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

Ooi, P.H.; Teoh, S.G.; Yeap, C.S.; Fun, H.-K.

doi:10.1107/S1600536810015229

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Pages m597-m598

https://doi.org/10.1107/S1600536810015229

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

Ping Howe Ooi,^a ‡ Siang Guan Teoh,^a Chin Sing Yeap ^b § and Hoong-Kun Fun ^b ^*¶

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 31 March 2010; accepted 26 April 2010; online 30 April 2010)

The asymmetric unit of the title complex, [Eu₂(C₇H₅O₂)₆(C₁₂H₈N₂)₂]·2C₆H₅COOH, contains one-half of the complex molecule, the complete molecule being generated by inversion symmetry, and one benzoic acid solvent molecule. The two Eu^III ions are linked by four bridging benzoate ions, with an Eu⋯Eu distance of 3.96041 (12) Å. Each Eu^III ion is coordinated by one phenanthroline heterocycle and a bidentate benzoate ion. The irregular nine-coordinated geometry of the metal ion is composed of seven O and two N atoms. The molecular structure is stabilized by intramolecular C—H⋯O hydrogen bonds. In the crystal structure, molecules are linked into chains by intermolecular C—H⋯O hydrogen bonds along the a axis. The crystal structure is further stabilized by intermolecular C—H⋯O and C—H⋯π interactions. Weak π–π interactions are also observed [centroid–centroid distances = 3.6962 (10)–3.6963 (10) Å].

Related literature

For general background to and applications of europium(III) complexes, see: Yam & Lo (1999 ); Beeby et al. (2003 ); Tang et al. (2008 ); Faulkner et al. (2005 ). For related Ln–benzoato complexes (Ln = lanthanide), see: Niu et al. (1999 , 2002 ); Shi et al. (2001 ); Ooi et al. (2010 ).

Experimental

Crystal data

[Eu₂(C₇H₅O₂)₆(C₁₂H₈N₂)₂]·2C₇H₆O₂
M_r = 1635.22
Triclinic, $[P \overline 1]$
a = 9.6688 (2) Å
b = 12.8260 (2) Å
c = 15.1460 (3) Å
α = 75.244 (1)°
β = 78.605 (1)°
γ = 76.072 (1)°
V = 1744.26 (6) Å³
Z = 1
Mo Kα radiation
μ = 1.86 mm⁻¹
T = 296 K
0.58 × 0.32 × 0.28 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.413, T_max = 0.628
51513 measured reflections
12557 independent reflections
11674 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.020
wR(F²) = 0.050
S = 1.04
12557 reflections
464 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.62 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Selected bond lengths (Å)

Eu1—O5	2.3667 (9)
Eu1—O3ⁱ	2.3669 (9)
Eu1—O6ⁱ	2.3818 (10)
Eu1—O4	2.4571 (11)
Eu1—O2	2.4933 (11)
Eu1—O1	2.4974 (11)
Eu1—N1	2.5636 (11)
Eu1—N2	2.6134 (11)
Eu1—O3	2.6394 (11)
Symmetry code: (i) -x+2, -y, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C35–C40 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H1O8⋯O1	0.86 (3)	1.82 (3)	2.660 (2)	166 (3)
C2—H2A⋯O6ⁱ	0.93	2.43	3.017 (2)	121
C9—H9A⋯O2ⁱⁱ	0.93	2.51	3.258 (2)	138
C11—H11A⋯O5	0.93	2.44	3.079 (2)	126
C25—H25A⋯Cg1ⁱⁱⁱ	0.93	2.65	3.551 (3)	164
Symmetry codes: (i) -x+2, -y, -z+1; (ii) x-1, y, z; (iii) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810015229/rz2435sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810015229/rz2435Isup2.hkl

checkCIF report

Comment top

Lanthanide complexes were widely used in biomedical field (Yam & Lo, 1999), sensing areas (Beeby et al., 2003) and optical imaging (Faulkner et al., 2005) because they exhibit intense luminescence, especially europium (III) and terbium (III) ions. In order to create high luminescence complexes, ligands which chelate to the lanthanide atoms should be able to protect lanthanide ions from solvent molecules and absorb energy to transfer it efficiently to the center metal atom (Tang et al., 2008). The title compound, (I) was synthesized and its structure was determined. Similar crystal structures with different lanthanides have been reported in the past, such as lanthanum(III) (Shi et al., 2001), samarium(III) (Niu et al., 1999), gadolinium(III) (Niu et al., 2002) and neodymium(III) (Ooi et al., 2010).

The asymmetric unit of the title complex (I) (Fig. 1) consists of one-half of the complex molecule and one benzoic acid. The complex molecule lies on a crystallographic inversion center. The two europium(III) ions are linked by four benzoate ions, with an Eu—Eu distance of 3.96041 (12) Å. Among the four benzoate ions, two of them also behave as chelating ligands to the europium(III) ions. Each metal ion is coordinated by one phenanthroline heterocycle and a bidentate benzoate ion. The irregular nine-coordinated geometry of the europium(III) ion is completed by seven benzoate O atoms and two phenanthroline N atoms. Bond lengths of Eu—O and Eu—N are listed in Table 1. All other bond lengths and angles are comparable to a closely La-benzoato complex (Shi et al., 2001).

In the crystal structure, intermolecular C9—H9A···O2 hydrogen bonds (Table 2) link the molecules into chains along the a axis (Fig. 2). The crystal structure is further stabilized by intermolecular O8—H1O8···O1 and C25A—H25A···Cg1 interactions (Table 2). Intramolecular C2—H2A···O6 and C11—H11A···O5 hydrogen bonds (Table 2) stabilize the molecular structure. Weak π–π interactions of Cg2···Cg3 = 3.6963 (10) Å and Cg3···Cg3 = 3.6962 (10) Å [Cg2 and Cg3 are centroids of benzene rings C1/N1/C2–C5 and C1/C5–C8/C12; symmetry code: 1-x, 1-y, 1-z] are observed.

Related literature top

For general background to and applications of europium(III) complexes, see: Yam & Lo (1999); Beeby et al. (2003); Tang et al. (2008); Faulkner et al. (2005). For related Ln–benzoato complexes, see: Niu et al. (1999); Niu et al. (2002); Shi et al. (2001); Ooi et al. (2010).

Experimental top

0.5 mmol of EuCl₃.6H₂O was dissolved in methanol and then was added into a solution (methanol-H₂O, 1.5:1) of 1,10-phenanthroline (0.5 mmol) and benzoic acid (1.5 mmol). The mixture was sealed in a tube, and heated directly to 403 K. After keeping at 403 K for 2 days, it was cooled to room temperature. Colourless block crystals (I) were obtained by filtration, and was washed with water and ethanol.

Structure description top

For general background to and applications of europium(III) complexes, see: Yam & Lo (1999); Beeby et al. (2003); Tang et al. (2008); Faulkner et al. (2005). For related Ln–benzoato complexes, see: Niu et al. (1999); Niu et al. (2002); Shi et al. (2001); Ooi et al. (2010).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title complex, showing 20% probability displacement ellipsoids for non-H atoms and the atom-numbering scheme. The suffix A corresponds to the symmetry code [-x+2, -y, -z+1].
	Fig. 2. The crystal structure of the title complex, viewed along the a axis, showing two chains along a axis. The benzoic acid solvent molecules have been omitted for clarity. Intermolecular hydrogen bonds are shown as dashed lines.

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

Crystal data top

[Eu₂(C₇H₅O₂)₆(C₁₂H₈N₂)₂]·2C₇H₆O₂	Z = 1
M_r = 1635.22	F(000) = 820
Triclinic, P1	D_x = 1.557 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6688 (2) Å	Cell parameters from 9857 reflections
b = 12.8260 (2) Å	θ = 2.2–35.2°
c = 15.1460 (3) Å	µ = 1.86 mm⁻¹
α = 75.244 (1)°	T = 296 K
β = 78.605 (1)°	Block, colourless
γ = 76.072 (1)°	0.58 × 0.32 × 0.28 mm
V = 1744.26 (6) Å³

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	12557 independent reflections
Radiation source: fine-focus sealed tube	11674 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
φ and ω scans	θ_max = 32.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
T_min = 0.413, T_max = 0.628	k = −19→19
51513 measured reflections	l = −22→22

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)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.050	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0249P)² + 0.3553P] where P = (F_o² + 2F_c²)/3
12557 reflections	(Δ/σ)_max = 0.004
464 parameters	Δρ_max = 0.62 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

[Eu₂(C₇H₅O₂)₆(C₁₂H₈N₂)₂]·2C₇H₆O₂	γ = 76.072 (1)°
M_r = 1635.22	V = 1744.26 (6) Å³
Triclinic, P1	Z = 1
a = 9.6688 (2) Å	Mo Kα radiation
b = 12.8260 (2) Å	µ = 1.86 mm⁻¹
c = 15.1460 (3) Å	T = 296 K
α = 75.244 (1)°	0.58 × 0.32 × 0.28 mm
β = 78.605 (1)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	12557 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	11674 reflections with I > 2σ(I)
T_min = 0.413, T_max = 0.628	R_int = 0.027
51513 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.020	0 restraints
wR(F²) = 0.050	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.62 e Å⁻³
12557 reflections	Δρ_min = −0.44 e Å⁻³
464 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 > 2sigma(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	0.855968 (6)	0.139628 (5)	0.482146 (4)	0.02529 (2)
O1	0.81802 (11)	0.27751 (9)	0.33491 (7)	0.0374 (2)
O2	0.99095 (13)	0.28905 (10)	0.40393 (8)	0.0415 (2)
O3	0.92345 (10)	−0.05431 (9)	0.59329 (7)	0.0340 (2)
O4	0.71990 (11)	0.05713 (10)	0.62752 (8)	0.0431 (2)
O5	0.79737 (11)	0.01384 (8)	0.41205 (7)	0.0357 (2)
O6	0.98042 (11)	−0.13176 (8)	0.41650 (7)	0.0360 (2)
N1	0.73487 (13)	0.30002 (10)	0.56106 (9)	0.0348 (2)
N2	0.58048 (12)	0.21295 (10)	0.47649 (8)	0.0332 (2)
C1	0.58983 (15)	0.33702 (11)	0.56896 (10)	0.0339 (3)
C2	0.8100 (2)	0.34414 (14)	0.60131 (13)	0.0450 (4)
H2A	0.9095	0.3203	0.5951	0.054*
C3	0.7467 (2)	0.42462 (15)	0.65248 (14)	0.0565 (5)
H3A	0.8033	0.4523	0.6804	0.068*
C4	0.6018 (2)	0.46191 (15)	0.66108 (13)	0.0549 (5)
H4A	0.5581	0.5152	0.6951	0.066*
C5	0.51860 (19)	0.41920 (13)	0.61810 (11)	0.0446 (4)
C6	0.3666 (2)	0.45696 (16)	0.62105 (14)	0.0586 (5)
H6A	0.3195	0.5114	0.6533	0.070*
C7	0.2904 (2)	0.41550 (17)	0.57823 (15)	0.0580 (5)
H7A	0.1914	0.4413	0.5818	0.070*
C8	0.35873 (16)	0.33214 (14)	0.52707 (12)	0.0438 (3)
C9	0.28376 (17)	0.28860 (16)	0.47982 (14)	0.0532 (4)
H9A	0.1850	0.3134	0.4805	0.064*
C10	0.35619 (19)	0.20981 (16)	0.43288 (15)	0.0538 (4)
H10A	0.3076	0.1802	0.4011	0.065*
C11	0.50501 (17)	0.17374 (14)	0.43291 (13)	0.0443 (3)
H11A	0.5533	0.1195	0.4007	0.053*
C12	0.50850 (15)	0.29219 (11)	0.52310 (10)	0.0341 (3)
C13	0.92857 (15)	0.31615 (11)	0.33417 (10)	0.0331 (3)
C14	0.98440 (17)	0.39252 (12)	0.25009 (10)	0.0369 (3)
C15	0.8962 (2)	0.45586 (14)	0.18589 (11)	0.0464 (4)
H15A	0.7999	0.4508	0.1943	0.056*
C16	0.9523 (3)	0.52675 (17)	0.10903 (13)	0.0637 (6)
H16A	0.8929	0.5704	0.0665	0.076*
C17	1.0955 (3)	0.5327 (2)	0.09555 (15)	0.0733 (7)
H17A	1.1322	0.5805	0.0439	0.088*
C18	1.1843 (3)	0.4690 (2)	0.15733 (14)	0.0650 (6)
H18A	1.2813	0.4725	0.1471	0.078*
C19	1.1292 (2)	0.39925 (16)	0.23535 (12)	0.0488 (4)
H19A	1.1891	0.3568	0.2780	0.059*
C20	0.81636 (14)	−0.02422 (11)	0.65167 (9)	0.0312 (2)
C21	0.80887 (15)	−0.08375 (12)	0.75001 (10)	0.0344 (3)
C22	0.93267 (18)	−0.12514 (15)	0.79046 (11)	0.0444 (3)
H22A	1.0219	−0.1178	0.7556	0.053*
C23	0.9241 (3)	−0.1774 (2)	0.88256 (13)	0.0621 (5)
H23A	1.0076	−0.2050	0.9097	0.074*
C24	0.7932 (3)	−0.1885 (2)	0.93387 (14)	0.0716 (6)
H24A	0.7881	−0.2243	0.9957	0.086*
C25	0.6697 (3)	−0.1473 (2)	0.89483 (15)	0.0732 (7)
H25A	0.5810	−0.1548	0.9304	0.088*
C26	0.6760 (2)	−0.09452 (18)	0.80281 (13)	0.0542 (4)
H26A	0.5920	−0.0664	0.7764	0.065*
C27	0.86800 (14)	−0.07267 (11)	0.38672 (9)	0.0298 (2)
C28	0.81424 (15)	−0.11023 (12)	0.31629 (10)	0.0340 (3)
C29	0.66775 (17)	−0.09528 (14)	0.31412 (11)	0.0404 (3)
H29A	0.6017	−0.0556	0.3532	0.048*
C30	0.6193 (2)	−0.13920 (18)	0.25387 (14)	0.0554 (5)
H30A	0.5211	−0.1313	0.2541	0.066*
C31	0.7167 (3)	−0.1941 (3)	0.19409 (17)	0.0785 (8)
H31A	0.6842	−0.2232	0.1535	0.094*
C32	0.8625 (3)	−0.2068 (3)	0.19349 (18)	0.0872 (9)
H32A	0.9279	−0.2428	0.1516	0.105*
C33	0.9119 (2)	−0.16586 (19)	0.25529 (14)	0.0583 (5)
H33A	1.0103	−0.1757	0.2558	0.070*
O7	0.5814 (2)	0.39064 (16)	0.15565 (15)	0.0873 (6)
O8	0.72156 (19)	0.22869 (14)	0.20067 (12)	0.0695 (4)
C34	0.6441 (2)	0.30199 (19)	0.14202 (15)	0.0574 (5)
C35	0.6454 (2)	0.2640 (2)	0.05692 (15)	0.0620 (5)
C36	0.5708 (3)	0.3347 (3)	−0.01171 (18)	0.0841 (9)
H36A	0.5192	0.4036	−0.0033	0.101*
C37	0.5733 (5)	0.3028 (4)	−0.0927 (2)	0.1221 (17)
H37A	0.5222	0.3501	−0.1382	0.147*
C38	0.6484 (5)	0.2046 (5)	−0.1061 (3)	0.135 (2)
H38A	0.6505	0.1849	−0.1615	0.162*
C39	0.7221 (4)	0.1329 (4)	−0.0395 (3)	0.1310 (17)
H39A	0.7730	0.0643	−0.0492	0.157*
C40	0.7205 (3)	0.1630 (3)	0.0436 (2)	0.0896 (9)
H40A	0.7703	0.1146	0.0893	0.108*
H1O8	0.743 (3)	0.255 (2)	0.242 (2)	0.089 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Eu1	0.02319 (3)	0.02625 (3)	0.02639 (3)	−0.00168 (2)	−0.00573 (2)	−0.00710 (2)
O1	0.0346 (5)	0.0412 (5)	0.0364 (5)	−0.0105 (4)	−0.0090 (4)	−0.0030 (4)
O2	0.0442 (6)	0.0451 (6)	0.0377 (5)	−0.0170 (5)	−0.0131 (4)	−0.0005 (5)
O3	0.0301 (4)	0.0394 (5)	0.0311 (5)	−0.0039 (4)	0.0004 (4)	−0.0116 (4)
O4	0.0322 (5)	0.0463 (6)	0.0375 (5)	0.0027 (4)	0.0008 (4)	0.0001 (5)
O5	0.0316 (5)	0.0362 (5)	0.0440 (5)	−0.0021 (4)	−0.0116 (4)	−0.0169 (4)
O6	0.0349 (5)	0.0360 (5)	0.0400 (5)	−0.0001 (4)	−0.0161 (4)	−0.0119 (4)
N1	0.0361 (6)	0.0325 (5)	0.0369 (6)	−0.0022 (4)	−0.0066 (5)	−0.0132 (5)
N2	0.0277 (5)	0.0329 (5)	0.0383 (6)	−0.0033 (4)	−0.0075 (4)	−0.0072 (5)
C1	0.0352 (6)	0.0286 (6)	0.0320 (6)	0.0005 (5)	−0.0016 (5)	−0.0052 (5)
C2	0.0497 (9)	0.0391 (8)	0.0524 (9)	−0.0029 (7)	−0.0176 (7)	−0.0190 (7)
C3	0.0783 (13)	0.0440 (9)	0.0559 (10)	−0.0044 (9)	−0.0228 (10)	−0.0236 (8)
C4	0.0786 (13)	0.0392 (8)	0.0440 (9)	0.0030 (8)	−0.0062 (8)	−0.0198 (7)
C5	0.0518 (9)	0.0349 (7)	0.0379 (7)	0.0034 (6)	0.0028 (6)	−0.0098 (6)
C6	0.0545 (10)	0.0489 (10)	0.0546 (10)	0.0116 (8)	0.0107 (8)	−0.0147 (8)
C7	0.0361 (8)	0.0528 (10)	0.0656 (12)	0.0086 (7)	0.0078 (8)	−0.0065 (9)
C8	0.0286 (6)	0.0411 (8)	0.0496 (9)	−0.0011 (6)	0.0005 (6)	0.0013 (6)
C9	0.0273 (7)	0.0531 (10)	0.0701 (12)	−0.0062 (7)	−0.0110 (7)	0.0043 (9)
C10	0.0367 (8)	0.0533 (10)	0.0745 (13)	−0.0119 (7)	−0.0241 (8)	−0.0048 (9)
C11	0.0358 (7)	0.0435 (8)	0.0576 (10)	−0.0052 (6)	−0.0176 (7)	−0.0125 (7)
C12	0.0280 (6)	0.0313 (6)	0.0363 (7)	−0.0017 (5)	−0.0016 (5)	−0.0020 (5)
C13	0.0346 (6)	0.0299 (6)	0.0337 (6)	−0.0051 (5)	−0.0040 (5)	−0.0069 (5)
C14	0.0469 (8)	0.0322 (6)	0.0326 (6)	−0.0115 (6)	−0.0018 (6)	−0.0084 (5)
C15	0.0595 (10)	0.0405 (8)	0.0358 (7)	−0.0071 (7)	−0.0066 (7)	−0.0052 (6)
C16	0.0993 (18)	0.0486 (10)	0.0379 (9)	−0.0153 (11)	−0.0103 (10)	0.0004 (8)
C17	0.111 (2)	0.0694 (14)	0.0427 (10)	−0.0494 (14)	0.0106 (11)	−0.0050 (9)
C18	0.0762 (14)	0.0797 (15)	0.0493 (10)	−0.0467 (12)	0.0072 (10)	−0.0152 (10)
C19	0.0532 (9)	0.0556 (10)	0.0434 (8)	−0.0253 (8)	−0.0025 (7)	−0.0112 (7)
C20	0.0272 (5)	0.0340 (6)	0.0310 (6)	−0.0067 (5)	−0.0010 (5)	−0.0067 (5)
C21	0.0348 (6)	0.0347 (6)	0.0307 (6)	−0.0067 (5)	−0.0007 (5)	−0.0050 (5)
C22	0.0399 (8)	0.0537 (9)	0.0361 (7)	−0.0031 (7)	−0.0069 (6)	−0.0084 (7)
C23	0.0649 (12)	0.0734 (14)	0.0403 (9)	−0.0016 (10)	−0.0174 (8)	−0.0029 (9)
C24	0.0862 (16)	0.0812 (16)	0.0349 (9)	−0.0182 (13)	−0.0055 (10)	0.0082 (9)
C25	0.0634 (13)	0.0953 (18)	0.0467 (11)	−0.0302 (13)	0.0106 (9)	0.0090 (11)
C26	0.0387 (8)	0.0701 (12)	0.0456 (9)	−0.0165 (8)	0.0015 (7)	0.0014 (8)
C27	0.0294 (6)	0.0320 (6)	0.0302 (6)	−0.0059 (5)	−0.0079 (5)	−0.0082 (5)
C28	0.0350 (6)	0.0371 (7)	0.0333 (6)	−0.0040 (5)	−0.0107 (5)	−0.0122 (5)
C29	0.0375 (7)	0.0447 (8)	0.0442 (8)	−0.0051 (6)	−0.0137 (6)	−0.0160 (6)
C30	0.0492 (9)	0.0703 (12)	0.0596 (11)	−0.0131 (9)	−0.0228 (8)	−0.0250 (10)
C31	0.0720 (14)	0.117 (2)	0.0725 (15)	−0.0194 (14)	−0.0213 (12)	−0.0584 (15)
C32	0.0660 (14)	0.139 (3)	0.0799 (16)	−0.0072 (15)	−0.0076 (12)	−0.0808 (18)
C33	0.0419 (9)	0.0859 (14)	0.0565 (11)	−0.0017 (9)	−0.0077 (8)	−0.0421 (11)
O7	0.0881 (13)	0.0763 (12)	0.1062 (15)	0.0128 (10)	−0.0490 (11)	−0.0364 (11)
O8	0.0750 (10)	0.0691 (10)	0.0727 (10)	0.0023 (8)	−0.0379 (8)	−0.0250 (8)
C34	0.0493 (10)	0.0676 (13)	0.0621 (12)	−0.0123 (9)	−0.0194 (9)	−0.0168 (10)
C35	0.0574 (11)	0.0837 (15)	0.0582 (11)	−0.0341 (11)	−0.0111 (9)	−0.0183 (11)
C36	0.103 (2)	0.101 (2)	0.0633 (14)	−0.0613 (18)	−0.0300 (14)	0.0085 (13)
C37	0.155 (4)	0.191 (4)	0.0526 (15)	−0.121 (4)	−0.0252 (19)	0.006 (2)
C38	0.127 (3)	0.246 (6)	0.083 (2)	−0.108 (4)	0.012 (2)	−0.081 (3)
C39	0.090 (2)	0.201 (5)	0.149 (4)	−0.038 (3)	−0.005 (2)	−0.123 (4)
C40	0.0670 (15)	0.119 (2)	0.107 (2)	−0.0156 (15)	−0.0216 (15)	−0.063 (2)

Geometric parameters (Å, º) top

Eu1—O5	2.3667 (9)	C15—H15A	0.9300
Eu1—O3ⁱ	2.3669 (9)	C16—C17	1.377 (4)
Eu1—O6ⁱ	2.3818 (10)	C16—H16A	0.9300
Eu1—O4	2.4571 (11)	C17—C18	1.368 (4)
Eu1—O2	2.4933 (11)	C17—H17A	0.9300
Eu1—O1	2.4974 (11)	C18—C19	1.387 (3)
Eu1—N1	2.5636 (11)	C18—H18A	0.9300
Eu1—N2	2.6134 (11)	C19—H19A	0.9300
Eu1—O3	2.6394 (11)	C20—C21	1.487 (2)
Eu1—C13	2.8637 (14)	C21—C22	1.381 (2)
Eu1—C20	2.8992 (14)	C21—C26	1.390 (2)
Eu1—Eu1ⁱ	3.9604 (1)	C22—C23	1.381 (3)
O1—C13	1.2789 (18)	C22—H22A	0.9300
O2—C13	1.2509 (18)	C23—C24	1.367 (3)
O3—C20	1.2739 (15)	C23—H23A	0.9300
O3—Eu1ⁱ	2.3668 (9)	C24—C25	1.368 (4)
O4—C20	1.2506 (17)	C24—H24A	0.9300
O5—C27	1.2623 (16)	C25—C26	1.382 (3)
O6—C27	1.2579 (16)	C25—H25A	0.9300
O6—Eu1ⁱ	2.3819 (10)	C26—H26A	0.9300
N1—C2	1.330 (2)	C27—C28	1.4971 (18)
N1—C1	1.3596 (18)	C28—C33	1.386 (2)
N2—C11	1.3256 (19)	C28—C29	1.389 (2)
N2—C12	1.3589 (18)	C29—C30	1.388 (2)
C1—C5	1.4096 (19)	C29—H29A	0.9300
C1—C12	1.438 (2)	C30—C31	1.368 (3)
C2—C3	1.399 (2)	C30—H30A	0.9300
C2—H2A	0.9300	C31—C32	1.379 (3)
C3—C4	1.359 (3)	C31—H31A	0.9300
C3—H3A	0.9300	C32—C33	1.389 (3)
C4—C5	1.404 (3)	C32—H32A	0.9300
C4—H4A	0.9300	C33—H33A	0.9300
C5—C6	1.428 (3)	O7—C34	1.200 (3)
C6—C7	1.341 (3)	O8—C34	1.316 (3)
C6—H6A	0.9300	O8—H1O8	0.86 (3)
C7—C8	1.435 (3)	C34—C35	1.486 (3)
C7—H7A	0.9300	C35—C40	1.366 (4)
C8—C9	1.397 (3)	C35—C36	1.387 (4)
C8—C12	1.410 (2)	C36—C37	1.383 (4)
C9—C10	1.359 (3)	C36—H36A	0.9300
C9—H9A	0.9300	C37—C38	1.336 (7)
C10—C11	1.401 (2)	C37—H37A	0.9300
C10—H10A	0.9300	C38—C39	1.367 (7)
C11—H11A	0.9300	C38—H38A	0.9300
C13—C14	1.490 (2)	C39—C40	1.405 (4)
C14—C15	1.387 (2)	C39—H39A	0.9300
C14—C19	1.394 (2)	C40—H40A	0.9300
C15—C16	1.387 (3)

O5—Eu1—O3ⁱ	74.07 (3)	C10—C9—C8	119.53 (15)
O5—Eu1—O6ⁱ	136.23 (4)	C10—C9—H9A	120.2
O3ⁱ—Eu1—O6ⁱ	78.20 (3)	C8—C9—H9A	120.2
O5—Eu1—O4	88.22 (4)	C9—C10—C11	119.19 (17)
O3ⁱ—Eu1—O4	126.28 (4)	C9—C10—H10A	120.4
O6ⁱ—Eu1—O4	81.61 (4)	C11—C10—H10A	120.4
O5—Eu1—O2	126.55 (4)	N2—C11—C10	123.32 (17)
O3ⁱ—Eu1—O2	73.68 (4)	N2—C11—H11A	118.3
O6ⁱ—Eu1—O2	74.81 (4)	C10—C11—H11A	118.3
O4—Eu1—O2	145.08 (4)	N2—C12—C8	122.47 (14)
O5—Eu1—O1	86.23 (4)	N2—C12—C1	118.12 (12)
O3ⁱ—Eu1—O1	89.18 (4)	C8—C12—C1	119.41 (14)
O6ⁱ—Eu1—O1	126.75 (4)	O2—C13—O1	119.97 (13)
O4—Eu1—O1	140.76 (4)	O2—C13—C14	119.79 (13)
O2—Eu1—O1	52.07 (3)	O1—C13—C14	120.23 (13)
O5—Eu1—N1	140.57 (4)	O2—C13—Eu1	60.31 (8)
O3ⁱ—Eu1—N1	144.07 (4)	O1—C13—Eu1	60.57 (7)
O6ⁱ—Eu1—N1	76.95 (4)	C14—C13—Eu1	169.95 (10)
O4—Eu1—N1	74.78 (4)	C15—C14—C19	119.41 (15)
O2—Eu1—N1	75.04 (4)	C15—C14—C13	121.60 (15)
O1—Eu1—N1	85.33 (4)	C19—C14—C13	118.98 (15)
O5—Eu1—N2	77.50 (4)	C16—C15—C14	119.73 (19)
O3ⁱ—Eu1—N2	145.74 (4)	C16—C15—H15A	120.1
O6ⁱ—Eu1—N2	136.06 (4)	C14—C15—H15A	120.1
O4—Eu1—N2	70.77 (4)	C17—C16—C15	120.2 (2)
O2—Eu1—N2	110.01 (4)	C17—C16—H16A	119.9
O1—Eu1—N2	70.10 (4)	C15—C16—H16A	119.9
N1—Eu1—N2	63.41 (4)	C18—C17—C16	120.69 (19)
O5—Eu1—O3	75.18 (3)	C18—C17—H17A	119.7
O3ⁱ—Eu1—O3	75.56 (4)	C16—C17—H17A	119.7
O6ⁱ—Eu1—O3	65.45 (3)	C17—C18—C19	119.8 (2)
O4—Eu1—O3	50.80 (3)	C17—C18—H18A	120.1
O2—Eu1—O3	133.58 (3)	C19—C18—H18A	120.1
O1—Eu1—O3	158.51 (3)	C18—C19—C14	120.20 (19)
N1—Eu1—O3	115.90 (3)	C18—C19—H19A	119.9
N2—Eu1—O3	115.03 (3)	C14—C19—H19A	119.9
O5—Eu1—C13	105.75 (4)	O4—C20—O3	120.53 (13)
O3ⁱ—Eu1—C13	77.90 (4)	O4—C20—C21	119.75 (12)
O6ⁱ—Eu1—C13	100.63 (4)	O3—C20—C21	119.68 (12)
O4—Eu1—C13	155.22 (4)	O4—C20—Eu1	57.16 (7)
O2—Eu1—C13	25.84 (4)	O3—C20—Eu1	65.51 (7)
O1—Eu1—C13	26.49 (4)	C21—C20—Eu1	162.76 (10)
N1—Eu1—C13	81.65 (4)	C22—C21—C26	119.52 (15)
N2—Eu1—C13	91.99 (4)	C22—C21—C20	120.52 (13)
O3—Eu1—C13	152.04 (3)	C26—C21—C20	119.92 (14)
O5—Eu1—C20	84.79 (4)	C23—C22—C21	120.07 (17)
O3ⁱ—Eu1—C20	101.47 (4)	C23—C22—H22A	120.0
O6ⁱ—Eu1—C20	68.28 (4)	C21—C22—H22A	120.0
O4—Eu1—C20	25.32 (4)	C24—C23—C22	120.1 (2)
O2—Eu1—C20	142.92 (4)	C24—C23—H23A	120.0
O1—Eu1—C20	163.61 (4)	C22—C23—H23A	120.0
N1—Eu1—C20	92.95 (4)	C23—C24—C25	120.45 (19)
N2—Eu1—C20	94.54 (4)	C23—C24—H24A	119.8
O3—Eu1—C20	26.05 (3)	C25—C24—H24A	119.8
C13—Eu1—C20	168.62 (4)	C24—C25—C26	120.28 (19)
O5—Eu1—Eu1ⁱ	70.46 (2)	C24—C25—H25A	119.9
O3ⁱ—Eu1—Eu1ⁱ	40.20 (3)	C26—C25—H25A	119.9
O6ⁱ—Eu1—Eu1ⁱ	66.47 (2)	C25—C26—C21	119.59 (19)
O4—Eu1—Eu1ⁱ	86.12 (3)	C25—C26—H26A	120.2
O2—Eu1—Eu1ⁱ	106.95 (3)	C21—C26—H26A	120.2
O1—Eu1—Eu1ⁱ	127.70 (3)	O6—C27—O5	125.43 (12)
N1—Eu1—Eu1ⁱ	140.81 (3)	O6—C27—C28	116.39 (12)
N2—Eu1—Eu1ⁱ	140.89 (3)	O5—C27—C28	118.18 (12)
O3—Eu1—Eu1ⁱ	35.36 (2)	C33—C28—C29	119.37 (14)
C13—Eu1—Eu1ⁱ	117.61 (3)	C33—C28—C27	119.47 (13)
C20—Eu1—Eu1ⁱ	61.32 (3)	C29—C28—C27	121.07 (13)
C13—O1—Eu1	92.94 (9)	C30—C29—C28	120.35 (15)
C13—O2—Eu1	93.86 (9)	C30—C29—H29A	119.8
C20—O3—Eu1ⁱ	165.77 (10)	C28—C29—H29A	119.8
C20—O3—Eu1	88.44 (8)	C31—C30—C29	119.75 (18)
Eu1ⁱ—O3—Eu1	104.44 (4)	C31—C30—H30A	120.1
C20—O4—Eu1	97.52 (8)	C29—C30—H30A	120.1
C27—O5—Eu1	133.44 (9)	C30—C31—C32	120.57 (18)
C27—O6—Eu1ⁱ	141.23 (9)	C30—C31—H31A	119.7
C2—N1—C1	117.91 (13)	C32—C31—H31A	119.7
C2—N1—Eu1	121.18 (10)	C31—C32—C33	120.08 (19)
C1—N1—Eu1	120.74 (9)	C31—C32—H32A	120.0
C11—N2—C12	117.65 (13)	C33—C32—H32A	120.0
C11—N2—Eu1	123.20 (10)	C28—C33—C32	119.82 (18)
C12—N2—Eu1	119.10 (9)	C28—C33—H33A	120.1
N1—C1—C5	122.16 (14)	C32—C33—H33A	120.1
N1—C1—C12	118.18 (12)	C34—O8—H1O8	114 (2)
C5—C1—C12	119.63 (14)	O7—C34—O8	123.2 (2)
N1—C2—C3	123.21 (17)	O7—C34—C35	124.0 (2)
N1—C2—H2A	118.4	O8—C34—C35	112.8 (2)
C3—C2—H2A	118.4	C40—C35—C36	119.4 (2)
C4—C3—C2	119.36 (17)	C40—C35—C34	122.0 (2)
C4—C3—H3A	120.3	C36—C35—C34	118.6 (2)
C2—C3—H3A	120.3	C37—C36—C35	119.9 (4)
C3—C4—C5	119.34 (15)	C37—C36—H36A	120.0
C3—C4—H4A	120.3	C35—C36—H36A	120.0
C5—C4—H4A	120.3	C38—C37—C36	120.6 (4)
C4—C5—C1	118.01 (16)	C38—C37—H37A	119.7
C4—C5—C6	122.71 (16)	C36—C37—H37A	119.7
C1—C5—C6	119.28 (17)	C37—C38—C39	120.7 (3)
C7—C6—C5	121.27 (16)	C37—C38—H38A	119.6
C7—C6—H6A	119.4	C39—C38—H38A	119.6
C5—C6—H6A	119.4	C38—C39—C40	119.7 (4)
C6—C7—C8	121.27 (16)	C38—C39—H39A	120.1
C6—C7—H7A	119.4	C40—C39—H39A	120.1
C8—C7—H7A	119.4	C35—C40—C39	119.6 (4)
C9—C8—C12	117.84 (16)	C35—C40—H40A	120.2
C9—C8—C7	123.03 (16)	C39—C40—H40A	120.2
C12—C8—C7	119.12 (17)

O5—Eu1—O1—C13	−137.91 (9)	C9—C8—C12—C1	178.47 (15)
O3ⁱ—Eu1—O1—C13	−63.82 (8)	C7—C8—C12—C1	−1.0 (2)
O6ⁱ—Eu1—O1—C13	10.75 (10)	N1—C1—C12—N2	1.8 (2)
O4—Eu1—O1—C13	139.55 (9)	C5—C1—C12—N2	−179.89 (13)
O2—Eu1—O1—C13	5.99 (8)	N1—C1—C12—C8	−177.52 (14)
N1—Eu1—O1—C13	80.64 (9)	C5—C1—C12—C8	0.8 (2)
N2—Eu1—O1—C13	144.02 (9)	Eu1—O2—C13—O1	10.94 (14)
O3—Eu1—O1—C13	−108.00 (11)	Eu1—O2—C13—C14	−168.42 (11)
C20—Eu1—O1—C13	165.19 (12)	Eu1—O1—C13—O2	−10.92 (14)
Eu1ⁱ—Eu1—O1—C13	−76.24 (9)	Eu1—O1—C13—C14	168.44 (11)
O5—Eu1—O2—C13	40.92 (10)	O5—Eu1—C13—O2	−146.86 (9)
O3ⁱ—Eu1—O2—C13	95.95 (9)	O3ⁱ—Eu1—C13—O2	−77.47 (9)
O6ⁱ—Eu1—O2—C13	177.82 (10)	O6ⁱ—Eu1—C13—O2	−2.14 (9)
O4—Eu1—O2—C13	−132.93 (9)	O4—Eu1—C13—O2	90.88 (13)
O1—Eu1—O2—C13	−6.13 (8)	O1—Eu1—C13—O2	169.12 (14)
N1—Eu1—O2—C13	−101.94 (9)	N1—Eu1—C13—O2	72.81 (9)
N2—Eu1—O2—C13	−48.13 (10)	N2—Eu1—C13—O2	135.56 (9)
O3—Eu1—O2—C13	146.34 (8)	O3—Eu1—C13—O2	−58.89 (12)
C20—Eu1—O2—C13	−176.56 (8)	C20—Eu1—C13—O2	10.6 (2)
Eu1ⁱ—Eu1—O2—C13	118.83 (8)	Eu1ⁱ—Eu1—C13—O2	−71.02 (9)
O5—Eu1—O3—C20	−109.12 (8)	O5—Eu1—C13—O1	44.02 (9)
O3ⁱ—Eu1—O3—C20	173.89 (10)	O3ⁱ—Eu1—C13—O1	113.41 (9)
O6ⁱ—Eu1—O3—C20	90.46 (8)	O6ⁱ—Eu1—C13—O1	−171.25 (8)
O4—Eu1—O3—C20	−9.08 (8)	O4—Eu1—C13—O1	−78.24 (13)
O2—Eu1—O3—C20	124.11 (8)	O2—Eu1—C13—O1	−169.12 (14)
O1—Eu1—O3—C20	−140.10 (10)	N1—Eu1—C13—O1	−96.31 (9)
N1—Eu1—O3—C20	30.32 (9)	N2—Eu1—C13—O1	−33.55 (9)
N2—Eu1—O3—C20	−40.86 (9)	O3—Eu1—C13—O1	131.99 (9)
C13—Eu1—O3—C20	155.12 (9)	C20—Eu1—C13—O1	−158.57 (16)
Eu1ⁱ—Eu1—O3—C20	173.88 (10)	Eu1ⁱ—Eu1—C13—O1	119.86 (8)
O5—Eu1—O3—Eu1ⁱ	77.00 (4)	O5—Eu1—C13—C14	−53.4 (6)
O3ⁱ—Eu1—O3—Eu1ⁱ	0.0	O3ⁱ—Eu1—C13—C14	16.0 (6)
O6ⁱ—Eu1—O3—Eu1ⁱ	−83.42 (4)	O6ⁱ—Eu1—C13—C14	91.3 (6)
O4—Eu1—O3—Eu1ⁱ	177.04 (6)	O4—Eu1—C13—C14	−175.7 (6)
O2—Eu1—O3—Eu1ⁱ	−49.77 (6)	O2—Eu1—C13—C14	93.4 (6)
O1—Eu1—O3—Eu1ⁱ	46.02 (10)	O1—Eu1—C13—C14	−97.4 (6)
N1—Eu1—O3—Eu1ⁱ	−143.56 (4)	N1—Eu1—C13—C14	166.3 (6)
N2—Eu1—O3—Eu1ⁱ	145.25 (4)	N2—Eu1—C13—C14	−131.0 (6)
C13—Eu1—O3—Eu1ⁱ	−18.77 (9)	O3—Eu1—C13—C14	34.6 (6)
C20—Eu1—O3—Eu1ⁱ	−173.88 (10)	C20—Eu1—C13—C14	104.0 (6)
O5—Eu1—O4—C20	81.57 (9)	Eu1ⁱ—Eu1—C13—C14	22.4 (6)
O3ⁱ—Eu1—O4—C20	12.88 (11)	O2—C13—C14—C15	−156.05 (15)
O6ⁱ—Eu1—O4—C20	−55.73 (9)	O1—C13—C14—C15	24.6 (2)
O2—Eu1—O4—C20	−103.37 (10)	Eu1—C13—C14—C15	116.3 (6)
O1—Eu1—O4—C20	163.41 (8)	O2—C13—C14—C19	24.7 (2)
N1—Eu1—O4—C20	−134.40 (10)	O1—C13—C14—C19	−154.66 (15)
N2—Eu1—O4—C20	158.96 (10)	Eu1—C13—C14—C19	−63.0 (6)
O3—Eu1—O4—C20	9.32 (8)	C19—C14—C15—C16	−1.4 (2)
C13—Eu1—O4—C20	−152.94 (10)	C13—C14—C15—C16	179.34 (15)
Eu1ⁱ—Eu1—O4—C20	11.04 (9)	C14—C15—C16—C17	1.3 (3)
O3ⁱ—Eu1—O5—C27	23.71 (13)	C15—C16—C17—C18	0.1 (3)
O6ⁱ—Eu1—O5—C27	−29.02 (15)	C16—C17—C18—C19	−1.3 (4)
O4—Eu1—O5—C27	−104.93 (13)	C17—C18—C19—C14	1.1 (3)
O2—Eu1—O5—C27	78.58 (14)	C15—C14—C19—C18	0.2 (3)
O1—Eu1—O5—C27	113.93 (13)	C13—C14—C19—C18	179.51 (16)
N1—Eu1—O5—C27	−168.10 (12)	Eu1—O4—C20—O3	−17.58 (15)
N2—Eu1—O5—C27	−175.63 (14)	Eu1—O4—C20—C21	160.12 (11)
O3—Eu1—O5—C27	−55.17 (13)	Eu1ⁱ—O3—C20—O4	171.4 (3)
C13—Eu1—O5—C27	95.84 (13)	Eu1—O3—C20—O4	16.19 (14)
C20—Eu1—O5—C27	−79.80 (13)	Eu1ⁱ—O3—C20—C21	−6.3 (5)
Eu1ⁱ—Eu1—O5—C27	−18.42 (12)	Eu1—O3—C20—C21	−161.51 (12)
O5—Eu1—N1—C2	172.83 (12)	Eu1ⁱ—O3—C20—Eu1	155.2 (4)
O3ⁱ—Eu1—N1—C2	−26.78 (16)	O5—Eu1—C20—O4	−96.87 (10)
O6ⁱ—Eu1—N1—C2	20.54 (13)	O3ⁱ—Eu1—C20—O4	−169.43 (9)
O4—Eu1—N1—C2	105.26 (13)	O6ⁱ—Eu1—C20—O4	118.36 (10)
O2—Eu1—N1—C2	−56.95 (13)	O2—Eu1—C20—O4	112.53 (10)
O1—Eu1—N1—C2	−108.89 (13)	O1—Eu1—C20—O4	−39.80 (18)
N2—Eu1—N1—C2	−178.95 (14)	N1—Eu1—C20—O4	43.66 (10)
O3—Eu1—N1—C2	74.62 (13)	N2—Eu1—C20—O4	−19.88 (10)
C13—Eu1—N1—C2	−82.48 (13)	O3—Eu1—C20—O4	−163.39 (14)
C20—Eu1—N1—C2	87.45 (13)	C13—Eu1—C20—O4	104.9 (2)
Eu1ⁱ—Eu1—N1—C2	41.66 (15)	Eu1ⁱ—Eu1—C20—O4	−167.42 (10)
O5—Eu1—N1—C1	−2.21 (14)	O5—Eu1—C20—O3	66.52 (8)
O3ⁱ—Eu1—N1—C1	158.18 (9)	O3ⁱ—Eu1—C20—O3	−6.04 (10)
O6ⁱ—Eu1—N1—C1	−154.50 (11)	O6ⁱ—Eu1—C20—O3	−78.25 (8)
O4—Eu1—N1—C1	−69.78 (11)	O4—Eu1—C20—O3	163.39 (14)
O2—Eu1—N1—C1	128.00 (11)	O2—Eu1—C20—O3	−84.08 (10)
O1—Eu1—N1—C1	76.07 (11)	O1—Eu1—C20—O3	123.60 (13)
N2—Eu1—N1—C1	6.01 (10)	N1—Eu1—C20—O3	−152.95 (8)
O3—Eu1—N1—C1	−100.42 (11)	N2—Eu1—C20—O3	143.51 (8)
C13—Eu1—N1—C1	102.48 (11)	C13—Eu1—C20—O3	−91.7 (2)
C20—Eu1—N1—C1	−87.60 (11)	Eu1ⁱ—Eu1—C20—O3	−4.03 (7)
Eu1ⁱ—Eu1—N1—C1	−133.38 (9)	O5—Eu1—C20—C21	178.1 (3)
O5—Eu1—N2—C11	−7.65 (13)	O3ⁱ—Eu1—C20—C21	105.6 (3)
O3ⁱ—Eu1—N2—C11	26.80 (16)	O6ⁱ—Eu1—C20—C21	33.3 (3)
O6ⁱ—Eu1—N2—C11	−154.38 (12)	O4—Eu1—C20—C21	−85.0 (3)
O4—Eu1—N2—C11	−100.15 (13)	O2—Eu1—C20—C21	27.5 (3)
O2—Eu1—N2—C11	116.99 (13)	O1—Eu1—C20—C21	−124.8 (3)
O1—Eu1—N2—C11	82.84 (13)	N1—Eu1—C20—C21	−41.4 (3)
N1—Eu1—N2—C11	177.69 (14)	N2—Eu1—C20—C21	−104.9 (3)
O3—Eu1—N2—C11	−74.53 (13)	O3—Eu1—C20—C21	111.6 (3)
C13—Eu1—N2—C11	98.04 (13)	C13—Eu1—C20—C21	19.9 (4)
C20—Eu1—N2—C11	−91.29 (13)	Eu1ⁱ—Eu1—C20—C21	107.6 (3)
Eu1ⁱ—Eu1—N2—C11	−43.01 (14)	O4—C20—C21—C22	−142.59 (16)
O5—Eu1—N2—C12	169.73 (11)	O3—C20—C21—C22	35.1 (2)
O3ⁱ—Eu1—N2—C12	−155.82 (9)	Eu1—C20—C21—C22	−68.0 (4)
O6ⁱ—Eu1—N2—C12	23.01 (13)	O4—C20—C21—C26	35.0 (2)
O4—Eu1—N2—C12	77.23 (10)	O3—C20—C21—C26	−147.24 (16)
O2—Eu1—N2—C12	−65.62 (11)	Eu1—C20—C21—C26	109.6 (3)
O1—Eu1—N2—C12	−99.77 (11)	C26—C21—C22—C23	0.4 (3)
N1—Eu1—N2—C12	−4.93 (10)	C20—C21—C22—C23	178.04 (17)
O3—Eu1—N2—C12	102.85 (10)	C21—C22—C23—C24	0.1 (3)
C13—Eu1—N2—C12	−84.57 (10)	C22—C23—C24—C25	−0.6 (4)
C20—Eu1—N2—C12	86.09 (10)	C23—C24—C25—C26	0.4 (4)
Eu1ⁱ—Eu1—N2—C12	134.37 (9)	C24—C25—C26—C21	0.1 (4)
C2—N1—C1—C5	−0.2 (2)	C22—C21—C26—C25	−0.5 (3)
Eu1—N1—C1—C5	175.00 (11)	C20—C21—C26—C25	−178.2 (2)
C2—N1—C1—C12	178.03 (14)	Eu1ⁱ—O6—C27—O5	−3.4 (3)
Eu1—N1—C1—C12	−6.77 (17)	Eu1ⁱ—O6—C27—C28	177.45 (10)
C1—N1—C2—C3	1.3 (3)	Eu1—O5—C27—O6	21.8 (2)
Eu1—N1—C2—C3	−173.87 (14)	Eu1—O5—C27—C28	−159.07 (10)
N1—C2—C3—C4	−1.1 (3)	O6—C27—C28—C33	−31.8 (2)
C2—C3—C4—C5	−0.2 (3)	O5—C27—C28—C33	148.90 (17)
C3—C4—C5—C1	1.3 (3)	O6—C27—C28—C29	144.80 (15)
C3—C4—C5—C6	−177.65 (19)	O5—C27—C28—C29	−34.4 (2)
N1—C1—C5—C4	−1.1 (2)	C33—C28—C29—C30	2.4 (3)
C12—C1—C5—C4	−179.27 (15)	C27—C28—C29—C30	−174.23 (17)
N1—C1—C5—C6	177.88 (15)	C28—C29—C30—C31	−2.3 (3)
C12—C1—C5—C6	−0.3 (2)	C29—C30—C31—C32	0.4 (4)
C4—C5—C6—C7	179.10 (19)	C30—C31—C32—C33	1.5 (5)
C1—C5—C6—C7	0.2 (3)	C29—C28—C33—C32	−0.6 (3)
C5—C6—C7—C8	−0.5 (3)	C27—C28—C33—C32	176.1 (2)
C6—C7—C8—C9	−178.54 (19)	C31—C32—C33—C28	−1.3 (4)
C6—C7—C8—C12	1.0 (3)	O7—C34—C35—C40	178.8 (3)
C12—C8—C9—C10	0.5 (3)	O8—C34—C35—C40	0.0 (3)
C7—C8—C9—C10	179.98 (18)	O7—C34—C35—C36	0.4 (3)
C8—C9—C10—C11	0.0 (3)	O8—C34—C35—C36	−178.4 (2)
C12—N2—C11—C10	−0.1 (3)	C40—C35—C36—C37	−0.1 (4)
Eu1—N2—C11—C10	177.34 (14)	C34—C35—C36—C37	178.3 (2)
C9—C10—C11—N2	−0.3 (3)	C35—C36—C37—C38	−0.8 (5)
C11—N2—C12—C8	0.7 (2)	C36—C37—C38—C39	1.3 (6)
Eu1—N2—C12—C8	−176.87 (11)	C37—C38—C39—C40	−0.8 (6)
C11—N2—C12—C1	−178.68 (14)	C36—C35—C40—C39	0.6 (4)
Eu1—N2—C12—C1	3.79 (17)	C34—C35—C40—C39	−177.8 (3)
C9—C8—C12—N2	−0.9 (2)	C38—C39—C40—C35	−0.1 (5)
C7—C8—C12—N2	179.62 (15)

Symmetry code: (i) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C35–C40 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O8—H1O8···O1	0.86 (3)	1.82 (3)	2.660 (2)	166 (3)
C2—H2A···O6ⁱ	0.93	2.43	3.017 (2)	121
C9—H9A···O2ⁱⁱ	0.93	2.51	3.258 (2)	138
C11—H11A···O5	0.93	2.44	3.079 (2)	126
C25—H25A···Cg1ⁱⁱⁱ	0.93	2.65	3.551 (3)	164

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

Experimental details

Crystal data
Chemical formula	[Eu₂(C₇H₅O₂)₆(C₁₂H₈N₂)₂]·2C₇H₆O₂
M_r	1635.22
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	9.6688 (2), 12.8260 (2), 15.1460 (3)
α, β, γ (°)	75.244 (1), 78.605 (1), 76.072 (1)
V (Å³)	1744.26 (6)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.86
Crystal size (mm)	0.58 × 0.32 × 0.28

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.413, 0.628
No. of measured, independent and observed [I > 2σ(I)] reflections	51513, 12557, 11674
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.756

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.020, 0.050, 1.04
No. of reflections	12557
No. of parameters	464
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.44

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Selected bond lengths (Å) top

Eu1—O5	2.3667 (9)	Eu1—O1	2.4974 (11)
Eu1—O3ⁱ	2.3669 (9)	Eu1—N1	2.5636 (11)
Eu1—O6ⁱ	2.3818 (10)	Eu1—N2	2.6134 (11)
Eu1—O4	2.4571 (11)	Eu1—O3	2.6394 (11)
Eu1—O2	2.4933 (11)

Symmetry code: (i) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C35–C40 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O8—H1O8···O1	0.86 (3)	1.82 (3)	2.660 (2)	166 (3)
C2—H2A···O6ⁱ	0.9300	2.4300	3.017 (2)	121.00
C9—H9A···O2ⁱⁱ	0.9300	2.5100	3.258 (2)	138.00
C11—H11A···O5	0.9300	2.4400	3.079 (2)	126.00
C25—H25A···Cg1ⁱⁱⁱ	0.9300	2.6500	3.551 (3)	164.00

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

Footnotes

‡Additional corresponding author, e-mail: howieooi83@gmail.com.

§Thomson Reuters ResearcherID: A-5523-2009.

¶Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

SGT and PHO thank Universiti Sains Malaysia (USM) for the University Grant (No. 1001/229/PKIMIA/815002) for this research. HKF and CSY thank USM for the Research University Golden Goose grant (No. 1001/PFIZIK/811012). CSY also thanks USM for the award of a USM fellowship.

References

Beeby, A., Botchway, S. W., Clarkson, I. M., Faulkner, S., Parker, A. W., Parker, D. & William, J. A. G. (2003). J. Photochem. Photobiol B Biol. 57, 83–89. Web of Science CrossRef Google Scholar
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Volume 66| Part 5| May 2010| Pages m597-m598

https://doi.org/10.1107/S1600536810015229

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