Tetrakis[μ-3-(3-pyridyl)acrylato-κ2O:O′]bis{(1,10-phenanthroline-κ2N,N′)[3-(3-pyridyl)acrylato-κ2O,O′]europium(III)} pentahydrate

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

doi:10.1107/S1600536807066263

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page m201

https://doi.org/10.1107/S1600536807066263

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Tetrakis[μ-3-(3-pyridyl)acrylato-κ²O:O′]bis{(1,10-phenanthroline-κ²N,N′)[3-(3-pyridyl)acrylato-κ²O,O′]europium(III)} pentahydrate

Chong-Bo Liu,^a Hui-Liang Wen,^b ^* Fang Deng ^a and Jun-Hui Zuo ^b

^aCollege of Environmental and Chemical Engineering, Nanchang University of Aeronautics, Nanchang 330063, People's Republic of China, and ^bState Key Laboratory of Food Science and Technology, Nanchang University, Nanchang 330047, People's Republic of China
^*Correspondence e-mail: hlwen70@163.com

(Received 8 November 2007; accepted 9 December 2007; online 18 December 2007)

The europium^III 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.

Related literature

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

Experimental

Crystal data

[Eu₂(C₈H₆NO₂)₆(C₁₂H₈N₂)₂]·5H₂O
M_r = 1643.24
Monoclinic, C 2/c
a = 25.434 (2) Å
b = 12.320 (10) Å
c = 22.595 (19) Å
β = 100.330 (10)°
V = 6965.4 (10) Å³
Z = 4
Mo Kα radiation
μ = 1.86 mm⁻¹
T = 293 (2) K
0.32 × 0.27 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.585, T_max = 0.791
25928 measured reflections
6480 independent reflections
5721 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.019
wR(F²) = 0.044
S = 1.03
6480 reflections
460 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H11W⋯O6	0.85	1.94	2.775 (3)	171
O1W—H12W⋯N2ⁱ	0.85	2.02	2.856 (3)	167
O2W—H21W⋯O1Wⁱⁱ	0.82	2.48	2.851 (4)	109
O3W—H31W⋯O2Wⁱⁱⁱ	0.82	2.20	2.655 (7)	116
Symmetry codes: (i) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (iii) x, y+1, z.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807066263/dn2276sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807066263/dn2276Isup2.hkl

checkCIF report

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 Eu^III 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%.

Structure description top

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

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

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]·5H₂O	F(000) = 3304
M_r = 1643.24	D_x = 1.567 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7048 reflections
a = 25.434 (2) Å	θ = 2.7–28.1°
b = 12.32 (1) Å	µ = 1.86 mm⁻¹
c = 22.595 (19) Å	T = 293 K
β = 100.33 (1)°	Block, colorless
V = 6965.4 (10) Å³	0.32 × 0.27 × 0.13 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	6480 independent reflections
Radiation source: fine-focus sealed tube	5721 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
φ and ω scans	θ_max = 25.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −30→30
T_min = 0.585, T_max = 0.791	k = −14→14
25928 measured reflections	l = −27→27

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)] = 0.019	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.044	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0183P)² + 8.1685P] where P = (F_o² + 2F_c²)/3
6480 reflections	(Δ/σ)_max = 0.006
460 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

[Eu₂(C₈H₆NO₂)₆(C₁₂H₈N₂)₂]·5H₂O	V = 6965.4 (10) Å³
M_r = 1643.24	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 25.434 (2) Å	µ = 1.86 mm⁻¹
b = 12.32 (1) Å	T = 293 K
c = 22.595 (19) Å	0.32 × 0.27 × 0.13 mm
β = 100.33 (1)°

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)
T_min = 0.585, T_max = 0.791	R_int = 0.022
25928 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.019	0 restraints
wR(F²) = 0.044	H-atom parameters constrained
S = 1.03	Δρ_max = 0.34 e Å⁻³
6480 reflections	Δρ_min = −0.25 e Å⁻³
460 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Eu1	0.528205 (4)	0.611291 (8)	0.562535 (4)	0.02456 (4)
O5	0.58593 (7)	0.57165 (15)	0.66055 (7)	0.0457 (4)
O6	0.62759 (6)	0.62061 (13)	0.58772 (7)	0.0417 (4)
N3	0.82161 (9)	0.3750 (2)	0.77152 (12)	0.0627 (7)
N4	0.55055 (7)	0.81740 (14)	0.56748 (8)	0.0312 (4)
N5	0.48983 (7)	0.72683 (15)	0.64279 (8)	0.0311 (4)
C17	0.62845 (9)	0.58151 (19)	0.63974 (11)	0.0375 (6)
C18	0.68033 (10)	0.5427 (2)	0.67463 (12)	0.0442 (6)
H18	0.7110	0.5515	0.6581	0.053*
C19	0.68467 (10)	0.4966 (2)	0.72778 (11)	0.0430 (6)
H19	0.6538	0.4954	0.7444	0.052*
C20	0.73241 (10)	0.4467 (2)	0.76421 (11)	0.0415 (6)
C21	0.73315 (12)	0.4186 (3)	0.82349 (13)	0.0589 (8)
H21	0.7035	0.4319	0.8412	0.071*
C22	0.77820 (14)	0.3705 (3)	0.85628 (14)	0.0729 (10)
H22	0.7796	0.3521	0.8964	0.087*
C23	0.82070 (13)	0.3506 (3)	0.82849 (15)	0.0664 (9)
H23	0.8508	0.3179	0.8509	0.080*
C24	0.77778 (10)	0.4222 (2)	0.74091 (12)	0.0500 (7)
H24	0.7777	0.4400	0.7009	0.060*
C25	0.58064 (10)	0.8617 (2)	0.53183 (11)	0.0418 (6)
H25	0.5997	0.8160	0.5106	0.050*
C26	0.58516 (12)	0.9740 (2)	0.52446 (12)	0.0531 (7)
H26	0.6067	1.0017	0.4988	0.064*
C27	0.55780 (12)	1.0418 (2)	0.55515 (13)	0.0562 (7)
H27	0.5599	1.1165	0.5501	0.067*
C28	0.52609 (10)	0.99896 (19)	0.59464 (12)	0.0450 (6)
C29	0.49626 (13)	1.0650 (2)	0.62910 (15)	0.0629 (8)
H29	0.4973	1.1401	0.6255	0.076*
C30	0.46693 (12)	1.0205 (2)	0.66633 (15)	0.0611 (8)
H30	0.4485	1.0655	0.6886	0.073*
C31	0.46320 (10)	0.9054 (2)	0.67276 (12)	0.0435 (6)
C32	0.43288 (10)	0.8555 (2)	0.71132 (12)	0.0505 (7)
H32	0.4134	0.8978	0.7338	0.061*
C33	0.43197 (10)	0.7457 (2)	0.71572 (11)	0.0472 (6)
H33	0.4124	0.7120	0.7415	0.057*
C34	0.46102 (9)	0.6843 (2)	0.68077 (10)	0.0395 (6)
H34	0.4602	0.6091	0.6842	0.047*
C35	0.49140 (8)	0.83702 (18)	0.63913 (10)	0.0318 (5)
C36	0.52348 (9)	0.88490 (17)	0.59938 (10)	0.0331 (5)
O1	0.44766 (7)	0.35404 (12)	0.53195 (7)	0.0375 (4)
O2	0.47138 (6)	0.48567 (12)	0.60014 (7)	0.0389 (4)
O3	0.44546 (6)	0.55841 (12)	0.47089 (7)	0.0367 (4)
O4	0.44788 (6)	0.71259 (12)	0.51991 (7)	0.0382 (4)
N1	0.40521 (14)	0.2529 (3)	0.83252 (12)	0.0830 (9)
N2	0.21675 (9)	0.92111 (19)	0.44666 (11)	0.0541 (6)
C1	0.44874 (9)	0.39752 (17)	0.58251 (10)	0.0328 (5)
C2	0.42104 (10)	0.33633 (19)	0.62482 (10)	0.0395 (5)
H2	0.3976	0.2814	0.6090	0.047*
C3	0.42757 (10)	0.35487 (19)	0.68318 (11)	0.0390 (6)
H3	0.4495	0.4129	0.6979	0.047*
C4	0.40369 (11)	0.2931 (2)	0.72740 (11)	0.0428 (6)
C5	0.36142 (13)	0.2224 (2)	0.71075 (14)	0.0632 (8)
H5	0.3466	0.2118	0.6704	0.076*
C6	0.34154 (17)	0.1676 (3)	0.75602 (19)	0.0866 (12)
H6	0.3129	0.1199	0.7466	0.104*
C7	0.36502 (18)	0.1855 (3)	0.81466 (18)	0.0882 (12)
H7	0.3516	0.1473	0.8442	0.106*
C8	0.42271 (12)	0.3066 (3)	0.78849 (12)	0.0584 (8)
H8	0.4498	0.3571	0.7997	0.070*
C9	0.42372 (9)	0.64675 (17)	0.48230 (9)	0.0295 (5)
C10	0.36825 (9)	0.67176 (18)	0.45216 (10)	0.0336 (5)
H10	0.3514	0.6266	0.4216	0.040*
C11	0.34228 (9)	0.75715 (18)	0.46803 (10)	0.0346 (5)
H11	0.3607	0.7998	0.4989	0.041*
C12	0.28771 (9)	0.79227 (19)	0.44256 (11)	0.0392 (6)
C13	0.25486 (11)	0.7384 (3)	0.39657 (14)	0.0658 (9)
H13	0.2674	0.6777	0.3789	0.079*
C14	0.20331 (12)	0.7750 (3)	0.37698 (17)	0.0795 (11)
H14	0.1807	0.7390	0.3464	0.095*
C15	0.18612 (11)	0.8654 (3)	0.40342 (15)	0.0651 (9)
H15	0.1512	0.8888	0.3904	0.078*
C16	0.26665 (10)	0.8837 (2)	0.46531 (12)	0.0457 (6)
H16	0.2886	0.9220	0.4956	0.055*
O1W	0.69847 (9)	0.61683 (17)	0.50760 (12)	0.0848 (8)
H11W	0.6788	0.6122	0.5340	0.127*
H12W	0.6986	0.5565	0.4895	0.127*
O2W	0.30658 (11)	0.1792 (3)	0.55009 (14)	0.1219 (11)
H21W	0.2805	0.2095	0.5594	0.183*
H22W	0.2973	0.1433	0.5193	0.183*
O3W	0.3341 (3)	0.9915 (5)	0.6047 (3)	0.133 (2)	0.50
H32W	0.3035	1.0082	0.6078	0.199*	0.50
H31W	0.3521	1.0410	0.5944	0.199*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Eu1	0.02668 (6)	0.02120 (6)	0.02471 (6)	−0.00104 (4)	0.00168 (4)	−0.00081 (4)
O5	0.0382 (10)	0.0595 (11)	0.0366 (9)	0.0112 (8)	−0.0010 (8)	0.0015 (8)
O6	0.0356 (9)	0.0442 (10)	0.0416 (10)	−0.0015 (7)	−0.0026 (7)	0.0035 (8)
N3	0.0460 (14)	0.0697 (17)	0.0676 (17)	0.0169 (12)	−0.0031 (12)	0.0009 (13)
N4	0.0331 (10)	0.0262 (10)	0.0332 (10)	−0.0044 (8)	0.0026 (8)	−0.0031 (8)
N5	0.0327 (10)	0.0322 (10)	0.0270 (9)	−0.0002 (8)	0.0018 (8)	−0.0025 (8)
C17	0.0348 (13)	0.0324 (13)	0.0411 (14)	0.0016 (10)	−0.0045 (11)	−0.0092 (10)
C18	0.0327 (13)	0.0459 (15)	0.0499 (15)	0.0015 (11)	−0.0033 (11)	−0.0014 (12)
C19	0.0366 (13)	0.0420 (14)	0.0471 (15)	0.0007 (11)	−0.0016 (11)	−0.0039 (12)
C20	0.0400 (14)	0.0367 (13)	0.0431 (14)	0.0008 (11)	−0.0057 (11)	−0.0026 (11)
C21	0.0577 (18)	0.068 (2)	0.0492 (17)	0.0100 (15)	0.0041 (14)	0.0027 (14)
C22	0.079 (2)	0.084 (2)	0.0483 (18)	0.0120 (19)	−0.0102 (17)	0.0169 (16)
C23	0.0566 (19)	0.0612 (19)	0.070 (2)	0.0155 (15)	−0.0192 (16)	0.0079 (16)
C24	0.0455 (15)	0.0541 (16)	0.0469 (15)	0.0046 (13)	−0.0013 (12)	0.0001 (12)
C25	0.0464 (15)	0.0380 (14)	0.0418 (14)	−0.0111 (11)	0.0102 (11)	−0.0053 (11)
C26	0.0648 (18)	0.0425 (15)	0.0533 (17)	−0.0208 (14)	0.0140 (14)	0.0019 (13)
C27	0.0678 (19)	0.0272 (14)	0.072 (2)	−0.0109 (13)	0.0082 (16)	0.0033 (13)
C28	0.0483 (15)	0.0273 (12)	0.0564 (16)	−0.0001 (11)	0.0012 (12)	−0.0037 (11)
C29	0.070 (2)	0.0292 (14)	0.090 (2)	0.0054 (14)	0.0161 (18)	−0.0103 (15)
C30	0.0621 (19)	0.0410 (16)	0.082 (2)	0.0117 (14)	0.0170 (17)	−0.0203 (15)
C31	0.0387 (14)	0.0424 (15)	0.0483 (15)	0.0069 (11)	0.0048 (11)	−0.0116 (11)
C32	0.0383 (14)	0.0632 (18)	0.0511 (16)	0.0081 (13)	0.0110 (12)	−0.0178 (14)
C33	0.0389 (14)	0.0665 (19)	0.0373 (14)	−0.0032 (13)	0.0099 (11)	−0.0062 (13)
C34	0.0429 (14)	0.0412 (14)	0.0346 (13)	−0.0038 (11)	0.0077 (11)	−0.0019 (10)
C35	0.0298 (11)	0.0306 (12)	0.0322 (12)	0.0016 (9)	−0.0025 (9)	−0.0049 (10)
C36	0.0326 (12)	0.0288 (12)	0.0348 (12)	0.0001 (10)	−0.0024 (9)	−0.0040 (10)
O1	0.0497 (10)	0.0332 (8)	0.0308 (8)	−0.0102 (7)	0.0099 (7)	−0.0043 (7)
O2	0.0511 (10)	0.0324 (9)	0.0353 (9)	−0.0135 (8)	0.0136 (8)	−0.0048 (7)
O3	0.0388 (9)	0.0252 (8)	0.0454 (9)	0.0047 (7)	0.0059 (7)	−0.0021 (7)
O4	0.0359 (9)	0.0310 (8)	0.0426 (9)	0.0043 (7)	−0.0074 (7)	−0.0062 (7)
N1	0.102 (2)	0.097 (2)	0.0588 (17)	0.014 (2)	0.0373 (17)	0.0253 (17)
N2	0.0400 (13)	0.0515 (14)	0.0725 (16)	0.0131 (11)	0.0148 (12)	0.0069 (12)
C1	0.0365 (12)	0.0291 (12)	0.0329 (12)	−0.0023 (10)	0.0064 (10)	0.0012 (10)
C2	0.0475 (14)	0.0341 (13)	0.0392 (13)	−0.0128 (11)	0.0136 (11)	−0.0034 (11)
C3	0.0453 (14)	0.0330 (13)	0.0413 (14)	−0.0038 (11)	0.0145 (11)	0.0005 (10)
C4	0.0541 (16)	0.0347 (13)	0.0443 (15)	0.0045 (11)	0.0215 (12)	0.0046 (11)
C5	0.085 (2)	0.0511 (18)	0.0599 (19)	−0.0153 (16)	0.0310 (17)	0.0009 (14)
C6	0.110 (3)	0.063 (2)	0.099 (3)	−0.032 (2)	0.053 (3)	0.003 (2)
C7	0.121 (3)	0.080 (3)	0.079 (3)	0.008 (2)	0.060 (3)	0.028 (2)
C8	0.0684 (19)	0.068 (2)	0.0432 (16)	0.0044 (15)	0.0209 (14)	0.0110 (14)
C9	0.0330 (12)	0.0250 (11)	0.0299 (11)	0.0008 (9)	0.0038 (9)	0.0039 (9)
C10	0.0329 (12)	0.0299 (12)	0.0354 (12)	−0.0021 (10)	−0.0011 (10)	−0.0044 (10)
C11	0.0327 (12)	0.0337 (12)	0.0354 (12)	−0.0028 (10)	0.0009 (10)	−0.0018 (10)
C12	0.0321 (13)	0.0388 (13)	0.0456 (14)	0.0026 (10)	0.0045 (11)	0.0012 (11)
C13	0.0437 (16)	0.065 (2)	0.080 (2)	0.0141 (14)	−0.0149 (15)	−0.0226 (17)
C14	0.0462 (18)	0.082 (2)	0.098 (3)	0.0138 (17)	−0.0224 (17)	−0.025 (2)
C15	0.0340 (15)	0.072 (2)	0.085 (2)	0.0112 (14)	−0.0021 (15)	0.0104 (18)
C16	0.0371 (13)	0.0432 (14)	0.0565 (16)	0.0046 (12)	0.0078 (12)	0.0001 (12)
O1W	0.0709 (15)	0.0684 (15)	0.128 (2)	−0.0128 (12)	0.0522 (15)	−0.0190 (14)
O2W	0.093 (2)	0.123 (3)	0.140 (3)	−0.0135 (19)	−0.0045 (19)	0.010 (2)
O3W	0.139 (5)	0.103 (5)	0.133 (5)	−0.017 (4)	−0.036 (4)	0.009 (4)

Geometric parameters (Å, º) top

Eu1—O3ⁱ	2.3604 (15)	C32—H32	0.9300
Eu1—O1ⁱ	2.3638 (15)	C33—C34	1.397 (3)
Eu1—O2	2.3763 (15)	C33—H33	0.9300
Eu1—O4	2.4400 (15)	C34—H34	0.9300
Eu1—O5	2.4765 (16)	C35—C36	1.443 (3)
Eu1—O6	2.4922 (16)	O1—C1	1.258 (3)
Eu1—N4	2.6001 (18)	O1—Eu1ⁱ	2.3638 (15)
Eu1—N5	2.6272 (18)	O2—C1	1.260 (3)
Eu1—O3	2.7530 (16)	O3—C9	1.268 (3)
Eu1—C17	2.843 (2)	O3—Eu1ⁱ	2.3604 (15)
Eu1—C9	2.969 (2)	O4—C9	1.253 (3)
Eu1—Eu1ⁱ	4.0137 (3)	N1—C7	1.322 (5)
O5—C17	1.260 (3)	N1—C8	1.336 (4)
O6—C17	1.267 (3)	N2—C15	1.327 (4)
N3—C23	1.326 (4)	N2—C16	1.345 (3)
N3—C24	1.335 (3)	C1—C2	1.490 (3)
N4—C25	1.324 (3)	C2—C3	1.319 (3)
N4—C36	1.365 (3)	C2—H2	0.9300
N5—C34	1.332 (3)	C3—C4	1.471 (3)
N5—C35	1.361 (3)	C3—H3	0.9300
C17—C18	1.489 (3)	C4—C5	1.382 (4)
C18—C19	1.315 (3)	C4—C8	1.388 (4)
C18—H18	0.9300	C5—C6	1.394 (4)
C19—C20	1.474 (3)	C5—H5	0.9300
C19—H19	0.9300	C6—C7	1.370 (5)
C20—C21	1.380 (4)	C6—H6	0.9300
C20—C24	1.385 (4)	C7—H7	0.9300
C21—C22	1.381 (4)	C8—H8	0.9300
C21—H21	0.9300	C9—C10	1.485 (3)
C22—C23	1.366 (5)	C10—C11	1.325 (3)
C22—H22	0.9300	C10—H10	0.9300
C23—H23	0.9300	C11—C12	1.469 (3)
C24—H24	0.9300	C11—H11	0.9300
C25—C26	1.400 (3)	C12—C13	1.381 (4)
C25—H25	0.9300	C12—C16	1.385 (3)
C26—C27	1.355 (4)	C13—C14	1.382 (4)
C26—H26	0.9300	C13—H13	0.9300
C27—C28	1.408 (4)	C14—C15	1.371 (4)
C27—H27	0.9300	C14—H14	0.9300
C28—C36	1.412 (3)	C15—H15	0.9300
C28—C29	1.434 (4)	C16—H16	0.9300
C29—C30	1.338 (4)	O1W—H11W	0.8462
C29—H29	0.9300	O1W—H12W	0.8481
C30—C31	1.431 (4)	O2W—H21W	0.8204
C30—H30	0.9300	O2W—H22W	0.8227
C31—C32	1.404 (4)	O3W—H32W	0.8204
C31—C35	1.413 (3)	O3W—H31W	0.8198
C32—C33	1.357 (4)

O3ⁱ—Eu1—O1ⁱ	74.72 (5)	N3—C24—H24	117.5
O3ⁱ—Eu1—O2	76.31 (5)	C20—C24—H24	117.5
O1ⁱ—Eu1—O2	135.54 (5)	N4—C25—C26	123.3 (2)
O3ⁱ—Eu1—O4	126.32 (5)	N4—C25—H25	118.4
O1ⁱ—Eu1—O4	83.44 (6)	C26—C25—H25	118.4
O2—Eu1—O4	87.38 (6)	C27—C26—C25	119.2 (3)
O3ⁱ—Eu1—O5	87.40 (6)	C27—C26—H26	120.4
O1ⁱ—Eu1—O5	129.42 (6)	C25—C26—H26	120.4
O2—Eu1—O5	81.54 (6)	C26—C27—C28	119.9 (2)
O4—Eu1—O5	140.72 (5)	C26—C27—H27	120.1
O3ⁱ—Eu1—O6	77.26 (5)	C28—C27—H27	120.1
O1ⁱ—Eu1—O6	77.34 (6)	C27—C28—C36	117.5 (2)
O2—Eu1—O6	127.26 (6)	C27—C28—C29	123.4 (2)
O4—Eu1—O6	144.08 (5)	C36—C28—C29	119.1 (3)
O5—Eu1—O6	52.45 (6)	C30—C29—C28	121.2 (3)
O3ⁱ—Eu1—N4	143.74 (6)	C30—C29—H29	119.4
O1ⁱ—Eu1—N4	76.83 (5)	C28—C29—H29	119.4
O2—Eu1—N4	139.73 (5)	C29—C30—C31	121.6 (3)
O4—Eu1—N4	71.25 (5)	C29—C30—H30	119.2
O5—Eu1—N4	93.68 (6)	C31—C30—H30	119.2
O6—Eu1—N4	74.94 (6)	C32—C31—C35	117.5 (2)
O3ⁱ—Eu1—N5	149.61 (6)	C32—C31—C30	123.4 (2)
O1ⁱ—Eu1—N5	135.59 (5)	C35—C31—C30	119.1 (3)
O2—Eu1—N5	77.35 (5)	C33—C32—C31	120.0 (2)
O4—Eu1—N5	66.85 (5)	C33—C32—H32	120.0
O5—Eu1—N5	73.95 (6)	C31—C32—H32	120.0
O6—Eu1—N5	107.73 (5)	C32—C33—C34	118.8 (2)
N4—Eu1—N5	63.04 (6)	C32—C33—H33	120.6
O3ⁱ—Eu1—O3	76.84 (5)	C34—C33—H33	120.6
O1ⁱ—Eu1—O3	69.55 (5)	N5—C34—C33	124.0 (2)
O2—Eu1—O3	71.51 (5)	N5—C34—H34	118.0
O4—Eu1—O3	49.54 (5)	C33—C34—H34	118.0
O5—Eu1—O3	151.25 (6)	N5—C35—C31	122.6 (2)
O6—Eu1—O3	142.18 (5)	N5—C35—C36	118.14 (19)
N4—Eu1—O3	113.28 (5)	C31—C35—C36	119.3 (2)
N5—Eu1—O3	108.60 (5)	N4—C36—C28	122.1 (2)
O3ⁱ—Eu1—C17	78.89 (6)	N4—C36—C35	118.33 (19)
O1ⁱ—Eu1—C17	103.18 (7)	C28—C36—C35	119.6 (2)
O2—Eu1—C17	103.45 (7)	C1—O1—Eu1ⁱ	140.95 (14)
O4—Eu1—C17	154.62 (6)	C1—O2—Eu1	136.14 (14)
O5—Eu1—C17	26.26 (6)	C9—O3—Eu1ⁱ	169.88 (14)
O6—Eu1—C17	26.44 (6)	C9—O3—Eu1	86.92 (12)
N4—Eu1—C17	86.25 (6)	Eu1ⁱ—O3—Eu1	103.16 (5)
N5—Eu1—C17	92.85 (6)	C9—O4—Eu1	102.16 (13)
O3—Eu1—C17	155.71 (6)	C7—N1—C8	115.2 (3)
O3ⁱ—Eu1—C9	102.08 (6)	C15—N2—C16	116.7 (2)
O1ⁱ—Eu1—C9	76.75 (6)	O1—C1—O2	126.1 (2)
O2—Eu1—C9	77.23 (6)	O1—C1—C2	115.56 (19)
O4—Eu1—C9	24.37 (5)	O2—C1—C2	118.4 (2)
O5—Eu1—C9	153.82 (6)	C3—C2—C1	124.4 (2)
O6—Eu1—C9	153.25 (6)	C3—C2—H2	117.8
N4—Eu1—C9	92.72 (6)	C1—C2—H2	117.8
N5—Eu1—C9	86.51 (6)	C2—C3—C4	126.6 (2)
O3—Eu1—C9	25.25 (5)	C2—C3—H3	116.7
C17—Eu1—C9	178.95 (6)	C4—C3—H3	116.7
O3ⁱ—Eu1—Eu1ⁱ	41.90 (4)	C5—C4—C8	117.5 (2)
O1ⁱ—Eu1—Eu1ⁱ	66.76 (4)	C5—C4—C3	122.5 (2)
O2—Eu1—Eu1ⁱ	69.10 (4)	C8—C4—C3	120.0 (2)
O4—Eu1—Eu1ⁱ	84.45 (4)	C4—C5—C6	118.2 (3)
O5—Eu1—Eu1ⁱ	125.08 (4)	C4—C5—H5	120.9
O6—Eu1—Eu1ⁱ	114.34 (4)	C6—C5—H5	120.9
N4—Eu1—Eu1ⁱ	138.18 (4)	C7—C6—C5	118.6 (3)
N5—Eu1—Eu1ⁱ	136.55 (4)	C7—C6—H6	120.7
O3—Eu1—Eu1ⁱ	34.93 (3)	C5—C6—H6	120.7
C17—Eu1—Eu1ⁱ	120.79 (5)	N1—C7—C6	125.1 (3)
C9—Eu1—Eu1ⁱ	60.18 (4)	N1—C7—H7	117.4
C17—O5—Eu1	93.33 (14)	C6—C7—H7	117.4
C17—O6—Eu1	92.42 (14)	N1—C8—C4	125.3 (3)
C23—N3—C24	116.3 (3)	N1—C8—H8	117.4
C25—N4—C36	118.12 (19)	C4—C8—H8	117.4
C25—N4—Eu1	121.48 (15)	O4—C9—O3	120.99 (19)
C36—N4—Eu1	119.38 (14)	O4—C9—C10	119.13 (19)
C34—N5—C35	117.2 (2)	O3—C9—C10	119.86 (19)
C34—N5—Eu1	123.15 (15)	O4—C9—Eu1	53.47 (10)
C35—N5—Eu1	118.67 (14)	O3—C9—Eu1	67.83 (11)
O5—C17—O6	120.7 (2)	C10—C9—Eu1	169.61 (15)
O5—C17—C18	120.6 (2)	C11—C10—C9	121.3 (2)
O6—C17—C18	118.6 (2)	C11—C10—H10	119.4
O5—C17—Eu1	60.41 (12)	C9—C10—H10	119.4
O6—C17—Eu1	61.14 (12)	C10—C11—C12	127.6 (2)
C18—C17—Eu1	168.00 (16)	C10—C11—H11	116.2
C19—C18—C17	122.9 (2)	C12—C11—H11	116.2
C19—C18—H18	118.5	C13—C12—C16	116.6 (2)
C17—C18—H18	118.5	C13—C12—C11	123.7 (2)
C18—C19—C20	128.0 (3)	C16—C12—C11	119.7 (2)
C18—C19—H19	116.0	C12—C13—C14	119.7 (3)
C20—C19—H19	116.0	C12—C13—H13	120.2
C21—C20—C24	116.6 (2)	C14—C13—H13	120.2
C21—C20—C19	120.9 (2)	C15—C14—C13	119.0 (3)
C24—C20—C19	122.5 (2)	C15—C14—H14	120.5
C20—C21—C22	119.6 (3)	C13—C14—H14	120.5
C20—C21—H21	120.2	N2—C15—C14	123.4 (3)
C22—C21—H21	120.2	N2—C15—H15	118.3
C23—C22—C21	118.6 (3)	C14—C15—H15	118.3
C23—C22—H22	120.7	N2—C16—C12	124.6 (3)
C21—C22—H22	120.7	N2—C16—H16	117.7
N3—C23—C22	123.9 (3)	C12—C16—H16	117.7
N3—C23—H23	118.0	H11W—O1W—H12W	109.4
C22—C23—H23	118.0	H21W—O2W—H22W	109.8
N3—C24—C20	125.0 (3)	H32W—O3W—H31W	115.1

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11W···O6	0.85	1.94	2.775 (3)	171
O1W—H12W···N2ⁱⁱ	0.85	2.02	2.856 (3)	167
O2W—H21W···O1Wⁱⁱⁱ	0.82	2.48	2.851 (4)	109
O3W—H31W···O2W^iv	0.82	2.20	2.655 (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.

Experimental details

Crystal data
Chemical formula	[Eu₂(C₈H₆NO₂)₆(C₁₂H₈N₂)₂]·5H₂O
M_r	1643.24
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	25.434 (2), 12.32 (1), 22.595 (19)
β (°)	100.33 (1)
V (Å³)	6965.4 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.86
Crystal size (mm)	0.32 × 0.27 × 0.13

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.585, 0.791
No. of measured, independent and observed [I > 2σ(I)] reflections	25928, 6480, 5721
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.019, 0.044, 1.03
No. of reflections	6480
No. of parameters	460
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.25

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996)and ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11W···O6	0.85	1.94	2.775 (3)	170.9
O1W—H12W···N2ⁱ	0.85	2.02	2.856 (3)	166.8
O2W—H21W···O1Wⁱⁱ	0.82	2.48	2.851 (4)	108.6
O3W—H31W···O2Wⁱⁱⁱ	0.82	2.20	2.655 (7)	115.5

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

Acknowledgements

This work is supported by the National Natural Science Foundation of China (20662007) and Nanchang University of Aeronautics (EA20072195).

References

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