metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 3| March 2011| Pages m335-m336

catena-Poly[4,4′-bipyridinium [[tetra­aqua­(pyridine-2,6-di­carboxyl­ato-κ3O2,N,O6)cerate(III)]-μ-pyridine-2,6-di­carboxyl­ato-κ4O2:O2′,N,O6-[(pyridine-2,6-di­carboxyl­ato-κ3O2,N,O6)cerate(III)]-μ-pyridine-2,6-di­carboxyl­ato-κ4O2,N,O6:O6′] penta­hydrate]

aFaculty of Chemistry, Islamic Azad University, North Tehran Branch, Tehran, Iran, bDepartment of Chemistry, School of Sciences, Ferdowsi University of Mashhad, Mashhad 917791436, Iran, and cDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran
*Correspondence e-mail: sara_omidvar_1384@yahoo.com

(Received 2 February 2011; accepted 9 February 2011; online 12 February 2011)

The title compound, {(C10H10N2)[Ce2(C7H3NO4)4(H2O)4]·5H2O}n, is composed of a one-dimensional anionic complex, a doubly protonated 4,4′-bipyridine mol­ecule as a counter-ion and five uncoordinated water mol­ecules. The anion bears two nine-coordinate CeIII ions, each with a distorted tricapped trigonal–prismatic geometry. In the crystal, inter­molecular C—H⋯O, N—H⋯O and O—H⋯O hydrogen bonds, as well as ππ inter­actions with centroid–centroid distances of 3.514 (3) Å connect the various components into a supra­molecular structure.

Related literature

For hydrogen-bonding inter­actions in proton-transfer compounds, see: Aghabozorg et al. (2008[Aghabozorg, H., Manteghi, F. & Sheshmani, S. (2008). J. Iran. Chem. Soc. 5, 184-227.], 2010a[Aghabozorg, H., Eshtiagh-Hosseini, H., Salimi, A. R. & Mirzaei, M. (2010a). J. Iran. Chem. Soc. 7, 289-300.],b[Aghabozorg, H., Moteieyan, E., Salimi, A. R., Mirzaei, M., Manteghi, F., Shokrollahi, A., Derki, S., Ghadermazi, M., Sheshmani, S. & Eshtiagh-Hosseini, H. (2010b). Polyhedron, 29, 1453-1464.]); Sheshmani et al. (2005[Sheshmani, S., Kheirollahi, P. D., Aghabozorg, H., Shokrollahi, A., Kickelbick, G., Shamsipur, M., Ramezanipour, F. & Moghimi, A. (2005). Z. Anorg. Allg. Chem. 631, 3058-3065.]); Soleimannejad et al. (2007[Soleimannejad, J., Aghabozorg, H., Hooshmand, S. & Adams, H. (2007). Acta Cryst. E63, m3089-m3090.]).

[Scheme 1]

Experimental

Crystal data
  • (C10H10N2)[Ce2(C7H3NO4)4(H2O)4]·5H2O

  • Mr = 1261

  • Triclinic, [P \overline 1]

  • a = 13.010 (3) Å

  • b = 13.453 (3) Å

  • c = 13.586 (3) Å

  • α = 99.95 (3)°

  • β = 99.87 (3)°

  • γ = 104.58 (3)°

  • V = 2208.3 (10) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 2.14 mm−1

  • T = 150 K

  • 0.40 × 0.40 × 0.10 mm

Data collection
  • Stoe IPDS II diffractometer

  • Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005[Stoe & Cie (2005). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.440, Tmax = 0.805

  • 25469 measured reflections

  • 11857 independent reflections

  • 10379 reflections with I > 2σ(I)

  • Rint = 0.078

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.120

  • S = 1.05

  • 11857 reflections

  • 716 parameters

  • 12 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 1.96 e Å−3

  • Δρmin = −2.01 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N5—H5A⋯O14 0.82 (3) 1.83 (4) 2.647 (5) 175 (6)
N6—H6A⋯O11i 0.88 (4) 1.63 (4) 2.514 (5) 177 (8)
O17—H17A⋯O2 0.82 (7) 2.05 (7) 2.866 (4) 175 (6)
O17—H17B⋯O13ii 0.83 (8) 1.88 (8) 2.681 (4) 161 (7)
O18—H18A⋯O1 0.88 (4) 2.15 (5) 2.983 (5) 157 (7)
O18—H18B⋯O16iii 0.90 (4) 1.95 (4) 2.837 (4) 171 (6)
O19—H19A⋯O15iii 0.82 (4) 1.93 (4) 2.736 (4) 167 (10)
O19—H19B⋯O21iv 0.88 (9) 1.81 (9) 2.689 (5) 171 (8)
O20—H20A⋯O22 0.85 (8) 2.17 (8) 2.894 (6) 142 (7)
O20—H20B⋯O23v 0.73 (10) 2.15 (10) 2.847 (5) 158 (10)
O21—H21A⋯O1ii 0.89 (4) 1.86 (4) 2.736 (5) 169 (6)
O21—H21B⋯O6vi 0.93 (9) 1.93 (9) 2.851 (5) 171 (8)
O22—H22A⋯O6vii 0.89 (8) 2.49 (8) 3.127 (5) 128 (6)
O22—H22A⋯O10vii 0.89 (8) 2.35 (8) 3.116 (5) 143 (7)
O22—H22B⋯O23iv 0.84 (4) 2.12 (7) 2.884 (7) 150 (6)
O23—H23A⋯O5vi 0.76 (10) 1.99 (10) 2.736 (6) 170 (12)
O23—H23B⋯O24v 0.71 (9) 2.30 (11) 2.926 (6) 149 (16)
O24—H24A⋯O15i 0.87 (15) 2.02 (15) 2.882 (5) 170 (15)
O24—H24B⋯O22 0.9 (2) 1.9 (2) 2.764 (6) 161
O25—H25A⋯O24 0.92 (11) 2.52 (11) 3.137 (7) 124 (10)
O25—H25B⋯O1i 0.91 (10) 2.43 (12) 3.120 (7) 133 (12)
O25—H25B⋯O17i 0.91 (10) 2.32 (13) 3.034 (7) 136 (15)
C5—H5⋯O16viii 0.93 2.46 3.380 (5) 170
C11—H11⋯O9ix 0.93 2.40 3.193 (6) 143
C24—H24⋯O8ii 0.93 2.45 3.172 (5) 135
C29—H29⋯O5ix 0.93 2.54 3.350 (6) 146
C30—H30⋯O7 0.93 2.28 3.001 (5) 134
C31—H31⋯O25v 0.93 2.45 3.225 (8) 141
C36—H36⋯O4x 0.93 2.34 3.178 (5) 150
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y+2, -z+1; (iii) -x+1, -y+2, -z; (iv) x, y, z-1; (v) -x+1, -y+1, -z+1; (vi) x+1, y, z+1; (vii) x+1, y, z; (viii) x-1, y, z; (ix) -x, -y+1, -z; (x) -x, -y+1, -z+1.

Data collection: X-AREA (Stoe & Cie, 2005[Stoe & Cie (2005). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

Through crystal engineering of some classes of crystalline compounds, one can conclude that inter- and/or intramolecular interctions such as hydrogen bonding, ππ stacking, ion pairing, and donor-acceptor interactions are famous for making aggregates of molecules. One or more of these interactions may result in the formation of specific and spontaneous self-associated compounds. Previous researches have shown that hydrogen bonding plays a key role in the preparation of self-assembled compounds. There is a very close relationship between hydrogen bonding and the formation of proton transfer compounds (Aghabozorg et al., 2008, 2010a,b; Sheshmani et al., 2005; Soleimannejad et al., 2007).

Herein, we report the synthesis and crystal structure of the title compound. The compound is composed of a one-dimensional anionic complex, [Ce2(pydc)4(H2O)4]2- (pydc = pyridine-2,6-dicarboxylate), a protonated 4,4'-bipyridine, (bipyH2)2+, as a counterion, and five uncoordinated water molecules (Fig. 1). The Ce1 atom is nine-coordinated by three pydc ligands, which act as tridentate ligands through two O atoms and one N atom. The Ce2 atom is nine-coordinated by one tridentate pydc ligand, four O atoms of coordinated water molecules and two O atoms from the carboxylate groups of the Ce1 coordination environment. By considering the angles between the atoms of coordination environment, the geometry around Ce atoms can be described as highly distorted tricapped trigonal-prismatic. The title compound shows a one-dimensional polymeric structure (Fig. 2). An important feature of the compound is the presence of extensive intermolecular O—H···O, N—H···O and C—H···O hydrogen bonds (Table 1, Fig. 2), which seem to be effective in the stabilization of the crystal structure. There is also ππ interaction, with centroid–centroid distance of 3.514 (3) Å between the pyridine ring of pydc and bipyridine (Fig. 3). This non-covalent interaction results in the formation of an interesting supramolecular structure.

Related literature top

For hydrogen-bonding interactions in proton-transfer compounds, see: Aghabozorg et al. (2008, 2010a,b); Sheshmani et al. (2005); Soleimannejad et al. (2007).

Experimental top

A solution of Ce(NO3)3 (109 mg, 0.25 mmol) in water (10 ml) was added to an aqueous solution of pyridine-2,6-dicarboxylic acid (85 mg, 0.50 mmol) and 4,4'-bipyridine (78 mg, 0.50 mmol) in water (35 ml) in a 1:2:2 molar ratio and refluxed for an hour. Plate yellow crystals of the title compound were obtained by allowing the mixture to stand at room temperature (yield: 40.5%; m. p.: 270°C).

Refinement top

H atoms of the protonated nitrogen of bipyridine and water molecules were found in a diference Fourier map and refined isotropically, except H24A, H24B, H25A and H25B which were refined with Uiso(H) = 1.5Ueq(O). The H atoms of the protonated nitrogen and water molecules, H5A, H6A, H18A, H18B, H19A, H21A, H22B, H23B, H25A and H25B were refined with distance restraints of N—H/O—H = 0.82 (3), 0.88 (4), 0.88 (4), 0.90 (4), 0.82 (4), 0.89 (4), 0.84 (4), 0.71 (9), 0.92 (11), 0.91 (10) Å, respectively. Also H···H distance restraints of 1.3 (4) and 1.6 (4) Å for H23A···H23B and H25A···H25B, respectively, were used. H atoms on C atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C). The highest residual electron density was found at 1.24 Å from Ce2 atom and the deepest hole at 0.55 Å from Ce2 atom.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound, with displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. The packing diagram of the title compound, showing polymeric structure. The intermolecular C—H···O, N—H···O and O—H···O hydrogen bonds are shown as dashed lines.
[Figure 3] Fig. 3. The packing diagram of the title compound, showing intermolecular ππ interactions (dashed lines) between pyridine rings of pydc ligands and bipy groups. Uncoordinated water molecules have been omitted for clarity.
catena-Poly[4,4'-bipyridinium [[tetraaqua(pyridine-2,6-dicarboxylato-κ3O2,N,O6) cerate(III)]-µ-pyridine-2,6-dicarboxylato-κ4O2:O2', N,O6-[(pyridine-2,6-dicarboxylato-κ3O2,N, O6)cerate(III)]-µ-pyridine-2,6-dicarboxylato-κ4O2, N,O6:O6'] pentahydrate] top
Crystal data top
(C10H10N2)[Ce2(C7H3NO4)4(H2O)4]·5H2OZ = 2
Mr = 1261F(000) = 1252
Triclinic, P1Dx = 1.896 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 13.010 (3) ÅCell parameters from 11857 reflections
b = 13.453 (3) Åθ = 2.5–29.1°
c = 13.586 (3) ŵ = 2.14 mm1
α = 99.95 (3)°T = 150 K
β = 99.87 (3)°Plate, yellow
γ = 104.58 (3)°0.40 × 0.40 × 0.10 mm
V = 2208.3 (10) Å3
Data collection top
Stoe IPDS II
diffractometer
11857 independent reflections
Radiation source: fine-focus sealed tube10379 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.078
ω scansθmax = 29.1°, θmin = 2.5°
Absorption correction: numerical
(X-SHAPE and X-RED32; Stoe & Cie, 2005)
h = 1517
Tmin = 0.440, Tmax = 0.805k = 1818
25469 measured reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.064P)2 + 5.1288P]
where P = (Fo2 + 2Fc2)/3
11857 reflections(Δ/σ)max = 0.001
716 parametersΔρmax = 1.96 e Å3
12 restraintsΔρmin = 2.01 e Å3
Crystal data top
(C10H10N2)[Ce2(C7H3NO4)4(H2O)4]·5H2Oγ = 104.58 (3)°
Mr = 1261V = 2208.3 (10) Å3
Triclinic, P1Z = 2
a = 13.010 (3) ÅMo Kα radiation
b = 13.453 (3) ŵ = 2.14 mm1
c = 13.586 (3) ÅT = 150 K
α = 99.95 (3)°0.40 × 0.40 × 0.10 mm
β = 99.87 (3)°
Data collection top
Stoe IPDS II
diffractometer
11857 independent reflections
Absorption correction: numerical
(X-SHAPE and X-RED32; Stoe & Cie, 2005)
10379 reflections with I > 2σ(I)
Tmin = 0.440, Tmax = 0.805Rint = 0.078
25469 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04512 restraints
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 1.96 e Å3
11857 reflectionsΔρmin = 2.01 e Å3
716 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O230.6037 (3)0.5090 (3)0.9068 (4)0.0387 (9)
Ce10.003047 (16)0.783224 (16)0.218322 (15)0.01548 (7)
Ce20.503761 (15)0.888641 (16)0.188431 (15)0.01464 (7)
O10.2143 (3)1.0504 (3)0.1004 (3)0.0322 (8)
O20.1494 (2)0.9110 (2)0.1619 (2)0.0218 (6)
O30.3036 (2)0.8972 (3)0.2097 (2)0.0224 (6)
O40.1754 (2)0.8143 (2)0.2351 (2)0.0209 (6)
O50.1869 (3)0.5884 (3)0.1116 (2)0.0318 (7)
O60.1349 (2)0.6945 (3)0.0453 (2)0.0231 (6)
O70.3383 (2)0.7579 (2)0.2004 (2)0.0219 (6)
O80.1860 (2)0.7463 (2)0.2582 (2)0.0206 (6)
O90.1245 (4)0.4852 (3)0.3346 (3)0.0468 (11)
O100.0903 (3)0.6100 (2)0.2430 (2)0.0258 (6)
O110.1350 (3)1.0213 (2)0.5401 (2)0.0252 (6)
O120.0911 (2)0.9458 (2)0.3715 (2)0.0220 (6)
O130.6021 (3)0.9301 (3)0.5394 (2)0.0246 (6)
O140.5409 (2)0.8720 (2)0.3707 (2)0.0214 (6)
O150.6315 (3)1.2353 (2)0.1697 (2)0.0267 (7)
O160.5796 (2)1.0588 (2)0.1370 (2)0.0188 (5)
O170.3761 (3)0.9864 (3)0.2614 (2)0.0236 (6)
O180.3581 (2)0.9170 (3)0.0496 (2)0.0231 (6)
O190.5152 (3)0.8104 (3)0.0138 (2)0.0307 (8)
O200.5305 (3)0.7001 (3)0.1861 (3)0.0252 (6)
O210.6923 (3)0.7702 (3)0.9590 (3)0.0336 (8)
O220.6705 (3)0.5749 (3)0.1273 (4)0.0424 (9)
O240.5617 (4)0.4218 (3)0.2152 (3)0.0414 (9)
O250.4130 (5)0.2170 (5)0.2555 (4)0.0704 (15)
N10.0380 (3)0.9504 (3)0.1641 (2)0.0166 (6)
N20.0640 (3)0.6775 (3)0.0686 (3)0.0176 (6)
N30.0062 (3)0.7581 (3)0.4076 (3)0.0168 (6)
N40.6135 (3)1.0587 (3)0.3339 (2)0.0175 (6)
N50.4495 (3)0.6883 (3)0.4101 (3)0.0284 (8)
N60.2235 (3)0.1985 (3)0.5090 (3)0.0248 (7)
C10.1421 (3)0.9929 (3)0.1318 (3)0.0187 (7)
C20.0364 (3)1.0209 (3)0.1351 (3)0.0175 (7)
C30.0183 (3)1.1118 (4)0.1106 (3)0.0241 (8)
H30.07211.16070.09260.029*
C40.0831 (4)1.1277 (4)0.1137 (4)0.0257 (9)
H40.09861.18680.09570.031*
C50.1604 (3)1.0556 (3)0.1437 (3)0.0224 (8)
H50.22801.06550.14710.027*
C60.1341 (3)0.9675 (3)0.1689 (3)0.0159 (7)
C70.2116 (3)0.8863 (3)0.2073 (3)0.0171 (7)
C80.1185 (3)0.6374 (3)0.0315 (3)0.0202 (8)
C90.0023 (3)0.6335 (3)0.0242 (3)0.0183 (7)
C100.0355 (3)0.5935 (4)0.1072 (3)0.0232 (8)
H100.01280.55990.16980.028*
C110.1463 (4)0.6042 (4)0.0960 (4)0.0258 (9)
H110.17390.58100.15170.031*
C120.2147 (3)0.6503 (3)0.0002 (3)0.0222 (8)
H120.28920.65830.01050.027*
C130.1700 (3)0.6841 (3)0.0808 (3)0.0184 (7)
C140.2363 (3)0.7337 (3)0.1887 (3)0.0186 (7)
C150.0873 (4)0.5764 (3)0.3261 (3)0.0269 (9)
C160.0324 (3)0.6614 (3)0.4231 (3)0.0201 (8)
C170.0270 (4)0.6413 (3)0.5207 (3)0.0235 (8)
H170.05230.57300.52930.028*
C180.0169 (4)0.7257 (4)0.6047 (3)0.0265 (9)
H180.02150.71470.67090.032*
C190.0540 (4)0.8269 (4)0.5891 (3)0.0239 (8)
H190.08170.88500.64420.029*
C200.0486 (3)0.8388 (3)0.4890 (3)0.0187 (7)
C210.0944 (3)0.9433 (3)0.4635 (3)0.0182 (7)
C220.5907 (3)0.9444 (3)0.4513 (3)0.0170 (7)
C230.6353 (3)1.0531 (3)0.4325 (3)0.0167 (7)
C240.6926 (3)1.1406 (3)0.5114 (3)0.0210 (8)
H240.70491.13510.57950.025*
C250.7310 (3)1.2366 (4)0.4853 (3)0.0231 (8)
H250.77121.29610.53600.028*
C260.7091 (3)1.2435 (3)0.3829 (3)0.0218 (8)
H260.73421.30690.36410.026*
C270.6485 (3)1.1525 (3)0.3101 (3)0.0178 (7)
C280.6175 (3)1.1501 (3)0.1968 (3)0.0193 (7)
C290.3327 (4)0.5148 (4)0.3526 (4)0.0292 (9)
H290.28520.46130.29950.035*
C300.3824 (4)0.6105 (4)0.3339 (4)0.0301 (10)
H300.36910.62110.26760.036*
C310.4700 (3)0.6775 (4)0.5069 (4)0.0251 (9)
H310.51580.73360.55860.030*
C320.4232 (4)0.5828 (3)0.5297 (3)0.0245 (8)
H320.43750.57500.59690.029*
C330.3541 (3)0.4985 (3)0.4518 (3)0.0214 (8)
C340.3074 (3)0.3929 (3)0.4717 (3)0.0223 (8)
C350.3043 (3)0.3822 (3)0.5715 (3)0.0237 (8)
H350.33030.44050.62640.028*
C360.2614 (3)0.2823 (4)0.5865 (4)0.0254 (9)
H360.25920.27380.65270.030*
C370.2270 (4)0.2074 (4)0.4136 (4)0.0285 (9)
H370.20100.14720.36060.034*
C380.2682 (4)0.3035 (4)0.3914 (3)0.0272 (9)
H380.26990.30870.32430.033*
H5A0.476 (4)0.743 (3)0.394 (4)0.031 (15)*
H6A0.193 (6)0.137 (4)0.522 (6)0.07 (3)*
H17A0.311 (6)0.965 (5)0.236 (5)0.040 (17)*
H18A0.333 (6)0.971 (4)0.070 (5)0.06 (2)*
H19A0.468 (6)0.804 (8)0.037 (5)0.10 (3)*
H20A0.592 (6)0.694 (6)0.176 (5)0.05 (2)*
H21A0.731 (5)0.826 (4)0.941 (5)0.039 (17)*
H22A0.741 (7)0.583 (6)0.130 (6)0.07 (2)*
H23A0.660 (8)0.526 (9)0.895 (9)0.11 (4)*
H24A0.577 (12)0.362 (12)0.206 (11)0.167*
H25A0.414 (11)0.255 (9)0.205 (8)0.167*
H17B0.378 (6)0.998 (6)0.324 (6)0.06 (2)*
H18B0.385 (5)0.928 (5)0.005 (4)0.048 (19)*
H19B0.575 (7)0.795 (7)0.002 (6)0.08 (3)*
H20B0.483 (8)0.654 (8)0.163 (7)0.09 (3)*
H21B0.743 (8)0.739 (7)0.985 (7)0.08 (3)*
H22B0.633 (9)0.566 (10)0.068 (5)0.14 (5)*
H23B0.560 (9)0.532 (11)0.898 (12)0.17 (7)*
H24B0.609 (17)0.464 (17)0.184 (16)0.260*
H25B0.365 (13)0.152 (7)0.243 (12)0.260*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O230.0246 (18)0.034 (2)0.052 (2)0.0025 (15)0.0044 (17)0.0073 (17)
Ce10.01187 (10)0.01963 (12)0.01492 (11)0.00337 (8)0.00220 (8)0.00646 (8)
Ce20.01032 (10)0.02055 (12)0.01249 (11)0.00290 (8)0.00114 (7)0.00601 (8)
O10.0192 (14)0.0407 (19)0.047 (2)0.0100 (13)0.0144 (14)0.0297 (17)
O20.0170 (13)0.0260 (15)0.0261 (15)0.0073 (11)0.0058 (11)0.0130 (12)
O30.0129 (12)0.0311 (16)0.0252 (15)0.0066 (11)0.0073 (11)0.0083 (12)
O40.0181 (13)0.0255 (15)0.0209 (14)0.0047 (11)0.0049 (11)0.0119 (12)
O50.0185 (14)0.046 (2)0.0232 (16)0.0043 (14)0.0029 (12)0.0013 (14)
O60.0156 (13)0.0306 (16)0.0209 (14)0.0061 (12)0.0002 (11)0.0049 (12)
O70.0120 (12)0.0260 (15)0.0249 (15)0.0030 (11)0.0011 (11)0.0073 (12)
O80.0163 (13)0.0297 (15)0.0173 (13)0.0083 (11)0.0021 (10)0.0084 (12)
O90.084 (3)0.0209 (17)0.0240 (17)0.0050 (18)0.0098 (19)0.0058 (14)
O100.0345 (17)0.0192 (14)0.0189 (14)0.0006 (12)0.0046 (12)0.0062 (11)
O110.0270 (15)0.0212 (15)0.0214 (14)0.0003 (12)0.0004 (12)0.0047 (12)
O120.0200 (14)0.0241 (15)0.0207 (14)0.0036 (11)0.0037 (11)0.0066 (12)
O130.0293 (16)0.0316 (16)0.0143 (13)0.0089 (13)0.0050 (12)0.0086 (12)
O140.0200 (13)0.0250 (15)0.0157 (13)0.0000 (11)0.0014 (11)0.0075 (11)
O150.0314 (16)0.0233 (15)0.0231 (15)0.0064 (13)0.0011 (13)0.0088 (12)
O160.0183 (13)0.0191 (13)0.0159 (13)0.0022 (11)0.0007 (10)0.0039 (11)
O170.0168 (14)0.0355 (17)0.0163 (14)0.0072 (12)0.0016 (11)0.0025 (13)
O180.0190 (13)0.0343 (17)0.0188 (14)0.0093 (12)0.0038 (11)0.0112 (13)
O190.0286 (17)0.055 (2)0.0164 (14)0.0262 (16)0.0035 (13)0.0091 (14)
O200.0196 (15)0.0231 (16)0.0325 (17)0.0052 (13)0.0051 (13)0.0078 (13)
O210.0273 (17)0.0367 (19)0.046 (2)0.0141 (15)0.0141 (15)0.0209 (17)
O220.0213 (17)0.044 (2)0.054 (3)0.0012 (16)0.0097 (17)0.0030 (19)
O240.047 (2)0.038 (2)0.038 (2)0.0150 (18)0.0022 (17)0.0082 (17)
O250.068 (4)0.074 (4)0.064 (3)0.008 (3)0.015 (3)0.021 (3)
N10.0115 (14)0.0223 (16)0.0149 (14)0.0036 (12)0.0017 (11)0.0048 (12)
N20.0146 (14)0.0213 (16)0.0161 (15)0.0028 (12)0.0020 (12)0.0073 (13)
N30.0135 (14)0.0186 (15)0.0182 (15)0.0038 (12)0.0030 (12)0.0059 (12)
N40.0130 (14)0.0234 (17)0.0157 (15)0.0057 (12)0.0015 (12)0.0044 (13)
N50.0245 (18)0.028 (2)0.040 (2)0.0082 (15)0.0157 (16)0.0189 (18)
N60.0173 (16)0.0251 (18)0.031 (2)0.0022 (14)0.0051 (14)0.0114 (16)
C10.0146 (16)0.0237 (19)0.0186 (18)0.0049 (14)0.0038 (14)0.0075 (15)
C20.0130 (16)0.0236 (19)0.0162 (17)0.0011 (14)0.0038 (13)0.0107 (15)
C30.0203 (19)0.028 (2)0.030 (2)0.0085 (16)0.0095 (16)0.0165 (18)
C40.025 (2)0.027 (2)0.030 (2)0.0119 (17)0.0060 (17)0.0139 (18)
C50.0176 (18)0.026 (2)0.026 (2)0.0073 (16)0.0050 (15)0.0108 (17)
C60.0136 (16)0.0203 (18)0.0143 (16)0.0051 (13)0.0017 (13)0.0065 (14)
C70.0126 (16)0.0205 (18)0.0138 (16)0.0013 (13)0.0017 (13)0.0018 (14)
C80.0182 (18)0.026 (2)0.0151 (17)0.0044 (15)0.0018 (14)0.0047 (15)
C90.0141 (16)0.0205 (18)0.0177 (17)0.0026 (14)0.0005 (14)0.0040 (14)
C100.0203 (19)0.027 (2)0.0175 (18)0.0029 (16)0.0000 (15)0.0024 (16)
C110.021 (2)0.027 (2)0.026 (2)0.0049 (16)0.0077 (16)0.0011 (17)
C120.0159 (17)0.024 (2)0.025 (2)0.0042 (15)0.0030 (15)0.0034 (16)
C130.0140 (16)0.0209 (18)0.0193 (18)0.0046 (14)0.0012 (14)0.0053 (15)
C140.0154 (17)0.0209 (18)0.0181 (18)0.0030 (14)0.0006 (14)0.0088 (15)
C150.033 (2)0.021 (2)0.023 (2)0.0001 (17)0.0067 (17)0.0047 (16)
C160.0177 (17)0.0240 (19)0.0195 (18)0.0051 (15)0.0046 (14)0.0086 (15)
C170.026 (2)0.025 (2)0.023 (2)0.0084 (16)0.0052 (16)0.0125 (17)
C180.028 (2)0.030 (2)0.0191 (19)0.0042 (17)0.0019 (16)0.0084 (17)
C190.026 (2)0.027 (2)0.0160 (18)0.0033 (16)0.0027 (15)0.0049 (16)
C200.0138 (16)0.0258 (19)0.0175 (17)0.0054 (14)0.0032 (14)0.0087 (15)
C210.0125 (16)0.0238 (19)0.0181 (17)0.0034 (14)0.0037 (13)0.0071 (15)
C220.0124 (15)0.0259 (19)0.0128 (16)0.0062 (14)0.0017 (13)0.0051 (14)
C230.0121 (15)0.0251 (19)0.0135 (16)0.0083 (14)0.0011 (13)0.0031 (14)
C240.0179 (17)0.028 (2)0.0163 (17)0.0064 (15)0.0015 (14)0.0044 (16)
C250.0149 (17)0.030 (2)0.0202 (19)0.0046 (15)0.0013 (14)0.0014 (16)
C260.0171 (17)0.0203 (19)0.0226 (19)0.0001 (15)0.0019 (15)0.0051 (16)
C270.0150 (16)0.0197 (18)0.0176 (17)0.0049 (14)0.0021 (13)0.0031 (14)
C280.0126 (16)0.027 (2)0.0182 (18)0.0039 (14)0.0017 (14)0.0080 (15)
C290.026 (2)0.032 (2)0.030 (2)0.0034 (18)0.0062 (18)0.0158 (19)
C300.031 (2)0.036 (3)0.031 (2)0.012 (2)0.0109 (19)0.017 (2)
C310.0186 (18)0.025 (2)0.034 (2)0.0056 (16)0.0092 (17)0.0117 (18)
C320.023 (2)0.026 (2)0.027 (2)0.0081 (17)0.0070 (16)0.0098 (17)
C330.0157 (17)0.026 (2)0.027 (2)0.0058 (15)0.0070 (15)0.0140 (17)
C340.0181 (18)0.0221 (19)0.025 (2)0.0014 (15)0.0043 (15)0.0097 (16)
C350.0215 (19)0.024 (2)0.025 (2)0.0023 (16)0.0054 (16)0.0097 (16)
C360.023 (2)0.026 (2)0.030 (2)0.0047 (16)0.0060 (17)0.0153 (18)
C370.026 (2)0.025 (2)0.031 (2)0.0041 (17)0.0027 (18)0.0075 (18)
C380.028 (2)0.029 (2)0.023 (2)0.0033 (17)0.0037 (17)0.0086 (17)
Geometric parameters (Å, º) top
O23—H23A0.76 (10)N4—C271.345 (5)
O23—H23B0.71 (9)N5—C301.336 (7)
Ce1—O102.450 (3)N5—C311.337 (6)
Ce1—O42.500 (3)N5—H5A0.82 (3)
Ce1—O82.540 (3)N6—C361.325 (6)
Ce1—O22.545 (3)N6—C371.330 (6)
Ce1—O62.584 (3)N6—H6A0.88 (4)
Ce1—O122.603 (3)C1—C21.520 (5)
Ce1—N22.629 (4)C2—C31.385 (6)
Ce1—N12.631 (3)C3—C41.396 (6)
Ce1—N32.646 (3)C3—H30.9300
Ce2—O3i2.444 (3)C4—C51.380 (6)
Ce2—O72.464 (3)C4—H40.9300
Ce2—O192.469 (3)C5—C61.393 (5)
Ce2—O142.501 (3)C5—H50.9300
Ce2—O162.520 (3)C6—C71.519 (5)
Ce2—O182.585 (3)C8—C91.512 (5)
Ce2—O172.585 (3)C9—C101.384 (6)
Ce2—O202.641 (3)C10—C111.391 (6)
Ce2—N42.646 (4)C10—H100.9300
O1—C11.244 (5)C11—C121.390 (6)
O2—C11.259 (5)C11—H110.9300
O3—C71.247 (5)C12—C131.387 (6)
O3—Ce2ii2.444 (3)C12—H120.9300
O4—C71.265 (5)C13—C141.509 (5)
O5—C81.239 (5)C15—C161.517 (6)
O6—C81.267 (5)C16—C171.392 (6)
O7—C141.258 (5)C17—C181.385 (6)
O8—C141.250 (5)C17—H170.9300
O9—C151.233 (5)C18—C191.392 (6)
O10—C151.285 (5)C18—H180.9300
O11—C211.273 (5)C19—C201.389 (5)
O12—C211.250 (5)C19—H190.9300
O13—C221.236 (5)C20—C211.507 (5)
O14—C221.279 (5)C22—C231.514 (6)
O15—C281.243 (5)C23—C241.393 (6)
O16—C281.275 (5)C24—C251.392 (6)
O17—H17A0.82 (7)C24—H240.9300
O17—H17B0.83 (8)C25—C261.395 (6)
O18—H18B0.90 (4)C25—H250.9300
O18—H18A0.88 (4)C26—C271.388 (6)
O18—H18B0.90 (4)C26—H260.9300
O19—H19A0.82 (4)C27—C281.515 (5)
O19—H19B0.88 (9)C29—C301.374 (6)
O20—H20A0.85 (8)C29—C331.395 (6)
O20—H20B0.73 (10)C29—H290.9300
O21—H21A0.89 (4)C30—H300.9300
O21—H21B0.93 (9)C31—C321.378 (6)
O22—H22A0.89 (8)C31—H310.9300
O22—H22B0.84 (4)C32—C331.401 (6)
O24—H24A0.87 (15)C32—H320.9300
O24—H24B0.9 (2)C33—C341.488 (6)
O25—H25A0.92 (11)C34—C381.394 (6)
O25—H25B0.91 (10)C34—C351.394 (6)
N1—C61.338 (5)C35—C361.384 (6)
N1—C21.338 (5)C35—H350.9300
N2—C131.339 (5)C36—H360.9300
N2—C91.339 (5)C37—C381.375 (6)
N3—C201.334 (5)C37—H370.9300
N3—C161.338 (5)C38—H380.9300
N4—C231.340 (5)
H23A—O23—H23B129 (10)C36—N6—H6A118 (5)
O10—Ce1—O481.20 (11)C37—N6—H6A121 (5)
O10—Ce1—O890.78 (11)O1—C1—O2124.6 (4)
O4—Ce1—O8162.20 (9)O1—C1—C2119.4 (4)
O10—Ce1—O2154.12 (11)O2—C1—C2116.1 (3)
O4—Ce1—O2123.00 (9)N1—C2—C3122.6 (4)
O8—Ce1—O268.38 (9)N1—C2—C1114.3 (3)
O10—Ce1—O676.37 (10)C3—C2—C1123.1 (3)
O4—Ce1—O672.21 (10)C2—C3—C4118.0 (4)
O8—Ce1—O6121.45 (10)C2—C3—H3121.0
O2—Ce1—O6100.91 (10)C4—C3—H3121.0
O10—Ce1—O12121.94 (10)C5—C4—C3119.9 (4)
O4—Ce1—O1286.20 (10)C5—C4—H4120.1
O8—Ce1—O1284.62 (10)C3—C4—H4120.1
O2—Ce1—O1272.93 (10)C4—C5—C6118.1 (4)
O6—Ce1—O12149.70 (10)C4—C5—H5121.0
O10—Ce1—N285.60 (11)C6—C5—H5121.0
O4—Ce1—N2132.60 (10)N1—C6—C5122.5 (4)
O8—Ce1—N261.78 (10)N1—C6—C7115.5 (3)
O2—Ce1—N271.26 (10)C5—C6—C7122.0 (3)
O6—Ce1—N260.45 (10)O3—C7—O4126.2 (4)
O12—Ce1—N2137.74 (10)O3—C7—C6117.6 (3)
O10—Ce1—N1141.05 (11)O4—C7—C6116.1 (3)
O4—Ce1—N162.18 (10)O5—C8—O6126.4 (4)
O8—Ce1—N1128.08 (10)O5—C8—C9118.1 (4)
O2—Ce1—N160.93 (10)O6—C8—C9115.5 (3)
O6—Ce1—N179.99 (10)N2—C9—C10121.9 (4)
O12—Ce1—N171.06 (10)N2—C9—C8114.6 (4)
N2—Ce1—N1108.86 (10)C10—C9—C8123.4 (4)
O10—Ce1—N361.35 (11)C9—C10—C11119.4 (4)
O4—Ce1—N381.32 (10)C9—C10—H10120.3
O8—Ce1—N380.89 (10)C11—C10—H10120.3
O2—Ce1—N3126.17 (10)C12—C11—C10118.4 (4)
O6—Ce1—N3132.92 (10)C12—C11—H11120.8
O12—Ce1—N360.77 (10)C10—C11—H11120.8
N2—Ce1—N3129.88 (10)C13—C12—C11118.8 (4)
N1—Ce1—N3120.63 (10)C13—C12—H12120.6
O3i—Ce2—O7134.99 (10)C11—C12—H12120.6
O3i—Ce2—O1977.20 (11)N2—C13—C12122.5 (4)
O7—Ce2—O1998.81 (12)N2—C13—C14114.3 (4)
O3i—Ce2—O1481.51 (10)C12—C13—C14123.2 (3)
O7—Ce2—O1475.82 (10)O8—C14—O7125.8 (4)
O19—Ce2—O14143.15 (11)O8—C14—C13117.7 (3)
O3i—Ce2—O1678.67 (10)O7—C14—C13116.4 (4)
O7—Ce2—O16146.02 (9)O9—C15—O10127.5 (4)
O19—Ce2—O1682.61 (12)O9—C15—C16118.2 (4)
O14—Ce2—O16122.17 (10)O10—C15—C16114.3 (4)
O3i—Ce2—O18135.63 (10)N3—C16—C17122.6 (4)
O7—Ce2—O1878.75 (10)N3—C16—C15114.7 (3)
O19—Ce2—O1868.25 (11)C17—C16—C15122.7 (4)
O14—Ce2—O18142.09 (10)C18—C17—C16118.4 (4)
O16—Ce2—O1870.25 (10)C18—C17—H17120.8
O3i—Ce2—O17141.35 (11)C16—C17—H17120.8
O7—Ce2—O1770.97 (11)C17—C18—C19119.3 (4)
O19—Ce2—O17134.26 (10)C17—C18—H18120.3
O14—Ce2—O1779.25 (10)C19—C18—H18120.3
O16—Ce2—O1783.74 (10)C20—C19—C18118.2 (4)
O18—Ce2—O1766.04 (10)C20—C19—H19120.9
O3i—Ce2—O2069.27 (11)C18—C19—H19120.9
O7—Ce2—O2067.13 (11)N3—C20—C19122.9 (4)
O19—Ce2—O2071.40 (12)N3—C20—C21114.4 (3)
O14—Ce2—O2073.06 (11)C19—C20—C21122.7 (4)
O16—Ce2—O20142.18 (10)O12—C21—O11126.3 (4)
O18—Ce2—O20121.16 (11)O12—C21—C20118.4 (4)
O17—Ce2—O20134.03 (11)O11—C21—C20115.3 (3)
O3i—Ce2—N473.33 (11)O13—C22—O14124.2 (4)
O7—Ce2—N4124.35 (11)O13—C22—C23120.6 (4)
O19—Ce2—N4136.81 (12)O14—C22—C23115.2 (3)
O14—Ce2—N461.05 (10)N4—C23—C24122.7 (4)
O16—Ce2—N461.28 (10)N4—C23—C22114.5 (3)
O18—Ce2—N4114.97 (11)C24—C23—C22122.8 (3)
O17—Ce2—N468.03 (10)C25—C24—C23117.9 (4)
O20—Ce2—N4123.80 (11)C25—C24—H24121.0
C1—O2—Ce1127.0 (2)C23—C24—H24121.0
C7—O3—Ce2ii169.2 (3)C24—C25—C26120.0 (4)
C7—O4—Ce1126.6 (2)C24—C25—H25120.0
C8—O6—Ce1126.4 (2)C26—C25—H25120.0
C14—O7—Ce2146.2 (3)C27—C26—C25117.8 (4)
C14—O8—Ce1119.8 (2)C27—C26—H26121.1
C15—O10—Ce1129.0 (3)C25—C26—H26121.1
C21—O12—Ce1124.5 (3)N4—C27—C26122.9 (4)
C22—O14—Ce2128.3 (2)N4—C27—C28114.2 (3)
C28—O16—Ce2126.0 (2)C26—C27—C28122.9 (4)
Ce2—O17—H17A119 (5)O15—C28—O16125.6 (4)
Ce2—O17—H17B120 (5)O15—C28—C27118.5 (4)
H17A—O17—H17B102 (7)O16—C28—C27115.9 (3)
H18B—O18—Ce2110 (4)C30—C29—C33119.6 (5)
H18B—O18—H18A107 (6)C30—C29—H29120.2
Ce2—O18—H18A115 (5)C33—C29—H29120.2
Ce2—O18—H18B110 (4)N5—C30—C29120.6 (4)
H18A—O18—H18B107 (6)N5—C30—H30119.7
Ce2—O19—H19A122 (7)C29—C30—H30119.7
Ce2—O19—H19B121 (5)N5—C31—C32119.7 (4)
H19A—O19—H19B116 (8)N5—C31—H31120.1
Ce2—O20—H20A116 (5)C32—C31—H31120.1
Ce2—O20—H20B119 (8)C31—C32—C33120.1 (4)
H20A—O20—H20B115 (9)C31—C32—H32120.0
H21A—O21—H21B105 (7)C33—C32—H32120.0
H22A—O22—H22B114 (10)C29—C33—C32117.9 (4)
H24A—O24—H24B104 (10)C29—C33—C34120.1 (4)
H25A—O25—H25B120 (7)C32—C33—C34121.9 (4)
C6—N1—C2118.9 (3)C38—C34—C35119.3 (4)
C6—N1—Ce1119.4 (2)C38—C34—C33120.6 (4)
C2—N1—Ce1121.7 (2)C35—C34—C33120.2 (4)
C13—N2—C9118.9 (4)C36—C35—C34118.2 (4)
C13—N2—Ce1117.7 (3)C36—C35—H35120.9
C9—N2—Ce1122.4 (3)C34—C35—H35120.9
C20—N3—C16118.6 (3)N6—C36—C35121.6 (4)
C20—N3—Ce1121.9 (3)N6—C36—H36119.2
C16—N3—Ce1119.5 (3)C35—C36—H36119.2
C23—N4—C27118.7 (4)N6—C37—C38121.5 (5)
C23—N4—Ce2120.8 (3)N6—C37—H37119.3
C27—N4—Ce2120.5 (2)C38—C37—H37119.3
C30—N5—C31122.0 (4)C37—C38—C34118.6 (4)
C30—N5—H5A116 (4)C37—C38—H38120.7
C31—N5—H5A122 (4)C34—C38—H38120.7
C36—N6—C37120.9 (4)
O10—Ce1—O2—C1151.7 (3)O3i—Ce2—N4—C2790.7 (3)
O4—Ce1—O2—C15.3 (4)O7—Ce2—N4—C27135.7 (3)
O8—Ce1—O2—C1169.9 (4)O19—Ce2—N4—C2741.8 (3)
O6—Ce1—O2—C170.4 (3)O14—Ce2—N4—C27179.9 (3)
O12—Ce1—O2—C178.9 (3)O16—Ce2—N4—C274.7 (3)
N2—Ce1—O2—C1123.9 (3)O18—Ce2—N4—C2742.4 (3)
N1—Ce1—O2—C11.5 (3)O17—Ce2—N4—C2790.3 (3)
N3—Ce1—O2—C1109.9 (3)O20—Ce2—N4—C27140.6 (3)
O10—Ce1—O4—C7161.8 (3)Ce1—O2—C1—O1176.5 (3)
O8—Ce1—O4—C7134.1 (3)Ce1—O2—C1—C23.4 (5)
O2—Ce1—O4—C78.2 (3)C6—N1—C2—C30.6 (6)
O6—Ce1—O4—C783.4 (3)Ce1—N1—C2—C3177.1 (3)
O12—Ce1—O4—C775.0 (3)C6—N1—C2—C1179.7 (3)
N2—Ce1—O4—C786.2 (3)Ce1—N1—C2—C12.7 (4)
N1—Ce1—O4—C74.5 (3)O1—C1—C2—N1176.1 (4)
N3—Ce1—O4—C7136.0 (3)O2—C1—C2—N13.8 (5)
O10—Ce1—O6—C889.2 (3)O1—C1—C2—C34.2 (6)
O4—Ce1—O6—C8174.1 (3)O2—C1—C2—C3176.0 (4)
O8—Ce1—O6—C86.7 (4)N1—C2—C3—C41.9 (7)
O2—Ce1—O6—C864.5 (3)C1—C2—C3—C4178.3 (4)
O12—Ce1—O6—C8139.2 (3)C2—C3—C4—C52.0 (7)
N2—Ce1—O6—C83.5 (3)C3—C4—C5—C60.8 (7)
N1—Ce1—O6—C8122.0 (3)C2—N1—C6—C50.7 (6)
N3—Ce1—O6—C8115.1 (3)Ce1—N1—C6—C5178.4 (3)
O3i—Ce2—O7—C14174.6 (5)C2—N1—C6—C7177.2 (3)
O19—Ce2—O7—C1494.0 (5)Ce1—N1—C6—C70.5 (4)
O14—Ce2—O7—C14123.3 (5)C4—C5—C6—N10.6 (6)
O16—Ce2—O7—C144.1 (6)C4—C5—C6—C7177.2 (4)
O18—Ce2—O7—C1428.4 (5)Ce2ii—O3—C7—O469.7 (16)
O17—Ce2—O7—C1440.0 (5)Ce2ii—O3—C7—C6111.2 (14)
O20—Ce2—O7—C14159.4 (5)Ce1—O4—C7—O3175.0 (3)
N4—Ce2—O7—C1484.3 (5)Ce1—O4—C7—C65.9 (5)
O10—Ce1—O8—C14111.4 (3)N1—C6—C7—O3177.6 (3)
O4—Ce1—O8—C14174.1 (3)C5—C6—C7—O34.4 (6)
O2—Ce1—O8—C1452.9 (3)N1—C6—C7—O43.2 (5)
O6—Ce1—O8—C1436.9 (3)C5—C6—C7—O4174.8 (4)
O12—Ce1—O8—C14126.6 (3)Ce1—O6—C8—O5174.2 (3)
N2—Ce1—O8—C1426.8 (3)Ce1—O6—C8—C98.4 (5)
N1—Ce1—O8—C1465.8 (3)C13—N2—C9—C100.8 (6)
N3—Ce1—O8—C14172.2 (3)Ce1—N2—C9—C10169.0 (3)
O4—Ce1—O10—C1595.0 (4)C13—N2—C9—C8175.7 (3)
O8—Ce1—O10—C1569.0 (4)Ce1—N2—C9—C87.5 (5)
O2—Ce1—O10—C15104.3 (4)O5—C8—C9—N2172.4 (4)
O6—Ce1—O10—C15168.7 (4)O6—C8—C9—N210.0 (5)
O12—Ce1—O10—C1515.1 (4)O5—C8—C9—C1011.2 (6)
N2—Ce1—O10—C15130.6 (4)O6—C8—C9—C10166.5 (4)
N1—Ce1—O10—C15114.5 (4)N2—C9—C10—C113.6 (6)
N3—Ce1—O10—C1510.2 (4)C8—C9—C10—C11172.6 (4)
O10—Ce1—O12—C213.1 (3)C9—C10—C11—C123.2 (7)
O4—Ce1—O12—C2180.2 (3)C10—C11—C12—C130.3 (7)
O8—Ce1—O12—C2184.5 (3)C9—N2—C13—C122.2 (6)
O2—Ce1—O12—C21153.5 (3)Ce1—N2—C13—C12166.5 (3)
O6—Ce1—O12—C21124.1 (3)C9—N2—C13—C14179.2 (3)
N2—Ce1—O12—C21120.4 (3)Ce1—N2—C13—C1412.1 (4)
N1—Ce1—O12—C21142.1 (3)C11—C12—C13—N22.5 (6)
N3—Ce1—O12—C211.9 (3)C11—C12—C13—C14179.1 (4)
O3i—Ce2—O14—C2276.6 (3)Ce1—O8—C14—O7148.6 (3)
O7—Ce2—O14—C22142.6 (3)Ce1—O8—C14—C1332.1 (5)
O19—Ce2—O14—C22131.7 (3)Ce2—O7—C14—O899.1 (5)
O16—Ce2—O14—C225.8 (4)Ce2—O7—C14—C1381.6 (6)
O18—Ce2—O14—C2293.3 (3)N2—C13—C14—O812.3 (5)
O17—Ce2—O14—C2269.7 (3)C12—C13—C14—O8169.2 (4)
O20—Ce2—O14—C22147.4 (3)N2—C13—C14—O7168.4 (3)
N4—Ce2—O14—C221.0 (3)C12—C13—C14—O710.2 (6)
O3i—Ce2—O16—C2889.7 (3)Ce1—O10—C15—O9170.5 (4)
O7—Ce2—O16—C2897.1 (3)Ce1—O10—C15—C1610.4 (6)
O19—Ce2—O16—C28168.1 (3)C20—N3—C16—C171.9 (6)
O14—Ce2—O16—C2817.4 (3)Ce1—N3—C16—C17175.8 (3)
O18—Ce2—O16—C28122.5 (3)C20—N3—C16—C15175.2 (4)
O17—Ce2—O16—C2855.7 (3)Ce1—N3—C16—C157.1 (5)
O20—Ce2—O16—C28121.8 (3)O9—C15—C16—N3179.8 (5)
N4—Ce2—O16—C2812.6 (3)O10—C15—C16—N31.0 (6)
O3i—Ce2—O18—H18B5 (5)O9—C15—C16—C173.1 (7)
O7—Ce2—O18—H18B141 (5)O10—C15—C16—C17176.1 (4)
O19—Ce2—O18—H18B36 (5)N3—C16—C17—C182.1 (6)
O14—Ce2—O18—H18B171 (5)C15—C16—C17—C18174.8 (4)
O16—Ce2—O18—H18B53 (5)C16—C17—C18—C190.0 (7)
O17—Ce2—O18—H18B145 (5)C17—C18—C19—C202.0 (7)
O20—Ce2—O18—H18B86 (5)C16—N3—C20—C190.3 (6)
N4—Ce2—O18—H18B96 (5)Ce1—N3—C20—C19178.0 (3)
O10—Ce1—N1—C619.7 (4)C16—N3—C20—C21177.2 (3)
O4—Ce1—N1—C62.2 (3)Ce1—N3—C20—C210.5 (4)
O8—Ce1—N1—C6164.8 (3)C18—C19—C20—N32.3 (6)
O2—Ce1—N1—C6178.5 (3)C18—C19—C20—C21175.1 (4)
O6—Ce1—N1—C672.9 (3)Ce1—O12—C21—O11178.7 (3)
O12—Ce1—N1—C698.0 (3)Ce1—O12—C21—C202.5 (5)
N2—Ce1—N1—C6126.8 (3)N3—C20—C21—O121.3 (5)
N3—Ce1—N1—C661.4 (3)C19—C20—C21—O12176.3 (4)
O10—Ce1—N1—C2162.7 (3)N3—C20—C21—O11179.8 (3)
O4—Ce1—N1—C2175.5 (3)C19—C20—C21—O112.6 (6)
O8—Ce1—N1—C212.9 (3)Ce2—O14—C22—O13177.2 (3)
O2—Ce1—N1—C20.9 (3)Ce2—O14—C22—C231.9 (5)
O6—Ce1—N1—C2109.5 (3)C27—N4—C23—C240.2 (6)
O12—Ce1—N1—C279.6 (3)Ce2—N4—C23—C24179.9 (3)
N2—Ce1—N1—C255.6 (3)C27—N4—C23—C22179.0 (3)
N3—Ce1—N1—C2116.2 (3)Ce2—N4—C23—C221.1 (4)
O10—Ce1—N2—C13112.1 (3)O13—C22—C23—N4177.4 (4)
O4—Ce1—N2—C13174.1 (2)O14—C22—C23—N41.8 (5)
O8—Ce1—N2—C1318.8 (3)O13—C22—C23—C241.5 (6)
O2—Ce1—N2—C1356.1 (3)O14—C22—C23—C24179.3 (4)
O6—Ce1—N2—C13171.1 (3)N4—C23—C24—C251.9 (6)
O12—Ce1—N2—C1322.7 (3)C22—C23—C24—C25179.3 (4)
N1—Ce1—N2—C13105.0 (3)C23—C24—C25—C261.7 (6)
N3—Ce1—N2—C1365.8 (3)C24—C25—C26—C270.2 (6)
O10—Ce1—N2—C979.6 (3)C23—N4—C27—C261.9 (6)
O4—Ce1—N2—C95.8 (4)Ce2—N4—C27—C26178.1 (3)
O8—Ce1—N2—C9172.9 (3)C23—N4—C27—C28178.9 (3)
O2—Ce1—N2—C9112.2 (3)Ce2—N4—C27—C281.1 (4)
O6—Ce1—N2—C92.8 (3)C25—C26—C27—N42.0 (6)
O12—Ce1—N2—C9145.6 (3)C25—C26—C27—C28178.8 (4)
N1—Ce1—N2—C963.3 (3)Ce2—O16—C28—O15162.5 (3)
N3—Ce1—N2—C9125.9 (3)Ce2—O16—C28—C2718.1 (5)
O10—Ce1—N3—C20174.1 (3)N4—C27—C28—O15169.0 (4)
O4—Ce1—N3—C2089.4 (3)C26—C27—C28—O1511.8 (6)
O8—Ce1—N3—C2090.0 (3)N4—C27—C28—O1611.6 (5)
O2—Ce1—N3—C2035.4 (3)C26—C27—C28—O16167.7 (4)
O6—Ce1—N3—C20145.1 (3)C31—N5—C30—C291.0 (7)
O12—Ce1—N3—C201.1 (3)C33—C29—C30—N51.0 (7)
N2—Ce1—N3—C20130.7 (3)C30—N5—C31—C321.6 (7)
N1—Ce1—N3—C2039.1 (3)N5—C31—C32—C330.2 (6)
O10—Ce1—N3—C168.3 (3)C30—C29—C33—C322.3 (7)
O4—Ce1—N3—C1692.9 (3)C30—C29—C33—C34175.5 (4)
O8—Ce1—N3—C1687.7 (3)C31—C32—C33—C291.7 (6)
O2—Ce1—N3—C16142.2 (3)C31—C32—C33—C34176.0 (4)
O6—Ce1—N3—C1637.3 (3)C29—C33—C34—C3817.7 (6)
O12—Ce1—N3—C16176.6 (3)C32—C33—C34—C38160.0 (4)
N2—Ce1—N3—C1647.0 (3)C29—C33—C34—C35163.5 (4)
N1—Ce1—N3—C16143.2 (3)C32—C33—C34—C3518.8 (6)
O3i—Ce2—N4—C2389.2 (3)C38—C34—C35—C360.4 (6)
O7—Ce2—N4—C2344.4 (3)C33—C34—C35—C36179.2 (4)
O19—Ce2—N4—C23138.1 (3)C37—N6—C36—C351.1 (7)
O14—Ce2—N4—C230.2 (3)C34—C35—C36—N60.4 (6)
O16—Ce2—N4—C23175.2 (3)C36—N6—C37—C381.1 (7)
O18—Ce2—N4—C23137.7 (3)N6—C37—C38—C340.3 (7)
O17—Ce2—N4—C2389.8 (3)C35—C34—C38—C370.4 (7)
O20—Ce2—N4—C2339.4 (3)C33—C34—C38—C37179.2 (4)
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5A···O140.82 (3)1.83 (4)2.647 (5)175 (6)
N6—H6A···O11iii0.88 (4)1.63 (4)2.514 (5)177 (8)
O17—H17A···O20.82 (7)2.05 (7)2.866 (4)175 (6)
O17—H17B···O13iv0.83 (8)1.88 (8)2.681 (4)161 (7)
O18—H18A···O10.88 (4)2.15 (5)2.983 (5)157 (7)
O18—H18B···O16v0.90 (4)1.95 (4)2.837 (4)171 (6)
O19—H19A···O15v0.82 (4)1.93 (4)2.736 (4)167 (10)
O19—H19B···O21vi0.88 (9)1.81 (9)2.689 (5)171 (8)
O20—H20A···O220.85 (8)2.17 (8)2.894 (6)142 (7)
O20—H20B···O23vii0.73 (10)2.15 (10)2.847 (5)158 (10)
O21—H21A···O1iv0.89 (4)1.86 (4)2.736 (5)169 (6)
O21—H21B···O6viii0.93 (9)1.93 (9)2.851 (5)171 (8)
O22—H22A···O6i0.89 (8)2.49 (8)3.127 (5)128 (6)
O22—H22A···O10i0.89 (8)2.35 (8)3.116 (5)143 (7)
O22—H22B···O23vi0.84 (4)2.12 (7)2.884 (7)150 (6)
O23—H23A···O5viii0.76 (10)1.99 (10)2.736 (6)170 (12)
O23—H23B···O24vii0.71 (9)2.30 (11)2.926 (6)149 (16)
O24—H24A···O15iii0.87 (15)2.02 (15)2.882 (5)170 (15)
O24—H24B···O220.9 (2)1.9 (2)2.764 (6)161
O25—H25A···O240.92 (11)2.52 (11)3.137 (7)124 (10)
O25—H25B···O1iii0.91 (10)2.43 (12)3.120 (7)133 (12)
O25—H25B···O17iii0.91 (10)2.32 (13)3.034 (7)136 (15)
C5—H5···O16ii0.932.463.380 (5)170
C11—H11···O9ix0.932.403.193 (6)143
C24—H24···O8iv0.932.453.172 (5)135
C29—H29···O5ix0.932.543.350 (6)146
C30—H30···O70.932.283.001 (5)134
C31—H31···O25vii0.932.453.225 (8)141
C36—H36···O4x0.932.343.178 (5)150
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z; (iii) x, y1, z; (iv) x+1, y+2, z+1; (v) x+1, y+2, z; (vi) x, y, z1; (vii) x+1, y+1, z+1; (viii) x+1, y, z+1; (ix) x, y+1, z; (x) x, y+1, z+1.

Experimental details

Crystal data
Chemical formula(C10H10N2)[Ce2(C7H3NO4)4(H2O)4]·5H2O
Mr1261
Crystal system, space groupTriclinic, P1
Temperature (K)150
a, b, c (Å)13.010 (3), 13.453 (3), 13.586 (3)
α, β, γ (°)99.95 (3), 99.87 (3), 104.58 (3)
V3)2208.3 (10)
Z2
Radiation typeMo Kα
µ (mm1)2.14
Crystal size (mm)0.40 × 0.40 × 0.10
Data collection
DiffractometerStoe IPDS II
diffractometer
Absorption correctionNumerical
(X-SHAPE and X-RED32; Stoe & Cie, 2005)
Tmin, Tmax0.440, 0.805
No. of measured, independent and
observed [I > 2σ(I)] reflections
25469, 11857, 10379
Rint0.078
(sin θ/λ)max1)0.685
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.120, 1.05
No. of reflections11857
No. of parameters716
No. of restraints12
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)1.96, 2.01

Computer programs: X-AREA (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5A···O140.82 (3)1.83 (4)2.647 (5)175 (6)
N6—H6A···O11i0.88 (4)1.63 (4)2.514 (5)177 (8)
O17—H17A···O20.82 (7)2.05 (7)2.866 (4)175 (6)
O17—H17B···O13ii0.83 (8)1.88 (8)2.681 (4)161 (7)
O18—H18A···O10.88 (4)2.15 (5)2.983 (5)157 (7)
O18—H18B···O16iii0.90 (4)1.95 (4)2.837 (4)171 (6)
O19—H19A···O15iii0.82 (4)1.93 (4)2.736 (4)167 (10)
O19—H19B···O21iv0.88 (9)1.81 (9)2.689 (5)171 (8)
O20—H20A···O220.85 (8)2.17 (8)2.894 (6)142 (7)
O20—H20B···O23v0.73 (10)2.15 (10)2.847 (5)158 (10)
O21—H21A···O1ii0.89 (4)1.86 (4)2.736 (5)169 (6)
O21—H21B···O6vi0.93 (9)1.93 (9)2.851 (5)171 (8)
O22—H22A···O6vii0.89 (8)2.49 (8)3.127 (5)128 (6)
O22—H22A···O10vii0.89 (8)2.35 (8)3.116 (5)143 (7)
O22—H22B···O23iv0.84 (4)2.12 (7)2.884 (7)150 (6)
O23—H23A···O5vi0.76 (10)1.99 (10)2.736 (6)170 (12)
O23—H23B···O24v0.71 (9)2.30 (11)2.926 (6)149 (16)
O24—H24A···O15i0.87 (15)2.02 (15)2.882 (5)170 (15)
O24—H24B···O220.9 (2)1.9 (2)2.764 (6)161
O25—H25A···O240.92 (11)2.52 (11)3.137 (7)124 (10)
O25—H25B···O1i0.91 (10)2.43 (12)3.120 (7)133 (12)
O25—H25B···O17i0.91 (10)2.32 (13)3.034 (7)136 (15)
C5—H5···O16viii0.932.463.380 (5)170
C11—H11···O9ix0.932.403.193 (6)143
C24—H24···O8ii0.932.453.172 (5)135
C29—H29···O5ix0.932.543.350 (6)146
C30—H30···O70.932.283.001 (5)134
C31—H31···O25v0.932.453.225 (8)141
C36—H36···O4x0.932.343.178 (5)150
Symmetry codes: (i) x, y1, z; (ii) x+1, y+2, z+1; (iii) x+1, y+2, z; (iv) x, y, z1; (v) x+1, y+1, z+1; (vi) x+1, y, z+1; (vii) x+1, y, z; (viii) x1, y, z; (ix) x, y+1, z; (x) x, y+1, z+1.
 

Acknowledgements

We are grateful to the Islamic Azad University, North Tehran Branch, for financial support.

References

First citationAghabozorg, H., Eshtiagh-Hosseini, H., Salimi, A. R. & Mirzaei, M. (2010a). J. Iran. Chem. Soc. 7, 289–300.  CrossRef CAS Google Scholar
First citationAghabozorg, H., Manteghi, F. & Sheshmani, S. (2008). J. Iran. Chem. Soc. 5, 184–227.  CrossRef CAS Google Scholar
First citationAghabozorg, H., Moteieyan, E., Salimi, A. R., Mirzaei, M., Manteghi, F., Shokrollahi, A., Derki, S., Ghadermazi, M., Sheshmani, S. & Eshtiagh-Hosseini, H. (2010b). Polyhedron, 29, 1453–1464.  Web of Science CSD CrossRef CAS Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSheshmani, S., Kheirollahi, P. D., Aghabozorg, H., Shokrollahi, A., Kickelbick, G., Shamsipur, M., Ramezanipour, F. & Moghimi, A. (2005). Z. Anorg. Allg. Chem. 631, 3058–3065.  Web of Science CSD CrossRef Google Scholar
First citationSoleimannejad, J., Aghabozorg, H., Hooshmand, S. & Adams, H. (2007). Acta Cryst. E63, m3089–m3090.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationStoe & Cie (2005). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany.  Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 3| March 2011| Pages m335-m336
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds