Diiodido{4-nitro-2-[2-(piperidin-1-yl)ethyl­imino­meth­yl]phenolato}zinc(II)

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

doi:10.1107/S1600536809040495

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Pages m1332-m1333

https://doi.org/10.1107/S1600536809040495

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Diiodido{4-nitro-2-[2-(piperidin-1-yl)ethyliminomethyl]phenolato}zinc(II)

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

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

(Received 19 September 2009; accepted 5 October 2009; online 10 October 2009)

In the title complex, [ZnI₂(C₁₄H₁₉N₃O₃)], the Zn^II atom is four-coordinated by the imine N and phenolate O atoms of the Schiff base ligand, and by two iodide ions in a distorted tetrahedral coordination. In the crystal structure, molecules are linked through intermolecular N—H⋯O hydrogen bonds, forming dimers.

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

[ZnI₂(C₁₄H₁₉N₃O₃)]
M_r = 596.49
Triclinic, $[P \overline 1]$
a = 8.7467 (2) Å
b = 10.7114 (3) Å
c = 10.9541 (2) Å
α = 89.553 (2)°
β = 89.334 (2)°
γ = 68.984 (2)°
V = 957.94 (4) Å³
Z = 2
Mo Kα radiation
μ = 4.52 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.465, T_max = 0.497
5795 measured reflections
4034 independent reflections
2994 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.080
S = 1.01
4034 reflections
211 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.62 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Zn1—O1	1.948 (3)
Zn1—N1	2.037 (3)
Zn1—I2	2.5666 (6)
Zn1—I1	2.5690 (6)

O1—Zn1—N1	94.96 (13)
O1—Zn1—I2	107.27 (10)
N1—Zn1—I2	113.81 (10)
O1—Zn1—I1	121.56 (10)
N1—Zn1—I1	102.97 (10)
I2—Zn1—I1	114.61 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2ⁱ	0.89 (4)	2.00 (3)	2.777 (5)	144 (5)
Symmetry code: (i) -x, -y+1, -z+1.

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: https://doi.org/10.1107/S1600536809040495/om2281sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809040495/om2281Isup2.hkl

checkCIF report

Comment top

Schiff bases are interesting 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 complexes have been investigated 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 phenolate O 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).

In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds, forming dimers (Table 2, Fig. 2).

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 5-nitrosalicylaldehyde with 2-piperidin-1-ylethylamine 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 (27.7 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.

Structure description top

In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds, forming dimers (Table 2, Fig. 2).

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).

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.
	Fig. 2. The crystal packing of the title complex, viewed along the c axis. Intermolecular hydrogen bonds are shown as dashed lines.

Diiodido{4-nitro-2-[2-(piperidin-1-yl)ethyliminomethyl]phenolato}zinc(II) top

Crystal data top

[ZnI₂(C₁₄H₁₉N₃O₃)]	Z = 2
M_r = 596.49	F(000) = 568
Triclinic, P1	D_x = 2.068 Mg m⁻³
a = 8.7467 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.7114 (3) Å	Cell parameters from 1800 reflections
c = 10.9541 (2) Å	θ = 2.6–25.5°
α = 89.553 (2)°	µ = 4.52 mm⁻¹
β = 89.334 (2)°	T = 298 K
γ = 68.984 (2)°	Block, colorless
V = 957.94 (4) Å³	0.20 × 0.20 × 0.18 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	4034 independent reflections
Radiation source: fine-focus sealed tube	2994 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ω scans	θ_max = 27.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −11→10
T_min = 0.465, T_max = 0.497	k = −11→13
5795 measured reflections	l = −13→13

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0311P)² + 0.4408P] where P = (F_o² + 2F_c²)/3
4034 reflections	(Δ/σ)_max = 0.001
211 parameters	Δρ_max = 0.50 e Å⁻³
1 restraint	Δρ_min = −0.62 e Å⁻³

Crystal data top

[ZnI₂(C₁₄H₁₉N₃O₃)]	γ = 68.984 (2)°
M_r = 596.49	V = 957.94 (4) Å³
Triclinic, P1	Z = 2
a = 8.7467 (2) Å	Mo Kα radiation
b = 10.7114 (3) Å	µ = 4.52 mm⁻¹
c = 10.9541 (2) Å	T = 298 K
α = 89.553 (2)°	0.20 × 0.20 × 0.18 mm
β = 89.334 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4034 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2994 reflections with I > 2σ(I)
T_min = 0.465, T_max = 0.497	R_int = 0.017
5795 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	1 restraint
wR(F²) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.50 e Å⁻³
4034 reflections	Δρ_min = −0.62 e Å⁻³
211 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	0.38637 (6)	0.75022 (5)	0.70365 (5)	0.04264 (14)
I1	0.26005 (4)	1.00680 (3)	0.70856 (3)	0.06259 (13)
I2	0.68572 (4)	0.65555 (4)	0.63039 (4)	0.07424 (14)
N1	0.2296 (4)	0.7001 (4)	0.5954 (3)	0.0390 (8)
N2	0.2722 (4)	0.8331 (3)	0.2827 (3)	0.0363 (8)
N3	0.0106 (4)	0.3085 (3)	0.8808 (3)	0.0435 (9)
O1	0.3662 (4)	0.6417 (3)	0.8421 (3)	0.0533 (8)
O2	−0.0766 (4)	0.3055 (3)	0.7938 (3)	0.0579 (9)
O3	0.0124 (4)	0.2483 (3)	0.9762 (3)	0.0587 (9)
C1	0.1913 (5)	0.5441 (4)	0.7469 (3)	0.0345 (9)
C2	0.2852 (5)	0.5627 (4)	0.8453 (4)	0.0355 (9)
C3	0.2900 (5)	0.4870 (4)	0.9535 (4)	0.0415 (10)
H3	0.3534	0.4954	1.0183	0.050*
C4	0.2054 (5)	0.4026 (4)	0.9657 (4)	0.0393 (10)
H4	0.2104	0.3549	1.0377	0.047*
C5	0.1107 (5)	0.3891 (4)	0.8682 (3)	0.0344 (9)
C6	0.1057 (5)	0.4572 (4)	0.7614 (4)	0.0378 (9)
H6	0.0438	0.4454	0.6970	0.045*
C7	0.1648 (5)	0.6156 (4)	0.6312 (4)	0.0378 (10)
H7	0.0934	0.5985	0.5774	0.045*
C8	0.1724 (5)	0.7702 (5)	0.4791 (4)	0.0482 (11)
H8A	0.1146	0.8647	0.4939	0.058*
H8B	0.0975	0.7346	0.4405	0.058*
C9	0.3181 (5)	0.7512 (5)	0.3965 (4)	0.0459 (11)
H9A	0.3989	0.7758	0.4401	0.055*
H9B	0.3676	0.6575	0.3748	0.055*
C10	0.2279 (6)	0.9798 (4)	0.3042 (4)	0.0508 (12)
H10A	0.3208	0.9959	0.3385	0.061*
H10B	0.1380	1.0103	0.3626	0.061*
C11	0.1785 (6)	1.0575 (5)	0.1866 (4)	0.0569 (13)
H11A	0.1527	1.1519	0.2022	0.068*
H11B	0.0809	1.0462	0.1553	0.068*
C12	0.3150 (6)	1.0100 (5)	0.0919 (4)	0.0537 (12)
H12A	0.2793	1.0582	0.0159	0.064*
H12B	0.4100	1.0277	0.1200	0.064*
C13	0.3597 (7)	0.8626 (5)	0.0713 (4)	0.0609 (14)
H13A	0.4504	0.8317	0.0137	0.073*
H13B	0.2672	0.8464	0.0362	0.073*
C14	0.4070 (6)	0.7853 (5)	0.1887 (4)	0.0609 (14)
H14A	0.4314	0.6911	0.1730	0.073*
H14B	0.5052	0.7954	0.2201	0.073*
H2	0.183 (4)	0.825 (5)	0.250 (4)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0420 (3)	0.0466 (3)	0.0436 (3)	−0.0209 (2)	−0.0078 (2)	0.0040 (2)
I1	0.0622 (2)	0.0466 (2)	0.0738 (3)	−0.01273 (16)	−0.01062 (18)	−0.00726 (17)
I2	0.03816 (19)	0.0782 (3)	0.0974 (3)	−0.00982 (18)	−0.00365 (18)	−0.0088 (2)
N1	0.0397 (19)	0.047 (2)	0.0332 (19)	−0.0191 (17)	−0.0049 (16)	0.0070 (16)
N2	0.040 (2)	0.039 (2)	0.0326 (19)	−0.0174 (16)	−0.0002 (15)	0.0030 (15)
N3	0.042 (2)	0.037 (2)	0.048 (2)	−0.0101 (17)	−0.0009 (18)	0.0072 (17)
O1	0.065 (2)	0.070 (2)	0.0409 (17)	−0.0426 (19)	−0.0175 (15)	0.0099 (16)
O2	0.068 (2)	0.062 (2)	0.060 (2)	−0.0424 (19)	−0.0181 (18)	0.0107 (17)
O3	0.063 (2)	0.055 (2)	0.059 (2)	−0.0233 (17)	−0.0031 (17)	0.0232 (17)
C1	0.033 (2)	0.042 (2)	0.026 (2)	−0.0120 (18)	−0.0035 (17)	0.0023 (17)
C2	0.033 (2)	0.040 (2)	0.034 (2)	−0.0144 (19)	−0.0044 (17)	0.0017 (18)
C3	0.039 (2)	0.051 (3)	0.032 (2)	−0.013 (2)	−0.0081 (18)	0.0002 (19)
C4	0.038 (2)	0.040 (2)	0.032 (2)	−0.0050 (19)	0.0018 (18)	0.0087 (18)
C5	0.037 (2)	0.032 (2)	0.033 (2)	−0.0111 (18)	−0.0016 (18)	0.0033 (17)
C6	0.039 (2)	0.040 (2)	0.035 (2)	−0.0142 (19)	−0.0066 (18)	0.0030 (18)
C7	0.038 (2)	0.048 (3)	0.029 (2)	−0.017 (2)	−0.0046 (18)	0.0038 (19)
C8	0.048 (3)	0.064 (3)	0.036 (2)	−0.025 (2)	−0.006 (2)	0.012 (2)
C9	0.046 (3)	0.047 (3)	0.042 (3)	−0.013 (2)	0.000 (2)	0.012 (2)
C10	0.068 (3)	0.041 (3)	0.043 (3)	−0.020 (2)	0.006 (2)	0.003 (2)
C11	0.063 (3)	0.043 (3)	0.056 (3)	−0.008 (2)	0.011 (3)	0.012 (2)
C12	0.053 (3)	0.062 (3)	0.048 (3)	−0.024 (3)	0.003 (2)	0.014 (2)
C13	0.071 (3)	0.066 (4)	0.044 (3)	−0.022 (3)	0.014 (3)	0.005 (2)
C14	0.067 (3)	0.049 (3)	0.055 (3)	−0.007 (3)	0.025 (3)	0.004 (2)

Geometric parameters (Å, º) top

Zn1—O1	1.948 (3)	C5—C6	1.367 (5)
Zn1—N1	2.037 (3)	C6—H6	0.9300
Zn1—I2	2.5666 (6)	C7—H7	0.9300
Zn1—I1	2.5690 (6)	C8—C9	1.508 (6)
N1—C7	1.284 (5)	C8—H8A	0.9700
N1—C8	1.473 (5)	C8—H8B	0.9700
N2—C9	1.492 (5)	C9—H9A	0.9700
N2—C10	1.496 (5)	C9—H9B	0.9700
N2—C14	1.503 (5)	C10—C11	1.509 (6)
N2—H2	0.89 (4)	C10—H10A	0.9700
N3—O3	1.220 (4)	C10—H10B	0.9700
N3—O2	1.235 (5)	C11—C12	1.518 (6)
N3—C5	1.439 (5)	C11—H11A	0.9700
O1—C2	1.285 (5)	C11—H11B	0.9700
C1—C6	1.396 (6)	C12—C13	1.502 (7)
C1—C2	1.420 (5)	C12—H12A	0.9700
C1—C7	1.452 (5)	C12—H12B	0.9700
C2—C3	1.423 (5)	C13—C14	1.503 (7)
C3—C4	1.363 (6)	C13—H13A	0.9700
C3—H3	0.9300	C13—H13B	0.9700
C4—C5	1.398 (6)	C14—H14A	0.9700
C4—H4	0.9300	C14—H14B	0.9700

O1—Zn1—N1	94.96 (13)	N1—C8—H8A	109.9
O1—Zn1—I2	107.27 (10)	C9—C8—H8A	109.9
N1—Zn1—I2	113.81 (10)	N1—C8—H8B	109.9
O1—Zn1—I1	121.56 (10)	C9—C8—H8B	109.9
N1—Zn1—I1	102.97 (10)	H8A—C8—H8B	108.3
I2—Zn1—I1	114.61 (2)	N2—C9—C8	112.2 (3)
C7—N1—C8	117.3 (4)	N2—C9—H9A	109.2
C7—N1—Zn1	121.3 (3)	C8—C9—H9A	109.2
C8—N1—Zn1	121.0 (3)	N2—C9—H9B	109.2
C9—N2—C10	113.3 (3)	C8—C9—H9B	109.2
C9—N2—C14	110.7 (3)	H9A—C9—H9B	107.9
C10—N2—C14	110.1 (3)	N2—C10—C11	110.8 (4)
C9—N2—H2	111 (3)	N2—C10—H10A	109.5
C10—N2—H2	105 (3)	C11—C10—H10A	109.5
C14—N2—H2	107 (3)	N2—C10—H10B	109.5
O3—N3—O2	122.8 (4)	C11—C10—H10B	109.5
O3—N3—C5	119.6 (4)	H10A—C10—H10B	108.1
O2—N3—C5	117.6 (3)	C10—C11—C12	110.9 (4)
C2—O1—Zn1	126.5 (3)	C10—C11—H11A	109.5
C6—C1—C2	119.3 (4)	C12—C11—H11A	109.5
C6—C1—C7	114.7 (4)	C10—C11—H11B	109.5
C2—C1—C7	125.8 (4)	C12—C11—H11B	109.5
O1—C2—C1	124.3 (4)	H11A—C11—H11B	108.0
O1—C2—C3	118.5 (4)	C13—C12—C11	109.5 (4)
C1—C2—C3	117.2 (4)	C13—C12—H12A	109.8
C4—C3—C2	122.4 (4)	C11—C12—H12A	109.8
C4—C3—H3	118.8	C13—C12—H12B	109.8
C2—C3—H3	118.8	C11—C12—H12B	109.8
C3—C4—C5	119.0 (4)	H12A—C12—H12B	108.2
C3—C4—H4	120.5	C12—C13—C14	111.2 (4)
C5—C4—H4	120.5	C12—C13—H13A	109.4
C6—C5—C4	120.6 (4)	C14—C13—H13A	109.4
C6—C5—N3	118.8 (4)	C12—C13—H13B	109.4
C4—C5—N3	120.5 (4)	C14—C13—H13B	109.4
C5—C6—C1	121.4 (4)	H13A—C13—H13B	108.0
C5—C6—H6	119.3	N2—C14—C13	111.4 (4)
C1—C6—H6	119.3	N2—C14—H14A	109.3
N1—C7—C1	126.9 (4)	C13—C14—H14A	109.3
N1—C7—H7	116.5	N2—C14—H14B	109.3
C1—C7—H7	116.5	C13—C14—H14B	109.3
N1—C8—C9	109.1 (4)	H14A—C14—H14B	108.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.89 (4)	2.00 (3)	2.777 (5)	144 (5)

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[ZnI₂(C₁₄H₁₉N₃O₃)]
M_r	596.49
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.7467 (2), 10.7114 (3), 10.9541 (2)
α, β, γ (°)	89.553 (2), 89.334 (2), 68.984 (2)
V (Å³)	957.94 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	4.52
Crystal size (mm)	0.20 × 0.20 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.465, 0.497
No. of measured, independent and observed [I > 2σ(I)] reflections	5795, 4034, 2994
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.080, 1.01
No. of reflections	4034
No. of parameters	211
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.62

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

Selected geometric parameters (Å, º) top

Zn1—O1	1.948 (3)	Zn1—I2	2.5666 (6)
Zn1—N1	2.037 (3)	Zn1—I1	2.5690 (6)

O1—Zn1—N1	94.96 (13)	O1—Zn1—I1	121.56 (10)
O1—Zn1—I2	107.27 (10)	N1—Zn1—I1	102.97 (10)
N1—Zn1—I2	113.81 (10)	I2—Zn1—I1	114.61 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.89 (4)	2.00 (3)	2.777 (5)	144 (5)

Symmetry code: (i) −x, −y+1, −z+1.

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Volume 65| Part 11| November 2009| Pages m1332-m1333

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