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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): m1612.
Published online 2010 November 20. doi:  10.1107/S1600536810047148
PMCID: PMC3011488

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

Abstract

The title mononuclear complex, [Eu(C7H5O3)2(NO3)(C12H8N2)2], is isostructural with those of other lanthanides. The Eu atom is in a pseudo-bicapped square-anti­prismatic geometry, formed by four N atoms from two chelating 1,10-phenanthroline (phen) ligands and by six O atoms, four from two 2,6-dihy­droxy­benzoate (DHB) ligands and the other two from a nitrate anion. π–π stacking inter­actions between phen and DHB ligands [centroid–centroid distances = 3.5312 (19) and 3.8347 (16) Å], and between phen and phen ligands [face-to-face separation = 3.433 (4) Å] of adjacent complexes stabilize the crystal structure. Intra­molecular O—H(...)O hydrogen bonds are observed in the DHB ligands.

Related literature

For background and details of a related structure, see: Zheng et al. (2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1612-scheme1.jpg

Experimental

Crystal data

  • [Eu(C7H5O3)2(NO3)(C12H8N2)2]
  • M r = 880.60
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1612-efi1.jpg
  • a = 11.1855 (2) Å
  • b = 26.7682 (5) Å
  • c = 14.3286 (4) Å
  • β = 127.557 (2)°
  • V = 3401.05 (16) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.92 mm−1
  • T = 298 K
  • 0.40 × 0.36 × 0.35 mm

Data collection

  • Oxford Diffraction Gemini S Ultra diffractometer
  • Absorption correction: multi-scan [ABSPACK in CrysAlis PRO RED (Oxford Diffraction, 2006 [triangle])] T min = 0.514, T max = 0.553
  • 22346 measured reflections
  • 6936 independent reflections
  • 5281 reflections with I > 2σ(I)
  • R int = 0.027

Refinement

  • R[F 2 > 2σ(F 2)] = 0.024
  • wR(F 2) = 0.043
  • S = 1.05
  • 6936 reflections
  • 496 parameters
  • 8 restraints
  • H-atom parameters constrained
  • Δρmax = 0.36 e Å−3
  • Δρmin = −0.49 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810047148/su2227sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047148/su2227Isup2.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

The description of the structure of the title compound is part of a series of papers on mononuclear complexes of the type [Ln(C12H8N2)2(C7H8O3)2 (NO3)], with Ln = Ce, Pr, Sm, Eu (this publication), and Dy. All five compounds are isostructural to the previously reported Nd complex (Zheng et al. 2010). The background to this study is given in the previous paper by Zheng et al. (2010).

Experimental

Each reagent was commercially available and of analytical grade. Eu(NO3)3.6H2O (0.224 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, 5:5). The solution was refluxed for 4 h, and filtered after cooling to room temperature. Orange single crystals were obtained from the filtrate after 3 d.

Refinement

H atoms were positioned geometrically (C—H = 0.93 Å and O—H = 0.82 Å) and refined as riding, with Uiso (H) = 1.2Ueq (C) and Uiso(H) = 1.5Ueq (O). The anisotropic displacement of the O10, N5, Eu1 and O9 atoms were restrained to be equal.

Figures

Fig. 1.
The molecular structure of title compound. Displacement ellipsoids are drawn at the 15% probablility level and H atoms are shown as small spheres of arbitraty radii. Some H atoms are omitted for clarity. Light orange lines show the intramolecular hydrogen ...

Crystal data

[Eu(C7H5O3)2(NO3)(C12H8N2)2]F(000) = 1760
Mr = 880.60Dx = 1.720 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 11999 reflections
a = 11.1855 (2) Åθ = 2.9–29.1°
b = 26.7682 (5) ŵ = 1.92 mm1
c = 14.3286 (4) ÅT = 298 K
β = 127.557 (2)°Block, orange
V = 3401.05 (16) Å30.40 × 0.36 × 0.35 mm
Z = 4

Data collection

Oxford Diffraction Gemini S Ultra diffractometer6936 independent reflections
Radiation source: Enhance (Mo) X-ray Source5281 reflections with I > 2σ(I)
graphiteRint = 0.027
Detector resolution: 15.9149 pixels mm-1θmax = 26.4°, θmin = 3.0°
ω scansh = −13→10
Absorption correction: multi-scan [ABSPACK in CrysAlis PRO RED (Oxford Diffraction, 2006)]k = −33→32
Tmin = 0.514, Tmax = 0.553l = −11→17
22346 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)] = 0.024Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.043H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0144P)2] where P = (Fo2 + 2Fc2)/3
6936 reflections(Δ/σ)max = 0.001
496 parametersΔρmax = 0.36 e Å3
8 restraintsΔρmin = −0.49 e Å3

Special details

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)

xyzUiso*/Ueq
Eu10.430778 (13)0.861975 (4)0.720853 (12)0.03240 (4)
O10.19590 (17)0.81211 (6)0.63374 (15)0.0437 (5)
O20.16583 (18)0.89279 (7)0.59806 (16)0.0492 (5)
O3−0.01921 (19)0.75869 (7)0.60271 (16)0.0535 (5)
H310.06240.76410.61660.080*
O4−0.0800 (2)0.93598 (7)0.5290 (2)0.0750 (7)
H270.00620.93330.54990.113*
O50.34598 (18)0.83820 (7)0.52114 (15)0.0447 (5)
O60.38918 (18)0.91856 (6)0.55787 (15)0.0448 (5)
O70.2549 (2)0.80247 (7)0.32044 (17)0.0606 (5)
H380.27890.80210.38710.091*
O80.3356 (3)0.97889 (7)0.39552 (19)0.0816 (7)
H340.35660.97050.45900.122*
O90.45362 (19)0.80112 (6)0.87237 (16)0.0469 (4)
O100.34644 (19)0.87175 (7)0.84764 (17)0.0503 (5)
O110.3634 (2)0.81721 (9)0.96677 (19)0.0823 (7)
N10.5570 (2)0.77913 (7)0.73843 (17)0.0347 (5)
N20.6809 (2)0.86747 (7)0.74804 (18)0.0370 (5)
N30.4755 (2)0.95459 (7)0.79134 (19)0.0370 (5)
N40.6651 (2)0.88072 (7)0.93947 (18)0.0355 (5)
N50.3879 (2)0.82911 (9)0.8983 (2)0.0463 (5)
C10.4920 (3)0.73535 (10)0.7235 (2)0.0427 (7)
H10.39460.73520.70130.051*
C20.5611 (3)0.68954 (10)0.7391 (2)0.0478 (7)
H20.50950.65980.72460.057*
C30.7046 (3)0.68922 (10)0.7756 (2)0.0480 (7)
H30.75320.65900.78770.058*
C40.7801 (3)0.73409 (10)0.7951 (2)0.0417 (7)
C50.7001 (3)0.77846 (9)0.7716 (2)0.0347 (6)
C60.9345 (3)0.73719 (12)0.8396 (2)0.0526 (8)
H60.99040.70800.86050.063*
C71.0004 (3)0.78094 (12)0.8518 (2)0.0538 (8)
H71.10090.78160.88120.065*
C80.9179 (3)0.82669 (11)0.8201 (2)0.0437 (7)
C90.7677 (3)0.82588 (10)0.7813 (2)0.0360 (6)
C100.7415 (3)0.91061 (10)0.7505 (2)0.0470 (7)
H100.68290.93930.72660.056*
C110.8890 (3)0.91501 (12)0.7871 (3)0.0552 (8)
H110.92700.94590.78710.066*
C120.9755 (3)0.87350 (12)0.8224 (3)0.0549 (8)
H121.07440.87610.84860.066*
C130.3819 (3)0.99087 (10)0.7204 (3)0.0465 (7)
H130.30590.98330.64180.056*
C140.3929 (3)1.03979 (10)0.7587 (3)0.0532 (8)
H140.32541.06400.70620.064*
C150.5022 (3)1.05169 (10)0.8724 (3)0.0520 (8)
H150.50991.08420.89850.062*
C160.6039 (3)1.01513 (9)0.9512 (3)0.0406 (7)
C170.5851 (3)0.96642 (9)0.9062 (2)0.0341 (6)
C180.6860 (3)0.92762 (9)0.9847 (2)0.0337 (6)
C190.8009 (3)0.93855 (10)1.1035 (2)0.0393 (6)
C200.8156 (3)0.98871 (11)1.1446 (3)0.0507 (8)
H200.89230.99621.22310.061*
C210.7213 (3)1.02491 (11)1.0723 (3)0.0509 (8)
H210.73261.05701.10170.061*
C220.8964 (3)0.89993 (11)1.1759 (3)0.0501 (8)
H220.97330.90601.25520.060*
C230.8775 (3)0.85332 (11)1.1308 (2)0.0477 (7)
H230.94150.82731.17800.057*
C240.7604 (3)0.84565 (10)1.0125 (2)0.0418 (7)
H240.74790.81370.98250.050*
C250.1141 (3)0.85088 (10)0.5999 (2)0.0405 (7)
C26−0.0402 (3)0.84766 (10)0.5660 (2)0.0388 (7)
C27−0.1308 (3)0.89040 (12)0.5326 (3)0.0521 (8)
C28−0.2734 (3)0.88738 (13)0.5031 (3)0.0586 (8)
H28−0.33310.91580.48060.070*
C29−0.3250 (3)0.84196 (14)0.5077 (3)0.0586 (9)
H29−0.42100.84000.48780.070*
C30−0.2418 (3)0.79931 (12)0.5402 (2)0.0516 (8)
H30−0.28070.76900.54220.062*
C31−0.0983 (3)0.80167 (11)0.5701 (2)0.0414 (7)
C320.3466 (3)0.88224 (11)0.4875 (2)0.0368 (6)
C330.2975 (2)0.89004 (10)0.3666 (2)0.0361 (6)
C340.2936 (3)0.93810 (11)0.3255 (3)0.0499 (7)
C350.2441 (3)0.94544 (12)0.2110 (3)0.0641 (9)
H350.23950.97750.18400.077*
C360.2023 (3)0.90549 (13)0.1386 (3)0.0609 (8)
H360.17030.91070.06230.073*
C370.2059 (3)0.85796 (12)0.1748 (2)0.0520 (7)
H370.17670.83130.12350.062*
C380.2537 (3)0.84956 (10)0.2888 (2)0.0409 (7)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Eu10.03389 (7)0.02771 (7)0.03845 (8)0.00054 (6)0.02352 (6)−0.00013 (7)
O10.0357 (9)0.0386 (11)0.0556 (12)0.0033 (8)0.0273 (10)0.0001 (9)
O20.0405 (10)0.0420 (12)0.0621 (13)0.0030 (9)0.0297 (10)0.0085 (10)
O30.0439 (11)0.0508 (13)0.0675 (14)0.0003 (9)0.0348 (11)0.0069 (11)
O40.0591 (13)0.0547 (14)0.1005 (19)0.0183 (11)0.0431 (13)0.0140 (13)
O50.0501 (11)0.0397 (11)0.0416 (12)−0.0016 (9)0.0265 (10)0.0019 (10)
O60.0564 (11)0.0396 (11)0.0391 (11)−0.0023 (9)0.0296 (10)−0.0027 (9)
O70.0716 (13)0.0416 (12)0.0486 (13)−0.0009 (10)0.0262 (11)−0.0062 (10)
O80.140 (2)0.0422 (13)0.0585 (15)−0.0165 (13)0.0586 (16)−0.0025 (12)
O90.0533 (11)0.0388 (10)0.0519 (12)0.0002 (8)0.0337 (10)0.0046 (8)
O100.0594 (11)0.0476 (10)0.0605 (13)0.0028 (8)0.0451 (11)−0.0043 (9)
O110.0823 (15)0.128 (2)0.0583 (14)−0.0063 (14)0.0539 (14)0.0139 (15)
N10.0360 (12)0.0318 (12)0.0384 (13)0.0002 (9)0.0237 (11)−0.0006 (10)
N20.0396 (11)0.0371 (13)0.0393 (13)−0.0055 (10)0.0266 (11)−0.0033 (11)
N30.0479 (13)0.0266 (12)0.0450 (14)0.0023 (10)0.0327 (13)0.0031 (10)
N40.0355 (11)0.0332 (12)0.0380 (13)0.0019 (9)0.0226 (11)−0.0005 (10)
N50.0444 (13)0.0586 (13)0.0406 (14)−0.0066 (10)0.0283 (12)−0.0014 (10)
C10.0478 (15)0.0354 (17)0.0466 (18)−0.0015 (13)0.0296 (15)−0.0042 (13)
C20.0647 (19)0.0301 (16)0.0493 (18)0.0017 (13)0.0350 (17)−0.0018 (13)
C30.0651 (19)0.0364 (17)0.0438 (18)0.0136 (14)0.0340 (17)0.0025 (14)
C40.0456 (16)0.0502 (18)0.0327 (16)0.0122 (13)0.0256 (15)0.0043 (13)
C50.0372 (14)0.0394 (16)0.0321 (15)0.0023 (11)0.0235 (13)−0.0010 (12)
C60.0502 (18)0.063 (2)0.0441 (19)0.0221 (15)0.0284 (16)0.0057 (16)
C70.0343 (15)0.085 (2)0.0408 (18)0.0103 (16)0.0225 (15)0.0000 (17)
C80.0352 (15)0.064 (2)0.0330 (16)−0.0059 (14)0.0212 (14)−0.0075 (15)
C90.0338 (14)0.0464 (17)0.0315 (15)−0.0006 (12)0.0217 (13)−0.0023 (13)
C100.0507 (17)0.0450 (17)0.0501 (18)−0.0075 (13)0.0331 (15)−0.0038 (15)
C110.0535 (18)0.057 (2)0.063 (2)−0.0255 (15)0.0395 (18)−0.0108 (17)
C120.0379 (16)0.083 (3)0.0469 (18)−0.0156 (16)0.0276 (15)−0.0108 (17)
C130.0572 (17)0.0358 (17)0.0544 (19)0.0067 (13)0.0381 (16)0.0061 (14)
C140.072 (2)0.0307 (17)0.077 (2)0.0110 (14)0.055 (2)0.0121 (16)
C150.078 (2)0.0277 (16)0.083 (2)−0.0057 (15)0.065 (2)−0.0058 (16)
C160.0485 (16)0.0307 (15)0.063 (2)−0.0079 (12)0.0446 (17)−0.0059 (14)
C170.0390 (14)0.0311 (15)0.0476 (18)−0.0050 (11)0.0343 (15)−0.0015 (13)
C180.0353 (14)0.0344 (15)0.0443 (17)−0.0052 (11)0.0309 (14)−0.0043 (13)
C190.0358 (14)0.0451 (17)0.0438 (17)−0.0078 (12)0.0278 (15)−0.0076 (14)
C200.0481 (17)0.058 (2)0.0510 (19)−0.0212 (15)0.0329 (16)−0.0210 (17)
C210.0608 (19)0.0393 (18)0.073 (2)−0.0197 (15)0.051 (2)−0.0208 (17)
C220.0344 (15)0.067 (2)0.0441 (18)−0.0054 (14)0.0215 (15)−0.0055 (16)
C230.0399 (15)0.055 (2)0.0453 (18)0.0058 (13)0.0246 (15)0.0067 (15)
C240.0468 (16)0.0373 (16)0.0457 (18)0.0033 (12)0.0305 (16)0.0011 (13)
C250.0392 (15)0.0458 (19)0.0357 (16)0.0008 (12)0.0225 (14)0.0008 (13)
C260.0311 (14)0.0479 (18)0.0332 (15)0.0050 (11)0.0173 (13)0.0018 (12)
C270.0479 (17)0.056 (2)0.0490 (19)0.0092 (15)0.0276 (16)0.0075 (16)
C280.0417 (17)0.079 (2)0.052 (2)0.0234 (16)0.0270 (16)0.0071 (18)
C290.0315 (15)0.100 (3)0.0434 (19)0.0068 (17)0.0222 (15)0.0006 (18)
C300.0381 (16)0.077 (2)0.0431 (18)−0.0037 (15)0.0263 (15)0.0016 (16)
C310.0345 (14)0.0577 (19)0.0290 (15)0.0024 (13)0.0178 (13)0.0011 (14)
C320.0294 (13)0.0420 (16)0.0394 (17)0.0022 (12)0.0212 (13)0.0022 (14)
C330.0283 (13)0.0411 (16)0.0367 (16)0.0014 (11)0.0188 (13)0.0018 (13)
C340.0619 (18)0.0447 (19)0.0458 (19)−0.0078 (14)0.0342 (17)−0.0021 (15)
C350.087 (2)0.058 (2)0.051 (2)−0.0151 (18)0.044 (2)0.0030 (18)
C360.066 (2)0.076 (2)0.0427 (19)−0.0080 (17)0.0346 (17)0.0005 (18)
C370.0486 (16)0.063 (2)0.0440 (18)−0.0028 (15)0.0280 (15)−0.0130 (17)
C380.0293 (13)0.0459 (19)0.0410 (17)0.0016 (11)0.0182 (14)−0.0014 (13)

Geometric parameters (Å, °)

Eu1—O52.4869 (17)C8—C121.400 (4)
Eu1—O22.4904 (16)C8—C91.413 (3)
Eu1—O12.4989 (16)C10—C111.399 (3)
Eu1—O102.5196 (17)C10—H100.9300
Eu1—N12.5574 (19)C11—C121.352 (4)
Eu1—O62.5767 (17)C11—H110.9300
Eu1—N22.5830 (18)C12—H120.9300
Eu1—O92.5991 (17)C13—C141.396 (3)
Eu1—N32.608 (2)C13—H130.9300
Eu1—N42.632 (2)C14—C151.350 (4)
Eu1—C252.856 (3)C14—H140.9300
Eu1—C322.919 (3)C15—C161.400 (4)
O1—C251.269 (3)C15—H150.9300
O2—C251.270 (3)C16—C171.412 (3)
O3—C311.349 (3)C16—C211.424 (4)
O3—H310.8199C17—C181.439 (3)
O4—C271.361 (3)C18—C191.403 (3)
O4—H270.8200C19—C221.391 (3)
O5—C321.275 (3)C19—C201.435 (4)
O6—C321.266 (3)C20—C211.339 (4)
O7—C381.337 (3)C20—H200.9300
O7—H380.8200C21—H210.9300
O8—C341.358 (3)C22—C231.361 (4)
O8—H340.8200C22—H220.9300
O9—N51.254 (3)C23—C241.387 (4)
O10—N51.278 (3)C23—H230.9300
O11—N51.211 (3)C24—H240.9300
N1—C11.326 (3)C25—C261.482 (3)
N1—C51.365 (3)C26—C271.405 (3)
N2—C101.329 (3)C26—C311.411 (3)
N2—C91.358 (3)C27—C281.381 (3)
N3—C131.332 (3)C28—C291.365 (4)
N3—C171.361 (3)C28—H280.9300
N4—C241.324 (3)C29—C301.363 (4)
N4—C181.366 (3)C29—H290.9300
C1—C21.393 (3)C30—C311.387 (3)
C1—H10.9300C30—H300.9300
C2—C31.352 (3)C32—C331.479 (3)
C2—H20.9300C33—C341.405 (3)
C3—C41.395 (4)C33—C381.411 (3)
C3—H30.9300C34—C351.390 (4)
C4—C51.399 (3)C35—C361.359 (4)
C4—C61.433 (3)C35—H350.9300
C5—C91.440 (3)C36—C371.365 (4)
C6—C71.337 (4)C36—H360.9300
C6—H60.9300C37—C381.394 (4)
C7—C81.430 (4)C37—H370.9300
C7—H70.9300
O5—Eu1—O279.45 (6)N1—C5—C9117.2 (2)
O5—Eu1—O174.99 (6)C4—C5—C9120.3 (2)
O2—Eu1—O152.27 (6)C7—C6—C4121.8 (3)
O5—Eu1—O10143.94 (6)C7—C6—H6119.1
O2—Eu1—O1070.59 (6)C4—C6—H6119.1
O1—Eu1—O1070.97 (6)C6—C7—C8120.7 (2)
O5—Eu1—N172.05 (6)C6—C7—H7119.6
O2—Eu1—N1134.78 (6)C8—C7—H7119.6
O1—Eu1—N186.28 (6)C12—C8—C9116.3 (3)
O10—Eu1—N1116.47 (6)C12—C8—C7124.1 (2)
O5—Eu1—O651.40 (6)C9—C8—C7119.6 (2)
O2—Eu1—O671.65 (5)N2—C9—C8123.3 (2)
O1—Eu1—O6107.90 (6)N2—C9—C5117.9 (2)
O10—Eu1—O6130.72 (6)C8—C9—C5118.7 (2)
N1—Eu1—O6112.52 (6)N2—C10—C11123.3 (3)
O5—Eu1—N278.84 (6)N2—C10—H10118.3
O2—Eu1—N2143.20 (6)C11—C10—H10118.3
O1—Eu1—N2144.89 (6)C12—C11—C10118.8 (3)
O10—Eu1—N2137.10 (6)C12—C11—H11120.6
N1—Eu1—N263.42 (6)C10—C11—H11120.6
O6—Eu1—N271.57 (6)C11—C12—C8120.9 (2)
O5—Eu1—O9125.11 (6)C11—C12—H12119.6
O2—Eu1—O9105.46 (6)C8—C12—H12119.6
O1—Eu1—O967.70 (6)N3—C13—C14122.9 (3)
O10—Eu1—O949.62 (6)N3—C13—H13118.5
N1—Eu1—O966.85 (6)C14—C13—H13118.5
O6—Eu1—O9175.49 (5)C15—C14—C13119.6 (3)
N2—Eu1—O9111.33 (6)C15—C14—H14120.2
O5—Eu1—N3122.52 (6)C13—C14—H14120.2
O2—Eu1—N379.83 (6)C14—C15—C16120.1 (3)
O1—Eu1—N3126.60 (6)C14—C15—H15120.0
O10—Eu1—N371.92 (6)C16—C15—H15120.0
N1—Eu1—N3145.31 (6)C15—C16—C17117.1 (3)
O6—Eu1—N371.23 (6)C15—C16—C21123.1 (3)
N2—Eu1—N387.31 (6)C17—C16—C21119.8 (3)
O9—Eu1—N3111.98 (6)N3—C17—C16122.7 (2)
O5—Eu1—N4145.39 (6)N3—C17—C18118.5 (2)
O2—Eu1—N4132.12 (6)C16—C17—C18118.8 (2)
O1—Eu1—N4132.65 (6)N4—C18—C19122.2 (2)
O10—Eu1—N470.18 (6)N4—C18—C17117.8 (2)
N1—Eu1—N487.63 (6)C19—C18—C17120.0 (2)
O6—Eu1—N4117.73 (6)C22—C19—C18118.0 (2)
N2—Eu1—N466.94 (6)C22—C19—C20123.1 (3)
O9—Eu1—N466.78 (6)C18—C19—C20119.0 (3)
N3—Eu1—N462.68 (6)C21—C20—C19121.4 (3)
O5—Eu1—C2579.24 (6)C21—C20—H20119.3
O2—Eu1—C2526.36 (6)C19—C20—H20119.3
O1—Eu1—C2526.34 (6)C20—C21—C16121.1 (3)
O10—Eu1—C2564.98 (7)C20—C21—H21119.4
N1—Eu1—C25112.06 (7)C16—C21—H21119.4
O6—Eu1—C2592.25 (6)C23—C22—C19120.1 (3)
N2—Eu1—C25157.87 (7)C23—C22—H22120.0
O9—Eu1—C2584.01 (7)C19—C22—H22120.0
N3—Eu1—C25102.00 (7)C22—C23—C24118.2 (3)
N4—Eu1—C25135.16 (7)C22—C23—H23120.9
O5—Eu1—C3225.73 (6)C24—C23—H23120.9
O2—Eu1—C3273.44 (6)N4—C24—C23124.5 (2)
O1—Eu1—C3291.15 (6)N4—C24—H24117.7
O10—Eu1—C32143.64 (6)C23—C24—H24117.7
N1—Eu1—C3292.71 (7)O1—C25—O2119.9 (2)
O6—Eu1—C3225.68 (6)O1—C25—C26120.1 (2)
N2—Eu1—C3274.09 (6)O2—C25—C26119.9 (2)
O9—Eu1—C32150.69 (7)O1—C25—Eu160.92 (12)
N3—Eu1—C3296.82 (7)O2—C25—Eu160.54 (12)
N4—Eu1—C32136.05 (6)C26—C25—Eu1165.99 (18)
C25—Eu1—C3284.81 (7)C27—C26—C31118.0 (2)
C25—O1—Eu192.74 (14)C27—C26—C25121.2 (2)
C25—O2—Eu193.09 (15)C31—C26—C25120.8 (2)
C31—O3—H31109.5O4—C27—C28118.2 (3)
C27—O4—H27109.4O4—C27—C26120.7 (2)
C32—O5—Eu196.44 (16)C28—C27—C26121.1 (3)
C32—O6—Eu192.45 (15)C29—C28—C27118.7 (3)
C38—O7—H38109.5C29—C28—H28120.6
C34—O8—H34109.5C27—C28—H28120.6
N5—O9—Eu195.51 (15)C30—C29—C28122.8 (3)
N5—O10—Eu198.68 (14)C30—C29—H29118.6
C1—N1—C5117.1 (2)C28—C29—H29118.6
C1—N1—Eu1122.35 (16)C29—C30—C31119.2 (3)
C5—N1—Eu1120.37 (15)C29—C30—H30120.4
C10—N2—C9117.3 (2)C31—C30—H30120.4
C10—N2—Eu1122.81 (17)O3—C31—C30117.3 (2)
C9—N2—Eu1118.85 (15)O3—C31—C26122.5 (2)
C13—N3—C17117.6 (2)C30—C31—C26120.2 (3)
C13—N3—Eu1121.43 (17)O6—C32—O5119.7 (2)
C17—N3—Eu1120.54 (15)O6—C32—C33121.0 (2)
C24—N4—C18117.0 (2)O5—C32—C33119.3 (2)
C24—N4—Eu1122.93 (16)O6—C32—Eu161.87 (13)
C18—N4—Eu1119.89 (16)O5—C32—Eu157.83 (13)
O11—N5—O9123.1 (3)C33—C32—Eu1176.62 (19)
O11—N5—O10120.8 (2)C34—C33—C38117.7 (2)
O9—N5—O10116.2 (2)C34—C33—C32121.0 (2)
O11—N5—Eu1176.5 (2)C38—C33—C32121.3 (2)
O9—N5—Eu159.84 (12)O8—C34—C35117.9 (3)
O10—N5—Eu156.35 (12)O8—C34—C33121.2 (3)
N1—C1—C2123.8 (2)C35—C34—C33120.9 (3)
N1—C1—H1118.1C36—C35—C34119.6 (3)
C2—C1—H1118.1C36—C35—H35120.2
C3—C2—C1118.7 (3)C34—C35—H35120.2
C3—C2—H2120.7C35—C36—C37121.8 (3)
C1—C2—H2120.7C35—C36—H36119.1
C2—C3—C4120.2 (2)C37—C36—H36119.1
C2—C3—H3119.9C36—C37—C38119.8 (3)
C4—C3—H3119.9C36—C37—H37120.1
C3—C4—C5117.6 (2)C38—C37—H37120.1
C3—C4—C6123.9 (2)O7—C38—C37117.9 (3)
C5—C4—C6118.6 (3)O7—C38—C33122.0 (2)
N1—C5—C4122.5 (2)C37—C38—C33120.2 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O8—H34···O60.821.862.585 (3)148
O4—H27···O20.821.832.561 (2)148
O7—H38···O50.821.852.579 (3)147
O3—H31···O10.821.872.594 (2)147

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2227).

References

  • Brandenburg, K. & Berndt, M. (1999). DIAMOND Crystal Impact GbR, Bonn, Germany.
  • Oxford Diffraction (2006). CrysAlis PRO CCD and CrysAlis PRO RED Oxford Diffraction Ltd, Abingdon, England.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zheng, J., Jin, H. & Ge, H. (2010). Acta Cryst. E66, m1469–m1470. [PMC free article] [PubMed]

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