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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): m1204.
Published online 2010 September 4. doi:  10.1107/S1600536810034215
PMCID: PMC2983210

Tetra­aqua­bis­(μ2-4,4′-bipyridine)­dodeca­kis­(μ2-2-methyl­prop-2-enoato)octa­kis­(2-methyl­prop-2-enoato)tetra­ytterbium(III)tetra­zinc(II)

Abstract

The asymmetric unit of the title compound, [Yb4Zn4(C4H5O2)20(C10H8N2)2(H2O)4], contains half of a centrosymmetric octa­nuclear mol­ecule in which each ZnII ion is four-coordinated by three O atoms from three 2-methyl­prop-2-enoate (L) ligands and one N atom from a 4,4′-bipyridine (bipy) ligand in a distorted pyramidal geometry. The two independent YbIII ions, each coordinated by eight O atoms in an irregular geometry, exhibit different coordination environments, viz. one water mol­ecule, five bridging bidentate and one chelating bidentate carboxyl­ate groups for one YbIII ion, and one water mol­ecule, three bridging bidentate and two chelating bidentate carboxyl­ate groups for the other YbIII ion. In the crystal structure, inter­molecular O—H(...)O and C—H(...)O hydrogen bonds help to establish the packing.

Related literature

For the crystal structures of analogous complexes, see: Wu et al. (2003 [triangle], 2004 [triangle]). For details of the preparation of YbL 3 (L = methacrylate), see: Lu et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1204-scheme1.jpg

Experimental

Crystal data

  • [Yb4Zn4(C4H5O2)20(C10H8N2)2(H2O)4]
  • M r = 1519.84
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1204-efi1.jpg
  • a = 13.398 (3) Å
  • b = 14.880 (3) Å
  • c = 16.408 (3) Å
  • α = 64.06 (3)°
  • β = 89.55 (3)°
  • γ = 85.54 (3)°
  • V = 2931.5 (10) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 4.05 mm−1
  • T = 293 K
  • 0.26 × 0.22 × 0.10 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.381, T max = 0.673
  • 22308 measured reflections
  • 10712 independent reflections
  • 8847 reflections with I > 2σ(I)
  • R int = 0.055

Refinement

  • R[F 2 > 2σ(F 2)] = 0.030
  • wR(F 2) = 0.066
  • S = 1.01
  • 10712 reflections
  • 714 parameters
  • H-atom parameters constrained
  • Δρmax = 0.57 e Å−3
  • Δρmin = −0.87 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 [triangle]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 [triangle]); 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]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810034215/cv2750sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034215/cv2750Isup2.hkl

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

supplementary crystallographic information

Comment

The study of heterometallic complexes containing d-transition metal and lanthanide(III) cations connected by bridging ligands is being actively pursued because of their relevance in solid-state technology and as models for magnetic studies. As a contribution to a structural study of heterometallic complexes containing d-transition metal and rare-earth(III) cations, herewith we report the synthesis and crystal structure of the title compound, (I).

The crystal structure of the title Yb—Zn complex is similar to the known crystal structures of the Gd—Zn and Tb—Zn complexes (Wu et al., 2003, 2004). As shown in Figure 1, the complex consists of a discrete octanuclear molecule, which possesses a symmetry center between the two ytterbium (III) ions. All bridges between the metallic ions are formed by two kinds of ligands. Two YbIII ions are linked by two carboxylato groups. ZnII and YbIII ions are bridged by three carboxylato groups, and two ZnII ions are linked by 4,4'-bipy molecule. There are two different coordination circumstances for the ytterbium ions in the titled complex. One ytterbium [Yb1] is coordinated by eight O atoms from one water molecule, three bridging bidentate and two chelating bidentate carboxylato groups. The other [Yb2] is also coordinated by eight O atoms, but from five bridging bidentate, one chelating bidentate carboxylato groups and a water molecule. The coordination sphere around each ytterbium (III) ion is irregular. Each zinc(II) ion is four-coordinated by three O atoms from three bridging carboxylato groups and one N atom from 4,4'-bipy group. The coordination polyhedron is a distorted tetrahedron. As is the common case, the carboxylato groups in the title complex serve as chelating or bridging bidentate ligands. The separations of Yb1···Zn1, Zn1···Zn2, Yb2···Zn2 and Yb2···Yb2* (symmetry code: -x, 1 - y, -z) are 3.870 (1), 11.189 (1), 4.012 (1) and 4.745 (1) Å, respectively. In the crystal, O—H···O and C—H···O hydrogen bonds (Table 1) help to establish the packing.

Experimental

YbL3 (HL = CH2C(CH3)COOH), has been prepared following the known procedure (Lu et al., 1995). YbL3 (860 mg, 2.0 mmol; HL=CH2C(Me)CO2H) and Zn(NO3)2.6H2O (240 mg, 0.8 mmol) were dissolved in H2O (20 ml) and adjusted pH=4.1 with HL (0.1 M). EtOH (3 ml) solution of 4,4'-bipy (60 mg, 0.4 mmol) was added to the mixed solution with stirring. After filtration, the filtrate was allowed to stand at room temperature and single crystals suitable for X-ray work were obtained after 2 weeks.

Refinement

All H-atoms were placed in idealized locations with C–H distances 0.93 - 0.96 Å and refined as riding, with Uiso(H) = 1.2 or 1.5 times Ueq(C). The water' H-atoms were located on a difference map and refined as riding, with Uiso(H) = 0.05 Å-2.

Figures

Fig. 1.
View of (I) showing the atomic numbering of the Yb and Zn atoms. The unlabelled atoms are related with the labelled ones by symmetry operation (-x, 1-y, -z). Displacement ellipsoids are drawn at the 20% probability level. H atoms have been omitted for ...

Crystal data

[Yb4Zn4(C4H5O2)20(C10H8N2)2(H2O)4]Z = 2
Mr = 1519.84F(000) = 1504
Triclinic, P1Dx = 1.722 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 13.398 (3) ÅCell parameters from 14142 reflections
b = 14.880 (3) Åθ = 1.5–27.5°
c = 16.408 (3) ŵ = 4.05 mm1
α = 64.06 (3)°T = 293 K
β = 89.55 (3)°Platelet, colourless
γ = 85.54 (3)°0.26 × 0.22 × 0.10 mm
V = 2931.5 (10) Å3

Data collection

Rigaku R-AXIS RAPID diffractometer10712 independent reflections
Radiation source: fine-focus sealed tube8847 reflections with I > 2σ(I)
graphiteRint = 0.055
Detector resolution: 10.00 pixels mm-1θmax = 25.7°, θmin = 2.1°
ω scansh = −16→15
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)k = −18→18
Tmin = 0.381, Tmax = 0.673l = −19→19
22308 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.066w = 1/[σ2(Fo2) + (0.0305P)2 + 4.1373P] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
10712 reflectionsΔρmax = 0.56 e Å3
714 parametersΔρmin = −0.87 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods

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
Yb10.508466 (13)−0.300505 (13)1.355980 (11)0.02897 (6)
Yb20.004178 (13)0.362808 (13)0.146271 (11)0.02782 (6)
Zn10.37941 (4)−0.14090 (4)1.12076 (3)0.03521 (12)
Zn20.05248 (4)0.20108 (4)0.41429 (3)0.03255 (12)
O10.4222 (2)−0.4461 (2)1.41376 (19)0.0388 (7)
O20.4903 (3)−0.3484 (3)1.5144 (2)0.0486 (9)
O30.5883 (3)−0.2324 (3)1.4400 (2)0.0607 (11)
O40.6321 (2)−0.4369 (2)1.4082 (2)0.0422 (8)
O50.6751 (2)−0.2949 (2)1.3032 (2)0.0447 (8)
O60.3458 (2)−0.2437 (2)1.3379 (2)0.0440 (8)
O70.2706 (2)−0.1904 (3)1.2026 (2)0.0430 (8)
O80.4883 (2)−0.3320 (2)1.23534 (19)0.0403 (7)
O90.4813 (3)−0.2225 (3)1.0916 (2)0.0519 (9)
O100.5116 (2)−0.1372 (2)1.2531 (2)0.0443 (8)
O110.4339 (2)−0.0260 (2)1.1270 (2)0.0435 (8)
O120.1318 (2)0.1243 (2)0.36295 (19)0.0409 (7)
O130.1356 (2)0.2590 (2)0.23113 (19)0.0369 (7)
O140.0948 (3)0.3303 (2)0.39321 (19)0.0431 (8)
O150.0481 (3)0.4258 (2)0.2485 (2)0.0465 (8)
O16−0.0884 (2)0.1816 (2)0.41191 (19)0.0433 (8)
O17−0.0915 (2)0.2780 (2)0.2644 (2)0.0444 (8)
O18−0.0054 (2)0.2014 (2)0.14016 (19)0.0375 (7)
O190.0683 (2)0.3203 (2)0.03094 (19)0.0387 (7)
O20−0.1357 (2)0.3832 (2)0.05811 (19)0.0423 (8)
O21−0.1044 (2)0.5200 (2)−0.0638 (2)0.0394 (7)
O22−0.0976 (2)0.5133 (2)0.12861 (19)0.0423 (8)
N10.2990 (3)−0.0752 (3)0.9994 (2)0.0352 (8)
N20.0968 (3)0.1303 (3)0.5499 (2)0.0311 (8)
C10.5478 (3)−0.2838 (4)1.5125 (3)0.0394 (11)
C20.5691 (4)−0.2710 (5)1.5954 (4)0.0592 (15)
C30.6218 (6)−0.1922 (8)1.5880 (6)0.129 (4)
H3A0.6349−0.18271.63910.155*
H3B0.6444−0.14851.53180.155*
C40.5330 (10)−0.3390 (9)1.6756 (5)0.166 (5)
H4A0.5645−0.40461.69030.250*
H4B0.4619−0.33951.66940.250*
H4C0.5474−0.32031.72310.250*
C50.6960 (3)−0.3867 (4)1.3531 (3)0.0393 (11)
C60.7951 (4)−0.4363 (4)1.3467 (3)0.0503 (13)
C70.8043 (5)−0.5372 (5)1.3754 (5)0.080 (2)
H7A0.8657−0.56931.37240.096*
H7B0.7493−0.57421.39810.096*
C80.8749 (5)−0.3738 (5)1.3112 (5)0.092 (2)
H8A0.9332−0.41311.30700.138*
H8B0.8898−0.34391.35060.138*
H8C0.8557−0.32201.25200.138*
C90.2693 (3)−0.2205 (3)1.2876 (3)0.0336 (10)
C100.1684 (4)−0.2281 (3)1.3292 (3)0.0446 (12)
C110.1633 (5)−0.2555 (5)1.4193 (4)0.0707 (18)
H11A0.1013−0.25961.44610.085*
H11B0.2218−0.27021.45440.085*
C120.0810 (4)−0.2040 (5)1.2696 (4)0.0681 (17)
H12A0.0217−0.20191.30230.102*
H12B0.0776−0.25421.24810.102*
H12C0.0857−0.13981.21900.102*
C130.5172 (3)−0.3026 (4)1.1559 (3)0.0378 (10)
C140.5975 (4)−0.3629 (4)1.1343 (3)0.0527 (13)
C150.6227 (6)−0.4576 (5)1.1916 (4)0.083 (2)
H15A0.6745−0.49391.17810.099*
H15B0.5887−0.48781.24530.099*
C160.6496 (6)−0.3128 (7)1.0490 (5)0.128 (4)
H16A0.7204−0.33011.05970.192*
H16B0.6362−0.24151.02590.192*
H16C0.6263−0.33401.00560.192*
C170.4874 (3)−0.0490 (3)1.1985 (3)0.0355 (10)
C180.5211 (3)0.0348 (3)1.2153 (3)0.0403 (11)
C190.5493 (5)0.0133 (5)1.3069 (4)0.0733 (19)
H19A0.5922−0.04781.33290.110*
H19B0.49030.00581.34210.110*
H19C0.58410.06731.30670.110*
C200.5244 (4)0.1279 (4)1.1437 (4)0.0552 (14)
H20A0.54560.18071.15320.066*
H20B0.50540.13811.08570.066*
C210.2442 (3)−0.1296 (4)0.9731 (3)0.0433 (12)
H210.2348−0.19491.01470.052*
C220.2005 (3)−0.0942 (3)0.8872 (3)0.0422 (12)
H220.1634−0.13510.87190.051*
C230.2130 (3)0.0040 (3)0.8243 (3)0.0305 (9)
C240.2674 (3)0.0619 (3)0.8531 (3)0.0350 (10)
H240.27520.12860.81400.042*
C250.3093 (3)0.0202 (3)0.9393 (3)0.0363 (10)
H250.34630.05950.95670.044*
C260.1713 (3)0.0460 (3)0.7295 (3)0.0300 (9)
C270.0940 (3)0.0057 (3)0.7037 (3)0.0347 (10)
H270.0655−0.05030.74630.042*
C280.0598 (3)0.0494 (3)0.6141 (3)0.0352 (10)
H280.00860.02100.59800.042*
C290.1710 (3)0.1685 (4)0.5750 (3)0.0417 (12)
H290.19740.22510.53120.050*
C300.2106 (4)0.1290 (3)0.6619 (3)0.0429 (12)
H300.26360.15770.67520.052*
C310.1603 (3)0.1684 (3)0.2823 (3)0.0311 (9)
C320.2290 (3)0.1077 (4)0.2499 (3)0.0407 (11)
C330.2556 (5)0.0025 (4)0.3141 (5)0.078 (2)
H33A0.2943−0.03050.28400.118*
H33B0.1956−0.03070.33610.118*
H33C0.29430.00000.36410.118*
C340.2629 (4)0.1506 (5)0.1663 (3)0.0586 (15)
H34A0.30610.11360.14550.070*
H34B0.24350.21750.12870.070*
C350.0932 (3)0.4102 (3)0.3202 (3)0.0349 (10)
C360.1514 (4)0.4908 (4)0.3226 (4)0.0472 (12)
C370.1837 (6)0.4796 (5)0.4124 (5)0.092 (2)
H37A0.23400.42460.43840.137*
H37B0.12730.46690.45120.137*
H37C0.21070.54020.40600.137*
C380.1730 (6)0.5662 (5)0.2448 (5)0.089 (2)
H38A0.21060.61610.24500.107*
H38B0.15050.56910.19010.107*
C39−0.1328 (3)0.2246 (3)0.3347 (3)0.0338 (10)
C40−0.2415 (4)0.2103 (4)0.3314 (3)0.0540 (14)
C41−0.2866 (5)0.1437 (6)0.4176 (4)0.091 (3)
H41A−0.35550.13800.40650.136*
H41B−0.28250.17150.46030.136*
H41C−0.25080.07850.44190.136*
C42−0.2898 (5)0.2550 (6)0.2518 (4)0.087 (2)
H42A−0.35700.24560.24730.104*
H42B−0.25660.29580.20050.104*
C430.0392 (3)0.2328 (3)0.0665 (3)0.0379 (10)
C440.0579 (4)0.1662 (4)0.0197 (3)0.0479 (12)
C450.0655 (5)0.0604 (4)0.0732 (4)0.0715 (17)
H45A0.07190.02750.03430.107*
H45B0.00650.04140.10830.107*
H45C0.12330.04100.11320.107*
C460.0688 (7)0.2109 (6)−0.0730 (4)0.099 (3)
H46A0.08190.1715−0.10350.119*
H46B0.06320.2805−0.10490.119*
C47−0.1625 (3)0.4572 (3)−0.0149 (3)0.0321 (9)
C48−0.2703 (4)0.4716 (4)−0.0459 (3)0.0473 (12)
C49−0.3324 (5)0.3943 (6)0.0011 (4)0.090 (2)
H49A−0.36860.40840.04540.136*
H49B−0.29220.33180.03080.136*
H49C−0.37890.3898−0.04100.136*
C50−0.3050 (5)0.5593 (5)−0.1184 (5)0.102 (3)
H50A−0.37160.5689−0.13800.123*
H50B−0.26180.6090−0.14800.123*
H110.3881−0.45671.46620.050*
H120.4449−0.48781.40710.050*
H221−0.09770.55820.08760.050*
H222−0.07580.52490.16990.050*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Yb10.03336 (11)0.02672 (11)0.02086 (9)−0.00583 (8)−0.00164 (7)−0.00436 (7)
Yb20.03188 (10)0.02507 (10)0.02023 (9)−0.00485 (7)−0.00078 (7)−0.00371 (7)
Zn10.0385 (3)0.0378 (3)0.0230 (2)−0.0006 (2)−0.00541 (19)−0.0078 (2)
Zn20.0398 (3)0.0327 (3)0.0220 (2)−0.0039 (2)−0.00316 (19)−0.0088 (2)
O10.0408 (17)0.0384 (18)0.0302 (16)−0.0134 (14)0.0035 (13)−0.0071 (14)
O20.063 (2)0.052 (2)0.0346 (18)−0.0232 (18)0.0095 (15)−0.0192 (16)
O30.083 (3)0.064 (2)0.041 (2)−0.037 (2)0.0079 (18)−0.0232 (18)
O40.0396 (17)0.0379 (18)0.0347 (17)−0.0034 (14)0.0049 (13)−0.0026 (14)
O50.0398 (18)0.0340 (19)0.052 (2)−0.0090 (15)0.0091 (15)−0.0103 (16)
O60.0442 (18)0.051 (2)0.0347 (17)0.0089 (16)−0.0061 (14)−0.0183 (16)
O70.0372 (17)0.054 (2)0.0322 (17)−0.0081 (15)0.0002 (13)−0.0132 (15)
O80.0495 (19)0.0397 (18)0.0297 (16)−0.0083 (15)0.0003 (13)−0.0126 (14)
O90.062 (2)0.057 (2)0.0233 (16)0.0184 (18)−0.0027 (14)−0.0088 (16)
O100.057 (2)0.0262 (17)0.0407 (18)−0.0075 (15)−0.0019 (15)−0.0059 (14)
O110.0485 (19)0.0404 (19)0.0361 (17)−0.0053 (15)−0.0078 (14)−0.0113 (15)
O120.057 (2)0.0312 (17)0.0310 (17)−0.0022 (15)0.0075 (14)−0.0107 (14)
O130.0365 (16)0.0326 (17)0.0351 (16)0.0003 (13)−0.0049 (13)−0.0092 (14)
O140.065 (2)0.0320 (17)0.0274 (16)−0.0075 (15)−0.0102 (14)−0.0076 (14)
O150.070 (2)0.0345 (18)0.0327 (17)0.0013 (16)−0.0168 (15)−0.0130 (15)
O160.0419 (18)0.053 (2)0.0277 (16)−0.0123 (16)−0.0020 (13)−0.0099 (15)
O170.0420 (18)0.049 (2)0.0309 (17)−0.0106 (15)0.0097 (13)−0.0066 (15)
O180.0474 (18)0.0314 (17)0.0314 (16)−0.0107 (14)0.0021 (13)−0.0103 (13)
O190.0533 (19)0.0304 (17)0.0279 (15)−0.0091 (15)0.0050 (13)−0.0077 (13)
O200.0411 (18)0.0414 (19)0.0314 (17)−0.0079 (15)−0.0094 (13)−0.0030 (15)
O210.0435 (18)0.0332 (17)0.0366 (17)−0.0138 (14)0.0048 (14)−0.0092 (14)
O220.055 (2)0.0366 (18)0.0280 (16)0.0050 (15)0.0004 (14)−0.0085 (14)
N10.036 (2)0.037 (2)0.0253 (18)0.0001 (16)−0.0086 (14)−0.0073 (16)
N20.0373 (19)0.0298 (19)0.0221 (17)−0.0039 (16)−0.0028 (14)−0.0073 (15)
C10.039 (3)0.042 (3)0.036 (3)0.003 (2)−0.0077 (19)−0.017 (2)
C20.058 (3)0.085 (4)0.044 (3)−0.001 (3)−0.008 (2)−0.038 (3)
C30.132 (7)0.216 (11)0.118 (7)−0.097 (8)0.043 (6)−0.132 (8)
C40.278 (15)0.189 (11)0.049 (5)−0.084 (11)0.021 (7)−0.057 (6)
C50.038 (2)0.046 (3)0.034 (2)−0.010 (2)0.0030 (19)−0.016 (2)
C60.042 (3)0.055 (3)0.049 (3)0.005 (2)0.003 (2)−0.019 (3)
C70.061 (4)0.057 (4)0.096 (5)0.018 (3)0.015 (3)−0.013 (4)
C80.057 (4)0.088 (5)0.120 (6)−0.009 (4)0.037 (4)−0.035 (5)
C90.037 (2)0.026 (2)0.037 (2)−0.0049 (19)0.0021 (19)−0.0122 (19)
C100.040 (3)0.032 (3)0.060 (3)−0.009 (2)0.012 (2)−0.017 (2)
C110.069 (4)0.081 (5)0.053 (4)−0.001 (3)0.029 (3)−0.023 (3)
C120.036 (3)0.074 (4)0.098 (5)−0.007 (3)0.008 (3)−0.041 (4)
C130.039 (2)0.044 (3)0.028 (2)−0.003 (2)−0.0026 (18)−0.014 (2)
C140.059 (3)0.058 (3)0.036 (3)0.019 (3)−0.007 (2)−0.019 (3)
C150.109 (6)0.055 (4)0.070 (4)0.022 (4)0.013 (4)−0.018 (3)
C160.116 (6)0.146 (8)0.061 (5)0.067 (6)0.034 (4)−0.001 (5)
C170.031 (2)0.035 (3)0.035 (2)−0.0074 (19)0.0042 (18)−0.010 (2)
C180.037 (2)0.034 (3)0.047 (3)−0.007 (2)−0.001 (2)−0.015 (2)
C190.110 (5)0.058 (4)0.056 (4)−0.015 (4)−0.016 (3)−0.027 (3)
C200.064 (3)0.040 (3)0.054 (3)−0.012 (3)−0.001 (3)−0.012 (3)
C210.047 (3)0.038 (3)0.032 (2)−0.012 (2)−0.007 (2)−0.002 (2)
C220.045 (3)0.040 (3)0.031 (2)−0.015 (2)−0.0101 (19)−0.004 (2)
C230.030 (2)0.032 (2)0.022 (2)−0.0040 (18)−0.0004 (16)−0.0053 (17)
C240.043 (3)0.030 (2)0.024 (2)−0.005 (2)−0.0034 (18)−0.0044 (18)
C250.041 (2)0.036 (3)0.028 (2)−0.003 (2)−0.0085 (18)−0.0102 (19)
C260.030 (2)0.032 (2)0.022 (2)−0.0007 (18)−0.0030 (16)−0.0071 (18)
C270.042 (2)0.028 (2)0.025 (2)−0.0108 (19)−0.0036 (17)−0.0028 (18)
C280.040 (2)0.034 (2)0.030 (2)−0.013 (2)−0.0044 (18)−0.0106 (19)
C290.046 (3)0.041 (3)0.024 (2)−0.017 (2)−0.0023 (18)0.0015 (19)
C300.049 (3)0.042 (3)0.025 (2)−0.020 (2)−0.0111 (19)0.0004 (19)
C310.034 (2)0.028 (2)0.027 (2)−0.0023 (18)−0.0046 (17)−0.0093 (18)
C320.041 (3)0.039 (3)0.043 (3)−0.001 (2)0.000 (2)−0.020 (2)
C330.099 (5)0.036 (3)0.089 (5)0.005 (3)0.035 (4)−0.018 (3)
C340.050 (3)0.071 (4)0.044 (3)0.018 (3)0.004 (2)−0.018 (3)
C350.041 (2)0.030 (2)0.032 (2)−0.0011 (19)−0.0019 (18)−0.012 (2)
C360.053 (3)0.034 (3)0.058 (3)−0.003 (2)−0.002 (2)−0.023 (2)
C370.109 (6)0.075 (5)0.102 (5)−0.023 (4)−0.039 (4)−0.046 (4)
C380.136 (7)0.050 (4)0.095 (5)−0.045 (4)0.041 (5)−0.039 (4)
C390.037 (2)0.036 (2)0.033 (2)−0.011 (2)0.0035 (18)−0.019 (2)
C400.051 (3)0.070 (4)0.039 (3)−0.028 (3)0.000 (2)−0.017 (3)
C410.068 (4)0.138 (7)0.056 (4)−0.058 (5)0.012 (3)−0.024 (4)
C420.059 (4)0.126 (6)0.061 (4)−0.040 (4)−0.010 (3)−0.022 (4)
C430.041 (3)0.035 (3)0.034 (2)0.001 (2)−0.0076 (19)−0.012 (2)
C440.055 (3)0.045 (3)0.051 (3)−0.003 (2)0.000 (2)−0.028 (3)
C450.087 (5)0.054 (4)0.083 (4)−0.011 (3)0.007 (4)−0.039 (3)
C460.186 (9)0.070 (5)0.054 (4)0.003 (5)0.008 (5)−0.040 (4)
C470.031 (2)0.033 (2)0.031 (2)−0.0052 (19)−0.0022 (17)−0.0126 (19)
C480.038 (3)0.057 (3)0.039 (3)−0.005 (2)−0.011 (2)−0.013 (2)
C490.059 (4)0.104 (6)0.082 (5)−0.039 (4)−0.016 (3)−0.011 (4)
C500.054 (4)0.085 (5)0.105 (6)−0.006 (4)−0.032 (4)0.017 (4)

Geometric parameters (Å, °)

Yb1—O82.247 (3)C12—H12A0.9600
Yb1—O62.249 (3)C12—H12B0.9600
Yb1—O102.276 (3)C12—H12C0.9600
Yb1—O32.342 (3)C13—C141.486 (7)
Yb1—O12.346 (3)C14—C151.325 (8)
Yb1—O42.361 (3)C14—C161.468 (8)
Yb1—O52.383 (3)C15—H15A0.9300
Yb1—O22.392 (3)C15—H15B0.9300
Yb1—H122.7404 (8)C16—H16A0.9600
Yb2—O21i2.224 (3)C16—H16B0.9600
Yb2—O172.250 (3)C16—H16C0.9600
Yb2—O132.271 (3)C17—C181.492 (6)
Yb2—O202.295 (3)C18—C201.373 (6)
Yb2—O152.349 (3)C18—C191.438 (7)
Yb2—O192.378 (3)C19—H19A0.9600
Yb2—O222.433 (3)C19—H19B0.9600
Yb2—O182.461 (3)C19—H19C0.9600
Yb2—H2222.7437 (7)C20—H20A0.9300
Zn1—O71.934 (3)C20—H20B0.9300
Zn1—O91.950 (4)C21—C221.386 (6)
Zn1—O111.954 (3)C21—H210.9300
Zn1—N12.061 (3)C22—C231.395 (6)
Zn2—O141.929 (3)C22—H220.9300
Zn2—O161.935 (3)C23—C241.399 (6)
Zn2—O121.945 (3)C23—C261.493 (5)
Zn2—N22.071 (3)C24—C251.375 (5)
O1—H110.927C24—H240.9300
O1—H120.720C25—H250.9300
O2—C11.267 (5)C26—C301.389 (5)
O3—C11.246 (5)C26—C271.392 (6)
O4—C51.267 (5)C27—C281.385 (5)
O5—C51.257 (5)C27—H270.9300
O6—C91.249 (5)C28—H280.9300
O7—C91.265 (5)C29—C301.374 (6)
O8—C131.249 (5)C29—H290.9300
O9—C131.259 (5)C30—H300.9300
O10—C171.241 (5)C31—C321.492 (6)
O11—C171.277 (5)C32—C341.328 (7)
O12—C311.265 (5)C32—C331.471 (7)
O13—C311.256 (5)C33—H33A0.9600
O14—C351.265 (5)C33—H33B0.9600
O15—C351.245 (5)C33—H33C0.9600
O16—C391.269 (5)C34—H34A0.9300
O17—C391.235 (5)C34—H34B0.9300
O18—C431.256 (5)C35—C361.495 (6)
O19—C431.265 (5)C36—C381.328 (8)
O20—C471.252 (5)C36—C371.473 (8)
O21—C471.253 (5)C37—H37A0.9600
O21—Yb2i2.224 (3)C37—H37B0.9600
O22—H2210.712C37—H37C0.9600
O22—H2220.830C38—H38A0.9300
N1—C211.335 (6)C38—H38B0.9300
N1—C251.346 (5)C39—C401.493 (6)
N2—C281.334 (5)C40—C421.324 (7)
N2—C291.333 (5)C40—C411.484 (7)
C1—C21.485 (6)C41—H41A0.9600
C2—C41.375 (10)C41—H41B0.9600
C2—C31.375 (9)C41—H41C0.9600
C3—H3A0.9300C42—H42A0.9300
C3—H3B0.9300C42—H42B0.9300
C4—H4A0.9600C43—C441.501 (7)
C4—H4B0.9600C44—C461.379 (8)
C4—H4C0.9600C44—C451.424 (7)
C5—C61.495 (7)C45—H45A0.9600
C6—C71.358 (8)C45—H45B0.9600
C6—C81.421 (8)C45—H45C0.9600
C7—H7A0.9300C46—H46A0.9300
C7—H7B0.9300C46—H46B0.9300
C8—H8A0.9600C47—C481.503 (6)
C8—H8B0.9600C48—C501.376 (8)
C8—H8C0.9600C48—C491.405 (7)
C9—C101.500 (6)C49—H49A0.9600
C10—C111.353 (7)C49—H49B0.9600
C10—C121.450 (7)C49—H49C0.9600
C11—H11A0.9300C50—H50A0.9300
C11—H11B0.9300C50—H50B0.9300
O8—Yb1—O687.66 (12)O7—C9—C10116.8 (4)
O8—Yb1—O1085.68 (11)C11—C10—C12123.6 (5)
O6—Yb1—O1077.08 (13)C11—C10—C9118.9 (5)
O8—Yb1—O3154.05 (12)C12—C10—C9117.6 (5)
O6—Yb1—O3108.06 (14)C10—C11—H11A120.0
O10—Yb1—O378.23 (12)C10—C11—H11B120.0
O8—Yb1—O176.44 (11)H11A—C11—H11B120.0
O6—Yb1—O175.57 (12)C10—C12—H12A109.5
O10—Yb1—O1147.73 (11)C10—C12—H12B109.5
O3—Yb1—O1126.74 (11)H12A—C12—H12B109.5
O8—Yb1—O486.29 (12)C10—C12—H12C109.5
O6—Yb1—O4149.31 (11)H12A—C12—H12C109.5
O10—Yb1—O4132.26 (11)H12B—C12—H12C109.5
O3—Yb1—O489.59 (14)O8—C13—O9122.7 (4)
O1—Yb1—O473.76 (11)O8—C13—C14120.0 (4)
O8—Yb1—O578.57 (12)O9—C13—C14117.3 (4)
O6—Yb1—O5151.91 (11)C15—C14—C16121.5 (6)
O10—Yb1—O577.56 (12)C15—C14—C13120.8 (5)
O3—Yb1—O578.16 (13)C16—C14—C13117.6 (5)
O1—Yb1—O5123.51 (11)C14—C15—H15A120.0
O4—Yb1—O554.73 (11)C14—C15—H15B120.0
O8—Yb1—O2149.68 (11)H15A—C15—H15B120.0
O6—Yb1—O287.13 (12)C14—C16—H16A109.5
O10—Yb1—O2122.00 (12)C14—C16—H16B109.5
O3—Yb1—O254.35 (11)H16A—C16—H16B109.5
O1—Yb1—O273.33 (11)C14—C16—H16C109.5
O4—Yb1—O283.13 (12)H16A—C16—H16C109.5
O5—Yb1—O2116.77 (12)H16B—C16—H16C109.5
O8—Yb1—H1268.90 (8)O10—C17—O11122.5 (4)
O6—Yb1—H1286.96 (9)O10—C17—C18120.0 (4)
O10—Yb1—H12150.56 (8)O11—C17—C18117.6 (4)
O3—Yb1—H12130.74 (9)C20—C18—C19123.2 (5)
O1—Yb1—H1213.64 (8)C20—C18—C17119.1 (4)
O4—Yb1—H1262.82 (8)C19—C18—C17117.6 (4)
O5—Yb1—H12110.10 (8)C18—C19—H19A109.5
O2—Yb1—H1281.01 (8)C18—C19—H19B109.5
O21i—Yb2—O17156.53 (12)H19A—C19—H19B109.5
O21i—Yb2—O1391.86 (11)C18—C19—H19C109.5
O17—Yb2—O1386.55 (11)H19A—C19—H19C109.5
O21i—Yb2—O20107.46 (11)H19B—C19—H19C109.5
O17—Yb2—O2085.43 (11)C18—C20—H20A120.0
O13—Yb2—O20147.43 (11)C18—C20—H20B120.0
O21i—Yb2—O1578.21 (12)H20A—C20—H20B120.0
O17—Yb2—O1578.83 (12)N1—C21—C22123.8 (4)
O13—Yb2—O1574.24 (11)N1—C21—H21118.1
O20—Yb2—O15134.39 (13)C22—C21—H21118.1
O21i—Yb2—O1972.77 (11)C21—C22—C23118.8 (4)
O17—Yb2—O19130.18 (11)C21—C22—H22120.6
O13—Yb2—O1984.25 (11)C23—C22—H22120.6
O20—Yb2—O1977.13 (12)C22—C23—C24117.3 (4)
O15—Yb2—O19143.07 (12)C22—C23—C26121.7 (4)
O21i—Yb2—O2279.59 (11)C24—C23—C26121.0 (4)
O17—Yb2—O2286.73 (12)C25—C24—C23119.9 (4)
O13—Yb2—O22140.30 (11)C25—C24—H24120.0
O20—Yb2—O2270.56 (12)C23—C24—H24120.0
O15—Yb2—O2266.07 (11)N1—C25—C24122.8 (4)
O19—Yb2—O22128.18 (10)N1—C25—H25118.6
O21i—Yb2—O18125.10 (11)C24—C25—H25118.6
O17—Yb2—O1876.73 (12)C30—C26—C27116.8 (4)
O13—Yb2—O1873.01 (11)C30—C26—C23119.8 (4)
O20—Yb2—O1874.43 (11)C27—C26—C23123.5 (4)
O15—Yb2—O18139.90 (10)C28—C27—C26119.7 (4)
O19—Yb2—O1853.76 (10)C28—C27—H27120.2
O22—Yb2—O18142.24 (11)C26—C27—H27120.2
O21i—Yb2—H22278.36 (9)N2—C28—C27123.1 (4)
O17—Yb2—H22282.96 (9)N2—C28—H28118.4
O13—Yb2—H222123.21 (8)C27—C28—H28118.4
O20—Yb2—H22286.98 (9)N2—C29—C30123.8 (4)
O15—Yb2—H22248.96 (8)N2—C29—H29118.1
O19—Yb2—H222140.72 (7)C30—C29—H29118.1
O22—Yb2—H22217.13 (7)C29—C30—C26119.6 (4)
O18—Yb2—H222153.31 (7)C29—C30—H30120.2
O7—Zn1—O9125.99 (15)C26—C30—H30120.2
O7—Zn1—O11112.47 (14)O13—C31—O12123.3 (4)
O9—Zn1—O11112.01 (15)O13—C31—C32120.2 (4)
O7—Zn1—N199.31 (14)O12—C31—C32116.5 (4)
O9—Zn1—N199.50 (14)C34—C32—C33123.7 (5)
O11—Zn1—N1102.42 (14)C34—C32—C31119.2 (5)
O14—Zn2—O16120.46 (15)C33—C32—C31117.1 (4)
O14—Zn2—O12117.56 (14)C32—C33—H33A109.5
O16—Zn2—O12111.17 (14)C32—C33—H33B109.5
O14—Zn2—N295.41 (13)H33A—C33—H33B109.5
O16—Zn2—N2105.31 (13)C32—C33—H33C109.5
O12—Zn2—N2102.77 (14)H33A—C33—H33C109.5
Yb1—O1—H11114.0 (2)H33B—C33—H33C109.5
Yb1—O1—H12116.1 (3)C32—C34—H34A120.0
H11—O1—H12120.6 (3)C32—C34—H34B120.0
C1—O2—Yb192.0 (3)H34A—C34—H34B120.0
C1—O3—Yb194.9 (3)O15—C35—O14125.5 (4)
C5—O4—Yb193.2 (3)O15—C35—C36118.9 (4)
C5—O5—Yb192.4 (3)O14—C35—C36115.6 (4)
C9—O6—Yb1145.4 (3)C38—C36—C37124.0 (5)
C9—O7—Zn1129.3 (3)C38—C36—C35118.9 (5)
C13—O8—Yb1139.5 (3)C37—C36—C35117.2 (5)
C13—O9—Zn1117.3 (3)C36—C37—H37A109.5
C17—O10—Yb1163.9 (3)C36—C37—H37B109.5
C17—O11—Zn1113.7 (3)H37A—C37—H37B109.5
C31—O12—Zn2119.1 (3)C36—C37—H37C109.5
C31—O13—Yb2141.7 (3)H37A—C37—H37C109.5
C35—O14—Zn2129.3 (3)H37B—C37—H37C109.5
C35—O15—Yb2147.5 (3)C36—C38—H38A120.0
C39—O16—Zn2115.9 (3)C36—C38—H38B120.0
C39—O17—Yb2171.8 (3)H38A—C38—H38B120.0
C43—O18—Yb291.0 (3)O17—C39—O16123.7 (4)
C43—O19—Yb294.7 (3)O17—C39—C40119.6 (4)
C47—O20—Yb2127.2 (3)O16—C39—C40116.8 (4)
C47—O21—Yb2i176.6 (3)C42—C40—C41124.8 (5)
Yb2—O22—H221120.8 (3)C42—C40—C39118.1 (5)
Yb2—O22—H222103.1 (2)C41—C40—C39117.1 (4)
H221—O22—H222107.8 (4)C40—C41—H41A109.5
C21—N1—C25117.4 (3)C40—C41—H41B109.5
C21—N1—Zn1120.8 (3)H41A—C41—H41B109.5
C25—N1—Zn1121.4 (3)C40—C41—H41C109.5
C28—N2—C29117.0 (3)H41A—C41—H41C109.5
C28—N2—Zn2126.5 (3)H41B—C41—H41C109.5
C29—N2—Zn2116.6 (3)C40—C42—H42A120.0
O3—C1—O2118.7 (4)C40—C42—H42B120.0
O3—C1—C2120.3 (4)H42A—C42—H42B120.0
O2—C1—C2121.0 (4)O18—C43—O19120.5 (4)
C4—C2—C3123.7 (6)O18—C43—C44119.9 (4)
C4—C2—C1117.3 (6)O19—C43—C44119.6 (4)
C3—C2—C1119.0 (6)C46—C44—C45123.3 (5)
C2—C3—H3A120.0C46—C44—C43118.2 (5)
C2—C3—H3B120.0C45—C44—C43118.5 (5)
H3A—C3—H3B120.0C44—C45—H45A109.5
C2—C4—H4A109.5C44—C45—H45B109.5
C2—C4—H4B109.5H45A—C45—H45B109.5
H4A—C4—H4B109.5C44—C45—H45C109.5
C2—C4—H4C109.5H45A—C45—H45C109.5
H4A—C4—H4C109.5H45B—C45—H45C109.5
H4B—C4—H4C109.5C44—C46—H46A120.0
O5—C5—O4119.6 (4)C44—C46—H46B120.0
O5—C5—C6120.1 (4)H46A—C46—H46B120.0
O4—C5—C6120.3 (4)O21—C47—O20123.7 (4)
C7—C6—C8124.0 (6)O21—C47—C48118.0 (4)
C7—C6—C5118.9 (5)O20—C47—C48118.3 (4)
C8—C6—C5117.1 (5)C50—C48—C49122.2 (5)
C6—C7—H7A120.0C50—C48—C47119.4 (5)
C6—C7—H7B120.0C49—C48—C47118.3 (5)
H7A—C7—H7B120.0C48—C49—H49A109.5
C6—C8—H8A109.5C48—C49—H49B109.5
C6—C8—H8B109.5H49A—C49—H49B109.5
H8A—C8—H8B109.5C48—C49—H49C109.5
C6—C8—H8C109.5H49A—C49—H49C109.5
H8A—C8—H8C109.5H49B—C49—H49C109.5
H8B—C8—H8C109.5C48—C50—H50A120.0
O6—C9—O7124.3 (4)C48—C50—H50B120.0
O6—C9—C10118.8 (4)H50A—C50—H50B120.0

Symmetry codes: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H11···O4ii0.932.012.795 (4)142
O1—H12···O2ii0.722.302.903 (5)142
O22—H221···O19i0.712.062.758 (4)169
C11—H11B···O60.932.442.758 (7)100
C16—H16B···O90.962.392.776 (10)104
C19—H19A···O30.962.543.339 (8)141
C22—H22···O18iii0.932.453.297 (5)152
C24—H24···O5iv0.932.523.435 (6)169
C27—H27···O18iii0.932.403.330 (5)175
C29—H29···O140.932.473.020 (5)118
C30—H30···O5iv0.932.423.256 (6)149
C34—H34B···O130.932.462.772 (7)100
C42—H42B···O170.932.402.726 (7)100
C49—H49B···O200.962.402.772 (7)103
C50—H50B···O13i0.932.593.521 (8)177

Symmetry codes: (ii) −x+1, −y−1, −z+3; (i) −x, −y+1, −z; (iii) −x, −y, −z+1; (iv) −x+1, −y, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2750).

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