Dichlorido(6,6′-dimethyl-2,2′-bipyridine-κ2N,N′)cobalt(II)

Akbarzadeh Torbati, N.; Rezvani, A.R.; Safari, N.; Saravani, H.; Amani, V.

doi:10.1107/S1600536810036846

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page m1284

doi:10.1107/S1600536810036846

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Dichlorido(6,6′-dimethyl-2,2′-bipyridine-κ²N,N′)cobalt(II)

Niloufar Akbarzadeh Torbati,^a Ali Reza Rezvani,^a ^* Nasser Safari,^b Hamideh Saravani ^a and Vahid Amani ^b

^aDepartment of Chemistry, University of Sistan and Baluchestan, PO Box 98135-674, Zahedan, Iran, and ^bDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran
^*Correspondence e-mail: ali@hamoon.usb.ac.ir

(Received 5 September 2010; accepted 14 September 2010; online 18 September 2010)

In the title compound, [CoCl₂(C₁₂H₁₂N₂)], the Co^II 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 ); Alizadeh et al. (2010 ); Alizadeh, Kalateh, Ebadi et al. (2009 ); Alizadeh, Kalateh, Khoshtarkib et al. (2009 ); Alizadeh, Khoshtarkib et al. (2009 ); Baker et al. (1988 ); Itoh et al. (2005 ); Kou et al. (2008 ); Onggo et al. (2005 ).

Experimental

Crystal data

[CoCl₂(C₁₂H₁₂N₂)]
M_r = 314.07
Monoclinic, P 2₁ /c
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 ) 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[F² > 2σ(F²)] = 0.064
wR(F²) = 0.226
S = 1.13
3609 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.92 e Å⁻³

Table 1
Selected bond lengths (Å)

Co1—N1	2.042 (3)
Co1—N2	2.053 (3)
Co1—Cl1	2.2193 (13)
Co1—Cl2	2.2269 (13)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯Cl1ⁱ	0.93	2.82	3.565 (7)	138
Symmetry code: (i) -x+1, -y+1, -z+1.

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

Supporting information

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

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

checkCIF report

Comment top

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 Co^II 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.

Related literature top

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

Experimental top

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%).

Computing details top

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

Figures top

	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.

Dichlorido(6,6'-dimethyl-2,2'-bipyridine-κ²N,N')cobalt(II) top

Crystal data top

[CoCl₂(C₁₂H₁₂N₂)]	F(000) = 636
M_r = 314.07	D_x = 1.555 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1009 reflections
a = 7.6292 (14) Å	θ = 2.3–29.3°
b = 9.8034 (14) Å	µ = 1.66 mm⁻¹
c = 17.980 (4) Å	T = 298 K
β = 93.990 (15)°	Block, blue
V = 1341.5 (4) Å³	0.50 × 0.19 × 0.13 mm
Z = 4

Data collection top

Bruker APEX CCD diffractometer	3609 independent reflections
Radiation source: fine-focus sealed tube	2642 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.100
ϕ and ω scans	θ_max = 29.3°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
T_min = 0.690, T_max = 0.810	k = −13→11
10258 measured reflections	l = −24→24

Refinement top

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.226	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.1251P)² + 0.225P] where P = (F_o² + 2F_c²)/3
3609 reflections	(Δ/σ)_max < 0.001
154 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.92 e Å⁻³

Crystal data top

[CoCl₂(C₁₂H₁₂N₂)]	V = 1341.5 (4) Å³
M_r = 314.07	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.6292 (14) Å	µ = 1.66 mm⁻¹
b = 9.8034 (14) Å	T = 298 K
c = 17.980 (4) Å	0.50 × 0.19 × 0.13 mm
β = 93.990 (15)°

Data collection top

Bruker APEX CCD diffractometer	3609 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2642 reflections with I > 2σ(I)
T_min = 0.690, T_max = 0.810	R_int = 0.100
10258 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.226	H-atom parameters constrained
S = 1.13	Δρ_max = 0.47 e Å⁻³
3609 reflections	Δρ_min = −0.92 e Å⁻³
154 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.3248 (9)	0.4581 (6)	0.2579 (3)	0.0900 (16)
H1A	0.4369	0.4668	0.2373	0.108*
H1B	0.2338	0.4866	0.2217	0.108*
H1C	0.3061	0.3646	0.2712	0.108*
C2	0.3209 (6)	0.5449 (5)	0.3254 (3)	0.0654 (10)
C3	0.3451 (8)	0.6844 (6)	0.3227 (4)	0.0832 (15)
H3	0.3656	0.7264	0.2777	0.100*
C4	0.3390 (8)	0.7594 (5)	0.3849 (4)	0.0857 (16)
H4	0.3592	0.8529	0.3835	0.103*
C5	0.3022 (7)	0.6964 (5)	0.4517 (4)	0.0778 (14)
H5	0.2945	0.7475	0.4950	0.093*
C6	0.2773 (5)	0.5568 (4)	0.4525 (2)	0.0572 (9)
C7	0.2356 (5)	0.4790 (4)	0.5193 (2)	0.0544 (8)
C8	0.2233 (6)	0.5387 (6)	0.5874 (3)	0.0719 (12)
H8	0.2462	0.6312	0.5940	0.086*
C9	0.1762 (7)	0.4593 (7)	0.6459 (3)	0.0807 (14)
H9	0.1637	0.4985	0.6924	0.097*
C10	0.1481 (7)	0.3233 (7)	0.6357 (3)	0.0765 (13)
H10	0.1156	0.2693	0.6749	0.092*
C11	0.1681 (7)	0.2654 (5)	0.5660 (3)	0.0661 (10)
C12	0.1486 (11)	0.1176 (6)	0.5507 (4)	0.100 (2)
H12A	0.0319	0.0892	0.5603	0.120*
H12B	0.2324	0.0678	0.5824	0.120*
H12C	0.1688	0.1000	0.4995	0.120*
N1	0.2875 (4)	0.4836 (3)	0.38883 (19)	0.0537 (7)
N2	0.2096 (4)	0.3440 (4)	0.50901 (18)	0.0541 (7)
Co1	0.24226 (7)	0.28007 (5)	0.40212 (3)	0.0549 (2)
Cl1	0.47387 (17)	0.14706 (13)	0.38988 (8)	0.0811 (4)
Cl2	0.01041 (17)	0.19582 (14)	0.33528 (8)	0.0769 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.124 (4)	0.079 (3)	0.071 (3)	−0.003 (3)	0.029 (3)	0.007 (3)
C2	0.068 (2)	0.058 (2)	0.071 (3)	−0.0068 (19)	0.0113 (19)	0.0074 (19)
C3	0.089 (3)	0.064 (3)	0.097 (4)	−0.021 (3)	0.006 (3)	0.021 (3)
C4	0.096 (4)	0.049 (2)	0.111 (5)	−0.018 (2)	0.003 (3)	0.005 (3)
C5	0.084 (3)	0.058 (2)	0.090 (3)	−0.010 (2)	−0.006 (3)	−0.013 (2)
C6	0.0507 (17)	0.0491 (19)	0.072 (2)	0.0005 (15)	0.0021 (16)	−0.0091 (17)
C7	0.0490 (17)	0.059 (2)	0.0559 (19)	0.0040 (15)	0.0048 (14)	−0.0108 (16)
C8	0.075 (3)	0.074 (3)	0.068 (3)	0.002 (2)	0.010 (2)	−0.019 (2)
C9	0.082 (3)	0.095 (4)	0.066 (3)	0.009 (3)	0.011 (2)	−0.018 (3)
C10	0.073 (3)	0.099 (4)	0.058 (2)	0.006 (3)	0.009 (2)	0.010 (2)
C11	0.073 (3)	0.069 (3)	0.057 (2)	0.001 (2)	0.0055 (18)	0.0050 (19)
C12	0.154 (6)	0.071 (3)	0.077 (3)	−0.019 (4)	0.017 (4)	0.014 (3)
N1	0.0525 (15)	0.0479 (16)	0.0617 (17)	−0.0034 (13)	0.0120 (13)	−0.0002 (13)
N2	0.0572 (16)	0.0543 (17)	0.0512 (16)	0.0003 (14)	0.0072 (13)	−0.0035 (13)
Co1	0.0631 (4)	0.0453 (3)	0.0569 (4)	−0.0020 (2)	0.0095 (2)	−0.0053 (2)
Cl1	0.0798 (7)	0.0659 (7)	0.0979 (9)	0.0142 (6)	0.0080 (6)	−0.0239 (6)
Cl2	0.0753 (7)	0.0790 (7)	0.0759 (7)	−0.0148 (6)	0.0013 (5)	−0.0134 (6)

Geometric parameters (Å, º) top

C1—C2	1.483 (7)	C8—C9	1.377 (8)
C1—H1A	0.9600	C8—H8	0.9300
C1—H1B	0.9600	C9—C10	1.361 (9)
C1—H1C	0.9600	C9—H9	0.9300
C2—N1	1.330 (5)	C10—C11	1.393 (7)
C2—C3	1.382 (7)	C10—H10	0.9300
C3—C4	1.342 (9)	C11—N2	1.338 (6)
C3—H3	0.9300	C11—C12	1.480 (8)
C4—C5	1.397 (9)	C12—H12A	0.9600
C4—H4	0.9300	C12—H12B	0.9600
C5—C6	1.382 (6)	C12—H12C	0.9600
C5—H5	0.9300	Co1—N1	2.042 (3)
C6—N1	1.358 (5)	Co1—N2	2.053 (3)
C6—C7	1.477 (6)	Co1—Cl1	2.2193 (13)
C7—N2	1.349 (5)	Co1—Cl2	2.2269 (13)
C7—C8	1.365 (5)

C2—C1—H1A	109.5	C10—C9—C8	119.8 (5)
C2—C1—H1B	109.5	C10—C9—H9	120.1
H1A—C1—H1B	109.5	C8—C9—H9	120.1
C2—C1—H1C	109.5	C9—C10—C11	119.7 (5)
H1A—C1—H1C	109.5	C9—C10—H10	120.2
H1B—C1—H1C	109.5	C11—C10—H10	120.2
N1—C2—C3	120.7 (5)	N2—C11—C10	120.0 (5)
N1—C2—C1	117.3 (4)	N2—C11—C12	116.6 (4)
C3—C2—C1	121.9 (5)	C10—C11—C12	123.4 (5)
C4—C3—C2	120.0 (5)	C11—C12—H12A	109.5
C4—C3—H3	120.0	C11—C12—H12B	109.5
C2—C3—H3	120.0	H12A—C12—H12B	109.5
C3—C4—C5	119.7 (5)	C11—C12—H12C	109.5
C3—C4—H4	120.1	H12A—C12—H12C	109.5
C5—C4—H4	120.1	H12B—C12—H12C	109.5
C6—C5—C4	118.8 (5)	C2—N1—C6	120.7 (4)
C6—C5—H5	120.6	C2—N1—Co1	125.8 (3)
C4—C5—H5	120.6	C6—N1—Co1	113.5 (3)
N1—C6—C5	120.0 (5)	C11—N2—C7	120.0 (4)
N1—C6—C7	116.2 (3)	C11—N2—Co1	126.3 (3)
C5—C6—C7	123.9 (4)	C7—N2—Co1	113.7 (3)
N2—C7—C8	121.6 (4)	N1—Co1—N2	81.00 (14)
N2—C7—C6	115.7 (3)	N1—Co1—Cl1	114.87 (10)
C8—C7—C6	122.7 (4)	N2—Co1—Cl1	114.93 (10)
C7—C8—C9	118.8 (5)	N1—Co1—Cl2	115.70 (10)
C7—C8—H8	120.6	N2—Co1—Cl2	118.35 (10)
C9—C8—H8	120.6	Cl1—Co1—Cl2	109.67 (5)

N1—C2—C3—C4	1.6 (8)	C5—C6—N1—Co1	−179.0 (3)
C1—C2—C3—C4	179.4 (6)	C7—C6—N1—Co1	−0.2 (4)
C2—C3—C4—C5	−2.2 (9)	C10—C11—N2—C7	1.3 (7)
C3—C4—C5—C6	1.7 (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—Co1	1.7 (7)
N1—C6—C7—N2	−1.0 (5)	C8—C7—N2—C11	1.0 (6)
C5—C6—C7—N2	177.7 (4)	C6—C7—N2—C11	−178.9 (4)
N1—C6—C7—C8	179.2 (4)	C8—C7—N2—Co1	−178.5 (3)
C5—C6—C7—C8	−2.1 (6)	C6—C7—N2—Co1	1.6 (4)
N2—C7—C8—C9	−2.6 (7)	C2—N1—Co1—N2	−178.0 (3)
C6—C7—C8—C9	177.2 (4)	C6—N1—Co1—N2	0.8 (3)
C7—C8—C9—C10	1.9 (8)	C2—N1—Co1—Cl1	68.6 (3)
C8—C9—C10—C11	0.4 (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—C12	177.0 (6)	C6—N1—Co1—Cl2	118.0 (2)
C3—C2—N1—C6	−0.4 (7)	C11—N2—Co1—N1	179.2 (4)
C1—C2—N1—C6	−178.3 (4)	C7—N2—Co1—N1	−1.4 (3)
C3—C2—N1—Co1	178.3 (4)	C11—N2—Co1—Cl1	−67.5 (4)
C1—C2—N1—Co1	0.4 (6)	C7—N2—Co1—Cl1	111.9 (3)
C5—C6—N1—C2	−0.1 (6)	C11—N2—Co1—Cl2	64.7 (4)
C7—C6—N1—C2	178.7 (3)	C7—N2—Co1—Cl2	−115.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cl1ⁱ	0.93	2.82	3.565 (7)	138

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[CoCl₂(C₁₂H₁₂N₂)]
M_r	314.07
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	7.6292 (14), 9.8034 (14), 17.980 (4)
β (°)	93.990 (15)
V (Å³)	1341.5 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.66
Crystal size (mm)	0.50 × 0.19 × 0.13

Data collection
Diffractometer	Bruker APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.690, 0.810
No. of measured, independent and observed [I > 2σ(I)] reflections	10258, 3609, 2642
R_int	0.100
(sin θ/λ)_max (Å⁻¹)	0.688

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.226, 1.13
No. of reflections	3609
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.92

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

Co1—N1	2.042 (3)	Co1—Cl1	2.2193 (13)
Co1—N2	2.053 (3)	Co1—Cl2	2.2269 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cl1ⁱ	0.93	2.82	3.565 (7)	138

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

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

References

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