃·6H₂O (148 mg, 0.42 mmol) in MeOH (5 ml) and allowed to stir for 5 min at room temperature. A solution of Hdbm (188 mg, 0.84 mmol) in MeOH (5 ml) with Et₃N (1 ml) was added and, after a further 5 min, water (20 ml) was added, generating a lime-green precipitate. The product was isolated by filtration and slowly recrystallized by the layering of hexanes onto a concentrated solution of the product in dichloromethane. After 5 d, the green crystals which formed were collected by filtration and washed with hexane and ether to give (I) in 67% yield. IR: ν_(B—H) 2444 cm⁻¹. Analysis found: C 62.2, H 4.0, N 12.0%; calculated for [Pr(C₂₄H₁₉BN₉)(C₁₅H₁₁O₄)₂]: C 61.8, H 4.1, N 12.0%. FAB–MS gave a strong peak at m/z = 808, corresponding to the loss of one dbm unit to give the fragment {Pr(Tp^2py)(dbm)}⁺; a weaker signal at m/z = 1029 suggested the presence of the {Pr(Tp^2py)(dbm)₂} unit minus two H atoms. The crystals were suitable for single-crystal X-ray diffraction and were completely air-stable. A suitable crystal was coated in engine oil to clean it of subsidiary grains.

Crystal data

[Pr(C₂₄H₁₉BN₉)(C₁₅H₁₁O₄)₂]
M_r = 1031.68
Triclinic, $[P \overline 1]$
a = 11.6308 (15) Å
b = 11.9248 (16) Å
c = 18.569 (2) Å
α = 96.558 (2)°
β = 106.782 (2)°
γ = 105.669 (2)°
V = 2321.9 (5) Å³
Z = 2
D_x = 1.476 Mg m⁻³
Mo Kα radiation
Cell parameters from 4832 reflections
θ = 4.7–54.6°
μ = 1.11 mm⁻¹
T = 150 (2) K
Block, green
0.34 × 0.25 × 0.18 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
ω scans
Absorption correction: multi-scan(SADABS; Sheldrick, 1996 )T_min = 0.705, T_max = 0.826
22 669 measured reflections
8143 independent reflections
7003 reflections with I > 2σ(I)
R_int = 0.032
θ_max = 25.0°
h = −13 → 13
k = −14 → 14
l = −22 → 22

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.074
S = 1.05
8143 reflections
680 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0285P)² + 2.7047P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.72 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Pr1—O55	2.448 (17)
Pr1—O25	2.454 (2)
Pr1—O51	2.464 (2)
Pr1—O55′	2.492 (17)
Pr1—O21	2.496 (2)
Pr1—N122	2.595 (3)
Pr1—N142	2.656 (3)
Pr1—N131	2.656 (3)
Pr1—N102	2.704 (3)
Pr1—N151	2.754 (3)
Pr1—N111	2.804 (3)

O55—Pr1—O25	128.4 (6)
O55—Pr1—O51	71.7 (5)
O25—Pr1—O51	65.89 (7)
O55—Pr1—O55′	9.0 (6)
O25—Pr1—O55′	126.1 (6)
O51—Pr1—O55′	65.2 (5)
O55—Pr1—O21	129.8 (4)
O25—Pr1—O21	65.98 (7)
O51—Pr1—O21	128.16 (7)
O55′—Pr1—O21	138.5 (4)
O55—Pr1—N122	69.4 (3)
O25—Pr1—N122	121.82 (9)
O51—Pr1—N122	131.58 (8)
O55′—Pr1—N122	78.1 (4)
O21—Pr1—N122	65.02 (9)
O55—Pr1—N142	121.4 (6)
O25—Pr1—N142	109.44 (8)
O51—Pr1—N142	154.01 (9)
O55′—Pr1—N142	124.5 (7)
O21—Pr1—N142	63.44 (9)
N122—Pr1—N142	73.55 (9)
O55—Pr1—N131	71.2 (6)
O25—Pr1—N131	73.08 (8)
O51—Pr1—N131	79.07 (8)
O55′—Pr1—N131	76.8 (6)
O21—Pr1—N131	69.66 (8)
N122—Pr1—N131	61.99 (9)
N142—Pr1—N131	125.31 (9)
O55—Pr1—N102	65.5 (6)
O25—Pr1—N102	163.61 (8)
O51—Pr1—N102	117.95 (9)
O55′—Pr1—N102	66.0 (7)
O21—Pr1—N102	113.69 (9)
N122—Pr1—N102	68.87 (11)
N142—Pr1—N102	59.51 (9)
N131—Pr1—N102	122.86 (9)
O55—Pr1—N151	150.3 (5)
O25—Pr1—N151	65.76 (8)
O51—Pr1—N151	98.08 (8)
O55′—Pr1—N151	142.4 (4)
O21—Pr1—N151	78.77 (8)
N122—Pr1—N151	129.64 (9)
N142—Pr1—N151	58.98 (9)
N131—Pr1—N151	135.59 (9)
N102—Pr1—N151	97.90 (9)
O55—Pr1—N111	74.0 (5)
O25—Pr1—N111	113.86 (9)
O51—Pr1—N111	68.63 (9)
O55′—Pr1—N111	66.3 (5)
O21—Pr1—N111	151.93 (8)
N122—Pr1—N111	124.18 (10)
N142—Pr1—N111	92.39 (10)
N131—Pr1—N111	138.32 (9)
N102—Pr1—N111	58.02 (11)
N151—Pr1—N111	76.31 (9)

One of the dbm units was shown to contain disorder about atom C52. The disordered phenyl ring was constrained to ideal geometry and the disorder was modelled over two sites, with refined site occupancies of 0.514 (3) and 0.486 (3). All H atoms were positioned geometrically and refined with a riding model, with C—H = 0.93 Å for aromatic rings and 0.96 Å for disordered rings, and with B—H = 1.07 Å. In all cases, U_iso(H) values were constrained to be 1.2U_eq of the carrier atom.

Data collection: XSCANS (Siemens, 1996 ); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 1997 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S0108270105007791/gd1380sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S0108270105007791/gd1380Isup2.hkl

Comment top

Since their introduction, poly(pyrazolyl)borate ligands [for a review, see Trofimenko (1993)] have proved extremely popular for the coordination chemistry of lanthanide(III) ions (Marques et al., 2002). This is largely for two reasons. Firstly, their multiple denticity, hard donor set and single negative charge are ideally attractive to the hard lanthanide(III) cations. Secondly, the ease with which substituents can be added at the 3- and 5-positions of the pyrazolyl rings allows fine-tuning of the size of the ligand cavity. We have been interested in both the structural and photophysical properties of such complexes (Amoroso et al., 1994; Bardwell et al., 1997; Jones et al., 1997; Armaroli et al., 1999; Reeves et al., 1999; Beeby et al., 2002), particularly with the ligand (Tp^2py), in which the pyrazolyl rings are functionalized with 2-pyridyl substituents, creating a hexadentate podand-type ligand.

We have used dbm (Hdbm is dibenzoylmethane) as a co-ligand, in order to exclude solvent molecules from the coordination sphere of the metal ion, which is essential for optimization of the photophysical properties of lanthanide(III) complexes, and have recently structurally characterized two types of mixed-ligand (Tp^2py/dbm) complex with lanthanide(III) ions. In eight-coordinate [Ln(Tp^2py)(dbm)₂] (Ln is Eu or Tb), one of the three bidentate arms of Tp^2py is pendant, such that this ligand is only tetradentate and the metal centre has an N₄O₄ coordination sphere (Ward et al., 1999; Davies et al., 2004). In contrast, [Nd(Tp^2py)₂][Nd(dbm)₄] contains 12-coordinate [Nd(Tp^2py)₂]⁺ cations and eight-coordinate [Nd(dbm)₄]⁻ anions, the former with an icosahedral N₁₂ coordination and the latter with unusual O₈ cubic geometry (Davies et al., 2004). In this paper, we report a new structural type in this series, the title compound, (I), [Pr(Tp^2py)(dbm)₂], which is ten-coordinate, with the Pr^III ion in an N₆O₄ environment with all three chelating arms of Tp^2py attached to the metal centre.

Complex (I) (Fig. 1) was prepared by reaction of praseodymium(III) chloride hydrate with KTp^2py and Hdbm (1:1:2 molar ratio) in aqueous methanol with a few drops of triethylamine added. By comparison with the analogous structures of Eu^III and Tb^III, the original concept of the ligand design is achieved in this case, with all three arms of the Tp^2py molecule chelating to the Pr^III ion. The larger ionic radius of Pr^III allows the two dbm units to coordinate without displacing one of the arms of the scorpionate, in contrast with the behaviour shown by the smaller ions Eu^III and Tb^III. This places the metal ion in a ten-coordinate N₆O₄ coordination environment, with all five chelating units (three pyrazolyl-pyridine units and two dbm ligands) being approximately parallel to one another.

Many ten-donor coordination spheres exist among Pr^III complexes, although only two previous examples of N₆O₄ environments have been reported to date (Jones et al., 1997; Tamboura et al., 2004). The Pr—N and Pr—O bond lengths are unremarkable, with averages of 2.652, 2.738, and 2.469 Å for the Pr—N_pz, Pr—N_py and Pr—O bonds, respectively, all of which are understandably longer than those of the Eu^III and Tb^III analogues.

The coordination geometry of (I) does not obviously match any of the `ideal' arrangments of ten-coordination (Kepert, 1987). The best way of looking at the coordination geometry is down the N122—Pr1 bond (Fig. 2). The other two pyrazole N atoms, N102 and N142, form a pentagon with pyridyl atom N131 and atoms O55 and O21 from each dbm unit. The average edge length and angle for this pentagon are 2.818 Å and 107.6°, respectively, using O55; if O55' is used instead, these figures become 2.871 Å and 106.9°, respectively. These five atoms display an average deviation from their mean plane of 0.095 Å (if O55 is used) or 0.180 Å (if O55' is used). The pentagon is capped with atom N122, while on the other side of the pentagon resides a distorted square described by atoms O25, N151, N111 and O51. This `square' has an average edge of 2.983 Å and an average angle of 89.5° at its corners, but is rather irregular, with the corner angles varying from 75.50 to 102.31°. The mean deviation from the plane of these four atoms is 0.135 Å.

Experimental top

KTp^2py was prepared according to the published method of Amoroso et al. (1994). KTp^2py (202 mg, 0.42 mmol) in MeOH (5 ml) was added to a solution of PrCl₃·6H₂O (148 mg, 0.42 mmol) in MeOH (5 ml) and allowed to stir for 5 min at room temperature. A solution of Hdbm (188 mg, 0.84 mmol) in MeOH (5 ml) with Et₃N (1 ml) was added and, after 5 min, addition of H₂O (20 ml) generated a lime-green precipitate. The product was isolated by filtration and slowly recrystallized by the layering of hexanes onto a concentrated solution of the product in dichloromethane. After 5 d, the green crystals were collected by filtration and washed with hexane and ether to give (I) in 67% yield. Spectroscopic analysis: IR: ν_(B—H) 2444 cm⁻¹. Analysis, found: C 62.2, H 4.0, N 12.0%; calculated for [Pr(C₂₄H₁₉N₉B)(C₁₅H₁₁O₄)₂]·H₂O No hydrate in other formulae?: C 61.8, H 4.1, N 12.0%. FAB-MS gave a strong peak at m/z 808, corresponding to the loss of one dbm unit to give the fragment {Pr(Tp^2py)(dbm)}⁺; a weaker signal at m/z 1029 suggested the presence of the {Pr(Tp^2py)(dbm)₂} unit, minus two H atoms. The crystals were suitable for single-crystal X-ray diffraction and were completely air-stable. A suitable crystal was coated in engine oil to clean it of subsidiary grains.

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. A view of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level and H atoms have been omitted for clarity.
	Fig. 2. The coordination geometry about the Pr^III ion in (I). Only the Which? component of the disorder is shown.

Bis(1,3-diphenyl-1,3-propanedionato-κ²O,O'){hydrotris[3-(2-pyridyl)pyrazol- 1-yl]borato}praseodymium(III) top

Crystal data top

[Pr(C₂₄H₁₉BN₉)(C₁₅H₁₁O₄)₂]	Z = 2
M_r = 1031.68	F(000) = 1048
Triclinic, P1	D_x = 1.476 Mg m⁻³
Hall symbol: -P1	Mo Kα radiation, λ = 0.71073 Å
a = 11.6308 (15) Å	Cell parameters from 4832 reflections
b = 11.9248 (16) Å	θ = 4.7–54.6°
c = 18.569 (2) Å	µ = 1.11 mm⁻¹
α = 96.558 (2)°	T = 150 K
β = 106.782 (2)°	Block, green
γ = 105.669 (2)°	0.34 × 0.25 × 0.18 mm
V = 2321.9 (5) Å³

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	8143 independent reflections
Radiation source: fine-focus sealed tube	7003 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
Detector resolution: 100 pixels mm^-1	θ_max = 25.0°, θ_min = 1.2°
ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −14→14
T_min = 0.705, T_max = 0.826	l = −22→22
22669 measured reflections

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.074	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0285P)² + 2.7047P] where P = (F_o² + 2F_c²)/3
8143 reflections	(Δ/σ)_max < 0.001
680 parameters	Δρ_max = 0.73 e Å⁻³
230 restraints	Δρ_min = −0.72 e Å⁻³

Crystal data top

[Pr(C₂₄H₁₉BN₉)(C₁₅H₁₁O₄)₂]	γ = 105.669 (2)°
M_r = 1031.68	V = 2321.9 (5) Å³
Triclinic, P1	Z = 2
a = 11.6308 (15) Å	Mo Kα radiation
b = 11.9248 (16) Å	µ = 1.11 mm⁻¹
c = 18.569 (2) Å	T = 150 K
α = 96.558 (2)°	0.34 × 0.25 × 0.18 mm
β = 106.782 (2)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	8143 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	7003 reflections with I > 2σ(I)
T_min = 0.705, T_max = 0.826	R_int = 0.032
22669 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	230 restraints
wR(F²) = 0.074	H-atom parameters constrained
S = 1.05	Δρ_max = 0.73 e Å⁻³
8143 reflections	Δρ_min = −0.72 e Å⁻³
680 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Pr1	−0.003830 (17)	0.130026 (17)	0.245282 (11)	0.02367 (7)
B1	0.2148 (5)	0.4280 (5)	0.2294 (3)	0.0548 (15)
H1	0.2645	0.5147	0.2249	0.066*
N101	0.2973 (3)	0.3481 (3)	0.25498 (18)	0.0515 (9)
N102	0.2392 (3)	0.2318 (3)	0.25452 (17)	0.0439 (8)
C103	0.3256 (4)	0.1768 (5)	0.2630 (2)	0.0580 (12)
C104	0.4439 (4)	0.2599 (6)	0.2708 (2)	0.0695 (12)
H104	0.5209	0.2458	0.2785	0.083*
C105	0.4208 (4)	0.3636 (6)	0.2647 (3)	0.0736 (14)
H105	0.4805	0.4349	0.2668	0.088*
N111	0.1559 (3)	−0.0054 (3)	0.23431 (17)	0.0399 (8)
C112	0.2831 (5)	0.0475 (6)	0.2541 (2)	0.0615 (11)
C113	0.3660 (5)	−0.0195 (6)	0.2592 (3)	0.0729 (11)
H113	0.4530	0.0177	0.2742	0.087*
C114	0.3162 (6)	−0.1406 (6)	0.2415 (3)	0.0773 (11)
H114	0.3702	−0.1862	0.2439	0.093*
C115	0.1875 (5)	−0.1972 (5)	0.2200 (3)	0.0701 (11)
H115	0.1530	−0.2797	0.2068	0.084*
C116	0.1123 (5)	−0.1243 (5)	0.2192 (2)	0.0601 (11)
H116	0.0257	−0.1607	0.2074	0.072*
N121	0.1488 (3)	0.4485 (3)	0.28738 (18)	0.0466 (9)
N122	0.0756 (3)	0.3555 (3)	0.30654 (17)	0.0356 (8)
C123	0.0213 (4)	0.4013 (3)	0.3519 (2)	0.0342 (9)
C124	0.0617 (5)	0.5260 (3)	0.3634 (2)	0.0520 (12)
H124	0.0394	0.5794	0.3929	0.062*
C125	0.1399 (5)	0.5508 (4)	0.3219 (3)	0.0586 (14)
H125	0.1816	0.6269	0.3177	0.070*
N131	−0.1018 (3)	0.2033 (2)	0.34729 (16)	0.0283 (7)
C132	−0.0718 (3)	0.3205 (3)	0.3761 (2)	0.0319 (8)
C133	−0.1314 (4)	0.3614 (4)	0.4241 (2)	0.0435 (10)
H133	−0.1082	0.4424	0.4444	0.052*
C134	−0.2241 (4)	0.2818 (4)	0.4410 (2)	0.0469 (11)
H134	−0.2646	0.3079	0.4728	0.056*
C135	−0.2566 (4)	0.1626 (4)	0.4103 (2)	0.0400 (10)
H135	−0.3207	0.1068	0.4198	0.048*
C136	−0.1919 (3)	0.1274 (3)	0.3651 (2)	0.0307 (8)
H136	−0.2122	0.0464	0.3459	0.037*
N141	0.1166 (3)	0.3611 (3)	0.14883 (18)	0.0446 (9)
N142	0.0488 (3)	0.2444 (3)	0.13829 (17)	0.0345 (7)
C143	−0.0178 (3)	0.2071 (3)	0.0635 (2)	0.0333 (9)
C144	0.0063 (4)	0.2998 (4)	0.0249 (2)	0.0453 (11)
H144	−0.0282	0.2975	−0.0273	0.054*
C145	0.0917 (4)	0.3948 (4)	0.0806 (2)	0.0526 (12)
H145	0.1269	0.4703	0.0727	0.063*
N151	−0.0974 (3)	0.0173 (3)	0.09259 (16)	0.0308 (7)
C152	−0.0963 (3)	0.0808 (3)	0.03713 (19)	0.0289 (8)
C153	−0.1649 (3)	0.0295 (4)	−0.0397 (2)	0.0374 (9)
H153	−0.1642	0.0752	−0.0770	0.045*
C154	−0.2338 (4)	−0.0890 (4)	−0.0601 (2)	0.0418 (10)
H154	−0.2795	−0.1246	−0.1114	0.050*
C155	−0.2350 (4)	−0.1552 (4)	−0.0039 (2)	0.0434 (10)
H155	−0.2803	−0.2361	−0.0165	0.052*
C156	−0.1670 (4)	−0.0980 (3)	0.0714 (2)	0.0380 (9)
H156	−0.1697	−0.1418	0.1095	0.046*
C11	−0.2929 (3)	0.3395 (3)	0.13755 (19)	0.0304 (8)
C12	−0.4145 (4)	0.3483 (3)	0.1162 (2)	0.0364 (9)
H12	−0.4818	0.2855	0.1170	0.044*
C13	−0.4363 (4)	0.4495 (4)	0.0940 (2)	0.0484 (11)
H13	−0.5180	0.4544	0.0799	0.058*
C14	−0.3376 (5)	0.5432 (4)	0.0925 (2)	0.0509 (12)
H14	−0.3528	0.6109	0.0772	0.061*
C15	−0.2171 (4)	0.5363 (3)	0.1135 (2)	0.0450 (10)
H15	−0.1506	0.5992	0.1122	0.054*
C16	−0.1941 (4)	0.4355 (3)	0.1368 (2)	0.0360 (9)
H16	−0.1118	0.4322	0.1520	0.043*
O21	−0.1480 (2)	0.2427 (2)	0.18909 (13)	0.0298 (6)
C22	−0.2633 (3)	0.2304 (3)	0.15983 (18)	0.0262 (8)
C23	−0.3604 (3)	0.1223 (3)	0.1448 (2)	0.0305 (8)
H23	−0.4437	0.1197	0.1217	0.037*
C24	−0.3370 (3)	0.0185 (3)	0.16304 (18)	0.0229 (7)
O25	−0.2295 (2)	0.01301 (19)	0.19963 (13)	0.0265 (5)
C31	−0.4428 (3)	−0.0978 (3)	0.13840 (19)	0.0253 (8)
C32	−0.5539 (3)	−0.1204 (3)	0.0768 (2)	0.0342 (9)
H32	−0.5669	−0.0604	0.0507	0.041*
C33	−0.6450 (4)	−0.2314 (4)	0.0543 (3)	0.0488 (12)
H33	−0.7189	−0.2461	0.0130	0.059*
C34	−0.6261 (4)	−0.3199 (4)	0.0927 (3)	0.0590 (14)
H34	−0.6870	−0.3949	0.0770	0.071*
C35	−0.5179 (4)	−0.2987 (3)	0.1545 (3)	0.0492 (11)
H35	−0.5067	−0.3587	0.1809	0.059*
C36	−0.4256 (3)	−0.1881 (3)	0.1772 (2)	0.0340 (9)
H36	−0.3521	−0.1742	0.2186	0.041*
C41	−0.0853 (3)	−0.2001 (3)	0.3697 (2)	0.0322 (8)
C42	−0.0834 (4)	−0.2241 (4)	0.4411 (2)	0.0440 (10)
H42	−0.0266	−0.1698	0.4854	0.053*
C43	−0.1654 (4)	−0.3283 (4)	0.4473 (2)	0.0486 (11)
H43	−0.1649	−0.3422	0.4956	0.058*
C44	−0.2473 (4)	−0.4110 (4)	0.3828 (2)	0.0426 (10)
H44	−0.3027	−0.4804	0.3872	0.051*
C45	−0.2469 (4)	−0.3905 (3)	0.3110 (2)	0.0415 (10)
H45	−0.2996	−0.4477	0.2671	0.050*
C46	−0.1681 (3)	−0.2850 (3)	0.3047 (2)	0.0336 (9)
H46	−0.1705	−0.2706	0.2562	0.040*
O51	−0.0531 (2)	−0.0478 (2)	0.30078 (13)	0.0276 (5)
C52	−0.0054 (3)	−0.0838 (3)	0.36064 (18)	0.0295 (7)
C53	0.1054 (5)	−0.0086 (6)	0.4198 (4)	0.0266 (14)	0.514 (3)
H53	0.1333	−0.0402	0.4626	0.032*	0.514 (3)
C54	0.1788 (5)	0.1078 (6)	0.4223 (4)	0.0256 (16)	0.514 (3)
O55	0.151 (3)	0.1707 (15)	0.3743 (9)	0.023 (3)	0.514 (3)
C61	0.3019 (3)	0.1745 (4)	0.4867 (2)	0.0320 (10)	0.514 (3)
C62	0.3263 (4)	0.1466 (4)	0.5592 (2)	0.0334 (12)	0.514 (3)
H62	0.2663	0.0816	0.5683	0.040*	0.514 (3)
C63	0.4374 (4)	0.2128 (4)	0.61836 (19)	0.0399 (13)	0.514 (3)
H63	0.4542	0.1935	0.6684	0.048*	0.514 (3)
C64	0.5242 (3)	0.3069 (4)	0.6052 (2)	0.0432 (12)	0.514 (3)
H64	0.6009	0.3526	0.6461	0.052*	0.514 (3)
C65	0.4998 (4)	0.3348 (4)	0.5328 (3)	0.0418 (11)	0.514 (3)
H65	0.5597	0.3999	0.5236	0.050*	0.514 (3)
C66	0.3887 (4)	0.2687 (4)	0.4736 (2)	0.0370 (11)	0.514 (3)
H66	0.3719	0.2879	0.4235	0.044*	0.514 (3)
C53'	0.1205 (5)	−0.0435 (7)	0.4088 (5)	0.0275 (15)	0.486 (3)
H53'	0.1534	−0.0910	0.4399	0.033*	0.486 (3)
C54'	0.1961 (5)	0.0697 (7)	0.4093 (5)	0.0277 (18)	0.486 (3)
O55'	0.155 (3)	0.1394 (16)	0.3710 (10)	0.023 (3)	0.486 (3)
C61'	0.3337 (3)	0.1051 (4)	0.4571 (3)	0.0313 (11)	0.486 (3)
C62'	0.3943 (4)	0.0206 (3)	0.4731 (3)	0.0305 (12)	0.486 (3)
H62'	0.3488	−0.0624	0.4522	0.037*	0.486 (3)
C63'	0.5209 (4)	0.0563 (4)	0.5193 (3)	0.0350 (13)	0.486 (3)
H63'	0.5627	−0.0021	0.5303	0.042*	0.486 (3)
C64'	0.5868 (3)	0.1765 (4)	0.5495 (3)	0.0408 (13)	0.486 (3)
H64'	0.6742	0.2012	0.5814	0.049*	0.486 (3)
C65'	0.5262 (4)	0.2611 (3)	0.5335 (3)	0.0422 (11)	0.486 (3)
H65'	0.5717	0.3441	0.5543	0.051*	0.486 (3)
C66'	0.3997 (4)	0.2253 (4)	0.4873 (3)	0.0381 (11)	0.486 (3)
H66'	0.3578	0.2837	0.4762	0.046*	0.486 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pr1	0.01723 (10)	0.02729 (11)	0.02189 (11)	0.00235 (7)	0.00419 (7)	0.00511 (7)
B1	0.043 (3)	0.051 (3)	0.039 (3)	−0.026 (2)	0.004 (2)	0.014 (2)
N101	0.0239 (16)	0.077 (2)	0.0308 (16)	−0.0162 (15)	0.0068 (13)	0.0091 (16)
N102	0.0204 (15)	0.072 (2)	0.0273 (15)	−0.0019 (14)	0.0058 (12)	0.0114 (15)
C103	0.0197 (17)	0.128 (4)	0.0240 (18)	0.017 (2)	0.0079 (15)	0.020 (2)
C104	0.0200 (16)	0.143 (3)	0.0313 (18)	0.006 (2)	0.0061 (14)	0.016 (2)
C105	0.025 (2)	0.138 (4)	0.035 (2)	−0.006 (2)	0.0050 (17)	0.019 (3)
N111	0.041 (2)	0.066 (2)	0.0292 (18)	0.0349 (18)	0.0164 (15)	0.0205 (17)
C112	0.056 (2)	0.134 (3)	0.032 (2)	0.066 (2)	0.0275 (18)	0.040 (2)
C113	0.070 (2)	0.139 (3)	0.047 (2)	0.072 (2)	0.0330 (18)	0.040 (2)
C114	0.089 (2)	0.133 (3)	0.056 (2)	0.084 (2)	0.0384 (19)	0.043 (2)
C115	0.096 (2)	0.111 (3)	0.053 (2)	0.077 (2)	0.046 (2)	0.045 (2)
C116	0.090 (3)	0.098 (3)	0.042 (2)	0.071 (2)	0.045 (2)	0.045 (2)
N121	0.049 (2)	0.035 (2)	0.0305 (18)	−0.0170 (16)	0.0043 (16)	0.0083 (15)
N122	0.0348 (18)	0.0271 (17)	0.0315 (17)	−0.0067 (14)	0.0056 (14)	0.0089 (14)
C123	0.041 (2)	0.027 (2)	0.0257 (19)	0.0062 (17)	0.0022 (17)	0.0052 (16)
C124	0.078 (3)	0.023 (2)	0.039 (2)	0.002 (2)	0.009 (2)	0.0057 (18)
C125	0.078 (3)	0.023 (2)	0.041 (3)	−0.012 (2)	−0.003 (2)	0.0046 (19)
N131	0.0326 (17)	0.0252 (16)	0.0268 (16)	0.0096 (13)	0.0087 (13)	0.0070 (13)
C132	0.036 (2)	0.030 (2)	0.0261 (19)	0.0127 (17)	0.0008 (16)	0.0090 (16)
C133	0.051 (3)	0.040 (2)	0.036 (2)	0.024 (2)	0.005 (2)	−0.0028 (18)
C134	0.046 (3)	0.065 (3)	0.037 (2)	0.026 (2)	0.019 (2)	0.006 (2)
C135	0.035 (2)	0.056 (3)	0.032 (2)	0.0142 (19)	0.0125 (17)	0.0127 (19)
C136	0.034 (2)	0.032 (2)	0.030 (2)	0.0116 (16)	0.0138 (16)	0.0114 (16)
N141	0.0343 (18)	0.050 (2)	0.0327 (18)	−0.0135 (16)	0.0097 (15)	0.0134 (16)
N142	0.0218 (16)	0.0427 (19)	0.0282 (17)	−0.0057 (14)	0.0062 (13)	0.0098 (14)
C143	0.0192 (18)	0.051 (2)	0.027 (2)	0.0054 (17)	0.0081 (15)	0.0092 (17)
C144	0.036 (2)	0.062 (3)	0.027 (2)	−0.002 (2)	0.0090 (18)	0.018 (2)
C145	0.041 (2)	0.063 (3)	0.041 (3)	−0.009 (2)	0.013 (2)	0.028 (2)
N151	0.0270 (16)	0.0388 (18)	0.0240 (16)	0.0117 (14)	0.0043 (13)	0.0053 (14)
C152	0.0210 (18)	0.043 (2)	0.0235 (18)	0.0097 (16)	0.0081 (15)	0.0075 (16)
C153	0.033 (2)	0.054 (3)	0.025 (2)	0.0111 (19)	0.0105 (17)	0.0129 (18)
C154	0.044 (2)	0.052 (3)	0.0207 (19)	0.011 (2)	0.0041 (17)	0.0005 (18)
C155	0.049 (3)	0.037 (2)	0.035 (2)	0.0108 (19)	0.0059 (19)	−0.0013 (18)
C156	0.046 (2)	0.039 (2)	0.029 (2)	0.0180 (19)	0.0085 (18)	0.0074 (17)
C11	0.041 (2)	0.0281 (19)	0.0248 (19)	0.0121 (17)	0.0126 (16)	0.0083 (15)
C12	0.041 (2)	0.033 (2)	0.040 (2)	0.0171 (18)	0.0146 (18)	0.0113 (17)
C13	0.058 (3)	0.047 (3)	0.055 (3)	0.032 (2)	0.022 (2)	0.021 (2)
C14	0.085 (4)	0.039 (3)	0.047 (3)	0.037 (2)	0.028 (2)	0.020 (2)
C15	0.064 (3)	0.030 (2)	0.046 (3)	0.012 (2)	0.027 (2)	0.0137 (19)
C16	0.043 (2)	0.031 (2)	0.036 (2)	0.0111 (18)	0.0165 (18)	0.0091 (17)
O21	0.0233 (13)	0.0276 (13)	0.0351 (14)	0.0036 (10)	0.0067 (11)	0.0117 (11)
C22	0.031 (2)	0.0297 (19)	0.0204 (17)	0.0109 (16)	0.0110 (15)	0.0077 (15)
C23	0.0183 (17)	0.034 (2)	0.034 (2)	0.0069 (15)	0.0025 (15)	0.0084 (16)
C24	0.0191 (17)	0.0275 (18)	0.0207 (17)	0.0052 (14)	0.0076 (14)	0.0031 (14)
O25	0.0205 (12)	0.0272 (13)	0.0288 (13)	0.0062 (10)	0.0038 (10)	0.0090 (10)
C31	0.0218 (18)	0.0254 (18)	0.0282 (19)	0.0044 (14)	0.0124 (15)	0.0011 (15)
C32	0.0221 (19)	0.040 (2)	0.033 (2)	0.0021 (16)	0.0074 (16)	−0.0019 (17)
C33	0.024 (2)	0.050 (3)	0.052 (3)	−0.0031 (19)	0.0078 (19)	−0.018 (2)
C34	0.034 (2)	0.033 (2)	0.098 (4)	−0.0083 (19)	0.032 (3)	−0.014 (3)
C35	0.047 (3)	0.025 (2)	0.086 (3)	0.0094 (19)	0.038 (3)	0.014 (2)
C36	0.031 (2)	0.029 (2)	0.046 (2)	0.0090 (16)	0.0197 (18)	0.0068 (17)
C41	0.0243 (19)	0.045 (2)	0.032 (2)	0.0155 (17)	0.0080 (16)	0.0195 (18)
C42	0.028 (2)	0.067 (3)	0.029 (2)	0.004 (2)	0.0030 (17)	0.020 (2)
C43	0.035 (2)	0.073 (3)	0.037 (2)	0.008 (2)	0.0113 (19)	0.033 (2)
C44	0.035 (2)	0.044 (2)	0.051 (3)	0.0112 (19)	0.013 (2)	0.025 (2)
C45	0.046 (2)	0.032 (2)	0.043 (2)	0.0098 (19)	0.0112 (19)	0.0087 (18)
C46	0.040 (2)	0.036 (2)	0.031 (2)	0.0182 (18)	0.0136 (17)	0.0132 (17)
O51	0.0270 (13)	0.0293 (13)	0.0238 (13)	0.0099 (10)	0.0034 (10)	0.0064 (10)
C52	0.0228 (14)	0.045 (2)	0.0262 (16)	0.0154 (14)	0.0092 (12)	0.0142 (15)
C53	0.021 (2)	0.043 (3)	0.024 (2)	0.018 (2)	0.0078 (19)	0.016 (2)
C54	0.020 (3)	0.044 (3)	0.021 (3)	0.015 (2)	0.011 (2)	0.011 (3)
O55	0.029 (4)	0.012 (8)	0.022 (4)	−0.001 (6)	0.007 (3)	−0.003 (4)
C61	0.0239 (18)	0.041 (2)	0.0281 (18)	0.0114 (16)	0.0042 (16)	0.0041 (17)
C62	0.027 (2)	0.041 (2)	0.028 (2)	0.0138 (19)	0.0008 (19)	0.0035 (19)
C63	0.032 (2)	0.046 (3)	0.032 (2)	0.014 (2)	−0.0028 (19)	0.001 (2)
C64	0.030 (2)	0.050 (2)	0.037 (2)	0.0093 (18)	−0.0006 (18)	−0.0030 (19)
C65	0.0284 (19)	0.048 (2)	0.0375 (18)	0.0061 (17)	0.0041 (17)	−0.0007 (18)
C66	0.0264 (18)	0.045 (2)	0.0319 (18)	0.0068 (17)	0.0050 (16)	0.0024 (18)
C53'	0.020 (2)	0.044 (3)	0.026 (3)	0.017 (2)	0.009 (2)	0.016 (2)
C54'	0.019 (3)	0.045 (4)	0.022 (3)	0.013 (2)	0.007 (2)	0.011 (3)
O55'	0.025 (4)	0.011 (8)	0.026 (4)	0.002 (6)	0.006 (3)	−0.003 (5)
C61'	0.0231 (19)	0.042 (2)	0.027 (2)	0.0097 (17)	0.0067 (17)	0.0061 (19)
C62'	0.022 (2)	0.043 (2)	0.027 (2)	0.0094 (19)	0.0099 (19)	0.009 (2)
C63'	0.023 (2)	0.050 (2)	0.031 (2)	0.010 (2)	0.010 (2)	0.007 (2)
C64'	0.026 (2)	0.052 (2)	0.035 (2)	0.0081 (19)	0.004 (2)	0.001 (2)
C65'	0.0281 (17)	0.049 (2)	0.0374 (18)	0.0073 (16)	0.0025 (16)	−0.0008 (18)
C66'	0.0269 (17)	0.045 (2)	0.0340 (18)	0.0086 (17)	0.0033 (16)	0.0012 (17)

Geometric parameters (Å, º) top

Pr1—O55	2.448 (17)	C12—C13	1.382 (5)
Pr1—O25	2.454 (2)	C12—H12	0.9300
Pr1—O51	2.464 (2)	C13—C14	1.377 (6)
Pr1—O55'	2.492 (17)	C13—H13	0.9300
Pr1—O21	2.496 (2)	C14—C15	1.370 (6)
Pr1—N122	2.595 (3)	C14—H14	0.9300
Pr1—N142	2.656 (3)	C15—C16	1.388 (5)
Pr1—N131	2.656 (3)	C15—H15	0.9300
Pr1—N102	2.704 (3)	C16—H16	0.9300
Pr1—N151	2.754 (3)	O21—C22	1.254 (4)
Pr1—N111	2.804 (3)	C22—C23	1.401 (5)
B1—N121	1.526 (7)	C23—C24	1.395 (5)
B1—N101	1.545 (7)	C23—H23	0.9300
B1—N141	1.557 (5)	C24—O25	1.262 (4)
B1—H1	1.0653	C24—C31	1.501 (4)
N101—C105	1.353 (6)	C31—C36	1.389 (5)
N101—N102	1.367 (5)	C31—C32	1.393 (5)
N102—C103	1.324 (6)	C32—C33	1.382 (5)
C103—C104	1.418 (6)	C32—H32	0.9300
C103—C112	1.460 (7)	C33—C34	1.371 (7)
C104—C105	1.344 (8)	C33—H33	0.9300
C104—H104	0.9300	C34—C35	1.375 (6)
C105—H105	0.9300	C34—H34	0.9300
N111—C116	1.337 (6)	C35—C36	1.384 (5)
N111—C112	1.360 (6)	C35—H35	0.9300
C112—C113	1.399 (6)	C36—H36	0.9300
C113—C114	1.364 (8)	C41—C42	1.384 (5)
C113—H113	0.9300	C41—C46	1.389 (5)
C114—C115	1.379 (8)	C41—C52	1.504 (5)
C114—H114	0.9300	C42—C43	1.387 (6)
C115—C116	1.388 (6)	C42—H42	0.9300
C115—H115	0.9300	C43—C44	1.370 (6)
C116—H116	0.9300	C43—H43	0.9300
N121—N122	1.354 (4)	C44—C45	1.383 (5)
N121—C125	1.356 (6)	C44—H44	0.9300
N122—C123	1.340 (5)	C45—C46	1.382 (5)
C123—C124	1.403 (5)	C45—H45	0.9300
C123—C132	1.455 (5)	C46—H46	0.9300
C124—C125	1.348 (7)	O51—C52	1.269 (4)
C124—H124	0.9300	C52—C53'	1.392 (5)
C125—H125	0.9300	C52—C53	1.416 (5)
N131—C136	1.336 (4)	C53—C54	1.407 (5)
N131—C132	1.348 (4)	C53—H53	0.9300
C132—C133	1.398 (5)	C54—O55	1.256 (5)
C133—C134	1.369 (6)	C54—C61	1.515 (5)
C133—H133	0.9300	C61—C62	1.3900
C134—C135	1.375 (6)	C61—C66	1.3900
C134—H134	0.9300	C62—C63	1.3900
C135—C136	1.378 (5)	C62—H62	0.9601
C135—H135	0.9300	C63—C64	1.3900
C136—H136	0.9300	C63—H63	0.9600
N141—C145	1.348 (5)	C64—C65	1.3900
N141—N142	1.361 (4)	C64—H64	0.9601
N142—C143	1.334 (4)	C65—C66	1.3900
C143—C144	1.394 (5)	C65—H65	0.9600
C143—C152	1.474 (5)	C66—H66	0.9600
C144—C145	1.369 (6)	C53'—C54'	1.396 (5)
C144—H144	0.9300	C53'—H53'	0.9300
C145—H145	0.9300	C54'—O55'	1.256 (5)
N151—C156	1.339 (5)	C54'—C61'	1.503 (4)
N151—C152	1.347 (4)	C61'—C62'	1.3900
C152—C153	1.387 (5)	C61'—C66'	1.3900
C153—C154	1.368 (5)	C62'—C63'	1.3900
C153—H153	0.9300	C62'—H62'	0.9601
C154—C155	1.379 (6)	C63'—C64'	1.3900
C154—H154	0.9300	C63'—H63'	0.9600
C155—C156	1.378 (5)	C64'—C65'	1.3900
C155—H155	0.9300	C64'—H64'	0.9600
C156—H156	0.9300	C65'—C66'	1.3900
C11—C12	1.391 (5)	C65'—H65'	0.9600
C11—C16	1.391 (5)	C66'—H66'	0.9601
C11—C22	1.504 (5)

O55—Pr1—O25	128.4 (6)	C156—N151—C152	117.8 (3)
O55—Pr1—O51	71.7 (5)	C156—N151—Pr1	120.2 (2)
O25—Pr1—O51	65.89 (7)	C152—N151—Pr1	120.6 (2)
O55—Pr1—O55'	9.0 (6)	N151—C152—C153	121.6 (3)
O25—Pr1—O55'	126.1 (6)	N151—C152—C143	115.7 (3)
O51—Pr1—O55'	65.2 (5)	C153—C152—C143	122.7 (3)
O55—Pr1—O21	129.8 (4)	C154—C153—C152	119.5 (4)
O25—Pr1—O21	65.98 (7)	C154—C153—H153	120.3
O51—Pr1—O21	128.16 (7)	C152—C153—H153	120.3
O55'—Pr1—O21	138.5 (4)	C153—C154—C155	119.5 (3)
O55—Pr1—N122	69.4 (3)	C153—C154—H154	120.2
O25—Pr1—N122	121.82 (9)	C155—C154—H154	120.2
O51—Pr1—N122	131.58 (8)	C156—C155—C154	118.0 (4)
O55'—Pr1—N122	78.1 (4)	C156—C155—H155	121.0
O21—Pr1—N122	65.02 (9)	C154—C155—H155	121.0
O55—Pr1—N142	121.4 (6)	N151—C156—C155	123.6 (4)
O25—Pr1—N142	109.44 (8)	N151—C156—H156	118.2
O51—Pr1—N142	154.01 (9)	C155—C156—H156	118.2
O55'—Pr1—N142	124.5 (7)	C12—C11—C16	118.3 (3)
O21—Pr1—N142	63.44 (9)	C12—C11—C22	123.3 (3)
N122—Pr1—N142	73.55 (9)	C16—C11—C22	118.4 (3)
O55—Pr1—N131	71.2 (6)	C13—C12—C11	120.6 (4)
O25—Pr1—N131	73.08 (8)	C13—C12—H12	119.7
O51—Pr1—N131	79.07 (8)	C11—C12—H12	119.7
O55'—Pr1—N131	76.8 (6)	C14—C13—C12	120.4 (4)
O21—Pr1—N131	69.66 (8)	C14—C13—H13	119.8
N122—Pr1—N131	61.99 (9)	C12—C13—H13	119.8
N142—Pr1—N131	125.31 (9)	C15—C14—C13	119.8 (4)
O55—Pr1—N102	65.5 (6)	C15—C14—H14	120.1
O25—Pr1—N102	163.61 (8)	C13—C14—H14	120.1
O51—Pr1—N102	117.95 (9)	C14—C15—C16	120.2 (4)
O55'—Pr1—N102	66.0 (7)	C14—C15—H15	119.9
O21—Pr1—N102	113.69 (9)	C16—C15—H15	119.9
N122—Pr1—N102	68.87 (11)	C15—C16—C11	120.6 (4)
N142—Pr1—N102	59.51 (9)	C15—C16—H16	119.7
N131—Pr1—N102	122.86 (9)	C11—C16—H16	119.7
O55—Pr1—N151	150.3 (5)	C22—O21—Pr1	141.2 (2)
O25—Pr1—N151	65.76 (8)	O21—C22—C23	123.6 (3)
O51—Pr1—N151	98.08 (8)	O21—C22—C11	115.6 (3)
O55'—Pr1—N151	142.4 (4)	C23—C22—C11	120.8 (3)
O21—Pr1—N151	78.77 (8)	C24—C23—C22	122.7 (3)
N122—Pr1—N151	129.64 (9)	C24—C23—H23	118.7
N142—Pr1—N151	58.98 (9)	C22—C23—H23	118.7
N131—Pr1—N151	135.59 (9)	O25—C24—C23	124.5 (3)
N102—Pr1—N151	97.90 (9)	O25—C24—C31	115.0 (3)
O55—Pr1—N111	74.0 (5)	C23—C24—C31	120.5 (3)
O25—Pr1—N111	113.86 (9)	C24—O25—Pr1	141.4 (2)
O51—Pr1—N111	68.63 (9)	C36—C31—C32	119.0 (3)
O55'—Pr1—N111	66.3 (5)	C36—C31—C24	117.9 (3)
O21—Pr1—N111	151.93 (8)	C32—C31—C24	123.1 (3)
N122—Pr1—N111	124.18 (10)	C33—C32—C31	120.3 (4)
N142—Pr1—N111	92.39 (10)	C33—C32—H32	119.8
N131—Pr1—N111	138.32 (9)	C31—C32—H32	119.8
N102—Pr1—N111	58.02 (11)	C34—C33—C32	119.9 (4)
N151—Pr1—N111	76.31 (9)	C34—C33—H33	120.0
N121—B1—N101	110.0 (4)	C32—C33—H33	120.0
N121—B1—N141	111.1 (4)	C33—C34—C35	120.5 (4)
N101—B1—N141	106.5 (4)	C33—C34—H34	119.7
N121—B1—H1	105.2	C35—C34—H34	119.7
N101—B1—H1	115.6	C34—C35—C36	120.1 (4)
N141—B1—H1	108.5	C34—C35—H35	120.0
C105—N101—N102	108.5 (4)	C36—C35—H35	120.0
C105—N101—B1	131.1 (4)	C35—C36—C31	120.1 (4)
N102—N101—B1	119.0 (3)	C35—C36—H36	120.0
C103—N102—N101	107.5 (3)	C31—C36—H36	120.0
C103—N102—Pr1	125.1 (3)	C42—C41—C46	118.2 (4)
N101—N102—Pr1	127.4 (3)	C42—C41—C52	122.1 (3)
N102—C103—C104	109.2 (5)	C46—C41—C52	119.6 (3)
N102—C103—C112	117.9 (4)	C41—C42—C43	120.6 (4)
C104—C103—C112	132.4 (5)	C41—C42—H42	119.7
C105—C104—C103	105.2 (5)	C43—C42—H42	119.7
C105—C104—H104	127.4	C44—C43—C42	120.6 (4)
C103—C104—H104	127.4	C44—C43—H43	119.7
C104—C105—N101	109.5 (5)	C42—C43—H43	119.7
C104—C105—H105	125.3	C43—C44—C45	119.5 (4)
N101—C105—H105	125.3	C43—C44—H44	120.3
C116—N111—C112	117.5 (4)	C45—C44—H44	120.3
C116—N111—Pr1	121.0 (3)	C46—C45—C44	119.9 (4)
C112—N111—Pr1	120.9 (3)	C46—C45—H45	120.0
N111—C112—C113	121.6 (6)	C44—C45—H45	120.0
N111—C112—C103	115.8 (4)	C45—C46—C41	121.1 (4)
C113—C112—C103	122.4 (5)	C45—C46—H46	119.5
C114—C113—C112	118.4 (6)	C41—C46—H46	119.5
C114—C113—H113	120.8	C52—O51—Pr1	138.1 (2)
C112—C113—H113	120.8	O51—C52—C53'	127.2 (5)
C113—C114—C115	121.5 (5)	O51—C52—C53	120.7 (4)
C113—C114—H114	119.2	O51—C52—C41	115.5 (3)
C115—C114—H114	119.2	C53'—C52—C41	115.6 (4)
C114—C115—C116	116.5 (6)	C53—C52—C41	123.0 (4)
C114—C115—H115	121.8	C54—C53—C52	128.5 (6)
C116—C115—H115	121.8	C54—C53—H53	115.8
N111—C116—C115	124.4 (5)	C52—C53—H53	115.8
N111—C116—H116	117.8	O55—C54—C53	125.8 (12)
C115—C116—H116	117.8	O55—C54—C61	111.4 (12)
N122—N121—C125	108.6 (4)	C53—C54—C61	122.8 (5)
N122—N121—B1	120.9 (3)	C54—O55—Pr1	134.2 (14)
C125—N121—B1	130.2 (4)	C62—C61—C66	120.0
C123—N122—N121	106.9 (3)	C62—C61—C54	121.1 (4)
C123—N122—Pr1	121.5 (2)	C66—C61—C54	118.8 (4)
N121—N122—Pr1	129.8 (2)	C54—C61—H66'	112.5
N122—C123—C124	110.1 (4)	C61—C62—C63	120.0
N122—C123—C132	118.9 (3)	C61—C62—H62	120.0
C124—C123—C132	130.9 (4)	C63—C62—H62	120.0
C125—C124—C123	104.5 (4)	C62—C63—C64	120.0
C125—C124—H124	127.8	C62—C63—H63	120.0
C123—C124—H124	127.8	C64—C63—H63	120.0
C124—C125—N121	110.0 (4)	C65—C64—C63	120.0
C124—C125—H125	125.0	C65—C64—H64	120.0
N121—C125—H125	125.0	C63—C64—H64	120.0
C136—N131—C132	117.9 (3)	C64—C65—C66	120.0
C136—N131—Pr1	121.3 (2)	C64—C65—H65	120.0
C132—N131—Pr1	120.4 (2)	C66—C65—H65	120.0
N131—C132—C133	121.2 (4)	C65—C66—C61	120.0
N131—C132—C123	116.5 (3)	C65—C66—H66	120.0
C133—C132—C123	122.2 (3)	C61—C66—H66	120.0
C134—C133—C132	119.7 (4)	C65—C66—H66'	107.0
C134—C133—H133	120.2	C52—C53'—C54'	118.5 (6)
C132—C133—H133	120.2	C52—C53'—H53'	120.7
C133—C134—C135	119.0 (4)	C54'—C53'—H53'	120.7
C133—C134—H134	120.5	O55'—C54'—C53'	123.3 (14)
C135—C134—H134	120.5	O55'—C54'—C61'	120.2 (14)
C134—C135—C136	118.6 (4)	C53'—C54'—C61'	116.5 (5)
C134—C135—H135	120.7	C54'—O55'—Pr1	139.0 (14)
C136—C135—H135	120.7	C62'—C61'—C66'	120.0
N131—C136—C135	123.6 (4)	C62'—C61'—C54'	121.5 (4)
N131—C136—H136	118.2	C66'—C61'—C54'	118.4 (4)
C135—C136—H136	118.2	C61'—C62'—C63'	120.0
C145—N141—N142	109.2 (3)	C61'—C62'—H62'	120.0
C145—N141—B1	131.0 (3)	C63'—C62'—H62'	120.0
N142—N141—B1	119.5 (3)	C62'—C63'—C64'	120.0
C143—N142—N141	106.8 (3)	C62'—C63'—H63'	120.0
C143—N142—Pr1	123.5 (2)	C64'—C63'—H63'	120.0
N141—N142—Pr1	127.0 (2)	C65'—C64'—C63'	120.0
N142—C143—C144	110.2 (3)	C65'—C64'—H64'	120.0
N142—C143—C152	117.0 (3)	C63'—C64'—H64'	120.0
C144—C143—C152	132.7 (3)	C64'—C65'—C66'	120.0
C145—C144—C143	104.9 (3)	C64'—C65'—H65'	120.0
C145—C144—H144	127.5	C66'—C65'—H65'	120.0
C143—C144—H144	127.5	C65'—C66'—C61'	120.0
N141—C145—C144	108.8 (4)	C65'—C66'—H66'	120.0
N141—C145—H145	125.6	C61'—C66'—H66'	120.0
C144—C145—H145	125.6

N121—B1—N101—C105	−127.5 (4)	C152—C143—C144—C145	−177.3 (4)
N141—B1—N101—C105	112.0 (5)	N142—N141—C145—C144	0.4 (5)
N121—B1—N101—N102	67.6 (4)	B1—N141—C145—C144	173.4 (5)
N141—B1—N101—N102	−52.9 (5)	C143—C144—C145—N141	−0.4 (5)
C105—N101—N102—C103	−0.6 (4)	O55—Pr1—N151—C156	77.7 (11)
B1—N101—N102—C103	167.4 (4)	O25—Pr1—N151—C156	−48.1 (3)
C105—N101—N102—Pr1	176.6 (3)	O51—Pr1—N151—C156	10.8 (3)
B1—N101—N102—Pr1	−15.4 (5)	O55'—Pr1—N151—C156	70.1 (11)
O55—Pr1—N102—C103	73.7 (4)	O21—Pr1—N151—C156	−116.7 (3)
O25—Pr1—N102—C103	−76.5 (5)	N122—Pr1—N151—C156	−160.3 (2)
O51—Pr1—N102—C103	23.0 (3)	N142—Pr1—N151—C156	177.7 (3)
O55'—Pr1—N102—C103	63.9 (5)	N131—Pr1—N151—C156	−71.8 (3)
O21—Pr1—N102—C103	−161.7 (3)	N102—Pr1—N151—C156	130.6 (3)
N122—Pr1—N102—C103	149.9 (3)	N111—Pr1—N151—C156	76.4 (3)
N142—Pr1—N102—C103	−127.3 (3)	O55—Pr1—N151—C152	−115.8 (11)
N131—Pr1—N102—C103	118.0 (3)	O25—Pr1—N151—C152	118.4 (3)
N151—Pr1—N102—C103	−80.6 (3)	O51—Pr1—N151—C152	177.3 (2)
N111—Pr1—N102—C103	−12.2 (3)	O55'—Pr1—N151—C152	−123.3 (10)
O55—Pr1—N102—N101	−103.1 (4)	O21—Pr1—N151—C152	49.9 (2)
O25—Pr1—N102—N101	106.7 (4)	N122—Pr1—N151—C152	6.2 (3)
O51—Pr1—N102—N101	−153.8 (3)	N142—Pr1—N151—C152	−15.7 (2)
O55'—Pr1—N102—N101	−112.9 (5)	N131—Pr1—N151—C152	94.7 (3)
O21—Pr1—N102—N101	21.5 (3)	N102—Pr1—N151—C152	−62.8 (3)
N122—Pr1—N102—N101	−26.9 (3)	N111—Pr1—N151—C152	−117.1 (3)
N142—Pr1—N102—N101	55.9 (3)	C156—N151—C152—C153	0.1 (5)
N131—Pr1—N102—N101	−58.8 (3)	Pr1—N151—C152—C153	−166.7 (3)
N151—Pr1—N102—N101	102.7 (3)	C156—N151—C152—C143	−179.8 (3)
N111—Pr1—N102—N101	171.1 (3)	Pr1—N151—C152—C143	13.4 (4)
N101—N102—C103—C104	1.2 (4)	N142—C143—C152—N151	3.3 (5)
Pr1—N102—C103—C104	−176.1 (2)	C144—C143—C152—N151	−179.3 (4)
N101—N102—C103—C112	−172.0 (3)	N142—C143—C152—C153	−176.6 (3)
Pr1—N102—C103—C112	10.7 (5)	C144—C143—C152—C153	0.8 (6)
N102—C103—C104—C105	−1.4 (5)	N151—C152—C153—C154	−1.2 (6)
C112—C103—C104—C105	170.6 (4)	C143—C152—C153—C154	178.7 (3)
C103—C104—C105—N101	1.0 (5)	C152—C153—C154—C155	0.7 (6)
N102—N101—C105—C104	−0.2 (5)	C153—C154—C155—C156	0.8 (6)
B1—N101—C105—C104	−166.3 (4)	C152—N151—C156—C155	1.4 (6)
O55—Pr1—N111—C116	113.7 (6)	Pr1—N151—C156—C155	168.4 (3)
O25—Pr1—N111—C116	−11.8 (3)	C154—C155—C156—N151	−1.9 (6)
O51—Pr1—N111—C116	37.5 (3)	C16—C11—C12—C13	0.8 (6)
O55'—Pr1—N111—C116	108.8 (7)	C22—C11—C12—C13	−177.9 (3)
O21—Pr1—N111—C116	−95.1 (3)	C11—C12—C13—C14	0.1 (6)
N122—Pr1—N111—C116	164.1 (3)	C12—C13—C14—C15	−0.3 (7)
N142—Pr1—N111—C116	−124.3 (3)	C13—C14—C15—C16	−0.4 (6)
N131—Pr1—N111—C116	79.3 (3)	C14—C15—C16—C11	1.3 (6)
N102—Pr1—N111—C116	−175.6 (3)	C12—C11—C16—C15	−1.5 (5)
N151—Pr1—N111—C116	−67.0 (3)	C22—C11—C16—C15	177.3 (3)
O55—Pr1—N111—C112	−57.5 (6)	O55—Pr1—O21—C22	−119.7 (9)
O25—Pr1—N111—C112	177.1 (3)	O25—Pr1—O21—C22	1.2 (3)
O51—Pr1—N111—C112	−133.7 (3)	O51—Pr1—O21—C22	−22.0 (4)
O55'—Pr1—N111—C112	−62.3 (7)	O55'—Pr1—O21—C22	−116.8 (10)
O21—Pr1—N111—C112	93.8 (3)	N122—Pr1—O21—C22	−146.4 (4)
N122—Pr1—N111—C112	−7.1 (3)	N142—Pr1—O21—C22	130.3 (4)
N142—Pr1—N111—C112	64.6 (3)	N131—Pr1—O21—C22	−78.7 (3)
N131—Pr1—N111—C112	−91.9 (3)	N102—Pr1—O21—C22	163.3 (3)
N102—Pr1—N111—C112	13.2 (3)	N151—Pr1—O21—C22	69.5 (3)
N151—Pr1—N111—C112	121.8 (3)	N111—Pr1—O21—C22	97.2 (4)
C116—N111—C112—C113	−0.4 (6)	Pr1—O21—C22—C23	−4.7 (6)
Pr1—N111—C112—C113	171.1 (3)	Pr1—O21—C22—C11	178.2 (2)
C116—N111—C112—C103	174.4 (3)	C12—C11—C22—O21	−169.1 (3)
Pr1—N111—C112—C103	−14.1 (4)	C16—C11—C22—O21	12.1 (5)
N102—C103—C112—N111	2.9 (5)	C12—C11—C22—C23	13.6 (5)
C104—C103—C112—N111	−168.5 (4)	C16—C11—C22—C23	−165.1 (3)
N102—C103—C112—C113	177.6 (4)	O21—C22—C23—C24	1.7 (5)
C104—C103—C112—C113	6.2 (7)	C11—C22—C23—C24	178.6 (3)
N111—C112—C113—C114	1.8 (7)	C22—C23—C24—O25	5.7 (5)
C103—C112—C113—C114	−172.6 (4)	C22—C23—C24—C31	−173.6 (3)
C112—C113—C114—C115	−0.8 (7)	C23—C24—O25—Pr1	−12.1 (6)
C113—C114—C115—C116	−1.5 (7)	C31—C24—O25—Pr1	167.2 (2)
C112—N111—C116—C115	−2.2 (6)	O55—Pr1—O25—C24	130.4 (5)
Pr1—N111—C116—C115	−173.6 (3)	O51—Pr1—O25—C24	167.8 (4)
C114—C115—C116—N111	3.1 (6)	O55'—Pr1—O25—C24	141.3 (6)
N101—B1—N121—N122	−55.3 (5)	O21—Pr1—O25—C24	7.7 (3)
N141—B1—N121—N122	62.4 (5)	N122—Pr1—O25—C24	42.5 (4)
N101—B1—N121—C125	131.5 (4)	N142—Pr1—O25—C24	−39.7 (3)
N141—B1—N121—C125	−110.8 (5)	N131—Pr1—O25—C24	82.5 (3)
C125—N121—N122—C123	0.6 (4)	N102—Pr1—O25—C24	−84.8 (5)
B1—N121—N122—C123	−173.9 (4)	N151—Pr1—O25—C24	−80.4 (3)
C125—N121—N122—Pr1	165.0 (3)	N111—Pr1—O25—C24	−141.5 (3)
B1—N121—N122—Pr1	−9.6 (5)	O25—C24—C31—C36	20.8 (4)
O55—Pr1—N122—C123	−86.4 (7)	C23—C24—C31—C36	−159.8 (3)
O25—Pr1—N122—C123	36.8 (3)	O25—C24—C31—C32	−156.4 (3)
O51—Pr1—N122—C123	−48.0 (3)	C23—C24—C31—C32	23.0 (5)
O55'—Pr1—N122—C123	−88.5 (7)	C36—C31—C32—C33	−0.7 (5)
O21—Pr1—N122—C123	71.9 (3)	C24—C31—C32—C33	176.5 (3)
N142—Pr1—N122—C123	139.8 (3)	C31—C32—C33—C34	0.1 (6)
N131—Pr1—N122—C123	−7.3 (2)	C32—C33—C34—C35	0.9 (6)
N102—Pr1—N122—C123	−157.2 (3)	C33—C34—C35—C36	−1.4 (7)
N151—Pr1—N122—C123	120.2 (3)	C34—C35—C36—C31	0.8 (6)
N111—Pr1—N122—C123	−138.7 (3)	C32—C31—C36—C35	0.3 (5)
O55—Pr1—N122—N121	111.2 (7)	C24—C31—C36—C35	−177.1 (3)
O25—Pr1—N122—N121	−125.6 (3)	C46—C41—C42—C43	−2.3 (6)
O51—Pr1—N122—N121	149.7 (3)	C52—C41—C42—C43	174.9 (4)
O55'—Pr1—N122—N121	109.1 (7)	C41—C42—C43—C44	1.9 (7)
O21—Pr1—N122—N121	−90.4 (3)	C42—C43—C44—C45	0.7 (6)
N142—Pr1—N122—N121	−22.6 (3)	C43—C44—C45—C46	−2.7 (6)
N131—Pr1—N122—N121	−169.7 (3)	C44—C45—C46—C41	2.3 (6)
N102—Pr1—N122—N121	40.5 (3)	C42—C41—C46—C45	0.2 (6)
N151—Pr1—N122—N121	−42.1 (3)	C52—C41—C46—C45	−177.1 (3)
N111—Pr1—N122—N121	58.9 (3)	O55—Pr1—O51—C52	−5.8 (6)
N121—N122—C123—C124	−1.0 (4)	O25—Pr1—O51—C52	−155.7 (3)
Pr1—N122—C123—C124	−166.8 (3)	O55'—Pr1—O51—C52	0.9 (7)
N121—N122—C123—C132	174.8 (3)	O21—Pr1—O51—C52	−132.5 (3)
Pr1—N122—C123—C132	8.9 (4)	N122—Pr1—O51—C52	−43.6 (4)
N122—C123—C124—C125	0.9 (5)	N142—Pr1—O51—C52	119.2 (3)
C132—C123—C124—C125	−174.1 (4)	N131—Pr1—O51—C52	−79.5 (3)
C123—C124—C125—N121	−0.5 (5)	N102—Pr1—O51—C52	42.1 (3)
N122—N121—C125—C124	−0.1 (5)	N151—Pr1—O51—C52	145.5 (3)
B1—N121—C125—C124	173.8 (4)	N111—Pr1—O51—C52	73.7 (3)
O55—Pr1—N131—C136	−105.9 (5)	Pr1—O51—C52—C53'	−21.7 (7)
O25—Pr1—N131—C136	36.2 (2)	Pr1—O51—C52—C53	3.7 (6)
O51—Pr1—N131—C136	−31.7 (2)	Pr1—O51—C52—C41	173.8 (2)
O55'—Pr1—N131—C136	−98.5 (6)	C42—C41—C52—O51	−147.7 (4)
O21—Pr1—N131—C136	106.3 (3)	C46—C41—C52—O51	29.4 (5)
N122—Pr1—N131—C136	178.0 (3)	C42—C41—C52—C53'	45.9 (6)
N142—Pr1—N131—C136	138.4 (2)	C46—C41—C52—C53'	−136.9 (5)
N102—Pr1—N131—C136	−148.0 (2)	C42—C41—C52—C53	22.1 (6)
N151—Pr1—N131—C136	58.7 (3)	C46—C41—C52—C53	−160.7 (5)
N111—Pr1—N131—C136	−70.9 (3)	O51—C52—C53—C54	−1.9 (10)
O55—Pr1—N131—C132	81.6 (5)	C53'—C52—C53—C54	112 (2)
O25—Pr1—N131—C132	−136.3 (3)	C41—C52—C53—C54	−171.3 (6)
O51—Pr1—N131—C132	155.8 (3)	C52—C53—C54—O55	7.4 (17)
O55'—Pr1—N131—C132	88.9 (6)	C52—C53—C54—C61	−174.7 (7)
O21—Pr1—N131—C132	−66.2 (2)	C53—C54—O55—Pr1	−14 (3)
N122—Pr1—N131—C132	5.5 (2)	C61—C54—O55—Pr1	167.9 (16)
N142—Pr1—N131—C132	−34.1 (3)	O25—Pr1—O55—C54	46 (2)
N102—Pr1—N131—C132	39.5 (3)	O51—Pr1—O55—C54	11 (2)
N151—Pr1—N131—C132	−113.8 (2)	O55'—Pr1—O55—C54	−32 (6)
N111—Pr1—N131—C132	116.6 (3)	O21—Pr1—O55—C54	135.5 (18)
C136—N131—C132—C133	1.1 (5)	N122—Pr1—O55—C54	161 (2)
Pr1—N131—C132—C133	173.8 (3)	N142—Pr1—O55—C54	−144 (2)
C136—N131—C132—C123	−176.4 (3)	N131—Pr1—O55—C54	95 (2)
Pr1—N131—C132—C123	−3.7 (4)	N102—Pr1—O55—C54	−123 (2)
N122—C123—C132—N131	−3.2 (5)	N151—Pr1—O55—C54	−63 (3)
C124—C123—C132—N131	171.4 (4)	N111—Pr1—O55—C54	−62 (2)
N122—C123—C132—C133	179.3 (3)	O55—C54—C61—C62	153.7 (12)
C124—C123—C132—C133	−6.0 (6)	C53—C54—C61—C62	−24.5 (8)
N131—C132—C133—C134	−1.5 (6)	O55—C54—C61—C66	−23.3 (13)
C123—C132—C133—C134	175.8 (4)	C53—C54—C61—C66	158.5 (6)
C132—C133—C134—C135	0.1 (6)	C66—C61—C62—C63	0.0
C133—C134—C135—C136	1.7 (6)	C54—C61—C62—C63	−177.0 (5)
C132—N131—C136—C135	0.8 (5)	C61—C62—C63—C64	0.0
Pr1—N131—C136—C135	−171.9 (3)	C62—C63—C64—C65	0.0
C134—C135—C136—N131	−2.2 (6)	C63—C64—C65—C66	0.0
N121—B1—N141—C145	117.1 (5)	C64—C65—C66—C61	0.0
N101—B1—N141—C145	−123.1 (5)	C62—C61—C66—C65	0.0
N121—B1—N141—N142	−70.4 (5)	C54—C61—C66—C65	177.0 (5)
N101—B1—N141—N142	49.4 (5)	O51—C52—C53'—C54'	22.3 (10)
C145—N141—N142—C143	−0.2 (4)	C53—C52—C53'—C54'	−58.0 (16)
B1—N141—N142—C143	−174.1 (4)	C41—C52—C53'—C54'	−173.2 (6)
C145—N141—N142—Pr1	−161.8 (3)	C52—C53'—C54'—O55'	3.3 (16)
B1—N141—N142—Pr1	24.2 (5)	C52—C53'—C54'—C61'	−175.0 (7)
O55—Pr1—N142—C143	163.3 (5)	C53'—C54'—O55'—Pr1	−34 (3)
O25—Pr1—N142—C143	−25.7 (3)	C61'—C54'—O55'—Pr1	144 (2)
O51—Pr1—N142—C143	48.9 (4)	O55—Pr1—O55'—C54'	163 (11)
O55'—Pr1—N142—C143	153.2 (5)	O25—Pr1—O55'—C54'	55 (3)
O21—Pr1—N142—C143	−74.5 (3)	O51—Pr1—O55'—C54'	28 (2)
N122—Pr1—N142—C143	−144.4 (3)	O21—Pr1—O55'—C54'	148 (2)
N131—Pr1—N142—C143	−108.4 (3)	N122—Pr1—O55'—C54'	175 (3)
N102—Pr1—N142—C143	140.9 (3)	N142—Pr1—O55'—C54'	−124 (3)
N151—Pr1—N142—C143	18.2 (3)	N131—Pr1—O55'—C54'	112 (3)
N111—Pr1—N142—C143	90.6 (3)	N102—Pr1—O55'—C54'	−113 (3)
O55—Pr1—N142—N141	−37.9 (6)	N151—Pr1—O55'—C54'	−42 (3)
O25—Pr1—N142—N141	133.1 (3)	N111—Pr1—O55'—C54'	−49 (2)
O51—Pr1—N142—N141	−152.2 (3)	O55'—C54'—C61'—C62'	−152.3 (12)
O55'—Pr1—N142—N141	−47.9 (6)	C53'—C54'—C61'—C62'	26.0 (9)
O21—Pr1—N142—N141	84.3 (3)	O55'—C54'—C61'—C66'	29.4 (13)
N122—Pr1—N142—N141	14.5 (3)	C53'—C54'—C61'—C66'	−152.2 (6)
N131—Pr1—N142—N141	50.4 (3)	C66'—C61'—C62'—C63'	0.0
N102—Pr1—N142—N141	−60.3 (3)	C54'—C61'—C62'—C63'	−178.2 (6)
N151—Pr1—N142—N141	177.0 (3)	C61'—C62'—C63'—C64'	0.0
N111—Pr1—N142—N141	−110.6 (3)	C62'—C63'—C64'—C65'	0.0
N141—N142—C143—C144	−0.1 (4)	C63'—C64'—C65'—C66'	0.0
Pr1—N142—C143—C144	162.4 (3)	C64'—C65'—C66'—C61'	0.0
N141—N142—C143—C152	177.9 (3)	C62'—C61'—C66'—C65'	0.0
Pr1—N142—C143—C152	−19.6 (4)	C54'—C61'—C66'—C65'	178.3 (6)
N142—C143—C144—C145	0.3 (5)

Experimental details

Crystal data
Chemical formula	[Pr(C₂₄H₁₉BN₉)(C₁₅H₁₁O₄)₂]
M_r	1031.68
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	11.6308 (15), 11.9248 (16), 18.569 (2)
α, β, γ (°)	96.558 (2), 106.782 (2), 105.669 (2)
V (Å³)	2321.9 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.11
Crystal size (mm)	0.34 × 0.25 × 0.18

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.705, 0.826
No. of measured, independent and observed [I > 2σ(I)] reflections	22669, 8143, 7003
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.074, 1.05
No. of reflections	8143
No. of parameters	680
No. of restraints	230
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.72

Computer programs: XSCANS (Siemens, 1996), XSCANS, SHELXTL (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL.

Selected geometric parameters (Å, º) top

Pr1—O55	2.448 (17)	Pr1—N142	2.656 (3)
Pr1—O25	2.454 (2)	Pr1—N131	2.656 (3)
Pr1—O51	2.464 (2)	Pr1—N102	2.704 (3)
Pr1—O55'	2.492 (17)	Pr1—N151	2.754 (3)
Pr1—O21	2.496 (2)	Pr1—N111	2.804 (3)
Pr1—N122	2.595 (3)

O55—Pr1—O25	128.4 (6)	O55—Pr1—N102	65.5 (6)
O55—Pr1—O51	71.7 (5)	O25—Pr1—N102	163.61 (8)
O25—Pr1—O51	65.89 (7)	O51—Pr1—N102	117.95 (9)
O55—Pr1—O55'	9.0 (6)	O55'—Pr1—N102	66.0 (7)
O25—Pr1—O55'	126.1 (6)	O21—Pr1—N102	113.69 (9)
O51—Pr1—O55'	65.2 (5)	N122—Pr1—N102	68.87 (11)
O55—Pr1—O21	129.8 (4)	N142—Pr1—N102	59.51 (9)
O25—Pr1—O21	65.98 (7)	N131—Pr1—N102	122.86 (9)
O51—Pr1—O21	128.16 (7)	O55—Pr1—N151	150.3 (5)
O55'—Pr1—O21	138.5 (4)	O25—Pr1—N151	65.76 (8)
O55—Pr1—N122	69.4 (3)	O51—Pr1—N151	98.08 (8)
O25—Pr1—N122	121.82 (9)	O55'—Pr1—N151	142.4 (4)
O51—Pr1—N122	131.58 (8)	O21—Pr1—N151	78.77 (8)
O55'—Pr1—N122	78.1 (4)	N122—Pr1—N151	129.64 (9)
O21—Pr1—N122	65.02 (9)	N142—Pr1—N151	58.98 (9)
O55—Pr1—N142	121.4 (6)	N131—Pr1—N151	135.59 (9)
O25—Pr1—N142	109.44 (8)	N102—Pr1—N151	97.90 (9)
O51—Pr1—N142	154.01 (9)	O55—Pr1—N111	74.0 (5)
O55'—Pr1—N142	124.5 (7)	O25—Pr1—N111	113.86 (9)
O21—Pr1—N142	63.44 (9)	O51—Pr1—N111	68.63 (9)
N122—Pr1—N142	73.55 (9)	O55'—Pr1—N111	66.3 (5)
O55—Pr1—N131	71.2 (6)	O21—Pr1—N111	151.93 (8)
O25—Pr1—N131	73.08 (8)	N122—Pr1—N111	124.18 (10)
O51—Pr1—N131	79.07 (8)	N142—Pr1—N111	92.39 (10)
O55'—Pr1—N131	76.8 (6)	N131—Pr1—N111	138.32 (9)
O21—Pr1—N131	69.66 (8)	N102—Pr1—N111	58.02 (11)
N122—Pr1—N131	61.99 (9)	N151—Pr1—N111	76.31 (9)
N142—Pr1—N131	125.31 (9)

Acknowledgements

The authors thank the EPSRC for financial support (to GMD).

References

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Volume 61| Part 5| May 2005| Pages m221-m223

doi:10.1107/S0108270105007791

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