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Acta Cryst. (2007). E63, m1668-m1669    [ doi:10.1107/S1600536807022350 ]

[13,27-Dimethyl-3,6,9,17,20,23-hexaazatricyclo[23.3.1.111,15]triaconta-1(29),2,9,11,13,15(30),16,23,25,27-decaene-29,30-diol-[kappa]5N3,N6,N9,O29,O30]bis(nitrato-[kappa]2O,O')lutetium(III)-nitrate-water-ethyl acetate (1/1/0.5/0.25)

X.-L. Hu, Z. Chen, L. Qiu and Z.-Q. Pan

Abstract top

In the asymmetric unit of the title compound, [LuIII(C26H34N6O2)(NO3)2]NO3·0.5H2O·0.25C4H8O2, there are two cations and two anions of the title complex, together with a water molecule and half a molecule of ethyl acetate. The Lu atom exhibits a nine-coordinate distorted tricapped trigonal-prismatic coordination geometry. The water molecule is disordered, with occupation factors of 0.4 and 0.6.

Comment top

Lanthanide macrocyclic complexes are of particular interest because they have many possible applications in biological systems, material science and chemical processes (Alexander, 1995). Our research is focused on the syntheses, crystal structures and properties of lanthanide(III) complexes with macrocyclic Schiff bases (Hu et al., 2003; Hu et al., 2004). Recently, we have reported the crystal structure of a gadolinium(III) complex with the macrocyclic ligand dervided from 2,6-diformyl-4-methylphenol and 1,5-diamino-3-azapentane ([Gd(III)(C26H34N6O2)(NO3)2]+.(NO3)-.H20), in which the central ion is nine-coordinate, being bound to five donor atoms from the cyclic polydentate ligand and to four O atoms of two bidentae nitrates (Hu et al., 2007). As a part of a continuing study, herein we report a new lutecium analogue [Lu(III)(C26H34N6O2)(NO3)2]+. (NO3)-. 0.5H20. 0.25CH3COOC2H5 (I), but which is a different solvate, belonging to a different space group (space group Cc, compared with C2/c).

In the asymmetric unit (Fig. 1), there are two molecules of the title complex (I) which exhibit a similar coordinate geometry with the previous complex (Hu et al., 2007)(Fig. 2). Lu1 is encapsulated within the macrocyclic ligand which provided five donor atoms (the two O atoms O1,O2 from the phenolates and the three N atoms N1, N2, N3 from one end of the macrocycle). The ninefold coordination is completed around Lu1 by two bidentate nitrates which locate on the opposite sides of the bisphenoidal positions. The third nitrate is ionic. At the free end of the macrocycle, a five-membered imidazole rings is formed. The coordination polyhedron can be described as a distorted tricapped trigonal prism in which N2, O3 and O6 are located at capped sites, as shown in Fig.2. When the phenol oxygen atoms coordinate to the lanthanide ion, the phenol H atoms dissociate and are transferred to the neigbouring imidazole nitrogen to give a zwitterionic structure. This proton transfer has been conformed by NMR study of the tetraiminodiphenol analogue (Spodine et al., 2000).

Related literature top

For related literature, see: Alexander (1995); Hu et al. (2003, 2004, 2007); Spodine et al. (2000).

Experimental top

To a methanolic solution (20 ml) of 2,6-diformyl-4-methylphenol(1 mmol) and Lu(NO3)3.6H2O (0.5 mmol), 1,5-diamino-3-azapentane (1 mmol) was added dropwise. After refluxing 3 h, the solvent was removed. The resultant yellow solid was recrystallized in methanol/ethyl acetate (4/1,v/v) to yield yellow crystals suitable for X-ray analysis.

Refinement top

The carbon-bound H atoms were generated geometrically (C—H 0.93 to 0.97 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2Ueq(C). The nitrogen H were located in a difference Fourier map, and were refined with an N—H distance restraint of 0.90 (1) Å for the sp3-N and 0.86 (1) Å for the sp2-N, their temperature factors were set to 1.2Ueq(C). The water H atoms were also located in a difference Fourier map, and was refined with an O—H distance restraint of 0.85 (1) Å.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot of (I). Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Coordination polyhedron in (I).
[13,27-Dimethyl-3,6,9,17,20,23-hexaazatricyclo[23.3.1.111,15]triaconta- 1(29),2,9,11,13,15 (30),16,23,25,27-decaene-29,30-diol- κ5N3,N6,N9,O29,O30]bis(nitrato-κ2O,O')lutetium(III)– nitrate–water–ethyl acetate (1/1/0.5/0.25) top
Crystal data top
[Lu(C26H34N6O2)(NO3)2]NO3·0.5H2O·0.25C4H8O2F(000) = 3432
Mr = 854.63Dx = 1.568 Mg m−3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 5188 reflections
a = 24.649 (3) Åθ = 2.7–25.6°
b = 14.0182 (11) ŵ = 2.80 mm−1
c = 21.4453 (17) ÅT = 291 K
β = 102.307 (2)°Block, yellow
V = 7239.8 (11) Å30.32 × 0.26 × 0.24 mm
Z = 8
Data collection top
Bruker SMART CCD area-detector
diffractometer		9791 independent reflections
Radiation source: sealed tube8284 reflections with I > 2σ(I)
graphiteRint = 0.046
φ and ω scansθmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −28→30
Tmin = 0.42, Tmax = 0.51k = −17→17
20514 measured reflectionsl = −26→18
Refinement top
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) = 0.104 w = 1/[σ2(Fo2) + (0.06P)2 + 1.55P]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max < 0.001
9791 reflectionsΔρmax = 1.07 e Å−3
913 parametersΔρmin = −1.58 e Å−3
2 restraintsAbsolute structure: Flack (1983), with 2678 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.016 (10)
Crystal data top
[Lu(C26H34N6O2)(NO3)2]NO3·0.5H2O·0.25C4H8O2V = 7239.8 (11) Å3
Mr = 854.63Z = 8
Monoclinic, CcMo Kα radiation
a = 24.649 (3) ŵ = 2.80 mm−1
b = 14.0182 (11) ÅT = 291 K
c = 21.4453 (17) Å0.32 × 0.26 × 0.24 mm
β = 102.307 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		9791 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		8284 reflections with I > 2σ(I)
Tmin = 0.42, Tmax = 0.51Rint = 0.046
20514 measured reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.104Δρmax = 1.07 e Å−3
S = 0.98Δρmin = −1.58 e Å−3
9791 reflectionsAbsolute structure: Flack (1983), with 2678 Friedel pairs
913 parametersFlack parameter: 0.016 (10)
2 restraints
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
xyzUiso*/UeqOcc. (<1)
C10.9197 (4)0.6393 (7)0.5542 (6)0.043 (2)
C20.9711 (4)0.6880 (7)0.5549 (6)0.040 (2)
C30.9722 (5)0.7835 (6)0.5339 (6)0.045 (3)
H31.00620.81250.53420.054*
C40.9244 (5)0.8340 (7)0.5132 (6)0.050 (3)
C50.8765 (5)0.7906 (8)0.5130 (6)0.055 (3)
H50.84420.82580.49950.066*
C60.8709 (4)0.6956 (8)0.5316 (6)0.045 (3)
C70.9282 (5)0.9340 (7)0.4926 (6)0.054 (3)
H7A0.89160.95820.47570.080*
H7B0.94970.93670.46020.080*
H7C0.94580.97200.52840.080*
C80.8162 (5)0.6599 (8)0.5362 (6)0.049 (3)
H80.78780.70490.52830.059*
C90.7438 (5)0.5612 (9)0.5532 (7)0.052 (3)
H9A0.72470.52440.51680.063*
H9B0.72510.62220.55280.063*
C100.7423 (5)0.5092 (8)0.6134 (6)0.049 (3)
H10A0.75990.54700.65000.059*
H10B0.70420.49710.61630.059*
C110.7781 (5)0.3693 (8)0.6744 (6)0.052 (3)
H11A0.74200.35990.68460.062*
H11B0.80070.40710.70800.062*
C120.8055 (5)0.2746 (9)0.6691 (6)0.057 (3)
H12A0.81780.24720.71120.069*
H12B0.77890.23120.64380.069*
C130.8871 (5)0.2180 (9)0.6469 (5)0.051 (3)
H130.88020.17120.67490.062*
C140.9349 (3)0.2014 (5)0.6188 (3)0.040 (3)
C150.9667 (3)0.1209 (4)0.6392 (3)0.054 (4)
H150.95730.08130.67010.065*
C161.0125 (3)0.0996 (4)0.6135 (4)0.059 (4)
C171.0265 (3)0.1588 (6)0.5674 (4)0.056 (3)
H171.05710.14460.55020.067*
C180.9947 (3)0.2393 (5)0.5470 (3)0.054 (3)
C190.9489 (3)0.2606 (4)0.5727 (3)0.046 (3)
C201.0465 (5)0.0076 (8)0.6313 (6)0.058 (3)
H20A1.0267−0.03450.65390.088*
H20B1.08180.02320.65800.088*
H20C1.0520−0.02310.59320.088*
C211.0143 (6)0.3040 (10)0.4989 (7)0.065 (4)
H211.04440.27330.48310.078*
C220.9861 (6)0.4177 (8)0.4176 (7)0.062 (3)
H22A0.99380.40660.37570.074*
H22B0.95780.46670.41420.074*
C231.0382 (5)0.4466 (8)0.4648 (6)0.049 (3)
H23A1.07130.42430.45160.059*
H23B1.04040.51530.47050.059*
C241.0743 (5)0.4001 (9)0.5807 (6)0.061 (3)
H24A1.10890.37730.57140.073*
H24B1.06400.35780.61210.073*
C251.0821 (5)0.5007 (8)0.6073 (7)0.054 (3)
H25A1.09680.49840.65300.064*
H25B1.10830.53500.58770.064*
C261.0234 (4)0.6374 (7)0.5722 (5)0.043 (2)
H261.05550.66870.56750.052*
C270.6628 (5)−0.0607 (8)0.8491 (6)0.051 (3)
C280.6884 (4)−0.1463 (7)0.8727 (5)0.043 (2)
C290.6701 (4)−0.2323 (7)0.8434 (7)0.051 (3)
H290.6879−0.28800.86040.061*
C300.6263 (5)−0.2399 (7)0.7895 (7)0.056 (3)
C310.5985 (5)−0.1562 (7)0.7699 (6)0.050 (3)
H310.5670−0.15920.73720.060*
C320.6154 (5)−0.0653 (7)0.7970 (5)0.042 (2)
C330.6069 (5)−0.3341 (8)0.7597 (7)0.062 (4)
H33A0.6329−0.35680.73550.093*
H33B0.5711−0.32650.73190.093*
H33C0.6044−0.37930.79260.093*
C340.5814 (4)0.0168 (8)0.7729 (6)0.049 (3)
H340.54610.00440.74860.059*
C350.5516 (4)0.1746 (8)0.7561 (6)0.050 (3)
H35A0.52710.14930.71820.060*
H35B0.52950.18730.78760.060*
C360.5767 (5)0.2641 (8)0.7401 (6)0.049 (3)
H36A0.59380.25460.70380.059*
H36B0.54860.31330.72930.059*
C370.6478 (5)0.3853 (7)0.7905 (6)0.050 (3)
H37A0.66240.38460.75190.060*
H37B0.62130.43720.78710.060*
C380.6937 (4)0.4018 (9)0.8460 (6)0.051 (3)
H38A0.67970.40460.88500.061*
H38B0.71230.46150.84120.061*
C390.7845 (5)0.3431 (8)0.8509 (6)0.049 (3)
H390.79360.40750.85550.059*
C400.8274 (5)0.2798 (8)0.8475 (6)0.053 (3)
C410.8802 (5)0.3194 (8)0.8479 (6)0.051 (3)
H410.88480.38500.85310.061*
C420.9261 (5)0.2645 (9)0.8407 (7)0.059 (3)
C430.9177 (5)0.1680 (9)0.8314 (6)0.056 (3)
H430.94690.13080.82410.067*
C440.8659 (5)0.1219 (8)0.8326 (6)0.050 (3)
C450.8203 (4)0.1779 (6)0.8436 (5)0.038 (2)
C460.9822 (5)0.3050 (9)0.8427 (7)0.058 (3)
H46A1.00250.26340.82040.088*
H46B1.00180.31110.88630.088*
H46C0.97860.36660.82270.088*
C470.8622 (4)0.0231 (7)0.8258 (6)0.045 (3)
H470.8922−0.01000.81660.054*
C480.8125 (6)−0.1293 (8)0.8313 (7)0.056 (3)
H48A0.8399−0.15810.81070.068*
H48B0.7759−0.14660.80710.068*
C490.8200 (6)−0.1655 (8)0.8978 (7)0.057 (3)
H49A0.8088−0.23200.89680.068*
H49B0.8589−0.16190.91860.068*
C500.8126 (5)−0.1082 (9)1.0030 (6)0.053 (3)
H50A0.8464−0.07071.01130.064*
H50B0.8206−0.17181.02020.064*
C510.7663 (5)−0.0596 (10)1.0305 (6)0.058 (3)
H51A0.7636−0.08691.07130.070*
H51B0.77220.00861.03530.070*
C520.7310 (5)−0.1478 (7)0.9330 (6)0.045 (3)
H520.7338−0.21260.95050.054*
C530.7210 (8)0.7880 (17)0.6733 (11)0.048 (5)0.50
H53A0.73060.77700.71850.072*0.50
H53B0.72310.72900.65120.072*0.50
H53C0.68390.81280.66170.072*0.50
C540.7593 (9)0.8558 (15)0.6559 (9)0.041 (5)0.50
H54A0.75860.91480.67930.049*0.50
H54B0.74880.86990.61060.049*0.50
C550.8599 (8)0.8684 (18)0.6700 (14)0.054 (7)0.50
C560.9091 (9)0.8130 (16)0.6889 (11)0.048 (5)0.50
H56A0.93840.85250.71200.072*0.50
H56B0.91980.78750.65180.072*0.50
H56C0.90230.76150.71580.072*0.50
Lu10.861690 (18)0.43572 (3)0.58012 (2)0.04135 (12)
Lu20.686348 (16)0.16395 (2)0.834229 (18)0.03540 (10)
N10.8014 (4)0.5761 (6)0.5494 (5)0.046 (2)
N20.7720 (4)0.4191 (6)0.6124 (5)0.046 (2)
H20.75020.38150.58270.055*
N30.8538 (4)0.2866 (6)0.6385 (4)0.045 (2)
N40.9676 (5)0.3261 (7)0.4451 (5)0.057 (3)
H4A0.93590.33510.45880.069*
H4B0.96250.27900.41590.069*
N51.0309 (4)0.3991 (6)0.5223 (5)0.055 (2)
N61.0278 (4)0.5506 (6)0.5939 (5)0.052 (2)
H6A0.99880.52160.60060.062*
N70.8102 (5)0.4138 (7)0.4465 (6)0.056 (3)
N80.9215 (4)0.4878 (8)0.7090 (5)0.057 (3)
N90.7326 (4)0.3201 (6)0.8481 (6)0.051 (3)
N100.6186 (4)0.2922 (6)0.7962 (5)0.048 (2)
H100.59970.30110.82790.058*
N110.5950 (3)0.1032 (6)0.7817 (4)0.042 (2)
N120.7163 (4)−0.0818 (6)0.9802 (5)0.050 (2)
H12C0.6901−0.10840.99810.061*
H12D0.7024−0.02750.96070.061*
N130.7873 (3)−0.1108 (6)0.9349 (4)0.041 (2)
N140.8188 (4)−0.0240 (6)0.8319 (4)0.042 (2)
H14A0.79050.00890.83680.050*
N150.7020 (4)0.1155 (7)0.7101 (5)0.049 (2)
N160.6773 (5)0.2001 (7)0.9653 (6)0.057 (3)
N170.6489 (4)0.7472 (7)0.0480 (5)0.056 (2)
N180.9898 (5)0.1321 (8)0.3560 (5)0.059 (3)
O10.9185 (3)0.5520 (5)0.5724 (4)0.0416 (17)
O20.9172 (3)0.3362 (5)0.5484 (4)0.0427 (17)
O30.8551 (4)0.4623 (6)0.4596 (4)0.057 (2)
O40.7950 (4)0.3748 (6)0.4930 (4)0.060 (2)
O50.7842 (4)0.4060 (6)0.3895 (5)0.070 (3)
O60.9455 (4)0.4326 (6)0.6774 (4)0.059 (2)
O70.8713 (3)0.5109 (5)0.6807 (4)0.051 (2)
O80.9429 (4)0.5204 (6)0.7596 (4)0.066 (2)
O90.7745 (3)0.1369 (5)0.8477 (4)0.0429 (17)
O100.6809 (3)0.0204 (5)0.8760 (3)0.0414 (17)
O110.6952 (3)0.1997 (5)0.7290 (4)0.050 (2)
O120.7000 (4)0.0487 (6)0.7474 (4)0.054 (2)
O130.7098 (4)0.1021 (6)0.6571 (4)0.056 (2)
O140.7238 (4)0.1754 (6)0.9538 (4)0.052 (2)
O150.6371 (4)0.2078 (6)0.9178 (4)0.054 (2)
O160.6708 (3)0.2150 (6)1.0200 (4)0.056 (2)
O170.6216 (3)0.6988 (5)0.0788 (4)0.052 (2)
O180.6296 (3)0.8255 (6)0.0222 (4)0.054 (2)
O190.6943 (3)0.7219 (6)0.0393 (4)0.054 (2)
O201.0301 (4)0.1780 (6)0.3784 (4)0.060 (2)
O210.9908 (3)0.0624 (6)0.3228 (5)0.059 (2)
O220.9461 (3)0.1601 (5)0.3690 (4)0.055 (2)
O230.8155 (6)0.8141 (9)0.6712 (7)0.039 (3)0.50
O240.8546 (6)0.9498 (14)0.6541 (10)0.065 (5)0.50
O250.8703 (6)0.6513 (10)0.8171 (8)0.066 (4)0.60
H25F0.87710.64970.77990.079*0.60
H25C0.83950.62380.81670.079*0.60
O260.5948 (7)0.5428 (14)0.9459 (10)0.056 (5)0.40
H26A0.60120.55070.98610.067*0.40
H26B0.58460.48560.93700.067*0.40
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.046 (6)0.027 (5)0.053 (7)−0.003 (4)0.006 (5)−0.004 (5)
C20.031 (5)0.038 (5)0.057 (7)−0.012 (4)0.019 (4)−0.010 (5)
C30.057 (6)0.024 (5)0.057 (7)−0.004 (4)0.018 (5)−0.006 (5)
C40.058 (7)0.032 (5)0.053 (7)−0.006 (5)−0.004 (5)−0.009 (5)
C50.061 (7)0.036 (6)0.065 (8)0.020 (5)0.009 (6)0.007 (6)
C60.041 (6)0.043 (6)0.053 (7)0.014 (5)0.015 (5)−0.004 (5)
C70.063 (7)0.038 (6)0.049 (7)0.007 (5)−0.010 (6)0.002 (5)
C80.044 (6)0.051 (6)0.050 (7)0.013 (5)0.005 (5)−0.014 (5)
C90.037 (6)0.057 (7)0.061 (9)0.007 (5)0.007 (6)0.001 (6)
C100.048 (6)0.041 (6)0.058 (8)0.004 (5)0.013 (5)0.006 (5)
C110.067 (8)0.044 (6)0.055 (7)−0.019 (5)0.037 (6)−0.016 (5)
C120.056 (7)0.062 (7)0.055 (8)−0.027 (6)0.015 (6)−0.002 (6)
C130.054 (7)0.061 (7)0.033 (6)−0.018 (6)−0.006 (5)0.007 (5)
C140.056 (7)0.018 (4)0.039 (6)0.002 (4)−0.005 (5)0.009 (4)
C150.066 (8)0.028 (5)0.055 (7)−0.003 (5)−0.020 (6)0.011 (5)
C160.068 (8)0.053 (7)0.046 (7)0.010 (6)−0.013 (6)−0.025 (6)
C170.039 (6)0.058 (7)0.062 (8)0.008 (5)−0.009 (5)−0.016 (6)
C180.065 (8)0.052 (7)0.040 (6)0.007 (5)−0.003 (6)−0.014 (5)
C190.049 (7)0.040 (6)0.040 (6)−0.002 (5)−0.010 (5)−0.008 (5)
C200.064 (8)0.046 (6)0.052 (8)0.017 (5)−0.015 (6)−0.011 (6)
C210.057 (8)0.066 (8)0.068 (9)0.024 (6)0.005 (7)−0.006 (7)
C220.073 (9)0.052 (7)0.066 (9)0.015 (6)0.032 (7)0.014 (6)
C230.048 (6)0.050 (6)0.055 (7)0.010 (5)0.027 (5)−0.020 (5)
C240.056 (7)0.065 (7)0.054 (8)0.019 (6)−0.003 (6)−0.015 (6)
C250.040 (6)0.048 (6)0.070 (9)0.006 (5)0.007 (5)0.006 (6)
C260.032 (5)0.046 (6)0.051 (7)−0.002 (4)0.010 (5)0.008 (5)
C270.047 (6)0.047 (6)0.058 (8)−0.012 (5)0.015 (6)0.019 (6)
C280.044 (6)0.042 (6)0.045 (6)−0.007 (4)0.014 (5)−0.012 (5)
C290.049 (6)0.022 (4)0.078 (9)0.002 (4)0.007 (6)0.011 (5)
C300.066 (7)0.019 (5)0.077 (9)−0.010 (4)0.006 (6)−0.013 (5)
C310.037 (6)0.040 (6)0.070 (8)−0.004 (4)0.007 (5)0.007 (6)
C320.044 (6)0.041 (5)0.039 (6)−0.001 (4)0.002 (5)−0.003 (5)
C330.057 (7)0.046 (6)0.070 (9)−0.014 (5)−0.015 (6)−0.018 (6)
C340.031 (5)0.058 (7)0.051 (7)−0.011 (5)−0.009 (5)−0.013 (6)
C350.038 (5)0.050 (6)0.057 (7)0.008 (4)0.003 (5)0.020 (6)
C360.055 (7)0.043 (6)0.048 (7)0.010 (5)0.009 (5)−0.003 (5)
C370.071 (8)0.034 (5)0.050 (7)0.009 (5)0.026 (6)0.018 (5)
C380.032 (6)0.067 (7)0.055 (8)−0.002 (5)0.011 (5)−0.003 (6)
C390.060 (7)0.039 (6)0.054 (8)−0.007 (5)0.022 (6)−0.014 (5)
C400.051 (7)0.049 (6)0.057 (8)−0.009 (5)0.007 (6)−0.004 (6)
C410.061 (7)0.039 (6)0.049 (7)−0.016 (5)0.005 (6)0.016 (5)
C420.040 (6)0.062 (7)0.078 (9)−0.013 (5)0.018 (6)0.023 (7)
C430.055 (7)0.062 (7)0.057 (8)0.001 (6)0.026 (6)0.002 (6)
C440.053 (7)0.042 (6)0.054 (7)−0.006 (5)0.006 (5)−0.002 (5)
C450.038 (5)0.030 (5)0.048 (6)−0.010 (4)0.018 (4)−0.006 (4)
C460.053 (7)0.048 (6)0.072 (9)−0.020 (5)0.008 (6)0.020 (6)
C470.034 (5)0.047 (6)0.053 (7)0.016 (5)0.008 (4)0.016 (6)
C480.066 (8)0.037 (6)0.074 (9)−0.011 (5)0.031 (7)0.003 (6)
C490.059 (8)0.048 (6)0.069 (9)0.011 (5)0.027 (7)0.025 (6)
C500.043 (6)0.052 (7)0.059 (8)−0.005 (5)−0.001 (5)0.002 (6)
C510.056 (7)0.074 (9)0.045 (7)−0.016 (6)0.010 (6)−0.003 (6)
C520.051 (6)0.039 (6)0.049 (7)0.001 (4)0.019 (5)0.014 (5)
C530.033 (10)0.067 (14)0.044 (12)−0.009 (9)0.007 (9)−0.022 (11)
C540.060 (14)0.044 (11)0.023 (10)0.030 (10)0.018 (9)0.013 (8)
C550.026 (10)0.053 (13)0.082 (19)0.015 (9)0.011 (11)−0.023 (13)
C560.037 (11)0.060 (13)0.049 (13)0.027 (10)0.011 (9)0.001 (11)
Lu10.0338 (2)0.0395 (2)0.0515 (3)−0.00315 (19)0.01054 (18)−0.0019 (2)
Lu20.0344 (2)0.02812 (18)0.0447 (2)−0.00110 (17)0.01064 (16)0.0027 (2)
N10.035 (5)0.045 (5)0.056 (6)0.005 (4)0.004 (4)−0.001 (4)
N20.042 (5)0.035 (4)0.062 (6)−0.010 (4)0.016 (4)−0.006 (4)
N30.045 (5)0.050 (5)0.038 (5)−0.015 (4)0.008 (4)0.009 (4)
N40.062 (6)0.070 (7)0.039 (6)0.004 (5)0.009 (5)0.000 (5)
N50.062 (6)0.042 (5)0.058 (6)0.004 (4)0.007 (5)0.000 (5)
N60.033 (5)0.044 (5)0.079 (7)−0.005 (4)0.011 (5)−0.002 (5)
N70.071 (7)0.040 (5)0.051 (7)0.001 (5)−0.001 (6)0.006 (5)
N80.041 (5)0.069 (6)0.059 (7)−0.018 (5)0.005 (5)−0.021 (6)
N90.046 (5)0.025 (4)0.080 (8)−0.008 (4)0.008 (5)−0.013 (5)
N100.033 (4)0.042 (5)0.069 (7)0.005 (4)0.008 (4)0.015 (5)
N110.030 (4)0.047 (5)0.043 (5)0.006 (4)−0.001 (4)0.009 (4)
N120.042 (5)0.035 (5)0.073 (7)0.003 (4)0.010 (5)0.002 (5)
N130.040 (5)0.036 (4)0.045 (5)−0.003 (3)0.002 (4)0.001 (4)
N140.039 (5)0.031 (4)0.054 (6)0.009 (3)0.008 (4)−0.002 (4)
N150.034 (5)0.069 (7)0.045 (6)−0.005 (4)0.014 (4)0.000 (5)
N160.070 (7)0.042 (5)0.063 (8)−0.024 (5)0.021 (6)0.005 (5)
N170.058 (6)0.062 (6)0.055 (6)0.010 (5)0.026 (5)0.007 (5)
N180.062 (7)0.062 (6)0.056 (7)−0.011 (5)0.022 (5)−0.012 (6)
O10.033 (3)0.041 (4)0.052 (5)−0.003 (3)0.011 (3)0.002 (3)
O20.053 (4)0.035 (4)0.041 (4)0.012 (3)0.011 (3)0.005 (3)
O30.055 (5)0.054 (5)0.059 (6)−0.007 (4)0.007 (4)−0.001 (4)
O40.062 (5)0.058 (5)0.054 (5)−0.007 (4)0.001 (4)0.002 (4)
O50.056 (5)0.066 (5)0.072 (7)0.005 (4)−0.020 (5)0.012 (5)
O60.059 (5)0.066 (5)0.051 (5)−0.005 (4)0.010 (4)0.000 (4)
O70.035 (4)0.055 (5)0.064 (5)−0.018 (3)0.011 (4)−0.018 (4)
O80.068 (6)0.063 (5)0.057 (6)−0.009 (4)−0.007 (4)−0.031 (5)
O90.046 (4)0.033 (3)0.053 (5)0.003 (3)0.017 (4)0.001 (3)
O100.044 (4)0.035 (3)0.041 (4)−0.012 (3)−0.001 (3)0.004 (3)
O110.052 (5)0.035 (4)0.068 (6)0.011 (3)0.021 (4)0.008 (4)
O120.060 (5)0.051 (5)0.056 (5)−0.002 (4)0.022 (4)0.004 (4)
O130.066 (5)0.062 (5)0.054 (5)−0.014 (4)0.044 (4)−0.011 (4)
O140.048 (5)0.056 (5)0.053 (5)−0.023 (4)0.012 (4)−0.014 (4)
O150.058 (5)0.052 (5)0.052 (5)0.002 (4)0.014 (4)−0.003 (4)
O160.054 (5)0.056 (5)0.057 (6)−0.012 (4)0.013 (4)−0.012 (4)
O170.054 (5)0.049 (4)0.057 (5)−0.010 (4)0.018 (4)0.017 (4)
O180.049 (5)0.053 (5)0.067 (6)0.015 (4)0.027 (4)0.027 (4)
O190.046 (4)0.063 (5)0.055 (5)0.013 (4)0.012 (4)0.022 (4)
O200.058 (5)0.065 (5)0.059 (6)−0.025 (4)0.015 (4)−0.023 (4)
O210.049 (5)0.058 (5)0.070 (6)−0.004 (4)0.015 (4)−0.009 (5)
O220.049 (5)0.054 (4)0.064 (6)−0.015 (4)0.014 (4)−0.016 (4)
O230.035 (7)0.036 (7)0.041 (8)0.011 (5)−0.006 (6)0.001 (6)
O240.031 (8)0.081 (13)0.082 (14)−0.011 (8)0.011 (8)0.008 (10)
O250.068 (10)0.061 (9)0.075 (11)−0.009 (7)0.028 (8)0.020 (8)
O260.034 (9)0.072 (13)0.061 (13)−0.028 (9)0.009 (9)−0.027 (11)
Geometric parameters (Å, °) top
C1—O11.286 (12)C39—C401.394 (17)
C1—C61.434 (14)C39—H390.9300
C1—C21.436 (14)C40—C411.414 (17)
C2—C31.416 (14)C40—C451.439 (14)
C2—C261.449 (14)C41—C421.404 (18)
C3—C41.365 (15)C41—H410.9300
C3—H30.9300C42—C431.376 (18)
C4—C51.328 (18)C42—C461.488 (15)
C4—C71.479 (15)C43—C441.434 (17)
C5—C61.405 (16)C43—H430.9300
C5—H50.9300C44—C471.393 (15)
C6—C81.460 (17)C44—C451.432 (16)
C7—H7A0.9600C45—O91.287 (12)
C7—H7B0.9600C46—H46A0.9600
C7—H7C0.9600C46—H46B0.9600
C8—N11.279 (15)C46—H46C0.9600
C8—H80.9300C47—N141.287 (14)
C9—N11.456 (15)C47—H470.9300
C9—C101.489 (18)C48—N141.483 (13)
C9—H9A0.9700C48—C491.489 (18)
C9—H9B0.9700C48—H48A0.9700
C10—N21.462 (13)C48—H48B0.9700
C10—H10A0.9700C49—N131.464 (15)
C10—H10B0.9700C49—H49A0.9700
C11—N21.479 (15)C49—H49B0.9700
C11—C121.504 (17)C50—N131.461 (15)
C11—H11A0.9700C50—C511.550 (19)
C11—H11B0.9700C50—H50A0.9700
C12—N31.486 (15)C50—H50B0.9700
C12—H12A0.9700C51—N121.486 (15)
C12—H12B0.9700C51—H51A0.9700
C13—N31.252 (15)C51—H51B0.9700
C13—C141.452 (14)C52—N131.472 (13)
C13—H130.9300C52—N121.474 (15)
C14—C151.3900C52—H520.9800
C14—C191.3900C53—C541.44 (3)
C15—C161.3900C53—H53A0.9600
C15—H150.9300C53—H53B0.9600
C16—C171.3900C53—H53C0.9600
C16—C201.541 (11)C54—O231.47 (2)
C17—C181.3900C54—H54A0.9700
C17—H170.9300C54—H54B0.9700
C18—C191.3900C55—O241.19 (3)
C18—C211.526 (17)C55—O231.34 (3)
C19—O21.353 (8)C55—C561.43 (3)
C20—H20A0.9600C56—H56A0.9600
C20—H20B0.9600C56—H56B0.9600
C20—H20C0.9600C56—H56C0.9600
C21—N51.452 (17)Lu1—O22.163 (7)
C21—N41.478 (16)Lu1—O12.178 (7)
C21—H210.9800Lu1—O72.366 (8)
C22—C231.512 (18)Lu1—O42.368 (8)
C22—N41.522 (15)Lu1—N22.465 (9)
C22—H22A0.9700Lu1—N32.466 (9)
C22—H22B0.9700Lu1—N12.469 (9)
C23—N51.446 (16)Lu1—O32.582 (9)
C23—H23A0.9700Lu1—O62.605 (8)
C23—H23B0.9700Lu1—N72.892 (11)
C24—N51.462 (14)Lu2—O92.163 (7)
C24—C251.519 (16)Lu2—O102.218 (7)
C24—H24A0.9700Lu2—O112.366 (9)
C24—H24B0.9700Lu2—N112.446 (8)
C25—N61.482 (13)Lu2—O152.447 (9)
C25—H25A0.9700Lu2—N92.457 (8)
C25—H25B0.9700Lu2—N102.471 (8)
C26—N61.299 (13)Lu2—O142.539 (9)
C26—H260.9300Lu2—O122.542 (9)
C27—O101.310 (13)Lu2—N152.852 (10)
C27—C281.399 (15)Lu2—N162.912 (12)
C27—C321.436 (16)N2—H20.9100
C28—C291.389 (14)N4—H4A0.9000
C28—C521.482 (15)N4—H4B0.9000
C29—C301.408 (16)N6—H6A0.8600
C29—H290.9300N7—O51.258 (14)
C30—C311.378 (15)N7—O41.263 (14)
C30—C331.500 (13)N7—O31.277 (13)
C31—C321.425 (15)N8—O81.191 (12)
C31—H310.9300N8—O61.257 (13)
C32—C341.453 (15)N8—O71.298 (12)
C33—H33A0.9600N10—H100.9100
C33—H33B0.9600N12—H12C0.9000
C33—H33C0.9600N12—H12D0.9000
C34—N111.260 (14)N14—H14A0.8600
C34—H340.9300N15—O131.209 (12)
C35—C361.472 (16)N15—O121.239 (12)
C35—N111.483 (12)N15—O111.271 (12)
C35—H35A0.9700N16—O161.234 (14)
C35—H35B0.9700N16—O151.265 (14)
C36—N101.462 (14)N16—O141.271 (14)
C36—H36A0.9700N17—O191.224 (12)
C36—H36B0.9700N17—O171.241 (12)
C37—C381.476 (16)N17—O181.275 (12)
C37—N101.508 (14)N18—O201.194 (12)
C37—H37A0.9700N18—O211.211 (13)
C37—H37B0.9700N18—O221.234 (13)
C38—N91.489 (15)O25—H25F0.8499
C38—H38A0.9700O25—H25C0.8500
C38—H38B0.9700O26—H26A0.8499
C39—N91.309 (15)O26—H26B0.8500
O1—C1—C6123.7 (10)N13—C52—C28120.6 (9)
O1—C1—C2121.7 (9)N12—C52—C28110.9 (9)
C6—C1—C2114.6 (9)N13—C52—H52109.1
C3—C2—C1121.6 (10)N12—C52—H52109.1
C3—C2—C26117.9 (9)C28—C52—H52109.1
C1—C2—C26120.3 (9)C54—C53—H53A109.5
C4—C3—C2121.3 (10)C54—C53—H53B109.5
C4—C3—H3119.4H53A—C53—H53B109.5
C2—C3—H3119.4C54—C53—H53C109.5
C5—C4—C3118.0 (10)H53A—C53—H53C109.5
C5—C4—C7123.1 (11)H53B—C53—H53C109.5
C3—C4—C7118.9 (11)C53—C54—O23108.4 (16)
C4—C5—C6125.2 (11)C53—C54—H54A110.0
C4—C5—H5117.4O23—C54—H54A110.0
C6—C5—H5117.4C53—C54—H54B110.0
C5—C6—C1119.4 (10)O23—C54—H54B110.0
C5—C6—C8119.6 (10)H54A—C54—H54B108.4
C1—C6—C8120.5 (10)O24—C55—O23120.7 (18)
C4—C7—H7A109.5O24—C55—C56130 (2)
C4—C7—H7B109.5O23—C55—C56110 (2)
H7A—C7—H7B109.5C55—C56—H56A109.5
C4—C7—H7C109.5C55—C56—H56B109.5
H7A—C7—H7C109.5H56A—C56—H56B109.5
H7B—C7—H7C109.5C55—C56—H56C109.5
N1—C8—C6129.8 (10)H56A—C56—H56C109.5
N1—C8—H8115.1H56B—C56—H56C109.5
C6—C8—H8115.1O2—Lu1—O190.0 (3)
N1—C9—C10108.9 (10)O2—Lu1—O7128.8 (3)
N1—C9—H9A109.9O1—Lu1—O778.1 (3)
C10—C9—H9A109.9O2—Lu1—O484.2 (3)
N1—C9—H9B109.9O1—Lu1—O4124.0 (3)
C10—C9—H9B109.9O7—Lu1—O4142.9 (3)
H9A—C9—H9B108.3O2—Lu1—N2133.9 (3)
N2—C10—C9107.8 (10)O1—Lu1—N2136.2 (3)
N2—C10—H10A110.1O7—Lu1—N273.0 (3)
C9—C10—H10A110.1O4—Lu1—N271.0 (3)
N2—C10—H10B110.1O2—Lu1—N374.7 (3)
C9—C10—H10B110.1O1—Lu1—N3142.6 (3)
H10A—C10—H10B108.5O7—Lu1—N385.3 (3)
N2—C11—C12108.1 (9)O4—Lu1—N388.7 (3)
N2—C11—H11A110.1N2—Lu1—N366.7 (3)
C12—C11—H11A110.1O2—Lu1—N1144.6 (3)
N2—C11—H11B110.1O1—Lu1—N175.1 (3)
C12—C11—H11B110.1O7—Lu1—N180.0 (3)
H11A—C11—H11B108.4O4—Lu1—N178.5 (3)
N3—C12—C11110.3 (9)N2—Lu1—N168.0 (3)
N3—C12—H12A109.6N3—Lu1—N1134.7 (3)
C11—C12—H12A109.6O2—Lu1—O371.8 (3)
N3—C12—H12B109.6O1—Lu1—O373.8 (3)
C11—C12—H12B109.6O7—Lu1—O3145.2 (3)
H12A—C12—H12B108.1O4—Lu1—O351.5 (3)
N3—C13—C14129.0 (10)N2—Lu1—O3115.2 (3)
N3—C13—H13115.5N3—Lu1—O3129.5 (3)
C14—C13—H13115.5N1—Lu1—O373.2 (3)
C15—C14—C19120.0O2—Lu1—O678.1 (3)
C15—C14—C13116.9 (6)O1—Lu1—O670.2 (3)
C19—C14—C13123.1 (6)O7—Lu1—O650.9 (3)
C14—C15—C16120.0O4—Lu1—O6157.5 (3)
C14—C15—H15120.0N2—Lu1—O6112.3 (3)
C16—C15—H15120.0N3—Lu1—O673.4 (3)
C17—C16—C15120.0N1—Lu1—O6123.8 (3)
C17—C16—C20118.2 (8)O3—Lu1—O6132.4 (3)
C15—C16—C20121.7 (8)O2—Lu1—N778.1 (3)
C18—C17—C16120.0O1—Lu1—N799.1 (3)
C18—C17—H17120.0O7—Lu1—N7152.6 (3)
C16—C17—H17120.0O4—Lu1—N725.4 (3)
C19—C18—C17120.0N2—Lu1—N792.2 (3)
C19—C18—C21122.7 (7)N3—Lu1—N7110.4 (3)
C17—C18—C21117.2 (7)N1—Lu1—N773.0 (3)
O2—C19—C18117.8 (6)O3—Lu1—N726.2 (3)
O2—C19—C14122.1 (6)O6—Lu1—N7153.8 (3)
C18—C19—C14120.0O9—Lu2—O1086.1 (3)
C16—C20—H20A109.5O9—Lu2—O1182.6 (3)
C16—C20—H20B109.5O10—Lu2—O11127.1 (3)
H20A—C20—H20B109.5O9—Lu2—N11143.1 (3)
C16—C20—H20C109.5O10—Lu2—N1175.0 (3)
H20A—C20—H20C109.5O11—Lu2—N1184.1 (3)
H20B—C20—H20C109.5O9—Lu2—O15125.9 (3)
N5—C21—N4101.2 (10)O10—Lu2—O1581.4 (3)
N5—C21—C18114.8 (11)O11—Lu2—O15143.7 (3)
N4—C21—C18110.3 (11)N11—Lu2—O1582.7 (3)
N5—C21—H21110.1O9—Lu2—N973.3 (3)
N4—C21—H21110.1O10—Lu2—N9145.6 (3)
C18—C21—H21110.1O11—Lu2—N978.0 (3)
C23—C22—N4104.4 (10)N11—Lu2—N9136.4 (3)
C23—C22—H22A110.9O15—Lu2—N988.7 (3)
N4—C22—H22A110.9O9—Lu2—N10139.5 (3)
C23—C22—H22B110.9O10—Lu2—N10134.3 (3)
N4—C22—H22B110.9O11—Lu2—N1074.0 (3)
H22A—C22—H22B108.9N11—Lu2—N1067.1 (3)
N5—C23—C22101.8 (10)O15—Lu2—N1069.7 (3)
N5—C23—H23A111.4N9—Lu2—N1069.9 (3)
C22—C23—H23A111.4O9—Lu2—O1474.8 (3)
N5—C23—H23B111.4O10—Lu2—O1471.9 (3)
C22—C23—H23B111.4O11—Lu2—O14149.6 (3)
H23A—C23—H23B109.3N11—Lu2—O14126.0 (3)
N5—C24—C25110.0 (10)O15—Lu2—O1451.3 (3)
N5—C24—H24A109.7N9—Lu2—O1476.2 (3)
C25—C24—H24A109.7N10—Lu2—O14111.2 (3)
N5—C24—H24B109.7O9—Lu2—O1272.6 (3)
C25—C24—H24B109.7O10—Lu2—O1275.4 (3)
H24A—C24—H24B108.2O11—Lu2—O1251.9 (3)
N6—C25—C24109.2 (9)N11—Lu2—O1272.2 (3)
N6—C25—H25A109.8O15—Lu2—O12149.3 (3)
C24—C25—H25A109.8N9—Lu2—O12121.7 (3)
N6—C25—H25B109.8N10—Lu2—O12114.0 (3)
C24—C25—H25B109.8O14—Lu2—O12134.8 (3)
H25A—C25—H25B108.3O9—Lu2—N1575.6 (3)
N6—C26—C2123.6 (9)O10—Lu2—N15101.1 (3)
N6—C26—H26118.2O11—Lu2—N1526.1 (3)
C2—C26—H26118.2N11—Lu2—N1577.4 (3)
O10—C27—C28120.0 (10)O15—Lu2—N15158.4 (3)
O10—C27—C32121.8 (10)N9—Lu2—N15100.0 (3)
C28—C27—C32118.2 (10)N10—Lu2—N1594.7 (3)
C29—C28—C27120.2 (10)O14—Lu2—N15150.0 (3)
C29—C28—C52118.9 (10)O12—Lu2—N1525.7 (3)
C27—C28—C52120.6 (9)O9—Lu2—N16100.5 (3)
C28—C29—C30123.7 (9)O10—Lu2—N1675.1 (3)
C28—C29—H29118.2O11—Lu2—N16157.7 (3)
C30—C29—H29118.2N11—Lu2—N16104.6 (3)
C31—C30—C29115.5 (9)O15—Lu2—N1625.5 (3)
C31—C30—C33121.8 (11)N9—Lu2—N1681.8 (3)
C29—C30—C33122.3 (10)N10—Lu2—N1690.4 (4)
C30—C31—C32123.6 (10)O14—Lu2—N1625.8 (3)
C30—C31—H31118.2O12—Lu2—N16150.2 (3)
C32—C31—H31118.2N15—Lu2—N16175.0 (3)
C31—C32—C27118.5 (10)C8—N1—C9118.1 (9)
C31—C32—C34117.8 (9)C8—N1—Lu1127.4 (7)
C27—C32—C34123.6 (9)C9—N1—Lu1114.2 (7)
C30—C33—H33A109.5C10—N2—C11110.5 (9)
C30—C33—H33B109.5C10—N2—Lu1113.8 (7)
H33A—C33—H33B109.5C11—N2—Lu1111.7 (7)
C30—C33—H33C109.5C10—N2—H2106.8
H33A—C33—H33C109.5C11—N2—H2106.8
H33B—C33—H33C109.5Lu1—N2—H2106.8
N11—C34—C32126.3 (9)C13—N3—C12114.3 (10)
N11—C34—H34116.8C13—N3—Lu1127.1 (8)
C32—C34—H34116.8C12—N3—Lu1118.5 (7)
C36—C35—N11110.8 (9)C21—N4—C22103.4 (11)
C36—C35—H35A109.5C21—N4—H4A111.1
N11—C35—H35A109.5C22—N4—H4A111.1
C36—C35—H35B109.5C21—N4—H4B111.1
N11—C35—H35B109.5C22—N4—H4B111.1
H35A—C35—H35B108.1H4A—N4—H4B109.0
N10—C36—C35107.2 (10)C23—N5—C21101.9 (10)
N10—C36—H36A110.3C23—N5—C24121.6 (11)
C35—C36—H36A110.3C21—N5—C24113.9 (9)
N10—C36—H36B110.3C26—N6—C25121.0 (9)
C35—C36—H36B110.3C26—N6—H6A119.5
H36A—C36—H36B108.5C25—N6—H6A119.5
C38—C37—N10111.6 (9)O5—N7—O4123.6 (11)
C38—C37—H37A109.3O5—N7—O3119.9 (12)
N10—C37—H37A109.3O4—N7—O3116.4 (10)
C38—C37—H37B109.3O5—N7—Lu1175.4 (10)
N10—C37—H37B109.3O4—N7—Lu153.4 (5)
H37A—C37—H37B108.0O3—N7—Lu163.2 (6)
C37—C38—N9106.4 (10)O8—N8—O6124.0 (11)
C37—C38—H38A110.5O8—N8—O7121.6 (11)
N9—C38—H38A110.5O6—N8—O7114.3 (9)
C37—C38—H38B110.5C39—N9—C38115.4 (9)
N9—C38—H38B110.5C39—N9—Lu2130.5 (7)
H38A—C38—H38B108.6C38—N9—Lu2113.8 (7)
N9—C39—C40125.8 (10)C36—N10—C37115.6 (9)
N9—C39—H39117.1C36—N10—Lu2112.6 (7)
C40—C39—H39117.1C37—N10—Lu2110.8 (6)
C39—C40—C41117.2 (11)C36—N10—H10105.7
C39—C40—C45123.4 (11)C37—N10—H10105.7
C41—C40—C45119.4 (11)Lu2—N10—H10105.7
C42—C41—C40123.1 (11)C34—N11—C35116.4 (9)
C42—C41—H41118.5C34—N11—Lu2126.4 (7)
C40—C41—H41118.5C35—N11—Lu2117.1 (6)
C43—C42—C41117.0 (10)C52—N12—C51110.1 (9)
C43—C42—C46119.4 (12)C52—N12—H12C109.6
C41—C42—C46123.6 (11)C51—N12—H12C109.6
C42—C43—C44123.2 (11)C52—N12—H12D109.6
C42—C43—H43118.4C51—N12—H12D109.6
C44—C43—H43118.4H12C—N12—H12D108.2
C47—C44—C45121.6 (10)C50—N13—C49112.9 (9)
C47—C44—C43119.1 (11)C50—N13—C52103.7 (9)
C45—C44—C43119.2 (10)C49—N13—C52115.1 (9)
O9—C45—C44119.8 (9)C47—N14—C48126.7 (9)
O9—C45—C40122.5 (9)C47—N14—H14A116.6
C44—C45—C40117.6 (9)C48—N14—H14A116.6
C42—C46—H46A109.5O13—N15—O12121.7 (11)
C42—C46—H46B109.5O13—N15—O11120.2 (10)
H46A—C46—H46B109.5O12—N15—O11118.1 (10)
C42—C46—H46C109.5O13—N15—Lu2175.0 (8)
H46A—C46—H46C109.5O12—N15—Lu263.0 (6)
H46B—C46—H46C109.5O11—N15—Lu255.1 (5)
N14—C47—C44122.6 (10)O16—N16—O15120.9 (12)
N14—C47—H47118.7O16—N16—O14122.3 (11)
C44—C47—H47118.7O15—N16—O14116.8 (11)
N14—C48—C49109.9 (11)O16—N16—Lu2177.0 (9)
N14—C48—H48A109.7O15—N16—Lu256.3 (6)
C49—C48—H48A109.7O14—N16—Lu260.5 (6)
N14—C48—H48B109.7O19—N17—O17122.7 (10)
C49—C48—H48B109.7O19—N17—O18116.9 (10)
H48A—C48—H48B108.2O17—N17—O18120.4 (10)
N13—C49—C48111.8 (10)O20—N18—O21123.6 (11)
N13—C49—H49A109.3O20—N18—O22115.3 (10)
C48—C49—H49A109.3O21—N18—O22121.2 (10)
N13—C49—H49B109.3C1—O1—Lu1142.3 (7)
C48—C49—H49B109.3C19—O2—Lu1137.4 (6)
H49A—C49—H49B107.9N7—O3—Lu190.6 (7)
N13—C50—C51101.5 (9)N7—O4—Lu1101.2 (7)
N13—C50—H50A111.5N8—O6—Lu192.2 (6)
C51—C50—H50A111.5N8—O7—Lu1102.5 (7)
N13—C50—H50B111.5C45—O9—Lu2141.6 (6)
C51—C50—H50B111.5C27—O10—Lu2130.8 (7)
H50A—C50—H50B109.3N15—O11—Lu298.8 (6)
N12—C51—C50101.3 (10)N15—O12—Lu291.2 (6)
N12—C51—H51A111.5N16—O14—Lu293.7 (7)
C50—C51—H51A111.5N16—O15—Lu298.2 (8)
N12—C51—H51B111.5C55—O23—C54120.3 (16)
C50—C51—H51B111.5H25F—O25—H25C109.5
H51A—C51—H51B109.3H26A—O26—H26B109.5
N13—C52—N1297.4 (8)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···O20.902.072.765 (13)133
N4—H4B···O220.901.942.826 (13)166
N4—H4B···O200.902.453.108 (14)130
N4—H4B···N180.902.593.435 (15)156
N6—H6A···O10.861.992.635 (11)131
N6—H6A···O60.862.633.407 (14)151
N10—H10···O150.912.352.810 (13)111
N12—H12D···O100.901.902.641 (12)138
N14—H14A···O90.861.862.560 (10)137
O25—H25F···O80.852.533.007 (19)116
O25—H25C···O5i0.852.322.992 (19)137
N2—H2···O19i0.912.082.959 (11)163
N10—H10···O20ii0.912.243.112 (14)161
N12—H12C···O18iii0.901.922.810 (13)170
N12—H12C···O19iii0.902.533.126 (12)124
N12—H12C···N17iii0.902.593.413 (14)152
Symmetry codes: (i) x, −y+1, z+1/2; (ii) x−1/2, −y+1/2, z+1/2; (iii) x, y−1, z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···O20.902.072.765 (13)133
N4—H4B···O220.901.942.826 (13)166
N4—H4B···O200.902.453.108 (14)130
N4—H4B···N180.902.593.435 (15)156
N6—H6A···O10.861.992.635 (11)131
N6—H6A···O60.862.633.407 (14)151
N10—H10···O150.912.352.810 (13)111
N12—H12D···O100.901.902.641 (12)138
N14—H14A···O90.861.862.560 (10)137
O25—H25F···O80.852.533.007 (19)116
O25—H25C···O5i0.852.322.992 (19)137
N2—H2···O19i0.912.082.959 (11)163
N10—H10···O20ii0.912.243.112 (14)161
N12—H12C···O18iii0.901.922.810 (13)170
N12—H12C···O19iii0.902.533.126 (12)124
N12—H12C···N17iii0.902.593.413 (14)152
Symmetry codes: (i) x, −y+1, z+1/2; (ii) x−1/2, −y+1/2, z+1/2; (iii) x, y−1, z+1.
Acknowledgements top

This work was supported by the Education Office of Hubei Province, China (grant No. D200515004), and Hubei Key Laboratory of Novel Chemical Reactor and Green Chemical Technology, Wuhan Institute of Technology, China (grant No. RCT2004007).

references
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