Dibromido(4,4'-dimethyl-2,2'-bipyridine-κN,N')zinc(II).

The asymmetric unit of the title compound, [ZnBr(2)(C(12)H(12)N(2))], contains two half-mol-ecules; both are completed by crystallographic twofold axes running through the Zn(II) atoms which are coordinated by an N,N'-bidentate 4,4'-dimethyl-2,2'-bipyridine ligand and two Br(-) ions, resulting in distorted ZnN(2)Br(2) tetra-hedral coordination geometries. In the crystal, C-H⋯Br inter-actions link the mol-ecules.

Related literature

For related structures, see: Ahmadi et al. (2008 ▶); Amani et al. (2009 ▶); Bellusci et al. (2008 ▶); Hojjat Kashani et al. (2008 ▶); Kalateh et al. (2008 ▶, 2010 ▶); Sakamoto et al. (2004 ▶); Sofetis et al. (2006 ▶); Willett et al. (2001 ▶); Yoshikawa et al. (2003 ▶); Yousefi et al. (2008 ▶).

Experimental

Crystal data

[ZnBr2(C12H12N2)]

M = 409.43

Monoclinic,

a = 13.801 (3) Å

b = 8.2454 (16) Å

c = 13.716 (3) Å

β = 117.47 (3)°

V = 1384.9 (6) Å3

Z = 4

Mo Kα radiation

μ = 7.52 mm−1

T = 120 K

0.30 × 0.22 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.157, T max = 0.479

8352 measured reflections

3560 independent reflections

2963 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.099

S = 1.07

3560 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.62 e Å−3

Δρmin = −1.04 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/S1600536810028692/hb5556sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810028692/hb5556Isup2.hkl

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

[ZnBr2(C12H12N2)]	F(000) = 792
Mr = 409.43	Dx = 1.964 Mg m−3
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 984 reflections
a = 13.801 (3) Å	θ = 2.5–29.2°
b = 8.2454 (16) Å	µ = 7.52 mm−1
c = 13.716 (3) Å	T = 120 K
β = 117.47 (3)°	Prism, colorless
V = 1384.9 (6) Å3	0.30 × 0.22 × 0.10 mm
Z = 4

Bruker SMART CCD diffractometer	3560 independent reflections
Radiation source: fine-focus sealed tube	2963 reflections with I > 2σ(I)
graphite	Rint = 0.050
phi and ω scans	θmax = 29.2°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −13→18
Tmin = 0.157, Tmax = 0.479	k = −11→11
8352 measured reflections	l = −18→17

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0449P)2 + 2.823P] where P = (Fo2 + 2Fc2)/3
3560 reflections	(Δ/σ)max = 0.001
156 parameters	Δρmax = 0.62 e Å−3
0 restraints	Δρmin = −1.04 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	0.3828 (3)	0.7308 (4)	0.0326 (3)	0.0225 (7)
H1	0.3650	0.8327	0.0001	0.027*
C2	0.3490 (3)	0.5946 (5)	−0.0343 (3)	0.0251 (8)
H2	0.3082	0.6056	−0.1101	0.030*
C3	0.3767 (3)	0.4417 (4)	0.0131 (3)	0.0234 (7)
C4	0.3428 (4)	0.2903 (5)	−0.0556 (4)	0.0313 (9)
H4A	0.2979	0.2252	−0.0345	0.038*
H4B	0.4065	0.2299	−0.0444	0.038*
H4C	0.3022	0.3191	−0.1318	0.038*
C5	0.4366 (3)	0.4324 (4)	0.1268 (3)	0.0220 (7)
H5	0.4562	0.3319	0.1611	0.026*
C6	0.4671 (3)	0.5733 (4)	0.1892 (3)	0.0185 (7)
C7	0.1273 (3)	0.7510 (4)	0.1512 (3)	0.0231 (7)
H7	0.1512	0.8521	0.1411	0.028*
C8	0.1556 (3)	0.6153 (5)	0.1110 (3)	0.0236 (7)
H8	0.1977	0.6260	0.0746	0.028*
C9	0.1209 (3)	0.4623 (4)	0.1250 (3)	0.0208 (7)
C10	0.1447 (4)	0.3130 (5)	0.0775 (4)	0.0287 (8)
H10C	0.1371	0.3370	0.0058	0.034*
H10B	0.0943	0.2289	0.0718	0.034*
H10A	0.2179	0.2774	0.1244	0.034*
C11	0.0594 (3)	0.4535 (4)	0.1817 (3)	0.0218 (7)
H11	0.0357	0.3534	0.1938	0.026*
C12	0.0334 (3)	0.5942 (4)	0.2202 (3)	0.0181 (7)
N1	0.4399 (3)	0.7211 (3)	0.1415 (3)	0.0186 (6)
N2	0.0668 (3)	0.7419 (3)	0.2042 (3)	0.0186 (6)
Zn1	0.5000	0.91089 (6)	0.2500	0.02024 (14)
Zn2	0.0000	0.93068 (6)	0.2500	0.01997 (14)
Br1	0.37461 (4)	1.05907 (4)	0.28513 (4)	0.02607 (11)
Br2	0.12396 (4)	1.07654 (4)	0.40271 (4)	0.02828 (11)

	U11	U22	U33	U12	U13	U23
C1	0.0274 (19)	0.0185 (15)	0.0221 (19)	0.0011 (14)	0.0119 (16)	0.0019 (13)
C2	0.0263 (19)	0.0284 (18)	0.0186 (18)	−0.0019 (15)	0.0085 (15)	−0.0024 (14)
C3	0.0261 (19)	0.0232 (16)	0.0232 (19)	−0.0021 (14)	0.0134 (16)	−0.0059 (14)
C4	0.035 (2)	0.0265 (18)	0.026 (2)	−0.0044 (17)	0.0089 (18)	−0.0115 (16)
C5	0.0271 (19)	0.0141 (14)	0.0249 (19)	−0.0016 (13)	0.0121 (16)	−0.0035 (12)
C6	0.0262 (18)	0.0125 (13)	0.0187 (18)	−0.0021 (12)	0.0118 (15)	−0.0013 (12)
C7	0.0268 (19)	0.0184 (15)	0.025 (2)	−0.0015 (14)	0.0127 (16)	0.0010 (13)
C8	0.028 (2)	0.0240 (16)	0.025 (2)	0.0003 (15)	0.0171 (17)	0.0010 (14)
C9	0.0227 (18)	0.0196 (15)	0.0191 (18)	0.0039 (13)	0.0087 (15)	−0.0007 (13)
C10	0.033 (2)	0.0238 (17)	0.033 (2)	0.0066 (16)	0.0183 (19)	−0.0023 (15)
C11	0.0289 (19)	0.0138 (14)	0.0249 (19)	0.0006 (13)	0.0142 (16)	−0.0001 (12)
C12	0.0227 (17)	0.0133 (14)	0.0192 (18)	0.0012 (12)	0.0104 (15)	0.0003 (11)
N1	0.0222 (15)	0.0147 (12)	0.0177 (15)	−0.0004 (11)	0.0082 (12)	−0.0013 (10)
N2	0.0253 (16)	0.0129 (12)	0.0175 (15)	−0.0004 (11)	0.0097 (13)	0.0004 (10)
Zn1	0.0277 (3)	0.0107 (2)	0.0231 (3)	0.000	0.0123 (3)	0.000
Zn2	0.0274 (3)	0.0106 (2)	0.0212 (3)	0.000	0.0106 (3)	0.000
Br1	0.0329 (2)	0.01709 (16)	0.0322 (2)	0.00397 (14)	0.01838 (17)	0.00109 (14)
Br2	0.0317 (2)	0.01954 (17)	0.0281 (2)	−0.00180 (14)	0.00900 (17)	−0.00723 (14)

C1—N1	1.332 (5)	C8—H8	0.9300
C1—C2	1.388 (5)	C9—C11	1.394 (5)
C1—H1	0.9300	C9—C10	1.498 (5)
C2—C3	1.388 (5)	C10—H10C	0.9600
C2—H2	0.9300	C10—H10B	0.9600
C3—C5	1.390 (6)	C10—H10A	0.9600
C3—C4	1.503 (5)	C11—C12	1.389 (5)
C4—H4A	0.9600	C11—H11	0.9300
C4—H4B	0.9600	C12—N2	1.355 (4)
C4—H4C	0.9600	C12—C12ii	1.488 (7)
C5—C6	1.387 (5)	Zn1—N1	2.053 (3)
C5—H5	0.9300	Zn2—N2	2.050 (3)
C6—N1	1.351 (4)	Zn1—N1i	2.053 (3)
C6—C6i	1.487 (8)	Zn1—Br1i	2.3428 (6)
C7—N2	1.339 (5)	Zn1—Br1	2.3428 (6)
C7—C8	1.380 (5)	Zn2—N2ii	2.050 (3)
C7—H7	0.9300	Zn2—Br2	2.3356 (9)
C8—C9	1.393 (5)	Zn2—Br2ii	2.3356 (9)
N1—C1—C2	122.5 (3)	C9—C10—H10C	109.5
N1—C1—H1	118.7	C9—C10—H10B	109.5
C2—C1—H1	118.7	H10C—C10—H10B	109.5
C1—C2—C3	119.3 (4)	C9—C10—H10A	109.5
C1—C2—H2	120.4	H10C—C10—H10A	109.5
C3—C2—H2	120.4	H10B—C10—H10A	109.5
C2—C3—C5	117.9 (3)	C12—C11—C9	120.0 (3)
C2—C3—C4	121.4 (4)	C12—C11—H11	120.0
C5—C3—C4	120.6 (4)	C9—C11—H11	120.0
C3—C4—H4A	109.5	N2—C12—C11	121.5 (3)
C3—C4—H4B	109.5	N2—C12—C12ii	115.6 (2)
H4A—C4—H4B	109.5	C11—C12—C12ii	122.9 (2)
C3—C4—H4C	109.5	C1—N1—C6	119.0 (3)
H4A—C4—H4C	109.5	C1—N1—Zn1	126.8 (2)
H4B—C4—H4C	109.5	C6—N1—Zn1	114.1 (2)
C6—C5—C3	120.0 (3)	C7—N2—C12	118.8 (3)
C6—C5—H5	120.0	C7—N2—Zn2	127.2 (2)
C3—C5—H5	120.0	C12—N2—Zn2	113.5 (2)
N1—C6—C5	121.3 (4)	N1—Zn1—N1i	80.61 (17)
N1—C6—C6i	115.6 (2)	N1—Zn1—Br1i	109.77 (9)
C5—C6—C6i	123.1 (2)	N1i—Zn1—Br1i	117.20 (9)
N2—C7—C8	122.2 (3)	N1—Zn1—Br1	117.20 (9)
N2—C7—H7	118.9	N1i—Zn1—Br1	109.77 (9)
C8—C7—H7	118.9	Br1i—Zn1—Br1	117.13 (3)
C7—C8—C9	120.1 (3)	N2—Zn2—N2ii	81.15 (17)
C7—C8—H8	119.9	N2—Zn2—Br2	114.76 (9)
C9—C8—H8	119.9	N2ii—Zn2—Br2	111.31 (9)
C8—C9—C11	117.4 (3)	N2—Zn2—Br2ii	111.31 (9)
C8—C9—C10	121.8 (3)	N2ii—Zn2—Br2ii	114.76 (9)
C11—C9—C10	120.8 (3)	Br2—Zn2—Br2ii	118.01 (4)
N1—C1—C2—C3	−1.1 (6)	C6i—C6—N1—Zn1	1.4 (5)
C1—C2—C3—C5	0.8 (6)	C8—C7—N2—C12	0.9 (6)
C1—C2—C3—C4	−179.6 (4)	C8—C7—N2—Zn2	−170.8 (3)
C2—C3—C5—C6	−0.2 (6)	C11—C12—N2—C7	−0.8 (6)
C4—C3—C5—C6	−179.9 (4)	C12ii—C12—N2—C7	179.9 (4)
C3—C5—C6—N1	−0.2 (6)	C11—C12—N2—Zn2	172.0 (3)
C3—C5—C6—C6i	−178.8 (4)	C12ii—C12—N2—Zn2	−7.3 (5)
N2—C7—C8—C9	0.0 (6)	C1—N1—Zn1—N1i	−177.6 (4)
C7—C8—C9—C11	−1.0 (6)	C6—N1—Zn1—N1i	−0.5 (2)
C7—C8—C9—C10	176.7 (4)	C1—N1—Zn1—Br1i	−62.0 (3)
C8—C9—C11—C12	1.0 (6)	C6—N1—Zn1—Br1i	115.1 (3)
C10—C9—C11—C12	−176.7 (4)	C1—N1—Zn1—Br1	74.9 (3)
C9—C11—C12—N2	−0.2 (6)	C6—N1—Zn1—Br1	−108.0 (3)
C9—C11—C12—C12ii	179.1 (4)	C7—N2—Zn2—N2ii	174.8 (4)
C2—C1—N1—C6	0.7 (6)	C12—N2—Zn2—N2ii	2.71 (19)
C2—C1—N1—Zn1	177.7 (3)	C7—N2—Zn2—Br2	−75.8 (3)
C5—C6—N1—C1	−0.1 (6)	C12—N2—Zn2—Br2	112.2 (3)
C6i—C6—N1—C1	178.7 (4)	C7—N2—Zn2—Br2ii	61.5 (3)
C5—C6—N1—Zn1	−177.4 (3)	C12—N2—Zn2—Br2ii	−110.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···Br1iii	0.96	2.89	3.772 (5)	152

Zn1—N1	2.053 (3)
Zn2—N2	2.050 (3)
Zn1—Br1	2.3428 (6)
Zn2—Br2	2.3356 (9)

N1—Zn1—N1i	80.61 (17)
N2—Zn2—N2ii	81.15 (17)

Symmetry codes: (i) ; (ii) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯Br1iii	0.96	2.89	3.772 (5)	152

Symmetry code: (iii) .