Acta Cryst. (2009). E65, m624 [ doi:10.1107/S1600536809016353 ]
![[mu]](/logos/entities/mu_rmgif.gif)
-1,1'-(ferrocene-1,1'-diyl)bis(butane-1,3-dionato)]di--methanol-diiron(II)The asymmetric unit of the title compound, [Fe4(C9H8O2)4(CH3OH)2], contains one half-molecule located on a twofold rotational axis. In the molecule, the two FeII ions bridged by two coordinating methanol molecules are separated by 3.1286 (7) Å. Two crystallographically independent methanol molecules are situated on a twofold rotational axis; all attached H atoms are rotationally disordered between two equal orientations.
The title complex was obtained by the treatment of iron(II) chloride tetrahydrate (0.5 mmol, 0.099 g) with 1,1'-bis(acetoacetyl)ferrocene (0.5 mmol, 0.177 g) in methanol. The first two reactants were stirred for 12 h. The resulting precipitates were filtered, washed with methanol several times and dried; The deep red crystals were grown by slow evaporation of methanol. Single crystals were obtained after several weeks. Analysis calculated for C38H38Fe4O10: C, 51.98; H, 4.36; found: C, 50.83; H, 4.02%.
All H atoms were placed in calculated positions (C—H = 0.93-0.97 Å, O—H = 0.82 Å) and treated as riding on their parent atoms, with Uiso(H) = 1.2-1.5Ueq(C, O).
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); 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: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./cv2543fig1thm.gif)
| Fig. 1. The molecular structure of (I) showing the atomic numbering and 66% probability displacement ellipsoids. Unlabelled atoms are related to labelled atoms by the symmetry code (-x, 2 - y, z). H atoms omitted for clarity. |
| [Fe4(C9H8O2)4(CH4O)2] | F000 = 1808 |
| Mr = 880.10 | Dx = 1.602 Mg m−3 |
| Orthorhombic, Aba2 | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: A 2 -2ac | Cell parameters from 13899 reflections |
| a = 14.599 (3) Å | θ = 3.2–27.5º |
| b = 19.290 (4) Å | µ = 1.62 mm−1 |
| c = 12.955 (3) Å | T = 291 K |
| V = 3648.5 (13) Å3 | Block, colourless |
| Z = 4 | 0.25 × 0.22 × 0.20 mm |
| Rigaku R-AXIS RAPID diffractometer | 4079 independent reflections |
| Radiation source: fine-focus sealed tube | 3473 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.042 |
| T = 291 K | θmax = 27.5º |
| ω scans | θmin = 3.1º |
| Absorption correction: Multi-scan (ABSCOR; Higashi, 1995) | h = −18→18 |
| Tmin = 0.685, Tmax = 0.737 | k = −24→24 |
| 16837 measured reflections | l = −16→16 |
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.031 | w = 1/[σ2(Fo2) + (0.0338P)2 + 0.1021P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.069 | (Δ/σ)max = 0.002 |
| S = 1.05 | Δρmax = 0.24 e Å−3 |
| 4079 reflections | Δρmin = −0.28 e Å−3 |
| 242 parameters | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| 13 restraints | Extinction coefficient: 0.00077 (11) |
| Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 1899 Friedel pairs |
| Secondary atom site location: difference Fourier map | Flack parameter: −0.001 (16) |
| [Fe4(C9H8O2)4(CH4O)2] | V = 3648.5 (13) Å3 |
| Mr = 880.10 | Z = 4 |
| Orthorhombic, Aba2 | Mo Kα |
| a = 14.599 (3) Å | µ = 1.62 mm−1 |
| b = 19.290 (4) Å | T = 291 K |
| c = 12.955 (3) Å | 0.25 × 0.22 × 0.20 mm |
| Rigaku R-AXIS RAPID diffractometer | 4079 independent reflections |
| Absorption correction: Multi-scan (ABSCOR; Higashi, 1995) | 3473 reflections with I > 2σ(I) |
| Tmin = 0.685, Tmax = 0.737 | Rint = 0.042 |
| 16837 measured reflections |
| R[F2 > 2σ(F2)] = 0.031 | H-atom parameters constrained |
| wR(F2) = 0.069 | Δρmax = 0.24 e Å−3 |
| S = 1.05 | Δρmin = −0.28 e Å−3 |
| 4079 reflections | Absolute structure: Flack (1983), 1899 Friedel pairs |
| 242 parameters | Flack parameter: −0.001 (16) |
| 13 restraints |
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 | Occ. (<1) | |
| C1 | 0.19291 (19) | 0.81289 (13) | 0.8190 (2) | 0.0354 (7) | |
| C2 | 0.26358 (18) | 0.76630 (12) | 0.7841 (4) | 0.0447 (7) | |
| H2 | 0.2613 | 0.7380 | 0.7213 | 0.054* | |
| C3 | 0.3373 (2) | 0.76887 (17) | 0.8546 (3) | 0.0512 (9) | |
| H3 | 0.3945 | 0.7425 | 0.8498 | 0.061* | |
| C4 | 0.3135 (2) | 0.81604 (17) | 0.9337 (3) | 0.0506 (8) | |
| H4 | 0.3518 | 0.8282 | 0.9931 | 0.061* | |
| C5 | 0.2264 (2) | 0.84401 (15) | 0.9114 (2) | 0.0407 (7) | |
| H5 | 0.1938 | 0.8784 | 0.9533 | 0.049* | |
| C6 | 0.3017 (2) | 0.93295 (15) | 0.6728 (2) | 0.0423 (7) | |
| H6 | 0.2494 | 0.9363 | 0.6257 | 0.051* | |
| C7 | 0.3795 (2) | 0.88989 (17) | 0.6594 (3) | 0.0504 (8) | |
| H7 | 0.3905 | 0.8584 | 0.6013 | 0.060* | |
| C8 | 0.4386 (2) | 0.90046 (18) | 0.7442 (3) | 0.0534 (9) | |
| H8 | 0.4974 | 0.8772 | 0.7553 | 0.064* | |
| C9 | 0.39808 (19) | 0.94907 (15) | 0.8111 (3) | 0.0445 (8) | |
| H9 | 0.4241 | 0.9658 | 0.8763 | 0.053* | |
| C10 | 0.31223 (18) | 0.96990 (14) | 0.7674 (2) | 0.0345 (7) | |
| C11 | 0.10328 (17) | 0.83008 (12) | 0.7745 (2) | 0.0330 (7) | |
| C12 | 0.0715 (2) | 0.79896 (15) | 0.6841 (2) | 0.0374 (7) | |
| H12 | 0.1085 | 0.7663 | 0.6518 | 0.045* | |
| C13 | −0.0128 (2) | 0.81460 (14) | 0.6404 (2) | 0.0360 (6) | |
| C14 | −0.0418 (2) | 0.77915 (17) | 0.5423 (3) | 0.0506 (8) | |
| H14A | −0.1028 | 0.7613 | 0.5503 | 0.076* | |
| H14B | −0.0005 | 0.7417 | 0.5276 | 0.076* | |
| H14C | −0.0406 | 0.8118 | 0.4864 | 0.076* | |
| C15 | 0.24318 (18) | 1.01769 (12) | 0.8099 (2) | 0.0318 (7) | |
| C16 | 0.2553 (2) | 1.04853 (15) | 0.9063 (3) | 0.0444 (7) | |
| H16 | 0.3070 | 1.0368 | 0.9445 | 0.053* | |
| C17 | 0.1943 (2) | 1.09561 (14) | 0.9477 (2) | 0.0387 (7) | |
| C18 | 0.2130 (3) | 1.12866 (18) | 1.0513 (3) | 0.0588 (10) | |
| H18A | 0.2171 | 1.1780 | 1.0432 | 0.088* | |
| H18B | 0.2696 | 1.1112 | 1.0785 | 0.088* | |
| H18C | 0.1640 | 1.1178 | 1.0980 | 0.088* | |
| C19 | 0.0000 | 1.0000 | 0.5883 (5) | 0.087 (2) | |
| H19A | −0.0225 | 1.0437 | 0.5636 | 0.130* | 0.50 |
| H19B | −0.0388 | 0.9634 | 0.5636 | 0.130* | 0.50 |
| H19C | 0.0613 | 0.9929 | 0.5636 | 0.130* | 0.50 |
| C20 | 0.0000 | 1.0000 | 0.9899 (4) | 0.078 (2) | |
| H20A | −0.0137 | 0.9542 | 1.0146 | 0.117* | 0.50 |
| H20B | −0.0455 | 1.0319 | 1.0146 | 0.117* | 0.50 |
| H20C | 0.0592 | 1.0139 | 1.0146 | 0.117* | 0.50 |
| Fe1 | −0.05321 (2) | 0.929603 (15) | 0.78857 (4) | 0.02974 (10) | |
| Fe2 | 0.31370 (2) | 0.865393 (17) | 0.79403 (4) | 0.03331 (10) | |
| O1 | 0.05773 (13) | 0.87374 (10) | 0.82598 (15) | 0.0409 (5) | |
| O2 | −0.06968 (14) | 0.85889 (10) | 0.67618 (17) | 0.0406 (5) | |
| O3 | 0.17416 (13) | 1.02878 (10) | 0.75155 (16) | 0.0367 (5) | |
| O4 | 0.11978 (14) | 1.11480 (9) | 0.90521 (16) | 0.0382 (5) | |
| O5 | 0.0000 | 1.0000 | 0.6928 (2) | 0.0346 (7) | |
| H20 | −0.0100 | 1.0397 | 0.7126 | 0.052* | 0.50 |
| O6 | 0.0000 | 1.0000 | 0.8820 (2) | 0.0319 (7) | |
| H21 | 0.0530 | 1.0026 | 0.8623 | 0.048* | 0.50 |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0409 (16) | 0.0301 (12) | 0.0351 (19) | 0.0054 (11) | 0.0030 (11) | 0.0041 (12) |
| C2 | 0.0463 (15) | 0.0309 (12) | 0.0568 (18) | 0.0085 (10) | 0.004 (2) | −0.0019 (19) |
| C3 | 0.0468 (19) | 0.0421 (17) | 0.065 (2) | 0.0151 (15) | −0.0060 (17) | 0.0099 (17) |
| C4 | 0.055 (2) | 0.059 (2) | 0.0379 (18) | 0.0072 (16) | −0.0096 (15) | 0.0118 (16) |
| C5 | 0.0437 (18) | 0.0459 (17) | 0.0327 (15) | 0.0087 (13) | −0.0019 (13) | 0.0055 (14) |
| C6 | 0.0486 (19) | 0.0465 (17) | 0.0320 (16) | 0.0059 (13) | 0.0039 (14) | 0.0056 (14) |
| C7 | 0.056 (2) | 0.0577 (19) | 0.0376 (17) | 0.0114 (16) | 0.0106 (15) | −0.0005 (16) |
| C8 | 0.0356 (17) | 0.058 (2) | 0.066 (2) | 0.0113 (15) | 0.0113 (16) | 0.0046 (18) |
| C9 | 0.0336 (14) | 0.0454 (15) | 0.055 (3) | 0.0009 (12) | −0.0060 (14) | −0.0036 (16) |
| C10 | 0.0340 (14) | 0.0336 (13) | 0.036 (2) | 0.0000 (10) | −0.0001 (12) | 0.0033 (12) |
| C11 | 0.0377 (14) | 0.0269 (11) | 0.0345 (18) | −0.0003 (10) | 0.0080 (13) | −0.0012 (13) |
| C12 | 0.0381 (16) | 0.0370 (15) | 0.0371 (16) | 0.0054 (12) | 0.0066 (13) | −0.0091 (13) |
| C13 | 0.0421 (17) | 0.0307 (13) | 0.0352 (15) | −0.0099 (12) | 0.0066 (13) | −0.0059 (12) |
| C14 | 0.049 (2) | 0.055 (2) | 0.0480 (19) | −0.0067 (15) | 0.0030 (15) | −0.0194 (17) |
| C15 | 0.0344 (14) | 0.0265 (11) | 0.0347 (19) | −0.0048 (9) | −0.0053 (12) | 0.0027 (12) |
| C16 | 0.0420 (17) | 0.0434 (15) | 0.0479 (19) | 0.0061 (13) | −0.0190 (15) | −0.0071 (16) |
| C17 | 0.0453 (18) | 0.0296 (14) | 0.0412 (17) | −0.0037 (12) | −0.0112 (14) | −0.0044 (13) |
| C18 | 0.066 (2) | 0.061 (2) | 0.0492 (19) | 0.0117 (16) | −0.023 (2) | −0.0177 (18) |
| C19 | 0.146 (7) | 0.085 (4) | 0.030 (3) | −0.044 (4) | 0.000 | 0.000 |
| C20 | 0.103 (5) | 0.102 (5) | 0.028 (3) | −0.047 (4) | 0.000 | 0.000 |
| Fe1 | 0.03050 (18) | 0.02938 (16) | 0.02933 (18) | −0.00004 (12) | 0.0040 (2) | −0.0034 (2) |
| Fe2 | 0.03464 (19) | 0.03372 (17) | 0.03157 (19) | 0.00768 (13) | −0.0017 (3) | −0.0015 (2) |
| O1 | 0.0402 (11) | 0.0450 (11) | 0.0374 (11) | 0.0151 (9) | −0.0024 (8) | −0.0119 (9) |
| O2 | 0.0365 (12) | 0.0411 (11) | 0.0442 (12) | 0.0003 (9) | −0.0024 (10) | −0.0119 (10) |
| O3 | 0.0345 (11) | 0.0389 (10) | 0.0366 (10) | 0.0042 (8) | −0.0050 (8) | −0.0024 (9) |
| O4 | 0.0397 (12) | 0.0296 (10) | 0.0452 (12) | 0.0028 (9) | −0.0111 (10) | −0.0053 (9) |
| O5 | 0.038 (2) | 0.0422 (18) | 0.0235 (15) | −0.0045 (14) | 0.000 | 0.000 |
| O6 | 0.042 (2) | 0.0326 (16) | 0.0215 (14) | −0.0051 (13) | 0.000 | 0.000 |
| C1—C5 | 1.426 (4) | C13—O2 | 1.279 (3) |
| C1—C2 | 1.441 (4) | C13—C14 | 1.503 (4) |
| C1—C11 | 1.468 (4) | C14—H14A | 0.9600 |
| C1—Fe2 | 2.059 (3) | C14—H14B | 0.9600 |
| C2—C3 | 1.412 (5) | C14—H14C | 0.9600 |
| C2—Fe2 | 2.051 (3) | C15—O3 | 1.278 (3) |
| C2—H2 | 0.9800 | C15—C16 | 1.394 (4) |
| C3—C4 | 1.413 (5) | C16—C17 | 1.381 (4) |
| C3—Fe2 | 2.050 (3) | C16—H16 | 0.9300 |
| C3—H3 | 0.9800 | C17—O4 | 1.274 (3) |
| C4—C5 | 1.412 (4) | C17—C18 | 1.511 (4) |
| C4—Fe2 | 2.044 (3) | C18—H18A | 0.9600 |
| C4—H4 | 0.9800 | C18—H18B | 0.9600 |
| C5—Fe2 | 2.027 (3) | C18—H18C | 0.9600 |
| C5—H5 | 0.9800 | C19—O5 | 1.355 (7) |
| C6—C7 | 1.418 (4) | C19—H19A | 0.9600 |
| C6—C10 | 1.426 (4) | C19—H19B | 0.9600 |
| C6—Fe2 | 2.048 (3) | C19—H19C | 0.9600 |
| C6—H6 | 0.9800 | C20—O6 | 1.398 (6) |
| C7—C8 | 1.412 (5) | C20—H20A | 0.9600 |
| C7—Fe2 | 2.047 (3) | C20—H20B | 0.9600 |
| C7—H7 | 0.9800 | C20—H20C | 0.9600 |
| C8—C9 | 1.407 (4) | Fe1—O6 | 1.9783 (17) |
| C8—Fe2 | 2.049 (3) | Fe1—O4i | 1.991 (2) |
| C8—H8 | 0.9800 | Fe1—O5 | 1.9964 (18) |
| C9—C10 | 1.433 (4) | Fe1—O3i | 1.9982 (19) |
| C9—Fe2 | 2.043 (3) | Fe1—O1 | 2.0048 (19) |
| C9—H9 | 0.9800 | Fe1—O2 | 2.010 (2) |
| C10—C15 | 1.473 (4) | O3—Fe1i | 1.9982 (19) |
| C10—Fe2 | 2.045 (3) | O4—Fe1i | 1.991 (2) |
| C11—O1 | 1.263 (3) | O5—Fe1i | 1.9964 (18) |
| C11—C12 | 1.395 (4) | O5—H20 | 0.8211 |
| C12—C13 | 1.389 (4) | O6—Fe1i | 1.9783 (17) |
| C12—H12 | 0.9300 | O6—H21 | 0.8158 |
| C5—C1—C2 | 106.3 (3) | H18B—C18—H18C | 109.5 |
| C5—C1—C11 | 122.7 (2) | O5—C19—H19A | 109.5 |
| C2—C1—C11 | 131.0 (3) | O5—C19—H19B | 109.5 |
| C5—C1—Fe2 | 68.37 (17) | H19A—C19—H19B | 109.5 |
| C2—C1—Fe2 | 69.16 (15) | O5—C19—H19C | 109.5 |
| C11—C1—Fe2 | 126.20 (18) | H19A—C19—H19C | 109.5 |
| C3—C2—C1 | 108.7 (3) | H19B—C19—H19C | 109.5 |
| C3—C2—Fe2 | 69.82 (18) | O6—C20—H20A | 109.5 |
| C1—C2—Fe2 | 69.79 (15) | O6—C20—H20B | 109.5 |
| C3—C2—H2 | 125.6 | H20A—C20—H20B | 109.5 |
| C1—C2—H2 | 125.6 | O6—C20—H20C | 109.5 |
| Fe2—C2—H2 | 125.6 | H20A—C20—H20C | 109.5 |
| C2—C3—C4 | 107.7 (3) | H20B—C20—H20C | 109.5 |
| C2—C3—Fe2 | 69.89 (16) | O6—Fe1—O4i | 91.29 (9) |
| C4—C3—Fe2 | 69.60 (18) | O6—Fe1—O5 | 76.14 (7) |
| C2—C3—H3 | 126.1 | O4i—Fe1—O5 | 162.62 (7) |
| C4—C3—H3 | 126.1 | O6—Fe1—O3i | 102.60 (6) |
| Fe2—C3—H3 | 126.1 | O4i—Fe1—O3i | 85.61 (8) |
| C5—C4—C3 | 108.6 (3) | O5—Fe1—O3i | 85.50 (6) |
| C5—C4—Fe2 | 69.05 (18) | O6—Fe1—O1 | 84.48 (6) |
| C3—C4—Fe2 | 70.0 (2) | O4i—Fe1—O1 | 88.83 (9) |
| C5—C4—H4 | 125.7 | O5—Fe1—O1 | 101.62 (6) |
| C3—C4—H4 | 125.7 | O3i—Fe1—O1 | 171.08 (8) |
| Fe2—C4—H4 | 125.7 | O6—Fe1—O2 | 163.02 (7) |
| C4—C5—C1 | 108.6 (3) | O4i—Fe1—O2 | 101.51 (8) |
| C4—C5—Fe2 | 70.37 (19) | O5—Fe1—O2 | 93.34 (9) |
| C1—C5—Fe2 | 70.80 (17) | O3i—Fe1—O2 | 89.60 (8) |
| C4—C5—H5 | 125.7 | O1—Fe1—O2 | 84.66 (8) |
| C1—C5—H5 | 125.7 | C5—Fe2—C9 | 117.30 (13) |
| Fe2—C5—H5 | 125.7 | C5—Fe2—C4 | 40.58 (12) |
| C7—C6—C10 | 108.2 (3) | C9—Fe2—C4 | 105.82 (14) |
| C7—C6—Fe2 | 69.68 (18) | C5—Fe2—C10 | 108.69 (11) |
| C10—C6—Fe2 | 69.52 (17) | C9—Fe2—C10 | 41.04 (11) |
| C7—C6—H6 | 125.9 | C4—Fe2—C10 | 127.46 (13) |
| C10—C6—H6 | 125.9 | C5—Fe2—C7 | 169.03 (13) |
| Fe2—C6—H6 | 125.9 | C9—Fe2—C7 | 68.09 (14) |
| C8—C7—C6 | 108.0 (3) | C4—Fe2—C7 | 149.56 (14) |
| C8—C7—Fe2 | 69.91 (19) | C10—Fe2—C7 | 68.51 (12) |
| C6—C7—Fe2 | 69.78 (18) | C5—Fe2—C6 | 130.60 (12) |
| C8—C7—H7 | 126.0 | C9—Fe2—C6 | 68.41 (14) |
| C6—C7—H7 | 126.0 | C4—Fe2—C6 | 167.07 (13) |
| Fe2—C7—H7 | 126.0 | C10—Fe2—C6 | 40.77 (12) |
| C9—C8—C7 | 108.6 (3) | C7—Fe2—C6 | 40.54 (12) |
| C9—C8—Fe2 | 69.65 (17) | C5—Fe2—C8 | 149.67 (14) |
| C7—C8—Fe2 | 69.76 (19) | C9—Fe2—C8 | 40.23 (13) |
| C9—C8—H8 | 125.7 | C4—Fe2—C8 | 115.68 (15) |
| C7—C8—H8 | 125.7 | C10—Fe2—C8 | 68.34 (12) |
| Fe2—C8—H8 | 125.7 | C7—Fe2—C8 | 40.33 (14) |
| C8—C9—C10 | 108.1 (3) | C6—Fe2—C8 | 67.97 (14) |
| C8—C9—Fe2 | 70.11 (18) | C5—Fe2—C3 | 68.49 (13) |
| C10—C9—Fe2 | 69.58 (15) | C9—Fe2—C3 | 125.10 (14) |
| C8—C9—H9 | 125.9 | C4—Fe2—C3 | 40.38 (14) |
| C10—C9—H9 | 125.9 | C10—Fe2—C3 | 164.08 (13) |
| Fe2—C9—H9 | 125.9 | C7—Fe2—C3 | 117.22 (14) |
| C6—C10—C9 | 107.1 (3) | C6—Fe2—C3 | 152.39 (14) |
| C6—C10—C15 | 124.1 (3) | C8—Fe2—C3 | 105.73 (14) |
| C9—C10—C15 | 128.8 (3) | C5—Fe2—C2 | 68.45 (15) |
| C6—C10—Fe2 | 69.71 (16) | C9—Fe2—C2 | 163.45 (11) |
| C9—C10—Fe2 | 69.37 (16) | C4—Fe2—C2 | 67.72 (17) |
| C15—C10—Fe2 | 124.13 (18) | C10—Fe2—C2 | 154.74 (12) |
| O1—C11—C12 | 123.7 (2) | C7—Fe2—C2 | 109.24 (16) |
| O1—C11—C1 | 114.4 (2) | C6—Fe2—C2 | 120.98 (16) |
| C12—C11—C1 | 121.9 (2) | C8—Fe2—C2 | 127.27 (13) |
| C13—C12—C11 | 123.0 (2) | C3—Fe2—C2 | 40.29 (14) |
| C13—C12—H12 | 118.5 | C5—Fe2—C1 | 40.83 (11) |
| C11—C12—H12 | 118.5 | C9—Fe2—C1 | 152.63 (12) |
| O2—C13—C12 | 124.9 (3) | C4—Fe2—C1 | 68.34 (12) |
| O2—C13—C14 | 115.3 (3) | C10—Fe2—C1 | 120.15 (10) |
| C12—C13—C14 | 119.7 (3) | C7—Fe2—C1 | 130.52 (13) |
| C13—C14—H14A | 109.5 | C6—Fe2—C1 | 111.11 (12) |
| C13—C14—H14B | 109.5 | C8—Fe2—C1 | 166.90 (13) |
| H14A—C14—H14B | 109.5 | C3—Fe2—C1 | 68.70 (12) |
| C13—C14—H14C | 109.5 | C2—Fe2—C1 | 41.05 (10) |
| H14A—C14—H14C | 109.5 | C11—O1—Fe1 | 131.01 (19) |
| H14B—C14—H14C | 109.5 | C13—O2—Fe1 | 129.69 (19) |
| O3—C15—C16 | 124.0 (3) | C15—O3—Fe1i | 128.48 (19) |
| O3—C15—C10 | 115.0 (2) | C17—O4—Fe1i | 128.29 (18) |
| C16—C15—C10 | 121.0 (3) | C19—O5—Fe1i | 128.41 (7) |
| C17—C16—C15 | 123.1 (3) | C19—O5—Fe1 | 128.41 (7) |
| C17—C16—H16 | 118.4 | Fe1i—O5—Fe1 | 103.19 (13) |
| C15—C16—H16 | 118.4 | C19—O5—H20 | 108.2 |
| O4—C17—C16 | 125.1 (3) | Fe1i—O5—H20 | 40.6 |
| O4—C17—C18 | 114.5 (3) | Fe1—O5—H20 | 111.8 |
| C16—C17—C18 | 120.4 (3) | C20—O6—Fe1 | 127.74 (6) |
| C17—C18—H18A | 109.5 | C20—O6—Fe1i | 127.74 (6) |
| C17—C18—H18B | 109.5 | Fe1—O6—Fe1i | 104.52 (13) |
| H18A—C18—H18B | 109.5 | C20—O6—H21 | 108.2 |
| C17—C18—H18C | 109.5 | Fe1—O6—H21 | 102.9 |
| H18A—C18—H18C | 109.5 | Fe1i—O6—H21 | 52.7 |
| Symmetry codes: (i) −x, −y+2, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C20—H20A···O4i | 0.96 | 2.49 | 3.028 (3) | 116 |
| C20—H20C···O4 | 0.96 | 2.57 | 3.028 (3) | 110 |
| C19—H19B···O2 | 0.96 | 2.53 | 3.121 (3) | 120 |
| C3—H3···O4ii | 0.98 | 2.57 | 3.107 (4) | 114 |
| O6—H21···O4 | 0.82 | 2.44 | 2.8377 (19) | 111 |
| O6—H21···O3 | 0.82 | 2.33 | 3.103 (3) | 158 |
| O5—H20···O1i | 0.82 | 2.33 | 3.101 (3) | 157 |
| O5—H20···O2i | 0.82 | 2.32 | 2.914 (2) | 129 |
| Symmetry codes: (i) −x, −y+2, z; (ii) −x+1/2, y−1/2, z. |
The authors gratefully acknowledge financial support from the National Natural Science Foundation of China (grant Nos. 20572018 and 20672032), Heilongjiang Province (grant Nos. 1055HZ001, ZJG0504 and JC200605) and Heilongjiang University.
Flack, H. D. (1983). Acta Cryst. A39, 876–881.
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Yan, C.-G., Zhu, M.-J., Sun, J., Liu, W.-L. & Shi, Y.-C. (2007). J. Coord. Chem. 60, 1083–1091.
Recently, the cobalt and manganese complexes of the specific beta-diketone were published by Yan et al. (2007). Herewith we present the crystal structure of the title FeII complex with the same ligand, (I),
In (I) (Fig. 1), the tetradentate ferrocene-containing bis-beta-diketones ligand links Fe atoms into a complex through four O atoms of the two beta-diketone from two ligands. The two FeII ions and two 1,1'-bis(acetoacetyl)ferrocenes are bridged by two methanols molecules, dividing this macrocyclic framework into two small cyclic subunits.The four atoms - C19, C20, O5 and O6 - of the two methanol molecules lie on a twofold axis.