Dibromido{2-[(4-bromo-phen-yl)imino-meth-yl]pyridine-κN,N'}zinc(II).

In the title complex, [ZnBr(2)(C(12)H(9)BrN(2))], the Zn(II) ion is in a distorted tetra-hedral coordination environment formed by two imine N atoms of the bis-chelating N-heterocyclic ligand and two Br atoms. The dihedral angle between the pyridine and benzene rings is 8.04 (17)°.

Related literature

For background information on diimine complexes, see: Small et al. (1998 ▶). For the use of imino­pyridine complexes as olefin polymerization catalysts, see: Ittel et al. (2000 ▶); Britovsek et al. (1999 ▶). For related structures, see Dehghanpour & Mahmoudi (2007 ▶); Dehghanpour et al. (2007 ▶).

Experimental

Crystal data

[ZnBr2(C12H9BrN2)]

M = 486.31

Triclinic,

a = 7.7506 (13) Å

b = 8.7413 (16) Å

c = 10.9846 (18) Å

α = 89.966 (5)°

β = 72.182 (6)°

γ = 88.665 (6)°

V = 708.3 (2) Å3

Z = 2

Mo Kα radiation

μ = 10.18 mm−1

T = 100 K

0.28 × 0.16 × 0.12 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (APEX2; Bruker, 2005 ▶) T min = 0.153, T max = 0.293

7668 measured reflections

3230 independent reflections

2703 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.095

S = 1.00

3230 reflections

163 parameters

H-atom parameters constrained

Δρmax = 2.06 e Å−3

Δρmin = −1.70 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: APEX2; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809025653/lh2845sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025653/lh2845Isup2.hkl

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

[ZnBr2(C12H9BrN2)]	Z = 2
Mr = 486.31	F(000) = 460
Triclinic, P1	Dx = 2.280 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7506 (13) Å	Cell parameters from 469 reflections
b = 8.7413 (16) Å	θ = 2.1–21.4°
c = 10.9846 (18) Å	µ = 10.18 mm−1
α = 89.966 (5)°	T = 100 K
β = 72.182 (6)°	Prism, colourless
γ = 88.665 (6)°	0.28 × 0.16 × 0.12 mm
V = 708.3 (2) Å3

Bruker APEXII CCD area-detector diffractometer	3230 independent reflections
Radiation source: fine-focus sealed tube	2703 reflections with I > 2σ(I)
graphite	Rint = 0.066
Detector resolution: 0 pixels mm-1	θmax = 27.5°, θmin = 2.0°
ω scans	h = −10→10
Absorption correction: multi-scan (APEX2; Bruker, 2005)	k = −11→11
Tmin = 0.153, Tmax = 0.293	l = −14→14
7668 measured reflections

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.02P)2 + 5.8P] where P = (Fo2 + 2Fc2)/3
3230 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 2.06 e Å−3
0 restraints	Δρmin = −1.70 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
Zn1	0.60716 (8)	0.80440 (7)	0.65671 (6)	0.01457 (15)
Br1	0.37048 (7)	0.65625 (6)	0.63756 (5)	0.01697 (13)
Br2	0.81619 (8)	0.67009 (7)	0.73568 (6)	0.02353 (15)
Br3	1.15053 (7)	0.69529 (6)	−0.03171 (5)	0.01971 (14)
N1	0.5509 (6)	1.0180 (5)	0.7411 (4)	0.0161 (9)
N2	0.7495 (6)	0.9383 (5)	0.5020 (4)	0.0135 (9)
C1	0.6485 (7)	1.1285 (6)	0.6650 (5)	0.0142 (10)
C2	0.6414 (7)	1.2794 (6)	0.7039 (5)	0.0175 (11)
H2	0.7116	1.3522	0.6505	0.021*
C3	0.5270 (8)	1.3201 (7)	0.8248 (5)	0.0193 (11)
H3	0.5181	1.4212	0.8530	0.023*
C4	0.4275 (7)	1.2091 (7)	0.9018 (6)	0.0205 (12)
H4	0.3510	1.2339	0.9830	0.025*
C5	0.4428 (7)	1.0584 (7)	0.8567 (5)	0.0188 (11)
H5	0.3752	0.9836	0.9093	0.023*
C6	0.7597 (7)	1.0777 (6)	0.5374 (5)	0.0154 (10)
H6	0.8369	1.1452	0.4824	0.018*
C7	0.8461 (7)	0.8856 (6)	0.3766 (5)	0.0150 (10)
C8	0.9339 (7)	0.9837 (7)	0.2784 (5)	0.0181 (11)
H8	0.9309	1.0884	0.2941	0.022*
C9	1.0255 (7)	0.9271 (6)	0.1580 (5)	0.0164 (11)
H9	1.0858	0.9929	0.0931	0.020*
C10	1.0264 (7)	0.7708 (6)	0.1348 (5)	0.0156 (11)
C11	0.9348 (7)	0.6706 (6)	0.2296 (5)	0.0173 (11)
H11	0.9336	0.5666	0.2125	0.021*
C12	0.8446 (7)	0.7298 (6)	0.3514 (5)	0.0171 (11)
H12	0.7829	0.6644	0.4160	0.020*

	U11	U22	U33	U12	U13	U23
Zn1	0.0158 (3)	0.0090 (3)	0.0168 (3)	−0.0017 (2)	−0.0018 (2)	−0.0003 (2)
Br1	0.0164 (3)	0.0128 (3)	0.0203 (3)	−0.00344 (19)	−0.0032 (2)	−0.0010 (2)
Br2	0.0240 (3)	0.0125 (3)	0.0378 (4)	−0.0022 (2)	−0.0148 (2)	0.0031 (2)
Br3	0.0235 (3)	0.0160 (3)	0.0157 (3)	−0.0026 (2)	0.0000 (2)	−0.0042 (2)
N1	0.016 (2)	0.013 (2)	0.018 (2)	0.0013 (17)	−0.0022 (17)	−0.0008 (18)
N2	0.014 (2)	0.010 (2)	0.015 (2)	0.0001 (16)	−0.0027 (17)	0.0004 (17)
C1	0.014 (2)	0.009 (2)	0.020 (3)	−0.0001 (19)	−0.006 (2)	0.001 (2)
C2	0.019 (3)	0.011 (3)	0.023 (3)	0.000 (2)	−0.007 (2)	−0.001 (2)
C3	0.027 (3)	0.011 (3)	0.020 (3)	0.000 (2)	−0.007 (2)	−0.006 (2)
C4	0.019 (3)	0.022 (3)	0.018 (3)	0.001 (2)	−0.002 (2)	−0.008 (2)
C5	0.017 (3)	0.017 (3)	0.019 (3)	−0.001 (2)	0.000 (2)	0.000 (2)
C6	0.014 (2)	0.014 (3)	0.017 (3)	−0.001 (2)	−0.004 (2)	0.000 (2)
C7	0.012 (2)	0.015 (3)	0.017 (3)	−0.0015 (19)	−0.0029 (19)	−0.001 (2)
C8	0.019 (3)	0.014 (3)	0.018 (3)	−0.004 (2)	0.000 (2)	−0.002 (2)
C9	0.021 (3)	0.011 (3)	0.015 (3)	−0.004 (2)	−0.002 (2)	0.002 (2)
C10	0.016 (2)	0.016 (3)	0.012 (2)	0.000 (2)	−0.0002 (19)	−0.003 (2)
C11	0.019 (3)	0.010 (3)	0.023 (3)	−0.001 (2)	−0.005 (2)	−0.001 (2)
C12	0.021 (3)	0.014 (3)	0.013 (2)	−0.005 (2)	−0.001 (2)	0.002 (2)

Zn1—N1	2.062 (5)	C4—C5	1.397 (8)
Zn1—N2	2.094 (4)	C4—H4	0.9300
Zn1—Br1	2.3310 (8)	C5—H5	0.9300
Zn1—Br2	2.3507 (9)	C6—H6	0.9300
Br3—C10	1.898 (5)	C7—C12	1.391 (8)
N1—C5	1.333 (7)	C7—C8	1.392 (8)
N1—C1	1.361 (7)	C8—C9	1.382 (7)
N2—C6	1.291 (7)	C8—H8	0.9300
N2—C7	1.422 (7)	C9—C10	1.389 (8)
C1—C2	1.381 (7)	C9—H9	0.9300
C1—C6	1.466 (8)	C10—C11	1.389 (8)
C2—C3	1.394 (8)	C11—C12	1.399 (8)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.374 (8)	C12—H12	0.9300
C3—H3	0.9300
N1—Zn1—N2	80.62 (18)	N1—C5—C4	122.3 (5)
N1—Zn1—Br1	119.57 (13)	N1—C5—H5	118.9
N2—Zn1—Br1	119.19 (13)	C4—C5—H5	118.9
N1—Zn1—Br2	110.14 (13)	N2—C6—C1	119.3 (5)
N2—Zn1—Br2	108.91 (12)	N2—C6—H6	120.3
Br1—Zn1—Br2	113.95 (3)	C1—C6—H6	120.3
C5—N1—C1	118.2 (5)	C12—C7—C8	119.4 (5)
C5—N1—Zn1	129.7 (4)	C12—C7—N2	117.7 (5)
C1—N1—Zn1	112.0 (3)	C8—C7—N2	122.8 (5)
C6—N2—C7	121.6 (5)	C9—C8—C7	120.7 (5)
C6—N2—Zn1	111.2 (4)	C9—C8—H8	119.6
C7—N2—Zn1	126.7 (4)	C7—C8—H8	119.6
N1—C1—C2	122.5 (5)	C8—C9—C10	119.2 (5)
N1—C1—C6	115.5 (5)	C8—C9—H9	120.4
C2—C1—C6	121.9 (5)	C10—C9—H9	120.4
C1—C2—C3	118.6 (5)	C9—C10—C11	121.4 (5)
C1—C2—H2	120.7	C9—C10—Br3	118.7 (4)
C3—C2—H2	120.7	C11—C10—Br3	119.9 (4)
C4—C3—C2	119.1 (5)	C10—C11—C12	118.5 (5)
C4—C3—H3	120.4	C10—C11—H11	120.7
C2—C3—H3	120.4	C12—C11—H11	120.7
C3—C4—C5	119.2 (5)	C7—C12—C11	120.6 (5)
C3—C4—H4	120.4	C7—C12—H12	119.7
C5—C4—H4	120.4	C11—C12—H12	119.7
N2—Zn1—N1—C5	175.0 (5)	Zn1—N1—C5—C4	176.4 (4)
Br1—Zn1—N1—C5	56.7 (5)	C3—C4—C5—N1	0.0 (9)
Br2—Zn1—N1—C5	−78.2 (5)	C7—N2—C6—C1	176.2 (5)
N2—Zn1—N1—C1	−8.2 (4)	Zn1—N2—C6—C1	−11.5 (6)
Br1—Zn1—N1—C1	−126.5 (3)	N1—C1—C6—N2	4.8 (7)
Br2—Zn1—N1—C1	98.6 (4)	C2—C1—C6—N2	−174.1 (5)
N1—Zn1—N2—C6	10.6 (4)	C6—N2—C7—C12	172.5 (5)
Br1—Zn1—N2—C6	129.4 (3)	Zn1—N2—C7—C12	1.4 (7)
Br2—Zn1—N2—C6	−97.6 (4)	C6—N2—C7—C8	−10.4 (8)
N1—Zn1—N2—C7	−177.5 (4)	Zn1—N2—C7—C8	178.5 (4)
Br1—Zn1—N2—C7	−58.8 (4)	C12—C7—C8—C9	−2.7 (8)
Br2—Zn1—N2—C7	74.3 (4)	N2—C7—C8—C9	−179.7 (5)
C5—N1—C1—C2	0.9 (8)	C7—C8—C9—C10	1.2 (8)
Zn1—N1—C1—C2	−176.3 (4)	C8—C9—C10—C11	1.0 (8)
C5—N1—C1—C6	−177.9 (5)	C8—C9—C10—Br3	179.3 (4)
Zn1—N1—C1—C6	4.8 (6)	C9—C10—C11—C12	−1.7 (8)
N1—C1—C2—C3	−1.3 (8)	Br3—C10—C11—C12	−180.0 (4)
C6—C1—C2—C3	177.5 (5)	C8—C7—C12—C11	1.9 (8)
C1—C2—C3—C4	1.0 (8)	N2—C7—C12—C11	179.2 (5)
C2—C3—C4—C5	−0.4 (9)	C10—C11—C12—C7	0.2 (8)
C1—N1—C5—C4	−0.2 (8)

Zn1—N1	2.062 (5)
Zn1—N2	2.094 (4)
Zn1—Br1	2.3310 (8)
Zn1—Br2	2.3507 (9)

N1—Zn1—N2	80.62 (18)
N1—Zn1—Br1	119.57 (13)
N2—Zn1—Br1	119.19 (13)
N1—Zn1—Br2	110.14 (13)
N2—Zn1—Br2	108.91 (12)
Br1—Zn1—Br2	113.95 (3)