supplementary materials


om2208 scheme

Acta Cryst. (2008). E64, m407    [ doi:10.1107/S1600536808001931 ]

Tris[6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinato]gadolinium(III) methanol hemisolvate 2.5-hydrate

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

Abstract top

In the title complex, [Gd(C11H10N3O2)3]·0.5CH4O·2.5H2O, the Gd atom is coordinated by six N atoms and three O atoms derived from three tridentate monoanionic 6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinate ligands. The molecules are linked together via hydrogen bonds involving the solvent water and methanol molecules.

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]cobalt(II) 2.5- hydrate (Zhao et al., 2007). As a continuation of these investigations, we report in this paper the crystal structure of tris(6-(3,5-dimethyl-1H-pyrazol-1-yl))picolinato)gadolinium(III) 2.5 hydrate 0.5 methanol solvate.

In the title complex, the gadolinium(III) ion is nine-coordinated by six N atoms and three O atoms derived from the tridentate ligands, 6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinate (DPP); the angles around Gd(III) atom range from 60.34 (15) to 149.67 (16) °, the Gd—O bond lengths are 2.320 (4), 2.343 (4) and 2.372 (4) Å, The Gd—N distances range from 2.512 (5) to 2.742 (5) Å, i.e. normal values. The C1—C2 bond length is 1.520 (9) Å, being in the normal C—C ranges for gadolinium carboxylate complexes.

In the crystal structure, the oxygen atoms contribute to the formation of intermolecular hydrogen bonds involving the solvate molecules that link the complex into a three-dimensional network. (Fig. 2; for symmetry codes see Table 2).

Related literature top

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

Experimental top

6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinic acid, and GdCl3. 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 methanol (AR, 99.9%) (15 ml). The mixture was stirred to give a clear solution, To this solution was added GdCl3.6H2O (0.33 mmol, 99 mg) in anhydrous methanol (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, washed with alcohol three times (yield, 75%). Elemental analysis: found: C, 46.31; H, 4.37; N, 14.46; calc. for C67H74Gd2N18O18: C, 46.41; H, 4.30; N, 14.54.

Refinement top

H atoms on C atoms were positoned geometrically and refined using a riding model with C—H = 0.96Å and Uiso(H) = 1.2Ueq(C). The water H atoms were located in difference Fourier maps and the O—H distances were constrained to 0.85 Å, with Uiso(H) = 1.2Ueq(O). The methanol O—H hydrogen atom was constrained with O—H distance of 0.82 Å. There are five waters of hydration sites and one methanol solvate site; all of these atoms were refined at half- occupancy. The largest difference map peaks are in the region of the disordered solvate molecules and probably represent alternative water and methanol sites that were not modeled.

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).

Figures top
[Figure 1] Fig. 1. The structure of the title compound showing 50% probability displacement ellipsoids and the atom-numbering scheme. All of the solvate sites contain atoms that were refined at half occupancy.
[Figure 2] Fig. 2. Crystal packing as viewed down the c-direction showing the hydrogen bonded interactions as dashed lines.
Tris[6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinato]gadolinium(III) methanol hemisolvate 2.5-hydrate top
Crystal data top
[Gd(C11H10N3O2)3]·0.5CH4O·2.5H2OF000 = 1748
Mr = 866.97Dx = 1.430 Mg m3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
a = 15.5217 (18) ÅCell parameters from 7251 reflections
b = 16.5515 (19) Åθ = 1.6–25.0º
c = 16.434 (2) ŵ = 1.71 mm1
β = 107.434 (2)ºT = 298 (2) K
V = 4028.0 (8) Å3Block, colorless
Z = 40.50 × 0.49 × 0.45 mm
Data collection top
Bruker SMART 1000
diffractometer
7101 independent reflections
Radiation source: fine-focus sealed tube5129 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.038
T = 298(2) Kθmax = 25.0º
φ and ω scansθmin = 1.6º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 18→17
Tmin = 0.483, Tmax = 0.514k = 19→19
19991 measured reflectionsl = 15→19
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)] = 0.044H-atom parameters constrained
wR(F2) = 0.147  w = 1/[σ2(Fo2) + (0.0899P)2 + 0.2214P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
7101 reflectionsΔρmax = 1.34 e Å3
505 parametersΔρmin = 1.00 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Gd(C11H10N3O2)3]·0.5CH4O·2.5H2OV = 4028.0 (8) Å3
Mr = 866.97Z = 4
Monoclinic, P21/nMo Kα
a = 15.5217 (18) ŵ = 1.71 mm1
b = 16.5515 (19) ÅT = 298 (2) K
c = 16.434 (2) Å0.50 × 0.49 × 0.45 mm
β = 107.434 (2)º
Data collection top
Bruker SMART 1000
diffractometer
7101 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
5129 reflections with I > 2σ(I)
Tmin = 0.483, Tmax = 0.514Rint = 0.038
19991 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.044505 parameters
wR(F2) = 0.147H-atom parameters constrained
S = 1.08Δρmax = 1.34 e Å3
7101 reflectionsΔρmin = 1.00 e Å3
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*/UeqOcc. (<1)
Gd10.704685 (17)0.060270 (16)0.866254 (18)0.03314 (13)
N10.8658 (3)0.0884 (3)0.9613 (3)0.0352 (11)
N20.9217 (3)0.0719 (3)0.8485 (3)0.0372 (12)
N30.8436 (3)0.0310 (3)0.8074 (3)0.0410 (12)
N40.5908 (3)0.0223 (3)0.9109 (3)0.0361 (11)
N50.4775 (3)0.0643 (3)0.8416 (4)0.0428 (13)
N60.5442 (3)0.1201 (3)0.8435 (4)0.0514 (14)
N70.6714 (3)0.1199 (3)0.7172 (3)0.0422 (12)
N80.7776 (4)0.2190 (3)0.7700 (3)0.0484 (13)
N90.7582 (4)0.2151 (3)0.8470 (3)0.0489 (13)
O10.7175 (3)0.1017 (3)1.0057 (3)0.0465 (11)
O20.7941 (3)0.1072 (5)1.1439 (3)0.0833 (19)
O30.7600 (3)0.0609 (2)0.9325 (3)0.0439 (11)
O40.7576 (3)0.1610 (3)1.0214 (3)0.0575 (12)
O50.6111 (3)0.0179 (2)0.7530 (3)0.0459 (10)
O60.5029 (4)0.0245 (3)0.6291 (4)0.0802 (18)
O70.1858 (7)0.2686 (7)0.6923 (8)0.090 (4)0.50
H7D0.20240.27210.74640.108*0.50
H7E0.21540.30300.67310.108*0.50
O80.2573 (8)0.2951 (7)0.8861 (8)0.100 (4)0.50
H8A0.27110.25220.91550.120*0.50
H8B0.30370.31240.87420.120*0.50
O90.1011 (9)0.3661 (10)0.8144 (10)0.125 (5)0.50
H9A0.15130.34920.84710.150*0.50
H9B0.07850.39910.84200.150*0.50
O100.1065 (14)0.1462 (12)0.5951 (12)0.191 (9)0.50
H10A0.14990.17910.60040.229*0.50
H10B0.06700.15580.54770.229*0.50
O110.3711 (10)0.3944 (12)0.8122 (10)0.131 (6)0.50
H110.36710.42490.77190.197*0.50
O120.692 (2)0.033 (2)0.417 (2)0.35 (3)0.50
H12A0.64140.01380.41810.426*0.50
H12B0.68140.07320.38380.426*0.50
C10.7885 (4)0.1022 (4)1.0680 (4)0.0479 (16)
C20.8756 (4)0.0975 (4)1.0439 (4)0.0387 (14)
C30.9603 (4)0.1085 (4)1.1044 (4)0.0504 (17)
H30.96610.11341.16220.060*
C41.0346 (4)0.1116 (4)1.0750 (4)0.0479 (16)
H41.09160.12021.11330.057*
C51.0253 (4)0.1023 (4)0.9908 (4)0.0441 (15)
H51.07530.10470.97080.053*
C60.9389 (4)0.0889 (3)0.9345 (4)0.0379 (14)
C71.0654 (5)0.1232 (6)0.8168 (5)0.086 (3)
H7A1.05870.17480.84080.129*
H7B1.08180.13080.76550.129*
H7C1.11180.09290.85710.129*
C80.9764 (4)0.0771 (5)0.7964 (5)0.059 (2)
C90.9325 (5)0.0386 (5)0.7233 (5)0.064 (2)
H90.95290.03250.67600.077*
C100.8515 (4)0.0099 (4)0.7313 (4)0.0490 (16)
C110.7833 (5)0.0415 (5)0.6708 (5)0.072 (2)
H11A0.75210.01020.62160.108*
H11B0.74080.06110.69820.108*
H11C0.81290.08640.65350.108*
C120.7212 (4)0.1057 (4)0.9742 (4)0.0368 (13)
C130.6208 (4)0.0897 (4)0.9568 (4)0.0375 (13)
C140.5651 (4)0.1426 (4)0.9806 (4)0.0456 (15)
H140.58810.18821.01280.055*
C150.4736 (4)0.1264 (4)0.9556 (5)0.0560 (19)
H150.43410.16140.97070.067*
C160.4410 (4)0.0585 (4)0.9081 (5)0.0493 (17)
H160.37950.04700.89030.059*
C170.5028 (4)0.0078 (4)0.8876 (4)0.0389 (14)
C180.3043 (5)0.0523 (6)0.7872 (7)0.105 (4)
H18A0.28440.05730.83690.157*
H18B0.31220.00380.77630.157*
H18C0.26000.07550.73900.157*
C190.3945 (4)0.0969 (5)0.8020 (5)0.063 (2)
C200.4093 (5)0.1734 (5)0.7808 (5)0.075 (2)
H200.36530.21090.75390.090*
C210.5023 (4)0.1859 (4)0.8064 (5)0.0600 (19)
C220.5512 (6)0.2626 (5)0.8014 (8)0.108 (4)
H22A0.51660.30770.81100.162*
H22B0.55940.26730.74600.162*
H22C0.60910.26220.84410.162*
C230.5688 (5)0.0082 (4)0.6795 (4)0.0512 (17)
C240.6078 (4)0.0844 (4)0.6530 (4)0.0466 (16)
C250.5839 (5)0.1123 (5)0.5715 (5)0.066 (2)
H250.53960.08600.52880.079*
C260.6265 (5)0.1809 (5)0.5527 (5)0.071 (2)
H260.61150.20110.49740.085*
C270.6910 (5)0.2178 (5)0.6176 (5)0.063 (2)
H270.72000.26410.60740.076*
C280.7124 (4)0.1845 (4)0.6996 (4)0.0480 (16)
C290.8930 (5)0.2784 (5)0.7065 (6)0.079 (3)
H29A0.95610.29020.73080.119*
H29B0.86380.32270.67120.119*
H29C0.88610.23030.67250.119*
C300.8508 (5)0.2659 (4)0.7767 (5)0.059 (2)
C310.8787 (5)0.2951 (4)0.8578 (6)0.066 (2)
H310.92770.32910.88100.079*
C320.8200 (5)0.2644 (4)0.8990 (5)0.059 (2)
C330.8156 (7)0.2833 (5)0.9858 (5)0.086 (3)
H33A0.76850.25200.99740.128*
H33B0.80300.33980.98940.128*
H33C0.87230.27051.02700.128*
C340.3849 (15)0.4409 (15)0.889 (2)0.145 (13)0.50
H34A0.41290.40760.93750.218*0.50
H34B0.32770.45990.89260.218*0.50
H34C0.42310.48620.88790.218*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Gd10.02672 (18)0.0401 (2)0.0335 (2)0.00086 (11)0.01038 (13)0.00180 (13)
N10.030 (3)0.035 (2)0.042 (3)0.001 (2)0.013 (2)0.001 (2)
N20.027 (3)0.048 (3)0.040 (3)0.001 (2)0.015 (2)0.004 (2)
N30.030 (3)0.049 (3)0.045 (3)0.002 (2)0.014 (2)0.004 (3)
N40.029 (2)0.047 (3)0.033 (3)0.001 (2)0.010 (2)0.000 (2)
N50.026 (2)0.057 (3)0.046 (3)0.004 (2)0.011 (2)0.003 (3)
N60.042 (3)0.057 (3)0.057 (4)0.009 (3)0.019 (3)0.013 (3)
N70.041 (3)0.047 (3)0.037 (3)0.001 (2)0.010 (2)0.007 (2)
N80.050 (3)0.049 (3)0.046 (3)0.002 (3)0.015 (3)0.012 (3)
N90.050 (3)0.046 (3)0.047 (3)0.002 (2)0.009 (3)0.006 (3)
O10.034 (2)0.069 (3)0.041 (3)0.004 (2)0.016 (2)0.006 (2)
O20.062 (4)0.145 (6)0.049 (4)0.017 (3)0.027 (3)0.021 (3)
O30.030 (2)0.048 (2)0.058 (3)0.0023 (17)0.020 (2)0.011 (2)
O40.050 (3)0.062 (3)0.061 (3)0.010 (2)0.017 (2)0.026 (3)
O50.049 (2)0.047 (2)0.041 (3)0.010 (2)0.011 (2)0.002 (2)
O60.069 (4)0.074 (3)0.072 (4)0.017 (3)0.017 (3)0.013 (3)
O70.065 (7)0.117 (10)0.093 (9)0.016 (6)0.029 (6)0.068 (8)
O80.091 (9)0.095 (9)0.130 (11)0.010 (7)0.058 (8)0.068 (8)
O90.093 (10)0.154 (14)0.128 (13)0.028 (10)0.032 (9)0.027 (11)
O100.21 (2)0.19 (2)0.138 (17)0.011 (16)0.001 (15)0.008 (15)
O110.104 (11)0.197 (17)0.086 (11)0.012 (11)0.019 (9)0.038 (12)
O120.26 (4)0.53 (6)0.36 (4)0.24 (4)0.23 (4)0.28 (5)
C10.049 (4)0.058 (4)0.039 (4)0.010 (3)0.017 (3)0.007 (3)
C20.035 (3)0.043 (3)0.037 (4)0.006 (3)0.010 (3)0.003 (3)
C30.047 (4)0.056 (4)0.043 (4)0.008 (3)0.006 (3)0.003 (3)
C40.031 (3)0.046 (4)0.058 (5)0.002 (3)0.001 (3)0.002 (3)
C50.033 (3)0.043 (3)0.057 (4)0.001 (3)0.014 (3)0.000 (3)
C60.030 (3)0.032 (3)0.054 (4)0.006 (2)0.016 (3)0.014 (3)
C70.054 (5)0.135 (8)0.075 (6)0.033 (5)0.027 (4)0.015 (6)
C80.035 (4)0.091 (5)0.057 (5)0.003 (3)0.025 (3)0.011 (4)
C90.056 (5)0.095 (6)0.050 (5)0.007 (4)0.030 (4)0.006 (4)
C100.047 (4)0.067 (4)0.040 (4)0.006 (3)0.023 (3)0.001 (3)
C110.061 (5)0.091 (6)0.061 (5)0.001 (4)0.014 (4)0.027 (5)
C120.033 (3)0.046 (3)0.034 (3)0.003 (3)0.013 (3)0.003 (3)
C130.035 (3)0.048 (3)0.033 (3)0.007 (3)0.015 (3)0.006 (3)
C140.049 (4)0.047 (4)0.047 (4)0.006 (3)0.023 (3)0.001 (3)
C150.049 (4)0.066 (5)0.066 (5)0.025 (3)0.036 (4)0.014 (4)
C160.028 (3)0.061 (4)0.064 (5)0.005 (3)0.020 (3)0.011 (4)
C170.030 (3)0.050 (4)0.036 (3)0.002 (3)0.009 (2)0.005 (3)
C180.030 (4)0.144 (10)0.119 (9)0.004 (4)0.011 (5)0.029 (7)
C190.026 (3)0.091 (6)0.066 (5)0.017 (4)0.006 (3)0.004 (5)
C200.047 (4)0.086 (6)0.089 (6)0.028 (4)0.018 (4)0.027 (5)
C210.046 (4)0.067 (5)0.068 (5)0.022 (4)0.020 (3)0.017 (4)
C220.090 (7)0.067 (6)0.182 (12)0.028 (5)0.064 (7)0.059 (7)
C230.054 (4)0.051 (4)0.045 (4)0.004 (3)0.009 (3)0.011 (3)
C240.043 (4)0.055 (4)0.040 (4)0.009 (3)0.009 (3)0.004 (3)
C250.076 (5)0.072 (5)0.041 (4)0.005 (4)0.003 (4)0.007 (4)
C260.080 (5)0.083 (6)0.042 (4)0.003 (5)0.008 (4)0.015 (4)
C270.073 (5)0.066 (5)0.058 (5)0.009 (4)0.031 (4)0.026 (4)
C280.042 (3)0.055 (4)0.048 (4)0.007 (3)0.014 (3)0.013 (3)
C290.064 (5)0.082 (6)0.095 (7)0.012 (4)0.029 (5)0.031 (5)
C300.050 (4)0.052 (4)0.080 (6)0.003 (3)0.025 (4)0.025 (4)
C310.064 (5)0.051 (4)0.074 (6)0.015 (4)0.007 (4)0.013 (4)
C320.068 (5)0.045 (4)0.052 (4)0.000 (3)0.003 (4)0.009 (3)
C330.131 (8)0.057 (5)0.053 (5)0.012 (5)0.004 (5)0.008 (4)
C340.055 (13)0.15 (3)0.21 (4)0.018 (13)0.014 (17)0.05 (2)
Geometric parameters (Å, °) top
Gd1—O32.320 (4)C7—C81.525 (9)
Gd1—O12.343 (4)C7—H7A0.9600
Gd1—O52.372 (4)C7—H7B0.9600
Gd1—N42.512 (5)C7—H7C0.9600
Gd1—N72.546 (5)C8—C91.349 (10)
Gd1—N12.563 (4)C9—C101.386 (9)
Gd1—N62.601 (5)C9—H90.9300
Gd1—N32.659 (5)C10—C111.483 (9)
Gd1—N92.742 (5)C11—H11A0.9600
N1—C21.329 (7)C11—H11B0.9600
N1—C61.334 (7)C11—H11C0.9600
N2—N31.377 (7)C12—C131.522 (8)
N2—C81.377 (8)C13—C141.367 (8)
N2—C61.387 (8)C14—C151.380 (9)
N3—C101.339 (8)C14—H140.9300
N4—C171.326 (7)C15—C161.375 (9)
N4—C131.348 (8)C15—H150.9300
N5—C191.368 (8)C16—C171.391 (9)
N5—N61.381 (7)C16—H160.9300
N5—C171.403 (7)C18—C191.536 (11)
N6—C211.321 (8)C18—H18A0.9600
N7—C281.321 (8)C18—H18B0.9600
N7—C241.345 (8)C18—H18C0.9600
N8—C301.353 (9)C19—C201.351 (11)
N8—N91.388 (8)C20—C211.393 (10)
N8—C281.409 (8)C20—H200.9300
N9—C321.350 (8)C21—C221.494 (11)
O1—C11.260 (7)C22—H22A0.9600
O2—C11.226 (8)C22—H22B0.9600
O3—C121.275 (7)C22—H22C0.9600
O4—C121.223 (7)C23—C241.518 (10)
O5—C231.265 (7)C24—C251.359 (9)
O6—C231.232 (7)C25—C261.395 (11)
O7—H7D0.8500C25—H250.9300
O7—H7E0.8501C26—C271.368 (10)
O8—H8A0.8500C26—H260.9300
O8—H8B0.8501C27—C281.400 (9)
O9—H9A0.8500C27—H270.9300
O9—H9B0.8500C29—C301.502 (11)
O10—H10A0.8500C29—H29A0.9600
O10—H10B0.8499C29—H29B0.9600
O11—C341.44 (3)C29—H29C0.9600
O11—H110.8200C30—C311.361 (11)
O12—H12A0.8501C31—C321.385 (11)
O12—H12B0.8400C31—H310.9300
C1—C21.520 (9)C32—C331.482 (11)
C2—C31.403 (8)C33—H33A0.9600
C3—C41.379 (9)C33—H33B0.9600
C3—H30.9300C33—H33C0.9600
C4—C51.357 (9)C34—H34A0.9600
C4—H40.9300C34—H34B0.9600
C5—C61.400 (8)C34—H34C0.9600
C5—H50.9300
O3—Gd1—O183.26 (16)N2—C8—C7125.5 (7)
O3—Gd1—O587.15 (14)C8—C9—C10108.0 (6)
O1—Gd1—O5141.23 (14)C8—C9—H9126.0
O3—Gd1—N465.55 (14)C10—C9—H9126.0
O1—Gd1—N474.60 (15)N3—C10—C9109.7 (6)
O5—Gd1—N467.26 (15)N3—C10—C11121.9 (6)
O3—Gd1—N7136.58 (16)C9—C10—C11128.2 (7)
O1—Gd1—N7139.55 (17)C10—C11—H11A109.5
O5—Gd1—N763.68 (15)C10—C11—H11B109.5
N4—Gd1—N7122.31 (15)H11A—C11—H11B109.5
O3—Gd1—N173.43 (15)C10—C11—H11C109.5
O1—Gd1—N164.52 (14)H11A—C11—H11C109.5
O5—Gd1—N1146.42 (15)H11B—C11—H11C109.5
N4—Gd1—N1124.37 (15)O4—C12—O3125.0 (5)
N7—Gd1—N1113.28 (16)O4—C12—C13120.0 (5)
O3—Gd1—N6126.86 (16)O3—C12—C13114.8 (5)
O1—Gd1—N679.98 (16)N4—C13—C14123.2 (5)
O5—Gd1—N676.13 (17)N4—C13—C12114.2 (5)
N4—Gd1—N661.43 (16)C14—C13—C12122.4 (6)
N7—Gd1—N678.75 (17)C13—C14—C15118.2 (6)
N1—Gd1—N6137.39 (17)C13—C14—H14120.9
O3—Gd1—N377.70 (15)C15—C14—H14120.9
O1—Gd1—N3124.68 (15)C16—C15—C14119.9 (6)
O5—Gd1—N389.28 (15)C16—C15—H15120.0
N4—Gd1—N3136.50 (15)C14—C15—H15120.0
N7—Gd1—N370.93 (16)C15—C16—C17117.9 (6)
N1—Gd1—N360.34 (15)C15—C16—H16121.1
N6—Gd1—N3149.67 (16)C17—C16—H16121.1
O3—Gd1—N9141.25 (15)N4—C17—C16123.1 (6)
O1—Gd1—N984.22 (16)N4—C17—N5114.1 (5)
O5—Gd1—N9123.70 (15)C16—C17—N5122.8 (5)
N4—Gd1—N9143.76 (16)C19—C18—H18A109.5
N7—Gd1—N960.52 (16)C19—C18—H18B109.5
N1—Gd1—N968.06 (15)H18A—C18—H18B109.5
N6—Gd1—N986.43 (16)C19—C18—H18C109.5
N3—Gd1—N979.74 (16)H18A—C18—H18C109.5
C2—N1—C6119.2 (5)H18B—C18—H18C109.5
C2—N1—Gd1115.7 (4)C20—C19—N5106.5 (6)
C6—N1—Gd1124.8 (4)C20—C19—C18128.8 (7)
N3—N2—C8110.0 (5)N5—C19—C18124.7 (7)
N3—N2—C6118.2 (5)C19—C20—C21107.6 (6)
C8—N2—C6130.9 (5)C19—C20—H20126.2
C10—N3—N2105.9 (5)C21—C20—H20126.2
C10—N3—Gd1134.3 (4)N6—C21—C20109.8 (7)
N2—N3—Gd1115.0 (4)N6—C21—C22122.6 (6)
C17—N4—C13117.7 (5)C20—C21—C22127.4 (7)
C17—N4—Gd1124.8 (4)C21—C22—H22A109.5
C13—N4—Gd1117.3 (3)C21—C22—H22B109.5
C19—N5—N6109.9 (6)H22A—C22—H22B109.5
C19—N5—C17131.5 (6)C21—C22—H22C109.5
N6—N5—C17118.0 (5)H22A—C22—H22C109.5
C21—N6—N5106.2 (5)H22B—C22—H22C109.5
C21—N6—Gd1134.3 (5)O6—C23—O5125.5 (7)
N5—N6—Gd1115.4 (3)O6—C23—C24119.6 (6)
C28—N7—C24118.1 (5)O5—C23—C24114.9 (5)
C28—N7—Gd1123.5 (4)N7—C24—C25123.0 (7)
C24—N7—Gd1118.4 (4)N7—C24—C23113.5 (5)
C30—N8—N9111.0 (6)C25—C24—C23123.4 (6)
C30—N8—C28132.7 (6)C24—C25—C26119.2 (7)
N9—N8—C28115.6 (5)C24—C25—H25120.4
C32—N9—N8104.0 (6)C26—C25—H25120.4
C32—N9—Gd1132.3 (4)C27—C26—C25118.4 (7)
N8—N9—Gd1107.7 (4)C27—C26—H26120.8
C1—O1—Gd1126.5 (4)C25—C26—H26120.8
C12—O3—Gd1125.9 (4)C26—C27—C28118.8 (7)
C23—O5—Gd1125.7 (4)C26—C27—H27120.6
H7D—O7—H7E108.2C28—C27—H27120.6
H8A—O8—H8B109.0N7—C28—C27122.6 (6)
H9A—O9—H9B108.8N7—C28—N8115.0 (5)
H10A—O10—H10B107.8C27—C28—N8122.4 (6)
C34—O11—H11109.5C30—C29—H29A109.5
H12A—O12—H12B107.6C30—C29—H29B109.5
O2—C1—O1127.3 (7)H29A—C29—H29B109.5
O2—C1—C2118.1 (6)C30—C29—H29C109.5
O1—C1—C2114.6 (6)H29A—C29—H29C109.5
N1—C2—C3122.3 (6)H29B—C29—H29C109.5
N1—C2—C1115.8 (5)N8—C30—C31107.3 (7)
C3—C2—C1121.8 (6)N8—C30—C29124.4 (8)
C4—C3—C2117.5 (6)C31—C30—C29128.3 (7)
C4—C3—H3121.2C30—C31—C32106.6 (7)
C2—C3—H3121.2C30—C31—H31126.7
C5—C4—C3120.5 (6)C32—C31—H31126.7
C5—C4—H4119.7N9—C32—C31111.0 (7)
C3—C4—H4119.7N9—C32—C33120.5 (8)
C4—C5—C6118.7 (6)C31—C32—C33128.3 (7)
C4—C5—H5120.6C32—C33—H33A109.5
C6—C5—H5120.6C32—C33—H33B109.5
N1—C6—N2114.3 (5)H33A—C33—H33B109.5
N1—C6—C5121.6 (6)C32—C33—H33C109.5
N2—C6—C5124.0 (6)H33A—C33—H33C109.5
C8—C7—H7A109.5H33B—C33—H33C109.5
C8—C7—H7B109.5O11—C34—H34A109.5
H7A—C7—H7B109.5O11—C34—H34B109.5
C8—C7—H7C109.5H34A—C34—H34B109.5
H7A—C7—H7C109.5O11—C34—H34C109.5
H7B—C7—H7C109.5H34A—C34—H34C109.5
C9—C8—N2106.4 (6)H34B—C34—H34C109.5
C9—C8—C7127.9 (7)
O3—Gd1—N1—C278.6 (4)N1—Gd1—O3—C12128.0 (5)
O1—Gd1—N1—C211.7 (4)N6—Gd1—O3—C129.5 (5)
O5—Gd1—N1—C2135.8 (4)N3—Gd1—O3—C12169.7 (5)
N4—Gd1—N1—C235.2 (5)N9—Gd1—O3—C12134.6 (4)
N7—Gd1—N1—C2147.2 (4)O3—Gd1—O5—C23165.5 (5)
N6—Gd1—N1—C248.3 (5)O1—Gd1—O5—C23119.0 (5)
N3—Gd1—N1—C2163.7 (5)N4—Gd1—O5—C23129.9 (5)
N9—Gd1—N1—C2105.9 (4)N7—Gd1—O5—C2318.7 (5)
O3—Gd1—N1—C696.7 (5)N1—Gd1—O5—C23111.7 (5)
O1—Gd1—N1—C6173.0 (5)N6—Gd1—O5—C2365.4 (5)
O5—Gd1—N1—C639.5 (6)N3—Gd1—O5—C2387.7 (5)
N4—Gd1—N1—C6140.1 (4)N9—Gd1—O5—C2310.6 (6)
N7—Gd1—N1—C637.5 (5)Gd1—O1—C1—O2163.4 (7)
N6—Gd1—N1—C6136.4 (4)Gd1—O1—C1—C217.6 (8)
N3—Gd1—N1—C611.6 (4)C6—N1—C2—C30.6 (9)
N9—Gd1—N1—C678.9 (5)Gd1—N1—C2—C3176.1 (5)
C8—N2—N3—C101.2 (7)C6—N1—C2—C1175.8 (5)
C6—N2—N3—C10169.1 (5)Gd1—N1—C2—C18.6 (7)
C8—N2—N3—Gd1157.8 (4)O2—C1—C2—N1176.9 (7)
C6—N2—N3—Gd131.9 (6)O1—C1—C2—N14.1 (9)
O3—Gd1—N3—C10109.9 (6)O2—C1—C2—C37.8 (10)
O1—Gd1—N3—C10177.4 (6)O1—C1—C2—C3171.2 (6)
O5—Gd1—N3—C1022.6 (6)N1—C2—C3—C41.7 (9)
N4—Gd1—N3—C1077.5 (6)C1—C2—C3—C4173.3 (6)
N7—Gd1—N3—C1039.7 (6)C2—C3—C4—C51.7 (9)
N1—Gd1—N3—C10172.4 (7)C3—C4—C5—C60.4 (9)
N6—Gd1—N3—C1037.6 (8)C2—N1—C6—N2174.7 (5)
N9—Gd1—N3—C10101.9 (6)Gd1—N1—C6—N20.4 (7)
O3—Gd1—N3—N298.9 (4)C2—N1—C6—C52.8 (9)
O1—Gd1—N3—N226.2 (4)Gd1—N1—C6—C5178.0 (4)
O5—Gd1—N3—N2173.8 (4)N3—N2—C6—N121.7 (7)
N4—Gd1—N3—N2131.3 (4)C8—N2—C6—N1170.5 (6)
N7—Gd1—N3—N2111.5 (4)N3—N2—C6—C5155.8 (5)
N1—Gd1—N3—N221.2 (3)C8—N2—C6—C512.0 (10)
N6—Gd1—N3—N2113.6 (4)C4—C5—C6—N12.8 (9)
N9—Gd1—N3—N249.3 (4)C4—C5—C6—N2174.5 (6)
O3—Gd1—N4—C17168.9 (5)N3—N2—C8—C90.5 (8)
O1—Gd1—N4—C17101.6 (5)C6—N2—C8—C9168.1 (6)
O5—Gd1—N4—C1771.3 (4)N3—N2—C8—C7175.3 (7)
N7—Gd1—N4—C1737.8 (5)C6—N2—C8—C716.1 (12)
N1—Gd1—N4—C17144.8 (4)N2—C8—C9—C100.3 (9)
N6—Gd1—N4—C1714.8 (4)C7—C8—C9—C10176.0 (8)
N3—Gd1—N4—C17133.9 (4)N2—N3—C10—C91.3 (7)
N9—Gd1—N4—C1745.1 (6)Gd1—N3—C10—C9151.6 (5)
O3—Gd1—N4—C136.0 (4)N2—N3—C10—C11174.9 (6)
O1—Gd1—N4—C1383.5 (4)Gd1—N3—C10—C1132.1 (10)
O5—Gd1—N4—C13103.6 (4)C8—C9—C10—N31.0 (9)
N7—Gd1—N4—C13137.1 (4)C8—C9—C10—C11174.9 (7)
N1—Gd1—N4—C1340.3 (5)Gd1—O3—C12—O4166.0 (5)
N6—Gd1—N4—C13170.3 (5)Gd1—O3—C12—C1318.1 (7)
N3—Gd1—N4—C1341.1 (5)C17—N4—C13—C140.5 (9)
N9—Gd1—N4—C13139.9 (4)Gd1—N4—C13—C14175.8 (5)
C19—N5—N6—C210.6 (8)C17—N4—C13—C12174.9 (5)
C17—N5—N6—C21171.4 (6)Gd1—N4—C13—C120.4 (6)
C19—N5—N6—Gd1159.8 (5)O4—C12—C13—N4173.6 (6)
C17—N5—N6—Gd128.2 (7)O3—C12—C13—N410.2 (7)
O3—Gd1—N6—C21178.4 (6)O4—C12—C13—C1410.9 (9)
O1—Gd1—N6—C21108.0 (7)O3—C12—C13—C14165.2 (6)
O5—Gd1—N6—C21102.8 (7)N4—C13—C14—C150.7 (9)
N4—Gd1—N6—C21174.2 (7)C12—C13—C14—C15174.3 (6)
N7—Gd1—N6—C2137.4 (7)C13—C14—C15—C160.2 (10)
N1—Gd1—N6—C2174.9 (7)C14—C15—C16—C170.5 (10)
N3—Gd1—N6—C2139.4 (8)C13—N4—C17—C160.2 (9)
N9—Gd1—N6—C2123.2 (7)Gd1—N4—C17—C16174.7 (5)
O3—Gd1—N6—N525.1 (5)C13—N4—C17—N5178.7 (5)
O1—Gd1—N6—N598.7 (4)Gd1—N4—C17—N56.4 (7)
O5—Gd1—N6—N550.5 (4)C15—C16—C17—N40.7 (10)
N4—Gd1—N6—N520.9 (4)C15—C16—C17—N5178.1 (6)
N7—Gd1—N6—N5115.9 (4)C19—N5—C17—N4174.7 (7)
N1—Gd1—N6—N5131.9 (4)N6—N5—C17—N415.4 (8)
N3—Gd1—N6—N5113.9 (5)C19—N5—C17—C166.4 (11)
N9—Gd1—N6—N5176.5 (4)N6—N5—C17—C16163.5 (6)
O3—Gd1—N7—C28117.8 (5)N6—N5—C19—C201.2 (9)
O1—Gd1—N7—C2849.9 (6)C17—N5—C19—C20169.4 (7)
O5—Gd1—N7—C28170.6 (5)N6—N5—C19—C18179.2 (8)
N4—Gd1—N7—C28154.8 (5)C17—N5—C19—C1810.2 (13)
N1—Gd1—N7—C2827.6 (5)N5—C19—C20—C211.3 (10)
N6—Gd1—N7—C28109.4 (5)C18—C19—C20—C21179.2 (9)
N3—Gd1—N7—C2871.7 (5)N5—N6—C21—C200.2 (8)
N9—Gd1—N7—C2817.1 (5)Gd1—N6—C21—C20155.2 (6)
O3—Gd1—N7—C2463.2 (5)N5—N6—C21—C22175.4 (8)
O1—Gd1—N7—C24129.2 (4)Gd1—N6—C21—C2229.6 (12)
O5—Gd1—N7—C2410.3 (4)C19—C20—C21—N60.9 (10)
N4—Gd1—N7—C2424.3 (5)C19—C20—C21—C22175.9 (9)
N1—Gd1—N7—C24153.4 (4)Gd1—O5—C23—O6159.2 (6)
N6—Gd1—N7—C2469.6 (5)Gd1—O5—C23—C2423.5 (8)
N3—Gd1—N7—C24109.3 (5)C28—N7—C24—C250.3 (10)
N9—Gd1—N7—C24161.9 (5)Gd1—N7—C24—C25178.8 (6)
C30—N8—N9—C322.7 (7)C28—N7—C24—C23176.9 (6)
C28—N8—N9—C32168.8 (5)Gd1—N7—C24—C234.0 (7)
C30—N8—N9—Gd1141.2 (4)O6—C23—C24—N7171.6 (6)
C28—N8—N9—Gd147.2 (6)O5—C23—C24—N711.0 (9)
O3—Gd1—N9—C3231.7 (8)O6—C23—C24—C2511.2 (11)
O1—Gd1—N9—C3239.9 (7)O5—C23—C24—C25166.2 (7)
O5—Gd1—N9—C32169.1 (6)N7—C24—C25—C260.1 (12)
N4—Gd1—N9—C3293.8 (7)C23—C24—C25—C26177.1 (7)
N7—Gd1—N9—C32160.7 (7)C24—C25—C26—C270.3 (12)
N1—Gd1—N9—C3224.9 (7)C25—C26—C27—C281.0 (12)
N6—Gd1—N9—C32120.2 (7)C24—N7—C28—C271.2 (10)
N3—Gd1—N9—C3286.9 (7)Gd1—N7—C28—C27177.9 (5)
O3—Gd1—N9—N897.7 (4)C24—N7—C28—N8179.4 (6)
O1—Gd1—N9—N8169.4 (4)Gd1—N7—C28—N80.3 (8)
O5—Gd1—N9—N839.6 (4)C26—C27—C28—N71.5 (11)
N4—Gd1—N9—N8136.7 (3)C26—C27—C28—N8179.6 (7)
N7—Gd1—N9—N831.2 (3)C30—N8—C28—N7155.9 (7)
N1—Gd1—N9—N8104.6 (4)N9—N8—C28—N734.9 (8)
N6—Gd1—N9—N8110.3 (4)C30—N8—C28—C2725.9 (11)
N3—Gd1—N9—N842.6 (4)N9—N8—C28—C27143.3 (6)
O3—Gd1—O1—C158.6 (5)N9—N8—C30—C311.7 (8)
O5—Gd1—O1—C1135.4 (5)C28—N8—C30—C31167.9 (7)
N4—Gd1—O1—C1125.0 (6)N9—N8—C30—C29176.0 (6)
N7—Gd1—O1—C1112.9 (5)C28—N8—C30—C2914.4 (12)
N1—Gd1—O1—C116.3 (5)N8—C30—C31—C320.1 (8)
N6—Gd1—O1—C1172.1 (6)C29—C30—C31—C32177.6 (7)
N3—Gd1—O1—C111.4 (6)N8—N9—C32—C312.7 (7)
N9—Gd1—O1—C184.7 (5)Gd1—N9—C32—C31128.0 (6)
O1—Gd1—O3—C1262.6 (5)N8—N9—C32—C33173.5 (6)
O5—Gd1—O3—C1279.8 (5)Gd1—N9—C32—C3355.8 (10)
N4—Gd1—O3—C1213.5 (4)C30—C31—C32—N91.8 (9)
N7—Gd1—O3—C12125.5 (5)C30—C31—C32—C33174.0 (7)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O7—H7D···O80.852.233.074 (19)172
O7—H7E···O2i0.852.072.914 (13)172
O8—H8A···O4ii0.851.962.740 (11)153
O8—H8B···O110.852.152.93 (2)153
O9—H9A···O80.851.812.633 (18)162
O9—H9B···O6iii0.851.942.765 (17)162
O10—H10A···O70.852.072.64 (2)124
O11—H11···O2i0.822.142.664 (17)122
O12—H12A···O6iv0.852.152.89 (3)146
O12—H12B···O9v0.841.742.49 (5)147
O12—H12B···O8v0.852.473.12 (4)133
Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) −x+1, −y, −z+2; (iii) −x+1/2, y+1/2, −z+3/2; (iv) −x+1, −y, −z+1; (v) x+1/2, −y+1/2, z−1/2.
Table 1
Hydrogen-bond geometry (Å, °)
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D—H···AD—HH···AD···AD—H···A
O7—H7D···O80.852.233.074 (19)172
O7—H7E···O2i0.852.072.914 (13)172
O8—H8A···O4ii0.851.962.740 (11)153
O8—H8B···O110.852.152.93 (2)153
O9—H9A···O80.851.812.633 (18)162
O9—H9B···O6iii0.851.942.765 (17)162
O10—H10A···O70.852.072.64 (2)124
O11—H11···O2i0.822.142.664 (17)122
O12—H12A···O6iv0.852.152.89 (3)146
O12—H12B···O9v0.841.742.49 (5)147
O12—H12B···O8v0.852.473.12 (4)133
Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) −x+1, −y, −z+2; (iii) −x+1/2, y+1/2, −z+3/2; (iv) −x+1, −y, −z+1; (v) x+1/2, −y+1/2, z−1/2.
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 Program 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 Nationlities (grant Nos. 0409032, 0409012,0509ZD047), People's Republic of China.

references
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