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Acta Cryst. (2007). E63, m2608-m2609    [ doi:10.1107/S1600536807046818 ]

Hexakis([mu]-naphthalene-1-acetato)bis[(1,10-phenanthroline)europium(III)] N,N-dimethylformamide disolvate

Y.-F. Liu, H.-T. Xia, D.-Q. Wang and S.-P. Yang

Abstract top

The title complex, [Eu2(C12H9O2)6(C12H8N2)2]·2C3H7NO, is centrosymmetric. The Eu atom is nine-coordinate. Molecules are linked into a chain by C-H...O hydrogen bonds parallel to the a-axis direction and into a sheet by C-H...[pi] hydrogen bonds parallel to the [100] plane, the combination of the chains and sheets generating a three-dimensional framework structure.

Comment top

The complexes between rare earth elements and organic ligands have received significant attention in recent years because of their potential fluorescence, magnetic and porous characteristics, are widely used in many fields (Yang et al., 2001). Among rare earth ions, the europium(III) has been extensively applied in the fluorimetric determination, electroluminescent devices, ultraviolet dosimeters and fluorescent labels and molecular biology (Xi et al., 2007). The carboxylate anions are versatile ligand, which produces various coordination modes, so we synthesize a europium complex with 1-naphthylacetic acid (NAA) and 1,10-phenanthroline (phen), we report here its crystal structure, (I).

The structure of (I) consists of centrosymmetric binuclear units. Each central Eu(III) ion is nine-coordinated by seven oxygen atoms of different NNA ligands and two nitrogen atoms of one phen ligand, the coordination geometry of Eu atom can be described as a cage geometry (Fig. 1). The bond distances of between the europium center and carboxylic oxygen atoms are 2.367 (5)–2.578 (5) Å. In addition, the dihedral angles between the least-square-plane Eu2O2 and naphthyl rings are 58.23(0.14)° (C3–C12 ring), 43.76(0.21)° (C15–C24 ring) and 71.71(0.18)° (C27–C36 ring), and the dihedral angle between Eu2O2 plane and phen ring is 81.71(0.14)°.

In the complex (I), the NNA ligands coordinated to the Eu(III) ion have three types of coordination modes, via, NNA acts as chelating-bridging tridentate ligand, chelating bidentate ligand and bidentate-bridging ligand. The O—C—O bond angles of three types of coordination modes are 121.3 (9)° (O1—C1—O2), 122.2 (7)° (O5—C25—O6), and 126.0 (8)° (O3—C13—O4), respectively.

In (I), the molecules are linked into sheets by means of C—H···π hydrogen bond (Fig. 2 and Table 2) and chains parallel to the a axis direction with R44(30) rings (Bernstein et al., 1995) surrounds an R22(14) ring centred at (n, 1/2, 1) (n = zero or integer) (Fig. 3) by C—H···O hydrogen bonds (Fig. 3 and Table 2). The action of a chains are to link adjacent [100] sheet into the three-dimensional framework structure.

Related literature top

For related literature, see: Bernstein et al. (1995); Yang et al. (2001); Xi et al. (2007).

Experimental top

To a stirred solution of 1-naphthylacetic acid (0.5586 g, 3 mmol) and 1,10-phenanthroline monohydrate (0.198 g, 1 mmol) in 30 ml me thanol, and a solution of Eu(NO3)3·6H2O (0.446 g, 1 mmol) in water (10 ml) was added. The mixed solution was heated to 333 K and stirred for 3 h, and then cooled to room temperature. The precipitate was washed with water and then dissolved in DMF. A colorless crystal suitable for X-ray diffraction was obtained by evaporation of DMF solution [m.p. 558–559 K]. IR (KBr, cm−1): ν 3440, 3052, 1610, 1422, 1360, 1290, 1256, 1140, 1100, 838, 778, 724, 628, 536.

Refinement top

The space group was uniquely assigned from the systematic absences. All H atoms were located in difference Fourier maps. H atoms bonded to C atoms were treated as riding atoms, with C—H distances of 0.93 Å (aryl, formyl), 0.97 Å (methylene) and 0.96 Å (methyl), and with Uiso(H) = 1.2Ueq(C) (aryl, formyl, methylene) or 1.5 Ueq(C) (methyl).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are at the 30% probability level. Unlabelled atoms in the molecule are related to labelled atoms by (1 − x, 1 − y, 2 − z).
[Figure 2] Fig. 2. A larger portion of the crystal structure of (I), showing the formation of a hydrogen-bonded chain built from C—H···π. For clarity, H atoms not involved in the hydrogen bonding have been omitted. Dashed lines indicate hydrogen bonds. [Symmetry codes: (A) 1 − x, −1/2 + y, 3/2 − z, (B) 1 − x, 1/2 + y, 3/2 − z].
[Figure 3] Fig. 3. A larger portion of the crystal structure of (I), showing the formation of a hydrogen-bonded chain built from C—H···O. For clarity, H atoms not involved in the hydrogen bonding have been omitted. Dashed lines indicate hydrogen bonds. [Symmetry codes: (C) x, y, 1 + z,, (D) − x, 1 − y, 1 − z, (E) − x, 1 − y, 2 − z].
Hexakis(µ-naphthalene-1-acetato)bis[(1,10-phenanthroline)europium(III)] N,N-dimethylformamide disolvate top
Crystal data top
[Eu2(C12H9O2)6(C12H8N2)2]·2C3H7NOF000 = 1952
Mr = 1921.67Dx = 1.452 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3934 reflections
a = 13.529 (2) Åθ = 2.4–25.3º
b = 15.095 (2) ŵ = 1.48 mm−1
c = 22.171 (3) ÅT = 298 (2) K
β = 103.866 (2)ºBlock, colourless
V = 4395.8 (11) Å30.41 × 0.14 × 0.11 mm
Z = 2
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer		7667 independent reflections
Radiation source: fine-focus sealed tube4416 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.077
T = 298(2) Kθmax = 25.0º
φ and ω scansθmin = 1.7º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −16→15
Tmin = 0.582, Tmax = 0.854k = −17→16
21103 measured reflectionsl = −20→26
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.117  w = 1/[σ2(Fo2) + 24.9916P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.004
7667 reflectionsΔρmax = 1.67 e Å−3
559 parametersΔρmin = −1.39 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Eu2(C12H9O2)6(C12H8N2)2]·2C3H7NOV = 4395.8 (11) Å3
Mr = 1921.67Z = 2
Monoclinic, P21/cMo Kα
a = 13.529 (2) ŵ = 1.48 mm−1
b = 15.095 (2) ÅT = 298 (2) K
c = 22.171 (3) Å0.41 × 0.14 × 0.11 mm
β = 103.866 (2)º
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer		7667 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4416 reflections with I > 2σ(I)
Tmin = 0.582, Tmax = 0.854Rint = 0.077
21103 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.117  w = 1/[σ2(Fo2) + 24.9916P]
where P = (Fo2 + 2Fc2)/3
S = 1.04Δρmax = 1.67 e Å−3
7667 reflectionsΔρmin = −1.39 e Å−3
559 parameters
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
Eu10.38256 (3)0.42912 (3)1.011917 (19)0.03380 (13)
N10.2282 (5)0.4434 (4)1.0646 (3)0.0408 (17)
N20.2103 (5)0.3629 (5)0.9541 (3)0.0473 (19)
N30.3673 (9)0.3365 (7)0.2527 (5)0.080 (3)
O10.4398 (4)0.5807 (3)0.9788 (2)0.0348 (12)
O20.2758 (4)0.5565 (4)0.9613 (2)0.0429 (14)
O30.4044 (4)0.4244 (4)0.9082 (2)0.0396 (13)
O40.5474 (4)0.4867 (4)0.8956 (2)0.0407 (14)
O50.4121 (5)0.2712 (4)0.9892 (3)0.0511 (16)
O60.4044 (4)0.3010 (4)1.0838 (3)0.0527 (16)
O70.2329 (9)0.2455 (8)0.2360 (5)0.152 (4)
C10.3479 (6)0.5990 (5)0.9511 (4)0.035 (2)
C20.3339 (6)0.6740 (6)0.9052 (4)0.051 (2)
H2A0.35890.72800.92740.061*
H2B0.37570.66260.87610.061*
C30.2264 (7)0.6893 (7)0.8691 (4)0.051 (3)
C40.1781 (8)0.7624 (7)0.8795 (5)0.064 (3)
H40.21220.80210.90940.077*
C50.0777 (8)0.7824 (8)0.8474 (5)0.072 (3)
H50.04620.83430.85560.087*
C60.0290 (8)0.7249 (8)0.8048 (5)0.067 (3)
H6−0.03820.73680.78440.081*
C70.0740 (8)0.6484 (7)0.7896 (5)0.062 (3)
C80.1765 (7)0.6296 (7)0.8229 (4)0.056 (3)
C90.2210 (8)0.5517 (7)0.8089 (5)0.071 (3)
H90.28680.53820.83100.085*
C100.1725 (10)0.4944 (8)0.7645 (5)0.093 (4)
H100.20470.44340.75540.111*
C110.0718 (10)0.5146 (9)0.7324 (6)0.095 (4)
H110.03670.47540.70250.114*
C120.0257 (9)0.5885 (8)0.7441 (5)0.084 (4)
H12−0.04020.60040.72140.100*
C130.4723 (6)0.4354 (6)0.8798 (3)0.0374 (19)
C140.4617 (7)0.3844 (6)0.8197 (4)0.054 (3)
H14A0.41370.33650.81920.065*
H14B0.43220.42380.78550.065*
C150.5582 (7)0.3455 (7)0.8076 (5)0.058 (3)
C160.5895 (8)0.3710 (7)0.7563 (5)0.070 (3)
H160.55240.41380.73020.084*
C170.6765 (9)0.3345 (8)0.7415 (5)0.077 (3)
H170.69710.35340.70650.093*
C180.7293 (9)0.2717 (8)0.7789 (6)0.078 (3)
H180.78780.24890.76960.094*
C190.7005 (8)0.2395 (8)0.8306 (6)0.069 (3)
C200.6133 (8)0.2796 (7)0.8466 (5)0.059 (3)
C210.5844 (8)0.2474 (7)0.8991 (5)0.067 (3)
H210.52900.27250.91080.080*
C220.6365 (9)0.1793 (8)0.9334 (6)0.085 (4)
H220.61540.15810.96770.102*
C230.7216 (10)0.1409 (8)0.9176 (6)0.091 (4)
H230.75690.09470.94100.109*
C240.7510 (9)0.1721 (8)0.8679 (6)0.082 (4)
H240.80800.14720.85800.098*
C250.4104 (7)0.2472 (6)1.0421 (5)0.049 (2)
C260.4134 (8)0.1476 (6)1.0558 (5)0.067 (3)
H26A0.47960.12421.05440.081*
H26B0.40410.13801.09740.081*
C270.3332 (10)0.0995 (7)1.0104 (6)0.075 (3)
C280.3575 (10)0.0461 (7)0.9655 (6)0.087 (4)
H280.42500.03820.96390.105*
C290.2783 (14)0.0038 (8)0.9222 (7)0.102 (4)
H290.2948−0.03380.89280.122*
C300.1817 (14)0.0155 (9)0.9219 (7)0.106 (5)
H300.1322−0.01270.89160.128*
C310.1516 (12)0.0680 (9)0.9648 (7)0.093 (4)
C320.2295 (10)0.1096 (7)1.0102 (6)0.078 (3)
C330.1995 (10)0.1613 (7)1.0562 (6)0.081 (4)
H330.24890.18791.08750.097*
C340.0969 (11)0.1725 (8)1.0550 (6)0.091 (4)
H340.07690.20641.08510.109*
C350.0267 (11)0.1329 (9)1.0089 (8)0.103 (5)
H35−0.04180.14211.00760.124*
C360.0488 (12)0.0830 (10)0.9664 (7)0.105 (5)
H36−0.00330.05670.93670.126*
C370.2361 (7)0.4825 (6)1.1183 (5)0.053 (3)
H370.29950.50431.13880.064*
C380.1536 (8)0.4935 (7)1.1472 (5)0.064 (3)
H380.16270.52161.18550.076*
C390.0615 (7)0.4618 (6)1.1171 (5)0.060 (3)
H390.00600.46781.13470.072*
C400.0497 (6)0.4202 (7)1.0598 (5)0.054 (2)
C410.1347 (6)0.4122 (6)1.0349 (4)0.048 (2)
C420.1262 (7)0.3708 (6)0.9760 (5)0.053 (3)
C430.0299 (8)0.3387 (7)0.9433 (5)0.066 (3)
C440.0262 (8)0.2989 (7)0.8856 (6)0.079 (4)
H44−0.03540.27740.86200.095*
C450.1105 (8)0.2915 (8)0.8642 (5)0.080 (3)
H450.10790.26470.82610.097*
C460.2017 (7)0.3245 (7)0.8998 (5)0.065 (3)
H460.25970.31920.88450.078*
C47−0.0453 (7)0.3864 (7)1.0257 (6)0.068 (3)
H47−0.10230.39111.04200.081*
C48−0.0538 (7)0.3482 (7)0.9709 (6)0.070 (3)
H48−0.11710.32680.94970.084*
C490.3093 (12)0.2756 (11)0.2205 (7)0.111 (5)
H490.32540.25390.18480.133*
C500.4563 (9)0.3670 (8)0.2346 (6)0.098 (4)
H50A0.46940.32920.20260.146*
H50B0.51350.36570.26980.146*
H50C0.44540.42650.21920.146*
C510.3418 (11)0.3734 (10)0.3059 (6)0.137 (6)
H51A0.27250.35900.30550.206*
H51B0.34960.43660.30550.206*
H51C0.38610.34950.34280.206*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Eu10.0235 (2)0.0386 (2)0.0409 (2)−0.0030 (2)0.01099 (15)−0.0029 (3)
N10.039 (4)0.039 (4)0.050 (4)0.009 (4)0.019 (3)0.003 (4)
N20.026 (4)0.058 (5)0.058 (5)−0.009 (4)0.010 (4)−0.008 (4)
N30.098 (9)0.076 (7)0.068 (7)0.013 (6)0.024 (6)0.008 (6)
O10.025 (3)0.038 (3)0.041 (3)0.001 (3)0.007 (2)−0.001 (3)
O20.020 (3)0.049 (4)0.060 (4)0.007 (3)0.009 (3)0.014 (3)
O30.032 (3)0.049 (3)0.041 (3)−0.006 (3)0.015 (2)−0.007 (3)
O40.034 (3)0.055 (4)0.036 (3)−0.008 (3)0.013 (3)−0.007 (3)
O50.059 (4)0.037 (4)0.062 (4)−0.003 (3)0.024 (4)−0.003 (3)
O60.057 (4)0.049 (4)0.054 (4)0.001 (3)0.017 (3)0.009 (3)
O70.106 (9)0.172 (11)0.169 (11)−0.009 (8)0.013 (8)0.051 (9)
C10.027 (5)0.044 (5)0.038 (5)0.001 (4)0.013 (4)−0.007 (4)
C20.043 (6)0.055 (6)0.055 (6)−0.001 (5)0.011 (5)0.020 (5)
C30.043 (6)0.059 (7)0.053 (6)0.002 (5)0.013 (5)0.023 (5)
C40.057 (7)0.065 (7)0.067 (7)0.004 (6)0.006 (6)0.015 (6)
C50.069 (8)0.074 (8)0.073 (8)0.019 (7)0.017 (6)0.016 (7)
C60.054 (7)0.076 (8)0.070 (8)0.009 (6)0.008 (6)0.031 (7)
C70.063 (7)0.068 (8)0.053 (7)−0.008 (6)0.008 (6)0.019 (6)
C80.051 (7)0.062 (7)0.053 (7)0.004 (6)0.008 (5)0.023 (6)
C90.070 (8)0.074 (8)0.060 (7)0.003 (6)−0.001 (6)0.010 (6)
C100.102 (10)0.084 (9)0.078 (9)0.006 (8)−0.006 (8)0.002 (7)
C110.102 (11)0.085 (10)0.079 (9)−0.008 (8)−0.014 (8)0.003 (8)
C120.079 (9)0.088 (10)0.073 (8)−0.004 (8)−0.003 (7)0.021 (7)
C130.036 (5)0.038 (5)0.038 (5)0.001 (5)0.008 (4)−0.005 (5)
C140.053 (6)0.063 (6)0.047 (6)−0.005 (5)0.014 (5)−0.017 (5)
C150.056 (7)0.066 (7)0.058 (7)−0.011 (6)0.025 (5)−0.022 (6)
C160.074 (8)0.071 (8)0.069 (8)−0.001 (6)0.026 (6)−0.014 (6)
C170.083 (9)0.091 (9)0.072 (8)−0.012 (7)0.045 (7)−0.020 (7)
C180.072 (8)0.085 (9)0.083 (9)−0.002 (7)0.030 (7)−0.029 (7)
C190.062 (8)0.068 (8)0.079 (9)−0.007 (6)0.023 (7)−0.021 (7)
C200.059 (7)0.056 (7)0.067 (7)−0.009 (6)0.022 (6)−0.018 (6)
C210.066 (8)0.064 (7)0.073 (8)0.001 (6)0.022 (6)−0.013 (6)
C220.083 (9)0.081 (9)0.090 (10)0.003 (8)0.016 (8)−0.008 (8)
C230.087 (10)0.077 (9)0.102 (11)0.008 (8)0.010 (8)−0.009 (8)
C240.074 (9)0.082 (9)0.092 (10)0.001 (7)0.023 (8)−0.024 (8)
C250.041 (6)0.034 (6)0.073 (7)−0.004 (4)0.015 (5)−0.004 (6)
C260.071 (8)0.047 (6)0.086 (8)0.001 (6)0.023 (6)0.009 (6)
C270.094 (10)0.043 (7)0.089 (9)−0.008 (6)0.021 (8)0.008 (6)
C280.106 (10)0.056 (8)0.100 (10)−0.008 (7)0.025 (9)0.010 (7)
C290.129 (13)0.070 (9)0.106 (12)−0.018 (10)0.028 (11)0.004 (8)
C300.120 (14)0.073 (10)0.112 (13)−0.023 (10)−0.001 (11)0.016 (9)
C310.101 (12)0.055 (8)0.116 (12)−0.020 (9)0.013 (9)0.023 (9)
C320.088 (10)0.046 (7)0.094 (10)−0.020 (7)0.014 (8)0.013 (7)
C330.077 (9)0.054 (7)0.111 (10)−0.012 (7)0.020 (8)0.013 (7)
C340.080 (10)0.073 (9)0.118 (12)−0.009 (8)0.022 (9)0.018 (8)
C350.089 (11)0.080 (11)0.129 (14)−0.014 (9)0.006 (11)0.022 (9)
C360.105 (13)0.077 (10)0.120 (13)−0.027 (10)0.003 (10)0.015 (10)
C370.036 (6)0.066 (7)0.069 (7)0.006 (5)0.034 (5)0.016 (6)
C380.055 (7)0.073 (7)0.073 (7)0.013 (6)0.036 (6)0.009 (6)
C390.048 (6)0.065 (7)0.082 (8)0.013 (5)0.043 (6)0.020 (6)
C400.035 (5)0.057 (6)0.076 (7)0.002 (5)0.028 (5)0.022 (6)
C410.031 (5)0.049 (6)0.068 (6)0.002 (5)0.020 (5)0.018 (5)
C420.034 (6)0.053 (6)0.075 (8)−0.005 (5)0.020 (5)0.011 (5)
C430.044 (7)0.066 (7)0.086 (9)−0.012 (6)0.015 (6)0.011 (6)
C440.052 (8)0.077 (8)0.097 (10)−0.025 (7)−0.002 (7)0.002 (7)
C450.061 (8)0.094 (9)0.080 (8)−0.025 (7)0.004 (6)−0.014 (7)
C460.045 (6)0.079 (8)0.070 (7)−0.021 (6)0.011 (5)−0.015 (6)
C470.038 (6)0.069 (7)0.100 (9)−0.004 (5)0.024 (6)0.030 (7)
C480.035 (6)0.068 (8)0.102 (10)−0.019 (6)0.006 (6)0.023 (7)
C490.105 (13)0.118 (13)0.105 (12)−0.005 (11)0.016 (10)0.021 (10)
C500.098 (11)0.091 (9)0.102 (10)0.001 (8)0.021 (8)0.026 (8)
C510.159 (15)0.146 (14)0.119 (13)0.043 (12)0.058 (11)0.001 (11)
Geometric parameters (Å, °) top
Eu1—O1i2.367 (5)C19—C241.384 (14)
Eu1—O32.389 (5)C19—C201.444 (13)
Eu1—O4i2.406 (5)C20—C211.401 (13)
Eu1—O62.477 (6)C21—C221.370 (13)
Eu1—O52.488 (6)C21—H210.9300
Eu1—O22.503 (5)C22—C231.407 (15)
Eu1—O12.578 (5)C22—H220.9300
Eu1—N22.578 (7)C23—C241.343 (15)
Eu1—N12.635 (6)C23—H230.9300
Eu1—Eu1i3.9700 (9)C24—H240.9300
N1—C371.309 (10)C25—C261.533 (12)
N1—C411.362 (10)C26—C271.481 (13)
N2—C461.315 (11)C26—H26A0.9700
N2—C421.345 (10)C26—H26B0.9700
N3—C491.304 (16)C27—C281.381 (14)
N3—C511.420 (14)C27—C321.409 (15)
N3—C501.434 (14)C28—C291.410 (16)
O1—C11.278 (8)C28—H280.9300
O1—Eu1i2.367 (5)C29—C301.317 (17)
O2—C11.233 (9)C29—H290.9300
O3—C131.242 (9)C30—C311.373 (18)
O4—C131.259 (9)C30—H300.9300
O4—Eu1i2.406 (5)C31—C321.418 (16)
O5—C251.234 (10)C31—C361.418 (18)
O6—C251.247 (10)C32—C331.419 (15)
O7—C491.250 (15)C33—C341.393 (15)
C1—C21.504 (10)C33—H330.9300
C2—C31.500 (11)C34—C351.358 (16)
C2—H2A0.9700C34—H340.9300
C2—H2B0.9700C35—C361.294 (17)
C3—C41.331 (12)C35—H350.9300
C3—C81.410 (13)C36—H360.9300
C4—C51.406 (12)C37—C381.424 (11)
C4—H40.9300C37—H370.9300
C5—C61.335 (13)C38—C391.353 (12)
C5—H50.9300C38—H380.9300
C6—C71.385 (13)C39—C401.391 (12)
C6—H60.9300C39—H390.9300
C7—C121.395 (14)C40—C411.395 (11)
C7—C81.434 (12)C40—C471.421 (12)
C8—C91.390 (13)C41—C421.427 (12)
C9—C101.356 (13)C42—C431.417 (12)
C9—H90.9300C43—C441.403 (14)
C10—C111.411 (15)C43—C481.416 (14)
C10—H100.9300C44—C451.342 (14)
C11—C121.334 (15)C44—H440.9300
C11—H110.9300C45—C461.388 (12)
C12—H120.9300C45—H450.9300
C13—C141.516 (10)C46—H460.9300
C14—C151.513 (12)C47—C481.324 (13)
C14—H14A0.9700C47—H470.9300
C14—H14B0.9700C48—H480.9300
C15—C161.362 (13)C49—H490.9300
C15—C201.409 (13)C50—H50A0.9600
C16—C171.407 (13)C50—H50B0.9600
C16—H160.9300C50—H50C0.9600
C17—C181.347 (14)C51—H51A0.9600
C17—H170.9300C51—H51B0.9600
C18—C191.383 (14)C51—H51C0.9600
C18—H180.9300
O1i—Eu1—O373.98 (16)C17—C16—H16119.0
O1i—Eu1—O4i77.01 (17)C18—C17—C16118.7 (11)
O3—Eu1—O4i136.22 (18)C18—C17—H17120.6
O1i—Eu1—O686.18 (19)C16—C17—H17120.6
O3—Eu1—O6124.9 (2)C17—C18—C19123.0 (12)
O4i—Eu1—O684.4 (2)C17—C18—H18118.5
O1i—Eu1—O575.43 (18)C19—C18—H18118.5
O3—Eu1—O573.3 (2)C18—C19—C24123.8 (12)
O4i—Eu1—O5129.0 (2)C18—C19—C20117.7 (11)
O6—Eu1—O551.9 (2)C24—C19—C20118.4 (12)
O1i—Eu1—O2123.48 (18)C21—C20—C15122.9 (10)
O3—Eu1—O277.43 (18)C21—C20—C19117.8 (11)
O4i—Eu1—O292.48 (18)C15—C20—C19119.2 (10)
O6—Eu1—O2148.75 (19)C22—C21—C20120.8 (11)
O5—Eu1—O2138.44 (19)C22—C21—H21119.6
O1i—Eu1—O173.28 (19)C20—C21—H21119.6
O3—Eu1—O168.75 (18)C21—C22—C23120.9 (13)
O4i—Eu1—O171.92 (17)C21—C22—H22119.6
O6—Eu1—O1151.40 (18)C23—C22—H22119.6
O5—Eu1—O1135.95 (19)C24—C23—C22118.8 (13)
O2—Eu1—O151.02 (16)C24—C23—H23120.6
O1i—Eu1—N2142.8 (2)C22—C23—H23120.6
O3—Eu1—N279.4 (2)C23—C24—C19123.2 (13)
O4i—Eu1—N2138.9 (2)C23—C24—H24118.4
O6—Eu1—N288.4 (2)C19—C24—H24118.4
O5—Eu1—N272.4 (2)O5—C25—O6122.2 (9)
O2—Eu1—N273.7 (2)O5—C25—C26118.1 (9)
O1—Eu1—N2120.01 (19)O6—C25—C26119.7 (10)
O1i—Eu1—N1149.65 (19)C27—C26—C25111.4 (8)
O3—Eu1—N1136.33 (19)C27—C26—H26A109.3
O4i—Eu1—N176.7 (2)C25—C26—H26A109.3
O6—Eu1—N176.3 (2)C27—C26—H26B109.3
O5—Eu1—N1110.6 (2)C25—C26—H26B109.3
O2—Eu1—N172.69 (18)H26A—C26—H26B108.0
O1—Eu1—N1112.18 (18)C28—C27—C32118.0 (12)
N2—Eu1—N162.2 (2)C28—C27—C26120.9 (13)
O1i—Eu1—Eu1i38.45 (13)C32—C27—C26121.1 (12)
O3—Eu1—Eu1i66.43 (12)C27—C28—C29118.8 (13)
O4i—Eu1—Eu1i70.40 (13)C27—C28—H28120.6
O6—Eu1—Eu1i122.03 (14)C29—C28—H28120.6
O5—Eu1—Eu1i108.46 (14)C30—C29—C28122.3 (15)
O2—Eu1—Eu1i85.44 (12)C30—C29—H29118.9
O1—Eu1—Eu1i34.83 (11)C28—C29—H29118.9
N2—Eu1—Eu1i143.13 (17)C29—C30—C31122.2 (16)
N1—Eu1—Eu1i139.44 (15)C29—C30—H30118.9
C37—N1—C41117.4 (7)C31—C30—H30118.9
C37—N1—Eu1122.6 (5)C30—C31—C32117.0 (15)
C41—N1—Eu1120.0 (6)C30—C31—C36124.5 (16)
C46—N2—C42118.3 (8)C32—C31—C36118.5 (16)
C46—N2—Eu1119.8 (6)C27—C32—C31121.7 (14)
C42—N2—Eu1121.8 (6)C27—C32—C33120.8 (12)
C49—N3—C51119.8 (14)C31—C32—C33117.5 (14)
C49—N3—C50120.5 (13)C34—C33—C32120.6 (12)
C51—N3—C50119.7 (12)C34—C33—H33119.7
C1—O1—Eu1i154.9 (5)C32—C33—H33119.7
C1—O1—Eu190.3 (5)C35—C34—C33118.3 (14)
Eu1i—O1—Eu1106.72 (19)C35—C34—H34120.8
C1—O2—Eu194.9 (5)C33—C34—H34120.8
C13—O3—Eu1139.5 (5)C36—C35—C34124.2 (17)
C13—O4—Eu1i133.5 (5)C36—C35—H35117.9
C25—O5—Eu192.8 (5)C34—C35—H35117.9
C25—O6—Eu192.9 (6)C35—C36—C31120.7 (16)
O2—C1—O1121.3 (7)C35—C36—H36119.6
O2—C1—C2122.6 (7)C31—C36—H36119.6
O1—C1—C2116.0 (7)N1—C37—C38124.1 (9)
C3—C2—C1115.2 (7)N1—C37—H37118.0
C3—C2—H2A108.5C38—C37—H37118.0
C1—C2—H2A108.5C39—C38—C37117.7 (10)
C3—C2—H2B108.5C39—C38—H38121.2
C1—C2—H2B108.5C37—C38—H38121.2
H2A—C2—H2B107.5C38—C39—C40120.1 (9)
C4—C3—C8119.1 (9)C38—C39—H39120.0
C4—C3—C2119.2 (9)C40—C39—H39120.0
C8—C3—C2121.6 (9)C39—C40—C41118.4 (9)
C3—C4—C5123.0 (10)C39—C40—C47122.6 (9)
C3—C4—H4118.5C41—C40—C47119.0 (10)
C5—C4—H4118.5N1—C41—C40122.4 (9)
C6—C5—C4118.2 (11)N1—C41—C42117.1 (8)
C6—C5—H5120.9C40—C41—C42120.4 (9)
C4—C5—H5120.9N2—C42—C43122.5 (10)
C5—C6—C7122.9 (10)N2—C42—C41118.7 (8)
C5—C6—H6118.6C43—C42—C41118.7 (9)
C7—C6—H6118.6C44—C43—C48125.4 (10)
C6—C7—C12124.0 (11)C44—C43—C42116.1 (10)
C6—C7—C8117.9 (10)C48—C43—C42118.5 (11)
C12—C7—C8118.1 (11)C45—C44—C43120.7 (10)
C9—C8—C3123.0 (9)C45—C44—H44119.6
C9—C8—C7118.1 (10)C43—C44—H44119.6
C3—C8—C7118.9 (10)C44—C45—C46119.0 (11)
C10—C9—C8122.7 (11)C44—C45—H45120.5
C10—C9—H9118.6C46—C45—H45120.5
C8—C9—H9118.6N2—C46—C45123.3 (10)
C9—C10—C11118.0 (12)N2—C46—H46118.3
C9—C10—H10121.0C45—C46—H46118.3
C11—C10—H10121.0C48—C47—C40120.9 (10)
C12—C11—C10121.5 (12)C48—C47—H47119.6
C12—C11—H11119.2C40—C47—H47119.6
C10—C11—H11119.2C47—C48—C43122.5 (10)
C11—C12—C7121.5 (12)C47—C48—H48118.7
C11—C12—H12119.2C43—C48—H48118.7
C7—C12—H12119.2O7—C49—N3122.3 (17)
O3—C13—O4126.0 (8)O7—C49—H49118.8
O3—C13—C14116.9 (7)N3—C49—H49118.8
O4—C13—C14117.1 (7)N3—C50—H50A109.5
C15—C14—C13116.7 (7)N3—C50—H50B109.5
C15—C14—H14A108.1H50A—C50—H50B109.5
C13—C14—H14A108.1N3—C50—H50C109.5
C15—C14—H14B108.1H50A—C50—H50C109.5
C13—C14—H14B108.1H50B—C50—H50C109.5
H14A—C14—H14B107.3N3—C51—H51A109.5
C16—C15—C20119.2 (10)N3—C51—H51B109.5
C16—C15—C14119.5 (10)H51A—C51—H51B109.5
C20—C15—C14121.2 (9)N3—C51—H51C109.5
C15—C16—C17122.0 (11)H51A—C51—H51C109.5
C15—C16—H16119.0H51B—C51—H51C109.5
O1i—Eu1—N1—C3728.0 (9)C6—C7—C8—C9178.3 (9)
O3—Eu1—N1—C37−148.6 (6)C12—C7—C8—C9−1.4 (14)
O4i—Eu1—N1—C37−2.8 (6)C6—C7—C8—C3−0.2 (14)
O6—Eu1—N1—C3784.6 (7)C12—C7—C8—C3−179.9 (9)
O5—Eu1—N1—C37124.3 (6)C3—C8—C9—C10180.0 (10)
O2—Eu1—N1—C37−99.7 (7)C7—C8—C9—C101.5 (16)
O1—Eu1—N1—C37−66.6 (7)C8—C9—C10—C11−1.6 (18)
N2—Eu1—N1—C37−180.0 (7)C9—C10—C11—C122(2)
Eu1i—Eu1—N1—C37−39.1 (7)C10—C11—C12—C7−1(2)
O1i—Eu1—N1—C41−154.3 (5)C6—C7—C12—C11−178.3 (11)
O3—Eu1—N1—C4129.1 (7)C8—C7—C12—C111.4 (17)
O4i—Eu1—N1—C41175.0 (6)Eu1—O3—C13—O4−30.2 (15)
O6—Eu1—N1—C41−97.7 (6)Eu1—O3—C13—C14151.8 (6)
O5—Eu1—N1—C41−58.0 (6)Eu1i—O4—C13—O310.3 (13)
O2—Eu1—N1—C4178.1 (6)Eu1i—O4—C13—C14−171.7 (5)
O1—Eu1—N1—C41111.1 (6)O3—C13—C14—C15−139.8 (9)
N2—Eu1—N1—C41−2.2 (6)O4—C13—C14—C1542.0 (12)
Eu1i—Eu1—N1—C41138.6 (5)C13—C14—C15—C16−119.9 (10)
O1i—Eu1—N2—C46−23.9 (9)C13—C14—C15—C2063.7 (12)
O3—Eu1—N2—C4620.7 (7)C20—C15—C16—C17−1.1 (15)
O4i—Eu1—N2—C46175.1 (6)C14—C15—C16—C17−177.6 (9)
O6—Eu1—N2—C46−105.4 (7)C15—C16—C17—C180.9 (17)
O5—Eu1—N2—C46−55.1 (7)C16—C17—C18—C191.7 (17)
O2—Eu1—N2—C46100.6 (7)C17—C18—C19—C24176.8 (11)
O1—Eu1—N2—C4678.4 (7)C17—C18—C19—C20−3.9 (17)
N1—Eu1—N2—C46179.2 (8)C16—C15—C20—C21−177.7 (10)
Eu1i—Eu1—N2—C4642.4 (8)C14—C15—C20—C21−1.3 (14)
O1i—Eu1—N2—C42160.1 (6)C16—C15—C20—C19−1.2 (14)
O3—Eu1—N2—C42−155.3 (7)C14—C15—C20—C19175.3 (8)
O4i—Eu1—N2—C42−0.9 (8)C18—C19—C20—C21−179.7 (9)
O6—Eu1—N2—C4278.6 (7)C24—C19—C20—C21−0.3 (14)
O5—Eu1—N2—C42128.9 (7)C18—C19—C20—C153.5 (14)
O2—Eu1—N2—C42−75.5 (7)C24—C19—C20—C15−177.1 (9)
O1—Eu1—N2—C42−97.7 (7)C15—C20—C21—C22175.8 (10)
N1—Eu1—N2—C423.2 (6)C19—C20—C21—C22−0.8 (15)
Eu1i—Eu1—N2—C42−133.6 (6)C20—C21—C22—C231.1 (17)
O1i—Eu1—O1—C1161.2 (5)C21—C22—C23—C24−0.1 (18)
O3—Eu1—O1—C182.3 (4)C22—C23—C24—C19−1.1 (19)
O4i—Eu1—O1—C1−117.3 (4)C18—C19—C24—C23−179.3 (12)
O6—Eu1—O1—C1−152.9 (5)C20—C19—C24—C231.4 (17)
O5—Eu1—O1—C1114.7 (5)Eu1—O5—C25—O6−5.4 (10)
O2—Eu1—O1—C1−8.5 (4)Eu1—O5—C25—C26173.2 (7)
N2—Eu1—O1—C119.3 (5)Eu1—O6—C25—O55.4 (10)
N1—Eu1—O1—C1−50.5 (5)Eu1—O6—C25—C26−173.1 (8)
Eu1i—Eu1—O1—C1161.2 (5)O5—C25—C26—C27−52.7 (13)
O1i—Eu1—O1—Eu1i0.0O6—C25—C26—C27125.9 (11)
O3—Eu1—O1—Eu1i−78.9 (2)C25—C26—C27—C28107.6 (11)
O4i—Eu1—O1—Eu1i81.4 (2)C25—C26—C27—C32−69.9 (13)
O6—Eu1—O1—Eu1i45.8 (5)C32—C27—C28—C29−0.5 (15)
O5—Eu1—O1—Eu1i−46.5 (3)C26—C27—C28—C29−178.2 (10)
O2—Eu1—O1—Eu1i−169.7 (3)C27—C28—C29—C302.1 (19)
N2—Eu1—O1—Eu1i−141.9 (2)C28—C29—C30—C31−2(2)
N1—Eu1—O1—Eu1i148.3 (2)C29—C30—C31—C320(2)
O1i—Eu1—O2—C1−3.0 (5)C29—C30—C31—C36179.9 (13)
O3—Eu1—O2—C1−63.9 (5)C28—C27—C32—C31−1.3 (16)
O4i—Eu1—O2—C173.1 (5)C26—C27—C32—C31176.3 (10)
O6—Eu1—O2—C1156.4 (5)C28—C27—C32—C33178.0 (10)
O5—Eu1—O2—C1−109.9 (5)C26—C27—C32—C33−4.3 (16)
O1—Eu1—O2—C18.8 (4)C30—C31—C32—C271.7 (17)
N2—Eu1—O2—C1−146.3 (5)C36—C31—C32—C27−178.3 (11)
N1—Eu1—O2—C1148.4 (5)C30—C31—C32—C33−177.7 (11)
Eu1i—Eu1—O2—C13.0 (4)C36—C31—C32—C332.4 (17)
O1i—Eu1—O3—C13−17.2 (9)C27—C32—C33—C34178.6 (10)
O4i—Eu1—O3—C1333.2 (10)C31—C32—C33—C34−2.0 (16)
O6—Eu1—O3—C13−90.6 (9)C32—C33—C34—C350.0 (17)
O5—Eu1—O3—C13−96.4 (9)C33—C34—C35—C362(2)
O2—Eu1—O3—C13113.5 (9)C34—C35—C36—C31−2(2)
O1—Eu1—O3—C1360.8 (9)C30—C31—C36—C35179.4 (13)
N2—Eu1—O3—C13−171.0 (9)C32—C31—C36—C35−1(2)
N1—Eu1—O3—C13161.1 (8)C41—N1—C37—C380.4 (13)
Eu1i—Eu1—O3—C1323.1 (9)Eu1—N1—C37—C38178.1 (7)
O1i—Eu1—O5—C2599.6 (6)N1—C37—C38—C39−0.2 (14)
O3—Eu1—O5—C25176.9 (6)C37—C38—C39—C40−0.2 (14)
O4i—Eu1—O5—C2540.2 (6)C38—C39—C40—C410.2 (14)
O6—Eu1—O5—C252.9 (5)C38—C39—C40—C47−179.4 (9)
O2—Eu1—O5—C25−135.9 (5)C37—N1—C41—C40−0.3 (12)
O1—Eu1—O5—C25145.5 (5)Eu1—N1—C41—C40−178.1 (6)
N2—Eu1—O5—C25−99.3 (6)C37—N1—C41—C42179.1 (8)
N1—Eu1—O5—C25−49.1 (6)Eu1—N1—C41—C421.3 (10)
Eu1i—Eu1—O5—C25119.6 (5)C39—C40—C41—N10.0 (14)
O1i—Eu1—O6—C25−77.3 (5)C47—C40—C41—N1179.6 (8)
O3—Eu1—O6—C25−9.9 (6)C39—C40—C41—C42−179.4 (8)
O4i—Eu1—O6—C25−154.6 (5)C47—C40—C41—C420.2 (13)
O5—Eu1—O6—C25−2.9 (5)C46—N2—C42—C430.6 (14)
O2—Eu1—O6—C25119.8 (6)Eu1—N2—C42—C43176.7 (7)
O1—Eu1—O6—C25−120.9 (6)C46—N2—C42—C41179.9 (8)
N2—Eu1—O6—C2565.9 (5)Eu1—N2—C42—C41−4.0 (11)
N1—Eu1—O6—C25127.7 (6)N1—C41—C42—N21.7 (12)
Eu1i—Eu1—O6—C25−92.0 (5)C40—C41—C42—N2−178.9 (8)
Eu1—O2—C1—O1−16.4 (8)N1—C41—C42—C43−179.0 (8)
Eu1—O2—C1—C2162.8 (7)C40—C41—C42—C430.4 (13)
Eu1i—O1—C1—O2149.4 (9)N2—C42—C43—C44−0.9 (15)
Eu1—O1—C1—O215.8 (7)C41—C42—C43—C44179.9 (9)
Eu1i—O1—C1—C2−29.9 (16)N2—C42—C43—C48178.5 (9)
Eu1—O1—C1—C2−163.4 (6)C41—C42—C43—C48−0.8 (14)
O2—C1—C2—C3−4.3 (12)C48—C43—C44—C45−178.5 (11)
O1—C1—C2—C3174.9 (8)C42—C43—C44—C450.8 (16)
C1—C2—C3—C4111.3 (10)C43—C44—C45—C46−0.5 (18)
C1—C2—C3—C8−70.9 (11)C42—N2—C46—C45−0.3 (15)
C8—C3—C4—C51.4 (15)Eu1—N2—C46—C45−176.4 (8)
C2—C3—C4—C5179.4 (9)C44—C45—C46—N20.2 (18)
C3—C4—C5—C60.4 (16)C39—C40—C47—C48179.1 (10)
C4—C5—C6—C7−2.2 (16)C41—C40—C47—C48−0.5 (15)
C5—C6—C7—C12−178.3 (11)C40—C47—C48—C430.1 (16)
C5—C6—C7—C82.1 (15)C44—C43—C48—C47179.8 (11)
C4—C3—C8—C9−179.9 (9)C42—C43—C48—C470.5 (16)
C2—C3—C8—C92.2 (14)C51—N3—C49—O7−3(2)
C4—C3—C8—C7−1.5 (14)C50—N3—C49—O7177.8 (13)
C2—C3—C8—C7−179.4 (8)
Symmetry codes: (i) −x+1, −y+1, −z+2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O7ii0.932.583.469 (15)161
C37—H37···O4i0.932.383.053 (10)130
C46—H46···O30.932.483.096 (11)124
C47—H47···O2iii0.932.463.314 (11)152
C50—H50A···O6iv0.962.603.397 (14)140
C18—H18···Cg1v0.932.913.682 (13)141
Symmetry codes: (ii) −x, −y+1, −z+1; (i) −x+1, −y+1, −z+2; (iii) −x, −y+1, −z+2; (iv) x, y, z−1; (v) −x+1, y+1/2, −z+1/2.
Table 1
Selected geometric parameters (Å) top
Eu1—O1i2.367 (5)Eu1—O22.503 (5)
Eu1—O32.389 (5)Eu1—O12.578 (5)
Eu1—O4i2.406 (5)Eu1—N22.578 (7)
Eu1—O62.477 (6)Eu1—N12.635 (6)
Eu1—O52.488 (6)
Symmetry codes: (i) −x+1, −y+1, −z+2.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O7ii0.932.583.469 (15)161
C37—H37···O4i0.932.383.053 (10)130
C46—H46···O30.932.483.096 (11)124
C47—H47···O2iii0.932.463.314 (11)152
C50—H50A···O6iv0.962.603.397 (14)140
C18—H18···Cg1v0.932.913.682 (13)141
Symmetry codes: (ii) −x, −y+1, −z+1; (i) −x+1, −y+1, −z+2; (iii) −x, −y+1, −z+2; (iv) x, y, z−1; (v) −x+1, y+1/2, −z+1/2.
Acknowledgements top

The authors acknowledge the financial support of the Huaihai Institute of Technology Science Foundation.

references
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