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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 9| September 2011| Pages m1218-m1219
doi:10.1107/S1600536811031503

Poly[di-μ-glycinato-copper(II)]: a two-dimensional coordination polymer

Fabienne Gschwinda* and Martin Jansena

aMax Planck Institute for Solid State Research, Heisenbergstrasse 1, 70569 Stuttgart, Germany
*Correspondence e-mail: f.gschwind@fkf.mpg.de

(Received 30 May 2011; accepted 4 August 2011; online 11 August 2011)

The title coordination polymer, [Cu(C2H4NO2)2]n, is two-dimensional and consists of a distorted octa­hedral copper coordination polyhedron with two bidentate glycine ligands chelating the metal through the O and N atoms in a trans-square-planar configuration. The two axial coordination sites are occupied by carbonyl O atoms of neighbouring glycine mol­ecules. The Cu—O distances for the axial O atoms [2.648 (2) and 2.837 (2) Å] are considerably longer than both the Cu—O [1.9475 (17) and 1.9483 (18) Å] and Cu—N [1.988 (2) and 1.948 (2) Å] distances in the equatorial plane, which indicates a strong Jahn–Teller effect. In the crystal, the two-dimensional networks are arranged parallel to (001) and are linked via N—H⋯O hydrogen bonds, forming a three-dimensional arrangement.

Related literature

For the first work on cadmium glycinato complexes, see: Low et al. (1959[Low, B. W., Hirshfeld, F. L. & Richard, F. M. (1959). J. Am. Chem. Soc. 36, 4412-4416.]). For similar mixed-metal glycinato complexes with copper(II), see: Papavinasam (1991[Papavinasam, E. (1991). Z. Kristallogr. 197, 217-222.]); Davies et al. (2003[Davies, O. H., Park, J. H. & Gillard, R. D. (2003). Inorg. Chim. Acta, 356, 69-84.]); Low et al. (1959[Low, B. W., Hirshfeld, F. L. & Richard, F. M. (1959). J. Am. Chem. Soc. 36, 4412-4416.]); Bi et al. (2006[Bi, W., Mercier, N., Louvain, N. & Latroche, M. (2006). Eur. J. Inorg. Chem. 21, 4225-4228.]); Zhang et al. (2005[Zhang, J. J., Hu, S. M., Xiang, S. C., Wang, L. S. & Wu, X. T. (2005). J. Mol. Struct. 748, 129-136.]). For further studies on cadmium–glycinato complexes, see: Barrie et al. (1993[Barrie, P. J., Gyani, A., Motevalli, M. & O'Brien, P. (1993). Inorg. Chem. 32, 3862-3867.]). For the properties and structure of a three-dimensional copper–glycinate polymer, see: Chen et al. (2009[Chen, P. J., Jiang, C., Yan, W. H., Liang, F. P. & Batten, S. R. (2009). Inorg. Chem. 48, 4674-4684.]). For the synthesis of [NaCu6(gly)3(ClO4)3(H2O)]n(ClO4)2n, see: Aromi et al. (2008[Aromi, G., Novoa, J. J., Ribas-Arino, J., Igarashi, S. & Yukawa, Y. (2008). Inorg. Chim. Acta, 361, 3919-3925.]).

[Scheme 1]

Experimental

Crystal data

  • [Cu(C2H4NO2)2]

  • Mr = 211.66

  • Monoclinic, P 21 /n

  • a = 9.4265 (19) Å

  • b = 5.1159 (10) Å

  • c = 13.912 (3) Å

  • β = 107.36 (3)°

  • V = 640.4 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 3.37 mm−1

  • T = 298 K

  • 0.21 × 0.15 × 0.09 mm
Data collection

  • Stoe IPDS 2 diffractometer

  • Absorption correction: integration (X-SHAPE and X-RED; Stoe & Cie, 2009[Stoe & Cie (2009). X-AREA, X-RED and X-SHAPE. Stoe & Cie GmBh, Damstadt, Germany,]) Tmin = 0.549, Tmax = 0.692

  • 9012 measured reflections

  • 1876 independent reflections

  • 1561 reflections with I > 2σ(I)

  • Rint = 0.048
Refinement

  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 0.075

  • S = 1.03

  • 1876 reflections

  • 116 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.42 e Å−3

  • Δρmin = −0.58 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H1A⋯O3i 0.94 (5) 2.12 (5) 3.029 (3) 162 (4)
N2—H1B⋯O2ii 0.80 (4) 2.49 (4) 3.223 (3) 154 (4)
N1—H3A⋯O1iii 0.90 (4) 2.17 (4) 2.994 (3) 152 (3)
N1—H3A⋯O1iv 0.90 (4) 2.44 (4) 3.003 (3) 121 (3)
N1—H3B⋯O4v 0.86 (4) 2.41 (4) 3.152 (3) 145 (3)
Symmetry codes: (i) x, y-1, z; (ii) [x+{\script{1\over 2}}, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]; (iii) x, y+1, z; (iv) [-x-{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (v) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: X-AREA (Stoe & Cie, 2009[Stoe & Cie (2009). X-AREA, X-RED and X-SHAPE. Stoe & Cie GmBh, Damstadt, Germany,]); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2009[Stoe & Cie (2009). X-AREA, X-RED and X-SHAPE. Stoe & Cie GmBh, Damstadt, Germany,]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811031503/su2280sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811031503/su2280Isup2.hkl

checkCIF report


Comment top

Different metal glycine complexes and polymeric structures have been known since the 1960's. The first work on a cadmium glycinato complexe was done by (Low et al., 1959), and further studies were reported by (Barrie et al., 1993). Mixed metal glycinato complexes with copper(II) were investigated by (Papavinasam, 1991; Davies et al., 2003; Low et al., 1959).

The complexation of simple copper salts to amino acids is a well investigated reaction and various complexes and clusters have been reported (Low et al., 1959; Davies et al., 2003; Aromi et al., 2008; Bi et al., 2006; Zhang et al., 2005). A three-dimensional copper-glycinate coordination polymer has been reported on by (Chen et al., 2009).

While redissolving the copper cluster [NaCu6(gly)3(ClO4)3(H2O)]n (ClO4)2n (Aromi et al., 2008) in DMSO, blue crystals of the title compound were obtained and were characterized by X-ray diffraction.

The title compound is a two-dimensional coordination polymer (Fig. 1). It consists of a distorted octahedral copper coordination polyhedron with two bidentate glycine ligands chelating the metal through the oxygen and nitrogen atoms (O1, O3, N1, N2) in a trans square planar configuration. The two axial coordination sites are occupied by carbonyl oxygen atoms of the neighbouring glycine molecules (O2 and O4). The Cu—O distances are 2.648 (2) Å (Cu1—O2i) and 2.837 (2) Å (Cu1—O4ii) for the axial oxygen atoms [symmetry codes: (i) -x-1/2, y+1/2, -z+1/2; (ii) -x+1/2, y-1/2, -z+1/2]. In the equatorial plane the Cu-O distances are 1.9474 (15) and 1.9483 (16) Å for Cu1—O1 and Cu1—O3, respectively, while the Cu—N distances are 1.9883 (19) and 1.948 (2) Å for Cu1-N1 and Cu1—N2, respectively. These bond length differences indicate a strong Jahn-Teller effect.

In the crystal the two dimensional networks are linked via N-H···O hydrogen bonds to form a three-dimensional arrangement (Table 1 and Fig. 2).

Related literature top

For the first work on cadmium glycinato complexes, see: Low et al. (1959). For similar mixed-metal glycinato complexes with copper(II), see: Papavinasam (1991); Davies et al. (2003); Low et al. (1959); Bi et al. (2006); Zhang et al. (2005). For further studies on cadmium–glycinato complexes, see: Barrie et al. (1993). For the properties and structure of a three-dimensional copper–glycinate polymer, see: Chen et al. (2009). For the synthesis of [NaCu6(gly)3(ClO4)3(H2O)]n(ClO4)2n, see: Aromi et al. (2008).

Experimental top

The title compound was prepared by dissolving 20 mg of [NaCu6(gly)3(ClO4)3(H2O)]n (ClO4)2n (Aromi et al., 2008) in 5 ml DMSO. Crystals could be grown out of the blue solution by slow diffusion of THF.

Refinement top

The NH-atoms were located in difference electron-density maps and were freely refined. The C-bound H-atoms were included in calculated positions and treated as riding atoms: C-H = 0.97 Å, with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2009); cell refinement: X-AREA (Stoe & Cie, 2009); data reduction: X-RED (Stoe & Cie, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Part of the polymeric structure of the title compound, showing the numbering scheme and the displacement ellipsoids drawn at the 50% probability level [H atoms have been omitted for clarity; symmetry codes: (i) -x-1/2, y+1/2, -z+1/2; (ii) -x+1/2, y-1/2, -z+1/2].
[Figure 2] Fig. 2. A view along the x-axis of the three-dimensional hydrogen bonded network of the title compound built up from the two-dimenional nets. The N-H···O hydrogen bonds are shown as dashed lines (see Table 1 for details; H-atoms not involved in these reactions have been omitted for clarity).
Poly[di-µ-glycinato-copper(II)] top
Crystal data top
[Cu(C2H4NO2)2]F(000) = 428
Mr = 211.66Dx = 2.195 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5867 reflections
a = 9.4265 (19) Åθ = 2.3–30.5°
b = 5.1159 (10) ŵ = 3.37 mm−1
c = 13.912 (3) ÅT = 298 K
β = 107.36 (3)°Block, blue
V = 640.4 (2) Å30.21 × 0.15 × 0.09 mm
Z = 4
Data collection top
Stoe IPDS 2
diffractometer		1876 independent reflections
Radiation source: fine-focus sealed tube1561 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
Detector resolution: 6.67 pixels mm-1θmax = 30.0°, θmin = 2.3°
rotation method scansh = −13→13
Absorption correction: integration
(X-SHAPE and X-RED; Stoe & Cie, 2009)		k = −7→6
Tmin = 0.549, Tmax = 0.692l = −19→17
9012 measured reflections
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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0447P)2]
where P = (Fo2 + 2Fc2)/3
1876 reflections(Δ/σ)max = 0.001
116 parametersΔρmax = 0.42 e Å−3
0 restraintsΔρmin = −0.58 e Å−3
Crystal data top
[Cu(C2H4NO2)2]V = 640.4 (2) Å3
Mr = 211.66Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.4265 (19) ŵ = 3.37 mm−1
b = 5.1159 (10) ÅT = 298 K
c = 13.912 (3) Å0.21 × 0.15 × 0.09 mm
β = 107.36 (3)°
Data collection top
Stoe IPDS 2
diffractometer		1876 independent reflections
Absorption correction: integration
(X-SHAPE and X-RED; Stoe & Cie, 2009)		1561 reflections with I > 2σ(I)
Tmin = 0.549, Tmax = 0.692Rint = 0.048
9012 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.075H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.42 e Å−3
1876 reflectionsΔρmin = −0.58 e Å−3
116 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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
Cu1−0.00228 (3)0.02678 (5)0.26465 (2)0.0301 (1)
O1−0.17587 (17)−0.1989 (3)0.21922 (12)0.0270 (4)
O2−0.3924 (2)−0.2410 (4)0.10081 (14)0.0408 (6)
O30.17471 (18)0.2461 (3)0.30307 (13)0.0317 (4)
O40.41730 (18)0.2283 (4)0.38098 (15)0.0392 (5)
N1−0.1151 (2)0.2642 (4)0.15535 (16)0.0283 (5)
N20.1137 (2)−0.2140 (4)0.37098 (17)0.0302 (6)
C1−0.2742 (2)−0.1247 (4)0.13882 (17)0.0260 (6)
C2−0.2384 (3)0.1181 (4)0.08778 (17)0.0304 (6)
C30.2916 (2)0.1351 (4)0.36051 (16)0.0253 (5)
C40.2694 (2)−0.1268 (4)0.40529 (17)0.0282 (6)
H1A0.112 (5)−0.378 (10)0.340 (3)0.076 (13)*
H1B0.082 (4)−0.233 (7)0.418 (3)0.045 (9)*
H2A−0.212400.067700.027900.0360*
H2B−0.325600.229300.067000.0360*
H3A−0.153 (4)0.393 (7)0.184 (2)0.045 (9)*
H3B−0.061 (4)0.342 (8)0.124 (3)0.061 (11)*
H4A0.33140−0.256700.386700.0340*
H4B0.30110−0.113000.478100.0340*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0249 (1)0.0214 (1)0.0380 (2)−0.0026 (1)−0.0001 (1)0.0078 (1)
O10.0262 (7)0.0191 (7)0.0334 (8)−0.0016 (5)0.0052 (6)0.0030 (6)
O20.0375 (9)0.0391 (10)0.0389 (10)−0.0142 (7)0.0010 (7)0.0043 (7)
O30.0277 (7)0.0216 (7)0.0408 (9)−0.0028 (6)0.0028 (6)0.0046 (6)
O40.0275 (8)0.0350 (9)0.0510 (11)−0.0060 (7)0.0057 (7)0.0016 (8)
N10.0274 (9)0.0214 (8)0.0340 (10)−0.0019 (7)0.0062 (7)0.0055 (7)
N20.0291 (9)0.0253 (9)0.0331 (11)−0.0023 (7)0.0046 (8)0.0068 (8)
C10.0282 (10)0.0234 (9)0.0262 (10)−0.0011 (7)0.0080 (8)−0.0020 (8)
C20.0351 (11)0.0263 (10)0.0264 (11)−0.0053 (8)0.0041 (8)0.0017 (8)
C30.0267 (9)0.0238 (9)0.0246 (10)−0.0018 (7)0.0066 (8)−0.0025 (7)
C40.0279 (10)0.0272 (10)0.0272 (11)0.0017 (8)0.0049 (8)0.0043 (8)
Geometric parameters (Å, º) top
Cu1—O11.9475 (17)N2—C41.471 (3)
Cu1—O31.9483 (18)N1—H3B0.86 (4)
Cu1—N11.988 (2)N1—H3A0.90 (4)
Cu1—N21.984 (2)N2—H1A0.94 (5)
Cu1—O2i2.648 (2)N2—H1B0.80 (4)
Cu1—O4ii2.837 (2)C1—C21.518 (3)
O1—C11.279 (3)C3—C41.518 (3)
O2—C11.234 (3)C2—H2A0.9700
O3—C31.284 (3)C2—H2B0.9700
O4—C31.229 (3)C4—H4A0.9700
N1—C21.463 (3)C4—H4B0.9700
O1—Cu1—O3176.59 (8)H3A—N1—H3B105 (4)
O1—Cu1—N184.73 (8)C4—N2—H1A107 (3)
O1—Cu1—N295.55 (8)Cu1—N2—H1A106 (3)
O1—Cu1—O2i92.26 (7)Cu1—N2—H1B115 (3)
O1—Cu1—O4ii80.68 (7)C4—N2—H1B111 (3)
O3—Cu1—N194.41 (8)H1A—N2—H1B108 (4)
O3—Cu1—N285.22 (8)O2—C1—C2119.5 (2)
O2i—Cu1—O391.07 (7)O1—C1—O2123.9 (2)
O3—Cu1—O4ii96.01 (7)O1—C1—C2116.60 (19)
N1—Cu1—N2178.27 (9)N1—C2—C1111.24 (19)
O2i—Cu1—N192.22 (8)O3—C3—O4124.2 (2)
O4ii—Cu1—N189.04 (8)O3—C3—C4116.60 (18)
O2i—Cu1—N289.48 (8)O4—C3—C4119.3 (2)
O4ii—Cu1—N289.32 (8)N2—C4—C3112.39 (18)
O2i—Cu1—O4ii172.69 (7)N1—C2—H2A109.00
Cu1—O1—C1115.30 (14)N1—C2—H2B109.00
Cu1iii—O2—C1113.23 (15)C1—C2—H2A109.00
Cu1—O3—C3114.93 (14)C1—C2—H2B109.00
Cu1iv—O4—C3120.10 (16)H2A—C2—H2B108.00
Cu1—N1—C2108.68 (14)N2—C4—H4A109.00
Cu1—N2—C4109.16 (15)N2—C4—H4B109.00
C2—N1—H3A108 (2)C3—C4—H4A109.00
Cu1—N1—H3A107.6 (18)C3—C4—H4B109.00
Cu1—N1—H3B114 (3)H4A—C4—H4B108.00
C2—N1—H3B113 (3)
N1—Cu1—O1—C16.99 (16)N2—Cu1—O2i—C1i−157.43 (17)
N2—Cu1—O1—C1−171.29 (16)O1—Cu1—O4ii—C3ii−133.24 (18)
O2i—Cu1—O1—C199.01 (15)O3—Cu1—O4ii—C3ii47.61 (18)
O4ii—Cu1—O1—C1−82.90 (15)N1—Cu1—O4ii—C3ii141.95 (18)
N1—Cu1—O3—C3−166.00 (16)N2—Cu1—O4ii—C3ii−37.51 (18)
N2—Cu1—O3—C312.30 (16)Cu1—O1—C1—O2−178.31 (18)
O2i—Cu1—O3—C3101.69 (16)Cu1—O1—C1—C23.1 (2)
O4ii—Cu1—O3—C3−76.51 (16)Cu1iii—O2—C1—O132.3 (3)
O1—Cu1—N1—C2−14.98 (16)Cu1iii—O2—C1—C2−149.11 (17)
O3—Cu1—N1—C2161.71 (16)Cu1—O3—C3—O4169.39 (19)
O2i—Cu1—N1—C2−107.04 (16)Cu1—O3—C3—C4−11.0 (2)
O4ii—Cu1—N1—C265.75 (16)Cu1iv—O4—C3—O3−34.4 (3)
O1—Cu1—N2—C4166.43 (15)Cu1iv—O4—C3—C4146.03 (16)
O3—Cu1—N2—C4−10.23 (15)Cu1—N1—C2—C119.8 (2)
O2i—Cu1—N2—C4−101.35 (15)Cu1—N2—C4—C37.4 (2)
O4ii—Cu1—N2—C485.86 (15)O1—C1—C2—N1−15.8 (3)
O1—Cu1—O2i—C1i−61.90 (17)O2—C1—C2—N1165.5 (2)
O3—Cu1—O2i—C1i117.36 (17)O3—C3—C4—N22.1 (3)
N1—Cu1—O2i—C1i22.91 (17)O4—C3—C4—N2−178.3 (2)
Symmetry codes: (i) −x−1/2, y+1/2, −z+1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x−1/2, y−1/2, −z+1/2; (iv) −x+1/2, y+1/2, −z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H1A···O3v0.94 (5)2.12 (5)3.029 (3)162 (4)
N2—H1B···O2vi0.80 (4)2.49 (4)3.223 (3)154 (4)
N1—H3A···O1vii0.90 (4)2.17 (4)2.994 (3)152 (3)
N1—H3A···O1i0.90 (4)2.44 (4)3.003 (3)121 (3)
N1—H3B···O4iv0.86 (4)2.41 (4)3.152 (3)145 (3)
Symmetry codes: (i) −x−1/2, y+1/2, −z+1/2; (iv) −x+1/2, y+1/2, −z+1/2; (v) x, y−1, z; (vi) x+1/2, −y−1/2, z+1/2; (vii) x, y+1, z.

Experimental details

Crystal data
Chemical formula[Cu(C2H4NO2)2]
Mr211.66
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)9.4265 (19), 5.1159 (10), 13.912 (3)
β (°) 107.36 (3)
V (Å3)640.4 (2)
Z4
Radiation typeMo Kα
µ (mm−1)3.37
Crystal size (mm)0.21 × 0.15 × 0.09
Data collection
DiffractometerStoe IPDS 2
diffractometer
Absorption correctionIntegration
(X-SHAPE and X-RED; Stoe & Cie, 2009)
Tmin, Tmax0.549, 0.692
No. of measured, independent and
observed [I > 2σ(I)] reflections		9012, 1876, 1561
Rint0.048
(sin θ/λ)max (Å−1)0.704
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.075, 1.03
No. of reflections1876
No. of parameters116
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.42, −0.58

Computer programs: X-AREA (Stoe & Cie, 2009), X-RED (Stoe & Cie, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H1A···O3i0.94 (5)2.12 (5)3.029 (3)162 (4)
N2—H1B···O2ii0.80 (4)2.49 (4)3.223 (3)154 (4)
N1—H3A···O1iii0.90 (4)2.17 (4)2.994 (3)152 (3)
N1—H3A···O1iv0.90 (4)2.44 (4)3.003 (3)121 (3)
N1—H3B···O4v0.86 (4)2.41 (4)3.152 (3)145 (3)
Symmetry codes: (i) x, y−1, z; (ii) x+1/2, −y−1/2, z+1/2; (iii) x, y+1, z; (iv) −x−1/2, y+1/2, −z+1/2; (v) −x+1/2, y+1/2, −z+1/2.
 

Acknowledgements

FG thanks the Swiss National Science Foundation for financial support.

References

First citationAromi, G., Novoa, J. J., Ribas-Arino, J., Igarashi, S. & Yukawa, Y. (2008). Inorg. Chim. Acta, 361, 3919–3925.  CAS Google Scholar
 First citationBarrie, P. J., Gyani, A., Motevalli, M. & O'Brien, P. (1993). Inorg. Chem. 32, 3862–3867.  CrossRef CAS Google Scholar
 First citationBi, W., Mercier, N., Louvain, N. & Latroche, M. (2006). Eur. J. Inorg. Chem. 21, 4225–4228.  CrossRef Google Scholar
 First citationBrandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationChen, P. J., Jiang, C., Yan, W. H., Liang, F. P. & Batten, S. R. (2009). Inorg. Chem. 48, 4674–4684.  CrossRef CAS Google Scholar
 First citationDavies, O. H., Park, J. H. & Gillard, R. D. (2003). Inorg. Chim. Acta, 356, 69–84.  CrossRef CAS Google Scholar
 First citationLow, B. W., Hirshfeld, F. L. & Richard, F. M. (1959). J. Am. Chem. Soc. 36, 4412-4416.  CrossRef Google Scholar
 First citationPapavinasam, E. (1991). Z. Kristallogr. 197, 217–222.  CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationStoe & Cie (2009). X-AREA, X-RED and X-SHAPE. Stoe & Cie GmBh, Damstadt, Germany,  Google Scholar
 First citationZhang, J. J., Hu, S. M., Xiang, S. C., Wang, L. S. & Wu, X. T. (2005). J. Mol. Struct. 748, 129–136.  CrossRef CAS Google Scholar

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ISSN: 2056-9890
Volume 67| Part 9| September 2011| Pages m1218-m1219
doi:10.1107/S1600536811031503
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