{2-Eth-oxy-6-[2-(piperidinium-1-yl)ethyl-imino-meth-yl]phenolato}diiodidozinc(II).

The title Schiff base complex, [ZnI(2)(C(16)H(24)N(2)O(2))], is a mononuclear zinc(II) compound. The Zn atom is four-coordinated in a distorted tetra-hedral geometry by one phenolate O atom and one imine N atom of the Schiff base ligand and by two iodide ions. In the crystal structure, mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds, forming chains running along the a axis.

Related literature

For background to the applications of Schiff bases, see: Averseng et al. (2001 ▶); Patra et al. (2002 ▶); Chen et al. (2003 ▶); Ruck & Jacobsen (2002 ▶). For the structures of related Schiff base zinc complexes, see: Wei et al. (2007 ▶); Zhu, Yang et al. (2009 ▶); Zhu, Yin, Li et al. (2009 ▶); Zhu, Yin, Yang et al. (2009 ▶).

Experimental

Crystal data

[ZnI2(C16H24N2O2)]

M = 595.54

Orthorhombic,

a = 13.5934 (10) Å

b = 10.2381 (8) Å

c = 14.7871 (11) Å

V = 2057.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 4.20 mm−1

T = 298 K

0.18 × 0.17 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.518, T max = 0.535

11751 measured reflections

4438 independent reflections

3763 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.068

S = 1.02

4438 reflections

212 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.58 e Å−3

Δρmin = −0.88 e Å−3

Absolute structure: Flack (1983 ▶), 2111 Friedel pairs

Flack parameter: 0.02 (2)

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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/S1600536809048491/sj2684sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048491/sj2684Isup2.hkl

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

[ZnI2(C16H24N2O2)]	F(000) = 1144
Mr = 595.54	Dx = 1.922 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 4921 reflections
a = 13.5934 (10) Å	θ = 2.4–27.9°
b = 10.2381 (8) Å	µ = 4.20 mm−1
c = 14.7871 (11) Å	T = 298 K
V = 2057.9 (3) Å3	Block, colourless
Z = 4	0.18 × 0.17 × 0.17 mm

Bruker SMART CCD area-detector diffractometer	4438 independent reflections
Radiation source: fine-focus sealed tube	3763 reflections with I > 2σ(I)
graphite	Rint = 0.029
ω scans	θmax = 27.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→17
Tmin = 0.518, Tmax = 0.535	k = −9→13
11751 measured reflections	l = −18→18

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.068	w = 1/[σ2(Fo2) + (0.0339P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
4438 reflections	Δρmax = 0.58 e Å−3
212 parameters	Δρmin = −0.88 e Å−3
2 restraints	Absolute structure: Flack (1983), 2111 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.02 (2)

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.

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 > σ(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	−0.02523 (3)	0.78151 (4)	0.73753 (7)	0.03660 (10)
I1	−0.07635 (3)	0.89935 (4)	0.881593 (19)	0.05811 (13)
I2	−0.07707 (3)	0.89530 (5)	0.590518 (18)	0.06408 (15)
N1	0.1209 (2)	0.7453 (3)	0.7350 (4)	0.0383 (6)
N2	0.2829 (3)	0.9941 (4)	0.8503 (2)	0.0380 (8)
O1	−0.06258 (15)	0.5977 (2)	0.7346 (4)	0.0386 (5)
O2	−0.1483 (3)	0.3910 (3)	0.6564 (2)	0.0567 (9)
C1	0.1005 (3)	0.5138 (4)	0.7039 (3)	0.0405 (10)
C2	−0.0040 (3)	0.5075 (4)	0.7033 (3)	0.0373 (9)
C3	−0.0463 (4)	0.3937 (4)	0.6658 (4)	0.0491 (11)
C4	0.0100 (5)	0.2871 (5)	0.6416 (4)	0.0660 (15)
H4	−0.0202	0.2112	0.6210	0.079*
C5	0.1109 (5)	0.2932 (5)	0.6478 (4)	0.0677 (16)
H5	0.1485	0.2207	0.6322	0.081*
C6	0.1556 (4)	0.4029 (5)	0.6762 (3)	0.0549 (13)
H6	0.2240	0.4063	0.6778	0.066*
C7	0.1560 (3)	0.6312 (4)	0.7217 (3)	0.0415 (12)
H7	0.2241	0.6229	0.7238	0.050*
C8	0.1907 (3)	0.8546 (4)	0.7423 (5)	0.0457 (9)
H8A	0.1612	0.9329	0.7174	0.055*
H8B	0.2495	0.8349	0.7078	0.055*
C9	0.2174 (3)	0.8774 (4)	0.8385 (3)	0.0417 (10)
H9A	0.2506	0.8007	0.8619	0.050*
H9B	0.1578	0.8901	0.8735	0.050*
C10	0.2269 (4)	1.1197 (4)	0.8443 (4)	0.0549 (12)
H10A	0.1750	1.1199	0.8893	0.066*
H10B	0.1965	1.1265	0.7851	0.066*
C11	0.2937 (5)	1.2366 (5)	0.8595 (4)	0.0739 (17)
H11A	0.3412	1.2418	0.8106	0.089*
H11B	0.2547	1.3159	0.8586	0.089*
C12	0.3470 (5)	1.2274 (6)	0.9474 (4)	0.0751 (17)
H12A	0.3002	1.2320	0.9968	0.090*
H12B	0.3921	1.3003	0.9532	0.090*
C13	0.4043 (5)	1.0991 (6)	0.9531 (5)	0.0674 (16)
H13A	0.4553	1.0984	0.9073	0.081*
H13B	0.4357	1.0927	1.0118	0.081*
C14	0.3384 (4)	0.9850 (5)	0.9397 (3)	0.0504 (12)
H14A	0.2916	0.9807	0.9891	0.060*
H14B	0.3772	0.9055	0.9405	0.060*
C15	−0.1804 (5)	0.4628 (8)	0.5756 (4)	0.083 (2)
H15A	−0.2514	0.4725	0.5771	0.099*
H15B	−0.1516	0.5495	0.5764	0.099*
C16	−0.1523 (7)	0.3969 (10)	0.4922 (6)	0.126 (4)
H16A	−0.0819	0.3911	0.4889	0.189*
H16B	−0.1764	0.4456	0.4413	0.189*
H16C	−0.1800	0.3107	0.4914	0.189*
H2	0.333 (3)	0.987 (6)	0.811 (3)	0.080*

	U11	U22	U33	U12	U13	U23
Zn1	0.02854 (19)	0.0357 (2)	0.0455 (2)	−0.00197 (15)	0.0007 (4)	−0.0052 (4)
I1	0.0524 (3)	0.0591 (2)	0.0628 (3)	−0.0002 (2)	0.0065 (2)	−0.0281 (2)
I2	0.0628 (4)	0.0766 (3)	0.0528 (3)	0.0076 (2)	0.0024 (2)	0.0169 (2)
N1	0.0261 (13)	0.0474 (16)	0.0414 (15)	−0.0071 (11)	−0.003 (3)	0.002 (3)
N2	0.0350 (19)	0.0452 (19)	0.0338 (18)	−0.0077 (16)	−0.0043 (15)	−0.0033 (15)
O1	0.0316 (12)	0.0381 (13)	0.0460 (13)	−0.0049 (9)	0.007 (2)	−0.005 (2)
O2	0.059 (2)	0.053 (2)	0.058 (2)	−0.0245 (15)	0.0061 (18)	−0.0095 (16)
C1	0.040 (2)	0.045 (2)	0.037 (2)	0.0128 (19)	−0.0005 (16)	0.0015 (17)
C2	0.042 (2)	0.034 (2)	0.036 (2)	0.0008 (18)	0.0030 (16)	0.0012 (15)
C3	0.062 (3)	0.039 (3)	0.046 (3)	−0.006 (2)	0.007 (2)	−0.004 (2)
C4	0.096 (5)	0.038 (3)	0.064 (4)	−0.002 (3)	0.009 (3)	−0.006 (2)
C5	0.092 (5)	0.045 (3)	0.067 (4)	0.028 (3)	0.006 (3)	−0.009 (3)
C6	0.058 (3)	0.060 (3)	0.047 (3)	0.025 (2)	0.002 (2)	0.000 (2)
C7	0.0279 (18)	0.061 (2)	0.036 (3)	0.0033 (16)	−0.0049 (18)	−0.004 (2)
C8	0.0343 (18)	0.055 (2)	0.048 (2)	−0.0151 (16)	−0.001 (3)	0.001 (4)
C9	0.037 (2)	0.044 (2)	0.045 (2)	−0.0062 (19)	−0.0032 (19)	0.0025 (18)
C10	0.067 (3)	0.049 (3)	0.049 (3)	0.008 (2)	−0.011 (3)	−0.002 (2)
C11	0.118 (5)	0.046 (3)	0.058 (3)	−0.005 (3)	−0.015 (3)	−0.002 (2)
C12	0.110 (5)	0.059 (3)	0.056 (3)	−0.020 (3)	−0.014 (3)	−0.007 (3)
C13	0.058 (4)	0.084 (4)	0.060 (4)	−0.019 (3)	−0.014 (3)	−0.012 (3)
C14	0.047 (3)	0.059 (3)	0.046 (3)	0.002 (2)	−0.017 (2)	0.000 (2)
C15	0.050 (4)	0.122 (6)	0.076 (4)	−0.021 (4)	0.002 (3)	−0.030 (4)
C16	0.073 (5)	0.214 (12)	0.091 (5)	0.007 (6)	−0.018 (5)	−0.051 (6)

Zn1—O1	1.950 (2)	C8—H8A	0.9700
Zn1—N1	2.021 (3)	C8—H8B	0.9700
Zn1—I1	2.5448 (9)	C9—H9A	0.9700
Zn1—I2	2.5651 (9)	C9—H9B	0.9700
N1—C7	1.277 (5)	C10—C11	1.520 (7)
N1—C8	1.471 (4)	C10—H10A	0.9700
N2—C10	1.498 (6)	C10—H10B	0.9700
N2—C9	1.500 (5)	C11—C12	1.491 (8)
N2—C14	1.524 (5)	C11—H11A	0.9700
N2—H2	0.90 (4)	C11—H11B	0.9700
O1—C2	1.304 (5)	C12—C13	1.529 (8)
O2—C3	1.394 (6)	C12—H12A	0.9700
O2—C15	1.470 (8)	C12—H12B	0.9700
C1—C6	1.421 (6)	C13—C14	1.485 (7)
C1—C2	1.421 (6)	C13—H13A	0.9700
C1—C7	1.444 (6)	C13—H13B	0.9700
C2—C3	1.412 (6)	C14—H14A	0.9700
C3—C4	1.381 (7)	C14—H14B	0.9700
C4—C5	1.376 (9)	C15—C16	1.457 (9)
C4—H4	0.9300	C15—H15A	0.9700
C5—C6	1.345 (7)	C15—H15B	0.9700
C5—H5	0.9300	C16—H16A	0.9600
C6—H6	0.9300	C16—H16B	0.9600
C7—H7	0.9300	C16—H16C	0.9600
C8—C9	1.486 (8)
O1—Zn1—N1	94.50 (10)	N2—C9—H9A	109.1
O1—Zn1—I1	113.89 (16)	C8—C9—H9B	109.1
N1—Zn1—I1	111.78 (16)	N2—C9—H9B	109.1
O1—Zn1—I2	110.37 (17)	H9A—C9—H9B	107.8
N1—Zn1—I2	109.73 (17)	N2—C10—C11	111.3 (4)
I1—Zn1—I2	114.776 (17)	N2—C10—H10A	109.4
C7—N1—C8	117.8 (3)	C11—C10—H10A	109.4
C7—N1—Zn1	122.5 (3)	N2—C10—H10B	109.4
C8—N1—Zn1	119.5 (2)	C11—C10—H10B	109.4
C10—N2—C9	112.0 (3)	H10A—C10—H10B	108.0
C10—N2—C14	110.8 (4)	C12—C11—C10	111.7 (5)
C9—N2—C14	110.3 (3)	C12—C11—H11A	109.3
C10—N2—H2	115 (4)	C10—C11—H11A	109.3
C9—N2—H2	108 (4)	C12—C11—H11B	109.3
C14—N2—H2	101 (4)	C10—C11—H11B	109.3
C2—O1—Zn1	122.1 (2)	H11A—C11—H11B	107.9
C3—O2—C15	111.5 (4)	C11—C12—C13	110.5 (5)
C6—C1—C2	119.3 (4)	C11—C12—H12A	109.6
C6—C1—C7	116.2 (4)	C13—C12—H12A	109.6
C2—C1—C7	124.1 (4)	C11—C12—H12B	109.6
O1—C2—C3	118.4 (4)	C13—C12—H12B	109.6
O1—C2—C1	125.1 (4)	H12A—C12—H12B	108.1
C3—C2—C1	116.5 (4)	C14—C13—C12	111.2 (5)
C4—C3—O2	120.7 (4)	C14—C13—H13A	109.4
C4—C3—C2	121.9 (5)	C12—C13—H13A	109.4
O2—C3—C2	117.4 (4)	C14—C13—H13B	109.4
C5—C4—C3	120.0 (5)	C12—C13—H13B	109.4
C5—C4—H4	120.0	H13A—C13—H13B	108.0
C3—C4—H4	120.0	C13—C14—N2	111.5 (4)
C6—C5—C4	120.6 (5)	C13—C14—H14A	109.3
C6—C5—H5	119.7	N2—C14—H14A	109.3
C4—C5—H5	119.7	C13—C14—H14B	109.3
C5—C6—C1	121.3 (5)	N2—C14—H14B	109.3
C5—C6—H6	119.4	H14A—C14—H14B	108.0
C1—C6—H6	119.4	C16—C15—O2	112.3 (7)
N1—C7—C1	126.5 (4)	C16—C15—H15A	109.1
N1—C7—H7	116.8	O2—C15—H15A	109.1
C1—C7—H7	116.8	C16—C15—H15B	109.1
N1—C8—C9	110.4 (5)	O2—C15—H15B	109.1
N1—C8—H8A	109.6	H15A—C15—H15B	107.9
C9—C8—H8A	109.6	C15—C16—H16A	109.5
N1—C8—H8B	109.6	C15—C16—H16B	109.5
C9—C8—H8B	109.6	H16A—C16—H16B	109.5
H8A—C8—H8B	108.1	C15—C16—H16C	109.5
C8—C9—N2	112.5 (3)	H16A—C16—H16C	109.5
C8—C9—H9A	109.1	H16B—C16—H16C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2i	0.90 (4)	2.61 (5)	3.237 (5)	127 (4)
N2—H2···O1i	0.90 (4)	2.01 (5)	2.867 (5)	159 (5)

Table 1

Selected bond lengths (Å)

Zn1—O1	1.950 (2)
Zn1—N1	2.021 (3)
Zn1—I1	2.5448 (9)
Zn1—I2	2.5651 (9)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.90 (4)	2.61 (5)	3.237 (5)	127 (4)
N2—H2⋯O1i	0.90 (4)	2.01 (5)	2.867 (5)	159 (5)

Symmetry code: (i) .