metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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 ππ 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[Gibson, V. C., Redshaw, C. & Solan, G. A. (2007). Chem. Rev. 107, 1745-1776.]); Ittel et al. (2000[Ittel, S. D., Johnson, L. K. & Brookhart, M. (2000). Chem. Rev. 100, 1169-1203.]); Gibson & Spitzmesser (2003[Gibson, V. C. & Spitzmesser, S. K. (2003). Chem. Rev. 103, 283-316.]); Bart et al. (2004[Bart, S. C., Lobkovsky, E. & Chirik, P. J. (2004). J. Am. Chem. Soc. 126, 13794-13807.]); Sugiyama et al. (2004[Sugiyama, I., Korobkov, I., Gambarotta, S., Mueller, A. & Budzelaar, P. H. M. (2004). Inorg. Chem. 43, 5771-5779.]); Kooistra et al. (2004[Kooistra, T. M., Hetterscheid, D. G. H., Schwartz, E., Knijnenburg, Q., Budzelaar, P. H. M. & Gal, A. W. (2004). Inorg. Chim. Acta, 357, 2945-2952.]); Bouwkamp et al. (2006[Bouwkamp, M. W., Lobkovsky, E. & Chirik, P. J. (2006). Inorg. Chem. 45, 2-4.]). For related literature, see: Dehghanpour et al. (2007[Dehghanpour, S., Mahmoudi, A., Khalaj, M., Salmanpour, S. & Adib, M. (2007). Acta Cryst. E63, m2841.]).

[Scheme 1]

Experimental

Crystal data
  • [ZnI2(C14H14N2)]

  • Mr = 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[Stoe & Cie (2005). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany.])] Tmin = 0.100, Tmax = 0.280

  • 10947 measured reflections

  • 4498 independent reflections

  • 4035 reflections with I > 2σ(I)

  • Rint = 0.098

Refinement
  • R[F2 > 2σ(F2)] = 0.071

  • wR(F2) = 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

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[Stoe & Cie (2005). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2005[Stoe & Cie (2005). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


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 ππ 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%.

Refinement top

H atoms were positioned geometrically, with C—H = 0.93 and 0.96 Å for aromatic and methyl H, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).

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
[Figure 1] 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
Mr = 529.46Dx = 2.068 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2112 reflections
a = 11.467 (5) Åθ = 2.5–29.4°
b = 9.627 (4) ŵ = 5.06 mm1
c = 15.868 (6) ÅT = 298 K
β = 103.88 (3)°Block, yellow
V = 1700.6 (12) Å30.5 × 0.4 × 0.25 mm
Z = 4
Data collection top
Stoe IPDSII
diffractometer
4035 reflections with I > 2σ(I)
rotation method scansRint = 0.098
Absorption correction: numerical
[X-RED and X-SHAPE (Stoe & Cie, 2005)]
θmax = 29.4°, θmin = 2.5°
Tmin = 0.100, Tmax = 0.280h = 1511
10947 measured reflectionsk = 1113
4498 independent reflectionsl = 2121
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.071 w = 1/[σ2(Fo2) + (0.1439P)2 + 2.419P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.230(Δ/σ)max = 0.007
S = 1.12Δρmax = 1.97 e Å3
4498 reflectionsΔρmin = 1.66 e Å3
172 parameters
Crystal data top
[ZnI2(C14H14N2)]V = 1700.6 (12) Å3
Mr = 529.46Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.467 (5) ŵ = 5.06 mm1
b = 9.627 (4) ÅT = 298 K
c = 15.868 (6) Å0.5 × 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)
Tmin = 0.100, Tmax = 0.280Rint = 0.098
10947 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0710 restraints
wR(F2) = 0.230H-atom parameters constrained
S = 1.12Δρmax = 1.97 e Å3
4498 reflectionsΔρmin = 1.66 e Å3
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
xyzUiso*/Ueq
Zn10.83553 (6)0.25679 (7)0.02157 (4)0.0406 (2)
I10.69958 (5)0.45620 (5)0.03661 (4)0.0622 (2)
I20.87622 (5)0.19974 (6)0.12580 (3)0.0617 (2)
N10.9989 (4)0.2665 (5)0.1106 (3)0.0400 (9)
N20.8103 (4)0.1007 (5)0.1083 (3)0.0366 (8)
C11.0919 (6)0.3467 (9)0.1080 (5)0.0524 (14)
H11.0860.40830.0620.063*
C21.1962 (6)0.3412 (9)0.1712 (5)0.0590 (18)
H21.26140.39670.16810.071*
C31.2026 (6)0.2495 (9)0.2411 (5)0.0596 (19)
H31.27210.24530.28560.072*
C41.1071 (5)0.1665 (8)0.2440 (4)0.0498 (13)
H41.11040.10420.28930.06*
C51.0055 (5)0.1786 (6)0.1771 (4)0.0411 (11)
C60.8989 (5)0.0951 (6)0.1752 (4)0.0412 (11)
H60.89520.03840.22190.049*
C70.7036 (5)0.0265 (5)0.1120 (3)0.0356 (9)
C80.6663 (5)0.0814 (6)0.0540 (3)0.0377 (10)
C90.7345 (7)0.1256 (8)0.0114 (5)0.0531 (14)
H9A0.81360.15540.01830.064*
H9B0.74040.04880.04870.064*
H9C0.6930.2010.04550.064*
C100.5634 (5)0.1522 (6)0.0595 (4)0.0440 (12)
H100.53520.22470.02130.053*
C110.5023 (5)0.1160 (7)0.1214 (5)0.0495 (13)
H110.43350.16520.12410.059*
C120.5402 (5)0.0092 (8)0.1791 (4)0.0491 (13)
C130.4725 (8)0.0300 (13)0.2483 (7)0.076 (3)
H13A0.44530.12440.23960.091*
H13B0.52530.02070.3050.091*
H13C0.40470.03040.24350.091*
C140.6415 (5)0.0638 (6)0.1732 (4)0.0416 (11)
H140.6680.1380.21040.05*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0414 (4)0.0406 (4)0.0392 (4)0.0024 (2)0.0082 (3)0.0058 (2)
I10.0607 (3)0.0455 (3)0.0819 (4)0.00774 (18)0.0200 (3)0.0016 (2)
I20.0745 (4)0.0713 (4)0.0442 (3)0.0013 (2)0.0239 (2)0.00481 (18)
N10.036 (2)0.038 (2)0.047 (2)0.0030 (17)0.0124 (18)0.0020 (18)
N20.041 (2)0.033 (2)0.0357 (19)0.0000 (16)0.0107 (16)0.0014 (16)
C10.048 (3)0.060 (4)0.052 (3)0.015 (3)0.019 (3)0.006 (3)
C20.039 (3)0.076 (5)0.064 (4)0.011 (3)0.016 (3)0.030 (4)
C30.039 (3)0.079 (5)0.055 (4)0.001 (3)0.001 (3)0.032 (4)
C40.040 (3)0.054 (3)0.050 (3)0.003 (2)0.001 (2)0.006 (3)
C50.041 (2)0.040 (3)0.041 (2)0.000 (2)0.006 (2)0.007 (2)
C60.040 (2)0.037 (2)0.044 (3)0.0001 (19)0.005 (2)0.006 (2)
C70.036 (2)0.031 (2)0.037 (2)0.0000 (17)0.0042 (17)0.0039 (17)
C80.045 (2)0.033 (2)0.034 (2)0.0013 (19)0.0083 (19)0.0027 (18)
C90.066 (4)0.048 (3)0.050 (3)0.003 (3)0.023 (3)0.011 (3)
C100.040 (2)0.036 (2)0.051 (3)0.005 (2)0.002 (2)0.001 (2)
C110.037 (2)0.050 (3)0.060 (3)0.002 (2)0.008 (2)0.006 (3)
C120.033 (2)0.064 (4)0.051 (3)0.002 (2)0.010 (2)0.001 (3)
C130.054 (4)0.105 (7)0.077 (5)0.010 (4)0.031 (4)0.010 (5)
C140.042 (3)0.042 (3)0.040 (2)0.002 (2)0.008 (2)0.006 (2)
Geometric parameters (Å, º) top
Zn1—I12.5201 (11)C7—C81.387 (7)
Zn1—I22.5517 (12)C7—N21.430 (7)
Zn1—N12.059 (5)C8—C101.384 (8)
Zn1—N22.104 (5)C8—C91.502 (9)
C1—N11.326 (8)C9—H9A0.96
C1—C21.365 (10)C9—H9B0.96
C1—H10.93C9—H9C0.96
C2—C31.406 (13)C10—C111.381 (10)
C2—H20.93C10—H100.93
C3—C41.365 (11)C11—C121.377 (10)
C3—H30.93C11—H110.93
C4—C51.380 (8)C12—C141.380 (9)
C4—H40.93C12—C131.535 (11)
C5—N11.341 (8)C13—H13A0.96
C5—C61.457 (8)C13—H13B0.96
C6—N21.283 (7)C13—H13C0.96
C6—H60.93C14—H140.93
C7—C141.382 (8)
I1—Zn1—I2120.26 (4)C14—C7—C8122.2 (5)
N1—Zn1—N280.16 (19)C14—C7—N2119.3 (5)
N1—Zn1—I1112.45 (14)C8—C7—N2118.5 (5)
N2—Zn1—I1107.27 (13)C10—C8—C7117.3 (5)
N1—Zn1—I2107.58 (15)C10—C8—C9119.8 (6)
N2—Zn1—I2121.99 (13)C7—C8—C9122.9 (5)
C1—N1—C5119.8 (6)C8—C9—H9A109.5
C1—N1—Zn1127.7 (5)C8—C9—H9B109.5
C5—N1—Zn1112.4 (4)H9A—C9—H9B109.5
C6—N2—C7117.4 (5)C8—C9—H9C109.5
C6—N2—Zn1111.5 (4)H9A—C9—H9C109.5
C7—N2—Zn1129.6 (3)H9B—C9—H9C109.5
N1—C1—C2121.7 (7)C11—C10—C8120.4 (6)
N1—C1—H1119.2C11—C10—H10119.8
C2—C1—H1119.2C8—C10—H10119.8
C1—C2—C3118.3 (7)C12—C11—C10121.9 (6)
C1—C2—H2120.8C12—C11—H11119
C3—C2—H2120.8C10—C11—H11119
C4—C3—C2120.2 (6)C11—C12—C14118.1 (6)
C4—C3—H3119.9C11—C12—C13121.8 (7)
C2—C3—H3119.9C14—C12—C13120.1 (7)
C3—C4—C5117.4 (7)C12—C13—H13A109.5
C3—C4—H4121.3C12—C13—H13B109.5
C5—C4—H4121.3H13A—C13—H13B109.5
N1—C5—C4122.5 (6)C12—C13—H13C109.5
N1—C5—C6116.3 (5)H13A—C13—H13C109.5
C4—C5—C6121.2 (6)H13B—C13—H13C109.5
N2—C6—C5119.2 (5)C12—C14—C7120.0 (6)
N2—C6—H6120.4C12—C14—H14120
C5—C6—H6120.4C7—C14—H14120
N1—C1—C2—C31.3 (11)C4—C5—N1—C10.7 (9)
C1—C2—C3—C41.4 (11)C6—C5—N1—C1179.5 (6)
C2—C3—C4—C51.1 (10)C4—C5—N1—Zn1179.3 (5)
C3—C4—C5—N10.8 (10)C6—C5—N1—Zn10.5 (6)
C3—C4—C5—C6179.5 (6)N2—Zn1—N1—C1177.4 (6)
N1—C5—C6—N25.8 (8)I1—Zn1—N1—C177.9 (6)
C4—C5—C6—N2174.0 (6)I2—Zn1—N1—C156.8 (6)
C14—C7—C8—C100.2 (8)N2—Zn1—N1—C52.6 (4)
N2—C7—C8—C10179.5 (5)I1—Zn1—N1—C5102.1 (4)
C14—C7—C8—C9178.4 (6)I2—Zn1—N1—C5123.2 (4)
N2—C7—C8—C91.3 (8)C5—C6—N2—C7174.8 (5)
C7—C8—C10—C110.6 (8)C5—C6—N2—Zn17.7 (7)
C9—C8—C10—C11177.6 (6)C14—C7—N2—C662.5 (7)
C8—C10—C11—C120.3 (10)C8—C7—N2—C6117.1 (6)
C10—C11—C12—C140.9 (10)C14—C7—N2—Zn1101.8 (6)
C10—C11—C12—C13179.5 (7)C8—C7—N2—Zn178.6 (6)
C11—C12—C14—C71.7 (9)N1—Zn1—N2—C65.6 (4)
C13—C12—C14—C7178.7 (7)I1—Zn1—N2—C6105.0 (4)
C8—C7—C14—C121.4 (9)I2—Zn1—N2—C6110.3 (4)
N2—C7—C14—C12178.3 (5)N1—Zn1—N2—C7170.6 (5)
C2—C1—N1—C50.9 (10)I1—Zn1—N2—C760.0 (5)
C2—C1—N1—Zn1179.0 (5)I2—Zn1—N2—C784.7 (5)

Experimental details

Crystal data
Chemical formula[ZnI2(C14H14N2)]
Mr529.46
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)11.467 (5), 9.627 (4), 15.868 (6)
β (°) 103.88 (3)
V3)1700.6 (12)
Z4
Radiation typeMo Kα
µ (mm1)5.06
Crystal size (mm)0.5 × 0.4 × 0.25
Data collection
DiffractometerStoe IPDSII
diffractometer
Absorption correctionNumerical
[X-RED and X-SHAPE (Stoe & Cie, 2005)]
Tmin, Tmax0.100, 0.280
No. of measured, independent and
observed [I > 2σ(I)] reflections
10947, 4498, 4035
Rint0.098
(sin θ/λ)max1)0.692
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.071, 0.230, 1.12
No. of reflections4498
No. of parameters172
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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—I12.5201 (11)Zn1—N12.059 (5)
Zn1—I22.5517 (12)Zn1—N22.104 (5)
I1—Zn1—I2120.26 (4)N2—Zn1—I1107.27 (13)
N1—Zn1—N280.16 (19)N1—Zn1—I2107.58 (15)
N1—Zn1—I1112.45 (14)N2—Zn1—I2121.99 (13)
 

Acknowledgements

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

References

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