metal-organic compounds
{2-Ethoxy-6-[2-(piperidinium-1-yl)ethyliminomethyl]phenolato}diiodidozinc(II)
aDepartment of Chemistry, Baicheng Normal College, Baicheng 137000, People's Republic of China
*Correspondence e-mail: lijingyan56@126.com
The title Schiff base complex, [ZnI2(C16H24N2O2)], is a mononuclear zinc(II) compound. The Zn atom is four-coordinated in a distorted tetrahedral geometry by one phenolate O atom and one imine N atom of the Schiff base ligand and by two iodide ions. In the molecules are linked through intermolecular N—H⋯O hydrogen bonds, forming chains running along the a axis.
Related literature
For background to the applications of 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).
see: AversengExperimental
Crystal data
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Data collection: SMART (Bruker, 2002); cell 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.
Supporting information
10.1107/S1600536809048491/sj2684sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809048491/sj2684Isup2.hkl
2-Ethoxysalicylaldehyde (1.0 mmol, 166 mg), 2-piperidin-1-ylethylamine (1.0 mmol, 128 mg), and ZnI2 (1.0 mmol, 319 mg) were mixed in a methanol solution (50 ml). The mixture was stirred at reflux for 30 min to give a colourless solution. The solution was left in air for a few days, yielding colourless block-shaped crystals.
The H2 atom was located from a difference Fourier map and refined isotropically, with Uiso restrained to 0.08 Å2. Other H atoms were constrained to ideal geometries, with d(C–H) = 0.93–0.97 Å, and with Uiso(H) = 1.2Ueq(C), 1.5Ueq(Cmethyl).
Data collection: SMART (Bruker, 2002); cell
SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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).[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 monochromator | 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 | Absolute structure parameter: 0.02 (2) |
[ZnI2(C16H24N2O2)] | V = 2057.9 (3) Å3 |
Mr = 595.54 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 13.5934 (10) Å | µ = 4.20 mm−1 |
b = 10.2381 (8) Å | T = 298 K |
c = 14.7871 (11) Å | 0.18 × 0.17 × 0.17 mm |
Bruker SMART CCD area-detector diffractometer | 4438 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3763 reflections with I > 2σ(I) |
Tmin = 0.518, Tmax = 0.535 | Rint = 0.029 |
11751 measured reflections |
R[F2 > 2σ(F2)] = 0.028 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.068 | Δρmax = 0.58 e Å−3 |
S = 1.02 | Δρmin = −0.88 e Å−3 |
4438 reflections | Absolute structure: Flack (1983), 2111 Friedel pairs |
212 parameters | Absolute structure parameter: 0.02 (2) |
2 restraints |
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) |
Symmetry code: (i) x+1/2, −y+3/2, z. |
Experimental details
Crystal data | |
Chemical formula | [ZnI2(C16H24N2O2)] |
Mr | 595.54 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 298 |
a, b, c (Å) | 13.5934 (10), 10.2381 (8), 14.7871 (11) |
V (Å3) | 2057.9 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 4.20 |
Crystal size (mm) | 0.18 × 0.17 × 0.17 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.518, 0.535 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11751, 4438, 3763 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.028, 0.068, 1.02 |
No. of reflections | 4438 |
No. of parameters | 212 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.58, −0.88 |
Absolute structure | Flack (1983), 2111 Friedel pairs |
Absolute structure parameter | 0.02 (2) |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
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) x+1/2, −y+3/2, z. |
Acknowledgements
The author thanks Baicheng Normal College for support of this work.
References
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Zhu, X.-W., Yin, Z.-G., Yang, X.-Z., Li, G.-S. & Zhang, C.-X. (2009). Acta Cryst. E65, m1293–m1294. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Schiff bases are versatile ligands for the preparation in the preparation of metal complexes (Averseng et al., 2001; Patra et al., 2002; Chen et al., 2003; Ruck & Jacobsen, 2002). In this paper, the new zinc(II)title complex with the Schiff base ligand 2-ethoxy-6-[(2-piperidin-1-ylethylimino)methyl]phenol is reported.
In the title complex, Fig. 1, the Zn atom is four-coordinated by one phenolate O and one imine N atoms of the Schiff base ligand, and by two iodide atoms, forming a tetrahedral coordination. The coordinate bond lengths (Table 1) and angles are comparable to those of similar zinc complexes (Wei et al., 2007; Zhu, Yang et al., 2009; Zhu, Yin, Li et al., 2009; Zhu, Yin, Yang et al., 2009).
In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 2), forming chains running along the a axis (Fig. 2).