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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): m1678.
Published online 2010 November 27. doi:  10.1107/S1600536810048166
PMCID: PMC3011412

catena-Poly[[{diaqua­[2-(4-hy­droxy­phen­yl)acetato-κ2 O,O′]cerium(III)}-bis­[μ-2-(4-hy­droxy­phen­yl)acetato]-κ3 O,O′:O3 O:O,O′] 4,4′-bipyridine disolvate monohydrate]

Abstract

In the polymeric title complex, {[Ce(C8H7O3)3(H2O)2]·2C10H8N2·H2O}n, the CeIII ion is coordinated by ten O atoms from four 2-(4-hy­droxy­phen­yl)acetate (HPAA) ligands and two water mol­ecules. One HPAA ligand coordinates just to one CeIII ion, whereas the remaining two bridge two CeIII ions. The 4,4′-bipyridine mol­ecule and one water mol­ecule are not coordinated to Ce. In the crystal, O—H(...)O and O—H(...)N hydrogen bonds link mol­ecules into a three-dimensional network.

Related literature

For the applications of carb­oxy­lic mental-organic complexes, see: Wang & Sevov (2008 [triangle]); Fang & Zhang (2006 [triangle]); Wang et al. (2010 [triangle]). For a related structure, see: Liu et al. (2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1678-scheme1.jpg

Experimental

Crystal data

  • [Ce(C8H7O3)3(H2O)2]·2C10H8N2·H2O
  • M r = 959.94
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1678-efi1.jpg
  • a = 9.0793 (2) Å
  • b = 12.8371 (3) Å
  • c = 19.5796 (4) Å
  • α = 78.534 (1)°
  • β = 76.716 (1)°
  • γ = 73.121 (1)°
  • V = 2103.82 (8) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.15 mm−1
  • T = 296 K
  • 0.32 × 0.16 × 0.06 mm

Data collection

  • Bruker APEXII area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.800, T max = 0.931
  • 32193 measured reflections
  • 9668 independent reflections
  • 8614 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.032
  • wR(F 2) = 0.109
  • S = 0.87
  • 9668 reflections
  • 550 parameters
  • H-atom parameters constrained
  • Δρmax = 2.13 e Å−3
  • Δρmin = −0.88 e Å−3

Data collection: APEX2 (Bruker, 2006 [triangle]); cell refinement: SAINT (Bruker, 2006 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: XP in SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810048166/bt5395sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048166/bt5395Isup2.hkl

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

supplementary crystallographic information

Comment

The design and synthesis of carboxylic mental-organic complexes have been an increasing interest for decades owing to their potential practical applications, such as fluorescence, magnetism (Wang, et al., 2010; Fang et al., 2006; Wang, et al., 2008). We have worked at it before (Liu, et al., 2010). In the paper, we report the crystal structure of a new ceriumIII complex with the ligand p- hydroxyphenylacetic acid. The title compound consist of six L ligands, two bipy molecules and five water molecules. In the bicentric structure compound, every centric atom is coordinated with nine O atoms from four L ligands and two water molecule. The centric atom is nine coordinated. The PAA ligands are coordinated by two modes, bridging and bridging tridentate. (Fig.1). Two 4,4'–bipyridine (bipy) molecules are dissociative.The ceriumIII atom is in a distort capped pentagonal prism environment. The Ce—O bond length range from 2.5069 (19) Å-2.860 (2) Å. The Ce—O(water) bond length range from 2.5224 (19) Å-2.540 (2) Å, is slightly shorter than other Ce—O bonds. In addition, there are plenty of hydrogen bonds in the crystal structure due to the existence of dissociative water and crystal water molecules. The occurrence of numerous O—H···O involving coordinated and non-coordinated water molecules build up an intricated three dimensionnal network.

Experimental

All reagents and solvents used were of commercially available quality and without purified before using. p-hydroxyphenylacetic acid (HPAA) (0.456 g, 3 mmol) and sodium hydroxide (0.12 g, 3 mmol) were mixed together in water (10 ml), then Ce[(NO3)3] (0.327 g, 1 mmol) dissolved in water(10 ml) was added into the above solution, after stirring for an hour, an ethanol (5 ml) solution of 4,4'-bipyridine (0.156 g, 1 mmol) was slowly dripped into the above solution with stirring for three hours. After filtration, the filtrate was allowed to stand at room temperature, and single crystals were obtained after one week.

Refinement

All H atoms were fixed geometrically and treated as riding with C—H = 0.97 Å (methylene) or 0.93 Å (aromatic) and O—H = 0.82 Å with Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(O).

Figures

Fig. 1.
The molecular structure of the title complex, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

[Ce(C8H7O3)3(H2O)2]·2C10H8N2·H2OZ = 2
Mr = 959.94F(000) = 978
Triclinic, P1Dx = 1.515 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.0793 (2) ÅCell parameters from 9983 reflections
b = 12.8371 (3) Åθ = 1.1–27.7°
c = 19.5796 (4) ŵ = 1.15 mm1
α = 78.534 (1)°T = 296 K
β = 76.716 (1)°Block, colourless
γ = 73.121 (1)°0.32 × 0.16 × 0.06 mm
V = 2103.82 (8) Å3

Data collection

Bruker APEXII area-detector diffractometer9668 independent reflections
Radiation source: fine-focus sealed tube8614 reflections with I > 2σ(I)
graphiteRint = 0.034
phi and ω scansθmax = 27.7°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→11
Tmin = 0.800, Tmax = 0.931k = −16→16
32193 measured reflectionsl = −25→25

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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 0.87w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
9668 reflections(Δ/σ)max = 0.003
550 parametersΔρmax = 2.13 e Å3
0 restraintsΔρmin = −0.88 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
Ce0.763886 (13)−0.024594 (10)0.502284 (7)0.02165 (7)
O10.5164 (2)−0.00623 (18)0.42935 (11)0.0311 (4)
O1W0.6869 (2)−0.20312 (17)0.52006 (11)0.0342 (5)
H10.5949−0.20240.52660.051*
H70.7230−0.25330.55000.051*
O20.7605 (2)−0.04863 (18)0.37493 (11)0.0330 (4)
O2W0.9859 (2)−0.19000 (18)0.46923 (13)0.0405 (5)
H21.0714−0.17620.45890.061*
H50.9845−0.22180.43700.061*
O30.7135 (3)0.1785 (3)0.04269 (14)0.0669 (8)
H15A0.81210.17110.02950.100*
O40.6313 (2)0.17990 (17)0.46325 (12)0.0353 (5)
O50.7312 (2)0.14537 (17)0.55952 (11)0.0331 (4)
O3W0.0235 (3)0.2327 (2)0.67074 (13)0.0496 (6)
H100.09060.17200.66320.074*
H11−0.05120.22500.70090.074*
O60.8176 (3)0.6417 (2)0.29794 (13)0.0520 (6)
H6A0.86480.67700.31130.078*
O70.8060 (2)−0.1038 (2)0.62835 (11)0.0379 (5)
O81.0105 (2)−0.04972 (17)0.56681 (11)0.0300 (4)
O90.8706 (4)−0.4737 (2)0.88856 (16)0.0643 (8)
H9A0.8225−0.45890.92680.096*
N10.3011 (4)0.3471 (3)0.35414 (16)0.0527 (8)
N20.7018 (5)0.5461 (3)0.02036 (19)0.0644 (9)
N30.9775 (4)0.8207 (3)0.01648 (18)0.0590 (8)
N40.2342 (4)0.8067 (3)0.2258 (2)0.0623 (9)
C10.6107 (3)0.0024 (3)0.24341 (15)0.0351 (6)
C20.7638 (4)0.0005 (4)0.21124 (18)0.0534 (10)
H2A0.8446−0.04170.23460.064*
C30.8000 (4)0.0595 (4)0.14557 (18)0.0558 (10)
H3A0.90410.05740.12580.067*
C40.6838 (4)0.1215 (3)0.10881 (17)0.0471 (8)
C50.5313 (4)0.1251 (4)0.1398 (2)0.0576 (10)
H5A0.45090.16690.11610.069*
C60.4958 (4)0.0662 (3)0.20698 (19)0.0493 (9)
H6C0.39150.07050.22750.059*
C70.5671 (4)−0.0639 (3)0.31479 (16)0.0380 (7)
H7A0.4544−0.05300.32530.046*
H7C0.6139−0.14130.31110.046*
C80.6167 (3)−0.0365 (2)0.37653 (14)0.0266 (5)
C90.6708 (3)0.4103 (2)0.46172 (18)0.0374 (7)
C100.6231 (4)0.4333 (3)0.3971 (2)0.0457 (8)
H10A0.55570.39600.38950.055*
C110.6725 (4)0.5099 (3)0.3433 (2)0.0451 (8)
H11A0.63810.52380.30040.054*
C120.7733 (4)0.5663 (3)0.35321 (18)0.0388 (7)
C12A0.9018 (4)−0.3842 (3)0.84258 (19)0.0434 (8)
C130.8237 (4)0.5439 (3)0.41697 (19)0.0431 (7)
H13A0.89200.58080.42420.052*
C140.7731 (4)0.4667 (3)0.4704 (2)0.0445 (7)
H14A0.80840.45230.51320.053*
C150.6064 (4)0.3334 (3)0.5228 (2)0.0488 (8)
H15B0.63560.34200.56560.059*
H15C0.49300.35560.52950.059*
C160.6609 (3)0.2132 (2)0.51396 (16)0.0296 (6)
C170.9711 (4)−0.2083 (3)0.74364 (16)0.0393 (7)
C180.9054 (4)−0.1947 (3)0.81334 (18)0.0437 (8)
H18B0.8836−0.12590.82730.052*
C190.8712 (4)−0.2823 (3)0.86307 (17)0.0431 (8)
H19A0.8279−0.27200.90990.052*
C210.9695 (5)−0.3997 (3)0.7736 (2)0.0504 (9)
H21A0.9923−0.46880.75980.061*
C221.0034 (4)−0.3116 (3)0.72483 (19)0.0482 (9)
H22A1.0490−0.32250.67830.058*
C231.0119 (5)−0.1149 (4)0.68953 (18)0.0559 (11)
H23A0.9810−0.04930.71230.067*
H23B1.1247−0.13210.67440.067*
C240.9378 (3)−0.0893 (2)0.62473 (14)0.0281 (6)
C250.4182 (6)0.2834 (3)0.3156 (2)0.0647 (11)
H25A0.44750.20900.33320.078*
C260.5000 (6)0.3192 (4)0.2510 (2)0.0621 (12)
H26A0.58410.27040.22740.075*
C270.4563 (4)0.4281 (3)0.22159 (19)0.0436 (8)
C280.3305 (4)0.4953 (3)0.2606 (2)0.0531 (9)
H28A0.29510.56930.24330.064*
C290.2579 (5)0.4513 (4)0.3255 (2)0.0559 (10)
H29A0.17350.49790.35070.067*
C300.7752 (6)0.4681 (5)0.0663 (2)0.0732 (14)
H30A0.88230.43850.05320.088*
C310.7007 (5)0.4287 (4)0.1324 (2)0.0635 (12)
H31A0.75740.37490.16270.076*
C320.5425 (5)0.4699 (3)0.15248 (19)0.0460 (8)
C330.4652 (5)0.5511 (3)0.1053 (2)0.0529 (9)
H33A0.35810.58170.11720.063*
C340.5484 (6)0.5862 (4)0.0404 (2)0.0607 (10)
H34A0.49450.64040.00930.073*
C350.9607 (5)0.7396 (4)0.0695 (2)0.0619 (11)
H35A1.05030.68640.07960.074*
C360.8189 (4)0.7299 (3)0.1101 (2)0.0562 (10)
H36A0.81430.67170.14670.067*
C370.6828 (4)0.8073 (3)0.09630 (18)0.0427 (7)
C380.7003 (5)0.8910 (3)0.0407 (2)0.0563 (10)
H38A0.61290.94460.02850.068*
C390.8473 (5)0.8943 (4)0.0038 (2)0.0643 (11)
H39A0.85590.9522−0.03270.077*
C400.3649 (5)0.7732 (4)0.2527 (2)0.0581 (10)
H40A0.35670.75120.30140.070*
C410.5119 (4)0.7694 (3)0.21208 (19)0.0488 (8)
H41A0.60000.74290.23320.059*
C420.5278 (4)0.8048 (3)0.14048 (18)0.0410 (7)
C430.3907 (4)0.8400 (3)0.1118 (2)0.0536 (9)
H43A0.39500.86370.06340.064*
C440.2499 (5)0.8389 (4)0.1563 (2)0.0627 (11)
H44A0.15990.86220.13650.075*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ce0.01870 (9)0.02339 (9)0.02159 (10)−0.00760 (6)−0.00219 (6)0.00130 (6)
O10.0275 (10)0.0399 (11)0.0244 (10)−0.0115 (8)0.0014 (8)−0.0041 (9)
O1W0.0256 (9)0.0320 (10)0.0437 (12)−0.0111 (8)−0.0075 (8)0.0049 (9)
O20.0260 (10)0.0457 (12)0.0287 (11)−0.0128 (8)−0.0021 (8)−0.0066 (9)
O2W0.0254 (10)0.0377 (11)0.0598 (15)−0.0059 (8)−0.0101 (9)−0.0110 (10)
O30.0549 (16)0.095 (2)0.0399 (15)−0.0192 (15)−0.0099 (12)0.0170 (15)
O40.0280 (10)0.0320 (10)0.0452 (13)−0.0091 (8)−0.0090 (9)0.0011 (9)
O50.0275 (10)0.0313 (10)0.0397 (12)−0.0059 (8)−0.0066 (8)−0.0052 (9)
O3W0.0434 (13)0.0503 (14)0.0555 (16)−0.0184 (11)0.0023 (11)−0.0118 (12)
O60.0633 (16)0.0468 (14)0.0495 (15)−0.0268 (12)−0.0112 (12)0.0051 (12)
O70.0308 (11)0.0530 (13)0.0316 (11)−0.0219 (10)−0.0087 (8)0.0102 (10)
O80.0277 (10)0.0363 (11)0.0238 (10)−0.0131 (8)−0.0024 (8)0.0050 (8)
O90.079 (2)0.0490 (15)0.0510 (17)−0.0221 (14)0.0018 (14)0.0174 (13)
N10.0580 (19)0.0592 (19)0.0413 (17)−0.0253 (16)−0.0049 (14)0.0023 (15)
N20.074 (2)0.078 (2)0.0431 (18)−0.039 (2)−0.0085 (16)0.0124 (17)
N30.0514 (18)0.063 (2)0.051 (2)−0.0127 (16)0.0030 (14)−0.0007 (16)
N40.053 (2)0.068 (2)0.064 (2)−0.0255 (17)0.0012 (16)−0.0064 (18)
C10.0346 (15)0.0517 (18)0.0245 (15)−0.0169 (13)−0.0033 (11)−0.0116 (13)
C20.0315 (16)0.095 (3)0.0296 (17)−0.0184 (18)−0.0070 (13)0.0055 (18)
C30.0309 (16)0.098 (3)0.0324 (18)−0.0164 (18)−0.0039 (13)0.0019 (19)
C40.0459 (19)0.065 (2)0.0280 (17)−0.0172 (16)−0.0064 (13)0.0021 (16)
C50.0355 (18)0.079 (3)0.047 (2)−0.0073 (17)−0.0085 (15)0.007 (2)
C60.0293 (16)0.071 (2)0.042 (2)−0.0117 (15)−0.0023 (13)−0.0030 (17)
C70.0358 (16)0.0577 (19)0.0272 (15)−0.0239 (14)−0.0020 (12)−0.0079 (14)
C80.0269 (13)0.0311 (13)0.0226 (13)−0.0129 (10)−0.0026 (10)0.0002 (11)
C90.0349 (15)0.0252 (13)0.0465 (19)−0.0042 (11)−0.0014 (13)−0.0044 (13)
C100.0454 (18)0.0369 (16)0.059 (2)−0.0154 (14)−0.0110 (16)−0.0078 (16)
C110.051 (2)0.0435 (18)0.047 (2)−0.0169 (15)−0.0166 (16)−0.0032 (15)
C120.0371 (16)0.0329 (15)0.0445 (18)−0.0104 (12)−0.0033 (13)−0.0035 (13)
C12A0.0363 (17)0.0494 (19)0.0364 (18)−0.0122 (14)−0.0058 (13)0.0134 (15)
C130.0400 (17)0.0414 (17)0.053 (2)−0.0170 (14)−0.0103 (14)−0.0056 (15)
C140.0490 (19)0.0403 (17)0.044 (2)−0.0108 (14)−0.0108 (15)−0.0045 (14)
C150.056 (2)0.0272 (14)0.052 (2)−0.0065 (14)0.0071 (16)−0.0065 (14)
C160.0182 (12)0.0291 (13)0.0388 (16)−0.0082 (10)0.0019 (11)−0.0037 (12)
C170.0375 (16)0.0552 (19)0.0288 (16)−0.0237 (14)−0.0156 (12)0.0146 (14)
C180.0474 (18)0.0488 (18)0.0356 (18)−0.0180 (15)−0.0133 (14)0.0073 (15)
C190.0453 (18)0.0497 (19)0.0266 (16)−0.0105 (15)−0.0030 (13)0.0057 (14)
C210.058 (2)0.0448 (19)0.040 (2)−0.0069 (17)−0.0055 (16)0.0014 (16)
C220.046 (2)0.063 (2)0.0276 (17)−0.0145 (17)−0.0009 (14)0.0043 (16)
C230.067 (2)0.082 (3)0.0358 (19)−0.055 (2)−0.0277 (17)0.0274 (18)
C240.0292 (13)0.0298 (13)0.0255 (14)−0.0114 (11)−0.0071 (10)0.0038 (11)
C250.092 (3)0.044 (2)0.047 (2)−0.019 (2)0.003 (2)0.0051 (18)
C260.088 (3)0.042 (2)0.045 (2)−0.016 (2)0.006 (2)−0.0031 (17)
C270.053 (2)0.0472 (19)0.0366 (18)−0.0232 (16)−0.0125 (15)0.0018 (15)
C280.057 (2)0.047 (2)0.053 (2)−0.0160 (17)−0.0134 (17)0.0054 (17)
C290.046 (2)0.066 (2)0.049 (2)−0.0094 (18)−0.0044 (17)−0.0048 (19)
C300.060 (3)0.105 (4)0.048 (2)−0.029 (3)−0.0100 (19)0.016 (2)
C310.054 (2)0.084 (3)0.045 (2)−0.021 (2)−0.0115 (18)0.016 (2)
C320.058 (2)0.0497 (19)0.0349 (18)−0.0256 (17)−0.0093 (15)0.0030 (15)
C330.061 (2)0.051 (2)0.046 (2)−0.0181 (17)−0.0127 (17)0.0042 (17)
C340.085 (3)0.055 (2)0.045 (2)−0.026 (2)−0.020 (2)0.0098 (18)
C350.050 (2)0.060 (2)0.064 (3)−0.0048 (18)−0.0095 (19)0.004 (2)
C360.052 (2)0.053 (2)0.055 (2)−0.0130 (17)−0.0110 (17)0.0115 (18)
C370.0490 (19)0.0445 (18)0.0346 (17)−0.0112 (14)−0.0092 (14)−0.0052 (14)
C380.050 (2)0.056 (2)0.049 (2)−0.0050 (17)−0.0049 (16)0.0071 (18)
C390.059 (2)0.067 (3)0.050 (2)−0.012 (2)0.0002 (18)0.013 (2)
C400.062 (2)0.074 (3)0.043 (2)−0.032 (2)−0.0031 (17)−0.0033 (19)
C410.054 (2)0.059 (2)0.0400 (19)−0.0263 (17)−0.0119 (15)−0.0023 (17)
C420.0478 (18)0.0409 (17)0.0368 (18)−0.0143 (14)−0.0087 (14)−0.0053 (14)
C430.051 (2)0.062 (2)0.045 (2)−0.0121 (18)−0.0144 (17)0.0013 (18)
C440.046 (2)0.068 (3)0.072 (3)−0.0138 (19)−0.0143 (19)−0.002 (2)

Geometric parameters (Å, °)

Ce—O8i2.5069 (19)C11—C121.385 (4)
Ce—O1W2.5224 (19)C11—H11A0.9300
Ce—O2W2.540 (2)C12—C131.377 (5)
Ce—O72.546 (2)C12A—C191.377 (5)
Ce—O1ii2.546 (2)C12A—C211.377 (5)
Ce—O52.559 (2)C13—C141.386 (5)
Ce—O22.581 (2)C13—H13A0.9300
Ce—O42.591 (2)C14—H14A0.9300
Ce—O82.726 (2)C15—C161.510 (4)
Ce—O12.860 (2)C15—H15B0.9700
Ce—C162.961 (3)C15—H15C0.9700
O1—C81.254 (3)C17—C221.378 (6)
O1—Ceii2.546 (2)C17—C181.381 (5)
O1W—H10.8129C17—C231.506 (4)
O1W—H70.8259C18—C191.391 (4)
O2—C81.263 (3)C18—H18B0.9300
O2W—H20.8167C19—H19A0.9300
O2W—H50.8211C21—C221.387 (5)
O3—C41.364 (4)C21—H21A0.9300
O3—H15A0.8554C22—H22A0.9300
O4—C161.265 (4)C23—C241.506 (4)
O5—C161.261 (3)C23—H23A0.9700
O3W—H100.8542C23—H23B0.9700
O3W—H110.8061C25—C261.377 (6)
O6—C121.371 (4)C25—H25A0.9300
O6—H6A0.8173C26—C271.381 (5)
O7—C241.248 (3)C26—H26A0.9300
O8—C241.266 (3)C27—C281.386 (5)
O8—Cei2.5069 (19)C27—C321.483 (5)
O9—C12A1.368 (4)C28—C291.384 (5)
O9—H9A0.8033C28—H28A0.9300
N1—C251.320 (5)C29—H29A0.9300
N1—C291.325 (6)C30—C311.388 (6)
N2—C341.331 (6)C30—H30A0.9300
N2—C301.336 (6)C31—C321.371 (6)
N3—C391.320 (5)C31—H31A0.9300
N3—C351.332 (5)C32—C331.386 (5)
N4—C441.328 (6)C33—C341.385 (5)
N4—C401.331 (5)C33—H33A0.9300
C1—C61.372 (5)C34—H34A0.9300
C1—C21.384 (4)C35—C361.374 (6)
C1—C71.517 (4)C35—H35A0.9300
C2—C31.378 (5)C36—C371.386 (5)
C2—H2A0.9300C36—H36A0.9300
C3—C41.378 (5)C37—C381.385 (5)
C3—H3A0.9300C37—C421.479 (5)
C4—C51.370 (5)C38—C391.373 (6)
C5—C61.399 (5)C38—H38A0.9300
C5—H5A0.9300C39—H39A0.9300
C6—H6C0.9300C40—C411.381 (5)
C7—C81.517 (4)C40—H40A0.9300
C7—H7A0.9700C41—C421.373 (5)
C7—H7C0.9700C41—H41A0.9300
C9—C101.381 (5)C42—C431.401 (5)
C9—C141.388 (4)C43—C441.374 (6)
C9—C151.514 (4)C43—H43A0.9300
C10—C111.380 (5)C44—H44A0.9300
C10—H10A0.9300
O8i—Ce—O1W136.43 (7)C10—C11—C12120.1 (3)
O8i—Ce—O2W73.65 (7)C10—C11—H11A120.0
O1W—Ce—O2W64.74 (7)C12—C11—H11A120.0
O8i—Ce—O7110.55 (6)O6—C12—C13123.6 (3)
O1W—Ce—O778.19 (7)O6—C12—C11117.4 (3)
O2W—Ce—O783.99 (8)C13—C12—C11119.0 (3)
O8i—Ce—O1ii150.34 (6)O9—C12A—C19122.8 (3)
O1W—Ce—O1ii72.33 (7)O9—C12A—C21117.2 (4)
O2W—Ce—O1ii136.01 (7)C19—C12A—C21120.0 (3)
O7—Ce—O1ii78.23 (7)C12—C13—C14120.2 (3)
O8i—Ce—O577.23 (7)C12—C13—H13A119.9
O1W—Ce—O5143.84 (7)C14—C13—H13A119.9
O2W—Ce—O5136.14 (6)C13—C14—C9121.6 (3)
O7—Ce—O576.35 (7)C13—C14—H14A119.2
O1ii—Ce—O577.63 (7)C9—C14—H14A119.2
O8i—Ce—O278.68 (6)C16—C15—C9115.2 (3)
O1W—Ce—O277.07 (7)C16—C15—H15B108.5
O2W—Ce—O272.36 (7)C9—C15—H15B108.5
O7—Ce—O2151.26 (8)C16—C15—H15C108.5
O1ii—Ce—O2107.60 (6)C9—C15—H15C108.5
O5—Ce—O2132.24 (7)H15B—C15—H15C107.5
O8i—Ce—O476.99 (6)O5—C16—O4120.1 (3)
O1W—Ce—O4134.93 (6)O5—C16—C15119.1 (3)
O2W—Ce—O4145.40 (7)O4—C16—C15120.7 (3)
O7—Ce—O4123.87 (8)O5—C16—Ce59.33 (14)
O1ii—Ce—O474.92 (7)O4—C16—Ce60.83 (14)
O5—Ce—O450.30 (6)C15—C16—Ce177.9 (2)
O2—Ce—O484.35 (7)C22—C17—C18118.0 (3)
O8i—Ce—O861.86 (7)C22—C17—C23120.2 (3)
O1W—Ce—O8110.71 (6)C18—C17—C23121.8 (4)
O2W—Ce—O868.19 (7)C17—C18—C19121.2 (3)
O7—Ce—O848.80 (6)C17—C18—H18B119.4
O1ii—Ce—O8121.96 (7)C19—C18—H18B119.4
O5—Ce—O869.35 (6)C12A—C19—C18119.7 (3)
O2—Ce—O8130.05 (6)C12A—C19—H19A120.2
O4—Ce—O8112.67 (6)C18—C19—H19A120.2
O8i—Ce—O1116.84 (6)C12A—C21—C22119.5 (4)
O1W—Ce—O168.04 (6)C12A—C21—H21A120.2
O2W—Ce—O1108.78 (6)C22—C21—H21A120.2
O7—Ce—O1132.61 (6)C17—C22—C21121.6 (4)
O1ii—Ce—O160.72 (7)C17—C22—H22A119.2
O5—Ce—O1113.44 (6)C21—C22—H22A119.2
O2—Ce—O147.09 (6)C24—C23—C17115.4 (3)
O4—Ce—O169.22 (6)C24—C23—H23A108.4
O8—Ce—O1176.85 (5)C17—C23—H23A108.4
O8i—Ce—C1675.45 (7)C24—C23—H23B108.4
O1W—Ce—C16147.01 (7)C17—C23—H23B108.4
O2W—Ce—C16148.25 (7)H23A—C23—H23B107.5
O7—Ce—C16100.25 (8)O7—C24—O8120.7 (2)
O1ii—Ce—C1675.09 (7)O7—C24—C23120.9 (3)
O5—Ce—C1625.09 (7)O8—C24—C23118.4 (2)
O2—Ce—C16108.46 (8)N1—C25—C26124.6 (4)
O4—Ce—C1625.22 (7)N1—C25—H25A117.7
O8—Ce—C1690.84 (7)C26—C25—H25A117.7
O1—Ce—C1691.55 (7)C25—C26—C27119.6 (4)
C8—O1—Ceii150.02 (17)C25—C26—H26A120.2
C8—O1—Ce89.20 (15)C27—C26—H26A120.2
Ceii—O1—Ce119.28 (7)C26—C27—C28116.4 (3)
Ce—O1W—H1119.7C26—C27—C32121.1 (4)
Ce—O1W—H7118.2C28—C27—C32122.5 (3)
H1—O1W—H7104.3C29—C28—C27119.4 (4)
C8—O2—Ce102.36 (17)C29—C28—H28A120.3
Ce—O2W—H2112.6C27—C28—H28A120.3
Ce—O2W—H5120.1N1—C29—C28124.2 (4)
H2—O2W—H5104.2N1—C29—H29A117.9
C4—O3—H15A109.7C28—C29—H29A117.9
C16—O4—Ce93.95 (16)N2—C30—C31123.7 (5)
C16—O5—Ce95.58 (17)N2—C30—H30A118.1
H10—O3W—H11113.1C31—C30—H30A118.1
C12—O6—H6A109.4C32—C31—C30119.2 (4)
C24—O7—Ce99.76 (16)C32—C31—H31A120.4
C24—O8—Cei150.65 (18)C30—C31—H31A120.4
C24—O8—Ce90.69 (15)C31—C32—C33117.6 (4)
Cei—O8—Ce118.14 (7)C31—C32—C27121.4 (3)
C12A—O9—H9A113.2C33—C32—C27121.1 (4)
C25—N1—C29115.8 (3)C34—C33—C32119.6 (4)
C34—N2—C30116.7 (4)C34—C33—H33A120.2
C39—N3—C35116.1 (3)C32—C33—H33A120.2
C44—N4—C40116.7 (3)N2—C34—C33123.2 (4)
C6—C1—C2116.9 (3)N2—C34—H34A118.4
C6—C1—C7120.0 (3)C33—C34—H34A118.4
C2—C1—C7123.1 (3)N3—C35—C36123.8 (4)
C3—C2—C1121.8 (3)N3—C35—H35A118.1
C3—C2—H2A119.1C36—C35—H35A118.1
C1—C2—H2A119.1C35—C36—C37119.7 (4)
C2—C3—C4120.8 (3)C35—C36—H36A120.1
C2—C3—H3A119.6C37—C36—H36A120.1
C4—C3—H3A119.6C38—C37—C36116.3 (3)
O3—C4—C5118.4 (3)C38—C37—C42121.3 (3)
O3—C4—C3123.1 (3)C36—C37—C42122.3 (3)
C5—C4—C3118.5 (3)C39—C38—C37119.6 (4)
C4—C5—C6120.2 (3)C39—C38—H38A120.2
C4—C5—H5A119.9C37—C38—H38A120.2
C6—C5—H5A119.9N3—C39—C38124.4 (4)
C1—C6—C5121.8 (3)N3—C39—H39A117.8
C1—C6—H6C119.1C38—C39—H39A117.8
C5—C6—H6C119.1N4—C40—C41123.3 (4)
C8—C7—C1115.4 (2)N4—C40—H40A118.3
C8—C7—H7A108.4C41—C40—H40A118.3
C1—C7—H7A108.4C42—C41—C40119.9 (3)
C8—C7—H7C108.4C42—C41—H41A120.1
C1—C7—H7C108.4C40—C41—H41A120.1
H7A—C7—H7C107.5C41—C42—C43117.1 (3)
O1—C8—O2120.9 (2)C41—C42—C37121.1 (3)
O1—C8—C7120.1 (2)C43—C42—C37121.9 (3)
O2—C8—C7119.0 (2)C44—C43—C42118.8 (4)
C10—C9—C14117.1 (3)C44—C43—H43A120.6
C10—C9—C15122.0 (3)C42—C43—H43A120.6
C14—C9—C15120.7 (3)N4—C44—C43124.2 (4)
C11—C10—C9122.0 (3)N4—C44—H44A117.9
C11—C10—H10A119.0C43—C44—H44A117.9
C9—C10—H10A119.0
O8i—Ce—O1—C843.46 (19)C15—C9—C10—C11174.8 (3)
O1W—Ce—O1—C8−88.73 (17)C9—C10—C11—C120.2 (6)
O2W—Ce—O1—C8−37.27 (17)C10—C11—C12—O6−179.7 (3)
O7—Ce—O1—C8−136.62 (16)C10—C11—C12—C130.5 (5)
O1ii—Ce—O1—C8−170.2 (2)O6—C12—C13—C14179.8 (3)
O5—Ce—O1—C8130.56 (16)C11—C12—C13—C14−0.5 (5)
O2—Ce—O1—C83.87 (15)C12—C13—C14—C9−0.2 (5)
O4—Ce—O1—C8105.94 (17)C10—C9—C14—C130.8 (5)
C16—Ce—O1—C8117.91 (17)C15—C9—C14—C13−174.9 (3)
O8i—Ce—O1—Ceii−146.38 (7)C10—C9—C15—C1671.5 (4)
O1W—Ce—O1—Ceii81.43 (9)C14—C9—C15—C16−113.1 (4)
O2W—Ce—O1—Ceii132.89 (9)Ce—O5—C16—O41.2 (3)
O7—Ce—O1—Ceii33.54 (14)Ce—O5—C16—C15178.4 (2)
O1ii—Ce—O1—Ceii0.0Ce—O4—C16—O5−1.2 (3)
O5—Ce—O1—Ceii−59.29 (10)Ce—O4—C16—C15−178.3 (2)
O2—Ce—O1—Ceii174.03 (14)C9—C15—C16—O5121.8 (3)
O4—Ce—O1—Ceii−83.90 (10)C9—C15—C16—O4−61.0 (4)
C16—Ce—O1—Ceii−71.93 (10)O8i—Ce—C16—O5−90.91 (16)
O8i—Ce—O2—C8−148.50 (18)O1W—Ce—C16—O5101.92 (18)
O1W—Ce—O2—C867.98 (17)O2W—Ce—C16—O5−77.3 (2)
O2W—Ce—O2—C8135.25 (18)O7—Ce—C16—O517.85 (16)
O7—Ce—O2—C899.2 (2)O1ii—Ce—C16—O592.63 (16)
O1ii—Ce—O2—C81.52 (19)O2—Ce—C16—O5−163.42 (15)
O5—Ce—O2—C8−87.59 (18)O4—Ce—C16—O5178.8 (3)
O4—Ce—O2—C8−70.68 (17)O8—Ce—C16—O5−30.32 (16)
O8—Ce—O2—C8174.30 (16)O1—Ce—C16—O5151.73 (15)
O1—Ce—O2—C8−3.94 (15)O8i—Ce—C16—O490.29 (16)
C16—Ce—O2—C8−78.19 (18)O1W—Ce—C16—O4−76.9 (2)
O8i—Ce—O4—C16−83.43 (16)O2W—Ce—C16—O4103.89 (19)
O1W—Ce—O4—C16131.50 (15)O7—Ce—C16—O4−160.95 (15)
O2W—Ce—O4—C16−115.90 (17)O1ii—Ce—C16—O4−86.18 (16)
O7—Ce—O4—C1622.76 (18)O5—Ce—C16—O4−178.8 (3)
O1ii—Ce—O4—C1686.95 (16)O2—Ce—C16—O417.77 (17)
O5—Ce—O4—C160.66 (14)O8—Ce—C16—O4150.87 (16)
O2—Ce—O4—C16−163.09 (16)O1—Ce—C16—O4−27.07 (16)
O8—Ce—O4—C16−31.83 (17)C22—C17—C18—C19−0.6 (5)
O1—Ce—O4—C16150.88 (17)C23—C17—C18—C19−178.7 (3)
O8i—Ce—O5—C1682.91 (16)O9—C12A—C19—C18−179.7 (3)
O1W—Ce—O5—C16−115.47 (17)C21—C12A—C19—C181.6 (5)
O2W—Ce—O5—C16132.19 (16)C17—C18—C19—C12A−0.6 (5)
O7—Ce—O5—C16−161.91 (17)O9—C12A—C21—C22179.9 (3)
O1ii—Ce—O5—C16−81.21 (16)C19—C12A—C21—C22−1.3 (6)
O2—Ce—O5—C1621.44 (19)C18—C17—C22—C210.9 (5)
O4—Ce—O5—C16−0.66 (14)C23—C17—C22—C21179.0 (3)
O8—Ce—O5—C16147.35 (17)C12A—C21—C22—C170.1 (6)
O1—Ce—O5—C16−31.07 (17)C22—C17—C23—C2458.3 (5)
O8i—Ce—O7—C24−2.2 (2)C18—C17—C23—C24−123.7 (4)
O1W—Ce—O7—C24133.2 (2)Ce—O7—C24—O8−3.1 (3)
O2W—Ce—O7—C2467.79 (19)Ce—O7—C24—C23174.8 (3)
O1ii—Ce—O7—C24−152.7 (2)Cei—O8—C24—O7172.5 (3)
O5—Ce—O7—C24−72.71 (19)Ce—O8—C24—O72.9 (3)
O2—Ce—O7—C24102.1 (2)Cei—O8—C24—C23−5.4 (6)
O4—Ce—O7—C24−90.04 (19)Ce—O8—C24—C23−175.1 (3)
O8—Ce—O7—C241.64 (17)C17—C23—C24—O731.7 (5)
O1—Ce—O7—C24177.85 (17)C17—C23—C24—O8−150.3 (3)
C16—Ce—O7—C24−80.40 (19)C29—N1—C25—C263.2 (7)
O8i—Ce—O8—C24174.3 (2)N1—C25—C26—C27−2.5 (8)
O1W—Ce—O8—C24−53.15 (18)C25—C26—C27—C280.4 (7)
O2W—Ce—O8—C24−103.16 (18)C25—C26—C27—C32179.5 (4)
O7—Ce—O8—C24−1.60 (16)C26—C27—C28—C290.6 (6)
O1ii—Ce—O8—C2428.4 (2)C32—C27—C28—C29−178.4 (3)
O5—Ce—O8—C2488.10 (17)C25—N1—C29—C28−2.0 (6)
O2—Ce—O8—C24−143.46 (17)C27—C28—C29—N10.2 (6)
O4—Ce—O8—C24114.31 (17)C34—N2—C30—C31−0.5 (8)
C16—Ce—O8—C24101.32 (17)N2—C30—C31—C320.9 (8)
O8i—Ce—O8—Cei0.0C30—C31—C32—C33−0.9 (7)
O1W—Ce—O8—Cei132.55 (9)C30—C31—C32—C27178.0 (4)
O2W—Ce—O8—Cei82.54 (10)C26—C27—C32—C31−33.7 (6)
O7—Ce—O8—Cei−175.89 (14)C28—C27—C32—C31145.2 (4)
O1ii—Ce—O8—Cei−145.87 (7)C26—C27—C32—C33145.2 (4)
O5—Ce—O8—Cei−86.20 (10)C28—C27—C32—C33−35.8 (5)
O2—Ce—O8—Cei42.25 (13)C31—C32—C33—C340.7 (6)
O4—Ce—O8—Cei−59.98 (11)C27—C32—C33—C34−178.3 (4)
C16—Ce—O8—Cei−72.97 (10)C30—N2—C34—C330.3 (7)
C6—C1—C2—C3−0.3 (6)C32—C33—C34—N2−0.4 (7)
C7—C1—C2—C3178.4 (4)C39—N3—C35—C36−0.2 (7)
C1—C2—C3—C4−1.1 (7)N3—C35—C36—C370.4 (7)
C2—C3—C4—O3−177.8 (4)C35—C36—C37—C380.3 (6)
C2—C3—C4—C51.5 (7)C35—C36—C37—C42−176.6 (4)
O3—C4—C5—C6178.8 (4)C36—C37—C38—C39−1.0 (6)
C3—C4—C5—C6−0.5 (7)C42—C37—C38—C39175.9 (4)
C2—C1—C6—C51.3 (6)C35—N3—C39—C38−0.6 (7)
C7—C1—C6—C5−177.4 (4)C37—C38—C39—N31.3 (8)
C4—C5—C6—C1−0.9 (7)C44—N4—C40—C41−0.9 (7)
C6—C1—C7—C8−119.9 (3)N4—C40—C41—C422.3 (7)
C2—C1—C7—C861.5 (5)C40—C41—C42—C43−2.2 (6)
Ceii—O1—C8—O2−169.4 (2)C40—C41—C42—C37176.7 (4)
Ce—O1—C8—O2−6.8 (3)C38—C37—C42—C41−142.8 (4)
Ceii—O1—C8—C77.8 (5)C36—C37—C42—C4134.0 (5)
Ce—O1—C8—C7170.5 (2)C38—C37—C42—C4336.1 (5)
Ce—O2—C8—O17.7 (3)C36—C37—C42—C43−147.2 (4)
Ce—O2—C8—C7−169.6 (2)C41—C42—C43—C441.0 (6)
C1—C7—C8—O1122.2 (3)C37—C42—C43—C44−177.9 (4)
C1—C7—C8—O2−60.5 (4)C40—N4—C44—C43−0.3 (7)
C14—C9—C10—C11−0.8 (5)C42—C43—C44—N40.3 (7)

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

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1W—H1···O4ii0.811.962.765 (3)172
O1W—H7···N1ii0.832.022.774 (4)151
O2W—H2···O5i0.821.892.703 (3)177
O2W—H5···O3Wii0.822.162.924 (3)155
O3—H15A···N3iii0.861.942.781 (4)168
O6—H6A···O3Wiv0.821.872.684 (3)172
O9—H9A···N2v0.801.912.700 (5)168
O3W—H10···O2ii0.851.912.752 (3)168
O3W—H11···N4vi0.812.012.817 (4)175

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5395).

References

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