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

In the title compound, [CdBr(2)(C(12)H(12)N(2))], the Cd(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 Br atoms. In the crystal, C-H⋯Br hydrogen bonds and π-π stacking inter-actions between the pyridine rings [centroid-centroid distance = 3.763 (5) Å] are present.

Related literature

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

Experimental

Crystal data

[CdBr2(C12H12N2)]

M = 456.45

Monoclinic,

a = 7.7606 (11) Å

b = 10.3832 (17) Å

c = 18.184 (2) Å

β = 97.460 (11)°

V = 1452.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 6.98 mm−1

T = 298 K

0.40 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.054, T max = 0.155

11844 measured reflections

2862 independent reflections

1945 reflections with I > 2σ(I)

R int = 0.098

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.124

S = 1.03

2862 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.61 e Å−3

Δρmin = −0.78 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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812033648/hy2576sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033648/hy2576Isup2.hkl

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

[CdBr2(C12H12N2)]	F(000) = 864
Mr = 456.45	Dx = 2.087 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11844 reflections
a = 7.7606 (11) Å	θ = 2.3–26.0°
b = 10.3832 (17) Å	µ = 6.98 mm−1
c = 18.184 (2) Å	T = 298 K
β = 97.460 (11)°	Block, colorless
V = 1452.8 (4) Å3	0.40 × 0.20 × 0.15 mm
Z = 4

Bruker APEXII CCD diffractometer	2862 independent reflections
Radiation source: fine-focus sealed tube	1945 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.098
φ and ω scans	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
Tmin = 0.054, Tmax = 0.155	k = −12→12
11844 measured reflections	l = −19→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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0602P)2] where P = (Fo2 + 2Fc2)/3
2862 reflections	(Δ/σ)max = 0.003
154 parameters	Δρmax = 0.61 e Å−3
0 restraints	Δρmin = −0.78 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	0.1386 (14)	0.4345 (10)	0.2292 (5)	0.081 (3)
H1A	0.2494	0.3951	0.2444	0.098*
H1B	0.0530	0.3689	0.2161	0.098*
H1C	0.1055	0.4852	0.2693	0.098*
C2	0.1505 (10)	0.5178 (8)	0.1648 (5)	0.060 (2)
C3	0.1116 (12)	0.6486 (9)	0.1659 (6)	0.077 (3)
H3	0.0782	0.6861	0.2083	0.092*
C4	0.1230 (12)	0.7210 (8)	0.1044 (7)	0.078 (3)
H4	0.0963	0.8083	0.1044	0.094*
C5	0.1750 (11)	0.6642 (8)	0.0409 (6)	0.071 (3)
H5	0.1835	0.7133	−0.0013	0.085*
C6	0.2136 (9)	0.5334 (7)	0.0417 (4)	0.0483 (17)
C7	0.2699 (8)	0.4638 (7)	−0.0232 (4)	0.0461 (17)
C8	0.2878 (11)	0.5254 (9)	−0.0896 (5)	0.066 (2)
H8	0.2613	0.6124	−0.0958	0.079*
C9	0.3445 (11)	0.4568 (11)	−0.1454 (5)	0.072 (3)
H9	0.3569	0.4969	−0.1902	0.087*
C10	0.3835 (11)	0.3288 (11)	−0.1359 (5)	0.070 (3)
H10	0.4226	0.2818	−0.1740	0.084*
C11	0.3646 (10)	0.2703 (8)	−0.0699 (5)	0.0543 (19)
C12	0.4037 (14)	0.1324 (10)	−0.0560 (6)	0.080 (3)
H12A	0.3013	0.0891	−0.0446	0.095*
H12B	0.4944	0.1241	−0.0150	0.095*
H12C	0.4410	0.0945	−0.0995	0.095*
N1	0.1993 (7)	0.4635 (6)	0.1027 (3)	0.0470 (14)
N2	0.3092 (7)	0.3379 (6)	−0.0136 (3)	0.0448 (13)
Cd1	0.27194 (7)	0.25065 (5)	0.09801 (3)	0.04813 (18)
Br1	0.01860 (13)	0.10203 (9)	0.10288 (6)	0.0775 (3)
Br2	0.54796 (12)	0.18801 (10)	0.17765 (5)	0.0693 (3)

	U11	U22	U33	U12	U13	U23
C1	0.105 (7)	0.093 (7)	0.049 (5)	0.005 (6)	0.024 (5)	−0.017 (5)
C2	0.053 (5)	0.056 (5)	0.069 (6)	0.005 (4)	−0.001 (4)	−0.020 (4)
C3	0.074 (6)	0.058 (6)	0.095 (8)	0.011 (5)	−0.002 (5)	−0.019 (5)
C4	0.064 (5)	0.040 (5)	0.123 (9)	0.016 (4)	−0.022 (6)	−0.027 (5)
C5	0.063 (5)	0.042 (4)	0.099 (7)	−0.005 (4)	−0.023 (5)	0.011 (5)
C6	0.042 (4)	0.039 (4)	0.060 (5)	−0.002 (3)	−0.010 (3)	0.004 (3)
C7	0.039 (4)	0.049 (4)	0.048 (4)	−0.011 (3)	−0.003 (3)	0.011 (3)
C8	0.062 (5)	0.069 (6)	0.066 (6)	−0.011 (4)	0.002 (4)	0.023 (5)
C9	0.066 (5)	0.103 (8)	0.048 (5)	−0.017 (5)	0.006 (4)	0.020 (5)
C10	0.060 (5)	0.109 (8)	0.042 (4)	−0.019 (5)	0.007 (4)	−0.003 (5)
C11	0.055 (4)	0.060 (5)	0.048 (4)	−0.002 (4)	0.009 (4)	−0.005 (4)
C12	0.093 (7)	0.079 (7)	0.067 (6)	0.007 (5)	0.013 (5)	−0.019 (5)
N1	0.042 (3)	0.048 (3)	0.051 (4)	−0.001 (3)	0.002 (3)	−0.007 (3)
N2	0.047 (3)	0.046 (3)	0.041 (3)	−0.008 (3)	0.004 (3)	0.001 (3)
Cd1	0.0576 (3)	0.0421 (3)	0.0456 (3)	0.0049 (3)	0.0102 (2)	0.0069 (2)
Br1	0.0804 (6)	0.0631 (6)	0.0900 (7)	−0.0163 (5)	0.0155 (5)	0.0197 (5)
Br2	0.0661 (5)	0.0808 (6)	0.0597 (5)	0.0161 (5)	0.0033 (4)	0.0171 (5)

C1—C2	1.469 (13)	C8—C9	1.358 (14)
C1—H1A	0.9600	C8—H8	0.9300
C1—H1B	0.9600	C9—C10	1.369 (15)
C1—H1C	0.9600	C9—H9	0.9300
C2—N1	1.360 (10)	C10—C11	1.369 (12)
C2—C3	1.392 (13)	C10—H10	0.9300
C3—C4	1.360 (15)	C11—N2	1.357 (10)
C3—H3	0.9300	C11—C12	1.479 (12)
C4—C5	1.402 (14)	C12—H12A	0.9600
C4—H4	0.9300	C12—H12B	0.9600
C5—C6	1.390 (11)	C12—H12C	0.9600
C5—H5	0.9300	N1—Cd1	2.285 (6)
C6—N1	1.341 (10)	N2—Cd1	2.274 (6)
C6—C7	1.498 (11)	Cd1—Br1	2.5099 (11)
C7—N2	1.349 (9)	Cd1—Br2	2.5106 (11)
C7—C8	1.389 (11)
C2—C1—H1A	109.5	C8—C9—C10	120.1 (8)
C2—C1—H1B	109.5	C8—C9—H9	119.9
H1A—C1—H1B	109.5	C10—C9—H9	119.9
C2—C1—H1C	109.5	C9—C10—C11	119.6 (9)
H1A—C1—H1C	109.5	C9—C10—H10	120.2
H1B—C1—H1C	109.5	C11—C10—H10	120.2
N1—C2—C3	120.1 (9)	N2—C11—C10	120.8 (8)
N1—C2—C1	118.2 (7)	N2—C11—C12	116.8 (7)
C3—C2—C1	121.8 (9)	C10—C11—C12	122.4 (8)
C4—C3—C2	119.3 (10)	C11—C12—H12A	109.5
C4—C3—H3	120.3	C11—C12—H12B	109.5
C2—C3—H3	120.3	H12A—C12—H12B	109.5
C3—C4—C5	120.1 (8)	C11—C12—H12C	109.5
C3—C4—H4	119.9	H12A—C12—H12C	109.5
C5—C4—H4	119.9	H12B—C12—H12C	109.5
C6—C5—C4	119.1 (9)	C6—N1—C2	121.6 (7)
C6—C5—H5	120.5	C6—N1—Cd1	116.5 (5)
C4—C5—H5	120.5	C2—N1—Cd1	121.9 (5)
N1—C6—C5	119.8 (8)	C7—N2—C11	119.4 (6)
N1—C6—C7	117.0 (6)	C7—N2—Cd1	116.7 (5)
C5—C6—C7	123.1 (8)	C11—N2—Cd1	123.8 (5)
N2—C7—C8	120.9 (7)	N2—Cd1—N1	73.0 (2)
N2—C7—C6	116.7 (6)	N2—Cd1—Br1	117.85 (15)
C8—C7—C6	122.4 (7)	N1—Cd1—Br1	113.28 (14)
C9—C8—C7	119.1 (9)	N2—Cd1—Br2	114.84 (15)
C9—C8—H8	120.4	N1—Cd1—Br2	115.17 (15)
C7—C8—H8	120.4	Br1—Cd1—Br2	115.72 (4)
N1—C2—C3—C4	0.0 (13)	C3—C2—N1—Cd1	178.3 (6)
C1—C2—C3—C4	−179.3 (9)	C1—C2—N1—Cd1	−2.4 (10)
C2—C3—C4—C5	−0.6 (15)	C8—C7—N2—C11	−0.9 (10)
C3—C4—C5—C6	0.3 (14)	C6—C7—N2—C11	−178.6 (7)
C4—C5—C6—N1	0.6 (12)	C8—C7—N2—Cd1	−179.7 (5)
C4—C5—C6—C7	179.9 (7)	C6—C7—N2—Cd1	2.6 (7)
N1—C6—C7—N2	−3.0 (9)	C10—C11—N2—C7	0.9 (11)
C5—C6—C7—N2	177.7 (7)	C12—C11—N2—C7	−179.4 (7)
N1—C6—C7—C8	179.3 (7)	C10—C11—N2—Cd1	179.7 (6)
C5—C6—C7—C8	0.0 (11)	C12—C11—N2—Cd1	−0.6 (10)
N2—C7—C8—C9	0.4 (12)	C7—N2—Cd1—N1	−1.2 (4)
C6—C7—C8—C9	178.0 (7)	C11—N2—Cd1—N1	180.0 (6)
C7—C8—C9—C10	−0.1 (13)	C7—N2—Cd1—Br1	106.6 (4)
C8—C9—C10—C11	0.2 (13)	C11—N2—Cd1—Br1	−72.2 (6)
C9—C10—C11—N2	−0.6 (13)	C7—N2—Cd1—Br2	−111.6 (4)
C9—C10—C11—C12	179.8 (8)	C11—N2—Cd1—Br2	69.6 (6)
C5—C6—N1—C2	−1.2 (11)	C6—N1—Cd1—N2	−0.5 (5)
C7—C6—N1—C2	179.4 (6)	C2—N1—Cd1—N2	−178.0 (6)
C5—C6—N1—Cd1	−178.8 (5)	C6—N1—Cd1—Br1	−114.1 (5)
C7—C6—N1—Cd1	1.9 (8)	C2—N1—Cd1—Br1	68.4 (6)
C3—C2—N1—C6	0.9 (11)	C6—N1—Cd1—Br2	109.5 (5)
C1—C2—N1—C6	−179.8 (8)	C2—N1—Cd1—Br2	−68.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1C···Br1i	0.96	2.90	3.848 (10)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1C⋯Br1i	0.96	2.90	3.848 (10)	171

Symmetry code: (i) .