PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 May 1; 66(Pt 5): m576–m577.
Published online 2010 April 28. doi:  10.1107/S1600536810014716
PMCID: PMC2979116

{μ-6,6′-Dimeth­oxy-2,2′-[butane-1,4-diylbis(nitrilo­methyl­idyne)]diphenolato-1:2κ8 O 6,O 1,O 1′,O 6′:O 1,N,N′,O 1′}tris­(nitrato-1κ2 O,O′)copper(II)gadolinium(III)

Abstract

In the title dinuclear complex, [CuGd(C20H22N2O4)(NO3)3], the CuII ion is located in the inner N2O2 cavity of the Schiff base ligand and adopts a distorted square-planar geometry. The GdIII ion is ten-coordinate being bound to ten O atoms, four from the Schiff base ligand and six from three bidentate nitrate anions. The CuII and GdIII ions are linked by two phenolate O atoms of the Schiff base ligand, with a separation of 3.5185 (9) Å.

Related literature

For general background to 3d–4f bimetallic complexes, see: Sakamoto et al. (2001 [triangle]); Winpenny (1998 [triangle]); Yang et al. (2005 [triangle]). For related structures, see: Fei & Fang (2008 [triangle]); Xing et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m576-scheme1.jpg

Experimental

Crystal data

  • [CuGd(C20H22N2O4)(NO3)3]
  • M r = 761.22
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m576-efi1.jpg
  • a = 11.795 (2) Å
  • b = 14.730 (3) Å
  • c = 14.892 (3) Å
  • β = 100.58 (3)°
  • V = 2543.4 (9) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 3.50 mm−1
  • T = 223 K
  • 0.56 × 0.13 × 0.13 mm

Data collection

  • Rigaku MiniFlexII CCD diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002 [triangle]) T min = 0.598, T max = 1.000
  • 14367 measured reflections
  • 4460 independent reflections
  • 4090 reflections with I > 2σ(I)
  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.033
  • wR(F 2) = 0.128
  • S = 1.20
  • 4460 reflections
  • 362 parameters
  • 6 restraints
  • H-atom parameters constrained
  • Δρmax = 2.69 e Å−3
  • Δρmin = −1.35 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2002 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810014716/hy2285sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014716/hy2285Isup2.hkl

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

Acknowledgments

The authors acknowledge the Freshman Research Initiative, funded in part by the HHMI Undergraduate Science Education Award (52005907) and the National Science Foundation (CHE-0629136). Single crystal X-ray data were collected using instrumentation purchased with funds provided by the National Science Foundation (CHE-0741973). BJH wishes to acknowledge the Welch Foundation (F-1631), the Petroleum Research Fund administered by the American Chemical Society (47022-G3), the National Science Foundation (CHE-0639239, CHE-0847763), the American Heart Association (0765078Y), and the UT-CNM and UT-Austin for financial support of this research. RAJ wishes to acknowledge the Welch Foundation (F-816), the Texas Higher Education Coordinating Board (ARP003658–0010-2006) and the Petroleum Research Fund, administered by the American Chemical Society (47014-AC5).

supplementary crystallographic information

Comment

Heteropolynuclear complexes containing d- and f-block elements are currently of great interest because of their interesting physicochemical properties and potential applications as new materials (Sakamoto et al., 2001; Winpenny, 1998). Compartmental Schiff bases with two dissimilar metal-binding sites, one being specific for the d-block metal ion and another for the f-block metal ion, are classical ligands used to synthesize such heteronuclear complexes. As part of our ongoing interests in 3d–4f complexes with Schiff-base ligands (Yang et al., 2005), the title complex was synthesized and its crystal structure is reported herein.

The molecular structure of the title complex is shown in Fig. 1. It has a similar structure to other two Cu–Ln complexes with the Schiff-base ligand N,N'-bis(3-methoxysalicylidene)propane-1,3-diamine (H2L), [CuLnL(NO3)3] [Ln = EuIII (Xing et al., 2008) and TbIII (Fei & Fang, 2008)]. The CuII ion is coordinated by two N atoms and two O atoms from the Schiff-base ligand. The GdIII ion is surrounded by ten O atoms, four from the Schiff-base ligand and six from three bidentate NO3- anions. CuII and GdIII ions are bridged by two phenolate O atoms of the Schiff-base ligand, with a separation of 3.5185 (9) Å. The average distances for the Cu—O(phenolate) and Cu—N are 1.942 Å and 1.982 Å, respectively. The Gd—O(phenolate) distance of 2.377 Å (av.) is shorter than the Gd—O (methoxy) distance of 2.574 Å (av.), no doubt reflecting the difference between ionic vs. dative bonding. The average distance for the Gd—O (nitrate) is 2.464 Å, which is comparable to those found in the literature (Fei & Fang, 2008; Xing et al., 2008).

Experimental

A mixture of the Schiff-base ligand (0.178 g, 0.5 mmol) and Cu(CH3CO2)2.H2O (0.10 g, 0.5 mmol) in EtOH (15 ml) was stirred and refluxed for 10 min. The reaction mixture was allowed to cool briefly and Gd(NO3)3.6H2O (0.226 g, 0.5 mmol) was added and the mixture again heated under reflux (15 min) and then filtered. Diethylether was allowed to diffuse slowly into the filtrate at room temperature and blue crystals were obtained after two weeks. The crystals were filtered off and washed with 5 ml of EtOH (yield 0.176 g, 46.32%). m. p. > 260°C (dec). ESI-MS(MeOH) m/z: 700 [M—NO3]+. IR(CH3OH, cm-1): 3429 m, 1636 s, 1473 s, 1439 w, 1362 m, 1295 w, 1227 m, 1171 w, 1099 w, 1077 m, 1013 m, 658 s. UV-VIS(CH3OH, 25°C) λmax/nm: 215, 275, 350.

Refinement

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.94 (CH), 0.98 (CH2) and 0.97 (CH3) Å and with Uiso(H) = 1.2(1.5 for methyl groups)Ueq(C). The highest residual electron density was found 1.83 Å from H1A and the deepest hole 0.72 Å from Cu1.

Figures

Fig. 1.
The molecular structure of the title complex, with displacement ellipsoids shown at the 40% probability level. H atoms have been excluded for clarity.

Crystal data

[CuGd(C20H22N2O4)(NO3)3]F(000) = 1496
Mr = 761.22Dx = 1.988 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 8776 reflections
a = 11.795 (2) Åθ = 1.8–31.9°
b = 14.730 (3) ŵ = 3.50 mm1
c = 14.892 (3) ÅT = 223 K
β = 100.58 (3)°Prism, blue
V = 2543.4 (9) Å30.56 × 0.13 × 0.13 mm
Z = 4

Data collection

Rigaku MiniFlexII CCD diffractometer4460 independent reflections
Radiation source: fine-focus sealed tube4090 reflections with I > 2σ(I)
graphiteRint = 0.032
Detector resolution: 13.6612 pixels mm-1θmax = 25.0°, θmin = 2.0°
thin–slice ω scansh = −14→14
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002)k = −17→17
Tmin = 0.598, Tmax = 1.000l = −17→16
14367 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.128w = 1/[σ2(Fo2) + (0.0793P)2 + 1.3271P] where P = (Fo2 + 2Fc2)/3
S = 1.20(Δ/σ)max = 0.001
4460 reflectionsΔρmax = 2.69 e Å3
362 parametersΔρmin = −1.35 e Å3
6 restraintsExtinction correction: SHELXTL (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0022 (4)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Gd10.261236 (19)0.750997 (12)0.066103 (16)0.02180 (16)
Cu10.54871 (5)0.76924 (4)0.03441 (4)0.02328 (19)
N10.6472 (3)0.6645 (3)0.0102 (3)0.0281 (9)
N20.6638 (3)0.8666 (3)0.0545 (3)0.0251 (8)
O10.2007 (3)0.6647 (3)−0.0860 (2)0.0345 (8)
O20.4094 (3)0.6988 (2)−0.0053 (2)0.0305 (7)
O30.4328 (3)0.8431 (2)0.0767 (2)0.0275 (7)
O40.2582 (3)0.9074 (2)0.1417 (2)0.0337 (8)
C10.0855 (5)0.6569 (5)−0.1376 (5)0.0605 (18)
H1A0.08500.6743−0.20050.091*
H1B0.03450.6967−0.11160.091*
H1C0.05930.5947−0.13560.091*
C20.2860 (4)0.6140 (3)−0.1153 (3)0.0294 (10)
C30.2659 (5)0.5475 (3)−0.1817 (3)0.0345 (11)
H3A0.19040.5355−0.21240.041*
C40.3593 (5)0.4980 (4)−0.2032 (4)0.0406 (13)
H4A0.34630.4524−0.24820.049*
C50.4697 (5)0.5162 (4)−0.1584 (4)0.0386 (12)
H5A0.53160.4820−0.17210.046*
C60.4913 (4)0.5862 (3)−0.0915 (3)0.0306 (10)
C70.3977 (4)0.6343 (3)−0.0690 (3)0.0277 (10)
C80.6085 (4)0.5997 (3)−0.0437 (3)0.0326 (11)
H8A0.66250.5556−0.05360.039*
C90.7715 (4)0.6524 (4)0.0540 (4)0.0402 (14)
H9A0.82030.66740.00950.048*
H9B0.78500.58860.07130.048*
C100.8059 (5)0.7113 (5)0.1378 (4)0.0426 (13)
H10A0.86400.67920.18200.051*
H10B0.73830.72150.16620.051*
C110.8552 (4)0.8039 (4)0.1151 (4)0.0433 (14)
H11A0.86230.84340.16880.052*
H11B0.93270.79480.10160.052*
C120.7812 (5)0.8503 (4)0.0350 (4)0.0338 (12)
H12A0.81640.90830.02300.041*
H12B0.77600.8123−0.01960.041*
C130.6435 (4)0.9476 (3)0.0807 (3)0.0263 (10)
H13A0.70290.99010.08060.032*
C140.5420 (4)0.9812 (3)0.1102 (3)0.0238 (9)
C150.5441 (4)1.0721 (3)0.1420 (3)0.0286 (10)
H15A0.60971.10820.14170.034*
C160.4500 (4)1.1079 (4)0.1733 (3)0.0349 (11)
H16A0.45121.16840.19370.042*
C170.3544 (4)1.0541 (3)0.1745 (3)0.0307 (10)
H17A0.29131.07790.19720.037*
C180.3500 (4)0.9666 (3)0.1433 (3)0.0261 (9)
C190.4434 (4)0.9281 (3)0.1088 (3)0.0219 (9)
C200.1675 (5)0.9375 (5)0.1878 (5)0.0593 (18)
H20A0.20080.95740.24910.089*
H20B0.11460.88770.19120.089*
H20C0.12620.98750.15420.089*
N30.3210 (8)0.7319 (5)0.2617 (4)0.085 (3)
O50.3967 (6)0.7260 (5)0.2116 (4)0.0811 (19)
O60.2209 (7)0.7391 (3)0.2219 (4)0.0643 (17)
O70.3486 (8)0.7274 (6)0.3444 (5)0.135 (3)
N40.1158 (4)0.8781 (3)−0.0484 (3)0.0408 (11)
O80.2183 (3)0.8626 (3)−0.0595 (2)0.0370 (9)
O90.0797 (3)0.8273 (3)0.0094 (3)0.0380 (8)
O100.0586 (5)0.9393 (4)−0.0899 (4)0.0827 (17)
N50.1497 (4)0.5795 (3)0.0913 (3)0.0397 (10)
O110.2586 (3)0.5895 (3)0.0994 (3)0.0396 (9)
O120.0899 (3)0.6504 (3)0.0719 (3)0.0421 (9)
O130.1069 (5)0.5050 (3)0.1020 (3)0.0727 (15)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Gd10.0171 (2)0.0226 (2)0.0268 (2)−0.00134 (7)0.00685 (14)−0.00039 (7)
Cu10.0182 (3)0.0237 (3)0.0291 (3)−0.0009 (2)0.0074 (2)−0.0030 (2)
N10.0213 (19)0.023 (2)0.042 (2)0.0040 (16)0.0126 (17)0.0029 (18)
N20.0184 (18)0.028 (2)0.031 (2)−0.0008 (16)0.0101 (15)−0.0004 (17)
O10.0271 (18)0.037 (2)0.0385 (18)−0.0008 (16)0.0028 (15)−0.0079 (17)
O20.0229 (16)0.0314 (18)0.0381 (18)−0.0031 (14)0.0085 (14)−0.0118 (15)
O30.0225 (16)0.0221 (16)0.0408 (18)−0.0048 (13)0.0132 (14)−0.0067 (14)
O40.0230 (16)0.0337 (19)0.049 (2)−0.0025 (15)0.0196 (15)−0.0092 (16)
C10.029 (3)0.078 (5)0.067 (4)−0.001 (3)−0.010 (3)−0.026 (4)
C20.027 (2)0.030 (3)0.031 (2)0.000 (2)0.0073 (19)0.001 (2)
C30.040 (3)0.033 (3)0.028 (2)−0.008 (2)0.002 (2)−0.005 (2)
C40.053 (3)0.037 (3)0.035 (3)−0.001 (3)0.016 (2)−0.009 (2)
C50.049 (3)0.029 (3)0.043 (3)−0.002 (2)0.022 (2)−0.005 (2)
C60.035 (3)0.024 (2)0.035 (3)−0.003 (2)0.014 (2)−0.002 (2)
C70.035 (3)0.022 (2)0.028 (2)−0.0046 (19)0.0119 (19)−0.0014 (19)
C80.031 (2)0.025 (2)0.046 (3)0.004 (2)0.017 (2)−0.003 (2)
C90.022 (3)0.033 (3)0.066 (4)0.006 (2)0.007 (3)0.007 (3)
C100.026 (3)0.058 (4)0.043 (3)0.004 (3)0.004 (2)0.010 (3)
C110.019 (2)0.057 (4)0.054 (3)0.000 (2)0.007 (2)−0.013 (3)
C120.028 (3)0.030 (3)0.050 (3)−0.005 (2)0.024 (2)−0.002 (2)
C130.026 (2)0.027 (2)0.027 (2)−0.0076 (19)0.0066 (18)0.0012 (19)
C140.025 (2)0.024 (2)0.023 (2)0.0006 (18)0.0039 (17)−0.0005 (18)
C150.031 (2)0.025 (2)0.030 (2)−0.002 (2)0.0064 (19)−0.005 (2)
C160.034 (3)0.029 (3)0.041 (3)0.002 (2)0.004 (2)−0.008 (2)
C170.026 (2)0.031 (2)0.038 (2)0.004 (2)0.0113 (19)−0.006 (2)
C180.026 (2)0.026 (2)0.028 (2)−0.0019 (18)0.0096 (18)−0.0008 (19)
C190.021 (2)0.022 (2)0.023 (2)0.0007 (18)0.0052 (16)−0.0005 (18)
C200.041 (3)0.065 (4)0.083 (5)−0.008 (3)0.041 (3)−0.030 (4)
N30.108 (7)0.111 (5)0.032 (3)−0.088 (5)−0.002 (4)0.011 (3)
O50.068 (4)0.113 (4)0.052 (3)−0.045 (4)−0.015 (3)0.027 (3)
O60.099 (5)0.056 (3)0.047 (3)−0.031 (3)0.037 (3)−0.004 (2)
O70.149 (6)0.203 (7)0.047 (3)−0.114 (5)0.000 (4)0.020 (4)
N40.038 (2)0.036 (3)0.048 (3)0.001 (2)0.008 (2)0.006 (2)
O80.0287 (18)0.035 (2)0.049 (2)−0.0025 (16)0.0136 (16)0.0100 (17)
O90.0300 (18)0.041 (2)0.044 (2)−0.0057 (16)0.0112 (16)0.0052 (17)
O100.081 (4)0.066 (3)0.102 (4)0.030 (3)0.019 (3)0.048 (3)
N50.044 (3)0.034 (2)0.040 (2)−0.016 (2)0.006 (2)−0.001 (2)
O110.037 (2)0.0297 (19)0.053 (2)0.0049 (16)0.0118 (17)0.0050 (18)
O120.0273 (19)0.042 (2)0.057 (2)−0.0071 (17)0.0080 (17)0.0070 (19)
O130.099 (4)0.041 (3)0.078 (3)−0.028 (3)0.014 (3)0.007 (2)

Geometric parameters (Å, °)

Gd1—O12.581 (4)C6—C81.447 (7)
Gd1—O22.336 (3)C8—H8A0.9400
Gd1—O32.418 (3)C9—C101.512 (9)
Gd1—O42.568 (3)C9—H9A0.9800
Gd1—O52.472 (5)C9—H9B0.9800
Gd1—O62.458 (5)C10—C111.544 (9)
Gd1—O82.472 (4)C10—H10A0.9800
Gd1—O92.428 (4)C10—H10B0.9800
Gd1—O112.431 (4)C11—C121.507 (8)
Gd1—O122.520 (3)C11—H11A0.9800
Cu1—O21.941 (3)C11—H11B0.9800
Cu1—O31.940 (3)C12—H12A0.9800
Cu1—N12.004 (4)C12—H12B0.9800
Cu1—N21.960 (4)C13—C141.436 (6)
N1—C81.276 (6)C13—H13A0.9400
N1—C91.502 (6)C14—C191.398 (6)
N2—C131.292 (6)C14—C151.419 (6)
N2—C121.486 (6)C15—C161.385 (7)
O1—C21.386 (6)C15—H15A0.9400
O1—C11.437 (6)C16—C171.382 (7)
O2—C71.332 (6)C16—H16A0.9400
O3—C191.338 (5)C17—C181.367 (7)
O4—C181.387 (6)C17—H17A0.9400
O4—C201.443 (6)C18—C191.417 (6)
C1—H1A0.9700C20—H20A0.9700
C1—H1B0.9700C20—H20B0.9700
C1—H1C0.9700C20—H20C0.9700
C2—C31.381 (7)N3—O71.218 (9)
C2—C71.403 (7)N3—O61.224 (11)
C3—C41.406 (7)N3—O51.266 (11)
C3—H3A0.9400N4—O101.224 (6)
C4—C51.377 (8)N4—O81.270 (6)
C4—H4A0.9400N4—O91.272 (5)
C5—C61.424 (7)N5—O131.230 (6)
C5—H5A0.9400N5—O121.264 (6)
C6—C71.404 (7)N5—O111.277 (6)
O2—Gd1—O361.77 (11)C2—C3—H3A120.2
O2—Gd1—O9132.81 (12)C4—C3—H3A120.2
O3—Gd1—O9115.90 (12)C5—C4—C3119.9 (5)
O2—Gd1—O1179.02 (12)C5—C4—H4A120.0
O3—Gd1—O11125.29 (12)C3—C4—H4A120.0
O9—Gd1—O11118.72 (12)C4—C5—C6120.8 (5)
O2—Gd1—O6134.1 (2)C4—C5—H5A119.6
O3—Gd1—O6106.44 (17)C6—C5—H5A119.6
O9—Gd1—O692.9 (2)C7—C6—C5119.0 (5)
O11—Gd1—O674.10 (14)C7—C6—C8122.4 (4)
O2—Gd1—O886.60 (12)C5—C6—C8118.4 (5)
O3—Gd1—O874.26 (12)O2—C7—C2117.9 (4)
O9—Gd1—O851.97 (12)O2—C7—C6123.2 (4)
O11—Gd1—O8142.79 (13)C2—C7—C6119.0 (4)
O6—Gd1—O8135.51 (17)N1—C8—C6127.7 (4)
O2—Gd1—O586.1 (2)N1—C8—H8A116.2
O3—Gd1—O568.18 (15)C6—C8—H8A116.2
O9—Gd1—O5139.5 (2)N1—C9—C10112.6 (5)
O11—Gd1—O572.88 (18)N1—C9—H9A109.1
O6—Gd1—O550.8 (2)C10—C9—H9A109.1
O8—Gd1—O5140.55 (16)N1—C9—H9B109.1
O2—Gd1—O12119.60 (12)C10—C9—H9B109.1
O3—Gd1—O12174.12 (12)H9A—C9—H9B107.8
O9—Gd1—O1267.83 (12)C9—C10—C11112.4 (5)
O11—Gd1—O1251.51 (13)C9—C10—H10A109.1
O6—Gd1—O1268.33 (17)C11—C10—H10A109.1
O8—Gd1—O12111.26 (12)C9—C10—H10B109.1
O5—Gd1—O12105.99 (16)C11—C10—H10B109.1
O2—Gd1—O4124.51 (11)H10A—C10—H10B107.9
O3—Gd1—O463.05 (10)C12—C11—C10112.8 (4)
O9—Gd1—O469.79 (12)C12—C11—H11A109.0
O11—Gd1—O4141.89 (12)C10—C11—H11A109.0
O6—Gd1—O468.24 (13)C12—C11—H11B109.0
O8—Gd1—O473.61 (12)C10—C11—H11B109.0
O5—Gd1—O478.95 (19)H11A—C11—H11B107.8
O12—Gd1—O4115.88 (12)N2—C12—C11110.1 (4)
O2—Gd1—O163.16 (11)N2—C12—H12A109.6
O3—Gd1—O1115.29 (11)C11—C12—H12A109.6
O9—Gd1—O180.71 (12)N2—C12—H12B109.6
O11—Gd1—O171.65 (13)C11—C12—H12B109.6
O6—Gd1—O1136.28 (15)H12A—C12—H12B108.2
O8—Gd1—O171.23 (12)N2—C13—C14128.4 (4)
O5—Gd1—O1136.5 (2)N2—C13—H13A115.8
O12—Gd1—O169.26 (13)C14—C13—H13A115.8
O4—Gd1—O1143.41 (12)C19—C14—C15119.7 (4)
O3—Cu1—O277.94 (13)C19—C14—C13122.7 (4)
O3—Cu1—N292.82 (14)C15—C14—C13117.6 (4)
O2—Cu1—N2164.02 (16)C16—C15—C14120.5 (5)
O3—Cu1—N1163.09 (15)C16—C15—H15A119.8
O2—Cu1—N191.16 (15)C14—C15—H15A119.8
N2—Cu1—N1100.54 (16)C17—C16—C15119.4 (5)
O3—Cu1—Gd141.03 (9)C17—C16—H16A120.3
O2—Cu1—Gd138.50 (9)C15—C16—H16A120.3
N2—Cu1—Gd1133.86 (11)C18—C17—C16121.1 (4)
N1—Cu1—Gd1124.78 (11)C18—C17—H17A119.4
C8—N1—C9113.1 (4)C16—C17—H17A119.4
C8—N1—Cu1122.5 (3)C17—C18—O4125.4 (4)
C9—N1—Cu1124.4 (3)C17—C18—C19121.2 (4)
C13—N2—C12116.1 (4)O4—C18—C19113.5 (4)
C13—N2—Cu1124.1 (3)O3—C19—C14123.5 (4)
C12—N2—Cu1119.7 (3)O3—C19—C18118.5 (4)
C2—O1—C1117.3 (4)C14—C19—C18118.1 (4)
C2—O1—Gd1116.2 (3)O4—C20—H20A109.5
C1—O1—Gd1126.2 (3)O4—C20—H20B109.5
C7—O2—Cu1124.7 (3)H20A—C20—H20B109.5
C7—O2—Gd1124.8 (3)O4—C20—H20C109.5
Cu1—O2—Gd1110.36 (14)H20A—C20—H20C109.5
C19—O3—Cu1128.0 (3)H20B—C20—H20C109.5
C19—O3—Gd1124.8 (3)O7—N3—O6123.3 (10)
Cu1—O3—Gd1107.17 (14)O7—N3—O5120.4 (10)
C18—O4—C20116.3 (4)O6—N3—O5116.2 (6)
C18—O4—Gd1119.9 (3)N3—O5—Gd195.4 (5)
C20—O4—Gd1123.7 (3)N3—O6—Gd197.3 (5)
O1—C1—H1A109.5O10—N4—O8121.1 (5)
O1—C1—H1B109.5O10—N4—O9123.6 (5)
H1A—C1—H1B109.5O8—N4—O9115.3 (4)
O1—C1—H1C109.5N4—O8—Gd195.1 (3)
H1A—C1—H1C109.5N4—O9—Gd197.2 (3)
H1B—C1—H1C109.5O13—N5—O12122.9 (5)
C3—C2—O1124.7 (4)O13—N5—O11121.3 (5)
C3—C2—C7121.7 (4)O12—N5—O11115.8 (4)
O1—C2—C7113.6 (4)N5—O11—Gd198.3 (3)
C2—C3—C4119.5 (5)N5—O12—Gd194.4 (3)
O2—Gd1—Cu1—O3159.0 (2)O12—Gd1—O4—C18178.8 (3)
O9—Gd1—Cu1—O359.78 (19)O1—Gd1—O4—C18−91.6 (4)
O11—Gd1—Cu1—O3−149.68 (18)N4—Gd1—O4—C18−102.1 (3)
O6—Gd1—Cu1—O3−73.1 (2)N3—Gd1—O4—C18101.7 (4)
O8—Gd1—Cu1—O367.60 (18)O2—Gd1—O4—C20−178.1 (4)
O5—Gd1—Cu1—O3−81.8 (2)O3—Gd1—O4—C20−171.7 (5)
O12—Gd1—Cu1—O3−168.9 (2)O9—Gd1—O4—C2053.2 (5)
O4—Gd1—Cu1—O3−5.48 (18)O11—Gd1—O4—C20−58.0 (5)
O1—Gd1—Cu1—O3138.55 (18)O6—Gd1—O4—C20−48.6 (5)
N4—Gd1—Cu1—O362.47 (19)O8—Gd1—O4—C20108.0 (5)
N3—Gd1—Cu1—O3−76.2 (2)O5—Gd1—O4—C20−100.7 (5)
O3—Gd1—Cu1—O2−159.0 (2)O12—Gd1—O4—C201.9 (5)
O9—Gd1—Cu1—O2−99.2 (2)O1—Gd1—O4—C2091.5 (5)
O11—Gd1—Cu1—O251.3 (2)N4—Gd1—O4—C2081.0 (5)
O6—Gd1—Cu1—O2127.9 (2)N3—Gd1—O4—C20−75.2 (5)
O8—Gd1—Cu1—O2−91.38 (19)C1—O1—C2—C3−9.8 (8)
O5—Gd1—Cu1—O2119.2 (2)Gd1—O1—C2—C3164.2 (4)
O12—Gd1—Cu1—O232.1 (2)C1—O1—C2—C7172.0 (5)
O4—Gd1—Cu1—O2−164.46 (19)Gd1—O1—C2—C7−14.0 (5)
O1—Gd1—Cu1—O2−20.43 (19)O1—C2—C3—C4−177.4 (5)
N4—Gd1—Cu1—O2−96.5 (2)C7—C2—C3—C40.7 (8)
N3—Gd1—Cu1—O2124.9 (2)C2—C3—C4—C5−0.3 (8)
O2—Gd1—Cu1—N2159.0 (2)C3—C4—C5—C6−1.3 (8)
O3—Gd1—Cu1—N20.0 (2)C4—C5—C6—C72.5 (8)
O9—Gd1—Cu1—N259.8 (2)C4—C5—C6—C8177.4 (5)
O11—Gd1—Cu1—N2−149.64 (19)Cu1—O2—C7—C2−155.9 (3)
O6—Gd1—Cu1—N2−73.1 (2)Gd1—O2—C7—C219.0 (6)
O8—Gd1—Cu1—N267.64 (18)Cu1—O2—C7—C624.1 (6)
O5—Gd1—Cu1—N2−81.7 (2)Gd1—O2—C7—C6−160.9 (3)
O12—Gd1—Cu1—N2−168.8 (2)C3—C2—C7—O2−179.4 (4)
O4—Gd1—Cu1—N2−5.44 (18)O1—C2—C7—O2−1.1 (6)
O1—Gd1—Cu1—N2138.59 (18)C3—C2—C7—C60.5 (7)
N4—Gd1—Cu1—N262.51 (19)O1—C2—C7—C6178.8 (4)
N3—Gd1—Cu1—N2−76.1 (2)C5—C6—C7—O2177.8 (4)
O2—Gd1—Cu1—N1−33.5 (2)C8—C6—C7—O23.2 (7)
O3—Gd1—Cu1—N1167.5 (2)C5—C6—C7—C2−2.1 (7)
O9—Gd1—Cu1—N1−132.7 (2)C8—C6—C7—C2−176.8 (4)
O11—Gd1—Cu1—N117.83 (18)C9—N1—C8—C6174.9 (5)
O6—Gd1—Cu1—N194.39 (19)Cu1—N1—C8—C6−3.7 (7)
O8—Gd1—Cu1—N1−124.89 (17)C7—C6—C8—N1−14.0 (8)
O5—Gd1—Cu1—N185.7 (2)C5—C6—C8—N1171.3 (5)
O12—Gd1—Cu1—N1−1.4 (2)C8—N1—C9—C10−162.0 (5)
O4—Gd1—Cu1—N1162.03 (17)Cu1—N1—C9—C1016.6 (7)
O1—Gd1—Cu1—N1−53.95 (17)N1—C9—C10—C11−92.0 (6)
N4—Gd1—Cu1—N1−130.02 (18)C9—C10—C11—C1248.1 (7)
N3—Gd1—Cu1—N191.3 (2)C13—N2—C12—C1199.6 (5)
O3—Cu1—N1—C870.4 (7)Cu1—N2—C12—C11−83.1 (5)
O2—Cu1—N1—C821.1 (4)C10—C11—C12—N259.9 (6)
N2—Cu1—N1—C8−147.9 (4)C12—N2—C13—C14−175.3 (5)
Gd1—Cu1—N1—C841.2 (4)Cu1—N2—C13—C147.6 (7)
O3—Cu1—N1—C9−108.1 (6)N2—C13—C14—C19−4.1 (7)
O2—Cu1—N1—C9−157.4 (4)N2—C13—C14—C15175.6 (5)
N2—Cu1—N1—C933.6 (4)C19—C14—C15—C161.3 (7)
Gd1—Cu1—N1—C9−137.3 (4)C13—C14—C15—C16−178.5 (4)
O3—Cu1—N2—C13−4.2 (4)C14—C15—C16—C170.8 (7)
O2—Cu1—N2—C1349.9 (7)C15—C16—C17—C18−1.5 (7)
N1—Cu1—N2—C13−173.7 (4)C16—C17—C18—O4180.0 (5)
Gd1—Cu1—N2—C13−4.2 (5)C16—C17—C18—C190.2 (7)
O3—Cu1—N2—C12178.8 (4)C20—O4—C18—C17−8.6 (7)
O2—Cu1—N2—C12−127.2 (5)Gd1—O4—C18—C17174.3 (4)
N1—Cu1—N2—C129.2 (4)C20—O4—C18—C19171.2 (5)
Gd1—Cu1—N2—C12178.8 (3)Gd1—O4—C18—C19−5.9 (5)
O2—Gd1—O1—C216.4 (3)Cu1—O3—C19—C145.4 (6)
O3—Gd1—O1—C250.7 (3)Gd1—O3—C19—C14−176.9 (3)
O9—Gd1—O1—C2165.1 (3)Cu1—O3—C19—C18−174.7 (3)
O11—Gd1—O1—C2−70.4 (3)Gd1—O3—C19—C182.9 (5)
O6—Gd1—O1—C2−110.5 (4)C15—C14—C19—O3177.3 (4)
O8—Gd1—O1—C2112.2 (3)C13—C14—C19—O3−3.0 (7)
O5—Gd1—O1—C2−33.6 (4)C15—C14—C19—C18−2.5 (6)
O12—Gd1—O1—C2−125.2 (3)C13—C14—C19—C18177.2 (4)
O4—Gd1—O1—C2128.9 (3)C17—C18—C19—O3−178.0 (4)
N4—Gd1—O1—C2138.9 (3)O4—C18—C19—O32.2 (6)
N3—Gd1—O1—C2−73.1 (5)C17—C18—C19—C141.9 (7)
O2—Gd1—O1—C1−170.3 (5)O4—C18—C19—C14−178.0 (4)
O3—Gd1—O1—C1−135.9 (5)O7—N3—O5—Gd1−177.0 (8)
O9—Gd1—O1—C1−21.6 (5)O6—N3—O5—Gd15.4 (7)
O11—Gd1—O1—C1103.0 (5)O2—Gd1—O5—N3−166.0 (5)
O6—Gd1—O1—C162.8 (6)O3—Gd1—O5—N3132.9 (5)
O8—Gd1—O1—C1−74.5 (5)O9—Gd1—O5—N328.1 (6)
O5—Gd1—O1—C1139.7 (5)O11—Gd1—O5—N3−86.3 (5)
O12—Gd1—O1—C148.1 (5)O6—Gd1—O5—N3−3.1 (4)
O4—Gd1—O1—C1−57.8 (5)O8—Gd1—O5—N3114.1 (4)
N4—Gd1—O1—C1−47.8 (5)O12—Gd1—O5—N3−46.3 (5)
N3—Gd1—O1—C1100.3 (6)O4—Gd1—O5—N367.7 (5)
O3—Cu1—O2—C7161.6 (4)O1—Gd1—O5—N3−122.8 (5)
N2—Cu1—O2—C7105.9 (6)N4—Gd1—O5—N370.5 (5)
N1—Cu1—O2—C7−31.4 (4)O7—N3—O6—Gd1177.0 (8)
Gd1—Cu1—O2—C7175.6 (5)O5—N3—O6—Gd1−5.5 (8)
O3—Cu1—O2—Gd1−13.93 (15)O2—Gd1—O6—N327.4 (5)
N2—Cu1—O2—Gd1−69.7 (6)O3—Gd1—O6—N3−39.0 (5)
N1—Cu1—O2—Gd1153.03 (17)O9—Gd1—O6—N3−157.0 (4)
O3—Gd1—O2—C7−163.2 (4)O11—Gd1—O6—N383.9 (5)
O9—Gd1—O2—C7−62.9 (4)O8—Gd1—O6—N3−123.0 (5)
O11—Gd1—O2—C756.3 (4)O5—Gd1—O6—N33.2 (5)
O6—Gd1—O2—C7111.0 (4)O12—Gd1—O6—N3138.2 (5)
O8—Gd1—O2—C7−89.2 (4)O4—Gd1—O6—N3−90.2 (5)
O5—Gd1—O2—C7129.6 (4)O1—Gd1—O6—N3123.4 (4)
O12—Gd1—O2—C723.4 (4)N4—Gd1—O6—N3−141.5 (4)
O4—Gd1—O2—C7−156.6 (3)O10—N4—O8—Gd1171.6 (5)
O1—Gd1—O2—C7−18.6 (3)O9—N4—O8—Gd1−6.9 (5)
N4—Gd1—O2—C7−79.8 (4)O2—Gd1—O8—N4159.8 (3)
N3—Gd1—O2—C7123.0 (4)O3—Gd1—O8—N4−138.6 (3)
O3—Gd1—O2—Cu112.39 (14)O9—Gd1—O8—N44.2 (3)
O9—Gd1—O2—Cu1112.66 (18)O11—Gd1—O8—N492.9 (3)
O11—Gd1—O2—Cu1−128.16 (19)O6—Gd1—O8—N4−41.0 (4)
O6—Gd1—O2—Cu1−73.4 (2)O5—Gd1—O8—N4−120.5 (4)
O8—Gd1—O2—Cu186.33 (17)O12—Gd1—O8—N439.2 (3)
O5—Gd1—O2—Cu1−54.9 (2)O4—Gd1—O8—N4−72.7 (3)
O12—Gd1—O2—Cu1−161.09 (14)O1—Gd1—O8—N497.0 (3)
O4—Gd1—O2—Cu118.9 (2)N3—Gd1—O8—N4−77.8 (5)
O1—Gd1—O2—Cu1157.0 (2)O10—N4—O9—Gd1−171.4 (5)
N4—Gd1—O2—Cu195.71 (18)O8—N4—O9—Gd17.1 (5)
N3—Gd1—O2—Cu1−61.4 (2)O2—Gd1—O9—N4−38.4 (4)
O2—Cu1—O3—C19−168.8 (4)O3—Gd1—O9—N436.1 (3)
N2—Cu1—O3—C19−2.0 (4)O11—Gd1—O9—N4−140.6 (3)
N1—Cu1—O3—C19140.3 (5)O6—Gd1—O9—N4146.0 (3)
Gd1—Cu1—O3—C19178.0 (4)O8—Gd1—O9—N4−4.2 (3)
O2—Cu1—O3—Gd113.20 (14)O5—Gd1—O9—N4122.3 (3)
N2—Cu1—O3—Gd1−179.97 (16)O12—Gd1—O9—N4−148.8 (3)
N1—Cu1—O3—Gd1−37.6 (6)O4—Gd1—O9—N480.5 (3)
O2—Gd1—O3—C19169.8 (4)O1—Gd1—O9—N4−77.5 (3)
O9—Gd1—O3—C1943.1 (4)N3—Gd1—O9—N4135.5 (3)
O11—Gd1—O3—C19−140.4 (3)O13—N5—O11—Gd1179.4 (5)
O6—Gd1—O3—C19−58.5 (4)O12—N5—O11—Gd1−0.7 (5)
O8—Gd1—O3—C1975.1 (3)O2—Gd1—O11—N5−142.4 (3)
O5—Gd1—O3—C19−92.6 (4)O3—Gd1—O11—N5174.3 (3)
O4—Gd1—O3—C19−4.2 (3)O9—Gd1—O11—N5−9.3 (3)
O1—Gd1—O3—C19134.9 (3)O6—Gd1—O11—N575.1 (3)
N4—Gd1—O3—C1958.2 (3)O8—Gd1—O11—N5−73.2 (4)
N3—Gd1—O3—C19−73.9 (4)O5—Gd1—O11—N5128.2 (3)
O2—Gd1—O3—Cu1−12.16 (13)O12—Gd1—O11—N50.4 (3)
O9—Gd1—O3—Cu1−138.80 (14)O4—Gd1—O11—N584.1 (3)
O11—Gd1—O3—Cu137.7 (2)O1—Gd1—O11—N5−77.3 (3)
O6—Gd1—O3—Cu1119.6 (2)N4—Gd1—O11—N5−33.3 (4)
O8—Gd1—O3—Cu1−106.83 (17)N3—Gd1—O11—N5101.1 (4)
O5—Gd1—O3—Cu185.5 (2)O13—N5—O12—Gd1−179.4 (5)
O4—Gd1—O3—Cu1173.9 (2)O11—N5—O12—Gd10.7 (4)
O1—Gd1—O3—Cu1−47.02 (19)O2—Gd1—O12—N542.6 (3)
N4—Gd1—O3—Cu1−123.76 (16)O9—Gd1—O12—N5170.3 (3)
N3—Gd1—O3—Cu1104.2 (3)O11—Gd1—O12—N5−0.4 (3)
O2—Gd1—O4—C18−1.2 (4)O6—Gd1—O12—N5−86.9 (3)
O3—Gd1—O4—C185.2 (3)O8—Gd1—O12—N5141.1 (3)
O9—Gd1—O4—C18−130.0 (3)O5—Gd1—O12—N5−52.2 (4)
O11—Gd1—O4—C18118.9 (3)O4—Gd1—O12—N5−137.4 (3)
O6—Gd1—O4—C18128.2 (4)O1—Gd1—O12—N582.2 (3)
O8—Gd1—O4—C18−75.1 (3)N4—Gd1—O12—N5157.2 (3)
O5—Gd1—O4—C1876.2 (3)N3—Gd1—O12—N5−70.6 (4)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2285).

References

  • Fei, L. & Fang, Z. (2008). Acta Cryst. E64, m406. [PMC free article] [PubMed]
  • Rigaku/MSC (2002). CrystalClear Rigaku/MSC, The Woodlands, Texas, USA.
  • Sakamoto, M., Manseki, K. & Okawa, H. (2001). Coord. Chem. Rev.219–221, 379–414.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Winpenny, R. E. P. (1998). Chem. Soc. Rev.27, 447–452.
  • Xing, J.-C., Wang, J.-H., Yan, P.-F. & Li, G.-M. (2008). Acta Cryst. E64, m1206. [PMC free article] [PubMed]
  • Yang, X., Jones, R. A., Lynch, V., Oye, M. M. & Holmes, A. L. (2005). Dalton Trans. pp. 849–851. [PubMed]

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