Dichlorido(6-methyl-2,2'-bipyridine-κ(2)N,N')cobalt(II).

In the title compound, [CoCl(2)(C(11)H(10)N(2))], the Co(II) atom is four-coordinated in a distorted tetra-hedral geometry by two N atoms from a 6-methyl-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 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

[CoCl2(C11n class="Species">H10N2)]

M = 300.04

Monoclinic,

a = 7.4395 (6) Å

b = 9.4723 (8) Å

c = 17.6439 (15) Å

β = 96.131 (7)°

V = 1236.24 (18) Å3

Z = 4

Mo Kα radiation

μ = 1.79 mm−1

T = 298 K

0.20 × 0.15 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.730, T max = 0.780

7959 measured reflections

3305 independent reflections

2481 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.131

S = 1.12

3305 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.85 e Å−3

Δρmin = −0.48 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: 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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536812041116/hy2591sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812041116/hy2591Isup2.hkl

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

[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

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

Table 1

Selected bond lengths (Å)

Co1—N1	2.034 (3)
Co1—N2	2.038 (3)
Co1—Cl1	2.2320 (13)
Co1—Cl2	2.2121 (11)

Table 2

Hydrogen-bond geometry (Å, °)

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) .