Diiodido{2-[(4-meth-oxy-phen-yl)imino-meth-yl]pyridine-κ(2)N,N'}zinc.

In the title complex, [ZnI(2)(C(13)H(12)N(2)O)], the Zn(II) atom has a distorted tetra-hedral coordination. The organic ligand is bidentate, coordinating the Zn(II) atom via the two N atoms. The benzene and pyridine rings are oriented at a dihedral angle of 11.67 (9)°. In the crystal, weak C-H⋯I and C-H⋯O hydrogen bonds are observed, in addition to π-π stacking inter-actions, with a centroid-centroid distance of 3.72 (5) Å.

Related literature

For the synthesis of the ligand, see: Dehghanpour et al. (2009 ▶). For related structures, see: Talei Bavil Olyai et al. (2008 ▶); Khalaj et al. (2008 ▶); Wriedt et al. (2008 ▶).

Experimental

Crystal data

[ZnI2(C13H12N2O)]

M = 531.42

Triclinic,

a = 8.0290 (15) Å

b = 10.002 (2) Å

c = 10.538 (2) Å

α = 83.498 (4)°

β = 80.208 (4)°

γ = 71.441 (4)°

V = 789.0 (3) Å3

Z = 2

Mo Kα radiation

μ = 5.46 mm−1

T = 150 K

0.25 × 0.12 × 0.08 mm

Data collection

Bruker APEX DUO diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.591, T max = 0.746

6595 measured reflections

3584 independent reflections

3165 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.061

S = 1.03

3584 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.97 e Å−3

Δρmin = −0.96 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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812030486/br2207sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030486/br2207Isup2.hkl

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

[ZnI2(C13H12N2O)]	Z = 2
Mr = 531.42	F(000) = 496
Triclinic, P1	Dx = 2.237 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0290 (15) Å	Cell parameters from 4756 reflections
b = 10.002 (2) Å	θ = 2.7–27.5°
c = 10.538 (2) Å	µ = 5.46 mm−1
α = 83.498 (4)°	T = 150 K
β = 80.208 (4)°	Needle, yellow
γ = 71.441 (4)°	0.25 × 0.12 × 0.08 mm
V = 789.0 (3) Å3

Bruker APEX DUO diffractometer	3584 independent reflections
Radiation source: fine-focus sealed tube	3165 reflections with I > 2σ(I)
Bruker Triumph monochromator	Rint = 0.019
φ and ω scans	θmax = 27.6°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.591, Tmax = 0.746	k = −12→12
6595 measured reflections	l = −13→13

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.061	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0321P)2 + 0.2822P] where P = (Fo2 + 2Fc2)/3
3584 reflections	(Δ/σ)max = 0.001
173 parameters	Δρmax = 0.97 e Å−3
0 restraints	Δρmin = −0.96 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	0.29826 (5)	0.21887 (4)	0.31555 (3)	0.02060 (9)
I1	0.03469 (3)	0.34732 (2)	0.19749 (2)	0.02706 (7)
I2	0.48121 (3)	0.36778 (2)	0.36178 (2)	0.02624 (7)
O1	−0.2104 (3)	0.2079 (3)	0.9260 (2)	0.0298 (5)
N1	0.4611 (3)	0.0328 (3)	0.2380 (2)	0.0209 (5)
N2	0.2355 (3)	0.0735 (3)	0.4600 (2)	0.0181 (5)
C1	0.5851 (4)	0.0129 (4)	0.1337 (3)	0.0272 (7)
H1A	0.6042	0.0931	0.0833	0.033*
C2	0.6867 (4)	−0.1210 (4)	0.0967 (3)	0.0298 (8)
H2A	0.7753	−0.1314	0.0231	0.036*
C3	0.6591 (4)	−0.2385 (4)	0.1666 (3)	0.0296 (7)
H3A	0.7263	−0.3308	0.1414	0.035*
C4	0.5294 (4)	−0.2188 (4)	0.2758 (3)	0.0271 (7)
H4A	0.5066	−0.2975	0.3265	0.033*
C5	0.4351 (4)	−0.0822 (3)	0.3085 (3)	0.0194 (6)
C6	0.3046 (4)	−0.0532 (3)	0.4257 (3)	0.0214 (6)
H6A	0.2717	−0.1283	0.4759	0.026*
C7	0.1168 (4)	0.1062 (3)	0.5786 (3)	0.0182 (6)
C8	0.0968 (4)	0.0023 (3)	0.6749 (3)	0.0222 (6)
H8A	0.1596	−0.0943	0.6620	0.027*
C9	−0.0142 (4)	0.0400 (3)	0.7885 (3)	0.0244 (7)
H9A	−0.0283	−0.0309	0.8537	0.029*
C10	−0.1054 (4)	0.1810 (3)	0.8083 (3)	0.0220 (6)
C11	−0.0880 (4)	0.2861 (3)	0.7136 (3)	0.0243 (7)
H11A	−0.1521	0.3825	0.7262	0.029*
C12	0.0264 (4)	0.2462 (3)	0.5993 (3)	0.0241 (7)
H12A	0.0422	0.3170	0.5344	0.029*
C13	−0.2999 (5)	0.3525 (4)	0.9528 (3)	0.0327 (8)
H13A	−0.3631	0.3573	1.0411	0.049*
H13B	−0.3849	0.3951	0.8920	0.049*
H13C	−0.2128	0.4041	0.9436	0.049*

	U11	U22	U33	U12	U13	U23
Zn1	0.02370 (17)	0.01803 (19)	0.01862 (18)	−0.00642 (14)	−0.00014 (13)	0.00062 (14)
I1	0.02842 (11)	0.02108 (12)	0.03186 (13)	−0.00595 (8)	−0.00941 (9)	0.00063 (9)
I2	0.03011 (12)	0.02100 (12)	0.02954 (12)	−0.00861 (8)	−0.00965 (8)	0.00107 (9)
O1	0.0389 (13)	0.0246 (13)	0.0197 (12)	−0.0077 (10)	0.0096 (10)	−0.0021 (10)
N1	0.0222 (12)	0.0215 (14)	0.0189 (12)	−0.0063 (10)	−0.0031 (10)	−0.0017 (11)
N2	0.0190 (11)	0.0183 (13)	0.0164 (12)	−0.0058 (10)	−0.0023 (9)	0.0018 (10)
C1	0.0308 (16)	0.0309 (19)	0.0207 (16)	−0.0142 (14)	0.0033 (13)	−0.0015 (14)
C2	0.0252 (15)	0.039 (2)	0.0240 (17)	−0.0089 (14)	0.0051 (13)	−0.0106 (15)
C3	0.0290 (16)	0.0281 (19)	0.0274 (18)	−0.0010 (14)	−0.0028 (13)	−0.0086 (15)
C4	0.0333 (16)	0.0208 (17)	0.0245 (17)	−0.0040 (13)	−0.0052 (13)	−0.0008 (13)
C5	0.0195 (13)	0.0199 (16)	0.0184 (14)	−0.0052 (11)	−0.0046 (11)	0.0013 (12)
C6	0.0237 (14)	0.0206 (16)	0.0183 (15)	−0.0060 (12)	−0.0010 (11)	−0.0004 (12)
C7	0.0177 (13)	0.0200 (15)	0.0165 (14)	−0.0069 (11)	−0.0013 (11)	0.0014 (12)
C8	0.0256 (15)	0.0164 (15)	0.0226 (15)	−0.0049 (12)	−0.0022 (12)	0.0010 (12)
C9	0.0283 (15)	0.0204 (16)	0.0225 (16)	−0.0084 (13)	0.0013 (12)	0.0027 (13)
C10	0.0234 (14)	0.0254 (17)	0.0171 (14)	−0.0092 (12)	0.0003 (11)	−0.0006 (13)
C11	0.0283 (15)	0.0163 (15)	0.0234 (16)	−0.0029 (12)	0.0013 (13)	−0.0006 (13)
C12	0.0293 (15)	0.0200 (16)	0.0209 (15)	−0.0085 (13)	0.0021 (12)	0.0023 (13)
C13	0.0432 (19)	0.0264 (19)	0.0227 (17)	−0.0080 (15)	0.0092 (14)	−0.0058 (14)

Zn1—N1	2.067 (3)	C4—H4A	0.9500
Zn1—N2	2.095 (3)	C5—C6	1.468 (4)
Zn1—I2	2.5326 (5)	C6—H6A	0.9500
Zn1—I1	2.5455 (5)	C7—C12	1.380 (4)
O1—C10	1.377 (3)	C7—C8	1.395 (4)
O1—C13	1.432 (4)	C8—C9	1.376 (4)
N1—C1	1.338 (4)	C8—H8A	0.9500
N1—C5	1.351 (4)	C9—C10	1.388 (4)
N2—C6	1.278 (4)	C9—H9A	0.9500
N2—C7	1.438 (4)	C10—C11	1.389 (4)
C1—C2	1.388 (5)	C11—C12	1.397 (4)
C1—H1A	0.9500	C11—H11A	0.9500
C2—C3	1.373 (5)	C12—H12A	0.9500
C2—H2A	0.9500	C13—H13A	0.9800
C3—C4	1.400 (5)	C13—H13B	0.9800
C3—H3A	0.9500	C13—H13C	0.9800
C4—C5	1.385 (4)
N1—Zn1—N2	80.45 (10)	N2—C6—C5	119.7 (3)
N1—Zn1—I2	110.55 (7)	N2—C6—H6A	120.1
N2—Zn1—I2	118.95 (7)	C5—C6—H6A	120.1
N1—Zn1—I1	114.61 (7)	C12—C7—C8	119.4 (3)
N2—Zn1—I1	111.29 (7)	C12—C7—N2	118.2 (3)
I2—Zn1—I1	116.02 (2)	C8—C7—N2	122.3 (3)
C10—O1—C13	117.6 (3)	C9—C8—C7	119.9 (3)
C1—N1—C5	118.3 (3)	C9—C8—H8A	120.1
C1—N1—Zn1	129.6 (2)	C7—C8—H8A	120.1
C5—N1—Zn1	112.07 (19)	C8—C9—C10	120.4 (3)
C6—N2—C7	121.8 (3)	C8—C9—H9A	119.8
C6—N2—Zn1	111.4 (2)	C10—C9—H9A	119.8
C7—N2—Zn1	126.6 (2)	O1—C10—C9	115.9 (3)
N1—C1—C2	122.1 (3)	O1—C10—C11	123.4 (3)
N1—C1—H1A	118.9	C9—C10—C11	120.7 (3)
C2—C1—H1A	118.9	C10—C11—C12	118.2 (3)
C3—C2—C1	120.0 (3)	C10—C11—H11A	120.9
C3—C2—H2A	120.0	C12—C11—H11A	120.9
C1—C2—H2A	120.0	C7—C12—C11	121.4 (3)
C2—C3—C4	118.2 (3)	C7—C12—H12A	119.3
C2—C3—H3A	120.9	C11—C12—H12A	119.3
C4—C3—H3A	120.9	O1—C13—H13A	109.5
C5—C4—C3	118.7 (3)	O1—C13—H13B	109.5
C5—C4—H4A	120.6	H13A—C13—H13B	109.5
C3—C4—H4A	120.6	O1—C13—H13C	109.5
N1—C5—C4	122.6 (3)	H13A—C13—H13C	109.5
N1—C5—C6	115.5 (3)	H13B—C13—H13C	109.5
C4—C5—C6	121.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···I2i	0.95	3.13	3.761 (3)	125
C1—H1A···O1ii	0.95	2.47	3.338 (4)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯I2i	0.95	3.13	3.761 (3)	125
C1—H1A⋯O1ii	0.95	2.47	3.338 (4)	152

Symmetry codes: (i) ; (ii) .