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The title compound, [Nd(C10H16O4)(C10H17O4)(H2O)]n, has a novel Nd–organic framework constructed from sebacic acid (C10H18O4) linkers, the longest aliphatic ligand used to date in lanthanide metal–organic framework compounds. The structure contains edge-shared chains of NdO8(H2O) tricapped trigonal prisms that propagate in the [100] direction, with Nd—O distances in the range 2.414 (4)–2.643 (4) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270104003427/fg1733sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270104003427/fg1733Isup2.hkl
Contains datablock I

CCDC reference: 221857

Comment top

Metal–organic frameworks (MOFs) have been the subject of increased study recently, due to the potential for designed architectures and their unique applicability to separations, gas storage, molecular recognition and catalysis (Moulton & Zaworotko, 2001). A subset of these materials are lanthanide-containing MOFs, the structures of which have the potential for unique topologies when one considers the rich and variable coordination chemistry of the Ln elements. Furthermore, the luminescent properties of these compounds, which result from Ln f-f electronic transitions, are being exploited for possible sensing applications (Ma et al., 1999).

A representative survey of Ln-MOFs with aliphatic carboxylate linkers reported since 1998 reveals some recurring structural features with respect to the building units of these materials (Dimos et al., 2002; Glowiak et al., 1986; Kim et al., 2004; Kiritsis et al., 1998; Michaelides et al., 2003; Serpaggi & Ferey, 1998; Vaidhyanathan et al., 2002). For example, many Ln-MOFs contain zero-dimensional Ln building units or isolated metal centers. That is, a single Ln ion (or at most a dimer) is coordinated to multifunctional organic linkers and/or water molecules to form the extended framework structures. Less common are one-dimensional chains of Ln polyhedra which are in turn cross-linked to form framework topologies.

We are concerned with understanding the principles of what factors influence the dimensionality of the Ln building units of these MOFs, and as such, have decided to explore the current limit of aliphatic chain length that can be incorporated into these structures. For this effort, we have used sebacic acid (C10H18O4), a flexible aliphatic dicarboxylic acid that is longer than previously reported for Ln-MOFs. This publication presents the synthesis, structure and thermal properties of the title compound, (C10H16O4)(C10H16O3OH)Nd(H2O), (I), a novel Ln-MOF with the longest aliphatic chain length to date. \sch

The structure of (I) contains a single crystallographically unique Nd site, within the coordination sphere of which there are two modes of bonding for the carboxylic acid (Fig. 1). Each carboxylic acid chain acts as a monodentate ligand at one end and a bridging tridentate ligand at the other. There is a bound water molecule (O9) at a distance of 2.535 (5) Å from the Nd center. Two of the O atoms (O3 and O5) are involved in the edge-sharing of the NdO8(H2O) polyhedra (Table 1). These O atoms, with their respective pairs (O4 and O6), form the bridging tridentate end of each acid. The remaining two O atoms in the coordination sphere are O1 and O7. Carboxyl atoms O2 and O8 are not coordinated to Nd but are linked via an O—H···O hydrogen bond (Table 2).

In the crystal structure of (I), there are edge-shared chains of NdO8(H2O) tricapped trigonal prisms that propagate in the [100] direction (Fig. 2). The edge sharing results from a polymerization of Nd3+ centers through bridging tridentate carboxylate groups on the sebacic acid molecules. The overall topology is thus a three-dimensional framework, as these chains are then cross-linked to each other by the difunctional acid groups.

One interesting aspect of Ln-MOFs is their thermal stability and retention of crystallinity once dehydrated (Reineke et al., 1999). Thermographic analysis of (I) reveals a weight loss of approximately 3% between 383 and 423 K (dehydration; loss of bound H2O group), followed by the complete breakdown of the structure beginning at 478 K. When compared with other Ln-MOFs, (I) appears to be less robust, presumably as a result of the acid chain length. Brzyska & Ozga (1991) have reported that Ln-sebacic acid complexes are stable up to approximately 553 K, but the structures of these compounds were not reported. Despite a low decomposition temperature, compound (I) does retain its crystalline structure upon dehydration at 423 K, as noted by a very similar powder diffraction pattern of the dehydrated material. The absence of H2O (O9) was confirmed with IR spectroscopy.

Several other structural features of (I) are of particular importance. For example, it is not common to observe a monodentate carboxylic acid ligand coordinated to a lanthanide center (Ouchi et al., 1988). A possible explanation as to why monodentate ligands are observed in (I) is the length of the acid. Even though the acid backbone is flexible, the chain length likely hampers its ability to `fold in' and become bi- or bridging tridentate, as seen in Ln-MOFs with shorter aliphatic chain lengths. Also of note is that the bound water molecule (O9) participates in a hydrogen-bonding scheme with atoms O2 and O8, which may be considered as an additional mode of connectivity between parallel NdO8(H2O) chains.

The packing of the acid chains in (I) closely resembles that of the acid molecules in pure crystalline sebacic acid (Bond et al., 2001). One noticeable difference is that in (I), alternating pairs of acid chains are rotated approximately 90° about the z crystallographic direction. Given this arrangement, it is conceivable that the geometry and disposition of the acid molecules have influenced the overall topology of (I), in that the Nd centers are assembled into a one-dimensional arrangement based on the location of the functional groups. Furthermore, it has been reported (Thalladi et al., 2000) that dibasic aliphatic chains with an even number of C atoms in the chains form `layers' in the solid state, due to the interactions of the methylene groups of neighboring acid chains. A similar assembly mechanism could be at work in the present system, in that a primary sebacic acid structure forms first, followed by Nd3+ centers filling in at the carboxylic acid ends of the chains.

Experimental top

Neodymium(III)nitrate hexahydrate and sebacic acid are available commercially and were used without any further purification. Neodymium(III)nitrate hexahydrate (0.271 g) and sebacic acid (C10H18O4, 0.071 g) were dissolved in water (1.36 g) in the presence of concentrated ammonium hydroxide (0.07 g). The solution (pH 7.38) was prepared in a 23 ml Teflon-lined Parr bomb and then heated statically at 393 K for 3 d. Light-purple crystals formed in situ (90% yield based on Nd) and are insoluble in water, ethanol and acetone. Phase purity was confirmed by comparison of the observed and calculated powder X-ray diffraction patterns (JADE; Materials Data, 2003). Elemental analysis (Galbraith Laboratories, Knoxville, Tennessee, USA) of (I) confirmed the contents of the structure [observed (calculated): C 42.84% (42.61%) and H 6.55% (6.27%)].

Refinement top

H atoms bonded to C were treated as riding atoms, with C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C). Atom H8 of the hydroxy group was visible in a difference map and then allowed for in the refinement, with O—H = 0.82 Å and Uiso(H) = 1.5Ueq(O8). The water atom O9 makes a number of possible hydrogen-bond contacts with nearby O atoms, but as no unambiguous locations for the water H atoms could be determined, their contributions were not included in the final refinement cycles.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalMaker (CrystalMaker Software, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I), along with some symmetry-equivalent atoms to complete the coordination sphere of the Nd atom. H atoms are not shown. Atoms labelled with the suffixes a-g are at the symmetry positions (x − 1, y − 1, z − 1), (x − 1, y, z − 1), (x + 1, y, z + 1), (1 − x, 1 − y, −z), (1 − x, 1 − y, 1 − z), (2 − x, 1 − y, 1 − z) and (1 + x, 1 + y, 1 + z), respectively.
[Figure 2] Fig. 2. A polyhedral representation of (I), shown down [100]. The polyhedra are chains of edge-shared NdO8(H2O) tricapped trigonal prisms and the black lines are the linking sebacic acid backbones. The unit cell of (I) is highlighted in the center. A framework is realised when parallel chains of polyhedra are cross-linked by the sebacic acid ligands.
(I) top
Crystal data top
[Nd(C10H16O4)(C10H17O4)(H2O)]Z = 2
Mr = 563.72F(000) = 574
Triclinic, P1Dx = 1.667 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.4365 (5) ÅCell parameters from 1466 reflections
b = 9.0109 (7) Åθ = 2.3–21.5°
c = 15.4080 (13) ŵ = 2.36 mm1
α = 97.991 (2)°T = 298 K
β = 100.883 (2)°Blade, purple
γ = 97.866 (2)°0.13 × 0.07 × 0.04 mm
V = 1122.95 (14) Å3
Data collection top
Bruker APEX CCD area-detector
diffractometer
5314 independent reflections
Radiation source: fine-focus sealed tube4396 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
ω and ϕ scansθmax = 27.9°, θmin = 2.3°
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 2002)
h = 114
Tmin = 0.820, Tmax = 0.910k = 1111
9349 measured reflectionsl = 1920
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)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H-atom parameters constrained
S = 0.98 w = 1/[σ2(Fo2) + (0.0276P)2]
where P = (Fo2 + 2Fc2)/3
5314 reflections(Δ/σ)max = 0.001
272 parametersΔρmax = 1.14 e Å3
0 restraintsΔρmin = 1.68 e Å3
Crystal data top
[Nd(C10H16O4)(C10H17O4)(H2O)]γ = 97.866 (2)°
Mr = 563.72V = 1122.95 (14) Å3
Triclinic, P1Z = 2
a = 8.4365 (5) ÅMo Kα radiation
b = 9.0109 (7) ŵ = 2.36 mm1
c = 15.4080 (13) ÅT = 298 K
α = 97.991 (2)°0.13 × 0.07 × 0.04 mm
β = 100.883 (2)°
Data collection top
Bruker APEX CCD area-detector
diffractometer
5314 independent reflections
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 2002)
4396 reflections with I > 2σ(I)
Tmin = 0.820, Tmax = 0.910Rint = 0.058
9349 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.108H-atom parameters constrained
S = 0.98Δρmax = 1.14 e Å3
5314 reflectionsΔρmin = 1.68 e Å3
272 parameters
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
Nd10.75067 (4)0.52135 (4)0.49793 (2)0.02235 (11)
O10.6374 (5)0.6903 (5)0.4025 (3)0.0382 (11)
O20.6247 (6)0.9290 (6)0.4577 (3)0.0475 (13)
O30.0268 (4)0.4484 (5)0.4203 (3)0.0304 (10)
O40.1578 (5)0.4908 (6)0.3418 (3)0.0397 (12)
O50.4550 (5)0.3875 (5)0.4245 (3)0.0305 (10)
O60.6403 (5)0.3627 (5)0.3429 (3)0.0348 (11)
O70.0773 (5)0.2391 (6)0.4279 (3)0.0449 (13)
O80.1466 (8)0.0130 (6)0.4114 (4)0.0670 (18)
H80.19880.03940.46320.101*
O90.7299 (6)0.2407 (5)0.5067 (4)0.0484 (13)
C10.5847 (7)0.8108 (8)0.3968 (4)0.0316 (15)
C20.4666 (8)0.8302 (8)0.3133 (4)0.0373 (16)
H2A0.36360.84580.32940.045*
H2B0.51040.92130.29300.045*
C30.4330 (8)0.6989 (8)0.2367 (4)0.0368 (16)
H3A0.37700.61020.25420.044*
H3B0.53650.67550.22460.044*
C40.3304 (8)0.7301 (9)0.1515 (5)0.0430 (18)
H4A0.22440.74650.16290.052*
H4B0.38270.82350.13700.052*
C50.3041 (8)0.6069 (8)0.0716 (5)0.0421 (18)
H5A0.24390.51570.08440.051*
H5B0.41010.58460.06340.051*
C60.2135 (9)0.6417 (9)0.0153 (4)0.049 (2)
H6A0.10540.65940.00830.059*
H6B0.27100.73500.02730.059*
C70.1953 (8)0.5187 (8)0.0948 (4)0.0410 (18)
H7A0.14010.42500.08220.049*
H7B0.30350.50270.10260.049*
C80.1011 (8)0.5517 (8)0.1820 (5)0.0420 (18)
H8A0.00890.56270.17520.050*
H8B0.15320.64800.19310.050*
C90.0897 (8)0.4331 (8)0.2619 (4)0.0365 (16)
H9A0.04750.33490.24880.044*
H9B0.19880.42920.27270.044*
C100.0181 (7)0.4602 (7)0.3460 (4)0.0284 (14)
C110.4945 (7)0.3421 (7)0.3505 (4)0.0281 (14)
C120.3637 (7)0.2572 (8)0.2728 (4)0.0336 (15)
H12A0.27090.31060.26760.040*
H12B0.32740.15750.28600.040*
C130.4144 (8)0.2366 (8)0.1823 (4)0.0393 (17)
H13A0.45960.33500.17070.047*
H13B0.49940.17390.18480.047*
C140.2719 (7)0.1633 (8)0.1064 (4)0.0364 (16)
H14A0.18600.22470.10570.044*
H14B0.22880.06420.11790.044*
C150.3144 (7)0.1436 (8)0.0140 (4)0.0392 (17)
H15A0.36050.24200.00300.047*
H15B0.39760.07920.01380.047*
C160.1691 (7)0.0745 (8)0.0614 (4)0.0355 (16)
H16A0.08650.13960.06140.043*
H16B0.12220.02330.04980.043*
C170.2094 (8)0.0523 (9)0.1543 (4)0.0404 (17)
H17A0.25670.14970.16620.048*
H17B0.29080.01400.15500.048*
C180.0616 (8)0.0152 (8)0.2277 (4)0.0356 (16)
H18A0.01910.05180.22730.043*
H18B0.01350.11190.21520.043*
C190.1005 (7)0.0399 (8)0.3206 (4)0.0391 (17)
H19A0.14950.05640.33330.047*
H19B0.17980.10830.32170.047*
C200.0513 (8)0.1060 (8)0.3929 (5)0.0353 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Nd10.01836 (15)0.02859 (19)0.01820 (18)0.00459 (12)0.00131 (12)0.00036 (13)
O10.039 (3)0.041 (3)0.029 (3)0.014 (2)0.007 (2)0.001 (2)
O20.059 (3)0.042 (3)0.030 (3)0.022 (3)0.015 (2)0.010 (2)
O30.022 (2)0.048 (3)0.020 (2)0.0057 (19)0.0033 (18)0.004 (2)
O40.027 (2)0.072 (4)0.022 (3)0.020 (2)0.004 (2)0.007 (2)
O50.025 (2)0.041 (3)0.023 (2)0.0068 (19)0.0014 (19)0.001 (2)
O60.027 (2)0.053 (3)0.019 (2)0.001 (2)0.0045 (19)0.006 (2)
O70.034 (3)0.041 (3)0.046 (3)0.005 (2)0.011 (2)0.011 (2)
O80.086 (4)0.048 (4)0.044 (4)0.020 (3)0.032 (3)0.016 (3)
O90.044 (3)0.035 (3)0.058 (4)0.007 (2)0.009 (3)0.006 (2)
C10.028 (3)0.041 (4)0.025 (4)0.005 (3)0.005 (3)0.004 (3)
C20.040 (4)0.046 (4)0.027 (4)0.018 (3)0.001 (3)0.008 (3)
C30.043 (4)0.047 (4)0.020 (3)0.011 (3)0.001 (3)0.009 (3)
C40.038 (4)0.057 (5)0.028 (4)0.012 (3)0.004 (3)0.001 (3)
C50.044 (4)0.052 (5)0.026 (4)0.007 (4)0.001 (3)0.003 (3)
C60.057 (5)0.067 (6)0.018 (4)0.020 (4)0.006 (3)0.003 (4)
C70.043 (4)0.056 (5)0.025 (4)0.018 (4)0.003 (3)0.009 (3)
C80.043 (4)0.048 (5)0.033 (4)0.014 (3)0.003 (3)0.008 (3)
C90.036 (4)0.057 (5)0.019 (3)0.018 (3)0.001 (3)0.012 (3)
C100.028 (3)0.036 (4)0.022 (3)0.007 (3)0.004 (3)0.004 (3)
C110.024 (3)0.031 (4)0.024 (3)0.002 (3)0.001 (3)0.001 (3)
C120.025 (3)0.046 (4)0.026 (4)0.004 (3)0.004 (3)0.002 (3)
C130.030 (3)0.053 (5)0.025 (4)0.004 (3)0.002 (3)0.009 (3)
C140.033 (3)0.051 (5)0.018 (3)0.006 (3)0.002 (3)0.007 (3)
C150.031 (3)0.054 (5)0.026 (4)0.006 (3)0.000 (3)0.007 (3)
C160.034 (3)0.043 (4)0.023 (4)0.001 (3)0.001 (3)0.003 (3)
C170.032 (3)0.055 (5)0.026 (4)0.003 (3)0.000 (3)0.006 (3)
C180.035 (4)0.045 (4)0.022 (4)0.005 (3)0.001 (3)0.003 (3)
C190.029 (3)0.054 (5)0.026 (4)0.006 (3)0.002 (3)0.004 (3)
C200.033 (3)0.043 (4)0.025 (4)0.002 (3)0.007 (3)0.003 (3)
Geometric parameters (Å, º) top
Nd1—O3i2.414 (4)C6—C71.503 (10)
Nd1—O12.426 (4)C6—H6A0.97
Nd1—O7ii2.429 (5)C6—H6B0.97
Nd1—O5iii2.453 (4)C7—C81.516 (9)
Nd1—O4iv2.509 (4)C7—H7A0.97
Nd1—O92.535 (5)C7—H7B0.97
Nd1—O62.542 (4)C8—C91.492 (9)
Nd1—O52.586 (4)C8—H8A0.97
Nd1—O3iv2.643 (4)C8—H8B0.97
Nd1—C112.935 (6)C9—C101.506 (8)
Nd1—C10iv2.964 (6)C9—H9A0.97
O1—C11.235 (7)C9—H9B0.97
O2—C11.279 (8)C10—Nd1v2.964 (6)
O3—C101.268 (7)C11—C121.500 (8)
O3—Nd1i2.414 (4)C12—C131.529 (9)
O3—Nd1v2.643 (4)C12—H12A0.97
O4—C101.258 (6)C12—H12B0.97
O4—Nd1v2.509 (4)C13—C141.513 (8)
O5—C111.276 (7)C13—H13A0.97
O5—Nd1iii2.453 (4)C13—H13B0.97
O6—C111.249 (6)C14—C151.524 (9)
O7—C201.217 (8)C14—H14A0.97
O7—Nd1vi2.429 (5)C14—H14B0.97
O8—C201.263 (8)C15—C161.514 (8)
O8—H80.82C15—H15A0.97
C1—C21.518 (9)C15—H15B0.97
C2—C31.507 (9)C16—C171.525 (9)
C2—H2A0.97C16—H16A0.97
C2—H2B0.97C16—H16B0.97
C3—C41.513 (9)C17—C181.508 (8)
C3—H3A0.97C17—H17A0.97
C3—H3B0.97C17—H17B0.97
C4—C51.500 (9)C18—C191.522 (9)
C4—H4A0.97C18—H18A0.97
C4—H4B0.97C18—H18B0.97
C5—C61.507 (9)C19—C201.518 (9)
C5—H5A0.97C19—H19A0.97
C5—H5B0.97C19—H19B0.97
O3i—Nd1—O183.76 (15)C4—C5—H5B108.4
O3i—Nd1—O7ii74.41 (16)C6—C5—H5B108.4
O1—Nd1—O7ii80.15 (16)H5A—C5—H5B107.4
O3i—Nd1—O5iii154.29 (15)C7—C6—C5114.3 (6)
O1—Nd1—O5iii77.68 (15)C7—C6—H6A108.7
O7ii—Nd1—O5iii84.92 (15)C5—C6—H6A108.7
O3i—Nd1—O4iv113.10 (13)C7—C6—H6B108.7
O1—Nd1—O4iv143.68 (16)C5—C6—H6B108.7
O7ii—Nd1—O4iv74.47 (17)H6A—C6—H6B107.6
O5iii—Nd1—O4iv74.62 (13)C6—C7—C8114.5 (6)
O3i—Nd1—O999.73 (16)C6—C7—H7A108.6
O1—Nd1—O9140.50 (16)C8—C7—H7A108.6
O7ii—Nd1—O9138.94 (16)C6—C7—H7B108.6
O5iii—Nd1—O9105.92 (15)C8—C7—H7B108.6
O4iv—Nd1—O970.83 (17)H7A—C7—H7B107.6
O3i—Nd1—O674.79 (13)C9—C8—C7114.7 (6)
O1—Nd1—O673.45 (15)C9—C8—H8A108.6
O7ii—Nd1—O6141.12 (16)C7—C8—H8A108.6
O5iii—Nd1—O6115.77 (13)C9—C8—H8B108.6
O4iv—Nd1—O6140.55 (16)C7—C8—H8B108.6
O9—Nd1—O669.73 (16)H8A—C8—H8B107.6
O3i—Nd1—O5124.94 (13)C8—C9—C10113.8 (6)
O1—Nd1—O574.56 (14)C8—C9—H9A108.8
O7ii—Nd1—O5145.22 (14)C10—C9—H9A108.8
O5iii—Nd1—O566.78 (16)C8—C9—H9B108.8
O4iv—Nd1—O5114.16 (14)C10—C9—H9B108.8
O9—Nd1—O571.38 (14)H9A—C9—H9B107.7
O6—Nd1—O550.76 (13)O4—C10—O3119.9 (6)
O3i—Nd1—O3iv65.03 (16)O4—C10—C9118.4 (6)
O1—Nd1—O3iv143.86 (14)O3—C10—C9121.7 (5)
O7ii—Nd1—O3iv74.45 (14)O4—C10—Nd1v56.9 (3)
O5iii—Nd1—O3iv124.18 (13)O3—C10—Nd1v63.0 (3)
O4iv—Nd1—O3iv50.14 (13)C9—C10—Nd1v175.2 (4)
O9—Nd1—O3iv66.69 (14)O6—C11—O5121.0 (6)
O6—Nd1—O3iv112.41 (13)O6—C11—C12119.8 (6)
O5—Nd1—O3iv138.06 (13)O5—C11—C12119.1 (5)
O3i—Nd1—C1199.36 (15)O6—C11—Nd159.6 (3)
O1—Nd1—C1170.91 (16)O5—C11—Nd161.7 (3)
O7ii—Nd1—C11150.94 (17)C12—C11—Nd1177.2 (5)
O5iii—Nd1—C1191.28 (16)C11—C12—C13115.4 (5)
O4iv—Nd1—C11132.12 (17)C11—C12—H12A108.4
O9—Nd1—C1169.70 (17)C13—C12—H12A108.4
O6—Nd1—C1125.08 (14)C11—C12—H12B108.4
O5—Nd1—C1125.75 (14)C13—C12—H12B108.4
O3iv—Nd1—C11129.44 (16)H12A—C12—H12B107.5
O3i—Nd1—C10iv89.11 (16)C14—C13—C12112.1 (5)
O1—Nd1—C10iv152.29 (17)C14—C13—H13A109.2
O7ii—Nd1—C10iv72.15 (17)C12—C13—H13A109.2
O5iii—Nd1—C10iv99.09 (15)C14—C13—H13B109.2
O4iv—Nd1—C10iv24.84 (14)C12—C13—H13B109.2
O9—Nd1—C10iv67.10 (16)H13A—C13—H13B107.9
O6—Nd1—C10iv130.20 (16)C13—C14—C15114.4 (5)
O5—Nd1—C10iv129.96 (16)C13—C14—H14A108.7
O3iv—Nd1—C10iv25.32 (13)C15—C14—H14A108.7
C11—Nd1—C10iv136.78 (18)C13—C14—H14B108.7
C1—O1—Nd1148.0 (4)C15—C14—H14B108.7
C10—O3—Nd1i147.5 (4)H14A—C14—H14B107.6
C10—O3—Nd1v91.7 (3)C16—C15—C14113.6 (5)
Nd1i—O3—Nd1v114.97 (16)C16—C15—H15A108.9
C10—O4—Nd1v98.3 (4)C14—C15—H15A108.9
C11—O5—Nd1iii148.2 (4)C16—C15—H15B108.9
C11—O5—Nd192.6 (3)C14—C15—H15B108.9
Nd1iii—O5—Nd1113.22 (16)H15A—C15—H15B107.7
C11—O6—Nd195.3 (4)C15—C16—C17114.4 (5)
C20—O7—Nd1vi154.7 (4)C15—C16—H16A108.7
C20—O8—H8109.5C17—C16—H16A108.7
O1—C1—O2124.5 (6)C15—C16—H16B108.7
O1—C1—C2121.3 (6)C17—C16—H16B108.7
O2—C1—C2114.1 (6)H16A—C16—H16B107.6
C3—C2—C1115.0 (5)C18—C17—C16112.9 (5)
C3—C2—H2A108.5C18—C17—H17A109.0
C1—C2—H2A108.5C16—C17—H17A109.0
C3—C2—H2B108.5C18—C17—H17B109.0
C1—C2—H2B108.5C16—C17—H17B109.0
H2A—C2—H2B107.5H17A—C17—H17B107.8
C2—C3—C4113.3 (6)C17—C18—C19113.4 (5)
C2—C3—H3A108.9C17—C18—H18A108.9
C4—C3—H3A108.9C19—C18—H18A108.9
C2—C3—H3B108.9C17—C18—H18B108.9
C4—C3—H3B108.9C19—C18—H18B108.9
H3A—C3—H3B107.7H18A—C18—H18B107.7
C5—C4—C3115.1 (6)C20—C19—C18112.0 (5)
C5—C4—H4A108.5C20—C19—H19A109.2
C3—C4—H4A108.5C18—C19—H19A109.2
C5—C4—H4B108.5C20—C19—H19B109.2
C3—C4—H4B108.5C18—C19—H19B109.2
H4A—C4—H4B107.5H19A—C19—H19B107.9
C4—C5—C6115.6 (6)O7—C20—O8124.0 (7)
C4—C5—H5A108.4O7—C20—C19121.4 (7)
C6—C5—H5A108.4O8—C20—C19114.6 (6)
O3i—Nd1—O1—C1123.0 (8)C7—C8—C9—C10174.3 (6)
O7ii—Nd1—O1—C147.8 (8)Nd1v—O4—C10—O32.8 (7)
O5iii—Nd1—O1—C139.1 (8)Nd1v—O4—C10—C9179.2 (5)
O4iv—Nd1—O1—C11.9 (9)Nd1i—O3—C10—O4148.9 (5)
O9—Nd1—O1—C1139.2 (8)Nd1v—O3—C10—O42.7 (6)
O6—Nd1—O1—C1161.0 (8)Nd1i—O3—C10—C933.2 (11)
O5—Nd1—O1—C1108.1 (8)Nd1v—O3—C10—C9179.5 (6)
O3iv—Nd1—O1—C193.5 (8)Nd1i—O3—C10—Nd1v146.2 (8)
C11—Nd1—O1—C1134.8 (8)C8—C9—C10—O448.4 (9)
C10iv—Nd1—O1—C147.0 (10)C8—C9—C10—O3133.8 (7)
O3i—Nd1—O5—C117.3 (4)Nd1—O6—C11—O55.8 (6)
O1—Nd1—O5—C1178.0 (4)Nd1—O6—C11—C12176.8 (5)
O7ii—Nd1—O5—C11122.8 (4)Nd1iii—O5—C11—O6150.9 (5)
O5iii—Nd1—O5—C11160.9 (5)Nd1—O5—C11—O65.6 (6)
O4iv—Nd1—O5—C11139.6 (4)Nd1iii—O5—C11—C1231.7 (11)
O9—Nd1—O5—C1181.7 (4)Nd1—O5—C11—C12176.9 (5)
O6—Nd1—O5—C113.1 (3)Nd1iii—O5—C11—Nd1145.3 (8)
O3iv—Nd1—O5—C1183.1 (4)O3i—Nd1—C11—O611.6 (4)
C10iv—Nd1—O5—C11116.8 (4)O1—Nd1—C11—O691.6 (4)
O3i—Nd1—O5—Nd1iii153.67 (16)O7ii—Nd1—C11—O686.3 (5)
O1—Nd1—O5—Nd1iii82.97 (19)O5iii—Nd1—C11—O6168.1 (4)
O7ii—Nd1—O5—Nd1iii38.1 (3)O4iv—Nd1—C11—O6121.6 (4)
O5iii—Nd1—O5—Nd1iii0.0O9—Nd1—C11—O685.4 (4)
O4iv—Nd1—O5—Nd1iii59.4 (2)O5—Nd1—C11—O6174.4 (6)
O9—Nd1—O5—Nd1iii117.3 (2)O3iv—Nd1—C11—O653.6 (4)
O6—Nd1—O5—Nd1iii164.0 (3)C10iv—Nd1—C11—O687.1 (4)
O3iv—Nd1—O5—Nd1iii115.93 (19)O3i—Nd1—C11—O5174.0 (3)
C11—Nd1—O5—Nd1iii160.9 (5)O1—Nd1—C11—O594.0 (4)
C10iv—Nd1—O5—Nd1iii82.2 (2)O7ii—Nd1—C11—O599.3 (5)
O3i—Nd1—O6—C11168.1 (4)O5iii—Nd1—C11—O517.5 (4)
O1—Nd1—O6—C1180.2 (4)O4iv—Nd1—C11—O552.8 (4)
O7ii—Nd1—O6—C11129.4 (4)O9—Nd1—C11—O589.0 (4)
O5iii—Nd1—O6—C1113.2 (4)O6—Nd1—C11—O5174.4 (6)
O4iv—Nd1—O6—C1183.9 (4)O3iv—Nd1—C11—O5120.8 (3)
O9—Nd1—O6—C1185.2 (4)C10iv—Nd1—C11—O587.3 (4)
O5—Nd1—O6—C113.1 (4)O6—C11—C12—C1314.8 (9)
O3iv—Nd1—O6—C11137.7 (4)O5—C11—C12—C13167.7 (6)
C10iv—Nd1—O6—C11116.4 (4)C11—C12—C13—C14174.6 (6)
Nd1—O1—C1—O225.9 (13)C12—C13—C14—C15178.5 (6)
Nd1—O1—C1—C2155.4 (6)C13—C14—C15—C16178.2 (6)
O1—C1—C2—C35.6 (9)C14—C15—C16—C17179.4 (6)
O2—C1—C2—C3173.2 (6)C15—C16—C17—C18179.4 (6)
C1—C2—C3—C4173.4 (6)C16—C17—C18—C19179.3 (6)
C2—C3—C4—C5175.8 (6)C17—C18—C19—C20179.3 (6)
C3—C4—C5—C6175.3 (6)Nd1vi—O7—C20—O827.7 (16)
C4—C5—C6—C7177.6 (6)Nd1vi—O7—C20—C19150.9 (8)
C5—C6—C7—C8178.7 (6)C18—C19—C20—O7104.7 (8)
C6—C7—C8—C9177.2 (6)C18—C19—C20—O874.0 (8)
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y+1, z+1; (iii) x+1, y+1, z+1; (iv) x+1, y, z+1; (v) x1, y, z1; (vi) x1, y1, z1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O8—H8···O2vi0.821.702.454 (7)152
Symmetry code: (vi) x1, y1, z1.

Experimental details

Crystal data
Chemical formula[Nd(C10H16O4)(C10H17O4)(H2O)]
Mr563.72
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)8.4365 (5), 9.0109 (7), 15.4080 (13)
α, β, γ (°)97.991 (2), 100.883 (2), 97.866 (2)
V3)1122.95 (14)
Z2
Radiation typeMo Kα
µ (mm1)2.36
Crystal size (mm)0.13 × 0.07 × 0.04
Data collection
DiffractometerBruker APEX CCD area-detector
diffractometer
Absorption correctionEmpirical (using intensity measurements)
(SADABS; Sheldrick, 2002)
Tmin, Tmax0.820, 0.910
No. of measured, independent and
observed [I > 2σ(I)] reflections
9349, 5314, 4396
Rint0.058
(sin θ/λ)max1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.108, 0.98
No. of reflections5314
No. of parameters272
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.14, 1.68

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 1997), CrystalMaker (CrystalMaker Software, 2003), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top
Nd1—O3i2.414 (4)Nd1—O92.535 (5)
Nd1—O12.426 (4)Nd1—O62.542 (4)
Nd1—O7ii2.429 (5)Nd1—O52.586 (4)
Nd1—O5iii2.453 (4)Nd1—O3iv2.643 (4)
Nd1—O4iv2.509 (4)
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y+1, z+1; (iii) x+1, y+1, z+1; (iv) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O8—H8···O2v0.821.702.454 (7)152
Symmetry code: (v) x1, y1, z1.
 

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