Diiodido[N′-(2-methoxy­benzyl­idene)-N,N-dimethyl­ethane-1,2-diamine]zinc(II)

Zhu, X.-W.; Yin, Z.-G.; Zhang, C.-X.; Yang, X.-Z.; Li, G.-S.

doi:10.1107/S1600536809037209

metal-organic compounds

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Volume 65| Part 10| October 2009| Page m1228

doi:10.1107/S1600536809037209

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Diiodido[N′-(2-methoxybenzylidene)-N,N-dimethylethane-1,2-diamine]zinc(II)

Xue-Wen Zhu,^a ^* Zhi-Gang Yin,^a Chun-Xia Zhang,^a Xu-Zhao Yang ^a and Gang-Sen Li ^a

^aKey Laboratory of Surface and Interface Science of Henan, School of Materials and Chemical Engineering, Zhengzhou University of Light Industry, Zhengzhou 450002, People's Republic of China
^*Correspondence e-mail: xuewen-zhu@163.com

(Received 10 September 2009; accepted 14 September 2009; online 19 September 2009)

In the title complex, [Zn(C₁₂H₁₈N₂O)I₂], the Zn^II ion is four-coordinated by the imine N and amine N atoms of the Schiff base ligand and by two iodide ions in a distorted tetrahedral coordination.

Related literature

For background to the chemistry of Schiff base complexes, see: Ali et al. (2008 ); Biswas et al. (2008 ); Chen et al. (2008 ); Darensbourg & Frantz (2007 ); Habibi et al. (2007 ); Kawamoto et al. (2008 ); Lipscomb & Sträter (1996 ); Tomat et al. (2007 ); Wu et al. (2008 ); Yuan et al. (2007 ). For related structures, see: Zhu (2008 ); Zhu & Yang (2008a ,b ,c ); Qiu (2006a ,b ); Wei et al. (2007 ); Zhu et al. (2007 ).

Experimental

Crystal data

[Zn(C₁₂H₁₈N₂O)I₂]
M_r = 525.45
Monoclinic, P 2₁ /n
a = 13.5215 (8) Å
b = 7.2806 (4) Å
c = 18.4224 (11) Å
β = 109.250 (3)°
V = 1712.19 (17) Å³
Z = 4
Mo Kα radiation
μ = 5.03 mm⁻¹
T = 298 K
0.30 × 0.27 × 0.27 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.314, T_max = 0.344
10129 measured reflections
3724 independent reflections
3128 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.069
S = 1.04
3724 reflections
166 parameters
H-atom parameters constrained
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.83 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Zn1—N1	2.070 (3)
Zn1—N2	2.099 (3)
Zn1—I1	2.5538 (5)
Zn1—I2	2.5542 (4)

N1—Zn1—N2	85.04 (11)
N1—Zn1—I1	105.44 (8)
N2—Zn1—I1	110.30 (8)
N1—Zn1—I2	121.86 (8)
N2—Zn1—I2	107.02 (8)
I1—Zn1—I2	121.063 (18)

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037209/om2277sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809037209/om2277Isup2.hkl

checkCIF report

Comment top

Schiff bases have widely been used as versatile ligands in coordination chemistry (Biswas et al., 2008; Wu et al., 2008; Kawamoto et al., 2008; Ali et al., 2008; Habibi et al., 2007), and their metal complexes are of great interest in many fields (Chen et al., 2008; Yuan et al., 2007; Tomat et al., 2007; Darensbourg & Frantz, 2007). Zinc(II) is an important element in biological systems and functions as the active site of hydrolytic enzymes, such as carboxypeptidase and carbonic anhydrase where it is in a hard-donor coordination environment of nitrogen and oxygen ligands (Lipscomb & Sträter, 1996). Recently, we have reported a few Schiff base zinc complexes (Zhu, 2008; Zhu & Yang, 2008a,b,c). In this paper, the title new zinc(II) complex, Fig. 1, is reported.

In the title complex, the Zn^II atom is four-coordinated by the imine N and amine N atoms of the Schiff base ligand, and by two iodide ions in a tetrahedral coordination. The coordinate bond lengths (Table 1) are typical and comparable to the corresponding values observed in the Schiff base zinc complexes we reported previously and other similar Schiff base zinc complexes (Zhu et al., 2007; Wei et al., 2007; Qiu, 2006a,b).

Related literature top

For background to the chemistry of Schiff base complexes, see: Ali et al. (2008); Biswas et al. (2008); Chen et al. (2008); Darensbourg & Frantz (2007); Habibi et al. (2007); Kawamoto et al. (2008); Lipscomb & Sträter (1996); Tomat et al. (2007); Wu et al. (2008); Yuan et al. (2007). For related structures, see: Zhu (2008); Zhu & Yang (2008a,b,c); Qiu (2006a,b); Wei et al. (2007); Zhu et al. (2007).

Experimental top

The Schiff base compound was prepared by the condensation of equimolar amounts of 2-methoxybenzaldehyde with N,N-dimethylethane-1,2-diamine in a methanol solution. The complex was prepared by the following method. To an anhydrous methanol solution (5 ml) of ZnI₂ (31.9 mg, 0.1 mmol) was added a methanol solution (10 ml) of the Schiff base compound (20.6 mg, 0.1 mmol) with stirring. The mixture was stirred for 30 min at room temperature and filtered. Upon keeping the filtrate in air for a few days, colorless block-shaped crystals were formed.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title complex, with ellipsoids drawn at the 30% probability level.

Diiodido[N'-(2-methoxybenzylidene)-N,N- dimethylethane-1,2-diamine]zinc(II) top

Crystal data top

[ZnI₂(C₁₂H₁₈N₂O)]	F(000) = 992
M_r = 525.45	D_x = 2.038 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4576 reflections
a = 13.5215 (8) Å	θ = 2.3–27.0°
b = 7.2806 (4) Å	µ = 5.03 mm⁻¹
c = 18.4224 (11) Å	T = 298 K
β = 109.250 (3)°	Block, colourless
V = 1712.19 (17) Å³	0.30 × 0.27 × 0.27 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	3724 independent reflections
Radiation source: fine-focus sealed tube	3128 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ω scans	θ_max = 27.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −14→17
T_min = 0.314, T_max = 0.344	k = −9→8
10129 measured reflections	l = −23→21

Refinement top

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.069	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0327P)² + 0.876P] where P = (F_o² + 2F_c²)/3
3724 reflections	(Δ/σ)_max = 0.001
166 parameters	Δρ_max = 0.65 e Å⁻³
0 restraints	Δρ_min = −0.83 e Å⁻³

Crystal data top

[ZnI₂(C₁₂H₁₈N₂O)]	V = 1712.19 (17) Å³
M_r = 525.45	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.5215 (8) Å	µ = 5.03 mm⁻¹
b = 7.2806 (4) Å	T = 298 K
c = 18.4224 (11) Å	0.30 × 0.27 × 0.27 mm
β = 109.250 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3724 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	3128 reflections with I > 2σ(I)
T_min = 0.314, T_max = 0.344	R_int = 0.022
10129 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.069	H-atom parameters constrained
S = 1.04	Δρ_max = 0.65 e Å⁻³
3724 reflections	Δρ_min = −0.83 e Å⁻³
166 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

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

	x	y	z	U_iso*/U_eq
Zn1	0.98491 (3)	0.05442 (5)	0.79559 (2)	0.04115 (11)
I1	1.14682 (2)	−0.09494 (4)	0.778684 (15)	0.05864 (9)
I2	0.84884 (2)	−0.13708 (4)	0.830527 (15)	0.05832 (9)
N1	0.9421 (2)	0.2610 (4)	0.71398 (14)	0.0415 (6)
N2	1.0290 (2)	0.2698 (4)	0.87555 (15)	0.0466 (7)
O1	0.9175 (2)	0.2845 (4)	0.49776 (13)	0.0643 (8)
C1	0.8782 (3)	0.1069 (5)	0.59019 (17)	0.0419 (8)
C2	0.8811 (3)	0.1219 (6)	0.51478 (19)	0.0497 (9)
C3	0.8492 (3)	−0.0254 (7)	0.4646 (2)	0.0626 (11)
H3	0.8534	−0.0178	0.4153	0.075*
C4	0.8115 (3)	−0.1815 (7)	0.4873 (2)	0.0676 (12)
H4	0.7887	−0.2782	0.4529	0.081*
C5	0.8068 (3)	−0.1974 (6)	0.5608 (3)	0.0666 (11)
H5	0.7820	−0.3048	0.5760	0.080*
C6	0.8392 (3)	−0.0529 (5)	0.6115 (2)	0.0509 (9)
H6	0.8348	−0.0628	0.6606	0.061*
C7	0.9110 (3)	0.2645 (5)	0.64089 (17)	0.0434 (8)
H7	0.9091	0.3785	0.6177	0.052*
C8	0.9669 (4)	0.4396 (5)	0.7536 (2)	0.0592 (10)
H8A	0.9051	0.4880	0.7626	0.071*
H8B	0.9881	0.5263	0.7215	0.071*
C9	1.0538 (3)	0.4168 (5)	0.8290 (2)	0.0545 (9)
H9A	1.1184	0.3870	0.8195	0.065*
H9B	1.0643	0.5316	0.8573	0.065*
C10	0.9436 (3)	0.3264 (6)	0.9035 (2)	0.0680 (12)
H10A	0.9593	0.4446	0.9277	0.102*
H10B	0.9363	0.2381	0.9401	0.102*
H10C	0.8793	0.3334	0.8610	0.102*
C11	1.1229 (3)	0.2261 (7)	0.9423 (2)	0.0701 (12)
H11A	1.1783	0.1852	0.9245	0.105*
H11B	1.1061	0.1309	0.9724	0.105*
H11C	1.1450	0.3340	0.9734	0.105*
C12	0.9178 (4)	0.3156 (8)	0.4208 (2)	0.0781 (14)
H12A	0.9665	0.2333	0.4099	0.117*
H12B	0.9382	0.4402	0.4160	0.117*
H12C	0.8488	0.2943	0.3851	0.117*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0480 (2)	0.0388 (2)	0.0354 (2)	−0.00454 (16)	0.01205 (17)	−0.00228 (15)
I1	0.05712 (17)	0.06509 (18)	0.05364 (16)	0.00639 (12)	0.01816 (12)	−0.00237 (12)
I2	0.06738 (18)	0.05101 (16)	0.06430 (17)	−0.01186 (12)	0.03217 (14)	−0.00014 (11)
N1	0.0504 (16)	0.0408 (15)	0.0324 (13)	−0.0016 (12)	0.0126 (12)	−0.0047 (11)
N2	0.0544 (17)	0.0496 (17)	0.0362 (14)	−0.0097 (14)	0.0154 (13)	−0.0080 (13)
O1	0.0774 (19)	0.082 (2)	0.0369 (13)	0.0063 (16)	0.0234 (13)	0.0029 (13)
C1	0.0382 (17)	0.054 (2)	0.0310 (15)	0.0080 (15)	0.0081 (13)	−0.0052 (14)
C2	0.0391 (18)	0.072 (3)	0.0357 (18)	0.0114 (17)	0.0085 (15)	−0.0034 (17)
C3	0.052 (2)	0.092 (3)	0.0386 (19)	0.015 (2)	0.0077 (17)	−0.017 (2)
C4	0.054 (2)	0.079 (3)	0.060 (3)	0.005 (2)	0.0060 (19)	−0.032 (2)
C5	0.059 (3)	0.062 (3)	0.071 (3)	0.000 (2)	0.009 (2)	−0.015 (2)
C6	0.047 (2)	0.060 (2)	0.0409 (18)	−0.0006 (17)	0.0071 (15)	−0.0091 (17)
C7	0.0468 (19)	0.0472 (19)	0.0363 (17)	0.0048 (15)	0.0139 (14)	0.0033 (14)
C8	0.093 (3)	0.0391 (19)	0.0430 (19)	−0.0089 (19)	0.018 (2)	−0.0042 (16)
C9	0.073 (3)	0.047 (2)	0.0431 (19)	−0.0207 (18)	0.0192 (18)	−0.0067 (16)
C10	0.080 (3)	0.069 (3)	0.066 (3)	−0.009 (2)	0.040 (2)	−0.023 (2)
C11	0.075 (3)	0.086 (3)	0.0367 (19)	−0.013 (2)	0.0007 (19)	−0.003 (2)
C12	0.075 (3)	0.123 (4)	0.041 (2)	0.017 (3)	0.026 (2)	0.015 (2)

Geometric parameters (Å, º) top

Zn1—N1	2.070 (3)	C5—C6	1.378 (5)
Zn1—N2	2.099 (3)	C5—H5	0.9300
Zn1—I1	2.5538 (5)	C6—H6	0.9300
Zn1—I2	2.5542 (4)	C7—H7	0.9300
N1—C7	1.272 (4)	C8—C9	1.504 (5)
N1—C8	1.475 (4)	C8—H8A	0.9700
N2—C10	1.471 (5)	C8—H8B	0.9700
N2—C9	1.477 (4)	C9—H9A	0.9700
N2—C11	1.482 (5)	C9—H9B	0.9700
O1—C2	1.358 (5)	C10—H10A	0.9600
O1—C12	1.437 (4)	C10—H10B	0.9600
C1—C6	1.386 (5)	C10—H10C	0.9600
C1—C2	1.407 (5)	C11—H11A	0.9600
C1—C7	1.454 (5)	C11—H11B	0.9600
C2—C3	1.388 (6)	C11—H11C	0.9600
C3—C4	1.366 (6)	C12—H12A	0.9600
C3—H3	0.9300	C12—H12B	0.9600
C4—C5	1.381 (6)	C12—H12C	0.9600
C4—H4	0.9300

N1—Zn1—N2	85.04 (11)	N1—C7—C1	126.1 (3)
N1—Zn1—I1	105.44 (8)	N1—C7—H7	117.0
N2—Zn1—I1	110.30 (8)	C1—C7—H7	117.0
N1—Zn1—I2	121.86 (8)	N1—C8—C9	109.9 (3)
N2—Zn1—I2	107.02 (8)	N1—C8—H8A	109.7
I1—Zn1—I2	121.063 (18)	C9—C8—H8A	109.7
C7—N1—C8	116.6 (3)	N1—C8—H8B	109.7
C7—N1—Zn1	134.4 (2)	C9—C8—H8B	109.7
C8—N1—Zn1	108.5 (2)	H8A—C8—H8B	108.2
C10—N2—C9	110.8 (3)	N2—C9—C8	111.0 (3)
C10—N2—C11	109.0 (3)	N2—C9—H9A	109.4
C9—N2—C11	110.0 (3)	C8—C9—H9A	109.4
C10—N2—Zn1	112.4 (2)	N2—C9—H9B	109.4
C9—N2—Zn1	101.56 (19)	C8—C9—H9B	109.4
C11—N2—Zn1	112.9 (3)	H9A—C9—H9B	108.0
C2—O1—C12	119.0 (4)	N2—C10—H10A	109.5
C6—C1—C2	118.8 (3)	N2—C10—H10B	109.5
C6—C1—C7	123.0 (3)	H10A—C10—H10B	109.5
C2—C1—C7	118.1 (3)	N2—C10—H10C	109.5
O1—C2—C3	125.2 (3)	H10A—C10—H10C	109.5
O1—C2—C1	115.2 (3)	H10B—C10—H10C	109.5
C3—C2—C1	119.6 (4)	N2—C11—H11A	109.5
C4—C3—C2	120.3 (4)	N2—C11—H11B	109.5
C4—C3—H3	119.9	H11A—C11—H11B	109.5
C2—C3—H3	119.9	N2—C11—H11C	109.5
C3—C4—C5	120.8 (4)	H11A—C11—H11C	109.5
C3—C4—H4	119.6	H11B—C11—H11C	109.5
C5—C4—H4	119.6	O1—C12—H12A	109.5
C6—C5—C4	119.5 (4)	O1—C12—H12B	109.5
C6—C5—H5	120.2	H12A—C12—H12B	109.5
C4—C5—H5	120.2	O1—C12—H12C	109.5
C5—C6—C1	121.0 (4)	H12A—C12—H12C	109.5
C5—C6—H6	119.5	H12B—C12—H12C	109.5
C1—C6—H6	119.5

Experimental details

Crystal data
Chemical formula	[ZnI₂(C₁₂H₁₈N₂O)]
M_r	525.45
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	13.5215 (8), 7.2806 (4), 18.4224 (11)
β (°)	109.250 (3)
V (Å³)	1712.19 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	5.03
Crystal size (mm)	0.30 × 0.27 × 0.27

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.314, 0.344
No. of measured, independent and observed [I > 2σ(I)] reflections	10129, 3724, 3128
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.069, 1.04
No. of reflections	3724
No. of parameters	166
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.83

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Zn1—N1	2.070 (3)	Zn1—I1	2.5538 (5)
Zn1—N2	2.099 (3)	Zn1—I2	2.5542 (4)

N1—Zn1—N2	85.04 (11)	N1—Zn1—I2	121.86 (8)
N1—Zn1—I1	105.44 (8)	N2—Zn1—I2	107.02 (8)
N2—Zn1—I1	110.30 (8)	I1—Zn1—I2	121.063 (18)

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