PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): m140–m141.
Published online 2007 December 12. doi:  10.1107/S1600536807064483
PMCID: PMC2915085

Poly[hexa­aqua­bis(μ3-naphthalene-2,6-dicarboxyl­ato)(μ2-naphthalene-2,6-dicarboxyl­ato)diholmium(III)]

Abstract

The crystal structure of the title compound, [Ho2(C12H6O4)3(H2O)6]n, contains binuclear centrosymmetric {Ho2O2(CO2)4(H2O)6} cores inter­connected via the naphthalene-2,6-dicarboxyl­ate (NDC2−) bridging ligands into a two-dimensional neutral plane net, ∞2[Ho2(NDC)3(H2O)6], exhibiting a typical (4,4)-topology. Inter­actions between adjacent layers are assured by a series of C—H(...)π contacts and a number of strong and highly directional O—H(...)O hydrogen bonds involving the coordinated water mol­ecules and neighbouring coordinated carboxyl­ate groups. One NDC2− bridging ligand has its centroid located at a crystallographic centre of inversion.

Related literature

For related structures see: Zheng, Sun et al. (2004 [triangle]); Zheng, Wang et al. (2004 [triangle]); Paz & Klinowski (2003 [triangle]); Min & Lee (2002 [triangle]); Wang et al. (2002 [triangle]). For related literature, see: Cunha-Silva, Mafra et al. (2007 [triangle]); Cunha-Silva, Shi et al. (2007 [triangle]); Shi et al. (2007 [triangle]); Mafra et al. (2006 [triangle]); Shi et al. (2006 [triangle]); Paz, Rocha, Klinowski et al. (2005 [triangle]); Almeida Paz, Shi, Mafra et al. (2005 [triangle]); Almeida Paz, Shi, Trindade et al. (2005 [triangle]); Shi et al. (2005 [triangle]); Paz & Klinowski (2004 [triangle]); Almeida Paz et al. (2002a [triangle],b [triangle],c [triangle]); Allen (2002 [triangle]); Allen & Motherwell (2002 [triangle]); Altomare et al. (1994 [triangle]); Deluzet et al. (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m140-scheme1.jpg

Experimental

Crystal data

  • [Ho2(C12H6O4)3(H2O)6]
  • M r = 540.23
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m140-efi1.jpg
  • a = 7.8856 (3) Å
  • b = 9.6537 (5) Å
  • c = 12.5438 (6) Å
  • α = 75.191 (2)°
  • β = 74.224 (2)°
  • γ = 75.352 (2)°
  • V = 870.98 (7) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 4.60 mm−1
  • T = 180 (2) K
  • 0.10 × 0.05 × 0.05 mm

Data collection

  • Nonius KappaCCD diffractometer
  • Absorption correction: multi-scan (SORTAV; Blessing, 1995 [triangle]) T min = 0.730, T max = 0.796
  • 11608 measured reflections
  • 3987 independent reflections
  • 3135 reflections with I > 2σ(I)
  • R int = 0.067

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.079
  • S = 1.00
  • 3987 reflections
  • 271 parameters
  • 9 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 1.51 e Å−3
  • Δρmin = −1.50 e Å−3

Data collection: COLLECT (Nonius, 1998 [triangle]); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997 [triangle]); data reduction: HKL DENZO (Otwinowski & Minor, 1997 [triangle]) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 [triangle]); program(s) used to refine structure: SHELXTL (Bruker, 2001 [triangle]); molecular graphics: DIAMOND (Brandenburg, 2006 [triangle]); software used to prepare material for publication: SHELXTL.

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

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807064483/hj2008sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064483/hj2008Isup2.hkl

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

Acknowledgments

The authors are grateful to Fundação para a Ciência e a Tecnologia (FCT, Portugal) for financial support under the POCI-PPCDT/QUI/58377/2004 research project supported by FEDER.

supplementary crystallographic information

Comment

In less than twenty years, the field of Crystal Engineering involving the synthesis and characterization of multi-dimensional metal-organic frameworks (also known as coordination polymers) has grown immensely to become one of the most active research areas in inorganic chemistry. These worldwide efforts are motivated by the new and often striking structural features obtained by varying the metal centres and the bridging organic ligands, and by the prospect of making materials with direct industrial applications. Following our efforts in the hydrothermal synthesis and structural characterization of highly crystalline materials of this kind, (Cunha-Silva, Mafra et al., 2007; Cunha-Silva, Shi et al., 2007; Shi et al., 2007; Mafra et al., 2006; Shi et al., 2006; Paz, Rocha, Klinowski et al., 2005; Almeida Paz, Shi, Mafra et al., 2005; Almeida Paz, Shi, Trindade et al., 2005; Shi et al., 2005; Paz & Klinowski, 2004; Paz & Klinowski, 2003; Almeida Paz et al. 2002a, 2002b, 2002c), we report here the low temperature crystal structure at 180 (2) K of a two-dimensional lanthanide-organic framework containing residues of naphthalene-2,6-dicarboxylic acid (H2NDC), [Ho2(NDC)3(H2O)6], which is analogous to that reported by Deluzet et al. (2003) but containing instead Er3+, [Er2(NDC)3(H2O)6]. A search in the literature and in the Cambridge Structural Database (CSD, Version 5.28 with three updates - August 2007; Allen, 2002; Allen & Motherwell, 2002) produced only a handful of reports in which lanthanide centres are coordinated to H2 - xNDC-x residues (Zheng, Sun et al., 2004; Zheng, Wang et al., 2004; Paz & Klinowski, 2003; Wang et al., 2002; Min & Lee, 2002).

The structure of the title compound, I, contains a single crystallographically independent metallic centre, Ho1, coordinated to three water molecules (O1W, O2W and O3W) and four NDC2-bridging ligands (Figure 1a), with a {HoO8} coordination geometry resembling a highly distorted dodecahedron (Figure 1 b). The Ho—O bond lengths were found in the 2.252 (3)–2.461 (4) Å range,in good agreement with those of related materials as revealed by a search in the CSD. The three crystallographically independent carboxylate groups coordinate to the Ho3+ centres in distinct coordination fashions as shown in Figure 1a. Notably, the C8 carboxylate group is coordinated via a typical syn,syn2-bridging coordination fashion leading to the formation of binuclear centrosymmetric anionic [Ho2(NDC)6(H2O)6]6- unit (Figure 1) with the Ho(1)···Ho(1)vi intermetallic distance being of 5.0172 (4) Å [symmetry code: (vi) 3 - x, -y, -z]. While the C1 carboxylate group is coordinated via a syn-unidentate coordination fashion, the C13 carboxylate is instead bound to Ho1 via a typical syn,syn-chelate bidentate mode with a bite angle of 54.22 (13)°.

{Ho2O2(CO2)4(H2O)6} cores are interconnected via the bridging NDC2-ligands into an inclined two-dimensional plane net (Figure 2). By taking the centre of gravity of each binuclear centrosymmetric anionic [Ho2(NDC)6(H2O)6]6- unit as a node of the network, the resulting ∞2[Ho2(NDC)3(H2O)6] plane net has a typical (4,4) topology with the inter-nodal distances being of 12.8742 (6) Å and 16.3127 (6) Å. As shown in Figures 3a and 3 b, individual ∞2[Ho2(NDC)3(H2O)6] plane nets close pack in a parallel fashion (not along a principal axis of the unit cell) to produce the crystal structure. Along the [010] crystallographic direction the packing occurs in an orderly ABAB··· fashion (Figure 3 b). Connections between adjacent layers are mainly assured by strong and highly directional O—H···.O hydrogen bonds involving the O2W and O3W coordinated water molecules from one layer and the coordinated carboxylate groups from the neighbouring layer (Figure 4 and Table in the main paper summarizing the geometrical parameters of the hydrogen bonding interactions). Moreover, these connections are reinforced by weak C—H···π interactions between coordinated NDC2- residues belonging to adjacent layers (not shown). It is important to stress that, within each ∞2[Ho2(NDC)3(H2O)6] layer, O1W is also engaged in strong O—H···.O hydrogen bonds which reinforce the connections between neighbouring binuclear units (Figure 4).

Experimental

Starting materials were purchased from commercial sources and were used as received without further purification: holmium(III) chloride hexahydrate (HoCl3.6H2O, 99.9%, Aldrich), naphthalene-2,6-dicarboxylic acid (H2NDC, 99%, Aldrich) and triethylamine (TEA, 99%, Avocado).

To a solution of HoCl3.6H2O (1.054 g, 2.778 mmol) in distilled water (6.88 g), naphthalene-2,6-dicarboxylic acid (0.100 g, 0.463 mmol) and triethylamine (0.097 g, 0.959 mmol) were added and the mixture was stirred thoroughly for 5 minutes at ambient temperature. The suspension, with a molar composition of 6.01 Ho3+: 1.00 H2NDC: 2.07 TEA: 137 H2O, was transferred to a Parr teflon-lined stainless steel vessel (ca 21 cm3) and placed for 8 h at 145 °C in a preheated oven. Before opening, the reaction vessel was allowed to cool slowly to ambient temperature at a rate of 10 ° per hour over a period of 14 h. The isolated crystalline material was mainly composed of crystals of the title compound which were preserved in a portion of the mother liquor before being manually selected under a polarized microscope for subsequent crystal mounting on a glass fibre.

A small amount of colourless plate-like crystals, which could not be physically separated from the title compound, were also investigated and revealed to be isostructural with the frameworks reported by Zheng, Sun et al. (2004). The crystal data for this material will be the subject of a separate communication.

Refinement

A slightly smeared-out electron density was found surrounding the carbon atoms of one bridging naphthalene-2,6-dicarboxylate ligand. However, the quality of the data set did not allow a sensible modelling of this disorder over, at least, two istinct crystallographic positions. C3, C4, C9 and C10 atoms were instead refined using anisotropic displacement parameters which define a typical prolate thermal motion for these atoms.

H atoms associated with the water molecules were clearly visible in difference Fourier maps and were included in the final structural model with the O—H and H···H restrained to 0.95 (1) and 1.55 (1) Å, respectively, in order to ensure a chemically reasonable geometry for these moieties. These H atoms were allowed to ride on their parent O atoms with Uiso fixed at 1.5×Ueq(O). H atoms bound to carbon were instead placed at idealized positions and allowed to ride on their parent atoms with Uiso fixed at 1.2×Ueq(C). All C—H distances are of 0.95 Å.

Figures

Fig. 1.
(a) Schematic representation of the binuclear centrosymmetric anionic [Ho2(NDC)6(H2O)6]6- unit showing the labelling scheme for all non-H atoms composing the asymmetric unit. Displacement ellipsoids are drawn at the 80% probability level and H atoms are ...
Fig. 2.
Mixed polyhedral and ball-and-stick schematic representation of the two-dimensional (4,4) plane net formed by the self-assembly of the binuclear centrosymmetric anionic [Ho2(NDC)6(H2O)6]6- units depicted in Fig. 1. The centres of gravity of the binuclear ...
Fig. 3.
(a) Mixed polyhedral and ball-and-stick and (b) and (c) topological representations of the crystal packing of the title compound. Hydrogen atoms have been omitted for clarity and adjacent (4,4) plane nets are represented with alternating colours.
Fig. 4.
O—H···O hydrogen bonding interactions connecting adjacent binuclear units within the two-dimensional layer (via O1W) and between adjacent layers (via O2W and O3W). Hydrogen bonds are represented as dashed purple lines. ...

Crystal data

[Ho2(C12H6O4)3(H2O)6]Z = 2
Mr = 540.23F(000) = 524
Triclinic, P1Dx = 2.060 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.8856 (3) ÅCell parameters from 14333 reflections
b = 9.6537 (5) Åθ = 1.0–27.5°
c = 12.5438 (6) ŵ = 4.60 mm1
α = 75.191 (2)°T = 180 K
β = 74.224 (2)°Block, white
γ = 75.352 (2)°0.10 × 0.05 × 0.05 mm
V = 870.98 (7) Å3

Data collection

Nonius Kappa CCD diffractometer3135 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.067
Thin slice ω and [var phi] scansθmax = 27.6°, θmin = 3.5°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)h = −10→9
Tmin = 0.730, Tmax = 0.796k = −9→12
11608 measured reflectionsl = −15→16
3987 independent reflections

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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079H atoms treated by a mixture of independent and constrained refinement
S = 1.00w = 1/[σ2(Fo2) + (0.0301P)2] where P = (Fo2 + 2Fc2)/3
3987 reflections(Δ/σ)max = 0.001
271 parametersΔρmax = 1.51 e Å3
9 restraintsΔρmin = −1.49 e Å3

Special details

Experimental. See dedicated section in the main paper
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
Ho11.23306 (3)0.20677 (3)−0.001555 (19)0.01786 (10)
O1W1.1573 (5)0.4195 (4)0.0764 (3)0.0232 (9)
H1A1.207 (6)0.504 (3)0.039 (4)0.035*
H1B1.039 (3)0.450 (5)0.118 (4)0.035*
O2W1.4902 (5)0.3308 (4)−0.0586 (3)0.0259 (10)
H2A1.506 (8)0.340 (5)0.011 (2)0.039*
H2B1.466 (8)0.425 (2)−0.105 (3)0.039*
O3W1.2069 (5)−0.0416 (4)0.0556 (3)0.0301 (10)
H3A1.104 (4)−0.083 (5)0.073 (5)0.045*
H3B1.311 (4)−0.116 (4)0.057 (5)0.045*
O10.9506 (5)0.2157 (4)0.1072 (3)0.0280 (10)
O20.6931 (5)0.3656 (4)0.0793 (3)0.0241 (9)
O30.6021 (5)−0.1174 (4)0.8691 (3)0.0269 (10)
O40.4373 (5)0.1075 (4)0.8570 (3)0.0251 (9)
O51.1644 (5)0.3945 (4)−0.1584 (3)0.0236 (9)
O61.0619 (5)0.1934 (5)−0.1337 (3)0.0264 (10)
C10.7893 (8)0.2736 (6)0.1411 (4)0.0199 (13)
C20.7080 (7)0.2329 (7)0.2662 (4)0.0228 (14)
C30.5563 (10)0.3242 (9)0.3151 (5)0.064 (3)
H30.49860.40700.26900.076*
C40.4889 (11)0.2952 (10)0.4304 (5)0.087 (4)
H40.38520.35850.46290.105*
C50.5711 (8)0.1739 (7)0.5001 (4)0.0257 (14)
C60.5125 (8)0.1470 (7)0.6203 (4)0.0317 (16)
H60.41390.21270.65490.038*
C70.5957 (8)0.0288 (6)0.6862 (4)0.0219 (13)
C80.5390 (7)0.0055 (6)0.8131 (4)0.0183 (12)
C90.7352 (12)−0.0676 (9)0.6357 (5)0.068 (3)
H90.7895−0.15300.68110.081*
C100.7972 (13)−0.0426 (9)0.5211 (5)0.084 (4)
H100.8956−0.11020.48860.101*
C110.7190 (8)0.0806 (6)0.4501 (4)0.0250 (14)
C120.7875 (9)0.1138 (7)0.3314 (4)0.0318 (15)
H120.89080.05120.29750.038*
C131.0862 (7)0.3182 (7)−0.1918 (4)0.0217 (13)
C141.0289 (8)0.3725 (7)−0.3018 (4)0.0242 (14)
C150.9115 (8)0.3065 (7)−0.3296 (4)0.0286 (15)
H150.86190.2299−0.27590.034*
C160.8682 (9)0.3509 (7)−0.4318 (4)0.0307 (15)
H160.78790.3056−0.44920.037*
C170.9428 (8)0.4657 (7)−0.5143 (4)0.0241 (13)
C181.0982 (8)0.4868 (6)−0.3770 (4)0.0264 (14)
H181.17320.5338−0.35620.032*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ho10.01942 (16)0.02085 (16)0.01278 (13)−0.00448 (11)−0.00501 (9)−0.00036 (9)
O1W0.024 (2)0.023 (2)0.0200 (19)−0.0050 (18)−0.0003 (16)−0.0053 (16)
O2W0.027 (2)0.030 (3)0.023 (2)−0.012 (2)−0.0058 (18)−0.0037 (17)
O3W0.022 (2)0.024 (2)0.042 (2)−0.0073 (19)−0.006 (2)−0.0011 (19)
O10.026 (2)0.034 (3)0.0193 (19)−0.008 (2)0.0008 (17)−0.0019 (17)
O20.024 (2)0.029 (2)0.0183 (18)−0.0072 (19)−0.0085 (17)0.0027 (17)
O30.034 (2)0.024 (2)0.0217 (19)−0.004 (2)−0.0144 (18)0.0037 (17)
O40.027 (2)0.026 (2)0.0197 (19)−0.004 (2)−0.0015 (17)−0.0053 (17)
O50.032 (2)0.023 (2)0.0164 (18)−0.0026 (19)−0.0130 (17)0.0011 (16)
O60.026 (2)0.037 (3)0.0165 (18)−0.013 (2)−0.0058 (16)0.0015 (17)
C10.023 (3)0.026 (3)0.016 (3)−0.015 (3)−0.002 (2)−0.004 (2)
C20.016 (3)0.035 (4)0.015 (3)−0.007 (3)−0.005 (2)0.002 (2)
C30.044 (5)0.080 (6)0.022 (3)0.029 (4)0.001 (3)0.019 (3)
C40.055 (5)0.111 (8)0.026 (4)0.061 (5)0.008 (3)0.013 (4)
C50.021 (3)0.034 (4)0.015 (3)−0.004 (3)−0.002 (2)0.004 (2)
C60.023 (3)0.042 (4)0.021 (3)0.000 (3)−0.002 (2)0.000 (3)
C70.025 (3)0.023 (3)0.016 (3)−0.004 (3)−0.003 (2)−0.003 (2)
C80.017 (3)0.026 (4)0.018 (3)−0.011 (3)−0.009 (2)−0.003 (2)
C90.088 (6)0.055 (5)0.019 (3)0.033 (5)−0.001 (4)0.006 (3)
C100.113 (8)0.058 (6)0.022 (3)0.059 (5)0.003 (4)0.001 (3)
C110.035 (4)0.023 (3)0.015 (3)−0.004 (3)−0.007 (2)−0.002 (2)
C120.039 (4)0.027 (4)0.024 (3)0.003 (3)−0.004 (3)−0.008 (3)
C130.013 (3)0.027 (4)0.024 (3)0.002 (3)−0.009 (2)−0.004 (3)
C140.026 (3)0.027 (4)0.018 (3)0.000 (3)−0.010 (2)−0.001 (2)
C150.039 (4)0.026 (4)0.023 (3)−0.003 (3)−0.015 (3)−0.003 (2)
C160.042 (4)0.028 (4)0.027 (3)−0.007 (3)−0.016 (3)−0.004 (3)
C170.030 (4)0.024 (4)0.019 (3)0.002 (3)−0.010 (2)−0.008 (2)
C180.032 (4)0.024 (4)0.026 (3)0.000 (3)−0.015 (3)−0.006 (3)

Geometric parameters (Å, °)

Ho1—O12.267 (4)C3—H30.9500
Ho1—O3i2.252 (3)C4—C51.399 (8)
Ho1—O4ii2.279 (4)C4—H40.9500
Ho1—O52.389 (3)C5—C111.387 (8)
Ho1—O62.450 (4)C5—C61.428 (7)
Ho1—O1W2.370 (4)C6—C71.359 (7)
Ho1—O2W2.461 (4)C6—H60.9500
Ho1—O3W2.366 (4)C7—C91.372 (9)
Ho1—C132.784 (5)C7—C81.504 (7)
O1W—H1A0.95 (4)C9—C101.365 (8)
O1W—H1B0.95 (4)C9—H90.9500
O2W—H2A0.95 (4)C10—C111.405 (8)
O2W—H2B0.95 (4)C10—H100.9500
O3W—H3A0.95 (4)C11—C121.420 (7)
O3W—H3B0.95 (4)C12—H120.9500
O1—C11.256 (6)C13—C141.494 (7)
O2—C11.262 (6)C14—C181.378 (8)
O3—C81.270 (6)C14—C151.404 (8)
O3—Ho1i2.252 (3)C15—C161.352 (7)
O4—C81.247 (7)C15—H150.9500
O4—Ho1iii2.279 (4)C16—C171.434 (8)
O5—C131.275 (7)C16—H160.9500
O6—C131.268 (7)C17—C17iv1.407 (12)
C1—C21.514 (7)C17—C18iv1.421 (7)
C2—C121.349 (7)C18—C17iv1.421 (7)
C2—C31.389 (9)C18—H180.9500
C3—C41.379 (8)
O1—Ho1—O4ii144.69 (15)C12—C2—C1120.6 (5)
O1—Ho1—O598.23 (13)C3—C2—C1119.5 (5)
O1—Ho1—O677.54 (13)C4—C3—C2120.2 (6)
O1—Ho1—O1W72.71 (14)C4—C3—H3119.9
O1—Ho1—O2W142.57 (14)C2—C3—H3119.9
O1—Ho1—O3W76.58 (14)C3—C4—C5121.0 (7)
O3i—Ho1—O1101.02 (13)C3—C4—H4119.5
O3i—Ho1—O4ii96.82 (14)C5—C4—H4119.5
O3i—Ho1—O5147.95 (14)C11—C5—C4118.4 (5)
O3i—Ho1—O6155.80 (14)C11—C5—C6119.3 (5)
O3i—Ho1—O1W83.38 (14)C4—C5—C6122.2 (6)
O3i—Ho1—O2W72.20 (13)C7—C6—C5121.0 (6)
O3i—Ho1—O3W76.60 (14)C7—C6—H6119.5
O4ii—Ho1—O581.43 (13)C5—C6—H6119.5
O4ii—Ho1—O673.82 (13)C6—C7—C9119.2 (5)
O4ii—Ho1—O1W140.01 (13)C6—C7—C8120.6 (5)
O4ii—Ho1—O2W72.11 (13)C9—C7—C8120.2 (5)
O4ii—Ho1—O3W78.31 (14)O4—C8—O3123.9 (5)
O5—Ho1—O654.22 (13)O4—C8—C7118.8 (5)
O5—Ho1—O2W76.91 (13)O3—C8—C7117.3 (5)
O6—Ho1—O2W123.35 (12)C10—C9—C7121.1 (6)
O1W—Ho1—O578.18 (13)C10—C9—H9119.5
O1W—Ho1—O6118.31 (14)C7—C9—H9119.5
O1W—Ho1—O2W69.97 (13)C9—C10—C11121.6 (7)
O3W—Ho1—O5133.18 (14)C9—C10—H10119.2
O3W—Ho1—O679.62 (14)C11—C10—H10119.2
O3W—Ho1—O2W133.39 (14)C5—C11—C10117.6 (5)
O3W—Ho1—O1W139.08 (13)C5—C11—C12119.6 (5)
O3i—Ho1—C13170.11 (14)C10—C11—C12122.7 (6)
O1—Ho1—C1388.87 (14)C2—C12—C11120.9 (6)
O4ii—Ho1—C1374.78 (15)C2—C12—H12119.6
O3W—Ho1—C13106.20 (17)C11—C12—H12119.6
O1W—Ho1—C1399.61 (15)O6—C13—O5120.3 (5)
O5—Ho1—C1327.19 (15)O6—C13—C14119.5 (5)
O6—Ho1—C1327.09 (15)O5—C13—C14120.2 (5)
O2W—Ho1—C1399.84 (15)O6—C13—Ho161.6 (3)
Ho1—O1W—H1A122 (3)O5—C13—Ho158.9 (2)
Ho1—O1W—H1B121 (3)C14—C13—Ho1173.3 (4)
H1A—O1W—H1B108 (4)C18—C14—C15120.6 (5)
Ho1—O2W—H2A103 (3)C18—C14—C13118.3 (5)
Ho1—O2W—H2B113 (4)C15—C14—C13121.1 (5)
H2A—O2W—H2B110 (4)C16—C15—C14120.8 (6)
Ho1—O3W—H3A129 (3)C16—C15—H15119.6
Ho1—O3W—H3B120 (3)C14—C15—H15119.6
H3A—O3W—H3B110 (4)C15—C16—C17120.4 (6)
C1—O1—Ho1155.6 (4)C15—C16—H16119.8
C8—O3—Ho1i138.9 (4)C17—C16—H16119.8
C8—O4—Ho1iii154.8 (3)C17iv—C17—C18iv119.4 (6)
C13—O5—Ho193.9 (3)C17iv—C17—C16118.9 (6)
C13—O6—Ho191.3 (3)C18iv—C17—C16121.7 (6)
O1—C1—O2124.8 (5)C14—C18—C17iv119.8 (6)
O1—C1—C2117.0 (5)C14—C18—H18120.1
O2—C1—C2118.2 (5)C17iv—C18—H18120.1
C12—C2—C3119.8 (5)
O3i—Ho1—O1—C1131.2 (9)C6—C7—C8—O3169.4 (5)
O4ii—Ho1—O1—C1−109.8 (9)C9—C7—C8—O3−12.2 (9)
O3W—Ho1—O1—C1−155.6 (9)C6—C7—C9—C103.3 (13)
O1W—Ho1—O1—C151.8 (9)C8—C7—C9—C10−175.1 (8)
O5—Ho1—O1—C1−23.0 (9)C7—C9—C10—C11−1.3 (16)
O6—Ho1—O1—C1−73.4 (9)C4—C5—C11—C10−178.5 (9)
O2W—Ho1—O1—C156.2 (9)C6—C5—C11—C104.2 (10)
C13—Ho1—O1—C1−48.6 (9)C4—C5—C11—C122.8 (10)
O3i—Ho1—O5—C13162.5 (3)C6—C5—C11—C12−174.5 (6)
O1—Ho1—O5—C13−71.0 (3)C9—C10—C11—C5−2.5 (14)
O4ii—Ho1—O5—C1373.3 (3)C9—C10—C11—C12176.2 (9)
O3W—Ho1—O5—C138.3 (4)C3—C2—C12—C11−0.5 (10)
O1W—Ho1—O5—C13−141.3 (3)C1—C2—C12—C11175.6 (6)
O6—Ho1—O5—C13−2.9 (3)C5—C11—C12—C2−1.6 (10)
O2W—Ho1—O5—C13146.8 (3)C10—C11—C12—C2179.7 (7)
O3i—Ho1—O6—C13−158.0 (3)Ho1—O6—C13—O5−5.1 (5)
O1—Ho1—O6—C13112.8 (3)Ho1—O6—C13—C14172.4 (4)
O4ii—Ho1—O6—C13−88.1 (3)Ho1—O5—C13—O65.3 (5)
O3W—Ho1—O6—C13−168.8 (3)Ho1—O5—C13—C14−172.3 (4)
O1W—Ho1—O6—C1350.5 (3)O1—Ho1—C13—O6−64.2 (3)
O5—Ho1—O6—C132.9 (3)O4ii—Ho1—C13—O684.1 (3)
O2W—Ho1—O6—C13−33.1 (4)O3W—Ho1—C13—O611.5 (3)
Ho1—O1—C1—O232.9 (12)O1W—Ho1—C13—O6−136.5 (3)
Ho1—O1—C1—C2−144.8 (7)O5—Ho1—C13—O6−174.8 (5)
O1—C1—C2—C12−16.9 (8)O2W—Ho1—C13—O6152.4 (3)
O2—C1—C2—C12165.2 (5)O1—Ho1—C13—O5110.6 (3)
O1—C1—C2—C3159.2 (6)O4ii—Ho1—C13—O5−101.0 (3)
O2—C1—C2—C3−18.7 (9)O3W—Ho1—C13—O5−173.7 (3)
C12—C2—C3—C41.3 (13)O1W—Ho1—C13—O538.4 (3)
C1—C2—C3—C4−174.8 (8)O6—Ho1—C13—O5174.8 (5)
C2—C3—C4—C5−0.1 (15)O2W—Ho1—C13—O5−32.8 (3)
C3—C4—C5—C11−2.0 (14)O6—C13—C14—C18−162.7 (5)
C3—C4—C5—C6175.3 (8)O5—C13—C14—C1814.9 (8)
C11—C5—C6—C7−2.3 (10)O6—C13—C14—C1515.6 (8)
C4—C5—C6—C7−179.5 (8)O5—C13—C14—C15−166.9 (5)
C5—C6—C7—C9−1.6 (10)C18—C14—C15—C162.0 (9)
C5—C6—C7—C8176.9 (5)C13—C14—C15—C16−176.2 (5)
Ho1iii—O4—C8—O3−23.0 (12)C14—C15—C16—C170.4 (9)
Ho1iii—O4—C8—C7158.7 (6)C15—C16—C17—C17iv−1.9 (11)
Ho1i—O3—C8—O4−57.1 (8)C15—C16—C17—C18iv179.1 (6)
Ho1i—O3—C8—C7121.2 (5)C15—C14—C18—C17iv−2.9 (9)
C6—C7—C8—O4−12.2 (8)C13—C14—C18—C17iv175.4 (5)
C9—C7—C8—O4166.2 (7)

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

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1W—H1A···O2v0.95 (4)1.82 (2)2.725 (5)157 (5)
O1W—H1B···O5v0.95 (4)1.95 (3)2.818 (5)150 (4)
O2W—H2A···O2vi0.95 (4)1.98 (4)2.782 (5)140 (5)
O2W—H2B···O2v0.95 (4)2.14 (4)2.901 (6)136 (4)
O3W—H3A···O6vii0.95 (4)1.78 (4)2.704 (5)165 (5)
O3W—H3B···O2Wviii0.95 (4)2.26 (4)3.181 (6)165 (4)
O3W—H3B···O4i0.95 (4)2.53 (5)3.145 (6)123 (4)

Symmetry codes: (v) −x+2, −y+1, −z; (vi) x+1, y, z; (vii) −x+2, −y, −z; (viii) −x+3, −y, −z; (i) −x+2, −y, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HJ2008).

References

  • Allen, F. H. (2002). Acta Cryst. B58, 380–388. [PubMed]
  • Allen, F. H. & Motherwell, W. D. S. (2002). Acta Cryst. B58, 407–422. [PubMed]
  • Almeida Paz, F. A., Bond, A. D., Khimyak, Y. Z. & Klinowski, J. (2002a). Acta Cryst. C58, m608–m610. [PubMed]
  • Almeida Paz, F. A., Bond, A. D., Khimyak, Y. Z. & Klinowski, J. (2002b). Acta Cryst. E58, m691–m693.
  • Almeida Paz, F. A., Bond, A. D., Khimyak, Y. Z. & Klinowski, J. (2002c). Acta Cryst. E58, m730–m732.
  • Almeida Paz, F. A., Shi, F.-N., Mafra, L., Makal, A., Wozniak, K., Trindade, T., Klinowski, J. & Rocha, J. (2005). Acta Cryst. E61, m1628–m1632.
  • Almeida Paz, F. A., Shi, F.-N., Trindade, T., Klinowski, J. & Rocha, J. (2005). Acta Cryst. E61, m2247–m2250.
  • Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst.27, 435.
  • Blessing, R. H. (1995). Acta Cryst. A51, 33–38. [PubMed]
  • Brandenburg, K. (2006). DIAMOND Version 3.1e. Crystal Impact GbR, Bonn, Germany.
  • Bruker (2001). SHELXTL Version 6.12. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cunha-Silva, L., Mafra, L., Ananias, D., Carlos, L. D., Rocha, J. & Paz, F. A. A. (2007). Chem. Mater.19, 3527–3538.
  • Cunha-Silva, L., Shi, F.-N., Klinowski, J., Trindade, T., Rocha, J. & Almeida Paz, F. A. (2007). Acta Cryst. E63, m372–m375.
  • Deluzet, A., Maudez, W., Daiguebonne, C. & Guillou, O. (2003). Cryst. Growth Des.3, 475–479.
  • Mafra, L., Paz, F. A. A., Shi, F.-N., Rocha, J., Trindade, T., Fernandez, C., Makal, A., Wozniak, K. & Klinowski, J. (2006). Chem. Eur. J.12, 363–375. [PubMed]
  • Min, D. & Lee, S. W. (2002). Bull. Korean Chem. Soc.23, 948–952.
  • Nonius (1998). COLLECT Nonius BV, Delft, The Netherlands.
  • Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.
  • Paz, F. A. A. & Klinowski, J. (2003). Chem. Commun. pp. 1484–1485.
  • Paz, F. A. A. & Klinowski, J. (2004). J. Solid State Chem.177, 3423–3432.
  • Paz, F. A. A., Rocha, J., Klinowski, J., Trindade, T., Shi, F.-N. & Mafra, L. (2005). Prog. Solid State Chem.33, 113–125.
  • Shi, F.-N., Almeida Paz, F. A., Trindade, T. & Rocha, J. (2006). Acta Cryst. E62, m335–m338.
  • Shi, F.-N., Cunha-Silva, L., Sá Ferreira, R. A., Mafra, L., Trindade, T., Carlos, L. D., Paz, F. A. A. & Rocha, J. (2007). J. Am. Chem. Soc. In the press. doi:10.1021/ja074119k.
  • Shi, F.-N., Paz, F. A. A., Girginova, P. I., Mafra, L., Amaral, V. S., Rocha, J., Makal, A., Wozniak, K., Klinowski, J. & Trindade, T. (2005). J. Mol. Struct.754, 51–60.
  • Wang, Z., Jin, C.-M., Shao, T., Li, Y.-Z., Zhang, K.-L., Zhang, H.-T. & You, X.-Z. (2002). Inorg. Chem. Commun.5, 642–648.
  • Zheng, X., Sun, C., Lu, S., Liao, F., Gao, S. & Jin, L. (2004). Eur. J. Inorg. Chem. pp. 3262–3268.
  • Zheng, X.-J., Wang, Z.-M., Gao, S., Liao, F.-H., Yan, C.-H. & Jin, L.-P. (2004). Eur. J. Inorg. Chem. pp. 2968–2973.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography