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

In the title compound, [ZnI(2)(C(12)H(9)BrN(2))], the metal centre displays a moderately distorted tetra-hedral coordination geometry defined by two iodide anions and two N atoms of the organic ligand. The dihedral angle between the pyridine and benzene rings is 15.15 (13)°.

Related literature

For the crystal structure of similar imino­pyridine complexes, see: Dehghanpour, Mahmoudi, Khalaj & Salmanpour (2007 ▶); Dehghanpour, Mahmoudi, Khalaj, Salmanpour & Adib (2007 ▶). For related structures see: Lee et al. (2008 ▶); Wriedt et al. (2008 ▶).

Experimental

Crystal data

[ZnI2(C12H9BrN2)]

M = 580.29

Triclinic,

a = 8.0749 (9) Å

b = 9.7323 (11) Å

c = 11.1884 (13) Å

α = 79.157 (2)°

β = 71.178 (3)°

γ = 67.325 (2)°

V = 765.87 (15) Å3

Z = 2

Mo Kα radiation

μ = 8.23 mm−1

T = 100 (2) K

0.45 × 0.21 × 0.12 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (APEX2; Bruker, 2005 ▶) T min = 0.135, T max = 0.378

9814 measured reflections

4449 independent reflections

3983 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.084

S = 1.01

4449 reflections

163 parameters

H-atom parameters constrained

Δρmax = 1.94 e Å−3

Δρmin = −1.96 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/S1600536808020680/rz2225sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020680/rz2225Isup2.hkl

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

[ZnI2(C12H9BrN2)]	Z = 2
Mr = 580.29	F000 = 532
Triclinic, P1	Dx = 2.516 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.0749 (9) Å	Cell parameters from 1953 reflections
b = 9.7323 (11) Å	θ = 2.8–34.4º
c = 11.1884 (13) Å	µ = 8.23 mm−1
α = 79.157 (2)º	T = 100 (2) K
β = 71.178 (3)º	Plate, yellow
γ = 67.325 (2)º	0.45 × 0.21 × 0.12 mm
V = 765.87 (15) Å3

Bruker APEXII CCD area-detector diffractometer	4449 independent reflections
Radiation source: fine-focus sealed tube	3983 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.040
T = 100(2) K	θmax = 30.0º
ω scans	θmin = 1.9º
Absorption correction: multi-scan(APEX2; Bruker, 2005)	h = −11→11
Tmin = 0.135, Tmax = 0.378	k = −13→13
9814 measured reflections	l = −15→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032	H-atom parameters constrained
wR(F2) = 0.084	w = 1/[σ2(Fo2) + (0.04P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
4449 reflections	Δρmax = 1.94 e Å−3
163 parameters	Δρmin = −1.96 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
I1	−0.28834 (3)	0.85145 (2)	0.60583 (2)	0.01640 (7)
I2	0.16700 (3)	0.84434 (2)	0.72880 (2)	0.01874 (7)
Br1	0.51281 (5)	0.79618 (4)	−0.04600 (3)	0.02005 (9)
Zn1	0.02685 (5)	0.70420 (4)	0.64300 (4)	0.01456 (9)
N1	0.0641 (4)	0.4960 (3)	0.7379 (3)	0.0178 (6)
N2	0.2315 (4)	0.5720 (3)	0.4997 (3)	0.0154 (5)
C1	0.2115 (5)	0.3877 (4)	0.6720 (3)	0.0159 (6)
C2	0.2711 (5)	0.2407 (4)	0.7206 (3)	0.0195 (7)
H2A	0.3754	0.1671	0.6722	0.023*
C3	0.1746 (6)	0.2034 (4)	0.8421 (4)	0.0234 (7)
H3A	0.2130	0.1039	0.8786	0.028*
C4	0.0213 (5)	0.3136 (4)	0.9090 (4)	0.0240 (8)
H4A	−0.0483	0.2900	0.9913	0.029*
C5	−0.0296 (5)	0.4594 (4)	0.8543 (3)	0.0225 (7)
H5A	−0.1335	0.5349	0.9010	0.027*
C6	0.3009 (5)	0.4359 (4)	0.5426 (3)	0.0158 (6)
H6A	0.4084	0.3675	0.4913	0.019*
C7	0.3033 (4)	0.6193 (4)	0.3715 (3)	0.0147 (6)
C8	0.4198 (5)	0.5200 (4)	0.2790 (3)	0.0169 (6)
H8A	0.4551	0.4155	0.3005	0.020*
C9	0.4848 (5)	0.5734 (4)	0.1550 (3)	0.0185 (7)
H9A	0.5671	0.5061	0.0920	0.022*
C10	0.4275 (5)	0.7263 (4)	0.1250 (3)	0.0165 (6)
C11	0.3091 (5)	0.8267 (4)	0.2146 (3)	0.0204 (7)
H11A	0.2710	0.9311	0.1921	0.024*
C12	0.2468 (5)	0.7728 (4)	0.3380 (3)	0.0195 (7)
H12A	0.1649	0.8407	0.4006	0.023*

	U11	U22	U33	U12	U13	U23
I1	0.01523 (11)	0.01337 (11)	0.02111 (12)	−0.00533 (8)	−0.00547 (8)	−0.00085 (8)
I2	0.01755 (12)	0.01407 (12)	0.02641 (13)	−0.00646 (9)	−0.00745 (9)	−0.00117 (9)
Br1	0.02369 (18)	0.01625 (17)	0.01622 (17)	−0.00571 (14)	−0.00288 (13)	0.00060 (13)
Zn1	0.01415 (18)	0.01008 (17)	0.01727 (19)	−0.00385 (14)	−0.00195 (14)	−0.00109 (14)
N1	0.0177 (13)	0.0139 (13)	0.0216 (14)	−0.0076 (11)	−0.0031 (11)	−0.0002 (11)
N2	0.0181 (13)	0.0132 (13)	0.0162 (13)	−0.0079 (11)	−0.0027 (10)	−0.0022 (10)
C1	0.0166 (14)	0.0140 (15)	0.0186 (15)	−0.0073 (12)	−0.0050 (12)	−0.0003 (12)
C2	0.0230 (16)	0.0138 (15)	0.0218 (16)	−0.0058 (13)	−0.0077 (13)	0.0001 (13)
C3	0.0318 (19)	0.0139 (16)	0.0265 (18)	−0.0090 (14)	−0.0136 (15)	0.0058 (14)
C4	0.0275 (19)	0.0201 (17)	0.0220 (17)	−0.0116 (15)	−0.0035 (14)	0.0056 (14)
C5	0.0230 (17)	0.0223 (18)	0.0200 (17)	−0.0092 (14)	−0.0034 (13)	0.0023 (14)
C6	0.0156 (14)	0.0111 (14)	0.0197 (16)	−0.0043 (12)	−0.0038 (12)	−0.0016 (12)
C7	0.0148 (14)	0.0123 (14)	0.0170 (15)	−0.0053 (12)	−0.0039 (11)	−0.0008 (12)
C8	0.0194 (15)	0.0097 (14)	0.0201 (16)	−0.0041 (12)	−0.0035 (12)	−0.0032 (12)
C9	0.0189 (15)	0.0138 (15)	0.0199 (16)	−0.0040 (13)	−0.0020 (12)	−0.0040 (12)
C10	0.0167 (14)	0.0178 (16)	0.0155 (15)	−0.0080 (13)	−0.0032 (12)	0.0001 (12)
C11	0.0248 (17)	0.0126 (15)	0.0206 (17)	−0.0055 (13)	−0.0031 (13)	−0.0018 (13)
C12	0.0210 (16)	0.0089 (14)	0.0213 (17)	−0.0034 (12)	0.0013 (13)	−0.0013 (12)

I1—Zn1	2.5201 (5)	C3—H3A	0.9500
I2—Zn1	2.5389 (5)	C4—C5	1.394 (5)
Zn1—N1	2.062 (3)	C4—H4A	0.9500
Zn1—N2	2.094 (3)	C5—H5A	0.9500
Br1—C10	1.902 (3)	C6—H6A	0.9500
Zn1—N1	2.062 (3)	C7—C8	1.391 (5)
Zn1—N2	2.094 (3)	C7—C12	1.398 (5)
N1—C5	1.339 (4)	C8—C9	1.392 (5)
N1—C1	1.353 (4)	C8—H8A	0.9500
N2—C6	1.289 (4)	C9—C10	1.387 (5)
N2—C7	1.424 (4)	C9—H9A	0.9500
C1—C2	1.385 (5)	C10—C11	1.381 (5)
C1—C6	1.473 (5)	C11—C12	1.385 (5)
C2—C3	1.391 (5)	C11—H11A	0.9500
C2—H2A	0.9500	C12—H12A	0.9500
C3—C4	1.387 (6)
N1—Zn1—N2	80.30 (11)	N1—C5—C4	121.8 (3)
N1—Zn1—I1	117.81 (8)	N1—C5—H5A	119.1
N2—Zn1—I1	117.60 (8)	C4—C5—H5A	119.1
N1—Zn1—I2	109.45 (8)	N2—C6—C1	119.2 (3)
N2—Zn1—I2	110.18 (8)	N2—C6—H6A	120.4
I1—Zn1—I2	116.210 (17)	C1—C6—H6A	120.4
C5—N1—C1	118.8 (3)	C8—C7—C12	119.5 (3)
C5—N1—Zn1	128.7 (3)	C8—C7—N2	123.0 (3)
C1—N1—Zn1	112.4 (2)	C12—C7—N2	117.5 (3)
C6—N2—C7	120.8 (3)	C7—C8—C9	120.2 (3)
C6—N2—Zn1	111.5 (2)	C7—C8—H8A	119.9
C7—N2—Zn1	127.5 (2)	C9—C8—H8A	119.9
N1—C1—C2	122.7 (3)	C10—C9—C8	118.9 (3)
N1—C1—C6	115.2 (3)	C10—C9—H9A	120.5
C2—C1—C6	122.1 (3)	C8—C9—H9A	120.5
C1—C2—C3	118.4 (3)	C11—C10—C9	121.8 (3)
C1—C2—H2A	120.8	C11—C10—Br1	120.0 (3)
C3—C2—H2A	120.8	C9—C10—Br1	118.1 (3)
C4—C3—C2	119.0 (3)	C10—C11—C12	118.9 (3)
C4—C3—H3A	120.5	C10—C11—H11A	120.6
C2—C3—H3A	120.5	C12—C11—H11A	120.6
C3—C4—C5	119.3 (3)	C11—C12—C7	120.6 (3)
C3—C4—H4A	120.3	C11—C12—H12A	119.7
C5—C4—H4A	120.3	C7—C12—H12A	119.7
N2—Zn1—N1—C5	−175.2 (3)	Zn1—N1—C5—C4	−175.4 (3)
I1—Zn1—N1—C5	−59.0 (3)	C3—C4—C5—N1	0.9 (6)
I2—Zn1—N1—C5	76.7 (3)	C7—N2—C6—C1	−174.2 (3)
N2—Zn1—N1—C1	9.0 (2)	Zn1—N2—C6—C1	10.1 (4)
I1—Zn1—N1—C1	125.1 (2)	N1—C1—C6—N2	−2.6 (5)
I2—Zn1—N1—C1	−99.1 (2)	C2—C1—C6—N2	175.4 (3)
N1—Zn1—N2—C6	−10.3 (2)	C6—N2—C7—C8	14.4 (5)
I1—Zn1—N2—C6	−126.7 (2)	Zn1—N2—C7—C8	−170.5 (3)
I2—Zn1—N2—C6	97.0 (2)	C6—N2—C7—C12	−168.0 (3)
N1—Zn1—N2—C7	174.3 (3)	Zn1—N2—C7—C12	7.0 (4)
I1—Zn1—N2—C7	57.9 (3)	C12—C7—C8—C9	2.2 (5)
I2—Zn1—N2—C7	−78.4 (3)	N2—C7—C8—C9	179.7 (3)
C5—N1—C1—C2	−0.8 (5)	C7—C8—C9—C10	−1.7 (5)
Zn1—N1—C1—C2	175.5 (3)	C8—C9—C10—C11	0.5 (5)
C5—N1—C1—C6	177.2 (3)	C8—C9—C10—Br1	−178.3 (3)
Zn1—N1—C1—C6	−6.5 (4)	C9—C10—C11—C12	0.3 (6)
N1—C1—C2—C3	0.2 (5)	Br1—C10—C11—C12	179.0 (3)
C6—C1—C2—C3	−177.6 (3)	C10—C11—C12—C7	0.2 (6)
C1—C2—C3—C4	0.9 (6)	C8—C7—C12—C11	−1.5 (5)
C2—C3—C4—C5	−1.5 (6)	N2—C7—C12—C11	−179.1 (3)
C1—N1—C5—C4	0.2 (5)

I1—Zn1	2.5201 (5)
I2—Zn1	2.5389 (5)
Zn1—N1	2.062 (3)
Zn1—N2	2.094 (3)

N1—Zn1—N2	80.30 (11)
N1—Zn1—I1	117.81 (8)
N2—Zn1—I1	117.60 (8)
N1—Zn1—I2	109.45 (8)
N2—Zn1—I2	110.18 (8)
I1—Zn1—I2	116.210 (17)