Dichlorido(6,6'-dimethyl-2,2'-bipyridine-κN,N')cobalt(II).

In the title compound, [CoCl(2)(C(12)H(12)N(2))], the Co(II) atom is four-coordinated in a distorted tetra-hedral geometry by two N atoms from a 6,6'-dimethyl-2,2'-bipyridine ligand and two terminal Cl atoms. Inter-molecular C-H⋯Cl hydrogen bonds and π-π stacking inter-actions 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 = 314.07

Monoclinic,

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[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 ▶); 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 ▶).

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

[CoCl2(C12H12N2)]	F(000) = 636
Mr = 314.07	Dx = 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

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

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(Fo2) + (0.1251P)2 + 0.225P] where P = (Fo2 + 2Fc2)/3
3609 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.92 e Å−3

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) .