{2-[(2,5-Dimethyl­phen­yl)imino­methyl]pyridine-κ2N,N′}diiodidozinc(II)

Talei Bavil Olyai, M.R.; Dehghanpour, S.; Hoormehr, B.; Gholami, F.; Khavasi, H.R.

doi:10.1107/S1600536808020230

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page m1191

doi:10.1107/S1600536808020230

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{2-[(2,5-Dimethylphenyl)iminomethyl]pyridine-κ²N,N′}diiodidozinc(II)

Mohamad Reza Talei Bavil Olyai,^a ^* Saeed Dehghanpour,^b Bita Hoormehr,^c Fahimeh Gholami ^c and Hamid Reza Khavasi ^d

^aDepartment of Chemistry, Islamic Azad University, South Tehran Branch, Tehran, Iran, ^bDepartment of Chemistry, Alzahra University, Vanak, Tehran, Iran, ^cDepartment of Chemistry, Islamic Azad University, Karaj Branch, Tehran, Iran, and ^dDepartment of Chemistry, Shahid Beheshti University, Evin, Tehran 1983963113, Iran
^*Correspondence e-mail: talei3@yahoo.com

(Received 30 June 2008; accepted 2 July 2008; online 23 August 2008)

In the molecule of the title compound, [ZnI₂(C₁₄H₁₄N₂)], the Zn atom is four-coordinated in a distorted tetrahedral 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 interaction 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_r = 529.46
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.071
wR(F²) = 0.230
S = 1.12
4498 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 1.97 e Å⁻³
Δρ_min = −1.66 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

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)

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 ).

Supporting information

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

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

checkCIF report

Comment top

Transition metal compounds containing Schiff base ligands have been of great interest for many years. These compounds play an important role in the development of coordination chemistry (Gibson et al., 2007). Aryl-substituted iminopyridine complexes have emerged as a powerful class of catalysts for a host of important bond-forming reactions including olefin polymerization (Ittel et al., 2000; Gibson & Spitzmesser, 2003), hydrogenation and hydrosilation (Bart et al., 2004). It is also now well established that iminopyridines are both redox (Sugiyama et al., 2004) and chemically active ligands (Kooistra et al., 2004) participating in electron transfer, addition reactions and deprotonation chemistry (Bouwkamp et al., 2006). We report herein the crystal structure of the title compound.

In the molecule of the title compound (Fig. 1), the Zn atom is four-coordinated in distorted tetrahedral geometry (Table 1) by two N atoms of the Schiff base ligand, and two I atoms. The bond angles around the Zn atom deviate from the ideal tetrahedral geometry (Dehghanpour et al., 2007). Rings A (N1/C1–C5) and B (C7/C8/C10/C11/C12/C14) are, of course, planar, and they are oriented at a dihedral angle of 70.75 (3)°. Ring C (Zn1/N1/N2/C5/C6) has envelope conformation, with N2 atom displaced by 0.104 (3) Å from the plane of the other ring atoms. The weak π–π interaction between B rings CgB···CgBⁱ [symmetry code: (iv) 1 - x, 1 - y, 1 - z] may stabilize the structure, with a centroid–centroid distance of 3.975 (4) Å.

Related literature top

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 top

For the preparation of the title compound, (2,5-dimethyl-N-phenyl)(pyridine-2-yl)methanimine (21.0 mg, 0.1 mmol), and ZnI₂ (31.9 mg, 0.1 mmol) were dissolved in acetonitrile (50 ml). The mixture was stirred for 10 min at room temperature. The resulting solution was left in air for a few days, giving yellow crystals of the title compound (yield; 79%). Calc.: C 31.75 H 2.67, N 5.29%, found: C 31.79, H 2.49, N 5.31%.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-RED (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).

Figures top

Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

{2-[(2,5-Dimethylphenyl)iminomethyl]pyridine-κ²N,N'}diiodidozinc(II) top

Crystal data top

[ZnI₂(C₁₄H₁₄N₂)]	F(000) = 992
M_r = 529.46	D_x = 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 = 2.5–29.4°
b = 9.627 (4) Å	µ = 5.06 mm⁻¹
c = 15.868 (6) Å	T = 298 K
β = 103.88 (3)°	Block, yellow
V = 1700.6 (12) Å³	0.5 × 0.4 × 0.25 mm
Z = 4

Data collection top

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

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.071	w = 1/[σ²(F_o²) + (0.1439P)² + 2.419P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.230	(Δ/σ)_max = 0.007
S = 1.12	Δρ_max = 1.97 e Å⁻³
4498 reflections	Δρ_min = −1.66 e Å⁻³
172 parameters

Crystal data top

[ZnI₂(C₁₄H₁₄N₂)]	V = 1700.6 (12) Å³
M_r = 529.46	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.467 (5) Å	µ = 5.06 mm⁻¹
b = 9.627 (4) Å	T = 298 K
c = 15.868 (6) Å	0.5 × 0.4 × 0.25 mm
β = 103.88 (3)°

Data collection top

Stoe IPDSII diffractometer	4498 independent reflections
Absorption correction: numerical [X-RED and X-SHAPE (Stoe & Cie, 2005)]	4035 reflections with I > 2σ(I)
T_min = 0.100, T_max = 0.280	R_int = 0.098
10947 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.071	0 restraints
wR(F²) = 0.230	H-atom parameters constrained
S = 1.12	Δρ_max = 1.97 e Å⁻³
4498 reflections	Δρ_min = −1.66 e Å⁻³
172 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	[ZnI₂(C₁₄H₁₄N₂)]
M_r	529.46
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	11.467 (5), 9.627 (4), 15.868 (6)
β (°)	103.88 (3)
V (Å³)	1700.6 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	5.06
Crystal size (mm)	0.5 × 0.4 × 0.25

Data collection
Diffractometer	Stoe IPDSII diffractometer
Absorption correction	Numerical [X-RED and X-SHAPE (Stoe & Cie, 2005)]
T_min, T_max	0.100, 0.280
No. of measured, independent and observed [I > 2σ(I)] reflections	10947, 4498, 4035
R_int	0.098
(sin θ/λ)_max (Å⁻¹)	0.692

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.071, 0.230, 1.12
No. of reflections	4498
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.97, −1.66

Computer programs: X-AREA (Stoe & Cie, 2005), X-RED (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

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

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

Acknowledgements

The authors acknowledge Isfahan University of Technology and Shahid Beheshti University for financial support.

References

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