Acta Cryst. (2008). E64, m844 [ doi:10.1107/S1600536808015559 ]
The Fe atom of the title compound, [Fe(C12H9ClNO2)2], lies on a crystallographic twofold rotation axis. The FeII atom is four-coordinated in a tetrahedral geometry by the O and N atoms of the two Schiff base ligands. The O atom of the furan substituent in the ligand unit is not involved in coordination to the Fe atom.
5-Chlorosalicylaldehyde (62.4 mg, 0.2 mmol), furan-2-ylmethylamine (19.4 mg, 0.2 mmol), and FeCl2 (12.6 mg, 0.1 mmol) were dissolved in methanol (30 ml). The mixture was stirred for 30 min at room temperature. The resulting solution was kept still in air for a few days, yielding brown crystals.
H atoms were placed in idealized positions and constrained to ride on their parent atoms with C–H distances in the range 0.93–0.97 Å, and with Uiso(H) set at 1.2Ueq(C).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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]](./sj2505fig1thm.gif)
| Fig. 1. The structure of (I) showing 30% probability displacement ellipsoids and the atom-numbering scheme. Numbered atoms are related to un-numbered atoms by the symmetry code 1-x, y, 1-z. |
| [Fe(C12H9ClNO2)2] | F000 = 536 |
| Mr = 525.15 | Dx = 1.529 Mg m−3 |
| Monoclinic, C2 | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: C 2y | Cell parameters from 823 reflections |
| a = 22.550 (4) Å | θ = 2.4–26.2º |
| b = 4.6270 (6) Å | µ = 0.93 mm−1 |
| c = 13.822 (3) Å | T = 298 (2) K |
| β = 127.73 (3)º | Block, brown |
| V = 1140.6 (4) Å3 | 0.21 × 0.21 × 0.20 mm |
| Z = 2 |
| Bruker SMART CCD area-detector diffractometer | 1262 independent reflections |
| Radiation source: fine-focus sealed tube | 973 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.035 |
| T = 298(2) K | θmax = 26.0º |
| ω scans | θmin = 1.9º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −21→27 |
| Tmin = 0.829, Tmax = 0.836 | k = −5→0 |
| 1314 measured reflections | l = −17→0 |
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.060 | w = 1/[σ2(Fo2) + (0.1149P)2 + 2.2051P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.203 | (Δ/σ)max = 0.001 |
| S = 1.06 | Δρmax = 0.60 e Å−3 |
| 1262 reflections | Δρmin = −0.40 e Å−3 |
| 151 parameters | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| 1 restraint | Extinction coefficient: 0.011 (3) |
| Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 0 Friedel pairs |
| Secondary atom site location: difference Fourier map | Flack parameter: −0.02 (9) |
| [Fe(C12H9ClNO2)2] | V = 1140.6 (4) Å3 |
| Mr = 525.15 | Z = 2 |
| Monoclinic, C2 | Mo Kα |
| a = 22.550 (4) Å | µ = 0.93 mm−1 |
| b = 4.6270 (6) Å | T = 298 (2) K |
| c = 13.822 (3) Å | 0.21 × 0.21 × 0.20 mm |
| β = 127.73 (3)º |
| Bruker SMART CCD area-detector diffractometer | 1262 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 973 reflections with I > 2σ(I) |
| Tmin = 0.829, Tmax = 0.836 | Rint = 0.035 |
| 1314 measured reflections |
| R[F2 > 2σ(F2)] = 0.060 | H-atom parameters constrained |
| wR(F2) = 0.203 | Δρmax = 0.60 e Å−3 |
| S = 1.06 | Δρmin = −0.40 e Å−3 |
| 1262 reflections | Absolute structure: Flack (1983), 0 Friedel pairs |
| 151 parameters | Flack parameter: −0.02 (9) |
| 1 restraint |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | 0.5044 (3) | 0.5000 | 0.0419 (6) | |
| Cl1 | 0.87863 (17) | 0.7649 (11) | 1.0179 (3) | 0.0929 (13) | |
| N1 | 0.5246 (5) | 0.728 (2) | 0.6435 (8) | 0.055 (2) | |
| O1 | 0.5933 (4) | 0.313 (2) | 0.5865 (7) | 0.067 (2) | |
| O2 | 0.4619 (6) | 0.600 (3) | 0.7844 (9) | 0.102 (4) | |
| C1 | 0.6584 (5) | 0.630 (3) | 0.7611 (9) | 0.053 (2) | |
| C2 | 0.6554 (5) | 0.419 (2) | 0.6848 (9) | 0.053 (3) | |
| C3 | 0.7253 (6) | 0.309 (3) | 0.7192 (11) | 0.069 (3) | |
| H3 | 0.7250 | 0.1686 | 0.6709 | 0.083* | |
| C4 | 0.7929 (6) | 0.406 (3) | 0.8218 (11) | 0.068 (3) | |
| H4 | 0.8377 | 0.3317 | 0.8429 | 0.081* | |
| C5 | 0.7933 (6) | 0.620 (3) | 0.8943 (10) | 0.065 (3) | |
| C6 | 0.7284 (6) | 0.737 (3) | 0.8663 (10) | 0.070 (3) | |
| H6 | 0.7300 | 0.8824 | 0.9145 | 0.084* | |
| C7 | 0.5937 (6) | 0.759 (3) | 0.7390 (10) | 0.066 (3) | |
| H7 | 0.6021 | 0.8786 | 0.8003 | 0.079* | |
| C8 | 0.4677 (6) | 0.890 (3) | 0.6455 (11) | 0.067 (3) | |
| H8A | 0.4926 | 1.0336 | 0.7100 | 0.080* | |
| H8B | 0.4329 | 0.9882 | 0.5681 | 0.080* | |
| C9 | 0.4259 (6) | 0.683 (3) | 0.6671 (10) | 0.061 (3) | |
| C10 | 0.4146 (12) | 0.427 (6) | 0.786 (2) | 0.137 (10) | |
| H10 | 0.4242 | 0.3498 | 0.8560 | 0.164* | |
| C11 | 0.3509 (10) | 0.381 (4) | 0.6710 (18) | 0.105 (6) | |
| H11 | 0.3109 | 0.2606 | 0.6466 | 0.126* | |
| C12 | 0.3594 (7) | 0.555 (4) | 0.5982 (13) | 0.087 (5) | |
| H12 | 0.3238 | 0.5781 | 0.5141 | 0.104* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Fe1 | 0.0384 (9) | 0.0462 (11) | 0.0399 (9) | 0.000 | 0.0233 (7) | 0.000 |
| Cl1 | 0.0661 (17) | 0.122 (3) | 0.0664 (18) | −0.012 (2) | 0.0279 (15) | 0.017 (2) |
| N1 | 0.062 (5) | 0.047 (5) | 0.065 (5) | 0.000 (5) | 0.044 (4) | −0.005 (4) |
| O1 | 0.065 (4) | 0.068 (6) | 0.066 (4) | −0.001 (4) | 0.040 (4) | −0.017 (4) |
| O2 | 0.093 (6) | 0.136 (12) | 0.089 (6) | 0.016 (7) | 0.062 (5) | 0.022 (7) |
| C1 | 0.052 (5) | 0.054 (6) | 0.053 (5) | 0.001 (5) | 0.032 (5) | 0.006 (5) |
| C2 | 0.053 (5) | 0.050 (8) | 0.053 (5) | 0.005 (5) | 0.031 (5) | 0.009 (5) |
| C3 | 0.061 (6) | 0.062 (8) | 0.088 (8) | −0.007 (6) | 0.048 (6) | −0.008 (7) |
| C4 | 0.056 (6) | 0.070 (9) | 0.081 (7) | 0.012 (6) | 0.043 (6) | 0.019 (7) |
| C5 | 0.048 (6) | 0.081 (9) | 0.055 (6) | 0.001 (6) | 0.026 (5) | 0.013 (6) |
| C6 | 0.071 (7) | 0.077 (9) | 0.059 (6) | −0.001 (7) | 0.038 (6) | 0.010 (7) |
| C7 | 0.074 (7) | 0.067 (8) | 0.054 (6) | −0.004 (7) | 0.038 (6) | 0.002 (6) |
| C8 | 0.070 (7) | 0.059 (7) | 0.079 (7) | 0.019 (6) | 0.049 (6) | 0.009 (6) |
| C9 | 0.061 (6) | 0.067 (8) | 0.070 (7) | 0.011 (6) | 0.048 (6) | 0.005 (6) |
| C10 | 0.161 (17) | 0.15 (3) | 0.199 (19) | 0.037 (18) | 0.158 (17) | 0.06 (2) |
| C11 | 0.112 (12) | 0.085 (11) | 0.167 (17) | 0.000 (11) | 0.110 (13) | −0.004 (13) |
| C12 | 0.080 (8) | 0.088 (14) | 0.102 (9) | −0.001 (9) | 0.061 (8) | −0.007 (9) |
| Fe1—O1 | 1.888 (8) | C3—H3 | 0.9300 |
| Fe1—O1i | 1.888 (8) | C4—C5 | 1.402 (17) |
| Fe1—N1 | 1.992 (8) | C4—H4 | 0.9300 |
| Fe1—N1i | 1.992 (8) | C5—C6 | 1.377 (16) |
| Cl1—C5 | 1.746 (12) | C6—H6 | 0.9300 |
| N1—C7 | 1.294 (13) | C7—H7 | 0.9300 |
| N1—C8 | 1.499 (12) | C8—C9 | 1.493 (16) |
| O1—C2 | 1.310 (12) | C8—H8A | 0.9700 |
| O2—C10 | 1.34 (2) | C8—H8B | 0.9700 |
| O2—C9 | 1.352 (14) | C9—C12 | 1.328 (18) |
| C1—C2 | 1.411 (14) | C10—C11 | 1.35 (2) |
| C1—C7 | 1.424 (15) | C10—H10 | 0.9300 |
| C1—C6 | 1.429 (15) | C11—C12 | 1.39 (2) |
| C2—C3 | 1.431 (15) | C11—H11 | 0.9300 |
| C3—C4 | 1.374 (16) | C12—H12 | 0.9300 |
| O1—Fe1—O1i | 124.0 (6) | C4—C5—Cl1 | 119.4 (9) |
| O1—Fe1—N1 | 95.2 (3) | C5—C6—C1 | 118.1 (13) |
| O1i—Fe1—N1 | 113.5 (3) | C5—C6—H6 | 121.0 |
| O1—Fe1—N1i | 113.5 (3) | C1—C6—H6 | 121.0 |
| O1i—Fe1—N1i | 95.2 (3) | N1—C7—C1 | 127.6 (11) |
| N1—Fe1—N1i | 117.3 (5) | N1—C7—H7 | 116.2 |
| C7—N1—C8 | 115.9 (9) | C1—C7—H7 | 116.2 |
| C7—N1—Fe1 | 120.0 (8) | C9—C8—N1 | 109.7 (10) |
| C8—N1—Fe1 | 123.9 (7) | C9—C8—H8A | 109.7 |
| C2—O1—Fe1 | 123.4 (7) | N1—C8—H8A | 109.7 |
| C10—O2—C9 | 106.7 (14) | C9—C8—H8B | 109.7 |
| C2—C1—C7 | 123.7 (10) | N1—C8—H8B | 109.7 |
| C2—C1—C6 | 121.3 (10) | H8A—C8—H8B | 108.2 |
| C7—C1—C6 | 115.0 (11) | C12—C9—O2 | 108.5 (12) |
| O1—C2—C1 | 124.5 (9) | C12—C9—C8 | 135.8 (12) |
| O1—C2—C3 | 118.3 (10) | O2—C9—C8 | 115.7 (11) |
| C1—C2—C3 | 117.3 (9) | O2—C10—C11 | 111.3 (16) |
| C4—C3—C2 | 121.8 (12) | O2—C10—H10 | 124.4 |
| C4—C3—H3 | 119.1 | C11—C10—H10 | 124.4 |
| C2—C3—H3 | 119.1 | C10—C11—C12 | 103.7 (16) |
| C3—C4—C5 | 119.1 (10) | C10—C11—H11 | 128.2 |
| C3—C4—H4 | 120.5 | C12—C11—H11 | 128.2 |
| C5—C4—H4 | 120.5 | C9—C12—C11 | 109.7 (14) |
| C6—C5—C4 | 122.4 (11) | C9—C12—H12 | 125.2 |
| C6—C5—Cl1 | 117.9 (11) | C11—C12—H12 | 125.2 |
| Symmetry codes: (i) −x+1, y, −z+1. |
| Fe1—O1 | 1.888 (8) | Fe1—N1 | 1.992 (8) |
| O1—Fe1—O1i | 124.0 (6) | O1—Fe1—N1i | 113.5 (3) |
| O1—Fe1—N1 | 95.2 (3) | N1—Fe1—N1i | 117.3 (5) |
| Symmetry codes: (i) −x+1, y, −z+1. |
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As part of our ongoing interest in the structure of iron complexes (Zhu et al., 2003), we report herein the crystal structure of the title compound, a new mononuclear iron(II) complex, (I), Fig. 1, derived from the Schiff base ligand 4-chloro-2-[(furan-2-ylmethylimino)methyl]phenol.
Compound (I) possesses crystallographic two-fold symmetry. The FeII atom in (I) is four-coordinate in a tetrahedral geometry, binding to the O and N atoms of two Schiff base ligands. The O atom of the furan substituent in the ligand lies well away from the coordination sphere of the Fe atom. The coordinate bond values (Table 1) are comparable to values observed in other iron(II) complexes (Chen & Wang, 2006; Chen et al., 2007; Ran et al., 2006; Ye et al., 2007).