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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): m419–m420.
Published online 2008 January 25. doi:  10.1107/S1600536808001499
PMCID: PMC2960306

(μ-6-Oxido-4-oxo-1,2-dihydro­pyrimidine-5-carboxyl­ato-κ4 O 5,O 6:O 2,N 3)bis­[aquabis­(4-oxido-2-oxo-1,2-dihydro­pyrimidin-3-ium-5-carboxyl­ato-κ2 O 4,O 5)­(1,10-phenanthroline-κ2 N,N′)neodymium(III)] hexa­hydrate

Abstract

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.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-64-0m419-scheme1.jpg

Experimental

Crystal data

  • [Nd2(C5H2N2O4)(C5H3N2O4)4(C12H8N2)2(H2O)2]·6H2O
  • M r = 1567.48
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m419-efi1.jpg
  • a = 10.1980 (7) Å
  • b = 12.8896 (9) Å
  • c = 13.3383 (9) Å
  • α = 118.711 (1)°
  • β = 90.010 (1)°
  • γ = 108.612 (1)°
  • V = 1432.25 (17) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 1.90 mm−1
  • T = 295 (2) K
  • 0.10 × 0.04 × 0.02 mm

Data collection

  • Bruker APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.724, T max = 0.963
  • 12405 measured reflections
  • 6377 independent reflections
  • 5349 reflections with I > 2σ(I)
  • R int = 0.039

Refinement

  • R[F 2 > 2σ(F 2)] = 0.054
  • wR(F 2) = 0.136
  • S = 1.04
  • 6377 reflections
  • 454 parameters
  • 84 restraints
  • H-atom parameters constrained
  • Δρmax = 1.23 e Å−3
  • Δρmin = −0.90 e Å−3

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

Table 1
Selected geometric parameters (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808001499/ci2552sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808001499/ci2552Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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.

supplementary crystallographic information

Comment

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.

Experimental

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

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.

Figures

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 ...
Fig. 2.
Geometry of Nd.

Crystal data

[Nd2(C5H2N2O4)(C5H3N2O4)4(C12H8N2)2(H2O)2]·6H2OZ = 1
Mr = 1567.48F000 = 782
Triclinic, P1Dx = 1.817 Mg m3
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 mm1
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

Bruker APEXII diffractometer6377 independent reflections
Radiation source: fine-focus sealed tube5349 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.039
T = 295(2) Kθmax = 27.5º
[var phi] 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

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 Å3
454 parametersΔρmin = −0.90 e Å3
84 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2552).

References

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  • Bruker (2006). APEX2 and SAINT Bruker AXS Inc., Madison, Winconsin, USA.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Sun, C.-Y. & Jin, L. P. (2004). Polyhedron, 23, 2085–2093.
  • Westrip, S. P. (2008). publCIF In preparation.
  • Xing, H.-H., Chen, Z.-L. & Ng, S. W. (2008). Acta Cryst. E64, m418. [PMC free article] [PubMed]

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