metal-organic papers
Acta Cryst.(2005). E61, m1337–m1339 doi:10.1107/S1600536805018271 Poulsenet al. [Gd
2(C8H4O4)3(C5H11NO)2]H2O
m1337
Acta Crystallographica Section E Structure Reports Online
ISSN 1600-5368
A gadolinium-based metal–organic framework,
poly[[tris(
l
4-benzene-1,4-dicarboxylato)-bis(
l
2-
N
,
N
-diethylformamide)digadolinium(III)]
monohydrate]
Rasmus D. Poulsen, Jacob Overgaard,* Marie-Agnes Chevallier, Henrik F. Clausen and Bo B. Iversen
Department of Chemistry, University of Aarhus, Langelandsgade 140, DK-8000 Aarhus C, Denmark
Correspondence e-mail: jacobo@chem.au.dk
Key indicators
Single-crystal X-ray study
T= 100 K
Mean(C–C) = 0.002 A˚ H-atom completeness 95% Disorder in main residue
Rfactor = 0.022
wRfactor = 0.054
Data-to-parameter ratio = 41.0
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2005 International Union of Crystallography Printed in Great Britain – all rights reserved
The crystal structure of the title compound, {[Gd2(C8H4O4)3(C5H11NO)2]H2O}n, consists of chains of Gd
atoms interconnected by a benzene-1,4-dicarboxylate (BDC) linker. The chains are also intraconnected by carboxylate groups from the BDC linker, thus generating a three-dimensional framework with large cavities. The coordination of the eight carboxylate O atoms around the GdIII ion is distorted dodecahedral, due to the steric constraints of the carboxylate groups. The large anisotropic displacement parameters of the atoms of the coordinated diethylformamide (DEF) and the disorder in their positions indicate loose bonding to the framework, and hence solvent exchange may be possible. Additionally, one water molecule is located in the cavity.
Comment
Metal–organic frameworks (MOFs) are of great scientific interest (Kitahawaet al., 2004; Lu, 2003; O0Keeffeet al., 2000).
Their potential use in gas storage has gained enormous attention worldwide. Our main research effort has so far been focused on the magnetic properties of these compounds (Zhanget al., 2005), and in this context the title structure, (I), is the first in a series of new MOFs which may combine interesting magnetic effects and potential gas storage, due to their electron-rich metal centres.
The structure of (I) consists of chains of carboxylate-bridged GdIII atoms interconnected by benzene-1,4-dicarboxylate (BDC) linkers. The Gd chains are aligned along the c axis and thus there appears to be a unique magnetic direction, as interchain distances (>9.7 A˚ ) are much larger than the intrachain Gd Gd distance of 4.0363 (1) A˚ .
The GdIII ion is coordinated by seven O atoms from the carboxylate groups and one O atom from the diethyl-formamide (DEF) molecule. There is one -bridging carboxylate atom, O31, which bridges two Gd atoms with a long [Gd—O 2.818 (1) A˚ ] and a short [Gd—O 2.381 (1) A˚] bond. Not taking the long bond into account, the average bond length of the remaining carboxylate O atoms, <Gd— O(carboxylate)>, is 2.339 (1) A˚ , while <Gd—O(DEF)> is 2.428 (1) A˚ . The intraconnection of the Gd atoms by bridging carboxylate (OCO)groups and only one bridging O31 atom gives rise to a disrupted Gd—O—Gd coupling.
The carboxylate groups in (I) are all delocalized, with an average C—O bond length of 1.260 (2) A˚ . This gives a net charge of0.5 efor each unique O atom. A formal electron count suggests that the Gd atom has a charge of +3, which is in agreement with the synthesis conditions.
In the crystal structure of (I), the inner parts of the voids are occupied by DEF molecules, which are bonded directly to the Gd atoms. As previously reported (Poulsenet al., 2004, 2005) DEF solvent molecules do not only occupy the voids but also bond directly to the metal centres. The ethyl groups of the DEF molecule are disordered, with no overlap of atoms in the two positions [occupancy factors of 0.622 (6) and 0.378 (6)]. A single water molecule is found in the void, disordered over two crystallographically equivalent positions (50:50%) only 1.086 A˚ apart. The two H atoms of this water molecule were not located or included in the refinement.
Due to the bonding of the DEF molecule to the framework, it has been possible to refine the anisotropic displacement parameters of all non-H atoms. The displacement ellipsoid of the methyl group atom C20 is highly elongated towards H20C. This is probably due to further unresolved disorder.
Experimental
The title compound was prepared in an autoclave by adding a mixture of benzene dicarboxylic acid (BDC; 1 mmol, 0.166 g) and diethyl-formamide (DEF; 7 ml) to a solution of Gd(NO3)35H2O (1.0 mmol,
0.434 g) in DEF (3 ml). The mixture was kept at 383 K for 72 h. White crystals of (I) suitable for single-crystal X-ray analysis were formed.
Crystal data
[Gd2(C8H4O4)3(C5H11NO)2]H2O
Mr= 1025.13 Monoclinic,C2=c a= 18.0582 (5) A˚
b= 11.4381 (3) A˚
c= 18.6791 (4) A˚ = 108.796 (1) V= 3652.44 (16) A˚3
Z= 4
Dx= 1.864 Mg m
3
MoKradiation Cell parameters from 7811
reflections = 2.8–42.4
= 3.67 mm1
T= 100 (2) K Block, white
0.200.050.05 mm
Data collection
Bruker X8 APEXII CCD-based diffractometer
’and!scans
Absorption correction: multi-scan (Blessing, 1995)
Tmin= 0.741,Tmax= 0.830
61459 measured reflections
11366 independent reflections 9378 reflections withI> 2(I)
Rint= 0.039
max= 43.0
h=33!29
k=20!20
l=33!32
Refinement
Refinement onF2
R[F2> 2(F2)] = 0.022
wR(F2) = 0.054
S= 0.95 11366 reflections 277 parameters
H-atom parameters constrained
w= 1/[2(F
o2) + (0.0284P)2]
whereP= (Fo2+ 2Fc2)/3
(/)max= 0.001 max= 2.59 e A˚3 min=0.96 e A˚
3
H atoms bonded to C atoms were included in calculated positions (C—H = 0.95–0.99 A˚ ) and refined in a riding-model approximation, with Uiso(H) = 1.2Ueq(C), or 1.5Ueq(C) for methyl groups. The
disorder in the DEF molecule has no overlapping positions, and the sum of the two disordered occupancies was fixed to unity. The nine largest residual peaks were distributed within 0.75 A˚ around the Gd atoms.
Data collection:APEX2(Bruker–Nonius, 2004); cell refinement: SAINT-Plus; data reduction: SAINT-Plus (Bruker–Nonius, 2004);
metal-organic papers
m1338
Poulsenet al. [Gd [image:2.610.45.301.68.311.2]2(C8H4O4)3(C5H11NO)2]H2O Acta Cryst.(2005). E61, m1337–m1339 Figure 1
[image:2.610.305.563.72.272.2]Part of the structure of the title compound. The disorder of the ethyl groups is shown with purple and turquoise bonds. For clarity, all ethyl H atoms except H20C have been omitted. Displacement ellipsoids are drawn at the 50% probability level.
Figure 2
program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure:SHELXL97(Sheldrick, 1997); molecular graphics: XSHELL (Bruker, 2004); software used to prepare material for publication: enCIFer(version 1.1; Allenet al., 2004).
Financial support of this work by the Carlsberg Foundation is gratefully acknowledged.
References
Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004).J. Appl. Cryst.37, 335–338.
Blessing, R. H. (1995).Acta Cryst.A51, 33–38.
Bruker–Nonius (2004).SAINT-Plus(Version 7.06a),XSHELL(Version 4.02) andAPEX2. Bruker–Nonius AXS Inc., Madison, Wisconsin, USA. Kitahawa, S., Kitaura, R. & Noro, S. (2004).Angew. Chem. Int. Ed.43, 2334–
2375.
Lu, J. Y. (2003).Coord. Chem. Rev.246, 327–347.
O’Keeffe, M., Eddaoudi, M., Li, H., Reineke, T. & Yaghi, O. M. (2000).J. Solid State Chem.152, 3–20.
Poulsen, R. D., Bentien, A., Chevalier. M. & Iversen, B. B. (2005).J. Am. Chem. Soc.In the press.
Poulsen, R. D., Bentien, A., Graber, T. & Iversen, B. B. (2004).Acta Cryst.
A60, 382–389.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Go¨ttingen, Germany.
Zhang, H., Song, Y., Li, Y., Zuo, J., Gao, S. & You, X. (2005).Eur. J. Inorg. Chem.pp. 766–772.
metal-organic papers
Acta Cryst.(2005). E61, m1337–m1339 Poulsenet al. [Gd
supporting information
sup-1
Acta Cryst. (2005). E61, m1337–m1339
supporting information
Acta Cryst. (2005). E61, m1337–m1339 [https://doi.org/10.1107/S1600536805018271]
A gadolinium-based metal
–
organic framework, poly[[tris(
µ
4-benzene-1,4-di-carboxylato)bis(
µ
2-
N
,
N
-diethylformamide)digadolinium(III)] monohydrate]
Rasmus D. Poulsen, Jacob Overgaard, Marie-Agnes Chevallier, Henrik F. Clausen and Bo B.
Iversen
poly[[tris(µ4-benzene-1,4-dicarboxylato)bis(µ2– N,N-diethylformamide)digadolinium(III)] monohydrate]
Crystal data
[Gd2(C8H4O4)3(C5H11NO)2]·H2O
Mr = 1025.13
Monoclinic, C2/c
Hall symbol: -C 2yc
a = 18.0582 (5) Å
b = 11.4381 (3) Å
c = 18.6791 (4) Å
β = 108.796 (1)°
V = 3652.44 (16) Å3
Z = 4
F(000) = 2000
Dx = 1.864 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 7811 reflections
θ = 2.8–42.4°
µ = 3.67 mm−1
T = 100 K
Block, white
0.20 × 0.05 × 0.05 mm
Data collection
Bruker SMART APEXII CCD-based diffractometer
Radiation source: fine-focus sealed tube, Siemens K FFMO 2K 90
Graphite monochromator
Detector resolution: 83.33 pixels mm-1
φ and ω scans
Absorption correction: multi-scan (Blessing, 1995)
Tmin = 0.741, Tmax = 0.830 61459 measured reflections 11366 independent reflections 9378 reflections with I > 2σ(I)
Rint = 0.039
θmax = 43.0°, θmin = 2.1°
h = −33→29
k = −20→20
l = −33→32
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.022
wR(F2) = 0.054
S = 0.95
11366 reflections 277 parameters 0 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) + (0.0284P)2] where P = (Fo2 + 2Fc2)/3 (Δ/σ)max = 0.001
supporting information
sup-2
Acta Cryst. (2005). E61, m1337–m1339 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)
Gd1 0.001829 (3) 0.559920 (4) 0.102180 (3) 0.00726 (2)
O1 0.08900 (6) 0.56023 (9) 0.22407 (6) 0.01713 (18)
O31 −0.07784 (6) 0.43229 (9) 0.00789 (7) 0.01854 (19)
C1 0.11733 (7) 0.56150 (10) 0.29411 (7) 0.01022 (17)
O11 −0.08653 (5) 0.51300 (8) 0.16110 (5) 0.01153 (14)
O14 0.10513 (6) 0.68267 (9) 0.09204 (6) 0.01663 (17)
O21 −0.02661 (7) 0.74494 (9) 0.15146 (6) 0.01815 (18)
O41 −0.07090 (6) 0.67660 (9) 0.00048 (5) 0.01924 (19)
C11 0.18656 (7) 0.69969 (11) 0.01577 (7) 0.0142 (2)
C2 0.19404 (7) 0.62278 (11) 0.32888 (7) 0.01196 (18)
C3 0.22907 (8) 0.68160 (13) 0.28281 (7) 0.0176 (2)
H3 0.2064 0.6782 0.2294 0.021*
C12 0.19865 (8) 0.67711 (12) −0.05289 (8) 0.0165 (2)
H12 0.1636 0.6276 −0.0891 0.020*
C7 0.22854 (8) 0.62536 (12) 0.40715 (7) 0.0144 (2)
H7 0.2053 0.5841 0.4386 0.017*
C10 0.11899 (7) 0.64679 (11) 0.03387 (7) 0.0142 (2)
O13 0.07687 (8) 0.39149 (12) 0.11365 (6) 0.0318 (3)
C6 0.29705 (8) 0.68840 (12) 0.43921 (7) 0.0169 (2)
H6 0.3209 0.6894 0.4926 0.020*
C13 0.23812 (8) 0.77300 (13) 0.06843 (8) 0.0182 (2)
H13 0.2299 0.7889 0.1152 0.022*
C5 0.33072 (9) 0.75001 (13) 0.39337 (7) 0.0188 (2)
C41 −0.09999 (9) 0.67298 (13) −0.07060 (8) 0.0216 (3)
C4 0.29713 (9) 0.74512 (14) 0.31507 (8) 0.0223 (3)
H4 0.3209 0.7854 0.2837 0.027*
N16 −0.05939 (13) 0.93673 (12) 0.13197 (13) 0.0370 (4)
C15 −0.02170 (15) 0.84050 (15) 0.12457 (15) 0.0436 (6)
H15 0.0126 0.8466 0.0954 0.052*
C19 −0.1864 (2) 0.9755 (4) 0.1531 (3) 0.0573 (14) 0.622 (6)
H19A −0.2109 0.9768 0.1929 0.086* 0.622 (6)
H19B −0.2134 0.9186 0.1143 0.086* 0.622 (6)
H19C −0.1901 1.0533 0.1303 0.086* 0.622 (6)
C20 −0.0182 (3) 1.1406 (4) 0.1242 (5) 0.105 (3) 0.622 (6)
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Acta Cryst. (2005). E61, m1337–m1339
H20B 0.0368 1.1165 0.1439 0.158* 0.622 (6)
H20C −0.0366 1.1620 0.1664 0.158* 0.622 (6)
C19A −0.1394 (7) 0.9902 (10) 0.2082 (7) 0.089 (4) 0.378 (6)
H19D −0.1923 0.9792 0.2108 0.134* 0.378 (6)
H19E −0.1298 1.0737 0.2034 0.134* 0.378 (6)
H19F −0.1011 0.9596 0.2544 0.134* 0.378 (6)
C20A −0.0652 (5) 1.0785 (6) 0.0379 (5) 0.056 (2) 0.378 (6)
H20D −0.0436 1.1513 0.0253 0.085* 0.378 (6)
H20E −0.1208 1.0894 0.0313 0.085* 0.378 (6)
H20F −0.0592 1.0158 0.0044 0.085* 0.378 (6)
C17 −0.0658 (3) 1.0433 (3) 0.0815 (3) 0.0497 (13) 0.626 (7)
H17A −0.0478 1.0226 0.0384 0.060* 0.626 (7)
H17B −0.1212 1.0680 0.0610 0.060* 0.626 (7)
C18 −0.1019 (2) 0.9415 (2) 0.1867 (2) 0.0290 (7) 0.626 (7)
H18A −0.0756 0.9984 0.2268 0.035* 0.626 (7)
H18B −0.0989 0.8639 0.2109 0.035* 0.626 (7)
C17A −0.0219 (4) 1.0459 (4) 0.1193 (4) 0.0326 (14) 0.374 (7)
H17C 0.0344 1.0332 0.1271 0.039* 0.374 (7)
H17D −0.0273 1.1080 0.1542 0.039* 0.374 (7)
C18A −0.1320 (5) 0.9287 (5) 0.1438 (5) 0.0387 (18) 0.374 (7)
H18C −0.1433 0.8450 0.1491 0.046* 0.374 (7)
H18D −0.1726 0.9584 0.0981 0.046* 0.374 (7)
O99 −0.0274 (3) 1.2785 (5) 0.2561 (4) 0.106 (2)* 0.50
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
Gd1 0.00684 (2) 0.00960 (2) 0.00528 (3) −0.00035 (2) 0.00190 (2) 0.00008 (2)
O1 0.0128 (4) 0.0305 (5) 0.0068 (4) −0.0046 (3) 0.0012 (3) 0.0011 (3)
O31 0.0150 (4) 0.0224 (5) 0.0208 (5) −0.0110 (3) 0.0094 (4) −0.0105 (4)
C1 0.0095 (4) 0.0136 (4) 0.0073 (4) 0.0013 (3) 0.0025 (3) 0.0000 (3)
O11 0.0112 (3) 0.0154 (4) 0.0095 (4) −0.0018 (3) 0.0053 (3) −0.0020 (3)
O14 0.0173 (4) 0.0220 (4) 0.0138 (4) −0.0087 (4) 0.0094 (3) −0.0059 (4)
O21 0.0257 (5) 0.0151 (4) 0.0142 (4) 0.0010 (4) 0.0071 (4) −0.0028 (3)
O41 0.0256 (5) 0.0213 (4) 0.0083 (4) 0.0115 (4) 0.0019 (3) 0.0022 (3)
C11 0.0137 (5) 0.0174 (5) 0.0140 (5) −0.0072 (4) 0.0080 (4) −0.0055 (4)
C2 0.0137 (5) 0.0140 (4) 0.0080 (4) −0.0027 (4) 0.0032 (4) −0.0006 (4)
C3 0.0208 (5) 0.0241 (6) 0.0072 (5) −0.0099 (5) 0.0034 (4) −0.0007 (4)
C12 0.0165 (5) 0.0216 (5) 0.0139 (5) −0.0096 (4) 0.0085 (4) −0.0069 (4)
C7 0.0162 (5) 0.0183 (5) 0.0080 (5) −0.0054 (4) 0.0030 (4) −0.0002 (4)
C10 0.0135 (5) 0.0174 (5) 0.0138 (5) −0.0062 (4) 0.0074 (4) −0.0035 (4)
O13 0.0444 (7) 0.0370 (6) 0.0103 (4) 0.0311 (6) 0.0038 (4) 0.0006 (4)
C6 0.0211 (5) 0.0197 (5) 0.0078 (5) −0.0082 (5) 0.0018 (4) −0.0006 (4)
C13 0.0186 (5) 0.0253 (6) 0.0142 (5) −0.0124 (5) 0.0101 (4) −0.0086 (5)
C5 0.0236 (6) 0.0216 (6) 0.0091 (5) −0.0128 (5) 0.0025 (4) −0.0012 (4)
C41 0.0292 (7) 0.0234 (6) 0.0100 (5) 0.0163 (5) 0.0032 (5) 0.0028 (5)
C4 0.0283 (7) 0.0281 (7) 0.0085 (5) −0.0173 (6) 0.0033 (5) −0.0003 (5)
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Acta Cryst. (2005). E61, m1337–m1339
C15 0.0628 (14) 0.0153 (6) 0.0760 (16) −0.0070 (7) 0.0546 (14) −0.0074 (8)
C19 0.0315 (18) 0.050 (2) 0.087 (4) 0.0063 (17) 0.014 (2) −0.009 (2)
C20 0.048 (2) 0.037 (2) 0.187 (7) −0.0153 (19) −0.024 (3) 0.056 (3)
C19A 0.092 (8) 0.099 (8) 0.106 (9) −0.034 (6) 0.074 (7) −0.067 (7)
C20A 0.049 (4) 0.045 (3) 0.070 (5) 0.012 (3) 0.013 (4) 0.037 (3)
C17 0.058 (3) 0.0241 (14) 0.070 (3) 0.0105 (16) 0.025 (3) 0.0231 (17)
C18 0.0346 (16) 0.0220 (11) 0.0317 (18) 0.0042 (10) 0.0127 (14) −0.0075 (11)
C17A 0.036 (3) 0.0129 (16) 0.051 (4) −0.0009 (16) 0.016 (3) 0.0037 (18)
C18A 0.046 (4) 0.025 (2) 0.058 (5) 0.000 (2) 0.034 (4) −0.003 (2)
Geometric parameters (Å, º)
Gd1—O11 2.2754 (9) C5—C41iv 1.5007 (19)
Gd1—O1 2.3135 (10) C41—O13i 1.2574 (17)
Gd1—O13 2.3253 (11) C41—C5v 1.5007 (19)
Gd1—O41 2.3468 (10) C4—H4 0.9500
Gd1—O31 2.3811 (10) N16—C15 1.325 (2)
Gd1—O14 2.3905 (9) N16—C18A 1.401 (6)
Gd1—O21 2.4278 (10) N16—C18 1.464 (4)
Gd1—O31i 2.8175 (11) N16—C17A 1.475 (5)
Gd1—Gd1i 4.0364 (1) N16—C17 1.522 (4)
O1—C1 1.2418 (15) C15—H15 0.9500
O31—C10i 1.2670 (15) C19—C18 1.503 (6)
O31—Gd1i 2.8175 (11) C19—H19A 0.9800
C1—O11ii 1.2715 (15) C19—H19B 0.9800
C1—C2 1.5007 (17) C19—H19C 0.9800
O11—C1ii 1.2715 (15) C20—C17 1.474 (8)
O14—C10 1.2598 (15) C20—H20A 0.9800
O21—C15 1.218 (2) C20—H20B 0.9800
O41—C41 1.2613 (17) C20—H20C 0.9800
C11—C12 1.3926 (17) C19A—C18A 1.436 (10)
C11—C13 1.3955 (18) C19A—H19D 0.9800
C11—C10 1.4952 (16) C19A—H19E 0.9800
C2—C7 1.3927 (17) C19A—H19F 0.9800
C2—C3 1.3944 (17) C20A—C17A 1.516 (11)
C3—C4 1.3872 (19) C20A—H20D 0.9800
C3—H3 0.9500 C20A—H20E 0.9800
C12—C13iii 1.3883 (17) C20A—H20F 0.9800
C12—H12 0.9500 C17—H17A 0.9900
C7—C6 1.3898 (18) C17—H17B 0.9900
C7—H7 0.9500 C18—H18A 0.9900
C10—O31i 1.2670 (15) C18—H18B 0.9900
O13—C41i 1.2574 (17) C17A—H17C 0.9900
C6—C5 1.3911 (19) C17A—H17D 0.9900
C6—H6 0.9500 C18A—H18C 0.9900
C13—C12iii 1.3883 (17) C18A—H18D 0.9900
C13—H13 0.9500 O99—O99ii 1.086 (11)
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Acta Cryst. (2005). E61, m1337–m1339
O11—Gd1—O1 83.40 (3) C6—C5—C41iv 119.21 (12)
O11—Gd1—O13 103.81 (5) C4—C5—C41iv 120.84 (12)
O1—Gd1—O13 73.68 (4) O13i—C41—O41 125.52 (13)
O11—Gd1—O41 103.23 (4) O13i—C41—C5v 117.27 (12)
O1—Gd1—O41 145.25 (4) O41—C41—C5v 117.20 (12)
O13—Gd1—O41 134.69 (4) C3—C4—C5 120.16 (12)
O11—Gd1—O31 82.09 (3) C3—C4—H4 119.9
O1—Gd1—O31 141.83 (4) C5—C4—H4 119.9
O13—Gd1—O31 75.85 (4) C15—N16—C18A 120.0 (3)
O41—Gd1—O31 72.71 (4) C15—N16—C18 120.43 (19)
O11—Gd1—O14 149.72 (3) C15—N16—C17A 114.1 (3)
O1—Gd1—O14 77.07 (3) C18A—N16—C17A 125.6 (3)
O13—Gd1—O14 92.72 (5) C18—N16—C17A 116.8 (3)
O41—Gd1—O14 81.33 (4) C15—N16—C17 122.7 (2)
O31—Gd1—O14 127.05 (3) C18A—N16—C17 105.2 (4)
O11—Gd1—O21 75.83 (3) C18—N16—C17 116.8 (2)
O1—Gd1—O21 77.61 (4) O21—C15—N16 126.48 (18)
O13—Gd1—O21 151.10 (4) O21—C15—H15 116.8
O41—Gd1—O21 71.31 (4) N16—C15—H15 116.8
O31—Gd1—O21 131.58 (4) C18—C19—H19A 109.5
O14—Gd1—O21 77.52 (4) C18—C19—H19B 109.5
O11—Gd1—O31i 160.55 (3) H19A—C19—H19B 109.5
O1—Gd1—O31i 112.41 (4) C18—C19—H19C 109.5
O13—Gd1—O31i 71.76 (4) H19A—C19—H19C 109.5
O41—Gd1—O31i 70.64 (4) H19B—C19—H19C 109.5
O31—Gd1—O31i 78.46 (3) C17—C20—H20A 109.5
O14—Gd1—O31i 49.27 (3) C17—C20—H20B 109.5
O21—Gd1—O31i 117.48 (3) H20A—C20—H20B 109.5
C1—O1—Gd1 162.85 (9) C17—C20—H20C 109.5
C10i—O31—Gd1 171.04 (10) H20A—C20—H20C 109.5
C10i—O31—Gd1i 84.27 (8) H20B—C20—H20C 109.5
Gd1—O31—Gd1i 101.54 (3) C18A—C19A—H19D 109.5
O1—C1—O11ii 124.68 (11) C18A—C19A—H19E 109.5
O1—C1—C2 118.10 (11) H19D—C19A—H19E 109.5
O11ii—C1—C2 117.22 (11) C18A—C19A—H19F 109.5
C1ii—O11—Gd1 137.64 (8) H19D—C19A—H19F 109.5
C10—O14—Gd1 104.71 (8) H19E—C19A—H19F 109.5
C15—O21—Gd1 125.00 (12) C17A—C20A—H20D 109.5
C41—O41—Gd1 140.18 (9) C17A—C20A—H20E 109.5
C12—C11—C13 119.59 (11) H20D—C20A—H20E 109.5
C12—C11—C10 120.97 (11) C17A—C20A—H20F 109.5
C13—C11—C10 119.44 (11) H20D—C20A—H20F 109.5
C7—C2—C3 119.95 (11) H20E—C20A—H20F 109.5
C7—C2—C1 120.17 (11) C20—C17—N16 110.8 (4)
C3—C2—C1 119.82 (11) C20—C17—H17A 109.5
C4—C3—C2 119.95 (12) N16—C17—H17A 109.5
supporting information
sup-6
Acta Cryst. (2005). E61, m1337–m1339
C2—C3—H3 120.0 N16—C17—H17B 109.5
C13iii—C12—C11 119.99 (12) H17A—C17—H17B 108.1
C13iii—C12—H12 120.0 N16—C18—C19 114.1 (4)
C11—C12—H12 120.0 N16—C18—H18A 108.7
C6—C7—C2 119.89 (11) C19—C18—H18A 108.7
C6—C7—H7 120.1 N16—C18—H18B 108.7
C2—C7—H7 120.1 C19—C18—H18B 108.7
O14—C10—O31i 121.57 (11) H18A—C18—H18B 107.6
O14—C10—C11 117.82 (11) N16—C17A—C20A 104.7 (5)
O31i—C10—C11 120.61 (11) N16—C17A—H17C 110.8
O14—C10—Gd1 51.08 (6) C20A—C17A—H17C 110.8
O31i—C10—Gd1 70.63 (7) N16—C17A—H17D 110.8
C11—C10—Gd1 168.03 (9) C20A—C17A—H17D 110.8
C41i—O13—Gd1 136.94 (10) H17C—C17A—H17D 108.9
C7—C6—C5 120.17 (12) N16—C18A—C19A 116.4 (7)
C7—C6—H6 119.9 N16—C18A—H18C 108.2
C5—C6—H6 119.9 C19A—C18A—H18C 108.2
C12iii—C13—C11 120.43 (12) N16—C18A—H18D 108.2
C12iii—C13—H13 119.8 C19A—C18A—H18D 108.2
C11—C13—H13 119.8 H18C—C18A—H18D 107.3
C6—C5—C4 119.83 (12)
