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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): m1514–m1515.
Published online 2010 November 6. doi:  10.1107/S1600536810044727
PMCID: PMC3011794

catena-Poly[[triaqua­chlorido-μ3-malonato-cerium(III)] hemihydrate]

Abstract

The asymmetric unit of the title compound, {[Ce(C3H2O4)Cl(H2O)3]·0.5H2O}n, contains a Ce3+ atom coordinated by a chloride anion, three water mol­ecules and a malonate ligand, and one water mol­ecule of crystallization with a factor of occupancy of 50%. The malonate ligand is bonded to three different symmetry-related metal atoms yielding a one-dimensional coordination polymer running parallel to the a axis. A supra­molecular network composed of strong and highly directional O—H(...)O and O—H(...)Cl hydrogen bonds ensures a close and effective packing of adjacent polymeric chains.

Related literature

For general background to coordination compounds of malonates with lanthanides, see: Cañadillas-Delgado et al. (2006 [triangle]); Doreswamy et al. (2003 [triangle], 2005 [triangle]); Hernández-Molina et al. (2000 [triangle], 2002 [triangle], 2003 [triangle]). For previous research from our group on coordination compounds of phospho­nates, see: Cunha-Silva et al. (2007 [triangle], 2009 [triangle]); Shi et al. (2008 [triangle]); Paz et al. (2004 [triangle], 2005 [triangle]). For general background to the synthesis of coordination polymers using microwave heating, see: Klinowski et al. (2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1514-scheme1.jpg

Experimental

Crystal data

  • [Ce(C3H2O4)Cl(H2O)3]·0.5H2O
  • M r = 681.34
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1514-efi1.jpg
  • a = 7.6340 (2) Å
  • b = 14.3065 (3) Å
  • c = 8.7370 (2) Å
  • β = 99.949 (1)°
  • V = 939.87 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 5.13 mm−1
  • T = 150 K
  • 0.26 × 0.16 × 0.16 mm

Data collection

  • Bruker X8 Kappa CCD APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1998 [triangle]) T min = 0.349, T max = 0.494
  • 8271 measured reflections
  • 2514 independent reflections
  • 2481 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.021
  • wR(F 2) = 0.053
  • S = 1.17
  • 2514 reflections
  • 143 parameters
  • 12 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 1.46 e Å−3
  • Δρmin = −1.77 e Å−3

Data collection: APEX2 (Bruker, 2006 [triangle]); cell refinement: SAINT-Plus (Bruker, 2005 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2009 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810044727/cv2789sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044727/cv2789Isup2.hkl

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

Acknowledgments

We are grateful to the Fundação para a Ciência e a Tecnologia (FCT, Portugal) for their financial support through the R&D project PTDC/QUI-QUI/098098/2008 (FCOMP-01–0124-FEDER-010785), the PhD and post-doctoral research grants Nos. SFRH/BD/46601/2008 (to PS) and SFRH/BPD/63736/2009 (to JAF), respectively, and also for specific funding for the purchase of the single-crystal diffractometer.

supplementary crystallographic information

Comment

The hydro-ionothermal reaction between tetraethyl-p-xylylenebisphosphonate (texbp) and CeCl3.6H2O in pre-prepared homogeneous eutectic mixtures of choline chloride and malonic acid is known to lead to the phase-pure crystalline material [Ce(Hpmd)(H2O)] [where H4pmd is 1,4-phenylenebis(methylene)diphosphonic acid, the hydrolysis product of texbp] (Shi et al., 2008). Following our continuous interest in the preparation and study of the properties of metal-organic frameworks based on phosphonates (Cunha-Silva et al., 2009; Cunha-Silva et al., 2007; Paz et al., 2005; Paz et al., 2004), and our recent motivation to employ microwaves as an alternative heating source (Klinowski et al., 2010), we decided to test the aforementioned synthetic conditions inside a microwave reactor. The use of microwave heating instead of hydro-ionothermal conditions resulted instead in the isolation of the title compound as a by-product, being composed of a one-dimensional polymer of Ce3+ with malonate residues. Noteworthy, this organic ligand can be found in a number of structures comprising lanthanide centres (Cañadillas-Delgado et al., 2006; Hernández-Molina et al., 2000; Hernández-Molina et al., 2002; Hernández -Molina et al., 2003; Doreswamy et al., 2003; Doreswamy et al. 2005) exhibiting several types of coordination modes such as unidentate, chelating and bridging.

The asymmetric unit of the title compound (see Scheme) comprises a chlorido, three water and one malonato (mal2-) entities coordinated to Ce3+, and one half-occupied water molecule of crystallization located in a generic crystallographic position: [CeCl(mal)(H2O)3].0.5(H2O). The coordination geometry of the metallic centre can be described as a highly distorted dodecahedron (Figure 1). For example, while the Ce1—Owater distances range from 2.4580 (17) to 2.5895 (17) Å (see Table 1), the Ce1—Cl1 bond is considerably longer [2.9086 (6) Å]. The malonate ligand is, on the one hand, bound to the central Ce3+via distal Ce—O bonds [distances of 2.5683 (16) and 2.4940 (16) Å], leading to the formation of a six-membered chelate ring. On the other, each carboxylate establishes a physical connection with a neighbouring metallic centre via proximal chelations [Ce—O distances in the 2.6083 (16) to 2.6793 (18) Å range - see Table 1], thus forming the four-membered chelate rings depicted in the chemical diagram. These two different coordination modes of the malonate ligand lead to the formation of a one-dimensional coordination polymer running parallel to the [100] direction (Figure 2). The intermetallic distances within the polymer are of 4.3832 (2) and 4.5091 (2) Å.

Due to the large number of donors and acceptors, the crystal structure of the title compound is rich in strong [D···A distances in the 2.652 (2)–3.326 (4) Å range] and highly directional [left angle bracket D—H···A larger than ca 141 (3)°] hydrogen bonds (see Table 2). The hydrogen bonding interactions can be divided in three different types concerning the connectivity in relation to the polymeric chain. Intra-chain hydrogen bonds add stability to the coordination polymer by connecting three adjacent metal centres through a O3W···O2W···Cl chain (blue dashed lines in Figure 2). The other two types of hydrogen bonds involve the crystal packing of adjacent coordination polymers: inter-chain interactions (green dashed lines in Figures 2 and 3) connect coordinated water molecules (O1W and O3W) of one polymer to the oxygen atoms of malonato ligands (O2 and O4, respectively) of an adjacent polymer; the second type of inter-chain interactions occur via the half-occupied crystallization water molecule (O4W) forming O4···O4W···Cl1 chains (pink dashed lines in Figures 2 and 3). The extensive hydrogen bonding network described above leads to a series of strong connections among adjacent coordination polymers as depicted in Figure 3.

Experimental

The title compound was prepared following the procedure described elsewhere (Shi et al., 2008), while replacing hydrothermal heating by microwave heating (Klinowski et al., 2010). The reactive homogeneous suspension was transferred to a 10 ml IntelliVent reactor which was placed inside a CEM Focused MicrowaveTM Synthesis System Discover S-Class equipment. The reaction took place with constant magnetic stirring (controlled by the microwave equipment) and by monitoring the temperature and pressure inside the vessel. Experimental conditions: i) temperature of 120 °C; ii) power of 50 W; iii) reaction time of 45 minutes of microwave irradiation. A constant flow of air (ca 10 psi) ensured a close control of the temperature inside the vessel. After reacting a colourless solution was obtained. The resulting solution was then left to stand at ambient temperature until large block crystals grew by slow evaporation of the solvent over a period of six months.

Refinement

C-bound H atoms were located at their idealized positions and were included in the final structural model in riding-motion approximation with C—H distances of 0.99 Å. The isotropic displacement parameters for these atoms were fixed at 1.2×Ueq of the carbon atom to which they are attached.

All hydrogen atoms associated with the water molecules were directly located from difference Fourier maps and included in the structure with the O—H and H···H distances restrained to 0.95 (1) and 1.55 (1) Å, and with Uiso fixed at 1.5×Ueq of the O atom to which they are attached.

Figures

Fig. 1.
Asymmetric unit of the title compound showing all non-hydrogen atoms as displacement ellipsoids drawn at the 50% probability level and hydrogen atoms as small spheres with arbitrary radius [symmetry codes: (i)2 - x, -y, 2 - z; (ii)1 - x, -y, 2 - z]. The ...
Fig. 2.
Schematic representation of the one-dimensional chain coordination polymer composing the crystal structure of the title compound. Hydrogen bonds are represented as dashed lines: blue - intra-chain interactions; pink - hydrogen bonds with the water molecule ...
Fig. 3.
Crystal packing viewed in perspective along the (a) [100] and (b) [001] directions of the unit cell. Hydrogen bonds represented as in Figure 2.

Crystal data

[Ce(C3H2O4)Cl(H2O)3]·0.5H2OF(000) = 648
Mr = 681.34Dx = 2.408 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6974 reflections
a = 7.6340 (2) Åθ = 3.1–29.1°
b = 14.3065 (3) ŵ = 5.13 mm1
c = 8.7370 (2) ÅT = 150 K
β = 99.949 (1)°Block, colourless
V = 939.87 (4) Å30.26 × 0.16 × 0.16 mm
Z = 2

Data collection

Bruker X8 Kappa CCD APEXII diffractometer2514 independent reflections
Radiation source: fine-focus sealed tube2481 reflections with I > 2σ(I)
graphiteRint = 0.028
ω and [var phi] scansθmax = 29.1°, θmin = 3.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)h = −7→10
Tmin = 0.349, Tmax = 0.494k = −19→18
8271 measured reflectionsl = −11→11

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.021H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.053w = 1/[σ2(Fo2) + (0.0241P)2 + 1.2954P] where P = (Fo2 + 2Fc2)/3
S = 1.17(Δ/σ)max = 0.001
2514 reflectionsΔρmax = 1.46 e Å3
143 parametersΔρmin = −1.77 e Å3
12 restraintsExtinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0139 (5)

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*/UeqOcc. (<1)
Ce10.742523 (15)−0.079259 (8)0.986480 (14)0.00713 (7)
Cl10.93077 (9)−0.10017 (4)1.30370 (7)0.01792 (13)
O10.9184 (2)0.07240 (11)1.0558 (2)0.0110 (3)
O21.1044 (2)0.14538 (12)1.23544 (19)0.0126 (3)
O30.5892 (2)0.03721 (11)1.12981 (19)0.0100 (3)
O40.4894 (2)0.16117 (13)1.2331 (2)0.0187 (4)
C10.9494 (3)0.11752 (15)1.1829 (3)0.0089 (4)
C20.8055 (3)0.14023 (19)1.2763 (3)0.0166 (5)
H2A0.83750.11001.37930.020*
H2B0.80660.20861.29380.020*
C30.6181 (3)0.11199 (16)1.2087 (3)0.0113 (4)
O1W0.8161 (3)−0.24629 (12)1.0159 (2)0.0186 (4)
H1X0.844 (5)−0.2811 (19)0.932 (2)0.028*
H1Y0.844 (5)−0.2812 (19)1.1084 (19)0.028*
O2W0.7066 (2)0.03997 (12)0.7602 (2)0.0139 (3)
H2X0.815 (2)0.065 (2)0.740 (3)0.021*
H2Y0.635 (3)0.021 (2)0.667 (2)0.021*
O3W0.5195 (3)−0.16461 (12)1.1230 (2)0.0185 (4)
H3X0.518 (5)−0.2259 (10)1.164 (4)0.028*
H3Y0.439 (4)−0.1266 (17)1.167 (4)0.028*
O4W0.4133 (5)0.0545 (3)0.5211 (4)0.0186 (7)0.50
H4X0.318 (7)0.066 (4)0.576 (8)0.028*0.50
H4Y0.435 (9)0.109 (3)0.465 (7)0.028*0.50

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ce10.00713 (9)0.00740 (9)0.00779 (9)−0.00056 (4)0.00394 (5)−0.00129 (3)
Cl10.0202 (3)0.0217 (3)0.0116 (3)−0.0073 (2)0.0020 (2)0.0043 (2)
O10.0114 (8)0.0119 (7)0.0108 (8)−0.0008 (6)0.0051 (6)−0.0046 (6)
O20.0086 (8)0.0182 (8)0.0116 (7)−0.0021 (6)0.0034 (6)−0.0050 (6)
O30.0094 (8)0.0096 (7)0.0118 (7)−0.0012 (6)0.0040 (6)−0.0031 (6)
O40.0094 (8)0.0192 (8)0.0285 (10)0.0005 (7)0.0062 (7)−0.0146 (7)
C10.0091 (10)0.0076 (9)0.0108 (9)0.0003 (7)0.0038 (8)0.0005 (7)
C20.0078 (11)0.0253 (12)0.0180 (11)−0.0024 (9)0.0061 (9)−0.0128 (10)
C30.0095 (10)0.0140 (10)0.0118 (10)−0.0024 (8)0.0062 (8)−0.0034 (8)
O1W0.0330 (11)0.0132 (8)0.0111 (8)0.0097 (8)0.0078 (7)0.0013 (6)
O2W0.0112 (8)0.0178 (8)0.0133 (8)−0.0016 (6)0.0036 (6)0.0001 (6)
O3W0.0198 (9)0.0112 (7)0.0288 (10)0.0021 (7)0.0159 (8)0.0049 (7)
O4W0.0189 (19)0.0240 (18)0.0134 (16)0.0028 (16)0.0043 (14)0.0011 (14)

Geometric parameters (Å, °)

Ce1—O1W2.4580 (17)O3—Ce1ii2.6304 (17)
Ce1—O32.4940 (16)O4—C31.256 (3)
Ce1—O3W2.5525 (18)O4—Ce1ii2.6487 (18)
Ce1—O12.5683 (16)C1—C21.512 (3)
Ce1—O2W2.5895 (17)C1—Ce1i3.038 (2)
Ce1—O2i2.6083 (16)C2—C31.505 (3)
Ce1—O3ii2.6304 (17)C2—H2A0.9900
Ce1—O4ii2.6487 (18)C2—H2B0.9900
Ce1—O1i2.6793 (18)C3—Ce1ii3.014 (2)
Ce1—Cl12.9086 (6)O1W—H1X0.943 (10)
Ce1—C3ii3.014 (2)O1W—H1Y0.943 (10)
Ce1—C1i3.038 (2)O2W—H2X0.944 (10)
O1—C11.271 (3)O2W—H2Y0.941 (10)
O1—Ce1i2.6793 (18)O3W—H3X0.947 (10)
O2—C11.258 (3)O3W—H3Y0.95 (3)
O2—Ce1i2.6083 (16)O4W—H4X0.947 (10)
O3—C31.271 (3)O4W—H4Y0.947 (10)
O1W—Ce1—O3135.69 (6)O3ii—Ce1—C3ii24.86 (5)
O1W—Ce1—O3W69.19 (6)O4ii—Ce1—C3ii24.56 (6)
O3—Ce1—O3W71.11 (5)O1i—Ce1—C3ii137.52 (6)
O1W—Ce1—O1134.11 (7)Cl1—Ce1—C3ii140.88 (5)
O3—Ce1—O165.71 (5)O1W—Ce1—C1i72.16 (6)
O3W—Ce1—O1131.12 (6)O3—Ce1—C1i146.63 (6)
O1W—Ce1—O2W135.43 (6)O3W—Ce1—C1i140.97 (6)
O3—Ce1—O2W86.92 (5)O1—Ce1—C1i81.37 (6)
O3W—Ce1—O2W132.90 (6)O2W—Ce1—C1i74.66 (6)
O1—Ce1—O2W66.78 (6)O2i—Ce1—C1i24.25 (6)
O1W—Ce1—O2i66.52 (6)O3ii—Ce1—C1i128.90 (6)
O3—Ce1—O2i157.66 (5)O4ii—Ce1—C1i92.55 (6)
O3W—Ce1—O2i126.49 (6)O1i—Ce1—C1i24.68 (6)
O1—Ce1—O2i101.46 (5)Cl1—Ce1—C1i98.57 (4)
O2W—Ce1—O2i70.93 (5)C3ii—Ce1—C1i113.88 (6)
O1W—Ce1—O3ii116.75 (6)C1—O1—Ce1130.24 (15)
O3—Ce1—O3ii62.43 (6)C1—O1—Ce1i93.64 (14)
O3W—Ce1—O3ii67.32 (6)Ce1—O1—Ce1i118.46 (6)
O1—Ce1—O3ii109.09 (5)C1—O2—Ce1i97.36 (13)
O2W—Ce1—O3ii65.58 (5)C3—O3—Ce1141.45 (15)
O2i—Ce1—O3ii108.72 (5)C3—O3—Ce1ii94.72 (14)
O1W—Ce1—O4ii75.98 (6)Ce1—O3—Ce1ii117.57 (6)
O3—Ce1—O4ii110.26 (5)C3—O4—Ce1ii94.24 (14)
O3W—Ce1—O4ii73.16 (6)O2—C1—O1120.1 (2)
O1—Ce1—O4ii143.27 (6)O2—C1—C2117.4 (2)
O2W—Ce1—O4ii76.65 (6)O1—C1—C2122.5 (2)
O2i—Ce1—O4ii68.32 (5)O2—C1—Ce1i58.39 (12)
O3ii—Ce1—O4ii48.92 (5)O1—C1—Ce1i61.67 (12)
O1W—Ce1—O1i80.87 (6)C2—C1—Ce1i175.81 (16)
O3—Ce1—O1i126.38 (5)C3—C2—C1117.41 (19)
O3W—Ce1—O1i145.13 (6)C3—C2—H2A107.9
O1—Ce1—O1i61.54 (6)C1—C2—H2A107.9
O2W—Ce1—O1i81.26 (6)C3—C2—H2B107.9
O2i—Ce1—O1i48.93 (5)C1—C2—H2B107.9
O3ii—Ce1—O1i145.80 (5)H2A—C2—H2B107.2
O4ii—Ce1—O1i117.21 (5)O4—C3—O3119.7 (2)
O1W—Ce1—Cl174.57 (5)O4—C3—C2120.1 (2)
O3—Ce1—Cl177.74 (4)O3—C3—C2120.2 (2)
O3W—Ce1—Cl176.42 (5)O4—C3—Ce1ii61.20 (12)
O1—Ce1—Cl173.15 (4)O3—C3—Ce1ii60.43 (12)
O2W—Ce1—Cl1139.90 (4)C2—C3—Ce1ii167.62 (17)
O2i—Ce1—Cl1117.38 (4)Ce1—O1W—H1X120.7 (18)
O3ii—Ce1—Cl1132.52 (4)Ce1—O1W—H1Y128.3 (18)
O4ii—Ce1—Cl1143.42 (5)H1X—O1W—H1Y109.8 (14)
O1i—Ce1—Cl178.76 (4)Ce1—O2W—H2X114 (2)
O1W—Ce1—C3ii94.47 (7)Ce1—O2W—H2Y116.0 (19)
O3—Ce1—C3ii85.75 (6)H2X—O2W—H2Y110.2 (15)
O3W—Ce1—C3ii64.67 (6)Ce1—O3W—H3X132.1 (19)
O1—Ce1—C3ii130.83 (6)Ce1—O3W—H3Y116.4 (19)
O2W—Ce1—C3ii72.81 (6)H3X—O3W—H3Y109 (3)
O2i—Ce1—C3ii90.33 (6)H4X—O4W—H4Y110.0 (16)
O1W—Ce1—O1—C1−84.6 (2)C1i—Ce1—O3—C3−23.8 (3)
O3—Ce1—O1—C146.42 (19)O1W—Ce1—O3—Ce1ii−101.07 (10)
O3W—Ce1—O1—C116.4 (2)O3W—Ce1—O3—Ce1ii−73.68 (8)
O2W—Ce1—O1—C1143.9 (2)O1—Ce1—O3—Ce1ii129.82 (8)
O2i—Ce1—O1—C1−152.87 (19)O2W—Ce1—O3—Ce1ii63.96 (7)
O3ii—Ce1—O1—C192.5 (2)O2i—Ce1—O3—Ce1ii71.47 (16)
O4ii—Ce1—O1—C1138.16 (18)O3ii—Ce1—O3—Ce1ii0.0
O1i—Ce1—O1—C1−123.6 (2)O4ii—Ce1—O3—Ce1ii−10.60 (9)
Cl1—Ce1—O1—C1−37.46 (19)O1i—Ce1—O3—Ce1ii140.74 (6)
C3ii—Ce1—O1—C1106.6 (2)Cl1—Ce1—O3—Ce1ii−153.33 (7)
C1i—Ce1—O1—C1−139.21 (18)C3ii—Ce1—O3—Ce1ii−9.01 (7)
O1W—Ce1—O1—Ce1i39.03 (11)C1i—Ce1—O3—Ce1ii119.68 (10)
O3—Ce1—O1—Ce1i170.01 (9)Ce1i—O2—C1—O1−0.2 (2)
O3W—Ce1—O1—Ce1i139.96 (7)Ce1i—O2—C1—C2179.99 (18)
O2W—Ce1—O1—Ce1i−92.54 (8)Ce1—O1—C1—O2133.00 (19)
O2i—Ce1—O1—Ce1i−29.27 (8)Ce1i—O1—C1—O20.2 (2)
O3ii—Ce1—O1—Ce1i−143.90 (7)Ce1—O1—C1—C2−47.2 (3)
O4ii—Ce1—O1—Ce1i−98.25 (10)Ce1i—O1—C1—C2180.0 (2)
O1i—Ce1—O1—Ce1i0.0Ce1—O1—C1—Ce1i132.79 (18)
Cl1—Ce1—O1—Ce1i86.13 (7)O2—C1—C2—C3176.4 (2)
C3ii—Ce1—O1—Ce1i−129.82 (8)O1—C1—C2—C3−3.4 (4)
C1i—Ce1—O1—Ce1i−15.61 (7)Ce1ii—O4—C3—O3−15.7 (2)
O1W—Ce1—O3—C3115.4 (2)Ce1ii—O4—C3—C2165.9 (2)
O3W—Ce1—O3—C3142.8 (3)Ce1—O3—C3—O4163.95 (17)
O1—Ce1—O3—C3−13.7 (2)Ce1ii—O3—C3—O415.9 (2)
O2W—Ce1—O3—C3−79.6 (2)Ce1—O3—C3—C2−17.7 (4)
O2i—Ce1—O3—C3−72.1 (3)Ce1ii—O3—C3—C2−165.7 (2)
O3ii—Ce1—O3—C3−143.5 (3)Ce1—O3—C3—Ce1ii148.1 (2)
O4ii—Ce1—O3—C3−154.1 (2)C1—C2—C3—O4−146.9 (2)
O1i—Ce1—O3—C3−2.8 (3)C1—C2—C3—O334.7 (3)
Cl1—Ce1—O3—C363.1 (2)C1—C2—C3—Ce1ii−54.5 (8)
C3ii—Ce1—O3—C3−152.5 (2)

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

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1W—H1X···Cl1iii0.94 (1)2.20 (2)3.0967 (18)159 (2)
O1W—H1Y···O2iv0.94 (1)1.71 (1)2.652 (2)174 (3)
O2W—H2X···Cl1i0.94 (1)2.11 (1)3.0416 (19)171 (3)
O2W—H2Y···O4Wv0.94 (1)1.94 (2)2.816 (4)153 (3)
O2W—H2Y···O4W0.94 (1)2.00 (2)2.793 (4)141 (3)
O3W—H3X···O4vi0.95 (1)1.86 (1)2.798 (2)173 (3)
O3W—H3Y···O2Wii0.95 (3)1.85 (3)2.794 (3)173 (3)
O4W—H4X···Cl1ii0.95 (1)2.38 (1)3.326 (4)176 (6)
O4W—H4Y···O4vii0.95 (1)2.26 (4)3.083 (4)144 (5)

Symmetry codes: (iii) x, −y−1/2, z−1/2; (iv) −x+2, y−1/2, −z+5/2; (i) −x+2, −y, −z+2; (v) −x+1, −y, −z+1; (vi) −x+1, y−1/2, −z+5/2; (ii) −x+1, −y, −z+2; (vii) x, y, z−1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2789).

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