metal-organic compounds
Tetrakis(μ-6-hydroxy-1-naphthoato)bis[(6-hydroxy-1-naphthoato)(1,10-phenanthroline)europium(III)] dihydrate
aZhengzhou University of Light Industry, Henan Provincial Key Laboratory of Surface & Interface Science, Henan, Zhengzhou 450002, People's Republic of China
*Correspondence e-mail: chunsenliu@zzuli.edu.cn
The title complex, [Eu2(C11H7O3)6(C12H8N2)2]·2H2O, has a centrosymmetric binuclear cage structure in which the two EuIII ions are both nine-coordinated and bridged by 6-hydroxy-1-naphthoate (L) ligands, with an Eu⋯ Eu separation of 4.1594 (4) Å. The remaining coordination sites are occupied by two N atoms from one 1,10-phenanthroline (phen) and two O atoms from an L ligand. The six 6-hydroxy-1-naphthoate groups coordinate each EuIII atom in three different ways, namely μ2-η1:η1-bridging, μ1-η1:η1-chelating, and μ2-η1:η2-chelating/bridging modes. Adjacent discrete dinuclear units are linked into a two-dimensional sheet parallel to (011) by intermolecular O—H⋯O hydrogen-bonding interactions. The sheets are cross-linked by water molecules, forming a three-dimensional network. In addition, π–π stacking interactions, with a centroid–centroid separation of 3.547 (2) Å are observed.
Related literature
For general background to functional rare-earth coordination complexes, see: Bünzli (2006); Edelmann (2009); Fang et al. (2006); Li & Yan (2009); Xu et al. (2009). For related structures, see: Bettencourt-Dias (2005); Bettencourt-Dias & Viswanathan (2006); Qu et al. (2005); Serre & Férey (2002); Wan et al. (2002); Yang et al. (2006); Ye et al. (2005); Zheng et al. (2005).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536809046091/ci2947sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809046091/ci2947Isup2.hkl
A mixed solution of 6-hydroxy-1-naphthoic acid (0.05 mmol) and 1,10-phenanthroline (0.05 mmol) in CH3OH (10 ml) in the presence of excess 2,6-dimethylpyridine (ca 0.05 ml for adjusting the pH value to basic condition) was carefully layered on top of a H2O solution (15 ml) of Eu(ClO4)3 (0.1 mmol) in a test tube. Yellow single crystals suitable for X-ray analysis of the title complex (I) appeared at the tube wall after ca two weeks at room temperature. Yield: ~40% based on 6-hydroxy-1-naphthoic acid. Elemental analysis calculated for C45H31EuN2O10: C 59.28, H 3.43, N 3.07%; found: C 59.36, H 3.50, N 3.03%.
The water H atoms were located in a difference Fourier map and treated as riding on their parent atoms, with O-H = 0.85 Å and Uiso(H) = 1.2Ueq(O). C-bound H-atoms were included in calculated positions and treated as riding atoms: C-H = 0.93 Å with Uiso(H) = 1.2 Ueq(C).
Data collection: SMART (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).[Eu2(C11H7O3)6(C12H8N2)2]·2H2O | Z = 1 |
Mr = 1823.36 | F(000) = 916 |
Triclinic, P1 | Dx = 1.602 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.7132 (9) Å | Cell parameters from 6015 reflections |
b = 12.7143 (10) Å | θ = 2.5–25.6° |
c = 14.8822 (12) Å | µ = 1.73 mm−1 |
α = 65.790 (1)° | T = 296 K |
β = 88.276 (1)° | Block, yellow |
γ = 70.437 (1)° | 0.30 × 0.21 × 0.17 mm |
V = 1889.8 (3) Å3 |
Bruker SMART CCD area-detector diffractometer | 6615 independent reflections |
Radiation source: fine-focus sealed tube | 5910 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→13 |
Tmin = 0.626, Tmax = 0.758 | k = −15→14 |
13943 measured reflections | l = −17→17 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.026 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.057 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0253P)2 + 0.306P] where P = (Fo2 + 2Fc2)/3 |
6615 reflections | (Δ/σ)max = 0.002 |
526 parameters | Δρmax = 0.66 e Å−3 |
0 restraints | Δρmin = −0.56 e Å−3 |
[Eu2(C11H7O3)6(C12H8N2)2]·2H2O | γ = 70.437 (1)° |
Mr = 1823.36 | V = 1889.8 (3) Å3 |
Triclinic, P1 | Z = 1 |
a = 11.7132 (9) Å | Mo Kα radiation |
b = 12.7143 (10) Å | µ = 1.73 mm−1 |
c = 14.8822 (12) Å | T = 296 K |
α = 65.790 (1)° | 0.30 × 0.21 × 0.17 mm |
β = 88.276 (1)° |
Bruker SMART CCD area-detector diffractometer | 6615 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 5910 reflections with I > 2σ(I) |
Tmin = 0.626, Tmax = 0.758 | Rint = 0.024 |
13943 measured reflections |
R[F2 > 2σ(F2)] = 0.026 | 0 restraints |
wR(F2) = 0.057 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.66 e Å−3 |
6615 reflections | Δρmin = −0.56 e Å−3 |
526 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Eu1 | 0.415191 (13) | 0.370163 (13) | 0.555623 (10) | 0.02734 (6) | |
C1 | 0.3329 (3) | 0.2031 (3) | 0.7084 (2) | 0.0355 (7) | |
C2 | 0.2925 (3) | 0.1144 (3) | 0.7940 (2) | 0.0411 (8) | |
C3 | 0.1694 (3) | 0.1376 (4) | 0.7937 (3) | 0.0572 (10) | |
H3A | 0.1152 | 0.2070 | 0.7424 | 0.069* | |
C4 | 0.1236 (4) | 0.0577 (4) | 0.8698 (3) | 0.0668 (12) | |
H4A | 0.0401 | 0.0730 | 0.8671 | 0.080* | |
C5 | 0.2004 (4) | −0.0405 (4) | 0.9465 (3) | 0.0622 (11) | |
H5A | 0.1682 | −0.0909 | 0.9968 | 0.075* | |
C6 | 0.3281 (3) | −0.0695 (3) | 0.9532 (2) | 0.0439 (8) | |
C7 | 0.4075 (3) | −0.1704 (3) | 1.0349 (2) | 0.0472 (9) | |
H7A | 0.3757 | −0.2195 | 1.0865 | 0.057* | |
C8 | 0.5305 (3) | −0.1969 (3) | 1.0391 (2) | 0.0420 (8) | |
C9 | 0.5790 (3) | −0.1237 (3) | 0.9611 (2) | 0.0472 (8) | |
H9A | 0.6631 | −0.1435 | 0.9636 | 0.057* | |
C10 | 0.5050 (3) | −0.0246 (3) | 0.8822 (2) | 0.0412 (8) | |
H10A | 0.5396 | 0.0233 | 0.8322 | 0.049* | |
C11 | 0.3765 (3) | 0.0082 (3) | 0.8737 (2) | 0.0390 (7) | |
C12 | 0.4939 (3) | 0.4799 (3) | 0.6816 (2) | 0.0386 (7) | |
C13 | 0.4849 (3) | 0.5442 (3) | 0.7483 (2) | 0.0381 (7) | |
C14 | 0.5856 (3) | 0.5138 (3) | 0.8151 (2) | 0.0364 (7) | |
C15 | 0.7022 (3) | 0.4254 (3) | 0.8225 (2) | 0.0456 (8) | |
H15A | 0.7149 | 0.3856 | 0.7808 | 0.055* | |
C16 | 0.7955 (3) | 0.3983 (3) | 0.8900 (3) | 0.0537 (9) | |
H16A | 0.8712 | 0.3399 | 0.8944 | 0.064* | |
C17 | 0.7784 (3) | 0.4578 (3) | 0.9528 (3) | 0.0560 (10) | |
C18 | 0.6692 (3) | 0.5442 (3) | 0.9478 (3) | 0.0540 (9) | |
H18A | 0.6595 | 0.5836 | 0.9896 | 0.065* | |
C19 | 0.5706 (3) | 0.5740 (3) | 0.8790 (2) | 0.0425 (8) | |
C20 | 0.4563 (3) | 0.6639 (3) | 0.8721 (3) | 0.0534 (9) | |
H20A | 0.4461 | 0.7046 | 0.9130 | 0.064* | |
C21 | 0.3608 (3) | 0.6917 (4) | 0.8058 (3) | 0.0613 (10) | |
H21A | 0.2861 | 0.7514 | 0.8015 | 0.074* | |
C22 | 0.3753 (3) | 0.6300 (3) | 0.7442 (3) | 0.0534 (9) | |
H22A | 0.3095 | 0.6480 | 0.7002 | 0.064* | |
C23 | 0.2781 (3) | 0.6807 (3) | 0.4551 (2) | 0.0356 (7) | |
C24 | 0.1583 (3) | 0.7857 (3) | 0.4238 (2) | 0.0413 (8) | |
C25 | 0.0743 (3) | 0.7802 (4) | 0.4887 (3) | 0.0709 (13) | |
H25A | 0.0888 | 0.7086 | 0.5468 | 0.085* | |
C26 | −0.0343 (4) | 0.8810 (4) | 0.4695 (4) | 0.108 (2) | |
H26A | −0.0907 | 0.8761 | 0.5150 | 0.130* | |
C27 | −0.0572 (4) | 0.9860 (4) | 0.3841 (4) | 0.0933 (17) | |
H27A | −0.1288 | 1.0526 | 0.3725 | 0.112* | |
C28 | 0.0259 (3) | 0.9956 (3) | 0.3128 (3) | 0.0559 (10) | |
C29 | 0.0020 (3) | 1.1045 (3) | 0.2234 (3) | 0.0591 (10) | |
H29A | −0.0678 | 1.1728 | 0.2124 | 0.071* | |
C30 | 0.0798 (3) | 1.1095 (3) | 0.1540 (3) | 0.0504 (9) | |
C31 | 0.1842 (3) | 1.0078 (3) | 0.1691 (2) | 0.0487 (9) | |
H31A | 0.2354 | 1.0112 | 0.1198 | 0.058* | |
C32 | 0.2123 (3) | 0.9030 (3) | 0.2558 (2) | 0.0439 (8) | |
H32A | 0.2835 | 0.8368 | 0.2651 | 0.053* | |
C33 | 0.1358 (3) | 0.8934 (3) | 0.3311 (2) | 0.0399 (8) | |
C34 | 0.1302 (3) | 0.4750 (3) | 0.4221 (3) | 0.0511 (9) | |
H34A | 0.1139 | 0.5224 | 0.4579 | 0.061* | |
C35 | 0.0351 (3) | 0.4935 (4) | 0.3564 (3) | 0.0626 (11) | |
H35A | −0.0424 | 0.5508 | 0.3492 | 0.075* | |
C36 | 0.0593 (4) | 0.4255 (4) | 0.3035 (3) | 0.0680 (12) | |
H36A | −0.0022 | 0.4368 | 0.2586 | 0.082* | |
C37 | 0.1750 (4) | 0.3386 (4) | 0.3153 (3) | 0.0560 (10) | |
C38 | 0.2077 (5) | 0.2633 (5) | 0.2623 (3) | 0.0789 (14) | |
H38A | 0.1489 | 0.2719 | 0.2166 | 0.095* | |
C39 | 0.3197 (5) | 0.1811 (5) | 0.2764 (3) | 0.0818 (14) | |
H39A | 0.3377 | 0.1344 | 0.2399 | 0.098* | |
C40 | 0.4123 (4) | 0.1636 (3) | 0.3465 (3) | 0.0573 (10) | |
C41 | 0.5305 (4) | 0.0754 (4) | 0.3656 (3) | 0.0681 (12) | |
H41A | 0.5522 | 0.0269 | 0.3307 | 0.082* | |
C42 | 0.6124 (4) | 0.0618 (3) | 0.4354 (3) | 0.0650 (12) | |
H42A | 0.6909 | 0.0039 | 0.4486 | 0.078* | |
C43 | 0.5789 (3) | 0.1348 (3) | 0.4875 (3) | 0.0520 (9) | |
H43A | 0.6360 | 0.1227 | 0.5363 | 0.062* | |
C44 | 0.3857 (3) | 0.2351 (3) | 0.4011 (2) | 0.0389 (8) | |
C45 | 0.2655 (3) | 0.3247 (3) | 0.3845 (2) | 0.0390 (8) | |
N1 | 0.2417 (2) | 0.3944 (2) | 0.43657 (18) | 0.0380 (6) | |
N2 | 0.4692 (2) | 0.2208 (2) | 0.47064 (19) | 0.0378 (6) | |
O1 | 0.25998 (19) | 0.3115 (2) | 0.66020 (16) | 0.0501 (6) | |
O2 | 0.4394 (2) | 0.16976 (18) | 0.68524 (16) | 0.0471 (6) | |
O3 | 0.4570 (2) | 0.3902 (2) | 0.70848 (15) | 0.0518 (6) | |
O4 | 0.4683 (2) | 0.48225 (19) | 0.40107 (15) | 0.0448 (5) | |
O5 | 0.37166 (18) | 0.70586 (18) | 0.42525 (16) | 0.0418 (5) | |
O6 | 0.27937 (18) | 0.57429 (18) | 0.51237 (15) | 0.0395 (5) | |
O7 | 0.8780 (3) | 0.4249 (3) | 1.0199 (2) | 0.0842 (10) | |
H7 | 0.8599 | 0.4675 | 1.0509 | 0.126* | |
O8 | 0.0629 (2) | 1.2126 (2) | 0.06669 (19) | 0.0710 (8) | |
H8 | 0.0006 | 1.2682 | 0.0649 | 0.106* | |
O9 | 0.6148 (2) | −0.2937 (2) | 1.11577 (16) | 0.0572 (7) | |
H9 | 0.5805 | −0.3185 | 1.1648 | 0.086* | |
O1W | 0.8555 (2) | 0.5914 (3) | 1.0912 (2) | 0.0806 (9) | |
H1W | 0.7933 | 0.6013 | 1.1220 | 0.097* | |
H2W | 0.8754 | 0.6550 | 1.0650 | 0.097* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Eu1 | 0.02963 (9) | 0.02244 (8) | 0.02384 (8) | −0.00843 (6) | 0.00206 (6) | −0.00460 (6) |
C1 | 0.0463 (19) | 0.0347 (18) | 0.0319 (17) | −0.0226 (16) | 0.0079 (15) | −0.0139 (15) |
C2 | 0.052 (2) | 0.0419 (19) | 0.0371 (18) | −0.0274 (17) | 0.0127 (16) | −0.0157 (16) |
C3 | 0.056 (2) | 0.062 (2) | 0.046 (2) | −0.033 (2) | 0.0063 (18) | −0.0076 (18) |
C4 | 0.055 (2) | 0.080 (3) | 0.058 (3) | −0.042 (2) | 0.011 (2) | −0.008 (2) |
C5 | 0.070 (3) | 0.075 (3) | 0.048 (2) | −0.050 (2) | 0.020 (2) | −0.014 (2) |
C6 | 0.063 (2) | 0.043 (2) | 0.0358 (18) | −0.0323 (18) | 0.0151 (17) | −0.0160 (16) |
C7 | 0.076 (3) | 0.042 (2) | 0.0326 (18) | −0.0370 (19) | 0.0170 (18) | −0.0117 (16) |
C8 | 0.064 (2) | 0.0336 (18) | 0.0280 (17) | −0.0199 (17) | 0.0107 (16) | −0.0112 (15) |
C9 | 0.055 (2) | 0.045 (2) | 0.0357 (19) | −0.0189 (18) | 0.0137 (16) | −0.0118 (16) |
C10 | 0.057 (2) | 0.0357 (18) | 0.0314 (17) | −0.0225 (16) | 0.0160 (16) | −0.0109 (15) |
C11 | 0.058 (2) | 0.0370 (18) | 0.0314 (17) | −0.0280 (16) | 0.0149 (15) | −0.0149 (15) |
C12 | 0.0442 (19) | 0.0394 (19) | 0.0265 (16) | −0.0155 (16) | 0.0006 (14) | −0.0079 (14) |
C13 | 0.0463 (19) | 0.0374 (18) | 0.0307 (17) | −0.0208 (16) | 0.0065 (14) | −0.0101 (14) |
C14 | 0.0437 (19) | 0.0288 (17) | 0.0323 (17) | −0.0149 (15) | 0.0043 (14) | −0.0073 (14) |
C15 | 0.050 (2) | 0.0366 (19) | 0.046 (2) | −0.0151 (16) | 0.0074 (17) | −0.0129 (16) |
C16 | 0.046 (2) | 0.042 (2) | 0.061 (2) | −0.0050 (17) | −0.0003 (18) | −0.0172 (19) |
C17 | 0.055 (2) | 0.043 (2) | 0.056 (2) | −0.0090 (19) | −0.0157 (19) | −0.0140 (19) |
C18 | 0.055 (2) | 0.051 (2) | 0.055 (2) | −0.0113 (19) | −0.0063 (18) | −0.0257 (19) |
C19 | 0.045 (2) | 0.0405 (19) | 0.0389 (18) | −0.0144 (16) | −0.0036 (15) | −0.0145 (16) |
C20 | 0.054 (2) | 0.057 (2) | 0.055 (2) | −0.0115 (19) | 0.0031 (18) | −0.034 (2) |
C21 | 0.041 (2) | 0.068 (3) | 0.068 (3) | −0.0015 (19) | 0.0005 (19) | −0.036 (2) |
C22 | 0.044 (2) | 0.063 (2) | 0.053 (2) | −0.0135 (19) | −0.0047 (17) | −0.029 (2) |
C23 | 0.0345 (17) | 0.0280 (17) | 0.0356 (17) | −0.0064 (14) | 0.0008 (14) | −0.0087 (14) |
C24 | 0.0289 (16) | 0.0310 (17) | 0.052 (2) | −0.0073 (14) | 0.0054 (15) | −0.0094 (15) |
C25 | 0.047 (2) | 0.048 (2) | 0.072 (3) | −0.0024 (19) | 0.018 (2) | 0.006 (2) |
C26 | 0.063 (3) | 0.073 (3) | 0.107 (4) | 0.010 (3) | 0.047 (3) | 0.009 (3) |
C27 | 0.054 (3) | 0.055 (3) | 0.105 (4) | 0.012 (2) | 0.033 (3) | 0.001 (3) |
C28 | 0.0325 (19) | 0.041 (2) | 0.065 (2) | −0.0042 (16) | 0.0066 (17) | −0.0018 (18) |
C29 | 0.037 (2) | 0.037 (2) | 0.070 (3) | 0.0006 (16) | −0.0014 (19) | −0.0016 (19) |
C30 | 0.043 (2) | 0.042 (2) | 0.047 (2) | −0.0131 (17) | −0.0076 (17) | −0.0019 (17) |
C31 | 0.0405 (19) | 0.050 (2) | 0.042 (2) | −0.0127 (17) | 0.0030 (16) | −0.0095 (17) |
C32 | 0.0358 (18) | 0.0393 (19) | 0.046 (2) | −0.0074 (15) | 0.0023 (16) | −0.0129 (16) |
C33 | 0.0280 (16) | 0.0324 (18) | 0.050 (2) | −0.0062 (14) | 0.0017 (15) | −0.0116 (15) |
C34 | 0.0355 (19) | 0.052 (2) | 0.059 (2) | −0.0102 (17) | −0.0020 (17) | −0.0201 (19) |
C35 | 0.040 (2) | 0.064 (3) | 0.066 (3) | −0.0164 (19) | −0.0068 (19) | −0.011 (2) |
C36 | 0.070 (3) | 0.074 (3) | 0.051 (2) | −0.039 (3) | −0.018 (2) | −0.005 (2) |
C37 | 0.076 (3) | 0.059 (2) | 0.038 (2) | −0.042 (2) | −0.0043 (19) | −0.0102 (18) |
C38 | 0.108 (4) | 0.101 (4) | 0.058 (3) | −0.060 (3) | 0.003 (3) | −0.043 (3) |
C39 | 0.131 (4) | 0.090 (4) | 0.068 (3) | −0.063 (4) | 0.024 (3) | −0.056 (3) |
C40 | 0.088 (3) | 0.049 (2) | 0.053 (2) | −0.039 (2) | 0.031 (2) | −0.0292 (19) |
C41 | 0.100 (4) | 0.052 (3) | 0.078 (3) | −0.039 (3) | 0.049 (3) | −0.045 (2) |
C42 | 0.065 (3) | 0.039 (2) | 0.094 (3) | −0.018 (2) | 0.040 (2) | −0.034 (2) |
C43 | 0.051 (2) | 0.0339 (19) | 0.071 (3) | −0.0171 (17) | 0.0185 (19) | −0.0210 (18) |
C44 | 0.059 (2) | 0.0321 (18) | 0.0330 (17) | −0.0274 (17) | 0.0149 (16) | −0.0129 (14) |
C45 | 0.053 (2) | 0.0360 (18) | 0.0305 (17) | −0.0260 (16) | 0.0038 (15) | −0.0087 (14) |
N1 | 0.0382 (15) | 0.0372 (15) | 0.0362 (15) | −0.0144 (13) | 0.0014 (12) | −0.0124 (12) |
N2 | 0.0421 (15) | 0.0268 (14) | 0.0415 (15) | −0.0131 (12) | 0.0091 (13) | −0.0112 (12) |
O1 | 0.0372 (13) | 0.0429 (14) | 0.0467 (14) | −0.0121 (11) | 0.0042 (11) | 0.0014 (11) |
O2 | 0.0591 (15) | 0.0282 (12) | 0.0416 (13) | −0.0132 (11) | 0.0227 (12) | −0.0062 (10) |
O3 | 0.0864 (18) | 0.0552 (15) | 0.0287 (12) | −0.0477 (14) | 0.0125 (12) | −0.0144 (11) |
O4 | 0.0575 (14) | 0.0386 (13) | 0.0289 (12) | −0.0168 (11) | 0.0123 (11) | −0.0062 (10) |
O5 | 0.0313 (12) | 0.0288 (12) | 0.0507 (14) | −0.0079 (10) | 0.0008 (10) | −0.0051 (10) |
O6 | 0.0363 (12) | 0.0281 (12) | 0.0441 (13) | −0.0094 (10) | 0.0057 (10) | −0.0076 (10) |
O7 | 0.0682 (18) | 0.066 (2) | 0.096 (2) | 0.0060 (15) | −0.0412 (17) | −0.0339 (17) |
O8 | 0.0625 (18) | 0.0504 (17) | 0.0587 (17) | −0.0106 (14) | −0.0044 (14) | 0.0091 (14) |
O9 | 0.0728 (17) | 0.0471 (15) | 0.0338 (13) | −0.0192 (13) | 0.0120 (12) | −0.0022 (12) |
O1W | 0.0645 (18) | 0.088 (2) | 0.083 (2) | −0.0247 (17) | −0.0049 (16) | −0.0317 (18) |
Eu1—O5i | 2.334 (2) | C23—O5 | 1.260 (3) |
Eu1—O4 | 2.351 (2) | C23—O6 | 1.265 (3) |
Eu1—O6 | 2.3680 (19) | C23—C24 | 1.497 (4) |
Eu1—O2 | 2.411 (2) | C24—C25 | 1.356 (5) |
Eu1—O1 | 2.464 (2) | C24—C33 | 1.442 (4) |
Eu1—O3 | 2.471 (2) | C25—C26 | 1.404 (5) |
Eu1—N1 | 2.591 (2) | C25—H25A | 0.93 |
Eu1—N2 | 2.593 (2) | C26—C27 | 1.363 (6) |
Eu1—C1 | 2.809 (3) | C26—H26A | 0.93 |
Eu1—O4i | 2.925 (2) | C27—C28 | 1.414 (5) |
Eu1—C12 | 3.070 (3) | C27—H27A | 0.93 |
Eu1—Eu1i | 4.1594 (4) | C28—C29 | 1.420 (5) |
C1—O1 | 1.257 (4) | C28—C33 | 1.425 (4) |
C1—O2 | 1.263 (4) | C29—C30 | 1.352 (5) |
C1—C2 | 1.503 (4) | C29—H29A | 0.93 |
C2—C3 | 1.372 (5) | C30—O8 | 1.375 (4) |
C2—C11 | 1.437 (4) | C30—C31 | 1.392 (4) |
C3—C4 | 1.409 (5) | C31—C32 | 1.367 (4) |
C3—H3A | 0.93 | C31—H31A | 0.93 |
C4—C5 | 1.346 (5) | C32—C33 | 1.406 (4) |
C4—H4A | 0.93 | C32—H32A | 0.93 |
C5—C6 | 1.412 (5) | C34—N1 | 1.320 (4) |
C5—H5A | 0.93 | C34—C35 | 1.399 (5) |
C6—C7 | 1.406 (5) | C34—H34A | 0.93 |
C6—C11 | 1.439 (4) | C35—C36 | 1.352 (6) |
C7—C8 | 1.362 (5) | C35—H35A | 0.93 |
C7—H7A | 0.93 | C36—C37 | 1.393 (6) |
C8—O9 | 1.376 (4) | C36—H36A | 0.93 |
C8—C9 | 1.402 (4) | C37—C45 | 1.416 (4) |
C9—C10 | 1.354 (4) | C37—C38 | 1.429 (6) |
C9—H9A | 0.93 | C38—C39 | 1.333 (6) |
C10—C11 | 1.415 (4) | C38—H38A | 0.93 |
C10—H10A | 0.93 | C39—C40 | 1.424 (6) |
C12—O4i | 1.252 (3) | C39—H39A | 0.93 |
C12—O3 | 1.261 (4) | C40—C41 | 1.406 (5) |
C12—C13 | 1.506 (4) | C40—C44 | 1.410 (5) |
C13—C22 | 1.361 (4) | C41—C42 | 1.353 (6) |
C13—C14 | 1.406 (4) | C41—H41A | 0.93 |
C14—C19 | 1.420 (4) | C42—C43 | 1.395 (5) |
C14—C15 | 1.422 (4) | C42—H42A | 0.93 |
C15—C16 | 1.361 (5) | C43—N2 | 1.327 (4) |
C15—H15A | 0.93 | C43—H43A | 0.93 |
C16—C17 | 1.398 (5) | C44—N2 | 1.359 (4) |
C16—H16A | 0.93 | C44—C45 | 1.434 (4) |
C17—C18 | 1.359 (5) | C45—N1 | 1.360 (4) |
C17—O7 | 1.390 (4) | O4—C12i | 1.252 (3) |
C18—C19 | 1.409 (4) | O4—Eu1i | 2.925 (2) |
C18—H18A | 0.93 | O5—Eu1i | 2.334 (2) |
C19—C20 | 1.413 (4) | O7—H7 | 0.82 |
C20—C21 | 1.366 (5) | O8—H8 | 0.82 |
C20—H20A | 0.93 | O9—H9 | 0.82 |
C21—C22 | 1.405 (5) | O1W—H1W | 0.85 |
C21—H21A | 0.93 | O1W—H2W | 0.85 |
C22—H22A | 0.93 | ||
O5i—Eu1—O4 | 74.98 (7) | C19—C14—C15 | 117.9 (3) |
O5i—Eu1—O6 | 129.05 (7) | C16—C15—C14 | 120.8 (3) |
O4—Eu1—O6 | 77.08 (7) | C16—C15—H15A | 119.6 |
O5i—Eu1—O2 | 84.06 (7) | C14—C15—H15A | 119.6 |
O4—Eu1—O2 | 146.76 (8) | C15—C16—C17 | 120.4 (3) |
O6—Eu1—O2 | 135.53 (7) | C15—C16—H16A | 119.8 |
O5i—Eu1—O1 | 134.24 (7) | C17—C16—H16A | 119.8 |
O4—Eu1—O1 | 150.25 (8) | C18—C17—O7 | 121.9 (3) |
O6—Eu1—O1 | 84.24 (7) | C18—C17—C16 | 121.1 (3) |
O2—Eu1—O1 | 53.17 (7) | O7—C17—C16 | 117.0 (3) |
O5i—Eu1—O3 | 80.21 (8) | C17—C18—C19 | 119.9 (3) |
O4—Eu1—O3 | 123.18 (7) | C17—C18—H18A | 120.1 |
O6—Eu1—O3 | 80.71 (8) | C19—C18—H18A | 120.1 |
O2—Eu1—O3 | 76.85 (7) | C18—C19—C20 | 120.8 (3) |
O1—Eu1—O3 | 75.27 (8) | C18—C19—C14 | 120.0 (3) |
O5i—Eu1—N1 | 136.29 (8) | C20—C19—C14 | 119.2 (3) |
O4—Eu1—N1 | 79.35 (8) | C21—C20—C19 | 120.6 (3) |
O6—Eu1—N1 | 76.81 (8) | C21—C20—H20A | 119.7 |
O2—Eu1—N1 | 99.70 (8) | C19—C20—H20A | 119.7 |
O1—Eu1—N1 | 73.93 (8) | C20—C21—C22 | 120.0 (3) |
O3—Eu1—N1 | 143.30 (8) | C20—C21—H21A | 120.0 |
O5i—Eu1—N2 | 76.11 (8) | C22—C21—H21A | 120.0 |
O4—Eu1—N2 | 75.88 (7) | C13—C22—C21 | 120.6 (3) |
O6—Eu1—N2 | 135.20 (8) | C13—C22—H22A | 119.7 |
O2—Eu1—N2 | 74.18 (7) | C21—C22—H22A | 119.7 |
O1—Eu1—N2 | 102.94 (8) | O5—C23—O6 | 124.5 (3) |
O3—Eu1—N2 | 144.07 (8) | O5—C23—C24 | 117.3 (3) |
N1—Eu1—N2 | 63.57 (8) | O6—C23—C24 | 118.1 (3) |
O5i—Eu1—C1 | 109.21 (8) | C25—C24—C33 | 120.7 (3) |
O4—Eu1—C1 | 163.08 (8) | C25—C24—C23 | 117.8 (3) |
O6—Eu1—C1 | 109.84 (8) | C33—C24—C23 | 121.4 (3) |
O2—Eu1—C1 | 26.63 (8) | C24—C25—C26 | 121.0 (3) |
O1—Eu1—C1 | 26.56 (8) | C24—C25—H25A | 119.5 |
O3—Eu1—C1 | 73.66 (8) | C26—C25—H25A | 119.5 |
N1—Eu1—C1 | 87.13 (8) | C27—C26—C25 | 120.0 (4) |
N2—Eu1—C1 | 89.05 (8) | C27—C26—H26A | 120.0 |
O5i—Eu1—O4i | 64.62 (7) | C25—C26—H26A | 120.0 |
O4—Eu1—O4i | 76.48 (7) | C26—C27—C28 | 121.3 (4) |
O6—Eu1—O4i | 67.92 (7) | C26—C27—H27A | 119.3 |
O2—Eu1—O4i | 117.37 (7) | C28—C27—H27A | 119.3 |
O1—Eu1—O4i | 117.53 (7) | C27—C28—C29 | 121.5 (3) |
O3—Eu1—O4i | 46.70 (6) | C27—C28—C33 | 119.0 (3) |
N1—Eu1—O4i | 140.72 (7) | C29—C28—C33 | 119.4 (3) |
N2—Eu1—O4i | 136.47 (7) | C30—C29—C28 | 120.5 (3) |
C1—Eu1—O4i | 120.32 (7) | C30—C29—H29A | 119.8 |
O5i—Eu1—C12 | 74.44 (8) | C28—C29—H29A | 119.8 |
O4—Eu1—C12 | 100.14 (8) | C29—C30—O8 | 123.3 (3) |
O6—Eu1—C12 | 69.68 (8) | C29—C30—C31 | 120.5 (3) |
O2—Eu1—C12 | 98.67 (8) | O8—C30—C31 | 116.2 (3) |
O1—Eu1—C12 | 94.69 (8) | C32—C31—C30 | 120.6 (3) |
O3—Eu1—C12 | 23.25 (7) | C32—C31—H31A | 119.7 |
N1—Eu1—C12 | 145.58 (8) | C30—C31—H31A | 119.7 |
N2—Eu1—C12 | 150.26 (8) | C31—C32—C33 | 121.3 (3) |
C1—Eu1—C12 | 96.76 (8) | C31—C32—H32A | 119.3 |
O4i—Eu1—C12 | 23.95 (7) | C33—C32—H32A | 119.3 |
O5i—Eu1—Eu1i | 63.39 (5) | C32—C33—C28 | 117.5 (3) |
O4—Eu1—Eu1i | 43.14 (5) | C32—C33—C24 | 124.6 (3) |
O6—Eu1—Eu1i | 67.00 (5) | C28—C33—C24 | 117.8 (3) |
O2—Eu1—Eu1i | 142.76 (6) | N1—C34—C35 | 124.1 (4) |
O1—Eu1—Eu1i | 144.67 (6) | N1—C34—H34A | 118.0 |
O3—Eu1—Eu1i | 80.04 (5) | C35—C34—H34A | 118.0 |
N1—Eu1—Eu1i | 116.10 (5) | C36—C35—C34 | 117.9 (4) |
N2—Eu1—Eu1i | 111.84 (5) | C36—C35—H35A | 121.0 |
C1—Eu1—Eu1i | 153.62 (6) | C34—C35—H35A | 121.0 |
O4i—Eu1—Eu1i | 33.34 (4) | C35—C36—C37 | 120.9 (4) |
C12—Eu1—Eu1i | 57.10 (6) | C35—C36—H36A | 119.6 |
O1—C1—O2 | 120.0 (3) | C37—C36—H36A | 119.6 |
O1—C1—C2 | 119.5 (3) | C36—C37—C45 | 117.5 (4) |
O2—C1—C2 | 120.5 (3) | C36—C37—C38 | 124.2 (4) |
O1—C1—Eu1 | 61.21 (15) | C45—C37—C38 | 118.3 (4) |
O2—C1—Eu1 | 58.82 (15) | C39—C38—C37 | 122.0 (4) |
C2—C1—Eu1 | 177.1 (2) | C39—C38—H38A | 119.0 |
C3—C2—C11 | 119.7 (3) | C37—C38—H38A | 119.0 |
C3—C2—C1 | 117.2 (3) | C38—C39—C40 | 121.0 (4) |
C11—C2—C1 | 123.1 (3) | C38—C39—H39A | 119.5 |
C2—C3—C4 | 121.0 (3) | C40—C39—H39A | 119.5 |
C2—C3—H3A | 119.5 | C41—C40—C44 | 117.5 (4) |
C4—C3—H3A | 119.5 | C41—C40—C39 | 122.8 (4) |
C5—C4—C3 | 120.2 (3) | C44—C40—C39 | 119.6 (4) |
C5—C4—H4A | 119.9 | C42—C41—C40 | 119.3 (4) |
C3—C4—H4A | 119.9 | C42—C41—H41A | 120.3 |
C4—C5—C6 | 122.2 (3) | C40—C41—H41A | 120.3 |
C4—C5—H5A | 118.9 | C41—C42—C43 | 119.9 (4) |
C6—C5—H5A | 118.9 | C41—C42—H42A | 120.1 |
C7—C6—C5 | 121.9 (3) | C43—C42—H42A | 120.1 |
C7—C6—C11 | 120.0 (3) | N2—C43—C42 | 122.9 (4) |
C5—C6—C11 | 118.1 (3) | N2—C43—H43A | 118.6 |
C8—C7—C6 | 120.7 (3) | C42—C43—H43A | 118.6 |
C8—C7—H7A | 119.6 | N2—C44—C40 | 122.4 (3) |
C6—C7—H7A | 119.6 | N2—C44—C45 | 118.6 (3) |
C7—C8—O9 | 124.7 (3) | C40—C44—C45 | 119.0 (3) |
C7—C8—C9 | 119.9 (3) | N1—C45—C37 | 121.7 (3) |
O9—C8—C9 | 115.4 (3) | N1—C45—C44 | 118.4 (3) |
C10—C9—C8 | 120.9 (3) | C37—C45—C44 | 120.0 (3) |
C10—C9—H9A | 119.5 | C34—N1—C45 | 118.0 (3) |
C8—C9—H9A | 119.5 | C34—N1—Eu1 | 122.3 (2) |
C9—C10—C11 | 121.9 (3) | C45—N1—Eu1 | 119.7 (2) |
C9—C10—H10A | 119.1 | C43—N2—C44 | 117.9 (3) |
C11—C10—H10A | 119.1 | C43—N2—Eu1 | 122.5 (2) |
C10—C11—C2 | 124.8 (3) | C44—N2—Eu1 | 119.4 (2) |
C10—C11—C6 | 116.6 (3) | C1—O1—Eu1 | 92.23 (18) |
C2—C11—C6 | 118.6 (3) | C1—O2—Eu1 | 94.56 (18) |
O4i—C12—O3 | 120.2 (3) | C12—O3—Eu1 | 106.07 (18) |
O4i—C12—C13 | 120.9 (3) | C12i—O4—Eu1 | 167.9 (2) |
O3—C12—C13 | 118.7 (3) | C12i—O4—Eu1i | 84.49 (18) |
O4i—C12—Eu1 | 71.56 (17) | Eu1—O4—Eu1i | 103.52 (7) |
O3—C12—Eu1 | 50.68 (15) | C23—O5—Eu1i | 144.72 (19) |
C13—C12—Eu1 | 159.4 (2) | C23—O6—Eu1 | 135.27 (19) |
C22—C13—C14 | 121.0 (3) | C17—O7—H7 | 109.5 |
C22—C13—C12 | 117.9 (3) | C30—O8—H8 | 109.5 |
C14—C13—C12 | 121.0 (3) | C8—O9—H9 | 109.5 |
C13—C14—C19 | 118.6 (3) | H1W—O1W—H2W | 113.7 |
C13—C14—C15 | 123.5 (3) | ||
O5i—Eu1—C1—O1 | 162.80 (17) | C39—C40—C41—C42 | −178.1 (4) |
O4—Eu1—C1—O1 | −95.5 (3) | C40—C41—C42—C43 | 0.1 (6) |
O6—Eu1—C1—O1 | 16.2 (2) | C41—C42—C43—N2 | −1.5 (6) |
O2—Eu1—C1—O1 | −177.2 (3) | C41—C40—C44—N2 | −0.5 (5) |
O3—Eu1—C1—O1 | 89.65 (19) | C39—C40—C44—N2 | 178.4 (3) |
N1—Eu1—C1—O1 | −58.69 (18) | C41—C40—C44—C45 | −179.1 (3) |
N2—Eu1—C1—O1 | −122.27 (18) | C39—C40—C44—C45 | −0.2 (5) |
O4i—Eu1—C1—O1 | 91.59 (19) | C36—C37—C45—N1 | −1.0 (5) |
C12—Eu1—C1—O1 | 86.97 (19) | C38—C37—C45—N1 | 179.0 (3) |
Eu1i—Eu1—C1—O1 | 94.2 (2) | C36—C37—C45—C44 | 178.9 (3) |
O5i—Eu1—C1—O2 | −20.0 (2) | C38—C37—C45—C44 | −1.1 (5) |
O4—Eu1—C1—O2 | 81.7 (3) | N2—C44—C45—N1 | 2.3 (4) |
O6—Eu1—C1—O2 | −166.67 (17) | C40—C44—C45—N1 | −179.0 (3) |
O1—Eu1—C1—O2 | 177.2 (3) | N2—C44—C45—C37 | −177.6 (3) |
O3—Eu1—C1—O2 | −93.20 (19) | C40—C44—C45—C37 | 1.1 (4) |
N1—Eu1—C1—O2 | 118.46 (18) | C35—C34—N1—C45 | −0.2 (5) |
N2—Eu1—C1—O2 | 54.88 (18) | C35—C34—N1—Eu1 | 178.0 (3) |
O4i—Eu1—C1—O2 | −91.26 (19) | C37—C45—N1—C34 | 1.1 (4) |
C12—Eu1—C1—O2 | −95.88 (18) | C44—C45—N1—C34 | −178.8 (3) |
Eu1i—Eu1—C1—O2 | −88.6 (2) | C37—C45—N1—Eu1 | −177.2 (2) |
O1—C1—C2—C3 | 23.8 (4) | C44—C45—N1—Eu1 | 3.0 (3) |
O2—C1—C2—C3 | −156.6 (3) | O5i—Eu1—N1—C34 | −157.7 (2) |
O1—C1—C2—C11 | −156.7 (3) | O4—Eu1—N1—C34 | −103.0 (2) |
O2—C1—C2—C11 | 22.8 (5) | O6—Eu1—N1—C34 | −23.9 (2) |
C11—C2—C3—C4 | −0.9 (5) | O2—Eu1—N1—C34 | 110.8 (2) |
C1—C2—C3—C4 | 178.6 (3) | O1—Eu1—N1—C34 | 63.8 (2) |
C2—C3—C4—C5 | 2.6 (6) | O3—Eu1—N1—C34 | 29.8 (3) |
C3—C4—C5—C6 | −1.5 (7) | N2—Eu1—N1—C34 | 177.6 (3) |
C4—C5—C6—C7 | 178.2 (4) | C1—Eu1—N1—C34 | 87.2 (2) |
C4—C5—C6—C11 | −1.3 (6) | O4i—Eu1—N1—C34 | −50.3 (3) |
C5—C6—C7—C8 | 179.5 (3) | C12—Eu1—N1—C34 | −10.6 (3) |
C11—C6—C7—C8 | −1.0 (5) | Eu1i—Eu1—N1—C34 | −79.8 (2) |
C6—C7—C8—O9 | −179.7 (3) | O5i—Eu1—N1—C45 | 20.5 (3) |
C6—C7—C8—C9 | −0.5 (5) | O4—Eu1—N1—C45 | 75.2 (2) |
C7—C8—C9—C10 | 1.7 (5) | O6—Eu1—N1—C45 | 154.2 (2) |
O9—C8—C9—C10 | −179.0 (3) | O2—Eu1—N1—C45 | −71.0 (2) |
C8—C9—C10—C11 | −1.3 (5) | O1—Eu1—N1—C45 | −118.0 (2) |
C9—C10—C11—C2 | 177.6 (3) | O3—Eu1—N1—C45 | −152.02 (19) |
C9—C10—C11—C6 | −0.2 (5) | N2—Eu1—N1—C45 | −4.2 (2) |
C3—C2—C11—C10 | −179.6 (3) | C1—Eu1—N1—C45 | −94.6 (2) |
C1—C2—C11—C10 | 0.9 (5) | O4i—Eu1—N1—C45 | 127.9 (2) |
C3—C2—C11—C6 | −1.8 (5) | C12—Eu1—N1—C45 | 167.61 (19) |
C1—C2—C11—C6 | 178.7 (3) | Eu1i—Eu1—N1—C45 | 98.4 (2) |
C7—C6—C11—C10 | 1.3 (4) | C42—C43—N2—C44 | 1.8 (5) |
C5—C6—C11—C10 | −179.2 (3) | C42—C43—N2—Eu1 | −173.8 (3) |
C7—C6—C11—C2 | −176.6 (3) | C40—C44—N2—C43 | −0.8 (4) |
C5—C6—C11—C2 | 2.9 (5) | C45—C44—N2—C43 | 177.9 (3) |
O5i—Eu1—C12—O4i | 62.03 (17) | C40—C44—N2—Eu1 | 174.9 (2) |
O4—Eu1—C12—O4i | −9.1 (2) | C45—C44—N2—Eu1 | −6.4 (3) |
O6—Eu1—C12—O4i | −81.16 (18) | O5i—Eu1—N2—C43 | 18.3 (2) |
O2—Eu1—C12—O4i | 143.34 (17) | O4—Eu1—N2—C43 | 96.0 (2) |
O1—Eu1—C12—O4i | −163.24 (17) | O6—Eu1—N2—C43 | 150.5 (2) |
O3—Eu1—C12—O4i | 163.6 (3) | O2—Eu1—N2—C43 | −69.4 (2) |
N1—Eu1—C12—O4i | −95.0 (2) | O1—Eu1—N2—C43 | −114.6 (2) |
N2—Eu1—C12—O4i | 70.1 (2) | O3—Eu1—N2—C43 | −31.9 (3) |
C1—Eu1—C12—O4i | 170.14 (18) | N1—Eu1—N2—C43 | −179.0 (3) |
Eu1i—Eu1—C12—O4i | −6.04 (14) | C1—Eu1—N2—C43 | −91.8 (2) |
O5i—Eu1—C12—O3 | −101.6 (2) | O4i—Eu1—N2—C43 | 43.9 (3) |
O4—Eu1—C12—O3 | −172.7 (2) | C12—Eu1—N2—C43 | 10.3 (3) |
O6—Eu1—C12—O3 | 115.2 (2) | Eu1i—Eu1—N2—C43 | 71.7 (2) |
O2—Eu1—C12—O3 | −20.3 (2) | O5i—Eu1—N2—C44 | −157.2 (2) |
O1—Eu1—C12—O3 | 33.1 (2) | O4—Eu1—N2—C44 | −79.5 (2) |
N1—Eu1—C12—O3 | 101.3 (2) | O6—Eu1—N2—C44 | −25.0 (2) |
N2—Eu1—C12—O3 | −93.5 (3) | O2—Eu1—N2—C44 | 115.1 (2) |
C1—Eu1—C12—O3 | 6.5 (2) | O1—Eu1—N2—C44 | 69.9 (2) |
O4i—Eu1—C12—O3 | −163.6 (3) | O3—Eu1—N2—C44 | 152.55 (19) |
Eu1i—Eu1—C12—O3 | −169.7 (2) | N1—Eu1—N2—C44 | 5.44 (19) |
O5i—Eu1—C12—C13 | −167.1 (6) | C1—Eu1—N2—C44 | 92.7 (2) |
O4—Eu1—C12—C13 | 121.7 (6) | O4i—Eu1—N2—C44 | −131.59 (19) |
O6—Eu1—C12—C13 | 49.7 (6) | C12—Eu1—N2—C44 | −165.26 (19) |
O2—Eu1—C12—C13 | −85.8 (6) | Eu1i—Eu1—N2—C44 | −103.8 (2) |
O1—Eu1—C12—C13 | −32.4 (6) | O2—C1—O1—Eu1 | −2.8 (3) |
O3—Eu1—C12—C13 | −65.5 (6) | C2—C1—O1—Eu1 | 176.7 (2) |
N1—Eu1—C12—C13 | 35.8 (6) | O5i—Eu1—O1—C1 | −22.9 (2) |
N2—Eu1—C12—C13 | −159.0 (5) | O4—Eu1—O1—C1 | 144.29 (18) |
C1—Eu1—C12—C13 | −59.0 (6) | O6—Eu1—O1—C1 | −164.72 (19) |
O4i—Eu1—C12—C13 | 130.8 (7) | O2—Eu1—O1—C1 | 1.60 (17) |
Eu1i—Eu1—C12—C13 | 124.8 (6) | O3—Eu1—O1—C1 | −82.84 (18) |
O4i—C12—C13—C22 | 95.3 (4) | N1—Eu1—O1—C1 | 117.37 (19) |
O3—C12—C13—C22 | −81.4 (4) | N2—Eu1—O1—C1 | 60.16 (19) |
Eu1—C12—C13—C22 | −28.0 (7) | O4i—Eu1—O1—C1 | −103.32 (18) |
O4i—C12—C13—C14 | −86.8 (4) | C12—Eu1—O1—C1 | −95.73 (18) |
O3—C12—C13—C14 | 96.6 (4) | Eu1i—Eu1—O1—C1 | −129.97 (16) |
Eu1—C12—C13—C14 | 150.0 (5) | O1—C1—O2—Eu1 | 2.9 (3) |
C22—C13—C14—C19 | 0.4 (5) | C2—C1—O2—Eu1 | −176.7 (2) |
C12—C13—C14—C19 | −177.5 (3) | O5i—Eu1—O2—C1 | 161.01 (19) |
C22—C13—C14—C15 | −179.8 (3) | O4—Eu1—O2—C1 | −148.32 (17) |
C12—C13—C14—C15 | 2.3 (5) | O6—Eu1—O2—C1 | 18.0 (2) |
C13—C14—C15—C16 | −178.8 (3) | O1—Eu1—O2—C1 | −1.59 (17) |
C19—C14—C15—C16 | 1.0 (5) | O3—Eu1—O2—C1 | 79.71 (18) |
C14—C15—C16—C17 | −0.5 (5) | N1—Eu1—O2—C1 | −62.98 (19) |
C15—C16—C17—C18 | −0.4 (6) | N2—Eu1—O2—C1 | −121.79 (19) |
C15—C16—C17—O7 | 179.8 (3) | O4i—Eu1—O2—C1 | 103.63 (18) |
O7—C17—C18—C19 | −179.6 (3) | C12—Eu1—O2—C1 | 87.79 (18) |
C16—C17—C18—C19 | 0.7 (6) | Eu1i—Eu1—O2—C1 | 132.77 (16) |
C17—C18—C19—C20 | −179.7 (3) | O4i—C12—O3—Eu1 | −18.0 (4) |
C17—C18—C19—C14 | −0.1 (5) | C13—C12—O3—Eu1 | 158.6 (2) |
C13—C14—C19—C18 | 179.1 (3) | O5i—Eu1—O3—C12 | 73.3 (2) |
C15—C14—C19—C18 | −0.7 (5) | O4—Eu1—O3—C12 | 8.5 (2) |
C13—C14—C19—C20 | −1.4 (5) | O6—Eu1—O3—C12 | −59.3 (2) |
C15—C14—C19—C20 | 178.8 (3) | O2—Eu1—O3—C12 | 159.4 (2) |
C18—C19—C20—C21 | −179.5 (4) | O1—Eu1—O3—C12 | −145.7 (2) |
C14—C19—C20—C21 | 1.0 (5) | N1—Eu1—O3—C12 | −112.0 (2) |
C19—C20—C21—C22 | 0.4 (6) | N2—Eu1—O3—C12 | 122.5 (2) |
C14—C13—C22—C21 | 0.9 (5) | C1—Eu1—O3—C12 | −173.3 (2) |
C12—C13—C22—C21 | 178.9 (3) | O4i—Eu1—O3—C12 | 9.05 (19) |
C20—C21—C22—C13 | −1.4 (6) | Eu1i—Eu1—O3—C12 | 8.8 (2) |
O5—C23—C24—C25 | −145.8 (3) | O5i—Eu1—O4—C12i | 63.5 (10) |
O6—C23—C24—C25 | 31.7 (5) | O6—Eu1—O4—C12i | −159.5 (10) |
O5—C23—C24—C33 | 29.7 (4) | O2—Eu1—O4—C12i | 10.7 (11) |
O6—C23—C24—C33 | −152.9 (3) | O1—Eu1—O4—C12i | −107.0 (10) |
C33—C24—C25—C26 | −2.8 (7) | O3—Eu1—O4—C12i | 130.8 (10) |
C23—C24—C25—C26 | 172.7 (4) | N1—Eu1—O4—C12i | −80.8 (10) |
C24—C25—C26—C27 | 0.7 (8) | N2—Eu1—O4—C12i | −15.6 (10) |
C25—C26—C27—C28 | 0.9 (9) | C1—Eu1—O4—C12i | −43.3 (12) |
C26—C27—C28—C29 | 179.5 (5) | O4i—Eu1—O4—C12i | 130.4 (11) |
C26—C27—C28—C33 | −0.3 (8) | C12—Eu1—O4—C12i | 134.2 (10) |
C27—C28—C29—C30 | −176.8 (4) | Eu1i—Eu1—O4—C12i | 130.4 (11) |
C33—C28—C29—C30 | 3.0 (6) | O5i—Eu1—O4—Eu1i | −66.92 (8) |
C28—C29—C30—O8 | −179.0 (3) | O6—Eu1—O4—Eu1i | 70.03 (7) |
C28—C29—C30—C31 | 0.3 (6) | O2—Eu1—O4—Eu1i | −119.73 (13) |
C29—C30—C31—C32 | −2.5 (5) | O1—Eu1—O4—Eu1i | 122.51 (14) |
O8—C30—C31—C32 | 176.8 (3) | O3—Eu1—O4—Eu1i | 0.38 (12) |
C30—C31—C32—C33 | 1.5 (5) | N1—Eu1—O4—Eu1i | 148.79 (9) |
C31—C32—C33—C28 | 1.8 (5) | N2—Eu1—O4—Eu1i | −146.04 (9) |
C31—C32—C33—C24 | 179.2 (3) | C1—Eu1—O4—Eu1i | −173.7 (3) |
C27—C28—C33—C32 | 175.8 (4) | O4i—Eu1—O4—Eu1i | 0.0 |
C29—C28—C33—C32 | −3.9 (5) | C12—Eu1—O4—Eu1i | 3.80 (9) |
C27—C28—C33—C24 | −1.8 (6) | O6—C23—O5—Eu1i | −9.4 (6) |
C29—C28—C33—C24 | 178.4 (3) | C24—C23—O5—Eu1i | 167.9 (2) |
C25—C24—C33—C32 | −174.1 (4) | O5—C23—O6—Eu1 | −21.9 (5) |
C23—C24—C33—C32 | 10.6 (5) | C24—C23—O6—Eu1 | 160.9 (2) |
C25—C24—C33—C28 | 3.3 (5) | O5i—Eu1—O6—C23 | 36.2 (3) |
C23—C24—C33—C28 | −172.0 (3) | O4—Eu1—O6—C23 | −21.9 (3) |
N1—C34—C35—C36 | −0.8 (6) | O2—Eu1—O6—C23 | 165.7 (3) |
C34—C35—C36—C37 | 0.8 (6) | O1—Eu1—O6—C23 | −178.6 (3) |
C35—C36—C37—C45 | 0.0 (5) | O3—Eu1—O6—C23 | 105.4 (3) |
C35—C36—C37—C38 | 180.0 (4) | N1—Eu1—O6—C23 | −103.8 (3) |
C36—C37—C38—C39 | −179.8 (4) | N2—Eu1—O6—C23 | −76.0 (3) |
C45—C37—C38—C39 | 0.1 (6) | C1—Eu1—O6—C23 | 174.2 (3) |
C37—C38—C39—C40 | 0.8 (7) | O4i—Eu1—O6—C23 | 58.5 (3) |
C38—C39—C40—C41 | 178.1 (4) | C12—Eu1—O6—C23 | 84.2 (3) |
C38—C39—C40—C44 | −0.7 (6) | Eu1i—Eu1—O6—C23 | 22.4 (3) |
C44—C40—C41—C42 | 0.8 (5) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W···O9ii | 0.85 | 2.05 | 2.799 (4) | 147 |
O1W—H2W···O8iii | 0.85 | 2.28 | 3.050 (4) | 150 |
O7—H7···O1W | 0.82 | 1.89 | 2.670 (5) | 159 |
O8—H8···O7iv | 0.82 | 1.88 | 2.664 (5) | 160 |
O9—H9···O3v | 0.82 | 1.84 | 2.642 (3) | 165 |
Symmetry codes: (ii) x, y+1, z; (iii) −x+1, −y+2, −z+1; (iv) x−1, y+1, z−1; (v) −x+1, −y, −z+2. |
Experimental details
Crystal data | |
Chemical formula | [Eu2(C11H7O3)6(C12H8N2)2]·2H2O |
Mr | 1823.36 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 11.7132 (9), 12.7143 (10), 14.8822 (12) |
α, β, γ (°) | 65.790 (1), 88.276 (1), 70.437 (1) |
V (Å3) | 1889.8 (3) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 1.73 |
Crystal size (mm) | 0.30 × 0.21 × 0.17 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.626, 0.758 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13943, 6615, 5910 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.026, 0.057, 1.04 |
No. of reflections | 6615 |
No. of parameters | 526 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.66, −0.56 |
Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
Eu1—O5i | 2.334 (2) | Eu1—O3 | 2.471 (2) |
Eu1—O4 | 2.351 (2) | Eu1—N1 | 2.591 (2) |
Eu1—O6 | 2.3680 (19) | Eu1—N2 | 2.593 (2) |
Eu1—O2 | 2.411 (2) | Eu1—O4i | 2.925 (2) |
Eu1—O1 | 2.464 (2) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W···O9ii | 0.85 | 2.05 | 2.799 (4) | 147 |
O1W—H2W···O8iii | 0.85 | 2.28 | 3.050 (4) | 150 |
O7—H7···O1W | 0.82 | 1.89 | 2.670 (5) | 159 |
O8—H8···O7iv | 0.82 | 1.88 | 2.664 (5) | 160 |
O9—H9···O3v | 0.82 | 1.84 | 2.642 (3) | 165 |
Symmetry codes: (ii) x, y+1, z; (iii) −x+1, −y+2, −z+1; (iv) x−1, y+1, z−1; (v) −x+1, −y, −z+2. |
Acknowledgements
This work was supported by the start-up fund for PhDs of the Natural Scientific Research of Zhengzhou University of Light Industry (Nos. 2007BSJJ001 and 20801049).
References
Bettencourt-Dias, A. (2005). Inorg. Chem. 44, 2734–2741. Web of Science PubMed Google Scholar
Bettencourt-Dias, A. & Viswanathan, S. (2006). Dalton Trans. pp. 4093–4103. Web of Science CSD CrossRef Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bünzli, J.-C. G. (2006). Acc. Chem. Res. 39, 53–61. Web of Science PubMed Google Scholar
Edelmann, F. T. (2009). Coord. Chem. Rev. 253, 2515–2587. Web of Science CrossRef CAS Google Scholar
Fang, J., You, H., Chen, J., Lin, J. & Ma, D. (2006). Inorg. Chem. 45, 3701–3704. Web of Science CrossRef PubMed CAS Google Scholar
Li, Y.-J. & Yan, B. (2009). Inorg. Chem. 48, 8276–8285. Web of Science CrossRef PubMed CAS Google Scholar
Qu, Y. L., Ke, Y. X., Lu, S. M., Fan, R., Pan, G. Q. & Li, J. M. (2005). J. Mol. Struct. 734, 7–13. Web of Science CSD CrossRef CAS Google Scholar
Serre, C. & Férey, G. (2002). J. Mater. Chem. 12, 3053–3057. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wan, Y., Jin, L., Wang, K., Zhang, L., Zheng, X. & Lu, S. (2002). New J. Chem. 26, 1590–1596. Web of Science CSD CrossRef CAS Google Scholar
Xu, J.-X., Ma, Y., Liao, D.-Z., Xu, G.-F., Tang, J., Wang, C., Zhou, N., Yan, S.-P., Cheng, P. & Li, L.-C. (2009). Inorg. Chem. 48, 8890–8896. Web of Science CSD CrossRef PubMed CAS Google Scholar
Yang, J., Yue, Q., Li, G.-D., Cao, J.-J., Li, G.-H. & Chen, J.-S. (2006). Inorg. Chem. 45, 2857–2865. Web of Science CSD CrossRef PubMed CAS Google Scholar
Ye, B. H., Tong, M. L. & Chen, X. M. (2005). Coord. Chem. Rev. 249, 545–565. Web of Science CrossRef CAS Google Scholar
Zheng, X.-J., Jin, L.-P., Gao, S. & Lu, S.-Z. (2005). New J. Chem. 29, 798–804. Web of Science CSD CrossRef CAS Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
In recent years, the rational design and synthesis of functional rare-earth (RE) coordination complexes with various N– and/or O-donor ligands has attracted great interest because of not only their fascinating structural diversities but also their potential applications as functional materials, for example, optical materials, electronic materials, catalytic materials, and molecular-based magnets (Bünzli, 2006; Edelmann, 2009; Fang et al., 2006; Li & Yan, 2009; Xu et al., 2009). In this field, the choice of suitable organic ligands favoring structure-specific self-assembly is crucial for the construction of prospective coordination structures with relevant properties and functions. Among various ligands, the versatile carboxylic acid ligands, especially the benzene- and naphthalene-based di- and multi-carboxylic acids, have been well used in the preparation of various rare-earth (RE) complexes owing to their rich coordination modes (Bettencourt-Dias, 2005; Bettencourt-Dias & Viswanathan, 2006; Qu et al., 2005; Serre & Férey, 2002; Yang et al., 2006). However, far less common has been the use of naphthalene-based monocarboxylic acids, such as the acid used herein, 6-hydroxy-1-naphthoic acid (HL). Besides, the introduction of 2,2'-bipyridyl-like bidentate chelating molecules (2,2'-bipyridine or 1,10-phenanthroline) into the reaction systems including various carboxylic acid ligands, as auxiliary ligands, can generate some interesting coordination architectures (Ye et al., 2005). We report here the crystal structure of the title complex (I), a EuIII complex with mixed 6-hydroxy-1-naphthoic acid (L) and chelating 1,10-phenanthroline (phen) ligands.
The structure of complex (I) consists of a centrosymmetric dinuclear unit [Eu2(L)6(phen)2] and two free water molecules. The EuIII ion is nine-coordinated by two N-atom donors from one chelating phen ligand and seven O atoms from five distinct L ligands (Fig. 1). The Eu—O distances are in the range of 2.334 (2)–2.925 (2) Å, which are normal and in agreement with those found in other carboxylato-containing EuIII complexes (Zheng et al., 2005; Wan et al., 2002). The phen ligand acts as a typical chelating ligand coordinating to the EuIII ion with Eu—N bond distances of 2.591 (2) and 2.593 (2) Å, and an N—Eu—N angle of 63.57 (8)°. For L, there exists three different kinds of carboxylate coordination modes with the EuIII center, namely syn-syn bridging (µ2-η1:η1-bridging), symmetric bidentate chelate (µ1-η1:η1-chelating), and tridentate chelating/bridging (µ2-η1:η2-chelating/bridging). In this case two EuIII ions are connected to form an eight-membered ring [Eu1/O6/C23/O5/Eu1A/O6A/C23A/O5A], as well as a four-membered ring [Eu1/O4/Eu1A/O4A]. The non-bonding Eu1···Eu1A separation is 4.1594 (4) Å (symmetry operation A = 1 - x, 1 - y, 1 - z).
Adjacent dinuclear [Eu2(L)6(phen)2] units are linked into two different chains running along the [011] (Fig.2) and [111] (Fig. 3) and thus generating a two-dimensional sheet parallel to the (011) by intermolecular O—H···O hydrogen-bonding interactions (Table 1) between different L ligands (Fig. 4). The sheets are cross-linked via O—H···O hydrogen bonds involving the water molecules. In addition, intermolecular π–π stacking interactions are observed between the N2/C43/C42/C41/C40/C44 pyridine rings of the phen ligands at (x, y, z) and (1-x, -y, 1-z), with a centroid-to-centroid separation of 3.547 (2) Å.