Dibromido(6-methyl-2,2′-bipyridine-κ2N,N′)cobalt(II)

Shirvan, S.A.; Haydari Dezfuli, S.; Khazali, F.; Borsalani, A.

doi:10.1107/S1600536812045230

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page m1460

doi:10.1107/S1600536812045230

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Dibromido(6-methyl-2,2′-bipyridine-κ²N,N′)cobalt(II)

Sadif A. Shirvan,^a ^* Sara Haydari Dezfuli,^a Fereydoon Khazali ^a and Ali Borsalani ^b

^aDepartment of Chemistry, Omidieh Branch, Islamic Azad University, Omidieh, Iran, and ^bDepartment of Petroleum Engineering, Omidieh Branch, Islamic Azad University, Omidieh, Iran
^*Correspondence e-mail: sadifchemist@hotmail.com

(Received 26 October 2012; accepted 1 November 2012; online 7 November 2012)

In the molecule of the title compound, [CoBr₂(C₁₁H₁₀N₂)], the Co^II atom is four-coordinated in a distorted tetrahedral geometry by two N atoms from a chelating 6-methyl-2,2′-bipyridine ligand and two terminal Br atoms. In the crystal, π–π stacking interactions between the pyridine rings along the a-axis direction [centroid–centroid distance = 3.761 (7) Å] and C—H⋯Br hydrogen bonds in the bc plane together generate the three-dimensional packing.

Related literature

For related structures, see: Ahmadi et al. (2008a ,b , 2009 ); Amani et al. (2009 ); Kalateh et al. (2010 ); Newkome et al. (1982 ); Onggo et al. (2005 ); Shirvan et al. (2012 ); Shirvan & Haydari Dezfuli (2012 ).

Experimental

Crystal data

[CoBr₂(C₁₁H₁₀N₂)]
M_r = 388.94
Monoclinic, P 2₁ /n
a = 7.5541 (7) Å
b = 9.7249 (7) Å
c = 17.7352 (16) Å
β = 97.392 (7)°
V = 1292.05 (19) Å³
Z = 4
Mo Kα radiation
μ = 7.49 mm⁻¹
T = 173 K
0.45 × 0.13 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.379, T_max = 0.512
6393 measured reflections
2519 independent reflections
1546 reflections with I > 2σ(I)
R_int = 0.099

Refinement

R[F² > 2σ(F²)] = 0.085
wR(F²) = 0.164
S = 1.05
2519 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 2.16 e Å⁻³
Δρ_min = −1.13 e Å⁻³

Table 1
Selected bond lengths (Å)

Co1—Br1	2.352 (2)
Co1—Br2	2.3698 (19)
Co1—N1	2.035 (10)
Co1—N2	2.029 (8)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯Br1ⁱ	0.96	2.89	3.849 (14)	178
C8—H8⋯Br2ⁱⁱ	0.93	2.89	3.771 (14)	158
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z.

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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812045230/hy2600sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812045230/hy2600Isup2.hkl

checkCIF report

Comment top

Recently, we reported the synthesis and crystal structure of [In(6-mbipy)Cl₃(DMSO)], (II) (Shirvan et al., 2012) and [Cd(6-mbipy)Br₂(DMSO)], (III) (Shirvan & Haydari Dezfuli, 2012) (6-mbipy = 6-methyl-2,2'-bipyridine, DMSO = dimethyl sulfoxide). 6-Methyl-2,2'-bipyridine is a good ligand and a few complexes with 6-mbipy have been prepared, such as that of [Hg(6-mbipy)Cl₂], (IV) (Ahmadi et al., 2008a), [Pt(6-mbipy)Cl₄], (V) (Amani et al., 2009), [Pb₄(NO₃)₈(6-mbipy)₄], (VI) (Ahmadi et al., 2009), [Zn(6-mbipy)Br₂], (VII) (Kalateh et al., 2010), [Zn(6-mbipy)Cl₂], (VIII) (Ahmadi et al., 2008b), [Pd(6-mbipy)Cl₂], (IX) (Newkome et al., 1982) and [Ru(6-mbipy)₃][BF₄]₂, (X) (Onggo et al., 2005). We report herein the synthesis and crystal structure of the title compound, (I).

In the title compound (Fig. 1), the Co^II atom is four-coordinated in a distorted tetrahedral geometry by two N atoms from a chelating 6-mbipy ligand and two terminal Br atoms (Table 1). In the crystal, intermolecular C—H···Br hydrogen bonds and π–π contacts (Table 2, Fig. 2) between the pyridine rings, Cg2···Cg3ⁱ [symmetry code: (i) 1-x, 1-y, -z, Cg2 and Cg3 are the centroids of the rings N1/C2–C6 and N2/C7–C11, respectively], with a centroid–centroid distance of 3.761 (7) Å, stabilize the structure.

Related literature top

For related structures, see: Ahmadi et al. (2008a,b, 2009); Amani et al. (2009); Kalateh et al. (2010); Newkome et al. (1982); Onggo et al. (2005); Shirvan et al. (2012); Shirvan & Haydari Dezfuli (2012).

Experimental top

For the preparation of the title compound, a solution of 6-mbipy (0.28 g, 0.26 ml, 1.65 mmol) in acetonitrile (10 ml) was added to a solution of CoBr₂ (0.36 g, 1.65 mmol) in acetonitrile (10 ml) and the resulting blue solution was stirred for 20 min at 313 K. This solution was left to evaporate slowly at room temperature. After one week, blue needle crystals of the title compound were isolated (yield: 0.47 g, 73.2%).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: 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: SHELXL97 (Sheldrick, 2008).

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. Hydrogen bonds are shown as dashed lines.

Dibromido(6-methyl-2,2'-bipyridine-κ²N,N')cobalt(II) top

Crystal data top

[CoBr₂(C₁₁H₁₀N₂)]	F(000) = 748
M_r = 388.94	D_x = 2.000 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6393 reflections
a = 7.5541 (7) Å	θ = 3.1–26.0°
b = 9.7249 (7) Å	µ = 7.49 mm⁻¹
c = 17.7352 (16) Å	T = 173 K
β = 97.392 (7)°	Needle, blue
V = 1292.05 (19) Å³	0.45 × 0.13 × 0.10 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2519 independent reflections
Radiation source: fine-focus sealed tube	1546 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.099
ϕ and ω scans	θ_max = 26.0°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −7→9
T_min = 0.379, T_max = 0.512	k = −10→11
6393 measured reflections	l = −21→21

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)] = 0.085	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.164	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0569P)² + 5.329P] where P = (F_o² + 2F_c²)/3
2519 reflections	(Δ/σ)_max = 0.002
145 parameters	Δρ_max = 2.16 e Å⁻³
0 restraints	Δρ_min = −1.13 e Å⁻³

Crystal data top

[CoBr₂(C₁₁H₁₀N₂)]	V = 1292.05 (19) Å³
M_r = 388.94	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.5541 (7) Å	µ = 7.49 mm⁻¹
b = 9.7249 (7) Å	T = 173 K
c = 17.7352 (16) Å	0.45 × 0.13 × 0.10 mm
β = 97.392 (7)°

Data collection top

Bruker APEXII CCD diffractometer	2519 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1546 reflections with I > 2σ(I)
T_min = 0.379, T_max = 0.512	R_int = 0.099
6393 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.085	0 restraints
wR(F²) = 0.164	H-atom parameters constrained
S = 1.05	Δρ_max = 2.16 e Å⁻³
2519 reflections	Δρ_min = −1.13 e Å⁻³
145 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
C3	0.1467 (17)	0.3377 (14)	0.1282 (7)	0.046 (3)
H3	0.1126	0.2832	0.1669	0.056*
C4	0.1737 (16)	0.2801 (14)	0.0583 (7)	0.046 (3)
H4	0.1588	0.1861	0.0501	0.055*
Br1	0.04264 (18)	0.91295 (15)	0.11995 (7)	0.0501 (4)
N2	0.2940 (12)	0.7342 (12)	−0.0213 (5)	0.042 (3)
C6	0.2426 (15)	0.5016 (13)	0.0149 (6)	0.034 (3)
C7	0.2897 (14)	0.6000 (13)	−0.0435 (6)	0.034 (3)
C8	0.3225 (16)	0.5617 (15)	−0.1157 (6)	0.045 (3)
H8	0.3190	0.4698	−0.1303	0.054*
C9	0.3607 (16)	0.6643 (16)	−0.1658 (6)	0.045 (4)
H9	0.3865	0.6417	−0.2142	0.055*
C10	0.3601 (18)	0.7992 (16)	−0.1431 (6)	0.049 (4)
H10	0.3798	0.8692	−0.1768	0.059*
N1	0.2173 (12)	0.5578 (10)	0.0835 (5)	0.031 (2)
C11	0.3303 (17)	0.8297 (15)	−0.0711 (6)	0.043 (3)
H11	0.3356	0.9212	−0.0558	0.052*
Br2	0.54925 (17)	0.79979 (15)	0.16326 (7)	0.0467 (4)
Co1	0.2680 (2)	0.76329 (17)	0.09004 (8)	0.0345 (4)
C5	0.2222 (17)	0.3629 (13)	0.0021 (6)	0.040 (3)
H5	0.2414	0.3255	−0.0444	0.047*
C2	0.1726 (16)	0.4806 (14)	0.1384 (7)	0.041 (3)
C1	0.144 (2)	0.5546 (17)	0.2094 (7)	0.070 (5)
H1A	0.2213	0.5171	0.2516	0.084*
H1B	0.0218	0.5439	0.2183	0.084*
H1C	0.1697	0.6505	0.2042	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C3	0.033 (7)	0.049 (9)	0.057 (7)	0.002 (7)	0.002 (6)	0.001 (6)
C4	0.036 (7)	0.036 (8)	0.061 (8)	0.007 (6)	−0.010 (6)	−0.022 (6)
Br1	0.0389 (8)	0.0543 (10)	0.0579 (8)	0.0073 (7)	0.0089 (6)	−0.0186 (6)
N2	0.023 (5)	0.072 (8)	0.029 (5)	0.002 (5)	0.002 (4)	−0.013 (5)
C6	0.020 (6)	0.042 (7)	0.038 (6)	0.008 (6)	−0.002 (4)	−0.013 (5)
C7	0.020 (6)	0.047 (8)	0.033 (6)	0.007 (6)	0.002 (4)	−0.009 (5)
C8	0.034 (7)	0.062 (9)	0.037 (6)	0.010 (7)	−0.002 (5)	−0.026 (6)
C9	0.025 (6)	0.077 (11)	0.035 (6)	0.010 (7)	0.005 (5)	−0.005 (6)
C10	0.053 (9)	0.060 (10)	0.035 (6)	0.019 (8)	0.005 (6)	−0.003 (6)
N1	0.021 (5)	0.034 (6)	0.039 (5)	−0.002 (4)	0.010 (4)	−0.007 (4)
C11	0.046 (8)	0.047 (9)	0.038 (6)	−0.012 (7)	0.011 (5)	−0.001 (6)
Br2	0.0342 (7)	0.0557 (9)	0.0488 (7)	0.0003 (7)	−0.0004 (5)	−0.0266 (6)
Co1	0.0306 (9)	0.0390 (11)	0.0347 (8)	−0.0018 (8)	0.0070 (6)	−0.0138 (7)
C5	0.042 (8)	0.034 (7)	0.042 (6)	0.001 (6)	0.002 (5)	−0.006 (6)
C2	0.026 (7)	0.046 (8)	0.049 (7)	−0.005 (6)	−0.001 (5)	−0.005 (6)
C1	0.095 (13)	0.077 (12)	0.040 (7)	−0.029 (10)	0.014 (7)	−0.001 (7)

Geometric parameters (Å, º) top

Co1—Br1	2.352 (2)	C7—C8	1.386 (14)
Co1—Br2	2.3698 (19)	C8—C9	1.391 (19)
Co1—N1	2.035 (10)	C8—H8	0.9300
Co1—N2	2.029 (8)	C9—C10	1.372 (19)
C3—C4	1.399 (17)	C9—H9	0.9300
C3—C2	1.411 (18)	C10—C11	1.357 (16)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.366 (18)	N1—C2	1.309 (15)
C4—H4	0.9300	C11—H11	0.9300
N2—C11	1.334 (16)	C5—H5	0.9300
N2—C7	1.362 (16)	C2—C1	1.491 (18)
C6—N1	1.369 (13)	C1—H1A	0.9600
C6—C5	1.373 (17)	C1—H1B	0.9600
C6—C7	1.487 (17)	C1—H1C	0.9600

C4—C3—C2	118.3 (13)	C2—N1—C6	120.7 (11)
C4—C3—H3	120.8	C2—N1—Co1	125.8 (8)
C2—C3—H3	120.8	C6—N1—Co1	113.3 (8)
C5—C4—C3	119.5 (13)	N2—C11—C10	123.0 (13)
C5—C4—H4	120.2	N2—C11—H11	118.5
C3—C4—H4	120.2	C10—C11—H11	118.5
C11—N2—C7	118.3 (10)	N2—Co1—N1	81.3 (4)
C11—N2—Co1	127.0 (9)	N2—Co1—Br1	118.0 (3)
C7—N2—Co1	114.4 (8)	N1—Co1—Br1	119.0 (3)
N1—C6—C5	120.9 (11)	N2—Co1—Br2	111.2 (3)
N1—C6—C7	115.8 (10)	N1—Co1—Br2	109.1 (3)
C5—C6—C7	123.3 (10)	Br1—Co1—Br2	114.06 (7)
N2—C7—C8	121.6 (12)	C4—C5—C6	119.6 (11)
N2—C7—C6	114.5 (9)	C4—C5—H5	120.2
C8—C7—C6	123.9 (12)	C6—C5—H5	120.2
C7—C8—C9	118.3 (13)	N1—C2—C3	120.9 (11)
C7—C8—H8	120.9	N1—C2—C1	115.6 (12)
C9—C8—H8	120.9	C3—C2—C1	123.4 (12)
C10—C9—C8	119.3 (11)	C2—C1—H1A	109.5
C10—C9—H9	120.3	C2—C1—H1B	109.5
C8—C9—H9	120.3	H1A—C1—H1B	109.5
C11—C10—C9	119.5 (13)	C2—C1—H1C	109.5
C11—C10—H10	120.3	H1A—C1—H1C	109.5
C9—C10—H10	120.3	H1B—C1—H1C	109.5

C2—C3—C4—C5	−0.6 (18)	C7—N2—Co1—N1	−7.8 (8)
C11—N2—C7—C8	0.2 (16)	C11—N2—Co1—Br1	60.6 (11)
Co1—N2—C7—C8	−173.8 (8)	C7—N2—Co1—Br1	−126.1 (7)
C11—N2—C7—C6	−178.2 (10)	C11—N2—Co1—Br2	−74.0 (10)
Co1—N2—C7—C6	7.8 (12)	C7—N2—Co1—Br2	99.4 (7)
N1—C6—C7—N2	−2.6 (14)	C2—N1—Co1—N2	−176.7 (10)
C5—C6—C7—N2	176.5 (11)	C6—N1—Co1—N2	6.3 (7)
N1—C6—C7—C8	179.1 (10)	C2—N1—Co1—Br1	−59.5 (10)
C5—C6—C7—C8	−1.8 (18)	C6—N1—Co1—Br1	123.5 (7)
N2—C7—C8—C9	0.1 (17)	C2—N1—Co1—Br2	73.7 (9)
C6—C7—C8—C9	178.3 (11)	C6—N1—Co1—Br2	−103.3 (7)
C7—C8—C9—C10	−1.7 (18)	C3—C4—C5—C6	−0.5 (18)
C8—C9—C10—C11	3.1 (19)	N1—C6—C5—C4	0.9 (18)
C5—C6—N1—C2	−0.2 (16)	C7—C6—C5—C4	−178.1 (10)
C7—C6—N1—C2	178.9 (10)	C6—N1—C2—C3	−0.9 (17)
C5—C6—N1—Co1	177.0 (9)	Co1—N1—C2—C3	−177.7 (9)
C7—C6—N1—Co1	−3.9 (11)	C6—N1—C2—C1	−178.3 (11)
C7—N2—C11—C10	1.2 (18)	Co1—N1—C2—C1	4.9 (15)
Co1—N2—C11—C10	174.3 (10)	C4—C3—C2—N1	1.3 (18)
C9—C10—C11—N2	−3 (2)	C4—C3—C2—C1	178.5 (13)
C11—N2—Co1—N1	178.8 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···Br1ⁱ	0.96	2.89	3.849 (14)	178
C8—H8···Br2ⁱⁱ	0.93	2.89	3.771 (14)	158

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[CoBr₂(C₁₁H₁₀N₂)]
M_r	388.94
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	7.5541 (7), 9.7249 (7), 17.7352 (16)
β (°)	97.392 (7)
V (Å³)	1292.05 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	7.49
Crystal size (mm)	0.45 × 0.13 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.379, 0.512
No. of measured, independent and observed [I > 2σ(I)] reflections	6393, 2519, 1546
R_int	0.099
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.085, 0.164, 1.05
No. of reflections	2519
No. of parameters	145
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.16, −1.13

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006).

Selected bond lengths (Å) top

Co1—Br1	2.352 (2)	Co1—N1	2.035 (10)
Co1—Br2	2.3698 (19)	Co1—N2	2.029 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···Br1ⁱ	0.96	2.89	3.849 (14)	178
C8—H8···Br2ⁱⁱ	0.93	2.89	3.771 (14)	158

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z.

Acknowledgements

We are grateful to the Islamic Azad University, Omidieh Branch, for financial support.

References

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