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

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catena-Poly[[(2,2′-bi­pyridine-κ2N,N′)cobalt(II)]-μ-oxalato-κ4O1,O2:O1′,O2′]

aCollege of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, People's Republic of China, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 14 September 2009; accepted 18 September 2009; online 26 September 2009)

In the title compound, [Co(C2O4)(C10H8N2)]n, the oxalate group chelates two adjacent metal atoms, resulting in a zigzag chain running along the a axis. The CoII centre exists in an all cis-octa­hedral coordination geometry.

Related literature

The Mn(II), Fe(II), Ni(II), Cu(II) and Zn(II) analogs are isostructural; see: Deguenon et al. (1990[Deguenon, D., Bernardinelli, G., Tucahgues, J. P. & Castan, P. (1990). Inorg. Chem. 29, 3031-3037.]); Fun et al. (1999[Fun, H.-K., Shanmuga Sundara Raj, S., Fang, X., Zheng, L.-M. & Xin, X.-Q. (1999). Acta Cryst. C55, 903-905.]); Lin et al. (2006[Lin, X.-R., Ye, B.-Z., Liu, J.-S., Wei, C.-X. & Chen, J.-X. (2006). Acta Cryst. E62, m2130-m2132.]); Luo et al. (2001[Luo, J.-H., Hong, M.-C., Liang, Y.-C. & Cao, R. (2001). Acta Cryst. E57, m361-m362.]); Yu et al. (2006[Yu, J.-H., Bi, M.-H., Lu, Z.-L., Zhang, X., Qu, X.-J., Lu, J. & Xu, J.-Q. (2006). J. Mol. Struct. 800, 69-73.]).

[Scheme 1]

Experimental

Crystal data
  • [Co(C2O4)(C10H8N2)]

  • Mr = 303.13

  • Orthorhombic, P n a 21

  • a = 9.1275 (8) Å

  • b = 9.2323 (8) Å

  • c = 14.1929 (12) Å

  • V = 1196.00 (18) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.45 mm−1

  • T = 293 K

  • 0.36 × 0.25 × 0.18 mm

Data collection
  • Bruker APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.624, Tmax = 0.781

  • 9371 measured reflections

  • 2698 independent reflections

  • 2456 reflections with I > 2σ(I)

  • Rint = 0.025

Refinement
  • R[F2 > 2σ(F2)] = 0.026

  • wR(F2) = 0.068

  • S = 1.01

  • 2698 reflections

  • 172 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.17 e Å−3

  • Δρmin = −0.23 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1277 Friedel pairs

  • Flack parameter: −0.02 (2)

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Comment top

The oxalate group chelates two adjacent metal atoms in Co(C10H8N2)(C2O4) resulting in a zigzag chain running along the a-axis of the orthorhombic unit cell. The cobalt atom exists in an all cis-octahedral coordination geometry.

Related literature top

The Mn(II), Fe(II), Ni(II), Cu(II) and Zn(II) analogs are isostructural; see: Deguenon et al. (1990); Fun et al. (1999); Lin et al. (2006); Luo et al. (2001); Yu et al. (2006).

Experimental top

An aqueous solution of 2M sodium hydroxide (0.2 ml) was added to a water/DMF (2:7 v/v) solution (9 ml) of cobalt(II) oxalate dihdyrate (0.01 g, 0.05 mmol) and 2,2'-bipyridine (0.01 g, 0.05 mmol). Pink blocks separated from the solution after several days in 30% yield. CH&N elemental analysis. Calculated for C12H8CoN2O4: C 47.55, H 2.66, N 9.24%. Found: C 47.27, H 2.94, N 9.40%.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of a section of the chain structure of Co(C10H8N2)(C2O4) at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
catena-Poly[[(2,2'-bipyridine-κ2N,N')cobalt(II)]-µ- oxalato-κ4O1,O2:O1',O2'] top
Crystal data top
[Co(C2O4)(C10H8N2)]F(000) = 612
Mr = 303.13Dx = 1.683 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 4493 reflections
a = 9.1275 (8) Åθ = 2.6–26.1°
b = 9.2323 (8) ŵ = 1.45 mm1
c = 14.1929 (12) ÅT = 293 K
V = 1196.00 (18) Å3Prism, pink
Z = 40.36 × 0.25 × 0.18 mm
Data collection top
Bruker APEXII
diffractometer
2698 independent reflections
Radiation source: fine-focus sealed tube2456 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
ϕ and ω scansθmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.624, Tmax = 0.781k = 1111
9371 measured reflectionsl = 1818
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)] = 0.026H-atom parameters constrained
wR(F2) = 0.068 w = 1/[σ2(Fo2) + (0.0436P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
2698 reflectionsΔρmax = 0.17 e Å3
172 parametersΔρmin = 0.23 e Å3
1 restraintAbsolute structure: Flack (1983), 1277 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.02 (2)
Crystal data top
[Co(C2O4)(C10H8N2)]V = 1196.00 (18) Å3
Mr = 303.13Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 9.1275 (8) ŵ = 1.45 mm1
b = 9.2323 (8) ÅT = 293 K
c = 14.1929 (12) Å0.36 × 0.25 × 0.18 mm
Data collection top
Bruker APEXII
diffractometer
2698 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2456 reflections with I > 2σ(I)
Tmin = 0.624, Tmax = 0.781Rint = 0.025
9371 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.026H-atom parameters constrained
wR(F2) = 0.068Δρmax = 0.17 e Å3
S = 1.01Δρmin = 0.23 e Å3
2698 reflectionsAbsolute structure: Flack (1983), 1277 Friedel pairs
172 parametersAbsolute structure parameter: 0.02 (2)
1 restraint
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Co10.38104 (3)0.58866 (2)0.49966 (4)0.03408 (9)
N10.3016 (2)0.4155 (2)0.41608 (15)0.0413 (5)
N20.4481 (2)0.40387 (19)0.57666 (14)0.0390 (4)
O10.27899 (18)0.75569 (19)0.42055 (11)0.0445 (4)
O20.07533 (18)0.88996 (17)0.42286 (12)0.0409 (4)
O30.19137 (17)0.61940 (16)0.57821 (11)0.0389 (3)
O40.00808 (15)0.75786 (19)0.58323 (12)0.0449 (4)
C10.2256 (3)0.4294 (3)0.3354 (2)0.0551 (7)
H10.19950.52180.31530.066*
C20.1847 (3)0.3113 (4)0.2810 (2)0.0674 (8)
H20.13340.32400.22500.081*
C30.2216 (4)0.1757 (4)0.3117 (2)0.0710 (9)
H30.19540.09480.27650.085*
C40.2974 (3)0.1594 (3)0.3946 (2)0.0574 (7)
H40.32220.06750.41620.069*
C50.3367 (3)0.2817 (3)0.44589 (16)0.0385 (5)
C60.4169 (3)0.2747 (3)0.53643 (18)0.0390 (5)
C70.4574 (4)0.1460 (3)0.5795 (2)0.0583 (7)
H70.43590.05780.55110.070*
C80.5303 (4)0.1498 (4)0.6653 (2)0.0661 (8)
H80.55870.06420.69470.079*
C90.5598 (3)0.2808 (4)0.70638 (19)0.0635 (8)
H90.60750.28570.76420.076*
C100.5172 (3)0.4054 (3)0.6601 (2)0.0531 (7)
H1100.53730.49440.68800.064*
C110.1593 (2)0.7943 (2)0.45489 (15)0.0329 (4)
C120.1106 (2)0.7173 (3)0.54720 (15)0.0329 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.03270 (14)0.03499 (14)0.03454 (13)0.00016 (11)0.00143 (14)0.00307 (16)
N10.0463 (11)0.0436 (11)0.0339 (10)0.0047 (8)0.0038 (8)0.0021 (8)
N20.0408 (11)0.0406 (11)0.0356 (10)0.0037 (8)0.0018 (8)0.0021 (8)
O10.0411 (9)0.0516 (10)0.0409 (9)0.0057 (7)0.0145 (8)0.0104 (8)
O20.0398 (8)0.0430 (9)0.0401 (9)0.0032 (7)0.0070 (7)0.0130 (7)
O30.0377 (8)0.0401 (8)0.0388 (8)0.0037 (7)0.0054 (7)0.0105 (7)
O40.0397 (9)0.0536 (10)0.0413 (9)0.0093 (7)0.0125 (8)0.0179 (8)
C10.0618 (17)0.0630 (17)0.0404 (13)0.0075 (13)0.0131 (12)0.0006 (12)
C20.0740 (19)0.085 (2)0.0435 (15)0.0175 (17)0.0170 (14)0.0103 (14)
C30.082 (2)0.069 (2)0.0628 (18)0.0255 (17)0.0066 (16)0.0259 (16)
C40.0692 (18)0.0465 (15)0.0565 (16)0.0145 (13)0.0005 (14)0.0107 (12)
C50.0407 (11)0.0403 (12)0.0346 (12)0.0044 (11)0.0034 (10)0.0051 (10)
C60.0429 (12)0.0341 (11)0.0402 (12)0.0035 (10)0.0077 (10)0.0023 (9)
C70.0777 (19)0.0428 (14)0.0544 (15)0.0149 (14)0.0004 (15)0.0044 (13)
C80.086 (2)0.0576 (17)0.0546 (16)0.0271 (16)0.0024 (16)0.0105 (15)
C90.0727 (18)0.077 (2)0.0406 (15)0.0236 (16)0.0064 (13)0.0052 (14)
C100.0622 (17)0.0555 (16)0.0416 (13)0.0124 (12)0.0082 (13)0.0062 (11)
C110.0342 (10)0.0332 (11)0.0312 (10)0.0055 (10)0.0024 (9)0.0017 (9)
C120.0318 (11)0.0349 (11)0.0321 (11)0.0025 (9)0.0030 (8)0.0025 (9)
Geometric parameters (Å, º) top
Co1—O32.0786 (16)C1—H10.9300
Co1—O2i2.0909 (16)C2—C31.367 (5)
Co1—O4i2.1068 (16)C2—H20.9300
Co1—N12.119 (2)C3—C41.374 (5)
Co1—N22.1165 (19)C3—H30.9300
Co1—O12.1228 (17)C4—C51.391 (4)
N1—C11.344 (3)C4—H40.9300
N1—C51.344 (3)C5—C61.480 (3)
N2—C101.342 (3)C6—C71.386 (4)
N2—C61.352 (3)C7—C81.388 (4)
O1—C111.248 (3)C7—H70.9300
O2—C111.255 (3)C8—C91.369 (5)
O2—Co1ii2.0909 (16)C8—H80.9300
O3—C121.247 (3)C9—C101.381 (4)
O4—C121.255 (2)C9—H90.9300
O4—Co1ii2.1068 (16)C10—H1100.9300
C1—C21.388 (4)C11—C121.555 (2)
O3—Co1—O2i166.68 (6)C2—C3—C4119.8 (3)
O3—Co1—O4i90.36 (6)C2—C3—H3120.1
O2i—Co1—O4i79.78 (6)C4—C3—H3120.1
O3—Co1—N196.78 (8)C3—C4—C5119.3 (3)
O2i—Co1—N194.00 (7)C3—C4—H4120.4
O4i—Co1—N1170.80 (7)C5—C4—H4120.4
O3—Co1—N294.24 (7)N1—C5—C4121.3 (2)
O2i—Co1—N295.74 (7)N1—C5—C6115.6 (2)
O4i—Co1—N296.46 (8)C4—C5—C6123.1 (3)
N1—Co1—N277.29 (7)N2—C6—C7120.9 (3)
O3—Co1—O179.57 (6)N2—C6—C5115.6 (2)
O2i—Co1—O191.60 (7)C7—C6—C5123.5 (3)
O4i—Co1—O191.15 (7)C8—C7—C6119.6 (3)
N1—Co1—O195.83 (8)C8—C7—H7120.2
N2—Co1—O1170.25 (7)C6—C7—H7120.2
C1—N1—C5118.6 (2)C9—C8—C7119.3 (3)
C1—N1—Co1125.54 (18)C9—C8—H8120.3
C5—N1—Co1115.80 (17)C7—C8—H8120.3
C10—N2—C6118.8 (2)C8—C9—C10118.6 (3)
C10—N2—Co1125.67 (16)C8—C9—H9120.7
C6—N2—Co1115.58 (17)C10—C9—H9120.7
C11—O1—Co1112.63 (14)N2—C10—C9122.9 (3)
C11—O2—Co1ii113.30 (14)N2—C10—H110118.5
C12—O3—Co1113.72 (14)C9—C10—H110118.5
C12—O4—Co1ii112.70 (15)O1—C11—O2126.4 (2)
N1—C1—C2122.5 (3)O1—C11—C12116.67 (18)
N1—C1—H1118.8O2—C11—C12116.88 (17)
C2—C1—H1118.8O3—C12—O4125.7 (2)
C3—C2—C1118.5 (3)O3—C12—C11117.35 (17)
C3—C2—H2120.8O4—C12—C11116.98 (18)
C1—C2—H2120.8
O3—Co1—N1—C186.2 (2)C1—N1—C5—C6178.5 (2)
O2i—Co1—N1—C186.0 (2)Co1—N1—C5—C64.1 (3)
N2—Co1—N1—C1179.0 (2)C3—C4—C5—N10.2 (4)
O1—Co1—N1—C16.0 (2)C3—C4—C5—C6179.3 (3)
O3—Co1—N1—C596.68 (18)C10—N2—C6—C71.1 (4)
O2i—Co1—N1—C591.16 (18)Co1—N2—C6—C7179.0 (2)
N2—Co1—N1—C53.84 (18)C10—N2—C6—C5178.2 (2)
O1—Co1—N1—C5176.83 (18)Co1—N2—C6—C51.7 (3)
O3—Co1—N2—C1081.0 (2)N1—C5—C6—N21.6 (3)
O2i—Co1—N2—C1090.2 (2)C4—C5—C6—N2179.2 (3)
O4i—Co1—N2—C109.8 (2)N1—C5—C6—C7177.7 (3)
N1—Co1—N2—C10177.0 (2)C4—C5—C6—C71.5 (4)
O3—Co1—N2—C698.92 (19)N2—C6—C7—C80.4 (5)
O2i—Co1—N2—C689.91 (18)C5—C6—C7—C8178.9 (2)
O4i—Co1—N2—C6170.23 (18)C6—C7—C8—C90.5 (5)
N1—Co1—N2—C62.91 (19)C7—C8—C9—C100.7 (5)
O3—Co1—O1—C110.09 (16)C6—N2—C10—C90.9 (4)
O2i—Co1—O1—C11169.87 (16)Co1—N2—C10—C9179.2 (2)
O4i—Co1—O1—C1190.06 (16)C8—C9—C10—N20.0 (4)
N1—Co1—O1—C1195.94 (17)Co1—O1—C11—O2179.71 (19)
O2i—Co1—O3—C1247.6 (4)Co1—O1—C11—C121.1 (2)
O4i—Co1—O3—C1289.55 (17)Co1ii—O2—C11—O1177.06 (19)
N1—Co1—O3—C1296.27 (17)Co1ii—O2—C11—C123.8 (2)
N2—Co1—O3—C12173.95 (17)Co1—O3—C12—O4178.58 (19)
O1—Co1—O3—C121.55 (16)Co1—O3—C12—C112.6 (2)
C5—N1—C1—C21.3 (4)Co1ii—O4—C12—O3174.00 (19)
Co1—N1—C1—C2175.8 (2)Co1ii—O4—C12—C114.9 (2)
N1—C1—C2—C30.9 (5)O1—C11—C12—O32.6 (3)
C1—C2—C3—C40.0 (5)O2—C11—C12—O3178.2 (2)
C2—C3—C4—C50.5 (5)O1—C11—C12—O4178.4 (2)
C1—N1—C5—C40.7 (4)O2—C11—C12—O40.8 (3)
Co1—N1—C5—C4176.7 (2)
Symmetry codes: (i) x+1/2, y+3/2, z; (ii) x1/2, y+3/2, z.

Experimental details

Crystal data
Chemical formula[Co(C2O4)(C10H8N2)]
Mr303.13
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)293
a, b, c (Å)9.1275 (8), 9.2323 (8), 14.1929 (12)
V3)1196.00 (18)
Z4
Radiation typeMo Kα
µ (mm1)1.45
Crystal size (mm)0.36 × 0.25 × 0.18
Data collection
DiffractometerBruker APEXII
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.624, 0.781
No. of measured, independent and
observed [I > 2σ(I)] reflections
9371, 2698, 2456
Rint0.025
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.026, 0.068, 1.01
No. of reflections2698
No. of parameters172
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.17, 0.23
Absolute structureFlack (1983), 1277 Friedel pairs
Absolute structure parameter0.02 (2)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

 

Acknowledgements

We thank Yangzhou University and the University of Malaya for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationDeguenon, D., Bernardinelli, G., Tucahgues, J. P. & Castan, P. (1990). Inorg. Chem. 29, 3031–3037.  CSD CrossRef CAS Web of Science Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationFun, H.-K., Shanmuga Sundara Raj, S., Fang, X., Zheng, L.-M. & Xin, X.-Q. (1999). Acta Cryst. C55, 903–905.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationLin, X.-R., Ye, B.-Z., Liu, J.-S., Wei, C.-X. & Chen, J.-X. (2006). Acta Cryst. E62, m2130–m2132.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationLuo, J.-H., Hong, M.-C., Liang, Y.-C. & Cao, R. (2001). Acta Cryst. E57, m361–m362.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar
First citationYu, J.-H., Bi, M.-H., Lu, Z.-L., Zhang, X., Qu, X.-J., Lu, J. & Xu, J.-Q. (2006). J. Mol. Struct. 800, 69–73.  Web of Science CSD CrossRef CAS Google Scholar

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