Dibromido(6,6'-dimethyl-2,2'-bipyridine-κN,N')zinc(II).

In the title compound, [ZnBr(2)(C(12)H(12)N(2))], the Zn(II) atom is four-coordinated in a distorted tetra-hedral arrangement by an N,N'-bidentate 6,6'-dimethyl-2,2'-bipyridine ligand and two bromide ions. In the crystal, there are aromatic π-π contacts between the pyridine rings [centroid-centroid distances = 3.818 (3) and 3.728 (4) Å].

Related literature

For related crystal structures containing a Zn atom coordin­ated by an N,N-bidentate bipyridine or phenanthroline-type ligand and two halide ions, see: Ahmadi et al. (2008 ▶, 2009 ▶); Alizadeh, Heidari, et al. (2009 ▶); Alizadeh, Kalateh, et al. (2009 ▶); Blake et al. (2007 ▶); Khalighi et al. (2008 ▶); Khan & Tuck (1984 ▶); Khavasi et al. (2008 ▶); Khoshtarkib et al. (2009 ▶); Lee et al. (2007 ▶); Marjani et al. (2009 ▶); Reimann et al. (1966 ▶); Wriedt et al. (2008 ▶).

Experimental

Crystal data

[ZnBr2(C12H12N2)]

M = 409.43

Monoclinic,

a = 7.6506 (15) Å

b = 10.279 (2) Å

c = 18.023 (4) Å

β = 95.93 (3)°

V = 1409.8 (5) Å3

Z = 4

Mo Kα radiation

μ = 7.39 mm−1

T = 298 K

0.17 × 0.16 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.300, T max = 0.418

11390 measured reflections

3822 independent reflections

2717 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.126

S = 1.11

3822 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.81 e Å−3

Δρmin = −0.68 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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/S1600536809039610/hb5122sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039610/hb5122Isup2.hkl

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

[ZnBr2(C12H12N2)]	F(000) = 792
Mr = 409.43	Dx = 1.929 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1342 reflections
a = 7.6506 (15) Å	θ = 2.3–29.3°
b = 10.279 (2) Å	µ = 7.39 mm−1
c = 18.023 (4) Å	T = 298 K
β = 95.93 (3)°	Prism, colourless
V = 1409.8 (5) Å3	0.17 × 0.16 × 0.12 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3822 independent reflections
Radiation source: fine-focus sealed tube	2717 reflections with I > 2σ(I)
graphite	Rint = 0.068
φ and ω scans	θmax = 29.3°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −9→10
Tmin = 0.300, Tmax = 0.418	k = −14→14
11390 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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0419P)2 + 2.306P] where P = (Fo2 + 2Fc2)/3
3822 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.81 e Å−3
0 restraints	Δρmin = −0.68 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	0.1523 (12)	0.9316 (8)	0.2403 (4)	0.077 (2)
H1A	0.2661	0.8940	0.2538	0.092*
H1B	0.0679	0.8635	0.2288	0.092*
H1C	0.1185	0.9824	0.2812	0.092*
C2	0.1591 (7)	1.0167 (6)	0.1736 (3)	0.0486 (13)
C3	0.1234 (9)	1.1474 (7)	0.1764 (4)	0.0614 (16)
H3	0.0946	1.1851	0.2204	0.074*
C4	0.1306 (9)	1.2221 (6)	0.1134 (4)	0.0654 (18)
H4	0.1055	1.3105	0.1144	0.078*
C5	0.1755 (8)	1.1645 (6)	0.0485 (4)	0.0578 (15)
H5	0.1801	1.2138	0.0054	0.069*
C6	0.2132 (7)	1.0330 (5)	0.0485 (3)	0.0425 (11)
C7	0.2666 (6)	0.9633 (5)	−0.0177 (3)	0.0388 (11)
C8	0.2796 (8)	1.0242 (6)	−0.0855 (3)	0.0535 (14)
H8	0.2510	1.1117	−0.0919	0.064*
C9	0.3356 (9)	0.9530 (8)	−0.1428 (4)	0.0668 (19)
H9	0.3455	0.9926	−0.1886	0.080*
C10	0.3770 (8)	0.8238 (8)	−0.1333 (3)	0.0581 (16)
H10	0.4156	0.7754	−0.1720	0.070*
C11	0.3597 (8)	0.7663 (6)	−0.0638 (3)	0.0490 (13)
C12	0.3987 (12)	0.6258 (7)	−0.0493 (4)	0.074 (2)
H12A	0.2942	0.5824	−0.0371	0.089*
H12B	0.4889	0.6177	−0.0084	0.089*
H12C	0.4380	0.5868	−0.0930	0.089*
N1	0.2039 (6)	0.9612 (4)	0.1102 (2)	0.0394 (9)
N2	0.3051 (6)	0.8366 (4)	−0.0080 (2)	0.0390 (9)
Zn1	0.26913 (8)	0.76759 (6)	0.09736 (3)	0.04134 (17)
Br1	0.03105 (10)	0.62512 (7)	0.10150 (4)	0.0682 (2)
Br2	0.52344 (8)	0.69964 (7)	0.17038 (3)	0.05791 (19)

	U11	U22	U33	U12	U13	U23
C1	0.119 (6)	0.070 (5)	0.045 (3)	0.017 (5)	0.023 (4)	−0.006 (3)
C2	0.048 (3)	0.047 (3)	0.051 (3)	0.006 (2)	0.007 (2)	−0.010 (2)
C3	0.064 (4)	0.052 (4)	0.067 (4)	0.014 (3)	0.002 (3)	−0.018 (3)
C4	0.071 (4)	0.036 (3)	0.085 (5)	0.012 (3)	−0.009 (4)	−0.013 (3)
C5	0.058 (3)	0.041 (3)	0.070 (4)	0.004 (3)	−0.014 (3)	0.015 (3)
C6	0.039 (3)	0.034 (3)	0.053 (3)	0.000 (2)	−0.003 (2)	0.004 (2)
C7	0.036 (2)	0.038 (3)	0.042 (3)	−0.004 (2)	−0.001 (2)	0.009 (2)
C8	0.057 (3)	0.054 (3)	0.048 (3)	−0.005 (3)	−0.001 (3)	0.017 (3)
C9	0.074 (4)	0.083 (5)	0.044 (3)	−0.013 (4)	0.008 (3)	0.020 (3)
C10	0.055 (3)	0.083 (5)	0.036 (3)	−0.003 (3)	0.005 (2)	−0.001 (3)
C11	0.055 (3)	0.056 (3)	0.036 (3)	−0.005 (3)	0.006 (2)	−0.002 (2)
C12	0.117 (6)	0.054 (4)	0.052 (4)	0.022 (4)	0.017 (4)	−0.006 (3)
N1	0.043 (2)	0.035 (2)	0.040 (2)	0.0048 (17)	0.0054 (18)	0.0015 (17)
N2	0.047 (2)	0.039 (2)	0.0310 (19)	−0.0009 (18)	0.0045 (17)	0.0043 (17)
Zn1	0.0537 (4)	0.0344 (3)	0.0365 (3)	0.0041 (3)	0.0078 (2)	0.0059 (2)
Br1	0.0718 (4)	0.0582 (4)	0.0742 (4)	−0.0162 (3)	0.0053 (3)	0.0207 (3)
Br2	0.0605 (4)	0.0634 (4)	0.0489 (3)	0.0125 (3)	0.0017 (3)	0.0138 (3)

C1—C2	1.492 (9)	C8—C9	1.370 (10)
C1—H1A	0.9600	C8—H8	0.9300
C1—H1B	0.9600	C9—C10	1.372 (11)
C1—H1C	0.9600	C9—H9	0.9300
C2—N1	1.352 (7)	C10—C11	1.403 (8)
C2—C3	1.373 (8)	C10—H10	0.9300
C3—C4	1.376 (10)	C11—N2	1.340 (7)
C3—H3	0.9300	C11—C12	1.492 (9)
C4—C5	1.386 (10)	C12—H12A	0.9600
C4—H4	0.9300	C12—H12B	0.9600
C5—C6	1.383 (8)	C12—H12C	0.9600
C5—H5	0.9300	Zn1—N1	2.071 (4)
C6—N1	1.342 (7)	Zn1—N2	2.072 (4)
C6—C7	1.486 (8)	Zn1—Br2	2.3400 (11)
C7—N2	1.343 (7)	Zn1—Br1	2.3444 (10)
C7—C8	1.384 (7)
C2—C1—H1A	109.5	C8—C9—C10	120.6 (6)
C2—C1—H1B	109.5	C8—C9—H9	119.7
H1A—C1—H1B	109.5	C10—C9—H9	119.7
C2—C1—H1C	109.5	C9—C10—C11	118.5 (6)
H1A—C1—H1C	109.5	C9—C10—H10	120.7
H1B—C1—H1C	109.5	C11—C10—H10	120.7
N1—C2—C3	120.8 (6)	N2—C11—C10	120.5 (6)
N1—C2—C1	117.8 (5)	N2—C11—C12	117.5 (5)
C3—C2—C1	121.4 (6)	C10—C11—C12	121.9 (6)
C2—C3—C4	119.4 (6)	C11—C12—H12A	109.5
C2—C3—H3	120.3	C11—C12—H12B	109.5
C4—C3—H3	120.3	H12A—C12—H12B	109.5
C3—C4—C5	119.5 (6)	C11—C12—H12C	109.5
C3—C4—H4	120.2	H12A—C12—H12C	109.5
C5—C4—H4	120.2	H12B—C12—H12C	109.5
C6—C5—C4	119.1 (6)	C6—N1—C2	120.5 (5)
C6—C5—H5	120.4	C6—N1—Zn1	113.7 (3)
C4—C5—H5	120.4	C2—N1—Zn1	125.8 (4)
N1—C6—C5	120.6 (5)	C11—N2—C7	120.4 (4)
N1—C6—C7	116.3 (4)	C11—N2—Zn1	125.8 (4)
C5—C6—C7	123.1 (5)	C7—N2—Zn1	113.8 (3)
N2—C7—C8	121.2 (5)	N1—Zn1—N2	80.22 (17)
N2—C7—C6	116.0 (4)	N1—Zn1—Br2	114.82 (13)
C8—C7—C6	122.8 (5)	N2—Zn1—Br2	115.86 (12)
C9—C8—C7	118.7 (6)	N1—Zn1—Br1	113.58 (12)
C9—C8—H8	120.7	N2—Zn1—Br1	114.84 (13)
C7—C8—H8	120.7	Br2—Zn1—Br1	113.53 (4)
N1—C2—C3—C4	1.1 (10)	C3—C2—N1—Zn1	178.0 (5)
C1—C2—C3—C4	−179.7 (7)	C1—C2—N1—Zn1	−1.2 (8)
C2—C3—C4—C5	−0.7 (10)	C10—C11—N2—C7	−0.2 (8)
C3—C4—C5—C6	−0.4 (10)	C12—C11—N2—C7	−179.5 (6)
C4—C5—C6—N1	1.0 (9)	C10—C11—N2—Zn1	179.2 (4)
C4—C5—C6—C7	−178.5 (5)	C12—C11—N2—Zn1	−0.1 (8)
N1—C6—C7—N2	−2.0 (7)	C8—C7—N2—C11	0.9 (8)
C5—C6—C7—N2	177.6 (5)	C6—C7—N2—C11	−178.0 (5)
N1—C6—C7—C8	179.2 (5)	C8—C7—N2—Zn1	−178.5 (4)
C5—C6—C7—C8	−1.3 (8)	C6—C7—N2—Zn1	2.6 (6)
N2—C7—C8—C9	−1.0 (9)	C6—N1—Zn1—N2	0.8 (4)
C6—C7—C8—C9	177.9 (6)	C2—N1—Zn1—N2	−177.8 (5)
C7—C8—C9—C10	0.3 (10)	C6—N1—Zn1—Br2	114.9 (3)
C8—C9—C10—C11	0.4 (10)	C2—N1—Zn1—Br2	−63.7 (5)
C9—C10—C11—N2	−0.5 (9)	C6—N1—Zn1—Br1	−112.2 (3)
C9—C10—C11—C12	178.8 (7)	C2—N1—Zn1—Br1	69.3 (5)
C5—C6—N1—C2	−0.6 (8)	C11—N2—Zn1—N1	178.7 (5)
C7—C6—N1—C2	179.0 (5)	C7—N2—Zn1—N1	−1.9 (4)
C5—C6—N1—Zn1	−179.3 (4)	C11—N2—Zn1—Br2	65.8 (5)
C7—C6—N1—Zn1	0.3 (6)	C7—N2—Zn1—Br2	−114.8 (3)
C3—C2—N1—C6	−0.4 (9)	C11—N2—Zn1—Br1	−69.7 (5)
C1—C2—N1—C6	−179.7 (6)	C7—N2—Zn1—Br1	109.7 (3)

Zn1—N1	2.071 (4)
Zn1—N2	2.072 (4)
Zn1—Br2	2.3400 (11)
Zn1—Br1	2.3444 (10)

N1—Zn1—N2

80.22 (17)