metal-organic compounds
Dichlorido(6-methyl-2,2′-bipyridine-κ2N,N′)cobalt(II)
aDepartment of Chemistry, University of Sistan and Baluchestan, PO Box 98135-674, Zahedan, Iran
*Correspondence e-mail: n.akbarzadeh@chem.usb.ac.ir
In the title compound, [CoCl2(C11H10N2)], the CoII atom is four-coordinated in a distorted tetrahedral geometry by two N atoms from a 6-methyl-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 distance = 3.745 (3) Å] are present in the crystal.
Related literature
For related structures, see: Ahmadi et al. (2009); Ahmadi, Ebadi et al. (2008); Ahmadi, Kalateh et al. (2008); Akbarzadeh Torbati et al. (2010a,b, 2011); Amani et al. (2009); Kalateh et al. (2010); Newkome et al. (1982); Onggo et al. (1990, 2005); Shirvan & Haydari Dezfuli (2012).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
Supporting information
10.1107/S1600536812041116/hy2591sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812041116/hy2591Isup2.hkl
For the preparation of the title compound, a solution of 6-methyl-2,2'-bipyridine (0.23 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: 0.30 g, 74.6%).
H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 (aromatic) and 0.96 (CH3) Å and with Uiso(H) = 1.2Ueq(C).
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).[CoCl2(C11H10N2)] | F(000) = 604 |
Mr = 300.04 | Dx = 1.612 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 998 reflections |
a = 7.4395 (6) Å | θ = 2.3–29.3° |
b = 9.4723 (8) Å | µ = 1.79 mm−1 |
c = 17.6439 (15) Å | T = 298 K |
β = 96.131 (7)° | Block, blue |
V = 1236.24 (18) Å3 | 0.20 × 0.15 × 0.14 mm |
Z = 4 |
Bruker APEXII CCD diffractometer | 3305 independent reflections |
Radiation source: fine-focus sealed tube | 2481 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
ϕ and ω scans | θmax = 29.3°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −10→10 |
Tmin = 0.730, Tmax = 0.780 | k = −11→12 |
7959 measured reflections | l = −24→23 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.131 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0444P)2 + 1.4058P] where P = (Fo2 + 2Fc2)/3 |
3305 reflections | (Δ/σ)max < 0.001 |
145 parameters | Δρmax = 0.85 e Å−3 |
0 restraints | Δρmin = −0.48 e Å−3 |
[CoCl2(C11H10N2)] | V = 1236.24 (18) Å3 |
Mr = 300.04 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.4395 (6) Å | µ = 1.79 mm−1 |
b = 9.4723 (8) Å | T = 298 K |
c = 17.6439 (15) Å | 0.20 × 0.15 × 0.14 mm |
β = 96.131 (7)° |
Bruker APEXII CCD diffractometer | 3305 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 2481 reflections with I > 2σ(I) |
Tmin = 0.730, Tmax = 0.780 | Rint = 0.043 |
7959 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | 0 restraints |
wR(F2) = 0.131 | H-atom parameters constrained |
S = 1.12 | Δρmax = 0.85 e Å−3 |
3305 reflections | Δρmin = −0.48 e Å−3 |
145 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.6700 (9) | 0.9546 (6) | 0.2127 (3) | 0.0841 (16) | |
H1A | 0.7822 | 0.9086 | 0.2296 | 0.101* | |
H1B | 0.5749 | 0.8858 | 0.2064 | 0.101* | |
H1C | 0.6430 | 1.0233 | 0.2498 | 0.101* | |
C2 | 0.6857 (6) | 1.0262 (5) | 0.1385 (3) | 0.0549 (10) | |
C3 | 0.6639 (6) | 1.1710 (5) | 0.1282 (3) | 0.0661 (12) | |
H3 | 0.6359 | 1.2279 | 0.1683 | 0.079* | |
C4 | 0.6843 (7) | 1.2286 (5) | 0.0589 (3) | 0.0679 (13) | |
H4 | 0.6706 | 1.3254 | 0.0518 | 0.081* | |
C5 | 0.7246 (6) | 1.1457 (4) | −0.0005 (3) | 0.0572 (10) | |
H5 | 0.7389 | 1.1850 | −0.0478 | 0.069* | |
C6 | 0.7439 (4) | 1.0016 (4) | 0.0116 (2) | 0.0430 (8) | |
C7 | 0.7826 (5) | 0.8999 (4) | −0.0480 (2) | 0.0446 (8) | |
C8 | 0.8106 (6) | 0.9397 (5) | −0.1220 (2) | 0.0582 (11) | |
H8 | 0.8110 | 1.0345 | −0.1357 | 0.070* | |
C9 | 0.8380 (7) | 0.8356 (6) | −0.1748 (3) | 0.0686 (13) | |
H9 | 0.8574 | 0.8599 | −0.2243 | 0.082* | |
C10 | 0.8363 (7) | 0.6973 (6) | −0.1535 (3) | 0.0703 (13) | |
H10 | 0.8512 | 0.6264 | −0.1888 | 0.084* | |
C11 | 0.8125 (6) | 0.6635 (5) | −0.0799 (3) | 0.0601 (11) | |
H11 | 0.8138 | 0.5690 | −0.0656 | 0.072* | |
N1 | 0.7245 (4) | 0.9445 (3) | 0.08066 (17) | 0.0431 (7) | |
N2 | 0.7872 (4) | 0.7629 (3) | −0.02746 (18) | 0.0465 (7) | |
Co1 | 0.76711 (7) | 0.73253 (5) | 0.08569 (3) | 0.04458 (16) | |
Cl1 | 1.03449 (15) | 0.68766 (14) | 0.15119 (7) | 0.0683 (3) | |
Cl2 | 0.54399 (16) | 0.59698 (13) | 0.11655 (7) | 0.0673 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.114 (5) | 0.085 (4) | 0.056 (3) | 0.010 (3) | 0.024 (3) | −0.014 (3) |
C2 | 0.049 (2) | 0.055 (2) | 0.061 (2) | 0.0011 (18) | 0.0059 (18) | −0.0083 (19) |
C3 | 0.056 (2) | 0.061 (3) | 0.081 (3) | 0.005 (2) | 0.005 (2) | −0.021 (2) |
C4 | 0.060 (3) | 0.040 (2) | 0.103 (4) | −0.0006 (19) | 0.004 (3) | 0.003 (2) |
C5 | 0.052 (2) | 0.046 (2) | 0.073 (3) | −0.0005 (17) | 0.003 (2) | 0.013 (2) |
C6 | 0.0343 (16) | 0.0436 (18) | 0.050 (2) | −0.0035 (14) | 0.0007 (14) | 0.0110 (15) |
C7 | 0.0353 (16) | 0.050 (2) | 0.048 (2) | −0.0082 (15) | 0.0024 (14) | 0.0068 (16) |
C8 | 0.054 (2) | 0.070 (3) | 0.049 (2) | −0.012 (2) | 0.0021 (18) | 0.018 (2) |
C9 | 0.066 (3) | 0.102 (4) | 0.039 (2) | −0.010 (3) | 0.0119 (19) | 0.003 (2) |
C10 | 0.073 (3) | 0.090 (4) | 0.050 (3) | −0.005 (3) | 0.015 (2) | −0.015 (2) |
C11 | 0.061 (2) | 0.063 (3) | 0.057 (3) | −0.003 (2) | 0.012 (2) | −0.009 (2) |
N1 | 0.0412 (15) | 0.0412 (15) | 0.0465 (17) | 0.0016 (12) | 0.0027 (13) | 0.0022 (13) |
N2 | 0.0442 (15) | 0.0499 (17) | 0.0458 (16) | −0.0021 (13) | 0.0070 (13) | 0.0040 (14) |
Co1 | 0.0474 (3) | 0.0416 (3) | 0.0458 (3) | 0.0009 (2) | 0.0098 (2) | 0.0099 (2) |
Cl1 | 0.0500 (5) | 0.0788 (8) | 0.0754 (7) | 0.0019 (5) | 0.0033 (5) | 0.0350 (6) |
Cl2 | 0.0590 (6) | 0.0654 (7) | 0.0786 (8) | −0.0129 (5) | 0.0130 (5) | 0.0186 (6) |
C1—C2 | 1.490 (7) | C7—N2 | 1.346 (5) |
C1—H1A | 0.9600 | C7—C8 | 1.397 (5) |
C1—H1B | 0.9600 | C8—C9 | 1.386 (7) |
C1—H1C | 0.9600 | C8—H8 | 0.9300 |
C2—N1 | 1.336 (5) | C9—C10 | 1.363 (8) |
C2—C3 | 1.391 (6) | C9—H9 | 0.9300 |
C3—C4 | 1.363 (7) | C10—C11 | 1.367 (6) |
C3—H3 | 0.9300 | C10—H10 | 0.9300 |
C4—C5 | 1.368 (7) | C11—N2 | 1.347 (5) |
C4—H4 | 0.9300 | C11—H11 | 0.9300 |
C5—C6 | 1.386 (5) | Co1—N1 | 2.034 (3) |
C5—H5 | 0.9300 | Co1—N2 | 2.038 (3) |
C6—N1 | 1.355 (5) | Co1—Cl1 | 2.2320 (13) |
C6—C7 | 1.477 (5) | Co1—Cl2 | 2.2121 (11) |
C2—C1—H1A | 109.5 | C9—C8—C7 | 118.9 (4) |
C2—C1—H1B | 109.5 | C9—C8—H8 | 120.6 |
H1A—C1—H1B | 109.5 | C7—C8—H8 | 120.6 |
C2—C1—H1C | 109.5 | C10—C9—C8 | 119.5 (4) |
H1A—C1—H1C | 109.5 | C10—C9—H9 | 120.2 |
H1B—C1—H1C | 109.5 | C8—C9—H9 | 120.2 |
N1—C2—C3 | 120.2 (4) | C9—C10—C11 | 119.5 (5) |
N1—C2—C1 | 116.8 (4) | C9—C10—H10 | 120.3 |
C3—C2—C1 | 122.9 (4) | C11—C10—H10 | 120.3 |
C4—C3—C2 | 119.3 (4) | N2—C11—C10 | 122.1 (5) |
C4—C3—H3 | 120.4 | N2—C11—H11 | 119.0 |
C2—C3—H3 | 120.4 | C10—C11—H11 | 119.0 |
C3—C4—C5 | 120.8 (4) | C2—N1—C6 | 120.6 (3) |
C3—C4—H4 | 119.6 | C2—N1—Co1 | 125.7 (3) |
C5—C4—H4 | 119.6 | C6—N1—Co1 | 113.7 (2) |
C4—C5—C6 | 118.4 (4) | C7—N2—C11 | 119.3 (3) |
C4—C5—H5 | 120.8 | C7—N2—Co1 | 113.4 (3) |
C6—C5—H5 | 120.8 | C11—N2—Co1 | 127.2 (3) |
N1—C6—C5 | 120.7 (4) | N1—Co1—N2 | 81.08 (13) |
N1—C6—C7 | 115.3 (3) | N1—Co1—Cl2 | 117.79 (9) |
C5—C6—C7 | 123.9 (4) | N2—Co1—Cl2 | 117.29 (10) |
N2—C7—C8 | 120.7 (4) | N1—Co1—Cl1 | 109.69 (10) |
N2—C7—C6 | 116.0 (3) | N2—Co1—Cl1 | 112.31 (10) |
C8—C7—C6 | 123.3 (4) | Cl2—Co1—Cl1 | 114.38 (5) |
N1—C2—C3—C4 | −0.6 (7) | C5—C6—N1—Co1 | −178.0 (3) |
C1—C2—C3—C4 | 178.6 (5) | C7—C6—N1—Co1 | 3.0 (4) |
C2—C3—C4—C5 | 0.4 (7) | C8—C7—N2—C11 | −2.5 (6) |
C3—C4—C5—C6 | 0.2 (7) | C6—C7—N2—C11 | 176.6 (3) |
C4—C5—C6—N1 | −0.5 (6) | C8—C7—N2—Co1 | 174.3 (3) |
C4—C5—C6—C7 | 178.4 (4) | C6—C7—N2—Co1 | −6.6 (4) |
N1—C6—C7—N2 | 2.4 (5) | C10—C11—N2—C7 | 0.9 (7) |
C5—C6—C7—N2 | −176.5 (4) | C10—C11—N2—Co1 | −175.4 (4) |
N1—C6—C7—C8 | −178.5 (3) | C2—N1—Co1—N2 | 176.8 (3) |
C5—C6—C7—C8 | 2.6 (6) | C6—N1—Co1—N2 | −5.0 (2) |
N2—C7—C8—C9 | 1.9 (6) | C2—N1—Co1—Cl2 | 60.6 (3) |
C6—C7—C8—C9 | −177.1 (4) | C6—N1—Co1—Cl2 | −121.3 (2) |
C7—C8—C9—C10 | 0.2 (7) | C2—N1—Co1—Cl1 | −72.6 (3) |
C8—C9—C10—C11 | −1.8 (8) | C6—N1—Co1—Cl1 | 105.6 (2) |
C9—C10—C11—N2 | 1.2 (8) | C7—N2—Co1—N1 | 6.3 (3) |
C3—C2—N1—C6 | 0.3 (6) | C11—N2—Co1—N1 | −177.1 (4) |
C1—C2—N1—C6 | −178.9 (4) | C7—N2—Co1—Cl2 | 123.1 (2) |
C3—C2—N1—Co1 | 178.3 (3) | C11—N2—Co1—Cl2 | −60.4 (4) |
C1—C2—N1—Co1 | −0.9 (6) | C7—N2—Co1—Cl1 | −101.4 (3) |
C5—C6—N1—C2 | 0.3 (5) | C11—N2—Co1—Cl1 | 75.2 (4) |
C7—C6—N1—C2 | −178.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1C···Cl1i | 0.96 | 2.78 | 3.706 (6) | 163 |
Symmetry code: (i) −x+3/2, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [CoCl2(C11H10N2)] |
Mr | 300.04 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 7.4395 (6), 9.4723 (8), 17.6439 (15) |
β (°) | 96.131 (7) |
V (Å3) | 1236.24 (18) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.79 |
Crystal size (mm) | 0.20 × 0.15 × 0.14 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.730, 0.780 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7959, 3305, 2481 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.688 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.131, 1.12 |
No. of reflections | 3305 |
No. of parameters | 145 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.85, −0.48 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1C···Cl1i | 0.96 | 2.78 | 3.706 (6) | 163 |
Symmetry code: (i) −x+3/2, y+1/2, −z+1/2. |
Acknowledgements
We are grateful to the University of Sistan and Baluchestan and Shahid Beheshti University for financial support.
References
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In recent years, we have reported the synthesis and crystal structures of [Co(6,6'-dmbipy)Cl2], (II) (Akbarzadeh Torbati et al., 2010b), [Co(Ph2phen)Cl2], (III) (Akbarzadeh Torbati et al., 2010a) and [Co(biq)Cl2], (IV) (Akbarzadeh Torbati et al., 2011) (6,6'-dmbipy = 6,6'-dimethyl-2,2'-bipyridine, Ph2phen = 2,9-dimethyl-1,10-phenanthroline, biq = 2,2'-biquinoline). 6-Methyl-2,2'-bipyridine (6-mbipy) is a good ligand and a few complexes with 6-mbipy have been prepared, such as that of [Hg(6-mbipy)Cl2], (V) (Ahmadi, Ebadi et al., 2008), [Pt(6-mbipy)Cl4], (VI) (Amani et al., 2009), [Pb4(NO3)8(6-mbipy)4], (VII) (Ahmadi et al., 2009), [Zn(6-mbipy)Br2], (VIII) (Kalateh et al., 2010), [Zn(6-mbipy)Cl2], (IX) (Ahmadi, Kalateh et al., 2008), [Pd(6-mbipy)Cl2], (X) (Newkome et al., 1982), [Ru(6-mbipy)3][BF4]2, (XI) (Onggo et al., 2005), [Fe(6-mbipy)3][ClO4]2.6-mbipy, (XII) (Onggo et al., 1990) and [Cd(6-mbipy)Br2(DMSO)], (XIII) (Shirvan & Haydari Dezfuli, 2012). We report herein the synthesis and crystal structure of the title compound, (I).
In the title compound (Fig. 1), the CoII atom is four-coordinated in a distorted tetrahedral geometry by two N atoms from a 6-methyl-2,2'-bipyridine ligand and two terminal Cl atoms (Table 1). In the crystal, intermolecular C—H···Cl hydrogen bonds (Table 2) and π–π contacts (Fig. 2) between the pyridine rings, Cg2···Cg3i [centroid–centroid distance = 3.745 (3) Å, symmetry code: (i) 2-x, 2-y, -z, Cg2 and Cg3 are the centroids of the N1/C2–C6 ring and N2/C7–C11 ring, respectively], stabilize the structure.