Tetra-μ-acetato-κ4O:O′;κ3O,O′:O′;κ3O:O,O′-bis­[(acetato-κ2O,O′)(1,10-phenanthroline-κ2N,N′)europium(III)]

Liu, W.-J.; Li, Z.-Y.; Wei, Z.-Q.; Yue, S.-T.

doi:10.1107/S1600536810015680

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page m606

https://doi.org/10.1107/S1600536810015680

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Tetra-μ-acetato-κ⁴O:O′;κ³O,O′:O′;κ³O:O,O′-bis[(acetato-κ²O,O′)(1,10-phenanthroline-κ²N,N′)europium(III)]

Wen-Jing Liu,^a Zhao-Yang Li,^a Zhi-Qiang Wei ^a and Shan-Tang Yue ^a ^*

^aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510006, People's Republic of China
^*Correspondence e-mail: yuesht@scnu.edu.cn

(Received 26 April 2010; accepted 28 April 2010; online 8 May 2010)

In the title centrosymmetric dinuclear Eu^III complex, [Eu₂(CH₃COO)₆(C₁₂H₈N₂)₂], each Eu^III cation is coordinated by seven O atoms from five acetate anions and two N atoms from one phenanthroline ligand in a distorted tricapped trigonal-prismatic geometry. Four acetate anions bridge two Eu^III cations to form the dinuclear complex, with an Eu⋯Eu distance of 3.9409 (8) Å. Weak intermolecular C—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For related lanthanide complexes with 1,10-phenanthroline and acetate ligands, see: Hu et al. (2006 ); Panagiotopoulos et al. (1995 ).

Experimental

Crystal data

[Eu₂(C₂H₃O₂)₆(C₁₂H₈N₂)₂]
M_r = 1018.61
Triclinic, $[P \overline 1]$
a = 8.7671 (19) Å
b = 8.9265 (19) Å
c = 12.992 (3) Å
α = 103.631 (2)°
β = 109.254 (2)°
γ = 98.300 (3)°
V = 905.1 (3) Å³
Z = 1
Mo Kα radiation
μ = 3.50 mm⁻¹
T = 298 K
0.20 × 0.19 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.541, T_max = 0.571
5010 measured reflections
3474 independent reflections
3062 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.062
S = 1.05
3474 reflections
247 parameters
H-atom parameters constrained
Δρ_max = 0.80 e Å⁻³
Δρ_min = −0.64 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2ⁱ	0.93	2.57	3.287 (6)	135
C12—H8⋯O6ⁱⁱ	0.93	2.44	3.078 (6)	126
C16—H10C⋯O1ⁱⁱⁱ	0.96	2.45	3.390 (6)	165
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+2, -z+1; (iii) x, y+1, z.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810015680/xu2753sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810015680/xu2753Isup2.hkl

checkCIF report

Comment top

Dinuclear lanthanide complexes with 1,10-phenanthroline and acetate ligands had previously been reported (Panagiotopoulos et al., 1995; Hu et al., 2006). In this title complex, each Eu atom is coordinated by two N atoms from one chelating phenanthroline ligand and seven oxygen atoms from acetate ions, to form a distorted tricapped trigonal prism, giving a dimeric structure with an inversion center (Fig.1). The result of the dinuclear centrosymmetric molecule with the Eu···Eu distance of 3.9409 (8) Å was that acetate ions exhibit three different coordination modes: common bidentate chelating mode, bidentate bridging mode and tridentate bridging mode. The Eu1—O bond distances vary from 2.359 (3) Å to 2.586 (3) Å and the Eu1—N bond length are 2.594 (3) Å and 2.649 (4) Å. The C—O distances of CH₃COO^- are within the range of 1.257 (5)Å to 1.273 (5) Å. This complex exhibits a three-dimensional structure via C—H···O hydrogen-bonds (Table 1).

Related literature top

For related lanthanide complexes with 1,10-phenanthroline and acetate ligands, see: Hu et al. (2006); Panagiotopoulos et al. (1995).

Experimental top

A stoichiometric amount of acetic acid and a quantitative amount of 1,10-phenanthroline (0.5 mmol) were mixed and then dissolved in 95% ethanol solution (20 ml). The pH value of the solution was adjusted to 6.5 by adding 1.0 M NaOH solution, and then added dropwise to the ethanol solution (20 ml) of Eu(NO₃)₃.6H₂O (0.5 mmol). The solution mixture was stirred continuously for 2 h at room temperature and then filtered. Single crystals were obtained by evaporation after one week.

Structure description top

For related lanthanide complexes with 1,10-phenanthroline and acetate ligands, see: Hu et al. (2006); Panagiotopoulos et al. (1995).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Displacement ellipsoid plot (40% probability level) of the title compound [symmetry code: (A) -x+1, -y+2, -z+1].

Tetra-µ-acetato-κ⁴O:O';κ³O,O':O'; κ³O:O,O'-bis[(acetato-κ²O,O')(1,10- phenanthroline-κ²N,N')europium(III)] top

Crystal data top

[Eu₂(C₂H₃O₂)₆(C₁₂H₈N₂)₂]	Z = 1
M_r = 1018.61	F(000) = 500
Triclinic, P1	D_x = 1.869 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7671 (19) Å	Cell parameters from 2079 reflections
b = 8.9265 (19) Å	θ = 0.7–25.2°
c = 12.992 (3) Å	µ = 3.50 mm⁻¹
α = 103.631 (2)°	T = 298 K
β = 109.254 (2)°	Block, colorless
γ = 98.300 (3)°	0.20 × 0.19 × 0.18 mm
V = 905.1 (3) Å³

Data collection top

Bruker SMART CCD diffractometer	3474 independent reflections
Radiation source: fine-focus sealed tube	3062 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω scans	θ_max = 26.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
T_min = 0.541, T_max = 0.571	k = −8→10
5010 measured reflections	l = −14→15

Refinement top

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.062	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.025P)²] where P = (F_o² + 2F_c²)/3
3474 reflections	(Δ/σ)_max < 0.001
247 parameters	Δρ_max = 0.80 e Å⁻³
0 restraints	Δρ_min = −0.64 e Å⁻³

Crystal data top

[Eu₂(C₂H₃O₂)₆(C₁₂H₈N₂)₂]	γ = 98.300 (3)°
M_r = 1018.61	V = 905.1 (3) Å³
Triclinic, P1	Z = 1
a = 8.7671 (19) Å	Mo Kα radiation
b = 8.9265 (19) Å	µ = 3.50 mm⁻¹
c = 12.992 (3) Å	T = 298 K
α = 103.631 (2)°	0.20 × 0.19 × 0.18 mm
β = 109.254 (2)°

Data collection top

Bruker SMART CCD diffractometer	3474 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3062 reflections with I > 2σ(I)
T_min = 0.541, T_max = 0.571	R_int = 0.021
5010 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.062	H-atom parameters constrained
S = 1.05	Δρ_max = 0.80 e Å⁻³
3474 reflections	Δρ_min = −0.64 e Å⁻³
247 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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

	x	y	z	U_iso*/U_eq
Eu1	0.47430 (3)	0.84412 (3)	0.356229 (17)	0.02341 (8)
O3	0.5788 (4)	1.1409 (4)	0.4756 (2)	0.0312 (7)
O4	0.6208 (4)	1.0735 (4)	0.3157 (2)	0.0336 (7)
O2	0.2565 (4)	0.5955 (4)	0.2687 (3)	0.0419 (8)
O1	0.5000 (4)	0.5829 (4)	0.3834 (3)	0.0373 (8)
O5	0.7449 (4)	0.8969 (4)	0.4988 (2)	0.0310 (7)
N1	0.6375 (4)	0.7194 (4)	0.2384 (3)	0.0277 (8)
C1	0.7671 (6)	0.6658 (5)	0.2863 (4)	0.0362 (11)
H1	0.7915	0.6637	0.3612	0.043*
C2	0.8702 (6)	0.6116 (6)	0.2307 (4)	0.0423 (12)
H2	0.9609	0.5753	0.2678	0.051*
C3	0.8341 (6)	0.6134 (6)	0.1215 (4)	0.0450 (13)
H3	0.9007	0.5782	0.0829	0.054*
C4	0.6972 (6)	0.6680 (6)	0.0664 (4)	0.0368 (11)
C7	0.4176 (6)	0.7809 (6)	−0.0387 (4)	0.0421 (13)
C6	0.4559 (6)	0.7750 (5)	0.0747 (3)	0.0294 (10)
N2	0.3612 (5)	0.8179 (4)	0.1353 (3)	0.0323 (9)
C12	0.2280 (6)	0.8637 (6)	0.0849 (4)	0.0437 (13)
H8	0.1601	0.8895	0.1249	0.052*
C11	0.1825 (7)	0.8757 (7)	−0.0271 (4)	0.0565 (16)
H7	0.0883	0.9110	−0.0592	0.068*
C10	0.2789 (7)	0.8348 (7)	−0.0871 (4)	0.0524 (15)
H6	0.2516	0.8431	−0.1607	0.063*
C5	0.6006 (6)	0.7203 (5)	0.1290 (4)	0.0299 (10)
C15	0.6463 (5)	1.1743 (5)	0.4079 (4)	0.0284 (10)
C13	0.3479 (6)	0.5207 (5)	0.3230 (4)	0.0327 (11)
C8	0.5223 (7)	0.7281 (7)	−0.0976 (4)	0.0534 (15)
H5	0.4986	0.7328	−0.1718	0.064*
O6	0.7627 (4)	1.0478 (4)	0.6690 (2)	0.0336 (7)
C14	0.2753 (7)	0.3534 (6)	0.3168 (5)	0.0506 (14)
H9A	0.1575	0.3255	0.2737	0.076*
H9B	0.2959	0.3470	0.3927	0.076*
H9C	0.3264	0.2814	0.2800	0.076*
C16	0.7559 (6)	1.3374 (6)	0.4417 (4)	0.0422 (12)
H10A	0.8097	1.3412	0.3886	0.063*
H10B	0.8385	1.3612	0.5172	0.063*
H10C	0.6894	1.4140	0.4409	0.063*
C9	0.6513 (7)	0.6730 (7)	−0.0494 (4)	0.0539 (15)
H4	0.7136	0.6367	−0.0914	0.065*
C18	0.9975 (5)	0.9554 (6)	0.6560 (4)	0.0395 (12)
H11A	1.0003	0.8457	0.6445	0.059*
H11B	1.0414	1.0106	0.7365	0.059*
H11C	1.0636	1.0025	0.6206	0.059*
C17	0.8220 (5)	0.9669 (5)	0.6038 (4)	0.0277 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Eu1	0.02392 (12)	0.02795 (13)	0.02150 (12)	0.00926 (9)	0.01093 (9)	0.00800 (9)
O3	0.0368 (18)	0.0376 (18)	0.0297 (16)	0.0146 (15)	0.0192 (14)	0.0159 (15)
O4	0.0410 (19)	0.0386 (19)	0.0242 (16)	0.0079 (15)	0.0181 (14)	0.0077 (15)
O2	0.039 (2)	0.038 (2)	0.045 (2)	0.0085 (16)	0.0110 (16)	0.0142 (17)
O1	0.038 (2)	0.0360 (19)	0.0442 (19)	0.0151 (15)	0.0170 (16)	0.0167 (16)
O5	0.0288 (17)	0.0393 (19)	0.0243 (16)	0.0108 (14)	0.0111 (13)	0.0056 (14)
N1	0.030 (2)	0.028 (2)	0.0260 (19)	0.0091 (16)	0.0132 (16)	0.0064 (16)
C1	0.044 (3)	0.038 (3)	0.032 (3)	0.017 (2)	0.019 (2)	0.011 (2)
C2	0.034 (3)	0.047 (3)	0.050 (3)	0.018 (2)	0.018 (2)	0.013 (3)
C3	0.046 (3)	0.047 (3)	0.048 (3)	0.016 (3)	0.031 (3)	0.004 (3)
C4	0.043 (3)	0.037 (3)	0.032 (3)	0.011 (2)	0.021 (2)	0.003 (2)
C7	0.050 (3)	0.048 (3)	0.025 (2)	0.007 (3)	0.014 (2)	0.010 (2)
C6	0.036 (3)	0.027 (2)	0.022 (2)	0.004 (2)	0.011 (2)	0.0032 (19)
N2	0.034 (2)	0.035 (2)	0.027 (2)	0.0104 (18)	0.0096 (17)	0.0088 (18)
C12	0.039 (3)	0.061 (4)	0.031 (3)	0.024 (3)	0.011 (2)	0.012 (3)
C11	0.064 (4)	0.074 (4)	0.033 (3)	0.033 (3)	0.009 (3)	0.021 (3)
C10	0.069 (4)	0.060 (4)	0.027 (3)	0.018 (3)	0.013 (3)	0.016 (3)
C5	0.037 (3)	0.025 (2)	0.028 (2)	0.005 (2)	0.015 (2)	0.005 (2)
C15	0.027 (2)	0.034 (3)	0.031 (2)	0.012 (2)	0.014 (2)	0.015 (2)
C13	0.043 (3)	0.033 (3)	0.029 (2)	0.012 (2)	0.024 (2)	0.006 (2)
C8	0.067 (4)	0.071 (4)	0.029 (3)	0.018 (3)	0.027 (3)	0.015 (3)
O6	0.0333 (18)	0.0416 (19)	0.0257 (16)	0.0171 (15)	0.0109 (14)	0.0052 (15)
C14	0.064 (4)	0.033 (3)	0.057 (3)	0.004 (3)	0.027 (3)	0.016 (3)
C16	0.049 (3)	0.036 (3)	0.046 (3)	0.007 (2)	0.027 (3)	0.009 (2)
C9	0.063 (4)	0.066 (4)	0.037 (3)	0.017 (3)	0.030 (3)	0.008 (3)
C18	0.030 (3)	0.044 (3)	0.041 (3)	0.013 (2)	0.009 (2)	0.009 (2)
C17	0.027 (2)	0.028 (2)	0.034 (3)	0.0086 (19)	0.014 (2)	0.014 (2)

Geometric parameters (Å, º) top

Eu1—O3ⁱ	2.358 (3)	C7—C10	1.384 (7)
Eu1—O6ⁱ	2.374 (3)	C7—C6	1.415 (6)
Eu1—O5	2.377 (3)	C7—C8	1.438 (7)
Eu1—O2	2.453 (3)	C6—N2	1.355 (5)
Eu1—O1	2.470 (3)	C6—C5	1.448 (6)
Eu1—O4	2.513 (3)	N2—C12	1.311 (6)
Eu1—O3	2.586 (3)	C12—C11	1.411 (7)
Eu1—N1	2.594 (3)	C12—H8	0.9300
Eu1—N2	2.649 (4)	C11—C10	1.358 (7)
Eu1—C13	2.815 (5)	C11—H7	0.9300
Eu1—C15	2.920 (4)	C10—H6	0.9300
Eu1—Eu1ⁱ	3.9409 (8)	C15—C16	1.500 (6)
O3—C15	1.276 (5)	C13—C14	1.508 (6)
O3—Eu1ⁱ	2.358 (3)	C8—C9	1.324 (8)
O4—C15	1.245 (5)	C8—H5	0.9300
O2—C13	1.262 (6)	O6—C17	1.273 (5)
O1—C13	1.262 (5)	O6—Eu1ⁱ	2.374 (3)
O5—C17	1.256 (5)	C14—H9A	0.9600
N1—C1	1.319 (6)	C14—H9B	0.9600
N1—C5	1.351 (5)	C14—H9C	0.9600
C1—C2	1.402 (6)	C16—H10A	0.9600
C1—H1	0.9300	C16—H10B	0.9600
C2—C3	1.352 (7)	C16—H10C	0.9600
C2—H2	0.9300	C9—H4	0.9300
C3—C4	1.399 (7)	C18—C17	1.492 (6)
C3—H3	0.9300	C18—H11A	0.9600
C4—C5	1.410 (6)	C18—H11B	0.9600
C4—C9	1.437 (7)	C18—H11C	0.9600

O3ⁱ—Eu1—O6ⁱ	75.03 (10)	C5—N1—Eu1	120.7 (3)
O3ⁱ—Eu1—O5	76.96 (10)	N1—C1—C2	123.7 (4)
O6ⁱ—Eu1—O5	137.07 (10)	N1—C1—H1	118.2
O3ⁱ—Eu1—O2	86.29 (10)	C2—C1—H1	118.2
O6ⁱ—Eu1—O2	81.08 (11)	C3—C2—C1	118.2 (5)
O5—Eu1—O2	128.67 (11)	C3—C2—H2	120.9
O3ⁱ—Eu1—O1	77.36 (10)	C1—C2—H2	120.9
O6ⁱ—Eu1—O1	127.36 (11)	C2—C3—C4	120.5 (4)
O5—Eu1—O1	75.84 (10)	C2—C3—H3	119.8
O2—Eu1—O1	53.10 (11)	C4—C3—H3	119.8
O3ⁱ—Eu1—O4	125.07 (10)	C3—C4—C5	117.4 (4)
O6ⁱ—Eu1—O4	90.28 (11)	C3—C4—C9	123.4 (5)
O5—Eu1—O4	79.96 (10)	C5—C4—C9	119.2 (5)
O2—Eu1—O4	144.17 (10)	C10—C7—C6	117.6 (5)
O1—Eu1—O4	141.79 (10)	C10—C7—C8	123.9 (5)
O3ⁱ—Eu1—O3	74.40 (11)	C6—C7—C8	118.5 (5)
O6ⁱ—Eu1—O3	72.72 (10)	N2—C6—C7	122.5 (4)
O5—Eu1—O3	68.79 (10)	N2—C6—C5	118.0 (4)
O2—Eu1—O3	150.59 (10)	C7—C6—C5	119.5 (4)
O1—Eu1—O3	138.62 (10)	C12—N2—C6	117.9 (4)
O4—Eu1—O3	50.80 (9)	C12—N2—Eu1	122.8 (3)
O3ⁱ—Eu1—N1	143.33 (11)	C6—N2—Eu1	118.7 (3)
O6ⁱ—Eu1—N1	139.90 (10)	N2—C12—C11	123.2 (5)
O5—Eu1—N1	77.84 (10)	N2—C12—H8	118.4
O2—Eu1—N1	89.07 (11)	C11—C12—H8	118.4
O1—Eu1—N1	70.92 (11)	C10—C11—C12	118.8 (5)
O4—Eu1—N1	75.40 (10)	C10—C11—H7	120.6
O3—Eu1—N1	119.64 (10)	C12—C11—H7	120.6
O3ⁱ—Eu1—N2	149.00 (11)	C11—C10—C7	120.0 (5)
O6ⁱ—Eu1—N2	77.11 (11)	C11—C10—H6	120.0
O5—Eu1—N2	133.80 (10)	C7—C10—H6	120.0
O2—Eu1—N2	76.19 (11)	N1—C5—C4	122.1 (4)
O1—Eu1—N2	110.07 (11)	N1—C5—C6	118.6 (4)
O4—Eu1—N2	67.99 (10)	C4—C5—C6	119.3 (4)
O3—Eu1—N2	109.76 (10)	O4—C15—O3	120.4 (4)
N1—Eu1—N2	62.79 (11)	O4—C15—C16	121.0 (4)
O3ⁱ—Eu1—C13	79.18 (11)	O3—C15—C16	118.5 (4)
O6ⁱ—Eu1—C13	103.79 (13)	O4—C15—Eu1	58.8 (2)
O5—Eu1—C13	102.11 (13)	O3—C15—Eu1	62.3 (2)
O2—Eu1—C13	26.59 (12)	C16—C15—Eu1	172.3 (3)
O1—Eu1—C13	26.61 (12)	O2—C13—O1	121.4 (4)
O4—Eu1—C13	154.90 (11)	O2—C13—C14	119.9 (4)
O3—Eu1—C13	153.35 (11)	O1—C13—C14	118.8 (5)
N1—Eu1—C13	80.57 (12)	O2—C13—Eu1	60.5 (2)
N2—Eu1—C13	94.65 (12)	O1—C13—Eu1	61.3 (2)
O3ⁱ—Eu1—C15	99.99 (11)	C14—C13—Eu1	173.6 (3)
O6ⁱ—Eu1—C15	82.87 (11)	C9—C8—C7	122.1 (5)
O5—Eu1—C15	70.72 (11)	C9—C8—H5	119.0
O2—Eu1—C15	160.62 (12)	C7—C8—H5	119.0
O1—Eu1—C15	146.09 (11)	C17—O6—Eu1ⁱ	136.1 (3)
O4—Eu1—C15	25.08 (10)	C13—C14—H9A	109.5
O3—Eu1—C15	25.89 (10)	C13—C14—H9B	109.5
N1—Eu1—C15	96.31 (11)	H9A—C14—H9B	109.5
N2—Eu1—C15	89.71 (11)	C13—C14—H9C	109.5
C13—Eu1—C15	172.71 (13)	H9A—C14—H9C	109.5
O3ⁱ—Eu1—Eu1ⁱ	39.20 (7)	H9B—C14—H9C	109.5
O6ⁱ—Eu1—Eu1ⁱ	69.54 (7)	C15—C16—H10A	109.5
O5—Eu1—Eu1ⁱ	68.14 (7)	C15—C16—H10B	109.5
O2—Eu1—Eu1ⁱ	122.20 (8)	H10A—C16—H10B	109.5
O1—Eu1—Eu1ⁱ	111.19 (7)	C15—C16—H10C	109.5
O4—Eu1—Eu1ⁱ	85.93 (7)	H10A—C16—H10C	109.5
O3—Eu1—Eu1ⁱ	35.19 (6)	H10B—C16—H10C	109.5
N1—Eu1—Eu1ⁱ	143.56 (8)	C8—C9—C4	121.4 (5)
N2—Eu1—Eu1ⁱ	137.30 (8)	C8—C9—H4	119.3
C13—Eu1—Eu1ⁱ	118.30 (9)	C4—C9—H4	119.3
C15—Eu1—Eu1ⁱ	60.89 (9)	C17—C18—H11A	109.5
C15—O3—Eu1ⁱ	160.5 (3)	C17—C18—H11B	109.5
C15—O3—Eu1	91.8 (3)	H11A—C18—H11B	109.5
Eu1ⁱ—O3—Eu1	105.60 (10)	C17—C18—H11C	109.5
C15—O4—Eu1	96.1 (2)	H11A—C18—H11C	109.5
C13—O2—Eu1	92.9 (3)	H11B—C18—H11C	109.5
C13—O1—Eu1	92.1 (3)	O5—C17—O6	125.1 (4)
C17—O5—Eu1	139.2 (3)	O5—C17—C18	117.4 (4)
C1—N1—C5	118.2 (4)	O6—C17—C18	117.5 (4)
C1—N1—Eu1	120.9 (3)

Symmetry code: (i) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ⁱⁱ	0.93	2.57	3.287 (6)	135
C12—H8···O6ⁱ	0.93	2.44	3.078 (6)	126
C16—H10C···O1ⁱⁱⁱ	0.96	2.45	3.390 (6)	165

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x+1, y, z; (iii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	[Eu₂(C₂H₃O₂)₆(C₁₂H₈N₂)₂]
M_r	1018.61
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.7671 (19), 8.9265 (19), 12.992 (3)
α, β, γ (°)	103.631 (2), 109.254 (2), 98.300 (3)
V (Å³)	905.1 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	3.50
Crystal size (mm)	0.20 × 0.19 × 0.18

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.541, 0.571
No. of measured, independent and observed [I > 2σ(I)] reflections	5010, 3474, 3062
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.062, 1.05
No. of reflections	3474
No. of parameters	247
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.80, −0.64

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ⁱ	0.93	2.57	3.287 (6)	134.5
C12—H8···O6ⁱⁱ	0.93	2.44	3.078 (6)	126.3
C16—H10C···O1ⁱⁱⁱ	0.96	2.45	3.390 (6)	164.6

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+2, −z+1; (iii) x, y+1, z.

Acknowledgements

This work was supported financially by Guangdong Provincial Science and Technology Bureau (grant No. 2008B010600009) and the NSFC (grant Nos. 20971047 and U0734005).

References

Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hu, X.-L., Qiu, L., Sun, W.-B. & Chen, Z. (2006). Acta Cryst. E62, m3213–m3214. Web of Science CSD CrossRef IUCr Journals Google Scholar
Panagiotopoulos, A., Zafiropoulos, T. F., Perlepes, S. P., Bakalbassis, E., Masson-Ramade, I., Kahn, O., Terzis, A. & Raptopoulou, C. P. (1995). Inorg. Chem. 34, 4918–4923. CSD CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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