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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): m1445.
Published online 2010 October 23. doi:  10.1107/S1600536810042194
PMCID: PMC3009253

Bis{[6-meth­oxy-2-(4-methyl­phen­yl)iminiometh­yl]phenolate-κ2 O,O′}tris­(nitrato-κ2 O,O′)europium(III)

Abstract

The crystal structure of title compound, [Eu(NO3)3(C15H15NO2)2], contains two Schiff base 6-meth­oxy-2-[(4-methyl­phen­yl)imino­meth­yl]phenolate (L) ligands and three independent nitrate ions that chelate to the europium(III) ion via the O atoms. The coordination number of the EuIII ion is ten. The L ligands chelate with a strong Eu—O(deprotonated phenolate) bond and a weak Eu—O(meth­oxy) contact, the latter can be inter­preted as the apices of the bicapped square-anti­prismatic EuIII polyhedron. Intra­molecular N—H(...)O hydrogen bonds occur.

Related literature

For Schiff base ligands derived from o-vanillin and aniline and their rare earth complexes, see: Burrows & Bailar (1966 [triangle]); Li et al. (2008 [triangle]); Liu et al. (2009 [triangle]); Xian et al. (2008 [triangle]); Zhao et al. (2005 [triangle], 2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1445-scheme1.jpg

Experimental

Crystal data

  • [Eu(NO3)3(C15H15NO2)2]
  • M r = 820.55
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1445-efi1.jpg
  • a = 9.7603 (7) Å
  • b = 10.0250 (7) Å
  • c = 18.4227 (16) Å
  • α = 98.165 (6)°
  • β = 101.665 (6)°
  • γ = 106.681 (4)°
  • V = 1652.2 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.97 mm−1
  • T = 296 K
  • 0.18 × 0.09 × 0.06 mm

Data collection

  • Bruker APEXII area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.801, T max = 0.892
  • 26273 measured reflections
  • 7610 independent reflections
  • 5570 reflections with I > 2σ(I)
  • R int = 0.051

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.094
  • S = 0.99
  • 7610 reflections
  • 442 parameters
  • H-atom parameters constrained
  • Δρmax = 0.85 e Å−3
  • Δρmin = −0.69 e Å−3

Data collection: APEX2 (Bruker, 2006 [triangle]); cell refinement: SAINT (Bruker, 2006 [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: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810042194/hg2728sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042194/hg2728Isup2.hkl

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

supplementary crystallographic information

Comment

It has well been confirmed that Schiff bases are important in multiple fields such as chemistry and biochemistry owing to their biological activities (Zhao et al., 2005). Schiff base complexes prepared by ligands from substituted o-vanillin have been absorbed considerable attention in the past decades due to the intriguing biological activities of o-vanillin and the convenience in Schiff bases synthesis (Burrows & Bailar, 1966). Interested in this field, we have been engaged in a major effort directed toward the development of syntheses of new analogous Schiff bases derived from o-vanillin and their rare metal complexes. In a few of articles we have reported our partial research results (Zhao et al., 2007; Xian et al. 2008; Li et al. 2008; Liu et al. 2009). Herein, we describe a new EuIII complex.

The structure of the title complex is shown in Fig.1, and the coordination environment of EuIII is shown in Fig. 2. In this complex the EuIII is eight-coordinated by O atoms, six of which come from three nitrate ions and two come from the Schiff base ligands (HL). The HL ligands coordinate to the EuIII ion using oxygen atoms from deprotonated phenolic hydroxyl groups. The ten Eu—O bond distances are listed in Table 1 (including weak Eu—O interactions). The distances between EuIII and methoxyl O atoms (2.743Å and 2.748Å for Eu—O2 and Eu—O4) are similar with reported complexe (Zhao et al., 2007).

The hydrogen bonds and π···π weak non-covalent interactions lend stability to the structure. The hydrogen bonds are listed in Table 2 and the stacking plot of this compound is shown in Fig. 3. There is π···π interactions exist in the crystal between symmetry-related molecules. In HL ligands, the proton of the phenolic hydroxyl group is considered to have transferred to N-imine atom, which involving in an intramolecular hydrogen bond (Table 2).

Experimental

Reagents and solvents used were of commercially available quality and without purified before using. The Schiff base ligand 2-[(4- methylphenyl)iminomethyl]-6-methoxy-phenol was prepared by condensation of o-vanillin and p-methylaniline with a high yield and which was purified by recrystallization in ethanol. The compound (1) was obtained by adding Eu(NO3)3 (1 mmol, dissolved in ethanol) to N-salicylidene-p-toluidine (2 mmol) in ethanol solution. The mixture solution was stirred at room temperature for 8 h to obtain a purplish red solution. At last, the deposit was filtered out and the solution was kept for evaporating. The red crystal was formed after several days.

Refinement

The structure was solved by direct methods and successive Fourier difference synthesis. The H atoms bonded to C and N atoms were positioned geometrically and refined using a riding model [aliphatic C—H =0.96 Å (Uiso(H) = 1.5Ueq(C)), aromatic C—H = 0.93 Å (Uiso(H) = 1.2Ueq(C)) and N—H = 0.86 Å with Uiso(H) = 1.2Ueq(N).

Figures

Fig. 1.
The molecular structure of the title complex, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
The coordination environment of the Europium(III) atom, showing the bicapped square antiprism.
Fig. 3.
The stacking plot of the title compound, showing H-bond interactions (dashed lines) and π···π stacking interactions.

Crystal data

[Eu(NO3)3(C15H15NO2)2]Z = 2
Mr = 820.55F(000) = 824
Triclinic, P1Dx = 1.649 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.7603 (7) ÅCell parameters from 4647 reflections
b = 10.0250 (7) Åθ = 1.2–27.7°
c = 18.4227 (16) ŵ = 1.97 mm1
α = 98.165 (6)°T = 296 K
β = 101.665 (6)°Block, red
γ = 106.681 (4)°0.18 × 0.09 × 0.06 mm
V = 1652.2 (2) Å3

Data collection

Bruker APEXII area-detector diffractometer7610 independent reflections
Radiation source: fine-focus sealed tube5570 reflections with I > 2σ(I)
graphiteRint = 0.051
phi and ω scansθmax = 27.7°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→11
Tmin = 0.801, Tmax = 0.892k = −12→13
26273 measured reflectionsl = −23→24

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094H-atom parameters constrained
S = 0.99w = 1/[σ2(Fo2) + (0.046P)2] where P = (Fo2 + 2Fc2)/3
7610 reflections(Δ/σ)max = 0.001
442 parametersΔρmax = 0.85 e Å3
0 restraintsΔρmin = −0.69 e Å3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

xyzUiso*/Ueq
Eu0.96447 (2)0.31215 (2)0.252484 (12)0.04432 (9)
N10.5030 (4)−0.0343 (4)0.2208 (2)0.0516 (9)
H1A0.59160.01210.22030.062*
N21.4594 (4)0.5536 (4)0.27769 (19)0.0507 (9)
H2A1.37070.51950.28210.061*
N30.9483 (6)0.5918 (5)0.2364 (3)0.0750 (13)
N40.8421 (5)0.2288 (4)0.0886 (2)0.0586 (10)
N51.1222 (4)0.2644 (5)0.3940 (2)0.0631 (10)
O10.7425 (3)0.1902 (3)0.27686 (16)0.0535 (7)
O20.8756 (3)0.4409 (3)0.36760 (17)0.0578 (8)
O31.2074 (3)0.3557 (3)0.24344 (16)0.0523 (7)
O41.0359 (3)0.0995 (3)0.17308 (18)0.0579 (8)
O50.8301 (4)0.4845 (4)0.2152 (2)0.0757 (10)
O61.0654 (4)0.5683 (3)0.2656 (2)0.0643 (9)
O70.9460 (6)0.7099 (5)0.2303 (3)0.1282 (19)
O80.9612 (4)0.3321 (3)0.11866 (17)0.0602 (8)
O90.7730 (3)0.1730 (3)0.13420 (18)0.0615 (8)
O100.7985 (5)0.1845 (4)0.0214 (2)0.0947 (13)
O111.0396 (4)0.1640 (4)0.3384 (2)0.0691 (9)
O121.1413 (4)0.3890 (4)0.38578 (18)0.0634 (8)
O131.1807 (4)0.2359 (4)0.4530 (2)0.0827 (11)
C10.5234 (4)0.1554 (5)0.3210 (2)0.0496 (10)
C20.6699 (4)0.2369 (4)0.3215 (2)0.0448 (10)
C30.7328 (5)0.3710 (5)0.3714 (2)0.0483 (10)
C40.6600 (6)0.4224 (5)0.4186 (3)0.0622 (12)
H4A0.70530.51120.45130.075*
C50.5163 (6)0.3401 (6)0.4177 (3)0.0732 (15)
H5A0.46570.37510.44930.088*
C60.4511 (5)0.2102 (6)0.3708 (3)0.0690 (14)
H6A0.35660.15600.37140.083*
C70.4493 (5)0.0238 (5)0.2709 (3)0.0531 (11)
H7A0.3547−0.02570.27360.064*
C80.9493 (6)0.5808 (5)0.4148 (3)0.0651 (13)
H8A0.89360.59880.45020.098*
H8B0.95720.65050.38380.098*
H8C1.04650.58670.44200.098*
C90.4335 (5)−0.1648 (5)0.1669 (2)0.0511 (11)
C100.3006 (5)−0.2604 (5)0.1683 (3)0.0601 (12)
H10A0.2545−0.24060.20610.072*
C110.2364 (5)−0.3845 (5)0.1140 (3)0.0642 (13)
H11A0.1460−0.44670.11530.077*
C120.3016 (6)−0.4197 (5)0.0579 (3)0.0631 (12)
C130.4352 (6)−0.3230 (6)0.0580 (3)0.0758 (15)
H13A0.4820−0.34360.02070.091*
C140.5010 (5)−0.1980 (5)0.1110 (3)0.0680 (14)
H14A0.5910−0.13550.10950.082*
C150.2269 (7)−0.5540 (6)−0.0017 (3)0.0884 (18)
H15A0.1359−0.60610.00830.133*
H15B0.2906−0.6114−0.00090.133*
H15C0.2062−0.5307−0.05060.133*
C161.4000 (4)0.3414 (4)0.1847 (2)0.0459 (10)
C171.2577 (4)0.2845 (4)0.1960 (2)0.0429 (9)
C181.1705 (5)0.1454 (4)0.1551 (2)0.0486 (10)
C191.2195 (5)0.0708 (5)0.1046 (3)0.0569 (11)
H19A1.1592−0.01970.07760.068*
C201.3599 (5)0.1289 (5)0.0929 (3)0.0610 (12)
H20A1.39250.07710.05800.073*
C211.4479 (5)0.2602 (5)0.1323 (3)0.0561 (11)
H21A1.54160.29770.12480.067*
C221.4960 (5)0.4756 (5)0.2272 (2)0.0506 (10)
H22A1.58950.51000.21890.061*
C230.9464 (6)−0.0471 (5)0.1409 (4)0.0907 (19)
H23A1.0022−0.09540.11650.136*
H23B0.8594−0.05060.10430.136*
H23C0.9179−0.09290.18040.136*
C241.5452 (5)0.6864 (4)0.3263 (2)0.0493 (10)
C251.6818 (5)0.7649 (5)0.3177 (3)0.0595 (12)
H25A1.71870.73180.27860.071*
C261.7611 (6)0.8923 (5)0.3679 (3)0.0680 (14)
H26A1.85240.94490.36240.082*
C271.7085 (6)0.9442 (5)0.4266 (3)0.0659 (13)
C281.5720 (6)0.8642 (5)0.4324 (3)0.0755 (15)
H28A1.53370.89750.47090.091*
C291.4908 (5)0.7368 (5)0.3831 (3)0.0654 (13)
H29A1.39900.68500.38840.078*
C301.7989 (7)1.0827 (5)0.4829 (3)0.0893 (18)
H30A1.74541.10120.51940.134*
H30B1.81701.15930.45640.134*
H30C1.89151.07520.50840.134*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Eu0.03130 (12)0.04488 (13)0.05244 (14)0.00468 (9)0.01419 (9)0.00783 (9)
N10.0319 (18)0.057 (2)0.061 (2)0.0053 (17)0.0129 (17)0.0180 (18)
N20.0349 (19)0.054 (2)0.057 (2)0.0092 (17)0.0097 (16)0.0059 (17)
N30.100 (4)0.069 (3)0.087 (3)0.041 (3)0.059 (3)0.034 (3)
N40.063 (3)0.060 (2)0.053 (3)0.027 (2)0.009 (2)0.007 (2)
N50.052 (2)0.089 (3)0.057 (3)0.028 (2)0.022 (2)0.021 (2)
O10.0402 (16)0.0565 (18)0.0618 (18)0.0086 (14)0.0225 (14)0.0078 (14)
O20.0434 (17)0.0566 (18)0.066 (2)0.0057 (15)0.0238 (15)−0.0005 (15)
O30.0370 (16)0.0557 (17)0.0576 (18)0.0094 (14)0.0150 (13)−0.0007 (14)
O40.0417 (17)0.0518 (18)0.072 (2)0.0033 (14)0.0157 (15)0.0111 (15)
O50.065 (2)0.096 (3)0.087 (3)0.044 (2)0.032 (2)0.034 (2)
O60.058 (2)0.0508 (19)0.091 (2)0.0152 (16)0.0378 (19)0.0172 (17)
O70.181 (5)0.090 (3)0.186 (5)0.085 (3)0.108 (4)0.083 (3)
O80.059 (2)0.0570 (19)0.0600 (19)0.0094 (17)0.0190 (16)0.0112 (15)
O90.0416 (17)0.068 (2)0.063 (2)0.0055 (15)0.0131 (15)0.0037 (16)
O100.120 (3)0.095 (3)0.052 (2)0.032 (3)0.002 (2)−0.003 (2)
O110.062 (2)0.063 (2)0.072 (2)0.0077 (18)0.0094 (18)0.0177 (18)
O120.068 (2)0.065 (2)0.0555 (19)0.0254 (18)0.0107 (16)0.0045 (16)
O130.078 (3)0.123 (3)0.063 (2)0.047 (2)0.0180 (19)0.037 (2)
C10.036 (2)0.058 (3)0.060 (3)0.015 (2)0.019 (2)0.020 (2)
C20.040 (2)0.056 (3)0.047 (2)0.018 (2)0.0197 (19)0.022 (2)
C30.041 (2)0.053 (3)0.053 (3)0.014 (2)0.016 (2)0.016 (2)
C40.064 (3)0.067 (3)0.058 (3)0.024 (3)0.021 (2)0.008 (2)
C50.065 (3)0.080 (4)0.086 (4)0.027 (3)0.043 (3)0.011 (3)
C60.048 (3)0.079 (4)0.089 (4)0.018 (3)0.037 (3)0.024 (3)
C70.037 (2)0.060 (3)0.067 (3)0.011 (2)0.023 (2)0.023 (2)
C80.062 (3)0.051 (3)0.070 (3)0.008 (2)0.016 (2)−0.003 (2)
C90.043 (2)0.051 (3)0.059 (3)0.014 (2)0.009 (2)0.019 (2)
C100.046 (3)0.064 (3)0.066 (3)0.003 (2)0.022 (2)0.019 (2)
C110.055 (3)0.060 (3)0.069 (3)0.003 (2)0.014 (3)0.024 (3)
C120.055 (3)0.061 (3)0.064 (3)0.012 (2)0.006 (2)0.011 (2)
C130.060 (3)0.089 (4)0.077 (4)0.025 (3)0.022 (3)0.004 (3)
C140.047 (3)0.071 (3)0.076 (3)0.006 (2)0.020 (3)0.004 (3)
C150.085 (4)0.079 (4)0.081 (4)0.018 (3)0.004 (3)−0.002 (3)
C160.037 (2)0.050 (2)0.053 (2)0.0172 (19)0.0125 (19)0.012 (2)
C170.036 (2)0.048 (2)0.045 (2)0.0147 (19)0.0102 (18)0.0102 (18)
C180.043 (2)0.049 (2)0.053 (3)0.013 (2)0.012 (2)0.013 (2)
C190.057 (3)0.052 (3)0.060 (3)0.021 (2)0.010 (2)0.007 (2)
C200.063 (3)0.069 (3)0.061 (3)0.033 (3)0.026 (2)0.006 (2)
C210.045 (3)0.069 (3)0.063 (3)0.024 (2)0.024 (2)0.017 (2)
C220.038 (2)0.061 (3)0.056 (3)0.018 (2)0.014 (2)0.015 (2)
C230.064 (4)0.052 (3)0.150 (6)0.006 (3)0.026 (4)0.029 (3)
C240.041 (2)0.045 (2)0.054 (3)0.009 (2)0.005 (2)0.009 (2)
C250.045 (3)0.059 (3)0.067 (3)0.006 (2)0.016 (2)0.011 (2)
C260.050 (3)0.056 (3)0.088 (4)0.004 (2)0.011 (3)0.024 (3)
C270.064 (3)0.047 (3)0.071 (3)0.009 (2)−0.001 (3)0.011 (2)
C280.076 (4)0.062 (3)0.077 (4)0.010 (3)0.024 (3)0.001 (3)
C290.053 (3)0.055 (3)0.080 (3)0.005 (2)0.023 (3)0.004 (2)
C300.086 (4)0.062 (3)0.089 (4)0.004 (3)−0.004 (3)−0.002 (3)

Geometric parameters (Å, °)

Eu—O12.328 (3)C8—H8B0.9600
Eu—O32.329 (3)C8—H8C0.9600
Eu—O62.429 (3)C9—C141.381 (6)
Eu—O112.464 (3)C9—C101.381 (6)
Eu—O92.486 (3)C10—C111.373 (6)
Eu—O82.496 (3)C10—H10A0.9300
Eu—O52.540 (3)C11—C121.374 (7)
Eu—O122.567 (3)C11—H11A0.9300
Eu—O22.743 (3)C12—C131.384 (7)
Eu—O42.748 (3)C12—C151.498 (7)
Eu—N32.906 (5)C13—C141.369 (7)
Eu—N42.914 (4)C13—H13A0.9300
N1—C71.297 (5)C14—H14A0.9300
N1—C91.416 (5)C15—H15A0.9600
N1—H1A0.8600C15—H15B0.9600
N2—C221.300 (5)C15—H15C0.9600
N2—C241.412 (5)C16—C221.408 (6)
N2—H2A0.8600C16—C211.411 (6)
N3—O71.210 (5)C16—C171.413 (5)
N3—O61.262 (6)C17—C181.413 (6)
N3—O51.275 (6)C18—C191.356 (6)
N4—O101.197 (5)C19—C201.401 (7)
N4—O81.271 (5)C19—H19A0.9300
N4—O91.273 (5)C20—C211.351 (6)
N5—O131.232 (5)C20—H20A0.9300
N5—O121.245 (5)C21—H21A0.9300
N5—O111.273 (5)C22—H22A0.9300
O1—C21.310 (5)C23—H23A0.9600
O2—C31.390 (5)C23—H23B0.9600
O2—C81.436 (5)C23—H23C0.9600
O3—C171.308 (5)C24—C291.364 (6)
O4—C181.385 (5)C24—C251.392 (6)
O4—C231.443 (6)C25—C261.376 (7)
C1—C71.397 (6)C25—H25A0.9300
C1—C61.407 (6)C26—C271.386 (7)
C1—C21.427 (5)C26—H26A0.9300
C2—C31.405 (6)C27—C281.378 (7)
C3—C41.365 (6)C27—C301.516 (7)
C4—C51.403 (7)C28—C291.372 (7)
C4—H4A0.9300C28—H28A0.9300
C5—C61.353 (7)C29—H29A0.9300
C5—H5A0.9300C30—H30A0.9600
C6—H6A0.9300C30—H30B0.9600
C7—H7A0.9300C30—H30C0.9600
C8—H8A0.9600
O1—Eu—O3156.86 (11)N5—O12—Eu93.7 (3)
O1—Eu—O6126.05 (10)C7—C1—C6119.5 (4)
O3—Eu—O674.56 (11)C7—C1—C2121.2 (4)
O1—Eu—O1177.22 (11)C6—C1—C2119.3 (4)
O3—Eu—O1181.19 (11)O1—C2—C3121.2 (4)
O6—Eu—O11128.28 (12)O1—C2—C1121.7 (4)
O1—Eu—O967.89 (10)C3—C2—C1117.1 (4)
O3—Eu—O9114.59 (10)C4—C3—O2125.1 (4)
O6—Eu—O9117.74 (12)C4—C3—C2122.5 (4)
O11—Eu—O9113.83 (11)O2—C3—C2112.4 (4)
O1—Eu—O8117.54 (10)C3—C4—C5119.5 (4)
O3—Eu—O873.74 (10)C3—C4—H4A120.2
O6—Eu—O878.23 (11)C5—C4—H4A120.2
O11—Eu—O8136.58 (11)C6—C5—C4120.2 (5)
O9—Eu—O851.36 (10)C6—C5—H5A119.9
O1—Eu—O583.97 (12)C4—C5—H5A119.9
O3—Eu—O5119.17 (12)C5—C6—C1121.3 (4)
O6—Eu—O551.38 (12)C5—C6—H6A119.3
O11—Eu—O5152.48 (12)C1—C6—H6A119.3
O9—Eu—O576.25 (12)N1—C7—C1124.8 (4)
O8—Eu—O570.27 (11)N1—C7—H7A117.6
O1—Eu—O12101.56 (11)C1—C7—H7A117.6
O3—Eu—O1270.19 (10)O2—C8—H8A109.5
O6—Eu—O1278.08 (12)O2—C8—H8B109.5
O11—Eu—O1250.66 (11)H8A—C8—H8B109.5
O9—Eu—O12164.00 (11)O2—C8—H8C109.5
O8—Eu—O12140.88 (11)H8A—C8—H8C109.5
O5—Eu—O12115.65 (12)H8B—C8—H8C109.5
O1—Eu—O261.53 (9)C14—C9—C10118.7 (4)
O3—Eu—O2126.07 (9)C14—C9—N1118.9 (4)
O6—Eu—O272.06 (10)C10—C9—N1122.3 (4)
O11—Eu—O287.61 (11)C11—C10—C9120.2 (5)
O9—Eu—O2118.15 (10)C11—C10—H10A119.9
O8—Eu—O2135.78 (10)C9—C10—H10A119.9
O5—Eu—O265.64 (11)C10—C11—C12122.1 (5)
O12—Eu—O262.36 (10)C10—C11—H11A119.0
O1—Eu—O4103.23 (9)C12—C11—H11A119.0
O3—Eu—O461.07 (9)C11—C12—C13116.8 (5)
O6—Eu—O4128.88 (10)C11—C12—C15120.8 (5)
O11—Eu—O470.39 (11)C13—C12—C15122.4 (5)
O9—Eu—O465.81 (10)C14—C13—C12122.3 (5)
O8—Eu—O466.53 (10)C14—C13—H13A118.8
O5—Eu—O4134.37 (11)C12—C13—H13A118.8
O12—Eu—O4106.99 (10)C13—C14—C9119.9 (5)
O2—Eu—O4156.14 (10)C13—C14—H14A120.0
O1—Eu—N3106.12 (13)C9—C14—H14A120.0
O3—Eu—N396.52 (13)C12—C15—H15A109.5
O6—Eu—N325.40 (13)C12—C15—H15B109.5
O11—Eu—N3147.00 (13)H15A—C15—H15B109.5
O9—Eu—N397.17 (13)C12—C15—H15C109.5
O8—Eu—N371.99 (11)H15A—C15—H15C109.5
O5—Eu—N325.98 (12)H15B—C15—H15C109.5
O12—Eu—N397.38 (13)C22—C16—C21119.9 (4)
O2—Eu—N367.05 (10)C22—C16—C17120.6 (4)
O4—Eu—N3136.81 (10)C21—C16—C17119.5 (4)
O1—Eu—N493.14 (11)O3—C17—C16121.9 (4)
O3—Eu—N493.38 (11)O3—C17—C18120.3 (4)
O6—Eu—N499.32 (12)C16—C17—C18117.7 (4)
O11—Eu—N4127.44 (11)C19—C18—O4126.4 (4)
O9—Eu—N425.74 (10)C19—C18—C17121.3 (4)
O8—Eu—N425.71 (10)O4—C18—C17112.3 (4)
O5—Eu—N472.97 (11)C18—C19—C20120.6 (4)
O12—Eu—N4163.52 (11)C18—C19—H19A119.7
O2—Eu—N4132.72 (10)C20—C19—H19A119.7
O4—Eu—N461.78 (10)C21—C20—C19119.8 (4)
N3—Eu—N485.49 (12)C21—C20—H20A120.1
C7—N1—C9128.0 (4)C19—C20—H20A120.1
C7—N1—H1A116.0C20—C21—C16121.1 (4)
C9—N1—H1A116.0C20—C21—H21A119.5
C22—N2—C24128.9 (4)C16—C21—H21A119.5
C22—N2—H2A115.5N2—C22—C16122.7 (4)
C24—N2—H2A115.5N2—C22—H22A118.7
O7—N3—O6122.5 (6)C16—C22—H22A118.7
O7—N3—O5121.1 (6)O4—C23—H23A109.5
O6—N3—O5116.4 (4)O4—C23—H23B109.5
O7—N3—Eu178.1 (5)H23A—C23—H23B109.5
O6—N3—Eu55.6 (2)O4—C23—H23C109.5
O5—N3—Eu60.8 (2)H23A—C23—H23C109.5
O10—N4—O8122.2 (4)H23B—C23—H23C109.5
O10—N4—O9121.7 (4)C29—C24—C25120.2 (4)
O8—N4—O9116.2 (4)C29—C24—N2117.9 (4)
O10—N4—Eu173.5 (3)C25—C24—N2121.9 (4)
O8—N4—Eu58.5 (2)C26—C25—C24118.9 (5)
O9—N4—Eu58.0 (2)C26—C25—H25A120.5
O13—N5—O12122.7 (5)C24—C25—H25A120.5
O13—N5—O11119.7 (5)C25—C26—C27121.7 (5)
O12—N5—O11117.6 (4)C25—C26—H26A119.1
O13—N5—Eu175.6 (4)C27—C26—H26A119.1
O12—N5—Eu61.1 (2)C28—C27—C26117.5 (5)
O11—N5—Eu56.5 (2)C28—C27—C30121.3 (5)
C2—O1—Eu128.8 (3)C26—C27—C30121.2 (5)
C3—O2—C8117.2 (3)C29—C28—C27122.0 (5)
C3—O2—Eu114.8 (2)C29—C28—H28A119.0
C8—O2—Eu127.1 (3)C27—C28—H28A119.0
C17—O3—Eu128.5 (2)C24—C29—C28119.8 (5)
C18—O4—C23116.4 (4)C24—C29—H29A120.1
C18—O4—Eu114.2 (2)C28—C29—H29A120.1
C23—O4—Eu128.9 (3)C27—C30—H30A109.5
N3—O5—Eu93.3 (3)C27—C30—H30B109.5
N3—O6—Eu99.0 (3)H30A—C30—H30B109.5
N4—O8—Eu95.8 (2)C27—C30—H30C109.5
N4—O9—Eu96.3 (2)H30A—C30—H30C109.5
N5—O11—Eu97.9 (3)H30B—C30—H30C109.5
O1—Eu—N3—O6145.0 (3)O12—Eu—O5—N348.7 (3)
O3—Eu—N3—O6−30.1 (3)O2—Eu—O5—N387.2 (3)
O11—Eu—N3—O653.7 (4)O4—Eu—O5—N3−108.7 (3)
O9—Eu—N3—O6−146.0 (3)N4—Eu—O5—N3−116.2 (3)
O8—Eu—N3—O6−100.6 (3)O7—N3—O6—Eu−179.6 (4)
O5—Eu—N3—O6177.6 (4)O5—N3—O6—Eu2.3 (4)
O12—Eu—N3—O640.7 (3)O1—Eu—O6—N3−42.9 (3)
O2—Eu—N3—O696.4 (3)O3—Eu—O6—N3148.9 (3)
O4—Eu—N3—O6−84.0 (3)O11—Eu—O6—N3−146.0 (3)
N4—Eu—N3—O6−123.0 (3)O9—Eu—O6—N338.8 (3)
O1—Eu—N3—O5−32.6 (3)O8—Eu—O6—N372.7 (3)
O3—Eu—N3—O5152.3 (3)O5—Eu—O6—N3−1.3 (2)
O6—Eu—N3—O5−177.6 (4)O12—Eu—O6—N3−138.6 (3)
O11—Eu—N3—O5−123.8 (3)O2—Eu—O6—N3−74.1 (3)
O9—Eu—N3—O536.4 (3)O4—Eu—O6—N3119.0 (3)
O8—Eu—N3—O581.8 (3)N4—Eu—O6—N357.9 (3)
O12—Eu—N3—O5−136.9 (3)O10—N4—O8—Eu−172.4 (4)
O2—Eu—N3—O5−81.2 (3)O9—N4—O8—Eu6.2 (4)
O4—Eu—N3—O598.4 (3)O1—Eu—O8—N4−19.8 (3)
N4—Eu—N3—O559.4 (3)O3—Eu—O8—N4138.3 (3)
O1—Eu—N4—O8162.5 (2)O6—Eu—O8—N4−144.5 (3)
O3—Eu—N4—O8−39.7 (2)O11—Eu—O8—N481.0 (3)
O6—Eu—N4—O835.2 (3)O9—Eu—O8—N4−3.7 (2)
O11—Eu—N4—O8−121.2 (2)O5—Eu—O8—N4−91.6 (3)
O9—Eu—N4—O8173.4 (4)O12—Eu—O8—N4161.7 (2)
O5—Eu—N4—O879.8 (2)O2—Eu—O8—N4−96.2 (3)
O12—Eu—N4—O8−44.3 (5)O4—Eu—O8—N473.4 (2)
O2—Eu—N4—O8109.3 (3)N3—Eu—O8—N4−119.0 (3)
O4—Eu—N4—O8−94.2 (3)O10—N4—O9—Eu172.4 (4)
N3—Eu—N4—O856.5 (3)O8—N4—O9—Eu−6.3 (4)
O1—Eu—N4—O9−10.9 (2)O1—Eu—O9—N4168.2 (3)
O3—Eu—N4—O9146.9 (2)O3—Eu—O9—N4−36.9 (3)
O6—Eu—N4—O9−138.2 (2)O6—Eu—O9—N448.0 (3)
O11—Eu—N4—O965.4 (3)O11—Eu—O9—N4−127.9 (2)
O8—Eu—N4—O9−173.4 (4)O8—Eu—O9—N43.7 (2)
O5—Eu—N4—O9−93.6 (3)O5—Eu—O9—N479.2 (2)
O12—Eu—N4—O9142.3 (4)O12—Eu—O9—N4−141.0 (4)
O2—Eu—N4—O9−64.1 (3)O2—Eu—O9—N4131.5 (2)
O4—Eu—N4—O992.4 (2)O4—Eu—O9—N4−74.8 (2)
N3—Eu—N4—O9−116.9 (3)N3—Eu—O9—N463.7 (3)
O1—Eu—N5—O12−121.2 (3)O13—N5—O11—Eu177.2 (3)
O3—Eu—N5—O1275.4 (2)O12—N5—O11—Eu−3.4 (4)
O6—Eu—N5—O125.6 (3)O1—Eu—O11—N5−115.0 (3)
O11—Eu—N5—O12176.6 (4)O3—Eu—O11—N573.4 (2)
O9—Eu—N5—O12−174.3 (2)O6—Eu—O11—N511.2 (3)
O8—Eu—N5—O1294.1 (3)O9—Eu—O11—N5−173.5 (2)
O5—Eu—N5—O12−41.3 (3)O8—Eu—O11—N5128.3 (2)
O2—Eu—N5—O12−60.7 (2)O5—Eu—O11—N5−66.9 (4)
O4—Eu—N5—O12135.5 (2)O12—Eu—O11—N51.9 (2)
N3—Eu—N5—O12−13.0 (3)O2—Eu—O11—N5−53.7 (2)
N4—Eu—N5—O12144.6 (3)O4—Eu—O11—N5135.7 (3)
O1—Eu—N5—O1162.2 (3)N3—Eu—O11—N5−15.0 (4)
O3—Eu—N5—O11−101.2 (3)N4—Eu—O11—N5160.9 (2)
O6—Eu—N5—O11−171.0 (2)O13—N5—O12—Eu−177.4 (4)
O9—Eu—N5—O119.1 (3)O11—N5—O12—Eu3.2 (4)
O8—Eu—N5—O11−82.5 (3)O1—Eu—O12—N560.7 (3)
O5—Eu—N5—O11142.1 (3)O3—Eu—O12—N5−96.8 (3)
O12—Eu—N5—O11−176.6 (4)O6—Eu—O12—N5−174.4 (3)
O2—Eu—N5—O11122.7 (3)O11—Eu—O12—N5−1.9 (2)
O4—Eu—N5—O11−41.1 (3)O9—Eu—O12—N513.6 (5)
N3—Eu—N5—O11170.4 (2)O8—Eu—O12—N5−120.6 (3)
N4—Eu—N5—O11−32.0 (4)O5—Eu—O12—N5149.6 (2)
O3—Eu—O1—C2125.4 (3)O2—Eu—O12—N5109.7 (3)
O6—Eu—O1—C2−24.5 (4)O4—Eu—O12—N5−47.1 (3)
O11—Eu—O1—C2103.9 (3)N3—Eu—O12—N5168.9 (3)
O9—Eu—O1—C2−133.5 (4)N4—Eu—O12—N5−91.9 (5)
O8—Eu—O1—C2−119.9 (3)Eu—O1—C2—C3−9.3 (6)
O5—Eu—O1—C2−55.9 (3)Eu—O1—C2—C1169.7 (3)
O12—Eu—O1—C259.1 (3)C7—C1—C2—O1−2.1 (6)
O2—Eu—O1—C29.6 (3)C6—C1—C2—O1179.4 (4)
O4—Eu—O1—C2169.9 (3)C7—C1—C2—C3177.0 (4)
N3—Eu—O1—C2−42.2 (4)C6—C1—C2—C3−1.5 (6)
N4—Eu—O1—C2−128.4 (3)C8—O2—C3—C4−3.0 (6)
O1—Eu—O2—C3−9.0 (3)Eu—O2—C3—C4−173.0 (4)
O3—Eu—O2—C3−163.0 (2)C8—O2—C3—C2178.4 (4)
O6—Eu—O2—C3142.6 (3)Eu—O2—C3—C28.4 (4)
O11—Eu—O2—C3−85.8 (3)O1—C2—C3—C4−179.9 (4)
O9—Eu—O2—C330.1 (3)C1—C2—C3—C41.1 (6)
O8—Eu—O2—C392.4 (3)O1—C2—C3—O2−1.2 (6)
O5—Eu—O2—C387.6 (3)C1—C2—C3—O2179.7 (4)
O12—Eu—O2—C3−131.8 (3)O2—C3—C4—C5−179.1 (4)
O4—Eu—O2—C3−63.4 (4)C2—C3—C4—C5−0.7 (7)
N3—Eu—O2—C3115.9 (3)C3—C4—C5—C60.7 (8)
N4—Eu—O2—C356.4 (3)C4—C5—C6—C1−1.3 (8)
O1—Eu—O2—C8−177.9 (4)C7—C1—C6—C5−176.8 (5)
O3—Eu—O2—C828.1 (4)C2—C1—C6—C51.7 (7)
O6—Eu—O2—C8−26.3 (3)C9—N1—C7—C1−178.1 (4)
O11—Eu—O2—C8105.4 (4)C6—C1—C7—N1177.3 (4)
O9—Eu—O2—C8−138.8 (3)C2—C1—C7—N1−1.2 (7)
O8—Eu—O2—C8−76.5 (4)C7—N1—C9—C14170.5 (5)
O5—Eu—O2—C8−81.3 (4)C7—N1—C9—C10−9.7 (7)
O12—Eu—O2—C859.3 (3)C14—C9—C10—C11−1.2 (7)
O4—Eu—O2—C8127.7 (3)N1—C9—C10—C11178.9 (4)
N3—Eu—O2—C8−52.9 (4)C9—C10—C11—C121.2 (8)
N4—Eu—O2—C8−112.5 (3)C10—C11—C12—C13−0.7 (8)
O1—Eu—O3—C1767.9 (4)C10—C11—C12—C15−178.4 (5)
O6—Eu—O3—C17−137.0 (3)C11—C12—C13—C140.1 (8)
O11—Eu—O3—C1789.1 (3)C15—C12—C13—C14177.8 (5)
O9—Eu—O3—C17−23.1 (4)C12—C13—C14—C9−0.1 (8)
O8—Eu—O3—C17−55.0 (3)C10—C9—C14—C130.7 (7)
O5—Eu—O3—C17−110.6 (3)N1—C9—C14—C13−179.5 (5)
O12—Eu—O3—C17140.4 (3)Eu—O3—C17—C16164.4 (3)
O2—Eu—O3—C17169.6 (3)Eu—O3—C17—C18−16.8 (5)
O4—Eu—O3—C1716.7 (3)C22—C16—C17—O32.9 (6)
N3—Eu—O3—C17−124.1 (3)C21—C16—C17—O3−179.5 (4)
N4—Eu—O3—C17−38.2 (3)C22—C16—C17—C18−175.9 (4)
O1—Eu—O4—C18−176.7 (3)C21—C16—C17—C181.7 (6)
O3—Eu—O4—C18−15.1 (2)C23—O4—C18—C197.1 (6)
O6—Eu—O4—C1818.2 (3)Eu—O4—C18—C19−166.2 (4)
O11—Eu—O4—C18−105.7 (3)C23—O4—C18—C17−173.1 (4)
O9—Eu—O4—C18125.2 (3)Eu—O4—C18—C1713.6 (4)
O8—Eu—O4—C1868.7 (3)O3—C17—C18—C19178.7 (4)
O5—Eu—O4—C1888.7 (3)C16—C17—C18—C19−2.4 (6)
O12—Eu—O4—C18−70.1 (3)O3—C17—C18—O4−1.1 (5)
O2—Eu—O4—C18−129.5 (3)C16—C17—C18—O4177.8 (4)
N3—Eu—O4—C1851.4 (3)O4—C18—C19—C20−178.7 (4)
N4—Eu—O4—C1896.8 (3)C17—C18—C19—C201.5 (7)
O1—Eu—O4—C2310.9 (4)C18—C19—C20—C210.2 (7)
O3—Eu—O4—C23172.6 (4)C19—C20—C21—C16−0.9 (7)
O6—Eu—O4—C23−154.1 (4)C22—C16—C21—C20177.5 (4)
O11—Eu—O4—C2382.0 (4)C17—C16—C21—C20−0.1 (7)
O9—Eu—O4—C23−47.1 (4)C24—N2—C22—C16177.3 (4)
O8—Eu—O4—C23−103.6 (4)C21—C16—C22—N2−178.2 (4)
O5—Eu—O4—C23−83.6 (4)C17—C16—C22—N2−0.6 (6)
O12—Eu—O4—C23117.6 (4)C22—N2—C24—C29−169.5 (5)
O2—Eu—O4—C2358.2 (5)C22—N2—C24—C2510.2 (7)
N3—Eu—O4—C23−120.9 (4)C29—C24—C25—C261.0 (7)
N4—Eu—O4—C23−75.5 (4)N2—C24—C25—C26−178.7 (4)
O7—N3—O5—Eu179.7 (4)C24—C25—C26—C27−0.1 (7)
O6—N3—O5—Eu−2.2 (4)C25—C26—C27—C28−0.8 (8)
O1—Eu—O5—N3148.7 (3)C25—C26—C27—C30178.3 (5)
O3—Eu—O5—N3−31.9 (3)C26—C27—C28—C290.9 (8)
O6—Eu—O5—N31.3 (2)C30—C27—C28—C29−178.2 (5)
O11—Eu—O5—N3101.8 (3)C25—C24—C29—C28−0.9 (7)
O9—Eu—O5—N3−142.7 (3)N2—C24—C29—C28178.8 (5)
O8—Eu—O5—N3−89.2 (3)C27—C28—C29—C240.0 (8)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O10.861.952.634 (4)136
N2—H2A···O30.861.862.569 (4)139

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2728).

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