supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers buy article online

Acta Cryst. (2007). E63, m1430    [ doi:10.1107/S1600536807019010 ]

catena-Poly[[[triaqua(4,4'-bipyridine N,N'-dioxide-[kappa]O)dichloridocerium(III)]-[mu]2-4,4'-bipyridine N,N'-dioxide-[kappa]2O:O'] chloride monohydrate]

D.-Q. Yuan, F.-Y. Lian and M.-C. Hong

Abstract top

In the title compound, [CeCl2(C10H8N2O2)2(H2O)3]Cl·H2O, each CeIII atom is coordinated by six O atoms [Ce-O = 2.454 (3)-2.454 (3) Å] and two chloride ions [Ce-Cl = 2.8277 (9) and 2.8721 (9) Å] in a distorted tetragonal-antiprismatic geometry. One of the 4,4'-bipyridine N,N'-dioxide ligands acts as a bridging ligand while the other acts a terminal ligand, leading to the formation of a linear polymeric structure. In the crystal structure, adjacent polymeric chains are cross-linked by O-H...O and O-H...Cl hydrogen bonds, forming a three-dimensional network.

Comment top

Recently, inorganic-organic coordination compounds attracted considerable attention due to their fascinating structure and potential applications as functional materials (Kitagawa & Kitaura, 2004; Yaghi et al., 2003). Multidentate O-donor ligands have been employed extensively as organic spacers in the construction of extended networks. 4,4'-Bipyridine N,N'-dioxide (L), a typical bridge ligand, can coordinate to lanthanide metal ions in five possible modes, and generate some predicted, controlled structural frameworks, including one-dimensional chains, two-dimensional layer, and three-dimensional network (Hill et al., 2004; Long et al., 2000, 2001, 2002, 2004; Ma et al., 2005). We report here the synthesis and crystal structure of the title compound, (I).

As illustrated in Fig. 1, in compound (I), each CeIII atom is coordinated by six O atoms [Ce—O = 2.454 (3)–2.545 (3) Å] from three L ligands and three water molecules, and two chloride ions [Ce—Cl = 2.8277 (9) and 2.8721 (9) Å] in a distorted tetragonal antiprism geometry. The interesting feature of (I) is that the asymmetric unit contains two L ligands, which exhibit two different coordination modes. One of the L acts as a bridging ligand, linking two CeIII ions, with a Ce···Cei distance of 13.1324 (8) Å [symmetry code: (i) x + 1, y - 1, z], and the other acts a terminal ligand. As a result of this coordination a linear polymeric chain is formed (Fig. 2), similar to that in catena-[bis(µ2-4,4'-bipyridine N,N'-dioxide)-tris (nitrato)-terbium(III)] (Long et al., 2002) but different from the wave-like chain in catena-[(µ2-4,4'-bipyridine N,N'-dioxide)-(methanol)-\ tris(nitrato)-terbium(III)] (Long et al., 2002). The pyridine rings in the L ligand are not coplanar; the dihedral angle between the N1- and N2-pyridine rings is 14.2 (2)° and that between the N3- and N4-pyridine rings is 10.5 (2)°.

In the polymeric chain, weak face-to face π-π interactions are observed between the adjacent bridging and terminal L ligands, with Cg3···Cg2i and Cg4···Cg1i distances of 3.596 (2) and 3.888 (2) Å, respectively (Cg1, Cg2, Cg3 and Cg4 denote the centroids of the N1/C1—C5, N2/C6—C10, N3/C11—C15 and N4/C16—C20 rings, respectively). The neighboring chains are cross-linked by O—H···O and O—H···Cl hydrogen bonds, involving three coordinated water molecules, one lattice water molecule, one uncoordinated chloride ion and the uncoordinated O atom of the L ligand (Table 1), forming a three-dimensional hydrogen-bonded network, as shown in Fig.3.

Related literature top

For related literature, see: Hill et al. (2004); Kitagawa & Kitaura (2004); Long et al. (2000, 2001, 2002, 2004); Ma et al. (2005); Yaghi et al. (2003).

Experimental top

A mixture of CeCl3.6H2O (0.20 mmol), 4,4'-bipyridine N,N'-dioxide (0.40 mmol) and water (10 ml) was stirred at ca 323 K for 3 h and then filtered. The filtrate was kept at room temperature and yellow crystals of the title compound (yield 53%, based on Ce) were obtained after several days.

Refinement top

The water H atoms were located in difference Fourier maps, and refined with O—H distances restrained at 0.85 Å and Uiso = 1.2Ueq(O). The remaining H atoms were positioned geometrically, with C—H = 0.93 Å, and were constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C)

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2004); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. Coordination environment of the Cerium atom in (I). Displacement ellipsoids are drawn at the 35% probability level. [Symmetry code: (i) x + 1, y - 1, z.]
[Figure 2] Fig. 2. Part of the polymeric chain of (I). H atoms have been omitted for clarity. [Symmetry code: (i) x + 1, y - 1, z.]
[Figure 3] Fig. 3. Part of the hydrogen-bonded (dashed lines) network in (I). [Symmetry codes: (i) x + 1, y - 1, z; (ii) x - 1, y + 1, z; (iii) -x - 1, -y + 2, -z + 2; (iv) -x, -y + 1, -z + 2; (v) -x + 1, -y, -z + 1; (vi) -x, -y + 1, -z + 1.]
catena-Poly[[[triaqua(4,4'-bipyridine N,N'-dioxide-κO)dichloridocerium(III)]-µ2-4,4'-bipyridine N,N'-dioxide-κ2O:O'] chloride monohydrate] top
Crystal data top
[CeCl2(C10H8N2O2)2(H2O)3]Cl·H2O)Z = 2
Mr = 694.90F(000) = 690
Triclinic, P1Dx = 1.813 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.6677 (1) ÅCell parameters from 3563 reflections
b = 10.4584 (3) Åθ = 2.3–27.5°
c = 14.7861 (3) ŵ = 2.16 mm−1
α = 83.362 (5)°T = 293 K
β = 73.027 (4)°Prism, orange
γ = 86.190 (6)°0.45 × 0.22 × 0.10 mm
V = 1272.63 (6) Å3
Data collection top
Rigaku Mercury CCD
diffractometer		5698 independent reflections
Radiation source: fine-focus sealed tube5315 reflections with I > 2σ(I)
graphiteRint = 0.019
Detector resolution: 14.6306 pixels mm-1θmax = 27.5°, θmin = 2.3°
ω scansh = −11→10
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2004)		k = −13→9
Tmin = 0.444, Tmax = 0.813l = −19→19
9756 measured reflections
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0423P)2 + 2.1096P]
where P = (Fo2 + 2Fc2)/3
5698 reflections(Δ/σ)max = 0.001
325 parametersΔρmax = 1.31 e Å−3
0 restraintsΔρmin = −1.13 e Å−3
Crystal data top
[CeCl2(C10H8N2O2)2(H2O)3]Cl·H2O)γ = 86.190 (6)°
Mr = 694.90V = 1272.63 (6) Å3
Triclinic, P1Z = 2
a = 8.6677 (1) ÅMo Kα radiation
b = 10.4584 (3) ŵ = 2.16 mm−1
c = 14.7861 (3) ÅT = 293 K
α = 83.362 (5)°0.45 × 0.22 × 0.10 mm
β = 73.027 (4)°
Data collection top
Rigaku Mercury CCD
diffractometer		5698 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2004)		5315 reflections with I > 2σ(I)
Tmin = 0.444, Tmax = 0.813Rint = 0.019
9756 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.084Δρmax = 1.31 e Å−3
S = 1.06Δρmin = −1.13 e Å−3
5698 reflectionsAbsolute structure: ?
325 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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) top
xyzUiso*/Ueq
Ce10.00594 (2)0.441087 (16)0.796133 (12)0.01936 (7)
Cl1−0.11177 (11)0.19676 (8)0.88064 (7)0.03122 (19)
Cl20.09043 (12)0.67876 (8)0.84625 (6)0.03285 (19)
Cl30.10399 (16)0.85283 (13)0.58040 (9)0.0563 (3)
O1−0.2380 (4)0.5682 (3)0.7862 (2)0.0387 (7)
O2−0.8044 (3)1.3811 (2)0.8983 (2)0.0350 (6)
O30.7408 (4)−0.5185 (3)0.5485 (2)0.0378 (6)
O40.2428 (3)0.3201 (3)0.6970 (2)0.0373 (6)
O5−0.1189 (4)0.3598 (3)0.6824 (2)0.0464 (8)
H5A−0.09350.28450.66530.056*
H5B−0.14660.39720.63510.056*
O6−0.1698 (3)0.4586 (3)0.96565 (18)0.0332 (6)
H6A−0.18120.52200.99840.040*
H6B−0.14650.39170.99830.040*
O70.1258 (4)0.5682 (2)0.63959 (18)0.0385 (7)
H7B0.11480.64820.62360.046*
H7A0.17310.53930.58670.046*
O8−0.0742 (3)0.10277 (19)0.62206 (14)0.0154 (4)
H8A−0.00280.07250.64850.018*
H8B−0.05260.08700.56450.018*
N1−0.3048 (4)0.6797 (3)0.8165 (2)0.0291 (7)
N2−0.7157 (4)1.2713 (3)0.8993 (2)0.0271 (6)
N30.3114 (4)0.2040 (3)0.6792 (2)0.0259 (6)
N40.6763 (4)−0.4033 (3)0.5714 (2)0.0284 (6)
C1−0.2279 (5)0.7893 (4)0.7815 (3)0.0357 (9)
H1−0.12420.78670.73990.043*
C2−0.4516 (5)0.6817 (4)0.8794 (3)0.0416 (10)
H2−0.50200.60480.90590.050*
C3−0.3012 (5)0.9058 (4)0.8068 (3)0.0335 (8)
H3−0.24550.98100.78250.040*
C4−0.5281 (5)0.7971 (4)0.9050 (3)0.0394 (10)
H4−0.63040.79720.94830.047*
C5−0.4557 (4)0.9133 (3)0.8673 (2)0.0236 (7)
C6−0.5413 (4)1.0395 (3)0.8856 (2)0.0232 (7)
C7−0.4733 (4)1.1541 (3)0.8356 (3)0.0299 (8)
H7−0.36751.15300.79660.036*
C8−0.6954 (4)1.0496 (4)0.9479 (3)0.0297 (8)
H8−0.74160.97690.98590.036*
C9−0.5622 (5)1.2680 (4)0.8442 (3)0.0320 (8)
H9−0.51571.34370.81140.038*
C10−0.7813 (5)1.1658 (4)0.9543 (3)0.0313 (8)
H10−0.88411.17120.99660.038*
C110.4609 (5)0.1976 (4)0.6179 (3)0.0304 (8)
H110.51400.27280.58950.037*
C120.2344 (4)0.0960 (3)0.7219 (3)0.0282 (7)
H120.13120.10220.76370.034*
C130.5353 (4)0.0786 (3)0.5975 (3)0.0290 (7)
H130.63720.07480.55400.035*
C140.3065 (4)−0.0234 (4)0.7045 (3)0.0276 (7)
H140.2523−0.09710.73550.033*
C150.4602 (4)−0.0351 (3)0.6406 (2)0.0231 (7)
C160.5370 (4)−0.1637 (3)0.6185 (2)0.0246 (7)
C170.6976 (5)−0.1775 (4)0.5648 (3)0.0343 (8)
H170.7603−0.10530.54370.041*
C180.4512 (5)−0.2754 (4)0.6482 (3)0.0338 (8)
H180.3443−0.27050.68510.041*
C190.7645 (5)−0.2979 (4)0.5423 (3)0.0361 (9)
H190.8719−0.30570.50670.043*
C200.5208 (5)−0.3933 (4)0.6241 (3)0.0368 (9)
H200.4602−0.46680.64430.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ce10.02181 (11)0.01415 (10)0.02068 (10)0.00357 (7)−0.00417 (7)−0.00329 (6)
Cl10.0306 (4)0.0229 (4)0.0348 (4)−0.0044 (3)−0.0010 (4)−0.0006 (3)
Cl20.0440 (5)0.0219 (4)0.0313 (4)−0.0052 (4)−0.0082 (4)−0.0018 (3)
Cl30.0570 (7)0.0563 (7)0.0524 (7)−0.0063 (6)−0.0124 (6)0.0020 (6)
O10.0418 (16)0.0312 (14)0.0461 (16)0.0220 (12)−0.0178 (13)−0.0154 (12)
O20.0448 (16)0.0252 (13)0.0402 (15)0.0187 (12)−0.0205 (13)−0.0144 (11)
O30.0529 (17)0.0228 (13)0.0358 (14)0.0162 (12)−0.0107 (13)−0.0102 (11)
O40.0410 (16)0.0239 (13)0.0414 (15)0.0138 (12)−0.0041 (12)−0.0098 (11)
O50.078 (2)0.0238 (13)0.0532 (18)0.0115 (14)−0.0437 (18)−0.0115 (13)
O60.0428 (15)0.0281 (13)0.0260 (13)0.0021 (11)−0.0042 (11)−0.0084 (10)
O70.0617 (19)0.0198 (12)0.0246 (13)0.0018 (12)0.0009 (12)−0.0012 (10)
O80.0277 (11)0.0113 (9)0.0100 (9)−0.0060 (8)−0.0094 (8)0.0005 (7)
N10.0283 (15)0.0276 (15)0.0313 (15)0.0147 (12)−0.0096 (13)−0.0084 (12)
N20.0329 (16)0.0223 (14)0.0302 (15)0.0113 (12)−0.0149 (13)−0.0112 (12)
N30.0283 (15)0.0237 (14)0.0255 (14)0.0099 (12)−0.0070 (12)−0.0096 (11)
N40.0368 (17)0.0217 (14)0.0265 (14)0.0096 (12)−0.0098 (13)−0.0063 (12)
C10.0287 (19)0.033 (2)0.035 (2)0.0093 (16)0.0029 (16)0.0026 (16)
C20.033 (2)0.0256 (19)0.057 (3)−0.0006 (16)0.0026 (19)−0.0050 (18)
C30.0281 (19)0.0261 (18)0.038 (2)0.0042 (15)0.0001 (16)0.0053 (15)
C40.0263 (19)0.0262 (19)0.055 (3)0.0031 (15)0.0064 (17)−0.0089 (17)
C50.0246 (16)0.0227 (16)0.0233 (16)0.0061 (13)−0.0077 (13)−0.0023 (13)
C60.0228 (16)0.0239 (16)0.0229 (15)0.0047 (13)−0.0074 (13)−0.0036 (13)
C70.0231 (17)0.0258 (18)0.040 (2)0.0023 (14)−0.0086 (15)−0.0034 (15)
C80.0294 (18)0.0284 (18)0.0264 (17)0.0065 (15)−0.0031 (14)0.0006 (14)
C90.033 (2)0.0234 (17)0.041 (2)−0.0006 (15)−0.0128 (17)−0.0020 (15)
C100.0299 (19)0.035 (2)0.0257 (17)0.0105 (16)−0.0047 (14)−0.0058 (15)
C110.0308 (19)0.0241 (17)0.0305 (18)0.0030 (14)−0.0012 (15)−0.0013 (14)
C120.0239 (17)0.0266 (17)0.0324 (18)0.0036 (14)−0.0037 (14)−0.0104 (14)
C130.0246 (17)0.0265 (17)0.0313 (18)0.0064 (14)−0.0009 (14)−0.0069 (14)
C140.0261 (17)0.0249 (17)0.0308 (18)0.0006 (14)−0.0053 (14)−0.0067 (14)
C150.0228 (16)0.0217 (16)0.0255 (16)0.0037 (13)−0.0075 (13)−0.0069 (13)
C160.0260 (17)0.0212 (16)0.0267 (16)0.0038 (13)−0.0072 (14)−0.0065 (13)
C170.0250 (18)0.0266 (18)0.049 (2)0.0024 (15)−0.0045 (16)−0.0122 (17)
C180.0271 (19)0.0249 (18)0.042 (2)0.0018 (15)0.0017 (16)−0.0047 (16)
C190.0257 (18)0.031 (2)0.048 (2)0.0072 (15)−0.0038 (17)−0.0124 (17)
C200.038 (2)0.0220 (18)0.044 (2)0.0005 (16)−0.0013 (17)−0.0039 (16)
Geometric parameters (Å, °) top
Ce1—O12.454 (3)C2—H20.93
Ce1—O52.498 (3)C3—C51.380 (5)
Ce1—O72.504 (3)C3—H30.93
Ce1—O42.508 (3)C4—C51.386 (5)
Ce1—O2i2.544 (3)C4—H40.93
Ce1—O62.545 (3)C5—C61.484 (4)
Ce1—Cl12.8277 (9)C6—C81.389 (5)
Ce1—Cl22.8721 (9)C6—C71.402 (5)
O1—N11.332 (4)C7—C91.373 (5)
O2—N21.340 (4)C7—H70.93
O3—N41.332 (4)C8—C101.380 (5)
O4—N31.336 (4)C8—H80.93
O5—H5A0.85C9—H90.93
O5—H5B0.85C10—H100.93
O6—H6A0.85C11—C131.387 (5)
O6—H6B0.85C11—H110.93
O7—H7B0.85C12—C141.377 (5)
O7—H7A0.85C12—H120.93
O8—H8A0.85C13—C151.389 (5)
O8—H8B0.85C13—H130.93
N1—C11.337 (5)C14—C151.397 (5)
N1—C21.340 (5)C14—H140.93
N2—C91.343 (5)C15—C161.488 (4)
N2—C101.344 (5)C16—C181.384 (5)
N3—C121.345 (5)C16—C171.395 (5)
N3—C111.350 (5)C17—C191.385 (5)
N4—C191.339 (5)C17—H170.93
N4—C201.350 (5)C18—C201.374 (5)
C1—C31.375 (5)C18—H180.93
C1—H10.93C19—H190.93
C2—C41.375 (5)C20—H200.93
O1—Ce1—O568.28 (9)N1—C2—H2119.9
O1—Ce1—O782.33 (10)C4—C2—H2119.9
O5—Ce1—O774.47 (10)C1—C3—C5121.3 (4)
O1—Ce1—O4141.78 (10)C1—C3—H3119.3
O5—Ce1—O479.52 (10)C5—C3—H3119.3
O7—Ce1—O469.30 (9)C2—C4—C5121.3 (4)
O1—Ce1—O2i144.12 (9)C2—C4—H4119.4
O5—Ce1—O2i144.07 (8)C5—C4—H4119.4
O7—Ce1—O2i115.80 (10)C3—C5—C4116.3 (3)
O4—Ce1—O2i73.45 (9)C3—C5—C6121.1 (3)
O1—Ce1—O672.90 (9)C4—C5—C6122.5 (3)
O5—Ce1—O6117.92 (10)C8—C6—C7116.8 (3)
O7—Ce1—O6143.72 (8)C8—C6—C5122.1 (3)
O4—Ce1—O6143.38 (9)C7—C6—C5120.9 (3)
O2i—Ce1—O675.39 (9)C9—C7—C6120.2 (3)
O1—Ce1—Cl1103.72 (8)C9—C7—H7119.9
O5—Ce1—Cl174.42 (8)C6—C7—H7119.9
O7—Ce1—Cl1143.21 (6)C10—C8—C6121.1 (4)
O4—Ce1—Cl186.13 (7)C10—C8—H8119.5
O2i—Ce1—Cl180.49 (7)C6—C8—H8119.5
O6—Ce1—Cl170.10 (6)N2—C9—C7120.8 (4)
O1—Ce1—Cl282.29 (7)N2—C9—H9119.6
O5—Ce1—Cl2140.34 (7)C7—C9—H9119.6
O7—Ce1—Cl275.80 (7)N2—C10—C8119.8 (3)
O4—Ce1—Cl2113.29 (7)N2—C10—H10120.1
O2i—Ce1—Cl273.59 (6)C8—C10—H10120.1
O6—Ce1—Cl274.96 (6)N3—C11—C13119.8 (3)
Cl1—Ce1—Cl2140.64 (3)N3—C11—H11120.1
N1—O1—Ce1134.5 (2)C13—C11—H11120.1
N2—O2—Ce1ii125.79 (19)N3—C12—C14120.7 (3)
N3—O4—Ce1145.4 (2)N3—C12—H12119.6
Ce1—O5—H5A119.7C14—C12—H12119.6
Ce1—O5—H5B132.0C11—C13—C15121.2 (3)
H5A—O5—H5B101.3C11—C13—H13119.4
Ce1—O6—H6A128.0C15—C13—H13119.4
Ce1—O6—H6B105.8C12—C14—C15120.7 (3)
H6A—O6—H6B108.1C12—C14—H14119.7
Ce1—O7—H7B129.1C15—C14—H14119.7
Ce1—O7—H7A127.5C13—C15—C14116.8 (3)
H7B—O7—H7A102.5C13—C15—C16122.0 (3)
H8A—O8—H8B113.1C14—C15—C16121.2 (3)
O1—N1—C1120.0 (3)C18—C16—C17116.6 (3)
O1—N1—C2119.6 (3)C18—C16—C15121.6 (3)
C1—N1—C2120.4 (3)C17—C16—C15121.8 (3)
O2—N2—C9119.2 (3)C19—C17—C16120.6 (4)
O2—N2—C10120.0 (3)C19—C17—H17119.7
C9—N2—C10120.8 (3)C16—C17—H17119.7
O4—N3—C12120.9 (3)C20—C18—C16121.4 (4)
O4—N3—C11118.3 (3)C20—C18—H18119.3
C12—N3—C11120.8 (3)C16—C18—H18119.3
O3—N4—C19120.5 (3)N4—C19—C17120.8 (4)
O3—N4—C20119.4 (3)N4—C19—H19119.6
C19—N4—C20120.1 (3)C17—C19—H19119.6
N1—C1—C3120.4 (3)N4—C20—C18120.5 (4)
N1—C1—H1119.8N4—C20—H20119.7
C3—C1—H1119.8C18—C20—H20119.7
N1—C2—C4120.2 (4)
O5—Ce1—O1—N1−168.3 (4)C8—C6—C7—C9−4.6 (5)
O7—Ce1—O1—N1−92.1 (3)C5—C6—C7—C9171.5 (3)
O4—Ce1—O1—N1−133.7 (3)C7—C6—C8—C104.8 (5)
O2i—Ce1—O1—N132.2 (4)C5—C6—C8—C10−171.2 (3)
O6—Ce1—O1—N161.1 (3)O2—N2—C9—C7−173.0 (3)
Cl1—Ce1—O1—N1124.9 (3)C10—N2—C9—C76.3 (5)
Cl2—Ce1—O1—N1−15.5 (3)C6—C7—C9—N2−0.8 (6)
O1—Ce1—O4—N3−108.8 (4)O2—N2—C10—C8173.3 (3)
O5—Ce1—O4—N3−76.3 (4)C9—N2—C10—C8−6.0 (5)
O7—Ce1—O4—N3−153.5 (4)C6—C8—C10—N20.3 (6)
O2i—Ce1—O4—N379.8 (4)O4—N3—C11—C13−179.7 (3)
O6—Ce1—O4—N347.0 (5)C12—N3—C11—C131.1 (5)
Cl1—Ce1—O4—N3−1.5 (4)O4—N3—C12—C14−179.0 (3)
Cl2—Ce1—O4—N3143.1 (4)C11—N3—C12—C140.2 (5)
Ce1—O1—N1—C164.5 (5)N3—C11—C13—C15−1.6 (6)
Ce1—O1—N1—C2−117.8 (4)N3—C12—C14—C15−1.1 (5)
Ce1ii—O2—N2—C994.6 (4)C11—C13—C15—C140.7 (5)
Ce1ii—O2—N2—C10−84.7 (4)C11—C13—C15—C16179.1 (3)
Ce1—O4—N3—C125.9 (6)C12—C14—C15—C130.6 (5)
Ce1—O4—N3—C11−173.3 (3)C12—C14—C15—C16−177.8 (3)
O1—N1—C1—C3175.0 (4)C13—C15—C16—C18−168.2 (4)
C2—N1—C1—C3−2.7 (6)C14—C15—C16—C1810.2 (5)
O1—N1—C2—C4−174.3 (4)C13—C15—C16—C1710.0 (5)
C1—N1—C2—C43.4 (7)C14—C15—C16—C17−171.7 (3)
N1—C1—C3—C5−0.9 (6)C18—C16—C17—C190.6 (6)
N1—C2—C4—C5−0.6 (7)C15—C16—C17—C19−177.7 (4)
C1—C3—C5—C43.5 (6)C17—C16—C18—C20−1.1 (6)
C1—C3—C5—C6−172.9 (4)C15—C16—C18—C20177.2 (4)
C2—C4—C5—C3−2.8 (6)O3—N4—C19—C17179.0 (4)
C2—C4—C5—C6173.5 (4)C20—N4—C19—C17−0.7 (6)
C3—C5—C6—C8−178.5 (3)C16—C17—C19—N40.3 (6)
C4—C5—C6—C85.3 (5)O3—N4—C20—C18−179.5 (4)
C3—C5—C6—C75.6 (5)C19—N4—C20—C180.2 (6)
C4—C5—C6—C7−170.5 (4)C16—C18—C20—N40.7 (7)
Symmetry codes: (i) x+1, y−1, z; (ii) x−1, y+1, z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···O80.852.062.896 (3)170
O5—H5B···O3ii0.851.932.763 (4)167
O6—H6A···O2iii0.851.902.716 (4)161
O6—H6B···Cl2iv0.852.503.214 (3)142
O7—H7A···O3v0.851.952.778 (4)164
O7—H7B···Cl30.852.173.014 (3)176
O8—H8B···Cl3vi0.852.323.059 (2)145
Symmetry codes: (ii) x−1, y+1, z; (iii) −x−1, −y+2, −z+2; (iv) −x, −y+1, −z+2; (v) −x+1, −y, −z+1; (vi) −x, −y+1, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···O80.852.062.896 (3)170
O5—H5B···O3i0.851.932.763 (4)167
O6—H6A···O2ii0.851.902.716 (4)161
O6—H6B···Cl2iii0.852.503.214 (3)142
O7—H7A···O3iv0.851.952.778 (4)164
O7—H7B···Cl30.852.173.014 (3)176
O8—H8B···Cl3v0.852.323.059 (2)145
Symmetry codes: (i) x−1, y+1, z; (ii) −x−1, −y+2, −z+2; (iii) −x, −y+1, −z+2; (iv) −x+1, −y, −z+1; (v) −x, −y+1, −z+1.
Acknowledgements top

This work was supported by the Natural Science Foundation of China, and the Natural Science Funds and the Young Scientist Funds of Fujian Province (No. 2006 F3130).

references
References top

Hill, R. J., Long, D. L., Turvey, M. S., Blake, A. J., Champness, N. R., Hubberstey, P., Wilson, C. & Schröer, M. (2004). Chem. Commun. pp. 1792–1793.

Kitagawa, S. & Kitaura, R. (2004). Angew. Chem. Int. Ed. 43, 2334–2375.

Long, D. L., Blake, A. J., Champness, N. R. & Schröer, M. (2000). Chem. Commun. pp. 1369–1370.

Long, D. L., Blake, A. J., Champness, N. R., Wilson, C. & Schröer, M. (2001). Angew. Chem. Int. Ed. 40, 2443–2447.

Long, D. L., Blake, A. J., Champness, N. R., Wilson, C. & Schröer, M. (2002). Chem. Eur. J. pp. 2026–2033.

Long, D. L., Hill, R. J., Blake, A. J., Champness, N. R., Hubberstey, P., Proserpio, D. M., Wilson, C. & Schröder, M. (2004). Angew. Chem. Int. Ed. 43, 1851–1854.

Ma, S. L., Qi, C. M., Guo, Q. L. & Zhao, M. X. (2005). J. Mol. Struct. 738, 99–104.

Rigaku/MSC (2004). CrystalClear. Version 1.3.6. Rigaku/MSC, The Woodlands, Texas, USA

Sheldrick, G. M. (1997). SHELXTL. Version 5.10. Bruker AXS Inc., Madison, Wisconsin, USA.

Yaghi, O. M., O'Keeffe, M., Ockwig, N. W., Chae, H. K. & Eddaoudi, M. (2003). Nature (London), 423, 705–714.