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Acta Cryst. (2008). E64, m1220    [ doi:10.1107/S1600536808027281 ]

catena-Poly[[[diaquacopper(II)]-bis[[mu]-1,1'-(butane-1,4-diyl)diimidazole-[kappa]2N3:N3']] dinitrate]

X.-F. Wang, J.-F. Wang and X.-Y. Liu

Abstract top

In the title compound, {[Cu(C10H14N4)2(H2O)2](NO3)2}n, the CuII ion lies on an inversion center and is six-coordinated in an octahedral environment by four N atoms from four different 1,1'-butane-1,4-diyldiimidazole ligands and two O atoms from the two water molecules. Bridging by the ligands results in a ribbon structure. Adjacent ribbons are linked to the nitrate anions via O-H...O hydrogen bonds, forming layers. One nitrate O atom is disordered equally over two positions.

Comment top

The 1,1'-butane-1,4-diyldiimidazole can be used as a flexible ligand to construct coordination polymeric compounds (Ma et al., 2003; Che et al., 2006). In this paper, we report the new title compound, (I), synthesized by the reaction of 1,1'-butane-1,4-diyldiimidazole ligands and copper dinitrate in methanol.

The CuII atom is located on an inversion centre and is hexacoordinated by four N atoms of four different 1,1'-butane-1,4-diyldiimidazole ligands and two O atoms of two water molecules (Fig. 1). Adjacent Cu(II) ions are linked by pairs of 1,1'-butane-1,4- diyldiimidazole molecules, resulting in a ribbon motif (Fig. 2).

In the crystal structure, uncoordinated nitrate anions link these ribbons into a layer structure via O—H···O hydrogen bonds (Table 1,Figure 3).

Related literature top

For background and the synthesis of 1,1'-butane-1,4-diyldiimidazole, see: Ma et al. (2003). For the crystal structure of metal adduct, see: Che et al. (2006).

Experimental top

1,1'-Butane-1,4-diyldiimidazole was prepared from imidazole and 1,4-dibromobutane in DMSO (Ma et al., 2003). 1,1'-(1,4-Butanediyl)diimidazole (0.380 g, 2 mmol) and copper dinitrate (0.188 g, 2 mmol) were dissolved in hot methanol solution (15 ml) to give a clear solution was obtained. The resulting solution was allowed to stand in a desiccator at room temperature for several days. Blue crystals of (I) were obtained.

Refinement top

The O3 atom of the nitrate is refined with a split model over two positions, with occupancy of 0.5 for O3 and O3'. H atoms bound to C atoms were placed in calculated positions and treated as riding on their parent atoms, with C—H = 0.93 Å (Caromatic); C—H = 0.97 Å (methylene) and with Uiso(H) = 1.2Ueq(C). Water H atoms were initially located in a difference Fourier map, but they were treated as riding on their parent atoms with O—H = 0.85 Å and with Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing displacement ellipsoids at the 30% probability level for non-H atoms. Dashed lines indicate the hydrogen-bonding interactions [Symmetry code: (I) -x + 1, y, -z + 3/2; (II) -x + 1/2, -y + 3/2, -z - 1;(III) x + 1/2, -y + 3/2, z + 1/2].
[Figure 2] Fig. 2. A partial packing view, showing the ribbon chain structure.
[Figure 3] Fig. 3. A partial packing view, showing the two-dimensional network. Dashed lines indicate the hydrogen-bonding interactions and H atoms have been omitted.
catena-Poly[[[diaquacopper(II)]-bis[µ-1,1'-(butane-1,4- diyl)diimidazole-κ2N3:N3']] dinitrate] top
Crystal data top
[Cu(C10H14N4)2(H2O)2](NO3)2F000 = 1260
Mr = 604.10Dx = 1.515 Mg m−3
Monoclinic, C2/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 11099 reflections
a = 22.161 (11) Åθ = 3.3–27.5º
b = 10.334 (4) ŵ = 0.89 mm−1
c = 14.366 (7) ÅT = 291 (2) K
β = 126.375 (18)ºBlock, blue
V = 2649 (2) Å30.48 × 0.36 × 0.25 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer		3023 independent reflections
Radiation source: fine-focus sealed tube2753 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.024
T = 291(2) Kθmax = 27.5º
ω scansθmin = 3.3º
Absorption correction: Multi-scan
(ABSCOR; Higashi, 1995)		h = −28→28
Tmin = 0.673, Tmax = 0.808k = −13→12
12704 measured reflectionsl = −18→18
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.113  w = 1/[σ2(Fo2) + (0.0644P)2 + 3.5066P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
3023 reflectionsΔρmax = 0.82 e Å−3
188 parametersΔρmin = −0.55 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Cu(C10H14N4)2(H2O)2](NO3)2V = 2649 (2) Å3
Mr = 604.10Z = 4
Monoclinic, C2/cMo Kα
a = 22.161 (11) ŵ = 0.89 mm−1
b = 10.334 (4) ÅT = 291 (2) K
c = 14.366 (7) Å0.48 × 0.36 × 0.25 mm
β = 126.375 (18)º
Data collection top
Rigaku R-AXIS RAPID
diffractometer		3023 independent reflections
Absorption correction: Multi-scan
(ABSCOR; Higashi, 1995)		2753 reflections with I > 2σ(I)
Tmin = 0.673, Tmax = 0.808Rint = 0.024
12704 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.039188 parameters
wR(F2) = 0.113H-atom parameters constrained
S = 1.07Δρmax = 0.82 e Å−3
3023 reflectionsΔρmin = −0.55 e Å−3
Special details top

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) top
xyzUiso*/UeqOcc. (<1)
C10.43494 (12)0.5667 (2)0.87357 (19)0.0360 (4)
H10.43870.48020.86000.043*
C20.40800 (13)0.6108 (2)0.9310 (2)0.0395 (5)
H20.39010.56110.96380.047*
C30.44106 (11)0.7749 (2)0.87476 (18)0.0321 (4)
H30.44950.85930.86270.038*
C40.38590 (14)0.8327 (3)0.9787 (2)0.0460 (6)
H4A0.40390.91900.98070.055*
H4B0.40690.80781.05760.055*
C50.30100 (14)0.8355 (3)0.9086 (2)0.0514 (7)
H5A0.28720.89260.94670.062*
H5B0.28360.74930.90840.062*
C60.26042 (14)0.8803 (3)0.7830 (2)0.0473 (6)
H6A0.21280.91860.75690.057*
H6B0.29020.94700.78040.057*
C70.24623 (12)0.7730 (2)0.70083 (18)0.0394 (5)
H7A0.29380.74050.72140.047*
H7B0.22050.70230.70820.047*
C80.22282 (12)0.9038 (3)0.5330 (2)0.0427 (5)
H80.26960.94270.56990.051*
C90.16308 (12)0.9201 (3)0.42203 (19)0.0402 (5)
H90.16190.97310.36870.048*
C100.12939 (11)0.7874 (2)0.49805 (18)0.0325 (4)
H100.10100.73150.50860.039*
Cu10.50000.66433 (3)0.75000.02769 (13)
N10.45588 (9)0.67011 (16)0.83845 (14)0.0293 (4)
N20.41221 (9)0.74259 (19)0.93120 (14)0.0328 (4)
N30.20075 (10)0.81828 (18)0.58036 (16)0.0342 (4)
N40.10424 (9)0.84658 (17)0.39970 (15)0.0317 (4)
N50.59796 (14)0.1501 (2)0.7259 (3)0.0516 (6)
O10.50000.9027 (3)0.75000.0740 (10)
H110.46280.95230.72540.111*
O20.5825 (2)0.0978 (4)0.6366 (3)0.1229 (13)
O30.5894 (5)0.2662 (7)0.7011 (8)0.089 (2)0.50
O40.61485 (19)0.0723 (3)0.8025 (3)0.0997 (10)
O50.50000.4120 (3)0.75000.0640 (8)
H120.46900.35730.74330.082 (13)*
O3'0.6140 (5)0.2592 (7)0.7753 (9)0.099 (3)0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0384 (11)0.0388 (11)0.0349 (10)0.0060 (9)0.0239 (9)0.0065 (9)
C20.0400 (11)0.0502 (13)0.0353 (11)0.0056 (10)0.0263 (10)0.0109 (10)
C30.0270 (9)0.0405 (11)0.0284 (9)−0.0014 (8)0.0162 (8)−0.0031 (8)
C40.0390 (12)0.0706 (17)0.0274 (11)0.0129 (11)0.0191 (10)−0.0063 (10)
C50.0388 (12)0.089 (2)0.0311 (12)0.0203 (12)0.0233 (11)0.0022 (11)
C60.0419 (12)0.0596 (14)0.0324 (11)0.0185 (11)0.0178 (10)0.0020 (11)
C70.0314 (10)0.0485 (13)0.0256 (10)0.0068 (9)0.0099 (9)0.0054 (9)
C80.0284 (10)0.0633 (15)0.0339 (11)−0.0104 (10)0.0170 (9)−0.0013 (10)
C90.0313 (10)0.0588 (14)0.0309 (10)−0.0083 (10)0.0187 (9)0.0017 (10)
C100.0263 (9)0.0397 (10)0.0281 (10)−0.0016 (8)0.0144 (8)0.0021 (8)
Cu10.02036 (18)0.0421 (2)0.02152 (19)0.0000.01289 (15)0.000
N10.0239 (8)0.0408 (9)0.0241 (8)0.0015 (6)0.0147 (7)−0.0004 (6)
N20.0254 (8)0.0509 (10)0.0216 (8)0.0055 (7)0.0135 (7)−0.0009 (7)
N30.0252 (8)0.0453 (10)0.0258 (9)0.0011 (7)0.0116 (7)0.0020 (7)
N40.0249 (8)0.0436 (9)0.0260 (8)−0.0019 (7)0.0147 (7)0.0002 (7)
N50.0477 (12)0.0460 (12)0.0739 (17)0.0010 (9)0.0430 (13)0.0065 (11)
O10.098 (2)0.0383 (14)0.134 (3)0.0000.095 (3)0.000
O20.162 (3)0.137 (3)0.090 (2)−0.032 (3)0.086 (3)−0.006 (2)
O30.112 (6)0.045 (3)0.150 (7)0.023 (4)0.098 (6)0.024 (5)
O40.109 (2)0.108 (2)0.0686 (16)−0.0290 (19)0.0449 (16)0.0012 (16)
O50.086 (2)0.0417 (14)0.097 (2)0.0000.072 (2)0.000
O3'0.085 (5)0.043 (3)0.158 (8)0.002 (3)0.066 (6)0.001 (5)
Geometric parameters (Å, °) top
C1—C21.352 (3)C8—C91.349 (3)
C1—N11.374 (3)C8—N31.370 (3)
C1—H10.9300C8—H80.9300
C2—N21.365 (3)C9—N41.372 (3)
C2—H20.9300C9—H90.9300
C3—N11.325 (3)C10—N41.322 (3)
C3—N21.339 (3)C10—N31.335 (3)
C3—H30.9300C10—H100.9300
C4—N21.465 (3)Cu1—N12.0120 (18)
C4—C51.519 (4)Cu1—N1i2.0120 (18)
C4—H4A0.9700Cu1—N4ii2.020 (2)
C4—H4B0.9700Cu1—N4iii2.020 (2)
C5—C61.535 (3)Cu1—O12.463 (3)
C5—H5A0.9700Cu1—O52.608 (3)
C5—H5B0.9700N4—Cu1ii2.0203 (19)
C6—C71.510 (3)N5—O41.228 (4)
C6—H6A0.9700N5—O31.234 (7)
C6—H6B0.9700N5—O21.239 (4)
C7—N31.470 (3)O1—H110.8500
C7—H7A0.9700O5—H120.8500
C7—H7B0.9700
C2—C1—N1109.2 (2)C8—C9—H9125.1
C2—C1—H1125.4N4—C9—H9125.1
N1—C1—H1125.4N4—C10—N3111.30 (19)
C1—C2—N2106.46 (19)N4—C10—H10124.3
C1—C2—H2126.8N3—C10—H10124.3
N2—C2—H2126.8N1—Cu1—N1i176.60 (10)
N1—C3—N2110.72 (19)N1—Cu1—N4ii89.82 (8)
N1—C3—H3124.6N1i—Cu1—N4ii90.37 (8)
N2—C3—H3124.6N1—Cu1—N4iii90.37 (8)
N2—C4—C5112.4 (2)N1i—Cu1—N4iii89.82 (8)
N2—C4—H4A109.1N4ii—Cu1—N4iii173.60 (10)
C5—C4—H4A109.1N1—Cu1—O188.30 (5)
N2—C4—H4B109.1N1i—Cu1—O188.30 (5)
C5—C4—H4B109.1N4ii—Cu1—O193.20 (5)
H4A—C4—H4B107.8N4iii—Cu1—O193.20 (5)
C4—C5—C6114.7 (2)N1—Cu1—O591.70 (5)
C4—C5—H5A108.6N1i—Cu1—O591.70 (5)
C6—C5—H5A108.6N4ii—Cu1—O586.80 (5)
C4—C5—H5B108.6N4iii—Cu1—O586.80 (5)
C6—C5—H5B108.6O1—Cu1—O5180.000 (1)
H5A—C5—H5B107.6C3—N1—C1105.91 (18)
C7—C6—C5113.8 (2)C3—N1—Cu1126.85 (14)
C7—C6—H6A108.8C1—N1—Cu1127.24 (14)
C5—C6—H6A108.8C3—N2—C2107.66 (18)
C7—C6—H6B108.8C3—N2—C4126.1 (2)
C5—C6—H6B108.8C2—N2—C4126.2 (2)
H6A—C6—H6B107.7C10—N3—C8107.36 (18)
N3—C7—C6111.5 (2)C10—N3—C7126.27 (19)
N3—C7—H7A109.3C8—N3—C7126.33 (19)
C6—C7—H7A109.3C10—N4—C9105.44 (18)
N3—C7—H7B109.3C10—N4—Cu1ii127.10 (15)
C6—C7—H7B109.3C9—N4—Cu1ii127.43 (15)
H7A—C7—H7B108.0O4—N5—O3144.0 (5)
C9—C8—N3106.16 (19)O4—N5—O2113.1 (3)
C9—C8—H8126.9O3—N5—O2103.0 (5)
N3—C8—H8126.9Cu1—O1—H11127.1
C8—C9—N4109.7 (2)Cu1—O5—H12131.6
Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+1/2, −y+3/2, −z+1; (iii) x+1/2, −y+3/2, z+1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H11···O4iv0.851.962.801 (4)170
O5—H12···O3i0.852.102.888 (8)153
Symmetry codes: (iv) −x+1, y+1, −z+3/2; (i) −x+1, y, −z+3/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H11···O4i0.851.962.801 (4)170
O5—H12···O3ii0.852.102.888 (8)153
Symmetry codes: (i) −x+1, y+1, −z+3/2; (ii) −x+1, y, −z+3/2.
Acknowledgements top

The authors thank Jilin University for supporting this study.

references
References top

Che, G.-B., Liu, H., Liu, C.-B. & Liu, B. (2006). Acta Cryst. E62, m286–m288.

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.

Ma, J.-F., Yang, J., Zheng, G.-L. & Liu, J.-F. (2003). Inorg. Chem. 42, 7531–7534.

Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.

Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.