Dibromido(6,6'-dimethyl-2,2'-bipyridine-κ(2)N,N')cobalt(II).

In the title compound, [CoBr(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 by two terminal Br atoms. Inter-molecular C-H⋯Br hydrogen bonds and π-π stacking between the pyridine rings in the bc plane [centroid-centroid distance = 3.725 (3) Å] are present in the crystal structure.

Related literature

For related structures, see: Akbarzadeh Torbati et al. (2010 ▶); Alizadeh et al. (2011 ▶, 2009 ▶); Itoh et al. (2005 ▶); Kou et al. (2008 ▶); Onggo et al. (2005 ▶); Shirvan & Haydari Dezfuli (2012 ▶).

Experimental

Crystal data

[CoBr2(C12H12N2)]

M = 402.97

Monoclinic,

a = 7.6550 (6) Å

b = 10.2577 (9) Å

c = 18.0030 (16) Å

β = 95.779 (7)°

V = 1406.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 6.88 mm−1

T = 298 K

0.30 × 0.24 × 0.18 mm

Data collection

Bruker APEXII CCD area detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.149, T max = 0.302

7259 measured reflections

2766 independent reflections

1753 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.089

S = 0.95

2766 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.56 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812041980/xu5630sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812041980/xu5630Isup2.hkl

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

[CoBr2(C12H12N2)]	F(000) = 780
Mr = 402.97	Dx = 1.903 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7259 reflections
a = 7.6550 (6) Å	θ = 2.3–26.0°
b = 10.2577 (9) Å	µ = 6.88 mm−1
c = 18.0030 (16) Å	T = 298 K
β = 95.779 (7)°	Block, blue
V = 1406.5 (2) Å3	0.30 × 0.24 × 0.18 mm
Z = 4

Bruker APEXII CCD area detector diffractometer	2766 independent reflections
Radiation source: fine-focus sealed tube	1753 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.068
ω scans	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→9
Tmin = 0.149, Tmax = 0.302	k = −12→11
7259 measured reflections	l = −22→22

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.0371P)2] where P = (Fo2 + 2Fc2)/3
2766 reflections	(Δ/σ)max = 0.005
154 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.56 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	0.3959 (11)	0.8727 (6)	−0.0503 (3)	0.074 (2)
H1A	0.4872	0.8803	−0.0098	0.089*
H1B	0.2921	0.9159	−0.0372	0.089*
H1C	0.4338	0.9122	−0.0942	0.089*
C2	0.3572 (8)	0.7343 (6)	−0.0648 (3)	0.0494 (14)
C3	0.3757 (8)	0.6766 (7)	−0.1338 (3)	0.0566 (16)
H3	0.4156	0.7252	−0.1723	0.068*
C4	0.3342 (9)	0.5468 (7)	−0.1441 (3)	0.0651 (18)
H4	0.3435	0.5077	−0.1901	0.078*
C5	0.2791 (8)	0.4753 (6)	−0.0865 (3)	0.0550 (15)
H5	0.2506	0.3876	−0.0930	0.066*
C6	0.2665 (7)	0.5352 (5)	−0.0188 (3)	0.0397 (12)
C7	0.2137 (7)	0.4644 (5)	0.0477 (3)	0.0421 (12)
C8	0.1766 (8)	0.3330 (5)	0.0476 (3)	0.0570 (16)
H8	0.1821	0.2838	0.0045	0.068*
C9	0.1312 (9)	0.2751 (6)	0.1121 (4)	0.0687 (19)
H9	0.1056	0.1865	0.1131	0.082*
C10	0.1245 (8)	0.3503 (6)	0.1744 (4)	0.0592 (16)
H10	0.0960	0.3120	0.2185	0.071*
C11	0.1592 (8)	0.4813 (6)	0.1731 (3)	0.0504 (14)
C12	0.1535 (10)	0.5666 (7)	0.2391 (3)	0.077 (2)
H12A	0.0704	0.6355	0.2275	0.092*
H12B	0.2677	0.6033	0.2525	0.092*
H12C	0.1187	0.5164	0.2801	0.092*
N1	0.3039 (6)	0.6627 (4)	−0.0087 (2)	0.0385 (10)
N2	0.2047 (6)	0.5381 (4)	0.1095 (2)	0.0387 (10)
Co1	0.26905 (10)	0.72871 (7)	0.09589 (3)	0.0414 (2)
Br1	0.03425 (10)	0.87570 (7)	0.10302 (4)	0.0703 (2)
Br2	0.52149 (9)	0.80174 (6)	0.17019 (3)	0.0598 (2)

	U11	U22	U33	U12	U13	U23
C1	0.109 (6)	0.062 (4)	0.054 (3)	−0.021 (4)	0.019 (4)	0.010 (3)
C2	0.053 (4)	0.056 (3)	0.039 (3)	0.008 (3)	0.002 (3)	0.006 (2)
C3	0.057 (4)	0.082 (5)	0.032 (3)	0.006 (3)	0.009 (3)	0.003 (3)
C4	0.067 (5)	0.085 (5)	0.043 (3)	0.013 (4)	0.007 (3)	−0.025 (3)
C5	0.056 (4)	0.058 (4)	0.051 (3)	0.002 (3)	0.005 (3)	−0.019 (3)
C6	0.034 (3)	0.043 (3)	0.040 (3)	0.003 (2)	−0.001 (2)	−0.011 (2)
C7	0.035 (3)	0.037 (3)	0.051 (3)	0.002 (2)	−0.007 (2)	−0.003 (2)
C8	0.056 (4)	0.041 (3)	0.070 (4)	−0.008 (3)	−0.012 (3)	−0.012 (3)
C9	0.066 (5)	0.038 (3)	0.099 (5)	−0.010 (3)	−0.010 (4)	0.012 (3)
C10	0.054 (4)	0.051 (4)	0.072 (4)	−0.013 (3)	0.001 (3)	0.018 (3)
C11	0.046 (4)	0.053 (4)	0.052 (3)	−0.005 (3)	0.006 (3)	0.011 (3)
C12	0.112 (6)	0.076 (5)	0.047 (3)	−0.018 (4)	0.027 (4)	0.006 (3)
N1	0.042 (3)	0.039 (2)	0.035 (2)	−0.002 (2)	0.0043 (19)	−0.0038 (17)
N2	0.038 (3)	0.034 (2)	0.043 (2)	−0.005 (2)	0.0007 (19)	−0.0013 (18)
Co1	0.0525 (5)	0.0357 (4)	0.0369 (3)	−0.0046 (3)	0.0083 (3)	−0.0058 (3)
Br1	0.0725 (5)	0.0601 (4)	0.0781 (4)	0.0177 (4)	0.0062 (3)	−0.0207 (3)
Br2	0.0619 (4)	0.0660 (4)	0.0508 (3)	−0.0135 (3)	0.0023 (3)	−0.0131 (3)

C1—C2	1.468 (8)	C8—C9	1.379 (8)
C1—H1A	0.9600	C8—H8	0.9300
C1—H1B	0.9600	C9—C10	1.367 (9)
C1—H1C	0.9600	C9—H9	0.9300
C2—N1	1.345 (6)	C10—C11	1.370 (8)
C2—C3	1.396 (7)	C10—H10	0.9300
C3—C4	1.377 (9)	C11—N2	1.360 (6)
C3—H3	0.9300	C11—C12	1.481 (8)
C4—C5	1.371 (9)	C12—H12A	0.9600
C4—H4	0.9300	C12—H12B	0.9600
C5—C6	1.378 (7)	C12—H12C	0.9600
C5—H5	0.9300	Co1—N1	2.044 (4)
C6—N1	1.347 (6)	Co1—N2	2.037 (4)
C6—C7	1.490 (7)	Co1—Br1	2.3594 (10)
C7—N2	1.354 (6)	Co1—Br2	2.3588 (10)
C7—C8	1.377 (7)
C2—C1—H1A	109.5	C10—C9—C8	118.8 (6)
C2—C1—H1B	109.5	C10—C9—H9	120.6
H1A—C1—H1B	109.5	C8—C9—H9	120.6
C2—C1—H1C	109.5	C9—C10—C11	121.0 (6)
H1A—C1—H1C	109.5	C9—C10—H10	119.5
H1B—C1—H1C	109.5	C11—C10—H10	119.5
N1—C2—C3	120.1 (5)	N2—C11—C10	120.1 (5)
N1—C2—C1	117.7 (5)	N2—C11—C12	116.9 (5)
C3—C2—C1	122.1 (5)	C10—C11—C12	122.9 (5)
C4—C3—C2	119.2 (5)	C11—C12—H12A	109.5
C4—C3—H3	120.4	C11—C12—H12B	109.5
C2—C3—H3	120.4	H12A—C12—H12B	109.5
C5—C4—C3	120.0 (5)	C11—C12—H12C	109.5
C5—C4—H4	120.0	H12A—C12—H12C	109.5
C3—C4—H4	120.0	H12B—C12—H12C	109.5
C4—C5—C6	119.0 (6)	C2—N1—C6	120.4 (4)
C4—C5—H5	120.5	C2—N1—Co1	126.0 (3)
C6—C5—H5	120.5	C6—N1—Co1	113.5 (3)
N1—C6—C5	121.3 (5)	C7—N2—C11	119.4 (4)
N1—C6—C7	115.9 (4)	C7—N2—Co1	113.8 (3)
C5—C6—C7	122.8 (5)	C11—N2—Co1	126.8 (3)
N2—C7—C8	121.3 (5)	N2—Co1—N1	81.30 (15)
N2—C7—C6	115.4 (4)	N2—Co1—Br2	115.50 (12)
C8—C7—C6	123.3 (5)	N1—Co1—Br2	116.88 (13)
C7—C8—C9	119.4 (6)	N2—Co1—Br1	114.33 (13)
C7—C8—H8	120.3	N1—Co1—Br1	115.65 (12)
C9—C8—H8	120.3	Br2—Co1—Br1	110.57 (4)
N1—C2—C3—C4	1.8 (9)	C5—C6—N1—Co1	178.5 (4)
C1—C2—C3—C4	−178.9 (6)	C7—C6—N1—Co1	−2.2 (6)
C2—C3—C4—C5	−1.4 (10)	C8—C7—N2—C11	0.4 (8)
C3—C4—C5—C6	−0.1 (10)	C6—C7—N2—C11	−179.4 (5)
C4—C5—C6—N1	1.3 (9)	C8—C7—N2—Co1	179.1 (5)
C4—C5—C6—C7	−177.9 (5)	C6—C7—N2—Co1	−0.6 (6)
N1—C6—C7—N2	1.9 (7)	C10—C11—N2—C7	0.6 (8)
C5—C6—C7—N2	−178.8 (5)	C12—C11—N2—C7	179.4 (5)
N1—C6—C7—C8	−177.9 (5)	C10—C11—N2—Co1	−177.9 (4)
C5—C6—C7—C8	1.4 (9)	C12—C11—N2—Co1	0.8 (8)
N2—C7—C8—C9	−0.7 (9)	C7—N2—Co1—N1	−0.4 (4)
C6—C7—C8—C9	179.0 (5)	C11—N2—Co1—N1	178.2 (5)
C7—C8—C9—C10	0.0 (10)	C7—N2—Co1—Br2	−116.1 (3)
C8—C9—C10—C11	1.1 (10)	C11—N2—Co1—Br2	62.5 (5)
C9—C10—C11—N2	−1.4 (10)	C7—N2—Co1—Br1	113.9 (3)
C9—C10—C11—C12	180.0 (6)	C11—N2—Co1—Br1	−67.5 (5)
C3—C2—N1—C6	−0.6 (8)	C2—N1—Co1—N2	−179.1 (5)
C1—C2—N1—C6	−180.0 (6)	C6—N1—Co1—N2	1.5 (4)
C3—C2—N1—Co1	180.0 (4)	C2—N1—Co1—Br2	−64.8 (5)
C1—C2—N1—Co1	0.6 (8)	C6—N1—Co1—Br2	115.7 (3)
C5—C6—N1—C2	−0.9 (8)	C2—N1—Co1—Br1	68.0 (5)
C7—C6—N1—C2	178.3 (5)	C6—N1—Co1—Br1	−111.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···Br1i	0.93	2.92	3.696 (5)	142
C12—H12C···Br1ii	0.96	2.89	3.847 (6)	172

Table 1

Selected bond lengths (Å)

Co1—N1	2.044 (4)
Co1—N2	2.037 (4)
Co1—Br1	2.3594 (10)
Co1—Br2	2.3588 (10)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯Br1i	0.93	2.92	3.696 (5)	142
C12—H12C⋯Br1ii	0.96	2.89	3.847 (6)	172

Symmetry codes: (i) ; (ii) .