metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

aEngineering Research Center for Clean Production of Textile Dyeing and Printing, Ministry of Education, Wuhan 430073, People's Republic of China
*Correspondence e-mail: qfzeng@wuse.edu.cn

(Received 10 August 2009; accepted 11 August 2009; online 15 August 2009)

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[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 et al. (2009[Xu, S.-P., Shi, L., Lv, P.-C., Fang, R.-Q. & Zhu, H.-L. (2009). J. Coord. Chem. 62, 2048-2057.]). For reference structural data, see: Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data
  • [Zn(C11H12NOSe2)2]

  • Mr = 729.64

  • Triclinic, [P \overline 1]

  • 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) Tmin = 0.209, Tmax = 0.269 (expected range = 0.131–0.168)

  • 6184 measured reflections

  • 4183 independent reflections

  • 3165 reflections with I > 2σ(I)

  • Rint = 0.024

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 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

Table 1
Selected bond lengths (Å)

Zn1—N1 2.002 (5)
Zn1—N2 1.987 (5)
Zn1—O1 1.908 (4)
Zn1—O2 1.911 (4)

Data collection: CAD-4 Software (Enraf–Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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.

Related literature top

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

Experimental top

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 top

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).

Computing details top

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).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsoids.
Bis(2-cyclobutyliminomethyl-4,6-dihydroselenophenolato)zinc(II) top
Crystal data top
[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 top
Enraf–Nonius CAD-4
diffractometer
3165 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
Graphite monochromatorθmax = 25.0°, θmin = 1.7°
ω/2θ scansh = 99
Absorption correction: ψ scan
(North et al., 1968)
k = 1114
Tmin = 0.209, Tmax = 0.269l = 1514
6184 measured reflections3 standard reflections every 200 reflections
4183 independent reflections intensity decay: 1%
Refinement top
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 = 1.05 w = 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
Crystal data top
[Zn(C11H12NOSe2)2]γ = 95.716 (6)°
Mr = 729.64V = 1197.9 (2) Å3
Triclinic, P1Z = 2
a = 8.0876 (6) ÅMo Kα radiation
b = 12.2986 (16) ŵ = 7.12 mm1
c = 12.7956 (16) ÅT = 296 K
α = 93.166 (6)°0.32 × 0.28 × 0.25 mm
β = 108.216 (6)°
Data collection top
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 = 0.2693 standard reflections every 200 reflections
6184 measured reflections intensity decay: 1%
4183 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.130H-atom parameters constrained
S = 1.05Δρmax = 0.73 e Å3
4183 reflectionsΔρmin = 1.48 e Å3
284 parameters
Special details top

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) top
xyzUiso*/Ueq
C30.0178 (8)0.4782 (5)0.1563 (5)0.0251 (13)
C40.1460 (8)0.5305 (5)0.0777 (5)0.0270 (14)
C50.1629 (8)0.6448 (5)0.0877 (5)0.0275 (14)
H50.24480.67030.02850.033*
C60.0144 (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)
H90.02880.70340.56920.040*
C100.2221 (9)0.6202 (6)0.3895 (6)0.0351 (16)
H100.29570.67430.35210.042*
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)
C170.1131 (9)0.8311 (5)0.1571 (6)0.0381 (17)
H170.20850.83650.08880.046*
C180.1400 (11)0.8977 (6)0.2528 (8)0.053 (2)
H18A0.26180.90520.24360.063*
H18B0.08170.87370.32460.063*
C190.0413 (11)0.9963 (6)0.2242 (8)0.059 (2)
H19A0.04101.04040.28790.071*
H19B0.11581.04150.17470.071*
C200.1314 (8)0.3059 (5)0.0389 (5)0.0298 (14)
H200.12640.23130.02650.036*
C210.2633 (8)0.4682 (5)0.0173 (5)0.0314 (15)
H210.34470.50250.06920.038*
C220.2581 (8)0.3579 (5)0.0336 (5)0.0313 (15)
C230.2772 (10)0.5116 (6)0.3183 (7)0.049 (2)
H23A0.18710.46290.33190.059*
H23B0.32850.51870.24000.059*
C240.4130 (10)0.4865 (7)0.3787 (7)0.048 (2)
H24A0.52830.50640.34050.058*
H24B0.42070.41210.39980.058*
C250.3008 (10)0.5711 (7)0.4725 (6)0.048 (2)
H25A0.36760.61960.50080.058*
H25B0.21750.54010.53200.058*
C260.0420 (13)0.9166 (6)0.1673 (9)0.066 (3)
H26A0.15350.89830.21420.079*
H26B0.05010.93790.09700.079*
N10.0797 (7)0.7162 (4)0.1679 (4)0.0288 (12)
N20.0372 (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)
Se10.41129 (11)0.27481 (7)0.16339 (7)0.0561 (3)
H10.51330.28040.16760.084*
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) top
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, º) top
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)

Experimental details

Crystal data
Chemical formula[Zn(C11H12NOSe2)2]
Mr729.64
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)8.0876 (6), 12.2986 (16), 12.7956 (16)
α, β, γ (°)93.166 (6), 108.216 (6), 95.716 (6)
V3)1197.9 (2)
Z2
Radiation typeMo Kα
µ (mm1)7.12
Crystal size (mm)0.32 × 0.28 × 0.25
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.209, 0.269
No. of measured, independent and
observed [I > 2σ(I)] reflections
6184, 4183, 3165
Rint0.024
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.130, 1.05
No. of reflections4183
No. of parameters284
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.73, 1.48

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top
Zn1—N12.002 (5)Zn1—O11.908 (4)
Zn1—N21.987 (5)Zn1—O21.911 (4)
 

Acknowledgements

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).

References

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