Acta Cryst. (2009). E65, m1076 [ doi:10.1107/S1600536809031596 ]
In the title complex, [Zn(C11H12NOSe2)2], the ZnII atom is four-coordinated by two O,N-bidentate Schiff base ligands in a distorted tetrahedral geometry.
A mixture of 3,5-dihydroseleno-2-hydroxybenzaldehyde (564 mg, 2 mmol), cyclobutanamine (142 mg, 2 mmol) and ZnCl2 (1 mmol, 134 mg) in methanol (10 ml) was stirred for 1 h. After keeping the filtrate in air for 8 d, colorless blocks of (I) were formed.
All H atoms were positioned geometrically (C—H = 0.93–0.96 Å, Se—H = 0.82Å) and refined as riding, with Uiso(H) = 1.2Ueq(carrier).
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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: SHELXTL (Sheldrick, 2008).
| [Zn(C11H12NOSe2)2] | Z = 2 |
| Mr = 729.64 | F(000) = 704 |
| Triclinic, P1 | Dx = 2.023 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 8.0876 (6) Å | Cell parameters from 25 reflections |
| b = 12.2986 (16) Å | θ = 9–12° |
| c = 12.7956 (16) Å | µ = 7.12 mm−1 |
| α = 93.166 (6)° | T = 296 K |
| β = 108.216 (6)° | Block, colorless |
| γ = 95.716 (6)° | 0.32 × 0.28 × 0.25 mm |
| V = 1197.9 (2) Å3 |
| Enraf–Nonius CAD-4 diffractometer | 3165 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.024 |
| graphite | θmax = 25.0°, θmin = 1.7° |
| ω/2θ scans | h = −9→9 |
| Absorption correction: ψ scan (North et al., 1968) | k = −11→14 |
| Tmin = 0.209, Tmax = 0.269 | l = −15→14 |
| 6184 measured reflections | 3 standard reflections every 200 reflections |
| 4183 independent reflections | intensity decay: 1% |
| 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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.130 | H-atom parameters constrained |
| S = 1.05 | w = 1/[σ2(Fo2) + (0.0591P)2 + 4.4413P] where P = (Fo2 + 2Fc2)/3 |
| 4183 reflections | (Δ/σ)max < 0.001 |
| 284 parameters | Δρmax = 0.73 e Å−3 |
| 0 restraints | Δρmin = −1.48 e Å−3 |
| [Zn(C11H12NOSe2)2] | γ = 95.716 (6)° |
| Mr = 729.64 | V = 1197.9 (2) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 8.0876 (6) Å | Mo Kα radiation |
| b = 12.2986 (16) Å | µ = 7.12 mm−1 |
| c = 12.7956 (16) Å | T = 296 K |
| α = 93.166 (6)° | 0.32 × 0.28 × 0.25 mm |
| β = 108.216 (6)° |
| Enraf–Nonius CAD-4 diffractometer | 3165 reflections with I > 2σ(I) |
| Absorption correction: ψ scan (North et al., 1968) | Rint = 0.024 |
| Tmin = 0.209, Tmax = 0.269 | θmax = 25.0° |
| 6184 measured reflections | 3 standard reflections every 200 reflections |
| 4183 independent reflections | intensity decay: 1% |
| R[F2 > 2σ(F2)] = 0.046 | H-atom parameters constrained |
| wR(F2) = 0.130 | Δρmax = 0.73 e Å−3 |
| S = 1.05 | Δρmin = −1.48 e Å−3 |
| 4183 reflections | Absolute structure: ? |
| 284 parameters | Flack parameter: ? |
| 0 restraints | 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 | ||
| C3 | −0.0178 (8) | 0.4782 (5) | 0.1563 (5) | 0.0251 (13) | |
| C4 | −0.1460 (8) | 0.5305 (5) | 0.0777 (5) | 0.0270 (14) | |
| C5 | −0.1629 (8) | 0.6448 (5) | 0.0877 (5) | 0.0275 (14) | |
| H5 | −0.2448 | 0.6703 | 0.0285 | 0.033* | |
| C6 | −0.0144 (8) | 0.3665 (5) | 0.1286 (5) | 0.0285 (14) | |
| C8 | 0.2692 (9) | 0.8003 (5) | 0.6800 (5) | 0.0334 (15) | |
| H8 | 0.1939 | 0.7846 | 0.7206 | 0.040* | |
| C9 | 0.0370 (9) | 0.7100 (5) | 0.5214 (5) | 0.0333 (15) | |
| H9 | −0.0288 | 0.7034 | 0.5692 | 0.040* | |
| C10 | −0.2221 (9) | 0.6202 (6) | 0.3895 (6) | 0.0351 (16) | |
| H10 | −0.2957 | 0.6743 | 0.3521 | 0.042* | |
| C12 | 0.2138 (8) | 0.7668 (5) | 0.5674 (5) | 0.0316 (15) | |
| C13 | 0.3264 (8) | 0.7890 (5) | 0.5038 (5) | 0.0301 (15) | |
| C14 | 0.5457 (9) | 0.8801 (6) | 0.6732 (6) | 0.0381 (17) | |
| H14 | 0.6567 | 0.9177 | 0.7088 | 0.046* | |
| C15 | 0.4932 (8) | 0.8481 (5) | 0.5614 (6) | 0.0323 (15) | |
| C16 | 0.4309 (9) | 0.8554 (6) | 0.7316 (6) | 0.0394 (17) | |
| C17 | −0.1131 (9) | 0.8311 (5) | 0.1571 (6) | 0.0381 (17) | |
| H17 | −0.2085 | 0.8365 | 0.0888 | 0.046* | |
| C18 | −0.1400 (11) | 0.8977 (6) | 0.2528 (8) | 0.053 (2) | |
| H18A | −0.2618 | 0.9052 | 0.2436 | 0.063* | |
| H18B | −0.0817 | 0.8737 | 0.3246 | 0.063* | |
| C19 | −0.0413 (11) | 0.9963 (6) | 0.2242 (8) | 0.059 (2) | |
| H19A | 0.0410 | 1.0404 | 0.2879 | 0.071* | |
| H19B | −0.1158 | 1.0415 | 0.1747 | 0.071* | |
| C20 | −0.1314 (8) | 0.3059 (5) | 0.0389 (5) | 0.0298 (14) | |
| H20 | −0.1264 | 0.2313 | 0.0265 | 0.036* | |
| C21 | −0.2633 (8) | 0.4682 (5) | −0.0173 (5) | 0.0314 (15) | |
| H21 | −0.3447 | 0.5025 | −0.0692 | 0.038* | |
| C22 | −0.2581 (8) | 0.3579 (5) | −0.0336 (5) | 0.0313 (15) | |
| C23 | −0.2772 (10) | 0.5116 (6) | 0.3183 (7) | 0.049 (2) | |
| H23A | −0.1871 | 0.4629 | 0.3319 | 0.059* | |
| H23B | −0.3285 | 0.5187 | 0.2400 | 0.059* | |
| C24 | −0.4130 (10) | 0.4865 (7) | 0.3787 (7) | 0.048 (2) | |
| H24A | −0.5283 | 0.5064 | 0.3405 | 0.058* | |
| H24B | −0.4207 | 0.4121 | 0.3998 | 0.058* | |
| C25 | −0.3008 (10) | 0.5711 (7) | 0.4725 (6) | 0.048 (2) | |
| H25A | −0.3676 | 0.6196 | 0.5008 | 0.058* | |
| H25B | −0.2175 | 0.5401 | 0.5320 | 0.058* | |
| C26 | 0.0420 (13) | 0.9166 (6) | 0.1673 (9) | 0.066 (3) | |
| H26A | 0.1535 | 0.8983 | 0.2142 | 0.079* | |
| H26B | 0.0501 | 0.9379 | 0.0970 | 0.079* | |
| N1 | −0.0797 (7) | 0.7162 (4) | 0.1679 (4) | 0.0288 (12) | |
| N2 | −0.0372 (7) | 0.6683 (4) | 0.4224 (4) | 0.0297 (12) | |
| O1 | 0.0927 (6) | 0.5283 (4) | 0.2458 (4) | 0.0331 (11) | |
| O2 | 0.2880 (6) | 0.7612 (4) | 0.3987 (4) | 0.0372 (11) | |
| Se1 | −0.41129 (11) | 0.27481 (7) | −0.16339 (7) | 0.0561 (3) | |
| H1 | −0.5133 | 0.2804 | −0.1676 | 0.084* | |
| Se2 | 0.16624 (10) | 0.29622 (6) | 0.22268 (6) | 0.0406 (2) | |
| H2 | 0.1451 | 0.2297 | 0.2068 | 0.061* | |
| Se3 | 0.50639 (12) | 0.89915 (10) | 0.88567 (7) | 0.0660 (3) | |
| H3 | 0.4248 | 0.9208 | 0.9027 | 0.099* | |
| Se4 | 0.64728 (10) | 0.88355 (6) | 0.48096 (7) | 0.0435 (2) | |
| H4 | 0.7125 | 0.9397 | 0.5105 | 0.065* | |
| Zn1 | 0.08132 (11) | 0.67103 (7) | 0.30778 (7) | 0.0407 (2) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C3 | 0.025 (3) | 0.026 (3) | 0.022 (3) | −0.005 (3) | 0.008 (3) | −0.002 (3) |
| C4 | 0.024 (3) | 0.031 (3) | 0.027 (3) | −0.002 (3) | 0.010 (3) | 0.001 (3) |
| C5 | 0.028 (3) | 0.026 (3) | 0.026 (3) | 0.002 (3) | 0.007 (3) | 0.004 (3) |
| C6 | 0.028 (3) | 0.032 (4) | 0.027 (3) | 0.002 (3) | 0.012 (3) | 0.002 (3) |
| C8 | 0.038 (4) | 0.041 (4) | 0.023 (3) | 0.011 (3) | 0.011 (3) | 0.000 (3) |
| C9 | 0.036 (4) | 0.037 (4) | 0.029 (4) | −0.002 (3) | 0.015 (3) | 0.001 (3) |
| C10 | 0.028 (4) | 0.039 (4) | 0.035 (4) | −0.002 (3) | 0.008 (3) | 0.001 (3) |
| C12 | 0.029 (3) | 0.031 (4) | 0.030 (4) | 0.003 (3) | 0.004 (3) | −0.002 (3) |
| C13 | 0.029 (3) | 0.026 (3) | 0.030 (4) | 0.002 (3) | 0.003 (3) | −0.004 (3) |
| C14 | 0.028 (4) | 0.040 (4) | 0.037 (4) | 0.008 (3) | −0.003 (3) | −0.009 (3) |
| C15 | 0.028 (3) | 0.029 (4) | 0.037 (4) | 0.003 (3) | 0.006 (3) | 0.000 (3) |
| C16 | 0.033 (4) | 0.046 (4) | 0.029 (4) | 0.006 (3) | −0.002 (3) | −0.012 (3) |
| C17 | 0.043 (4) | 0.023 (3) | 0.039 (4) | 0.004 (3) | 0.002 (3) | 0.002 (3) |
| C18 | 0.050 (5) | 0.035 (4) | 0.076 (6) | 0.009 (4) | 0.023 (4) | 0.002 (4) |
| C19 | 0.046 (5) | 0.035 (4) | 0.090 (7) | 0.002 (4) | 0.018 (5) | −0.009 (4) |
| C20 | 0.033 (4) | 0.022 (3) | 0.032 (4) | −0.005 (3) | 0.012 (3) | −0.003 (3) |
| C21 | 0.026 (3) | 0.035 (4) | 0.030 (4) | 0.002 (3) | 0.004 (3) | −0.002 (3) |
| C22 | 0.026 (3) | 0.032 (4) | 0.030 (4) | −0.007 (3) | 0.005 (3) | −0.005 (3) |
| C23 | 0.043 (5) | 0.048 (5) | 0.055 (5) | −0.011 (4) | 0.021 (4) | −0.014 (4) |
| C24 | 0.039 (4) | 0.047 (5) | 0.060 (5) | −0.009 (3) | 0.023 (4) | 0.002 (4) |
| C25 | 0.037 (4) | 0.066 (5) | 0.041 (4) | −0.010 (4) | 0.019 (3) | 0.000 (4) |
| C26 | 0.076 (7) | 0.038 (5) | 0.100 (8) | 0.006 (4) | 0.052 (6) | 0.008 (5) |
| N1 | 0.033 (3) | 0.024 (3) | 0.028 (3) | 0.002 (2) | 0.007 (2) | 0.004 (2) |
| N2 | 0.031 (3) | 0.030 (3) | 0.025 (3) | −0.003 (2) | 0.007 (2) | −0.002 (2) |
| O1 | 0.034 (3) | 0.033 (3) | 0.026 (2) | 0.004 (2) | 0.003 (2) | −0.005 (2) |
| O2 | 0.035 (3) | 0.043 (3) | 0.030 (3) | −0.009 (2) | 0.011 (2) | −0.006 (2) |
| Se1 | 0.0466 (5) | 0.0481 (5) | 0.0492 (5) | −0.0046 (4) | −0.0123 (4) | −0.0193 (4) |
| Se2 | 0.0428 (4) | 0.0318 (4) | 0.0409 (4) | 0.0097 (3) | 0.0028 (3) | 0.0024 (3) |
| Se3 | 0.0512 (5) | 0.1048 (8) | 0.0278 (4) | 0.0108 (5) | −0.0035 (4) | −0.0202 (4) |
| Se4 | 0.0340 (4) | 0.0438 (5) | 0.0533 (5) | −0.0036 (3) | 0.0181 (3) | 0.0005 (4) |
| Zn1 | 0.0417 (5) | 0.0415 (5) | 0.0346 (5) | 0.0002 (4) | 0.0088 (4) | −0.0034 (4) |
| C3—O1 | 1.290 (7) | C17—H17 | 0.9800 |
| C3—C6 | 1.405 (9) | C18—C19 | 1.509 (12) |
| C3—C4 | 1.432 (9) | C18—H18A | 0.9700 |
| C4—C21 | 1.413 (9) | C18—H18B | 0.9700 |
| C4—C5 | 1.429 (9) | C19—C26 | 1.518 (12) |
| C5—N1 | 1.276 (8) | C19—H19A | 0.9700 |
| C5—H5 | 0.9300 | C19—H19B | 0.9700 |
| C6—C20 | 1.361 (9) | C20—C22 | 1.386 (9) |
| C6—Se2 | 1.896 (6) | C20—H20 | 0.9300 |
| C8—C16 | 1.356 (10) | C21—C22 | 1.368 (9) |
| C8—C12 | 1.393 (9) | C21—H21 | 0.9300 |
| C8—H8 | 0.9300 | C22—Se1 | 1.900 (6) |
| C9—N2 | 1.272 (8) | C23—C24 | 1.545 (10) |
| C9—C12 | 1.452 (9) | C23—H23A | 0.9700 |
| C9—H9 | 0.9300 | C23—H23B | 0.9700 |
| C10—N2 | 1.472 (8) | C24—C25 | 1.530 (11) |
| C10—C23 | 1.518 (10) | C24—H24A | 0.9700 |
| C10—C25 | 1.522 (10) | C24—H24B | 0.9700 |
| C10—H10 | 0.9800 | C25—H25A | 0.9700 |
| C12—C13 | 1.416 (9) | C25—H25B | 0.9700 |
| C13—O2 | 1.299 (8) | C26—H26A | 0.9700 |
| C13—C15 | 1.420 (9) | C26—H26B | 0.9700 |
| C14—C15 | 1.380 (9) | Zn1—N1 | 2.002 (5) |
| C14—C16 | 1.384 (11) | Zn1—N2 | 1.987 (5) |
| C14—H14 | 0.9300 | Zn1—O1 | 1.908 (4) |
| C15—Se4 | 1.883 (7) | Zn1—O2 | 1.911 (4) |
| C16—Se3 | 1.902 (7) | Se1—H1 | 0.8200 |
| C17—N1 | 1.470 (8) | Se2—H2 | 0.8200 |
| C17—C18 | 1.519 (11) | Se3—H3 | 0.8200 |
| C17—C26 | 1.522 (11) | Se4—H4 | 0.8200 |
| O1—C3—C6 | 120.5 (6) | C18—C19—H19B | 114.1 |
| O1—C3—C4 | 123.8 (6) | C26—C19—H19B | 114.1 |
| C6—C3—C4 | 115.6 (5) | H19A—C19—H19B | 111.3 |
| C21—C4—C5 | 116.3 (6) | C6—C20—C22 | 118.6 (6) |
| C21—C4—C3 | 119.7 (6) | C6—C20—H20 | 120.7 |
| C5—C4—C3 | 124.0 (6) | C22—C20—H20 | 120.7 |
| N1—C5—C4 | 128.0 (6) | C22—C21—C4 | 120.6 (6) |
| N1—C5—H5 | 116.0 | C22—C21—H21 | 119.7 |
| C4—C5—H5 | 116.0 | C4—C21—H21 | 119.7 |
| C20—C6—C3 | 124.4 (6) | C21—C22—C20 | 120.9 (6) |
| C20—C6—Se2 | 118.2 (5) | C21—C22—Se1 | 120.6 (5) |
| C3—C6—Se2 | 117.5 (5) | C20—C22—Se1 | 118.3 (5) |
| C16—C8—C12 | 121.3 (7) | C10—C23—C24 | 86.9 (6) |
| C16—C8—H8 | 119.3 | C10—C23—H23A | 114.2 |
| C12—C8—H8 | 119.3 | C24—C23—H23A | 114.2 |
| N2—C9—C12 | 126.8 (6) | C10—C23—H23B | 114.2 |
| N2—C9—H9 | 116.6 | C24—C23—H23B | 114.2 |
| C12—C9—H9 | 116.6 | H23A—C23—H23B | 111.3 |
| N2—C10—C23 | 118.6 (6) | C25—C24—C23 | 88.1 (5) |
| N2—C10—C25 | 121.4 (6) | C25—C24—H24A | 114.0 |
| C23—C10—C25 | 89.4 (6) | C23—C24—H24A | 114.0 |
| N2—C10—H10 | 108.6 | C25—C24—H24B | 114.0 |
| C23—C10—H10 | 108.6 | C23—C24—H24B | 114.0 |
| C25—C10—H10 | 108.6 | H24A—C24—H24B | 111.2 |
| C8—C12—C13 | 120.5 (6) | C10—C25—C24 | 87.4 (6) |
| C8—C12—C9 | 116.2 (6) | C10—C25—H25A | 114.1 |
| C13—C12—C9 | 123.3 (6) | C24—C25—H25A | 114.1 |
| O2—C13—C12 | 125.4 (6) | C10—C25—H25B | 114.1 |
| O2—C13—C15 | 118.6 (6) | C24—C25—H25B | 114.1 |
| C12—C13—C15 | 116.0 (6) | H25A—C25—H25B | 111.3 |
| C15—C14—C16 | 119.1 (6) | C19—C26—C17 | 88.0 (6) |
| C15—C14—H14 | 120.5 | C19—C26—H26A | 114.0 |
| C16—C14—H14 | 120.5 | C17—C26—H26A | 114.0 |
| C14—C15—C13 | 122.6 (6) | C19—C26—H26B | 114.0 |
| C14—C15—Se4 | 119.3 (5) | C17—C26—H26B | 114.0 |
| C13—C15—Se4 | 118.1 (5) | H26A—C26—H26B | 111.2 |
| C8—C16—C14 | 120.6 (6) | C5—N1—C17 | 118.3 (5) |
| C8—C16—Se3 | 121.0 (6) | C5—N1—Zn1 | 120.5 (4) |
| C14—C16—Se3 | 118.4 (5) | C17—N1—Zn1 | 121.0 (4) |
| N1—C17—C18 | 119.7 (6) | C9—N2—C10 | 118.7 (6) |
| N1—C17—C26 | 117.8 (6) | C9—N2—Zn1 | 123.1 (5) |
| C18—C17—C26 | 87.0 (6) | C10—N2—Zn1 | 118.2 (4) |
| N1—C17—H17 | 110.1 | C3—O1—Zn1 | 125.6 (4) |
| C18—C17—H17 | 110.1 | C13—O2—Zn1 | 125.8 (4) |
| C26—C17—H17 | 110.1 | C22—Se1—H1 | 109.5 |
| C19—C18—C17 | 88.5 (7) | C6—Se2—H2 | 109.5 |
| C19—C18—H18A | 113.9 | C16—Se3—H3 | 109.5 |
| C17—C18—H18A | 113.9 | C15—Se4—H4 | 109.5 |
| C19—C18—H18B | 113.9 | O1—Zn1—O2 | 121.3 (2) |
| C17—C18—H18B | 113.9 | O1—Zn1—N2 | 113.3 (2) |
| H18A—C18—H18B | 111.1 | O2—Zn1—N2 | 94.9 (2) |
| C18—C19—C26 | 87.5 (6) | O1—Zn1—N1 | 94.9 (2) |
| C18—C19—H19A | 114.1 | O2—Zn1—N1 | 123.5 (2) |
| C26—C19—H19A | 114.1 | N2—Zn1—N1 | 109.6 (2) |
| Zn1—N1 | 2.002 (5) | Zn1—O1 | 1.908 (4) |
| Zn1—N2 | 1.987 (5) | Zn1—O2 | 1.911 (4) |
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![[Figure 1]](./hb5040fig1thm.gif)
There has been much research interest in Schiff base metal complexes due to their molecular architectures and biological activities (Shi et al., 2008; Xu et al., 2009). In this work, we report here the crystal structure of the title compound, (I). In (I), all bond lengths are within normal ranges (Allen et al., 1987) (Fig. 1). The Zn(II) is four-coordinated in a distorted tetrahedral coordination by two N atoms and two O atoms of the Schiff base ligands.