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Acta Cryst. (2009). E65, m650    [ doi:10.1107/S1600536809016808 ]

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

J.-F. Liu, H.-D. Xian and G.-L. Zhao

Abstract top

The asymmetric unit of the title compound, [Ce(NCS)3(C15H15NO2)3], contains three Schiff base 2-methoxy-6-[(4-methylphenyl)iminomethyl]phenol (HL) ligands and three independent thiocyanate ions that coordinate the cerium ion via their N atoms. The protonated imine N atoms are involved in an intramolecular hydrogen bond with the respective phenoxide group. The Ce(III) ion exhibits a coordination number of nine.

Comment top

Schiff base ligands derived from substituted o-vanillin and aniline and their rare earth metal complexes have been absorbed considerable attention in the past decades due to their intriguing novel structural features (Burrows & Bailar, 1966; Zhao et al., 2007; Xian et al., 2008; Li et al., 2008) and promising applications in various fields such as catalysis, optoelectronic devices, and so on (Leadbeater & Marco, 2002; Quici et al., 2004). Interested in this field, we have been engaged in a major effort directed toward the development syntheses of new analogous Schiff base derived from o-vanillin and their rare metal complexes. In a few of articles we have reported our partial research results (Zhao et al., 2007; Xian et al., 2008; Li et al., 2008). Herein, we describe a new Ce(III) complex, (I).

The single-crystal structure of (I) is shown in Fig.1, which illustrates that the Ce(III) ion in this complex is nine-coordinated by three nitrogen atoms from three thiocyanate ions and six O atoms from the Schiff bases. The Schiff bases coordinated to the Ce(III) ion by didentate mode using O atoms from methoxyl groups and deprotonated phenolic hydroxyl groups. The bonds between Ce(III) and O atoms from phenolic hydroxyl groups are 2.408 (2) Å-2.436 (3) Å, which are longer than the ones between Ce(III) and O atoms of methoxyl groups [2.792 (3) Å-2.838 (3) Å]. And the Ce—N bonds are 2.519 (4)Å -2.576 (4) Å. Because of the geometric and chemical environment requirements of the chelating groups, the coordination geometry deviates considerably from the distorted capped square antiprism geometry (Fig. 2) that gives the lowest energy configuration for nine monodentate ligands surrounding a metal centre (Liu et al., 2001). In one ligand the proton from the phenolic hydroxyl group transfers to imine N atom involving in an intramolecular hydrogen.

Related literature top

For background to Schiff bases and their applications, see: Burrows & Bailar (1966); Leadbeater & Marco (2002); Quici et al. (2004); Liu et al. (2001). For related structures, see: Li et al. (2008); Xian et al. (2008); Zhao et al. (2007).

Experimental top

Reagents and solvents used were of commercially available quality and without purified before using. The Schiff base ligand 2-[(4- methylphenyl)iminomethyl]-6-methoxy-phenol was sythesized from condensation of o-vanillin and p-methylaniline. The compound (I) was obtained by adding Ce(NO3)3 (1 mmol, dissolved in methanol) to N-salicylidene-p-toluidine)3 (3 mmol) in methanol solution. The mixture solution was stirred for 2 h at room temperature. Then 3 mmol NH4SCN (dissolved in methanol) was added to the upper solution and the mixture was stirred again for 8 h at room temperature. At last, deposit was filted out and the reddish-brown solution was kept aside. The red crystal was obtained after several days.

Refinement top

The H atoms were positioned geometrically and refined using a riding model [aromatic C—H 0.93 Å, methyl C—H = 0.96 Å, and Uiso(H) = 1.2 or 1.5Ueq(C)].

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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title complex, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Coordination environment of Ce3+ ion.
Tris{2-methoxy-6-[(4-methylphenyl)iminiomethyl]phenolato- κ2O,O'}tris(thiocyanato-κN)cerium(III) top
Crystal data top
[Ce(NCS)3(C15H15NO2)3]F000 = 2116
Mr = 1038.23Dx = 1.361 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5835 reflections
a = 16.6730 (3) Åθ = 1.9–27.5º
b = 14.2407 (2) ŵ = 1.07 mm−1
c = 22.1918 (4) ÅT = 296 K
β = 105.9790 (10)ºBlock, red
V = 5065.53 (15) Å30.32 × 0.11 × 0.09 mm
Z = 4
Data collection top
Bruker APEX2 area-detector
diffractometer		11645 independent reflections
Radiation source: fine-focus sealed tube7080 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.093
T = 296 Kθmax = 27.5º
phi and ω scansθmin = 1.9º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −21→21
Tmin = 0.868, Tmax = 0.909k = −18→18
78580 measured reflectionsl = −28→28
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.117  w = 1/[σ2(Fo2) + (0.0507P)2 + 0.4997P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
11645 reflectionsΔρmax = 0.70 e Å−3
577 parametersΔρmin = −0.44 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Ce(NCS)3(C15H15NO2)3]V = 5065.53 (15) Å3
Mr = 1038.23Z = 4
Monoclinic, P21/cMo Kα
a = 16.6730 (3) ŵ = 1.07 mm−1
b = 14.2407 (2) ÅT = 296 K
c = 22.1918 (4) Å0.32 × 0.11 × 0.09 mm
β = 105.9790 (10)º
Data collection top
Bruker APEX2 area-detector
diffractometer		11645 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		7080 reflections with I > 2σ(I)
Tmin = 0.868, Tmax = 0.909Rint = 0.093
78580 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.045577 parameters
wR(F2) = 0.117H-atom parameters constrained
S = 1.01Δρmax = 0.70 e Å−3
11645 reflectionsΔρmin = −0.44 e Å−3
Special details top

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ce0.288150 (12)0.224761 (16)0.107530 (10)0.04892 (9)
N10.0435 (2)0.3991 (2)0.06891 (17)0.0628 (9)
H1A0.08890.37570.06410.075*
N20.01915 (18)0.1230 (2)−0.00249 (14)0.0515 (8)
H2A0.07250.12600.01220.062*
N30.52454 (18)0.0772 (2)0.08149 (14)0.0514 (8)
H3A0.47560.09470.08250.062*
N40.2818 (2)0.0638 (3)0.0534 (2)0.0775 (11)
N50.2213 (2)0.2751 (3)−0.00586 (18)0.0709 (10)
N60.3894 (3)0.1422 (4)0.1973 (2)0.1028 (16)
O10.19791 (16)0.35765 (19)0.11193 (12)0.0588 (7)
O20.33583 (18)0.3607 (2)0.20127 (13)0.0738 (8)
O40.21751 (17)0.1993 (2)0.20688 (12)0.0667 (8)
O30.14905 (14)0.16000 (19)0.08899 (11)0.0551 (7)
O50.41707 (15)0.20818 (18)0.07955 (13)0.0584 (7)
O60.37866 (18)0.3824 (2)0.08337 (14)0.0704 (8)
C10.1272 (3)0.4575 (3)0.1663 (2)0.0677 (12)
C20.1980 (3)0.4088 (3)0.16063 (19)0.0578 (10)
C30.2725 (3)0.4159 (3)0.2102 (2)0.0682 (12)
C40.2754 (4)0.4707 (4)0.2615 (2)0.0977 (17)
H4A0.32480.47540.29350.117*
C50.2048 (5)0.5196 (5)0.2658 (3)0.115 (2)
H5B0.20760.55700.30070.138*
C60.1323 (4)0.5135 (4)0.2200 (3)0.0987 (17)
H6B0.08560.54620.22370.118*
C70.0516 (3)0.4487 (3)0.1193 (2)0.0709 (13)
H7A0.00500.47990.12450.085*
C80.4179 (3)0.3720 (4)0.2433 (2)0.1012 (18)
H8A0.41790.42370.27100.152*
H8B0.45700.38420.21950.152*
H8C0.43370.31560.26730.152*
C9−0.0297 (3)0.3785 (3)0.0208 (2)0.0632 (11)
C10−0.1078 (3)0.3844 (4)0.0299 (3)0.0831 (14)
H10A−0.11390.40470.06820.100*
C11−0.1764 (3)0.3603 (4)−0.0173 (3)0.1001 (18)
H11A−0.22890.3642−0.01040.120*
C12−0.1700 (3)0.3303 (4)−0.0751 (3)0.0920 (17)
C13−0.0910 (3)0.3242 (4)−0.0832 (3)0.0849 (14)
H13A−0.08480.3032−0.12140.102*
C14−0.0204 (3)0.3487 (3)−0.0358 (2)0.0703 (12)
H14A0.03230.3451−0.04230.084*
C15−0.2448 (4)0.3010 (5)−0.1284 (3)0.139 (3)
H15A−0.29500.3093−0.11580.208*
H15B−0.23930.2362−0.13850.208*
H15C−0.24730.3391−0.16460.208*
C160.5569 (2)0.2400 (3)0.0806 (2)0.0575 (11)
C170.4755 (2)0.2682 (3)0.08106 (18)0.0508 (9)
C180.4593 (3)0.3654 (3)0.08333 (19)0.0592 (10)
C190.5198 (3)0.4287 (3)0.0850 (3)0.0869 (15)
H19A0.50790.49230.08670.104*
C200.5990 (3)0.4020 (4)0.0841 (3)0.1019 (19)
H20A0.63960.44730.08530.122*
C210.6177 (3)0.3092 (4)0.0815 (3)0.0882 (16)
H21A0.67090.29140.08030.106*
C220.5762 (2)0.1438 (3)0.0800 (2)0.0602 (11)
H22A0.62960.12740.07840.072*
C230.3494 (3)0.4778 (3)0.0765 (3)0.0939 (17)
H23A0.39170.51770.06860.141*
H23B0.33690.49750.11430.141*
H23C0.29990.48180.04210.141*
C240.5377 (2)−0.0203 (3)0.08167 (17)0.0501 (9)
C250.6082 (3)−0.0598 (3)0.07191 (19)0.0609 (11)
H25A0.6500−0.02170.06490.073*
C260.6169 (3)−0.1559 (3)0.07255 (19)0.0651 (11)
H26A0.6651−0.18160.06590.078*
C270.5570 (3)−0.2153 (3)0.0826 (2)0.0644 (11)
C280.4859 (3)−0.1741 (3)0.0922 (2)0.0737 (13)
H28A0.4443−0.21250.09920.088*
C290.4753 (3)−0.0776 (3)0.0916 (2)0.0649 (11)
H29A0.4270−0.05160.09770.078*
C300.5667 (3)−0.3199 (3)0.0834 (2)0.0914 (16)
H30A0.6192−0.33580.07620.137*
H30B0.5221−0.34710.05120.137*
H30C0.5649−0.34380.12350.137*
C310.0119 (2)0.1586 (3)0.10127 (17)0.0494 (9)
C320.0991 (2)0.1697 (3)0.12478 (18)0.0490 (9)
C330.1316 (2)0.1910 (3)0.18852 (18)0.0536 (10)
C340.0806 (3)0.2031 (3)0.2268 (2)0.0669 (12)
H34A0.10330.21790.26890.080*
C35−0.0054 (3)0.1933 (3)0.2027 (2)0.0712 (13)
H35A−0.04000.20200.22870.085*
C36−0.0391 (3)0.1712 (3)0.1416 (2)0.0666 (12)
H36A−0.09660.16430.12620.080*
C37−0.0236 (2)0.1367 (3)0.03787 (18)0.0530 (10)
H37A−0.08130.13150.02370.064*
C380.2568 (3)0.2028 (4)0.2727 (2)0.0942 (18)
H38A0.21620.19100.29520.141*
H38B0.28090.26380.28370.141*
H38C0.29980.15600.28360.141*
C39−0.0113 (2)0.1037 (3)−0.06771 (18)0.0519 (9)
C400.0419 (3)0.1132 (3)−0.1039 (2)0.0717 (12)
H40A0.09740.1292−0.08550.086*
C410.0142 (4)0.0993 (4)−0.1678 (2)0.0879 (16)
H41A0.05130.1056−0.19210.106*
C42−0.0673 (4)0.0762 (3)−0.1959 (2)0.0792 (14)
C43−0.1204 (3)0.0658 (3)−0.1590 (2)0.0753 (13)
H43A−0.17560.0488−0.17740.090*
C44−0.0934 (3)0.0801 (3)−0.0949 (2)0.0639 (11)
H44A−0.13030.0737−0.07050.077*
C45−0.0990 (4)0.0618 (5)−0.2663 (2)0.120 (2)
H45A−0.05420.0716−0.28500.180*
H45B−0.14310.1057−0.28350.180*
H45C−0.1199−0.0011−0.27480.180*
C460.2665 (2)−0.0051 (3)0.0259 (2)0.0626 (11)
C470.1987 (3)0.3255 (3)−0.0465 (2)0.0617 (11)
C480.4580 (4)0.1386 (4)0.2277 (2)0.0909 (16)
S10.24756 (8)−0.10483 (11)−0.01078 (8)0.1025 (5)
S20.16650 (12)0.39843 (13)−0.10448 (7)0.1192 (6)
S30.55281 (11)0.13689 (15)0.27002 (10)0.1500 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ce0.04068 (12)0.05215 (15)0.04987 (15)0.00344 (10)0.00563 (9)0.00376 (12)
N10.055 (2)0.059 (2)0.071 (2)0.0126 (17)0.0131 (19)0.006 (2)
N20.0464 (17)0.056 (2)0.0494 (19)−0.0025 (15)0.0082 (15)−0.0033 (16)
N30.0471 (17)0.048 (2)0.058 (2)0.0034 (15)0.0128 (15)0.0025 (16)
N40.063 (2)0.068 (3)0.106 (3)−0.005 (2)0.030 (2)−0.016 (2)
N50.073 (2)0.081 (3)0.055 (2)0.010 (2)0.011 (2)0.006 (2)
N60.076 (3)0.142 (5)0.079 (3)0.033 (3)0.004 (2)0.038 (3)
O10.0658 (17)0.0602 (18)0.0464 (16)0.0091 (13)0.0089 (13)−0.0029 (14)
O20.0677 (19)0.087 (2)0.0532 (18)−0.0037 (17)−0.0063 (15)0.0047 (16)
O40.0588 (17)0.092 (2)0.0427 (16)−0.0094 (15)0.0025 (13)0.0086 (15)
O30.0458 (14)0.0679 (19)0.0523 (16)−0.0030 (13)0.0146 (12)−0.0054 (14)
O50.0473 (15)0.0460 (17)0.083 (2)−0.0026 (12)0.0200 (14)0.0005 (14)
O60.0742 (19)0.0475 (18)0.090 (2)0.0081 (14)0.0242 (17)0.0017 (16)
C10.080 (3)0.062 (3)0.064 (3)0.006 (2)0.025 (3)−0.008 (2)
C20.075 (3)0.051 (3)0.047 (2)0.000 (2)0.016 (2)0.002 (2)
C30.080 (3)0.067 (3)0.053 (3)−0.005 (3)0.010 (2)−0.001 (2)
C40.113 (4)0.116 (5)0.058 (3)−0.023 (4)0.014 (3)−0.025 (3)
C50.140 (6)0.128 (6)0.081 (4)−0.017 (5)0.037 (4)−0.051 (4)
C60.119 (5)0.095 (4)0.090 (4)0.010 (4)0.041 (4)−0.029 (3)
C70.079 (3)0.056 (3)0.084 (3)0.013 (2)0.033 (3)−0.002 (3)
C80.079 (3)0.104 (4)0.093 (4)−0.015 (3)−0.021 (3)0.003 (3)
C90.062 (3)0.048 (3)0.073 (3)0.015 (2)0.009 (2)0.006 (2)
C100.064 (3)0.080 (4)0.103 (4)0.023 (3)0.019 (3)0.002 (3)
C110.064 (3)0.096 (4)0.133 (5)0.022 (3)0.015 (4)0.008 (4)
C120.062 (3)0.069 (4)0.123 (5)0.013 (3)−0.011 (3)0.024 (3)
C130.090 (4)0.061 (3)0.090 (4)0.009 (3)0.001 (3)0.004 (3)
C140.066 (3)0.056 (3)0.083 (3)0.007 (2)0.010 (3)0.009 (3)
C150.093 (4)0.114 (5)0.163 (6)0.008 (4)−0.043 (4)0.001 (5)
C160.050 (2)0.052 (3)0.072 (3)−0.0047 (18)0.019 (2)0.000 (2)
C170.055 (2)0.044 (2)0.052 (2)−0.0066 (19)0.0131 (19)−0.0009 (19)
C180.064 (3)0.049 (3)0.065 (3)0.001 (2)0.018 (2)−0.001 (2)
C190.088 (4)0.050 (3)0.125 (5)−0.012 (3)0.034 (3)−0.004 (3)
C200.084 (4)0.063 (4)0.165 (6)−0.031 (3)0.046 (4)−0.014 (4)
C210.062 (3)0.071 (3)0.136 (5)−0.012 (3)0.035 (3)−0.005 (3)
C220.050 (2)0.056 (3)0.075 (3)0.001 (2)0.019 (2)−0.004 (2)
C230.113 (4)0.045 (3)0.131 (5)0.024 (3)0.046 (4)0.017 (3)
C240.050 (2)0.050 (2)0.045 (2)0.0018 (18)0.0046 (18)0.0014 (19)
C250.066 (3)0.055 (3)0.064 (3)−0.002 (2)0.022 (2)0.001 (2)
C260.076 (3)0.062 (3)0.055 (3)0.014 (2)0.013 (2)−0.003 (2)
C270.083 (3)0.047 (3)0.051 (3)0.004 (2)−0.001 (2)0.000 (2)
C280.072 (3)0.059 (3)0.080 (3)−0.013 (2)0.004 (3)0.006 (3)
C290.054 (2)0.061 (3)0.073 (3)−0.001 (2)0.006 (2)0.002 (2)
C300.122 (4)0.052 (3)0.087 (4)0.000 (3)0.006 (3)−0.007 (3)
C310.047 (2)0.053 (2)0.048 (2)−0.0025 (17)0.0124 (18)−0.0020 (19)
C320.050 (2)0.049 (2)0.049 (2)−0.0006 (18)0.0152 (18)0.0036 (19)
C330.057 (2)0.051 (2)0.051 (2)−0.0061 (19)0.013 (2)0.0070 (19)
C340.079 (3)0.073 (3)0.049 (2)−0.004 (2)0.018 (2)−0.001 (2)
C350.072 (3)0.084 (3)0.068 (3)−0.008 (2)0.036 (3)−0.009 (3)
C360.053 (2)0.083 (3)0.068 (3)−0.002 (2)0.024 (2)−0.002 (3)
C370.047 (2)0.053 (2)0.058 (3)0.0000 (18)0.013 (2)0.002 (2)
C380.077 (3)0.153 (6)0.040 (3)−0.018 (3)−0.005 (2)0.014 (3)
C390.057 (2)0.049 (2)0.047 (2)0.0000 (18)0.0089 (19)−0.0025 (19)
C400.069 (3)0.081 (3)0.067 (3)−0.015 (2)0.022 (2)−0.015 (3)
C410.115 (4)0.092 (4)0.065 (3)−0.026 (3)0.040 (3)−0.019 (3)
C420.114 (4)0.066 (3)0.054 (3)−0.013 (3)0.018 (3)−0.009 (2)
C430.074 (3)0.075 (3)0.064 (3)−0.010 (2)−0.002 (3)−0.012 (3)
C440.060 (3)0.068 (3)0.061 (3)−0.005 (2)0.013 (2)−0.006 (2)
C450.176 (6)0.114 (5)0.059 (3)−0.029 (4)0.014 (4)−0.020 (3)
C460.043 (2)0.068 (3)0.080 (3)−0.011 (2)0.021 (2)−0.012 (3)
C470.070 (3)0.072 (3)0.043 (2)0.017 (2)0.015 (2)−0.008 (2)
C480.092 (4)0.094 (4)0.077 (4)0.035 (3)0.008 (3)0.017 (3)
S10.0706 (8)0.0955 (10)0.1541 (14)−0.0343 (7)0.0519 (9)−0.0574 (10)
S20.1679 (15)0.1299 (14)0.0722 (9)0.0734 (12)0.0540 (10)0.0403 (9)
S30.0956 (12)0.1407 (17)0.1694 (18)0.0401 (11)−0.0382 (12)−0.0171 (14)
Geometric parameters (Å, °) top
Ce—O52.408 (2)C16—C211.410 (6)
Ce—O32.423 (2)C16—C171.418 (5)
Ce—O12.436 (3)C17—C181.414 (5)
Ce—N62.519 (4)C18—C191.346 (6)
Ce—N52.558 (4)C19—C201.379 (7)
Ce—N42.576 (4)C19—H19A0.9300
Ce—O22.792 (3)C20—C211.363 (7)
Ce—O42.795 (3)C20—H20A0.9300
Ce—O62.838 (3)C21—H21A0.9300
N1—C71.297 (5)C22—H22A0.9300
N1—C91.414 (5)C23—H23A0.9600
N1—H1A0.8600C23—H23B0.9600
N2—C371.303 (4)C23—H23C0.9600
N2—C391.422 (5)C24—C251.373 (5)
N2—H2A0.8600C24—C291.386 (5)
N3—C221.288 (5)C25—C261.376 (6)
N3—C241.406 (5)C25—H25A0.9300
N3—H3A0.8600C26—C271.373 (6)
N4—C461.148 (5)C26—H26A0.9300
N5—C471.132 (5)C27—C281.391 (6)
N6—C481.158 (6)C27—C301.498 (6)
O1—C21.303 (4)C28—C291.385 (6)
O2—C31.374 (5)C28—H28A0.9300
O2—C81.437 (5)C29—H29A0.9300
O4—C331.383 (4)C30—H30A0.9600
O4—C381.429 (5)C30—H30B0.9600
O3—C321.307 (4)C30—H30C0.9600
O5—C171.289 (4)C31—C371.403 (5)
O6—C181.367 (5)C31—C361.406 (5)
O6—C231.436 (5)C31—C321.411 (5)
C1—C71.403 (6)C32—C331.402 (5)
C1—C21.405 (6)C33—C341.368 (5)
C1—C61.417 (6)C34—C351.393 (6)
C2—C31.418 (6)C34—H34A0.9300
C3—C41.369 (6)C35—C361.354 (6)
C4—C51.394 (8)C35—H35A0.9300
C4—H4A0.9300C36—H36A0.9300
C5—C61.351 (8)C37—H37A0.9300
C5—H5B0.9300C38—H38A0.9600
C6—H6B0.9300C38—H38B0.9600
C7—H7A0.9300C38—H38C0.9600
C8—H8A0.9600C39—C401.358 (5)
C8—H8B0.9600C39—C441.377 (5)
C8—H8C0.9600C40—C411.379 (6)
C9—C141.375 (6)C40—H40A0.9300
C9—C101.374 (6)C41—C421.370 (7)
C10—C111.364 (7)C41—H41A0.9300
C10—H10A0.9300C42—C431.368 (6)
C11—C121.385 (8)C42—C451.519 (6)
C11—H11A0.9300C43—C441.384 (6)
C12—C131.380 (7)C43—H43A0.9300
C12—C151.522 (8)C44—H44A0.9300
C13—C141.390 (6)C45—H45A0.9600
C13—H13A0.9300C45—H45B0.9600
C14—H14A0.9300C45—H45C0.9600
C15—H15A0.9600C46—S11.623 (5)
C15—H15B0.9600C47—S21.626 (5)
C15—H15C0.9600C48—S31.601 (6)
C16—C221.409 (5)
O5—Ce—O3143.08 (9)C12—C15—H15C109.5
O5—Ce—O1133.75 (9)H15A—C15—H15C109.5
O3—Ce—O174.32 (9)H15B—C15—H15C109.5
O5—Ce—N672.93 (12)C22—C16—C21120.9 (4)
O3—Ce—N6111.00 (13)C22—C16—C17119.9 (3)
O1—Ce—N6128.14 (12)C21—C16—C17119.2 (4)
O5—Ce—N587.26 (11)O5—C17—C18120.0 (3)
O3—Ce—N578.58 (11)O5—C17—C16122.0 (4)
O1—Ce—N573.43 (10)C18—C17—C16118.0 (4)
N6—Ce—N5157.54 (13)C19—C18—O6127.7 (4)
O5—Ce—N473.60 (10)C19—C18—C17120.6 (4)
O3—Ce—N470.59 (10)O6—C18—C17111.8 (3)
O1—Ce—N4139.75 (10)C18—C19—C20121.9 (5)
N6—Ce—N483.45 (15)C18—C19—H19A119.1
N5—Ce—N480.81 (13)C20—C19—H19A119.1
O5—Ce—O299.72 (9)C21—C20—C19119.9 (4)
O3—Ce—O2116.95 (8)C21—C20—H20A120.0
O1—Ce—O258.93 (9)C19—C20—H20A120.0
N6—Ce—O275.11 (14)C20—C21—C16120.4 (4)
N5—Ce—O2119.74 (11)C20—C21—H21A119.8
N4—Ce—O2158.56 (11)C16—C21—H21A119.8
O5—Ce—O4142.27 (9)N3—C22—C16124.0 (4)
O3—Ce—O459.54 (8)N3—C22—H22A118.0
O1—Ce—O470.74 (9)C16—C22—H22A118.0
N6—Ce—O469.64 (11)O6—C23—H23A109.5
N5—Ce—O4130.40 (10)O6—C23—H23B109.5
N4—Ce—O4106.26 (10)H23A—C23—H23B109.5
O2—Ce—O466.27 (9)O6—C23—H23C109.5
O5—Ce—O657.99 (8)H23A—C23—H23C109.5
O3—Ce—O6143.41 (9)H23B—C23—H23C109.5
O1—Ce—O676.07 (9)C25—C24—C29119.8 (4)
N6—Ce—O6104.06 (13)C25—C24—N3122.9 (3)
N5—Ce—O672.71 (11)C29—C24—N3117.3 (3)
N4—Ce—O6124.87 (10)C24—C25—C26119.8 (4)
O2—Ce—O662.29 (8)C24—C25—H25A120.1
O4—Ce—O6127.83 (8)C26—C25—H25A120.1
C7—N1—C9128.8 (4)C27—C26—C25122.4 (4)
C7—N1—H1A115.6C27—C26—H26A118.8
C9—N1—H1A115.6C25—C26—H26A118.8
C37—N2—C39128.2 (3)C26—C27—C28117.0 (4)
C37—N2—H2A115.9C26—C27—C30122.3 (4)
C39—N2—H2A115.9C28—C27—C30120.7 (4)
C22—N3—C24128.5 (3)C29—C28—C27122.0 (4)
C22—N3—H3A115.7C29—C28—H28A119.0
C24—N3—H3A115.7C27—C28—H28A119.0
C46—N4—Ce169.8 (3)C28—C29—C24119.1 (4)
C47—N5—Ce157.0 (4)C28—C29—H29A120.5
C48—N6—Ce145.1 (5)C24—C29—H29A120.5
C2—O1—Ce127.4 (2)C27—C30—H30A109.5
C3—O2—C8118.3 (4)C27—C30—H30B109.5
C3—O2—Ce115.6 (2)H30A—C30—H30B109.5
C8—O2—Ce125.8 (3)C27—C30—H30C109.5
C33—O4—C38116.8 (3)H30A—C30—H30C109.5
C33—O4—Ce114.0 (2)H30B—C30—H30C109.5
C38—O4—Ce128.9 (2)C37—C31—C36120.3 (3)
C32—O3—Ce126.7 (2)C37—C31—C32120.2 (3)
C17—O5—Ce130.5 (2)C36—C31—C32119.5 (4)
C18—O6—C23118.3 (3)O3—C32—C33120.1 (3)
C18—O6—Ce115.7 (2)O3—C32—C31121.8 (3)
C23—O6—Ce125.8 (3)C33—C32—C31118.1 (3)
C7—C1—C2119.6 (4)C34—C33—O4125.2 (4)
C7—C1—C6120.7 (5)C34—C33—C32121.4 (4)
C2—C1—C6119.7 (5)O4—C33—C32113.4 (3)
O1—C2—C1122.8 (4)C33—C34—C35119.8 (4)
O1—C2—C3119.0 (4)C33—C34—H34A120.1
C1—C2—C3118.3 (4)C35—C34—H34A120.1
C4—C3—O2126.4 (5)C36—C35—C34120.6 (4)
C4—C3—C2120.6 (5)C36—C35—H35A119.7
O2—C3—C2113.0 (4)C34—C35—H35A119.7
C3—C4—C5120.3 (5)C35—C36—C31120.6 (4)
C3—C4—H4A119.8C35—C36—H36A119.7
C5—C4—H4A119.8C31—C36—H36A119.7
C6—C5—C4120.9 (5)N2—C37—C31124.3 (3)
C6—C5—H5B119.6N2—C37—H37A117.9
C4—C5—H5B119.6C31—C37—H37A117.9
C5—C6—C1120.3 (5)O4—C38—H38A109.5
C5—C6—H6B119.9O4—C38—H38B109.5
C1—C6—H6B119.9H38A—C38—H38B109.5
N1—C7—C1123.3 (4)O4—C38—H38C109.5
N1—C7—H7A118.4H38A—C38—H38C109.5
C1—C7—H7A118.4H38B—C38—H38C109.5
O2—C8—H8A109.5C40—C39—C44119.8 (4)
O2—C8—H8B109.5C40—C39—N2118.3 (4)
H8A—C8—H8B109.5C44—C39—N2121.8 (3)
O2—C8—H8C109.5C39—C40—C41120.3 (4)
H8A—C8—H8C109.5C39—C40—H40A119.8
H8B—C8—H8C109.5C41—C40—H40A119.8
C14—C9—C10120.2 (5)C42—C41—C40120.8 (4)
C14—C9—N1117.5 (4)C42—C41—H41A119.6
C10—C9—N1122.2 (4)C40—C41—H41A119.6
C11—C10—C9120.0 (5)C43—C42—C41118.5 (4)
C11—C10—H10A120.0C43—C42—C45120.0 (5)
C9—C10—H10A120.0C41—C42—C45121.4 (5)
C10—C11—C12121.7 (5)C42—C43—C44121.2 (4)
C10—C11—H11A119.1C42—C43—H43A119.4
C12—C11—H11A119.1C44—C43—H43A119.4
C13—C12—C11117.4 (5)C39—C44—C43119.3 (4)
C13—C12—C15119.3 (6)C39—C44—H44A120.4
C11—C12—C15123.3 (6)C43—C44—H44A120.4
C12—C13—C14121.7 (5)C42—C45—H45A109.5
C12—C13—H13A119.2C42—C45—H45B109.5
C14—C13—H13A119.2H45A—C45—H45B109.5
C9—C14—C13118.9 (4)C42—C45—H45C109.5
C9—C14—H14A120.5H45A—C45—H45C109.5
C13—C14—H14A120.5H45B—C45—H45C109.5
C12—C15—H15A109.5N4—C46—S1177.7 (5)
C12—C15—H15B109.5N5—C47—S2179.5 (4)
H15A—C15—H15B109.5N6—C48—S3178.3 (6)
O5—Ce—N4—C46−145 (2)C8—O2—C3—C4−11.6 (7)
O3—Ce—N4—C4626 (2)Ce—O2—C3—C4163.4 (4)
O1—Ce—N4—C46−5(2)C8—O2—C3—C2170.8 (4)
N6—Ce—N4—C46141 (2)Ce—O2—C3—C2−14.2 (4)
N5—Ce—N4—C46−55 (2)O1—C2—C3—C4178.5 (4)
O2—Ce—N4—C46141 (2)C1—C2—C3—C4−1.6 (7)
O4—Ce—N4—C4674 (2)O1—C2—C3—O2−3.8 (6)
O6—Ce—N4—C46−117 (2)C1—C2—C3—O2176.1 (4)
O5—Ce—N5—C47−93.6 (9)O2—C3—C4—C5−176.7 (5)
O3—Ce—N5—C47120.7 (9)C2—C3—C4—C50.7 (8)
O1—Ce—N5—C4743.8 (9)C3—C4—C5—C60.4 (10)
N6—Ce—N5—C47−121.4 (9)C4—C5—C6—C1−0.5 (10)
N4—Ce—N5—C47−167.4 (9)C7—C1—C6—C5178.3 (5)
O2—Ce—N5—C476.0 (9)C2—C1—C6—C5−0.5 (8)
O4—Ce—N5—C4789.0 (9)C9—N1—C7—C1174.4 (4)
O6—Ce—N5—C47−36.4 (9)C2—C1—C7—N1−1.9 (7)
O5—Ce—N6—C4839.4 (8)C6—C1—C7—N1179.3 (4)
O3—Ce—N6—C48−179.5 (8)C7—N1—C9—C14161.3 (4)
O1—Ce—N6—C48−93.3 (8)C7—N1—C9—C10−20.9 (7)
N5—Ce—N6—C4868.6 (10)C14—C9—C10—C110.2 (7)
N4—Ce—N6—C48114.2 (8)N1—C9—C10—C11−177.5 (5)
O2—Ce—N6—C48−65.9 (8)C9—C10—C11—C12−0.4 (8)
O4—Ce—N6—C48−135.7 (8)C10—C11—C12—C130.9 (8)
O6—Ce—N6—C48−10.1 (8)C10—C11—C12—C15178.8 (5)
O5—Ce—O1—C2−95.1 (3)C11—C12—C13—C14−1.1 (8)
O3—Ce—O1—C2113.1 (3)C15—C12—C13—C14−179.1 (5)
N6—Ce—O1—C28.5 (4)C10—C9—C14—C13−0.4 (7)
N5—Ce—O1—C2−164.4 (3)N1—C9—C14—C13177.4 (4)
N4—Ce—O1—C2143.2 (3)C12—C13—C14—C90.9 (7)
O2—Ce—O1—C2−22.8 (3)Ce—O5—C17—C18−18.9 (6)
O4—Ce—O1—C250.5 (3)Ce—O5—C17—C16161.0 (3)
O6—Ce—O1—C2−88.6 (3)C22—C16—C17—O5−1.5 (6)
O5—Ce—O2—C3153.7 (3)C21—C16—C17—O5179.1 (4)
O3—Ce—O2—C3−30.7 (3)C22—C16—C17—C18178.4 (4)
O1—Ce—O2—C318.0 (3)C21—C16—C17—C18−1.0 (6)
N6—Ce—O2—C3−137.0 (3)C23—O6—C18—C198.5 (7)
N5—Ce—O2—C361.3 (3)Ce—O6—C18—C19−166.5 (4)
N4—Ce—O2—C3−136.7 (3)C23—O6—C18—C17−171.3 (4)
O4—Ce—O2—C3−63.1 (3)Ce—O6—C18—C1713.7 (4)
O6—Ce—O2—C3107.9 (3)O5—C17—C18—C19180.0 (4)
O5—Ce—O2—C8−31.8 (4)C16—C17—C18—C190.1 (6)
O3—Ce—O2—C8143.8 (3)O5—C17—C18—O6−0.2 (6)
O1—Ce—O2—C8−167.5 (4)C16—C17—C18—O6179.9 (4)
N6—Ce—O2—C837.5 (3)O6—C18—C19—C20−179.4 (5)
N5—Ce—O2—C8−124.2 (3)C17—C18—C19—C200.4 (8)
N4—Ce—O2—C837.9 (5)C18—C19—C20—C210.0 (9)
O4—Ce—O2—C8111.5 (4)C19—C20—C21—C16−1.0 (9)
O6—Ce—O2—C8−77.5 (3)C22—C16—C21—C20−177.9 (5)
O5—Ce—O4—C33−158.6 (2)C17—C16—C21—C201.4 (8)
O3—Ce—O4—C33−19.6 (2)C24—N3—C22—C16−179.3 (4)
O1—Ce—O4—C3363.2 (3)C21—C16—C22—N3177.4 (4)
N6—Ce—O4—C33−151.0 (3)C17—C16—C22—N3−2.0 (7)
N5—Ce—O4—C3317.1 (3)C22—N3—C24—C25−8.8 (6)
N4—Ce—O4—C33−74.6 (3)C22—N3—C24—C29171.9 (4)
O2—Ce—O4—C33126.8 (3)C29—C24—C25—C26−0.6 (6)
O6—Ce—O4—C33116.7 (3)N3—C24—C25—C26−179.8 (4)
O5—Ce—O4—C3828.0 (4)C24—C25—C26—C270.1 (7)
O3—Ce—O4—C38167.1 (4)C25—C26—C27—C280.1 (6)
O1—Ce—O4—C38−110.2 (4)C25—C26—C27—C30−179.8 (4)
N6—Ce—O4—C3835.7 (4)C26—C27—C28—C290.2 (7)
N5—Ce—O4—C38−156.2 (4)C30—C27—C28—C29−179.9 (4)
N4—Ce—O4—C38112.1 (4)C27—C28—C29—C24−0.6 (7)
O2—Ce—O4—C38−46.5 (4)C25—C24—C29—C280.8 (6)
O6—Ce—O4—C38−56.6 (4)N3—C24—C29—C28−179.9 (4)
O5—Ce—O3—C32160.2 (3)Ce—O3—C32—C33−22.8 (5)
O1—Ce—O3—C32−54.5 (3)Ce—O3—C32—C31157.6 (3)
N6—Ce—O3—C3270.9 (3)C37—C31—C32—O30.0 (6)
N5—Ce—O3—C32−130.3 (3)C36—C31—C32—O3−179.0 (4)
N4—Ce—O3—C32145.6 (3)C37—C31—C32—C33−179.6 (4)
O2—Ce—O3—C32−12.5 (3)C36—C31—C32—C331.3 (6)
O4—Ce—O3—C3222.1 (3)C38—O4—C33—C3412.6 (6)
O6—Ce—O3—C32−91.6 (3)Ce—O4—C33—C34−161.6 (3)
O3—Ce—O5—C17156.3 (3)C38—O4—C33—C32−168.2 (4)
O1—Ce—O5—C1725.6 (4)Ce—O4—C33—C3217.6 (4)
N6—Ce—O5—C17−101.3 (4)O3—C32—C33—C34178.9 (4)
N5—Ce—O5—C1789.4 (3)C31—C32—C33—C34−1.5 (6)
N4—Ce—O5—C17170.7 (4)O3—C32—C33—O4−0.3 (5)
O2—Ce—O5—C17−30.3 (3)C31—C32—C33—O4179.3 (3)
O4—Ce—O5—C17−93.8 (3)O4—C33—C34—C35179.7 (4)
O6—Ce—O5—C1718.2 (3)C32—C33—C34—C350.6 (7)
O5—Ce—O6—C18−15.5 (3)C33—C34—C35—C360.5 (7)
O3—Ce—O6—C18−153.3 (2)C34—C35—C36—C31−0.6 (7)
O1—Ce—O6—C18170.0 (3)C37—C31—C36—C35−179.4 (4)
N6—Ce—O6—C1843.6 (3)C32—C31—C36—C35−0.3 (7)
N5—Ce—O6—C18−113.3 (3)C39—N2—C37—C31−177.6 (4)
N4—Ce—O6—C18−48.2 (3)C36—C31—C37—N2−179.3 (4)
O2—Ce—O6—C18108.0 (3)C32—C31—C37—N21.6 (6)
O4—Ce—O6—C18118.5 (3)C37—N2—C39—C40165.0 (4)
O5—Ce—O6—C23169.9 (4)C37—N2—C39—C44−12.1 (6)
O3—Ce—O6—C2332.2 (4)C44—C39—C40—C410.0 (7)
O1—Ce—O6—C23−4.6 (3)N2—C39—C40—C41−177.1 (4)
N6—Ce—O6—C23−131.0 (4)C39—C40—C41—C420.3 (8)
N5—Ce—O6—C2372.1 (4)C40—C41—C42—C43−1.0 (8)
N4—Ce—O6—C23137.2 (4)C40—C41—C42—C45179.3 (5)
O2—Ce—O6—C23−66.6 (4)C41—C42—C43—C441.4 (8)
O4—Ce—O6—C23−56.1 (4)C45—C42—C43—C44−178.9 (5)
Ce—O1—C2—C1−154.3 (3)C40—C39—C44—C430.3 (7)
Ce—O1—C2—C325.6 (5)N2—C39—C44—C43177.4 (4)
C7—C1—C2—O12.6 (7)C42—C43—C44—C39−1.0 (7)
C6—C1—C2—O1−178.6 (4)Ce—N4—C46—S1−141 (8)
C7—C1—C2—C3−177.3 (4)Ce—N5—C47—S2−10 (53)
C6—C1—C2—C31.5 (6)Ce—N6—C48—S350 (19)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O10.861.852.556 (4)138
N2—H2A···O30.861.892.583 (4)137
N3—H3A···O50.861.882.579 (4)137
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O10.861.852.556 (4)138
N2—H2A···O30.861.892.583 (4)137
N3—H3A···O50.861.882.579 (4)137
references
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