{2-[(2,5-Dimethyl-phen-yl)imino-methyl]pyridine-κN,N'}diiodidozinc(II).

In the mol-ecule of the title compound, [ZnI(2)(C(14)H(14)N(2))], the Zn atom is four-coordinated in a distorted tetra-hedral geometry by two N atoms of the Schiff base ligand and by two I atoms. The benzene and pyridine rings are oriented at a dihedral angle of 70.75 (3)°. The five-membered ring has an envelope conformation. There is a weak π-π inter-action between benzene rings, with a centroid-to-centroid distance of 3.975 (4) Å.

Related literature

For general background, see: Gibson et al. (2007 ▶); Ittel et al. (2000 ▶); Gibson & Spitzmesser (2003 ▶); Bart et al. (2004 ▶); Sugiyama et al. (2004 ▶); Kooistra et al. (2004 ▶); Bouwkamp et al. (2006 ▶). For related literature, see: Dehghanpour et al. (2007 ▶).

Experimental

Crystal data

[ZnI2(C14H14N2)]

M = 529.46

Monoclinic,

a = 11.467 (5) Å

b = 9.627 (4) Å

c = 15.868 (6) Å

β = 103.88 (3)°

V = 1700.6 (12) Å3

Z = 4

Mo Kα radiation

μ = 5.06 mm−1

T = 298 (2) K

0.5 × 0.4 × 0.25 mm

Data collection

Stoe IPDSII diffractometer

Absorption correction: numerical [X-RED32 and X-SHAPE (Stoe & Cie, 2005 ▶)] T min = 0.100, T max = 0.280

10947 measured reflections

4498 independent reflections

4035 reflections with I > 2σ(I)

R int = 0.098

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.230

S = 1.12

4498 reflections

172 parameters

H-atom parameters constrained

Δρmax = 1.97 e Å−3

Δρmin = −1.66 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2005 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808020230/hk2486sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020230/hk2486Isup2.hkl

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

[ZnI2(C14H14N2)]	F000 = 992
Mr = 529.46	Dx = 2.068 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2112 reflections
a = 11.467 (5) Å	θ = 2.5–29.4º
b = 9.627 (4) Å	µ = 5.06 mm−1
c = 15.868 (6) Å	T = 298 (2) K
β = 103.88 (3)º	Block, yellow
V = 1700.6 (12) Å3	0.5 × 0.4 × 0.25 mm
Z = 4

Stoe IPDSII diffractometer	Rint = 0.098
rotation method scans	θmax = 29.4º
Absorption correction: numerical[X-RED and X-SHAPE (Stoe & Cie, 2005)]	θmin = 2.5º
Tmin = 0.100, Tmax = 0.280	h = −15→11
10947 measured reflections	k = −11→13
4498 independent reflections	l = −21→21
4035 reflections with I > 2σ(I)

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.1439P)2 + 2.419P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.071	(Δ/σ)max = 0.007
wR(F2) = 0.230	Δρmax = 1.97 e Å−3
S = 1.12	Δρmin = −1.66 e Å−3
4498 reflections	Extinction correction: none
172 parameters

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.

	x	y	z	Uiso*/Ueq
Zn1	0.83553 (6)	0.25679 (7)	0.02157 (4)	0.0406 (2)
I1	0.69958 (5)	0.45620 (5)	0.03661 (4)	0.0622 (2)
I2	0.87622 (5)	0.19974 (6)	−0.12580 (3)	0.0617 (2)
N1	0.9989 (4)	0.2665 (5)	0.1106 (3)	0.0400 (9)
N2	0.8103 (4)	0.1007 (5)	0.1083 (3)	0.0366 (8)
C1	1.0919 (6)	0.3467 (9)	0.1080 (5)	0.0524 (14)
H1	1.086	0.4083	0.062	0.063*
C2	1.1962 (6)	0.3412 (9)	0.1712 (5)	0.0590 (18)
H2	1.2614	0.3967	0.1681	0.071*
C3	1.2026 (6)	0.2495 (9)	0.2411 (5)	0.0596 (19)
H3	1.2721	0.2453	0.2856	0.072*
C4	1.1071 (5)	0.1665 (8)	0.2440 (4)	0.0498 (13)
H4	1.1104	0.1042	0.2893	0.06*
C5	1.0055 (5)	0.1786 (6)	0.1771 (4)	0.0411 (11)
C6	0.8989 (5)	0.0951 (6)	0.1752 (4)	0.0412 (11)
H6	0.8952	0.0384	0.2219	0.049*
C7	0.7036 (5)	0.0265 (5)	0.1120 (3)	0.0356 (9)
C8	0.6663 (5)	−0.0814 (6)	0.0540 (3)	0.0377 (10)
C9	0.7345 (7)	−0.1256 (8)	−0.0114 (5)	0.0531 (14)
H9A	0.8136	−0.1554	0.0183	0.064*
H9B	0.7404	−0.0488	−0.0487	0.064*
H9C	0.693	−0.201	−0.0455	0.064*
C10	0.5634 (5)	−0.1522 (6)	0.0595 (4)	0.0440 (12)
H10	0.5352	−0.2247	0.0213	0.053*
C11	0.5023 (5)	−0.1160 (7)	0.1214 (5)	0.0495 (13)
H11	0.4335	−0.1652	0.1241	0.059*
C12	0.5402 (5)	−0.0092 (8)	0.1791 (4)	0.0491 (13)
C13	0.4725 (8)	0.0300 (13)	0.2483 (7)	0.076 (3)
H13A	0.4453	0.1244	0.2396	0.091*
H13B	0.5253	0.0207	0.305	0.091*
H13C	0.4047	−0.0304	0.2435	0.091*
C14	0.6415 (5)	0.0638 (6)	0.1732 (4)	0.0416 (11)
H14	0.668	0.138	0.2104	0.05*

	U11	U22	U33	U12	U13	U23
Zn1	0.0414 (4)	0.0406 (4)	0.0392 (4)	−0.0024 (2)	0.0082 (3)	0.0058 (2)
I1	0.0607 (3)	0.0455 (3)	0.0819 (4)	0.00774 (18)	0.0200 (3)	0.0016 (2)
I2	0.0745 (4)	0.0713 (4)	0.0442 (3)	0.0013 (2)	0.0239 (2)	0.00481 (18)
N1	0.036 (2)	0.038 (2)	0.047 (2)	−0.0030 (17)	0.0124 (18)	−0.0020 (18)
N2	0.041 (2)	0.033 (2)	0.0357 (19)	0.0000 (16)	0.0107 (16)	0.0014 (16)
C1	0.048 (3)	0.060 (4)	0.052 (3)	−0.015 (3)	0.019 (3)	−0.006 (3)
C2	0.039 (3)	0.076 (5)	0.064 (4)	−0.011 (3)	0.016 (3)	−0.030 (4)
C3	0.039 (3)	0.079 (5)	0.055 (4)	0.001 (3)	0.001 (3)	−0.032 (4)
C4	0.040 (3)	0.054 (3)	0.050 (3)	0.003 (2)	0.001 (2)	−0.006 (3)
C5	0.041 (2)	0.040 (3)	0.041 (2)	0.000 (2)	0.006 (2)	−0.007 (2)
C6	0.040 (2)	0.037 (2)	0.044 (3)	0.0001 (19)	0.005 (2)	0.006 (2)
C7	0.036 (2)	0.031 (2)	0.037 (2)	0.0000 (17)	0.0042 (17)	0.0039 (17)
C8	0.045 (2)	0.033 (2)	0.034 (2)	0.0013 (19)	0.0083 (19)	0.0027 (18)
C9	0.066 (4)	0.048 (3)	0.050 (3)	−0.003 (3)	0.023 (3)	−0.011 (3)
C10	0.040 (2)	0.036 (2)	0.051 (3)	−0.005 (2)	0.002 (2)	0.001 (2)
C11	0.037 (2)	0.050 (3)	0.060 (3)	−0.002 (2)	0.008 (2)	0.006 (3)
C12	0.033 (2)	0.064 (4)	0.051 (3)	0.002 (2)	0.010 (2)	0.001 (3)
C13	0.054 (4)	0.105 (7)	0.077 (5)	0.010 (4)	0.031 (4)	−0.010 (5)
C14	0.042 (3)	0.042 (3)	0.040 (2)	−0.002 (2)	0.008 (2)	−0.006 (2)

Zn1—I1	2.5201 (11)	C7—C8	1.387 (7)
Zn1—I2	2.5517 (12)	C7—N2	1.430 (7)
Zn1—N1	2.059 (5)	C8—C10	1.384 (8)
Zn1—N2	2.104 (5)	C8—C9	1.502 (9)
C1—N1	1.326 (8)	C9—H9A	0.96
C1—C2	1.365 (10)	C9—H9B	0.96
C1—H1	0.93	C9—H9C	0.96
C2—C3	1.406 (13)	C10—C11	1.381 (10)
C2—H2	0.93	C10—H10	0.93
C3—C4	1.365 (11)	C11—C12	1.377 (10)
C3—H3	0.93	C11—H11	0.93
C4—C5	1.380 (8)	C12—C14	1.380 (9)
C4—H4	0.93	C12—C13	1.535 (11)
C5—N1	1.341 (8)	C13—H13A	0.96
C5—C6	1.457 (8)	C13—H13B	0.96
C6—N2	1.283 (7)	C13—H13C	0.96
C6—H6	0.93	C14—H14	0.93
C7—C14	1.382 (8)
I1—Zn1—I2	120.26 (4)	C14—C7—C8	122.2 (5)
N1—Zn1—N2	80.16 (19)	C14—C7—N2	119.3 (5)
N1—Zn1—I1	112.45 (14)	C8—C7—N2	118.5 (5)
N2—Zn1—I1	107.27 (13)	C10—C8—C7	117.3 (5)
N1—Zn1—I2	107.58 (15)	C10—C8—C9	119.8 (6)
N2—Zn1—I2	121.99 (13)	C7—C8—C9	122.9 (5)
C1—N1—C5	119.8 (6)	C8—C9—H9A	109.5
C1—N1—Zn1	127.7 (5)	C8—C9—H9B	109.5
C5—N1—Zn1	112.4 (4)	H9A—C9—H9B	109.5
C6—N2—C7	117.4 (5)	C8—C9—H9C	109.5
C6—N2—Zn1	111.5 (4)	H9A—C9—H9C	109.5
C7—N2—Zn1	129.6 (3)	H9B—C9—H9C	109.5
N1—C1—C2	121.7 (7)	C11—C10—C8	120.4 (6)
N1—C1—H1	119.2	C11—C10—H10	119.8
C2—C1—H1	119.2	C8—C10—H10	119.8
C1—C2—C3	118.3 (7)	C12—C11—C10	121.9 (6)
C1—C2—H2	120.8	C12—C11—H11	119
C3—C2—H2	120.8	C10—C11—H11	119
C4—C3—C2	120.2 (6)	C11—C12—C14	118.1 (6)
C4—C3—H3	119.9	C11—C12—C13	121.8 (7)
C2—C3—H3	119.9	C14—C12—C13	120.1 (7)
C3—C4—C5	117.4 (7)	C12—C13—H13A	109.5
C3—C4—H4	121.3	C12—C13—H13B	109.5
C5—C4—H4	121.3	H13A—C13—H13B	109.5
N1—C5—C4	122.5 (6)	C12—C13—H13C	109.5
N1—C5—C6	116.3 (5)	H13A—C13—H13C	109.5
C4—C5—C6	121.2 (6)	H13B—C13—H13C	109.5
N2—C6—C5	119.2 (5)	C12—C14—C7	120.0 (6)
N2—C6—H6	120.4	C12—C14—H14	120
C5—C6—H6	120.4	C7—C14—H14	120
N1—C1—C2—C3	−1.3 (11)	C4—C5—N1—C1	−0.7 (9)
C1—C2—C3—C4	1.4 (11)	C6—C5—N1—C1	179.5 (6)
C2—C3—C4—C5	−1.1 (10)	C4—C5—N1—Zn1	179.3 (5)
C3—C4—C5—N1	0.8 (10)	C6—C5—N1—Zn1	−0.5 (6)
C3—C4—C5—C6	−179.5 (6)	N2—Zn1—N1—C1	177.4 (6)
N1—C5—C6—N2	5.8 (8)	I1—Zn1—N1—C1	−77.9 (6)
C4—C5—C6—N2	−174.0 (6)	I2—Zn1—N1—C1	56.8 (6)
C14—C7—C8—C10	−0.2 (8)	N2—Zn1—N1—C5	−2.6 (4)
N2—C7—C8—C10	179.5 (5)	I1—Zn1—N1—C5	102.1 (4)
C14—C7—C8—C9	−178.4 (6)	I2—Zn1—N1—C5	−123.2 (4)
N2—C7—C8—C9	1.3 (8)	C5—C6—N2—C7	−174.8 (5)
C7—C8—C10—C11	−0.6 (8)	C5—C6—N2—Zn1	−7.7 (7)
C9—C8—C10—C11	177.6 (6)	C14—C7—N2—C6	62.5 (7)
C8—C10—C11—C12	0.3 (10)	C8—C7—N2—C6	−117.1 (6)
C10—C11—C12—C14	0.9 (10)	C14—C7—N2—Zn1	−101.8 (6)
C10—C11—C12—C13	−179.5 (7)	C8—C7—N2—Zn1	78.6 (6)
C11—C12—C14—C7	−1.7 (9)	N1—Zn1—N2—C6	5.6 (4)
C13—C12—C14—C7	178.7 (7)	I1—Zn1—N2—C6	−105.0 (4)
C8—C7—C14—C12	1.4 (9)	I2—Zn1—N2—C6	110.3 (4)
N2—C7—C14—C12	−178.3 (5)	N1—Zn1—N2—C7	170.6 (5)
C2—C1—N1—C5	0.9 (10)	I1—Zn1—N2—C7	60.0 (5)
C2—C1—N1—Zn1	−179.0 (5)	I2—Zn1—N2—C7	−84.7 (5)

Zn1—I1	2.5201 (11)
Zn1—I2	2.5517 (12)
Zn1—N1	2.059 (5)
Zn1—N2	2.104 (5)

I1—Zn1—I2	120.26 (4)
N1—Zn1—N2	80.16 (19)
N1—Zn1—I1	112.45 (14)
N2—Zn1—I1	107.27 (13)
N1—Zn1—I2	107.58 (15)
N2—Zn1—I2	121.99 (13)