Acta Cryst. (2007). E63, m1992 [ doi:10.1107/S1600536807030206 ]
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2N,O1]zinc(II)In the title complex, [Zn(C10H12NO3)2], the ZnII ion is coordinated by two N,O-bidentate ligands in a distorted tetrahedral geometry. The crystal packing is stabilized by intermolecular O-H
O hydrogen bonds and C-HCg interactions (Cg is an aromatic ring centroid). The hydroxy substituent of one ethanolamine group is disordered over two sites with the ratio of refined occupancies being 0.844 (4): 0.156 (4).
Ethanolamine(1 mmol, 0.059 ml) was dissolved in hot methanol (10 ml) and added in portions to a methanol solution(3 ml) of o-vanillin (1 mmol, 152.14 mg). The mixture was then stirred at 323 K for 2 h. Subsequently, an aqueous solution(2 ml) of zinc acetate dihydrate(1 mmol, 219.5 mg) was added dropwise and stirred for another 5 h. The solution was held at room temperature for ten days, where upon yellow blocks were obtained.
Difference Fourier maps revealed that the hydroxy substituent of one ethanolamine group is disordered over two sites. The subsequent refinement of their occupancies gave the values of 0.844 (4) and 0.156 (4), respectively. All the H atoms were placed in geometrically calculated positions (C—H = 0.93 − 0.97Å and O—H = 0.82 Å) and allowed to ride on their respective parent atoms, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl).
In the crystal structure, there are solvent accesible voids of 121.0 Å3. These voids may initially have contained solvent, but this has been lost without degradation of the structure. There is no significant residual electron density to suggest the presence of solvent of crystallization.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
![[Figure 1]](./lh2415fig1thm.gif)
| Fig. 1. The structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. Open bonds indicate the minor component of disorder. |
![[Figure 2]](./lh2415fig2thm.gif)
| Fig. 2. The packing of the title compound. Hydrogen bond are shown as dashed lines. |
| [Zn(C10H12NO3)2] | F000 = 1888 |
| Mr = 453.78 | Dx = 1.363 Mg m−3 |
| Orthorhombic, Pbca | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P 2ac 2ab | Cell parameters from 3930 reflections |
| a = 17.624 (2) Å | θ = 2.3–23.2º |
| b = 7.2013 (14) Å | µ = 1.15 mm−1 |
| c = 34.853 (3) Å | T = 298 (2) K |
| V = 4423.3 (11) Å3 | Block, yellow |
| Z = 8 | 0.59 × 0.26 × 0.24 mm |
| Bruker SMART CCD diffractometer | 3904 independent reflections |
| Radiation source: fine-focus sealed tube | 2485 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.059 |
| T = 298(2) K | θmax = 25.0º |
| φ and ω scans | θmin = 1.2º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −15→20 |
| Tmin = 0.551, Tmax = 0.770 | k = −8→6 |
| 20138 measured reflections | l = −40→41 |
| 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)] = 0.078 | H-atom parameters constrained |
| wR(F2) = 0.170 | w = 1/[σ2(Fo2) + (0.0382P)2 + 21.0111P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.08 | (Δ/σ)max = 0.002 |
| 3904 reflections | Δρmax = 0.58 e Å−3 |
| 266 parameters | Δρmin = −1.04 e Å−3 |
| 6 restraints | Extinction correction: none |
| Primary atom site location: structure-invariant direct methods |
| [Zn(C10H12NO3)2] | V = 4423.3 (11) Å3 |
| Mr = 453.78 | Z = 8 |
| Orthorhombic, Pbca | Mo Kα |
| a = 17.624 (2) Å | µ = 1.15 mm−1 |
| b = 7.2013 (14) Å | T = 298 (2) K |
| c = 34.853 (3) Å | 0.59 × 0.26 × 0.24 mm |
| Bruker SMART CCD diffractometer | 3904 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2485 reflections with I > 2σ(I) |
| Tmin = 0.551, Tmax = 0.770 | Rint = 0.059 |
| 20138 measured reflections |
| R[F2 > 2σ(F2)] = 0.078 | 6 restraints |
| wR(F2) = 0.170 | H-atom parameters constrained |
| S = 1.08 | w = 1/[σ2(Fo2) + (0.0382P)2 + 21.0111P] where P = (Fo2 + 2Fc2)/3 |
| 3904 reflections | Δρmax = 0.58 e Å−3 |
| 266 parameters | Δρmin = −1.04 e Å−3 |
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 | Occ. (<1) | |
| Zn1 | 0.50272 (4) | 0.33878 (10) | 0.12373 (2) | 0.0460 (3) | |
| N1 | 0.4934 (3) | 0.1249 (6) | 0.15934 (15) | 0.0429 (13) | |
| N2 | 0.5700 (3) | 0.3369 (8) | 0.07788 (17) | 0.0514 (14) | |
| O1 | 0.5436 (3) | 0.5126 (6) | 0.16004 (13) | 0.0561 (13) | |
| O2 | 0.6315 (3) | 0.7510 (7) | 0.19242 (18) | 0.0809 (19) | |
| O3 | 0.5677 (3) | −0.1683 (7) | 0.11585 (15) | 0.0645 (14) | |
| H3 | 0.5721 | −0.2384 | 0.1343 | 0.097* | |
| O4 | 0.4108 (2) | 0.3744 (6) | 0.09550 (13) | 0.0514 (12) | |
| O5 | 0.2730 (3) | 0.3516 (8) | 0.07015 (18) | 0.0788 (17) | |
| O6 | 0.6846 (4) | 0.0466 (11) | 0.0930 (3) | 0.112 (3) | 0.844 (10) |
| H6 | 0.6437 | −0.0027 | 0.0977 | 0.168* | 0.844 (10) |
| O6' | 0.658 (2) | 0.109 (5) | 0.1366 (9) | 0.112 (3) | 0.156 (10) |
| H6' | 0.6377 | 0.0179 | 0.1272 | 0.168* | 0.156 (10) |
| C1 | 0.5196 (3) | 0.1339 (10) | 0.1936 (2) | 0.0490 (18) | |
| H1 | 0.5110 | 0.0311 | 0.2091 | 0.059* | |
| C2 | 0.5610 (4) | 0.2867 (10) | 0.21073 (19) | 0.0481 (17) | |
| C3 | 0.5730 (4) | 0.4594 (10) | 0.1931 (2) | 0.0490 (17) | |
| C4 | 0.6204 (4) | 0.5901 (11) | 0.2130 (2) | 0.057 (2) | |
| C5 | 0.6516 (4) | 0.5473 (14) | 0.2473 (2) | 0.069 (2) | |
| H5 | 0.6826 | 0.6340 | 0.2594 | 0.083* | |
| C6 | 0.6389 (5) | 0.3790 (15) | 0.2649 (2) | 0.070 (2) | |
| H6A | 0.6611 | 0.3525 | 0.2885 | 0.084* | |
| C7 | 0.5936 (4) | 0.2518 (12) | 0.2473 (2) | 0.058 (2) | |
| H7A | 0.5836 | 0.1396 | 0.2595 | 0.070* | |
| C8 | 0.6948 (5) | 0.8650 (12) | 0.2030 (3) | 0.090 (3) | |
| H8A | 0.6881 | 0.9091 | 0.2287 | 0.135* | |
| H8B | 0.6981 | 0.9689 | 0.1858 | 0.135* | |
| H8C | 0.7407 | 0.7934 | 0.2015 | 0.135* | |
| C9 | 0.4568 (4) | −0.0470 (9) | 0.14736 (19) | 0.0507 (18) | |
| H9A | 0.4031 | −0.0245 | 0.1432 | 0.061* | |
| H9B | 0.4617 | −0.1390 | 0.1675 | 0.061* | |
| C10 | 0.4916 (4) | −0.1202 (8) | 0.11123 (18) | 0.0482 (18) | |
| H10A | 0.4635 | −0.2287 | 0.1029 | 0.058* | |
| H10B | 0.4875 | −0.0267 | 0.0913 | 0.058* | |
| C11 | 0.5428 (4) | 0.3142 (10) | 0.0441 (2) | 0.0559 (19) | |
| H11 | 0.5779 | 0.3098 | 0.0241 | 0.067* | |
| C12 | 0.4643 (4) | 0.2946 (9) | 0.03341 (18) | 0.0465 (17) | |
| C13 | 0.4036 (4) | 0.3298 (8) | 0.05885 (19) | 0.0421 (15) | |
| C14 | 0.3285 (4) | 0.3176 (10) | 0.0440 (2) | 0.0535 (19) | |
| C15 | 0.3167 (6) | 0.2739 (12) | 0.0058 (3) | 0.077 (3) | |
| H15 | 0.2674 | 0.2674 | −0.0036 | 0.093* | |
| C16 | 0.3767 (6) | 0.2399 (13) | −0.0186 (2) | 0.082 (3) | |
| H16 | 0.3677 | 0.2088 | −0.0441 | 0.099* | |
| C17 | 0.4493 (5) | 0.2520 (12) | −0.0053 (2) | 0.074 (2) | |
| H17 | 0.4895 | 0.2317 | −0.0220 | 0.088* | |
| C18 | 0.1962 (4) | 0.3283 (14) | 0.0591 (3) | 0.107 (4) | |
| H18A | 0.1813 | 0.4291 | 0.0427 | 0.160* | |
| H18B | 0.1647 | 0.3269 | 0.0815 | 0.160* | |
| H18C | 0.1907 | 0.2130 | 0.0455 | 0.160* | |
| C19 | 0.6518 (3) | 0.3659 (11) | 0.0824 (2) | 0.068 (2) | |
| H19A | 0.6609 | 0.4877 | 0.0933 | 0.081* | |
| H19B | 0.6761 | 0.3613 | 0.0574 | 0.081* | |
| C20 | 0.6857 (5) | 0.2195 (11) | 0.1080 (3) | 0.091 (3) | |
| H20A | 0.7378 | 0.2531 | 0.1137 | 0.109* | 0.844 (10) |
| H20B | 0.6580 | 0.2184 | 0.1321 | 0.109* | 0.844 (10) |
| H20C | 0.7024 | 0.1211 | 0.0910 | 0.109* | 0.156 (10) |
| H20D | 0.7317 | 0.2751 | 0.1181 | 0.109* | 0.156 (10) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Zn1 | 0.0508 (4) | 0.0403 (4) | 0.0471 (4) | −0.0061 (4) | −0.0087 (4) | 0.0018 (4) |
| N1 | 0.045 (3) | 0.031 (3) | 0.053 (3) | −0.009 (3) | 0.007 (3) | 0.000 (2) |
| N2 | 0.041 (3) | 0.053 (4) | 0.060 (4) | −0.009 (3) | 0.003 (3) | 0.011 (3) |
| O1 | 0.071 (3) | 0.034 (3) | 0.063 (3) | 0.000 (2) | −0.025 (3) | −0.002 (2) |
| O2 | 0.083 (4) | 0.048 (3) | 0.112 (5) | −0.007 (3) | −0.060 (4) | −0.005 (3) |
| O3 | 0.062 (3) | 0.052 (3) | 0.079 (4) | −0.002 (3) | 0.010 (3) | 0.002 (3) |
| O4 | 0.043 (3) | 0.059 (3) | 0.052 (3) | 0.002 (2) | −0.001 (2) | −0.006 (2) |
| O5 | 0.038 (3) | 0.085 (4) | 0.113 (5) | −0.004 (3) | −0.009 (3) | −0.003 (4) |
| O6 | 0.056 (4) | 0.081 (6) | 0.200 (10) | 0.003 (4) | 0.010 (5) | −0.025 (6) |
| O6' | 0.056 (4) | 0.081 (6) | 0.200 (10) | 0.003 (4) | 0.010 (5) | −0.025 (6) |
| C1 | 0.043 (4) | 0.049 (4) | 0.056 (4) | 0.005 (3) | 0.010 (3) | 0.007 (4) |
| C2 | 0.041 (4) | 0.058 (5) | 0.046 (4) | 0.005 (3) | 0.006 (3) | 0.001 (4) |
| C3 | 0.047 (4) | 0.050 (4) | 0.050 (4) | 0.013 (3) | −0.009 (3) | −0.014 (4) |
| C4 | 0.049 (4) | 0.067 (5) | 0.055 (5) | 0.015 (4) | −0.013 (4) | −0.022 (4) |
| C5 | 0.050 (5) | 0.100 (7) | 0.056 (5) | 0.015 (5) | −0.014 (4) | −0.037 (5) |
| C6 | 0.057 (5) | 0.108 (8) | 0.045 (4) | 0.014 (5) | −0.002 (4) | −0.013 (5) |
| C7 | 0.055 (4) | 0.081 (6) | 0.038 (4) | 0.009 (4) | 0.009 (4) | 0.007 (4) |
| C8 | 0.077 (6) | 0.054 (5) | 0.139 (9) | −0.013 (5) | −0.042 (6) | −0.015 (6) |
| C9 | 0.051 (4) | 0.036 (4) | 0.065 (5) | −0.010 (3) | 0.006 (4) | 0.001 (4) |
| C10 | 0.073 (5) | 0.026 (3) | 0.046 (4) | −0.009 (3) | −0.009 (4) | −0.008 (3) |
| C11 | 0.055 (5) | 0.057 (5) | 0.056 (5) | 0.007 (4) | 0.018 (4) | 0.009 (4) |
| C12 | 0.059 (4) | 0.044 (4) | 0.037 (4) | −0.003 (3) | 0.001 (3) | 0.002 (3) |
| C13 | 0.049 (4) | 0.029 (3) | 0.049 (4) | −0.007 (3) | −0.008 (3) | −0.001 (3) |
| C14 | 0.051 (4) | 0.038 (4) | 0.072 (5) | −0.004 (4) | −0.020 (4) | 0.003 (4) |
| C15 | 0.090 (7) | 0.069 (6) | 0.073 (6) | −0.011 (5) | −0.044 (5) | 0.000 (5) |
| C16 | 0.119 (8) | 0.084 (7) | 0.044 (5) | −0.015 (6) | −0.025 (5) | −0.009 (5) |
| C17 | 0.090 (6) | 0.085 (7) | 0.046 (5) | −0.007 (5) | 0.004 (5) | −0.002 (4) |
| C18 | 0.040 (5) | 0.090 (7) | 0.189 (11) | −0.007 (5) | −0.026 (6) | 0.020 (8) |
| C19 | 0.042 (4) | 0.063 (5) | 0.098 (6) | −0.007 (4) | 0.009 (4) | 0.018 (5) |
| C20 | 0.044 (5) | 0.070 (6) | 0.157 (10) | 0.006 (4) | −0.031 (6) | −0.003 (7) |
| Zn1—O4 | 1.913 (4) | C7—H7A | 0.9300 |
| Zn1—O1 | 1.921 (4) | C8—H8A | 0.9600 |
| Zn1—N1 | 1.985 (5) | C8—H8B | 0.9600 |
| Zn1—N2 | 1.990 (6) | C8—H8C | 0.9600 |
| N1—C1 | 1.281 (8) | C9—C10 | 1.497 (8) |
| N1—C9 | 1.458 (7) | C9—H9A | 0.9700 |
| N2—C11 | 1.283 (9) | C9—H9B | 0.9700 |
| N2—C19 | 1.465 (7) | C10—H10A | 0.9700 |
| O1—C3 | 1.319 (8) | C10—H10B | 0.9700 |
| O2—C4 | 1.378 (9) | C11—C12 | 1.440 (10) |
| O2—C8 | 1.433 (8) | C11—H11 | 0.9300 |
| O3—C10 | 1.394 (7) | C12—C17 | 1.408 (10) |
| O3—H3 | 0.8200 | C12—C13 | 1.412 (9) |
| O4—C13 | 1.323 (7) | C13—C14 | 1.425 (9) |
| O5—C14 | 1.358 (9) | C14—C15 | 1.383 (11) |
| O5—C18 | 1.417 (8) | C15—C16 | 1.379 (12) |
| O6—C20 | 1.352 (8) | C15—H15 | 0.9300 |
| O6—H6 | 0.8200 | C16—C17 | 1.362 (12) |
| O6—H20C | 0.6256 | C16—H16 | 0.9300 |
| O6'—C20 | 1.361 (11) | C17—H17 | 0.9300 |
| O6'—H6' | 0.8200 | C18—H18A | 0.9600 |
| C1—C2 | 1.450 (10) | C18—H18B | 0.9600 |
| C1—H1 | 0.9300 | C18—H18C | 0.9600 |
| C2—C3 | 1.404 (10) | C19—C20 | 1.506 (9) |
| C2—C7 | 1.421 (9) | C19—H19A | 0.9700 |
| C3—C4 | 1.437 (9) | C19—H19B | 0.9700 |
| C4—C5 | 1.351 (10) | C20—H20A | 0.9700 |
| C5—C6 | 1.376 (11) | C20—H20B | 0.9700 |
| C5—H5 | 0.9300 | C20—H20C | 0.9700 |
| C6—C7 | 1.362 (11) | C20—H20D | 0.9700 |
| C6—H6A | 0.9300 | ||
| O4—Zn1—O1 | 124.7 (2) | C9—C10—H10A | 109.1 |
| O4—Zn1—N1 | 110.8 (2) | O3—C10—H10B | 109.1 |
| O1—Zn1—N1 | 97.2 (2) | C9—C10—H10B | 109.1 |
| O4—Zn1—N2 | 95.3 (2) | H10A—C10—H10B | 107.8 |
| O1—Zn1—N2 | 108.1 (2) | N2—C11—C12 | 127.4 (6) |
| N1—Zn1—N2 | 123.1 (2) | N2—C11—H11 | 116.3 |
| C1—N1—C9 | 118.0 (6) | C12—C11—H11 | 116.3 |
| C1—N1—Zn1 | 120.9 (4) | C17—C12—C13 | 119.9 (7) |
| C9—N1—Zn1 | 121.1 (4) | C17—C12—C11 | 116.7 (7) |
| C11—N2—C19 | 118.9 (6) | C13—C12—C11 | 123.3 (6) |
| C11—N2—Zn1 | 121.1 (5) | O4—C13—C12 | 125.3 (6) |
| C19—N2—Zn1 | 120.0 (5) | O4—C13—C14 | 117.0 (6) |
| C3—O1—Zn1 | 122.2 (4) | C12—C13—C14 | 117.7 (6) |
| C4—O2—C8 | 117.4 (6) | O5—C14—C15 | 125.3 (7) |
| C10—O3—H3 | 109.5 | O5—C14—C13 | 114.5 (6) |
| C13—O4—Zn1 | 123.0 (4) | C15—C14—C13 | 120.2 (8) |
| C14—O5—C18 | 118.9 (7) | C16—C15—C14 | 121.3 (8) |
| C20—O6—H6 | 109.5 | C16—C15—H15 | 119.4 |
| H6—O6—H20C | 146.5 | C14—C15—H15 | 119.4 |
| C20—O6'—H6' | 109.5 | C17—C16—C15 | 119.9 (8) |
| N1—C1—C2 | 127.2 (6) | C17—C16—H16 | 120.1 |
| N1—C1—H1 | 116.4 | C15—C16—H16 | 120.1 |
| C2—C1—H1 | 116.4 | C16—C17—C12 | 121.1 (8) |
| C3—C2—C7 | 119.3 (7) | C16—C17—H17 | 119.4 |
| C3—C2—C1 | 124.6 (6) | C12—C17—H17 | 119.4 |
| C7—C2—C1 | 116.1 (7) | O5—C18—H18A | 109.5 |
| O1—C3—C2 | 125.5 (6) | O5—C18—H18B | 109.5 |
| O1—C3—C4 | 117.4 (7) | H18A—C18—H18B | 109.5 |
| C2—C3—C4 | 117.1 (7) | O5—C18—H18C | 109.5 |
| C5—C4—O2 | 126.5 (8) | H18A—C18—H18C | 109.5 |
| C5—C4—C3 | 121.0 (8) | H18B—C18—H18C | 109.5 |
| O2—C4—C3 | 112.4 (6) | N2—C19—C20 | 110.7 (6) |
| C4—C5—C6 | 121.9 (8) | N2—C19—H19A | 109.5 |
| C4—C5—H5 | 119.1 | C20—C19—H19A | 109.5 |
| C6—C5—H5 | 119.1 | N2—C19—H19B | 109.5 |
| C7—C6—C5 | 119.2 (8) | C20—C19—H19B | 109.5 |
| C7—C6—H6A | 120.4 | H19A—C19—H19B | 108.1 |
| C5—C6—H6A | 120.4 | O6—C20—O6' | 75.0 (19) |
| C6—C7—C2 | 121.5 (8) | O6—C20—C19 | 114.2 (9) |
| C6—C7—H7A | 119.3 | O6'—C20—C19 | 134.6 (18) |
| C2—C7—H7A | 119.3 | O6—C20—H20A | 108.7 |
| O2—C8—H8A | 109.5 | O6'—C20—H20A | 109.4 |
| O2—C8—H8B | 109.5 | C19—C20—H20A | 108.7 |
| H8A—C8—H8B | 109.5 | O6—C20—H20B | 108.7 |
| O2—C8—H8C | 109.5 | C19—C20—H20B | 108.7 |
| H8A—C8—H8C | 109.5 | H20A—C20—H20B | 107.6 |
| H8B—C8—H8C | 109.5 | O6'—C20—H20C | 97.4 |
| N1—C9—C10 | 111.0 (5) | C19—C20—H20C | 105.6 |
| N1—C9—H9A | 109.4 | H20A—C20—H20C | 91.0 |
| C10—C9—H9A | 109.4 | H20B—C20—H20C | 132.5 |
| N1—C9—H9B | 109.4 | O6—C20—H20D | 122.1 |
| C10—C9—H9B | 109.4 | O6'—C20—H20D | 105.8 |
| H9A—C9—H9B | 108.0 | C19—C20—H20D | 104.9 |
| O3—C10—C9 | 112.7 (5) | H20B—C20—H20D | 96.3 |
| O3—C10—H10A | 109.1 | H20C—C20—H20D | 105.5 |
| O4—Zn1—N1—C1 | −137.9 (5) | C3—C4—C5—C6 | −0.9 (11) |
| O1—Zn1—N1—C1 | −6.4 (5) | C4—C5—C6—C7 | 0.0 (12) |
| N2—Zn1—N1—C1 | 110.7 (5) | C5—C6—C7—C2 | 2.0 (11) |
| O4—Zn1—N1—C9 | 42.2 (5) | C3—C2—C7—C6 | −3.0 (10) |
| O1—Zn1—N1—C9 | 173.7 (5) | C1—C2—C7—C6 | 174.5 (6) |
| N2—Zn1—N1—C9 | −69.3 (5) | C1—N1—C9—C10 | −126.1 (6) |
| O4—Zn1—N2—C11 | −16.0 (6) | Zn1—N1—C9—C10 | 53.9 (7) |
| O1—Zn1—N2—C11 | −145.2 (6) | N1—C9—C10—O3 | 63.3 (7) |
| N1—Zn1—N2—C11 | 103.1 (6) | C19—N2—C11—C12 | −176.1 (7) |
| O4—Zn1—N2—C19 | 162.6 (5) | Zn1—N2—C11—C12 | 2.5 (11) |
| O1—Zn1—N2—C19 | 33.4 (6) | N2—C11—C12—C17 | −173.6 (8) |
| N1—Zn1—N2—C19 | −78.3 (6) | N2—C11—C12—C13 | 11.3 (12) |
| O4—Zn1—O1—C3 | 138.0 (5) | Zn1—O4—C13—C12 | −16.3 (9) |
| N1—Zn1—O1—C3 | 16.4 (5) | Zn1—O4—C13—C14 | 164.1 (4) |
| N2—Zn1—O1—C3 | −111.9 (5) | C17—C12—C13—O4 | −178.7 (7) |
| O1—Zn1—O4—C13 | 139.0 (5) | C11—C12—C13—O4 | −3.8 (11) |
| N1—Zn1—O4—C13 | −105.8 (5) | C17—C12—C13—C14 | 0.9 (10) |
| N2—Zn1—O4—C13 | 22.6 (5) | C11—C12—C13—C14 | 175.8 (7) |
| C9—N1—C1—C2 | 176.8 (6) | C18—O5—C14—C15 | 5.0 (12) |
| Zn1—N1—C1—C2 | −3.1 (9) | C18—O5—C14—C13 | −174.9 (7) |
| N1—C1—C2—C3 | 6.4 (11) | O4—C13—C14—O5 | −0.9 (9) |
| N1—C1—C2—C7 | −171.1 (6) | C12—C13—C14—O5 | 179.5 (6) |
| Zn1—O1—C3—C2 | −18.0 (9) | O4—C13—C14—C15 | 179.2 (7) |
| Zn1—O1—C3—C4 | 163.0 (5) | C12—C13—C14—C15 | −0.5 (10) |
| C7—C2—C3—O1 | −177.0 (6) | O5—C14—C15—C16 | −179.4 (8) |
| C1—C2—C3—O1 | 5.6 (11) | C13—C14—C15—C16 | 0.5 (12) |
| C7—C2—C3—C4 | 2.0 (9) | C14—C15—C16—C17 | −1.0 (14) |
| C1—C2—C3—C4 | −175.3 (6) | C15—C16—C17—C12 | 1.5 (14) |
| C8—O2—C4—C5 | 15.9 (11) | C13—C12—C17—C16 | −1.4 (12) |
| C8—O2—C4—C3 | −161.0 (7) | C11—C12—C17—C16 | −176.7 (8) |
| O1—C3—C4—C5 | 179.0 (6) | C11—N2—C19—C20 | −122.0 (8) |
| C2—C3—C4—C5 | −0.1 (10) | Zn1—N2—C19—C20 | 59.4 (9) |
| O1—C3—C4—O2 | −4.0 (9) | N2—C19—C20—O6 | 67.2 (11) |
| C2—C3—C4—O2 | 176.9 (6) | N2—C19—C20—O6' | −25 (3) |
| O2—C4—C5—C6 | −177.5 (7) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O3—H3···O1i | 0.82 | 2.07 | 2.799 (7) | 148 |
| O3—H3···O2i | 0.82 | 2.28 | 2.954 (8) | 139 |
| Symmetry codes: (i) x, y−1, z. |
| Zn1—O4 | 1.913 (4) | Zn1—N1 | 1.985 (5) |
| Zn1—O1 | 1.921 (4) | Zn1—N2 | 1.990 (6) |
| O4—Zn1—O1 | 124.7 (2) | O4—Zn1—N2 | 95.3 (2) |
| O4—Zn1—N1 | 110.8 (2) | O1—Zn1—N2 | 108.1 (2) |
| O1—Zn1—N1 | 97.2 (2) | N1—Zn1—N2 | 123.1 (2) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O3—H3···O1i | 0.82 | 2.07 | 2.799 (7) | 148 |
| O3—H3···O2i | 0.82 | 2.28 | 2.954 (8) | 139 |
| Symmetry codes: (i) x, y−1, z. |
The authors thank the Natural Science Foundation of Shandong Province (No. Y2004B02) for a research grant.
Dong, J.-F., Li, L.-Z., Xu, L.-L., Xu, T. & Wang, D.-Q. (2007). Acta Cryst. E63, m1731–?.
Hokelek, T., Kilic, Z., Isiklan, M. & Toy, M. (2000). J. Mol. Struct. 523, 61–69.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (1997a). SHELXL97 and SHELXS97. University of Göttingen, Germany.
Sheldrick, G. M. (1997b). SHELXTL. Version 5.10. Bruker AXS Inc., Madison, Wisconsin, USA.
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Systems Inc., Madison, Wisconsin, USA.
Tatar, L., Canel, E., Atakol, O. & Ulku, D. (1999). Anal. Sci. 15, 103–104.
As part of our ongoing studies of Schiff bases, we reported here the synthesis and crystal structure of the title compound (Fig. 1), a new zinc(II) complex with a bidentate Schiff base ligand derived from the condensation of o-vanillin and ethanolamine.
The coordination around zinc is a distored tetrahedral involving two O and N atoms of the ligands. These bond lengths and angles values are similar to the reported values for related structures (Hokelek et al., 2000, Tatar et al., 1999, Dong et al., 2007).
In the crystal structure, the intermolecular hydrogen bonds of O3—H3···O1i and O3—H3···O2i(symmetry code: (i) x, y − 1, Z) (Fig. 2) and the relatively short intermolecular distances H18a···Cgii of 2.962Å (symmetry code: 0.5 − x, 1/2 + y, Z; Cg is the centroid of the C12—17 ring) indicating the prescence of weak C—H···π interaction, stabilize the crystal packing along with van der Waals forces.