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Acta Cryst. (2008). E64, m408-m409    [ doi:10.1107/S1600536808001943 ]

Aquatris[6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinato]-[kappa]6N,N',O;[kappa]O-dysprosium(III) trihydrate

Z. Kai, F. Yu, X.-H. Yin, Z. Jie and C.-W. Lin

Abstract top

In the title complex, [Dy(C11H10N3O2)3(H2O)]·3H2O, the DyIII atom is coordinated by four N atoms and four O atoms derived from three tridentate deprotonated 6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinate ligands and one water molecule. The complex and solvent water molecules are linked together via O-H...O, O-H...N, C-H...O and C-H...[pi] hydrogen-bonding interactions, forming a three-dimensional network structure.

Comment top

Recently we reported the crystal structures of bis[6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinato]zinc(II) trihydrate (Yin et al., 2007) and bis[3-chloro-6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinato]nickel(II) tetrahydrate (Zhao et al., 2008). The title compound consists of the central asymmetric mononuclear dysprosium(III) complex and three uncoordinated water molecules. The Dy atom is eight-coordinated by four N atoms and four O atoms derived from three tridentate, deprotonated 6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinate ligands (DPP) and one water molecule, that define a pseudo-tricapped trigonal environment for the dysprosium atom. The angles around the Dy(III) atom range from 61.39 (18) to 155.29 (19)°, the Dy—O distances range between 2.235 (5) and 2.368 (5) Å, and the Dy—N distances range between 2.511 (6) and 2.598 (6) Å, i.e. normal values. The C1—C2, C12—C13 and C23—C24 bond lengths range between 1.515 (11) and 1.518 (10) Å, being in the normal C—C ranges found in dysprosium carboxylate complexes (Baggio et al. (2003) and literature cited therein).

In the crystal structure, the oxygen atoms contribute to the formation of intermolecular hydrogen bonds involving the solvate water molecules. Four water molecules, two DDP O atoms and one DDP N atom form rings via intermolecular H···O—H···O and H···O—H···N hydrogen bonds (Fig. 2). These interactions and two intermolecular C—H···O hydrogen bonds and a C—H···π contact (Cgviii is the centroid of ring atoms N2, N3, C8, C9, C10) link the complexes into a three-dimensional network (Table 1). Two weak intramolecular Cmethyl—H···O/N hydrogen bonds contribute to the conformational stability of the title complex.

Related literature top

For related literature, see: Zhao et al. (2008); Yin et al. (2007); Baggio et al. (2003).

Experimental top

6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinic acid, and Dy(NO3)3. 6H2O were available commercially and were used without further purification. Equimolar 6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinic acid (1 mmol, 217 mg) was dissolved in anhydrous ethyl alcohol (AR,99.9%) (15 ml). The mixture was stirred to give a clear solution. To this solution was added Dy(NO3)3. 6H2O (0.33 mmol,151 mg) in anhydrous alcohol (10 ml). After keeping the resulting solution in air to evaporate about half of the solvents, colorless blocks of the title complex were formed. The crystals were isolated and washed with alcohol three times (Yield75%). Elemental analysis: found: C, 44.63; H, 4.42; N, 14.18; calc. for C33H38DyN9O10: C, 44.88; H, 4.34; N, 14.27.

Refinement top

H atoms on C atoms were positoned geometrically and refined using a riding model with C—H = 0.96 Å and Uiso(H) = 1.2Ueq(C). The water H atoms were located in difference Fourier maps and the O—H distances were constrained 0.85 Å, with Uiso(H) = 1.2Ueq(O).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. Crystal packing of the title compound showing the hydrogen bonding interactions as dashed lines.
Aquatris[6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinato]- κ6N,N',O;κO-dysprosium(III) trihydrate top
Crystal data top
[Dy(C11H10N3O2)3(H2O)]·3H2OF000 = 1780
Mr = 883.22Dx = 1.615 Mg m−3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5527 reflections
a = 15.4709 (18) Åθ = 2.2–27.0º
b = 12.8466 (12) ŵ = 2.13 mm−1
c = 18.543 (2) ÅT = 298 (2) K
β = 99.741 (2)ºBlock, colorless
V = 3632.3 (7) Å30.30 × 0.24 × 0.17 mm
Z = 4
Data collection top
Siemens CCD area-detector
diffractometer		6277 independent reflections
Radiation source: fine-focus sealed tube4009 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.063
T = 298(2) Kθmax = 25.0º
φ and ω scansθmin = 1.6º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −17→18
Tmin = 0.568, Tmax = 0.714k = −15→11
17074 measured reflectionsl = −20→22
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)] = 0.050H-atom parameters constrained
wR(F2) = 0.118  w = 1/[σ2(Fo2) + (0.0405P)2 + 8.4683P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
6277 reflectionsΔρmax = 1.45 e Å−3
478 parametersΔρmin = −0.93 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Dy(C11H10N3O2)3(H2O)]·3H2OV = 3632.3 (7) Å3
Mr = 883.22Z = 4
Monoclinic, P21/nMo Kα
a = 15.4709 (18) ŵ = 2.13 mm−1
b = 12.8466 (12) ÅT = 298 (2) K
c = 18.543 (2) Å0.30 × 0.24 × 0.17 mm
β = 99.741 (2)º
Data collection top
Siemens CCD area-detector
diffractometer		6277 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4009 reflections with I > 2σ(I)
Tmin = 0.568, Tmax = 0.714Rint = 0.063
17074 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.050478 parameters
wR(F2) = 0.118H-atom parameters constrained
S = 1.04Δρmax = 1.45 e Å−3
6277 reflectionsΔρmin = −0.93 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
Dy10.75071 (2)0.66687 (2)1.003769 (16)0.03410 (12)
N10.6309 (4)0.5937 (4)1.0664 (3)0.0361 (14)
N20.5241 (4)0.6864 (5)0.9895 (3)0.0396 (15)
N30.5898 (4)0.7133 (5)0.9520 (3)0.0386 (14)
N40.8662 (4)0.5887 (5)0.9402 (3)0.0414 (15)
N50.9742 (4)0.6866 (5)1.0092 (4)0.0506 (17)
N60.9143 (4)0.7066 (5)1.0545 (3)0.0485 (17)
N70.8795 (4)0.8013 (5)0.8338 (3)0.0455 (16)
N80.9188 (4)0.7169 (5)0.7327 (3)0.0485 (16)
N90.9861 (5)0.6876 (5)0.6967 (3)0.0524 (18)
O10.7997 (4)0.5476 (5)1.0950 (3)0.0616 (16)
O20.7858 (4)0.4614 (5)1.1964 (3)0.084 (2)
O30.7008 (3)0.5403 (4)0.9230 (3)0.0567 (15)
O40.7111 (5)0.4224 (6)0.8381 (4)0.094 (2)
O50.7797 (3)0.8105 (4)0.9442 (2)0.0444 (13)
O60.8256 (5)0.9737 (5)0.9672 (4)0.087 (2)
O70.7206 (3)0.7929 (4)1.0893 (2)0.0492 (13)
H7D0.68880.76981.11890.059*
H7E0.69920.84881.06920.059*
O80.8288 (4)0.2837 (4)0.2749 (3)0.0619 (15)
H8A0.81040.33740.25020.074*
H8B0.88440.28730.28550.074*
O90.7072 (5)−0.0051 (5)0.0552 (3)0.094 (3)
H9A0.7490−0.00740.03080.113*
H9B0.72320.03150.09330.113*
O100.7578 (5)0.6130 (6)0.3125 (3)0.099 (2)
H10A0.73190.66440.28940.119*
H10B0.76700.56740.28140.119*
C10.7554 (6)0.5094 (7)1.1399 (4)0.054 (2)
C20.6573 (5)0.5279 (6)1.1235 (4)0.0439 (19)
C30.6000 (6)0.4839 (7)1.1636 (4)0.055 (2)
H30.61970.44011.20290.066*
C40.5124 (6)0.5070 (7)1.1436 (4)0.059 (2)
H40.47160.47591.16830.071*
C50.4849 (5)0.5744 (7)1.0883 (4)0.052 (2)
H50.42590.59211.07610.063*
C60.5470 (5)0.6171 (6)1.0500 (4)0.0406 (18)
C70.3586 (5)0.7125 (8)0.9814 (5)0.069 (3)
H7A0.34010.64120.97630.103*
H7B0.31580.75600.95220.103*
H7C0.36440.73291.03180.103*
C80.4452 (5)0.7243 (7)0.9564 (4)0.049 (2)
C90.4607 (5)0.7774 (7)0.8958 (4)0.053 (2)
H90.41960.81260.86210.064*
C100.5501 (5)0.7684 (6)0.8948 (4)0.047 (2)
C110.5989 (6)0.8110 (7)0.8377 (4)0.060 (2)
H11A0.61770.88080.85050.090*
H11B0.56100.81130.79100.090*
H11C0.64910.76820.83510.090*
C120.7414 (6)0.4911 (7)0.8808 (4)0.052 (2)
C130.8373 (5)0.5204 (6)0.8873 (4)0.048 (2)
C140.8902 (6)0.4777 (7)0.8429 (4)0.059 (2)
H140.86810.43030.80650.071*
C150.9773 (6)0.5071 (7)0.8537 (5)0.063 (2)
H151.01450.48020.82390.075*
C161.0093 (6)0.5766 (7)0.9088 (5)0.060 (2)
H161.06800.59610.91740.072*
C170.9503 (5)0.6165 (6)0.9511 (4)0.046 (2)
C181.1332 (6)0.7357 (9)0.9999 (6)0.094 (4)
H18A1.15390.66570.99660.142*
H18B1.17810.77691.02880.142*
H18C1.11890.76490.95170.142*
C191.0545 (6)0.7351 (8)1.0347 (5)0.068 (3)
C201.0409 (7)0.7832 (8)1.0969 (6)0.080 (3)
H201.08220.82311.12720.096*
C210.9556 (6)0.7636 (8)1.1085 (5)0.065 (3)
C220.9154 (7)0.7962 (9)1.1728 (5)0.091 (4)
H22A0.86910.84511.15730.136*
H22B0.95930.82801.20880.136*
H22C0.89190.73621.19370.136*
C230.8286 (5)0.8888 (7)0.9366 (4)0.0481 (19)
C240.8961 (5)0.8752 (6)0.8868 (4)0.0472 (19)
C250.9700 (6)0.9355 (7)0.8983 (4)0.060 (2)
H250.97880.98470.93560.073*
C261.0319 (6)0.9207 (7)0.8524 (5)0.066 (3)
H261.08370.95900.85920.080*
C271.0154 (6)0.8492 (7)0.7972 (4)0.060 (2)
H271.05540.83890.76560.072*
C280.9382 (5)0.7923 (6)0.7890 (4)0.0464 (19)
C290.7571 (6)0.6856 (7)0.7301 (4)0.062 (2)
H29A0.71390.63850.70520.092*
H29B0.73820.75600.71950.092*
H29C0.76420.67370.78180.092*
C300.8417 (6)0.6681 (7)0.7049 (4)0.051 (2)
C310.8611 (6)0.6068 (7)0.6500 (4)0.062 (2)
H310.82210.56360.62020.074*
C320.9491 (6)0.6201 (7)0.6464 (4)0.058 (2)
C331.0021 (7)0.5682 (8)0.5948 (5)0.081 (3)
H33A1.06310.56890.61630.121*
H33B0.99410.60540.54930.121*
H33C0.98280.49760.58620.121*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Dy10.02830 (17)0.03581 (18)0.03982 (18)−0.0007 (2)0.01043 (12)0.00066 (18)
N10.035 (4)0.035 (4)0.042 (3)−0.007 (3)0.015 (3)0.001 (3)
N20.028 (3)0.048 (4)0.045 (3)−0.004 (3)0.013 (3)−0.004 (3)
N30.024 (3)0.045 (4)0.048 (3)0.003 (3)0.009 (3)−0.002 (3)
N40.041 (4)0.041 (4)0.046 (3)0.002 (3)0.016 (3)0.003 (3)
N50.033 (4)0.052 (5)0.066 (4)−0.006 (3)0.005 (3)0.005 (3)
N60.033 (4)0.057 (5)0.052 (4)0.000 (3)−0.003 (3)0.003 (3)
N70.048 (4)0.047 (4)0.044 (3)0.005 (3)0.016 (3)0.006 (3)
N80.051 (4)0.050 (4)0.046 (3)0.006 (3)0.015 (3)0.001 (3)
N90.054 (5)0.050 (5)0.058 (4)0.003 (3)0.024 (3)−0.002 (3)
O10.045 (4)0.074 (4)0.068 (3)0.012 (3)0.015 (3)0.023 (3)
O20.077 (5)0.092 (5)0.082 (4)0.023 (4)0.011 (4)0.050 (4)
O30.042 (4)0.063 (4)0.069 (3)−0.011 (3)0.019 (3)−0.027 (3)
O40.070 (5)0.096 (6)0.121 (5)−0.017 (4)0.025 (4)−0.061 (5)
O50.043 (3)0.049 (3)0.044 (3)−0.007 (2)0.013 (2)0.003 (2)
O60.102 (6)0.070 (5)0.104 (5)−0.026 (4)0.061 (4)−0.037 (4)
O70.055 (4)0.052 (3)0.046 (3)−0.003 (3)0.022 (2)−0.003 (2)
O80.062 (4)0.066 (4)0.060 (3)0.012 (3)0.020 (3)0.013 (3)
O90.135 (7)0.073 (5)0.093 (4)−0.003 (4)0.069 (5)−0.015 (4)
O100.107 (7)0.105 (6)0.077 (4)0.014 (5)−0.007 (4)0.001 (4)
C10.051 (6)0.059 (6)0.052 (4)0.004 (4)0.011 (4)0.017 (4)
C20.044 (5)0.043 (5)0.045 (4)−0.005 (4)0.012 (3)0.004 (3)
C30.062 (6)0.060 (6)0.046 (4)−0.010 (5)0.019 (4)0.010 (4)
C40.058 (6)0.069 (6)0.056 (5)−0.020 (5)0.026 (4)0.004 (5)
C50.037 (5)0.066 (6)0.057 (5)−0.015 (4)0.017 (4)−0.002 (4)
C60.032 (5)0.045 (5)0.046 (4)−0.007 (4)0.010 (3)−0.010 (3)
C70.035 (5)0.081 (7)0.093 (6)0.013 (5)0.017 (4)−0.002 (5)
C80.032 (5)0.053 (5)0.062 (5)0.000 (4)0.008 (4)−0.006 (4)
C90.033 (5)0.056 (6)0.068 (5)0.004 (4)0.001 (4)0.005 (4)
C100.036 (5)0.050 (5)0.054 (4)0.002 (4)0.006 (4)0.009 (4)
C110.050 (5)0.067 (6)0.061 (5)0.003 (5)0.002 (4)0.020 (4)
C120.052 (5)0.049 (5)0.057 (4)−0.002 (4)0.015 (4)−0.018 (4)
C130.044 (5)0.052 (6)0.053 (4)0.008 (4)0.019 (4)−0.001 (4)
C140.060 (6)0.060 (6)0.062 (5)0.012 (5)0.025 (4)−0.006 (4)
C150.056 (6)0.069 (7)0.069 (5)0.017 (5)0.026 (5)0.002 (5)
C160.044 (6)0.067 (7)0.071 (5)0.006 (5)0.019 (4)0.012 (5)
C170.036 (5)0.049 (5)0.056 (4)0.001 (4)0.014 (4)0.018 (4)
C180.047 (7)0.100 (9)0.135 (9)−0.011 (6)0.013 (6)0.012 (7)
C190.035 (6)0.073 (7)0.092 (7)−0.009 (5)0.000 (5)0.007 (6)
C200.052 (7)0.075 (8)0.103 (8)−0.007 (6)−0.017 (6)−0.004 (6)
C210.045 (6)0.068 (7)0.075 (6)−0.005 (5)−0.013 (5)0.000 (5)
C220.077 (8)0.107 (9)0.077 (6)0.013 (7)−0.018 (6)−0.029 (6)
C230.046 (5)0.053 (5)0.047 (4)−0.004 (4)0.015 (4)−0.002 (4)
C240.052 (5)0.047 (5)0.043 (4)−0.004 (4)0.011 (4)0.004 (4)
C250.059 (6)0.064 (6)0.061 (5)−0.011 (5)0.019 (4)−0.005 (4)
C260.062 (6)0.066 (7)0.075 (6)−0.013 (5)0.022 (5)−0.008 (5)
C270.060 (6)0.065 (6)0.062 (5)−0.008 (5)0.028 (4)−0.006 (4)
C280.049 (5)0.048 (5)0.045 (4)0.003 (4)0.015 (4)0.005 (3)
C290.051 (5)0.073 (7)0.060 (5)0.001 (5)0.008 (4)0.000 (4)
C300.058 (5)0.054 (5)0.042 (4)0.008 (4)0.011 (3)0.006 (4)
C310.073 (7)0.055 (6)0.055 (5)0.004 (5)0.009 (4)−0.001 (4)
C320.067 (6)0.051 (6)0.059 (5)0.007 (5)0.022 (5)−0.001 (4)
C330.093 (8)0.070 (7)0.088 (6)0.001 (6)0.041 (6)−0.023 (6)
Geometric parameters (Å, °) top
Dy1—O52.235 (5)C7—H7A0.9600
Dy1—O32.256 (5)C7—H7B0.9600
Dy1—O12.313 (5)C7—H7C0.9600
Dy1—O72.368 (5)C8—C91.370 (11)
Dy1—N42.511 (6)C9—C101.391 (11)
Dy1—N12.530 (5)C9—H90.9300
Dy1—N32.582 (6)C10—C111.504 (10)
Dy1—N62.598 (6)C11—H11A0.9600
N1—C61.317 (9)C11—H11B0.9600
N1—C21.362 (8)C11—H11C0.9600
N2—C81.360 (9)C12—C131.515 (11)
N2—N31.369 (7)C13—C141.371 (10)
N2—C61.429 (9)C14—C151.380 (12)
N3—C101.335 (9)C14—H140.9300
N4—C171.331 (9)C15—C161.384 (12)
N4—C131.337 (9)C15—H150.9300
N5—N61.375 (8)C16—C171.396 (11)
N5—C191.399 (11)C16—H160.9300
N5—C171.405 (10)C18—C191.470 (12)
N6—C211.315 (10)C18—H18A0.9600
N7—C281.335 (9)C18—H18B0.9600
N7—C241.358 (9)C18—H18C0.9600
N8—C301.369 (10)C19—C201.356 (13)
N8—N91.380 (8)C20—C211.395 (13)
N8—C281.418 (9)C20—H200.9300
N9—C321.331 (10)C21—C221.496 (12)
O1—C11.262 (9)C22—H22A0.9600
O2—C11.239 (9)C22—H22B0.9600
O3—C121.254 (8)C22—H22C0.9600
O4—C121.226 (9)C23—C241.518 (10)
O5—C231.280 (9)C24—C251.368 (11)
O6—C231.233 (9)C25—C261.399 (11)
O7—H7D0.8499C25—H250.9300
O7—H7E0.8501C26—C271.365 (11)
O8—H8A0.8500C26—H260.9300
O8—H8B0.8500C27—C281.388 (11)
O9—H9A0.8499C27—H270.9300
O9—H9B0.8500C29—C301.479 (11)
O10—H10A0.8500C29—H29A0.9600
O10—H10B0.8499C29—H29B0.9600
C1—C21.515 (11)C29—H29C0.9600
C2—C31.371 (10)C30—C311.361 (10)
C3—C41.377 (12)C31—C321.385 (12)
C3—H30.9300C31—H310.9300
C4—C51.355 (11)C32—C331.516 (11)
C4—H40.9300C33—H33A0.9600
C5—C61.399 (10)C33—H33B0.9600
C5—H50.9300C33—H33C0.9600
C7—C81.498 (10)
O5—Dy1—O3109.97 (18)C10—C9—H9126.8
O5—Dy1—O1147.2 (2)N3—C10—C9111.0 (7)
O3—Dy1—O192.3 (2)N3—C10—C11122.3 (7)
O5—Dy1—O781.11 (18)C9—C10—C11126.7 (7)
O3—Dy1—O7148.61 (19)C10—C11—H11A109.5
O1—Dy1—O792.30 (19)C10—C11—H11B109.5
O5—Dy1—N483.08 (18)H11A—C11—H11B109.5
O3—Dy1—N465.86 (19)C10—C11—H11C109.5
O1—Dy1—N484.69 (19)H11A—C11—H11C109.5
O7—Dy1—N4145.5 (2)H11B—C11—H11C109.5
O5—Dy1—N1139.29 (19)O4—C12—O3126.1 (8)
O3—Dy1—N180.91 (18)O4—C12—C13119.5 (7)
O1—Dy1—N165.95 (19)O3—C12—C13114.3 (7)
O7—Dy1—N172.77 (17)N4—C13—C14123.0 (8)
N4—Dy1—N1134.60 (18)N4—C13—C12115.0 (6)
O5—Dy1—N383.51 (18)C14—C13—C12122.0 (8)
O3—Dy1—N373.73 (19)C13—C14—C15118.0 (9)
O1—Dy1—N3126.92 (19)C13—C14—H14121.0
O7—Dy1—N378.72 (18)C15—C14—H14121.0
N4—Dy1—N3129.51 (18)C14—C15—C16120.2 (8)
N1—Dy1—N361.39 (18)C14—C15—H15119.9
O5—Dy1—N675.63 (19)C16—C15—H15119.9
O3—Dy1—N6125.8 (2)C15—C16—C17117.7 (8)
O1—Dy1—N671.8 (2)C15—C16—H16121.2
O7—Dy1—N685.02 (19)C17—C16—H16121.2
N4—Dy1—N661.4 (2)N4—C17—C16122.1 (8)
N1—Dy1—N6130.68 (19)N4—C17—N5114.2 (7)
N3—Dy1—N6155.29 (19)C16—C17—N5123.6 (8)
C6—N1—C2118.4 (6)C19—C18—H18A109.5
C6—N1—Dy1125.4 (5)C19—C18—H18B109.5
C2—N1—Dy1116.1 (5)H18A—C18—H18B109.5
C8—N2—N3111.6 (6)C19—C18—H18C109.5
C8—N2—C6131.4 (6)H18A—C18—H18C109.5
N3—N2—C6116.7 (6)H18B—C18—H18C109.5
C10—N3—N2104.8 (6)C20—C19—N5103.5 (8)
C10—N3—Dy1134.6 (5)C20—C19—C18129.0 (10)
N2—N3—Dy1120.3 (4)N5—C19—C18127.5 (9)
C17—N4—C13119.0 (6)C19—C20—C21109.6 (9)
C17—N4—Dy1125.3 (5)C19—C20—H20125.2
C13—N4—Dy1115.5 (5)C21—C20—H20125.2
N6—N5—C19111.2 (7)N6—C21—C20109.5 (9)
N6—N5—C17118.1 (6)N6—C21—C22123.3 (9)
C19—N5—C17130.3 (8)C20—C21—C22127.2 (9)
C21—N6—N5106.2 (7)C21—C22—H22A109.5
C21—N6—Dy1134.6 (6)C21—C22—H22B109.5
N5—N6—Dy1117.3 (4)H22A—C22—H22B109.5
C28—N7—C24116.5 (7)C21—C22—H22C109.5
C30—N8—N9112.0 (6)H22A—C22—H22C109.5
C30—N8—C28130.6 (7)H22B—C22—H22C109.5
N9—N8—C28117.4 (7)O6—C23—O5125.2 (7)
C32—N9—N8104.3 (7)O6—C23—C24117.7 (7)
C1—O1—Dy1126.3 (5)O5—C23—C24117.1 (7)
C12—O3—Dy1128.8 (5)N7—C24—C25124.0 (7)
C23—O5—Dy1151.0 (5)N7—C24—C23117.1 (7)
Dy1—O7—H7D113.2C25—C24—C23118.8 (7)
Dy1—O7—H7E112.9C24—C25—C26117.9 (8)
H7D—O7—H7E110.6C24—C25—H25121.0
H8A—O8—H8B108.2C26—C25—H25121.0
H9A—O9—H9B108.6C27—C26—C25119.1 (9)
H10A—O10—H10B108.3C27—C26—H26120.4
O2—C1—O1125.5 (8)C25—C26—H26120.4
O2—C1—C2118.1 (7)C26—C27—C28119.0 (8)
O1—C1—C2116.4 (7)C26—C27—H27120.5
N1—C2—C3122.7 (8)C28—C27—H27120.5
N1—C2—C1114.3 (6)N7—C28—C27123.3 (7)
C3—C2—C1123.0 (7)N7—C28—N8115.9 (7)
C2—C3—C4117.6 (8)C27—C28—N8120.8 (7)
C2—C3—H3121.2C30—C29—H29A109.5
C4—C3—H3121.2C30—C29—H29B109.5
C5—C4—C3120.7 (7)H29A—C29—H29B109.5
C5—C4—H4119.7C30—C29—H29C109.5
C3—C4—H4119.7H29A—C29—H29C109.5
C4—C5—C6118.7 (8)H29B—C29—H29C109.5
C4—C5—H5120.6C31—C30—N8104.9 (8)
C6—C5—H5120.6C31—C30—C29130.0 (9)
N1—C6—C5121.8 (7)N8—C30—C29125.0 (7)
N1—C6—N2115.3 (6)C30—C31—C32107.9 (8)
C5—C6—N2122.8 (7)C30—C31—H31126.0
C8—C7—H7A109.5C32—C31—H31126.0
C8—C7—H7B109.5N9—C32—C31110.9 (7)
H7A—C7—H7B109.5N9—C32—C33120.9 (9)
C8—C7—H7C109.5C31—C32—C33128.2 (9)
H7A—C7—H7C109.5C32—C33—H33A109.5
H7B—C7—H7C109.5C32—C33—H33B109.5
N2—C8—C9106.2 (7)H33A—C33—H33B109.5
N2—C8—C7127.3 (7)C32—C33—H33C109.5
C9—C8—C7126.5 (8)H33A—C33—H33C109.5
C8—C9—C10106.4 (7)H33B—C33—H33C109.5
C8—C9—H9126.8
O5—Dy1—N1—C628.1 (7)O2—C1—C2—C3−7.8 (13)
O3—Dy1—N1—C6−82.1 (6)O1—C1—C2—C3174.3 (8)
O1—Dy1—N1—C6−178.8 (6)N1—C2—C3—C41.1 (12)
O7—Dy1—N1—C680.6 (6)C1—C2—C3—C4179.8 (8)
N4—Dy1—N1—C6−124.4 (5)C2—C3—C4—C5−2.9 (13)
N3—Dy1—N1—C6−5.7 (5)C3—C4—C5—C62.6 (13)
N6—Dy1—N1—C6147.9 (5)C2—N1—C6—C5−1.5 (11)
O5—Dy1—N1—C2−149.3 (4)Dy1—N1—C6—C5−178.8 (5)
O3—Dy1—N1—C2100.5 (5)C2—N1—C6—N2−180.0 (6)
O1—Dy1—N1—C23.9 (5)Dy1—N1—C6—N22.7 (9)
O7—Dy1—N1—C2−96.8 (5)C4—C5—C6—N1−0.3 (12)
N4—Dy1—N1—C258.2 (6)C4—C5—C6—N2178.0 (7)
N3—Dy1—N1—C2176.9 (5)C8—N2—C6—N1177.8 (7)
N6—Dy1—N1—C2−29.5 (6)N3—N2—C6—N15.3 (9)
C8—N2—N3—C10−0.3 (8)C8—N2—C6—C5−0.6 (12)
C6—N2—N3—C10173.7 (6)N3—N2—C6—C5−173.1 (6)
C8—N2—N3—Dy1175.3 (5)N3—N2—C8—C9−0.1 (9)
C6—N2—N3—Dy1−10.7 (8)C6—N2—C8—C9−172.9 (7)
O5—Dy1—N3—C1023.7 (7)N3—N2—C8—C7−179.1 (8)
O3—Dy1—N3—C10−89.3 (7)C6—N2—C8—C78.1 (14)
O1—Dy1—N3—C10−169.7 (7)N2—C8—C9—C100.4 (9)
O7—Dy1—N3—C10105.9 (7)C7—C8—C9—C10179.4 (8)
N4—Dy1—N3—C10−51.7 (8)N2—N3—C10—C90.5 (9)
N1—Dy1—N3—C10−177.7 (8)Dy1—N3—C10—C9−174.2 (5)
N6—Dy1—N3—C1056.1 (9)N2—N3—C10—C11−178.3 (7)
O5—Dy1—N3—N2−150.3 (5)Dy1—N3—C10—C117.0 (12)
O3—Dy1—N3—N296.7 (5)C8—C9—C10—N3−0.6 (10)
O1—Dy1—N3—N216.2 (6)C8—C9—C10—C11178.2 (8)
O7—Dy1—N3—N2−68.1 (5)Dy1—O3—C12—O4179.7 (7)
N4—Dy1—N3—N2134.2 (4)Dy1—O3—C12—C131.6 (11)
N1—Dy1—N3—N28.3 (4)C17—N4—C13—C14−0.5 (12)
N6—Dy1—N3—N2−117.9 (6)Dy1—N4—C13—C14174.0 (6)
O5—Dy1—N4—C1764.5 (6)C17—N4—C13—C12178.1 (7)
O3—Dy1—N4—C17−180.0 (6)Dy1—N4—C13—C12−7.4 (8)
O1—Dy1—N4—C17−85.0 (6)O4—C12—C13—N4−173.8 (8)
O7—Dy1—N4—C171.3 (7)O3—C12—C13—N44.4 (11)
N1—Dy1—N4—C17−133.2 (5)O4—C12—C13—C144.8 (13)
N3—Dy1—N4—C17140.1 (5)O3—C12—C13—C14−177.0 (8)
N6—Dy1—N4—C17−12.9 (5)N4—C13—C14—C150.0 (13)
O5—Dy1—N4—C13−109.6 (5)C12—C13—C14—C15−178.5 (8)
O3—Dy1—N4—C135.9 (5)C13—C14—C15—C161.0 (13)
O1—Dy1—N4—C13100.9 (5)C14—C15—C16—C17−1.3 (13)
O7—Dy1—N4—C13−172.8 (5)C13—N4—C17—C160.1 (11)
N1—Dy1—N4—C1352.7 (6)Dy1—N4—C17—C16−173.8 (5)
N3—Dy1—N4—C13−34.0 (6)C13—N4—C17—N5−178.5 (6)
N6—Dy1—N4—C13173.0 (6)Dy1—N4—C17—N57.6 (9)
C19—N5—N6—C21−1.7 (9)C15—C16—C17—N40.8 (12)
C17—N5—N6—C21172.6 (7)C15—C16—C17—N5179.3 (7)
C19—N5—N6—Dy1164.8 (5)N6—N5—C17—N49.5 (10)
C17—N5—N6—Dy1−20.8 (8)C19—N5—C17—N4−177.4 (8)
O5—Dy1—N6—C2188.3 (8)N6—N5—C17—C16−169.1 (7)
O3—Dy1—N6—C21−167.2 (8)C19—N5—C17—C163.9 (13)
O1—Dy1—N6—C21−87.9 (8)N6—N5—C19—C200.8 (10)
O7—Dy1—N6—C216.2 (8)C17—N5—C19—C20−172.6 (8)
N4—Dy1—N6—C21178.2 (9)N6—N5—C19—C18−177.3 (9)
N1—Dy1—N6—C21−55.9 (9)C17—N5—C19—C189.3 (16)
N3—Dy1—N6—C2155.0 (10)N5—C19—C20—C210.4 (11)
O5—Dy1—N6—N5−73.4 (5)C18—C19—C20—C21178.4 (10)
O3—Dy1—N6—N531.1 (6)N5—N6—C21—C201.9 (10)
O1—Dy1—N6—N5110.5 (5)Dy1—N6—C21—C20−161.2 (6)
O7—Dy1—N6—N5−155.5 (5)N5—N6—C21—C22−175.6 (9)
N4—Dy1—N6—N516.5 (5)Dy1—N6—C21—C2221.3 (14)
N1—Dy1—N6—N5142.4 (5)C19—C20—C21—N6−1.5 (12)
N3—Dy1—N6—N5−106.7 (6)C19—C20—C21—C22175.9 (10)
C30—N8—N9—C320.1 (8)Dy1—O5—C23—O6−86.0 (14)
C28—N8—N9—C32−178.2 (7)Dy1—O5—C23—C2493.2 (10)
O5—Dy1—O1—C1138.2 (6)C28—N7—C24—C25−3.3 (12)
O3—Dy1—O1—C1−87.9 (7)C28—N7—C24—C23178.1 (7)
O7—Dy1—O1—C161.1 (7)O6—C23—C24—N7−156.2 (8)
N4—Dy1—O1—C1−153.4 (7)O5—C23—C24—N724.5 (10)
N1—Dy1—O1—C1−8.9 (7)O6—C23—C24—C2525.1 (12)
N3—Dy1—O1—C1−16.5 (8)O5—C23—C24—C25−154.1 (8)
N6—Dy1—O1—C1145.1 (7)N7—C24—C25—C260.6 (13)
O5—Dy1—O3—C1268.4 (7)C23—C24—C25—C26179.2 (8)
O1—Dy1—O3—C12−87.1 (7)C24—C25—C26—C271.5 (14)
O7—Dy1—O3—C12174.6 (6)C25—C26—C27—C28−0.9 (14)
N4—Dy1—O3—C12−4.0 (7)C24—N7—C28—C274.1 (11)
N1—Dy1—O3—C12−152.3 (7)C24—N7—C28—N8−178.2 (6)
N3—Dy1—O3—C12145.0 (7)C26—C27—C28—N7−2.1 (13)
N6—Dy1—O3—C12−18.0 (8)C26—C27—C28—N8−179.7 (8)
O3—Dy1—O5—C23−137.7 (10)C30—N8—C28—N717.3 (12)
O1—Dy1—O5—C23−7.7 (12)N9—N8—C28—N7−164.8 (6)
O7—Dy1—O5—C2372.7 (10)C30—N8—C28—C27−164.9 (8)
N4—Dy1—O5—C23−76.6 (10)N9—N8—C28—C2713.0 (11)
N1—Dy1—O5—C23122.8 (10)N9—N8—C30—C31−0.2 (9)
N3—Dy1—O5—C23152.2 (10)C28—N8—C30—C31177.8 (7)
N6—Dy1—O5—C23−14.4 (10)N9—N8—C30—C29−177.9 (7)
Dy1—O1—C1—O2−165.7 (7)C28—N8—C30—C290.0 (13)
Dy1—O1—C1—C212.1 (11)N8—C30—C31—C320.2 (9)
C6—N1—C2—C31.1 (11)C29—C30—C31—C32177.8 (8)
Dy1—N1—C2—C3178.7 (6)N8—N9—C32—C310.0 (9)
C6—N1—C2—C1−177.7 (7)N8—N9—C32—C33−179.6 (7)
Dy1—N1—C2—C1−0.1 (8)C30—C31—C32—N9−0.2 (10)
O2—C1—C2—N1171.0 (8)C30—C31—C32—C33179.5 (8)
O1—C1—C2—N1−6.9 (11)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O7—H7D···O8i0.852.042.754 (6)141
O7—H7E···O9ii0.851.902.670 (9)150
O8—H8A···O2iii0.851.882.728 (8)172
O8—H8B···N9iv0.852.002.847 (10)173
O9—H9A···O6v0.851.822.665 (8)170
O9—H9B···O10vi0.852.022.858 (9)171
O10—H10A···O8vii0.852.072.915 (9)175
O10—H10B···O2iii0.852.142.988 (10)175
C27—H27···O8iv0.932.593.406 (11)147
C29—H29B···O4i0.962.573.363 (12)140
C22—H22A···O70.962.523.147 (11)123
C29—H29C···N70.962.492.874 (10)104
C33—H33B···Cgviii0.962.973.893161
Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) x, y+1, z+1; (iii) x, y, z−1; (iv) −x+2, −y+1, −z+1; (v) x, y−1, z−1; (vi) −x+3/2, y−1/2, −z+1/2; (vii) −x+3/2, y+1/2, −z+1/2; (viii) x−1/2, −y+1/2, z−3/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O7—H7D···O8i0.852.042.754 (6)141
O7—H7E···O9ii0.851.902.670 (9)150
O8—H8A···O2iii0.851.882.728 (8)172
O8—H8B···N9iv0.852.002.847 (10)173
O9—H9A···O6v0.851.822.665 (8)170
O9—H9B···O10vi0.852.022.858 (9)171
O10—H10A···O8vii0.852.072.915 (9)175
O10—H10B···O2iii0.852.142.988 (10)175
C27—H27···O8iv0.932.593.406 (11)147
C29—H29B···O4i0.962.573.363 (12)140
C22—H22A···O70.962.523.147 (11)123
C29—H29C···N70.962.492.874 (10)104
C33—H33B···Cgviii0.962.973.893161
Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) x, y+1, z+1; (iii) x, y, z−1; (iv) −x+2, −y+1, −z+1; (v) x, y−1, z−1; (vi) −x+3/2, y−1/2, −z+1/2; (vii) −x+3/2, y+1/2, −z+1/2; (viii) x−1/2, −y+1/2, z−3/2.
Acknowledgements top

The authors thank the National Natural Science Foundation of China (grant No. 20761002). This research was sponsored by the Fund of the Talented Highland Research Programme of Guangxi University (grant No. 205121), the Science Foundation of the State Ethnic Affairs Commission (grant No. 07GX05), the Ministry of Education Science and Technology Key Projects (grant No. 205121), the Development Foundation Guangxi Research Institute of Chemical Industry and the Science Foundation of Guangxi University for Nationalities (grant Nos. 0409032, 0409012 and 0509ZD047).

references
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