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Acta Cryst. (2010). E66, m72    [ doi:10.1107/S1600536809053124 ]

Tris[2-methoxy-6-(4-methylphenyliminiomethyl)phenolato-[kappa]2O,O']tris(thiocyanato-[kappa]N)neodymium(III)

J.-L. Liu, J.-B. Shen and G.-L. Zhao

Abstract top

In the title compound, [Nd(NCS)3(C15H15NO2)3], the NdIII ion is coordinated by three thiocyanate anions [Nd-N = 2.489 (8)-2.530 (7) Å] and six O atoms [Nd-O = 2.375 (4)-2.843 (5) Å] from three zwitterionic 2-methoxy-6-(4-methylphenyliminiomethyl)phenolate ligands in a tricapped trigonal-prismatic geometry. Intramolecular N-H...O hydrogen bonds occur. The crystal packing exhibits weak intermolecular C-H...S hydrogen bonds, [pi]-[pi] interactions with a distance of 3.904 (7) Å between the centroids of the aromatic rings, and voids of 101 Å3.

Comment top

Schiff base ligands derived from substituted salicylaldehyde and their metal complexes have been widely investigated because of their structural features (Wang et al.,1994). In this aspect we have been synthesized several analogous Schiff bases transitional and rare metal complexes. In recent articles we have reported our research results (Zhao et al., 2007; Xian et al., 2008; Li et al., 2008). Herein, we report the crystal structure of the title Nd3+ complex, (I).

In (I) (Fig. 1), the NdIII is nine- coordinated by three nitrogen atoms from three thiocyanate ions and six O atoms from 2-(4-methylphenyliminomethyl)-6-methoxyphenolato) (L). L ligands coordinate the Nd center with bidentate-chelate mode using oxygen atoms from deprotonated phenolic hydroxyl groups and methoxyl groups. The imino H atoms in L are involved in intramolecular N—H···O hydrogen bonds (Table 1). The bonds between NdIII and O atoms from phenolic hydroxyl groups are 2.375 (2) -2.393 (3) Å, which are shorter than those between Nd and O atoms of methoxyl groups (2.742 (3) - 2.843 (3) Å). The Nd—N bond lengths are 2.489 (4) -2.530 (4) Å. The structure of (I) is similar to the structures of analogous complexes (Zhao et al., 2007; Li et al., 2008).

The crystal packing exhibits weak intermolecular C—H···S hydrogen bonds (Table 1) and π-π interaction with the distance of 3.904 (7) Å between the centroids of aromatic rings.

Related literature top

For related structures, see: Wang et al. (1994); Zhao et al. (2007); Xian et al. (2008); 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 prepare in a high yield synthesis by condensation of o-vanillin and p-methyllaniline and was recrystallized in ethanol before being used. 1 mmol N d(NO3)3 (dissolved in methanol) was added dropwise into a methanol solution with 3 mmol 3-methoxy-N-salicylidene-p-toluidine under stirring and the mixture was continuously stirred at room temperature for 8 h to obtain a red solution. The deposit was filtered off and the solution was left standing for slow evaporation. Red crystals of the title compound were obtained after several days.

Refinement top

All H atoms were positioned geometrically (C—H 0.93–0.96 Å, N—H 0.86 Å), and refined as riding, with Uiso(H) = 1.2–1.5Ueq(C, N). The crystal packing exhibits voids of 101 Å3 centered at (0.19, 0.67, 0.24).

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-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms omitted for clarity.
Tris[2-methoxy-6-(4-methylphenyliminiomethyl)phenolato- κ2O,O']tris(thiocyanato-κN)neodymium(III) top
Crystal data top
[Nd(NCS)3(C15H15NO2)3]F(000) = 2124
Mr = 1042.35Dx = 1.374 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2091 reflections
a = 16.6107 (3) Åθ = 1.4–27.6°
b = 14.2425 (3) ŵ = 1.21 mm−1
c = 22.1582 (4) ÅT = 296 K
β = 105.972 (1)°Block, red
V = 5039.77 (17) Å30.14 × 0.08 × 0.05 mm
Z = 4
Data collection top
Bruker APEXII
diffractometer		5189 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.114
graphiteθmax = 27.6°, θmin = 1.3°
ω scansh = −21→21
44769 measured reflectionsk = −18→18
11604 independent reflectionsl = −28→28
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)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.190H-atom parameters constrained
S = 0.86 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
11604 reflections(Δ/σ)max = 0.001
562 parametersΔρmax = 0.66 e Å−3
0 restraintsΔρmin = −0.84 e Å−3
Crystal data top
[Nd(NCS)3(C15H15NO2)3]V = 5039.77 (17) Å3
Mr = 1042.35Z = 4
Monoclinic, P21/cMo Kα radiation
a = 16.6107 (3) ŵ = 1.21 mm−1
b = 14.2425 (3) ÅT = 296 K
c = 22.1582 (4) Å0.14 × 0.08 × 0.05 mm
β = 105.972 (1)°
Data collection top
Bruker APEXII
diffractometer		Rint = 0.114
44769 measured reflectionsθmax = 27.6°
11604 independent reflectionsStandard reflections: none
5189 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.060H-atom parameters constrained
wR(F2) = 0.190Δρmax = 0.66 e Å−3
S = 0.86Δρmin = −0.84 e Å−3
11604 reflectionsAbsolute structure: ?
562 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
Nd1.21267 (2)0.27661 (3)1.393189 (17)0.04942 (15)
C11.7474 (6)0.2005 (8)1.6278 (6)0.132 (4)
H1B1.79700.19351.61400.197*
H1C1.75170.16161.66390.197*
H1D1.74160.26491.63860.197*
C21.6709 (6)0.1709 (6)1.5751 (5)0.090 (3)
C31.6775 (5)0.1410 (7)1.5180 (6)0.098 (3)
H3B1.73030.13681.51150.118*
C41.6086 (5)0.1167 (6)1.4699 (4)0.079 (2)
H4A1.61500.09691.43150.095*
C51.5300 (5)0.1220 (5)1.4793 (4)0.064 (2)
C61.5214 (5)0.1515 (5)1.5365 (4)0.066 (2)
H6A1.46860.15521.54300.079*
C71.5906 (6)0.1754 (6)1.5834 (4)0.082 (2)
H7A1.58420.19511.62180.099*
C81.4479 (5)0.0514 (5)1.3821 (4)0.065 (2)
H8A1.49390.01821.37720.078*
C91.3712 (5)0.0448 (5)1.3347 (4)0.069 (2)
C101.3636 (7)−0.0112 (6)1.2797 (5)0.097 (3)
H10A1.4097−0.04481.27520.116*
C111.2900 (8)−0.0158 (8)1.2340 (5)0.110 (4)
H11A1.2860−0.05311.19880.132*
C121.2212 (7)0.0342 (7)1.2392 (4)0.096 (3)
H12A1.17130.03071.20730.115*
C131.2253 (5)0.0892 (5)1.2909 (4)0.066 (2)
C141.3004 (5)0.0943 (5)1.3399 (4)0.0613 (19)
C151.0798 (5)0.1339 (7)1.2583 (4)0.098 (3)
H15A1.07910.08221.23040.147*
H15B1.06420.19041.23440.147*
H15C1.04080.12211.28230.147*
C160.9337 (6)0.8193 (6)1.4168 (4)0.092 (3)
H16A0.98160.84871.40850.138*
H16B0.92890.83931.45700.138*
H16C0.88410.83681.38480.138*
C170.9441 (5)0.7145 (5)1.4168 (3)0.0619 (19)
C180.8840 (5)0.6555 (6)1.4276 (4)0.069 (2)
H18A0.83600.68091.43480.083*
C190.8936 (4)0.5584 (5)1.4279 (3)0.0601 (19)
H19A0.85240.51951.43540.072*
C200.9633 (4)0.5209 (5)1.4171 (3)0.0523 (17)
C211.0259 (4)0.5778 (5)1.4075 (3)0.0604 (19)
H21A1.07460.55201.40180.072*
C221.0147 (5)0.6738 (5)1.4067 (4)0.071 (2)
H22A1.05600.71241.39910.085*
C230.9246 (4)0.3560 (5)1.4198 (3)0.0612 (19)
H23A0.87110.37261.42170.073*
C240.9442 (4)0.2599 (5)1.4191 (3)0.0576 (19)
C250.8829 (5)0.1900 (6)1.4185 (5)0.089 (3)
H25A0.82960.20761.42000.107*
C260.9016 (6)0.0991 (7)1.4158 (5)0.105 (3)
H26A0.86060.05391.41420.126*
C270.9813 (5)0.0716 (6)1.4151 (4)0.083 (3)
H27A0.99260.00791.41320.099*
C281.0438 (4)0.1343 (5)1.4174 (4)0.0600 (19)
C291.0261 (4)0.2302 (5)1.4194 (3)0.0495 (16)
C301.1531 (5)0.0226 (5)1.4252 (4)0.086 (3)
H30A1.1104−0.01691.43330.129*
H30B1.20270.01881.45980.129*
H30C1.16560.00221.38750.129*
C311.6013 (7)0.4363 (7)1.7675 (4)0.122 (4)
H31A1.55650.42741.78660.183*
H31B1.62380.49841.77650.183*
H31C1.64460.39101.78400.183*
C321.5683 (6)0.4236 (6)1.6970 (4)0.079 (2)
C331.4863 (6)0.3989 (6)1.6687 (4)0.085 (3)
H33A1.44960.39041.69330.102*
C341.4576 (5)0.3865 (6)1.6047 (4)0.073 (2)
H34A1.40180.37141.58620.088*
C351.5109 (4)0.3963 (5)1.5688 (3)0.0514 (17)
C361.5935 (4)0.4198 (5)1.5956 (4)0.063 (2)
H36A1.63010.42661.57070.075*
C371.6216 (5)0.4334 (6)1.6600 (4)0.075 (2)
H37A1.67730.44931.67830.090*
C381.5238 (4)0.3633 (4)1.4624 (3)0.0523 (17)
H38A1.58190.36741.47650.063*
C391.4875 (4)0.3426 (4)1.3990 (3)0.0482 (16)
C401.5387 (4)0.3304 (5)1.3584 (4)0.064 (2)
H40A1.59640.33731.37390.077*
C411.5055 (5)0.3089 (6)1.2974 (4)0.072 (2)
H41A1.54030.30051.27140.087*
C421.4185 (5)0.2993 (5)1.2729 (3)0.0610 (19)
H42A1.39530.28651.23050.073*
C431.3680 (4)0.3090 (5)1.3120 (3)0.0522 (17)
C441.4000 (4)0.3316 (5)1.3758 (3)0.0483 (16)
C451.2416 (5)0.3000 (7)1.2278 (4)0.091 (3)
H45A1.28210.31121.20500.137*
H45B1.19930.34781.21780.137*
H45C1.21620.23971.21660.137*
C461.2340 (4)0.5040 (5)1.4736 (3)0.0591 (19)
C471.0439 (6)0.3648 (7)1.2736 (4)0.090 (3)
C481.3000 (4)0.1762 (5)1.5462 (3)0.0577 (18)
N11.4566 (4)0.1018 (4)1.4318 (3)0.0628 (16)
H1A1.41130.12621.43650.075*
N20.9766 (3)0.4219 (4)1.4181 (2)0.0510 (14)
H2A1.02580.40411.41750.061*
N31.4809 (3)0.3773 (4)1.5032 (3)0.0499 (14)
H3A1.42740.37481.48830.060*
N41.2184 (4)0.4345 (5)1.4465 (3)0.0754 (18)*
N51.1129 (5)0.3612 (5)1.3056 (4)0.094 (2)*
N61.2775 (4)0.2273 (5)1.5051 (3)0.0677 (17)*
S11.25218 (13)0.60404 (18)1.51067 (13)0.0996 (9)
S20.94976 (19)0.3689 (2)1.23046 (17)0.1467 (14)
S31.3324 (2)0.1029 (2)1.60350 (12)0.1132 (10)
O11.1632 (3)0.1444 (4)1.3004 (2)0.0752 (15)
O21.3015 (3)0.1459 (3)1.3889 (2)0.0561 (12)
O31.1243 (3)0.1167 (3)1.4178 (2)0.0674 (14)
O41.0848 (3)0.2913 (3)1.4208 (2)0.0595 (13)
O51.2824 (3)0.3020 (4)1.2938 (2)0.0641 (13)
O61.3500 (2)0.3412 (3)1.4114 (2)0.0538 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Nd0.0425 (2)0.0534 (3)0.0489 (3)0.00325 (17)0.00670 (16)0.0035 (2)
C10.084 (7)0.122 (9)0.152 (11)0.005 (6)−0.028 (7)0.001 (8)
C20.073 (6)0.069 (6)0.104 (8)0.013 (5)−0.016 (6)−0.005 (6)
C30.053 (5)0.092 (7)0.134 (10)0.022 (5)0.000 (6)0.007 (7)
C40.066 (5)0.084 (6)0.088 (7)0.018 (4)0.019 (5)0.007 (5)
C50.072 (5)0.040 (4)0.078 (6)0.018 (4)0.016 (5)0.015 (4)
C60.061 (5)0.068 (5)0.063 (5)0.001 (4)0.009 (4)0.007 (4)
C70.091 (6)0.059 (5)0.083 (7)0.012 (5)0.001 (5)0.010 (5)
C80.074 (5)0.048 (5)0.073 (6)0.015 (4)0.023 (5)0.001 (4)
C90.092 (6)0.062 (5)0.058 (5)0.003 (4)0.029 (5)−0.010 (4)
C100.116 (8)0.086 (7)0.099 (8)0.001 (6)0.045 (7)−0.031 (6)
C110.140 (10)0.117 (9)0.074 (7)−0.021 (8)0.031 (7)−0.051 (6)
C120.118 (8)0.094 (7)0.073 (7)−0.016 (6)0.023 (6)−0.016 (6)
C130.084 (6)0.059 (5)0.050 (5)−0.002 (4)0.013 (4)−0.005 (4)
C140.076 (5)0.050 (4)0.057 (5)0.002 (4)0.018 (4)0.004 (4)
C150.079 (6)0.099 (7)0.086 (7)−0.020 (5)−0.029 (5)0.007 (6)
C160.122 (7)0.054 (5)0.085 (7)0.000 (5)0.003 (6)0.002 (5)
C170.078 (5)0.047 (5)0.049 (5)0.005 (4)−0.003 (4)−0.002 (4)
C180.074 (5)0.065 (5)0.067 (5)0.011 (4)0.019 (4)−0.001 (4)
C190.062 (4)0.055 (5)0.065 (5)−0.003 (3)0.021 (4)0.002 (4)
C200.055 (4)0.052 (4)0.049 (4)−0.006 (3)0.012 (3)−0.001 (3)
C210.056 (4)0.054 (5)0.066 (5)0.001 (4)0.009 (4)0.000 (4)
C220.063 (5)0.057 (5)0.083 (6)−0.006 (4)0.003 (4)0.011 (5)
C230.052 (4)0.060 (5)0.075 (5)−0.001 (4)0.023 (4)−0.006 (4)
C240.053 (4)0.063 (5)0.059 (5)−0.004 (3)0.018 (4)−0.002 (4)
C250.076 (5)0.072 (6)0.136 (9)−0.014 (5)0.056 (6)−0.012 (6)
C260.091 (7)0.070 (7)0.161 (10)−0.026 (5)0.046 (7)−0.023 (7)
C270.096 (6)0.047 (5)0.104 (7)−0.007 (5)0.027 (6)−0.002 (5)
C280.063 (4)0.036 (4)0.079 (6)−0.004 (3)0.017 (4)0.003 (4)
C290.056 (4)0.051 (4)0.042 (4)−0.012 (3)0.013 (3)0.003 (3)
C300.098 (6)0.042 (5)0.128 (8)0.020 (4)0.045 (6)0.014 (5)
C310.189 (11)0.114 (9)0.051 (6)−0.040 (8)0.012 (7)−0.017 (6)
C320.111 (7)0.070 (6)0.049 (5)−0.015 (5)0.013 (5)−0.015 (4)
C330.112 (7)0.090 (7)0.064 (6)−0.031 (5)0.042 (6)−0.018 (5)
C340.074 (5)0.088 (6)0.062 (6)−0.017 (4)0.026 (5)−0.017 (5)
C350.057 (4)0.046 (4)0.050 (4)−0.004 (3)0.011 (4)−0.007 (3)
C360.057 (4)0.072 (5)0.060 (5)−0.013 (4)0.018 (4)−0.006 (4)
C370.075 (5)0.077 (6)0.063 (6)−0.010 (4)0.001 (5)−0.022 (5)
C380.048 (4)0.053 (4)0.058 (5)0.003 (3)0.018 (4)−0.004 (4)
C390.050 (4)0.045 (4)0.050 (4)−0.002 (3)0.015 (3)0.003 (3)
C400.052 (4)0.074 (5)0.071 (6)−0.003 (4)0.024 (4)−0.016 (4)
C410.077 (5)0.088 (6)0.061 (6)−0.002 (4)0.034 (5)−0.011 (5)
C420.074 (5)0.065 (5)0.042 (4)−0.003 (4)0.013 (4)0.005 (4)
C430.060 (4)0.054 (4)0.040 (4)−0.007 (3)0.009 (3)0.002 (3)
C440.053 (4)0.046 (4)0.046 (4)−0.002 (3)0.013 (3)0.006 (3)
C450.078 (6)0.133 (8)0.054 (5)−0.017 (5)0.001 (4)0.025 (5)
C460.045 (4)0.064 (5)0.066 (5)−0.010 (3)0.012 (4)−0.007 (4)
C470.079 (6)0.102 (7)0.080 (7)0.013 (5)0.007 (5)−0.003 (5)
C480.068 (4)0.064 (5)0.043 (4)0.012 (4)0.018 (4)−0.003 (4)
N10.062 (4)0.050 (4)0.074 (5)0.010 (3)0.016 (4)0.003 (4)
N20.044 (3)0.047 (3)0.062 (4)0.005 (3)0.014 (3)0.003 (3)
N30.044 (3)0.052 (3)0.052 (4)0.000 (2)0.010 (3)−0.006 (3)
S10.0686 (13)0.0964 (17)0.145 (2)−0.0332 (12)0.0477 (15)−0.0558 (17)
S20.094 (2)0.142 (3)0.161 (3)0.0396 (18)−0.038 (2)−0.016 (2)
S30.158 (3)0.122 (2)0.0708 (17)0.066 (2)0.0515 (17)0.0365 (16)
O10.073 (3)0.082 (4)0.059 (4)−0.009 (3)−0.002 (3)0.003 (3)
O20.059 (3)0.061 (3)0.044 (3)0.010 (2)0.007 (2)−0.003 (2)
O30.066 (3)0.048 (3)0.089 (4)0.009 (2)0.021 (3)0.005 (3)
O40.051 (3)0.046 (3)0.084 (4)−0.001 (2)0.023 (3)−0.002 (3)
O50.060 (3)0.084 (4)0.043 (3)−0.012 (2)0.005 (2)0.006 (3)
O60.048 (2)0.069 (3)0.046 (3)−0.002 (2)0.015 (2)−0.009 (2)
Geometric parameters (Å, °) top
Nd—O42.375 (4)C23—H23A0.9300
Nd—O62.388 (4)C24—C251.421 (10)
Nd—O22.393 (4)C24—C291.423 (9)
Nd—N52.489 (8)C25—C261.336 (12)
Nd—N62.517 (7)C25—H25A0.9300
Nd—N42.530 (7)C26—C271.385 (12)
Nd—O12.742 (5)C26—H26A0.9300
Nd—O52.778 (5)C27—C281.359 (10)
Nd—O32.843 (5)C27—H27A0.9300
C1—C21.530 (12)C28—O31.357 (8)
C1—H1B0.9600C28—C291.400 (9)
C1—H1C0.9600C29—O41.302 (7)
C1—H1D0.9600C30—O31.417 (8)
C2—C31.366 (12)C30—H30A0.9600
C2—C71.397 (12)C30—H30B0.9600
C3—C41.376 (12)C30—H30C0.9600
C3—H3B0.9300C31—C321.518 (10)
C4—C51.380 (10)C31—H31A0.9600
C4—H4A0.9300C31—H31B0.9600
C5—C61.379 (10)C31—H31C0.9600
C5—N11.405 (9)C32—C371.369 (10)
C6—C71.363 (10)C32—C331.380 (11)
C6—H6A0.9300C33—C341.379 (10)
C7—H7A0.9300C33—H33A0.9300
C8—N11.289 (9)C34—C351.350 (9)
C8—C91.413 (10)C34—H34A0.9300
C8—H8A0.9300C35—C361.379 (9)
C9—C141.403 (10)C35—N31.427 (8)
C9—C101.435 (11)C36—C371.388 (9)
C10—C111.358 (13)C36—H36A0.9300
C10—H10A0.9300C37—H37A0.9300
C11—C121.380 (13)C38—N31.311 (7)
C11—H11A0.9300C38—C391.400 (9)
C12—C131.373 (11)C38—H38A0.9300
C12—H12A0.9300C39—C401.409 (9)
C13—O11.358 (9)C39—C441.410 (8)
C13—C141.412 (10)C40—C411.347 (10)
C14—O21.307 (8)C40—H40A0.9300
C15—O11.450 (8)C41—C421.403 (10)
C15—H15A0.9600C41—H41A0.9300
C15—H15B0.9600C42—C431.369 (9)
C15—H15C0.9600C42—H42A0.9300
C16—C171.503 (10)C43—O51.371 (8)
C16—H16A0.9600C43—C441.403 (9)
C16—H16B0.9600C44—O61.301 (7)
C16—H16C0.9600C45—O51.433 (8)
C17—C181.374 (10)C45—H45A0.9600
C17—C221.380 (10)C45—H45B0.9600
C18—C191.391 (10)C45—H45C0.9600
C18—H18A0.9300C46—N41.150 (8)
C19—C201.355 (9)C46—S11.630 (8)
C19—H19A0.9300C47—N51.171 (10)
C20—C211.379 (9)C47—S21.594 (9)
C20—N21.426 (8)C48—N61.145 (8)
C21—C221.379 (10)C48—S31.617 (8)
C21—H21A0.9300N1—H1A0.8600
C22—H22A0.9300N2—H2A0.8600
C23—N21.284 (8)N3—H3A0.8600
C23—C241.408 (9)
O4—Nd—O6143.38 (15)C21—C22—C17122.1 (7)
O4—Nd—O2133.12 (15)C21—C22—H22A119.0
O6—Nd—O274.67 (15)C17—C22—H22A119.0
O4—Nd—N573.0 (2)N2—C23—C24123.4 (6)
O6—Nd—N5110.2 (2)N2—C23—H23A118.3
O2—Nd—N5129.1 (2)C24—C23—H23A118.3
O4—Nd—N686.67 (18)C23—C24—C25120.9 (7)
O6—Nd—N679.11 (18)C23—C24—C29120.9 (6)
O2—Nd—N673.77 (18)C25—C24—C29118.2 (7)
N5—Nd—N6156.4 (2)C26—C25—C24120.3 (8)
O4—Nd—N473.90 (18)C26—C25—H25A119.8
O6—Nd—N470.59 (17)C24—C25—H25A119.8
O2—Nd—N4139.96 (18)C25—C26—C27120.6 (8)
N5—Nd—N482.2 (2)C25—C26—H26A119.7
N6—Nd—N480.6 (2)C27—C26—H26A119.7
O4—Nd—O198.57 (16)C28—C27—C26122.4 (8)
O6—Nd—O1117.78 (15)C28—C27—H27A118.8
O2—Nd—O159.79 (16)C26—C27—H27A118.8
N5—Nd—O175.5 (2)O3—C28—C27128.3 (7)
N6—Nd—O1120.39 (18)O3—C28—C29113.2 (6)
N4—Nd—O1157.76 (19)C27—C28—C29118.5 (7)
O4—Nd—O5142.12 (16)O4—C29—C28119.4 (6)
O6—Nd—O559.78 (14)O4—C29—C24120.7 (6)
O2—Nd—O570.97 (15)C28—C29—C24119.9 (6)
N5—Nd—O569.7 (2)O3—C30—H30A109.5
N6—Nd—O5131.17 (17)O3—C30—H30B109.5
N4—Nd—O5106.50 (18)H30A—C30—H30B109.5
O1—Nd—O566.39 (15)O3—C30—H30C109.5
O4—Nd—O358.38 (13)H30A—C30—H30C109.5
O6—Nd—O3142.73 (15)H30B—C30—H30C109.5
O2—Nd—O375.00 (15)C32—C31—H31A109.5
N5—Nd—O3105.6 (2)C32—C31—H31B109.5
N6—Nd—O372.00 (18)H31A—C31—H31B109.5
N4—Nd—O3125.27 (17)C32—C31—H31C109.5
O1—Nd—O361.95 (15)H31A—C31—H31C109.5
O5—Nd—O3127.32 (14)H31B—C31—H31C109.5
C2—C1—H1B109.5C37—C32—C33118.4 (8)
C2—C1—H1C109.5C37—C32—C31119.6 (8)
H1B—C1—H1C109.5C33—C32—C31122.0 (9)
C2—C1—H1D109.5C34—C33—C32121.2 (8)
H1B—C1—H1D109.5C34—C33—H33A119.4
H1C—C1—H1D109.5C32—C33—H33A119.4
C3—C2—C7117.3 (9)C35—C34—C33119.8 (8)
C3—C2—C1122.1 (10)C35—C34—H34A120.1
C7—C2—C1120.7 (11)C33—C34—H34A120.1
C2—C3—C4122.3 (9)C34—C35—C36120.6 (7)
C2—C3—H3B118.8C34—C35—N3118.6 (6)
C4—C3—H3B118.8C36—C35—N3120.8 (6)
C3—C4—C5119.2 (9)C35—C36—C37119.3 (7)
C3—C4—H4A120.4C35—C36—H36A120.3
C5—C4—H4A120.4C37—C36—H36A120.3
C6—C5—C4119.8 (8)C32—C37—C36120.8 (7)
C6—C5—N1117.6 (7)C32—C37—H37A119.6
C4—C5—N1122.5 (8)C36—C37—H37A119.6
C7—C6—C5119.8 (8)N3—C38—C39123.9 (6)
C7—C6—H6A120.1N3—C38—H38A118.0
C5—C6—H6A120.1C39—C38—H38A118.0
C6—C7—C2121.6 (9)C38—C39—C40119.9 (6)
C6—C7—H7A119.2C38—C39—C44120.4 (6)
C2—C7—H7A119.2C40—C39—C44119.7 (6)
N1—C8—C9122.6 (7)C41—C40—C39121.1 (7)
N1—C8—H8A118.7C41—C40—H40A119.5
C9—C8—H8A118.7C39—C40—H40A119.5
C14—C9—C8120.7 (7)C40—C41—C42120.3 (7)
C14—C9—C10118.0 (8)C40—C41—H41A119.9
C8—C9—C10121.3 (8)C42—C41—H41A119.9
C11—C10—C9120.7 (9)C43—C42—C41119.4 (7)
C11—C10—H10A119.6C43—C42—H42A120.3
C9—C10—H10A119.6C41—C42—H42A120.3
C10—C11—C12120.7 (9)C42—C43—O5125.0 (6)
C10—C11—H11A119.7C42—C43—C44122.2 (6)
C12—C11—H11A119.7O5—C43—C44112.8 (6)
C13—C12—C11120.8 (10)O6—C44—C43120.4 (6)
C13—C12—H12A119.6O6—C44—C39122.2 (6)
C11—C12—H12A119.6C43—C44—C39117.4 (6)
O1—C13—C12126.4 (8)O5—C45—H45A109.5
O1—C13—C14113.4 (7)O5—C45—H45B109.5
C12—C13—C14120.1 (8)H45A—C45—H45B109.5
O2—C14—C9122.0 (7)O5—C45—H45C109.5
O2—C14—C13118.4 (7)H45A—C45—H45C109.5
C9—C14—C13119.6 (7)H45B—C45—H45C109.5
O1—C15—H15A109.5N4—C46—S1177.7 (7)
O1—C15—H15B109.5N5—C47—S2179.4 (11)
H15A—C15—H15B109.5N6—C48—S3179.1 (7)
O1—C15—H15C109.5C8—N1—C5128.6 (7)
H15A—C15—H15C109.5C8—N1—H1A115.7
H15B—C15—H15C109.5C5—N1—H1A115.7
C17—C16—H16A109.5C23—N2—C20128.4 (6)
C17—C16—H16B109.5C23—N2—H2A115.8
H16A—C16—H16B109.5C20—N2—H2A115.8
C17—C16—H16C109.5C38—N3—C35128.9 (6)
H16A—C16—H16C109.5C38—N3—H3A115.6
H16B—C16—H16C109.5C35—N3—H3A115.6
C18—C17—C22117.5 (7)C46—N4—Nd169.5 (6)
C18—C17—C16121.3 (7)C47—N5—Nd145.5 (7)
C22—C17—C16121.3 (7)C48—N6—Nd156.7 (6)
C17—C18—C19121.4 (7)C13—O1—C15118.2 (7)
C17—C18—H18A119.3C13—O1—Nd115.5 (4)
C19—C18—H18A119.3C15—O1—Nd126.1 (5)
C20—C19—C18119.5 (7)C14—O2—Nd127.0 (4)
C20—C19—H19A120.2C28—O3—C30118.4 (6)
C18—C19—H19A120.2C28—O3—Nd114.2 (4)
C19—C20—C21120.8 (7)C30—O3—Nd127.1 (4)
C19—C20—N2121.5 (6)C29—O4—Nd130.7 (4)
C21—C20—N2117.6 (6)C43—O5—C45117.5 (6)
C20—C21—C22118.7 (7)C43—O5—Nd113.7 (4)
C20—C21—H21A120.6C45—O5—Nd128.6 (4)
C22—C21—H21A120.6C44—O6—Nd126.7 (4)
C7—C2—C3—C40.6 (14)O5—Nd—N5—C47131.5 (13)
C1—C2—C3—C4−178.2 (9)O3—Nd—N5—C476.9 (13)
C2—C3—C4—C5−0.5 (14)O4—Nd—N6—C4893.5 (14)
C3—C4—C5—C60.1 (12)O6—Nd—N6—C48−120.4 (14)
C3—C4—C5—N1177.5 (7)O2—Nd—N6—C48−43.4 (14)
C4—C5—C6—C70.0 (11)N5—Nd—N6—C48123.6 (14)
N1—C5—C6—C7−177.5 (7)N4—Nd—N6—C48167.7 (14)
C5—C6—C7—C20.2 (12)O1—Nd—N6—C48−4.5 (15)
C3—C2—C7—C6−0.5 (13)O5—Nd—N6—C48−88.5 (14)
C1—C2—C7—C6178.4 (8)O3—Nd—N6—C4835.7 (14)
N1—C8—C9—C140.5 (12)C12—C13—O1—C1511.3 (12)
N1—C8—C9—C10179.5 (8)C14—C13—O1—C15−170.5 (7)
C14—C9—C10—C110.1 (13)C12—C13—O1—Nd−163.8 (7)
C8—C9—C10—C11−178.9 (9)C14—C13—O1—Nd14.4 (8)
C9—C10—C11—C120.8 (16)O4—Nd—O1—C13−153.4 (5)
C10—C11—C12—C13−0.5 (16)O6—Nd—O1—C1331.3 (5)
C11—C12—C13—O1177.3 (9)O2—Nd—O1—C13−18.0 (4)
C11—C12—C13—C14−0.8 (13)N5—Nd—O1—C13136.8 (5)
C8—C9—C14—O2−2.0 (11)N6—Nd—O1—C13−62.2 (5)
C10—C9—C14—O2179.0 (7)N4—Nd—O1—C13138.5 (6)
C8—C9—C14—C13177.7 (7)O5—Nd—O1—C1363.0 (5)
C10—C9—C14—C13−1.3 (11)O3—Nd—O1—C13−106.3 (5)
O1—C13—C14—O23.0 (10)O4—Nd—O1—C1532.0 (6)
C12—C13—C14—O2−178.7 (7)O6—Nd—O1—C15−143.3 (6)
O1—C13—C14—C9−176.6 (7)O2—Nd—O1—C15167.4 (6)
C12—C13—C14—C91.7 (11)N5—Nd—O1—C15−37.8 (6)
C22—C17—C18—C19−0.4 (12)N6—Nd—O1—C15123.2 (6)
C16—C17—C18—C19−179.8 (7)N4—Nd—O1—C15−36.1 (8)
C17—C18—C19—C20−0.3 (12)O5—Nd—O1—C15−111.6 (6)
C18—C19—C20—C211.8 (11)O3—Nd—O1—C1579.1 (6)
C18—C19—C20—N2178.8 (6)C9—C14—O2—Nd155.3 (5)
C19—C20—C21—C22−2.5 (11)C13—C14—O2—Nd−24.4 (9)
N2—C20—C21—C22−179.6 (6)O4—Nd—O2—C1494.2 (6)
C20—C21—C22—C171.8 (12)O6—Nd—O2—C14−113.8 (5)
C18—C17—C22—C21−0.4 (12)N5—Nd—O2—C14−10.0 (6)
C16—C17—C22—C21179.0 (7)N6—Nd—O2—C14163.3 (6)
N2—C23—C24—C25−177.4 (8)N4—Nd—O2—C14−144.3 (5)
N2—C23—C24—C293.1 (12)O1—Nd—O2—C1422.2 (5)
C23—C24—C25—C26177.8 (9)O5—Nd—O2—C14−51.0 (5)
C29—C24—C25—C26−2.7 (14)O3—Nd—O2—C1488.1 (5)
C24—C25—C26—C271.8 (16)C27—C28—O3—C30−9.3 (12)
C25—C26—C27—C280.1 (16)C29—C28—O3—C30170.8 (7)
C26—C27—C28—O3179.2 (9)C27—C28—O3—Nd165.9 (7)
C26—C27—C28—C29−0.9 (14)C29—C28—O3—Nd−14.0 (8)
O3—C28—C29—O40.8 (10)O4—Nd—O3—C2815.7 (5)
C27—C28—C29—O4−179.1 (7)O6—Nd—O3—C28154.0 (4)
O3—C28—C29—C24179.9 (6)O2—Nd—O3—C28−169.5 (5)
C27—C28—C29—C240.0 (11)N5—Nd—O3—C28−42.4 (5)
C23—C24—C29—O40.4 (11)N6—Nd—O3—C28113.0 (5)
C25—C24—C29—O4−179.1 (7)N4—Nd—O3—C2849.1 (5)
C23—C24—C29—C28−178.7 (7)O1—Nd—O3—C28−106.1 (5)
C25—C24—C29—C281.8 (11)O5—Nd—O3—C28−118.4 (5)
C37—C32—C33—C34−1.6 (14)O4—Nd—O3—C30−169.6 (7)
C31—C32—C33—C34−179.1 (9)O6—Nd—O3—C30−31.3 (7)
C32—C33—C34—C351.7 (13)O2—Nd—O3—C305.2 (6)
C33—C34—C35—C36−0.9 (12)N5—Nd—O3—C30132.3 (6)
C33—C34—C35—N3176.1 (7)N6—Nd—O3—C30−72.3 (6)
C34—C35—C36—C370.0 (11)N4—Nd—O3—C30−136.2 (6)
N3—C35—C36—C37−176.9 (7)O1—Nd—O3—C3068.6 (6)
C33—C32—C37—C360.8 (13)O5—Nd—O3—C3056.2 (6)
C31—C32—C37—C36178.4 (8)C28—C29—O4—Nd18.9 (9)
C35—C36—C37—C320.0 (12)C24—C29—O4—Nd−160.2 (5)
N3—C38—C39—C40178.8 (6)O6—Nd—O4—C29−155.9 (5)
N3—C38—C39—C44−2.8 (10)O2—Nd—O4—C29−25.1 (7)
C38—C39—C40—C41178.9 (7)N5—Nd—O4—C29103.0 (6)
C44—C39—C40—C410.5 (11)N6—Nd—O4—C29−89.1 (6)
C39—C40—C41—C420.7 (12)N4—Nd—O4—C29−170.3 (6)
C40—C41—C42—C43−2.1 (12)O1—Nd—O4—C2931.1 (6)
C41—C42—C43—O5179.5 (7)O5—Nd—O4—C2993.3 (6)
C41—C42—C43—C442.2 (11)O3—Nd—O4—C29−18.3 (5)
C42—C43—C44—O6179.3 (6)C42—C43—O5—C45−11.0 (10)
O5—C43—C44—O61.7 (9)C44—C43—O5—C45166.5 (6)
C42—C43—C44—C39−1.0 (10)C42—C43—O5—Nd163.6 (6)
O5—C43—C44—C39−178.6 (6)C44—C43—O5—Nd−18.9 (7)
C38—C39—C44—O60.9 (10)O4—Nd—O5—C43160.4 (4)
C40—C39—C44—O6179.4 (6)O6—Nd—O5—C4320.6 (4)
C38—C39—C44—C43−178.8 (6)O2—Nd—O5—C43−62.4 (4)
C40—C39—C44—C43−0.3 (10)N5—Nd—O5—C43150.5 (5)
C9—C8—N1—C5−173.3 (7)N6—Nd—O5—C43−16.3 (5)
C6—C5—N1—C8−160.0 (7)N4—Nd—O5—C4375.6 (5)
C4—C5—N1—C822.5 (11)O1—Nd—O5—C43−126.9 (5)
C24—C23—N2—C20178.3 (7)O3—Nd—O5—C43−115.0 (4)
C19—C20—N2—C2310.6 (11)O4—Nd—O5—C45−25.8 (7)
C21—C20—N2—C23−172.3 (7)O6—Nd—O5—C45−165.6 (7)
C39—C38—N3—C35178.2 (6)O2—Nd—O5—C45111.5 (6)
C34—C35—N3—C38−164.5 (7)N5—Nd—O5—C45−35.7 (6)
C36—C35—N3—C3812.5 (10)N6—Nd—O5—C45157.5 (6)
O4—Nd—N4—C46150 (3)N4—Nd—O5—C45−110.6 (6)
O6—Nd—N4—C46−21 (3)O1—Nd—O5—C4546.9 (6)
O2—Nd—N4—C4610 (4)O3—Nd—O5—C4558.8 (7)
N5—Nd—N4—C46−136 (3)C43—C44—O6—Nd22.3 (9)
N6—Nd—N4—C4661 (3)C39—C44—O6—Nd−157.3 (5)
O1—Nd—N4—C46−137 (3)O4—Nd—O6—C44−160.7 (5)
O5—Nd—N4—C46−70 (3)O2—Nd—O6—C4454.3 (5)
O3—Nd—N4—C46121 (3)N5—Nd—O6—C44−72.3 (5)
O4—Nd—N5—C47−42.1 (12)N6—Nd—O6—C44130.2 (5)
O6—Nd—N5—C47176.5 (12)N4—Nd—O6—C44−146.0 (5)
O2—Nd—N5—C4790.1 (13)O1—Nd—O6—C4411.5 (5)
N6—Nd—N5—C47−73.7 (15)O5—Nd—O6—C44−22.3 (5)
N4—Nd—N5—C47−117.6 (13)O3—Nd—O6—C4490.8 (5)
O1—Nd—N5—C4761.8 (13)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O20.861.862.566 (7)138
N2—H2A···O40.861.872.576 (6)138
N3—H3A···O60.861.892.589 (7)137
C38—H38A···S1i0.932.723.633 (6)166
Symmetry codes: (i) −x+3, −y+1, −z+3.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O20.861.862.566 (7)138
N2—H2A···O40.861.872.576 (6)138
N3—H3A···O60.861.892.589 (7)137
C38—H38A···S1i0.932.723.633 (6)166
Symmetry codes: (i) −x+3, −y+1, −z+3.
references
References top

Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Li, H.-Q., Xian, H.-D., Liu, J.-F. & Zhao, G.-L. (2008). Acta Cryst. E64, m1593–m1594.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Wang, G. & Chang, J.-C. (1994). Synth. React. Inorg. Met. Org. Chem. 24, 623–627.

Xian, H.-D., Liu, J.-F., Li, H.-Q. & Zhao, G.-L. (2008). Acta Cryst. E64, m1422.

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