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Acta Cryst. (2008). E64, m1334    [ doi:10.1107/S1600536808030778 ]

catena-Poly[[bis(1-ethylimidazole-[kappa]N3)cobalt(II)]-[mu]-isophthalato-[kappa]2O1:O3\]

J. Zhao

Abstract top

In the title compound, [Co(C8H4O4)(C5H8N2)2]n, each cobalt(II) ion is coordinated by two N and two O atoms in a distorted tetrahedral geometry. The isophthalate ligands bridge the metal ions to form polymeric zigzag chains extending along the b axis. Weak C-H...O interactions contribute to the crystal packing stability.

Comment top

In the title compound (Fig. 1), the cobalt(II) ion is coordinated by two N and two O atoms in a distorted tetrahedral geometry. The values of bond distances and angles (Table 1) agree well with those observed in [Co(isophthalato)(1-H-imidazole)2] (Song, et al., 2007). Each isophthalate dianion acts as a bidentate ligand to bridge two cobalt(II) atoms through the monodentate carboxylate groups, building a zigzag chain structure along the b axis (Fig. 2). The metal-metal distance across the polymer backbone is 9.665 (7) Å. Weak C—H···O hydrogen interactions contribute to the crystal packing stability (Table 2).

Related literature top

For the crystal structures of related copper and cobalt compounds, see: Song et al. (2007).

Experimental top

The reaction of CoCl2.6H2O (1.19 g, 5 mmol) with isophthalic acid (0.83 g, 5 mmol) in a water/ethanol (3:1 v/v) solution (40 ml) at 363 K for 30 minutes produced a blue solution, to which 1-ethylimidazole (0.84 g,10 mmol) was added. The reaction solution was kept at room temperature after stirring for an hour at 333 K. Pink crystals were obtained after a few days on slow evaporation of he solvent.

Refinement top

H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93-0.97 Å and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C) for methyl H atoms.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound showing the atom numbering scheme and 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. Packing diagram of the title compound viewed down the b axis.
catena-Poly[[bis(1-ethylimidazole-κN3)cobalt(II]-µ-isophthalato- κ2O1:O3] top
Crystal data top
[Co(C8H4O4)(C5H8N2)2]F(000) = 860
Mr = 415.31Dx = 1.475 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 15.174 (3) Åθ = 10–14°
b = 9.6650 (19) ŵ = 0.95 mm−1
c = 13.183 (3) ÅT = 293 K
β = 104.63 (3)°Block, pink
V = 1870.7 (7) Å30.20 × 0.10 × 0.10 mm
Z = 4
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer		3276 independent reflections
Radiation source: fine-focus sealed tube2711 reflections with I > 2σ(I)
graphiteRint = 0.034
Thin–slice ω scansθmax = 25.2°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		h = −18→17
Tmin = 0.833, Tmax = 0.911k = 0→11
3360 measured reflectionsl = 0→15
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)] = 0.057H-atom parameters constrained
wR(F2) = 0.152 w = 1/[σ2(Fo2) + (0.08P)2 + 3.5P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
3276 reflectionsΔρmax = 0.73 e Å−3
233 parametersΔρmin = −1.49 e Å−3
40 restraintsExtinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0109 (14)
Crystal data top
[Co(C8H4O4)(C5H8N2)2]V = 1870.7 (7) Å3
Mr = 415.31Z = 4
Monoclinic, P21/cMo Kα radiation
a = 15.174 (3) ŵ = 0.95 mm−1
b = 9.6650 (19) ÅT = 293 K
c = 13.183 (3) Å0.20 × 0.10 × 0.10 mm
β = 104.63 (3)°
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer		3276 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		2711 reflections with I > 2σ(I)
Tmin = 0.833, Tmax = 0.911Rint = 0.034
3360 measured reflectionsθmax = 25.2°
Refinement top
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.152Δρmax = 0.73 e Å−3
S = 1.02Δρmin = −1.49 e Å−3
3276 reflectionsAbsolute structure: ?
233 parametersFlack parameter: ?
40 restraintsRogers parameter: ?
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
Co0.26136 (4)0.30808 (5)0.53367 (4)0.0305 (2)
O10.2699 (2)0.1668 (3)0.6419 (2)0.0427 (8)
N10.0386 (3)0.3053 (5)0.2750 (4)0.0612 (12)
C1−0.0178 (5)0.3839 (7)0.0953 (5)0.083
H1A−0.04690.35390.02540.124*
H1B0.04040.42370.09630.124*
H1C−0.05520.45180.11740.124*
N20.1440 (2)0.3249 (3)0.4223 (3)0.0393 (8)
O20.2455 (2)0.0313 (3)0.5018 (2)0.0454 (8)
C2−0.0054 (5)0.2678 (8)0.1649 (6)0.089
H2A0.03180.19910.14150.107*
H2B−0.06420.22630.16170.107*
N30.4528 (2)0.2000 (4)0.3686 (3)0.0393 (8)
C30.1228 (3)0.2707 (5)0.3287 (4)0.0561 (13)
H3A0.16160.21450.30240.067*
O30.1949 (2)−0.5482 (3)0.6821 (3)0.0489 (8)
N40.3661 (2)0.2814 (3)0.4648 (3)0.0351 (8)
C40.0695 (4)0.4016 (6)0.4269 (5)0.0667 (15)
H4A0.06510.45500.48410.080*
O40.2898 (2)−0.4975 (3)0.5853 (2)0.0401 (7)
C50.0032 (4)0.3894 (7)0.3373 (5)0.0772 (18)
H5A−0.05420.42980.32160.093*
C60.5078 (4)−0.0300 (6)0.3365 (6)0.0754 (18)
H6A0.5275−0.08540.28590.113*
H6B0.4559−0.07270.35290.113*
H6C0.5563−0.02260.39910.113*
C70.4823 (3)0.1117 (5)0.2922 (4)0.0512 (12)
H7A0.53420.15370.27380.061*
H7B0.43330.10420.22890.061*
C80.5036 (3)0.2923 (5)0.4353 (4)0.0535 (13)
H8A0.56390.31620.44000.064*
C90.4501 (3)0.3430 (5)0.4934 (4)0.0506 (12)
H9A0.46740.41000.54520.061*
C100.3710 (3)0.1963 (4)0.3889 (3)0.0386 (10)
H10A0.32320.14020.35360.046*
C110.2681 (4)−0.1647 (4)0.8394 (3)0.0476 (12)
H11A0.2741−0.15010.91050.057*
C120.2682 (3)−0.0546 (4)0.7746 (3)0.0434 (11)
H12A0.27330.03470.80180.052*
C130.2608 (3)−0.0744 (4)0.6689 (3)0.0303 (8)
C140.2555 (3)−0.2084 (4)0.6290 (3)0.0283 (8)
H14A0.2528−0.22260.55850.034*
C150.2541 (3)−0.3208 (4)0.6941 (3)0.0284 (8)
C160.2593 (3)−0.2984 (4)0.7997 (3)0.0423 (11)
H16A0.2568−0.37280.84360.051*
C170.2589 (3)0.0479 (4)0.5977 (3)0.0318 (9)
C180.2449 (3)−0.4664 (4)0.6524 (3)0.0309 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co0.0457 (4)0.0143 (3)0.0364 (3)0.0020 (2)0.0193 (2)0.0006 (2)
O10.072 (2)0.0137 (13)0.0492 (17)0.0018 (13)0.0275 (16)0.0019 (12)
N10.053 (2)0.061 (3)0.063 (3)0.017 (2)0.0013 (19)−0.015 (2)
C10.0830.0830.0830.0000.0240.000
N20.047 (2)0.0293 (18)0.0450 (19)0.0059 (15)0.0176 (16)0.0005 (15)
O20.071 (2)0.0290 (15)0.0397 (16)−0.0045 (14)0.0194 (14)0.0074 (13)
C20.0890.0890.0890.0000.0220.000
N30.045 (2)0.0357 (19)0.0419 (19)−0.0005 (16)0.0201 (16)−0.0050 (16)
C30.047 (3)0.052 (3)0.066 (3)0.012 (2)0.009 (2)−0.021 (2)
O30.066 (2)0.0172 (14)0.075 (2)−0.0053 (14)0.0375 (18)0.0017 (14)
N40.045 (2)0.0225 (16)0.0430 (19)0.0001 (14)0.0211 (16)−0.0021 (14)
C40.061 (3)0.079 (4)0.064 (3)0.027 (3)0.023 (2)−0.013 (3)
O40.069 (2)0.0155 (13)0.0435 (16)0.0009 (13)0.0284 (15)−0.0034 (12)
C50.058 (3)0.087 (4)0.084 (4)0.028 (3)0.015 (3)−0.012 (3)
C60.074 (4)0.046 (3)0.120 (5)0.007 (3)0.050 (4)−0.017 (3)
C70.053 (3)0.053 (3)0.055 (3)0.006 (2)0.027 (2)−0.013 (2)
C80.047 (3)0.061 (3)0.060 (3)−0.017 (2)0.028 (2)−0.014 (3)
C90.063 (3)0.043 (3)0.054 (3)−0.022 (2)0.031 (2)−0.017 (2)
C100.043 (2)0.030 (2)0.047 (2)−0.0020 (18)0.0191 (19)−0.0082 (19)
C110.088 (4)0.030 (2)0.029 (2)0.003 (2)0.024 (2)−0.0025 (18)
C120.082 (3)0.0154 (18)0.038 (2)0.001 (2)0.025 (2)−0.0050 (17)
C130.045 (2)0.0152 (17)0.033 (2)0.0021 (16)0.0156 (17)0.0009 (15)
C140.041 (2)0.0208 (18)0.0267 (18)0.0020 (16)0.0141 (16)−0.0008 (15)
C150.039 (2)0.0169 (18)0.033 (2)0.0019 (15)0.0156 (16)−0.0003 (15)
C160.076 (3)0.022 (2)0.036 (2)0.003 (2)0.026 (2)0.0046 (17)
C170.043 (2)0.0185 (18)0.038 (2)−0.0002 (16)0.0164 (17)0.0023 (16)
C180.045 (2)0.0134 (17)0.037 (2)0.0051 (16)0.0143 (17)0.0026 (15)
Geometric parameters (Å, °) top
Co—O11.956 (3)O4—C181.281 (5)
Co—N22.008 (4)O4—Coii2.008 (3)
Co—O4i2.008 (3)C5—H5A0.9300
Co—N42.035 (3)C6—C71.501 (8)
O1—C171.281 (5)C6—H6A0.9600
N1—C31.337 (7)C6—H6B0.9600
N1—C51.358 (7)C6—H6C0.9600
N1—C21.481 (8)C7—H7A0.9700
C1—C21.432 (9)C7—H7B0.9700
C1—H1A0.9600C8—C91.341 (7)
C1—H1B0.9600C8—H8A0.9300
C1—H1C0.9600C9—H9A0.9300
N2—C31.303 (6)C10—H10A0.9300
N2—C41.366 (6)C11—C121.365 (6)
O2—C171.239 (5)C11—C161.387 (6)
C2—H2A0.9700C11—H11A0.9300
C2—H2B0.9700C12—C131.382 (6)
N3—C101.336 (6)C12—H12A0.9300
N3—C81.349 (6)C13—C141.393 (5)
N3—C71.473 (6)C13—C171.505 (5)
C3—H3A0.9300C14—C151.387 (5)
O3—C181.227 (5)C14—H14A0.9300
N4—C101.312 (5)C15—C161.391 (6)
N4—C91.370 (6)C15—C181.505 (5)
C4—C51.350 (8)C16—H16A0.9300
C4—H4A0.9300
O1—Co—N2118.23 (14)H6A—C6—H6B109.5
O1—Co—O4i115.92 (12)C7—C6—H6C109.5
N2—Co—O4i104.31 (13)H6A—C6—H6C109.5
O1—Co—N4108.77 (13)H6B—C6—H6C109.5
N2—Co—N4109.39 (15)N3—C7—C6110.8 (4)
O4i—Co—N498.31 (13)N3—C7—H7A109.5
C17—O1—Co108.5 (2)C6—C7—H7A109.5
C3—N1—C5107.5 (5)N3—C7—H7B109.5
C3—N1—C2126.2 (5)C6—C7—H7B109.5
C5—N1—C2126.2 (5)H7A—C7—H7B108.1
C2—C1—H1A109.5C9—C8—N3106.6 (4)
C2—C1—H1B109.5C9—C8—H8A126.7
H1A—C1—H1B109.5N3—C8—H8A126.7
C2—C1—H1C109.5C8—C9—N4109.9 (4)
H1A—C1—H1C109.5C8—C9—H9A125.1
H1B—C1—H1C109.5N4—C9—H9A125.1
C3—N2—C4104.5 (4)N4—C10—N3111.8 (4)
C3—N2—Co128.4 (3)N4—C10—H10A124.1
C4—N2—Co127.0 (3)N3—C10—H10A124.1
C1—C2—N1113.0 (6)C12—C11—C16120.4 (4)
C1—C2—H2A109.0C12—C11—H11A119.8
N1—C2—H2A109.0C16—C11—H11A119.8
C1—C2—H2B109.0C11—C12—C13120.6 (4)
N1—C2—H2B109.0C11—C12—H12A119.7
H2A—C2—H2B107.8C13—C12—H12A119.7
C10—N3—C8107.1 (4)C12—C13—C14119.5 (3)
C10—N3—C7125.4 (4)C12—C13—C17120.3 (3)
C8—N3—C7127.4 (4)C14—C13—C17120.3 (3)
N2—C3—N1112.1 (4)C15—C14—C13120.2 (3)
N2—C3—H3A124.0C15—C14—H14A119.9
N1—C3—H3A124.0C13—C14—H14A119.9
C10—N4—C9104.7 (3)C14—C15—C16119.4 (3)
C10—N4—Co128.3 (3)C14—C15—C18121.4 (3)
C9—N4—Co126.8 (3)C16—C15—C18119.2 (3)
C5—C4—N2110.8 (5)C11—C16—C15119.8 (4)
C5—C4—H4A124.6C11—C16—H16A120.1
N2—C4—H4A124.6C15—C16—H16A120.1
C18—O4—Coii110.3 (2)O2—C17—O1123.3 (3)
C4—C5—N1105.1 (5)O2—C17—C13120.5 (3)
C4—C5—H5A127.4O1—C17—C13116.2 (3)
N1—C5—H5A127.4O3—C18—O4123.3 (4)
C7—C6—H6A109.5O3—C18—C15119.6 (3)
C7—C6—H6B109.5O4—C18—C15117.1 (3)
N2—Co—O1—C1761.4 (3)N3—C8—C9—N41.0 (6)
O4i—Co—O1—C17−173.7 (3)C10—N4—C9—C8−0.8 (6)
N4—Co—O1—C17−64.1 (3)Co—N4—C9—C8175.2 (3)
O1—Co—N2—C3−95.9 (4)C9—N4—C10—N30.4 (5)
O4i—Co—N2—C3133.6 (4)Co—N4—C10—N3−175.6 (3)
N4—Co—N2—C329.3 (5)C8—N3—C10—N40.2 (5)
O1—Co—N2—C487.1 (4)C7—N3—C10—N4176.4 (4)
O4i—Co—N2—C4−43.4 (5)C16—C11—C12—C13−1.0 (8)
N4—Co—N2—C4−147.7 (4)C11—C12—C13—C14−1.6 (7)
C3—N1—C2—C1−110.4 (7)C11—C12—C13—C17178.7 (4)
C5—N1—C2—C164.5 (9)C12—C13—C14—C152.4 (6)
C4—N2—C3—N1−1.7 (6)C17—C13—C14—C15−177.8 (4)
Co—N2—C3—N1−179.2 (3)C13—C14—C15—C16−0.8 (6)
C5—N1—C3—N21.0 (7)C13—C14—C15—C18177.7 (4)
C2—N1—C3—N2176.6 (5)C12—C11—C16—C152.6 (8)
O1—Co—N4—C1083.3 (4)C14—C15—C16—C11−1.7 (7)
N2—Co—N4—C10−47.2 (4)C18—C15—C16—C11179.8 (4)
O4i—Co—N4—C10−155.7 (4)Co—O1—C17—O20.2 (5)
O1—Co—N4—C9−91.9 (4)Co—O1—C17—C13−178.5 (3)
N2—Co—N4—C9137.7 (4)C12—C13—C17—O2−174.6 (4)
O4i—Co—N4—C929.2 (4)C14—C13—C17—O25.6 (6)
C3—N2—C4—C51.8 (7)C12—C13—C17—O14.0 (6)
Co—N2—C4—C5179.4 (4)C14—C13—C17—O1−175.7 (4)
N2—C4—C5—N1−1.3 (8)Coii—O4—C18—O32.6 (5)
C3—N1—C5—C40.2 (7)Coii—O4—C18—C15−176.4 (3)
C2—N1—C5—C4−175.5 (6)C14—C15—C18—O3−138.0 (4)
C10—N3—C7—C6−78.9 (6)C16—C15—C18—O340.5 (6)
C8—N3—C7—C696.6 (6)C14—C15—C18—O441.0 (6)
C10—N3—C8—C9−0.7 (6)C16—C15—C18—O4−140.5 (4)
C7—N3—C8—C9−176.8 (5)
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C12—H12A···O10.932.452.768 (5)100
C3—H3A···O3iii0.932.403.260 (6)154
C5—H5A···O3iv0.932.413.327 (7)168
Symmetry codes: (iii) x, −y−1/2, z−1/2; (iv) −x, −y, −z+1.
Table 1
Selected geometric parameters (Å, °) top
Co—O11.956 (3)Co—O4i2.008 (3)
Co—N22.008 (4)Co—N42.035 (3)
O1—Co—N2118.23 (14)O1—Co—N4108.77 (13)
O1—Co—O4i115.92 (12)N2—Co—N4109.39 (15)
N2—Co—O4i104.31 (13)O4i—Co—N498.31 (13)
Symmetry codes: (i) x, y+1, z.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C12—H12A···O10.932.452.768 (5)100
C3—H3A···O3ii0.932.403.260 (6)154
C5—H5A···O3iii0.932.413.327 (7)168
Symmetry codes: (ii) x, −y−1/2, z−1/2; (iii) −x, −y, −z+1.
Acknowledgements top

This work was supported by the National Natural Science Foundation of China (grant No. 20601015) and the Natural Science Foundation of Shandong Province (Y2006B12).

references
References top

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.

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

Song, J., Chen, Y., Li, Z., Zhou, R., Xu, X. & Xu, J. (2007). J. Mol. Struct. 842, 125–131.