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Acta Cryst. (2009). E65, m1651    [ doi:10.1107/S1600536809049125 ]

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

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

Abstract top

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 EuIII 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 CeIII analogue [Liu et al. (2009). Acta Cryst. E65, m650].

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 EuIII 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 EuIII 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 EuIII 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 EuIII 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 CeIII complex (Liu et al. 2009), which can be attributed to the ionic radius decrease from CeIII to EuIII 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.

Refinement top

The structure was solved by direct methods and successive Fourier difference synthesis and the atom numbering scheme was adopted from the isostructural CeIII complex (Liu et al. 2009). The H atoms bonded to C and N atoms were positioned geometrically and refined using a riding model [aliphatic C—H =0.96 Å (Uiso(H) = 1.5Ueq(C)), aromatic C—H = 0.93 Å (Uiso(H) = 1.2Ueq(C)) and N—H = 0.86 Å with Uiso(H) = 1.2Ueq(N)].

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
[Figure 1] Fig. 1. The molecular structure of the title complex, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] 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
Mr = 1050.04Dx = 1.380 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7369 reflections
a = 16.6445 (2) Åθ = 2.0–25.0°
b = 14.2411 (2) ŵ = 1.42 mm−1
c = 22.1678 (3) ÅT = 296 K
β = 105.912 (1)°Block, red
V = 5053.23 (12) Å30.31 × 0.16 × 0.13 mm
Z = 4
Data collection top
Bruker APEXII CCD area-detector
diffractometer		8882 independent reflections
Radiation source: fine-focus sealed tube6762 reflections with I > 2σ(I)
graphiteRint = 0.046
phi and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −19→19
Tmin = 0.757, Tmax = 0.834k = −16→16
37461 measured reflectionsl = −23→26
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0857P)2]
where P = (Fo2 + 2Fc2)/3
8882 reflections(Δ/σ)max = 0.001
577 parametersΔρmax = 0.87 e Å−3
0 restraintsΔρmin = −0.41 e Å−3
Crystal data top
[Eu(NCS)3(C15H15NO2)3]V = 5053.23 (12) Å3
Mr = 1050.04Z = 4
Monoclinic, P21/cMo Kα radiation
a = 16.6445 (2) ŵ = 1.42 mm−1
b = 14.2411 (2) ÅT = 296 K
c = 22.1678 (3) Å0.31 × 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)
Tmin = 0.757, Tmax = 0.834Rint = 0.046
37461 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.137Δρmax = 0.87 e Å−3
S = 1.06Δρmin = −0.41 e Å−3
8882 reflectionsAbsolute structure: ?
577 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

Geometry. All e.s.d.s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.s are taken into account individually in the estimation of e.s.d.s in distances, angles and torsion angles; correlations between e.s.d.s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.s is used for estimating e.s.d.s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Eu0.212188 (12)0.775828 (17)0.392808 (11)0.04651 (12)
C1−0.0555 (3)0.7601 (3)0.4198 (2)0.0496 (12)
C20.0249 (3)0.7317 (3)0.4190 (2)0.0419 (10)
C30.0421 (3)0.6343 (3)0.4173 (2)0.0482 (11)
C4−0.0183 (4)0.5697 (4)0.4158 (3)0.0741 (17)
H4A−0.00630.50620.41430.089*
C5−0.0979 (4)0.5975 (4)0.4164 (3)0.089 (2)
H5A−0.13860.55230.41520.107*
C6−0.1172 (3)0.6901 (4)0.4186 (3)0.0768 (18)
H6A−0.17070.70770.41940.092*
C7−0.0755 (3)0.8557 (3)0.4200 (2)0.0510 (12)
H7A−0.12910.87200.42130.061*
C80.1514 (4)0.5228 (4)0.4240 (3)0.0787 (18)
H8A0.10880.48290.43170.118*
H8B0.20060.51890.45880.118*
H8C0.16450.50280.38640.118*
C9−0.0370 (2)1.0207 (3)0.41823 (19)0.0417 (10)
C100.0249 (3)1.0782 (4)0.4082 (2)0.0537 (12)
H10A0.07311.05220.40170.064*
C110.0150 (3)1.1736 (4)0.4081 (3)0.0618 (13)
H11A0.05731.21180.40170.074*
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−0.16421.18210.43390.067*
C14−0.1071 (3)1.0589 (3)0.4279 (2)0.0512 (11)
H14A−0.14881.02040.43490.061*
C15−0.0667 (4)1.3191 (4)0.4163 (3)0.0801 (18)
H15A−0.01921.34900.40800.120*
H15B−0.07191.33940.45640.120*
H15C−0.11631.33580.38420.120*
C160.4877 (2)0.8421 (3)0.3996 (2)0.0417 (10)
C170.4005 (2)0.8307 (3)0.3755 (2)0.0401 (10)
C180.3682 (3)0.8078 (3)0.3111 (2)0.0466 (11)
C190.4192 (3)0.7976 (4)0.2730 (2)0.0552 (12)
H19A0.39670.78390.23070.066*
C200.5051 (3)0.8079 (4)0.2974 (3)0.0600 (13)
H20A0.53950.80010.27110.072*
C210.5395 (3)0.8290 (4)0.3585 (2)0.0561 (13)
H21A0.59720.83490.37380.067*
C220.5236 (3)0.8642 (3)0.4622 (2)0.0452 (11)
H22A0.58150.86990.47630.054*
C230.2420 (4)0.7996 (5)0.2274 (2)0.082 (2)
H23A0.28250.81110.20470.123*
H23B0.19960.84720.21720.123*
H23C0.21700.73910.21620.123*
C240.5109 (3)0.8965 (3)0.5674 (2)0.0447 (10)
C250.5932 (3)0.9208 (4)0.5954 (2)0.0533 (12)
H25A0.63030.92850.57120.064*
C260.6195 (3)0.9335 (4)0.6590 (2)0.0630 (14)
H26A0.67490.95010.67740.076*
C270.5675 (4)0.9228 (4)0.6963 (3)0.0688 (15)
C280.4859 (4)0.9002 (4)0.6681 (3)0.0739 (16)
H28A0.44880.89410.69250.089*
C290.4578 (3)0.8862 (4)0.6044 (2)0.0635 (14)
H29A0.40230.86960.58640.076*
C300.5990 (5)0.9382 (5)0.7666 (3)0.105 (2)
H30A0.55410.92860.78540.158*
H30B0.61961.00120.77480.158*
H30C0.64320.89460.78420.158*
C310.3719 (3)0.5437 (4)0.3346 (2)0.0576 (13)
C320.3006 (3)0.5925 (3)0.3394 (2)0.0496 (11)
C330.2273 (3)0.5862 (4)0.2897 (2)0.0571 (12)
C340.2241 (5)0.5321 (5)0.2387 (3)0.087 (2)
H34A0.17500.52860.20630.105*
C350.2944 (6)0.4814 (6)0.2347 (3)0.103 (2)
H35A0.29080.44320.20010.123*
C360.3666 (5)0.4865 (5)0.2794 (3)0.0869 (19)
H36A0.41320.45370.27530.104*
C370.4482 (3)0.5515 (4)0.3816 (3)0.0591 (13)
H37A0.49450.51920.37670.071*
C380.0808 (4)0.6303 (5)0.2585 (3)0.088 (2)
H38A0.08010.57890.23030.133*
H38B0.06420.68680.23470.133*
H38C0.04260.61760.28300.133*
C390.5297 (3)0.6218 (3)0.4791 (3)0.0554 (13)
C400.6085 (3)0.6166 (4)0.4702 (3)0.0703 (15)
H40A0.61530.59650.43200.084*
C410.6768 (3)0.6413 (5)0.5182 (4)0.086 (2)
H41A0.72960.63820.51160.104*
C420.6700 (3)0.6700 (4)0.5745 (4)0.0795 (18)
C430.5901 (3)0.6761 (4)0.5832 (3)0.0730 (16)
H43A0.58380.69710.62140.088*
C440.5208 (3)0.6515 (4)0.5359 (3)0.0631 (14)
H44A0.46790.65500.54240.076*
C450.7453 (4)0.7002 (6)0.6284 (4)0.119 (3)
H45A0.79570.69220.61590.179*
H45B0.74790.66220.66470.179*
H45C0.73930.76500.63830.179*
C460.3000 (3)0.6760 (4)0.5457 (2)0.0527 (12)
C470.0442 (4)0.8630 (5)0.2737 (3)0.0781 (17)
C480.2338 (3)1.0044 (4)0.4741 (3)0.0538 (12)
S10.33288 (14)0.60173 (15)0.60390 (8)0.1038 (7)
S2−0.05210 (12)0.86508 (18)0.23051 (12)0.1316 (9)
S30.25269 (9)1.10435 (12)0.51097 (9)0.0882 (6)
N1−0.0237 (2)0.9224 (3)0.41848 (16)0.0427 (9)
H1A0.02540.90490.41750.051*
N20.4802 (2)0.8774 (2)0.50229 (16)0.0418 (8)
H2A0.42680.87420.48760.050*
N30.4561 (2)0.6018 (3)0.43120 (19)0.0531 (10)
H3A0.41090.62630.43570.064*
N40.2777 (3)0.7258 (3)0.5055 (2)0.0592 (11)
N50.1114 (3)0.8592 (4)0.3037 (2)0.0935 (18)
N60.2185 (2)0.9354 (3)0.4477 (2)0.0652 (12)
O10.08463 (17)0.7912 (2)0.42051 (16)0.0475 (8)
O20.1224 (2)0.6171 (2)0.41675 (17)0.0593 (9)
O30.35011 (16)0.8406 (2)0.41093 (13)0.0443 (7)
O40.28219 (19)0.8018 (3)0.29336 (14)0.0553 (8)
O50.30193 (18)0.6438 (2)0.38871 (14)0.0474 (7)
O60.1634 (2)0.6416 (3)0.29926 (15)0.0611 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Eu0.03922 (15)0.05006 (19)0.04699 (18)0.00313 (9)0.00630 (11)0.00323 (11)
C10.046 (2)0.042 (3)0.062 (3)−0.007 (2)0.017 (2)−0.002 (2)
C20.043 (2)0.039 (3)0.042 (3)−0.0024 (19)0.0084 (19)0.001 (2)
C30.060 (3)0.037 (3)0.049 (3)−0.003 (2)0.018 (2)−0.001 (2)
C40.075 (4)0.041 (3)0.106 (5)−0.011 (3)0.023 (3)−0.005 (3)
C50.083 (4)0.057 (4)0.131 (6)−0.032 (3)0.038 (4)−0.007 (4)
C60.055 (3)0.058 (3)0.123 (5)−0.015 (3)0.032 (3)−0.004 (4)
C70.041 (2)0.053 (3)0.061 (3)0.000 (2)0.017 (2)−0.008 (2)
C80.097 (4)0.040 (3)0.110 (5)0.022 (3)0.045 (4)0.012 (3)
C90.043 (2)0.043 (3)0.036 (2)0.0028 (19)0.0059 (18)0.000 (2)
C100.045 (2)0.053 (3)0.056 (3)0.000 (2)0.002 (2)−0.001 (2)
C110.061 (3)0.048 (3)0.069 (4)−0.010 (2)0.005 (2)0.002 (3)
C120.078 (3)0.047 (3)0.038 (3)0.006 (3)−0.005 (2)−0.002 (2)
C130.066 (3)0.048 (3)0.053 (3)0.011 (2)0.015 (2)−0.003 (2)
C140.058 (3)0.043 (3)0.054 (3)0.003 (2)0.018 (2)0.003 (2)
C150.112 (5)0.043 (3)0.074 (4)0.001 (3)0.005 (3)−0.002 (3)
C160.042 (2)0.043 (3)0.043 (3)−0.0041 (18)0.0156 (19)−0.002 (2)
C170.045 (2)0.034 (2)0.042 (3)−0.0011 (18)0.0140 (19)0.0045 (19)
C180.053 (2)0.046 (3)0.041 (3)−0.005 (2)0.013 (2)0.006 (2)
C190.071 (3)0.059 (3)0.036 (3)−0.003 (2)0.015 (2)0.000 (2)
C200.062 (3)0.074 (4)0.055 (3)−0.001 (3)0.034 (3)−0.003 (3)
C210.044 (2)0.070 (4)0.057 (3)−0.001 (2)0.019 (2)−0.005 (3)
C220.037 (2)0.046 (3)0.054 (3)−0.0017 (18)0.015 (2)0.001 (2)
C230.068 (3)0.139 (6)0.031 (3)−0.019 (4)0.001 (2)0.018 (3)
C240.052 (2)0.039 (3)0.042 (3)0.0001 (19)0.013 (2)−0.002 (2)
C250.048 (2)0.058 (3)0.054 (3)−0.009 (2)0.014 (2)−0.007 (2)
C260.069 (3)0.055 (3)0.056 (3)−0.009 (3)0.002 (3)−0.010 (3)
C270.104 (4)0.053 (3)0.047 (3)−0.013 (3)0.017 (3)−0.009 (3)
C280.098 (4)0.083 (4)0.048 (3)−0.024 (3)0.032 (3)−0.013 (3)
C290.064 (3)0.070 (4)0.062 (3)−0.016 (3)0.025 (3)−0.016 (3)
C300.161 (7)0.099 (6)0.050 (4)−0.034 (5)0.020 (4)−0.015 (4)
C310.072 (3)0.053 (3)0.054 (3)0.004 (2)0.027 (3)−0.007 (2)
C320.066 (3)0.045 (3)0.041 (3)−0.001 (2)0.019 (2)0.005 (2)
C330.067 (3)0.055 (3)0.046 (3)−0.004 (2)0.009 (2)0.003 (2)
C340.111 (5)0.091 (5)0.049 (4)−0.024 (4)0.006 (3)−0.021 (3)
C350.135 (6)0.105 (6)0.072 (5)−0.016 (5)0.034 (5)−0.044 (4)
C360.112 (5)0.079 (5)0.079 (5)0.003 (4)0.044 (4)−0.019 (4)
C370.065 (3)0.042 (3)0.076 (4)0.014 (2)0.029 (3)0.003 (3)
C380.071 (4)0.090 (5)0.078 (4)−0.011 (3)−0.023 (3)0.007 (4)
C390.055 (3)0.040 (3)0.067 (3)0.014 (2)0.010 (2)0.011 (2)
C400.060 (3)0.062 (4)0.091 (4)0.022 (3)0.025 (3)0.005 (3)
C410.050 (3)0.080 (5)0.121 (6)0.018 (3)0.010 (3)0.005 (4)
C420.062 (3)0.053 (4)0.104 (5)0.012 (3)−0.010 (3)0.012 (4)
C430.080 (4)0.049 (3)0.075 (4)0.010 (3)−0.005 (3)0.001 (3)
C440.059 (3)0.049 (3)0.077 (4)0.011 (2)0.013 (3)0.010 (3)
C450.077 (4)0.100 (5)0.146 (7)0.008 (4)−0.028 (4)0.000 (5)
C460.061 (3)0.061 (3)0.037 (3)0.017 (2)0.017 (2)−0.006 (3)
C470.084 (4)0.082 (4)0.060 (4)0.028 (3)0.006 (3)0.009 (3)
C480.036 (2)0.057 (3)0.071 (3)−0.008 (2)0.020 (2)−0.007 (3)
S10.1488 (16)0.1137 (15)0.0626 (10)0.0676 (13)0.0518 (10)0.0386 (10)
S20.0849 (12)0.1219 (17)0.148 (2)0.0366 (12)−0.0365 (12)−0.0150 (15)
S30.0592 (8)0.0801 (11)0.1363 (15)−0.0291 (7)0.0455 (9)−0.0507 (11)
N10.0374 (17)0.043 (2)0.048 (2)0.0043 (16)0.0115 (15)0.0024 (17)
N20.0366 (17)0.043 (2)0.043 (2)−0.0041 (15)0.0067 (15)−0.0012 (17)
N30.049 (2)0.045 (2)0.064 (3)0.0140 (17)0.0140 (19)0.004 (2)
N40.061 (3)0.068 (3)0.048 (3)0.012 (2)0.012 (2)0.009 (2)
N50.065 (3)0.131 (5)0.076 (4)0.032 (3)0.005 (3)0.038 (3)
N60.052 (2)0.057 (3)0.093 (3)−0.004 (2)0.029 (2)−0.014 (3)
O10.0397 (15)0.0340 (17)0.072 (2)−0.0014 (12)0.0208 (15)0.0004 (15)
O20.066 (2)0.0378 (18)0.076 (2)0.0080 (16)0.0216 (17)0.0007 (17)
O30.0363 (14)0.056 (2)0.0420 (17)−0.0025 (13)0.0138 (13)−0.0035 (15)
O40.0519 (18)0.073 (2)0.0360 (18)−0.0073 (16)0.0040 (14)0.0065 (16)
O50.0531 (17)0.0491 (19)0.0367 (17)0.0077 (14)0.0069 (13)−0.0026 (15)
O60.062 (2)0.070 (2)0.0397 (19)−0.0064 (18)−0.0051 (15)0.0018 (17)
Geometric parameters (Å, °) top
Eu—O12.376 (3)C23—H23C0.9600
Eu—O32.404 (3)C24—C291.369 (6)
Eu—O52.418 (3)C24—C251.383 (6)
Eu—N52.512 (5)C24—N21.420 (5)
Eu—N42.538 (4)C25—C261.369 (7)
Eu—N62.566 (5)C25—H25A0.9300
Eu—O62.773 (3)C26—C271.359 (7)
Eu—O42.786 (3)C26—H26A0.9300
Eu—O22.839 (3)C27—C281.368 (8)
C1—C21.403 (6)C27—C301.519 (8)
C1—C71.402 (7)C28—C291.374 (7)
C1—C61.427 (7)C28—H28A0.9300
C2—O11.299 (5)C29—H29A0.9300
C2—C31.419 (6)C30—H30A0.9600
C3—C41.356 (7)C30—H30B0.9600
C3—O21.362 (5)C30—H30C0.9600
C4—C51.385 (8)C31—C321.405 (7)
C4—H4A0.9300C31—C371.409 (7)
C5—C61.361 (8)C31—C361.452 (8)
C5—H5A0.9300C32—O51.310 (5)
C6—H6A0.9300C32—C331.406 (7)
C7—N11.289 (6)C33—C341.356 (8)
C7—H7A0.9300C33—O61.386 (6)
C8—O21.422 (6)C34—C351.398 (10)
C8—H8A0.9600C34—H34A0.9300
C8—H8B0.9600C35—C361.333 (9)
C8—H8C0.9600C35—H35A0.9300
C9—C141.357 (6)C36—H36A0.9300
C9—C101.380 (6)C37—N31.289 (6)
C9—N11.417 (6)C37—H37A0.9300
C10—C111.369 (7)C38—O61.433 (6)
C10—H10A0.9300C38—H38A0.9600
C11—C121.369 (8)C38—H38B0.9600
C11—H11A0.9300C38—H38C0.9600
C12—C131.376 (7)C39—C441.376 (7)
C12—C151.503 (7)C39—C401.380 (7)
C13—C141.392 (7)C39—N31.413 (6)
C13—H13A0.9300C40—C411.374 (8)
C14—H14A0.9300C40—H40A0.9300
C15—H15A0.9600C41—C421.347 (9)
C15—H15B0.9600C41—H41A0.9300
C15—H15C0.9600C42—C431.399 (9)
C16—C221.389 (6)C42—C451.536 (9)
C16—C171.413 (6)C43—C441.374 (7)
C16—C211.429 (6)C43—H43A0.9300
C17—O31.305 (5)C44—H44A0.9300
C17—C181.418 (6)C45—H45A0.9600
C18—C191.359 (7)C45—H45B0.9600
C18—O41.380 (5)C45—H45C0.9600
C19—C201.390 (7)C46—N41.121 (6)
C19—H19A0.9300C46—S11.641 (6)
C20—C211.352 (7)C47—N51.135 (7)
C20—H20A0.9300C47—S21.626 (6)
C21—H21A0.9300C48—N61.137 (6)
C22—N21.304 (5)C48—S31.628 (6)
C22—H22A0.9300N1—H1A0.8600
C23—O41.431 (6)N2—H2A0.8600
C23—H23A0.9600N3—H3A0.8600
C23—H23B0.9600
O1—Eu—O3143.27 (10)O4—C23—H23A109.5
O1—Eu—O5133.32 (10)O4—C23—H23B109.5
O3—Eu—O574.53 (10)H23A—C23—H23B109.5
O1—Eu—N573.04 (14)O4—C23—H23C109.5
O3—Eu—N5110.57 (15)H23A—C23—H23C109.5
O5—Eu—N5128.62 (15)H23B—C23—H23C109.5
O1—Eu—N486.82 (13)C29—C24—C25118.8 (4)
O3—Eu—N479.07 (12)C29—C24—N2118.4 (4)
O5—Eu—N473.48 (12)C25—C24—N2122.7 (4)
N5—Eu—N4157.03 (16)C26—C25—C24119.5 (5)
O1—Eu—N673.71 (11)C26—C25—H25A120.2
O3—Eu—N670.59 (11)C24—C25—H25A120.2
O5—Eu—N6139.54 (12)C27—C26—C25122.2 (5)
N5—Eu—N683.44 (18)C27—C26—H26A118.9
N4—Eu—N680.30 (15)C25—C26—H26A118.9
O1—Eu—O699.07 (10)C26—C27—C28117.9 (5)
O3—Eu—O6117.38 (10)C26—C27—C30120.6 (6)
O5—Eu—O659.55 (10)C28—C27—C30121.5 (6)
N5—Eu—O675.07 (16)C27—C28—C29121.3 (5)
N4—Eu—O6120.07 (12)C27—C28—H28A119.3
N6—Eu—O6158.50 (13)C29—C28—H28A119.3
O1—Eu—O4142.12 (10)C24—C29—C28120.3 (5)
O3—Eu—O459.59 (9)C24—C29—H29A119.8
O5—Eu—O471.15 (11)C28—C29—H29A119.8
N5—Eu—O469.46 (14)C27—C30—H30A109.5
N4—Eu—O4131.00 (12)C27—C30—H30B109.5
N6—Eu—O4106.60 (12)H30A—C30—H30B109.5
O6—Eu—O466.42 (10)C27—C30—H30C109.5
O1—Eu—O258.09 (9)H30A—C30—H30C109.5
O3—Eu—O2143.34 (10)H30B—C30—H30C109.5
O5—Eu—O275.55 (10)C32—C31—C37120.9 (5)
N5—Eu—O2104.53 (16)C32—C31—C36119.0 (5)
N4—Eu—O272.46 (13)C37—C31—C36120.1 (5)
N6—Eu—O2124.88 (12)O5—C32—C31121.2 (4)
O6—Eu—O261.96 (10)O5—C32—C33120.2 (4)
O4—Eu—O2127.55 (10)C31—C32—C33118.6 (5)
C2—C1—C7120.6 (4)C34—C33—O6126.5 (5)
C2—C1—C6118.9 (5)C34—C33—C32121.1 (5)
C7—C1—C6120.6 (5)O6—C33—C32112.3 (4)
O1—C2—C1122.5 (4)C33—C34—C35120.2 (6)
O1—C2—C3118.7 (4)C33—C34—H34A119.9
C1—C2—C3118.8 (4)C35—C34—H34A119.9
C4—C3—O2126.9 (4)C36—C35—C34121.7 (6)
C4—C3—C2120.7 (5)C36—C35—H35A119.2
O2—C3—C2112.4 (4)C34—C35—H35A119.2
C3—C4—C5120.7 (5)C35—C36—C31119.3 (6)
C3—C4—H4A119.7C35—C36—H36A120.3
C5—C4—H4A119.7C31—C36—H36A120.3
C6—C5—C4120.9 (5)N3—C37—C31122.3 (4)
C6—C5—H5A119.6N3—C37—H37A118.8
C4—C5—H5A119.6C31—C37—H37A118.8
C5—C6—C1120.1 (5)O6—C38—H38A109.5
C5—C6—H6A119.9O6—C38—H38B109.5
C1—C6—H6A119.9H38A—C38—H38B109.5
N1—C7—C1123.6 (4)O6—C38—H38C109.5
N1—C7—H7A118.2H38A—C38—H38C109.5
C1—C7—H7A118.2H38B—C38—H38C109.5
O2—C8—H8A109.5C44—C39—C40119.5 (5)
O2—C8—H8B109.5C44—C39—N3117.4 (4)
H8A—C8—H8B109.5C40—C39—N3123.0 (5)
O2—C8—H8C109.5C41—C40—C39119.5 (6)
H8A—C8—H8C109.5C41—C40—H40A120.2
H8B—C8—H8C109.5C39—C40—H40A120.2
C14—C9—C10119.9 (4)C42—C41—C40122.2 (6)
C14—C9—N1122.4 (4)C42—C41—H41A118.9
C10—C9—N1117.7 (4)C40—C41—H41A118.9
C11—C10—C9119.7 (5)C41—C42—C43118.1 (5)
C11—C10—H10A120.2C41—C42—C45123.2 (7)
C9—C10—H10A120.2C43—C42—C45118.6 (7)
C12—C11—C10121.9 (5)C44—C43—C42120.7 (6)
C12—C11—H11A119.1C44—C43—H43A119.6
C10—C11—H11A119.1C42—C43—H43A119.6
C11—C12—C13117.7 (5)C43—C44—C39119.8 (5)
C11—C12—C15122.1 (5)C43—C44—H44A120.1
C13—C12—C15120.3 (5)C39—C44—H44A120.1
C12—C13—C14121.3 (5)C42—C45—H45A109.5
C12—C13—H13A119.3C42—C45—H45B109.5
C14—C13—H13A119.3H45A—C45—H45B109.5
C9—C14—C13119.5 (5)C42—C45—H45C109.5
C9—C14—H14A120.3H45A—C45—H45C109.5
C13—C14—H14A120.3H45B—C45—H45C109.5
C12—C15—H15A109.5N4—C46—S1179.1 (5)
C12—C15—H15B109.5N5—C47—S2178.2 (7)
H15A—C15—H15B109.5N6—C48—S3178.2 (5)
C12—C15—H15C109.5C7—N1—C9128.5 (4)
H15A—C15—H15C109.5C7—N1—H1A115.7
H15B—C15—H15C109.5C9—N1—H1A115.7
C22—C16—C17121.4 (4)C22—N2—C24127.4 (4)
C22—C16—C21119.8 (4)C22—N2—H2A116.3
C17—C16—C21118.8 (4)C24—N2—H2A116.3
O3—C17—C16121.5 (4)C37—N3—C39128.1 (4)
O3—C17—C18120.2 (4)C37—N3—H3A115.9
C16—C17—C18118.3 (4)C39—N3—H3A115.9
C19—C18—O4126.3 (4)C46—N4—Eu157.0 (4)
C19—C18—C17121.4 (4)C47—N5—Eu145.2 (5)
O4—C18—C17112.2 (4)C48—N6—Eu169.8 (4)
C18—C19—C20119.8 (5)C2—O1—Eu131.6 (3)
C18—C19—H19A120.1C3—O2—C8118.3 (4)
C20—C19—H19A120.1C3—O2—Eu115.3 (3)
C21—C20—C19121.5 (5)C8—O2—Eu126.3 (3)
C21—C20—H20A119.2C17—O3—Eu126.8 (3)
C19—C20—H20A119.2C18—O4—C23116.7 (4)
C20—C21—C16120.2 (4)C18—O4—Eu114.2 (3)
C20—C21—H21A119.9C23—O4—Eu128.7 (3)
C16—C21—H21A119.9C32—O5—Eu126.6 (3)
N2—C22—C16123.1 (4)C33—O6—C38118.9 (4)
N2—C22—H22A118.4C33—O6—Eu115.3 (3)
C16—C22—H22A118.5C38—O6—Eu125.7 (4)
C7—C1—C2—O12.4 (8)O4—Eu—N5—C47135.1 (10)
C6—C1—C2—O1−179.4 (5)O2—Eu—N5—C4710.0 (10)
C7—C1—C2—C3−178.5 (4)O1—Eu—N6—C48154 (3)
C6—C1—C2—C3−0.3 (8)O3—Eu—N6—C48−17 (3)
O1—C2—C3—C4179.9 (5)O5—Eu—N6—C4815 (3)
C1—C2—C3—C40.8 (8)N5—Eu—N6—C48−132 (3)
O1—C2—C3—O2−0.8 (6)N4—Eu—N6—C4865 (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—C48125 (3)
C3—C4—C5—C6−0.1 (11)C1—C2—O1—Eu−161.0 (3)
C4—C5—C6—C10.6 (11)C3—C2—O1—Eu19.9 (6)
C2—C1—C6—C5−0.4 (9)O3—Eu—O1—C2−156.8 (3)
C7—C1—C6—C5177.8 (6)O5—Eu—O1—C2−26.2 (4)
C2—C1—C7—N11.1 (8)N5—Eu—O1—C2101.3 (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—C230.1 (4)
C9—C10—C11—C12−0.6 (8)O4—Eu—O1—C293.1 (4)
C10—C11—C12—C131.0 (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—C8171.3 (4)
C15—C12—C13—C14179.8 (5)C4—C3—O2—Eu166.7 (5)
C10—C9—C14—C130.4 (7)C2—C3—O2—Eu−12.6 (5)
N1—C9—C14—C13179.8 (4)O1—Eu—O2—C315.0 (3)
C12—C13—C14—C90.0 (8)O3—Eu—O2—C3153.1 (3)
C22—C16—C17—O30.2 (7)O5—Eu—O2—C3−170.7 (3)
C21—C16—C17—O3179.2 (4)N5—Eu—O2—C3−43.9 (3)
C22—C16—C17—C18−179.8 (4)N4—Eu—O2—C3112.4 (3)
C21—C16—C17—C18−0.8 (6)N6—Eu—O2—C348.2 (4)
O3—C17—C18—C19179.5 (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—O42.1 (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—C20178.4 (5)O5—Eu—O2—C85.0 (4)
C17—C18—C19—C201.3 (8)N5—Eu—O2—C8131.8 (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—C867.9 (4)
C17—C16—C21—C201.3 (8)O4—Eu—O2—C856.8 (4)
C17—C16—C22—N2−1.2 (7)C16—C17—O3—Eu−157.3 (3)
C21—C16—C22—N2179.8 (4)C18—C17—O3—Eu22.6 (6)
C29—C24—C25—C260.3 (7)O1—Eu—O3—C17−160.9 (3)
N2—C24—C25—C26−176.6 (4)O5—Eu—O3—C1754.1 (3)
C24—C25—C26—C270.2 (8)N5—Eu—O3—C17−71.9 (4)
C25—C26—C27—C28−1.1 (9)N4—Eu—O3—C17129.8 (3)
C25—C26—C27—C30−179.6 (6)N6—Eu—O3—C17−146.8 (4)
C26—C27—C28—C291.7 (9)O6—Eu—O3—C1711.4 (4)
C30—C27—C28—C29−179.9 (6)O4—Eu—O3—C17−22.9 (3)
C25—C24—C29—C280.2 (8)O2—Eu—O3—C1790.4 (3)
N2—C24—C29—C28177.3 (5)C19—C18—O4—C23−10.6 (8)
C27—C28—C29—C24−1.3 (9)C17—C18—O4—C23166.7 (5)
C37—C31—C32—O5−2.5 (8)C19—C18—O4—Eu163.0 (4)
C36—C31—C32—O5178.9 (5)C17—C18—O4—Eu−19.7 (5)
C37—C31—C32—C33176.7 (5)O1—Eu—O4—C18160.7 (3)
C36—C31—C32—C33−1.8 (7)O3—Eu—O4—C1821.3 (3)
O5—C32—C33—C34−178.8 (5)O5—Eu—O4—C18−61.4 (3)
C31—C32—C33—C341.9 (8)N5—Eu—O4—C18152.2 (4)
O5—C32—C33—O62.5 (6)N4—Eu—O4—C18−15.5 (4)
C31—C32—C33—O6−176.8 (4)N6—Eu—O4—C1876.0 (3)
O6—C33—C34—C35178.4 (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—C311.9 (12)O3—Eu—O4—C23−166.0 (5)
C32—C31—C36—C35−0.1 (9)O5—Eu—O4—C23111.3 (5)
C37—C31—C36—C35−178.6 (6)N5—Eu—O4—C23−35.1 (5)
C32—C31—C37—N31.1 (8)N4—Eu—O4—C23157.2 (5)
C36—C31—C37—N3179.6 (5)N6—Eu—O4—C23−111.3 (5)
C44—C39—C40—C41−0.1 (8)O6—Eu—O4—C2347.1 (5)
N3—C39—C40—C41176.9 (5)O2—Eu—O4—C2357.8 (5)
C39—C40—C41—C420.7 (9)C31—C32—O5—Eu154.9 (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—C3294.5 (4)
C41—C42—C43—C441.4 (9)O3—Eu—O5—C32−113.6 (3)
C45—C42—C43—C44178.8 (6)N5—Eu—O5—C32−9.4 (4)
C42—C43—C44—C39−0.9 (8)N4—Eu—O5—C32163.5 (4)
C40—C39—C44—C430.2 (8)N6—Eu—O5—C32−144.7 (3)
N3—C39—C44—C43−177.0 (5)O6—Eu—O5—C3222.2 (3)
C1—C7—N1—C9179.7 (4)O4—Eu—O5—C32−51.0 (3)
C14—C9—N1—C78.8 (7)O2—Eu—O5—C3287.9 (3)
C10—C9—N1—C7−171.8 (5)C34—C33—O6—C3812.3 (8)
C16—C22—N2—C24177.3 (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—C2212.3 (7)C32—C33—O6—Eu15.2 (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—C3330.8 (3)
C40—C39—N3—C3722.6 (8)O5—Eu—O6—C33−18.5 (3)
O1—Eu—N4—C4694.1 (10)N5—Eu—O6—C33136.5 (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—C33137.8 (4)
N5—Eu—N4—C46122.6 (10)O4—Eu—O6—C3362.8 (3)
N6—Eu—N4—C46168.1 (11)O2—Eu—O6—C33−107.6 (3)
O6—Eu—N4—C46−4.5 (11)O1—Eu—O6—C3830.8 (4)
O4—Eu—N4—C46−88.3 (10)O3—Eu—O6—C38−144.6 (4)
O2—Eu—N4—C4636.6 (10)O5—Eu—O6—C38166.2 (4)
O1—Eu—N5—C47−39.5 (9)N5—Eu—O6—C38−38.8 (4)
O3—Eu—N5—C47179.2 (9)N4—Eu—O6—C38122.4 (4)
O5—Eu—N5—C4792.9 (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—C3877.0 (4)
O6—Eu—N5—C4765.1 (9)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O10.861.892.588 (4)138
N2—H2A···O30.861.892.580 (4)137
N3—H3A···O50.861.842.550 (4)138
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O10.861.892.588 (4)138
N2—H2A···O30.861.892.580 (4)137
N3—H3A···O50.861.842.550 (4)138
references
References top

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Zhao, G.-L., Shi, X. & Ng, S. W. (2007). Acta Cryst. E63, m267–m268.