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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): m1076.
Published online 2009 August 15. doi:  10.1107/S1600536809031596
PMCID: PMC2969920

Bis(2-cyclo­butyl­imino­methyl-4,6-dihydro­seleno­phenolato)zinc(II)

Abstract

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.

Related literature

For background to Schiff bases, see: Shi et al. (2008 [triangle]); Xu et al. (2009 [triangle]). For reference structural data, see: Allen et al. (1987 [triangle]).

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Object name is e-65-m1076-scheme1.jpg

Experimental

Crystal data

  • [Zn(C11H12NOSe2)2]
  • M r = 729.64
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1076-efi1.jpg
  • a = 8.0876 (6) Å
  • b = 12.2986 (16) Å
  • c = 12.7956 (16) Å
  • α = 93.166 (6)°
  • β = 108.216 (6)°
  • γ = 95.716 (6)°
  • V = 1197.9 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 7.12 mm−1
  • T = 296 K
  • 0.32 × 0.28 × 0.25 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968) T min = 0.209, T max = 0.269 (expected range = 0.131–0.168)
  • 6184 measured reflections
  • 4183 independent reflections
  • 3165 reflections with I > 2σ(I)
  • R int = 0.024
  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.130
  • S = 1.05
  • 4183 reflections
  • 284 parameters
  • H-atom parameters constrained
  • Δρmax = 0.73 e Å−3
  • Δρmin = −1.48 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 [triangle]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809031596/hb5040sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809031596/hb5040Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The project was supported by the Scientific Research Foundation for Returned Overseas Chinese Scholars, State Education Ministry, Educational Commission of Hubei Province (D20091703) and the Natural Science Foundation of Hubei Province (2008CDB038).

supplementary crystallographic information

Comment

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.

Experimental

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.

Refinement

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).

Figures

Fig. 1.
The molecular structure of (I) showing 30% probability displacement ellipsoids.

Crystal data

[Zn(C11H12NOSe2)2]Z = 2
Mr = 729.64F(000) = 704
Triclinic, P1Dx = 2.023 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.0876 (6) ÅCell parameters from 25 reflections
b = 12.2986 (16) Åθ = 9–12°
c = 12.7956 (16) ŵ = 7.12 mm1
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

Data collection

Enraf–Nonius CAD-4 diffractometer3165 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
graphiteθmax = 25.0°, θmin = 1.7°
ω/2θ scansh = −9→9
Absorption correction: ψ scan (North et al., 1968)k = −11→14
Tmin = 0.209, Tmax = 0.269l = −15→14
6184 measured reflections3 standard reflections every 200 reflections
4183 independent reflections intensity decay: 1%

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0591P)2 + 4.4413P] where P = (Fo2 + 2Fc2)/3
4183 reflections(Δ/σ)max < 0.001
284 parametersΔρmax = 0.73 e Å3
0 restraintsΔρmin = −1.48 e Å3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/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)
H5−0.24480.67030.02850.033*
C6−0.0144 (8)0.3665 (5)0.1286 (5)0.0285 (14)
C80.2692 (9)0.8003 (5)0.6800 (5)0.0334 (15)
H80.19390.78460.72060.040*
C90.0370 (9)0.7100 (5)0.5214 (5)0.0333 (15)
H9−0.02880.70340.56920.040*
C10−0.2221 (9)0.6202 (6)0.3895 (6)0.0351 (16)
H10−0.29570.67430.35210.042*
C120.2138 (8)0.7668 (5)0.5674 (5)0.0316 (15)
C130.3264 (8)0.7890 (5)0.5038 (5)0.0301 (15)
C140.5457 (9)0.8801 (6)0.6732 (6)0.0381 (17)
H140.65670.91770.70880.046*
C150.4932 (8)0.8481 (5)0.5614 (6)0.0323 (15)
C160.4309 (9)0.8554 (6)0.7316 (6)0.0394 (17)
C17−0.1131 (9)0.8311 (5)0.1571 (6)0.0381 (17)
H17−0.20850.83650.08880.046*
C18−0.1400 (11)0.8977 (6)0.2528 (8)0.053 (2)
H18A−0.26180.90520.24360.063*
H18B−0.08170.87370.32460.063*
C19−0.0413 (11)0.9963 (6)0.2242 (8)0.059 (2)
H19A0.04101.04040.28790.071*
H19B−0.11581.04150.17470.071*
C20−0.1314 (8)0.3059 (5)0.0389 (5)0.0298 (14)
H20−0.12640.23130.02650.036*
C21−0.2633 (8)0.4682 (5)−0.0173 (5)0.0314 (15)
H21−0.34470.5025−0.06920.038*
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−0.18710.46290.33190.059*
H23B−0.32850.51870.24000.059*
C24−0.4130 (10)0.4865 (7)0.3787 (7)0.048 (2)
H24A−0.52830.50640.34050.058*
H24B−0.42070.41210.39980.058*
C25−0.3008 (10)0.5711 (7)0.4725 (6)0.048 (2)
H25A−0.36760.61960.50080.058*
H25B−0.21750.54010.53200.058*
C260.0420 (13)0.9166 (6)0.1673 (9)0.066 (3)
H26A0.15350.89830.21420.079*
H26B0.05010.93790.09700.079*
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)
O10.0927 (6)0.5283 (4)0.2458 (4)0.0331 (11)
O20.2880 (6)0.7612 (4)0.3987 (4)0.0372 (11)
Se1−0.41129 (11)0.27481 (7)−0.16339 (7)0.0561 (3)
H1−0.51330.2804−0.16760.084*
Se20.16624 (10)0.29622 (6)0.22268 (6)0.0406 (2)
H20.14510.22970.20680.061*
Se30.50639 (12)0.89915 (10)0.88567 (7)0.0660 (3)
H30.42480.92080.90270.099*
Se40.64728 (10)0.88355 (6)0.48096 (7)0.0435 (2)
H40.71250.93970.51050.065*
Zn10.08132 (11)0.67103 (7)0.30778 (7)0.0407 (2)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C30.025 (3)0.026 (3)0.022 (3)−0.005 (3)0.008 (3)−0.002 (3)
C40.024 (3)0.031 (3)0.027 (3)−0.002 (3)0.010 (3)0.001 (3)
C50.028 (3)0.026 (3)0.026 (3)0.002 (3)0.007 (3)0.004 (3)
C60.028 (3)0.032 (4)0.027 (3)0.002 (3)0.012 (3)0.002 (3)
C80.038 (4)0.041 (4)0.023 (3)0.011 (3)0.011 (3)0.000 (3)
C90.036 (4)0.037 (4)0.029 (4)−0.002 (3)0.015 (3)0.001 (3)
C100.028 (4)0.039 (4)0.035 (4)−0.002 (3)0.008 (3)0.001 (3)
C120.029 (3)0.031 (4)0.030 (4)0.003 (3)0.004 (3)−0.002 (3)
C130.029 (3)0.026 (3)0.030 (4)0.002 (3)0.003 (3)−0.004 (3)
C140.028 (4)0.040 (4)0.037 (4)0.008 (3)−0.003 (3)−0.009 (3)
C150.028 (3)0.029 (4)0.037 (4)0.003 (3)0.006 (3)0.000 (3)
C160.033 (4)0.046 (4)0.029 (4)0.006 (3)−0.002 (3)−0.012 (3)
C170.043 (4)0.023 (3)0.039 (4)0.004 (3)0.002 (3)0.002 (3)
C180.050 (5)0.035 (4)0.076 (6)0.009 (4)0.023 (4)0.002 (4)
C190.046 (5)0.035 (4)0.090 (7)0.002 (4)0.018 (5)−0.009 (4)
C200.033 (4)0.022 (3)0.032 (4)−0.005 (3)0.012 (3)−0.003 (3)
C210.026 (3)0.035 (4)0.030 (4)0.002 (3)0.004 (3)−0.002 (3)
C220.026 (3)0.032 (4)0.030 (4)−0.007 (3)0.005 (3)−0.005 (3)
C230.043 (5)0.048 (5)0.055 (5)−0.011 (4)0.021 (4)−0.014 (4)
C240.039 (4)0.047 (5)0.060 (5)−0.009 (3)0.023 (4)0.002 (4)
C250.037 (4)0.066 (5)0.041 (4)−0.010 (4)0.019 (3)0.000 (4)
C260.076 (7)0.038 (5)0.100 (8)0.006 (4)0.052 (6)0.008 (5)
N10.033 (3)0.024 (3)0.028 (3)0.002 (2)0.007 (2)0.004 (2)
N20.031 (3)0.030 (3)0.025 (3)−0.003 (2)0.007 (2)−0.002 (2)
O10.034 (3)0.033 (3)0.026 (2)0.004 (2)0.003 (2)−0.005 (2)
O20.035 (3)0.043 (3)0.030 (3)−0.009 (2)0.011 (2)−0.006 (2)
Se10.0466 (5)0.0481 (5)0.0492 (5)−0.0046 (4)−0.0123 (4)−0.0193 (4)
Se20.0428 (4)0.0318 (4)0.0409 (4)0.0097 (3)0.0028 (3)0.0024 (3)
Se30.0512 (5)0.1048 (8)0.0278 (4)0.0108 (5)−0.0035 (4)−0.0202 (4)
Se40.0340 (4)0.0438 (5)0.0533 (5)−0.0036 (3)0.0181 (3)0.0005 (4)
Zn10.0417 (5)0.0415 (5)0.0346 (5)0.0002 (4)0.0088 (4)−0.0034 (4)

Geometric parameters (Å, °)

C3—O11.290 (7)C17—H170.9800
C3—C61.405 (9)C18—C191.509 (12)
C3—C41.432 (9)C18—H18A0.9700
C4—C211.413 (9)C18—H18B0.9700
C4—C51.429 (9)C19—C261.518 (12)
C5—N11.276 (8)C19—H19A0.9700
C5—H50.9300C19—H19B0.9700
C6—C201.361 (9)C20—C221.386 (9)
C6—Se21.896 (6)C20—H200.9300
C8—C161.356 (10)C21—C221.368 (9)
C8—C121.393 (9)C21—H210.9300
C8—H80.9300C22—Se11.900 (6)
C9—N21.272 (8)C23—C241.545 (10)
C9—C121.452 (9)C23—H23A0.9700
C9—H90.9300C23—H23B0.9700
C10—N21.472 (8)C24—C251.530 (11)
C10—C231.518 (10)C24—H24A0.9700
C10—C251.522 (10)C24—H24B0.9700
C10—H100.9800C25—H25A0.9700
C12—C131.416 (9)C25—H25B0.9700
C13—O21.299 (8)C26—H26A0.9700
C13—C151.420 (9)C26—H26B0.9700
C14—C151.380 (9)Zn1—N12.002 (5)
C14—C161.384 (11)Zn1—N21.987 (5)
C14—H140.9300Zn1—O11.908 (4)
C15—Se41.883 (7)Zn1—O21.911 (4)
C16—Se31.902 (7)Se1—H10.8200
C17—N11.470 (8)Se2—H20.8200
C17—C181.519 (11)Se3—H30.8200
C17—C261.522 (11)Se4—H40.8200
O1—C3—C6120.5 (6)C18—C19—H19B114.1
O1—C3—C4123.8 (6)C26—C19—H19B114.1
C6—C3—C4115.6 (5)H19A—C19—H19B111.3
C21—C4—C5116.3 (6)C6—C20—C22118.6 (6)
C21—C4—C3119.7 (6)C6—C20—H20120.7
C5—C4—C3124.0 (6)C22—C20—H20120.7
N1—C5—C4128.0 (6)C22—C21—C4120.6 (6)
N1—C5—H5116.0C22—C21—H21119.7
C4—C5—H5116.0C4—C21—H21119.7
C20—C6—C3124.4 (6)C21—C22—C20120.9 (6)
C20—C6—Se2118.2 (5)C21—C22—Se1120.6 (5)
C3—C6—Se2117.5 (5)C20—C22—Se1118.3 (5)
C16—C8—C12121.3 (7)C10—C23—C2486.9 (6)
C16—C8—H8119.3C10—C23—H23A114.2
C12—C8—H8119.3C24—C23—H23A114.2
N2—C9—C12126.8 (6)C10—C23—H23B114.2
N2—C9—H9116.6C24—C23—H23B114.2
C12—C9—H9116.6H23A—C23—H23B111.3
N2—C10—C23118.6 (6)C25—C24—C2388.1 (5)
N2—C10—C25121.4 (6)C25—C24—H24A114.0
C23—C10—C2589.4 (6)C23—C24—H24A114.0
N2—C10—H10108.6C25—C24—H24B114.0
C23—C10—H10108.6C23—C24—H24B114.0
C25—C10—H10108.6H24A—C24—H24B111.2
C8—C12—C13120.5 (6)C10—C25—C2487.4 (6)
C8—C12—C9116.2 (6)C10—C25—H25A114.1
C13—C12—C9123.3 (6)C24—C25—H25A114.1
O2—C13—C12125.4 (6)C10—C25—H25B114.1
O2—C13—C15118.6 (6)C24—C25—H25B114.1
C12—C13—C15116.0 (6)H25A—C25—H25B111.3
C15—C14—C16119.1 (6)C19—C26—C1788.0 (6)
C15—C14—H14120.5C19—C26—H26A114.0
C16—C14—H14120.5C17—C26—H26A114.0
C14—C15—C13122.6 (6)C19—C26—H26B114.0
C14—C15—Se4119.3 (5)C17—C26—H26B114.0
C13—C15—Se4118.1 (5)H26A—C26—H26B111.2
C8—C16—C14120.6 (6)C5—N1—C17118.3 (5)
C8—C16—Se3121.0 (6)C5—N1—Zn1120.5 (4)
C14—C16—Se3118.4 (5)C17—N1—Zn1121.0 (4)
N1—C17—C18119.7 (6)C9—N2—C10118.7 (6)
N1—C17—C26117.8 (6)C9—N2—Zn1123.1 (5)
C18—C17—C2687.0 (6)C10—N2—Zn1118.2 (4)
N1—C17—H17110.1C3—O1—Zn1125.6 (4)
C18—C17—H17110.1C13—O2—Zn1125.8 (4)
C26—C17—H17110.1C22—Se1—H1109.5
C19—C18—C1788.5 (7)C6—Se2—H2109.5
C19—C18—H18A113.9C16—Se3—H3109.5
C17—C18—H18A113.9C15—Se4—H4109.5
C19—C18—H18B113.9O1—Zn1—O2121.3 (2)
C17—C18—H18B113.9O1—Zn1—N2113.3 (2)
H18A—C18—H18B111.1O2—Zn1—N294.9 (2)
C18—C19—C2687.5 (6)O1—Zn1—N194.9 (2)
C18—C19—H19A114.1O2—Zn1—N1123.5 (2)
C26—C19—H19A114.1N2—Zn1—N1109.6 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5040).

References

  • 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.
  • Enraf–Nonius (1989). CAD-4 Software Enraf–Nonius, Delft, The Netherlands.
  • Harms, K. & Wocadlo, S. (1995). XCAD4 University of Marburg, Germany.
  • North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Shi, L., Fang, R.-Q., Xue, J.-Y., Xiao, Z.-P., Tan, S.-H. & Zhu, H.-L. (2008). Aust. J. Chem.61, 288–296.
  • Xu, S.-P., Shi, L., Lv, P.-C., Fang, R.-Q. & Zhu, H.-L. (2009). J. Coord. Chem.62, 2048–2057.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography