Diiodido{4-nitro-2-[2-(piperidin-1-yl)ethyl-imino-meth-yl]phenolato}zinc(II).

In the title complex, [ZnI(2)(C(14)H(19)N(3)O(3))], 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 tetra-hedral coordination. In the crystal structure, mol-ecules are linked through inter-molecular 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 = 596.49

Triclinic,

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[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.080

S = 1.01

4034 reflections

211 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 e Å−3

Δρmin = −0.62 e Å−3

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809040495/om2281sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040495/om2281Isup2.hkl

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

[ZnI2(C14H19N3O3)]	Z = 2
Mr = 596.49	F(000) = 568
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0311P)2 + 0.4408P] where P = (Fo2 + 2Fc2)/3
4034 reflections	(Δ/σ)max = 0.001
211 parameters	Δρmax = 0.50 e Å−3
1 restraint	Δρmin = −0.62 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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)

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) .