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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): m1044–m1045.
Published online 2010 July 31. doi:  10.1107/S1600536810029752
PMCID: PMC3007362

Bis(2,2′-bi-1H-imidazole)­copper(II) bis­(1,1,3,3-tetra­cyano-2-eth­oxy­propenide)

Abstract

In the title compound, [Cu(C6H6N4)2](C9H5N4O)2, the Cu2+ ion (site symmetry An external file that holds a picture, illustration, etc.
Object name is e-66-m1044-efi1.jpg) is coordinated by two N,N′-bidentate 2,2′-biimidazole (H2biim) ligands, generating a square-planar CuN4 geometry. The dihedral angle between the aromatic rings in the ligand is 0.70 (9)°. In the polynitrile 1,1,3,3-tetra­cyano-2-eth­oxy­propenide (tcnoet) anion, the C—N, C—C and C—O bond lengths indicate extensive electronic delocalization. An alternative description for the metal-ion geometry is an extremely distorted CuN6 octa­hedron, with two N-bonded tcnoet anions completing the coordination. In the crystal, the components are linked by N—H(...)N and C—H(...)N inter­actions.

Related literature

For the structures and properties of related compounds containing polynitrile anions, see: Atmani et al. (2008 [triangle]); Batten & Murray (2003 [triangle]); Bencini & Mani (1988 [triangle]); Benmansour et al. (2007 [triangle]); Cancela et al. (2001 [triangle]); Cromer et al. (1987 [triangle]); Jones et al. (2006 [triangle]); Setifi et al. (2006 [triangle], 2007 [triangle]); Thétiot et al. (2003 [triangle]); Triki et al. (2005 [triangle]); Yuste et al. (2007 [triangle]). For the synthesis of the H2biim and Ktcnoet ligands, see: Bernarducci et al. (1983 [triangle]) and Middleton & Engelhardt (1958 [triangle]), respecively.

An external file that holds a picture, illustration, etc.
Object name is e-66-m1044-scheme1.jpg

Experimental

Crystal data

  • [Cu(C6H6N4)2](C9H5N4O)2
  • M r = 702.18
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1044-efi2.jpg
  • a = 8.1001 (8) Å
  • b = 26.1834 (11) Å
  • c = 8.2185 (7) Å
  • β = 117.086 (11)°
  • V = 1551.9 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.76 mm−1
  • T = 170 K
  • 0.40 × 0.30 × 0.20 mm

Data collection

  • Oxford Diffraction Xcalibur CCD diffractometer
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 [triangle]) T min = 0.750, T max = 0.862
  • 8646 measured reflections
  • 3002 independent reflections
  • 1854 reflections with I > 2σ(I)
  • R int = 0.037

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.077
  • S = 0.93
  • 3002 reflections
  • 223 parameters
  • H-atom parameters constrained
  • Δρmax = 0.38 e Å−3
  • Δρmin = −0.28 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SIR97 (Altomare et al., 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]) and CAMERON (Watkin et al., 1993 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON (Spek, 2009 [triangle]).

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810029752/hb5555sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029752/hb5555Isup2.hkl

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

Acknowledgments

The X-ray data were collected at the University of Bretagne Occidentale (UBO; UMR CNRS 6521). FS thanks Professor S. Triki for providing diffraction facilities and the Université Ferhat Abbas de Sétif, Algérie, for financial support.

supplementary crystallographic information

Comment

Polynitrile anions are known to be interesting ligands in coordination chemistry because of their high electronic delocalization and their cyano groups juxtaposed in such a way that they cannot all coordinate to the same metal ion. They adopt different bridging or nonbridging coordination modes wich afford discrete or extended molecular architectures (Atmani et al., 2008; Benmansour et al., 2007; Triki et al., 2005; Thétiot et al., 2003). Following these structural and electronic characteristics, several series of binary systems "polynitrile/M(II)" with only polynitrile bridges or ternary systems "polynitrile/co-ligand/M(II)" (M(II), transition metal ion) involving an additional bridging or chelate co-ligand have been reported. Most of them display one-dimensional, two-dimensional and three-dimensional polymeric assemblies, in which the polynitrile anions act as µ2-, µ3- and/or µ4- bridging ligands and exhibit unusual magnetic properties (Batten & Murray, 2003; Jones et al., 2006; Yuste et al., 2007; Setifi et al., 2006; Setifi et al., 2007).

In our case we have chosen to investigate the ternary system including 2,2'-biimidazole (H2bim) selected as co-ligand because it is bifunctional: the imino moieties can be coordinated to a metal ion acting as the first coordination sphere and the amino N—H and C—H groups, as the second coordination sphere, may donate multifold hydrogen bonds to tcnoet anions, extending the structure into a high-dimensional network. In this contribution we report the synthesis and the crystal structure of a new copper(II) compound with neutral 2,2'-biimidazole, Cu(H2biim)2] (tcnoet)2, (I).

The crystal of (I) is built of [Cu(H2biim)2]2+ cations and (tcnoet)- anions interconnected by hydrogen bonds. As shown in Fig. 1, the Cu(II) ion has a square coordination geometry, it locates on a symmetry inversion center and relates four nitrogen atoms of two symmetry-related 2,2'-biimidazole molecules which bind bidentately arranged trans to each other in the square plane [Cu1—N1 = 1.973 (2) Å and Cu1—N2 = 2.040 (2) Å] and interacts with two nitrogen atoms belonging to tcnoet ligands occupying the apical coordination sites [Cu1—N7 = 2.821 (3) Å]. Selected interatomic distances and angles are listed in Table 1.

The Cu—N bond distances to H2biim and inter-ring C1—C2 bond length in (I) present no unusual features and are consistent with the previous report in [Cu(H2biim)2]Cl2 [Bencini & Mani, 1988], [Cu(Me4biim)ONO2]Cl [Bernarducci et al., 1983] and [VOCl(H2Biim)2]Cl [Cancela et al., 2001] complexes. In our case the principal coordination is planar and the Cu atom lies within that plane. Both imidazole rings are planar, with no atoms deviating by more than 0.007 A° from the least-squares plane. The two rings of H2biim are nearly coplanar, making an angle of 0.70 (9)°. This value compares well with that found in the mononuclear copper(II) species [Cu(H2biim)2]2+ which are in a strictly planar environment (Bencini & Mani, 1988) and that observed in the free H2biim molecule (Cromer et al., 1987), but it is smaller than that found for the mononuclear oxovanadium(IV) species [VOCl(H2biim)2]Cl (Cancela et al., 2001).

[Cu(H2biim)2](tcnoet)2 units are connected to each other via hydrogen bonds N—H···N resulting in a one-dimensional chains as shown in Fig. 2. Furthermore these chains are maintained through van der Waals interactions on the (ab) plane and connect each other via C—H···N hydrogen bonds into a two-dimensional network (Fig. 3). Interestingly, each tcnoet- anion help to sustain the one-dimensional assembly and at the same time the final two-dimensional array.

In this complex, the three central C atoms (C11, C12 and C13) of the anionic ligand present an sp2 hybridization as indicated by the sum of the three angles around them (359.98° or 360.0°). Two additional facts support the idea of electron delocalization over the three central C atoms: (i) the six central C—C bond distances (1.389 A° -1.428 A°) are longer than a normal C═C double bond (1.340 A°) and close to those of benzene and (ii) the C11—O1 bond distance 1.352 A° is much shorter than tne normal C—O single bond, suggesting that the two central and the C11—O1 bond present a partial double character.

Experimental

H2biim and Ktcnoet ligands were synthesized with the published procedures respectively (Bernarducci et al., 1983; Middleton et al., 1958). To a methanolic suspension of H2biim (0.025 g, 5 ml) was added drowpize a solution of CuCl2.2H2O (0.032 g, 5 ml) resulting in a green solution. Ktcnoet was dissolved in water (0.084 g, 10 ml) and was added quickly to the former solution. The final solution was filtred and allowed to evaporate for a week, giving green blocks of (I). X band EPR spectrum from a polycristalline powdred sample of (I) recorded at room temperature exhibits a well defined axial signal with gparallel = 2.27 > gperpendicular = 2.07 consistent with a Cu(II) monomer.

Refinement

All H atoms were placed in geometrical positions and refined using a riding model, with C—H distances in the range 0.95–0.99 Å and their displacement parameters were set to Uiso(H) = 1.5Ueq(C) for methyl group and Uiso(H) = 1.2Ueq (C) for all others, while N—H bond lengths were fixed to 0.88 Å with Uiso(H) = 1.2Ueq(carrier N atom).

Figures

Fig. 1.
The metal environnement in (I), with displacement ellipsoids drawn at the 50% probability level. Unlabelled atoms are related to labelled atoms by the symmetry operation 1 - x, 1 - y, 1 - z.
Fig. 2.
View of the one one-dimensional hydrogen bonded chain on the ab plane. Symmetry codes: i(-1 + x,y,z), ii(1 + x,y,z)
Fig. 3.
View of the hydrogen bonded maintaining the chains along the c axis. Symmetry codes i(1 - x,1 - y,1 - z), ii(1 - x,1 - y,-z), iii(x,y,1 + z), VIi(x,y,-1 +z), Vi(1 - x,1 - y,2 - z).

Crystal data

[Cu(C6H6N4)2](C9H5N4O)2F(000) = 718
Mr = 702.18Dx = 1.503 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3092 reflections
a = 8.1001 (8) Åθ = 2.8–31.5°
b = 26.1834 (11) ŵ = 0.76 mm1
c = 8.2185 (7) ÅT = 170 K
β = 117.086 (11)°Block, green
V = 1551.9 (2) Å30.40 × 0.30 × 0.20 mm
Z = 2

Data collection

Oxford Diffraction Xcalibur CCD diffractometer3002 independent reflections
Radiation source: Enhance (Mo) X-ray Source1854 reflections with I > 2σ(I)
graphiteRint = 0.037
Detector resolution: 8.3622 pixels mm-1θmax = 26.0°, θmin = 2.8°
ω and [var phi] scansh = −9→9
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)k = −30→32
Tmin = 0.750, Tmax = 0.862l = −10→9
8646 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077H-atom parameters constrained
S = 0.93w = 1/[σ2(Fo2) + (0.0371P)2] where P = (Fo2 + 2Fc2)/3
3002 reflections(Δ/σ)max < 0.001
223 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = −0.28 e Å3

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)

xyzUiso*/Ueq
Cu10.50000.50000.50000.02739 (14)
O10.5765 (2)0.72753 (6)0.7896 (2)0.0279 (4)
N10.3433 (3)0.55852 (7)0.3669 (3)0.0270 (5)
N20.3432 (3)0.50383 (7)0.6359 (2)0.0250 (4)
N30.1123 (3)0.54298 (7)0.6550 (3)0.0276 (5)
H30.01980.56420.63110.033*
N40.1107 (3)0.60926 (7)0.3218 (3)0.0301 (5)
H40.01890.62350.33460.036*
N70.7829 (4)0.55883 (8)0.7720 (3)0.0473 (7)
N80.3624 (4)0.63047 (9)0.8836 (3)0.0523 (7)
N90.8650 (3)0.63404 (8)0.4902 (3)0.0431 (6)
N100.9040 (3)0.79164 (8)0.6867 (3)0.0388 (6)
C10.2179 (3)0.57061 (8)0.4219 (3)0.0240 (6)
C20.2177 (3)0.54105 (8)0.5686 (3)0.0235 (6)
C30.3131 (4)0.59086 (9)0.2255 (4)0.0362 (7)
H3A0.38200.59120.15790.043*
C40.1704 (4)0.62228 (9)0.1967 (4)0.0365 (7)
H4A0.12110.64840.10690.044*
C50.3157 (4)0.48229 (9)0.7740 (3)0.0306 (6)
H50.38580.45480.84900.037*
C60.1746 (3)0.50594 (9)0.7877 (3)0.0306 (6)
H60.12780.49850.87210.037*
C70.7098 (4)0.59593 (10)0.7744 (3)0.0312 (7)
C80.4741 (4)0.63526 (9)0.8363 (3)0.0335 (7)
C90.8243 (4)0.66396 (10)0.5669 (4)0.0297 (6)
C100.8449 (3)0.75144 (10)0.6727 (3)0.0286 (6)
C110.6541 (3)0.68945 (8)0.7366 (3)0.0234 (6)
C120.6126 (3)0.64089 (8)0.7755 (3)0.0255 (6)
C130.7714 (3)0.70132 (8)0.6596 (3)0.0241 (6)
C140.4716 (3)0.76732 (9)0.6587 (3)0.0303 (6)
H14A0.53440.77620.58360.036*
H14B0.46690.79840.72520.036*
C150.2811 (4)0.74960 (11)0.5388 (4)0.0507 (8)
H15A0.21250.77660.45170.076*
H15B0.21850.74130.61320.076*
H15C0.28600.71910.47200.076*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cu10.0314 (3)0.0214 (2)0.0359 (3)0.0069 (2)0.0209 (2)0.0044 (2)
O10.0385 (11)0.0222 (8)0.0283 (9)0.0026 (8)0.0200 (9)0.0005 (8)
N10.0270 (13)0.0232 (11)0.0362 (13)0.0033 (10)0.0191 (11)0.0019 (10)
N20.0249 (12)0.0226 (10)0.0291 (11)0.0045 (10)0.0137 (9)0.0026 (10)
N30.0281 (13)0.0241 (11)0.0352 (12)0.0040 (10)0.0183 (11)−0.0030 (10)
N40.0303 (13)0.0236 (11)0.0426 (14)0.0087 (10)0.0221 (11)0.0039 (10)
N70.0602 (18)0.0228 (12)0.0658 (17)0.0040 (12)0.0348 (14)0.0053 (12)
N80.078 (2)0.0439 (15)0.0591 (17)−0.0250 (14)0.0521 (16)−0.0141 (13)
N90.0543 (17)0.0358 (13)0.0539 (15)0.0115 (12)0.0376 (14)0.0048 (12)
N100.0317 (14)0.0336 (13)0.0491 (15)−0.0085 (12)0.0165 (12)0.0003 (12)
C10.0268 (16)0.0156 (12)0.0318 (15)0.0018 (11)0.0154 (13)−0.0030 (11)
C20.0231 (15)0.0173 (12)0.0320 (15)−0.0031 (11)0.0141 (12)−0.0067 (11)
C30.0447 (19)0.0298 (15)0.0478 (18)0.0104 (14)0.0330 (16)0.0119 (14)
C40.0472 (19)0.0245 (14)0.0442 (18)0.0081 (14)0.0263 (15)0.0093 (13)
C50.0335 (17)0.0273 (14)0.0319 (15)0.0063 (12)0.0156 (13)0.0069 (11)
C60.0330 (16)0.0345 (15)0.0304 (14)0.0003 (13)0.0198 (12)0.0007 (13)
C70.0423 (19)0.0214 (14)0.0312 (16)−0.0089 (14)0.0180 (14)0.0014 (12)
C80.053 (2)0.0215 (13)0.0309 (15)−0.0099 (13)0.0231 (15)−0.0060 (11)
C90.0281 (17)0.0274 (14)0.0380 (16)0.0020 (12)0.0187 (13)0.0087 (13)
C100.0212 (16)0.0343 (15)0.0291 (15)0.0023 (13)0.0105 (12)0.0035 (12)
C110.0257 (16)0.0216 (13)0.0184 (12)−0.0003 (11)0.0062 (11)−0.0009 (10)
C120.0315 (16)0.0198 (13)0.0280 (14)−0.0024 (12)0.0160 (12)−0.0011 (11)
C130.0257 (15)0.0178 (12)0.0309 (14)0.0012 (11)0.0147 (12)0.0008 (11)
C140.0320 (17)0.0243 (13)0.0353 (16)0.0066 (12)0.0158 (13)0.0033 (12)
C150.039 (2)0.0549 (19)0.048 (2)−0.0006 (16)0.0106 (16)−0.0014 (16)

Geometric parameters (Å, °)

Cu1—N11.9727 (19)N10—C101.140 (3)
Cu1—N1i1.9727 (19)C1—C21.433 (3)
Cu1—N2i2.0397 (18)C3—C41.349 (3)
Cu1—N22.0397 (18)C3—H3A0.9500
Cu1—N72.821 (2)C4—H4A0.9500
O1—C111.352 (3)C5—C61.349 (3)
O1—C141.460 (3)C5—H50.9500
N1—C11.324 (3)C6—H60.9500
N1—C31.367 (3)C7—C121.419 (3)
N2—C21.333 (3)C8—C121.428 (4)
N2—C51.374 (3)C9—C131.421 (3)
N3—C21.337 (3)C10—C131.425 (3)
N3—C61.372 (3)C11—C121.389 (3)
N3—H30.8800C11—C131.395 (3)
N4—C11.343 (3)C14—C151.477 (3)
N4—C41.364 (3)C14—H14A0.9900
N4—H40.8800C14—H14B0.9900
N7—C71.143 (3)C15—H15A0.9800
N8—C81.143 (3)C15—H15B0.9800
N9—C91.144 (3)C15—H15C0.9800
N1—Cu1—N1i180.00C3—C4—H4A126.7
N1—Cu1—N2i97.96 (8)N4—C4—H4A126.7
N1i—Cu1—N2i82.04 (8)C6—C5—N2110.0 (2)
N1—Cu1—N282.04 (8)C6—C5—H5125.0
N1i—Cu1—N297.96 (8)N2—C5—H5125.0
N2i—Cu1—N2180.0C5—C6—N3106.1 (2)
N1—Cu1—N795.79 (7)C5—C6—H6126.9
N1i—Cu1—N784.21 (7)N3—C6—H6126.9
N2i—Cu1—N788.69 (7)N7—C7—C12177.8 (3)
N2—Cu1—N791.31 (7)N8—C8—C12179.4 (3)
C11—O1—C14119.25 (18)N9—C9—C13179.1 (3)
C1—N1—C3105.9 (2)N10—C10—C13178.6 (3)
C1—N1—Cu1113.35 (16)O1—C11—C12113.8 (2)
C3—N1—Cu1140.66 (17)O1—C11—C13119.61 (19)
C2—N2—C5105.23 (19)C12—C11—C13126.5 (2)
C2—N2—Cu1110.87 (15)C11—C12—C7124.4 (2)
C5—N2—Cu1143.89 (17)C11—C12—C8119.1 (2)
C2—N3—C6107.6 (2)C7—C12—C8116.3 (2)
C2—N3—H3126.2C11—C13—C9121.6 (2)
C6—N3—H3126.2C11—C13—C10121.2 (2)
C1—N4—C4107.3 (2)C9—C13—C10117.2 (2)
C1—N4—H4126.3O1—C14—C15110.4 (2)
C4—N4—H4126.3O1—C14—H14A109.6
C7—N7—Cu1103.7 (2)C15—C14—H14A109.6
N1—C1—N4110.7 (2)O1—C14—H14B109.6
N1—C1—C2116.9 (2)C15—C14—H14B109.6
N4—C1—C2132.4 (2)H14A—C14—H14B108.1
N2—C2—N3111.0 (2)C14—C15—H15A109.5
N2—C2—C1116.8 (2)C14—C15—H15B109.5
N3—C2—C1132.2 (2)H15A—C15—H15B109.5
C4—C3—N1109.5 (2)C14—C15—H15C109.5
C4—C3—H3A125.2H15A—C15—H15C109.5
N1—C3—H3A125.2H15B—C15—H15C109.5
C3—C4—N4106.6 (2)
N2i—Cu1—N1—C1178.54 (16)C6—N3—C2—N21.3 (3)
N2—Cu1—N1—C1−1.46 (16)C6—N3—C2—C1−179.2 (2)
N7—Cu1—N1—C1−91.98 (17)N1—C1—C2—N2−0.4 (3)
N2i—Cu1—N1—C32.7 (3)N4—C1—C2—N2178.3 (2)
N2—Cu1—N1—C3−177.3 (3)N1—C1—C2—N3−179.9 (2)
N7—Cu1—N1—C392.2 (3)N4—C1—C2—N3−1.2 (4)
N1i—Cu1—N2—C2−178.76 (15)C1—N1—C3—C40.2 (3)
N7—Cu1—N2—C296.90 (16)Cu1—N1—C3—C4176.3 (2)
N1—Cu1—N2—C5−178.8 (3)N1—C3—C4—N4−0.1 (3)
N1i—Cu1—N2—C51.2 (3)C1—N4—C4—C3−0.1 (3)
N7—Cu1—N2—C5−83.1 (3)C2—N2—C5—C60.7 (3)
N1—Cu1—N7—C724.02 (19)Cu1—N2—C5—C6−179.3 (2)
N1i—Cu1—N7—C7−155.98 (19)N2—C5—C6—N30.1 (3)
N2i—Cu1—N7—C7121.89 (19)C2—N3—C6—C5−0.9 (3)
N2—Cu1—N7—C7−58.11 (19)C14—O1—C11—C12−129.2 (2)
C3—N1—C1—N4−0.2 (3)C14—O1—C11—C1354.0 (3)
Cu1—N1—C1—N4−177.52 (15)O1—C11—C12—C7−164.3 (2)
C3—N1—C1—C2178.7 (2)C13—C11—C12—C712.3 (4)
Cu1—N1—C1—C21.4 (3)O1—C11—C12—C810.1 (3)
C4—N4—C1—N10.2 (3)C13—C11—C12—C8−173.3 (2)
C4—N4—C1—C2−178.6 (2)O1—C11—C13—C9−166.3 (2)
C5—N2—C2—N3−1.2 (3)C12—C11—C13—C917.2 (4)
Cu1—N2—C2—N3178.75 (15)O1—C11—C13—C1014.4 (4)
C5—N2—C2—C1179.2 (2)C12—C11—C13—C10−162.0 (2)
Cu1—N2—C2—C1−0.8 (2)C11—O1—C14—C1581.6 (3)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3···N9ii0.882.223.011 (3)149
N4—H4···N9ii0.882.172.967 (3)150
C3—H3A···N8iii0.952.423.187 (3)138

Symmetry codes: (ii) x−1, y, z; (iii) x, y, z−1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5555).

References

  • Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst.32, 115–119.
  • Atmani, C., Setifi, F., Benmansour, S., Triki, S., Marchivie, M., Salaün, J.-Y. & Gómez-García, C. J. (2008). Inorg. Chem. Commun.11, 921–924.
  • Batten, S. R. & Murray, K. S. (2003). Coord. Chem. Rev.246, 103–130.
  • Bencini, A. & Mani, F. (1988). Inorg. Chim. Acta, 154, 215–219.
  • Benmansour, S., Setifi, F., Triki, S., Salaün, J.-Y., Vandevelde, F., Sala-Pala, J., Gómez-García, C. J. & Roisnel, T. (2007). Eur. J. Inorg. Chem. pp. 186–194.
  • Bernarducci, E. B., Bharadwaj, P. K., Lalancette, R. A., Krogh-Jespersen, K., Potenza, J. A. & Schugar, H. J. (1983). Inorg. Chem.22, 3911–3920.
  • Cancela, J., Gonalez Garmendia, M. J. & Qurs, M. (2001). Inorg. Chim. Acta, 313, 156–159.
  • Cromer, D. T., Ryan, R. R. & Storm, C. B. (1987). Acta Cryst. C43, 1435–1437.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Jones, L. F., O’Dea, L., Offermann, D. A., Jensen, P., Moubaraki, B. & Murray, K. S. (2006). Polyhedron, 25, 360–372.
  • Middleton, W. J. & Engelhardt, V. A. (1958). J. Am. Chem. Soc.80, 2788–2795.
  • Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED Oxford Diffraction Ltd, Abingdon, England.
  • Setifi, F., Benmansour, S., Triki, S., Gómez-García, C. J., Marchivie, M., Salaün, J.-Y. & Maamache, M. (2007). Inorg. Chim. Acta, 360, 3879–3886.
  • Setifi, F., Bouchama, A., Sala-Pala, J., Salaün, J.-Y. & Triki, S. (2006). Inorg. Chim. Acta, 359, 3269–3274.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Thétiot, F., Triki, S., Sala-Pala, J. & Golhen, S. (2003). Inorg. Chim. Acta, 350, 314–320.
  • Triki, S., Thétiot, F., Vandevelde, F., Sala-Pala, J. & Gómez-García, C. J. (2005). Inorg. Chem.44, 4086–4093. [PubMed]
  • Watkin, D. M., Pearce, L. & Prout, C. K. (1993). CAMERON Chemical Crystallography Laboratory, University of Oxford, England.
  • Yuste, C., Bentama, A., Stiriba, S.-E., Armentano, D., De Munno, G., Lloret, F. & Julve, M. (2007). Dalton Trans. pp. 5190–5200. [PubMed]

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