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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): m1284.
Published online 2010 September 18. doi:  10.1107/S1600536810036846
PMCID: PMC2983300

Dichlorido(6,6′-dimethyl-2,2′-bipyridine-κ2 N,N′)cobalt(II)

Abstract

In the title compound, [CoCl2(C12H12N2)], the CoII atom is four-coordinated in a distorted tetra­hedral geometry by two N atoms from a 6,6′-dimethyl-2,2′-bipyridine ligand and two terminal Cl atoms. Inter­molecular C—H(...)Cl hydrogen bonds and π–π stacking inter­actions between the pyridine rings [centroid–centroid distances = 3.788 (1) and 3.957 (1) Å] are present in the crystal structure.

Related literature

For related structures, see: Akbarzadeh Torbati et al. (2010 [triangle]); Alizadeh et al. (2010 [triangle]); Alizadeh, Kalateh, Ebadi et al. (2009 [triangle]); Alizadeh, Kalateh, Khoshtarkib et al. (2009 [triangle]); Alizadeh, Khoshtarkib et al. (2009 [triangle]); Baker et al. (1988 [triangle]); Itoh et al. (2005 [triangle]); Kou et al. (2008 [triangle]); Onggo et al. (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1284-scheme1.jpg

Experimental

Crystal data

  • [CoCl2(C12H12N2)]
  • M r = 314.07
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1284-efi1.jpg
  • a = 7.6292 (14) Å
  • b = 9.8034 (14) Å
  • c = 17.980 (4) Å
  • β = 93.990 (15)°
  • V = 1341.5 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.66 mm−1
  • T = 298 K
  • 0.50 × 0.19 × 0.13 mm

Data collection

  • Bruker APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.690, T max = 0.810
  • 10258 measured reflections
  • 3609 independent reflections
  • 2642 reflections with I > 2σ(I)
  • R int = 0.100

Refinement

  • R[F 2 > 2σ(F 2)] = 0.064
  • wR(F 2) = 0.226
  • S = 1.13
  • 3609 reflections
  • 154 parameters
  • H-atom parameters constrained
  • Δρmax = 0.47 e Å−3
  • Δρmin = −0.92 e Å−3

Data collection: SMART (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

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

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810036846/hy2353sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810036846/hy2353Isup2.hkl

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

Acknowledgments

We are grateful to the University of Sistan and Baluchestan, and Shahid Beheshti University for financial support.

supplementary crystallographic information

Comment

6,6'-Dimethyl-2,2'-bipyridine (6,6'-dmbipy) is a good bidentate ligand, and numerous complexes with 6,6'-dmbipy have been prepared, such as that of zinc (Alizadeh, Kalateh, Ebadi et al., 2009; Alizadeh, Kalateh, Khoshtarkib et al., 2009; Alizadeh, Khoshtarkib et al., 2009), copper (Itoh et al., 2005), nickel (Kou et al., 2008), cadmium (Alizadeh et al., 2010) and ruthenium (Onggo et al., 2005). We report here the synthesis and crystal structure of the title compound.

In the title compound (Fig. 1), the CoII atom is four-coordinated in a distorted tetrahedral geometry by two N atoms from a 6,6'-dmbipy ligand and two terminal Cl atoms. The Co—N and Co—Cl bond lengths and angles (Table 1) are within normal range as observed in [Co(6,6'-dmbpy)Cl2].1/2(C6H6) (Baker et al., 1988) and [Co(dmphen)Cl2] (dmphen = 2,9-dimethyl-1,10-phenanthroline) (Akbarzadeh Torbati et al., 2010) .

In the crystal structure, intermolecular C—H···Cl hydrogen bonds (Table 2) and π–π contacts (Fig. 2) between the pyridine rings, Cg1···Cg2i and Cg1···Cg2ii [symmetry codes: (i) 1-x, 1-y, 1-z; (ii) -x, 1-y, 1-z. Cg1 and Cg2 are the centroids of the N1, C2–C6 ring and N2, C7–C11 ring], stabilize the structure, with centroid–centroid distances of 3.788 (1) and 3.957 (1) Å.

Experimental

For the preparation of the title compound, a solution of 6,6'-dmbipy (0.25 g, 1.34 mmol) in methanol (15 ml) was added to a solution of CoCl2.6H2O (0.37 g, 1.34 mmol) in acetonitrile (15 ml) and the resulting blue solution was stirred for 15 min at 313 K. This solution was left to evaporate slowly at room temperature. After one week, blue block crystals of the title compound were isolated (yield: 0.32 g, 76%).

Refinement

All H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 (aromatic) and 0.96 (methyl) Å and with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
Crystal packing diagram for the title compound. Dashed lines denote hydrogen bonds.

Crystal data

[CoCl2(C12H12N2)]F(000) = 636
Mr = 314.07Dx = 1.555 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1009 reflections
a = 7.6292 (14) Åθ = 2.3–29.3°
b = 9.8034 (14) ŵ = 1.66 mm1
c = 17.980 (4) ÅT = 298 K
β = 93.990 (15)°Block, blue
V = 1341.5 (4) Å30.50 × 0.19 × 0.13 mm
Z = 4

Data collection

Bruker APEX CCD diffractometer3609 independent reflections
Radiation source: fine-focus sealed tube2642 reflections with I > 2σ(I)
graphiteRint = 0.100
[var phi] and ω scansθmax = 29.3°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −10→10
Tmin = 0.690, Tmax = 0.810k = −13→11
10258 measured reflectionsl = −24→24

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)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.226H-atom parameters constrained
S = 1.13w = 1/[σ2(Fo2) + (0.1251P)2 + 0.225P] where P = (Fo2 + 2Fc2)/3
3609 reflections(Δ/σ)max < 0.001
154 parametersΔρmax = 0.47 e Å3
0 restraintsΔρmin = −0.92 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
C10.3248 (9)0.4581 (6)0.2579 (3)0.0900 (16)
H1A0.43690.46680.23730.108*
H1B0.23380.48660.22170.108*
H1C0.30610.36460.27120.108*
C20.3209 (6)0.5449 (5)0.3254 (3)0.0654 (10)
C30.3451 (8)0.6844 (6)0.3227 (4)0.0832 (15)
H30.36560.72640.27770.100*
C40.3390 (8)0.7594 (5)0.3849 (4)0.0857 (16)
H40.35920.85290.38350.103*
C50.3022 (7)0.6964 (5)0.4517 (4)0.0778 (14)
H50.29450.74750.49500.093*
C60.2773 (5)0.5568 (4)0.4525 (2)0.0572 (9)
C70.2356 (5)0.4790 (4)0.5193 (2)0.0544 (8)
C80.2233 (6)0.5387 (6)0.5874 (3)0.0719 (12)
H80.24620.63120.59400.086*
C90.1762 (7)0.4593 (7)0.6459 (3)0.0807 (14)
H90.16370.49850.69240.097*
C100.1481 (7)0.3233 (7)0.6357 (3)0.0765 (13)
H100.11560.26930.67490.092*
C110.1681 (7)0.2654 (5)0.5660 (3)0.0661 (10)
C120.1486 (11)0.1176 (6)0.5507 (4)0.100 (2)
H12A0.03190.08920.56030.120*
H12B0.23240.06780.58240.120*
H12C0.16880.10000.49950.120*
N10.2875 (4)0.4836 (3)0.38883 (19)0.0537 (7)
N20.2096 (4)0.3440 (4)0.50901 (18)0.0541 (7)
Co10.24226 (7)0.28007 (5)0.40212 (3)0.0549 (2)
Cl10.47387 (17)0.14706 (13)0.38988 (8)0.0811 (4)
Cl20.01041 (17)0.19582 (14)0.33528 (8)0.0769 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.124 (4)0.079 (3)0.071 (3)−0.003 (3)0.029 (3)0.007 (3)
C20.068 (2)0.058 (2)0.071 (3)−0.0068 (19)0.0113 (19)0.0074 (19)
C30.089 (3)0.064 (3)0.097 (4)−0.021 (3)0.006 (3)0.021 (3)
C40.096 (4)0.049 (2)0.111 (5)−0.018 (2)0.003 (3)0.005 (3)
C50.084 (3)0.058 (2)0.090 (3)−0.010 (2)−0.006 (3)−0.013 (2)
C60.0507 (17)0.0491 (19)0.072 (2)0.0005 (15)0.0021 (16)−0.0091 (17)
C70.0490 (17)0.059 (2)0.0559 (19)0.0040 (15)0.0048 (14)−0.0108 (16)
C80.075 (3)0.074 (3)0.068 (3)0.002 (2)0.010 (2)−0.019 (2)
C90.082 (3)0.095 (4)0.066 (3)0.009 (3)0.011 (2)−0.018 (3)
C100.073 (3)0.099 (4)0.058 (2)0.006 (3)0.009 (2)0.010 (2)
C110.073 (3)0.069 (3)0.057 (2)0.001 (2)0.0055 (18)0.0050 (19)
C120.154 (6)0.071 (3)0.077 (3)−0.019 (4)0.017 (4)0.014 (3)
N10.0525 (15)0.0479 (16)0.0617 (17)−0.0034 (13)0.0120 (13)−0.0002 (13)
N20.0572 (16)0.0543 (17)0.0512 (16)0.0003 (14)0.0072 (13)−0.0035 (13)
Co10.0631 (4)0.0453 (3)0.0569 (4)−0.0020 (2)0.0095 (2)−0.0053 (2)
Cl10.0798 (7)0.0659 (7)0.0979 (9)0.0142 (6)0.0080 (6)−0.0239 (6)
Cl20.0753 (7)0.0790 (7)0.0759 (7)−0.0148 (6)0.0013 (5)−0.0134 (6)

Geometric parameters (Å, °)

C1—C21.483 (7)C8—C91.377 (8)
C1—H1A0.9600C8—H80.9300
C1—H1B0.9600C9—C101.361 (9)
C1—H1C0.9600C9—H90.9300
C2—N11.330 (5)C10—C111.393 (7)
C2—C31.382 (7)C10—H100.9300
C3—C41.342 (9)C11—N21.338 (6)
C3—H30.9300C11—C121.480 (8)
C4—C51.397 (9)C12—H12A0.9600
C4—H40.9300C12—H12B0.9600
C5—C61.382 (6)C12—H12C0.9600
C5—H50.9300Co1—N12.042 (3)
C6—N11.358 (5)Co1—N22.053 (3)
C6—C71.477 (6)Co1—Cl12.2193 (13)
C7—N21.349 (5)Co1—Cl22.2269 (13)
C7—C81.365 (5)
C2—C1—H1A109.5C10—C9—C8119.8 (5)
C2—C1—H1B109.5C10—C9—H9120.1
H1A—C1—H1B109.5C8—C9—H9120.1
C2—C1—H1C109.5C9—C10—C11119.7 (5)
H1A—C1—H1C109.5C9—C10—H10120.2
H1B—C1—H1C109.5C11—C10—H10120.2
N1—C2—C3120.7 (5)N2—C11—C10120.0 (5)
N1—C2—C1117.3 (4)N2—C11—C12116.6 (4)
C3—C2—C1121.9 (5)C10—C11—C12123.4 (5)
C4—C3—C2120.0 (5)C11—C12—H12A109.5
C4—C3—H3120.0C11—C12—H12B109.5
C2—C3—H3120.0H12A—C12—H12B109.5
C3—C4—C5119.7 (5)C11—C12—H12C109.5
C3—C4—H4120.1H12A—C12—H12C109.5
C5—C4—H4120.1H12B—C12—H12C109.5
C6—C5—C4118.8 (5)C2—N1—C6120.7 (4)
C6—C5—H5120.6C2—N1—Co1125.8 (3)
C4—C5—H5120.6C6—N1—Co1113.5 (3)
N1—C6—C5120.0 (5)C11—N2—C7120.0 (4)
N1—C6—C7116.2 (3)C11—N2—Co1126.3 (3)
C5—C6—C7123.9 (4)C7—N2—Co1113.7 (3)
N2—C7—C8121.6 (4)N1—Co1—N281.00 (14)
N2—C7—C6115.7 (3)N1—Co1—Cl1114.87 (10)
C8—C7—C6122.7 (4)N2—Co1—Cl1114.93 (10)
C7—C8—C9118.8 (5)N1—Co1—Cl2115.70 (10)
C7—C8—H8120.6N2—Co1—Cl2118.35 (10)
C9—C8—H8120.6Cl1—Co1—Cl2109.67 (5)
N1—C2—C3—C41.6 (8)C5—C6—N1—Co1−179.0 (3)
C1—C2—C3—C4179.4 (6)C7—C6—N1—Co1−0.2 (4)
C2—C3—C4—C5−2.2 (9)C10—C11—N2—C71.3 (7)
C3—C4—C5—C61.7 (9)C12—C11—N2—C7−177.7 (5)
C4—C5—C6—N1−0.5 (7)C10—C11—N2—Co1−179.2 (4)
C4—C5—C6—C7−179.2 (5)C12—C11—N2—Co11.7 (7)
N1—C6—C7—N2−1.0 (5)C8—C7—N2—C111.0 (6)
C5—C6—C7—N2177.7 (4)C6—C7—N2—C11−178.9 (4)
N1—C6—C7—C8179.2 (4)C8—C7—N2—Co1−178.5 (3)
C5—C6—C7—C8−2.1 (6)C6—C7—N2—Co11.6 (4)
N2—C7—C8—C9−2.6 (7)C2—N1—Co1—N2−178.0 (3)
C6—C7—C8—C9177.2 (4)C6—N1—Co1—N20.8 (3)
C7—C8—C9—C101.9 (8)C2—N1—Co1—Cl168.6 (3)
C8—C9—C10—C110.4 (8)C6—N1—Co1—Cl1−112.6 (2)
C9—C10—C11—N2−2.0 (8)C2—N1—Co1—Cl2−60.8 (3)
C9—C10—C11—C12177.0 (6)C6—N1—Co1—Cl2118.0 (2)
C3—C2—N1—C6−0.4 (7)C11—N2—Co1—N1179.2 (4)
C1—C2—N1—C6−178.3 (4)C7—N2—Co1—N1−1.4 (3)
C3—C2—N1—Co1178.3 (4)C11—N2—Co1—Cl1−67.5 (4)
C1—C2—N1—Co10.4 (6)C7—N2—Co1—Cl1111.9 (3)
C5—C6—N1—C2−0.1 (6)C11—N2—Co1—Cl264.7 (4)
C7—C6—N1—C2178.7 (3)C7—N2—Co1—Cl2−115.8 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C5—H5···Cl1i0.932.823.565 (7)138

Symmetry codes: (i) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2353).

References

  • Akbarzadeh Torbati, N., Rezvani, A. R., Safari, N., Amani, V. & Khavasi, H. R. (2010). Acta Cryst. E66, m1236. [PMC free article] [PubMed]
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  • Alizadeh, R., Khoshtarkib, Z., Chegeni, K., Ebadi, A. & Amani, V. (2009). Acta Cryst. E65, m1311. [PMC free article] [PubMed]
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  • Bruker (2001). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
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  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
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  • Onggo, D., Scudder, M. L., Craig, D. C. & Goodwin, H. A. (2005). J. Mol. Struct.738, 129–136.
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