Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807040640/hg2281sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807040640/hg2281Isup2.hkl |
CCDC reference: 1140966
A mixture of 1,2-bis{[(2-hydroxy-phenyl)-methyl]-imino}benzene (0.341 g,0.001 mol) and ZnSO4 (0.161 g, 0.001 mol) was added to methanol. The mixture was heated for 5 h under reflux with stirring. The resulting solution was then filtered off. Single crystals suitable for X-ray diffraction analysis formed after a week by slow evaporation of the solvent.
All H atoms were located at calculated positions and refined as riding on their parent C atoms with the C—H bond length fixed to 0.93 Å with Uiso(H) = 1.2 times Ueq(C).
In the title complex, each zinc(II) ion is four-coordinated in a square-planar geometry by two imine N and two phenolate O atoms from the Schiff base 1,2-bis{[(2-hydroxy-phenyl)-methyl]-imino}benzene (Fig. 1). The Zn—N and Zn—O bond lengths are Zn1—N1 1.859 (4) Å, Zn1—N2 1.852 (4) Å, Zn1—O1 1.839 (3) Å and Zn1—O2 1.831 (4) Å. Atoms O1, O2, N1 and N2 are approximately coplanar with the central Zn1 ion, the maximum deviation from the least-squares plane through all five atoms being 0.0140 Å for atom O1. No strong hydrogen bonds are found to exist in the crystal.
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL (Siemens, 1996).
Fig. 1. The asymmetric unit of (I), showing 50% probability displacement ellipsoids. | |
Fig. 2. The packing diagram of (I), viewed along the a axis. |
[Zn(C20H14N2O2)] | F(000) = 776.0 |
Mr = 379.72 | Dx = 1.594 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 2762 reflections |
a = 5.5103 (4) Å | θ = 2.5–22.3° |
b = 16.5871 (13) Å | µ = 1.57 mm−1 |
c = 17.3146 (13) Å | T = 293 K |
V = 1582.6 (2) Å3 | Block, colourless |
Z = 4 | 0.16 × 0.04 × 0.02 mm |
Bruker SMART CCD area-detector diffractometer | 1906 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.046 |
Graphite monochromator | θmax = 26.5°, θmin = 2.4° |
φ and ω scans | h = −6→6 |
10667 measured reflections | k = −20→20 |
3235 independent reflections | l = −21→21 |
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)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.118 | w = 1/[σ2(Fo2) + (0.0632P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max < 0.001 |
3235 reflections | Δρmax = 0.29 e Å−3 |
226 parameters | Δρmin = −0.33 e Å−3 |
0 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.05 (2) |
[Zn(C20H14N2O2)] | V = 1582.6 (2) Å3 |
Mr = 379.72 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 5.5103 (4) Å | µ = 1.57 mm−1 |
b = 16.5871 (13) Å | T = 293 K |
c = 17.3146 (13) Å | 0.16 × 0.04 × 0.02 mm |
Bruker SMART CCD area-detector diffractometer | 1906 reflections with I > 2σ(I) |
10667 measured reflections | Rint = 0.046 |
3235 independent reflections |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.118 | Δρmax = 0.29 e Å−3 |
S = 0.97 | Δρmin = −0.33 e Å−3 |
3235 reflections | Absolute structure: Flack (1983) |
226 parameters | Absolute structure parameter: 0.05 (2) |
0 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 | ||
C1 | 1.0111 (11) | 0.0983 (3) | 0.0897 (3) | 0.0547 (13) | |
C2 | 0.9856 (10) | 0.0192 (3) | 0.0609 (3) | 0.0574 (14) | |
H2 | 0.8507 | −0.0111 | 0.0749 | 0.069* | |
C3 | 1.1570 (12) | −0.0140 (3) | 0.0123 (3) | 0.0603 (13) | |
H3 | 1.1355 | −0.0662 | −0.0060 | 0.072* | |
C4 | 1.3618 (12) | 0.0294 (3) | −0.0097 (3) | 0.0619 (14) | |
H4 | 1.4774 | 0.0061 | −0.0418 | 0.074* | |
C5 | 1.3912 (11) | 0.1057 (3) | 0.0160 (3) | 0.0587 (15) | |
H5 | 1.5264 | 0.1349 | 0.0003 | 0.070* | |
C6 | 1.2217 (10) | 0.1421 (3) | 0.0663 (3) | 0.0537 (14) | |
C7 | 1.2639 (9) | 0.2214 (3) | 0.0924 (3) | 0.0518 (12) | |
H7 | 1.4021 | 0.2472 | 0.0739 | 0.062* | |
C8 | 1.1889 (11) | 0.3417 (3) | 0.1633 (3) | 0.0516 (13) | |
C9 | 1.3812 (11) | 0.3882 (3) | 0.1364 (3) | 0.0565 (14) | |
H9 | 1.4856 | 0.3680 | 0.0989 | 0.068* | |
C10 | 1.4155 (11) | 0.4645 (3) | 0.1659 (3) | 0.0599 (15) | |
H10 | 1.5444 | 0.4956 | 0.1482 | 0.072* | |
C11 | 1.2633 (11) | 0.4950 (3) | 0.2206 (3) | 0.0602 (16) | |
H11 | 1.2920 | 0.5464 | 0.2399 | 0.072* | |
C12 | 1.0689 (11) | 0.4519 (3) | 0.2478 (3) | 0.0570 (15) | |
H12 | 0.9626 | 0.4742 | 0.2837 | 0.068* | |
C13 | 1.0345 (10) | 0.3726 (3) | 0.2200 (3) | 0.0524 (13) | |
C14 | 0.7065 (10) | 0.3357 (3) | 0.3027 (3) | 0.0531 (13) | |
H14 | 0.7328 | 0.3841 | 0.3285 | 0.064* | |
C15 | 0.5211 (10) | 0.2870 (3) | 0.3292 (3) | 0.0552 (13) | |
C16 | 0.3782 (11) | 0.3131 (3) | 0.3946 (3) | 0.0609 (15) | |
H16 | 0.4175 | 0.3615 | 0.4187 | 0.073* | |
C17 | 0.1874 (10) | 0.2691 (3) | 0.4223 (3) | 0.0639 (14) | |
H17 | 0.0991 | 0.2869 | 0.4647 | 0.077* | |
C18 | 0.1295 (12) | 0.1991 (3) | 0.3868 (3) | 0.0626 (15) | |
H18 | −0.0010 | 0.1694 | 0.4055 | 0.075* | |
C19 | 0.2578 (10) | 0.1699 (3) | 0.3234 (3) | 0.0594 (15) | |
H19 | 0.2109 | 0.1219 | 0.3000 | 0.071* | |
C20 | 0.4579 (10) | 0.2129 (3) | 0.2946 (3) | 0.0547 (13) | |
Zn1 | 0.84969 (12) | 0.22299 (3) | 0.18870 (3) | 0.0573 (2) | |
N1 | 1.1265 (8) | 0.2622 (2) | 0.1402 (2) | 0.0489 (10) | |
N2 | 0.8498 (9) | 0.3188 (2) | 0.2436 (2) | 0.0498 (10) | |
O1 | 0.8500 (7) | 0.12647 (18) | 0.13644 (18) | 0.0567 (9) | |
O2 | 0.5762 (7) | 0.18339 (18) | 0.2353 (2) | 0.0543 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.062 (4) | 0.052 (3) | 0.050 (3) | 0.000 (3) | 0.001 (3) | −0.003 (2) |
C2 | 0.067 (4) | 0.053 (3) | 0.053 (3) | 0.000 (3) | 0.002 (3) | −0.002 (3) |
C3 | 0.070 (4) | 0.056 (3) | 0.055 (3) | 0.004 (3) | 0.000 (3) | −0.006 (2) |
C4 | 0.068 (4) | 0.061 (3) | 0.057 (3) | 0.006 (3) | 0.002 (3) | −0.006 (2) |
C5 | 0.064 (4) | 0.059 (3) | 0.053 (3) | 0.004 (3) | 0.002 (3) | −0.004 (3) |
C6 | 0.061 (4) | 0.052 (3) | 0.049 (3) | 0.001 (3) | 0.001 (3) | −0.002 (2) |
C7 | 0.061 (3) | 0.049 (3) | 0.046 (3) | 0.000 (3) | −0.001 (2) | 0.002 (3) |
C8 | 0.064 (4) | 0.046 (3) | 0.044 (3) | 0.001 (3) | −0.005 (3) | 0.001 (2) |
C9 | 0.069 (4) | 0.051 (3) | 0.049 (3) | −0.003 (3) | −0.003 (3) | 0.000 (2) |
C10 | 0.071 (4) | 0.053 (3) | 0.055 (3) | −0.006 (3) | −0.001 (3) | −0.001 (2) |
C11 | 0.073 (4) | 0.051 (3) | 0.057 (3) | −0.005 (3) | −0.002 (3) | −0.002 (3) |
C12 | 0.070 (5) | 0.049 (3) | 0.052 (3) | 0.000 (3) | −0.002 (3) | 0.000 (2) |
C13 | 0.064 (4) | 0.046 (3) | 0.047 (3) | 0.003 (3) | −0.004 (3) | 0.003 (2) |
C14 | 0.061 (4) | 0.050 (3) | 0.048 (3) | 0.009 (2) | −0.003 (3) | 0.004 (2) |
C15 | 0.060 (4) | 0.055 (3) | 0.052 (3) | 0.011 (3) | 0.001 (3) | 0.004 (2) |
C16 | 0.065 (4) | 0.064 (3) | 0.055 (3) | 0.011 (3) | 0.003 (3) | 0.002 (2) |
C17 | 0.064 (4) | 0.069 (4) | 0.058 (3) | 0.011 (4) | 0.005 (3) | 0.008 (3) |
C18 | 0.061 (4) | 0.065 (4) | 0.062 (3) | 0.010 (3) | 0.005 (3) | 0.013 (3) |
C19 | 0.059 (4) | 0.057 (3) | 0.062 (4) | 0.012 (3) | 0.002 (3) | 0.010 (3) |
C20 | 0.057 (4) | 0.051 (3) | 0.057 (3) | 0.012 (3) | 0.002 (3) | 0.007 (3) |
Zn1 | 0.0659 (4) | 0.0518 (3) | 0.0543 (3) | 0.0037 (3) | 0.0003 (3) | 0.0012 (3) |
N1 | 0.061 (3) | 0.044 (2) | 0.041 (2) | 0.000 (2) | −0.005 (2) | 0.0025 (18) |
N2 | 0.060 (3) | 0.044 (2) | 0.045 (2) | 0.006 (2) | −0.005 (3) | 0.0060 (18) |
O1 | 0.060 (2) | 0.0532 (19) | 0.057 (2) | −0.004 (2) | 0.004 (2) | −0.0051 (16) |
O2 | 0.057 (3) | 0.0471 (18) | 0.058 (2) | 0.0070 (16) | 0.0021 (19) | 0.0035 (16) |
C1—O1 | 1.289 (6) | C11—H11 | 0.9300 |
C1—C2 | 1.411 (7) | C12—C13 | 1.415 (6) |
C1—C6 | 1.427 (7) | C12—H12 | 0.9300 |
C2—C3 | 1.379 (7) | C13—N2 | 1.414 (7) |
C2—H2 | 0.9300 | C14—N2 | 1.322 (6) |
C3—C4 | 1.392 (7) | C14—C15 | 1.381 (7) |
C3—H3 | 0.9300 | C14—H14 | 0.9300 |
C4—C5 | 1.351 (6) | C15—C20 | 1.410 (7) |
C4—H4 | 0.9300 | C15—C16 | 1.446 (7) |
C5—C6 | 1.412 (7) | C16—C17 | 1.367 (8) |
C5—H5 | 0.9300 | C16—H16 | 0.9300 |
C6—C7 | 1.411 (7) | C17—C18 | 1.350 (7) |
C7—N1 | 1.309 (6) | C17—H17 | 0.9300 |
C7—H7 | 0.9300 | C18—C19 | 1.394 (7) |
C8—C9 | 1.391 (7) | C18—H18 | 0.9300 |
C8—C13 | 1.396 (7) | C19—C20 | 1.404 (7) |
C8—N1 | 1.420 (6) | C19—H19 | 0.9300 |
C9—C10 | 1.377 (6) | C20—O2 | 1.311 (6) |
C9—H9 | 0.9300 | Zn1—O2 | 1.831 (4) |
C10—C11 | 1.363 (7) | Zn1—O1 | 1.839 (3) |
C10—H10 | 0.9300 | Zn1—N2 | 1.852 (4) |
C11—C12 | 1.372 (7) | Zn1—N1 | 1.858 (4) |
O1—C1—C2 | 119.4 (5) | C8—C13—C12 | 120.0 (5) |
O1—C1—C6 | 123.7 (4) | N2—C13—C12 | 125.7 (5) |
C2—C1—C6 | 116.9 (5) | N2—C14—C15 | 125.1 (5) |
C3—C2—C1 | 121.3 (5) | N2—C14—H14 | 117.4 |
C3—C2—H2 | 119.4 | C15—C14—H14 | 117.4 |
C1—C2—H2 | 119.4 | C14—C15—C20 | 123.5 (5) |
C2—C3—C4 | 121.1 (5) | C14—C15—C16 | 119.2 (5) |
C2—C3—H3 | 119.5 | C20—C15—C16 | 117.3 (5) |
C4—C3—H3 | 119.5 | C17—C16—C15 | 122.2 (5) |
C5—C4—C3 | 119.4 (5) | C17—C16—H16 | 118.9 |
C5—C4—H4 | 120.3 | C15—C16—H16 | 118.9 |
C3—C4—H4 | 120.3 | C18—C17—C16 | 118.8 (5) |
C4—C5—C6 | 121.6 (5) | C18—C17—H17 | 120.6 |
C4—C5—H5 | 119.2 | C16—C17—H17 | 120.6 |
C6—C5—H5 | 119.2 | C17—C18—C19 | 122.5 (6) |
C7—C6—C5 | 119.2 (5) | C17—C18—H18 | 118.8 |
C7—C6—C1 | 121.2 (5) | C19—C18—H18 | 118.8 |
C5—C6—C1 | 119.7 (5) | C18—C19—C20 | 120.1 (5) |
N1—C7—C6 | 126.0 (5) | C18—C19—H19 | 120.0 |
N1—C7—H7 | 117.0 | C20—C19—H19 | 120.0 |
C6—C7—H7 | 117.0 | O2—C20—C19 | 118.6 (5) |
C9—C8—C13 | 119.7 (5) | O2—C20—C15 | 122.4 (5) |
C9—C8—N1 | 127.3 (5) | C19—C20—C15 | 119.0 (5) |
C13—C8—N1 | 113.0 (5) | O2—Zn1—O1 | 84.56 (15) |
C10—C9—C8 | 119.3 (5) | O2—Zn1—N2 | 94.70 (18) |
C10—C9—H9 | 120.3 | O1—Zn1—N2 | 178.58 (15) |
C8—C9—H9 | 120.3 | O2—Zn1—N1 | 179.15 (16) |
C11—C10—C9 | 121.0 (5) | O1—Zn1—N1 | 94.66 (16) |
C11—C10—H10 | 119.5 | N2—Zn1—N1 | 86.09 (19) |
C9—C10—H10 | 119.5 | C7—N1—C8 | 121.1 (5) |
C10—C11—C12 | 121.7 (5) | C7—N1—Zn1 | 125.4 (3) |
C10—C11—H11 | 119.1 | C8—N1—Zn1 | 113.3 (3) |
C12—C11—H11 | 119.1 | C14—N2—C13 | 121.4 (4) |
C11—C12—C13 | 118.2 (5) | C14—N2—Zn1 | 125.3 (4) |
C11—C12—H12 | 120.9 | C13—N2—Zn1 | 113.1 (3) |
C13—C12—H12 | 120.9 | C1—O1—Zn1 | 128.7 (3) |
C8—C13—N2 | 114.3 (4) | C20—O2—Zn1 | 128.3 (3) |
Experimental details
Crystal data | |
Chemical formula | [Zn(C20H14N2O2)] |
Mr | 379.72 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 293 |
a, b, c (Å) | 5.5103 (4), 16.5871 (13), 17.3146 (13) |
V (Å3) | 1582.6 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.57 |
Crystal size (mm) | 0.16 × 0.04 × 0.02 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10667, 3235, 1906 |
Rint | 0.046 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.118, 0.97 |
No. of reflections | 3235 |
No. of parameters | 226 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.29, −0.33 |
Absolute structure | Flack (1983) |
Absolute structure parameter | 0.05 (2) |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996).
In the title complex, each zinc(II) ion is four-coordinated in a square-planar geometry by two imine N and two phenolate O atoms from the Schiff base 1,2-bis{[(2-hydroxy-phenyl)-methyl]-imino}benzene (Fig. 1). The Zn—N and Zn—O bond lengths are Zn1—N1 1.859 (4) Å, Zn1—N2 1.852 (4) Å, Zn1—O1 1.839 (3) Å and Zn1—O2 1.831 (4) Å. Atoms O1, O2, N1 and N2 are approximately coplanar with the central Zn1 ion, the maximum deviation from the least-squares plane through all five atoms being 0.0140 Å for atom O1. No strong hydrogen bonds are found to exist in the crystal.