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In the crystal structure of the title compound, [Eu2(C8H8NO2)6(C12H8N2)2]n, the EuIII atoms are bridged by two tridentate, two bidentate and four mondentate carboxylate groups with an inversion centre between the two EuIII ions of this dinuclear structural unit. Each Eu atom is nine-coordinated by two 1,10-phenanthroline N atoms and seven O atoms of four anilinoacetate ligands. In the crystal structure, the chains are linked by C—H...N and C—H...O hydrogen bonds into a polymeric ribbon structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807060643/at2497sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807060643/at2497Isup2.hkl
Contains datablock I

CCDC reference: 1303498

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.012 Å
  • R factor = 0.047
  • wR factor = 0.127
  • Data-to-parameter ratio = 18.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for N5 - C23 .. 8.31 su PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for N5
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.99 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.03 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - C21 .. 6.17 su PLAT230_ALERT_2_C Hirshfeld Test Diff for N5 - C22 .. 6.00 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Eu1 - O2 .. 6.55 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C6 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C23 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C33 PLAT335_ALERT_2_C Large Benzene C-C Range ....... C4 -C6 0.23 Ang. PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 12 PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C4 - C6 ... 1.54 Ang. PLAT420_ALERT_2_C D-H Without Acceptor N3 - H3A ... ? PLAT420_ALERT_2_C D-H Without Acceptor N4 - H4A ... ? PLAT420_ALERT_2_C D-H Without Acceptor N5 - H5A ... ? PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 78.00 A   3
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 5
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 19 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 15 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The crystal structure of [RE2(C8H8NO2)6(C12H8N2)2]n (RE = Sm, Nd and La), (II), have previously been reported (Zhong et al., 2007a,b,c). The crystal structure determination of the title compound, (I), has been carried out in order to elucidate the molecular conformation and to compare it with that of (II). We report herein the crystal structure of (I).

In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). The title compound, [Eu2(C8H8NO2)6(C12H8N2)2]n, which are bridged by two terdentate, two bidentate and four mondentate carboxyl groups with an inversion centre between the two EuIII ions. Each Eu atom is nine-coordinated by two N atoms of 1,10-phenanthroline (phen) ligand and seven O atoms of four anilinoacetate ligands (Table 1). The Eu—O and Eu bonds are in the range of [2.435 (3)–2.916 (4) Å] and [2.700 (4) to 2.776 (4) Å], respectively, as in (II).

In the crystal structure, C—H···N and C—H···O hydrogen bonds (Fig. 2 and Table 2) seem to be effective in the stabilization of the structure, resulting in the formation of a supramolecular network structure, as in (II).

The four compounds, (I) and (II), are isostructural.

Related literature top

For a related structure, see: Zhong et al. (2007a,b,c). For bond-length data, see: Allen et al. (1987).

Experimental top

Crystals of the title compound were synthesized using hydrothermal method in a 23 ml Teflon-lined Parr bomb, which was then sealed. Europium (III) nitrate hexahydrate (206.7 mg, 0.5 mmol), phen (198 mg, 1 mmol), anilinoacetic acid (292.4 mg, 2 mmol), ammonia (0.5 mol/l, 4 ml) and distilled water (8 g) were placed into the bomb and sealed. The bomb was then heated under autogenous pressure up to 453 K over the course of 7 d and allowed to cool at room temperature for 24 h. Upon opening the bomb, a clear colorless solution was decanted from small colorless crystals. These crystals were washed with distilled water followed by ethanol, and allowed to air-dry at room temperature.

Refinement top

H3A and H4A (for NH) were located in difference syntheses and refined isotropically [N—H = 0.78 (3) and 0.83 (6) Å, Uiso(H) = 0.07 (1) and 0.08 (2) Å2]. The H atoms were positioned geometrically, with N—H = 0.86 Å (for NH) and C—H = 0.93 - 0.97 Å (for CH), and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,N), where x = 1.2 for aromatic and NH H atoms and x = 1.5 for methyl H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL (Siemens, 1996).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level [symmetry code (A): 2 - x, -y, 2 - z]. All H atoms have been omitted for clarity.
[Figure 2] Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines.
catena-Poly[[tetra-µ-anilinoacetato-bis(1,10- phenanthroline)dieuropium(III)]-di-µ-anilinoacetato] top
Crystal data top
[Eu2(C8H8NO2)6(C12H8N2)2]F(000) = 1576
Mr = 1565.26Dx = 1.464 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9044 reflections
a = 19.783 (2) Åθ = 2.7–26.1°
b = 8.8013 (14) ŵ = 1.82 mm1
c = 21.2014 (12) ÅT = 273 K
β = 105.816 (5)°Plane, colourless
V = 3551.8 (7) Å30.34 × 0.12 × 0.09 mm
Z = 2
Data collection top
Bruker APEXII area-detector
diffractometer
7520 independent reflections
Radiation source: fine-focus sealed tube4961 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
ϕ and ω scansθmax = 27.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2524
Tmin = 0.581, Tmax = 0.859k = 1011
27025 measured reflectionsl = 2626
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0708P)2 + 1.1179P]
where P = (Fo2 + 2Fc2)/3
7520 reflections(Δ/σ)max = 0.002
411 parametersΔρmax = 1.49 e Å3
5 restraintsΔρmin = 0.85 e Å3
Crystal data top
[Eu2(C8H8NO2)6(C12H8N2)2]V = 3551.8 (7) Å3
Mr = 1565.26Z = 2
Monoclinic, P21/nMo Kα radiation
a = 19.783 (2) ŵ = 1.82 mm1
b = 8.8013 (14) ÅT = 273 K
c = 21.2014 (12) Å0.34 × 0.12 × 0.09 mm
β = 105.816 (5)°
Data collection top
Bruker APEXII area-detector
diffractometer
7520 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4961 reflections with I > 2σ(I)
Tmin = 0.581, Tmax = 0.859Rint = 0.043
27025 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0475 restraints
wR(F2) = 0.127H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 1.49 e Å3
7520 reflectionsΔρmin = 0.85 e Å3
411 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
Eu10.931209 (13)0.19067 (3)0.964289 (11)0.04106 (11)
O10.84657 (16)0.0352 (4)0.91894 (16)0.0422 (8)
O20.94691 (17)0.1382 (4)0.97736 (16)0.0476 (8)
O30.97044 (17)0.0609 (4)0.87446 (15)0.0452 (8)
O40.93985 (18)0.4212 (4)1.03389 (15)0.0448 (8)
O51.06684 (18)0.0828 (4)0.92183 (16)0.0473 (8)
O61.0076 (2)0.6122 (4)1.09116 (16)0.0539 (9)
N10.7970 (2)0.2338 (5)0.9672 (2)0.0455 (10)
N20.8341 (2)0.3067 (4)0.8547 (2)0.0468 (10)
N31.1191 (2)0.0134 (6)0.8228 (2)0.0469 (11)
N50.7853 (2)0.3271 (4)0.8984 (2)0.0450 (10)
H5A0.76280.34170.85800.054*
N40.9877 (2)0.5262 (5)1.20640 (19)0.0436 (10)
C10.7784 (3)0.1908 (7)1.0196 (3)0.0620 (16)
H10.81330.16711.05760.074*
C20.7090 (3)0.1799 (9)1.0198 (4)0.083 (2)
H20.69640.15301.05750.100*
C30.6584 (4)0.2107 (9)0.9612 (5)0.092 (3)
H30.61130.19820.95990.110*
C40.6742 (3)0.2585 (9)0.9055 (4)0.077 (2)
C50.7465 (3)0.2678 (6)0.9087 (3)0.0507 (13)
C60.6224 (4)0.2954 (11)0.8388 (5)0.109 (3)
H60.57460.28290.83430.131*
C70.6419 (4)0.3435 (10)0.7880 (4)0.100 (3)
H70.60810.37100.74980.120*
C80.7132 (3)0.3537 (8)0.7907 (3)0.0671 (18)
C90.7661 (3)0.3098 (6)0.8509 (3)0.0499 (13)
C100.7359 (5)0.4045 (8)0.7374 (3)0.087 (2)
H100.70360.44000.69980.104*
C110.8044 (5)0.4017 (8)0.7407 (3)0.080 (2)
H110.82030.43210.70530.096*
C120.8528 (3)0.3502 (7)0.8007 (3)0.0610 (15)
H120.90020.34680.80240.073*
C131.0285 (3)0.0026 (6)0.8770 (2)0.0409 (11)
C141.0524 (3)0.0510 (7)0.8173 (3)0.0512 (13)
H14A1.01910.01600.77750.061*
H14B1.05520.16090.81560.061*
C151.1463 (3)0.0138 (7)0.7702 (3)0.0610 (15)
C161.2071 (3)0.0572 (9)0.7757 (3)0.0765 (19)
H161.22690.11890.81160.092*
C171.2400 (4)0.0367 (10)0.7266 (5)0.093 (2)
H171.28300.08330.73010.111*
C181.2100 (5)0.0521 (10)0.6723 (5)0.106 (3)
H181.23300.06240.63970.128*
C191.1477 (5)0.1245 (11)0.6655 (4)0.109 (3)
H191.12780.18410.62890.131*
C201.1147 (4)0.1063 (9)0.7152 (4)0.083 (2)
H201.07220.15460.71240.100*
C210.8840 (3)0.1515 (6)0.9389 (2)0.0431 (12)
C220.8583 (3)0.3150 (6)0.9197 (3)0.0545 (14)
H22A0.87800.35010.88520.065*
H22B0.87560.38090.95730.065*
C230.7535 (7)0.3143 (10)0.9462 (7)0.1243 (16)
C240.7846 (6)0.2767 (10)1.0124 (7)0.1243 (16)
H240.83260.25841.02770.149*
C250.7421 (6)0.2681 (11)1.0536 (7)0.1243 (16)
H250.76020.24511.09780.149*
C260.6719 (6)0.2946 (10)1.0268 (7)0.1243 (16)
H260.64310.28431.05470.149*
C270.6385 (6)0.3358 (10)0.9615 (6)0.1243 (16)
H270.59080.35790.94760.149*
C280.6802 (6)0.3414 (10)0.9198 (6)0.1243 (16)
H280.66130.36230.87550.149*
C290.9697 (3)0.4996 (6)1.0863 (2)0.0417 (11)
C300.9484 (3)0.4461 (7)1.1474 (2)0.0542 (14)
H30A0.89860.46341.14080.065*
H30B0.95700.33781.15330.065*
C310.9743 (3)0.4892 (6)1.2657 (2)0.0521 (13)
C320.9280 (3)0.3784 (9)1.2720 (3)0.0706 (18)
H320.90270.32361.23570.085*
C330.9196 (5)0.3497 (12)1.3341 (4)0.109 (3)
H330.88930.27301.33930.130*
C340.9573 (5)0.4368 (12)1.3906 (3)0.102 (3)
H340.94970.41961.43140.122*
C351.0033 (4)0.5429 (9)1.3832 (3)0.086 (2)
H351.02840.59841.41930.103*
C361.0139 (3)0.5704 (8)1.3220 (3)0.0705 (17)
H361.04700.64201.31770.085*
H4A0.959 (3)0.596 (6)1.204 (3)0.08 (2)*
H3A1.1044 (17)0.091 (3)0.8091 (16)0.07 (1)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Eu10.04517 (16)0.03736 (17)0.03679 (15)0.00155 (12)0.00464 (10)0.00065 (11)
O10.0382 (17)0.0343 (19)0.0479 (19)0.0005 (15)0.0008 (14)0.0027 (15)
O20.0393 (18)0.051 (2)0.045 (2)0.0022 (16)0.0000 (15)0.0083 (16)
O30.050 (2)0.049 (2)0.0379 (18)0.0054 (17)0.0138 (15)0.0020 (16)
O40.061 (2)0.0342 (19)0.0396 (18)0.0046 (16)0.0139 (15)0.0048 (15)
O50.055 (2)0.049 (2)0.0406 (19)0.0089 (17)0.0176 (16)0.0107 (16)
O60.074 (2)0.050 (2)0.039 (2)0.025 (2)0.0186 (17)0.0034 (16)
N10.042 (2)0.040 (2)0.049 (3)0.0031 (19)0.0033 (19)0.0093 (19)
N20.057 (3)0.039 (2)0.036 (2)0.003 (2)0.0015 (18)0.0002 (18)
N30.047 (2)0.054 (3)0.045 (3)0.006 (2)0.022 (2)0.010 (2)
N50.037 (2)0.032 (2)0.056 (3)0.0128 (17)0.0045 (18)0.0075 (18)
N40.061 (3)0.043 (3)0.028 (2)0.021 (2)0.0151 (19)0.0060 (18)
C10.051 (3)0.077 (5)0.058 (4)0.008 (3)0.015 (3)0.002 (3)
C20.051 (4)0.116 (7)0.087 (5)0.005 (4)0.027 (4)0.010 (4)
C30.043 (4)0.109 (7)0.122 (7)0.006 (4)0.020 (4)0.014 (5)
C40.046 (3)0.085 (5)0.083 (5)0.008 (3)0.009 (3)0.021 (4)
C50.048 (3)0.035 (3)0.062 (4)0.007 (2)0.002 (3)0.011 (2)
C60.049 (4)0.146 (9)0.107 (7)0.017 (5)0.021 (4)0.027 (6)
C70.075 (5)0.115 (7)0.078 (5)0.039 (5)0.031 (4)0.015 (5)
C80.067 (4)0.068 (4)0.046 (4)0.018 (3)0.018 (3)0.010 (3)
C90.054 (3)0.033 (3)0.050 (3)0.006 (2)0.009 (2)0.003 (2)
C100.113 (6)0.070 (5)0.050 (4)0.018 (4)0.024 (4)0.001 (3)
C110.116 (6)0.074 (5)0.038 (3)0.002 (4)0.002 (3)0.009 (3)
C120.075 (4)0.055 (4)0.046 (3)0.002 (3)0.004 (3)0.010 (3)
C130.050 (3)0.034 (3)0.038 (3)0.008 (2)0.011 (2)0.004 (2)
C140.060 (3)0.051 (3)0.045 (3)0.007 (3)0.018 (2)0.011 (2)
C150.064 (4)0.069 (4)0.057 (4)0.009 (3)0.029 (3)0.000 (3)
C160.072 (4)0.094 (5)0.074 (4)0.005 (4)0.037 (4)0.001 (4)
C170.082 (5)0.097 (6)0.117 (6)0.008 (5)0.057 (5)0.010 (5)
C180.138 (8)0.085 (6)0.133 (8)0.018 (6)0.101 (7)0.001 (6)
C190.148 (8)0.115 (7)0.092 (6)0.021 (6)0.078 (6)0.035 (5)
C200.096 (5)0.089 (5)0.082 (5)0.004 (4)0.056 (4)0.023 (4)
C210.043 (3)0.052 (3)0.031 (2)0.007 (2)0.004 (2)0.005 (2)
C220.057 (3)0.043 (3)0.059 (3)0.003 (3)0.007 (3)0.008 (3)
C230.132 (4)0.090 (3)0.174 (5)0.015 (3)0.082 (4)0.031 (3)
C240.132 (4)0.090 (3)0.174 (5)0.015 (3)0.082 (4)0.031 (3)
C250.132 (4)0.090 (3)0.174 (5)0.015 (3)0.082 (4)0.031 (3)
C260.132 (4)0.090 (3)0.174 (5)0.015 (3)0.082 (4)0.031 (3)
C270.132 (4)0.090 (3)0.174 (5)0.015 (3)0.082 (4)0.031 (3)
C280.132 (4)0.090 (3)0.174 (5)0.015 (3)0.082 (4)0.031 (3)
C290.055 (3)0.032 (3)0.039 (3)0.001 (2)0.013 (2)0.004 (2)
C300.070 (3)0.054 (3)0.040 (3)0.021 (3)0.017 (2)0.007 (2)
C310.068 (3)0.054 (3)0.034 (3)0.002 (3)0.014 (2)0.004 (2)
C320.071 (4)0.094 (5)0.049 (3)0.031 (4)0.020 (3)0.002 (3)
C330.122 (7)0.142 (8)0.078 (5)0.050 (6)0.053 (5)0.001 (5)
C340.114 (6)0.151 (8)0.047 (4)0.030 (6)0.035 (4)0.003 (5)
C350.106 (5)0.106 (6)0.041 (3)0.021 (5)0.013 (3)0.010 (4)
C360.082 (4)0.075 (5)0.051 (3)0.019 (4)0.013 (3)0.010 (3)
Geometric parameters (Å, º) top
Eu1—O12.608 (3)C10—C111.337 (10)
Eu1—O2i2.435 (3)C10—H100.9300
Eu1—O22.916 (4)C11—C121.441 (8)
Eu1—O32.518 (3)C11—H110.9300
Eu1—O42.487 (3)C12—H120.9300
Eu1—O5i2.585 (3)C13—C141.528 (7)
Eu1—O6ii2.576 (3)C14—H14A0.9700
Eu1—N12.700 (4)C14—H14B0.9700
Eu1—N22.776 (4)C15—C161.332 (9)
Eu1—Eu1i4.3265 (7)C15—C201.420 (9)
O1—C211.267 (6)C16—C171.382 (10)
O2—C211.293 (6)C16—H160.9300
O2—Eu1i2.435 (3)C17—C181.384 (12)
O3—C131.245 (6)C17—H170.9300
O4—C291.304 (6)C18—C191.361 (12)
O5—C131.284 (6)C18—H180.9300
O5—Eu1i2.585 (3)C19—C201.391 (9)
O6—C291.230 (6)C19—H190.9300
O6—Eu1ii2.576 (3)C20—H200.9300
N1—C11.317 (7)C21—C221.544 (7)
N1—C51.395 (7)C22—H22A0.9700
N2—C91.325 (7)C22—H22B0.9700
N2—C121.350 (7)C23—C241.410 (17)
N3—C151.386 (7)C23—C281.426 (16)
N3—C141.411 (6)C24—C251.368 (14)
N3—H3A0.78 (3)C24—H240.9300
N5—C231.337 (12)C25—C261.371 (16)
N5—C221.393 (7)C25—H250.9300
N5—H5A0.8600C26—C271.410 (16)
N4—C311.392 (6)C26—H260.9300
N4—C301.461 (6)C27—C281.364 (13)
N4—H4A0.83 (6)C27—H270.9300
C1—C21.379 (9)C28—H280.9300
C1—H10.9300C29—C301.541 (7)
C2—C31.393 (12)C30—H30A0.9700
C2—H20.9300C30—H30B0.9700
C3—C41.369 (12)C31—C321.369 (8)
C3—H30.9300C31—C361.428 (8)
C4—C51.414 (9)C32—C331.394 (9)
C4—C61.538 (11)C32—H320.9300
C5—C91.431 (8)C33—C341.445 (11)
C6—C71.309 (13)C33—H330.9300
C6—H60.9300C34—C351.344 (10)
C7—C81.398 (11)C34—H340.9300
C7—H70.9300C35—C361.390 (9)
C8—C101.399 (10)C35—H350.9300
C8—C91.466 (7)C36—H360.9300
O1—Eu1—O247.12 (9)C5—C9—C8121.2 (5)
O1—Eu1—O371.02 (11)C11—C10—C8119.7 (6)
O1—Eu1—O4140.70 (11)C11—C10—H10120.1
O2—Eu1—O364.84 (10)C8—C10—H10120.1
O2—Eu1—O4139.91 (10)C10—C11—C12118.2 (7)
O3—Eu1—O4146.44 (11)C10—C11—H11120.9
O1—Eu1—N165.09 (12)C12—C11—H11120.9
O1—Eu1—N275.12 (11)N2—C12—C11124.6 (6)
O2—Eu1—N1102.55 (12)N2—C12—H12117.7
O2—Eu1—N2118.44 (11)C11—C12—H12117.7
O3—Eu1—N1126.06 (12)O3—C13—O5128.7 (4)
O3—Eu1—N279.59 (12)O3—C13—C14109.8 (4)
O4—Eu1—N177.35 (12)O5—C13—C14121.4 (4)
O4—Eu1—N296.70 (11)N3—C14—C13108.3 (4)
N1—Eu1—N260.42 (14)N3—C14—H14A110.0
O2i—Eu1—O487.41 (12)C13—C14—H14A110.0
O2i—Eu1—O380.31 (11)N3—C14—H14B110.0
O2i—Eu1—O6ii80.57 (12)C13—C14—H14B110.0
O4—Eu1—O6ii75.90 (11)H14A—C14—H14B108.4
O3—Eu1—O6ii71.35 (11)C16—C15—N3112.8 (6)
O2i—Eu1—O5i72.25 (11)C16—C15—C20121.8 (6)
O4—Eu1—O5i76.37 (11)N3—C15—C20125.4 (6)
O3—Eu1—O5i127.64 (11)C15—C16—C17118.1 (7)
O6ii—Eu1—O5i141.68 (11)C15—C16—H16120.9
O2i—Eu1—O1119.34 (12)C17—C16—H16120.9
O6ii—Eu1—O1132.82 (11)C16—C17—C18121.2 (7)
O5i—Eu1—O184.78 (11)C16—C17—H17119.4
O2i—Eu1—N1149.20 (12)C18—C17—H17119.4
O6ii—Eu1—N1120.21 (14)C19—C18—C17121.5 (7)
O5i—Eu1—N178.16 (12)C19—C18—H18119.2
O2i—Eu1—N2149.19 (13)C17—C18—H18119.2
O6ii—Eu1—N270.99 (13)C18—C19—C20117.6 (8)
O5i—Eu1—N2138.42 (12)C18—C19—H19121.2
O2i—Eu1—O272.45 (13)C20—C19—H19121.2
O6ii—Eu1—O2131.37 (11)C19—C20—C15119.7 (7)
O5i—Eu1—O264.69 (10)C19—C20—H20120.1
O2i—Eu1—Eu1i39.99 (9)C15—C20—H20120.1
O4—Eu1—Eu1i119.35 (8)O1—C21—O2120.8 (5)
O3—Eu1—Eu1i67.59 (8)O1—C21—C22122.9 (4)
O6ii—Eu1—Eu1i110.69 (9)O2—C21—C22116.3 (5)
O5i—Eu1—Eu1i62.63 (7)N5—C22—C21113.3 (4)
O1—Eu1—Eu1i79.46 (7)N5—C22—H22A108.9
N1—Eu1—Eu1i129.05 (10)C21—C22—H22A108.9
N2—Eu1—Eu1i143.56 (8)N5—C22—H22B108.9
O2—Eu1—Eu1i32.46 (6)C21—C22—H22B108.9
C21—O1—Eu1103.5 (3)H22A—C22—H22B107.7
C21—O2—Eu1i162.2 (4)N5—C23—C24127.4 (11)
C21—O2—Eu188.3 (3)N5—C23—C28109.1 (12)
Eu1i—O2—Eu1107.55 (13)C24—C23—C28123.5 (11)
C13—O3—Eu1128.7 (3)C25—C24—C23118.1 (12)
C29—O4—Eu1151.5 (3)C25—C24—H24121.0
C13—O5—Eu1i139.5 (3)C23—C24—H24121.0
C29—O6—Eu1ii148.9 (3)C24—C25—C26117.2 (13)
C1—N1—C5120.9 (5)C24—C25—H25121.4
C1—N1—Eu1118.7 (4)C26—C25—H25121.4
C5—N1—Eu1118.7 (3)C25—C26—C27126.9 (11)
C9—N2—C12116.9 (5)C25—C26—H26116.5
C9—N2—Eu1121.1 (3)C27—C26—H26116.5
C12—N2—Eu1121.8 (4)C28—C27—C26116.2 (12)
C15—N3—C14115.1 (4)C28—C27—H27121.9
C15—N3—H3A92 (3)C26—C27—H27121.9
C14—N3—H3A95 (3)C27—C28—C23118.0 (13)
C23—N5—C22114.0 (7)C27—C28—H28121.0
C23—N5—H5A123.0C23—C28—H28121.0
C22—N5—H5A123.0O6—C29—O4128.5 (4)
C31—N4—C30118.2 (4)O6—C29—C30118.4 (4)
C31—N4—H4A86 (5)O4—C29—C30113.0 (4)
C30—N4—H4A96 (5)N4—C30—C29111.7 (4)
N1—C1—C2122.0 (6)N4—C30—H30A109.3
N1—C1—H1119.0C29—C30—H30A109.3
C2—C1—H1119.0N4—C30—H30B109.3
C1—C2—C3117.2 (7)C29—C30—H30B109.3
C1—C2—H2121.4H30A—C30—H30B107.9
C3—C2—H2121.4C32—C31—N4123.5 (5)
C4—C3—C2123.5 (6)C32—C31—C36120.3 (5)
C4—C3—H3118.3N4—C31—C36116.2 (5)
C2—C3—H3118.3C32—C31—H4A122 (3)
C3—C4—C5116.2 (6)C36—C31—H4A109 (2)
C3—C4—C6127.3 (7)C31—C32—C33118.4 (6)
C5—C4—C6116.4 (8)C31—C32—H32120.8
N1—C5—C4120.0 (6)C33—C32—H32120.8
N1—C5—C9121.3 (5)C32—C33—C34121.3 (7)
C4—C5—C9118.6 (6)C32—C33—H33119.4
C7—C6—C4123.5 (8)C34—C33—H33119.4
C7—C6—H6118.2C35—C34—C33119.0 (6)
C4—C6—H6118.2C35—C34—H34120.5
C6—C7—C8120.5 (7)C33—C34—H34120.5
C6—C7—H7119.8C34—C35—C36120.6 (7)
C8—C7—H7119.8C34—C35—H35119.7
C7—C8—C10122.0 (7)C36—C35—H35119.7
C7—C8—C9119.5 (7)C35—C36—C31120.3 (6)
C10—C8—C9118.5 (6)C35—C36—H36119.8
N2—C9—C5116.8 (4)C31—C36—H36119.8
N2—C9—C8122.0 (6)
Symmetry codes: (i) x+2, y, z+2; (ii) x+2, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C22—H22B···O4iii0.972.483.424 (7)164
C12—H12···N4ii0.932.533.380 (8)151
C12—H12···O6ii0.932.513.089 (7)121
C10—H10···O1iv0.932.453.314 (7)154
C1—H1···O5i0.932.413.121 (7)134
Symmetry codes: (i) x+2, y, z+2; (ii) x+2, y+1, z+2; (iii) x, y1, z; (iv) x+3/2, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formula[Eu2(C8H8NO2)6(C12H8N2)2]
Mr1565.26
Crystal system, space groupMonoclinic, P21/n
Temperature (K)273
a, b, c (Å)19.783 (2), 8.8013 (14), 21.2014 (12)
β (°) 105.816 (5)
V3)3551.8 (7)
Z2
Radiation typeMo Kα
µ (mm1)1.82
Crystal size (mm)0.34 × 0.12 × 0.09
Data collection
DiffractometerBruker APEXII area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.581, 0.859
No. of measured, independent and
observed [I > 2σ(I)] reflections
27025, 7520, 4961
Rint0.043
(sin θ/λ)max1)0.638
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.127, 1.02
No. of reflections7520
No. of parameters411
No. of restraints5
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)1.49, 0.85

Computer programs: APEX2 (Bruker, 2005), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996).

Selected geometric parameters (Å, º) top
Eu1—O12.608 (3)Eu1—O5i2.585 (3)
Eu1—O2i2.435 (3)Eu1—O6ii2.576 (3)
Eu1—O22.916 (4)Eu1—N12.700 (4)
Eu1—O32.518 (3)Eu1—N22.776 (4)
Eu1—O42.487 (3)
O1—Eu1—O247.12 (9)O2—Eu1—N1102.55 (12)
O1—Eu1—O371.02 (11)O2—Eu1—N2118.44 (11)
O1—Eu1—O4140.70 (11)O3—Eu1—N1126.06 (12)
O2—Eu1—O364.84 (10)O3—Eu1—N279.59 (12)
O2—Eu1—O4139.91 (10)O4—Eu1—N177.35 (12)
O3—Eu1—O4146.44 (11)O4—Eu1—N296.70 (11)
O1—Eu1—N165.09 (12)N1—Eu1—N260.42 (14)
O1—Eu1—N275.12 (11)
Symmetry codes: (i) x+2, y, z+2; (ii) x+2, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C22—H22B···O4iii0.972.483.424 (7)164
C12—H12···N4ii0.932.533.380 (8)151
C12—H12···O6ii0.932.513.089 (7)121
C10—H10···O1iv0.932.453.314 (7)154
C1—H1···O5i0.932.413.121 (7)134
Symmetry codes: (i) x+2, y, z+2; (ii) x+2, y+1, z+2; (iii) x, y1, z; (iv) x+3/2, y+1/2, z+3/2.
 

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