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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): m1050.
Published online 2009 August 8. doi:  10.1107/S1600536809030700
PMCID: PMC2969912

Tris(dibenzoyl­methanido-κ2 O,O′)[(6S,8S)-(+)-7,7-dimethyl-3-(2-pyrid­yl)-5,6,7,8-tetra­hydro-6,8-methano­isoquinoline-κ2 N,N′]gadolinium(III)

Abstract

In the title compound, [Gd(C15H11O2)3(C17H18N2)], the GdIII atom is coordinated by six O atoms from three β-diketonate ligands and two N atoms from a chiral ligand LS,S-(+)-7,7-dimethyl-3-(2-pyrid­yl)-5,6,7,8-tetra­hydro-6,8-methano­iso­quinoline, in a coordination geometry best described as distorted square-anti­prismatic.

Related literature

For general background, see: Kaneko et al. (2006 [triangle]); Kimura et al. (2003 [triangle]). For related structures, see: Li et al. (2007 [triangle]). For the synthesis, see: Carles & Ohlmann (1965 [triangle]); Hayoz & Zelewsky (1992 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1050-scheme1.jpg

Experimental

Crystal data

  • [Gd(C15H11O2)3(C17H18N2)]
  • M r = 1077.30
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1050-efi1.jpg
  • a = 9.5303 (19) Å
  • b = 20.814 (4) Å
  • c = 12.735 (2) Å
  • β = 92.421 (4)°
  • V = 2523.9 (8) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.37 mm−1
  • T = 298 K
  • 0.30 × 0.24 × 0.22 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.680, T max = 0.742
  • 13247 measured reflections
  • 9009 independent reflections
  • 8750 reflections with I > 2σ(I)
  • R int = 0.019

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.074
  • S = 1.04
  • 9009 reflections
  • 642 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 1.40 e Å−3
  • Δρmin = −0.46 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 3943 Friedel pairs
  • Flack parameter: 0.029 (10)

Data collection: SMART (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809030700/hy2214sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030700/hy2214Isup2.hkl

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

Acknowledgments

This work was supported financially by the Doctoral Foundation (grant No. 000491) of Zhengzhou University of Light Industry.

supplementary crystallographic information

Comment

In the coordination chemistry field, chiral ligands play a key role in designing noncentrosymmetric complexes. In particular, many useful physical properties such as ferroelectricity, piezoelectricity, magneto-chiral dichroism and second harmony generation etc. are only based on noncentrosymmetric crystal lattices (Kaneko et al., 2006; Kimura et al., 2003). An effective and facile method to prepare such kind of complexes is the introducing of chiral motifs in molecule. Based on this strategy, as a continuance of our research (Li et al., 2007), we employed a chiral ligands LS,S, (+)7,7-dimethyl-3-(2-pyridyl)-5,6,7,8-tetrahydro-6,8-methanoisoquinoline, to react with Gd(dbm)3.2H2O (dbm = dibenzoylmethanide), and an enantiomerically pure compound with formula Gd(dbm)3LS,S was obtained.

As shown in Fig. 1, the title compound contains three β-diketonate ligands, a chiral bipyridine derivative ligand and a GdIII atom, which is isostructural with our previously reported Eu(dbm)3LS,S (Li et al., 2007). The GdIII atom is coordinated by six O atoms from three β-diketonate ligands and two N atoms from a chiral bipyridine derivative in an eight-coordinated distorted square-antiprismatic environment. The Gd—O bond distances rang from 2.338 (4) to 2.371 (5) Å, while two Gd—N bond distances are 2.587 (4) and 2.601 (3) Å. The two square planes defined by O5, O6, N1, N2 (top face) and O1, O2, O3, O4 (bottom face) (Fig.2) with mean deviations of 0.121 (3) and 0.063 (3) Å, respectively, make a dihedral angle of 1.40 (1)°. The title compound crystallizes in the chiral space group P21 and the chirality is dominated by two chiral centers (C57 and C58) of bipyridine derivative.

Experimental

The chiral ligand LS,S was prepared by the documented procedures (Hayoz & Zelewsky, 1992) and Gd(dbm)3.2H2O was synthesized according to literature method (Carles & Ohlmann, 1965). A solution of Gd(dbm)3.2H2O (0.086 g, 0.1 mmol) in ethanol was added to a solution of LS,S in acetone. The mixture was kept at room temperature. Yellow single crystals of the title compound, suitable for X-ray analysis, were obtained in 79% yield by slow evaporation of the solvent over two weeks. Analysis calculated for C62H51GdN2O6: C 69.00, H 4.77, N 2.60%; found: C 71.02, H 4.67, N 2.86%.

Refinement

H atoms were positioned geometrically and treated as riding atoms, with C—H = 0.93 (aromatic), 0.98 (tertiary), 0.97 (methylene) and 0.96 (methyl) Å and with Uiso(H) = 1.2(1.5 for methyl)Ueq(C). The highest residual electron density was found 0.92 Å from Gd1 and the deepest hole 0.52 Å from H55.

Figures

Fig. 1.
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.
Fig. 2.
Coordination geometry of GdIII atom in the title compound.

Crystal data

[Gd(C15H11O2)3(C17H18N2)]F(000) = 1098
Mr = 1077.30Dx = 1.418 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 13247 reflections
a = 9.5303 (19) Åθ = 2.5–22.5°
b = 20.814 (4) ŵ = 1.37 mm1
c = 12.735 (2) ÅT = 298 K
β = 92.421 (4)°Block, yellow
V = 2523.9 (8) Å30.30 × 0.24 × 0.22 mm
Z = 2

Data collection

Bruker SMART APEX CCD diffractometer9009 independent reflections
Radiation source: fine-focus sealed tube8750 reflections with I > 2σ(I)
graphiteRint = 0.019
[var phi] and ω scansθmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −11→8
Tmin = 0.680, Tmax = 0.742k = −25→24
13247 measured reflectionsl = −15→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)] = 0.034H-atom parameters constrained
wR(F2) = 0.074w = 1/[σ2(Fo2) + (0.015P)2 + 1.990P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.002
9009 reflectionsΔρmax = 1.40 e Å3
642 parametersΔρmin = −0.46 e Å3
1 restraintAbsolute structure: Flack (1983), 3943 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.029 (10)

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

xyzUiso*/Ueq
C10.1984 (6)0.2577 (3)0.6357 (6)0.0406 (15)
C20.2001 (6)0.2429 (3)0.5220 (6)0.0450 (16)
C30.2043 (8)0.2949 (3)0.4518 (6)0.0657 (18)
H30.20270.33690.47660.079*
C40.2108 (10)0.2829 (5)0.3455 (8)0.086 (3)
H40.21870.31700.29890.103*
C50.2058 (9)0.2200 (8)0.3072 (6)0.088 (4)
H50.20600.21250.23520.106*
C60.2005 (7)0.1701 (4)0.3742 (5)0.0768 (18)
H60.19840.12820.34860.092*
C70.1983 (6)0.1813 (3)0.4818 (4)0.0588 (13)
H70.19550.14660.52760.071*
C80.2526 (5)0.2128 (2)0.7094 (4)0.0481 (11)
H80.27970.17280.68450.058*
C90.2687 (5)0.2240 (2)0.8176 (4)0.0450 (11)
C100.3456 (5)0.1766 (2)0.8871 (4)0.0499 (11)
C110.4313 (7)0.1291 (3)0.8488 (5)0.0734 (17)
H110.43860.12450.77660.088*
C120.5056 (8)0.0886 (4)0.9156 (7)0.091 (2)
H120.56340.05730.88820.109*
C130.4954 (7)0.0937 (4)1.0210 (6)0.087 (2)
H130.54660.06651.06600.104*
C140.4097 (10)0.1390 (5)1.0604 (6)0.105 (3)
H140.40090.14211.13270.126*
C150.3353 (8)0.1808 (4)0.9942 (5)0.085 (2)
H150.27790.21191.02240.102*
C16−0.0584 (5)0.4176 (2)0.9698 (4)0.0452 (10)
C17−0.0895 (5)0.4255 (3)1.0831 (4)0.0517 (12)
C18−0.0309 (5)0.3839 (5)1.1566 (3)0.0616 (11)
H180.03120.35251.13530.074*
C19−0.0621 (7)0.3877 (6)1.2611 (4)0.0850 (19)
H19−0.02400.35801.30890.102*
C20−0.1479 (9)0.4345 (4)1.2944 (5)0.098 (3)
H20−0.17010.43661.36480.118*
C21−0.2013 (9)0.4781 (4)1.2251 (5)0.100 (3)
H21−0.25750.51111.24890.120*
C22−0.1742 (7)0.4746 (3)1.1202 (4)0.0735 (18)
H22−0.21230.50501.07370.088*
C23−0.1440 (5)0.4482 (3)0.8941 (4)0.0500 (12)
H23−0.21430.47500.91720.060*
C24−0.1316 (5)0.4415 (2)0.7853 (4)0.0436 (10)
C25−0.2364 (6)0.4742 (2)0.7126 (4)0.0428 (11)
C26−0.3633 (6)0.4979 (3)0.7450 (5)0.0586 (14)
H26−0.38610.49360.81500.070*
C27−0.4553 (6)0.5274 (3)0.6756 (6)0.0751 (18)
H27−0.54020.54320.69830.090*
C28−0.4226 (8)0.5337 (3)0.5724 (6)0.085 (2)
H28−0.48560.55370.52510.102*
C29−0.2989 (9)0.5112 (4)0.5386 (5)0.073 (2)
H29−0.27740.51550.46840.087*
C30−0.2042 (6)0.4814 (3)0.6091 (4)0.0549 (12)
H30−0.11890.46640.58610.066*
C310.1593 (5)0.5411 (2)0.8180 (4)0.0431 (10)
C320.1256 (5)0.5972 (2)0.8867 (4)0.0442 (10)
C330.0830 (7)0.5865 (3)0.9877 (4)0.0640 (15)
H330.07940.54471.01350.077*
C340.0461 (7)0.6369 (3)1.0503 (5)0.0794 (19)
H340.01510.62871.11720.095*
C350.0539 (7)0.6987 (3)1.0163 (5)0.0721 (17)
H350.02870.73251.05940.086*
C360.0990 (8)0.7100 (3)0.9186 (5)0.0818 (19)
H360.10650.75210.89490.098*
C370.1340 (8)0.6599 (3)0.8537 (5)0.0719 (16)
H370.16360.66870.78650.086*
C380.1460 (5)0.5486 (2)0.7089 (4)0.0459 (11)
H380.10790.58680.68270.055*
C390.1864 (7)0.5022 (3)0.6366 (6)0.0470 (16)
C400.1748 (7)0.5178 (3)0.5201 (5)0.0479 (16)
C410.0875 (6)0.5645 (3)0.4778 (4)0.0594 (13)
H410.03100.58790.52170.071*
C420.0823 (8)0.5772 (3)0.3717 (5)0.0764 (18)
H420.02090.60820.34390.092*
C430.1682 (12)0.5441 (7)0.3072 (6)0.094 (4)
H430.16450.55230.23540.112*
C440.2580 (12)0.4996 (5)0.3476 (7)0.104 (4)
H440.31860.47830.30390.125*
C450.2603 (9)0.4853 (3)0.4538 (5)0.073 (2)
H450.32020.45350.48060.088*
C460.3468 (6)0.3970 (3)1.0578 (4)0.066 (2)
H460.26350.41921.06670.080*
C470.4284 (6)0.3824 (7)1.1449 (4)0.0866 (17)
H470.40140.39451.21140.104*
C480.5500 (8)0.3499 (4)1.1324 (5)0.099 (3)
H480.60770.33941.19060.119*
C490.5869 (7)0.3329 (4)1.0343 (5)0.084 (2)
H490.66960.31031.02500.100*
C500.5004 (5)0.3495 (3)0.9479 (4)0.0518 (12)
C510.5374 (5)0.3343 (2)0.8389 (4)0.0452 (11)
C520.6568 (5)0.3007 (3)0.8165 (4)0.0565 (13)
H520.71520.28500.87100.068*
C530.6904 (6)0.2902 (3)0.7133 (5)0.0504 (13)
C540.6027 (5)0.3156 (2)0.6349 (4)0.0507 (12)
C550.4842 (5)0.3477 (2)0.6641 (4)0.0479 (11)
H550.42460.36390.61090.057*
C560.8148 (5)0.2501 (3)0.6833 (5)0.0644 (15)
H56A0.80620.20700.71150.077*
H56B0.90090.26890.71270.077*
C570.8199 (6)0.2472 (3)0.5639 (5)0.0682 (16)
H570.89950.22310.53750.082*
C580.6414 (7)0.3041 (3)0.5241 (5)0.0710 (17)
H580.58220.32450.46880.085*
C590.8038 (8)0.3159 (3)0.5210 (6)0.086 (2)
H59A0.83790.32180.45100.104*
H59B0.83920.34900.56870.104*
C600.6760 (7)0.2310 (3)0.5093 (5)0.0646 (17)
C610.5839 (6)0.1819 (3)0.5623 (6)0.0771 (18)
H61A0.49490.17900.52430.116*
H61B0.56940.19510.63330.116*
H61C0.62920.14070.56260.116*
C620.6851 (10)0.2136 (4)0.3939 (6)0.106 (3)
H62A0.73250.24720.35800.160*
H62B0.59210.20830.36310.160*
H62C0.73630.17410.38780.160*
Gd10.191494 (18)0.38195 (2)0.805878 (13)0.03808 (6)
N10.3797 (3)0.3811 (4)0.9598 (2)0.0506 (7)
N20.4487 (4)0.35710 (18)0.7629 (3)0.0438 (9)
O10.1581 (4)0.31363 (18)0.6612 (3)0.0491 (9)
O20.2229 (5)0.2740 (2)0.8617 (4)0.0487 (11)
O30.0450 (3)0.3816 (3)0.95033 (19)0.0506 (6)
O4−0.0349 (3)0.41022 (15)0.7441 (2)0.0481 (8)
O50.1972 (5)0.4897 (2)0.8640 (4)0.0477 (11)
O60.2329 (4)0.44748 (18)0.6600 (3)0.0498 (9)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.034 (3)0.034 (3)0.053 (4)−0.002 (2)0.004 (3)−0.005 (3)
C20.035 (3)0.048 (4)0.052 (4)0.008 (2)−0.001 (2)−0.001 (3)
C30.087 (5)0.054 (4)0.056 (4)0.012 (3)0.002 (3)0.002 (3)
C40.105 (6)0.092 (7)0.061 (4)0.011 (5)0.008 (4)0.017 (4)
C50.106 (7)0.110 (10)0.047 (5)0.035 (6)0.007 (4)−0.003 (4)
C60.086 (5)0.083 (5)0.061 (4)0.021 (4)−0.002 (3)−0.023 (3)
C70.060 (3)0.057 (3)0.060 (3)0.004 (3)0.004 (3)−0.008 (3)
C80.053 (3)0.034 (3)0.058 (3)0.007 (2)0.010 (2)−0.005 (2)
C90.044 (3)0.037 (3)0.055 (3)−0.0030 (19)0.010 (2)0.005 (2)
C100.051 (3)0.040 (3)0.059 (3)−0.001 (2)0.006 (2)0.008 (2)
C110.088 (4)0.064 (4)0.069 (4)0.024 (3)0.011 (3)0.013 (3)
C120.090 (5)0.075 (5)0.109 (6)0.035 (4)0.015 (4)0.027 (4)
C130.073 (4)0.090 (5)0.097 (5)0.011 (4)0.000 (4)0.037 (4)
C140.130 (7)0.124 (8)0.063 (4)0.045 (6)0.002 (4)0.024 (4)
C150.098 (5)0.090 (5)0.067 (4)0.031 (4)0.009 (3)0.006 (3)
C160.051 (3)0.037 (3)0.049 (3)0.001 (2)0.011 (2)0.005 (2)
C170.053 (3)0.056 (3)0.047 (3)−0.002 (2)0.014 (2)−0.002 (2)
C180.069 (3)0.060 (3)0.058 (2)0.009 (5)0.014 (2)0.004 (5)
C190.111 (4)0.092 (5)0.054 (3)0.017 (6)0.024 (3)0.021 (5)
C200.142 (7)0.108 (6)0.047 (3)0.030 (5)0.032 (4)−0.004 (4)
C210.138 (7)0.110 (6)0.054 (3)0.056 (5)0.023 (4)−0.010 (4)
C220.093 (5)0.077 (4)0.051 (3)0.029 (3)0.015 (3)−0.001 (3)
C230.040 (2)0.059 (3)0.051 (3)0.015 (2)0.010 (2)−0.007 (2)
C240.044 (3)0.038 (3)0.049 (3)−0.0015 (19)0.008 (2)−0.005 (2)
C250.037 (3)0.040 (3)0.051 (3)−0.002 (2)0.000 (2)−0.006 (2)
C260.045 (3)0.063 (4)0.068 (4)0.004 (2)0.001 (3)−0.004 (3)
C270.047 (3)0.072 (4)0.105 (5)0.015 (3)−0.010 (3)−0.009 (4)
C280.088 (5)0.060 (4)0.103 (6)0.016 (4)−0.043 (4)0.002 (4)
C290.103 (6)0.061 (5)0.053 (4)0.007 (4)−0.012 (3)0.004 (3)
C300.059 (3)0.045 (3)0.060 (3)0.006 (2)0.001 (3)−0.005 (3)
C310.043 (3)0.039 (3)0.048 (3)−0.0010 (19)0.009 (2)−0.001 (2)
C320.045 (3)0.041 (3)0.047 (2)0.0007 (19)0.002 (2)−0.003 (2)
C330.089 (4)0.052 (3)0.052 (3)0.002 (3)0.009 (3)0.002 (2)
C340.104 (5)0.079 (5)0.056 (3)0.007 (4)0.015 (3)−0.019 (3)
C350.075 (4)0.067 (4)0.075 (4)0.012 (3)0.002 (3)−0.030 (3)
C360.122 (6)0.038 (3)0.086 (4)0.012 (3)0.008 (4)−0.004 (3)
C370.111 (5)0.046 (3)0.060 (3)0.003 (3)0.011 (3)0.001 (3)
C380.061 (3)0.031 (2)0.046 (3)0.007 (2)0.010 (2)0.0083 (19)
C390.047 (4)0.051 (4)0.044 (4)−0.003 (3)0.014 (3)0.004 (3)
C400.054 (4)0.045 (4)0.045 (3)−0.002 (3)0.011 (3)0.003 (3)
C410.073 (4)0.058 (4)0.048 (3)0.005 (3)0.010 (3)0.005 (2)
C420.100 (5)0.070 (4)0.058 (4)−0.001 (4)−0.003 (3)0.013 (3)
C430.152 (9)0.085 (8)0.044 (5)0.008 (6)0.006 (5)0.004 (4)
C440.174 (10)0.088 (7)0.054 (5)0.033 (7)0.037 (6)−0.005 (4)
C450.116 (6)0.048 (4)0.057 (4)0.016 (4)0.019 (4)−0.002 (3)
C460.063 (3)0.078 (6)0.058 (3)0.009 (3)0.007 (2)−0.015 (3)
C470.087 (4)0.120 (5)0.052 (3)0.001 (7)0.003 (3)−0.018 (7)
C480.090 (5)0.151 (8)0.056 (3)0.026 (5)−0.009 (3)−0.006 (4)
C490.064 (4)0.125 (6)0.061 (4)0.030 (4)−0.004 (3)−0.007 (4)
C500.046 (3)0.052 (3)0.058 (3)0.002 (2)0.007 (2)−0.003 (2)
C510.040 (2)0.040 (3)0.055 (3)0.0012 (19)0.006 (2)−0.003 (2)
C520.047 (3)0.056 (3)0.066 (3)0.009 (2)0.000 (2)−0.008 (3)
C530.034 (3)0.046 (3)0.072 (4)0.005 (2)0.012 (3)−0.009 (3)
C540.053 (3)0.039 (3)0.061 (3)−0.003 (2)0.022 (2)−0.003 (2)
C550.053 (3)0.040 (3)0.051 (3)0.011 (2)0.012 (2)0.008 (2)
C560.038 (3)0.070 (4)0.086 (4)0.005 (2)0.011 (3)−0.018 (3)
C570.049 (3)0.059 (4)0.100 (5)0.002 (3)0.033 (3)−0.010 (3)
C580.090 (4)0.066 (4)0.060 (3)0.020 (3)0.035 (3)0.002 (3)
C590.099 (5)0.061 (4)0.105 (5)−0.003 (3)0.063 (4)−0.006 (4)
C600.070 (4)0.059 (4)0.066 (4)0.012 (3)0.024 (3)−0.018 (3)
C610.055 (3)0.067 (4)0.110 (5)−0.006 (3)0.009 (3)−0.023 (4)
C620.133 (7)0.107 (6)0.081 (5)0.042 (5)0.020 (4)−0.030 (4)
Gd10.04094 (10)0.03390 (10)0.04003 (9)0.00921 (12)0.00911 (6)0.00091 (15)
N10.0537 (19)0.0507 (19)0.0479 (17)−0.004 (3)0.0085 (14)−0.006 (4)
N20.044 (2)0.043 (2)0.046 (2)0.0035 (15)0.0115 (17)0.0020 (15)
O10.054 (2)0.041 (2)0.052 (2)0.0123 (17)0.0020 (18)−0.0002 (15)
O20.060 (2)0.042 (2)0.045 (3)0.0052 (18)0.0094 (19)−0.001 (2)
O30.0519 (15)0.0512 (16)0.0496 (14)0.016 (3)0.0123 (12)0.007 (3)
O40.0523 (18)0.0517 (19)0.0410 (16)0.0099 (14)0.0107 (14)−0.0060 (13)
O50.060 (3)0.037 (2)0.046 (3)0.0077 (17)0.0071 (18)0.0028 (19)
O60.061 (2)0.042 (2)0.0484 (19)0.0111 (18)0.0178 (18)0.0027 (15)

Geometric parameters (Å, °)

C1—O11.273 (7)C35—H350.9300
C1—C81.408 (8)C36—C371.381 (8)
C1—C21.480 (10)C36—H360.9300
C2—C71.381 (9)C37—H370.9300
C2—C31.406 (10)C38—C391.399 (9)
C3—C41.381 (12)C38—H380.9300
C3—H30.9300C39—O61.253 (8)
C4—C51.397 (18)C39—C401.519 (10)
C4—H40.9300C40—C451.376 (9)
C5—C61.346 (15)C40—C411.374 (9)
C5—H50.9300C41—C421.375 (8)
C6—C71.391 (8)C41—H410.9300
C6—H60.9300C42—C431.370 (13)
C7—H70.9300C42—H420.9300
C8—C91.400 (7)C43—C441.348 (16)
C8—H80.9300C43—H430.9300
C9—O21.269 (6)C44—C451.384 (11)
C9—C101.498 (7)C44—H440.9300
C10—C151.374 (8)C45—H450.9300
C10—C111.384 (8)C46—N11.340 (6)
C11—C121.372 (9)C46—C471.362 (8)
C11—H110.9300C46—H460.9300
C12—C131.355 (10)C47—C481.356 (11)
C12—H120.9300C47—H470.9300
C13—C141.357 (11)C48—C491.360 (9)
C13—H130.9300C48—H480.9300
C14—C151.386 (9)C49—C501.390 (8)
C14—H140.9300C49—H490.9300
C15—H150.9300C50—N11.340 (7)
C16—O31.269 (6)C50—C511.481 (7)
C16—C231.392 (7)C51—N21.344 (6)
C16—C171.495 (6)C51—C521.376 (7)
C17—C181.376 (8)C52—C531.383 (8)
C17—C221.397 (7)C52—H520.9300
C18—C191.378 (6)C53—C541.379 (8)
C18—H180.9300C53—C561.513 (7)
C19—C201.352 (11)C54—C551.376 (7)
C19—H190.9300C54—C581.493 (7)
C20—C211.350 (10)C55—N21.331 (6)
C20—H200.9300C55—H550.9300
C21—C221.373 (8)C56—C571.525 (9)
C21—H210.9300C56—H56A0.9700
C22—H220.9300C56—H56B0.9700
C23—C241.402 (6)C57—C591.537 (9)
C23—H230.9300C57—C601.548 (9)
C24—O41.261 (5)C57—H570.9800
C24—C251.496 (7)C58—C591.570 (10)
C25—C301.375 (8)C58—C601.569 (9)
C25—C261.385 (7)C58—H580.9800
C26—C271.365 (8)C59—H59A0.9700
C26—H260.9300C59—H59B0.9700
C27—C281.370 (10)C60—C621.519 (9)
C27—H270.9300C60—C611.524 (10)
C28—C291.356 (10)C61—H61A0.9600
C28—H280.9300C61—H61B0.9600
C29—C301.391 (9)C61—H61C0.9600
C29—H290.9300C62—H62A0.9600
C30—H300.9300C62—H62B0.9600
C31—O51.266 (6)C62—H62C0.9600
C31—C381.399 (6)Gd1—O12.338 (4)
C31—C321.502 (6)Gd1—O22.371 (5)
C32—C371.374 (8)Gd1—O32.356 (2)
C32—C331.383 (7)Gd1—O42.340 (3)
C33—C341.374 (8)Gd1—O52.361 (5)
C33—H330.9300Gd1—O62.351 (4)
C34—C351.358 (9)Gd1—N12.601 (3)
C34—H340.9300Gd1—N22.587 (4)
C35—C361.355 (9)
O1—C1—C8122.9 (6)C43—C42—H42120.2
O1—C1—C2117.1 (6)C41—C42—H42120.2
C8—C1—C2119.7 (6)C44—C43—C42120.2 (7)
C7—C2—C3118.6 (6)C44—C43—H43119.9
C7—C2—C1123.7 (6)C42—C43—H43119.9
C3—C2—C1117.7 (6)C43—C44—C45120.2 (8)
C4—C3—C2119.2 (7)C43—C44—H44119.9
C4—C3—H3120.4C45—C44—H44119.9
C2—C3—H3120.4C40—C45—C44120.6 (8)
C3—C4—C5120.6 (8)C40—C45—H45119.7
C3—C4—H4119.7C44—C45—H45119.7
C5—C4—H4119.7N1—C46—C47123.7 (6)
C6—C5—C4120.3 (7)N1—C46—H46118.1
C6—C5—H5119.9C47—C46—H46118.1
C4—C5—H5119.9C48—C47—C46118.5 (6)
C5—C6—C7119.8 (8)C48—C47—H47120.8
C5—C6—H6120.1C46—C47—H47120.8
C7—C6—H6120.1C47—C48—C49119.5 (6)
C2—C7—C6121.4 (6)C47—C48—H48120.2
C2—C7—H7119.3C49—C48—H48120.2
C6—C7—H7119.3C48—C49—C50119.7 (6)
C9—C8—C1124.5 (5)C48—C49—H49120.2
C9—C8—H8117.7C50—C49—H49120.2
C1—C8—H8117.7N1—C50—C49121.0 (5)
O2—C9—C8123.2 (5)N1—C50—C51116.8 (4)
O2—C9—C10116.7 (5)C49—C50—C51122.2 (5)
C8—C9—C10120.1 (4)N2—C51—C52122.1 (4)
C15—C10—C11117.6 (5)N2—C51—C50115.6 (4)
C15—C10—C9119.4 (5)C52—C51—C50122.3 (5)
C11—C10—C9123.0 (5)C51—C52—C53120.2 (5)
C12—C11—C10121.1 (6)C51—C52—H52119.9
C12—C11—H11119.4C53—C52—H52119.9
C10—C11—H11119.4C54—C53—C52118.1 (5)
C13—C12—C11120.6 (7)C54—C53—C56119.1 (5)
C13—C12—H12119.7C52—C53—C56122.8 (5)
C11—C12—H12119.7C55—C54—C53118.0 (5)
C12—C13—C14119.4 (6)C55—C54—C58124.8 (5)
C12—C13—H13120.3C53—C54—C58117.2 (5)
C14—C13—H13120.3N2—C55—C54124.8 (5)
C13—C14—C15120.8 (7)N2—C55—H55117.6
C13—C14—H14119.6C54—C55—H55117.6
C15—C14—H14119.6C53—C56—C57109.4 (5)
C10—C15—C14120.5 (7)C53—C56—H56A109.8
C10—C15—H15119.8C57—C56—H56A109.8
C14—C15—H15119.8C53—C56—H56B109.8
O3—C16—C23124.9 (4)C57—C56—H56B109.8
O3—C16—C17116.2 (4)H56A—C56—H56B108.2
C23—C16—C17118.9 (4)C56—C57—C59108.1 (5)
C18—C17—C22117.0 (5)C56—C57—C60113.0 (4)
C18—C17—C16119.7 (5)C59—C57—C6088.2 (5)
C22—C17—C16123.2 (5)C56—C57—H57114.8
C19—C18—C17121.5 (8)C59—C57—H57114.8
C19—C18—H18119.2C60—C57—H57114.8
C17—C18—H18119.2C54—C58—C59106.4 (6)
C20—C19—C18120.2 (8)C54—C58—C60109.3 (5)
C20—C19—H19119.9C59—C58—C6086.3 (5)
C18—C19—H19119.9C54—C58—H58116.9
C19—C20—C21119.7 (6)C59—C58—H58116.9
C19—C20—H20120.2C60—C58—H58116.9
C21—C20—H20120.2C57—C59—C5885.9 (5)
C20—C21—C22121.3 (6)C57—C59—H59A114.3
C20—C21—H21119.4C58—C59—H59A114.3
C22—C21—H21119.4C57—C59—H59B114.3
C21—C22—C17120.2 (6)C58—C59—H59B114.3
C21—C22—H22119.9H59A—C59—H59B111.5
C17—C22—H22119.9C62—C60—C61109.0 (6)
C16—C23—C24124.6 (4)C62—C60—C57113.6 (6)
C16—C23—H23117.7C61—C60—C57117.6 (6)
C24—C23—H23117.7C62—C60—C58111.6 (6)
O4—C24—C23123.7 (4)C61—C60—C58118.0 (5)
O4—C24—C25117.3 (4)C57—C60—C5885.6 (5)
C23—C24—C25119.0 (4)C60—C61—H61A109.5
C30—C25—C26118.7 (5)C60—C61—H61B109.5
C30—C25—C24118.2 (5)H61A—C61—H61B109.5
C26—C25—C24123.1 (5)C60—C61—H61C109.5
C27—C26—C25120.8 (6)H61A—C61—H61C109.5
C27—C26—H26119.6H61B—C61—H61C109.5
C25—C26—H26119.6C60—C62—H62A109.5
C26—C27—C28119.9 (6)C60—C62—H62B109.5
C26—C27—H27120.0H62A—C62—H62B109.5
C28—C27—H27120.0C60—C62—H62C109.5
C29—C28—C27120.5 (6)H62A—C62—H62C109.5
C29—C28—H28119.8H62B—C62—H62C109.5
C27—C28—H28119.8O1—Gd1—O478.18 (11)
C28—C29—C30119.9 (7)O1—Gd1—O675.64 (11)
C28—C29—H29120.0O4—Gd1—O676.79 (12)
C30—C29—H29120.0O1—Gd1—O3123.22 (16)
C25—C30—C29120.2 (6)O4—Gd1—O372.24 (10)
C25—C30—H30119.9O6—Gd1—O3138.02 (15)
C29—C30—H30119.9O1—Gd1—O5145.58 (14)
O5—C31—C38124.4 (4)O4—Gd1—O582.84 (14)
O5—C31—C32116.9 (4)O6—Gd1—O572.19 (14)
C38—C31—C32118.7 (4)O3—Gd1—O576.41 (19)
C37—C32—C33117.5 (5)O1—Gd1—O270.82 (14)
C37—C32—C31122.9 (4)O4—Gd1—O2116.22 (14)
C33—C32—C31119.7 (4)O6—Gd1—O2139.74 (14)
C34—C33—C32120.6 (6)O3—Gd1—O280.47 (18)
C34—C33—H33119.7O5—Gd1—O2143.59 (9)
C32—C33—H33119.7O1—Gd1—N279.06 (12)
C35—C34—C33121.3 (6)O4—Gd1—N2147.95 (11)
C35—C34—H34119.3O6—Gd1—N275.92 (12)
C33—C34—H34119.3O3—Gd1—N2139.73 (11)
C36—C35—C34118.7 (5)O5—Gd1—N2104.29 (14)
C36—C35—H35120.6O2—Gd1—N276.43 (13)
C34—C35—H35120.6O1—Gd1—N1131.03 (17)
C35—C36—C37120.8 (6)O4—Gd1—N1148.41 (12)
C35—C36—H36119.6O6—Gd1—N1117.77 (16)
C37—C36—H36119.6O3—Gd1—N179.88 (9)
C32—C37—C36121.0 (6)O5—Gd1—N176.3 (2)
C32—C37—H37119.5O2—Gd1—N172.2 (2)
C36—C37—H37119.5N2—Gd1—N161.87 (11)
C31—C38—C39124.1 (5)C46—N1—C50117.5 (4)
C31—C38—H38117.9C46—N1—Gd1121.2 (3)
C39—C38—H38117.9C50—N1—Gd1119.1 (3)
O6—C39—C38125.1 (6)C55—N2—C51116.8 (4)
O6—C39—C40115.9 (6)C55—N2—Gd1120.7 (3)
C38—C39—C40118.9 (6)C51—N2—Gd1119.4 (3)
C45—C40—C41118.2 (6)C1—O1—Gd1136.5 (4)
C45—C40—C39118.3 (6)C9—O2—Gd1133.3 (4)
C41—C40—C39123.5 (6)C16—O3—Gd1129.9 (3)
C42—C41—C40121.1 (6)C24—O4—Gd1132.1 (3)
C42—C41—H41119.4C31—O5—Gd1131.0 (4)
C40—C41—H41119.4C39—O6—Gd1130.2 (4)
C43—C42—C41119.6 (7)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2214).

References

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  • Hayoz, P. & Zelewsky, A. V. (1992). Tetrahedron Lett.33, 5165–5170.
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