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Acta Cryst. (2008). E64, m419-m420    [ doi:10.1107/S1600536808001499 ]

([mu]-6-Oxido-4-oxo-1,2-dihydropyrimidine-5-carboxylato-[kappa]4O5,O6:O2,N3)bis[aquabis(4-oxido-2-oxo-1,2-dihydropyrimidin-3-ium-5-carboxylato-[kappa]2O4,O5)(1,10-phenanthroline-[kappa]2N,N')neodymium(III)] hexahydrate

H.-H. Xing, Z.-L. Chen and S. W. Ng

Abstract top

The water-coordinated neodymium(III) atom in the centrosymmetric title compound, [Nd2(C5H2N2O4)(C5H3N2O4)4(C12H8N2)2(H2O)2]·6H2O is chelated by a 1,10-phenanthroline heterocycle and two 2,4-dihydroxypyrimidine-5-carboxylate dianions. Two tris-chelated water-coordinated units are bridged by a 2,4-dihydroxypyrimidine-5-carboxylate dianion, which is disordered about a center of inversion. The metal center has a monocapped square-antiprismatic coordination.

Comment top

The 1,10-phenanthroline-chelated rare-earth compound, Pr2(C12H8N2)2(C5H2N2O4)(C5H3N2O4)4(H2O)2– .3H2O, represents the first example of dinculear lanthanum derivatives of 2,4-dihydroxpyrimidine-5-carboxylic acid (Sun & Jin, 2004). The present neodymium compound is isostructural with the praseodymium analog.

Related literature top

The title neodymium compound is isostructural with the praesodymium analog (Sun & Jin, 2004). For a related structure, see: Xing et al. (2008).

Experimental top

2,4-Dihydroxypyrimidine-5-carboxylic acid (0.044 g, 0.25 mmol), neodymium trichloride hexahydrate (0.090 g, 0.25 mmol), 1,10-phenanthroline (0.050 g, 0.25 mmol), sodium hydroxide (0.010 g, 0.25 mmol) and water (15 ml) was sealed in a 25-ml, Teflon-lined, stainless-steel Parr bomb. The bomb was heated to 383 K for 120 h. It was then cooled over 48 h to give lilac crystals in 70% yield. CH&N elemental analysis. Found (Calculated) for C49H46N14O28Nd2: C 37.37, H 3.07, N 12.62% (37.54, 2.96, 12.51%).

Refinement top

The bridging dianion is disordered about a center of inversion; all atoms were assigned only half site-occupancy except for O2, which had full site occupancy. The pyrimidine ring was refined as a rigid hexagon of 1.39 Å sides.

Carbon-bound H atoms were generated geometrically, and were included in the refinements in the riding model approximation, as well the nitrogen-bound ones. For the water molecules, only those on the coordinated water were were placed in chemically sensible positions on the basis of hydrogen bonding interactions. TWo of the lattice water molecules are each disordered over two positions. The displacement parameters of the two components were restrained to be equal. The H atoms bound to the lattice water molecules could not be located. The final difference Fourier map had a large peak near Nd1.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: atomic coordinates taken from the Pr analog (Sun & Jin, 2004); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top
[Figure 1] Fig. 1. Displacement ellipsoid plot of Nd2(C12H8N2)2(C5H2N2O4)(C5H3N2O4)4(H2O)2 .6H2O drawn at the 50% probability level. Unlabelled atoms are related to labelled atoms by the symmetry operation (1 - x, 1 - y, 1 - z). Lattice water molecules have been omitted for clarity. Only one disorder component is shown.
[Figure 2] Fig. 2. Geometry of Nd.
(µ-6-Oxido-4-oxo-1,2-dihydropyrimidine-5-carboxylato- κ4O5,O6:O2,N3)bis[aquabis(4-oxido- 2-oxo-1,2-dihydropyrimidin-3-ium-5-carboxylato- κ2O4,O5)(1,10-phenanthroline- κ2N,N')neodymium(III)] hexahydrate top
Crystal data top
[Nd2(C5H2N2O4)(C5H3N2O4)4(C12H8N2)2(H2O)2]·6H2OZ = 1
Mr = 1567.48F000 = 782
Triclinic, P1Dx = 1.817 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 10.1980 (7) ÅCell parameters from 2901 reflections
b = 12.8896 (9) Åθ = 2.3–22.7º
c = 13.3383 (9) ŵ = 1.90 mm−1
α = 118.711 (1)ºT = 295 (2) K
β = 90.010 (1)ºPrism, lilac
γ = 108.612 (1)º0.10 × 0.04 × 0.02 mm
V = 1432.25 (17) Å3
Data collection top
Bruker APEXII
diffractometer		6377 independent reflections
Radiation source: fine-focus sealed tube5349 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.039
T = 295(2) Kθmax = 27.5º
φ and ω scansθmin = 1.8º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −13→13
Tmin = 0.724, Tmax = 0.963k = −16→16
12405 measured reflectionsl = −17→17
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)] = 0.054H-atom parameters constrained
wR(F2) = 0.136  w = 1/[σ2(Fo2) + (0.0735P)2 + 0.4633P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
6377 reflectionsΔρmax = 1.23 e Å−3
454 parametersΔρmin = −0.90 e Å−3
84 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Nd2(C5H2N2O4)(C5H3N2O4)4(C12H8N2)2(H2O)2]·6H2Oγ = 108.612 (1)º
Mr = 1567.48V = 1432.25 (17) Å3
Triclinic, P1Z = 1
a = 10.1980 (7) ÅMo Kα
b = 12.8896 (9) ŵ = 1.90 mm−1
c = 13.3383 (9) ÅT = 295 (2) K
α = 118.711 (1)º0.10 × 0.04 × 0.02 mm
β = 90.010 (1)º
Data collection top
Bruker APEXII
diffractometer		6377 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		5349 reflections with I > 2σ(I)
Tmin = 0.724, Tmax = 0.963Rint = 0.039
12405 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05484 restraints
wR(F2) = 0.136H-atom parameters constrained
S = 1.04Δρmax = 1.23 e Å−3
6377 reflectionsΔρmin = −0.90 e Å−3
454 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Nd10.26520 (3)0.27712 (3)0.14686 (3)0.02555 (12)
O40.2306 (5)−0.1369 (4)−0.0511 (5)0.0486 (12)
O50.2203 (5)0.0542 (4)0.0456 (4)0.0400 (11)
O60.3131 (5)0.1959 (4)−0.0621 (4)0.0349 (10)
O70.6565 (7)0.1207 (7)−0.2689 (7)0.090 (2)
O80.5206 (5)0.6553 (4)0.2061 (5)0.0490 (13)
O90.3726 (4)0.4550 (4)0.1277 (4)0.0370 (10)
O100.5209 (4)0.3057 (4)0.1378 (4)0.0334 (9)
O110.9276 (5)0.3690 (5)0.0047 (5)0.0535 (14)
O1W0.0466 (5)0.1916 (4)0.0068 (4)0.0442 (11)
H1W1−0.03050.15570.02120.066*
H1W20.03890.25260.00130.066*
O2W−0.0203 (12)0.1690 (10)−0.2139 (10)0.156 (4)
O3W0.212 (2)0.192 (2)−0.3809 (18)0.149 (5)0.50
O4W0.483 (2)0.789 (2)0.4468 (18)0.155 (5)0.50
O3'0.144 (2)−0.0260 (19)−0.5588 (18)0.149 (5)0.50
O4'0.418 (2)0.918 (2)0.4944 (18)0.155 (5)0.50
N30.5421 (7)−0.0189 (6)−0.2106 (6)0.0512 (16)
H3N0.5912−0.0654−0.24330.061*
N40.4768 (6)0.1499 (5)−0.1699 (5)0.0415 (13)
H4N0.48300.2124−0.17970.050*
N50.8306 (5)0.5190 (5)0.0582 (5)0.0373 (13)
H5N0.89860.56470.04160.045*
N60.7237 (5)0.3425 (5)0.0743 (5)0.0325 (11)
H6N0.72510.27360.06890.039*
N70.0616 (5)0.2175 (5)0.2535 (5)0.0359 (12)
N80.1220 (6)0.4365 (5)0.2479 (5)0.0404 (13)
C60.2655 (6)−0.0264 (6)−0.0300 (5)0.0302 (13)
C70.3654 (6)0.0150 (5)−0.0962 (5)0.0282 (12)
C80.3800 (6)0.1251 (5)−0.1048 (5)0.0291 (12)
C90.5642 (8)0.0857 (8)−0.2206 (7)0.053 (2)
C100.4462 (7)−0.0521 (6)−0.1512 (6)0.0386 (15)
H100.4356−0.1249−0.14820.046*
C110.4953 (7)0.5402 (6)0.1568 (5)0.0319 (13)
C120.6137 (6)0.4941 (5)0.1250 (5)0.0300 (13)
C130.6123 (6)0.3775 (5)0.1135 (5)0.0279 (12)
C140.8335 (6)0.4081 (6)0.0429 (6)0.0379 (15)
C150.7258 (6)0.5607 (6)0.0983 (5)0.0338 (14)
H150.73030.63830.10810.041*
C160.0321 (8)0.1146 (7)0.2595 (6)0.0479 (17)
H160.08520.06400.22600.057*
C17−0.0746 (8)0.0765 (8)0.3131 (7)0.058 (2)
H17−0.09150.00240.31540.069*
C18−0.1540 (8)0.1494 (9)0.3626 (7)0.061 (2)
H18−0.22550.12510.39890.073*
C19−0.1288 (7)0.2575 (8)0.3586 (6)0.0489 (18)
C20−0.0184 (6)0.2911 (7)0.3026 (5)0.0382 (15)
C21−0.2097 (8)0.3371 (10)0.4055 (7)0.067 (3)
H21−0.28340.31490.44100.080*
C22−0.1824 (8)0.4419 (9)0.3998 (7)0.062 (2)
H22−0.23820.49060.42990.074*
C23−0.0688 (8)0.4805 (8)0.3481 (6)0.0499 (18)
C240.0120 (7)0.4047 (6)0.2980 (5)0.0376 (15)
C25−0.0328 (9)0.5927 (8)0.3471 (7)0.059 (2)
H25−0.08490.64470.37890.071*
C260.0792 (9)0.6270 (8)0.2994 (7)0.059 (2)
H260.10580.70360.30050.071*
C270.1537 (8)0.5466 (7)0.2491 (7)0.0483 (18)
H270.22840.57000.21490.058*
O10.3919 (11)0.1911 (9)0.4221 (9)0.059 (3)0.50
O20.3542 (4)0.2234 (4)0.2860 (4)0.0383 (10)
O30.3932 (12)0.4700 (9)0.3390 (8)0.042 (3)0.50
C10.3988 (6)0.2642 (7)0.3854 (7)0.034 (3)0.50
C20.4626 (9)0.4027 (5)0.4640 (6)0.021 (3)0.50
C30.4558 (9)0.4923 (6)0.4366 (5)0.032 (3)0.50
N20.5211 (9)0.6211 (6)0.5170 (6)0.028 (3)0.50
H2N0.51690.67660.50010.034*0.50
C40.5931 (8)0.6601 (5)0.6250 (6)0.033 (3)0.50
N10.5999 (9)0.5705 (8)0.6524 (5)0.033 (3)0.50
C50.5346 (9)0.4417 (7)0.5719 (7)0.040 (3)0.50
H50.53910.38170.59030.048*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Nd10.02497 (18)0.02326 (18)0.03442 (19)0.01369 (13)0.01123 (12)0.01601 (14)
O40.057 (3)0.030 (2)0.071 (3)0.022 (2)0.022 (3)0.030 (3)
O50.051 (3)0.025 (2)0.047 (3)0.015 (2)0.021 (2)0.019 (2)
O60.048 (3)0.033 (2)0.041 (2)0.027 (2)0.019 (2)0.023 (2)
O70.103 (5)0.095 (5)0.133 (6)0.066 (4)0.085 (5)0.084 (5)
O80.059 (3)0.028 (2)0.074 (3)0.024 (2)0.031 (3)0.031 (2)
O90.038 (2)0.035 (2)0.057 (3)0.026 (2)0.021 (2)0.030 (2)
O100.030 (2)0.032 (2)0.052 (3)0.0154 (18)0.0149 (19)0.029 (2)
O110.038 (3)0.046 (3)0.100 (4)0.025 (2)0.036 (3)0.048 (3)
O1W0.035 (2)0.046 (3)0.058 (3)0.021 (2)0.011 (2)0.026 (2)
O2W0.174 (8)0.147 (7)0.156 (7)0.074 (6)0.026 (6)0.075 (6)
O3W0.195 (10)0.126 (8)0.143 (8)0.064 (7)0.005 (7)0.077 (7)
O4W0.177 (10)0.163 (9)0.127 (8)0.035 (7)0.036 (7)0.092 (7)
O3'0.195 (10)0.126 (8)0.143 (8)0.064 (7)0.005 (7)0.077 (7)
O4'0.177 (10)0.163 (9)0.127 (8)0.035 (7)0.036 (7)0.092 (7)
N30.063 (4)0.052 (4)0.070 (4)0.042 (3)0.036 (3)0.041 (3)
N40.051 (3)0.037 (3)0.057 (4)0.025 (3)0.027 (3)0.034 (3)
N50.029 (3)0.035 (3)0.064 (4)0.012 (2)0.016 (3)0.036 (3)
N60.028 (3)0.027 (3)0.053 (3)0.011 (2)0.012 (2)0.027 (3)
N70.033 (3)0.040 (3)0.040 (3)0.016 (2)0.010 (2)0.023 (3)
N80.038 (3)0.044 (3)0.045 (3)0.025 (3)0.015 (3)0.021 (3)
C60.029 (3)0.028 (3)0.037 (3)0.012 (2)0.005 (2)0.018 (3)
C70.030 (3)0.024 (3)0.031 (3)0.013 (2)0.003 (2)0.013 (3)
C80.031 (3)0.023 (3)0.032 (3)0.011 (2)0.007 (2)0.013 (3)
C90.057 (5)0.060 (5)0.067 (5)0.037 (4)0.037 (4)0.040 (4)
C100.046 (4)0.035 (3)0.046 (4)0.021 (3)0.012 (3)0.024 (3)
C110.041 (4)0.033 (3)0.038 (3)0.020 (3)0.016 (3)0.026 (3)
C120.033 (3)0.027 (3)0.036 (3)0.012 (3)0.009 (3)0.019 (3)
C130.023 (3)0.027 (3)0.035 (3)0.009 (2)0.005 (2)0.017 (3)
C140.027 (3)0.034 (3)0.061 (4)0.012 (3)0.011 (3)0.030 (3)
C150.037 (3)0.023 (3)0.045 (4)0.010 (3)0.006 (3)0.020 (3)
C160.043 (4)0.049 (4)0.053 (4)0.017 (3)0.014 (3)0.027 (4)
C170.050 (5)0.060 (5)0.063 (5)0.010 (4)0.014 (4)0.038 (4)
C180.043 (4)0.077 (6)0.057 (5)0.013 (4)0.018 (4)0.036 (5)
C190.036 (4)0.064 (5)0.035 (4)0.014 (4)0.011 (3)0.019 (4)
C200.028 (3)0.054 (4)0.030 (3)0.020 (3)0.010 (3)0.016 (3)
C210.041 (4)0.104 (8)0.054 (5)0.037 (5)0.031 (4)0.032 (5)
C220.048 (5)0.086 (7)0.061 (5)0.044 (5)0.026 (4)0.031 (5)
C230.047 (4)0.058 (5)0.041 (4)0.031 (4)0.009 (3)0.015 (4)
C240.035 (3)0.047 (4)0.032 (3)0.027 (3)0.010 (3)0.014 (3)
C250.063 (5)0.063 (5)0.051 (5)0.047 (4)0.016 (4)0.014 (4)
C260.065 (5)0.050 (5)0.070 (5)0.039 (4)0.014 (4)0.025 (4)
C270.053 (4)0.040 (4)0.064 (5)0.030 (4)0.022 (4)0.027 (4)
O10.076 (6)0.042 (5)0.057 (6)0.020 (5)0.013 (5)0.025 (4)
O20.036 (2)0.028 (2)0.048 (3)0.0158 (19)0.010 (2)0.015 (2)
O30.050 (6)0.027 (5)0.046 (5)0.017 (4)0.006 (4)0.015 (4)
C10.040 (6)0.024 (5)0.046 (6)0.014 (5)0.011 (5)0.022 (5)
C20.028 (5)0.023 (5)0.029 (6)0.017 (4)0.009 (4)0.022 (5)
C30.030 (6)0.033 (6)0.029 (6)0.014 (5)0.014 (4)0.011 (5)
N20.040 (5)0.027 (5)0.030 (5)0.021 (4)0.002 (4)0.018 (4)
C40.024 (5)0.038 (6)0.035 (6)0.017 (5)0.012 (4)0.014 (5)
N10.039 (6)0.029 (6)0.034 (6)0.021 (5)0.004 (4)0.013 (5)
C50.041 (6)0.043 (7)0.037 (6)0.019 (5)0.016 (5)0.018 (5)
Geometric parameters (Å, °) top
Nd1—O22.526 (4)C10—H100.93
Nd1—O32.502 (9)C11—C121.485 (8)
Nd1—O52.392 (4)C12—C151.355 (8)
Nd1—O62.575 (4)C12—C131.431 (8)
Nd1—O92.341 (4)C15—H150.93
Nd1—O102.526 (4)C16—C171.391 (10)
Nd1—O1W2.475 (4)C16—H160.93
Nd1—N1i2.478 (6)C17—C181.366 (11)
Nd1—N72.638 (5)C17—H170.93
Nd1—N82.725 (5)C18—C191.361 (11)
O4—C61.234 (7)C18—H180.93
O5—C61.268 (7)C19—C201.419 (9)
O6—C81.233 (7)C19—C211.431 (11)
O7—C91.229 (8)C20—C241.427 (9)
O8—C111.232 (7)C21—C221.330 (12)
O9—C111.279 (7)C21—H210.93
O10—C131.252 (7)C22—C231.424 (11)
O11—C141.222 (7)C22—H220.93
O1W—H1W10.85C23—C251.381 (11)
O1W—H1W20.85C23—C241.402 (9)
N3—C101.351 (8)C25—C261.361 (12)
N3—C91.366 (9)C25—H250.93
N3—H3N0.86C26—C271.391 (9)
N4—C91.367 (8)C26—H260.93
N4—C81.378 (7)C27—H270.93
N4—H4N0.86O1—C11.238 (8)
N5—C151.345 (8)O2—C11.191 (8)
N5—C141.354 (7)O3—C31.307 (8)
N5—H5N0.86C1—C21.473 (8)
N6—C131.368 (7)C2—C31.39
N6—C141.371 (7)C2—C51.39
N6—H6N0.86C3—N21.39
N7—C161.305 (9)N2—C41.39
N7—C201.375 (8)N2—H2N0.86
N8—C271.343 (9)C4—N11.39
N8—C241.358 (8)N1—C51.39
C6—C71.487 (8)N1—Nd1i2.478 (6)
C7—C101.346 (8)C5—H50.93
C7—C81.438 (8)
O2—Nd1—O367.5 (2)O7—C9—N4122.9 (7)
O2—Nd1—O571.6 (1)N3—C9—N4114.1 (6)
O2—Nd1—O6123.5 (1)C7—C10—N3123.2 (6)
O2—Nd1—O9127.7 (1)C7—C10—H10118.4
O2—Nd1—O1071.8 (1)N3—C10—H10118.4
O2—Nd1—O1W136.6 (2)O8—C11—O9124.9 (6)
O2—Nd1—N770.6 (2)O8—C11—C12118.8 (6)
O2—Nd1—N8111.7 (2)O9—C11—C12116.3 (5)
O3—Nd1—O5138.7 (2)C15—C12—C13117.4 (5)
O3—Nd1—O6133.6 (3)C15—C12—C11119.2 (5)
O3—Nd1—O968.6 (3)C13—C12—C11123.3 (5)
O3—Nd1—O1076.5 (3)O10—C13—N6116.8 (5)
O3—Nd1—O1W138.2 (3)O10—C13—C12126.6 (5)
O3—Nd1—N787.9 (3)N6—C13—C12116.6 (5)
O3—Nd1—N865.6 (3)O11—C14—N5122.8 (6)
O5—Nd1—O667.9 (1)O11—C14—N6122.0 (6)
O5—Nd1—O9139.7 (2)N5—C14—N6115.2 (5)
O5—Nd1—O1085.9 (1)N5—C15—C12122.7 (5)
O5—Nd1—O1W78.2 (2)N5—C15—H15118.7
O5—Nd1—N783.8 (2)C12—C15—H15118.7
O5—Nd1—N8138.8 (2)N7—C16—C17123.6 (7)
O6—Nd1—O972.6 (1)N7—C16—H16118.2
O6—Nd1—O1067.7 (1)C17—C16—H16118.2
O6—Nd1—O1W69.0 (1)C18—C17—C16119.1 (8)
O6—Nd1—N7138.2 (2)C18—C17—H17120.5
O6—Nd1—N8124.8 (2)C16—C17—H17120.5
O9—Nd1—O1071.5 (1)C19—C18—C17120.1 (7)
O9—Nd1—O1W95.5 (2)C19—C18—H18120.0
O9—Nd1—N7133.8 (2)C17—C18—H18120.0
O9—Nd1—N872.8 (2)C18—C19—C20118.1 (7)
O10—Nd1—O1W136.7 (2)C18—C19—C21123.4 (7)
O10—Nd1—N7142.5 (2)C20—C19—C21118.5 (8)
O10—Nd1—N8135.1 (2)N7—C20—C19121.5 (7)
O1W—Nd1—N775.78 (16)N7—C20—C24119.0 (6)
O1W—Nd1—N872.93 (16)C19—C20—C24119.5 (6)
N7—Nd1—N861.14 (16)C22—C21—C19121.9 (7)
O9—Nd1—N1i80.8 (3)C22—C21—H21119.1
O5—Nd1—N1i124.7 (3)C19—C21—H21119.1
O1W—Nd1—N1i147.5 (3)C21—C22—C23120.8 (7)
N1i—Nd1—O314.1 (3)C21—C22—H22119.6
N1i—Nd1—O1073.0 (3)C23—C22—H22119.6
N1i—Nd1—O253.4 (2)C25—C23—C24118.0 (7)
N1i—Nd1—O6137.7 (4)C25—C23—C22122.0 (7)
N1i—Nd1—N783.6 (4)C24—C23—C22119.9 (8)
N1i—Nd1—N875.1 (3)N8—C24—C23122.7 (7)
C6—O5—Nd1140.6 (4)N8—C24—C20117.9 (5)
C8—O6—Nd1123.2 (4)C23—C24—C20119.4 (6)
C11—O9—Nd1137.2 (4)C26—C25—C23119.8 (7)
C13—O10—Nd1130.2 (4)C26—C25—H25120.1
Nd1—O1W—H1W1117.9C23—C25—H25120.1
Nd1—O1W—H1W2107.8C25—C26—C27119.5 (8)
H1W1—O1W—H1W2107.7C25—C26—H26120.2
C10—N3—C9122.5 (6)C27—C26—H26120.2
C10—N3—H3N118.7N8—C27—C26122.6 (7)
C9—N3—H3N118.7N8—C27—H27118.7
C9—N4—C8126.9 (6)C26—C27—H27118.7
C9—N4—H4N116.5C1—O2—Nd1143.9 (5)
C8—N4—H4N116.5C3—O3—Nd1135.9 (6)
C15—N5—C14122.6 (5)O2—C1—O1120.4 (8)
C15—N5—H5N118.7O2—C1—C2119.1 (7)
C14—N5—H5N118.7O1—C1—C2120.5 (8)
C13—N6—C14125.4 (5)C3—C2—C5120.0
C13—N6—H6N117.3C3—C2—C1124.7 (6)
C14—N6—H6N117.3C5—C2—C1115.3 (6)
C16—N7—C20117.7 (6)O3—C3—N2113.1 (6)
C16—N7—Nd1120.3 (4)O3—C3—C2126.9 (6)
C20—N7—Nd1121.9 (4)N2—C3—C2120.0
C27—N8—C24117.3 (6)C4—N2—C3120.0
C27—N8—Nd1122.7 (4)C4—N2—H2N120.0
C24—N8—Nd1119.9 (4)C3—N2—H2N120.0
O4—C6—O5123.3 (6)N2—C4—N1120.0
O4—C6—C7118.8 (5)N2—C4—Nd1i175.4 (3)
O5—C6—C7117.9 (5)N1—C4—Nd1i55.6 (3)
C10—C7—C8117.7 (6)C5—N1—C4120.0
C10—C7—C6119.6 (5)C5—N1—Nd1i143.1 (4)
C8—C7—C6122.7 (5)C4—N1—Nd1i96.8 (4)
O6—C8—N4118.1 (5)N1—C5—C2120.0
O6—C8—C7126.6 (5)N1—C5—H5120.0
N4—C8—C7115.3 (5)C2—C5—H5120.0
O7—C9—N3123.0 (7)
O9—Nd1—O5—C621.5 (8)C9—N3—C10—C7−0.6 (11)
O1W—Nd1—O5—C6106.0 (7)Nd1—O9—C11—O8−131.1 (6)
N1i—Nd1—O5—C6−99.5 (8)Nd1—O9—C11—C1250.7 (8)
O3—Nd1—O5—C6−97.6 (8)O8—C11—C12—C15−30.9 (9)
O10—Nd1—O5—C6−33.4 (6)O9—C11—C12—C15147.5 (6)
O2—Nd1—O5—C6−105.6 (7)O8—C11—C12—C13153.3 (6)
O6—Nd1—O5—C634.1 (6)O9—C11—C12—C13−28.4 (9)
N7—Nd1—O5—C6−177.3 (7)Nd1—O10—C13—N6−156.8 (4)
N8—Nd1—O5—C6152.1 (6)Nd1—O10—C13—C1224.7 (9)
C4i—Nd1—O5—C6−104.4 (7)C14—N6—C13—O10179.7 (6)
O9—Nd1—O6—C8125.4 (5)C14—N6—C13—C12−1.7 (9)
O5—Nd1—O6—C8−46.1 (4)C15—C12—C13—O10177.3 (6)
O1W—Nd1—O6—C8−131.5 (5)C11—C12—C13—O10−6.8 (10)
N1i—Nd1—O6—C871.6 (6)C15—C12—C13—N6−1.2 (8)
O3—Nd1—O6—C890.9 (5)C11—C12—C13—N6174.7 (5)
O10—Nd1—O6—C848.7 (4)C15—N5—C14—O11178.8 (7)
O2—Nd1—O6—C81.2 (5)C15—N5—C14—N6−1.8 (10)
N7—Nd1—O6—C8−97.0 (5)C13—N6—C14—O11−177.5 (6)
N8—Nd1—O6—C8179.0 (4)C13—N6—C14—N53.1 (10)
C4i—Nd1—O6—C830.3 (6)C14—N5—C15—C12−1.0 (10)
O5—Nd1—O9—C11−89.4 (6)C13—C12—C15—N52.5 (9)
O1W—Nd1—O9—C11−167.6 (6)C11—C12—C15—N5−173.6 (6)
N1i—Nd1—O9—C1145.0 (6)C20—N7—C16—C17−0.5 (10)
O3—Nd1—O9—C1152.3 (6)Nd1—N7—C16—C17−179.3 (6)
O10—Nd1—O9—C11−30.0 (6)N7—C16—C17—C180.2 (12)
O2—Nd1—O9—C1117.6 (6)C16—C17—C18—C190.2 (12)
O6—Nd1—O9—C11−101.6 (6)C17—C18—C19—C20−0.2 (11)
N7—Nd1—O9—C11116.9 (6)C17—C18—C19—C21178.3 (8)
N8—Nd1—O9—C11122.2 (6)C16—N7—C20—C190.5 (9)
C4i—Nd1—O9—C1133.9 (6)Nd1—N7—C20—C19179.3 (5)
O9—Nd1—O10—C13−10.0 (5)C16—N7—C20—C24179.6 (6)
O5—Nd1—O10—C13136.0 (5)Nd1—N7—C20—C24−1.6 (8)
O1W—Nd1—O10—C1368.0 (6)C18—C19—C20—N7−0.1 (10)
N1i—Nd1—O10—C13−95.8 (6)C21—C19—C20—N7−178.7 (6)
O3—Nd1—O10—C13−81.7 (5)C18—C19—C20—C24−179.3 (7)
O2—Nd1—O10—C13−152.0 (5)C21—C19—C20—C242.2 (10)
O6—Nd1—O10—C1368.3 (5)C18—C19—C21—C22−179.8 (8)
N7—Nd1—O10—C13−149.7 (5)C20—C19—C21—C22−1.3 (12)
N8—Nd1—O10—C13−49.2 (6)C19—C21—C22—C23−1.2 (13)
C4i—Nd1—O10—C13−124.7 (5)C21—C22—C23—C25−176.1 (8)
O9—Nd1—N7—C16−173.0 (5)C21—C22—C23—C242.8 (12)
O5—Nd1—N7—C1623.8 (5)C27—N8—C24—C231.0 (10)
O1W—Nd1—N7—C16103.2 (5)Nd1—N8—C24—C23−177.9 (5)
N1i—Nd1—N7—C16−102.2 (6)C27—N8—C24—C20−176.9 (6)
O3—Nd1—N7—C16−115.7 (5)Nd1—N8—C24—C204.2 (8)
O10—Nd1—N7—C16−51.2 (6)C25—C23—C24—N8−0.8 (10)
O2—Nd1—N7—C16−48.8 (5)C22—C23—C24—N8−179.7 (7)
O6—Nd1—N7—C1670.1 (6)C25—C23—C24—C20177.1 (7)
N8—Nd1—N7—C16−178.7 (6)C22—C23—C24—C20−1.8 (10)
C4i—Nd1—N7—C16−75.8 (5)N7—C20—C24—N8−1.8 (9)
O9—Nd1—N7—C208.2 (6)C19—C20—C24—N8177.3 (6)
O5—Nd1—N7—C20−155.0 (5)N7—C20—C24—C23−179.8 (6)
O1W—Nd1—N7—C20−75.6 (5)C19—C20—C24—C23−0.6 (9)
N1i—Nd1—N7—C2079.0 (5)C24—C23—C25—C26−0.7 (11)
O3—Nd1—N7—C2065.6 (5)C22—C23—C25—C26178.2 (8)
O10—Nd1—N7—C20130.0 (4)C23—C25—C26—C271.9 (12)
O2—Nd1—N7—C20132.4 (5)C24—N8—C27—C260.3 (11)
O6—Nd1—N7—C20−108.7 (5)Nd1—N8—C27—C26179.2 (6)
N8—Nd1—N7—C202.5 (4)C25—C26—C27—N8−1.8 (12)
C4i—Nd1—N7—C20105.4 (5)O9—Nd1—O2—C150.4 (6)
O9—Nd1—N8—C272.1 (5)O5—Nd1—O2—C1−170.3 (6)
O5—Nd1—N8—C27−147.0 (5)O1W—Nd1—O2—C1−122.0 (6)
O1W—Nd1—N8—C27−99.4 (6)N1i—Nd1—O2—C116.0 (8)
N1i—Nd1—N8—C2786.9 (6)O3—Nd1—O2—C115.5 (6)
O3—Nd1—N8—C2775.9 (6)O10—Nd1—O2—C198.0 (6)
O10—Nd1—N8—C2740.9 (6)O6—Nd1—O2—C1143.8 (6)
O2—Nd1—N8—C27126.6 (5)N7—Nd1—O2—C1−80.5 (6)
O6—Nd1—N8—C27−51.4 (6)N8—Nd1—O2—C1−34.2 (6)
N7—Nd1—N8—C27177.7 (6)C4i—Nd1—O2—C112.6 (9)
C4i—Nd1—N8—C27108.0 (6)O9—Nd1—O3—C3−151.4 (14)
O9—Nd1—N8—C24−179.1 (5)O5—Nd1—O3—C3−8.8 (16)
O5—Nd1—N8—C2431.9 (6)O1W—Nd1—O3—C3135.1 (11)
O1W—Nd1—N8—C2479.4 (5)N1i—Nd1—O3—C3−2(2)
N1i—Nd1—N8—C24−94.3 (6)O10—Nd1—O3—C3−76.2 (13)
O3—Nd1—N8—C24−105.3 (5)O2—Nd1—O3—C3−0.5 (12)
O10—Nd1—N8—C24−140.3 (4)O6—Nd1—O3—C3−116.0 (12)
O2—Nd1—N8—C24−54.6 (5)N7—Nd1—O3—C369.4 (13)
O6—Nd1—N8—C24127.4 (4)N8—Nd1—O3—C3128.4 (14)
N7—Nd1—N8—C24−3.4 (4)C4i—Nd1—O3—C31.4 (13)
C4i—Nd1—N8—C24−73.2 (5)Nd1—O2—C1—O1158.2 (7)
Nd1—O5—C6—O4168.0 (5)Nd1—O2—C1—C2−21.9 (7)
Nd1—O5—C6—C7−12.1 (9)O2—C1—C2—C310.7 (6)
O4—C6—C7—C10−19.2 (9)O1—C1—C2—C3−169.4 (6)
O5—C6—C7—C10160.9 (6)O2—C1—C2—C5−168.7 (5)
O4—C6—C7—C8160.7 (6)O1—C1—C2—C511.2 (5)
O5—C6—C7—C8−19.2 (8)Nd1—O3—C3—N2175.8 (8)
Nd1—O6—C8—N4−137.4 (5)Nd1—O3—C3—C2−3.7 (18)
Nd1—O6—C8—C744.3 (8)C5—C2—C3—O3179.5 (12)
C9—N4—C8—O6177.5 (7)C1—C2—C3—O30.1 (11)
C9—N4—C8—C7−4.0 (10)C5—C2—C3—N20.0
C10—C7—C8—O6178.5 (6)C1—C2—C3—N2−179.4 (6)
C6—C7—C8—O6−1.3 (9)O3—C3—N2—C4−179.6 (11)
C10—C7—C8—N40.2 (8)C2—C3—N2—C40.0
C6—C7—C8—N4−179.7 (5)C3—N2—C4—N10.0
C10—N3—C9—O7175.9 (8)N2—C4—N1—C50.0
C10—N3—C9—N4−2.7 (11)N2—C4—N1—Nd1i−178.2 (5)
C8—N4—C9—O7−173.4 (8)C4—N1—C5—C20.0
C8—N4—C9—N35.2 (11)Nd1i—N1—C5—C2177.1 (8)
C8—C7—C10—N31.9 (10)C3—C2—C5—N10.0
C6—C7—C10—N3−178.2 (6)C1—C2—C5—N1179.4 (6)
Symmetry codes: (i) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3N···O1ii0.862.192.877 (13)136
N3—H3N···O2ii0.862.102.883 (7)152
N4—H4N···O8iii0.861.912.768 (7)175
N5—H5N···O11iv0.861.952.786 (7)164
N6—H6N···O4ii0.861.862.709 (6)167
O1W—H1W1···O4v0.852.042.822 (7)153
O1W—H1W2···O11vi0.852.142.921 (6)153
Symmetry codes: (ii) −x+1, −y, −z; (iii) −x+1, −y+1, −z; (iv) −x+2, −y+1, −z; (v) −x, −y, −z; (vi) x−1, y, z.
Table 1
Selected geometric parameters (Å, °) top
Nd1—O22.526 (4)Nd1—O102.526 (4)
Nd1—O32.502 (9)Nd1—O1W2.475 (4)
Nd1—O52.392 (4)Nd1—N72.638 (5)
Nd1—O62.575 (4)Nd1—N82.725 (5)
Nd1—O92.341 (4)
O2—Nd1—O367.5 (2)O5—Nd1—O1W78.2 (2)
O2—Nd1—O571.6 (1)O5—Nd1—N783.8 (2)
O2—Nd1—O6123.5 (1)O5—Nd1—N8138.8 (2)
O2—Nd1—O9127.7 (1)O6—Nd1—O972.6 (1)
O2—Nd1—O1071.8 (1)O6—Nd1—O1067.7 (1)
O2—Nd1—O1W136.6 (2)O6—Nd1—O1W69.0 (1)
O2—Nd1—N770.6 (2)O6—Nd1—N7138.2 (2)
O2—Nd1—N8111.7 (2)O6—Nd1—N8124.8 (2)
O3—Nd1—O5138.7 (2)O9—Nd1—O1071.5 (1)
O3—Nd1—O6133.6 (3)O9—Nd1—O1W95.5 (2)
O3—Nd1—O968.6 (3)O9—Nd1—N7133.8 (2)
O3—Nd1—O1076.5 (3)O9—Nd1—N872.8 (2)
O3—Nd1—O1W138.2 (3)O10—Nd1—O1W136.7 (2)
O3—Nd1—N787.9 (3)O10—Nd1—N7142.5 (2)
O3—Nd1—N865.6 (3)O10—Nd1—N8135.1 (2)
O5—Nd1—O667.9 (1)O1W—Nd1—N775.78 (16)
O5—Nd1—O9139.7 (2)O1W—Nd1—N872.93 (16)
O5—Nd1—O1085.9 (1)N7—Nd1—N861.14 (16)
Acknowledgements top

The authors thank the Scientifc Research Foundation of Guangxi Normal University, the Science Foundation of Guangxi (Grant No. 0542021) and the University of Malaya for supporting this study.

references
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