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Tetra­kis(μ2 2,6 di­formyl 4 methyl­phenolato)tetra μ3 hydroxo tetra­kis[di­aqua­neodymium(III)] tetra­kis(perchlorate) ethanol disolvate

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metal-organic papers

Acta Cryst.(2006). E62, m113–m115 doi:10.1107/S1600536805041139 Singh-Wilmotet al. [Nd

4(C9H7O3)4(OH)4(H2O)8](ClO4)4

m113

Acta Crystallographica Section E Structure Reports Online

ISSN 1600-5368

Tetrakis(

l

2

-2,6-diformyl-4-methylphenolato)tetra-l

3

-hydroxo-tetrakis[diaquaneodymium(III)]

tetrakis(perchlorate) ethanol disolvate

Marvadeen A. Singh-Wilmot,a* Ishenkumba A. Kahwaaand Alan J. Loughb

aChemistry Department, University of the West

Indies, Mona Campus, Kingston 7, Jamaica, and

bDepartment of Chemistry, University of

Toronto, Toronto, Ontario, Canada M5S 3H6

Correspondence e-mail:

marvadeen.singhwilmot@uwimona.edu.jm

Key indicators

Single-crystal X-ray study

T= 150 K

Mean(C–C) = 0.009 A˚ Some non-H atoms missing Disorder in main residue

Rfactor = 0.043

wRfactor = 0.122

Data-to-parameter ratio = 22.5

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

#2006 International Union of Crystallography Printed in Great Britain – all rights reserved

The title compound, [Nd4(2-C9H7O3)4(3-OH)4(H2O)8

]-(ClO4)42C2H6O, was synthesized from the ligand-controlled

hydrolysis of Nd(ClO4)3. The cation, which lies on a

crystal-lographic twofold axis, has four ninefold coordinated NdIII ions and four triply bridging hydroxy groups occupying alternate vertices of a distorted cube and supported by four

2-C9H7O3 ligands. The crystal structure indicates that

2,6-diformyl-4-methylphenol is a useful supporting ligand in the synthesis of high-nuclearity LnIIIclusters.

Comment

There is currently tremendous interest in the synthesis and characterization of finite polylanthanide(III) entities with nanoscopic dimensions (Zheng, 2001; Wanget al., 2002). This interest lies in several application fields, since lanthanide clusters are potential precurors for ceramics, catalysts and thin-film coatings (Hubert-Pfalzgraf, 1995). Nanoclusters with mutually interacting LnIIIions are also expected to yield new materials with greater versatility resulting from unusual enhancements in magnetic, catalytic, optical and electronic properties (Thompsonet al., 2003, 2001). The title compound, (I), is one of a series of similar LnIIIcompounds synthesized in an investigation into the formation chemistry of nanoclusters which feature commonly encountered aggregation motifs such as [Ln4(OH)4]

8+

. We have previously determined the structure of the cation in the title structure as the trifluoromethane-sulfonate (Singh-Wilmotet al., 2005).

The cation in (I) features four NdIIIand four

3-hydroxo

groups occupying alternate vertices of a distorted cube (Fig. 1). Selected bond distances are given in Table 1. Each NdIIIion is in a ninefold coordination polyhedron of an approximate

(2)

tricapped trigonal prism and approximateD3hsymmetry, with

a shortest metal–metal contact of Nd2 Nd2i= 3.7003 (4) A˚ [symmetry code: (i)x,y,1

2z]. This distance is comparable

with metal–metal distances seen in other complexes containing a similar cubane-type [Ln4(3-OH)4]

8+

core, for example ca 3.83 A˚ for the shortest Sm Sm distance in [Sm4(3-OH)4(Gly)5(H2O)11]) (Evans et al., 2000). Nd—

O(phenolate) distances are in the range 2.546 (3)–2.597 (3) A˚ , while the Nd—O(carbonyl) distances are in the range 2.441 (4)–2.484 (4) A˚ . The range of Nd—O(3-OH) distances

[2.393 (3)–2.472 (3) A˚ ] compares well with those in [Nd4(3

-OH)4(Ala)6(H2O)10] (ca2.43 A˚ ; Zheng & Wang, 2000).

Experimental

NaOH (2 mmol, 0.08 g) in methanol (10 ml) was added in five portions to a boiling solution of Nd(ClO4)3.nH2O (8 mmol, 1.346 g

Nd2O3) in methanol (10 ml). A solution of

2,6-diformyl-4-methyl-phenol (4 mmol, 0.6566 g) and NaOH (4 mmol, 0.16 g) in methanol (150 ml) was then added to the boiling solution in 20 ml portions. After each addition of sodium cresolate, the mixture was boiled until approximately 10 ml of solution remained before adding the next 20 ml portion. The pH of the mixture at this point was approximately 6.5. The final mixture was boiled until 5 ml of solution remained. It was then cooled and filtered and approximately 10 ml of ethanol was added. The resulting mixture was left in an open flask at room temperature. The onset of crystallization was obvious after 3 d but a further 2 d were allowed for the process to proceed to completion. Yellow blocks of (I) were recovered in 20% yield (calculation based on LnIII). The crystals lost solvent and crumbled to an amorphous solid on exposure to air. CAUTION: Although no problems were encountered in this work, perchlorate compounds are potentially explosive. They should be prepared in small amounts and handled with care.

Crystal data

[Nd4(C9H7O3)4(OH)4(H2O)8]-(ClO4)42C2H6O

Mr= 1931.64

Monoclinic,C2=c a= 20.9933 (3) A˚ b= 24.7385 (5) A˚ c= 17.6893 (3) A˚

= 120.469 (1) V= 7918.1 (2) A˚3 Z= 4

Dx= 1.620 Mg m 3 MoKradiation Cell parameters from 8715

reflections

= 2.6–27.5 = 2.80 mm1 T= 150 (1) K Block, yellow 0.320.280.25 mm

Data collection

Bruker Nonius KappaCCD area detector diffractometer

’scans and!scans withoffsets Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)

Tmin= 0.430,Tmax= 0.497 31251 measured reflections

8998 independent reflections 7708 reflections withI> 2(I) Rint= 0.037

max= 27.5 h=27!27 k=32!32 l=22!19

Refinement

Refinement onF2 R[F2> 2(F2)] = 0.043 wR(F2) = 0.122 S= 1.06 8998 reflections 400 parameters

w= 1/[2(F

o2) + (0.0625P)2 + 41.2001P]

whereP= (Fo2+ 2Fc2)/3 (/)max< 0.001

max= 1.64 e A˚

3 min=1.16 e A˚

[image:2.610.317.563.70.302.2]

3

Table 1

Selected bond lengths (A˚ ).

Nd1—O9 2.416 (3) Nd1—O4Ai

2.429 (12) Nd1—O4 2.456 (12) Nd1—O9i

2.467 (3) Nd1—O8 2.472 (3) Nd1—O10 2.478 (4) Nd1—O3 2.484 (4) Nd1—O11 2.512 (3) Nd1—O2 2.546 (3) Nd1—O5 2.565 (3)

Nd2—O8 2.392 (3) Nd2—O6 2.441 (4) Nd2—O9 2.447 (3) Nd2—O1 2.452 (3) Nd2—O8i

2.453 (3) Nd2—O13 2.516 (4) Nd2—O7 2.559 (3) Nd2—O2 2.597 (3) Nd2—O12 2.627 (3)

[image:2.610.312.563.412.503.2]

Symmetry code: (i)x;y;zþ1 2.

Table 2

Hydrogen-bond geometry (A˚ ,).

D—H A D—H H A D A D—H A

O8—H8 O19i 1.00 1.98 2.969 (10) 168 O9—H9 O15i

1.00 1.93 2.922 (7) 170 O10—H10C O3ii

0.84 2.05 2.884 (5) 170 O10—H10D O12i 0.84 1.98 2.764 (5) 155 O11—H11A O14i

0.84 2.49 3.331 (14) 180 O12—H12A O19A 0.84 2.10 2.945 (8) 180 O12—H12B O16i

0.84 1.98 2.819 (6) 180 O13—H13C O20i

0.84 2.01 2.845 (12) 180 O13—H13D O19Aiii

0.84 2.10 2.943 (8) 180

Symmetry codes: (i)x;y;zþ1 2; (ii)x

1 2;yþ

1

2;z; (iii)x;y;zþ1.

One of the perchlorate anions (Cl2/O18/O19/O20/O21) is disor-dered over two sites, with an occupancy ratio of 0.577 (4)/0.423 (4) for the major and minor components. Both components of the disorder have the site of O18 in common. In addition, one of the2-C9H7O3 Figure 1

A view of the cation of (I), with displacement ellipsoids drawn at the 30% probability level. H atoms bonded to C atoms are not shown. Atoms labelled with the suffix A are related by the symmetry operator (x,y,

z+1

[image:2.610.314.566.572.673.2]
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is also disordered; initial refinement gave equal values within experimental error for the two disorder components; the occupancy ratio was therefore fixed at 0.5:0.5 in the final cycles. This disordered ligand is bisected by the crystallographic twofold axis but the disorder is not imposed by the crystallographic symmetry. All H atoms bonded to C atoms were placed in calculated positions, with C—H distances of 0.95 or 0.98 A˚ (methyl), and were included in the refinement in the riding-model approximation, withUiso(H) = 1.2Ueq(C), or 1.5Ueq(C)

for methyl H atoms. The H atoms of the bridging hydroxyl ligands were included with O—H = 1.00 A˚ and Uiso(H) = 1.2Ueq(O). All

other H atoms bonded to O atoms were placed in calculated positions based on an ideal location for O—H O hydrogen bonding. The O— H distance was fixed at 0.84 A˚ withUiso(H) = 1.5Ueq(O). During the

refinement, areas of electron density were located in difference Fourier maps that were assigned as ethanol solvent molecules. The peak pattern of electron density suggested that the solvent molecules were highly disordered, and attempts to model the disorder were unsuccessful. In the final cycles of refinement, the contribution to electron density corresesponding to the disordered ethanol molecules was removed from the observed data using the SQUEEZE option in

PLATON (Spek, 2003). The resulting data vastly improved the precision of the geometric parameters of the remaining structure. The contributions of two molecules of ethanol have been included in the molecular formula. The hydroxy groups of the ethanol molecules, if present, would contribute to the hydrogen-bonding motif, and for this reason the hydrogen bonding in the title structure is not discussed in detail. In the final difference Fourier map, the three largest density peaks in the range 1.64–1.06 e A˚3are located within 1.23 A˚ of the disordered perchlorate anion, and the deepest hole of1.16 e A˚3is

0.80 A˚ from Nd1.

Data collection: COLLECT (Nonius, 2002); cell refinement:

DENZO-SMN (Otwinowski & Minor, 1997); data reduction:

DENZO-SMN; program(s) used to solve structure:SHELXTL/PC

(Sheldrick, 2001); program(s) used to refine structure:SHELXTL/

PC; molecular graphics: SHELXTL/PC; software used to prepare material for publication:SHELXTL/PC.

The authors acknowledge NSERC, Canada, and the University of Toronto for funding, and Graduate Studies and Research, The University of the West Indies, Mona Campus, for supporting MASW and IAK.

References

Evans, W. J., Greci, M. A. & Ziller, J. W. (2000).Inorg. Chem.39, 3213–3220. Hubert-Pfalzgraf, L. G. (1995).New J. Chem.19, 727–750.

Nonius (2002).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.

Sheldrick, G. M. (2001).SHELXTL/PC. Version 6.10 for Windows NT. Bruker AXS Inc., Madison, Wisconsin, USA.

Singh-Wilmot, M. A., Kahwa, I. A. & Lough, A. J. (2005).Acta Cryst.E61, m970–m972.

Spek, A. L. (2003).J. Appl. Cryst.36, 7–13.

Thompson, M. K., Lough, A. J., White, J. P., Williams, D. J. & Kahwa, I. A. (2003).Inorg. Chem.42, 4828–4841.

Thompson, M. K., Vuchkov, M. & Kahwa, I. A. (2001).Inorg. Chem.40, 4332– 4341.

Wang, R., Selby, H. D., Liu, H., Carducci, M., Jin, T., Zheng, Z., Anthis, J. W., Staples, R. J. (2002).Inorg. Chem.41, 278–286.

Zheng, Z. (2001).Chem. Commun.pp. 2521–2529.

Zheng, Z. & Wang, R. (2000).Comments Inorg. Chem.22, 1–30.

metal-organic papers

Acta Cryst.(2006). E62, m113–m115 Singh-Wilmotet al. [Nd

(4)

supporting information

Acta Cryst. (2006). E62, m113–m115 [doi:10.1107/S1600536805041139]

Tetrakis(

µ

2

-2,6-diformyl-4-methylphenolato)tetra-

µ

3

-hydroxo-tetrakis[diaqua-neodymium(III)] tetrakis(perchlorate) ethanol disolvate

Marvadeen A. Singh-Wilmot, Ishenkumba A. Kahwa and Alan J. Lough

S1. Comment

There is currently tremendous interest in the synthesis and characterization of finite polylanthanide(III) entities with

nanoscopic dimensions (Zheng, 2001; Wang et al., 2002). This interest lies in several application fields, since lanthanide

clusters are potential precurors for ceramics, catalysts and thin-film coatings (Hubert-Pfalzgraf, 1995). Nanoclusters with

mutually interacting LnIII ions are also expected to yield new materials with greater versatility resulting from unusual

enhancements in magnetic, catalytic, optical and electronic properties (Thompson et al., 2003, 2001). The title

compound, (I), is one of a series of similar LnIII compounds synthesized in an investigation into the formation chemistry

of nanoclusters which feature commonly encountered aggregation motifs such as [Ln4(OH)4]8+. We have previously

determined the structure of the cation in the title structure as the trifluoromethanesulfonate (Singh-Wilmot et al., 2005).

The cation in (I) features four NdIII and four µ3-hydroxo groups occupying alternate vertices of a distorted cube (Fig. 1).

Selected bond distances are given in Table 1. Each NdIII ion is in a ninefold coordination polyhedron of an approximate

tricapped trigonal prism and approximate D3 h symmetry, with a shortest metal–metal contact of Nd2···Nd2i = 3.7003 (4)

Å [symmetry code: (i) −x, y, 1/2 − z]. This distance is comparable with metal–metal distances seen in other complexes

containing a similar cubane-type [Ln4(µ3-OH)4]8+ core, for example ca 3.83 Å for the shortest Sm···Sm distance in

[Sm4(µ3-OH)4(Gly)5(H2O)11]) (Evans et al., 2000). Nd—O(phenolate) distances are in the range 2.546 (3)–2.597 (3) Å,

while the Nd—O(carbonyl) distances are in the range 2.441 (4)–2.484 (4) Å. The range of Nd—O(µ3-OH) distances

[2.393 (3)–2.472 (3) Å] compares well with those in [Nd4(µ3-OH)4(Ala)6(H2O)10] (ca 2.43 Å; Zheng & Wang, 2000).

S2. Experimental

NaOH (2 mmol, 0.08 g) in methanol (10 ml) was added in five portions to a boiling solution of Nd(ClO4)3.nH2O (8 mmol,

1.346 g N d2O3) in methanol (10 ml). A solution of 2,6-diformyl-4-methylphenol (4 mmol, 0.6566 g) and NaOH (4 mmol,

0.16 g) in methanol (150 ml) was then added to the boiling solution in 20 ml portions. After each addition of sodium

cresolate, the mixture was boiled until approximately 10 ml of solution remained before adding the next 20 ml portion.

The pH of the mixture at this point was approximately 6.5. The final mixture was boiled until 5 ml of solution remained.

It was then cooled and filtered and approximately 10 ml of ethanol was added. The resulting mixture was left in an open

flask at room temperature. The onset of crystallization was obvious after 3 d but a further 2 d were allowed for the

process to proceed to completion. Yellow blocks of (I) were recovered in 20% yield (calculation based on LnIII). The

crystals lost solvent and crumbled to an amorphous solid on exposure to air. CAUTION: Although no problems were

encountered in this work, perchlorate compounds are potentially explosive. They should be prepared in small amounts

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supporting information

sup-2

Acta Cryst. (2006). E62, m113–m115

S3. Refinement

One of the percholate anions (Cl2/O18/O19/O20/O21) is disordered over two sites, with an occupancy ratio of

0.577 (4)/0.423 (4) for the major and minor components. Both components of disorder have the site of O18 in common.

In addition, one of the µ2-C9H7O3 ligands (containing the benzene ring C11/C11A/C12/C13/C13A/C14) is also disordered;

initial refinement gave equal values within experimental error for the two disorder components; the occupancy ratio was

therefore fixed at 0.5:0.5 in the final cycles. This disordered ligand is bisected by the crystallographic twofold axis but the

disorder is not imposed by the crystallographic symmetry. All H atoms bonded to C atoms were placed in calculated

positions, with C—H distances of 0.95 or 0.98 Å (methyl), and were included in the refinement in the riding-model

approximation, with Uiso(H) = 1.2Ueq(C), or 1.5Ueq(C) for methyl H atoms. The H atoms of the bridging hydroxyl ligands

were included with O—H = 1.00 Å and Uiso(H) = 1.2Ueq(O). All other H atoms bonded to O atoms were placed in

calculated positions based on an ideal location for O—H···O hydrogen bonding. The O—H distance was fixed at 0.84 Å

with Uiso(H) = 1.5Ueq(O). During the refinement, areas of electron density were located in difference Fourier maps that

were assigned as ethanol solvent molecules. The peak pattern of electron density suggested that the solvent molecules

were highly disordered, and attempts to model the disorder were unsuccessful. In the final cycles of refinement, the

contribution to electron density corresesponding to the disordered ethanol molecules was removed from the observed

data using the SQUEEZE option in PLATON (Spek, 2003). The resulting data vastly improved the precision of the

geometric parameters of the remaining structure. The contributions of two molecules of ethanol have been included in the

molecular formula. The hydroxy groups of the ethanol molecules, if present, would contribute to the hydrogen-bonding

motif, and for that reason the hydrogen bonding in the title structure is not discussed in detail. In the final difference

Fourier map, the three largest density peaks in the range 1.64–1.06 e Å3 were located within 1.23 Å of the disordered

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[image:6.610.126.488.69.404.2]

Figure 1

A view of the cation of (I), with displacement ellipsoids drawn at the 30% probability level. H atoms bonded to C atoms

are not shown. Atoms labelled with the suffix ′A′ are related by the symmetry operator (−x, y, −z + 1/2)

Tetrakis(µ2-2,6-diformyl-4-methylphenolato)tetra-µ3-hydroxo- tetrakis[diaquaneodymium(III)]

tetrakis(perchlorate) ethanol disolvate

Crystal data

[Nd4(C9H7O3)4(OH)4(H2O)8](ClO4)4·2C2H6O

Mr = 1931.64

Monoclinic, C2/c

Hall symbol: -C 2yc

a = 20.9933 (3) Å

b = 24.7385 (5) Å

c = 17.6893 (3) Å

β = 120.469 (1)°

V = 7918.1 (2) Å3

Z = 4

F(000) = 3776

Dx = 1.620 Mg m−3

Mo radiation, λ = 0.71073 Å

Cell parameters from 8715 reflections

θ = 2.6–27.5°

µ = 2.80 mm−1

T = 150 K

Block, yellow

0.32 × 0.28 × 0.25 mm

Data collection

Bruker Nonius KappaCCD area detector diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

Detector resolution: 9 pixels mm-1

φ scans and ω scans with κ offsets Absorption correction: multi-scan

(DENZO-SMN; Otwinowski & Minor, 1997)

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supporting information

sup-4

Acta Cryst. (2006). E62, m113–m115

8998 independent reflections 7708 reflections with I > 2σ(I)

Rint = 0.037

θmax = 27.5°, θmin = 2.6°

h = −27→27

k = −32→32

l = −22→19

Refinement

Refinement on F2

Least-squares matrix: full

R[F2 > 2σ(F2)] = 0.043

wR(F2) = 0.122

S = 1.06

8998 reflections 400 parameters 55 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrained

w = 1/[σ2(F

o2) + (0.0625P)2 + 41.2001P] where P = (Fo2 + 2Fc2)/3

(Δ/σ)max < 0.001 Δρmax = 1.64 e Å−3 Δρmin = −1.16 e Å−3

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)

x y z Uiso*/Ueq Occ. (<1)

Nd1 −0.103278 (13) 0.226744 (11) 0.186982 (16) 0.02998 (10)

Nd2 −0.027319 (12) 0.108328 (10) 0.334350 (15) 0.02776 (10)

O1 −0.0765 (2) 0.11184 (16) 0.4338 (2) 0.0395 (8)

O2 −0.14590 (17) 0.16722 (15) 0.2703 (2) 0.0344 (7)

O3 −0.2398 (2) 0.23177 (18) 0.1173 (2) 0.0439 (9)

O4 −0.1409 (7) 0.3076 (5) 0.0936 (8) 0.052 (3)* 0.50

O4A 0.1476 (7) 0.3110 (4) 0.3937 (8) 0.052 (3)* 0.50

O5 0.0000 0.2977 (2) 0.2500 0.0396 (11)*

O6 0.0205 (2) 0.02579 (15) 0.4208 (2) 0.0391 (8)

O7 0.0000 0.03688 (18) 0.2500 0.0324 (10)

O8 −0.07912 (17) 0.12937 (14) 0.1823 (2) 0.0284 (6)

H8 −0.1244 0.1079 0.1426 0.034*

O9 −0.00252 (16) 0.20477 (14) 0.3318 (2) 0.0285 (7)

H9 −0.0032 0.2259 0.3796 0.034*

O10 −0.1661 (2) 0.20022 (19) 0.0304 (2) 0.0482 (10)

H10C −0.1925 0.2232 −0.0078 0.072*

H10D −0.1512 0.1759 0.0098 0.072*

O11 −0.13126 (15) 0.28884 (12) 0.27878 (18) 0.0536 (10)

H11A −0.1219 0.2757 0.3271 0.080*

H11B −0.1052 0.3137 0.2761 0.080*

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H12A 0.0967 0.1057 0.5312 0.058*

H12B 0.0611 0.1550 0.5180 0.058*

O13 −0.1336 (2) 0.04277 (17) 0.2737 (3) 0.0479 (9)

H13C −0.1477 0.0260 0.2265 0.072*

H13D −0.1381 0.0188 0.3043 0.072*

C1 −0.2034 (2) 0.1666 (2) 0.2790 (3) 0.0326 (10)

C2 −0.2017 (3) 0.1420 (2) 0.3531 (3) 0.0347 (10)

C3 −0.2658 (3) 0.1411 (2) 0.3600 (4) 0.0437 (13)

H3A −0.2628 0.1250 0.4105 0.052*

C4 −0.3324 (3) 0.1625 (3) 0.2971 (5) 0.0513 (15)

C5 −0.3348 (3) 0.1861 (3) 0.2255 (4) 0.0534 (16)

H5A −0.3804 0.2007 0.1811 0.064*

C6 −0.2728 (3) 0.1895 (3) 0.2149 (4) 0.0420 (12)

C7 −0.1373 (3) 0.1197 (2) 0.4260 (3) 0.0386 (11)

H7A −0.1420 0.1096 0.4748 0.046*

C8 −0.3995 (4) 0.1604 (4) 0.3076 (6) 0.073 (2)

H8A −0.4444 0.1618 0.2497 0.109*

H8B −0.3987 0.1914 0.3426 0.109*

H8C −0.3988 0.1268 0.3374 0.109*

C9 −0.2853 (3) 0.2185 (3) 0.1380 (4) 0.0512 (15)

H9A −0.3350 0.2287 0.0983 0.061*

C10 −0.1264 (8) 0.3536 (7) 0.1237 (8) 0.103 (11)* 0.50

H10A −0.1662 0.3777 0.0904 0.123* 0.50

C11 −0.0651 (4) 0.3807 (4) 0.1961 (5) 0.057 (3)* 0.50

C12 −0.0002 (5) 0.3493 (3) 0.2531 (6) 0.060 (2)* 0.50

C13 −0.0683 (8) 0.4366 (5) 0.2112 (8) 0.073 (4)* 0.50

H13A −0.1120 0.4558 0.1722 0.087* 0.50

C10A 0.1278 (6) 0.3582 (5) 0.3887 (8) 0.052 (4)* 0.50

H10B 0.1619 0.3824 0.4321 0.063* 0.50

C11A 0.0578 (6) 0.3803 (5) 0.3235 (7) 0.066 (4)* 0.50

C13A 0.0519 (8) 0.4362 (5) 0.3357 (9) 0.078 (4)* 0.50

H13B 0.0921 0.4544 0.3833 0.094* 0.50

C14 −0.0113 (6) 0.4648 (6) 0.2795 (7) 0.085 (5)* 0.50

C15 −0.0180 (10) 0.5246 (7) 0.2923 (11) 0.177 (14)* 0.50

H15A 0.0175 0.5447 0.2826 0.266* 0.50

H15B −0.0075 0.5311 0.3522 0.266* 0.50

H15C −0.0682 0.5368 0.2504 0.266* 0.50

C16 0.0191 (3) −0.0224 (2) 0.4036 (3) 0.0389 (11)

H16A 0.0264 −0.0470 0.4485 0.047*

C17 0.0000 −0.0147 (2) 0.2500 0.0324 (14)

C18 0.0074 (3) −0.0459 (2) 0.3228 (3) 0.0378 (11)

C19 0.0070 (4) −0.1030 (2) 0.3205 (4) 0.0516 (15)

H19A 0.0118 −0.1222 0.3696 0.062*

C20 0.0000 −0.1322 (4) 0.2500 0.061 (2)

C21 0.0000 −0.1934 (4) 0.2500 0.085 (4)

H21A −0.0242 −0.2066 0.1894 0.127* 0.50

H21B −0.0268 −0.2066 0.2783 0.127* 0.50

(9)

supporting information

sup-6

Acta Cryst. (2006). E62, m113–m115

Cl1 0.02244 (8) 0.25412 (7) −0.02193 (10) 0.0527 (4)

O14 0.0939 (4) 0.2368 (3) 0.0294 (8) 0.155 (5)

O15 −0.0054 (6) 0.2765 (3) 0.0325 (5) 0.115 (3)

O16 −0.0269 (3) 0.2106 (2) −0.0698 (3) 0.0719 (15)

O17 0.0176 (3) 0.2957 (2) −0.0789 (3) 0.0623 (12)

Cl2 0.22322 (13) 0.01002 (11) 0.47137 (18) 0.0525 (8) 0.577 (4)

O18 0.2017 (5) −0.0118 (3) 0.5303 (5) 0.120 (3)

O19 0.2059 (5) 0.0655 (4) 0.4521 (11) 0.141 (7) 0.577 (4)

O20 0.1816 (6) −0.0144 (5) 0.3858 (6) 0.093 (3) 0.577 (4)

O21 0.2993 (4) −0.0008 (6) 0.5071 (8) 0.102 (4) 0.577 (4)

Cl2A 0.2145 (3) 0.0225 (2) 0.6070 (3) 0.0799 (16) 0.423 (4)

O19A 0.1495 (4) 0.0416 (4) 0.6196 (5) 0.037 (2) 0.423 (4)

O20A 0.2328 (15) 0.0773 (7) 0.5976 (19) 0.152 (9)* 0.423 (4)

O21A 0.2763 (14) 0.0035 (13) 0.6900 (14) 0.195 (12)* 0.423 (4)

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23

Nd1 0.02135 (14) 0.04034 (17) 0.02491 (15) 0.00338 (9) 0.00928 (11) 0.00406 (10)

Nd2 0.02325 (14) 0.03795 (16) 0.02207 (14) 0.00186 (9) 0.01149 (11) 0.00229 (9)

O1 0.0303 (17) 0.058 (2) 0.0329 (19) 0.0096 (16) 0.0180 (16) 0.0085 (16)

O2 0.0217 (15) 0.051 (2) 0.0314 (17) 0.0047 (14) 0.0140 (14) 0.0071 (15)

O3 0.0270 (17) 0.070 (3) 0.0312 (19) 0.0066 (16) 0.0121 (15) 0.0104 (18)

O6 0.046 (2) 0.041 (2) 0.0283 (18) 0.0045 (16) 0.0171 (16) 0.0026 (15)

O7 0.032 (2) 0.036 (2) 0.029 (2) 0.000 0.016 (2) 0.000

O8 0.0220 (14) 0.0371 (17) 0.0242 (15) −0.0003 (13) 0.0104 (13) 0.0022 (13)

O9 0.0216 (14) 0.0388 (17) 0.0240 (15) −0.0007 (12) 0.0108 (13) −0.0050 (13)

O10 0.041 (2) 0.069 (3) 0.0272 (18) 0.0221 (19) 0.0117 (16) 0.0093 (18)

O11 0.045 (2) 0.066 (3) 0.048 (2) 0.007 (2) 0.022 (2) −0.006 (2)

O12 0.0358 (18) 0.051 (2) 0.0270 (17) 0.0054 (16) 0.0139 (15) 0.0021 (16)

O13 0.042 (2) 0.055 (2) 0.048 (2) −0.0087 (18) 0.0232 (19) −0.0044 (19)

C1 0.022 (2) 0.046 (3) 0.027 (2) 0.0007 (19) 0.0113 (18) 0.000 (2)

C2 0.028 (2) 0.045 (3) 0.035 (3) 0.003 (2) 0.019 (2) 0.001 (2)

C3 0.037 (3) 0.056 (3) 0.052 (3) 0.001 (2) 0.032 (3) 0.007 (3)

C4 0.034 (3) 0.063 (4) 0.067 (4) 0.003 (3) 0.033 (3) 0.010 (3)

C5 0.028 (3) 0.076 (4) 0.056 (4) 0.008 (3) 0.022 (3) 0.016 (3)

C6 0.023 (2) 0.061 (3) 0.041 (3) 0.005 (2) 0.015 (2) 0.010 (3)

C7 0.038 (3) 0.052 (3) 0.032 (3) 0.004 (2) 0.022 (2) 0.008 (2)

C8 0.042 (3) 0.099 (6) 0.097 (6) 0.016 (3) 0.050 (4) 0.037 (5)

C9 0.025 (2) 0.081 (4) 0.041 (3) 0.009 (3) 0.011 (2) 0.014 (3)

C16 0.040 (3) 0.044 (3) 0.030 (2) 0.006 (2) 0.016 (2) 0.008 (2)

C17 0.028 (3) 0.036 (3) 0.031 (3) 0.000 0.013 (3) 0.000

C18 0.043 (3) 0.036 (3) 0.033 (3) 0.004 (2) 0.018 (2) 0.004 (2)

C19 0.071 (4) 0.040 (3) 0.051 (4) 0.001 (3) 0.037 (3) 0.006 (3)

C20 0.093 (8) 0.041 (5) 0.064 (6) 0.000 0.051 (6) 0.000

C21 0.152 (13) 0.045 (5) 0.079 (8) 0.000 0.074 (9) 0.000

Cl1 0.0417 (7) 0.0663 (9) 0.0414 (7) −0.0043 (6) 0.0147 (6) 0.0137 (7)

(10)

O15 0.219 (9) 0.081 (4) 0.105 (5) 0.006 (5) 0.126 (7) 0.008 (4)

O16 0.091 (4) 0.074 (3) 0.054 (3) −0.029 (3) 0.039 (3) −0.002 (3)

O17 0.058 (3) 0.080 (3) 0.054 (3) −0.011 (2) 0.032 (2) 0.015 (2)

Cl2 0.0381 (13) 0.0563 (15) 0.0496 (15) 0.0048 (10) 0.0123 (11) 0.0068 (11)

O18 0.169 (8) 0.100 (5) 0.122 (7) 0.028 (5) 0.096 (6) 0.030 (5)

O19 0.051 (5) 0.059 (6) 0.211 (16) 0.000 (5) −0.007 (7) 0.070 (8)

O20 0.090 (7) 0.089 (7) 0.056 (6) −0.004 (6) 0.006 (5) −0.006 (5)

O21 0.036 (5) 0.136 (11) 0.108 (9) 0.009 (5) 0.018 (5) −0.018 (8)

Cl2A 0.071 (3) 0.089 (3) 0.068 (3) −0.013 (2) 0.026 (2) 0.018 (3)

O19A 0.019 (3) 0.063 (6) 0.024 (4) 0.006 (3) 0.007 (3) 0.028 (4)

Geometric parameters (Å, º)

Nd1—O9 2.416 (3) C3—H3A 0.9500

Nd1—O4Ai 2.429 (12) C4—C5 1.372 (9)

Nd1—O4 2.456 (12) C4—C8 1.512 (7)

Nd1—O9i 2.467 (3) C5—C6 1.410 (7)

Nd1—O8 2.472 (3) C5—H5A 0.9500

Nd1—O10 2.478 (4) C6—C9 1.440 (8)

Nd1—O3 2.484 (4) C7—H7A 0.9500

Nd1—O11 2.512 (3) C8—H8A 0.9800

Nd1—O2 2.546 (3) C8—H8B 0.9800

Nd1—O5 2.565 (3) C8—H8C 0.9800

Nd1—Nd2 3.7019 (4) C9—H9A 0.9500

Nd1—Nd1i 3.7376 (5) C10—C11 1.441 (6)

Nd2—O8 2.392 (3) C10—H10A 0.9500

Nd2—O6 2.441 (4) C11—C13 1.415 (7)

Nd2—O9 2.447 (3) C11—C12 1.444 (6)

Nd2—O1 2.452 (3) C12—C11A 1.444 (6)

Nd2—O8i 2.453 (3) C13—C14 1.382 (7)

Nd2—O13 2.516 (4) C13—H13A 0.9500

Nd2—O7 2.559 (3) C10A—C11A 1.440 (6)

Nd2—O2 2.597 (3) C10A—H10B 0.9500

Nd2—O12 2.627 (3) C11A—C13A 1.415 (7)

Nd2—Nd2i 3.7003 (4) C13A—C14 1.383 (7)

O1—C7 1.228 (6) C13A—H13B 0.9500

O2—C1 1.292 (5) C14—C15 1.515 (13)

O3—C9 1.228 (7) C15—H15A 0.9800

O4—C10 1.227 (6) C15—H15B 0.9800

O4A—C10A 1.227 (6) C15—H15C 0.9800

O4A—Nd1i 2.429 (12) C16—C18 1.444 (6)

O5—C12 1.276 (7) C16—H16A 0.9500

O5—C12i 1.276 (7) C17—C18 1.440 (5)

O5—Nd1i 2.565 (3) C17—C18i 1.440 (5)

O6—C16 1.227 (6) C18—C19 1.414 (7)

O7—C17 1.276 (7) C19—C20 1.383 (7)

O7—Nd2i 2.559 (3) C19—H19A 0.9500

(11)

supporting information

sup-8

Acta Cryst. (2006). E62, m113–m115

O8—H8 1.0000 C20—C21 1.515 (13)

O9—Nd1i 2.467 (3) C21—H21A 0.9800

O9—H9 1.0000 C21—H21B 0.9800

O10—H10C 0.8399 C21—H21C 0.9800

O10—H10D 0.8400 Cl1—O14 1.370 (6)

O11—H11A 0.8401 Cl1—O17 1.406 (5)

O11—H11B 0.8398 Cl1—O16 1.436 (5)

O12—H12A 0.8399 Cl1—O15 1.464 (6)

O12—H12B 0.8399 Cl2—O21 1.414 (8)

O13—H13C 0.8402 Cl2—O19 1.417 (8)

O13—H13D 0.8401 Cl2—O18 1.436 (7)

C1—C2 1.429 (7) Cl2—O20 1.442 (9)

C1—C6 1.431 (7) O18—Cl2A 1.505 (9)

C2—C3 1.411 (6) Cl2A—O20A 1.440 (14)

C2—C7 1.424 (7) Cl2A—O21A 1.458 (15)

C3—C4 1.376 (9) Cl2A—O19A 1.563 (8)

O9—Nd1—O4Ai 133.2 (3) C12—O5—C12i 5.1 (7)

O9—Nd1—O4 135.0 (3) C12—O5—Nd1 133.0 (4)

O4Ai—Nd1—O4 7.7 (4) C12i—O5—Nd1 133.3 (4)

O9—Nd1—O9i 74.28 (12) C12—O5—Nd1i 133.3 (4)

O4Ai—Nd1—O9i 102.3 (3) C12i—O5—Nd1i 133.0 (4)

O4—Nd1—O9i 95.4 (3) Nd1—O5—Nd1i 93.56 (16)

O9—Nd1—O8 74.46 (11) C16—O6—Nd2 135.0 (3)

O4Ai—Nd1—O8 147.2 (3) C17—O7—Nd2 133.69 (7)

O4—Nd1—O8 140.6 (3) C17—O7—Nd2i 133.69 (7)

O9i—Nd1—O8 64.32 (11) Nd2—O7—Nd2i 92.62 (15)

O9—Nd1—O10 144.03 (12) Nd2—O8—Nd2i 99.58 (11)

O4Ai—Nd1—O10 75.1 (3) Nd2—O8—Nd1 99.10 (12)

O4—Nd1—O10 69.9 (3) Nd2i—O8—Nd1 115.20 (12)

O9i—Nd1—O10 78.24 (12) Nd2—O8—H8 113.7

O8—Nd1—O10 72.92 (12) Nd2i—O8—H8 113.7

O9—Nd1—O3 135.02 (11) Nd1—O8—H8 113.7

O4Ai—Nd1—O3 70.3 (3) Nd1—O9—Nd2 99.14 (11)

O4—Nd1—O3 74.3 (3) Nd1—O9—Nd1i 99.90 (12)

O9i—Nd1—O3 146.66 (12) Nd2—O9—Nd1i 115.59 (12)

O8—Nd1—O3 103.70 (12) Nd1—O9—H9 113.5

O10—Nd1—O3 68.43 (13) Nd2—O9—H9 113.5

O9—Nd1—O11 79.53 (10) Nd1i—O9—H9 113.5

O4Ai—Nd1—O11 73.1 (3) Nd1—O10—H10C 118.7

O4—Nd1—O11 80.6 (3) Nd1—O10—H10D 124.7

O9i—Nd1—O11 138.01 (10) H10C—O10—H10D 112.0

O8—Nd1—O11 137.48 (10) Nd1—O11—H11A 114.3

O10—Nd1—O11 135.93 (11) Nd1—O11—H11B 92.2

O3—Nd1—O11 72.60 (12) H11A—O11—H11B 121.2

O9—Nd1—O2 68.39 (11) Nd2—O12—H12A 118.5

O4Ai—Nd1—O2 134.0 (3) Nd2—O12—H12B 111.3

(12)

O9i—Nd1—O2 123.73 (11) Nd2—O13—H13C 122.0

O8—Nd1—O2 66.06 (11) Nd2—O13—H13D 123.1

O10—Nd1—O2 110.52 (13) H13C—O13—H13D 101.2

O3—Nd1—O2 70.15 (12) O2—C1—C2 121.5 (4)

O11—Nd1—O2 73.33 (11) O2—C1—C6 122.5 (4)

O9—Nd1—O5 66.45 (10) C2—C1—C6 115.9 (4)

O4Ai—Nd1—O5 69.8 (3) C3—C2—C7 115.1 (5)

O4—Nd1—O5 69.3 (3) C3—C2—C1 120.3 (5)

O9i—Nd1—O5 65.73 (10) C7—C2—C1 124.5 (4)

O8—Nd1—O5 122.64 (11) C4—C3—C2 123.1 (5)

O10—Nd1—O5 121.37 (11) C4—C3—H3A 118.4

O3—Nd1—O5 133.64 (13) C2—C3—H3A 118.4

O11—Nd1—O5 73.94 (8) C5—C4—C3 117.2 (5)

O2—Nd1—O5 127.76 (8) C5—C4—C8 121.8 (6)

O9—Nd1—Nd2 40.75 (8) C3—C4—C8 121.1 (6)

O4Ai—Nd1—Nd2 173.1 (3) C4—C5—C6 122.9 (5)

O4—Nd1—Nd2 174.3 (3) C4—C5—H5A 118.5

O9i—Nd1—Nd2 79.90 (7) C6—C5—H5A 118.5

O8—Nd1—Nd2 39.65 (7) C5—C6—C1 120.5 (5)

O10—Nd1—Nd2 111.89 (10) C5—C6—C9 114.6 (5)

O3—Nd1—Nd2 111.46 (9) C1—C6—C9 124.8 (5)

O11—Nd1—Nd2 100.79 (7) O1—C7—C2 128.2 (5)

O2—Nd1—Nd2 44.51 (7) O1—C7—H7A 115.9

O5—Nd1—Nd2 105.57 (7) C2—C7—H7A 115.9

O9—Nd1—Nd1i 40.56 (7) C4—C8—H8A 109.5

O4Ai—Nd1—Nd1i 109.5 (3) C4—C8—H8B 109.5

O4—Nd1—Nd1i 106.3 (3) H8A—C8—H8B 109.5

O9i—Nd1—Nd1i 39.55 (7) C4—C8—H8C 109.5

O8—Nd1—Nd1i 79.88 (7) H8A—C8—H8C 109.5

O10—Nd1—Nd1i 117.74 (9) H8B—C8—H8C 109.5

O3—Nd1—Nd1i 173.74 (10) O3—C9—C6 128.1 (5)

O11—Nd1—Nd1i 101.26 (6) O3—C9—H9A 115.9

O2—Nd1—Nd1i 107.26 (7) C6—C9—H9A 115.9

O5—Nd1—Nd1i 43.22 (8) O4—C10—C11 137.0 (18)

Nd2—Nd1—Nd1i 67.960 (6) O4—C10—H10A 111.5

O8—Nd2—O6 133.98 (12) C11—C10—H10A 111.5

O8—Nd2—O9 75.33 (11) C13—C11—C10 121.1 (11)

O6—Nd2—O9 143.45 (12) C13—C11—C12 120.8 (10)

O8—Nd2—O1 133.04 (11) C10—C11—C12 118.0 (13)

O6—Nd2—O1 76.66 (12) O5—C12—C11A 123.3 (8)

O9—Nd2—O1 98.62 (12) O5—C12—C11 122.1 (9)

O8—Nd2—O8i 75.01 (12) C11A—C12—C11 113.5 (7)

O6—Nd2—O8i 98.18 (12) C14—C13—C11 123.8 (13)

O9—Nd2—O8i 64.89 (11) C14—C13—H13A 118.1

O1—Nd2—O8i 145.01 (12) C11—C13—H13A 118.1

O8—Nd2—O13 82.05 (13) O4A—C10A—C11A 126.2 (14)

O6—Nd2—O13 73.86 (14) O4A—C10A—H10B 116.9

(13)

supporting information

sup-10

Acta Cryst. (2006). E62, m113–m115

O1—Nd2—O13 73.95 (14) C13A—C11A—C10A 112.5 (10)

O8i—Nd2—O13 138.63 (12) C13A—C11A—C12 123.5 (11)

O8—Nd2—O7 66.61 (10) C10A—C11A—C12 124.1 (12)

O6—Nd2—O7 69.20 (10) C14—C13A—C11A 121.1 (14)

O9—Nd2—O7 123.36 (10) C14—C13A—H13B 119.5

O1—Nd2—O7 138.02 (12) C11A—C13A—H13B 119.5

O8i—Nd2—O7 65.76 (9) C13—C14—C13A 117.4 (15)

O13—Nd2—O7 73.67 (11) C13—C14—C15 121.3 (8)

O8—Nd2—O2 66.36 (11) C13A—C14—C15 121.3 (8)

O6—Nd2—O2 137.84 (12) O6—C16—C18 127.4 (5)

O9—Nd2—O2 67.10 (11) O6—C16—H16A 116.3

O1—Nd2—O2 68.50 (11) C18—C16—H16A 116.3

O8i—Nd2—O2 123.97 (11) O7—C17—C18 122.4 (3)

O13—Nd2—O2 74.27 (13) O7—C17—C18i 122.4 (3)

O7—Nd2—O2 125.60 (8) C18—C17—C18i 115.2 (6)

O8—Nd2—O12 146.21 (10) C19—C18—C17 120.9 (5)

O6—Nd2—O12 69.45 (11) C19—C18—C16 115.2 (5)

O9—Nd2—O12 75.19 (10) C17—C18—C16 123.8 (5)

O1—Nd2—O12 67.92 (11) C20—C19—C18 123.0 (6)

O8i—Nd2—O12 77.80 (9) C20—C19—H19A 118.5

O13—Nd2—O12 131.68 (12) C18—C19—H19A 118.5

O7—Nd2—O12 118.72 (6) C19—C20—C19i 117.1 (8)

O2—Nd2—O12 115.50 (10) C19—C20—C21 121.5 (4)

O8—Nd2—Nd2i 40.82 (7) C19i—C20—C21 121.5 (4)

O6—Nd2—Nd2i 107.94 (8) C20—C21—H21A 109.5

O9—Nd2—Nd2i 80.16 (7) C20—C21—H21B 109.5

O1—Nd2—Nd2i 173.85 (8) H21A—C21—H21B 109.5

O8i—Nd2—Nd2i 39.61 (7) C20—C21—H21C 109.5

O13—Nd2—Nd2i 103.11 (10) H21A—C21—H21C 109.5

O7—Nd2—Nd2i 43.69 (7) H21B—C21—H21C 109.5

O2—Nd2—Nd2i 105.60 (7) O14—Cl1—O17 111.1 (4)

O12—Nd2—Nd2i 117.26 (6) O14—Cl1—O16 112.0 (5)

O8—Nd2—Nd1 41.25 (8) O17—Cl1—O16 110.9 (3)

O6—Nd2—Nd1 175.23 (8) O14—Cl1—O15 110.5 (7)

O9—Nd2—Nd1 40.11 (7) O17—Cl1—O15 106.6 (4)

O1—Nd2—Nd1 106.83 (9) O16—Cl1—O15 105.2 (4)

O8i—Nd2—Nd1 80.85 (8) O21—Cl2—O19 112.7 (7)

O13—Nd2—Nd1 103.75 (10) O21—Cl2—O18 107.7 (7)

O7—Nd2—Nd1 106.25 (6) O19—Cl2—O18 113.7 (9)

O2—Nd2—Nd1 43.41 (7) O21—Cl2—O20 109.6 (8)

O12—Nd2—Nd1 114.73 (7) O19—Cl2—O20 102.1 (8)

Nd2i—Nd2—Nd1 68.352 (6) O18—Cl2—O20 111.0 (7)

C7—O1—Nd2 135.8 (3) Cl2—O18—Cl2A 117.7 (6)

C1—O2—Nd1 134.4 (3) O20A—Cl2A—O21A 105.5 (18)

C1—O2—Nd2 133.6 (3) O20A—Cl2A—O18 111.2 (12)

Nd1—O2—Nd2 92.08 (10) O21A—Cl2A—O18 112.8 (14)

(14)

C10—O4—Nd1 122.6 (10) O21A—Cl2A—O19A 110.4 (14)

C10A—O4A—Nd1i 139.4 (11) O18—Cl2A—O19A 121.9 (6)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A

O8—H8···O19i 1.00 1.98 2.969 (10) 168

O9—H9···O15i 1.00 1.93 2.922 (7) 170

O10—H10C···O3ii 0.84 2.05 2.884 (5) 170

O10—H10D···O12i 0.84 1.98 2.764 (5) 155

O11—H11A···O14i 0.84 2.49 3.331 (14) 180

O12—H12A···O19A 0.84 2.10 2.945 (8) 180

O12—H12B···O16i 0.84 1.98 2.819 (6) 180

O13—H13C···O20i 0.84 2.01 2.845 (12) 180

O13—H13D···O19Aiii 0.84 2.10 2.943 (8) 180

Figure

Figure 1
Figure 1

References

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Given our DADT model, we assume that the test text was written by a “new” author, and infer this author’s topic distribution, the author/document topic ratio, and the document

As a hybrid representation, we also tested the ef- fect of merging words with their corresponding SF (e.g. This is a form of seman- tic specialization rather than generalization,