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Acta Cryst. (2007). E63, m1619-m1620    [ doi:10.1107/S160053680702137X ]

(N-Phenyl-2-{2'-[(phenylethylcarbamoyl)methoxy]biphenyl-2-yloxy}-N-ethylacetamide-[kappa]4O)(2,4,6-trinitrophenolato-[kappa]O)bis(2,4,6-trinitrophenolato-[kappa]2O,O')gadolinium(III)

Y.-L. Guo, Y.-W. Wang, W. Dou, W.-S. Liu and D.-Q. Wang

Abstract top

In the title compound, [Gd(C6H2N3O7)3(C32H32N2O4)], the GdIII ion is nine-coordinated by four O atoms from the N-phenyl-2-{2'-[(phenylethylcarbamoyl)methoxy]biphenyl-2-yloxy}-N-ethylacetamide ligand and five from two bidentate and one monodentate 2,4,6-trinitrophenolate (picrate) ligands. The coordination polyhedron around the GdIII ion is a distorted tricapped trigonal prism. The tetradentate ligand wraps around the metal ion with its O atoms and forms a ring-like coordination structure together with the Gd atom. The mean distance between the Gd atom and the coordinated carbonyl O atoms is shorter than that between the Gd atom and the coordinated ether atoms. This suggests that the Gd-O (C=O) bond is stronger than the Gd-O (C-O-C) bond.

Comment top

Metal-directed self-assembly of organic ligands and metal ions, or organometallic moieties, to form well defined structures has been a very attractive field in recent years (Lehn, 1995; Steed & Atwood, 2000; Bourne et al., 2001;), for their fascinating structural diversities and potential application in functional materials, nanotechnology and biological recognition (Evan & Lin, 2002; Janiak, 2003; Carlucci et al., 2003; Gutschke et al., 1996;). We have now investigated the assembly of the ligand N-phenyl-2-{2'-[(phenyl- ethyl-carbamoyl)-methoxy]-biphenyl-2-yloxy}-N-ethyl-acetamide with gadolinium picrate.

In the title complex I, The Gd(III) ion is coordinated by 9 oxygen donor atoms, five of them belonging to two bidentate and one monodentate picrate groups whereas the remaining four are from the tetradentate ligand L(Fig. 1). The coordination polyhedron around Gd(III) ion is a distorted tricapped trigonal prism (Fig. 2) (Wang et al., 2003). The quadridentate ligand wraps around the metal ion with its oxygen atoms and forms a ring-like coordination structure together with the Gd atom. The two phenyl rings about the central bond in the molecule have a drastic twisting, with the dihedral angle between them being 61.18°. The mean distances between the Gd atom and the coordinated ether and carbonyl oxygen atoms are 2.575 Å and 2.3105 Å, respectively. This suggests that the Gd—O (C?O) bond is stronger than the Gd—O (C—O—C) bond.

Related literature top

For general backgound, see: Lehn, 1995; Steed & Atwood, 2000; Bourne et al., 2001; Evan & Lin, 2002; Janiak, 2003; Carlucci et al., 2003; Gutschke et al., 1996. For related structures, see: Wang et al., 2003.

Experimental top

To a solution of 0.2 mmol gadolinium picrate in 5 ml of ethanol was added dropwise the solution of 0.2 mmol ligand in 10 ml of ethanol. The mixture was stirred at room temperature for 6 h. The precipitated solid complex was filtered, washed with ethanol and dried in vacuo over P2O5 for 72 h. The complex was obtained as yellow powder. Single crystal of the gadolinium complex grew from CH3Cl and CH3CH2OH by slow evaporation at room temperature. After about two weeks, yellow crystal formed from the solution.

Refinement top

All H atoms attached were fixed geometrically and treated as riding with C—H = 0.93 Å (Caromatic), 0.97 Å (Cmethylene) and C—H =0.96 Å (Cmethyl) with Uiso(H) = 1.2Ueq(Caromatic or Cmethylene) and Uiso(H) = 1.5Ueq(Cmethyl).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The independent components of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. The coordination polyhedron of (I), showing the distorted tricapped trigonal prism.
(N-Phenyl-2-{2'-[(phenylethylcarbamoyl)methoxy]biphenyl-2-yloxy}- N-ethylacetamide-κ4O)(2,4,6-trinitrophenolato-κO) bis(2,4,6-trinitrophenolato-κ2O,O')gadolinium(III) top
Crystal data top
[Gd(C6H2N3O7)3(C32H32N2O4)]F(000) = 2716
Mr = 1350.16Dx = 1.652 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8109 reflections
a = 20.125 (2) Åθ = 2.2–25.3°
b = 16.7778 (18) ŵ = 1.32 mm−1
c = 16.6491 (18) ÅT = 298 K
β = 105.051 (2)°Block, yellow
V = 5428.9 (10) Å30.40 × 0.37 × 0.29 mm
Z = 4
Data collection top
Bruker SMART CCD area detector
diffractometer		9559 independent reflections
Radiation source: fine-focus sealed tube6585 reflections with I > 2σ(I)
graphiteRint = 0.036
phi and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −16→23
Tmin = 0.620, Tmax = 0.701k = −19→19
28190 measured reflectionsl = −19→17
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0225P)2 + 8.0112P]
where P = (Fo2 + 2Fc2)/3
9559 reflections(Δ/σ)max = 0.002
786 parametersΔρmax = 1.50 e Å−3
0 restraintsΔρmin = −0.58 e Å−3
Crystal data top
[Gd(C6H2N3O7)3(C32H32N2O4)]V = 5428.9 (10) Å3
Mr = 1350.16Z = 4
Monoclinic, P21/cMo Kα radiation
a = 20.125 (2) ŵ = 1.32 mm−1
b = 16.7778 (18) ÅT = 298 K
c = 16.6491 (18) Å0.40 × 0.37 × 0.29 mm
β = 105.051 (2)°
Data collection top
Bruker SMART CCD area detector
diffractometer		9559 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		6585 reflections with I > 2σ(I)
Tmin = 0.620, Tmax = 0.701Rint = 0.036
28190 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.087Δρmax = 1.50 e Å−3
S = 1.08Δρmin = −0.58 e Å−3
9559 reflectionsAbsolute structure: ?
786 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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*/Ueq
Gd0.749509 (11)0.628330 (12)0.769967 (14)0.03694 (8)
N10.9530 (2)0.7437 (2)0.8655 (3)0.0527 (11)
N20.5485 (2)0.7472 (3)0.6819 (3)0.0604 (12)
N30.6661 (2)0.4428 (3)0.7896 (3)0.0558 (11)
N40.7446 (4)0.1794 (3)0.7376 (3)0.0817 (17)
N50.8962 (2)0.4044 (3)0.7360 (3)0.0580 (11)
N60.8047 (2)0.5775 (2)0.5830 (3)0.0526 (11)
N70.7101 (3)0.3392 (3)0.4317 (3)0.0794 (15)
N80.5725 (2)0.4815 (3)0.5851 (3)0.0649 (13)
N90.9043 (3)0.5088 (3)0.9422 (3)0.0657 (13)
N100.7864 (4)0.3033 (3)1.0554 (3)0.0798 (16)
N110.6777 (3)0.5639 (3)0.9963 (4)0.0712 (14)
O10.85746 (15)0.68313 (18)0.7941 (2)0.0476 (8)
O20.77451 (14)0.75760 (16)0.85945 (19)0.0421 (8)
O30.64424 (14)0.69007 (17)0.75993 (19)0.0411 (7)
O40.72718 (14)0.75474 (16)0.68295 (18)0.0398 (7)
O50.79637 (15)0.50497 (16)0.7700 (2)0.0456 (8)
O60.66987 (17)0.51556 (19)0.7911 (2)0.0602 (10)
O70.6175 (2)0.4090 (2)0.8044 (3)0.1057 (17)
O80.6861 (3)0.1556 (2)0.7312 (3)0.1065 (17)
O90.7935 (3)0.1368 (2)0.7345 (3)0.1079 (17)
O100.9479 (2)0.3659 (2)0.7687 (3)0.0836 (12)
O110.8964 (2)0.4630 (2)0.6944 (3)0.0776 (12)
O120.68209 (16)0.58803 (18)0.6408 (2)0.0524 (9)
O130.81129 (17)0.62156 (19)0.6441 (2)0.0576 (9)
O140.8431 (2)0.5811 (2)0.5371 (3)0.0747 (11)
O150.7645 (3)0.3316 (3)0.4143 (3)0.1159 (19)
O160.6607 (3)0.2947 (3)0.4072 (3)0.0965 (15)
O170.5489 (2)0.4223 (3)0.6085 (3)0.1105 (17)
O180.5445 (2)0.5463 (3)0.5762 (3)0.0924 (14)
O190.78189 (17)0.60133 (18)0.9109 (2)0.0557 (9)
O200.9221 (2)0.5779 (3)0.9556 (3)0.0882 (13)
O210.9358 (2)0.4588 (3)0.9138 (3)0.0891 (13)
O220.8388 (3)0.2635 (3)1.0675 (3)0.1086 (17)
O230.7321 (3)0.2800 (2)1.0683 (3)0.0938 (14)
O240.6489 (2)0.5496 (3)1.0510 (3)0.0947 (15)
O250.6636 (3)0.6196 (3)0.9512 (4)0.135 (2)
C10.7289 (2)0.8213 (3)0.8567 (3)0.0438 (12)
C20.6850 (3)0.8186 (3)0.9071 (3)0.0571 (14)
H20.68820.77750.94550.069*
C30.6358 (3)0.8777 (4)0.9003 (4)0.0713 (17)
H30.60480.87590.93300.086*
C40.6330 (3)0.9391 (4)0.8450 (4)0.081 (2)
H40.60050.97920.84130.097*
C50.6779 (3)0.9420 (3)0.7950 (4)0.0713 (17)
H50.67590.98450.75870.086*
C60.7264 (2)0.8814 (3)0.7984 (3)0.0495 (12)
C70.7730 (2)0.8811 (3)0.7422 (3)0.0495 (12)
C80.8195 (3)0.9428 (3)0.7435 (4)0.0711 (17)
H80.82030.98630.77840.085*
C90.8642 (3)0.9402 (4)0.6938 (5)0.083 (2)
H90.89560.98140.69630.099*
C100.8633 (3)0.8781 (3)0.6406 (4)0.0692 (16)
H100.89400.87690.60740.083*
C110.8165 (2)0.8170 (3)0.6364 (3)0.0546 (13)
H110.81530.77450.60010.066*
C120.7720 (2)0.8196 (3)0.6860 (3)0.0421 (11)
C130.8865 (2)0.7291 (3)0.8501 (3)0.0404 (11)
C140.8455 (2)0.7713 (3)0.9012 (3)0.0466 (12)
H14A0.85620.74980.95720.056*
H14B0.85560.82790.90430.056*
C150.9900 (2)0.7912 (3)0.9347 (3)0.0534 (13)
C161.0082 (3)0.7587 (4)1.0134 (4)0.0774 (18)
H160.99590.70671.02260.093*
C171.0449 (4)0.8047 (6)1.0778 (5)0.112 (3)
H171.05720.78411.13140.135*
C181.0633 (4)0.8798 (6)1.0638 (6)0.114 (3)
H181.08850.91001.10810.137*
C191.0456 (3)0.9123 (4)0.9861 (6)0.093 (2)
H191.05860.96410.97740.112*
C201.0086 (3)0.8675 (3)0.9206 (4)0.0669 (15)
H200.99620.88870.86720.080*
C210.9901 (3)0.7119 (4)0.8036 (5)0.093 (2)
H21A0.96090.71920.74780.111*
H21B1.03170.74270.80830.111*
C221.0076 (4)0.6313 (4)0.8152 (5)0.115 (3)
H22A1.03550.62330.87090.173*
H22B1.03290.61550.77630.173*
H22C0.96650.59990.80650.173*
C230.6152 (2)0.7319 (3)0.6994 (3)0.0406 (11)
C240.6557 (2)0.7696 (3)0.6443 (3)0.0429 (11)
H24A0.64260.74620.58920.052*
H24B0.64690.82650.63940.052*
C250.5145 (2)0.7904 (3)0.6082 (4)0.0600 (15)
C260.4971 (3)0.7523 (4)0.5331 (4)0.0774 (18)
H260.50780.69880.52950.093*
C270.4633 (3)0.7942 (5)0.4619 (5)0.097 (2)
H270.45090.76880.41050.117*
C280.4486 (3)0.8726 (6)0.4686 (5)0.102 (3)
H280.42640.90090.42120.122*
C290.4658 (3)0.9104 (4)0.5432 (5)0.096 (2)
H290.45490.96390.54660.115*
C300.4995 (3)0.8692 (4)0.6143 (4)0.0760 (17)
H300.51180.89500.66550.091*
C310.5076 (3)0.7199 (4)0.7423 (4)0.0829 (19)
H31A0.53530.72650.79910.100*
H31B0.46660.75250.73510.100*
C320.4882 (4)0.6369 (5)0.7274 (5)0.113 (3)
H32A0.46360.62990.67020.169*
H32B0.45920.62150.76240.169*
H32C0.52880.60430.73980.169*
C330.7823 (2)0.4308 (3)0.7624 (3)0.0403 (11)
C340.7199 (2)0.3955 (3)0.7704 (3)0.0435 (11)
C350.7077 (3)0.3137 (3)0.7636 (3)0.0553 (13)
H350.66650.29250.76940.066*
C360.7573 (3)0.2654 (3)0.7482 (3)0.0585 (15)
C370.8195 (3)0.2949 (3)0.7425 (3)0.0569 (14)
H370.85360.26050.73510.068*
C380.8307 (2)0.3745 (3)0.7477 (3)0.0446 (11)
C390.6896 (2)0.5324 (3)0.5928 (3)0.0420 (11)
C400.7487 (2)0.5201 (3)0.5628 (3)0.0422 (11)
C410.7559 (3)0.4577 (3)0.5115 (3)0.0529 (13)
H410.79570.45240.49360.063*
C420.7036 (3)0.4038 (3)0.4877 (3)0.0548 (14)
C430.6442 (3)0.4111 (3)0.5133 (3)0.0537 (13)
H430.60920.37360.49740.064*
C440.6373 (2)0.4742 (3)0.5623 (3)0.0463 (12)
C450.7854 (3)0.5374 (3)0.9522 (3)0.0495 (13)
C460.8420 (3)0.4827 (3)0.9640 (3)0.0503 (13)
C470.8420 (3)0.4077 (3)0.9951 (3)0.0576 (14)
H470.87860.37330.99740.069*
C480.7870 (3)0.3842 (3)1.0228 (3)0.0586 (14)
C490.7337 (3)0.4356 (3)1.0239 (3)0.0597 (14)
H490.69850.42001.04720.072*
C500.7336 (3)0.5102 (3)0.9904 (3)0.0539 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Gd0.03632 (13)0.02908 (11)0.04381 (13)0.00121 (11)0.00754 (9)−0.00233 (11)
N10.037 (2)0.055 (3)0.070 (3)−0.009 (2)0.021 (2)−0.017 (2)
N20.037 (2)0.070 (3)0.076 (3)0.010 (2)0.017 (2)0.027 (2)
N30.060 (3)0.051 (3)0.061 (3)−0.011 (2)0.024 (2)0.003 (2)
N40.141 (5)0.024 (2)0.083 (4)−0.008 (3)0.034 (4)0.005 (2)
N50.058 (3)0.053 (3)0.068 (3)0.014 (2)0.025 (2)−0.007 (2)
N60.055 (3)0.052 (3)0.049 (3)0.006 (2)0.010 (2)0.010 (2)
N70.082 (4)0.082 (4)0.067 (4)0.012 (3)0.006 (3)−0.030 (3)
N80.056 (3)0.078 (4)0.059 (3)−0.008 (3)0.013 (2)−0.019 (3)
N90.068 (3)0.074 (3)0.053 (3)0.006 (3)0.013 (2)0.007 (3)
N100.110 (5)0.067 (4)0.062 (3)−0.006 (4)0.021 (3)0.016 (3)
N110.075 (4)0.057 (3)0.085 (4)−0.009 (3)0.028 (3)−0.014 (3)
O10.0425 (19)0.0457 (18)0.055 (2)−0.0046 (15)0.0132 (15)−0.0132 (16)
O20.0371 (18)0.0340 (16)0.053 (2)0.0047 (13)0.0076 (14)−0.0029 (14)
O30.0390 (18)0.0380 (17)0.047 (2)0.0055 (14)0.0124 (15)0.0019 (15)
O40.0328 (17)0.0326 (16)0.053 (2)0.0002 (13)0.0082 (14)0.0022 (14)
O50.0463 (19)0.0267 (16)0.067 (2)0.0026 (14)0.0214 (16)−0.0031 (15)
O60.057 (2)0.0381 (19)0.093 (3)0.0003 (17)0.032 (2)0.0017 (18)
O70.090 (3)0.070 (3)0.186 (5)−0.021 (2)0.087 (3)−0.001 (3)
O80.148 (5)0.054 (3)0.123 (4)−0.038 (3)0.044 (4)−0.008 (2)
O90.167 (5)0.037 (2)0.123 (4)0.029 (3)0.043 (3)−0.003 (2)
O100.062 (3)0.086 (3)0.103 (3)0.030 (2)0.022 (2)0.005 (3)
O110.075 (3)0.064 (3)0.109 (3)0.010 (2)0.052 (2)0.017 (2)
O120.056 (2)0.0490 (19)0.048 (2)0.0068 (16)0.0069 (16)−0.0169 (16)
O130.061 (2)0.048 (2)0.060 (2)−0.0081 (18)0.0088 (17)−0.0074 (19)
O140.077 (3)0.084 (3)0.070 (3)−0.011 (2)0.032 (2)0.004 (2)
O150.089 (4)0.146 (5)0.108 (4)0.025 (3)0.018 (3)−0.072 (3)
O160.111 (4)0.080 (3)0.091 (3)−0.011 (3)0.013 (3)−0.047 (3)
O170.102 (4)0.116 (4)0.132 (5)−0.034 (3)0.064 (3)−0.001 (3)
O180.058 (3)0.103 (4)0.114 (4)0.010 (3)0.019 (2)−0.039 (3)
O190.076 (2)0.0409 (19)0.048 (2)0.0006 (17)0.0120 (17)0.0030 (16)
O200.084 (3)0.082 (3)0.100 (4)−0.020 (3)0.025 (2)0.006 (3)
O210.077 (3)0.104 (3)0.092 (3)0.019 (3)0.033 (3)0.006 (3)
O220.130 (4)0.076 (3)0.121 (4)0.031 (3)0.034 (3)0.041 (3)
O230.128 (4)0.072 (3)0.082 (3)−0.026 (3)0.027 (3)0.015 (2)
O240.093 (3)0.084 (3)0.124 (4)−0.014 (3)0.059 (3)−0.024 (3)
O250.138 (5)0.114 (4)0.176 (6)0.071 (4)0.081 (4)0.067 (4)
C10.038 (3)0.033 (3)0.056 (3)0.003 (2)0.005 (2)−0.016 (2)
C20.052 (3)0.060 (3)0.060 (4)0.000 (3)0.016 (3)−0.021 (3)
C30.056 (4)0.082 (4)0.077 (4)0.004 (3)0.018 (3)−0.035 (4)
C40.064 (4)0.077 (4)0.094 (5)0.027 (3)0.007 (4)−0.038 (4)
C50.075 (4)0.045 (3)0.085 (5)0.016 (3)0.005 (4)−0.008 (3)
C60.048 (3)0.029 (3)0.066 (3)0.005 (2)0.005 (3)−0.007 (2)
C70.050 (3)0.031 (3)0.062 (3)−0.002 (2)0.005 (3)0.006 (2)
C80.086 (5)0.036 (3)0.086 (5)−0.016 (3)0.013 (4)0.006 (3)
C90.076 (5)0.059 (4)0.106 (6)−0.034 (3)0.010 (4)0.024 (4)
C100.056 (3)0.067 (4)0.087 (5)−0.011 (3)0.023 (3)0.027 (4)
C110.053 (3)0.054 (3)0.058 (4)−0.001 (3)0.015 (3)0.013 (3)
C120.035 (3)0.035 (3)0.053 (3)−0.002 (2)0.005 (2)0.010 (2)
C130.039 (3)0.035 (2)0.048 (3)−0.003 (2)0.014 (2)−0.002 (2)
C140.039 (3)0.049 (3)0.050 (3)0.000 (2)0.007 (2)−0.011 (2)
C150.034 (3)0.058 (3)0.066 (4)−0.009 (2)0.011 (2)−0.013 (3)
C160.064 (4)0.081 (4)0.080 (5)−0.008 (3)0.007 (3)0.000 (4)
C170.094 (6)0.153 (8)0.070 (5)−0.008 (6)−0.012 (4)−0.007 (5)
C180.081 (5)0.134 (8)0.113 (7)−0.037 (5)0.001 (5)−0.053 (6)
C190.069 (5)0.077 (5)0.137 (7)−0.028 (4)0.030 (5)−0.030 (5)
C200.048 (3)0.067 (4)0.088 (4)−0.012 (3)0.023 (3)−0.009 (3)
C210.057 (4)0.085 (5)0.147 (7)−0.010 (4)0.044 (4)−0.019 (5)
C220.084 (5)0.109 (6)0.154 (8)0.010 (5)0.033 (5)−0.011 (6)
C230.038 (3)0.034 (2)0.049 (3)0.000 (2)0.012 (2)−0.005 (2)
C240.033 (3)0.046 (3)0.048 (3)0.005 (2)0.009 (2)0.003 (2)
C250.034 (3)0.068 (4)0.078 (4)0.008 (3)0.015 (3)0.019 (3)
C260.057 (4)0.084 (4)0.087 (5)−0.003 (3)0.010 (3)0.012 (4)
C270.070 (5)0.128 (7)0.088 (6)0.001 (5)0.010 (4)0.004 (5)
C280.068 (4)0.144 (8)0.094 (6)0.027 (5)0.020 (4)0.052 (6)
C290.074 (5)0.095 (5)0.123 (7)0.034 (4)0.031 (5)0.046 (5)
C300.054 (3)0.082 (4)0.094 (5)0.021 (3)0.021 (3)0.021 (4)
C310.054 (4)0.094 (5)0.101 (5)0.006 (3)0.020 (3)0.028 (4)
C320.092 (5)0.128 (7)0.120 (7)−0.025 (5)0.033 (5)−0.014 (5)
C330.049 (3)0.034 (3)0.036 (3)0.003 (2)0.008 (2)0.003 (2)
C340.051 (3)0.040 (3)0.042 (3)0.000 (2)0.016 (2)0.000 (2)
C350.073 (4)0.047 (3)0.048 (3)−0.007 (3)0.021 (3)0.005 (2)
C360.093 (4)0.029 (2)0.054 (4)0.000 (3)0.021 (3)0.001 (2)
C370.075 (4)0.044 (3)0.051 (3)0.016 (3)0.016 (3)−0.002 (2)
C380.056 (3)0.032 (2)0.047 (3)0.005 (2)0.015 (2)0.000 (2)
C390.051 (3)0.038 (3)0.034 (3)0.005 (2)0.005 (2)0.001 (2)
C400.048 (3)0.037 (3)0.036 (3)0.000 (2)0.002 (2)0.001 (2)
C410.055 (3)0.059 (3)0.043 (3)0.010 (3)0.009 (2)0.000 (3)
C420.067 (4)0.054 (3)0.040 (3)0.007 (3)0.008 (3)−0.016 (2)
C430.067 (4)0.042 (3)0.048 (3)−0.009 (3)0.008 (3)−0.006 (2)
C440.053 (3)0.045 (3)0.040 (3)0.002 (2)0.011 (2)−0.002 (2)
C450.061 (3)0.045 (3)0.038 (3)−0.002 (3)0.005 (2)−0.003 (2)
C460.056 (3)0.050 (3)0.045 (3)−0.001 (3)0.012 (2)0.005 (2)
C470.069 (4)0.055 (3)0.047 (3)0.010 (3)0.011 (3)0.010 (3)
C480.075 (4)0.049 (3)0.049 (3)0.003 (3)0.011 (3)0.015 (3)
C490.063 (4)0.064 (4)0.052 (3)−0.008 (3)0.016 (3)0.004 (3)
C500.060 (3)0.048 (3)0.052 (3)0.000 (3)0.010 (3)−0.003 (3)
Geometric parameters (Å, °) top
Gd—O52.274 (3)C10—C111.380 (7)
Gd—O12.296 (3)C10—H100.9300
Gd—O192.311 (3)C11—C121.369 (7)
Gd—O32.325 (3)C11—H110.9300
Gd—O122.326 (3)C13—C141.508 (6)
Gd—O42.542 (3)C14—H14A0.9700
Gd—O62.562 (3)C14—H14B0.9700
Gd—O22.605 (3)C15—C201.370 (7)
Gd—O132.703 (4)C15—C161.378 (7)
N1—C131.318 (5)C16—C171.371 (9)
N1—C151.440 (6)C16—H160.9300
N1—C211.517 (7)C17—C181.350 (10)
N2—C231.321 (5)C17—H170.9300
N2—C251.436 (6)C18—C191.363 (10)
N2—C311.527 (7)C18—H180.9300
N3—O71.209 (5)C19—C201.373 (8)
N3—O61.223 (5)C19—H190.9300
N3—C341.445 (6)C20—H200.9300
N4—O81.221 (6)C21—C221.397 (8)
N4—O91.228 (7)C21—H21A0.9700
N4—C361.468 (6)C21—H21B0.9700
N5—O111.203 (5)C22—H22A0.9600
N5—O101.225 (5)C22—H22B0.9600
N5—C381.469 (6)C22—H22C0.9600
N6—O141.221 (5)C23—C241.515 (6)
N6—O131.236 (5)C24—H24A0.9700
N6—C401.454 (6)C24—H24B0.9700
N7—O151.210 (6)C25—C261.365 (8)
N7—O161.224 (6)C25—C301.367 (7)
N7—C421.458 (6)C26—C271.394 (9)
N8—O171.208 (6)C26—H260.9300
N8—O181.216 (6)C27—C281.360 (10)
N8—C441.453 (6)C27—H270.9300
N9—O201.218 (6)C28—C291.357 (10)
N9—O211.219 (6)C28—H280.9300
N9—C461.460 (7)C29—C301.386 (8)
N10—O221.221 (6)C29—H290.9300
N10—O231.230 (6)C30—H300.9300
N10—C481.462 (7)C31—C321.451 (8)
N11—O251.186 (6)C31—H31A0.9700
N11—O241.223 (6)C31—H31B0.9700
N11—C501.466 (7)C32—H32A0.9600
O1—C131.234 (5)C32—H32B0.9600
O2—C11.402 (5)C32—H32C0.9600
O2—C141.436 (5)C33—C381.424 (6)
O3—C231.243 (5)C33—C341.426 (6)
O4—C121.405 (5)C34—C351.393 (6)
O4—C241.437 (5)C35—C361.360 (7)
O5—C331.275 (5)C35—H350.9300
O12—C391.262 (5)C36—C371.372 (7)
O19—C451.266 (5)C37—C381.354 (6)
C1—C21.368 (7)C37—H370.9300
C1—C61.391 (7)C39—C401.420 (6)
C2—C31.385 (7)C39—C441.429 (6)
C2—H20.9300C40—C411.382 (6)
C3—C41.371 (8)C41—C421.365 (7)
C3—H30.9300C41—H410.9300
C4—C51.379 (8)C42—C431.375 (7)
C4—H40.9300C43—C441.367 (6)
C5—C61.400 (7)C43—H430.9300
C5—H50.9300C45—C501.429 (7)
C6—C71.487 (7)C45—C461.436 (7)
C7—C121.390 (6)C46—C471.361 (6)
C7—C81.392 (7)C47—C481.363 (7)
C8—C91.373 (8)C47—H470.9300
C8—H80.9300C48—C491.380 (7)
C9—C101.364 (8)C49—C501.369 (7)
C9—H90.9300C49—H490.9300
O5—Gd—O189.48 (10)C13—C14—H14B110.6
O5—Gd—O1979.26 (11)H14A—C14—H14B108.7
O1—Gd—O1984.06 (12)C20—C15—C16121.0 (5)
O5—Gd—O3140.85 (10)C20—C15—N1119.2 (5)
O1—Gd—O3129.59 (10)C16—C15—N1119.7 (5)
O19—Gd—O399.89 (11)C17—C16—C15118.4 (6)
O5—Gd—O1282.99 (11)C17—C16—H16120.8
O1—Gd—O12125.18 (12)C15—C16—H16120.8
O19—Gd—O12145.59 (12)C18—C17—C16120.5 (8)
O3—Gd—O1276.19 (11)C18—C17—H17119.8
O5—Gd—O4140.48 (10)C16—C17—H17119.8
O1—Gd—O477.57 (10)C17—C18—C19121.4 (7)
O19—Gd—O4134.73 (10)C17—C18—H18119.3
O3—Gd—O464.17 (10)C19—C18—H18119.3
O12—Gd—O474.99 (10)C18—C19—C20119.2 (7)
O5—Gd—O666.55 (11)C18—C19—H19120.4
O1—Gd—O6150.32 (11)C20—C19—H19120.4
O19—Gd—O674.79 (12)C15—C20—C19119.5 (6)
O3—Gd—O675.41 (10)C15—C20—H20120.3
O12—Gd—O671.14 (12)C19—C20—H20120.3
O4—Gd—O6132.07 (10)C22—C21—N1113.4 (6)
O5—Gd—O2137.64 (10)C22—C21—H21A108.9
O1—Gd—O262.18 (10)N1—C21—H21A108.9
O19—Gd—O267.72 (10)C22—C21—H21B108.9
O3—Gd—O272.98 (9)N1—C21—H21B108.9
O12—Gd—O2138.64 (10)H21A—C21—H21B107.7
O4—Gd—O267.09 (9)C21—C22—H22A109.5
O6—Gd—O2124.83 (10)C21—C22—H22B109.5
O5—Gd—O1371.81 (11)H22A—C22—H22B109.5
O1—Gd—O1363.09 (10)C21—C22—H22C109.5
O19—Gd—O13135.55 (11)H22A—C22—H22C109.5
O3—Gd—O13123.85 (10)H22B—C22—H22C109.5
O12—Gd—O1362.99 (11)O3—C23—N2121.7 (4)
O4—Gd—O1369.02 (10)O3—C23—C24120.8 (4)
O6—Gd—O13120.36 (10)N2—C23—C24117.4 (4)
O2—Gd—O13114.77 (10)O4—C24—C23106.9 (3)
C13—N1—C15123.1 (4)O4—C24—H24A110.3
C13—N1—C21117.1 (4)C23—C24—H24A110.3
C15—N1—C21119.7 (4)O4—C24—H24B110.3
C23—N2—C25121.2 (4)C23—C24—H24B110.3
C23—N2—C31119.1 (4)H24A—C24—H24B108.6
C25—N2—C31119.7 (4)C26—C25—C30120.8 (6)
O7—N3—O6120.9 (5)C26—C25—N2119.9 (5)
O7—N3—C34118.6 (4)C30—C25—N2119.3 (6)
O6—N3—C34120.5 (4)C25—C26—C27119.7 (7)
O8—N4—O9124.7 (5)C25—C26—H26120.1
O8—N4—C36117.8 (6)C27—C26—H26120.1
O9—N4—C36117.5 (6)C28—C27—C26119.1 (7)
O11—N5—O10123.9 (5)C28—C27—H27120.5
O11—N5—C38119.4 (4)C26—C27—H27120.5
O10—N5—C38116.7 (5)C29—C28—C27121.2 (7)
O14—N6—O13122.4 (5)C29—C28—H28119.4
O14—N6—C40117.8 (5)C27—C28—H28119.4
O13—N6—C40119.8 (4)C28—C29—C30120.1 (7)
O15—N7—O16124.3 (5)C28—C29—H29120.0
O15—N7—C42117.8 (5)C30—C29—H29120.0
O16—N7—C42117.9 (6)C25—C30—C29119.2 (7)
O17—N8—O18124.4 (6)C25—C30—H30120.4
O17—N8—C44118.1 (5)C29—C30—H30120.4
O18—N8—C44117.5 (5)C32—C31—N2110.0 (6)
O20—N9—O21124.6 (6)C32—C31—H31A109.7
O20—N9—C46118.1 (5)N2—C31—H31A109.7
O21—N9—C46117.3 (5)C32—C31—H31B109.7
O22—N10—O23124.4 (6)N2—C31—H31B109.7
O22—N10—C48118.6 (6)H31A—C31—H31B108.2
O23—N10—C48117.0 (6)C31—C32—H32A109.5
O25—N11—O24123.0 (6)C31—C32—H32B109.5
O25—N11—C50120.3 (6)H32A—C32—H32B109.5
O24—N11—C50116.7 (5)C31—C32—H32C109.5
C13—O1—Gd128.6 (3)H32A—C32—H32C109.5
C1—O2—C14117.0 (3)H32B—C32—H32C109.5
C1—O2—Gd126.1 (2)O5—C33—C38121.3 (4)
C14—O2—Gd115.5 (2)O5—C33—C34125.1 (4)
C23—O3—Gd122.6 (3)C38—C33—C34113.5 (4)
C12—O4—C24116.1 (3)C35—C34—C33122.9 (4)
C12—O4—Gd127.5 (2)C35—C34—N3115.7 (4)
C24—O4—Gd114.1 (2)C33—C34—N3121.4 (4)
C33—O5—Gd143.8 (3)C36—C35—C34118.6 (5)
N3—O6—Gd140.6 (3)C36—C35—H35120.7
C39—O12—Gd131.5 (3)C34—C35—H35120.7
N6—O13—Gd133.7 (3)C35—C36—C37121.7 (5)
C45—O19—Gd132.8 (3)C35—C36—N4119.6 (6)
C2—C1—C6122.7 (4)C37—C36—N4118.7 (5)
C2—C1—O2118.4 (4)C38—C37—C36119.5 (5)
C6—C1—O2118.7 (4)C38—C37—H37120.2
C1—C2—C3119.1 (6)C36—C37—H37120.2
C1—C2—H2120.5C37—C38—C33123.7 (5)
C3—C2—H2120.5C37—C38—N5118.0 (4)
C4—C3—C2119.8 (6)C33—C38—N5118.3 (4)
C4—C3—H3120.1O12—C39—C40125.4 (4)
C2—C3—H3120.1O12—C39—C44122.1 (4)
C3—C4—C5120.8 (6)C40—C39—C44112.5 (4)
C3—C4—H4119.6C41—C40—C39124.0 (4)
C5—C4—H4119.6C41—C40—N6116.5 (5)
C4—C5—C6120.6 (6)C39—C40—N6119.5 (4)
C4—C5—H5119.7C42—C41—C40119.1 (5)
C6—C5—H5119.7C42—C41—H41120.5
C1—C6—C5116.9 (5)C40—C41—H41120.5
C1—C6—C7121.5 (4)C41—C42—C43121.1 (5)
C5—C6—C7121.6 (5)C41—C42—N7119.3 (5)
C12—C7—C8117.1 (5)C43—C42—N7119.5 (5)
C12—C7—C6121.6 (4)C44—C43—C42119.1 (5)
C8—C7—C6121.3 (5)C44—C43—H43120.5
C9—C8—C7120.7 (6)C42—C43—H43120.5
C9—C8—H8119.7C43—C44—C39124.1 (5)
C7—C8—H8119.7C43—C44—N8117.3 (5)
C10—C9—C8121.0 (5)C39—C44—N8118.6 (4)
C10—C9—H9119.5O19—C45—C50124.7 (5)
C8—C9—H9119.5O19—C45—C46123.1 (5)
C9—C10—C11119.7 (6)C50—C45—C46112.2 (4)
C9—C10—H10120.2C47—C46—C45124.4 (5)
C11—C10—H10120.2C47—C46—N9117.2 (5)
C12—C11—C10119.4 (5)C45—C46—N9118.4 (4)
C12—C11—H11120.3C46—C47—C48118.5 (5)
C10—C11—H11120.3C46—C47—H47120.8
C11—C12—C7122.1 (4)C48—C47—H47120.8
C11—C12—O4117.9 (4)C47—C48—C49121.6 (5)
C7—C12—O4119.8 (4)C47—C48—N10118.7 (5)
O1—C13—N1121.4 (4)C49—C48—N10119.6 (6)
O1—C13—C14119.9 (4)C50—C49—C48119.0 (5)
N1—C13—C14118.7 (4)C50—C49—H49120.5
O2—C14—C13105.9 (3)C48—C49—H49120.5
O2—C14—H14A110.6C49—C50—C45123.3 (5)
C13—C14—H14A110.6C49—C50—N11117.0 (5)
O2—C14—H14B110.6C45—C50—N11119.6 (5)
Table 1
Selected geometric parameters (Å, °) top
Gd—O12.296 (3)Gd—O42.542 (3)
Gd—O32.325 (3)Gd—O22.605 (3)
O1—Gd—O477.57 (10)O3—Gd—O272.98 (9)
O3—Gd—O464.17 (10)O4—Gd—O267.09 (9)
O1—Gd—O262.18 (10)
Acknowledgements top

We are grateful to the NSFC (grants 20371022, 20431010 and 20021001), the Specialized Research Fund for the Doctoral Program of Higher Education (200307300015), and the Key Project of the Ministry of Education of China (grant 01170) for financial support.

references
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