Tris{2-meth­oxy-6-[(4-methyl­phen­yl)iminiometh­yl]phenolate-κ2O,O′}tris­(thio­cyanato-κN)europium(III)

Liu, J.-F.; Liu, J.-L.; Zhao, G.-L.

doi:10.1107/S1600536809049125

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page m1651

doi:10.1107/S1600536809049125

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Tris{2-methoxy-6-[(4-methylphenyl)iminiomethyl]phenolate-κ²O,O′}tris(thiocyanato-κN)europium(III)

Jian-Feng Liu,^a Jia-Lu Liu ^a and Guo-Liang Zhao ^a ^*

^aZhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Institute of Physical Chemistry, Zhejiang Normal University, Jinhua, Zhejiang 321004, People's Republic of China, and College of Chemistry and Life Science, Zhejiang Normal University, Jinhua 321004, Zhejiang, People's Republic of China
^*Correspondence e-mail: sky53@zjnu.cn

(Received 6 October 2009; accepted 18 November 2009; online 21 November 2009)

The metal center in the structure of the title compound, [Eu(NCS)₃(C₁₅H₁₅NO₂)₃], is coordinated by three Schiff base 2-methoxy-6-[(4-methylphenyl)iminiomethyl]phenolate (L) ligands and three independent thiocyanate ions. In the crystal structure, the acidic H atom is located on the Schiff base N atom and hydrogen bonded to the phenolate O atom. The coordination environment of the Eu^III ion is nine-coordinate by three chelating methoxyphenolate pairs of O atoms and three N-atom terminals of the thiocyanate ions. The compound is isostructural with the Ce^III analogue [Liu et al. (2009 ). Acta Cryst. E65, m650].

Related literature

For background to Schiff bases and their applications, see: Liu et al. (1997 ); Mihara et al. (2009 ). For related structures, see: Liu et al. (2009); Zhao et al. (2007 ). For a zigzag chain cadmium(II) complex, see: Li et al. (2008 ).

Experimental

Crystal data

[Eu(NCS)₃(C₁₅H₁₅NO₂)₃]
M_r = 1050.04
Monoclinic, P 2₁ /c
a = 16.6445 (2) Å
b = 14.2411 (2) Å
c = 22.1678 (3) Å
β = 105.912 (1)°
V = 5053.23 (12) Å³
Z = 4
Mo Kα radiation
μ = 1.42 mm⁻¹
T = 296 K
0.31 × 0.16 × 0.13 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.757, T_max = 0.834
37461 measured reflections
8882 independent reflections
6762 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.137
S = 1.06
8882 reflections
577 parameters
H-atom parameters constrained
Δρ_max = 0.87 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.86	1.89	2.588 (4)	138
N2—H2A⋯O3	0.86	1.89	2.580 (4)	137
N3—H3A⋯O5	0.86	1.84	2.550 (4)	138

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809049125/zl2242sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809049125/zl2242Isup2.hkl

checkCIF report

Comment top

Rare earth complexes with Schiff ligands derived from o-vanillin have been investigated over many years. Liu et al. (1997) for example describe structural and chemical properties of vanilline derived complexes, and (Mihara et al., 2009) investigated them as catalytsts for asymmetric α-additions of isocyanides to aldehydes. Over the last years we have been engaged in the syntheses of new analogous Schiff bases derived from o-vanillin and their rare metal complexes. In prvious articles we have reported partial results (Zhao et al., 2007; Li et al. 2008; Liu et al. 2009). Herein, we would like to describe a new Eu^III complex.

The structure of the title complex is shown in Fig.1. The structure of [Eu(NCS)₃.(C₁₅H₁₅NO₂)₃] contains three (HL) ligands and three independent thiocyanate ions. The Eu^III is nine-coordinated by three N terminals from three thiocyanate ions and six O atoms from the HL ligands (shown in Fig. 2). The HL ligands chelate the Eu^III ion with the methoxy O atoms and the deprotonated phenolic hydroxyl O atoms. The Eu—O (phenolic) bonds are 2.773 (3) - 2.839 (3) Å, which are longer than the ones between Eu^III and methoxy O atoms (2.376 (3) - 2.418 (3) Å). The Eu—N bonds are 2.512 (5) - 2.566 (5) Å. The Eu—O (phenolic) and Eu—N bonds are shorter than in the isostructural Ce^III complex (Liu et al. 2009), which can be attributed to the ionic radius decrease from Ce^III to Eu^III due to the lanthanide contraction. Because of the geometric and chemical environment requirements of the chelating groups, the coordination geometry deviates considerably from that of a distorted capped square antiprismatic geometry (Fig. 2). In the HL ligands, the acidic proton has been transferred from the phenolic group to the N-imine atom, which is involved in an intramolecular hydrogen bond. All hydrogen bonds are listed in Table 1.

Related literature top

For background to Schiff bases and their applications, see: Liu et al. (1997); Mihara et al. (2009). For related structures, see: Liu et al. (2009); Zhao et al. (2007). For a zigzag chain cadmium(II) complex, see: Li et al. (2008).

Experimental top

Reagents and solvents were of commercially available quality and were used without further purification. The Schiff base ligand was prepared in a high yield synthesis by condensation of o-vanillin and p-methylaniline and was recrystallized in ethanol before being used. 1 mmol Eu(NO₃)₃ (dissolved in methanol) was added dropwise into a methanol solution with 3 mmol N-salicylidene-p-toluidine under stirring and the mixture was continuously stirred at room temperature for 8 h to obtain a purplish red solution. The deposit was filtered off and the solution was left standing for slow evaporation. Red crystal of the title compound formed after several days.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title complex, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The coordination environment of the europium(III) atom, showing the distorted monocapped square antiprismatic geometry.

Tris{2-methoxy-6-[(4-methylphenyl)iminiomethyl]phenolate- κ²O,O'}tris(thiocyanato-κN)europium(III) top

Crystal data top

[Eu(NCS)₃(C₁₅H₁₅NO₂)₃]	F(000) = 2136
M_r = 1050.04	D_x = 1.380 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7369 reflections
a = 16.6445 (2) Å	θ = 2.0–25.0°
b = 14.2411 (2) Å	µ = 1.42 mm⁻¹
c = 22.1678 (3) Å	T = 296 K
β = 105.912 (1)°	Block, red
V = 5053.23 (12) Å³	0.31 × 0.16 × 0.13 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	8882 independent reflections
Radiation source: fine-focus sealed tube	6762 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
phi and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→19
T_min = 0.757, T_max = 0.834	k = −16→16
37461 measured reflections	l = −23→26

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0857P)²] where P = (F_o² + 2F_c²)/3
8882 reflections	(Δ/σ)_max = 0.001
577 parameters	Δρ_max = 0.87 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

[Eu(NCS)₃(C₁₅H₁₅NO₂)₃]	V = 5053.23 (12) Å³
M_r = 1050.04	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.6445 (2) Å	µ = 1.42 mm⁻¹
b = 14.2411 (2) Å	T = 296 K
c = 22.1678 (3) Å	0.31 × 0.16 × 0.13 mm
β = 105.912 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	8882 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	6762 reflections with I > 2σ(I)
T_min = 0.757, T_max = 0.834	R_int = 0.046
37461 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.06	Δρ_max = 0.87 e Å⁻³
8882 reflections	Δρ_min = −0.41 e Å⁻³
577 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
Eu	0.212188 (12)	0.775828 (17)	0.392808 (11)	0.04651 (12)
C1	−0.0555 (3)	0.7601 (3)	0.4198 (2)	0.0496 (12)
C2	0.0249 (3)	0.7317 (3)	0.4190 (2)	0.0419 (10)
C3	0.0421 (3)	0.6343 (3)	0.4173 (2)	0.0482 (11)
C4	−0.0183 (4)	0.5697 (4)	0.4158 (3)	0.0741 (17)
H4A	−0.0063	0.5062	0.4143	0.089*
C5	−0.0979 (4)	0.5975 (4)	0.4164 (3)	0.089 (2)
H5A	−0.1386	0.5523	0.4152	0.107*
C6	−0.1172 (3)	0.6901 (4)	0.4186 (3)	0.0768 (18)
H6A	−0.1707	0.7077	0.4194	0.092*
C7	−0.0755 (3)	0.8557 (3)	0.4200 (2)	0.0510 (12)
H7A	−0.1291	0.8720	0.4213	0.061*
C8	0.1514 (4)	0.5228 (4)	0.4240 (3)	0.0787 (18)
H8A	0.1088	0.4829	0.4317	0.118*
H8B	0.2006	0.5189	0.4588	0.118*
H8C	0.1645	0.5028	0.3864	0.118*
C9	−0.0370 (2)	1.0207 (3)	0.41823 (19)	0.0417 (10)
C10	0.0249 (3)	1.0782 (4)	0.4082 (2)	0.0537 (12)
H10A	0.0731	1.0522	0.4017	0.064*
C11	0.0150 (3)	1.1736 (4)	0.4081 (3)	0.0618 (13)
H11A	0.0573	1.2118	0.4017	0.074*
C12	−0.0553 (4)	1.2144 (3)	0.4170 (2)	0.0585 (14)
C13	−0.1161 (3)	1.1561 (4)	0.4272 (2)	0.0560 (12)
H13A	−0.1642	1.1821	0.4339	0.067*
C14	−0.1071 (3)	1.0589 (3)	0.4279 (2)	0.0512 (11)
H14A	−0.1488	1.0204	0.4349	0.061*
C15	−0.0667 (4)	1.3191 (4)	0.4163 (3)	0.0801 (18)
H15A	−0.0192	1.3490	0.4080	0.120*
H15B	−0.0719	1.3394	0.4564	0.120*
H15C	−0.1163	1.3358	0.3842	0.120*
C16	0.4877 (2)	0.8421 (3)	0.3996 (2)	0.0417 (10)
C17	0.4005 (2)	0.8307 (3)	0.3755 (2)	0.0401 (10)
C18	0.3682 (3)	0.8078 (3)	0.3111 (2)	0.0466 (11)
C19	0.4192 (3)	0.7976 (4)	0.2730 (2)	0.0552 (12)
H19A	0.3967	0.7839	0.2307	0.066*
C20	0.5051 (3)	0.8079 (4)	0.2974 (3)	0.0600 (13)
H20A	0.5395	0.8001	0.2711	0.072*
C21	0.5395 (3)	0.8290 (4)	0.3585 (2)	0.0561 (13)
H21A	0.5972	0.8349	0.3738	0.067*
C22	0.5236 (3)	0.8642 (3)	0.4622 (2)	0.0452 (11)
H22A	0.5815	0.8699	0.4763	0.054*
C23	0.2420 (4)	0.7996 (5)	0.2274 (2)	0.082 (2)
H23A	0.2825	0.8111	0.2047	0.123*
H23B	0.1996	0.8472	0.2172	0.123*
H23C	0.2170	0.7391	0.2162	0.123*
C24	0.5109 (3)	0.8965 (3)	0.5674 (2)	0.0447 (10)
C25	0.5932 (3)	0.9208 (4)	0.5954 (2)	0.0533 (12)
H25A	0.6303	0.9285	0.5712	0.064*
C26	0.6195 (3)	0.9335 (4)	0.6590 (2)	0.0630 (14)
H26A	0.6749	0.9501	0.6774	0.076*
C27	0.5675 (4)	0.9228 (4)	0.6963 (3)	0.0688 (15)
C28	0.4859 (4)	0.9002 (4)	0.6681 (3)	0.0739 (16)
H28A	0.4488	0.8941	0.6925	0.089*
C29	0.4578 (3)	0.8862 (4)	0.6044 (2)	0.0635 (14)
H29A	0.4023	0.8696	0.5864	0.076*
C30	0.5990 (5)	0.9382 (5)	0.7666 (3)	0.105 (2)
H30A	0.5541	0.9286	0.7854	0.158*
H30B	0.6196	1.0012	0.7748	0.158*
H30C	0.6432	0.8946	0.7842	0.158*
C31	0.3719 (3)	0.5437 (4)	0.3346 (2)	0.0576 (13)
C32	0.3006 (3)	0.5925 (3)	0.3394 (2)	0.0496 (11)
C33	0.2273 (3)	0.5862 (4)	0.2897 (2)	0.0571 (12)
C34	0.2241 (5)	0.5321 (5)	0.2387 (3)	0.087 (2)
H34A	0.1750	0.5286	0.2063	0.105*
C35	0.2944 (6)	0.4814 (6)	0.2347 (3)	0.103 (2)
H35A	0.2908	0.4432	0.2001	0.123*
C36	0.3666 (5)	0.4865 (5)	0.2794 (3)	0.0869 (19)
H36A	0.4132	0.4537	0.2753	0.104*
C37	0.4482 (3)	0.5515 (4)	0.3816 (3)	0.0591 (13)
H37A	0.4945	0.5192	0.3767	0.071*
C38	0.0808 (4)	0.6303 (5)	0.2585 (3)	0.088 (2)
H38A	0.0801	0.5789	0.2303	0.133*
H38B	0.0642	0.6868	0.2347	0.133*
H38C	0.0426	0.6176	0.2830	0.133*
C39	0.5297 (3)	0.6218 (3)	0.4791 (3)	0.0554 (13)
C40	0.6085 (3)	0.6166 (4)	0.4702 (3)	0.0703 (15)
H40A	0.6153	0.5965	0.4320	0.084*
C41	0.6768 (3)	0.6413 (5)	0.5182 (4)	0.086 (2)
H41A	0.7296	0.6382	0.5116	0.104*
C42	0.6700 (3)	0.6700 (4)	0.5745 (4)	0.0795 (18)
C43	0.5901 (3)	0.6761 (4)	0.5832 (3)	0.0730 (16)
H43A	0.5838	0.6971	0.6214	0.088*
C44	0.5208 (3)	0.6515 (4)	0.5359 (3)	0.0631 (14)
H44A	0.4679	0.6550	0.5424	0.076*
C45	0.7453 (4)	0.7002 (6)	0.6284 (4)	0.119 (3)
H45A	0.7957	0.6922	0.6159	0.179*
H45B	0.7479	0.6622	0.6647	0.179*
H45C	0.7393	0.7650	0.6383	0.179*
C46	0.3000 (3)	0.6760 (4)	0.5457 (2)	0.0527 (12)
C47	0.0442 (4)	0.8630 (5)	0.2737 (3)	0.0781 (17)
C48	0.2338 (3)	1.0044 (4)	0.4741 (3)	0.0538 (12)
S1	0.33288 (14)	0.60173 (15)	0.60390 (8)	0.1038 (7)
S2	−0.05210 (12)	0.86508 (18)	0.23051 (12)	0.1316 (9)
S3	0.25269 (9)	1.10435 (12)	0.51097 (9)	0.0882 (6)
N1	−0.0237 (2)	0.9224 (3)	0.41848 (16)	0.0427 (9)
H1A	0.0254	0.9049	0.4175	0.051*
N2	0.4802 (2)	0.8774 (2)	0.50229 (16)	0.0418 (8)
H2A	0.4268	0.8742	0.4876	0.050*
N3	0.4561 (2)	0.6018 (3)	0.43120 (19)	0.0531 (10)
H3A	0.4109	0.6263	0.4357	0.064*
N4	0.2777 (3)	0.7258 (3)	0.5055 (2)	0.0592 (11)
N5	0.1114 (3)	0.8592 (4)	0.3037 (2)	0.0935 (18)
N6	0.2185 (2)	0.9354 (3)	0.4477 (2)	0.0652 (12)
O1	0.08463 (17)	0.7912 (2)	0.42051 (16)	0.0475 (8)
O2	0.1224 (2)	0.6171 (2)	0.41675 (17)	0.0593 (9)
O3	0.35011 (16)	0.8406 (2)	0.41093 (13)	0.0443 (7)
O4	0.28219 (19)	0.8018 (3)	0.29336 (14)	0.0553 (8)
O5	0.30193 (18)	0.6438 (2)	0.38871 (14)	0.0474 (7)
O6	0.1634 (2)	0.6416 (3)	0.29926 (15)	0.0611 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Eu	0.03922 (15)	0.05006 (19)	0.04699 (18)	0.00313 (9)	0.00630 (11)	0.00323 (11)
C1	0.046 (2)	0.042 (3)	0.062 (3)	−0.007 (2)	0.017 (2)	−0.002 (2)
C2	0.043 (2)	0.039 (3)	0.042 (3)	−0.0024 (19)	0.0084 (19)	0.001 (2)
C3	0.060 (3)	0.037 (3)	0.049 (3)	−0.003 (2)	0.018 (2)	−0.001 (2)
C4	0.075 (4)	0.041 (3)	0.106 (5)	−0.011 (3)	0.023 (3)	−0.005 (3)
C5	0.083 (4)	0.057 (4)	0.131 (6)	−0.032 (3)	0.038 (4)	−0.007 (4)
C6	0.055 (3)	0.058 (3)	0.123 (5)	−0.015 (3)	0.032 (3)	−0.004 (4)
C7	0.041 (2)	0.053 (3)	0.061 (3)	0.000 (2)	0.017 (2)	−0.008 (2)
C8	0.097 (4)	0.040 (3)	0.110 (5)	0.022 (3)	0.045 (4)	0.012 (3)
C9	0.043 (2)	0.043 (3)	0.036 (2)	0.0028 (19)	0.0059 (18)	0.000 (2)
C10	0.045 (2)	0.053 (3)	0.056 (3)	0.000 (2)	0.002 (2)	−0.001 (2)
C11	0.061 (3)	0.048 (3)	0.069 (4)	−0.010 (2)	0.005 (2)	0.002 (3)
C12	0.078 (3)	0.047 (3)	0.038 (3)	0.006 (3)	−0.005 (2)	−0.002 (2)
C13	0.066 (3)	0.048 (3)	0.053 (3)	0.011 (2)	0.015 (2)	−0.003 (2)
C14	0.058 (3)	0.043 (3)	0.054 (3)	0.003 (2)	0.018 (2)	0.003 (2)
C15	0.112 (5)	0.043 (3)	0.074 (4)	0.001 (3)	0.005 (3)	−0.002 (3)
C16	0.042 (2)	0.043 (3)	0.043 (3)	−0.0041 (18)	0.0156 (19)	−0.002 (2)
C17	0.045 (2)	0.034 (2)	0.042 (3)	−0.0011 (18)	0.0140 (19)	0.0045 (19)
C18	0.053 (2)	0.046 (3)	0.041 (3)	−0.005 (2)	0.013 (2)	0.006 (2)
C19	0.071 (3)	0.059 (3)	0.036 (3)	−0.003 (2)	0.015 (2)	0.000 (2)
C20	0.062 (3)	0.074 (4)	0.055 (3)	−0.001 (3)	0.034 (3)	−0.003 (3)
C21	0.044 (2)	0.070 (4)	0.057 (3)	−0.001 (2)	0.019 (2)	−0.005 (3)
C22	0.037 (2)	0.046 (3)	0.054 (3)	−0.0017 (18)	0.015 (2)	0.001 (2)
C23	0.068 (3)	0.139 (6)	0.031 (3)	−0.019 (4)	0.001 (2)	0.018 (3)
C24	0.052 (2)	0.039 (3)	0.042 (3)	0.0001 (19)	0.013 (2)	−0.002 (2)
C25	0.048 (2)	0.058 (3)	0.054 (3)	−0.009 (2)	0.014 (2)	−0.007 (2)
C26	0.069 (3)	0.055 (3)	0.056 (3)	−0.009 (3)	0.002 (3)	−0.010 (3)
C27	0.104 (4)	0.053 (3)	0.047 (3)	−0.013 (3)	0.017 (3)	−0.009 (3)
C28	0.098 (4)	0.083 (4)	0.048 (3)	−0.024 (3)	0.032 (3)	−0.013 (3)
C29	0.064 (3)	0.070 (4)	0.062 (3)	−0.016 (3)	0.025 (3)	−0.016 (3)
C30	0.161 (7)	0.099 (6)	0.050 (4)	−0.034 (5)	0.020 (4)	−0.015 (4)
C31	0.072 (3)	0.053 (3)	0.054 (3)	0.004 (2)	0.027 (3)	−0.007 (2)
C32	0.066 (3)	0.045 (3)	0.041 (3)	−0.001 (2)	0.019 (2)	0.005 (2)
C33	0.067 (3)	0.055 (3)	0.046 (3)	−0.004 (2)	0.009 (2)	0.003 (2)
C34	0.111 (5)	0.091 (5)	0.049 (4)	−0.024 (4)	0.006 (3)	−0.021 (3)
C35	0.135 (6)	0.105 (6)	0.072 (5)	−0.016 (5)	0.034 (5)	−0.044 (4)
C36	0.112 (5)	0.079 (5)	0.079 (5)	0.003 (4)	0.044 (4)	−0.019 (4)
C37	0.065 (3)	0.042 (3)	0.076 (4)	0.014 (2)	0.029 (3)	0.003 (3)
C38	0.071 (4)	0.090 (5)	0.078 (4)	−0.011 (3)	−0.023 (3)	0.007 (4)
C39	0.055 (3)	0.040 (3)	0.067 (3)	0.014 (2)	0.010 (2)	0.011 (2)
C40	0.060 (3)	0.062 (4)	0.091 (4)	0.022 (3)	0.025 (3)	0.005 (3)
C41	0.050 (3)	0.080 (5)	0.121 (6)	0.018 (3)	0.010 (3)	0.005 (4)
C42	0.062 (3)	0.053 (4)	0.104 (5)	0.012 (3)	−0.010 (3)	0.012 (4)
C43	0.080 (4)	0.049 (3)	0.075 (4)	0.010 (3)	−0.005 (3)	0.001 (3)
C44	0.059 (3)	0.049 (3)	0.077 (4)	0.011 (2)	0.013 (3)	0.010 (3)
C45	0.077 (4)	0.100 (5)	0.146 (7)	0.008 (4)	−0.028 (4)	0.000 (5)
C46	0.061 (3)	0.061 (3)	0.037 (3)	0.017 (2)	0.017 (2)	−0.006 (3)
C47	0.084 (4)	0.082 (4)	0.060 (4)	0.028 (3)	0.006 (3)	0.009 (3)
C48	0.036 (2)	0.057 (3)	0.071 (3)	−0.008 (2)	0.020 (2)	−0.007 (3)
S1	0.1488 (16)	0.1137 (15)	0.0626 (10)	0.0676 (13)	0.0518 (10)	0.0386 (10)
S2	0.0849 (12)	0.1219 (17)	0.148 (2)	0.0366 (12)	−0.0365 (12)	−0.0150 (15)
S3	0.0592 (8)	0.0801 (11)	0.1363 (15)	−0.0291 (7)	0.0455 (9)	−0.0507 (11)
N1	0.0374 (17)	0.043 (2)	0.048 (2)	0.0043 (16)	0.0115 (15)	0.0024 (17)
N2	0.0366 (17)	0.043 (2)	0.043 (2)	−0.0041 (15)	0.0067 (15)	−0.0012 (17)
N3	0.049 (2)	0.045 (2)	0.064 (3)	0.0140 (17)	0.0140 (19)	0.004 (2)
N4	0.061 (3)	0.068 (3)	0.048 (3)	0.012 (2)	0.012 (2)	0.009 (2)
N5	0.065 (3)	0.131 (5)	0.076 (4)	0.032 (3)	0.005 (3)	0.038 (3)
N6	0.052 (2)	0.057 (3)	0.093 (3)	−0.004 (2)	0.029 (2)	−0.014 (3)
O1	0.0397 (15)	0.0340 (17)	0.072 (2)	−0.0014 (12)	0.0208 (15)	0.0004 (15)
O2	0.066 (2)	0.0378 (18)	0.076 (2)	0.0080 (16)	0.0216 (17)	0.0007 (17)
O3	0.0363 (14)	0.056 (2)	0.0420 (17)	−0.0025 (13)	0.0138 (13)	−0.0035 (15)
O4	0.0519 (18)	0.073 (2)	0.0360 (18)	−0.0073 (16)	0.0040 (14)	0.0065 (16)
O5	0.0531 (17)	0.0491 (19)	0.0367 (17)	0.0077 (14)	0.0069 (13)	−0.0026 (15)
O6	0.062 (2)	0.070 (2)	0.0397 (19)	−0.0064 (18)	−0.0051 (15)	0.0018 (17)

Geometric parameters (Å, º) top

Eu—O1	2.376 (3)	C23—H23C	0.9600
Eu—O3	2.404 (3)	C24—C29	1.369 (6)
Eu—O5	2.418 (3)	C24—C25	1.383 (6)
Eu—N5	2.512 (5)	C24—N2	1.420 (5)
Eu—N4	2.538 (4)	C25—C26	1.369 (7)
Eu—N6	2.566 (5)	C25—H25A	0.9300
Eu—O6	2.773 (3)	C26—C27	1.359 (7)
Eu—O4	2.786 (3)	C26—H26A	0.9300
Eu—O2	2.839 (3)	C27—C28	1.368 (8)
C1—C2	1.403 (6)	C27—C30	1.519 (8)
C1—C7	1.402 (7)	C28—C29	1.374 (7)
C1—C6	1.427 (7)	C28—H28A	0.9300
C2—O1	1.299 (5)	C29—H29A	0.9300
C2—C3	1.419 (6)	C30—H30A	0.9600
C3—C4	1.356 (7)	C30—H30B	0.9600
C3—O2	1.362 (5)	C30—H30C	0.9600
C4—C5	1.385 (8)	C31—C32	1.405 (7)
C4—H4A	0.9300	C31—C37	1.409 (7)
C5—C6	1.361 (8)	C31—C36	1.452 (8)
C5—H5A	0.9300	C32—O5	1.310 (5)
C6—H6A	0.9300	C32—C33	1.406 (7)
C7—N1	1.289 (6)	C33—C34	1.356 (8)
C7—H7A	0.9300	C33—O6	1.386 (6)
C8—O2	1.422 (6)	C34—C35	1.398 (10)
C8—H8A	0.9600	C34—H34A	0.9300
C8—H8B	0.9600	C35—C36	1.333 (9)
C8—H8C	0.9600	C35—H35A	0.9300
C9—C14	1.357 (6)	C36—H36A	0.9300
C9—C10	1.380 (6)	C37—N3	1.289 (6)
C9—N1	1.417 (6)	C37—H37A	0.9300
C10—C11	1.369 (7)	C38—O6	1.433 (6)
C10—H10A	0.9300	C38—H38A	0.9600
C11—C12	1.369 (8)	C38—H38B	0.9600
C11—H11A	0.9300	C38—H38C	0.9600
C12—C13	1.376 (7)	C39—C44	1.376 (7)
C12—C15	1.503 (7)	C39—C40	1.380 (7)
C13—C14	1.392 (7)	C39—N3	1.413 (6)
C13—H13A	0.9300	C40—C41	1.374 (8)
C14—H14A	0.9300	C40—H40A	0.9300
C15—H15A	0.9600	C41—C42	1.347 (9)
C15—H15B	0.9600	C41—H41A	0.9300
C15—H15C	0.9600	C42—C43	1.399 (9)
C16—C22	1.389 (6)	C42—C45	1.536 (9)
C16—C17	1.413 (6)	C43—C44	1.374 (7)
C16—C21	1.429 (6)	C43—H43A	0.9300
C17—O3	1.305 (5)	C44—H44A	0.9300
C17—C18	1.418 (6)	C45—H45A	0.9600
C18—C19	1.359 (7)	C45—H45B	0.9600
C18—O4	1.380 (5)	C45—H45C	0.9600
C19—C20	1.390 (7)	C46—N4	1.121 (6)
C19—H19A	0.9300	C46—S1	1.641 (6)
C20—C21	1.352 (7)	C47—N5	1.135 (7)
C20—H20A	0.9300	C47—S2	1.626 (6)
C21—H21A	0.9300	C48—N6	1.137 (6)
C22—N2	1.304 (5)	C48—S3	1.628 (6)
C22—H22A	0.9300	N1—H1A	0.8600
C23—O4	1.431 (6)	N2—H2A	0.8600
C23—H23A	0.9600	N3—H3A	0.8600
C23—H23B	0.9600

O1—Eu—O3	143.27 (10)	O4—C23—H23A	109.5
O1—Eu—O5	133.32 (10)	O4—C23—H23B	109.5
O3—Eu—O5	74.53 (10)	H23A—C23—H23B	109.5
O1—Eu—N5	73.04 (14)	O4—C23—H23C	109.5
O3—Eu—N5	110.57 (15)	H23A—C23—H23C	109.5
O5—Eu—N5	128.62 (15)	H23B—C23—H23C	109.5
O1—Eu—N4	86.82 (13)	C29—C24—C25	118.8 (4)
O3—Eu—N4	79.07 (12)	C29—C24—N2	118.4 (4)
O5—Eu—N4	73.48 (12)	C25—C24—N2	122.7 (4)
N5—Eu—N4	157.03 (16)	C26—C25—C24	119.5 (5)
O1—Eu—N6	73.71 (11)	C26—C25—H25A	120.2
O3—Eu—N6	70.59 (11)	C24—C25—H25A	120.2
O5—Eu—N6	139.54 (12)	C27—C26—C25	122.2 (5)
N5—Eu—N6	83.44 (18)	C27—C26—H26A	118.9
N4—Eu—N6	80.30 (15)	C25—C26—H26A	118.9
O1—Eu—O6	99.07 (10)	C26—C27—C28	117.9 (5)
O3—Eu—O6	117.38 (10)	C26—C27—C30	120.6 (6)
O5—Eu—O6	59.55 (10)	C28—C27—C30	121.5 (6)
N5—Eu—O6	75.07 (16)	C27—C28—C29	121.3 (5)
N4—Eu—O6	120.07 (12)	C27—C28—H28A	119.3
N6—Eu—O6	158.50 (13)	C29—C28—H28A	119.3
O1—Eu—O4	142.12 (10)	C24—C29—C28	120.3 (5)
O3—Eu—O4	59.59 (9)	C24—C29—H29A	119.8
O5—Eu—O4	71.15 (11)	C28—C29—H29A	119.8
N5—Eu—O4	69.46 (14)	C27—C30—H30A	109.5
N4—Eu—O4	131.00 (12)	C27—C30—H30B	109.5
N6—Eu—O4	106.60 (12)	H30A—C30—H30B	109.5
O6—Eu—O4	66.42 (10)	C27—C30—H30C	109.5
O1—Eu—O2	58.09 (9)	H30A—C30—H30C	109.5
O3—Eu—O2	143.34 (10)	H30B—C30—H30C	109.5
O5—Eu—O2	75.55 (10)	C32—C31—C37	120.9 (5)
N5—Eu—O2	104.53 (16)	C32—C31—C36	119.0 (5)
N4—Eu—O2	72.46 (13)	C37—C31—C36	120.1 (5)
N6—Eu—O2	124.88 (12)	O5—C32—C31	121.2 (4)
O6—Eu—O2	61.96 (10)	O5—C32—C33	120.2 (4)
O4—Eu—O2	127.55 (10)	C31—C32—C33	118.6 (5)
C2—C1—C7	120.6 (4)	C34—C33—O6	126.5 (5)
C2—C1—C6	118.9 (5)	C34—C33—C32	121.1 (5)
C7—C1—C6	120.6 (5)	O6—C33—C32	112.3 (4)
O1—C2—C1	122.5 (4)	C33—C34—C35	120.2 (6)
O1—C2—C3	118.7 (4)	C33—C34—H34A	119.9
C1—C2—C3	118.8 (4)	C35—C34—H34A	119.9
C4—C3—O2	126.9 (4)	C36—C35—C34	121.7 (6)
C4—C3—C2	120.7 (5)	C36—C35—H35A	119.2
O2—C3—C2	112.4 (4)	C34—C35—H35A	119.2
C3—C4—C5	120.7 (5)	C35—C36—C31	119.3 (6)
C3—C4—H4A	119.7	C35—C36—H36A	120.3
C5—C4—H4A	119.7	C31—C36—H36A	120.3
C6—C5—C4	120.9 (5)	N3—C37—C31	122.3 (4)
C6—C5—H5A	119.6	N3—C37—H37A	118.8
C4—C5—H5A	119.6	C31—C37—H37A	118.8
C5—C6—C1	120.1 (5)	O6—C38—H38A	109.5
C5—C6—H6A	119.9	O6—C38—H38B	109.5
C1—C6—H6A	119.9	H38A—C38—H38B	109.5
N1—C7—C1	123.6 (4)	O6—C38—H38C	109.5
N1—C7—H7A	118.2	H38A—C38—H38C	109.5
C1—C7—H7A	118.2	H38B—C38—H38C	109.5
O2—C8—H8A	109.5	C44—C39—C40	119.5 (5)
O2—C8—H8B	109.5	C44—C39—N3	117.4 (4)
H8A—C8—H8B	109.5	C40—C39—N3	123.0 (5)
O2—C8—H8C	109.5	C41—C40—C39	119.5 (6)
H8A—C8—H8C	109.5	C41—C40—H40A	120.2
H8B—C8—H8C	109.5	C39—C40—H40A	120.2
C14—C9—C10	119.9 (4)	C42—C41—C40	122.2 (6)
C14—C9—N1	122.4 (4)	C42—C41—H41A	118.9
C10—C9—N1	117.7 (4)	C40—C41—H41A	118.9
C11—C10—C9	119.7 (5)	C41—C42—C43	118.1 (5)
C11—C10—H10A	120.2	C41—C42—C45	123.2 (7)
C9—C10—H10A	120.2	C43—C42—C45	118.6 (7)
C12—C11—C10	121.9 (5)	C44—C43—C42	120.7 (6)
C12—C11—H11A	119.1	C44—C43—H43A	119.6
C10—C11—H11A	119.1	C42—C43—H43A	119.6
C11—C12—C13	117.7 (5)	C43—C44—C39	119.8 (5)
C11—C12—C15	122.1 (5)	C43—C44—H44A	120.1
C13—C12—C15	120.3 (5)	C39—C44—H44A	120.1
C12—C13—C14	121.3 (5)	C42—C45—H45A	109.5
C12—C13—H13A	119.3	C42—C45—H45B	109.5
C14—C13—H13A	119.3	H45A—C45—H45B	109.5
C9—C14—C13	119.5 (5)	C42—C45—H45C	109.5
C9—C14—H14A	120.3	H45A—C45—H45C	109.5
C13—C14—H14A	120.3	H45B—C45—H45C	109.5
C12—C15—H15A	109.5	N4—C46—S1	179.1 (5)
C12—C15—H15B	109.5	N5—C47—S2	178.2 (7)
H15A—C15—H15B	109.5	N6—C48—S3	178.2 (5)
C12—C15—H15C	109.5	C7—N1—C9	128.5 (4)
H15A—C15—H15C	109.5	C7—N1—H1A	115.7
H15B—C15—H15C	109.5	C9—N1—H1A	115.7
C22—C16—C17	121.4 (4)	C22—N2—C24	127.4 (4)
C22—C16—C21	119.8 (4)	C22—N2—H2A	116.3
C17—C16—C21	118.8 (4)	C24—N2—H2A	116.3
O3—C17—C16	121.5 (4)	C37—N3—C39	128.1 (4)
O3—C17—C18	120.2 (4)	C37—N3—H3A	115.9
C16—C17—C18	118.3 (4)	C39—N3—H3A	115.9
C19—C18—O4	126.3 (4)	C46—N4—Eu	157.0 (4)
C19—C18—C17	121.4 (4)	C47—N5—Eu	145.2 (5)
O4—C18—C17	112.2 (4)	C48—N6—Eu	169.8 (4)
C18—C19—C20	119.8 (5)	C2—O1—Eu	131.6 (3)
C18—C19—H19A	120.1	C3—O2—C8	118.3 (4)
C20—C19—H19A	120.1	C3—O2—Eu	115.3 (3)
C21—C20—C19	121.5 (5)	C8—O2—Eu	126.3 (3)
C21—C20—H20A	119.2	C17—O3—Eu	126.8 (3)
C19—C20—H20A	119.2	C18—O4—C23	116.7 (4)
C20—C21—C16	120.2 (4)	C18—O4—Eu	114.2 (3)
C20—C21—H21A	119.9	C23—O4—Eu	128.7 (3)
C16—C21—H21A	119.9	C32—O5—Eu	126.6 (3)
N2—C22—C16	123.1 (4)	C33—O6—C38	118.9 (4)
N2—C22—H22A	118.4	C33—O6—Eu	115.3 (3)
C16—C22—H22A	118.5	C38—O6—Eu	125.7 (4)

C7—C1—C2—O1	2.4 (8)	O4—Eu—N5—C47	135.1 (10)
C6—C1—C2—O1	−179.4 (5)	O2—Eu—N5—C47	10.0 (10)
C7—C1—C2—C3	−178.5 (4)	O1—Eu—N6—C48	154 (3)
C6—C1—C2—C3	−0.3 (8)	O3—Eu—N6—C48	−17 (3)
O1—C2—C3—C4	179.9 (5)	O5—Eu—N6—C48	15 (3)
C1—C2—C3—C4	0.8 (8)	N5—Eu—N6—C48	−132 (3)
O1—C2—C3—O2	−0.8 (6)	N4—Eu—N6—C48	65 (3)
C1—C2—C3—O2	−179.9 (4)	O6—Eu—N6—C48	−133 (2)
O2—C3—C4—C5	−179.8 (6)	O4—Eu—N6—C48	−65 (3)
C2—C3—C4—C5	−0.6 (9)	O2—Eu—N6—C48	125 (3)
C3—C4—C5—C6	−0.1 (11)	C1—C2—O1—Eu	−161.0 (3)
C4—C5—C6—C1	0.6 (11)	C3—C2—O1—Eu	19.9 (6)
C2—C1—C6—C5	−0.4 (9)	O3—Eu—O1—C2	−156.8 (3)
C7—C1—C6—C5	177.8 (6)	O5—Eu—O1—C2	−26.2 (4)
C2—C1—C7—N1	1.1 (8)	N5—Eu—O1—C2	101.3 (4)
C6—C1—C7—N1	−177.1 (5)	N4—Eu—O1—C2	−89.9 (4)
C14—C9—C10—C11	−0.1 (7)	N6—Eu—O1—C2	−170.7 (4)
N1—C9—C10—C11	−179.5 (4)	O6—Eu—O1—C2	30.1 (4)
C9—C10—C11—C12	−0.6 (8)	O4—Eu—O1—C2	93.1 (4)
C10—C11—C12—C13	1.0 (8)	O2—Eu—O1—C2	−18.6 (4)
C10—C11—C12—C15	−179.5 (5)	C4—C3—O2—C8	−9.5 (8)
C11—C12—C13—C14	−0.7 (8)	C2—C3—O2—C8	171.3 (4)
C15—C12—C13—C14	179.8 (5)	C4—C3—O2—Eu	166.7 (5)
C10—C9—C14—C13	0.4 (7)	C2—C3—O2—Eu	−12.6 (5)
N1—C9—C14—C13	179.8 (4)	O1—Eu—O2—C3	15.0 (3)
C12—C13—C14—C9	0.0 (8)	O3—Eu—O2—C3	153.1 (3)
C22—C16—C17—O3	0.2 (7)	O5—Eu—O2—C3	−170.7 (3)
C21—C16—C17—O3	179.2 (4)	N5—Eu—O2—C3	−43.9 (3)
C22—C16—C17—C18	−179.8 (4)	N4—Eu—O2—C3	112.4 (3)
C21—C16—C17—C18	−0.8 (6)	N6—Eu—O2—C3	48.2 (4)
O3—C17—C18—C19	179.5 (4)	O6—Eu—O2—C3	−107.8 (3)
C16—C17—C18—C19	−0.5 (7)	O4—Eu—O2—C3	−119.0 (3)
O3—C17—C18—O4	2.1 (6)	O1—Eu—O2—C8	−169.3 (5)
C16—C17—C18—O4	−178.0 (4)	O3—Eu—O2—C8	−31.1 (5)
O4—C18—C19—C20	178.4 (5)	O5—Eu—O2—C8	5.0 (4)
C17—C18—C19—C20	1.3 (8)	N5—Eu—O2—C8	131.8 (4)
C18—C19—C20—C21	−0.8 (9)	N4—Eu—O2—C8	−71.9 (4)
C19—C20—C21—C16	−0.6 (9)	N6—Eu—O2—C8	−136.1 (4)
C22—C16—C21—C20	−179.6 (5)	O6—Eu—O2—C8	67.9 (4)
C17—C16—C21—C20	1.3 (8)	O4—Eu—O2—C8	56.8 (4)
C17—C16—C22—N2	−1.2 (7)	C16—C17—O3—Eu	−157.3 (3)
C21—C16—C22—N2	179.8 (4)	C18—C17—O3—Eu	22.6 (6)
C29—C24—C25—C26	0.3 (7)	O1—Eu—O3—C17	−160.9 (3)
N2—C24—C25—C26	−176.6 (4)	O5—Eu—O3—C17	54.1 (3)
C24—C25—C26—C27	0.2 (8)	N5—Eu—O3—C17	−71.9 (4)
C25—C26—C27—C28	−1.1 (9)	N4—Eu—O3—C17	129.8 (3)
C25—C26—C27—C30	−179.6 (6)	N6—Eu—O3—C17	−146.8 (4)
C26—C27—C28—C29	1.7 (9)	O6—Eu—O3—C17	11.4 (4)
C30—C27—C28—C29	−179.9 (6)	O4—Eu—O3—C17	−22.9 (3)
C25—C24—C29—C28	0.2 (8)	O2—Eu—O3—C17	90.4 (3)
N2—C24—C29—C28	177.3 (5)	C19—C18—O4—C23	−10.6 (8)
C27—C28—C29—C24	−1.3 (9)	C17—C18—O4—C23	166.7 (5)
C37—C31—C32—O5	−2.5 (8)	C19—C18—O4—Eu	163.0 (4)
C36—C31—C32—O5	178.9 (5)	C17—C18—O4—Eu	−19.7 (5)
C37—C31—C32—C33	176.7 (5)	O1—Eu—O4—C18	160.7 (3)
C36—C31—C32—C33	−1.8 (7)	O3—Eu—O4—C18	21.3 (3)
O5—C32—C33—C34	−178.8 (5)	O5—Eu—O4—C18	−61.4 (3)
C31—C32—C33—C34	1.9 (8)	N5—Eu—O4—C18	152.2 (4)
O5—C32—C33—O6	2.5 (6)	N4—Eu—O4—C18	−15.5 (4)
C31—C32—C33—O6	−176.8 (4)	N6—Eu—O4—C18	76.0 (3)
O6—C33—C34—C35	178.4 (6)	O6—Eu—O4—C18	−125.6 (3)
C32—C33—C34—C35	−0.1 (9)	O2—Eu—O4—C18	−114.9 (3)
C33—C34—C35—C36	−1.9 (12)	O1—Eu—O4—C23	−26.6 (5)
C34—C35—C36—C31	1.9 (12)	O3—Eu—O4—C23	−166.0 (5)
C32—C31—C36—C35	−0.1 (9)	O5—Eu—O4—C23	111.3 (5)
C37—C31—C36—C35	−178.6 (6)	N5—Eu—O4—C23	−35.1 (5)
C32—C31—C37—N3	1.1 (8)	N4—Eu—O4—C23	157.2 (5)
C36—C31—C37—N3	179.6 (5)	N6—Eu—O4—C23	−111.3 (5)
C44—C39—C40—C41	−0.1 (8)	O6—Eu—O4—C23	47.1 (5)
N3—C39—C40—C41	176.9 (5)	O2—Eu—O4—C23	57.8 (5)
C39—C40—C41—C42	0.7 (9)	C31—C32—O5—Eu	154.9 (4)
C40—C41—C42—C43	−1.3 (10)	C33—C32—O5—Eu	−24.3 (6)
C40—C41—C42—C45	−178.6 (6)	O1—Eu—O5—C32	94.5 (4)
C41—C42—C43—C44	1.4 (9)	O3—Eu—O5—C32	−113.6 (3)
C45—C42—C43—C44	178.8 (6)	N5—Eu—O5—C32	−9.4 (4)
C42—C43—C44—C39	−0.9 (8)	N4—Eu—O5—C32	163.5 (4)
C40—C39—C44—C43	0.2 (8)	N6—Eu—O5—C32	−144.7 (3)
N3—C39—C44—C43	−177.0 (5)	O6—Eu—O5—C32	22.2 (3)
C1—C7—N1—C9	179.7 (4)	O4—Eu—O5—C32	−51.0 (3)
C14—C9—N1—C7	8.8 (7)	O2—Eu—O5—C32	87.9 (3)
C10—C9—N1—C7	−171.8 (5)	C34—C33—O6—C38	12.3 (8)
C16—C22—N2—C24	177.3 (4)	C32—C33—O6—C38	−169.1 (5)
C29—C24—N2—C22	−164.6 (5)	C34—C33—O6—Eu	−163.4 (5)
C25—C24—N2—C22	12.3 (7)	C32—C33—O6—Eu	15.2 (5)
C31—C37—N3—C39	−174.4 (5)	O1—Eu—O6—C33	−153.9 (3)
C44—C39—N3—C37	−160.3 (5)	O3—Eu—O6—C33	30.8 (3)
C40—C39—N3—C37	22.6 (8)	O5—Eu—O6—C33	−18.5 (3)
O1—Eu—N4—C46	94.1 (10)	N5—Eu—O6—C33	136.5 (3)
O3—Eu—N4—C46	−120.0 (10)	N4—Eu—O6—C33	−62.3 (3)
O5—Eu—N4—C46	−43.0 (10)	N6—Eu—O6—C33	137.8 (4)
N5—Eu—N4—C46	122.6 (10)	O4—Eu—O6—C33	62.8 (3)
N6—Eu—N4—C46	168.1 (11)	O2—Eu—O6—C33	−107.6 (3)
O6—Eu—N4—C46	−4.5 (11)	O1—Eu—O6—C38	30.8 (4)
O4—Eu—N4—C46	−88.3 (10)	O3—Eu—O6—C38	−144.6 (4)
O2—Eu—N4—C46	36.6 (10)	O5—Eu—O6—C38	166.2 (4)
O1—Eu—N5—C47	−39.5 (9)	N5—Eu—O6—C38	−38.8 (4)
O3—Eu—N5—C47	179.2 (9)	N4—Eu—O6—C38	122.4 (4)
O5—Eu—N5—C47	92.9 (9)	N6—Eu—O6—C38	−37.5 (6)
N4—Eu—N5—C47	−69.3 (12)	O4—Eu—O6—C38	−112.6 (4)
N6—Eu—N5—C47	−114.4 (10)	O2—Eu—O6—C38	77.0 (4)
O6—Eu—N5—C47	65.1 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.86	1.89	2.588 (4)	138
N2—H2A···O3	0.86	1.89	2.580 (4)	137
N3—H3A···O5	0.86	1.84	2.550 (4)	138

Experimental details

Crystal data
Chemical formula	[Eu(NCS)₃(C₁₅H₁₅NO₂)₃]
M_r	1050.04
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	16.6445 (2), 14.2411 (2), 22.1678 (3)
β (°)	105.912 (1)
V (Å³)	5053.23 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.42
Crystal size (mm)	0.31 × 0.16 × 0.13

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.757, 0.834
No. of measured, independent and observed [I > 2σ(I)] reflections	37461, 8882, 6762
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.137, 1.06
No. of reflections	8882
No. of parameters	577
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.87, −0.41

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.86	1.89	2.588 (4)	137.6
N2—H2A···O3	0.86	1.89	2.580 (4)	136.8
N3—H3A···O5	0.86	1.84	2.550 (4)	138.2

References

Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, H.-Q., Xian, H.-D., Liu, J.-F. & Zhao, G.-L. (2008). Acta Cryst. E64, m1593–m1594. Web of Science CrossRef IUCr Journals Google Scholar
Liu, G.-F., Shi, T.-S. & Zhao, Y.-N. (1997). J. Mol. Struct. 412, 75–81. CAS Google Scholar
Liu, J.-F., Xian, H.-D. & Zhao, G.-L. (2009). Acta Cryst. E65, m650. Web of Science CSD CrossRef IUCr Journals Google Scholar
Mihara, H., Xu, Y.-J., Shepherd, N. E., Matsunaga, S. & Shibasaki, M. (2009). J. Am. Chem. Soc. 131, 8384–8385. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhao, G.-L., Shi, X. & Ng, S. W. (2007). Acta Cryst. E63, m267–m268. CSD CrossRef IUCr Journals Google Scholar

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Volume 65| Part 12| December 2009| Page m1651

doi:10.1107/S1600536809049125

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