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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): m1469–m1470.
Published online 2010 October 30. doi:  10.1107/S1600536810042583
PMCID: PMC3009246

Bis(2,6-dihy­droxy­benzoato-κ2 O 1,O 1′)(nitrato-κ2 O,O′)bis­(1,10-phenanthroline-κ2 N,N′)neodymium(III)

Abstract

In the mononuclear title complex, [Nd(C7H5O4)2(NO3)(C12H8N2)2], the NdIII atom is in a distorted bicapped square-anti­prismatic geometry formed by four N atoms from two chelating 1,10-phenanthroline (phen) ligands, four O atoms from two 2,6-dihy­droxy­benzoate (DHB) ligands and two O atoms from a nitrate anion. π–π stacking inter­actions between the phen and DHB ligands of adjacent complexes [centroid–centroid distances = 3.520 (6) and 3.798 (6) Å] stabilize the crystal structure. Intra­molecular O—H(...)O hydrogen bonds are observed in the DHB ligands.

Related literature

For applications of rare earth complexes, see: de Sa et al. (2000 [triangle]). For related structures, see: Ma et al. (2010 [triangle]); Yang et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1469-scheme1.jpg

Experimental

Crystal data

  • [Nd(C7H5O4)2(NO3)(C12H8N2)2]
  • M r = 872.89
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1469-efi1.jpg
  • a = 11.2359 (2) Å
  • b = 26.7878 (5) Å
  • c = 14.3710 (4) Å
  • β = 127.790 (2)°
  • V = 3418.24 (16) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.59 mm−1
  • T = 298 K
  • 0.28 × 0.21 × 0.15 mm

Data collection

  • Oxford Diffraction Gemini S Ultra CCD diffractometer
  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006 [triangle]) T min = 0.664, T max = 0.796
  • 18058 measured reflections
  • 6139 independent reflections
  • 4859 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.023
  • wR(F 2) = 0.049
  • S = 0.95
  • 6139 reflections
  • 496 parameters
  • H-atom parameters constrained
  • Δρmax = 0.38 e Å−3
  • Δρmin = −0.37 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2006 [triangle]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]) and DIAMOND (Brandenburg & Berndt, 1999 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810042583/hy2364sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042583/hy2364Isup2.hkl

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

Acknowledgments

The authors are grateful for financial support from the Natural Science Foundation of Zhejiang Province (project No. 2010 Y4100495).

supplementary crystallographic information

Comment

Luminescent materials based on lanthanide complexes have been extensively studied owing to their unique structures and potential applications as luminescent polymer films, active optical fibers for data transmission and light-emitting devices (Ma et al., 2010; Sa et al., 2000; Yang et al., 2008). Herein, the title compound is synthesized and its crystal structure is reported.

The mononuclear structure of the title compound is shown in Fig. 1. The ten-coordinated geometry of the NdIII ion is completed by four 2,6-dihydroxybenzoate (DHB) O atoms, four phenanthroline N atoms and two nitrate O atoms. The complex forms a ten-coordinated distorted bicapped square antiprismatic structure (Fig. 2), in which the set of O6, O10, N4 and N1 and the set of O1, O5, N2 and N3 form two approximate square planes, respectively. The ninth coordinate atom O2 and tenth coordinate atom O9 are located above and under the two planes at the bicapped positions. The O2—Nd1–O9 bond angle is 175.69 (6)° close to 180°, which indicates the O2, Nd1 and O9 lying almost on a line and being regarded as an axis. Because the coordinate O2 and O9 atoms are excluded by O6, O10, N4 and N1 (formed the above plane) and O1, O5, N2 and N3 (formed the under plane), respectively, the bond distances of Nd1—O2 [2.5991 (16) Å] and Nd1—O9 [2.6060 (17) Å] are consumedly longer than the ones of Nd1—O1 [2.5256 (17) Å] and Nd1—O10 [2.5573 (17) Å].

In the crystal structure, π–π stacking interactions between the pyridine ring of phen and the benzene ring of DHB link the discrete mononuclear complexes into a two-dimensional layer (Fig. 3). The centroid–centroid distances between the rings are 3.520 (6) and 3.798 (6) Å, which obviously helps to stabilize the structure.

Experimental

All reagents are commercially available and of analytical grade. NdNO3.6H2O (0.219 g, 0.5 mmol), 2,6-dihydroxybenzoic acid (0.074 g, 0.5 mmol),1,10-phenanthroline (0.090 g, 0.5 mmol) and NaHCO3 (0.042 g, 0.5 mmol) were dissolved in water–ethanol solution (10 ml, 1:1). The solution was refluxed for 4 h, and filtered after cooling to room temperature. Orange single crystals were obtained from the filtrate after 2 d.

Refinement

H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 and O—H = 0.82 Å and with Uiso(H) = 1.2(1.5 for hydroxy)Ueq(C,O).

Figures

Fig. 1.
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
Coordination geometry around Nd.
Fig. 3.
Crystal packing of the title compound. Dashed lines denote π–π stacking interactions.

Crystal data

[Nd(C7H5O4)2(NO3)(C12H8N2)2]F(000) = 1748
Mr = 872.89Dx = 1.696 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 11150 reflections
a = 11.2359 (2) Åθ = 2.9–29.1°
b = 26.7878 (5) ŵ = 1.59 mm1
c = 14.3710 (4) ÅT = 298 K
β = 127.790 (2)°Block, orange
V = 3418.24 (16) Å30.28 × 0.21 × 0.15 mm
Z = 4

Data collection

Oxford Diffraction Gemini S Ultra CCD diffractometer6139 independent reflections
Radiation source: Enhance (Mo) X-ray Source4859 reflections with I > 2σ(I)
graphiteRint = 0.023
Detector resolution: 15.9149 pixels mm-1θmax = 25.2°, θmin = 2.9°
ω scansh = −13→13
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)k = −32→31
Tmin = 0.664, Tmax = 0.796l = −17→15
18058 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.023Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.049H-atom parameters constrained
S = 0.95w = 1/[σ2(Fo2) + (0.026P)2] where P = (Fo2 + 2Fc2)/3
6139 reflections(Δ/σ)max = 0.001
496 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = −0.37 e Å3

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

xyzUiso*/Ueq
Nd10.068277 (15)0.638621 (5)0.280312 (12)0.03184 (5)
O10.1545 (2)0.66194 (7)0.48337 (15)0.0445 (5)
O20.1118 (2)0.58179 (7)0.44526 (15)0.0458 (5)
O30.2418 (2)0.69710 (7)0.68349 (17)0.0597 (5)
H310.21820.69790.61700.090*
O40.1664 (3)0.52057 (7)0.60604 (19)0.0828 (8)
H270.15390.52880.54560.124*
O50.3377 (2)0.60803 (7)0.40378 (17)0.0521 (5)
O60.3064 (2)0.68871 (7)0.36811 (16)0.0441 (4)
O70.5201 (2)0.74239 (7)0.39922 (17)0.0535 (5)
H340.43520.73650.37810.080*
O80.5823 (3)0.56507 (8)0.4709 (2)0.0737 (6)
H380.49630.56740.44990.111*
O90.0412 (2)0.69978 (7)0.12734 (16)0.0471 (5)
O100.1513 (2)0.62994 (7)0.15044 (18)0.0525 (5)
O110.1319 (3)0.68609 (10)0.03319 (19)0.0831 (8)
N1−0.1692 (2)0.61789 (8)0.05894 (18)0.0349 (5)
N20.0231 (2)0.54467 (7)0.20773 (19)0.0375 (5)
N3−0.1856 (2)0.63390 (8)0.25221 (18)0.0381 (5)
N4−0.0620 (2)0.72232 (8)0.26242 (18)0.0360 (5)
N50.1082 (3)0.67266 (10)0.1013 (2)0.0478 (6)
C10.1163 (3)0.50855 (10)0.2787 (3)0.0454 (7)
H10.19140.51620.35750.055*
C20.1072 (4)0.45960 (10)0.2408 (3)0.0546 (8)
H20.17490.43550.29380.066*
C30.0000 (4)0.44770 (11)0.1275 (3)0.0511 (8)
H3−0.00640.41530.10140.061*
C4−0.1016 (3)0.48396 (10)0.0488 (3)0.0414 (7)
C5−0.0854 (3)0.53267 (9)0.0931 (2)0.0351 (6)
C6−0.1877 (3)0.57118 (9)0.0147 (2)0.0337 (6)
C7−0.3023 (3)0.55995 (10)−0.1047 (2)0.0404 (7)
C8−0.3149 (4)0.51012 (12)−0.1458 (3)0.0520 (8)
H8−0.39050.5025−0.22450.062*
C9−0.2196 (4)0.47427 (11)−0.0729 (3)0.0501 (8)
H9−0.23040.4422−0.10210.060*
C10−0.3989 (3)0.59882 (12)−0.1773 (2)0.0499 (8)
H10−0.47480.5930−0.25690.060*
C11−0.3823 (3)0.64493 (11)−0.1319 (2)0.0467 (7)
H11−0.44760.6707−0.17900.056*
C12−0.2661 (3)0.65268 (10)−0.0140 (2)0.0420 (7)
H12−0.25510.68450.01630.050*
C13−0.2459 (3)0.59062 (11)0.2495 (2)0.0474 (7)
H13−0.18720.56190.27380.057*
C14−0.3934 (4)0.58626 (13)0.2119 (3)0.0570 (8)
H14−0.43150.55530.21110.068*
C15−0.4805 (4)0.62816 (13)0.1762 (3)0.0583 (9)
H15−0.57940.62570.14960.070*
C16−0.4216 (3)0.67480 (11)0.1796 (2)0.0428 (7)
C17−0.2723 (3)0.67573 (10)0.2186 (2)0.0358 (6)
C18−0.2042 (3)0.72281 (9)0.2286 (2)0.0341 (6)
C19−0.2843 (3)0.76743 (10)0.2050 (2)0.0424 (7)
C20−0.4380 (3)0.76430 (12)0.1606 (2)0.0531 (8)
H20−0.49380.79350.13980.064*
C21−0.5034 (3)0.72081 (13)0.1482 (2)0.0568 (8)
H21−0.60370.72020.11880.068*
C22−0.2088 (4)0.81226 (11)0.2244 (2)0.0485 (7)
H22−0.25710.84250.21220.058*
C23−0.0669 (4)0.81185 (10)0.2605 (2)0.0495 (7)
H23−0.01570.84160.27490.059*
C240.0033 (3)0.76606 (10)0.2764 (2)0.0436 (7)
H240.09990.76620.29770.052*
C250.1535 (3)0.61801 (11)0.5154 (2)0.0372 (6)
C260.2018 (3)0.60945 (10)0.6361 (2)0.0355 (6)
C270.2063 (4)0.56095 (11)0.6757 (3)0.0512 (8)
C280.2554 (4)0.55331 (13)0.7898 (3)0.0643 (9)
H280.26030.52120.81640.077*
C290.2962 (4)0.59309 (13)0.8626 (3)0.0605 (9)
H290.32780.58760.93860.073*
C300.2920 (3)0.64062 (12)0.8275 (3)0.0543 (8)
H300.32130.66710.87940.065*
C310.2439 (3)0.64953 (10)0.7139 (2)0.0406 (7)
C320.3881 (3)0.65023 (11)0.4013 (2)0.0411 (7)
C330.5412 (3)0.65354 (10)0.4341 (2)0.0386 (6)
C340.5980 (3)0.69969 (11)0.4303 (2)0.0418 (7)
C350.7421 (3)0.70261 (13)0.4607 (2)0.0510 (8)
H350.78050.73300.45880.061*
C360.8260 (3)0.65970 (14)0.4937 (2)0.0580 (9)
H360.92220.66180.51450.070*
C370.7746 (3)0.61407 (14)0.4972 (3)0.0584 (8)
H370.83440.58580.51950.070*
C380.6316 (3)0.61079 (12)0.4670 (2)0.0515 (7)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Nd10.03283 (8)0.02688 (8)0.03861 (8)0.00037 (7)0.02331 (7)−0.00004 (7)
O10.0526 (12)0.0346 (11)0.0431 (11)−0.0009 (10)0.0278 (10)0.0030 (10)
O20.0568 (13)0.0393 (11)0.0430 (11)−0.0027 (10)0.0314 (10)−0.0018 (10)
O30.0674 (15)0.0414 (13)0.0479 (12)−0.0016 (11)0.0238 (11)−0.0069 (11)
O40.146 (2)0.0402 (13)0.0605 (14)−0.0189 (15)0.0625 (16)−0.0032 (12)
O50.0407 (12)0.0417 (12)0.0685 (13)0.0049 (10)0.0307 (10)0.0136 (11)
O60.0354 (11)0.0367 (11)0.0588 (12)0.0021 (9)0.0282 (10)−0.0007 (10)
O70.0435 (12)0.0499 (13)0.0683 (14)0.0004 (10)0.0349 (11)0.0067 (11)
O80.0554 (14)0.0518 (14)0.1003 (18)0.0167 (12)0.0408 (14)0.0153 (13)
O90.0530 (12)0.0367 (11)0.0562 (12)0.0017 (10)0.0359 (11)0.0040 (10)
O100.0614 (14)0.0442 (13)0.0665 (13)0.0032 (10)0.0467 (12)−0.0047 (11)
O110.0840 (18)0.128 (2)0.0584 (14)−0.0030 (16)0.0541 (14)0.0151 (15)
N10.0368 (12)0.0315 (12)0.0400 (12)0.0019 (11)0.0253 (11)0.0013 (11)
N20.0473 (14)0.0268 (12)0.0439 (14)0.0031 (11)0.0307 (12)0.0037 (11)
N30.0405 (13)0.0399 (14)0.0403 (12)−0.0058 (11)0.0282 (11)−0.0035 (11)
N40.0402 (13)0.0298 (12)0.0427 (12)−0.0020 (10)0.0278 (11)−0.0025 (10)
N50.0425 (14)0.0634 (18)0.0385 (14)−0.0123 (13)0.0253 (12)−0.0061 (13)
C10.0560 (19)0.0344 (17)0.0525 (18)0.0059 (15)0.0367 (16)0.0062 (14)
C20.075 (2)0.0324 (18)0.077 (2)0.0114 (16)0.057 (2)0.0138 (17)
C30.076 (2)0.0260 (16)0.078 (2)−0.0052 (16)0.061 (2)−0.0055 (16)
C40.0520 (18)0.0300 (16)0.0636 (19)−0.0086 (14)0.0464 (17)−0.0055 (15)
C50.0423 (16)0.0284 (15)0.0494 (17)−0.0044 (13)0.0356 (15)−0.0007 (13)
C60.0356 (15)0.0348 (16)0.0417 (15)−0.0079 (12)0.0293 (13)−0.0049 (13)
C70.0352 (15)0.0464 (18)0.0456 (17)−0.0092 (14)0.0278 (14)−0.0082 (15)
C80.0499 (19)0.055 (2)0.0563 (19)−0.0194 (17)0.0352 (17)−0.0196 (17)
C90.062 (2)0.0365 (17)0.072 (2)−0.0207 (16)0.0507 (19)−0.0218 (17)
C100.0322 (16)0.073 (2)0.0395 (16)−0.0069 (15)0.0194 (14)−0.0076 (16)
C110.0387 (16)0.055 (2)0.0450 (17)0.0062 (15)0.0249 (15)0.0064 (15)
C120.0457 (17)0.0394 (17)0.0452 (17)0.0054 (13)0.0301 (15)0.0009 (13)
C130.0514 (18)0.0438 (18)0.0537 (17)−0.0093 (15)0.0356 (16)−0.0020 (15)
C140.054 (2)0.061 (2)0.063 (2)−0.0262 (18)0.0391 (18)−0.0114 (18)
C150.0391 (17)0.091 (3)0.0480 (18)−0.0172 (18)0.0284 (15)−0.0110 (18)
C160.0323 (15)0.065 (2)0.0313 (14)−0.0046 (15)0.0192 (13)−0.0063 (14)
C170.0333 (15)0.0470 (17)0.0308 (14)−0.0013 (13)0.0216 (13)−0.0031 (13)
C180.0371 (15)0.0378 (16)0.0298 (14)0.0040 (13)0.0216 (12)0.0002 (12)
C190.0492 (18)0.0476 (18)0.0329 (15)0.0141 (15)0.0265 (14)0.0038 (14)
C200.0500 (19)0.063 (2)0.0458 (18)0.0210 (17)0.0289 (16)0.0048 (17)
C210.0353 (17)0.091 (3)0.0410 (17)0.0132 (18)0.0215 (15)0.0016 (18)
C220.065 (2)0.0362 (17)0.0453 (17)0.0148 (16)0.0344 (16)0.0031 (14)
C230.069 (2)0.0297 (16)0.0495 (17)0.0005 (15)0.0361 (17)−0.0021 (14)
C240.0484 (17)0.0334 (17)0.0494 (17)−0.0017 (14)0.0301 (15)−0.0045 (14)
C250.0294 (14)0.0419 (17)0.0405 (16)−0.0018 (13)0.0215 (13)−0.0021 (14)
C260.0284 (14)0.0373 (16)0.0368 (15)−0.0001 (12)0.0179 (12)0.0003 (13)
C270.062 (2)0.0481 (19)0.0456 (18)−0.0102 (16)0.0344 (16)−0.0044 (16)
C280.086 (3)0.060 (2)0.050 (2)−0.013 (2)0.043 (2)0.0065 (18)
C290.066 (2)0.076 (2)0.0423 (18)−0.0125 (19)0.0348 (17)−0.0001 (19)
C300.0472 (18)0.068 (2)0.0433 (17)−0.0009 (17)0.0252 (15)−0.0125 (17)
C310.0290 (14)0.0433 (19)0.0424 (17)0.0017 (12)0.0183 (13)−0.0021 (14)
C320.0361 (16)0.048 (2)0.0367 (15)−0.0019 (14)0.0213 (13)−0.0011 (13)
C330.0306 (14)0.0460 (17)0.0337 (15)0.0067 (13)0.0170 (13)0.0034 (13)
C340.0353 (15)0.0536 (19)0.0322 (14)−0.0008 (14)0.0185 (13)−0.0014 (14)
C350.0351 (17)0.078 (2)0.0401 (16)−0.0053 (16)0.0234 (14)−0.0009 (16)
C360.0356 (17)0.095 (3)0.0448 (18)0.0039 (19)0.0253 (15)−0.0009 (18)
C370.0397 (18)0.078 (3)0.0521 (18)0.0230 (18)0.0255 (16)0.0069 (18)
C380.0462 (19)0.055 (2)0.0471 (17)0.0083 (16)0.0253 (15)0.0053 (16)

Geometric parameters (Å, °)

Nd1—O12.5256 (17)C9—H90.9300
Nd1—O22.5991 (16)C10—C111.355 (4)
Nd1—O52.5297 (18)C10—H100.9300
Nd1—O62.5325 (17)C11—C121.382 (4)
Nd1—O92.6060 (17)C11—H110.9300
Nd1—O102.5573 (17)C12—H120.9300
Nd1—N12.673 (2)C13—C141.397 (4)
Nd1—N22.651 (2)C13—H130.9300
Nd1—N32.628 (2)C14—C151.366 (4)
Nd1—N42.603 (2)C14—H140.9300
O1—C251.266 (3)C15—C161.401 (4)
O2—C251.264 (3)C15—H150.9300
O3—C311.343 (3)C16—C171.406 (3)
O3—H310.8200C16—C211.435 (4)
O4—C271.350 (3)C17—C181.436 (3)
O4—H270.8200C18—C191.406 (3)
O5—C321.275 (3)C19—C221.396 (4)
O6—C321.264 (3)C19—C201.431 (4)
O7—C341.340 (3)C20—C211.330 (4)
O7—H340.8200C20—H200.9300
O8—C381.359 (3)C21—H210.9300
O8—H380.8200C22—C231.341 (4)
O9—N51.257 (3)C22—H220.9300
O10—N51.274 (3)C23—C241.399 (4)
O11—N51.215 (3)C23—H230.9300
N1—C121.324 (3)C24—H240.9300
N1—C61.360 (3)C25—C261.484 (3)
N2—C11.328 (3)C26—C271.407 (4)
N2—C51.357 (3)C26—C311.407 (3)
N3—C131.332 (3)C27—C281.388 (4)
N3—C171.364 (3)C28—C291.361 (4)
N4—C241.331 (3)C28—H280.9300
N4—C181.356 (3)C29—C301.359 (4)
C1—C21.399 (4)C29—H290.9300
C1—H10.9300C30—C311.390 (4)
C2—C31.342 (4)C30—H300.9300
C2—H20.9300C32—C331.481 (4)
C3—C41.394 (4)C33—C381.406 (4)
C3—H30.9300C33—C341.408 (4)
C4—C51.414 (3)C34—C351.396 (4)
C4—C91.429 (4)C35—C361.374 (4)
C5—C61.438 (3)C35—H350.9300
C6—C71.409 (4)C36—C371.366 (4)
C7—C101.401 (4)C36—H360.9300
C7—C81.431 (4)C37—C381.387 (4)
C8—C91.339 (4)C37—H370.9300
C8—H80.9300
O1—Nd1—O579.78 (6)N1—C6—C7121.9 (2)
O1—Nd1—O675.70 (6)N1—C6—C5118.3 (2)
O5—Nd1—O651.50 (6)C7—C6—C5119.8 (2)
O1—Nd1—O10144.32 (6)C10—C7—C6117.5 (2)
O5—Nd1—O1070.60 (6)C10—C7—C8123.4 (3)
O6—Nd1—O1070.45 (6)C6—C7—C8119.1 (3)
O1—Nd1—O250.70 (6)C9—C8—C7121.1 (3)
O5—Nd1—O272.24 (6)C9—C8—H8119.4
O6—Nd1—O2107.76 (6)C7—C8—H8119.4
O10—Nd1—O2131.55 (6)C8—C9—C4121.6 (3)
O1—Nd1—N472.27 (6)C8—C9—H9119.2
O5—Nd1—N4135.00 (7)C4—C9—H9119.2
O6—Nd1—N487.22 (6)C11—C10—C7120.2 (3)
O10—Nd1—N4116.16 (6)C11—C10—H10119.9
O2—Nd1—N4112.01 (6)C7—C10—H10119.9
O1—Nd1—O9125.66 (6)C10—C11—C12118.4 (3)
O5—Nd1—O9105.44 (6)C10—C11—H11120.8
O6—Nd1—O968.20 (6)C12—C11—H11120.8
O10—Nd1—O949.28 (6)N1—C12—C11124.4 (3)
O2—Nd1—O9175.69 (6)N1—C12—H12117.8
N4—Nd1—O966.89 (6)C11—C12—H12117.8
O1—Nd1—N378.54 (6)N3—C13—C14123.1 (3)
O5—Nd1—N3144.28 (6)N3—C13—H13118.5
O6—Nd1—N3144.89 (6)C14—C13—H13118.5
O10—Nd1—N3136.93 (7)C15—C14—C13119.0 (3)
O2—Nd1—N372.06 (6)C15—C14—H14120.5
N4—Nd1—N362.24 (6)C13—C14—H14120.5
O9—Nd1—N3110.26 (6)C14—C15—C16120.3 (3)
O1—Nd1—N2122.32 (6)C14—C15—H15119.8
O5—Nd1—N280.03 (7)C16—C15—H15119.8
O6—Nd1—N2126.03 (6)C15—C16—C17116.9 (3)
O10—Nd1—N272.20 (6)C15—C16—C21123.8 (3)
O2—Nd1—N271.72 (6)C17—C16—C21119.2 (3)
N4—Nd1—N2144.90 (7)N3—C17—C16123.0 (2)
O9—Nd1—N2111.70 (6)N3—C17—C18117.7 (2)
N3—Nd1—N288.03 (6)C16—C17—C18119.2 (2)
O1—Nd1—N1145.39 (6)N4—C18—C19122.2 (2)
O5—Nd1—N1131.30 (6)N4—C18—C17117.7 (2)
O6—Nd1—N1133.02 (6)C19—C18—C17120.0 (2)
O10—Nd1—N169.93 (6)C22—C19—C18117.5 (3)
O2—Nd1—N1117.17 (6)C22—C19—C20124.0 (3)
N4—Nd1—N188.32 (6)C18—C19—C20118.4 (3)
O9—Nd1—N167.12 (6)C21—C20—C19121.9 (3)
N3—Nd1—N167.01 (6)C21—C20—H20119.1
N2—Nd1—N161.55 (7)C19—C20—H20119.1
O1—Nd1—C3279.81 (6)C20—C21—C16121.0 (3)
O5—Nd1—C3226.09 (6)C20—C21—H21119.5
O6—Nd1—C3225.84 (6)C16—C21—H21119.5
O10—Nd1—C3264.82 (7)C23—C22—C19120.2 (3)
O2—Nd1—C3292.54 (7)C23—C22—H22119.9
N4—Nd1—C32112.52 (7)C19—C22—H22119.9
O9—Nd1—C3284.22 (7)C22—C23—C24119.2 (3)
N3—Nd1—C32158.25 (7)C22—C23—H23120.4
N2—Nd1—C32101.91 (7)C24—C23—H23120.4
N1—Nd1—C32134.73 (6)N4—C24—C23123.0 (3)
O1—Nd1—C2525.31 (7)N4—C24—H24118.5
O5—Nd1—C2574.12 (6)C23—C24—H24118.5
O6—Nd1—C2591.50 (6)O2—C25—O1120.3 (2)
O10—Nd1—C25144.35 (7)O2—C25—C26120.3 (2)
O2—Nd1—C2525.39 (6)O1—C25—C26119.4 (2)
N4—Nd1—C2592.44 (7)O2—C25—Nd161.82 (13)
O9—Nd1—C25150.88 (7)O1—C25—Nd158.49 (13)
N3—Nd1—C2574.13 (6)C26—C25—Nd1177.36 (19)
N2—Nd1—C2597.04 (7)C27—C26—C31118.2 (2)
N1—Nd1—C25135.42 (6)C27—C26—C25120.8 (2)
C32—Nd1—C2585.39 (7)C31—C26—C25121.0 (2)
C25—O1—Nd196.19 (15)O4—C27—C28118.0 (3)
C25—O2—Nd192.78 (15)O4—C27—C26121.8 (2)
C31—O3—H31109.5C28—C27—C26120.2 (3)
C27—O4—H27109.5C29—C28—C27119.7 (3)
C32—O5—Nd193.14 (16)C29—C28—H28120.1
C32—O6—Nd193.28 (15)C27—C28—H28120.1
C34—O7—H34109.5C30—C29—C28122.0 (3)
C38—O8—H38109.5C30—C29—H29119.0
N5—O9—Nd196.10 (15)C28—C29—H29119.0
N5—O10—Nd197.96 (13)C29—C30—C31119.8 (3)
C12—N1—C6117.5 (2)C29—C30—H30120.1
C12—N1—Nd1122.17 (17)C31—C30—H30120.1
C6—N1—Nd1120.16 (16)O3—C31—C30117.5 (3)
C1—N2—C5117.3 (2)O3—C31—C26122.3 (2)
C1—N2—Nd1121.25 (17)C30—C31—C26120.1 (3)
C5—N2—Nd1121.03 (16)O6—C32—O5120.1 (2)
C13—N3—C17117.7 (2)O6—C32—C33120.3 (2)
C13—N3—Nd1122.11 (18)O5—C32—C33119.6 (2)
C17—N3—Nd1119.16 (15)O6—C32—Nd160.87 (13)
C24—N4—C18117.7 (2)O5—C32—Nd160.78 (14)
C24—N4—Nd1121.24 (17)C33—C32—Nd1165.83 (17)
C18—N4—Nd1120.79 (16)C38—C33—C34118.4 (2)
O11—N5—O9122.4 (3)C38—C33—C32121.1 (3)
O11—N5—O10121.1 (3)C34—C33—C32120.4 (2)
O9—N5—O10116.6 (2)O7—C34—C35116.9 (3)
N2—C1—C2123.3 (3)O7—C34—C33122.9 (2)
N2—C1—H1118.3C35—C34—C33120.2 (3)
C2—C1—H1118.3C36—C35—C34118.7 (3)
C3—C2—C1119.5 (3)C36—C35—H35120.7
C3—C2—H2120.3C34—C35—H35120.7
C1—C2—H2120.3C37—C36—C35123.0 (3)
C2—C3—C4119.9 (3)C37—C36—H36118.5
C2—C3—H3120.0C35—C36—H36118.5
C4—C3—H3120.0C36—C37—C38118.7 (3)
C3—C4—C5117.5 (3)C36—C37—H37120.7
C3—C4—C9123.4 (3)C38—C37—H37120.7
C5—C4—C9119.1 (3)O8—C38—C37117.9 (3)
N2—C5—C4122.5 (3)O8—C38—C33121.3 (3)
N2—C5—C6118.2 (2)C37—C38—C33120.9 (3)
C4—C5—C6119.2 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H31···O10.821.862.581 (2)147
O4—H27···O20.821.872.582 (3)145
O7—H34···O60.821.872.592 (2)146
O8—H38···O50.821.832.562 (3)148

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2364).

References

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