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

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Bis(2-benzyl­imino­methyl-4,6-di­hydro­seleno­phenolato)iron(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 14 August 2009; accepted 15 August 2009; online 22 August 2009)

In the title compound, [Fe(C14H12NOSe2)2], the FeII ion (site symmetry [\overline{1}]) is four-coordinated by two N,O-bidentate Schiff base ligands, resulting in a slightly distorted trans-FeN2O2 square-planar coordination for the metal ion.

Related literature

For background, 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
  • [Fe(C14H12NOSe2)2]

  • Mr = 792.18

  • Monoclinic, P 21 /c

  • a = 10.6065 (5) Å

  • b = 6.1055 (5) Å

  • c = 20.7125 (15) Å

  • β = 102.435 (5)°

  • V = 1309.83 (16) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 6.16 mm−1

  • T = 296 K

  • 0.32 × 0.26 × 0.24 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: ψ scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.243, Tmax = 0.319 (expected range = 0.174–0.228)

  • 8208 measured reflections

  • 3231 independent reflections

  • 2133 reflections with I > 2σ(I)

  • Rint = 0.044

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

Refinement
  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.105

  • S = 1.05

  • 3231 reflections

  • 175 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.68 e Å−3

  • Δρmin = −0.61 e Å−3

Table 1
Selected geometric parameters (Å, °)

Fe1—O1 1.845 (2)
Fe1—N1 1.945 (3)
O1—Fe1—N1 91.85 (12)

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 FeII is four-coordinated in a slightly distort square-planar configuration by two N atoms and two O atoms of the Schiff base ligands.

Related literature top

For background, 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), phenylmethanamine (107 mg, 2 mmol) and FeCl2.4H2O (1 mmol, 198 mg) in methanol (10 ml) was stirred for 1 h. After keeping the filtrate in air for 7 d, green blocks of (I) were formed.

Refinement top

All H atoms were positioned geometrically (C—H = 0.93 Å for the aromatic H atoms and C—H = 0.96 Å for the aliphatic H atoms) and were refined as riding, with Uiso(H) = 1.2Ueq(C) and Uiso(H) = 1.2Ueq(N).

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, Atoms with an A suffix to their labels are generated by the symmetry operation (1–x, 1–y, –z).
Bis(2-benzyliminomethyl-4,6-dihydroselenophenolato)iron(II) top
Crystal data top
[Fe(C14H12NOSe2)2]F(000) = 768
Mr = 792.18Dx = 2.009 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 10.6065 (5) Åθ = 9–12°
b = 6.1055 (5) ŵ = 6.16 mm1
c = 20.7125 (15) ÅT = 296 K
β = 102.435 (5)°Block, green
V = 1309.83 (16) Å30.32 × 0.26 × 0.24 mm
Z = 2
Data collection top
Enraf–Nonius CAD-4
diffractometer
2133 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.044
Graphite monochromatorθmax = 28.6°, θmin = 2.0°
ω/2θ scansh = 1312
Absorption correction: ψ scan
(North et al., 1968)
k = 88
Tmin = 0.243, Tmax = 0.319l = 2724
8208 measured reflections3 standard reflections every 200 reflections
3231 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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0464P)2]
where P = (Fo2 + 2Fc2)/3
3231 reflections(Δ/σ)max = 0.015
175 parametersΔρmax = 0.68 e Å3
2 restraintsΔρmin = 0.61 e Å3
Crystal data top
[Fe(C14H12NOSe2)2]V = 1309.83 (16) Å3
Mr = 792.18Z = 2
Monoclinic, P21/cMo Kα radiation
a = 10.6065 (5) ŵ = 6.16 mm1
b = 6.1055 (5) ÅT = 296 K
c = 20.7125 (15) Å0.32 × 0.26 × 0.24 mm
β = 102.435 (5)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
2133 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.044
Tmin = 0.243, Tmax = 0.3193 standard reflections every 200 reflections
8208 measured reflections intensity decay: 1%
3231 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0402 restraints
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.68 e Å3
3231 reflectionsΔρmin = 0.61 e Å3
175 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
Fe10.50000.50000.00000.02627 (19)
Se10.39624 (5)1.46692 (8)0.19627 (3)0.06046 (19)
Se20.11313 (4)0.76022 (9)0.06333 (3)0.05734 (19)
N10.6354 (3)0.6850 (5)0.05035 (16)0.0338 (7)
O10.3733 (2)0.6579 (5)0.02791 (13)0.0383 (7)
C30.6153 (4)0.8701 (7)0.0771 (2)0.0370 (9)
H30.68770.95620.09300.044*
C40.4943 (3)0.9565 (6)0.08496 (19)0.0333 (9)
C50.8814 (4)0.1903 (9)0.2276 (2)0.0519 (12)
H50.90440.09600.26350.062*
C60.3792 (3)0.8364 (6)0.06265 (18)0.0322 (9)
C70.8111 (3)0.4726 (6)0.12025 (19)0.0339 (9)
C80.8905 (4)0.2934 (7)0.1180 (2)0.0433 (10)
H80.92060.26640.07980.052*
C90.3884 (4)1.2227 (6)0.1388 (2)0.0393 (9)
C100.2727 (4)1.1107 (7)0.11830 (19)0.0403 (10)
H100.19781.16350.12930.048*
C120.7746 (3)0.6234 (7)0.0611 (2)0.0359 (9)
H12A0.82750.75440.06840.043*
H12B0.79050.55040.02200.043*
C130.2689 (4)0.9232 (7)0.08202 (19)0.0370 (9)
C140.4963 (4)1.1457 (6)0.1226 (2)0.0398 (10)
H140.57371.22040.13680.048*
C150.7687 (4)0.5074 (7)0.1783 (2)0.0425 (10)
H150.71670.62740.18200.051*
C160.8040 (4)0.3632 (8)0.2308 (2)0.0504 (12)
H160.77340.38640.26910.061*
C170.9257 (4)0.1547 (8)0.1713 (2)0.0498 (11)
H170.97980.03640.16890.060*
H10.318 (3)1.461 (7)0.2300 (18)0.060*
H20.064 (4)0.795 (7)0.1091 (14)0.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0184 (3)0.0306 (4)0.0295 (4)0.0017 (3)0.0046 (3)0.0018 (3)
Se10.0802 (4)0.0432 (3)0.0599 (4)0.0061 (2)0.0195 (3)0.0142 (2)
Se20.0286 (2)0.0838 (4)0.0631 (4)0.0073 (2)0.0177 (2)0.0260 (3)
N10.0228 (15)0.0406 (19)0.0364 (19)0.0003 (13)0.0028 (13)0.0025 (15)
O10.0262 (13)0.0458 (17)0.0436 (17)0.0017 (11)0.0092 (12)0.0112 (14)
C30.0283 (19)0.035 (2)0.047 (3)0.0040 (16)0.0069 (18)0.004 (2)
C40.0310 (19)0.032 (2)0.037 (2)0.0006 (15)0.0079 (17)0.0007 (18)
C50.047 (3)0.066 (3)0.039 (3)0.003 (2)0.000 (2)0.006 (2)
C60.0314 (19)0.035 (2)0.030 (2)0.0012 (16)0.0070 (16)0.0023 (18)
C70.0201 (16)0.044 (2)0.035 (2)0.0050 (16)0.0009 (15)0.0045 (18)
C80.037 (2)0.055 (3)0.038 (2)0.0061 (19)0.0076 (18)0.005 (2)
C90.051 (2)0.034 (2)0.035 (2)0.0071 (18)0.0113 (19)0.0010 (18)
C100.040 (2)0.048 (3)0.035 (2)0.0138 (19)0.0132 (19)0.006 (2)
C120.0211 (17)0.041 (2)0.046 (2)0.0033 (15)0.0070 (17)0.0012 (19)
C130.033 (2)0.046 (3)0.034 (2)0.0039 (17)0.0106 (17)0.0013 (19)
C140.042 (2)0.034 (2)0.043 (2)0.0020 (18)0.0059 (19)0.003 (2)
C150.040 (2)0.046 (3)0.041 (3)0.0009 (19)0.0073 (19)0.011 (2)
C160.048 (3)0.072 (3)0.030 (2)0.009 (2)0.007 (2)0.005 (2)
C170.046 (2)0.054 (3)0.046 (3)0.010 (2)0.003 (2)0.003 (2)
Geometric parameters (Å, º) top
Fe1—O11.845 (2)C6—C131.419 (5)
Fe1—O1i1.845 (2)C7—C81.387 (5)
Fe1—N1i1.945 (3)C7—C151.388 (5)
Fe1—N11.945 (3)C7—C121.516 (5)
Se1—C91.898 (4)C8—C171.378 (6)
Se1—H11.191 (10)C8—H80.9300
Se2—C131.896 (4)C9—C141.345 (5)
Se2—H21.196 (10)C9—C101.390 (6)
N1—C31.296 (5)C10—C131.365 (6)
N1—C121.493 (4)C10—H100.9300
O1—C61.300 (4)C12—H12A0.9700
C3—C41.429 (5)C12—H12B0.9700
C3—H30.9300C14—H140.9300
C4—C141.391 (5)C15—C161.387 (6)
C4—C61.414 (5)C15—H150.9300
C5—C161.348 (6)C16—H160.9300
C5—C171.366 (6)C17—H170.9300
C5—H50.9300
O1—Fe1—O1i180.0C7—C8—H8119.3
O1—Fe1—N1i88.15 (12)C14—C9—C10119.6 (4)
O1i—Fe1—N1i91.85 (12)C14—C9—Se1120.5 (3)
O1—Fe1—N191.85 (12)C10—C9—Se1119.7 (3)
O1i—Fe1—N188.15 (12)C13—C10—C9120.1 (4)
N1i—Fe1—N1180.0C13—C10—H10120.0
C9—Se1—H1114 (2)C9—C10—H10120.0
C13—Se2—H2105 (2)N1—C12—C7110.2 (3)
C3—N1—C12113.9 (3)N1—C12—H12A109.6
C3—N1—Fe1124.4 (3)C7—C12—H12A109.6
C12—N1—Fe1121.7 (3)N1—C12—H12B109.6
C6—O1—Fe1131.3 (2)C7—C12—H12B109.6
N1—C3—C4127.2 (4)H12A—C12—H12B108.1
N1—C3—H3116.4C10—C13—C6122.7 (4)
C4—C3—H3116.4C10—C13—Se2118.3 (3)
C14—C4—C6121.4 (3)C6—C13—Se2118.8 (3)
C14—C4—C3117.7 (3)C9—C14—C4121.3 (4)
C6—C4—C3120.4 (3)C9—C14—H14119.4
C16—C5—C17119.4 (4)C4—C14—H14119.4
C16—C5—H5120.3C16—C15—C7119.9 (4)
C17—C5—H5120.3C16—C15—H15120.0
O1—C6—C4123.4 (3)C7—C15—H15120.0
O1—C6—C13121.7 (3)C5—C16—C15121.6 (4)
C4—C6—C13114.9 (4)C5—C16—H16119.2
C8—C7—C15117.5 (4)C15—C16—H16119.2
C8—C7—C12120.2 (3)C5—C17—C8120.2 (4)
C15—C7—C12122.2 (3)C5—C17—H17119.9
C17—C8—C7121.3 (4)C8—C17—H17119.9
C17—C8—H8119.3
Symmetry code: (i) x+1, y+1, z.

Experimental details

Crystal data
Chemical formula[Fe(C14H12NOSe2)2]
Mr792.18
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)10.6065 (5), 6.1055 (5), 20.7125 (15)
β (°) 102.435 (5)
V3)1309.83 (16)
Z2
Radiation typeMo Kα
µ (mm1)6.16
Crystal size (mm)0.32 × 0.26 × 0.24
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.243, 0.319
No. of measured, independent and
observed [I > 2σ(I)] reflections
8208, 3231, 2133
Rint0.044
(sin θ/λ)max1)0.672
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.105, 1.05
No. of reflections3231
No. of parameters175
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.68, 0.61

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

Selected geometric parameters (Å, º) top
Fe1—O11.845 (2)Fe1—N11.945 (3)
O1—Fe1—N191.85 (12)
 

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

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationEnraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
First citationHarms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.  Google Scholar
First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationShi, L., Fang, R.-Q., Xue, J.-Y., Xiao, Z.-P., Tan, S.-H. & Zhu, H.-L. (2008). Aust. J. Chem. 61, 288–296.  Web of Science CSD CrossRef CAS Google Scholar
First citationXu, S.-P., Shi, L., Lv, P.-C., Fang, R.-Q. & Zhu, H.-L. (2009). J. Coord. Chem. 62, 2048–2057.  Web of Science CSD CrossRef CAS Google Scholar

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