Acta Cryst. (2009). E65, m1112 [ doi:10.1107/S1600536809032413 ]
In the title compound, [Fe(C14H12NOSe2)2], the FeII ion (site symmetry 
) 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.
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.
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).
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).
![[Figure 1]](./hb5048fig1thm.gif)
| 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). |
| [Fe(C14H12NOSe2)2] | F(000) = 768 |
| Mr = 792.18 | Dx = 2.009 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
| a = 10.6065 (5) Å | θ = 9–12° |
| b = 6.1055 (5) Å | µ = 6.16 mm−1 |
| c = 20.7125 (15) Å | T = 296 K |
| β = 102.435 (5)° | Block, green |
| V = 1309.83 (16) Å3 | 0.32 × 0.26 × 0.24 mm |
| Z = 2 |
| Enraf–Nonius CAD-4 diffractometer | 2133 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.044 |
| graphite | θmax = 28.6°, θmin = 2.0° |
| ω/2θ scans | h = −13→12 |
| Absorption correction: ψ scan (North et al., 1968) | k = −8→8 |
| Tmin = 0.243, Tmax = 0.319 | l = −27→24 |
| 8208 measured reflections | 3 standard reflections every 200 reflections |
| 3231 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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.105 | H 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 parameters | Δρmax = 0.68 e Å−3 |
| 2 restraints | Δρmin = −0.61 e Å−3 |
| [Fe(C14H12NOSe2)2] | V = 1309.83 (16) Å3 |
| Mr = 792.18 | Z = 2 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 10.6065 (5) Å | µ = 6.16 mm−1 |
| b = 6.1055 (5) Å | T = 296 K |
| c = 20.7125 (15) Å | 0.32 × 0.26 × 0.24 mm |
| β = 102.435 (5)° |
| 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 = 0.319 | θmax = 28.6° |
| 8208 measured reflections | 3 standard reflections every 200 reflections |
| 3231 independent reflections | intensity decay: 1% |
| R[F2 > 2σ(F2)] = 0.040 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.105 | Δρmax = 0.68 e Å−3 |
| S = 1.05 | Δρmin = −0.61 e Å−3 |
| 3231 reflections | Absolute structure: ? |
| 175 parameters | Flack parameter: ? |
| 2 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 | ||
| Fe1 | 0.5000 | 0.5000 | 0.0000 | 0.02627 (19) | |
| Se1 | 0.39624 (5) | 1.46692 (8) | 0.19627 (3) | 0.06046 (19) | |
| Se2 | 0.11313 (4) | 0.76022 (9) | 0.06333 (3) | 0.05734 (19) | |
| N1 | 0.6354 (3) | 0.6850 (5) | 0.05035 (16) | 0.0338 (7) | |
| O1 | 0.3733 (2) | 0.6579 (5) | 0.02791 (13) | 0.0383 (7) | |
| C3 | 0.6153 (4) | 0.8701 (7) | 0.0771 (2) | 0.0370 (9) | |
| H3 | 0.6877 | 0.9562 | 0.0930 | 0.044* | |
| C4 | 0.4943 (3) | 0.9565 (6) | 0.08496 (19) | 0.0333 (9) | |
| C5 | 0.8814 (4) | 0.1903 (9) | 0.2276 (2) | 0.0519 (12) | |
| H5 | 0.9044 | 0.0960 | 0.2635 | 0.062* | |
| C6 | 0.3792 (3) | 0.8364 (6) | 0.06265 (18) | 0.0322 (9) | |
| C7 | 0.8111 (3) | 0.4726 (6) | 0.12025 (19) | 0.0339 (9) | |
| C8 | 0.8905 (4) | 0.2934 (7) | 0.1180 (2) | 0.0433 (10) | |
| H8 | 0.9206 | 0.2664 | 0.0798 | 0.052* | |
| C9 | 0.3884 (4) | 1.2227 (6) | 0.1388 (2) | 0.0393 (9) | |
| C10 | 0.2727 (4) | 1.1107 (7) | 0.11830 (19) | 0.0403 (10) | |
| H10 | 0.1978 | 1.1635 | 0.1293 | 0.048* | |
| C12 | 0.7746 (3) | 0.6234 (7) | 0.0611 (2) | 0.0359 (9) | |
| H12A | 0.8275 | 0.7544 | 0.0684 | 0.043* | |
| H12B | 0.7905 | 0.5504 | 0.0220 | 0.043* | |
| C13 | 0.2689 (4) | 0.9232 (7) | 0.08202 (19) | 0.0370 (9) | |
| C14 | 0.4963 (4) | 1.1457 (6) | 0.1226 (2) | 0.0398 (10) | |
| H14 | 0.5737 | 1.2204 | 0.1368 | 0.048* | |
| C15 | 0.7687 (4) | 0.5074 (7) | 0.1783 (2) | 0.0425 (10) | |
| H15 | 0.7167 | 0.6274 | 0.1820 | 0.051* | |
| C16 | 0.8040 (4) | 0.3632 (8) | 0.2308 (2) | 0.0504 (12) | |
| H16 | 0.7734 | 0.3864 | 0.2691 | 0.061* | |
| C17 | 0.9257 (4) | 0.1547 (8) | 0.1713 (2) | 0.0498 (11) | |
| H17 | 0.9798 | 0.0364 | 0.1689 | 0.060* | |
| H1 | 0.318 (3) | 1.461 (7) | 0.2300 (18) | 0.060* | |
| H2 | 0.064 (4) | 0.795 (7) | 0.1091 (14) | 0.060* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Fe1 | 0.0184 (3) | 0.0306 (4) | 0.0295 (4) | −0.0017 (3) | 0.0046 (3) | −0.0018 (3) |
| Se1 | 0.0802 (4) | 0.0432 (3) | 0.0599 (4) | 0.0061 (2) | 0.0195 (3) | −0.0142 (2) |
| Se2 | 0.0286 (2) | 0.0838 (4) | 0.0631 (4) | −0.0073 (2) | 0.0177 (2) | −0.0260 (3) |
| N1 | 0.0228 (15) | 0.0406 (19) | 0.0364 (19) | 0.0003 (13) | 0.0028 (13) | 0.0025 (15) |
| O1 | 0.0262 (13) | 0.0458 (17) | 0.0436 (17) | −0.0017 (11) | 0.0092 (12) | −0.0112 (14) |
| C3 | 0.0283 (19) | 0.035 (2) | 0.047 (3) | −0.0040 (16) | 0.0069 (18) | 0.004 (2) |
| C4 | 0.0310 (19) | 0.032 (2) | 0.037 (2) | −0.0006 (15) | 0.0079 (17) | 0.0007 (18) |
| C5 | 0.047 (3) | 0.066 (3) | 0.039 (3) | 0.003 (2) | 0.000 (2) | 0.006 (2) |
| C6 | 0.0314 (19) | 0.035 (2) | 0.030 (2) | 0.0012 (16) | 0.0070 (16) | 0.0023 (18) |
| C7 | 0.0201 (16) | 0.044 (2) | 0.035 (2) | −0.0050 (16) | −0.0009 (15) | −0.0045 (18) |
| C8 | 0.037 (2) | 0.055 (3) | 0.038 (2) | 0.0061 (19) | 0.0076 (18) | −0.005 (2) |
| C9 | 0.051 (2) | 0.034 (2) | 0.035 (2) | 0.0071 (18) | 0.0113 (19) | 0.0010 (18) |
| C10 | 0.040 (2) | 0.048 (3) | 0.035 (2) | 0.0138 (19) | 0.0132 (19) | 0.006 (2) |
| C12 | 0.0211 (17) | 0.041 (2) | 0.046 (2) | −0.0033 (15) | 0.0070 (17) | −0.0012 (19) |
| C13 | 0.033 (2) | 0.046 (3) | 0.034 (2) | 0.0039 (17) | 0.0106 (17) | 0.0013 (19) |
| C14 | 0.042 (2) | 0.034 (2) | 0.043 (2) | −0.0020 (18) | 0.0059 (19) | 0.003 (2) |
| C15 | 0.040 (2) | 0.046 (3) | 0.041 (3) | 0.0009 (19) | 0.0073 (19) | −0.011 (2) |
| C16 | 0.048 (3) | 0.072 (3) | 0.030 (2) | −0.009 (2) | 0.007 (2) | −0.005 (2) |
| C17 | 0.046 (2) | 0.054 (3) | 0.046 (3) | 0.010 (2) | 0.003 (2) | 0.003 (2) |
| Fe1—O1 | 1.845 (2) | C6—C13 | 1.419 (5) |
| Fe1—O1i | 1.845 (2) | C7—C8 | 1.387 (5) |
| Fe1—N1i | 1.945 (3) | C7—C15 | 1.388 (5) |
| Fe1—N1 | 1.945 (3) | C7—C12 | 1.516 (5) |
| Se1—C9 | 1.898 (4) | C8—C17 | 1.378 (6) |
| Se1—H1 | 1.191 (10) | C8—H8 | 0.9300 |
| Se2—C13 | 1.896 (4) | C9—C14 | 1.345 (5) |
| Se2—H2 | 1.196 (10) | C9—C10 | 1.390 (6) |
| N1—C3 | 1.296 (5) | C10—C13 | 1.365 (6) |
| N1—C12 | 1.493 (4) | C10—H10 | 0.9300 |
| O1—C6 | 1.300 (4) | C12—H12A | 0.9700 |
| C3—C4 | 1.429 (5) | C12—H12B | 0.9700 |
| C3—H3 | 0.9300 | C14—H14 | 0.9300 |
| C4—C14 | 1.391 (5) | C15—C16 | 1.387 (6) |
| C4—C6 | 1.414 (5) | C15—H15 | 0.9300 |
| C5—C16 | 1.348 (6) | C16—H16 | 0.9300 |
| C5—C17 | 1.366 (6) | C17—H17 | 0.9300 |
| C5—H5 | 0.9300 | ||
| O1—Fe1—O1i | 180.0 | C7—C8—H8 | 119.3 |
| O1—Fe1—N1i | 88.15 (12) | C14—C9—C10 | 119.6 (4) |
| O1i—Fe1—N1i | 91.85 (12) | C14—C9—Se1 | 120.5 (3) |
| O1—Fe1—N1 | 91.85 (12) | C10—C9—Se1 | 119.7 (3) |
| O1i—Fe1—N1 | 88.15 (12) | C13—C10—C9 | 120.1 (4) |
| N1i—Fe1—N1 | 180.0 | C13—C10—H10 | 120.0 |
| C9—Se1—H1 | 114 (2) | C9—C10—H10 | 120.0 |
| C13—Se2—H2 | 105 (2) | N1—C12—C7 | 110.2 (3) |
| C3—N1—C12 | 113.9 (3) | N1—C12—H12A | 109.6 |
| C3—N1—Fe1 | 124.4 (3) | C7—C12—H12A | 109.6 |
| C12—N1—Fe1 | 121.7 (3) | N1—C12—H12B | 109.6 |
| C6—O1—Fe1 | 131.3 (2) | C7—C12—H12B | 109.6 |
| N1—C3—C4 | 127.2 (4) | H12A—C12—H12B | 108.1 |
| N1—C3—H3 | 116.4 | C10—C13—C6 | 122.7 (4) |
| C4—C3—H3 | 116.4 | C10—C13—Se2 | 118.3 (3) |
| C14—C4—C6 | 121.4 (3) | C6—C13—Se2 | 118.8 (3) |
| C14—C4—C3 | 117.7 (3) | C9—C14—C4 | 121.3 (4) |
| C6—C4—C3 | 120.4 (3) | C9—C14—H14 | 119.4 |
| C16—C5—C17 | 119.4 (4) | C4—C14—H14 | 119.4 |
| C16—C5—H5 | 120.3 | C16—C15—C7 | 119.9 (4) |
| C17—C5—H5 | 120.3 | C16—C15—H15 | 120.0 |
| O1—C6—C4 | 123.4 (3) | C7—C15—H15 | 120.0 |
| O1—C6—C13 | 121.7 (3) | C5—C16—C15 | 121.6 (4) |
| C4—C6—C13 | 114.9 (4) | C5—C16—H16 | 119.2 |
| C8—C7—C15 | 117.5 (4) | C15—C16—H16 | 119.2 |
| C8—C7—C12 | 120.2 (3) | C5—C17—C8 | 120.2 (4) |
| C15—C7—C12 | 122.2 (3) | C5—C17—H17 | 119.9 |
| C17—C8—C7 | 121.3 (4) | C8—C17—H17 | 119.9 |
| C17—C8—H8 | 119.3 |
| Symmetry codes: (i) −x+1, −y+1, −z. |
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.
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.
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.