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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): m705.
Published online 2009 June 6. doi:  10.1107/S1600536809019783
PMCID: PMC2969283

Tris(dibenzoyl­methanido-κ2 O,O′)[(6R,8R)-(−)-7,7-dimethyl-3-(2-pyrid­yl)-5,6,7,8-tetra­hydro-6,8-methano­isoquinoline-κ2 N,N′]terbium(III)

Abstract

In the title compound, [Tb(C15H11O2)3(C17H18N2)], the 7,7-dimethyl-3-(2-pyrid­yl)-5,6,7,8-tetra­hydro-6,8-methano­iso­quin­oline (LRR) ligand coordinates to TbIII through the two N atoms of the heterocycle. The metal centre is also chelated by three deprotonated 1,3-diphenyl­propane-1,3-dione (dbm) ligands, forming enanti­omerically pure [Tb(dbm)3 LRR]. The TbIII atom is located in a distorted square anti­prism of eight coordinating atoms (six O and two N atoms).

Related literature

For a general background to lanthanide complexes, see: Aspinall (2002 [triangle]); Li, Chen et al. (2007 [triangle]); Li & Zhang (2008 [triangle]). For a related structure, see: Li, Zheng et al. (2007 [triangle]). For the synthesis, see: Hayoz et al. (1993 [triangle]); Lennartson et al. (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m705-scheme1.jpg

Experimental

Crystal data

  • [Tb(C15H11O2)3(C17H18N2)]
  • M r = 1078.97
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m705-efi1.jpg
  • a = 9.5158 (19) Å
  • b = 20.790 (4) Å
  • c = 12.769 (3) Å
  • β = 92.47 (3)°
  • V = 2523.7 (9) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.46 mm−1
  • T = 296 K
  • 0.51 × 0.43 × 0.34 mm

Data collection

  • Rigaku R-AXIS SPIDER IP diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.524, T max = 0.637
  • 19632 measured reflections
  • 8346 independent reflections
  • 5624 reflections with I > 2σ(I)
  • R int = 0.090

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.093
  • S = 0.95
  • 8346 reflections
  • 640 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 1.04 e Å−3
  • Δρmin = −1.22 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 3779 Friedel pairs
  • Flack parameter: −0.008 (14)

Data collection: PROCESS-AUTO (Rigaku, 1998 [triangle]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Selected geometric parameters (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809019783/ng2576sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019783/ng2576Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank the National Science Foundation of China (grant No. 20773098) and the Project of Innovation Foundation of Xiamen University (Series 2, No. XDKJCX20061027) for supporting this work.

supplementary crystallographic information

Comment

Due to the potential applications as luminescence, ferroelectric material and NMR shift reagents, the stereoselective synthesis and characterization of labile lanthanide β-diketonate complexes have obtained a great deal of attentions (Aspinall, 2002; Li, Chen et al., 2007); Li & Zhang, 2008). Herein, we report a chiral complex, [Tb(dbm)3LRR] (Fig. 1), which is isostructural with the previously reported [Eu(dbm)3LRR] (Li, Zheng et al., 2007). For the intrducing of chiral ligand LRR, the complex was obtained as an enatiopure compound and crystallized in a chiral space group P21. The title compound, was synthesized under mild condition. LRR is introduced as a second ligand, which coordinates to TbIII with three dbm to form enantiomerically pure complex [Tb(dbm)3LRR]. The absolute configuration of the stereocenters in the ligand LRR remains unchanged during the synthetic procedure.

As indicated in Fig. 1, six O atoms and two N atoms come from the three diketone anions and a chiral 2,2-bipyridine derivative ligand, LRR, coordinate to a TbIII cation to form a mononuclear neutral eight-coordinated TbIII-based complex. In the distorted square antiprism around the TbIII cation, O1, O2, N1, N2 and O3, O4, O5, O6 compose the top and bottom planes of the antiprism. The mean deviations from the two planes are 0.122 and 0.069 Å, and their dihedral angle is 1.83 (1)°. And the top plane is rotated by 37° relative to the bottom plane, which is smaller than 45° for a regular square antipism.

Experimental

The title compound was prepared via a modification of a previously reported method (Hayoz et al., 1993; Lennartson et al., 2005). The LRR ligand and [Tb(dbm)3H2O] was synthesized according to reported procedures.

A solution of [Tb(dbm)3H2O] (15 mg, 0.0178 mmol) in acetone (2 ml) was combined with a solution of (8R,10R)-(-)-[4,5]-pineno-2,2'-bipyridine (4.45 mg, 0.0178 mmol) in ethanol (2 ml). And the mixture was stand at room temperature for two days. Yellow block crystals of the title complex were obtained in 75% yield.

Refinement

The hydrogen atoms were positioned geometrically (C—H = 0.93, 0.98, 0.97 or 0.96Å for phenyl, tertiary, methylene or methyl H atoms respectively) and were included in the refinement in the riding model approximation. The displacement parameters of methyl H atoms were set to 1.5Ueq(C), while those of other H atoms were set to 1.2Ueq(C).

Figures

Fig. 1.
The structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids at the 50% probability level. The H atoms have been omited for charity.

Crystal data

[Tb(C15H11O2)3(C17H18N2)]F(000) = 1100
Mr = 1078.97Dx = 1.420 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 11553 reflections
a = 9.5158 (19) Åθ = 3.2–27.5°
b = 20.790 (4) ŵ = 1.46 mm1
c = 12.769 (3) ÅT = 296 K
β = 92.47 (3)°Block, yellow
V = 2523.7 (9) Å30.51 × 0.43 × 0.34 mm
Z = 2

Data collection

Rigaku R-AXIS SPIDER IP diffractometer8346 independent reflections
Radiation source: fine-focus sealed tube5624 reflections with I > 2σ(I)
graphiteRint = 0.090
ω scansθmax = 25.0°, θmin = 3.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −11→11
Tmin = 0.524, Tmax = 0.637k = −23→24
19632 measured reflectionsl = −14→15

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.093w = 1/[σ2(Fo2) + (0.0094P)2 + 1.367P] where P = (Fo2 + 2Fc2)/3
S = 0.95(Δ/σ)max = 0.003
8346 reflectionsΔρmax = 1.03 e Å3
640 parametersΔρmin = −1.22 e Å3
1 restraintAbsolute structure: Flack (1983), 3779 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.008 (14)

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 (Å2)

xyzUiso*/Ueq
C10.3453 (11)0.4955 (5)1.0559 (7)0.061 (4)
H1A0.26270.47251.06400.073*
N10.3795 (6)0.5115 (7)0.9587 (4)0.0455 (15)
O10.2344 (7)0.4463 (3)0.6603 (6)0.044 (2)
Tb10.19194 (4)0.51094 (3)0.80567 (3)0.03880 (11)
C20.4251 (12)0.5109 (10)1.1437 (7)0.085 (3)
H2A0.39630.50001.21010.102*
N20.4480 (7)0.5358 (3)0.7640 (6)0.0378 (19)
O20.1996 (9)0.4047 (4)0.8634 (8)0.049 (3)
C30.5473 (15)0.5427 (6)1.1313 (10)0.099 (5)
H3A0.60480.55271.18970.118*
O3−0.0322 (7)0.4832 (2)0.7448 (5)0.0479 (17)
C40.5867 (12)0.5599 (5)1.0347 (9)0.076 (3)
H4A0.66970.58271.02660.091*
O40.0459 (5)0.5113 (5)0.9497 (3)0.0460 (13)
C50.5009 (11)0.5429 (4)0.9467 (7)0.049 (3)
O50.1579 (7)0.5793 (3)0.6611 (6)0.0403 (18)
C60.5388 (9)0.5584 (4)0.8388 (8)0.040 (2)
O60.2217 (10)0.6188 (3)0.8630 (8)0.047 (3)
C70.6570 (10)0.5914 (4)0.8162 (9)0.056 (3)
H7A0.71620.60670.87050.068*
C80.6903 (13)0.6027 (5)0.7130 (10)0.046 (3)
C90.6051 (10)0.5767 (4)0.6343 (8)0.047 (3)
C100.4818 (10)0.5450 (3)0.6637 (7)0.041 (2)
H10A0.42040.52950.61080.049*
C110.8151 (11)0.6428 (5)0.6816 (10)0.062 (3)
H11A0.90160.62370.71000.075*
H11B0.80770.68590.71000.075*
C120.8186 (12)0.6461 (5)0.5617 (10)0.060 (3)
H12A0.89770.67050.53520.072*
C130.6755 (16)0.6621 (6)0.5090 (11)0.065 (4)
C140.6401 (12)0.5886 (4)0.5235 (8)0.058 (3)
H14A0.58030.56810.46870.070*
C150.8052 (12)0.5770 (5)0.5200 (10)0.083 (4)
H15A0.84160.54430.56810.099*
H15B0.83920.57100.45010.099*
C160.5843 (11)0.7116 (5)0.5623 (9)0.069 (3)
H16A0.61690.75410.54670.104*
H16B0.59030.70490.63670.104*
H16C0.48840.70700.53700.104*
C170.6831 (14)0.6796 (6)0.3934 (9)0.104 (5)
H17A0.70390.72460.38700.155*
H17B0.59450.67050.35780.155*
H17C0.75580.65480.36260.155*
C180.1838 (15)0.3886 (6)0.6372 (12)0.047 (4)
C190.1776 (16)0.3760 (6)0.5217 (13)0.050 (4)
C200.2664 (15)0.4081 (6)0.4562 (11)0.067 (4)
H20A0.32960.43860.48320.080*
C210.260 (2)0.3937 (7)0.3468 (14)0.100 (7)
H21A0.31910.41490.30210.120*
C220.166 (2)0.3486 (9)0.3073 (14)0.094 (7)
H22A0.15970.34040.23570.113*
C230.0827 (14)0.3161 (5)0.3729 (10)0.076 (4)
H23A0.02060.28500.34630.091*
C240.0900 (13)0.3290 (4)0.4782 (8)0.059 (3)
H24A0.03400.30540.52210.070*
C250.1452 (11)0.3446 (4)0.7094 (7)0.043 (3)
H25A0.10670.30610.68460.052*
C260.1589 (10)0.3527 (4)0.8162 (7)0.037 (2)
C270.1249 (9)0.2964 (3)0.8876 (7)0.038 (2)
C280.0840 (12)0.3068 (4)0.9875 (7)0.062 (3)
H28A0.07950.34851.01330.074*
C290.0499 (13)0.2565 (5)1.0495 (8)0.085 (4)
H29A0.02170.26451.11710.102*
C300.0559 (12)0.1946 (4)1.0152 (9)0.067 (3)
H30A0.02970.16101.05830.080*
C310.1002 (13)0.1823 (5)0.9180 (10)0.079 (4)
H31A0.10890.14030.89440.095*
C320.1324 (13)0.2336 (4)0.8546 (8)0.073 (4)
H32A0.16020.22540.78690.087*
C33−0.1299 (10)0.4515 (4)0.7860 (7)0.038 (2)
C34−0.2340 (12)0.4184 (5)0.7124 (9)0.043 (3)
C35−0.2038 (11)0.4120 (4)0.6077 (10)0.052 (3)
H35A−0.11900.42770.58450.062*
C36−0.2997 (17)0.3822 (6)0.5360 (12)0.074 (5)
H36A−0.27990.37950.46540.089*
C37−0.4207 (15)0.3576 (6)0.5704 (12)0.085 (4)
H37A−0.48160.33550.52430.101*
C38−0.4543 (12)0.3653 (5)0.6740 (12)0.076 (4)
H38A−0.53960.34960.69630.091*
C39−0.3618 (11)0.3964 (5)0.7463 (9)0.052 (3)
H39A−0.38590.40220.81540.063*
C40−0.1415 (10)0.4455 (4)0.8923 (8)0.046 (2)
H40A−0.21160.41840.91520.055*
C41−0.0589 (10)0.4760 (4)0.9682 (7)0.042 (2)
C42−0.0893 (10)0.4674 (4)1.0826 (7)0.048 (2)
C43−0.0303 (9)0.5112 (9)1.1547 (6)0.061 (2)
H43A0.02940.54341.13260.073*
C44−0.0616 (11)0.5064 (9)1.2606 (7)0.080 (3)
H44A−0.02410.53601.30860.096*
C45−0.1463 (15)0.4586 (6)1.2936 (9)0.094 (4)
H45A−0.16470.45531.36430.112*
C46−0.2038 (14)0.4162 (6)1.2253 (9)0.089 (4)
H46A−0.26420.38481.24920.107*
C47−0.1749 (13)0.4182 (5)1.1191 (8)0.075 (4)
H47A−0.21190.38721.07320.089*
C480.2014 (13)0.6338 (6)0.6362 (12)0.039 (4)
C490.1978 (14)0.6503 (6)0.5226 (13)0.041 (4)
C500.2037 (14)0.5989 (6)0.4524 (12)0.061 (4)
H50A0.20330.55700.47770.073*
C510.2099 (19)0.6093 (8)0.3490 (14)0.085 (5)
H51A0.21730.57450.30370.103*
C520.2054 (16)0.6708 (10)0.3091 (14)0.081 (6)
H52A0.20590.67740.23710.097*
C530.2004 (14)0.7212 (5)0.3744 (10)0.073 (4)
H53A0.19870.76280.34770.088*
C540.1977 (12)0.7112 (5)0.4813 (9)0.061 (3)
H54A0.19570.74640.52610.073*
C550.2517 (10)0.6806 (4)0.7104 (7)0.039 (2)
H55A0.27430.72120.68570.047*
C560.2688 (11)0.6690 (4)0.8176 (8)0.041 (2)
C570.3457 (10)0.7162 (4)0.8887 (8)0.049 (3)
C580.3327 (13)0.7120 (5)0.9947 (9)0.077 (4)
H58A0.27280.68161.02210.092*
C590.4101 (18)0.7536 (8)1.0620 (12)0.106 (5)
H59A0.40280.75041.13430.127*
C600.4949 (13)0.7981 (6)1.0211 (12)0.082 (4)
H60A0.54840.82481.06570.098*
C610.5031 (16)0.8045 (6)0.9181 (12)0.089 (5)
H61A0.55860.83690.89130.106*
C620.4301 (12)0.7636 (4)0.8507 (9)0.072 (3)
H62B0.43810.76800.77870.087*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.073 (8)0.068 (10)0.041 (6)−0.002 (5)0.011 (5)0.009 (5)
N10.046 (4)0.046 (3)0.045 (4)0.001 (8)0.006 (3)−0.008 (9)
O10.039 (5)0.045 (4)0.049 (4)−0.009 (3)0.016 (4)0.001 (3)
Tb10.0427 (2)0.03169 (16)0.0427 (2)−0.0053 (4)0.01018 (15)0.0003 (4)
C20.100 (9)0.116 (8)0.039 (6)−0.024 (15)0.003 (6)0.013 (15)
N20.028 (5)0.037 (4)0.050 (5)−0.007 (3)0.010 (4)−0.007 (3)
O20.051 (6)0.047 (5)0.049 (7)−0.014 (4)0.002 (5)−0.013 (4)
C30.097 (12)0.143 (12)0.054 (9)−0.036 (9)−0.010 (8)0.006 (7)
O30.054 (5)0.049 (3)0.042 (4)−0.001 (3)0.014 (3)0.007 (3)
C40.058 (9)0.122 (9)0.048 (8)−0.019 (7)−0.001 (6)0.007 (7)
O40.046 (3)0.050 (3)0.043 (3)−0.015 (6)0.014 (3)−0.004 (7)
C50.050 (7)0.057 (5)0.042 (6)−0.001 (5)0.012 (5)0.008 (4)
O50.045 (5)0.034 (3)0.042 (4)−0.009 (3)0.002 (4)0.002 (3)
C60.026 (6)0.035 (4)0.060 (7)−0.004 (4)0.006 (5)0.003 (4)
O60.072 (7)0.024 (4)0.047 (7)−0.011 (4)0.014 (5)−0.015 (4)
C70.037 (7)0.062 (6)0.069 (8)−0.007 (5)−0.014 (6)0.021 (6)
C80.031 (8)0.053 (6)0.055 (8)−0.010 (6)0.022 (7)0.008 (5)
C90.048 (7)0.033 (5)0.063 (7)−0.005 (4)0.022 (6)−0.006 (4)
C100.048 (7)0.042 (4)0.034 (6)−0.006 (4)0.007 (5)−0.014 (4)
C110.033 (6)0.062 (6)0.091 (10)−0.004 (5)0.004 (6)0.031 (7)
C120.041 (8)0.052 (7)0.089 (10)0.000 (5)0.026 (7)0.007 (6)
C130.078 (10)0.048 (7)0.070 (10)−0.013 (6)0.035 (8)0.010 (6)
C140.076 (9)0.054 (6)0.047 (7)−0.022 (5)0.023 (6)−0.001 (5)
C150.076 (10)0.058 (7)0.117 (11)0.005 (6)0.050 (9)0.003 (7)
C160.047 (7)0.059 (6)0.102 (10)0.012 (5)0.002 (7)0.024 (7)
C170.117 (12)0.122 (10)0.073 (10)−0.041 (9)0.015 (9)0.038 (8)
C180.067 (11)0.020 (7)0.055 (10)−0.011 (5)0.015 (8)−0.023 (6)
C190.067 (11)0.037 (8)0.048 (10)0.004 (6)0.014 (8)−0.006 (7)
C200.096 (12)0.057 (7)0.047 (8)−0.020 (7)0.003 (8)0.007 (6)
C210.18 (2)0.076 (11)0.052 (11)−0.023 (11)0.040 (11)0.014 (8)
C220.156 (18)0.075 (12)0.052 (13)−0.010 (10)0.002 (12)0.007 (8)
C230.094 (12)0.070 (8)0.063 (9)0.004 (7)0.004 (8)−0.016 (6)
C240.086 (10)0.044 (6)0.047 (7)0.000 (6)0.012 (7)−0.006 (5)
C250.060 (8)0.033 (5)0.039 (6)−0.004 (5)0.015 (6)−0.004 (4)
C260.036 (7)0.028 (4)0.048 (6)−0.005 (4)0.001 (5)0.007 (4)
C270.040 (6)0.026 (4)0.049 (6)−0.005 (4)0.003 (5)−0.002 (4)
C280.092 (10)0.053 (6)0.041 (7)−0.013 (6)0.011 (6)0.003 (5)
C290.119 (13)0.081 (8)0.057 (8)−0.003 (7)0.034 (8)0.006 (7)
C300.075 (9)0.048 (6)0.077 (9)−0.014 (5)−0.009 (7)0.023 (6)
C310.111 (11)0.044 (6)0.082 (9)−0.006 (6)0.003 (8)0.013 (6)
C320.118 (11)0.049 (6)0.052 (7)0.004 (6)0.017 (7)−0.003 (5)
C330.046 (7)0.040 (5)0.029 (5)0.004 (4)−0.001 (5)0.000 (4)
C340.041 (8)0.037 (5)0.052 (7)−0.003 (5)0.007 (6)0.003 (4)
C350.048 (7)0.032 (5)0.074 (9)0.000 (4)−0.005 (6)0.010 (6)
C360.092 (13)0.064 (10)0.063 (10)−0.011 (8)−0.021 (8)−0.016 (7)
C370.071 (11)0.071 (8)0.108 (13)−0.023 (7)−0.043 (9)−0.003 (8)
C380.043 (8)0.063 (7)0.120 (12)−0.008 (5)−0.005 (8)0.008 (7)
C390.028 (7)0.075 (7)0.054 (8)−0.007 (5)0.001 (6)0.012 (6)
C400.034 (6)0.046 (5)0.057 (7)−0.021 (4)0.004 (5)0.003 (4)
C410.034 (6)0.042 (5)0.052 (6)0.000 (4)0.024 (5)0.008 (4)
C420.042 (7)0.057 (5)0.044 (6)0.002 (4)0.012 (5)−0.001 (5)
C430.077 (6)0.057 (4)0.049 (5)0.002 (12)0.016 (5)0.009 (12)
C440.114 (9)0.082 (7)0.046 (6)−0.029 (12)0.018 (6)−0.010 (10)
C450.127 (13)0.113 (10)0.042 (8)−0.036 (9)0.020 (8)−0.005 (7)
C460.114 (12)0.103 (9)0.052 (8)−0.041 (8)0.026 (8)0.014 (6)
C470.100 (10)0.075 (7)0.051 (7)−0.028 (6)0.025 (7)−0.014 (5)
C480.015 (7)0.046 (8)0.054 (10)0.005 (5)0.000 (6)−0.008 (7)
C490.033 (8)0.046 (8)0.043 (10)−0.005 (6)−0.002 (7)−0.004 (7)
C500.067 (10)0.055 (7)0.060 (9)−0.002 (6)−0.008 (7)0.003 (6)
C510.123 (14)0.083 (10)0.051 (10)−0.009 (9)0.005 (9)0.003 (7)
C520.083 (13)0.114 (17)0.047 (12)−0.029 (10)0.007 (9)0.004 (10)
C530.096 (11)0.062 (7)0.063 (9)−0.019 (7)−0.002 (8)0.023 (6)
C540.071 (9)0.049 (6)0.064 (8)−0.007 (6)0.010 (7)0.004 (5)
C550.049 (7)0.025 (4)0.043 (6)−0.009 (4)0.008 (5)0.006 (4)
C560.041 (7)0.029 (5)0.055 (7)0.002 (4)0.012 (5)0.006 (4)
C570.055 (7)0.037 (5)0.055 (7)−0.001 (4)0.005 (5)−0.015 (4)
C580.104 (11)0.070 (7)0.057 (8)−0.039 (7)0.010 (7)−0.006 (6)
C590.130 (16)0.131 (14)0.056 (9)−0.052 (11)0.006 (10)−0.028 (9)
C600.067 (10)0.089 (9)0.090 (11)−0.009 (7)−0.008 (8)−0.039 (8)
C610.104 (13)0.078 (9)0.085 (12)−0.046 (8)0.016 (10)−0.027 (8)
C620.093 (10)0.063 (6)0.061 (8)−0.033 (6)0.007 (7)−0.013 (6)

Geometric parameters (Å, °)

C1—N11.338 (10)C25—H25A0.9300
C1—C21.365 (13)C26—C271.525 (10)
C1—H1A0.9300C27—C281.367 (11)
N1—C51.342 (12)C27—C321.375 (11)
N1—Tb12.589 (6)C28—C291.360 (12)
O1—C181.321 (13)C28—H28A0.9300
O1—Tb12.341 (7)C29—C301.360 (13)
Tb1—O22.328 (9)C29—H29A0.9300
Tb1—O32.312 (7)C30—C311.352 (14)
Tb1—O52.341 (7)C30—H30A0.9300
Tb1—O42.353 (4)C31—C321.382 (12)
Tb1—O62.372 (7)C31—H31A0.9300
Tb1—N22.569 (6)C32—H32A0.9300
C2—C31.352 (16)C33—C401.372 (11)
C2—H2A0.9300C33—C341.503 (14)
N2—C61.344 (11)C34—C351.385 (16)
N2—C101.348 (10)C34—C391.386 (13)
O2—C261.290 (11)C35—C361.409 (16)
C3—C41.353 (14)C35—H35A0.9300
C3—H3A0.9300C36—C371.350 (18)
O3—C331.272 (9)C36—H36A0.9300
C4—C51.405 (14)C37—C381.384 (16)
C4—H4A0.9300C37—H37A0.9300
O4—C411.267 (10)C38—C391.405 (15)
C5—C61.475 (12)C38—H38A0.9300
O5—C481.253 (14)C39—H39A0.9300
C6—C71.360 (11)C40—C411.376 (12)
O6—C561.284 (11)C40—H40A0.9300
C7—C81.388 (15)C41—C421.513 (12)
C7—H7A0.9300C42—C431.395 (16)
C8—C91.374 (15)C42—C471.401 (12)
C8—C111.519 (13)C43—C441.400 (10)
C9—C101.411 (11)C43—H43A0.9300
C9—C141.489 (12)C44—C451.357 (18)
C10—H10A0.9300C44—H44A0.9300
C11—C121.533 (16)C45—C461.340 (15)
C11—H11A0.9700C45—H45A0.9300
C11—H11B0.9700C46—C471.396 (13)
C12—C131.530 (18)C46—H46A0.9300
C12—C151.535 (13)C47—H47A0.9300
C12—H12A0.9800C48—C551.425 (16)
C13—C161.524 (16)C48—C491.49 (2)
C13—C171.526 (16)C49—C541.372 (16)
C13—C141.577 (13)C49—C501.397 (18)
C14—C151.592 (15)C50—C511.34 (2)
C14—H14A0.9800C50—H50A0.9300
C15—H15A0.9700C51—C521.38 (2)
C15—H15B0.9700C51—H51A0.9300
C16—H16A0.9600C52—C531.34 (2)
C16—H16B0.9600C52—H52A0.9300
C16—H16C0.9600C53—C541.382 (14)
C17—H17A0.9600C53—H53A0.9300
C17—H17B0.9600C54—H54A0.9300
C17—H17C0.9600C55—C561.393 (12)
C18—C251.361 (16)C55—H55A0.9300
C18—C191.50 (2)C56—C571.506 (12)
C19—C241.385 (17)C57—C581.367 (13)
C19—C201.385 (17)C57—C621.372 (12)
C20—C211.43 (2)C58—C591.406 (16)
C20—H20A0.9300C58—H58A0.9300
C21—C221.38 (2)C59—C601.348 (17)
C21—H21A0.9300C59—H59A0.9300
C22—C231.358 (19)C60—C611.328 (17)
C22—H22A0.9300C60—H60A0.9300
C23—C241.370 (14)C61—C621.377 (15)
C23—H23A0.9300C61—H61A0.9300
C24—H24A0.9300C62—H62B0.9300
C25—C261.374 (12)
N1—C1—C2123.6 (10)C23—C22—C21120.0 (17)
N1—C1—H1A118.2C23—C22—H22A120.0
C2—C1—H1A118.2C21—C22—H22A120.0
C5—N1—C1118.2 (8)C22—C23—C24120.1 (14)
C5—N1—Tb1119.0 (7)C22—C23—H23A120.0
C1—N1—Tb1120.8 (6)C24—C23—H23A120.0
C18—O1—Tb1128.7 (7)C19—C24—C23122.4 (12)
O2—Tb1—O383.4 (3)C19—C24—H24A118.8
O2—Tb1—O5145.8 (3)C23—C24—H24A118.8
O3—Tb1—O578.0 (2)C18—C25—C26125.0 (9)
O2—Tb1—O172.7 (3)C18—C25—H25A117.5
O3—Tb1—O177.2 (2)C26—C25—H25A117.5
O5—Tb1—O175.32 (17)O2—C26—C25125.4 (8)
O2—Tb1—O476.5 (3)O2—C26—C27115.5 (9)
O3—Tb1—O472.31 (19)C25—C26—C27119.0 (8)
O5—Tb1—O4123.3 (3)C28—C27—C32117.1 (8)
O1—Tb1—O4138.5 (3)C28—C27—C26120.9 (7)
O2—Tb1—O6142.88 (17)C32—C27—C26122.0 (8)
O3—Tb1—O6115.8 (3)C27—C28—C29120.5 (9)
O5—Tb1—O671.3 (3)C27—C28—H28A119.8
O1—Tb1—O6139.9 (3)C29—C28—H28A119.8
O4—Tb1—O679.8 (3)C30—C29—C28121.7 (10)
O2—Tb1—N2103.9 (3)C30—C29—H29A119.1
O3—Tb1—N2148.2 (2)C28—C29—H29A119.1
O5—Tb1—N279.3 (2)C29—C30—C31119.5 (9)
O1—Tb1—N275.7 (2)C29—C30—H30A120.2
O4—Tb1—N2139.4 (2)C31—C30—H30A120.2
O6—Tb1—N276.8 (2)C30—C31—C32118.6 (10)
O2—Tb1—N175.8 (4)C30—C31—H31A120.7
O3—Tb1—N1148.3 (2)C32—C31—H31A120.7
O5—Tb1—N1131.3 (3)C27—C32—C31122.5 (10)
O1—Tb1—N1117.7 (3)C27—C32—H32A118.7
O4—Tb1—N179.69 (17)C31—C32—H32A118.7
O6—Tb1—N172.2 (4)O3—C33—C40123.2 (9)
N2—Tb1—N161.7 (2)O3—C33—C34116.8 (8)
C3—C2—C1118.0 (10)C40—C33—C34120.0 (8)
C3—C2—H2A121.0C35—C34—C39119.4 (11)
C1—C2—H2A121.0C35—C34—C33119.3 (9)
C6—N2—C10117.0 (7)C39—C34—C33121.2 (10)
C6—N2—Tb1120.7 (5)C34—C35—C36120.9 (11)
C10—N2—Tb1119.5 (6)C34—C35—H35A119.5
C26—O2—Tb1130.0 (8)C36—C35—H35A119.5
C2—C3—C4120.7 (12)C37—C36—C35119.6 (14)
C2—C3—H3A119.7C37—C36—H36A120.2
C4—C3—H3A119.7C35—C36—H36A120.2
C33—O3—Tb1132.1 (6)C36—C37—C38120.2 (12)
C3—C4—C5119.2 (11)C36—C37—H37A119.9
C3—C4—H4A120.4C38—C37—H37A119.9
C5—C4—H4A120.4C37—C38—C39121.1 (11)
C41—O4—Tb1129.8 (6)C37—C38—H38A119.4
N1—C5—C4120.3 (8)C39—C38—H38A119.4
N1—C5—C6117.3 (9)C34—C39—C38118.7 (11)
C4—C5—C6122.4 (9)C34—C39—H39A120.6
C48—O5—Tb1135.5 (8)C38—C39—H39A120.6
N2—C6—C7122.6 (9)C33—C40—C41126.0 (8)
N2—C6—C5114.3 (8)C33—C40—H40A117.0
C7—C6—C5123.1 (10)C41—C40—H40A117.0
C56—O6—Tb1132.0 (7)O4—C41—C40124.5 (8)
C6—C7—C8120.8 (11)O4—C41—C42115.7 (9)
C6—C7—H7A119.6C40—C41—C42119.9 (8)
C8—C7—H7A119.6C43—C42—C47118.7 (9)
C9—C8—C7118.4 (9)C43—C42—C41118.1 (8)
C9—C8—C11117.8 (10)C47—C42—C41123.1 (9)
C7—C8—C11123.8 (12)C42—C43—C44119.6 (14)
C8—C9—C10117.5 (9)C42—C43—H43A120.2
C8—C9—C14118.7 (9)C44—C43—H43A120.2
C10—C9—C14123.6 (10)C45—C44—C43120.4 (15)
N2—C10—C9123.6 (9)C45—C44—H44A119.8
N2—C10—H10A118.2C43—C44—H44A119.8
C9—C10—H10A118.2C46—C45—C44120.7 (11)
C8—C11—C12109.8 (10)C46—C45—H45A119.6
C8—C11—H11A109.7C44—C45—H45A119.6
C12—C11—H11A109.7C45—C46—C47121.4 (11)
C8—C11—H11B109.7C45—C46—H46A119.3
C12—C11—H11B109.7C47—C46—H46A119.3
H11A—C11—H11B108.2C46—C47—C42119.1 (10)
C13—C12—C11113.1 (9)C46—C47—H47A120.4
C13—C12—C1589.5 (10)C42—C47—H47A120.4
C11—C12—C15107.4 (9)O5—C48—C55123.6 (13)
C13—C12—H12A114.7O5—C48—C49117.4 (12)
C11—C12—H12A114.7C55—C48—C49119.0 (12)
C15—C12—H12A114.7C54—C49—C50117.3 (14)
C16—C13—C17108.8 (10)C54—C49—C48125.8 (13)
C16—C13—C12117.6 (12)C50—C49—C48116.8 (13)
C17—C13—C12113.5 (10)C51—C50—C49120.9 (14)
C16—C13—C14118.2 (9)C51—C50—H50A119.6
C17—C13—C14111.3 (11)C49—C50—H50A119.6
C12—C13—C1485.9 (9)C50—C51—C52120.7 (16)
C9—C14—C13109.3 (8)C50—C51—H51A119.6
C9—C14—C15105.3 (9)C52—C51—H51A119.6
C13—C14—C1585.9 (8)C53—C52—C51119.8 (16)
C9—C14—H14A117.3C53—C52—H52A120.1
C13—C14—H14A117.3C51—C52—H52A120.1
C15—C14—H14A117.3C52—C53—C54120.0 (12)
C12—C15—C1485.2 (7)C52—C53—H53A120.0
C12—C15—H15A114.5C54—C53—H53A120.0
C14—C15—H15A114.5C49—C54—C53121.2 (11)
C12—C15—H15B114.5C49—C54—H54A119.4
C14—C15—H15B114.5C53—C54—H54A119.4
H15A—C15—H15B111.6C56—C55—C48123.8 (9)
C13—C16—H16A109.5C56—C55—H55A118.1
C13—C16—H16B109.5C48—C55—H55A118.1
H16A—C16—H16B109.5O6—C56—C55123.8 (9)
C13—C16—H16C109.5O6—C56—C57115.4 (9)
H16A—C16—H16C109.5C55—C56—C57120.9 (8)
H16B—C16—H16C109.5C58—C57—C62118.4 (9)
C13—C17—H17A109.5C58—C57—C56119.5 (9)
C13—C17—H17B109.5C62—C57—C56122.1 (9)
H17A—C17—H17B109.5C57—C58—C59119.9 (11)
C13—C17—H17C109.5C57—C58—H58A120.1
H17A—C17—H17C109.5C59—C58—H58A120.1
H17B—C17—H17C109.5C60—C59—C58119.5 (13)
O1—C18—C25124.4 (12)C60—C59—H59A120.3
O1—C18—C19112.2 (12)C58—C59—H59A120.3
C25—C18—C19123.4 (11)C61—C60—C59120.9 (13)
C24—C19—C20118.0 (14)C61—C60—H60A119.5
C24—C19—C18121.0 (13)C59—C60—H60A119.5
C20—C19—C18120.8 (14)C60—C61—C62120.5 (12)
C19—C20—C21119.2 (14)C60—C61—H61A119.7
C19—C20—H20A120.4C62—C61—H61A119.7
C21—C20—H20A120.4C61—C62—C57120.6 (11)
C22—C21—C20120.1 (15)C61—C62—H62B119.7
C22—C21—H21A119.9C57—C62—H62B119.7
C20—C21—H21A119.9
C2—C1—N1—C52(2)C8—C9—C14—C13−45.9 (14)
C2—C1—N1—Tb1−161.5 (13)C10—C9—C14—C13128.2 (10)
C18—O1—Tb1—O236.6 (11)C8—C9—C14—C1545.0 (12)
C18—O1—Tb1—O3−50.4 (11)C10—C9—C14—C15−140.9 (9)
C18—O1—Tb1—O5−131.1 (11)C16—C13—C14—C9−41.5 (16)
C18—O1—Tb1—O4−7.1 (12)C17—C13—C14—C9−168.5 (11)
C18—O1—Tb1—O6−165.4 (10)C12—C13—C14—C977.8 (10)
C18—O1—Tb1—N2146.4 (11)C16—C13—C14—C15−146.2 (13)
C18—O1—Tb1—N199.7 (11)C17—C13—C14—C1586.7 (11)
C5—N1—Tb1—O2135.2 (9)C12—C13—C14—C15−26.9 (8)
C1—N1—Tb1—O2−61.4 (10)C13—C12—C15—C14−27.7 (8)
C5—N1—Tb1—O3−174.3 (6)C11—C12—C15—C1486.4 (9)
C1—N1—Tb1—O3−10.8 (14)C9—C14—C15—C12−82.0 (8)
C5—N1—Tb1—O5−20.7 (10)C13—C14—C15—C1226.9 (9)
C1—N1—Tb1—O5142.8 (9)Tb1—O1—C18—C25−28.7 (19)
C5—N1—Tb1—O173.9 (10)Tb1—O1—C18—C19153.1 (9)
C1—N1—Tb1—O1−122.7 (9)O1—C18—C19—C24−159.4 (12)
C5—N1—Tb1—O4−146.3 (9)C25—C18—C19—C2422 (2)
C1—N1—Tb1—O417.2 (10)O1—C18—C19—C2025 (2)
C5—N1—Tb1—O6−63.8 (9)C25—C18—C19—C20−153.2 (13)
C1—N1—Tb1—O699.7 (10)C24—C19—C20—C213(2)
C5—N1—Tb1—N220.6 (7)C18—C19—C20—C21178.5 (15)
C1—N1—Tb1—N2−176.0 (12)C19—C20—C21—C220(3)
N1—C1—C2—C3−2(3)C20—C21—C22—C23−2(3)
O2—Tb1—N2—C6−88.2 (6)C21—C22—C23—C241(3)
O3—Tb1—N2—C6171.8 (5)C20—C19—C24—C23−4(2)
O5—Tb1—N2—C6126.7 (6)C18—C19—C24—C23−179.5 (13)
O1—Tb1—N2—C6−155.9 (6)C22—C23—C24—C192(2)
O4—Tb1—N2—C6−2.9 (8)O1—C18—C25—C26−3(2)
O6—Tb1—N2—C653.6 (6)C19—C18—C25—C26175.1 (13)
N1—Tb1—N2—C6−23.0 (6)Tb1—O2—C26—C2523.7 (16)
O2—Tb1—N2—C10111.7 (5)Tb1—O2—C26—C27−156.6 (6)
O3—Tb1—N2—C1011.6 (7)C18—C25—C26—O25.8 (19)
O5—Tb1—N2—C10−33.4 (5)C18—C25—C26—C27−173.8 (11)
O1—Tb1—N2—C1043.9 (5)O2—C26—C27—C2825.8 (14)
O4—Tb1—N2—C10−163.0 (6)C25—C26—C27—C28−154.6 (10)
O6—Tb1—N2—C10−106.6 (6)O2—C26—C27—C32−154.9 (10)
N1—Tb1—N2—C10176.8 (6)C25—C26—C27—C3224.8 (15)
O3—Tb1—O2—C2644.0 (9)C32—C27—C28—C29−1.3 (17)
O5—Tb1—O2—C26−13.2 (12)C26—C27—C28—C29178.0 (11)
O1—Tb1—O2—C26−34.6 (9)C27—C28—C29—C300.4 (19)
O4—Tb1—O2—C26117.4 (9)C28—C29—C30—C312(2)
O6—Tb1—O2—C26169.1 (9)C29—C30—C31—C32−2.8 (19)
N2—Tb1—O2—C26−104.5 (9)C28—C27—C32—C310.2 (18)
N1—Tb1—O2—C26−160.0 (10)C26—C27—C32—C31−179.2 (11)
C1—C2—C3—C42(3)C30—C31—C32—C272(2)
O2—Tb1—O3—C3343.7 (7)Tb1—O3—C33—C4024.6 (12)
O5—Tb1—O3—C33−165.2 (7)Tb1—O3—C33—C34−154.1 (6)
O1—Tb1—O3—C33117.4 (7)O3—C33—C34—C3513.6 (14)
O4—Tb1—O3—C33−34.1 (7)C40—C33—C34—C35−165.1 (9)
O6—Tb1—O3—C33−103.0 (7)O3—C33—C34—C39−163.8 (9)
N2—Tb1—O3—C33149.5 (6)C40—C33—C34—C3917.4 (14)
N1—Tb1—O3—C33−5.1 (9)C39—C34—C35—C36−1.5 (17)
C2—C3—C4—C5−2(2)C33—C34—C35—C36−179.0 (10)
O2—Tb1—O4—C41−53.6 (9)C34—C35—C36—C37−2(2)
O3—Tb1—O4—C4133.7 (8)C35—C36—C37—C384(2)
O5—Tb1—O4—C4195.7 (10)C36—C37—C38—C39−2.4 (19)
O1—Tb1—O4—C41−10.9 (11)C35—C34—C39—C383.2 (16)
O6—Tb1—O4—C41155.2 (10)C33—C34—C39—C38−179.4 (9)
N2—Tb1—O4—C41−149.2 (7)C37—C38—C39—C34−1.3 (17)
N1—Tb1—O4—C41−131.3 (10)O3—C33—C40—C415.3 (15)
C1—N1—C5—C4−1.9 (17)C34—C33—C40—C41−176.0 (9)
Tb1—N1—C5—C4161.9 (8)Tb1—O4—C41—C40−24.9 (14)
C1—N1—C5—C6178.1 (9)Tb1—O4—C41—C42153.9 (6)
Tb1—N1—C5—C6−18.0 (12)C33—C40—C41—O4−4.4 (16)
C3—C4—C5—N11.8 (17)C33—C40—C41—C42176.8 (8)
C3—C4—C5—C6−178.2 (10)O4—C41—C42—C4318.0 (13)
O2—Tb1—O5—C48−150.4 (10)C40—C41—C42—C43−163.1 (9)
O3—Tb1—O5—C48151.0 (10)O4—C41—C42—C47−162.8 (10)
O1—Tb1—O5—C48−129.3 (10)C40—C41—C42—C4716.1 (14)
O4—Tb1—O5—C4891.7 (11)C47—C42—C43—C44−2.2 (18)
O6—Tb1—O5—C4828.2 (10)C41—C42—C43—C44177.1 (12)
N2—Tb1—O5—C48−51.4 (10)C42—C43—C44—C451(2)
N1—Tb1—O5—C48−15.2 (11)C43—C44—C45—C46−1(2)
C10—N2—C6—C72.7 (12)C44—C45—C46—C472(2)
Tb1—N2—C6—C7−157.9 (7)C45—C46—C47—C42−3(2)
C10—N2—C6—C5−176.0 (7)C43—C42—C47—C463.0 (16)
Tb1—N2—C6—C523.4 (9)C41—C42—C47—C46−176.2 (10)
N1—C5—C6—N2−3.1 (12)Tb1—O5—C48—C55−23.3 (18)
C4—C5—C6—N2176.9 (9)Tb1—O5—C48—C49157.7 (9)
N1—C5—C6—C7178.2 (10)O5—C48—C49—C54158.3 (12)
C4—C5—C6—C7−1.8 (14)C55—C48—C49—C54−21 (2)
O2—Tb1—O6—C56146.4 (10)O5—C48—C49—C50−25.9 (19)
O3—Tb1—O6—C56−98.2 (10)C55—C48—C49—C50155.0 (11)
O5—Tb1—O6—C56−32.2 (10)C54—C49—C50—C510(2)
O1—Tb1—O6—C562.9 (13)C48—C49—C50—C51−175.8 (15)
O4—Tb1—O6—C56−162.7 (11)C49—C50—C51—C52−2(3)
N2—Tb1—O6—C5650.8 (10)C50—C51—C52—C533(3)
N1—Tb1—O6—C56114.9 (11)C51—C52—C53—C54−1(2)
N2—C6—C7—C8−0.9 (15)C50—C49—C54—C531(2)
C5—C6—C7—C8177.7 (9)C48—C49—C54—C53177.1 (13)
C6—C7—C8—C9−3.4 (16)C52—C53—C54—C49−1(2)
C6—C7—C8—C11175.9 (9)O5—C48—C55—C565.6 (18)
C7—C8—C9—C105.5 (16)C49—C48—C55—C56−175.4 (11)
C11—C8—C9—C10−173.9 (9)Tb1—O6—C56—C5533.0 (16)
C7—C8—C9—C14180.0 (9)Tb1—O6—C56—C57−147.2 (8)
C11—C8—C9—C140.6 (15)C48—C55—C56—O6−11.1 (17)
C6—N2—C10—C9−0.3 (12)C48—C55—C56—C57169.2 (10)
Tb1—N2—C10—C9160.6 (6)O6—C56—C57—C58−15.3 (14)
C8—C9—C10—N2−3.9 (14)C55—C56—C57—C58164.5 (10)
C14—C9—C10—N2−178.0 (8)O6—C56—C57—C62164.1 (10)
C9—C8—C11—C120.4 (14)C55—C56—C57—C62−16.1 (15)
C7—C8—C11—C12−179.0 (10)C62—C57—C58—C59−2.9 (19)
C8—C11—C12—C1347.2 (12)C56—C57—C58—C59176.5 (12)
C8—C11—C12—C15−50.0 (12)C57—C58—C59—C601(2)
C11—C12—C13—C1639.0 (13)C58—C59—C60—C612(2)
C15—C12—C13—C16147.8 (10)C59—C60—C61—C62−3(2)
C11—C12—C13—C17167.7 (10)C60—C61—C62—C571(2)
C15—C12—C13—C17−83.6 (11)C58—C57—C62—C611.9 (18)
C11—C12—C13—C14−80.8 (10)C56—C57—C62—C61−177.5 (11)
C15—C12—C13—C1427.9 (8)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2576).

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