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Acta Cryst. (2008). E64, m201    [ doi:10.1107/S1600536807066263 ]

Tetrakis[[mu]-3-(3-pyridyl)acrylato-[kappa]2O:O']bis{(1,10-phenanthroline-[kappa]2N,N')[3-(3-pyridyl)acrylato-[kappa]2O,O']europium(III)} pentahydrate

C.-B. Liu, H.-L. Wen, F. Deng and J.-H. Zuo

Abstract top

The europiumIII ion in the title compound, [Eu2(C8H6NO2)6(C12H8N2)2]·5H2O, is coordinated by seven carboxylate O atoms and two N atoms from one phenanthroline molecule. The carboxylate groups of 3-(3-pyridyl)acrylate link pairs of europium(III) ions, forming centrosymmetric dinuclear units, which further assemble into a sheet parallel to the (001) plane through hydrogen-bonding interactions involving the uncoordinated water molecules. One water molecule is disordered.

Comment top

Recently, assembly of high-dimensional supramolecular coordination polymers have attracted considerable attention by exploiting coordination bonds, hydrogen bondings, and π-π stacks [Ye et al., 2005], not only because of their intriguing sructural diversity, but also for their potential application as smart opotoelectronic, magnetic, and porous materials. 1,10-phenanthroline has been widely used to construct stable supramolecular structures via C—H···O or C—H···N hydrogen bonds and π-π stackings, and 3-pyridylacrylic acid (HTPA) is a potential multidentate ligand, (Gunning et al., 2005; Liu et al., 2006). Here, we report the synthesis and structure of a europium supramolecular complex with 3-(3-pyridyl)acrylato and 1,10-phenanthroline, [Eu2 (C8H6NO2)6 (C12H8N2)]2.(H2O)5 (I).

Each EuIII centre is coordinated by seven carboxylate oxygen atoms and two nitrogen atoms from one phenanthroline molecule; the carboxylate groups of 3-(3-pyridyl)acrylato adopt bridging bidentate, chelating and bridging-chlelating tridentate modes respectively (Fig. 1). the dihedral angles between them are 59.229 (73), 84.724 (65) and 72.190 (56) ° respectively. The carboxylate groups of 3-(3-pyridyl)acrylato link pairs of europium(III) ions to form dinuclear units, which further build up a sheet parallel to the (0 0 1) plane through hydrogen bondings involving the uncoordinated water molecules (Table 1).

Related literature top

For related literature, see: Gunning & Cahill (2005); Liu et al. (2006); Ye et al. (2005).

Experimental top

A mixture of EuCl3.6H2O (0.1 mmol), 3-pyridylacrylic acid (0.1 mmol), 1,10-phenanthroline (0.1 mmol), H2O (10 ml), and 0.65 M NaOH aqueous solution (0.1 mmol) was sealed in a 25 ml Teflon-lined stainless reactor and heated at 393 K for 72 h under autogenous pressure, then cooled to room temperature, when a few colourless crystals were obtained. Analysis: found C 52.33, H 3.96, N 8.73%; C72H62Eu2N10O17 requires C 52.01, H 3.85, N 8.43%.

Refinement top

All H atoms attached to C atoms were fixed geometrically and treated as riding with C—H = 0.93 Å with Uiso(H) = 1.2Ueq(C). H atoms of water molecule were located in difference Fourier maps and included in the subsequent refinement using restraints (O—H= 0.82 (1)Å and H···H= 1.39 (2) Å) with Uiso(H) = 1.5Ueq(O). In the last stage of refinement they were treated as riding on their parent O atoms.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996)and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. : The molecular structure of complex (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are represented as small spheres of arbitrary radius. [Symmetry code: (i) 1 - x, 1 - y, 1 - z.]
tetrakis[µ-3-(3-pyridyl)acrylato-κ2O:O']bis{(1,10-phenanthroline- κ2N,N')[3-(3-pyridyl)acrylato-κ2O,O']europium(III)] pentahydrate top
Crystal data top
[Eu2(C8H6NO2)6(C12H8N2)2]·5H2OF000 = 3304
Mr = 1643.24Dx = 1.567 Mg m−3
Monoclinic, C2/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 7048 reflections
a = 25.434 (2) Åθ = 2.7–28.1º
b = 12.320 (10) ŵ = 1.86 mm−1
c = 22.595 (19) ÅT = 293 (2) K
β = 100.330 (10)ºBlock, colorless
V = 6965.4 (10) Å30.32 × 0.27 × 0.13 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		6480 independent reflections
Radiation source: fine-focus sealed tube5721 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.022
T = 293(2) Kθmax = 25.5º
φ and ω scansθmin = 2.5º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −30→30
Tmin = 0.585, Tmax = 0.791k = −14→14
25928 measured reflectionsl = −27→27
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)] = 0.019H-atom parameters constrained
wR(F2) = 0.044  w = 1/[σ2(Fo2) + (0.0183P)2 + 8.1685P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.006
6480 reflectionsΔρmax = 0.34 e Å−3
460 parametersΔρmin = −0.25 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Eu2(C8H6NO2)6(C12H8N2)2]·5H2OV = 6965.4 (10) Å3
Mr = 1643.24Z = 4
Monoclinic, C2/cMo Kα
a = 25.434 (2) ŵ = 1.86 mm−1
b = 12.320 (10) ÅT = 293 (2) K
c = 22.595 (19) Å0.32 × 0.27 × 0.13 mm
β = 100.330 (10)º
Data collection top
Bruker SMART CCD area-detector
diffractometer		6480 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		5721 reflections with I > 2σ(I)
Tmin = 0.585, Tmax = 0.791Rint = 0.022
25928 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.019460 parameters
wR(F2) = 0.044H-atom parameters constrained
S = 1.03Δρmax = 0.34 e Å−3
6480 reflectionsΔρmin = −0.25 e Å−3
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*/UeqOcc. (<1)
Eu10.528205 (4)0.611291 (8)0.562535 (4)0.02456 (4)
O50.58593 (7)0.57165 (15)0.66055 (7)0.0457 (4)
O60.62759 (6)0.62061 (13)0.58772 (7)0.0417 (4)
N30.82161 (9)0.3750 (2)0.77152 (12)0.0627 (7)
N40.55055 (7)0.81740 (14)0.56748 (8)0.0312 (4)
N50.48983 (7)0.72683 (15)0.64279 (8)0.0311 (4)
C170.62845 (9)0.58151 (19)0.63974 (11)0.0375 (6)
C180.68033 (10)0.5427 (2)0.67463 (12)0.0442 (6)
H180.71100.55150.65810.053*
C190.68467 (10)0.4966 (2)0.72778 (11)0.0430 (6)
H190.65380.49540.74440.052*
C200.73241 (10)0.4467 (2)0.76421 (11)0.0415 (6)
C210.73315 (12)0.4186 (3)0.82349 (13)0.0589 (8)
H210.70350.43190.84120.071*
C220.77820 (14)0.3705 (3)0.85628 (14)0.0729 (10)
H220.77960.35210.89640.087*
C230.82070 (13)0.3506 (3)0.82849 (15)0.0664 (9)
H230.85080.31790.85090.080*
C240.77778 (10)0.4222 (2)0.74091 (12)0.0500 (7)
H240.77770.44000.70090.060*
C250.58064 (10)0.8617 (2)0.53183 (11)0.0418 (6)
H250.59970.81600.51060.050*
C260.58516 (12)0.9740 (2)0.52446 (12)0.0531 (7)
H260.60671.00170.49880.064*
C270.55780 (12)1.0418 (2)0.55515 (13)0.0562 (7)
H270.55991.11650.55010.067*
C280.52609 (10)0.99896 (19)0.59464 (12)0.0450 (6)
C290.49626 (13)1.0650 (2)0.62910 (15)0.0629 (8)
H290.49731.14010.62550.076*
C300.46693 (12)1.0205 (2)0.66633 (15)0.0611 (8)
H300.44851.06550.68860.073*
C310.46320 (10)0.9054 (2)0.67276 (12)0.0435 (6)
C320.43288 (10)0.8555 (2)0.71132 (12)0.0505 (7)
H320.41340.89780.73380.061*
C330.43197 (10)0.7457 (2)0.71572 (11)0.0472 (6)
H330.41240.71200.74150.057*
C340.46102 (9)0.6843 (2)0.68077 (10)0.0395 (6)
H340.46020.60910.68420.047*
C350.49140 (8)0.83702 (18)0.63913 (10)0.0318 (5)
C360.52348 (9)0.88490 (17)0.59938 (10)0.0331 (5)
O10.44766 (7)0.35404 (12)0.53195 (7)0.0375 (4)
O20.47138 (6)0.48567 (12)0.60014 (7)0.0389 (4)
O30.44546 (6)0.55841 (12)0.47089 (7)0.0367 (4)
O40.44788 (6)0.71259 (12)0.51991 (7)0.0382 (4)
N10.40521 (14)0.2529 (3)0.83252 (12)0.0830 (9)
N20.21675 (9)0.92111 (19)0.44666 (11)0.0541 (6)
C10.44874 (9)0.39752 (17)0.58251 (10)0.0328 (5)
C20.42104 (10)0.33633 (19)0.62482 (10)0.0395 (5)
H20.39760.28140.60900.047*
C30.42757 (10)0.35487 (19)0.68318 (11)0.0390 (6)
H30.44950.41290.69790.047*
C40.40369 (11)0.2931 (2)0.72740 (11)0.0428 (6)
C50.36142 (13)0.2224 (2)0.71075 (14)0.0632 (8)
H50.34660.21180.67040.076*
C60.34154 (17)0.1676 (3)0.75602 (19)0.0866 (12)
H60.31290.11990.74660.104*
C70.36502 (18)0.1855 (3)0.81466 (18)0.0882 (12)
H70.35160.14730.84420.106*
C80.42271 (12)0.3066 (3)0.78849 (12)0.0584 (8)
H80.44980.35710.79970.070*
C90.42372 (9)0.64675 (17)0.48230 (9)0.0295 (5)
C100.36825 (9)0.67176 (18)0.45216 (10)0.0336 (5)
H100.35140.62660.42160.040*
C110.34228 (9)0.75715 (18)0.46803 (10)0.0346 (5)
H110.36070.79980.49890.041*
C120.28771 (9)0.79227 (19)0.44256 (11)0.0392 (6)
C130.25486 (11)0.7384 (3)0.39657 (14)0.0658 (9)
H130.26740.67770.37890.079*
C140.20331 (12)0.7750 (3)0.37698 (17)0.0795 (11)
H140.18070.73900.34640.095*
C150.18612 (11)0.8654 (3)0.40342 (15)0.0651 (9)
H150.15120.88880.39040.078*
C160.26665 (10)0.8837 (2)0.46531 (12)0.0457 (6)
H160.28860.92200.49560.055*
O1W0.69847 (9)0.61683 (17)0.50760 (12)0.0848 (8)
H11W0.67880.61220.53400.127*
H12W0.69860.55650.48950.127*
O2W0.30658 (11)0.1792 (3)0.55009 (14)0.1219 (11)
H21W0.28050.20950.55940.183*
H22W0.29730.14330.51930.183*
O3W0.3341 (3)0.9915 (5)0.6047 (3)0.133 (2)0.50
H32W0.30351.00820.60780.199*0.50
H31W0.35211.04100.59440.199*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Eu10.02668 (6)0.02120 (6)0.02471 (6)−0.00104 (4)0.00168 (4)−0.00081 (4)
O50.0382 (10)0.0595 (11)0.0366 (9)0.0112 (8)−0.0010 (8)0.0015 (8)
O60.0356 (9)0.0442 (10)0.0416 (10)−0.0015 (7)−0.0026 (7)0.0035 (8)
N30.0460 (14)0.0697 (17)0.0676 (17)0.0169 (12)−0.0031 (12)0.0009 (13)
N40.0331 (10)0.0262 (10)0.0332 (10)−0.0044 (8)0.0026 (8)−0.0031 (8)
N50.0327 (10)0.0322 (10)0.0270 (9)−0.0002 (8)0.0018 (8)−0.0025 (8)
C170.0348 (13)0.0324 (13)0.0411 (14)0.0016 (10)−0.0045 (11)−0.0092 (10)
C180.0327 (13)0.0459 (15)0.0499 (15)0.0015 (11)−0.0033 (11)−0.0014 (12)
C190.0366 (13)0.0420 (14)0.0471 (15)0.0007 (11)−0.0016 (11)−0.0039 (12)
C200.0400 (14)0.0367 (13)0.0431 (14)0.0008 (11)−0.0057 (11)−0.0026 (11)
C210.0577 (18)0.068 (2)0.0492 (17)0.0100 (15)0.0041 (14)0.0027 (14)
C220.079 (2)0.084 (2)0.0483 (18)0.0120 (19)−0.0102 (17)0.0169 (16)
C230.0566 (19)0.0612 (19)0.070 (2)0.0155 (15)−0.0192 (16)0.0079 (16)
C240.0455 (15)0.0541 (16)0.0469 (15)0.0046 (13)−0.0013 (12)0.0001 (12)
C250.0464 (15)0.0380 (14)0.0418 (14)−0.0111 (11)0.0102 (11)−0.0053 (11)
C260.0648 (18)0.0425 (15)0.0533 (17)−0.0208 (14)0.0140 (14)0.0019 (13)
C270.0678 (19)0.0272 (14)0.072 (2)−0.0109 (13)0.0082 (16)0.0033 (13)
C280.0483 (15)0.0273 (12)0.0564 (16)−0.0001 (11)0.0012 (12)−0.0037 (11)
C290.070 (2)0.0292 (14)0.090 (2)0.0054 (14)0.0161 (18)−0.0103 (15)
C300.0621 (19)0.0410 (16)0.082 (2)0.0117 (14)0.0170 (17)−0.0203 (15)
C310.0387 (14)0.0424 (15)0.0483 (15)0.0069 (11)0.0048 (11)−0.0116 (11)
C320.0383 (14)0.0632 (18)0.0511 (16)0.0081 (13)0.0110 (12)−0.0178 (14)
C330.0389 (14)0.0665 (19)0.0373 (14)−0.0032 (13)0.0099 (11)−0.0062 (13)
C340.0429 (14)0.0412 (14)0.0346 (13)−0.0038 (11)0.0077 (11)−0.0019 (10)
C350.0298 (11)0.0306 (12)0.0322 (12)0.0016 (9)−0.0025 (9)−0.0049 (10)
C360.0326 (12)0.0288 (12)0.0348 (12)0.0001 (10)−0.0024 (9)−0.0040 (10)
O10.0497 (10)0.0332 (8)0.0308 (8)−0.0102 (7)0.0099 (7)−0.0043 (7)
O20.0511 (10)0.0324 (9)0.0353 (9)−0.0135 (8)0.0136 (8)−0.0048 (7)
O30.0388 (9)0.0252 (8)0.0454 (9)0.0047 (7)0.0059 (7)−0.0021 (7)
O40.0359 (9)0.0310 (8)0.0426 (9)0.0043 (7)−0.0074 (7)−0.0062 (7)
N10.102 (2)0.097 (2)0.0588 (17)0.014 (2)0.0373 (17)0.0253 (17)
N20.0400 (13)0.0515 (14)0.0725 (16)0.0131 (11)0.0148 (12)0.0069 (12)
C10.0365 (12)0.0291 (12)0.0329 (12)−0.0023 (10)0.0064 (10)0.0012 (10)
C20.0475 (14)0.0341 (13)0.0392 (13)−0.0128 (11)0.0136 (11)−0.0034 (11)
C30.0453 (14)0.0330 (13)0.0413 (14)−0.0038 (11)0.0145 (11)0.0005 (10)
C40.0541 (16)0.0347 (13)0.0443 (15)0.0045 (11)0.0215 (12)0.0046 (11)
C50.085 (2)0.0511 (18)0.0599 (19)−0.0153 (16)0.0310 (17)0.0009 (14)
C60.110 (3)0.063 (2)0.099 (3)−0.032 (2)0.053 (3)0.003 (2)
C70.121 (3)0.080 (3)0.079 (3)0.008 (2)0.060 (3)0.028 (2)
C80.0684 (19)0.068 (2)0.0432 (16)0.0044 (15)0.0209 (14)0.0110 (14)
C90.0330 (12)0.0250 (11)0.0299 (11)0.0008 (9)0.0038 (9)0.0039 (9)
C100.0329 (12)0.0299 (12)0.0354 (12)−0.0021 (10)−0.0011 (10)−0.0044 (10)
C110.0327 (12)0.0337 (12)0.0354 (12)−0.0028 (10)0.0009 (10)−0.0018 (10)
C120.0321 (13)0.0388 (13)0.0456 (14)0.0026 (10)0.0045 (11)0.0012 (11)
C130.0437 (16)0.065 (2)0.080 (2)0.0141 (14)−0.0149 (15)−0.0226 (17)
C140.0462 (18)0.082 (2)0.098 (3)0.0138 (17)−0.0224 (17)−0.025 (2)
C150.0340 (15)0.072 (2)0.085 (2)0.0112 (14)−0.0021 (15)0.0104 (18)
C160.0371 (13)0.0432 (14)0.0565 (16)0.0046 (12)0.0078 (12)0.0001 (12)
O1W0.0709 (15)0.0684 (15)0.128 (2)−0.0128 (12)0.0522 (15)−0.0190 (14)
O2W0.093 (2)0.123 (3)0.140 (3)−0.0135 (19)−0.0045 (19)0.010 (2)
O3W0.139 (5)0.103 (5)0.133 (5)−0.017 (4)−0.036 (4)0.009 (4)
Geometric parameters (Å, °) top
Eu1—O3i2.3604 (15)C32—H320.9300
Eu1—O1i2.3638 (15)C33—C341.397 (3)
Eu1—O22.3763 (15)C33—H330.9300
Eu1—O42.4400 (15)C34—H340.9300
Eu1—O52.4765 (16)C35—C361.443 (3)
Eu1—O62.4922 (16)O1—C11.258 (3)
Eu1—N42.6001 (18)O1—Eu1i2.3638 (15)
Eu1—N52.6272 (18)O2—C11.260 (3)
Eu1—O32.7530 (16)O3—C91.268 (3)
Eu1—C172.843 (2)O3—Eu1i2.3604 (15)
Eu1—C92.969 (2)O4—C91.253 (3)
Eu1—Eu1i4.0137 (3)N1—C71.322 (5)
O5—C171.260 (3)N1—C81.336 (4)
O6—C171.267 (3)N2—C151.327 (4)
N3—C231.326 (4)N2—C161.345 (3)
N3—C241.335 (3)C1—C21.490 (3)
N4—C251.324 (3)C2—C31.319 (3)
N4—C361.365 (3)C2—H20.9300
N5—C341.332 (3)C3—C41.471 (3)
N5—C351.361 (3)C3—H30.9300
C17—C181.489 (3)C4—C51.382 (4)
C18—C191.315 (3)C4—C81.388 (4)
C18—H180.9300C5—C61.394 (4)
C19—C201.474 (3)C5—H50.9300
C19—H190.9300C6—C71.370 (5)
C20—C211.380 (4)C6—H60.9300
C20—C241.385 (4)C7—H70.9300
C21—C221.381 (4)C8—H80.9300
C21—H210.9300C9—C101.485 (3)
C22—C231.366 (5)C10—C111.325 (3)
C22—H220.9300C10—H100.9300
C23—H230.9300C11—C121.469 (3)
C24—H240.9300C11—H110.9300
C25—C261.400 (3)C12—C131.381 (4)
C25—H250.9300C12—C161.385 (3)
C26—C271.355 (4)C13—C141.382 (4)
C26—H260.9300C13—H130.9300
C27—C281.408 (4)C14—C151.371 (4)
C27—H270.9300C14—H140.9300
C28—C361.412 (3)C15—H150.9300
C28—C291.434 (4)C16—H160.9300
C29—C301.338 (4)O1W—H11W0.8462
C29—H290.9300O1W—H12W0.8481
C30—C311.431 (4)O2W—H21W0.8204
C30—H300.9300O2W—H22W0.8227
C31—C321.404 (4)O3W—H32W0.8204
C31—C351.413 (3)O3W—H31W0.8198
C32—C331.357 (4)
O3i—Eu1—O1i74.72 (5)N3—C24—H24117.5
O3i—Eu1—O276.31 (5)C20—C24—H24117.5
O1i—Eu1—O2135.54 (5)N4—C25—C26123.3 (2)
O3i—Eu1—O4126.32 (5)N4—C25—H25118.4
O1i—Eu1—O483.44 (6)C26—C25—H25118.4
O2—Eu1—O487.38 (6)C27—C26—C25119.2 (3)
O3i—Eu1—O587.40 (6)C27—C26—H26120.4
O1i—Eu1—O5129.42 (6)C25—C26—H26120.4
O2—Eu1—O581.54 (6)C26—C27—C28119.9 (2)
O4—Eu1—O5140.72 (5)C26—C27—H27120.1
O3i—Eu1—O677.26 (5)C28—C27—H27120.1
O1i—Eu1—O677.34 (6)C27—C28—C36117.5 (2)
O2—Eu1—O6127.26 (6)C27—C28—C29123.4 (2)
O4—Eu1—O6144.08 (5)C36—C28—C29119.1 (3)
O5—Eu1—O652.45 (6)C30—C29—C28121.2 (3)
O3i—Eu1—N4143.74 (6)C30—C29—H29119.4
O1i—Eu1—N476.83 (5)C28—C29—H29119.4
O2—Eu1—N4139.73 (5)C29—C30—C31121.6 (3)
O4—Eu1—N471.25 (5)C29—C30—H30119.2
O5—Eu1—N493.68 (6)C31—C30—H30119.2
O6—Eu1—N474.94 (6)C32—C31—C35117.5 (2)
O3i—Eu1—N5149.61 (6)C32—C31—C30123.4 (2)
O1i—Eu1—N5135.59 (5)C35—C31—C30119.1 (3)
O2—Eu1—N577.35 (5)C33—C32—C31120.0 (2)
O4—Eu1—N566.85 (5)C33—C32—H32120.0
O5—Eu1—N573.95 (6)C31—C32—H32120.0
O6—Eu1—N5107.73 (5)C32—C33—C34118.8 (2)
N4—Eu1—N563.04 (6)C32—C33—H33120.6
O3i—Eu1—O376.84 (5)C34—C33—H33120.6
O1i—Eu1—O369.55 (5)N5—C34—C33124.0 (2)
O2—Eu1—O371.51 (5)N5—C34—H34118.0
O4—Eu1—O349.54 (5)C33—C34—H34118.0
O5—Eu1—O3151.25 (6)N5—C35—C31122.6 (2)
O6—Eu1—O3142.18 (5)N5—C35—C36118.14 (19)
N4—Eu1—O3113.28 (5)C31—C35—C36119.3 (2)
N5—Eu1—O3108.60 (5)N4—C36—C28122.1 (2)
O3i—Eu1—C1778.89 (6)N4—C36—C35118.33 (19)
O1i—Eu1—C17103.18 (7)C28—C36—C35119.6 (2)
O2—Eu1—C17103.45 (7)C1—O1—Eu1i140.95 (14)
O4—Eu1—C17154.62 (6)C1—O2—Eu1136.14 (14)
O5—Eu1—C1726.26 (6)C9—O3—Eu1i169.88 (14)
O6—Eu1—C1726.44 (6)C9—O3—Eu186.92 (12)
N4—Eu1—C1786.25 (6)Eu1i—O3—Eu1103.16 (5)
N5—Eu1—C1792.85 (6)C9—O4—Eu1102.16 (13)
O3—Eu1—C17155.71 (6)C7—N1—C8115.2 (3)
O3i—Eu1—C9102.08 (6)C15—N2—C16116.7 (2)
O1i—Eu1—C976.75 (6)O1—C1—O2126.1 (2)
O2—Eu1—C977.23 (6)O1—C1—C2115.56 (19)
O4—Eu1—C924.37 (5)O2—C1—C2118.4 (2)
O5—Eu1—C9153.82 (6)C3—C2—C1124.4 (2)
O6—Eu1—C9153.25 (6)C3—C2—H2117.8
N4—Eu1—C992.72 (6)C1—C2—H2117.8
N5—Eu1—C986.51 (6)C2—C3—C4126.6 (2)
O3—Eu1—C925.25 (5)C2—C3—H3116.7
C17—Eu1—C9178.95 (6)C4—C3—H3116.7
O3i—Eu1—Eu1i41.90 (4)C5—C4—C8117.5 (2)
O1i—Eu1—Eu1i66.76 (4)C5—C4—C3122.5 (2)
O2—Eu1—Eu1i69.10 (4)C8—C4—C3120.0 (2)
O4—Eu1—Eu1i84.45 (4)C4—C5—C6118.2 (3)
O5—Eu1—Eu1i125.08 (4)C4—C5—H5120.9
O6—Eu1—Eu1i114.34 (4)C6—C5—H5120.9
N4—Eu1—Eu1i138.18 (4)C7—C6—C5118.6 (3)
N5—Eu1—Eu1i136.55 (4)C7—C6—H6120.7
O3—Eu1—Eu1i34.93 (3)C5—C6—H6120.7
C17—Eu1—Eu1i120.79 (5)N1—C7—C6125.1 (3)
C9—Eu1—Eu1i60.18 (4)N1—C7—H7117.4
C17—O5—Eu193.33 (14)C6—C7—H7117.4
C17—O6—Eu192.42 (14)N1—C8—C4125.3 (3)
C23—N3—C24116.3 (3)N1—C8—H8117.4
C25—N4—C36118.12 (19)C4—C8—H8117.4
C25—N4—Eu1121.48 (15)O4—C9—O3120.99 (19)
C36—N4—Eu1119.38 (14)O4—C9—C10119.13 (19)
C34—N5—C35117.2 (2)O3—C9—C10119.86 (19)
C34—N5—Eu1123.15 (15)O4—C9—Eu153.47 (10)
C35—N5—Eu1118.67 (14)O3—C9—Eu167.83 (11)
O5—C17—O6120.7 (2)C10—C9—Eu1169.61 (15)
O5—C17—C18120.6 (2)C11—C10—C9121.3 (2)
O6—C17—C18118.6 (2)C11—C10—H10119.4
O5—C17—Eu160.41 (12)C9—C10—H10119.4
O6—C17—Eu161.14 (12)C10—C11—C12127.6 (2)
C18—C17—Eu1168.00 (16)C10—C11—H11116.2
C19—C18—C17122.9 (2)C12—C11—H11116.2
C19—C18—H18118.5C13—C12—C16116.6 (2)
C17—C18—H18118.5C13—C12—C11123.7 (2)
C18—C19—C20128.0 (3)C16—C12—C11119.7 (2)
C18—C19—H19116.0C12—C13—C14119.7 (3)
C20—C19—H19116.0C12—C13—H13120.2
C21—C20—C24116.6 (2)C14—C13—H13120.2
C21—C20—C19120.9 (2)C15—C14—C13119.0 (3)
C24—C20—C19122.5 (2)C15—C14—H14120.5
C20—C21—C22119.6 (3)C13—C14—H14120.5
C20—C21—H21120.2N2—C15—C14123.4 (3)
C22—C21—H21120.2N2—C15—H15118.3
C23—C22—C21118.6 (3)C14—C15—H15118.3
C23—C22—H22120.7N2—C16—C12124.6 (3)
C21—C22—H22120.7N2—C16—H16117.7
N3—C23—C22123.9 (3)C12—C16—H16117.7
N3—C23—H23118.0H11W—O1W—H12W109.4
C22—C23—H23118.0H21W—O2W—H22W109.8
N3—C24—C20125.0 (3)H32W—O3W—H31W115.1
Symmetry codes: (i) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H11W···O60.851.942.775 (3)171
O1W—H12W···N2ii0.852.022.856 (3)167
O2W—H21W···O1Wiii0.822.482.851 (4)109
O3W—H31W···O2Wiv0.822.202.655 (7)116
Symmetry codes: (ii) x+1/2, y−1/2, z; (iii) x−1/2, y−1/2, z; (iv) x, y+1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H11W···O60.851.942.775 (3)171
O1W—H12W···N2i0.852.022.856 (3)167
O2W—H21W···O1Wii0.822.482.851 (4)109
O3W—H31W···O2Wiii0.822.202.655 (7)116
Symmetry codes: (i) x+1/2, y−1/2, z; (ii) x−1/2, y−1/2, z; (iii) x, y+1, z.
Acknowledgements top

This work is supported by the National Natural Science Foundation of China (20662007).

references
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