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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 65| Part 3| March 2009| Pages m313-m314
doi:10.1107/S1600536809005881

Poly[[[di­aqua­cobalt(II)]-bis­­[μ2-1,1′-(butane-1,4-di­yl)di­imidazole-κ2N3:N3′]] dinitrate]

Yu Su,a Chuan He,b Zhi-Zhong Sun,a Guang-Feng Houa and Jin-Sheng Gaoa*

aCollege of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China, and bSchool of Resources and Safety Engineering, China University of Mining and Technology (Beijing Campus), Beijing 100083, People's Republic of China
*Correspondence e-mail: hgf1000@163.com

(Received 17 February 2009; accepted 19 February 2009; online 25 February 2009)

In the title compound, {[Co(C10H14N4)2(H2O)2](NO3)2}n, the CoII 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. The CoII atoms are bridged by ligands, generating a two-dimensional (4,4)-network. Adjacent fishnet planes are linked to the nitrate anions via O—H⋯O hydrogen bonds, forming a three-dimensional supra­molecular structure.

Related literature

For the synthesis of 1,1′-butane-1,4-diyldiimidazole, see: Ma et al. (2003[Ma, J.-F., Yang, J., Zheng, G.-L. & Liu, J.-F. (2003). Inorg. Chem. 42, 7531-7534.]); Yu et al. (2008[Yu, Y.-H., Shi, A.-E., Su, Y., Hou, G.-F. & Gao, J.-S. (2008). Acta Cryst. E64, m628.]) For a related Co complex, see: Dong & Zhang (2006[Dong, G.-C. & Zhang, R.-C. (2006). Acta Cryst. E62, m1847-m1849.]).

[Scheme 1]

Experimental

Crystal data

  • [Co(C10H14N4)2(H2O)2](NO3)2

  • Mr = 599.49

  • Triclinic, [P \overline 1]

  • a = 8.574 (7) Å

  • b = 8.692 (6) Å

  • c = 9.666 (5) Å

  • α = 104.71 (2)°

  • β = 97.14 (3)°

  • γ = 98.89 (3)°

  • V = 678.2 (8) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 0.70 mm−1

  • T = 291 K

  • 0.45 × 0.28 × 0.26 mm
Data collection

  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.745, Tmax = 0.842

  • 6717 measured reflections

  • 3073 independent reflections

  • 2888 reflections with I > 2σ(I)

  • Rint = 0.015
Refinement

  • R[F2 > 2σ(F2)] = 0.031

  • wR(F2) = 0.096

  • S = 1.16

  • 3073 reflections

  • 178 parameters

  • H-atom parameters constrained

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Selected geometric parameters (Å, °)

Co1—N3 2.109 (2)
Co1—N1 2.1697 (18)
Co1—O1 2.1838 (16)
N3—Co1—N1 86.99 (7)
N3—Co1—O1 90.67 (7)
N1—Co1—O1 89.79 (6)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H15⋯O4i 0.85 1.94 2.775 (3) 167
O1—H16⋯O2ii 0.85 2.09 2.930 (3) 171
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x-1, y, z.

Data collection: RAPID-AUTO (Rigaku, 1998[Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809005881/ng2547sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809005881/ng2547Isup2.hkl

checkCIF report


Comment top

The 1,1'-butane-1,4-diyldiimidazole as a flexible ligand exhibit a variety of supramolecular aggregation patterns (Ma et al., 2003; Dong et al., 2006; Yu et al., 2008). In this paper, we report the new title compound, (I), synthssized by the reaction of 1,1'-butane-1,4-diyldiimidazole ligand and cobalt dinitrate in aqua solution.

In (I), each CoII atom is located on a inversion centre 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 form the two water molecules (Fig. 1). The Co—N and Co—O distances are normal (Table 1). The CoII atoms are bridged by ligands, generating a two-dimensional (4,4)-network (Fig. 2).

In the crystal, a R44(12) motif is built up by O—H···O hydrogen bonding interaction between the uncoordinated nitrate anions and the coordinated water molecules,which linke the adjacent fishnet planes to a three-dimensional supramolecular structure (Fig. 3, Table 2).

Related literature top

For the synthesis of 1,1'-butane-1,4-diyldiimidazole, see: Ma et al. (2003); Yu et al. (2008) For a related Co complex, see: Dong et al. (2006).

Experimental top

1,1'-Butane-1,4-diyldiimidazole ligand was prepared from imidazole and 1,4-dibromobutane in DMSO (Ma et al., 2003a). 1,1'-Butane-1,4-diyldiimidazole (0.76 g, 4 mmol) and cobalt dinitrate (0.73 g, 4 mmol) were dissolved in hot aqua solution (10 ml) to give a clear solution. The resulting solution was allowed to stand in a desiccator at room temperature for a week, pink crystals of (I) were obtained.

Refinement top

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 (aromatic), 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 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 + 1; (II) -x + 1, -y + 2, -z + 2: (III) -x, -y + 1, -z + 1]
[Figure 2] Fig. 2. A partial packing view, showing the two-dimensional (4,4)-network. Dashed lines indicate the hydrogen-bonding interactions and no involving H atoms have beeb omitted.
[Figure 3] Fig. 3. A Partial packing view, shoving the three-dimensional supramolecular structure. Dashed lines indicate the hydrogen-bonding interactions and no involving H atoms have beeb omitted.
Poly[[[diaquacobalt(II)]-bis[µ2-1,1'-(butane-1,4-diyl)diimidazole- κ2N3:N3']] dinitrate] top
Crystal data top
[Co(C10H14N4)2(H2O)2](NO3)2Z = 1
Mr = 599.49F(000) = 313
Triclinic, P1Dx = 1.468 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.574 (7) ÅCell parameters from 6295 reflections
b = 8.692 (6) Åθ = 3.0–27.5°
c = 9.666 (5) ŵ = 0.70 mm−1
α = 104.71 (2)°T = 291 K
β = 97.14 (3)°Block, brown
γ = 98.89 (3)°0.45 × 0.28 × 0.26 mm
V = 678.2 (8) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer		3073 independent reflections
Radiation source: fine-focus sealed tube2888 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.015
ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		h = −11→11
Tmin = 0.745, Tmax = 0.842k = −11→11
6717 measured reflectionsl = −12→12
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H-atom parameters constrained
S = 1.16 w = 1/[σ2(Fo2) + (0.0539P)2 + 0.1966P]
where P = (Fo2 + 2Fc2)/3
3073 reflections(Δ/σ)max < 0.001
178 parametersΔρmax = 0.35 e Å−3
0 restraintsΔρmin = −0.22 e Å−3
Crystal data top
[Co(C10H14N4)2(H2O)2](NO3)2γ = 98.89 (3)°
Mr = 599.49V = 678.2 (8) Å3
Triclinic, P1Z = 1
a = 8.574 (7) ÅMo Kα radiation
b = 8.692 (6) ŵ = 0.70 mm−1
c = 9.666 (5) ÅT = 291 K
α = 104.71 (2)°0.45 × 0.28 × 0.26 mm
β = 97.14 (3)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer		3073 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		2888 reflections with I > 2σ(I)
Tmin = 0.745, Tmax = 0.842Rint = 0.015
6717 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0310 restraints
wR(F2) = 0.096H-atom parameters constrained
S = 1.16Δρmax = 0.35 e Å−3
3073 reflectionsΔρmin = −0.22 e Å−3
178 parameters
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*/Ueq
C10.1755 (2)0.2246 (2)0.53022 (19)0.0325 (4)
H10.21060.28220.62720.039*
C20.0680 (2)0.1572 (2)0.30656 (19)0.0336 (4)
H20.01310.16050.21840.040*
C30.1346 (2)0.0324 (2)0.3277 (2)0.0372 (4)
H30.1343−0.06420.25860.045*
C40.2858 (2)−0.0192 (3)0.5505 (2)0.0424 (5)
H40.2518−0.13330.49890.051*
H50.2548−0.00330.64550.051*
C50.4672 (2)0.0257 (2)0.5695 (2)0.0386 (4)
H60.49970.14230.60920.046*
H70.5142−0.02410.63930.046*
C60.2528 (2)0.6569 (2)0.77832 (18)0.0304 (3)
H80.17360.66500.83590.036*
C70.3724 (2)0.6120 (2)0.59375 (19)0.0315 (3)
H90.39040.58250.49850.038*
C80.4887 (2)0.6696 (2)0.7135 (2)0.0352 (4)
H100.59890.68660.71590.042*
C90.4832 (3)0.7684 (3)0.9839 (2)0.0437 (5)
H110.56430.70911.00920.052*
H120.40180.75841.04410.052*
C100.5592 (2)0.9465 (3)1.0135 (2)0.0449 (5)
H130.61300.98681.11370.054*
H140.63980.95500.95230.054*
Co10.00000.50000.50000.02274 (11)
N10.09324 (17)0.27910 (17)0.43482 (15)0.0296 (3)
N20.20264 (17)0.07610 (18)0.47097 (17)0.0318 (3)
N30.22398 (16)0.60381 (16)0.63499 (15)0.0273 (3)
N40.41025 (18)0.69767 (19)0.83026 (16)0.0329 (3)
N50.8937 (2)0.6642 (2)0.02300 (18)0.0456 (4)
O10.08701 (16)0.57801 (16)0.32103 (13)0.0362 (3)
H150.12990.51430.26190.054*
H160.02150.61770.27340.054*
O20.8432 (2)0.6759 (3)0.13902 (17)0.0653 (5)
O31.0374 (3)0.7011 (3)0.0241 (2)0.0777 (6)
O40.7986 (3)0.6117 (3)−0.09384 (18)0.0784 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0368 (9)0.0342 (9)0.0280 (8)0.0154 (7)0.0043 (6)0.0069 (6)
C20.0329 (9)0.0340 (9)0.0296 (8)0.0099 (7)−0.0003 (6)0.0018 (7)
C30.0351 (9)0.0295 (8)0.0410 (10)0.0095 (7)0.0044 (7)−0.0016 (7)
C40.0378 (10)0.0439 (10)0.0616 (12)0.0199 (8)0.0163 (9)0.0325 (9)
C50.0347 (9)0.0401 (10)0.0481 (11)0.0173 (8)0.0071 (8)0.0188 (8)
C60.0275 (8)0.0326 (8)0.0281 (8)0.0071 (6)0.0016 (6)0.0040 (6)
C70.0294 (8)0.0352 (9)0.0289 (8)0.0104 (7)0.0043 (6)0.0050 (6)
C80.0252 (8)0.0408 (9)0.0361 (9)0.0074 (7)0.0022 (7)0.0052 (7)
C90.0417 (10)0.0535 (12)0.0264 (9)0.0104 (9)−0.0092 (7)0.0006 (8)
C100.0347 (10)0.0518 (12)0.0331 (10)0.0069 (8)−0.0095 (7)−0.0068 (8)
Co10.02260 (16)0.02296 (16)0.02042 (16)0.00763 (11)−0.00069 (10)0.00224 (11)
N10.0317 (7)0.0279 (7)0.0289 (7)0.0123 (6)0.0024 (5)0.0046 (5)
N20.0292 (7)0.0300 (7)0.0415 (8)0.0124 (6)0.0095 (6)0.0137 (6)
N30.0256 (7)0.0269 (7)0.0267 (7)0.0074 (5)−0.0003 (5)0.0034 (5)
N40.0286 (7)0.0367 (8)0.0273 (7)0.0071 (6)−0.0034 (5)0.0017 (6)
N50.0577 (11)0.0593 (11)0.0302 (8)0.0315 (9)0.0132 (7)0.0166 (7)
O10.0396 (7)0.0424 (7)0.0261 (6)0.0096 (5)0.0033 (5)0.0091 (5)
O20.0727 (12)0.0991 (15)0.0351 (8)0.0308 (11)0.0235 (8)0.0233 (9)
O30.0612 (12)0.1029 (17)0.0649 (12)0.0139 (11)0.0261 (10)0.0096 (11)
O40.0786 (13)0.1321 (19)0.0324 (8)0.0623 (13)0.0048 (8)0.0143 (10)
Geometric parameters (Å, º) top
C1—N11.318 (2)C8—N41.373 (2)
C1—N21.341 (2)C8—H100.9300
C1—H10.9300C9—N41.470 (2)
C2—C31.350 (3)C9—C101.523 (3)
C2—N11.379 (2)C9—H110.9700
C2—H20.9300C9—H120.9700
C3—N21.366 (3)C10—C10ii1.521 (4)
C3—H30.9300C10—H130.9700
C4—N21.469 (2)C10—H140.9700
C4—C51.519 (3)Co1—N32.109 (2)
C4—H40.9700Co1—N3iii2.109 (2)
C4—H50.9700Co1—N1iii2.1697 (18)
C5—C5i1.510 (4)Co1—N12.1697 (18)
C5—H60.9700Co1—O1iii2.1838 (16)
C5—H70.9700Co1—O12.1838 (16)
C6—N31.322 (2)N5—O31.222 (3)
C6—N41.339 (2)N5—O21.238 (2)
C6—H80.9300N5—O41.243 (3)
C7—C81.360 (3)O1—H150.8501
C7—N31.377 (2)O1—H160.8500
C7—H90.9300
N1—C1—N2112.01 (16)C9—C10—H13108.7
N1—C1—H1124.0C10ii—C10—H14108.7
N2—C1—H1124.0C9—C10—H14108.7
C3—C2—N1110.00 (16)H13—C10—H14107.6
C3—C2—H2125.0N3—Co1—N3iii180.0
N1—C2—H2125.0N3—Co1—N1iii93.01 (7)
C2—C3—N2106.29 (15)N3iii—Co1—N1iii86.99 (7)
C2—C3—H3126.9N3—Co1—N186.99 (7)
N2—C3—H3126.9N3iii—Co1—N193.01 (7)
N2—C4—C5113.21 (16)N1iii—Co1—N1180.0
N2—C4—H4108.9N3—Co1—O1iii89.33 (7)
C5—C4—H4108.9N3iii—Co1—O1iii90.67 (7)
N2—C4—H5108.9N1iii—Co1—O1iii89.79 (6)
C5—C4—H5108.9N1—Co1—O1iii90.21 (6)
H4—C4—H5107.8N3—Co1—O190.67 (7)
C5i—C5—C4113.9 (2)N3iii—Co1—O189.33 (7)
C5i—C5—H6108.8N1iii—Co1—O190.21 (6)
C4—C5—H6108.8N1—Co1—O189.79 (6)
C5i—C5—H7108.8O1iii—Co1—O1180.0
C4—C5—H7108.8C1—N1—C2104.72 (15)
H6—C5—H7107.7C1—N1—Co1121.60 (12)
N3—C6—N4111.57 (16)C2—N1—Co1133.01 (12)
N3—C6—H8124.2C1—N2—C3106.97 (15)
N4—C6—H8124.2C1—N2—C4124.90 (17)
C8—C7—N3109.66 (16)C3—N2—C4128.10 (16)
C8—C7—H9125.2C6—N3—C7105.41 (14)
N3—C7—H9125.2C6—N3—Co1127.19 (12)
C7—C8—N4105.97 (16)C7—N3—Co1126.95 (12)
C7—C8—H10127.0C6—N4—C8107.39 (15)
N4—C8—H10127.0C6—N4—C9125.56 (17)
N4—C9—C10110.98 (17)C8—N4—C9126.96 (16)
N4—C9—H11109.4O3—N5—O2119.7 (2)
C10—C9—H11109.4O3—N5—O4120.4 (2)
N4—C9—H12109.4O2—N5—O4119.8 (2)
C10—C9—H12109.4Co1—O1—H15119.0
H11—C9—H12108.0Co1—O1—H16115.0
C10ii—C10—C9114.1 (2)H15—O1—H16109.0
C10ii—C10—H13108.7
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+2, −z+2; (iii) −x, −y+1, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H15···O4iv0.851.942.775 (3)167
O1—H16···O2v0.852.092.930 (3)171
Symmetry codes: (iv) −x+1, −y+1, −z; (v) x−1, y, z.

Experimental details

Crystal data
Chemical formula[Co(C10H14N4)2(H2O)2](NO3)2
Mr599.49
Crystal system, space groupTriclinic, P1
Temperature (K)291
a, b, c (Å)8.574 (7), 8.692 (6), 9.666 (5)
α, β, γ (°)104.71 (2), 97.14 (3), 98.89 (3)
V (Å3)678.2 (8)
Z1
Radiation typeMo Kα
µ (mm−1)0.70
Crystal size (mm)0.45 × 0.28 × 0.26
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.745, 0.842
No. of measured, independent and
observed [I > 2σ(I)] reflections		6717, 3073, 2888
Rint0.015
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.096, 1.16
No. of reflections3073
No. of parameters178
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.35, −0.22

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top
Co1—N32.109 (2)Co1—O12.1838 (16)
Co1—N12.1697 (18)
N3—Co1—N186.99 (7)N1—Co1—O189.79 (6)
N3—Co1—O190.67 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H15···O4i0.851.942.775 (3)166.6
O1—H16···O2ii0.852.092.930 (3)170.7
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1, y, z.
 

Acknowledgements

The authors thank Heilongjiang University for supporting this study.

References

First citationDong, G.-C. & Zhang, R.-C. (2006). Acta Cryst. E62, m1847–m1849.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationMa, J.-F., Yang, J., Zheng, G.-L. & Liu, J.-F. (2003). Inorg. Chem. 42, 7531–7534.  Web of Science CSD CrossRef PubMed CAS Google Scholar
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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 65| Part 3| March 2009| Pages m313-m314
doi:10.1107/S1600536809005881
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