Acta Cryst. (2009). E65, m444 [ doi:10.1107/S1600536809010344 ]
The molecule of the title compound, [Zn(C20H22N2O4)]·H2O, deviates from planarity with a dihedral angle between the two benzene rings is 18.3 (1)°. The four-coordinate ZnII ion has a distorted square-planar coordination and is N2O2-chelated by the Schiff base ligand. The ZnII ion and solvent water molecule are located on a twofold rotation axis. The structure displays intermolecular O-H
O hydrogen bonding.
A mixture of 6,6'-Diethoxy-2,2'-(ethane-1,2-diyldiiminodimethylene)diphenol (0.1 mmol) and zinc acetate (0.1 mmol) in absolute methanol (20 ml) was heated at 50 centidegree and stirred for 30 min, then filtered. The resulting clear orange solution was moved to a tube, some ethyl ether was added, and then after 14 days, block-shaped crystals of the title complex suitable for X-ray diffraction analysis were obtained(yield: about 40%).
The H atoms were fixed geometrically and were treated as riding on their parent C atoms, with C–H distances in the range of 0.93–0.97Å and with Uiso(H) = 1.2Ueq(parent atom), or Uiso(H) = 1.5Ueq(Cmethyl). The coordinates of the water H atom were found in a difference Fourier map and refined with Uiso(H) = 1.2Ueq(O).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: XP in SHELXTL (Sheldrick, 2008).
![[Figure 1]](./pk2159fig1thm.gif)
| Fig. 1. The independent molecules of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. |
| [Zn(C20H22N2O4)]·H2O | F(000) = 912 |
| Mr = 437.78 | Dx = 1.461 Mg m−3 |
| Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2n 2ab | Cell parameters from 2488 reflections |
| a = 12.6512 (16) Å | θ = 3.3–24.0° |
| b = 19.986 (3) Å | µ = 1.27 mm−1 |
| c = 7.8708 (10) Å | T = 273 K |
| V = 1990.1 (4) Å3 | Needle, colourless |
| Z = 4 | 0.25 × 0.21 × 0.17 mm |
| Bruker APEXII CCD area-detector diffractometer | 1855 independent reflections |
| Radiation source: fine-focus sealed tube | 1423 reflections with I > 2σ(I) |
| graphite | Rint = 0.031 |
| φ and ω scans | θmax = 25.5°, θmin = 1.9° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −15→13 |
| Tmin = 0.742, Tmax = 0.813 | k = −24→23 |
| 9492 measured reflections | l = −9→9 |
| 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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.101 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.04 | w = 1/[σ2(Fo2) + (0.0592P)2 + 0.4077P] where P = (Fo2 + 2Fc2)/3 |
| 1855 reflections | (Δ/σ)max = 0.034 |
| 133 parameters | Δρmax = 0.24 e Å−3 |
| 1 restraint | Δρmin = −0.46 e Å−3 |
| [Zn(C20H22N2O4)]·H2O | V = 1990.1 (4) Å3 |
| Mr = 437.78 | Z = 4 |
| Orthorhombic, Pbcn | Mo Kα radiation |
| a = 12.6512 (16) Å | µ = 1.27 mm−1 |
| b = 19.986 (3) Å | T = 273 K |
| c = 7.8708 (10) Å | 0.25 × 0.21 × 0.17 mm |
| Bruker APEXII CCD area-detector diffractometer | 1855 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | 1423 reflections with I > 2σ(I) |
| Tmin = 0.742, Tmax = 0.813 | Rint = 0.031 |
| 9492 measured reflections | θmax = 25.5° |
| R[F2 > 2σ(F2)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.101 | Δρmax = 0.24 e Å−3 |
| S = 1.04 | Δρmin = −0.46 e Å−3 |
| 1855 reflections | Absolute structure: ? |
| 133 parameters | Flack parameter: ? |
| 1 restraint | Rogers parameter: ? |
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 | 0.5000 | 0.475277 (19) | 0.2500 | 0.04314 (18) | |
| O1 | 0.40642 (12) | 0.40659 (8) | 0.1698 (2) | 0.0441 (4) | |
| O2 | 0.31927 (13) | 0.29902 (8) | 0.0342 (2) | 0.0491 (4) | |
| O3 | 0.5000 | 0.26838 (19) | 0.2500 | 0.0940 (13) | |
| N1 | 0.40920 (19) | 0.54832 (10) | 0.1725 (3) | 0.0519 (6) | |
| C1 | 0.2641 (2) | 0.47896 (14) | 0.0770 (3) | 0.0530 (7) | |
| C2 | 0.31464 (18) | 0.41541 (12) | 0.0957 (3) | 0.0422 (6) | |
| C3 | 0.26222 (19) | 0.35776 (13) | 0.0260 (3) | 0.0468 (6) | |
| C4 | 0.1632 (2) | 0.36235 (17) | −0.0434 (4) | 0.0619 (8) | |
| H4 | 0.1294 | 0.3244 | −0.0849 | 0.074* | |
| C5 | 0.1133 (2) | 0.4253 (2) | −0.0514 (4) | 0.0800 (10) | |
| H5 | 0.0453 | 0.4284 | −0.0957 | 0.096* | |
| C6 | 0.1628 (3) | 0.48188 (19) | 0.0045 (4) | 0.0740 (10) | |
| H6 | 0.1289 | 0.5230 | −0.0055 | 0.089* | |
| C7 | 0.3159 (2) | 0.54153 (14) | 0.1154 (4) | 0.0588 (8) | |
| H7 | 0.2774 | 0.5805 | 0.0967 | 0.071* | |
| C8 | 0.2840 (2) | 0.24216 (14) | −0.0638 (4) | 0.0590 (8) | |
| H8A | 0.2683 | 0.2559 | −0.1792 | 0.071* | |
| H8B | 0.2201 | 0.2238 | −0.0142 | 0.071* | |
| C9 | 0.3688 (3) | 0.19045 (15) | −0.0647 (4) | 0.0726 (9) | |
| H9A | 0.4320 | 0.2090 | −0.1130 | 0.109* | |
| H9B | 0.3463 | 0.1528 | −0.1312 | 0.109* | |
| H9C | 0.3827 | 0.1762 | 0.0496 | 0.109* | |
| C10 | 0.4568 (3) | 0.61556 (13) | 0.1843 (4) | 0.0651 (8) | |
| H10A | 0.4030 | 0.6479 | 0.2152 | 0.078* | |
| H10B | 0.4857 | 0.6283 | 0.0748 | 0.078* | |
| H3A | 0.487 (4) | 0.2934 (18) | 0.172 (4) | 0.126 (18)* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Zn1 | 0.0450 (3) | 0.0357 (3) | 0.0487 (3) | 0.000 | 0.00991 (18) | 0.000 |
| O1 | 0.0357 (9) | 0.0407 (9) | 0.0558 (11) | 0.0034 (7) | −0.0043 (8) | 0.0012 (8) |
| O2 | 0.0455 (10) | 0.0505 (10) | 0.0513 (10) | −0.0085 (8) | −0.0114 (8) | 0.0028 (8) |
| O3 | 0.096 (3) | 0.054 (2) | 0.132 (4) | 0.000 | −0.064 (3) | 0.000 |
| N1 | 0.0604 (15) | 0.0394 (11) | 0.0558 (14) | 0.0128 (11) | 0.0222 (12) | 0.0062 (11) |
| C1 | 0.0456 (15) | 0.0639 (18) | 0.0496 (16) | 0.0188 (12) | 0.0072 (13) | 0.0064 (13) |
| C2 | 0.0342 (12) | 0.0563 (15) | 0.0361 (13) | 0.0052 (11) | 0.0062 (10) | 0.0073 (11) |
| C3 | 0.0378 (14) | 0.0650 (17) | 0.0376 (13) | 0.0001 (12) | 0.0031 (10) | 0.0109 (12) |
| C4 | 0.0378 (15) | 0.095 (2) | 0.0526 (17) | −0.0027 (15) | −0.0049 (12) | 0.0055 (16) |
| C5 | 0.0401 (17) | 0.126 (3) | 0.074 (2) | 0.0183 (19) | −0.0085 (15) | 0.012 (2) |
| C6 | 0.054 (2) | 0.091 (2) | 0.077 (2) | 0.0321 (17) | −0.0010 (15) | 0.011 (2) |
| C7 | 0.0645 (19) | 0.0545 (17) | 0.0575 (17) | 0.0282 (15) | 0.0164 (15) | 0.0095 (14) |
| C8 | 0.0666 (18) | 0.0623 (18) | 0.0481 (15) | −0.0252 (15) | −0.0096 (14) | 0.0051 (13) |
| C9 | 0.092 (2) | 0.0575 (18) | 0.068 (2) | −0.0142 (17) | −0.0122 (18) | −0.0091 (15) |
| C10 | 0.090 (2) | 0.0338 (14) | 0.071 (2) | 0.0088 (13) | 0.0375 (16) | 0.0048 (13) |
| Zn1—O1 | 1.9195 (16) | C4—C5 | 1.410 (5) |
| Zn1—O1i | 1.9195 (16) | C4—H4 | 0.9300 |
| Zn1—N1i | 1.955 (2) | C5—C6 | 1.365 (5) |
| Zn1—N1 | 1.955 (2) | C5—H5 | 0.9300 |
| O1—C2 | 1.311 (3) | C6—H6 | 0.9300 |
| O2—C3 | 1.380 (3) | C7—H7 | 0.9300 |
| O2—C8 | 1.444 (3) | C8—C9 | 1.489 (4) |
| O3—H3A | 0.807 (10) | C8—H8A | 0.9700 |
| N1—C7 | 1.270 (4) | C8—H8B | 0.9700 |
| N1—C10 | 1.476 (3) | C9—H9A | 0.9600 |
| C1—C6 | 1.404 (4) | C9—H9B | 0.9600 |
| C1—C2 | 1.429 (3) | C9—H9C | 0.9600 |
| C1—C7 | 1.444 (4) | C10—C10i | 1.505 (7) |
| C2—C3 | 1.438 (3) | C10—H10A | 0.9700 |
| C3—C4 | 1.369 (4) | C10—H10B | 0.9700 |
| O1—Zn1—O1i | 88.69 (9) | C4—C5—H5 | 119.4 |
| O1—Zn1—N1i | 177.35 (8) | C5—C6—C1 | 121.0 (3) |
| O1i—Zn1—N1i | 93.95 (9) | C5—C6—H6 | 119.5 |
| O1—Zn1—N1 | 93.95 (9) | C1—C6—H6 | 119.5 |
| O1i—Zn1—N1 | 177.35 (8) | N1—C7—C1 | 126.1 (2) |
| N1i—Zn1—N1 | 83.40 (15) | N1—C7—H7 | 117.0 |
| C2—O1—Zn1 | 126.60 (15) | C1—C7—H7 | 117.0 |
| C3—O2—C8 | 118.9 (2) | O2—C8—C9 | 109.0 (2) |
| C7—N1—C10 | 119.9 (2) | O2—C8—H8A | 109.9 |
| C7—N1—Zn1 | 125.21 (19) | C9—C8—H8A | 109.9 |
| C10—N1—Zn1 | 114.9 (2) | O2—C8—H8B | 109.9 |
| C6—C1—C2 | 119.1 (3) | C9—C8—H8B | 109.9 |
| C6—C1—C7 | 117.6 (3) | H8A—C8—H8B | 108.3 |
| C2—C1—C7 | 123.0 (3) | C8—C9—H9A | 109.5 |
| O1—C2—C1 | 124.1 (2) | C8—C9—H9B | 109.5 |
| O1—C2—C3 | 118.0 (2) | H9A—C9—H9B | 109.5 |
| C1—C2—C3 | 117.8 (2) | C8—C9—H9C | 109.5 |
| C4—C3—O2 | 123.6 (3) | H9A—C9—H9C | 109.5 |
| C4—C3—C2 | 121.3 (2) | H9B—C9—H9C | 109.5 |
| O2—C3—C2 | 115.0 (2) | N1—C10—C10i | 109.85 (18) |
| C3—C4—C5 | 119.2 (3) | N1—C10—H10A | 109.7 |
| C3—C4—H4 | 120.4 | C10i—C10—H10A | 109.7 |
| C5—C4—H4 | 120.4 | N1—C10—H10B | 109.7 |
| C6—C5—C4 | 121.3 (3) | C10i—C10—H10B | 109.7 |
| C6—C5—H5 | 119.4 | H10A—C10—H10B | 108.2 |
| Symmetry codes: (i) −x+1, y, −z+1/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O3—H3A···O1i | 0.81 (1) | 2.91 (5) | 3.071 (4) | 94 (3) |
| Symmetry codes: (i) −x+1, y, −z+1/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O3—H3A···O1i | 0.81 (1) | 2.91 (5) | 3.071 (4) | 94 (3) |
| Symmetry codes: (i) −x+1, y, −z+1/2. |
This work was supported by the Zhejiang Provincial Natural Science Foundation (Y4080395).
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Correia, I., Pessoa, J. C., Duarte, M. T., da Piedade, M. F. M., Jackush, T., Kiss, T., Castro, M. M. C. A., Geraldes, C. F. G. C. & Avecilla, F. (2005). Eur. J. Inorg. Chem. pp. 732–744.
Cunningham, D., McArdle, P., Mitchell, M., Chonchubhair, N. N., Gara, M. O., Franceschi, F. & Floriani, C. (2000). Inorg. Chem. 39, 1639–1649.
Lindoy, L. F., Lip, H. C., Power, L. F. & Rea, T. H. (1976). Inorg. Chem. 15, 1724–1727.
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
The schiff bases have been extensively studied as effective ligands for metal ions and used in the mechanism of many biochemical processes (Lindoy et al., 1976). N,N-disalicylideneethylenediamine type schiff bases ligands present versatile steric, electronic and lipophilic properties (Correia et al. 2005; Cunningham et al. 2000). We report here the synthesis and crystal structure of the title compound. The molecular structure is shown in Fig.1. The values of the geometric parameters in the structure are normal (Allen et al., 1987). The interplanar angles beween the the two phenyl group is 18.3 (1)°. The four-coordinate Zn gives plane coordination.