Acta Cryst. (2009). E65, m461 [ doi:10.1107/S1600536809011039 ]
The title compound, [Fe(C5H5)(C13H9F3N)], was prepared by a condensation reaction from ferrocenylcarbaldehyde and 4-(trifluoromethyl)aniline. The cyclopentadienyl (Cp) rings are coplanar [dihedral angle = 1.4 (3)°] and the imine function is situated in the same plane. The aromatic substituent is bent out of the plane of the Cp ring to which the imine group is attached by 44.5 (4)°. The F atoms of the trifluoromethyl substituent are disordered [occupancies 0.52 (2)/0.48 (2)].
500 mg ferrocenylcarbaldehyde (2.34 mmol) were dissolved in 20 ml of anhydrous ethanol together with an equimolar amount of 4-trifluoromethyl-aniline (376 mg) and 10 mg of p-toluenesulfonic acid. The solution was stirred at room temperature for 1 h. After evaporation of 15 ml of the solvent the remaining solution was put into the refrigerator at 277 K resulting in the precipitation of the title compound as crystalline material (yield: 600 mg, 72%). MS (EI) [m/z, %]: 357 (M+, 100), 338 (M+ - F, 11), 292 (M+ - Cp, 3), 236 (M+ - CpFe, 3), 216 (C12H8NF2+, 71), 186 (C10H10Fe+, 11), 167 (C12H9N+, 49, 121 (CpFe+, 19), 56 (Fe+, 13); 1H-NMR (CDCl3, 298 K) [p.p.m.]: 4.12 (s, 5H, Cp), 4.18–4.45 (m, 4H, Cp), 7.14–7.19 (m, 2H, CHar), 7.58–7.61 (m, 2H, CHar), 8.08 (m, 1H, CH=N).
Hydrogen atoms were positioned geometrically at distances of 0.95 Å for aromatic C—H functions and the imine C—H group and were refined riding on their parent atoms with isotropic thermal parameters of 1.2 times the corresponding values of their parent atoms.
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Siemens, 1990); software used to prepare material for publication: XP (Siemens, 1990).
![[Figure 1]](./hg2490fig1thm.gif)
| Fig. 1. Molecular structure of the title compound with displacement ellipsoids at the 40% probability level. |
| [Fe(C5H5)(C13H9F3N)] | Z = 2 |
| Mr = 357.15 | F(000) = 364 |
| Triclinic, P1 | Dx = 1.555 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 5.8446 (7) Å | Cell parameters from 2064 reflections |
| b = 10.383 (1) Å | θ = 3.2–23.3° |
| c = 12.972 (2) Å | µ = 1.02 mm−1 |
| α = 100.467 (8)° | T = 183 K |
| β = 91.670 (5)° | Plate, red |
| γ = 99.152 (8)° | 0.12 × 0.08 × 0.02 mm |
| V = 762.9 (2) Å3 |
| Nonius KappaCCD diffractometer | 1937 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | θmax = 23.3°, θmin = 3.5° |
| graphite | h = 0→6 |
| ω and φ scans | k = −11→11 |
| 2064 measured reflections | l = −14→14 |
| 2064 independent reflections |
| 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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.099 | H-atom parameters constrained |
| S = 0.79 | w = 1/[σ2(Fo2) + (0.0772P)2 + 0.4666P] where P = (Fo2 + 2Fc2)/3 |
| 2064 reflections | (Δ/σ)max = 0.003 |
| 236 parameters | Δρmax = 0.25 e Å−3 |
| 0 restraints | Δρmin = −0.41 e Å−3 |
| [Fe(C5H5)(C13H9F3N)] | γ = 99.152 (8)° |
| Mr = 357.15 | V = 762.9 (2) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 5.8446 (7) Å | Mo Kα radiation |
| b = 10.383 (1) Å | µ = 1.02 mm−1 |
| c = 12.972 (2) Å | T = 183 K |
| α = 100.467 (8)° | 0.12 × 0.08 × 0.02 mm |
| β = 91.670 (5)° |
| Nonius KappaCCD diffractometer | 1937 reflections with I > 2σ(I) |
| 2064 measured reflections | Rint = ? |
| 2064 independent reflections | θmax = 23.3° |
| R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
| wR(F2) = 0.099 | Δρmax = 0.25 e Å−3 |
| S = 0.79 | Δρmin = −0.41 e Å−3 |
| 2064 reflections | Absolute structure: ? |
| 236 parameters | Flack parameter: ? |
| 0 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 | Occ. (<1) | |
| Fe1 | 0.48698 (5) | 0.24098 (3) | 0.23674 (3) | 0.03550 (19) | |
| C1 | 0.3215 (5) | 0.3525 (3) | 0.0515 (2) | 0.0442 (6) | |
| H1 | 0.4421 | 0.3603 | 0.0043 | 0.053* | |
| N1 | 0.1114 (4) | 0.3180 (2) | 0.01264 (18) | 0.0461 (6) | |
| C2 | 0.0736 (5) | 0.2917 (3) | −0.0978 (2) | 0.0420 (6) | |
| C3 | 0.2148 (5) | 0.2243 (3) | −0.1663 (2) | 0.0467 (7) | |
| H3 | 0.3436 | 0.1928 | −0.1391 | 0.056* | |
| C4 | 0.1667 (5) | 0.2035 (3) | −0.2739 (2) | 0.0483 (7) | |
| H4 | 0.2636 | 0.1586 | −0.3202 | 0.058* | |
| C5 | −0.0220 (5) | 0.2480 (3) | −0.3142 (2) | 0.0463 (7) | |
| C6 | −0.1655 (5) | 0.3124 (3) | −0.2467 (2) | 0.0467 (7) | |
| H6 | −0.2961 | 0.3420 | −0.2740 | 0.056* | |
| C7 | −0.1173 (4) | 0.3332 (3) | −0.1395 (2) | 0.0463 (7) | |
| H7 | −0.2167 | 0.3767 | −0.0935 | 0.056* | |
| C8 | −0.0774 (7) | 0.2247 (4) | −0.4301 (3) | 0.0617 (9) | |
| F1 | −0.056 (3) | 0.3334 (12) | −0.4661 (11) | 0.101 (5) | 0.52 (2) |
| F2 | 0.1063 (14) | 0.1998 (13) | −0.4864 (8) | 0.108 (4) | 0.52 (2) |
| F3 | −0.312 (3) | 0.184 (3) | −0.4518 (9) | 0.170 (8) | 0.52 (2) |
| F1X | −0.140 (4) | 0.3235 (14) | −0.4636 (12) | 0.124 (6) | 0.48 (2) |
| F2X | 0.020 (5) | 0.144 (2) | −0.4837 (9) | 0.195 (9) | 0.48 (2) |
| F3X | −0.225 (3) | 0.1227 (9) | −0.4659 (7) | 0.097 (4) | 0.48 (2) |
| C9 | 0.3850 (4) | 0.3802 (3) | 0.1628 (2) | 0.0417 (6) | |
| C10 | 0.2396 (5) | 0.3601 (3) | 0.2476 (2) | 0.0440 (6) | |
| H10 | 0.0763 | 0.3315 | 0.2418 | 0.053* | |
| C11 | 0.3828 (5) | 0.3903 (3) | 0.3413 (2) | 0.0492 (7) | |
| H11 | 0.3318 | 0.3855 | 0.4096 | 0.059* | |
| C12 | 0.6162 (5) | 0.4291 (3) | 0.3163 (2) | 0.0494 (7) | |
| H12 | 0.7474 | 0.4546 | 0.3649 | 0.059* | |
| C13 | 0.6191 (5) | 0.4234 (3) | 0.2070 (2) | 0.0463 (7) | |
| H13 | 0.7524 | 0.4443 | 0.1692 | 0.056* | |
| C14 | 0.4441 (5) | 0.0678 (3) | 0.1292 (2) | 0.0520 (7) | |
| H14 | 0.3790 | 0.0548 | 0.0594 | 0.062* | |
| C15 | 0.6824 (5) | 0.1108 (3) | 0.1618 (2) | 0.0477 (7) | |
| H15 | 0.8049 | 0.1312 | 0.1178 | 0.057* | |
| C16 | 0.7044 (5) | 0.1177 (3) | 0.2719 (2) | 0.0455 (7) | |
| H16 | 0.8444 | 0.1435 | 0.3149 | 0.055* | |
| C17 | 0.4799 (5) | 0.0790 (3) | 0.3063 (2) | 0.0498 (7) | |
| H17 | 0.4436 | 0.0748 | 0.3767 | 0.060* | |
| C18 | 0.3203 (5) | 0.0479 (3) | 0.2188 (3) | 0.0503 (7) | |
| H18 | 0.1579 | 0.0187 | 0.2195 | 0.060* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Fe1 | 0.0315 (3) | 0.0357 (3) | 0.0406 (3) | 0.00535 (17) | 0.00559 (16) | 0.01043 (17) |
| C1 | 0.0399 (15) | 0.0416 (15) | 0.0553 (17) | 0.0084 (12) | 0.0093 (12) | 0.0175 (12) |
| N1 | 0.0393 (13) | 0.0502 (14) | 0.0516 (14) | 0.0081 (10) | 0.0064 (10) | 0.0159 (11) |
| C2 | 0.0398 (14) | 0.0418 (16) | 0.0456 (15) | 0.0028 (12) | 0.0052 (11) | 0.0147 (12) |
| C3 | 0.0395 (14) | 0.0425 (16) | 0.0614 (18) | 0.0096 (12) | 0.0051 (13) | 0.0160 (13) |
| C4 | 0.0481 (16) | 0.0436 (16) | 0.0538 (17) | 0.0066 (13) | 0.0155 (13) | 0.0100 (13) |
| C5 | 0.0520 (16) | 0.0393 (16) | 0.0486 (16) | 0.0025 (13) | 0.0053 (12) | 0.0147 (12) |
| C6 | 0.0414 (15) | 0.0453 (16) | 0.0550 (17) | 0.0041 (12) | −0.0011 (12) | 0.0174 (13) |
| C7 | 0.0376 (14) | 0.0494 (17) | 0.0545 (17) | 0.0081 (12) | 0.0080 (12) | 0.0149 (13) |
| C8 | 0.079 (2) | 0.053 (2) | 0.0518 (18) | −0.002 (2) | 0.0017 (18) | 0.0162 (17) |
| F1 | 0.148 (8) | 0.086 (7) | 0.061 (4) | −0.032 (7) | −0.020 (4) | 0.042 (4) |
| F2 | 0.082 (5) | 0.202 (12) | 0.053 (4) | 0.038 (5) | 0.032 (3) | 0.040 (5) |
| F3 | 0.102 (7) | 0.304 (19) | 0.065 (5) | −0.074 (10) | −0.022 (4) | 0.032 (9) |
| F1X | 0.217 (15) | 0.110 (11) | 0.062 (5) | 0.098 (10) | −0.029 (7) | 0.008 (6) |
| F2X | 0.39 (3) | 0.175 (14) | 0.056 (5) | 0.198 (16) | −0.015 (11) | −0.023 (7) |
| F3X | 0.126 (9) | 0.094 (6) | 0.048 (3) | −0.055 (5) | 0.000 (5) | 0.015 (3) |
| C9 | 0.0396 (14) | 0.0378 (14) | 0.0508 (16) | 0.0084 (11) | 0.0056 (12) | 0.0141 (12) |
| C10 | 0.0394 (14) | 0.0407 (15) | 0.0544 (17) | 0.0117 (12) | 0.0072 (12) | 0.0102 (12) |
| C11 | 0.0588 (18) | 0.0424 (16) | 0.0493 (17) | 0.0145 (13) | 0.0102 (13) | 0.0100 (13) |
| C12 | 0.0495 (16) | 0.0392 (15) | 0.0571 (18) | 0.0056 (12) | −0.0043 (13) | 0.0060 (13) |
| C13 | 0.0400 (14) | 0.0403 (15) | 0.0596 (18) | 0.0019 (12) | 0.0045 (12) | 0.0162 (13) |
| C14 | 0.0546 (17) | 0.0437 (16) | 0.0561 (18) | 0.0146 (13) | −0.0041 (14) | 0.0010 (13) |
| C15 | 0.0458 (16) | 0.0470 (17) | 0.0532 (17) | 0.0145 (13) | 0.0115 (13) | 0.0094 (13) |
| C16 | 0.0424 (15) | 0.0432 (16) | 0.0544 (17) | 0.0123 (12) | 0.0019 (12) | 0.0140 (12) |
| C17 | 0.0567 (18) | 0.0427 (16) | 0.0560 (17) | 0.0136 (13) | 0.0108 (14) | 0.0193 (13) |
| C18 | 0.0386 (15) | 0.0353 (15) | 0.076 (2) | 0.0027 (12) | 0.0068 (14) | 0.0112 (13) |
| Fe1—C9 | 2.027 (3) | C8—F3X | 1.260 (10) |
| Fe1—C10 | 2.038 (3) | C8—F1X | 1.284 (14) |
| Fe1—C13 | 2.037 (3) | C8—F1 | 1.288 (11) |
| Fe1—C15 | 2.038 (3) | C8—F2 | 1.348 (8) |
| Fe1—C16 | 2.039 (3) | C8—F3 | 1.372 (13) |
| Fe1—C14 | 2.041 (3) | F2X—F3X | 1.44 (4) |
| Fe1—C17 | 2.043 (3) | C9—C10 | 1.434 (4) |
| Fe1—C11 | 2.049 (3) | C9—C13 | 1.438 (4) |
| Fe1—C12 | 2.050 (3) | C10—C11 | 1.412 (4) |
| Fe1—C18 | 2.054 (3) | C10—H10 | 0.9500 |
| C1—N1 | 1.284 (3) | C11—C12 | 1.424 (4) |
| C1—C9 | 1.446 (4) | C11—H11 | 0.9500 |
| C1—H1 | 0.9500 | C12—C13 | 1.408 (4) |
| N1—C2 | 1.413 (4) | C12—H12 | 0.9500 |
| C2—C7 | 1.388 (4) | C13—H13 | 0.9500 |
| C2—C3 | 1.400 (4) | C14—C18 | 1.416 (4) |
| C3—C4 | 1.386 (4) | C14—C15 | 1.420 (4) |
| C3—H3 | 0.9500 | C14—H14 | 0.9500 |
| C4—C5 | 1.385 (4) | C15—C16 | 1.418 (4) |
| C4—H4 | 0.9500 | C15—H15 | 0.9500 |
| C5—C6 | 1.387 (4) | C16—C17 | 1.419 (4) |
| C5—C8 | 1.496 (4) | C16—H16 | 0.9500 |
| C6—C7 | 1.381 (4) | C17—C18 | 1.404 (4) |
| C6—H6 | 0.9500 | C17—H17 | 0.9500 |
| C7—H7 | 0.9500 | C18—H18 | 0.9500 |
| C8—F2X | 1.213 (12) | ||
| C9—Fe1—C10 | 41.32 (11) | F1X—C8—F2 | 103.8 (11) |
| C9—Fe1—C13 | 41.45 (11) | F1—C8—F2 | 85.3 (10) |
| C10—Fe1—C13 | 69.23 (11) | F2X—C8—F3 | 107 (2) |
| C9—Fe1—C15 | 119.87 (12) | F3X—C8—F3 | 38.2 (9) |
| C10—Fe1—C15 | 155.72 (12) | F1X—C8—F3 | 77.4 (10) |
| C13—Fe1—C15 | 106.89 (12) | F1—C8—F3 | 98.7 (10) |
| C9—Fe1—C16 | 155.40 (12) | F2—C8—F3 | 131.5 (11) |
| C10—Fe1—C16 | 162.11 (11) | F2X—C8—C5 | 116.2 (7) |
| C13—Fe1—C16 | 120.16 (11) | F3X—C8—C5 | 114.9 (5) |
| C15—Fe1—C16 | 40.69 (12) | F1X—C8—C5 | 114.7 (7) |
| C9—Fe1—C14 | 106.89 (12) | F1—C8—C5 | 112.6 (7) |
| C10—Fe1—C14 | 120.63 (12) | F2—C8—C5 | 112.7 (5) |
| C13—Fe1—C14 | 124.95 (12) | F3—C8—C5 | 110.0 (6) |
| C15—Fe1—C14 | 40.75 (11) | C8—F2X—F3X | 55.8 (11) |
| C16—Fe1—C14 | 68.29 (12) | C8—F3X—F2X | 52.8 (9) |
| C9—Fe1—C17 | 161.88 (12) | C10—C9—C13 | 107.4 (2) |
| C10—Fe1—C17 | 125.05 (11) | C10—C9—C1 | 128.3 (2) |
| C13—Fe1—C17 | 155.74 (12) | C13—C9—C1 | 124.1 (2) |
| C15—Fe1—C17 | 68.32 (12) | C10—C9—Fe1 | 69.78 (15) |
| C16—Fe1—C17 | 40.68 (11) | C13—C9—Fe1 | 69.64 (15) |
| C14—Fe1—C17 | 67.88 (12) | C1—C9—Fe1 | 121.78 (19) |
| C9—Fe1—C11 | 68.69 (12) | C11—C10—C9 | 107.8 (2) |
| C10—Fe1—C11 | 40.42 (12) | C11—C10—Fe1 | 70.21 (17) |
| C13—Fe1—C11 | 68.35 (12) | C9—C10—Fe1 | 68.91 (14) |
| C15—Fe1—C11 | 162.24 (12) | C11—C10—H10 | 126.1 |
| C16—Fe1—C11 | 125.61 (12) | C9—C10—H10 | 126.1 |
| C14—Fe1—C11 | 155.91 (13) | Fe1—C10—H10 | 126.3 |
| C17—Fe1—C11 | 108.56 (12) | C10—C11—C12 | 108.5 (3) |
| C9—Fe1—C12 | 68.79 (11) | C10—C11—Fe1 | 69.37 (16) |
| C10—Fe1—C12 | 68.55 (11) | C12—C11—Fe1 | 69.71 (16) |
| C13—Fe1—C12 | 40.31 (12) | C10—C11—H11 | 125.7 |
| C15—Fe1—C12 | 124.85 (12) | C12—C11—H11 | 125.7 |
| C16—Fe1—C12 | 107.87 (12) | Fe1—C11—H11 | 126.8 |
| C14—Fe1—C12 | 161.84 (13) | C13—C12—C11 | 108.3 (3) |
| C17—Fe1—C12 | 121.59 (12) | C13—C12—Fe1 | 69.33 (16) |
| C11—Fe1—C12 | 40.65 (12) | C11—C12—Fe1 | 69.64 (16) |
| C9—Fe1—C18 | 124.84 (12) | C13—C12—H12 | 125.9 |
| C10—Fe1—C18 | 107.73 (11) | C11—C12—H12 | 125.9 |
| C13—Fe1—C18 | 162.30 (13) | Fe1—C12—H12 | 126.7 |
| C15—Fe1—C18 | 68.31 (12) | C12—C13—C9 | 108.0 (2) |
| C16—Fe1—C18 | 68.09 (11) | C12—C13—Fe1 | 70.36 (16) |
| C14—Fe1—C18 | 40.46 (12) | C9—C13—Fe1 | 68.90 (15) |
| C17—Fe1—C18 | 40.09 (12) | C12—C13—H13 | 126.0 |
| C11—Fe1—C18 | 121.37 (12) | C9—C13—H13 | 126.0 |
| C12—Fe1—C18 | 156.31 (13) | Fe1—C13—H13 | 126.3 |
| N1—C1—C9 | 123.8 (2) | C18—C14—C15 | 108.2 (3) |
| N1—C1—H1 | 118.1 | C18—C14—Fe1 | 70.27 (16) |
| C9—C1—H1 | 118.1 | C15—C14—Fe1 | 69.53 (16) |
| C1—N1—C2 | 118.0 (2) | C18—C14—H14 | 125.9 |
| C7—C2—C3 | 118.9 (3) | C15—C14—H14 | 125.9 |
| C7—C2—N1 | 117.4 (3) | Fe1—C14—H14 | 125.9 |
| C3—C2—N1 | 123.6 (3) | C16—C15—C14 | 107.6 (3) |
| C4—C3—C2 | 120.0 (3) | C16—C15—Fe1 | 69.69 (16) |
| C4—C3—H3 | 120.0 | C14—C15—Fe1 | 69.72 (16) |
| C2—C3—H3 | 120.0 | C16—C15—H15 | 126.2 |
| C3—C4—C5 | 120.4 (3) | C14—C15—H15 | 126.2 |
| C3—C4—H4 | 119.8 | Fe1—C15—H15 | 126.0 |
| C5—C4—H4 | 119.8 | C15—C16—C17 | 107.8 (3) |
| C4—C5—C6 | 120.0 (3) | C15—C16—Fe1 | 69.62 (17) |
| C4—C5—C8 | 120.8 (3) | C17—C16—Fe1 | 69.82 (16) |
| C6—C5—C8 | 119.2 (3) | C15—C16—H16 | 126.1 |
| C7—C6—C5 | 119.7 (3) | C17—C16—H16 | 126.1 |
| C7—C6—H6 | 120.2 | Fe1—C16—H16 | 126.0 |
| C5—C6—H6 | 120.2 | C18—C17—C16 | 108.5 (3) |
| C6—C7—C2 | 121.1 (3) | C18—C17—Fe1 | 70.35 (17) |
| C6—C7—H7 | 119.4 | C16—C17—Fe1 | 69.50 (16) |
| C2—C7—H7 | 119.4 | C18—C17—H17 | 125.8 |
| F2X—C8—F3X | 71.3 (19) | C16—C17—H17 | 125.8 |
| F2X—C8—F1X | 122.9 (13) | Fe1—C17—H17 | 126.0 |
| F3X—C8—F1X | 108.1 (9) | C17—C18—C14 | 107.9 (2) |
| F2X—C8—F1 | 110.8 (16) | C17—C18—Fe1 | 69.56 (16) |
| F3X—C8—F1 | 124.4 (8) | C14—C18—Fe1 | 69.28 (16) |
| F1X—C8—F1 | 22.1 (12) | C17—C18—H18 | 126.0 |
| F2X—C8—F2 | 31.8 (15) | C14—C18—H18 | 126.0 |
| F3X—C8—F2 | 101.3 (9) | Fe1—C18—H18 | 126.7 |
| C9—C1—N1—C2 | −178.9 (2) | C18—Fe1—C12—C11 | −48.3 (3) |
| C1—N1—C2—C7 | −141.5 (3) | C11—C12—C13—C9 | −0.1 (3) |
| C1—N1—C2—C3 | 39.9 (4) | Fe1—C12—C13—C9 | 58.81 (19) |
| C7—C2—C3—C4 | 1.9 (4) | C11—C12—C13—Fe1 | −58.9 (2) |
| N1—C2—C3—C4 | −179.5 (2) | C10—C9—C13—C12 | 0.1 (3) |
| C2—C3—C4—C5 | −0.6 (4) | C1—C9—C13—C12 | −175.0 (3) |
| C3—C4—C5—C6 | −0.7 (4) | Fe1—C9—C13—C12 | −59.7 (2) |
| C3—C4—C5—C8 | −179.2 (3) | C10—C9—C13—Fe1 | 59.83 (18) |
| C4—C5—C6—C7 | 0.8 (4) | C1—C9—C13—Fe1 | −115.3 (3) |
| C8—C5—C6—C7 | 179.3 (3) | C9—Fe1—C13—C12 | 119.3 (2) |
| C5—C6—C7—C2 | 0.5 (4) | C10—Fe1—C13—C12 | 80.94 (18) |
| C3—C2—C7—C6 | −1.8 (4) | C15—Fe1—C13—C12 | −124.41 (18) |
| N1—C2—C7—C6 | 179.4 (2) | C16—Fe1—C13—C12 | −82.1 (2) |
| C4—C5—C8—F2X | 14.3 (19) | C14—Fe1—C13—C12 | −165.50 (16) |
| C6—C5—C8—F2X | −164.2 (19) | C17—Fe1—C13—C12 | −49.8 (3) |
| C4—C5—C8—F3X | 94.9 (9) | C11—Fe1—C13—C12 | 37.44 (17) |
| C6—C5—C8—F3X | −83.7 (9) | C18—Fe1—C13—C12 | 164.2 (3) |
| C4—C5—C8—F1X | −139.0 (12) | C10—Fe1—C13—C9 | −38.38 (16) |
| C6—C5—C8—F1X | 42.5 (12) | C15—Fe1—C13—C9 | 116.27 (17) |
| C4—C5—C8—F1 | −114.9 (8) | C16—Fe1—C13—C9 | 158.53 (16) |
| C6—C5—C8—F1 | 66.5 (9) | C14—Fe1—C13—C9 | 75.2 (2) |
| C4—C5—C8—F2 | −20.5 (7) | C17—Fe1—C13—C9 | −169.2 (2) |
| C6—C5—C8—F2 | 161.0 (6) | C11—Fe1—C13—C9 | −81.87 (18) |
| C4—C5—C8—F3 | 136.1 (14) | C12—Fe1—C13—C9 | −119.3 (2) |
| C6—C5—C8—F3 | −42.5 (14) | C18—Fe1—C13—C9 | 44.9 (4) |
| F1X—C8—F2X—F3X | −99.9 (19) | C9—Fe1—C14—C18 | −124.34 (17) |
| F1—C8—F2X—F3X | −120.7 (11) | C10—Fe1—C14—C18 | −81.4 (2) |
| F2—C8—F2X—F3X | −160 (2) | C13—Fe1—C14—C18 | −166.32 (17) |
| F3—C8—F2X—F3X | −14.1 (12) | C15—Fe1—C14—C18 | 119.2 (3) |
| C5—C8—F2X—F3X | 109.2 (9) | C16—Fe1—C14—C18 | 81.25 (18) |
| F1X—C8—F3X—F2X | 119.5 (12) | C17—Fe1—C14—C18 | 37.24 (17) |
| F1—C8—F3X—F2X | 102.8 (12) | C11—Fe1—C14—C18 | −48.9 (4) |
| F2—C8—F3X—F2X | 10.8 (11) | C12—Fe1—C14—C18 | 162.4 (3) |
| F3—C8—F3X—F2X | 157.8 (16) | C9—Fe1—C14—C15 | 116.43 (18) |
| C5—C8—F3X—F2X | −110.9 (10) | C10—Fe1—C14—C15 | 159.34 (17) |
| N1—C1—C9—C10 | 8.2 (4) | C13—Fe1—C14—C15 | 74.4 (2) |
| N1—C1—C9—C13 | −177.7 (3) | C16—Fe1—C14—C15 | −37.99 (17) |
| N1—C1—C9—Fe1 | 96.6 (3) | C17—Fe1—C14—C15 | −81.99 (19) |
| C13—Fe1—C9—C10 | −118.5 (2) | C11—Fe1—C14—C15 | −168.1 (2) |
| C15—Fe1—C9—C10 | 159.84 (16) | C12—Fe1—C14—C15 | 43.1 (4) |
| C16—Fe1—C9—C10 | −167.9 (2) | C18—Fe1—C14—C15 | −119.2 (3) |
| C14—Fe1—C9—C10 | 117.46 (17) | C18—C14—C15—C16 | −0.2 (3) |
| C17—Fe1—C9—C10 | 47.2 (4) | Fe1—C14—C15—C16 | 59.6 (2) |
| C11—Fe1—C9—C10 | −37.45 (16) | C18—C14—C15—Fe1 | −59.9 (2) |
| C12—Fe1—C9—C10 | −81.22 (17) | C9—Fe1—C15—C16 | 160.10 (16) |
| C18—Fe1—C9—C10 | 76.70 (19) | C10—Fe1—C15—C16 | −166.3 (2) |
| C10—Fe1—C9—C13 | 118.5 (2) | C13—Fe1—C15—C16 | 116.89 (17) |
| C15—Fe1—C9—C13 | −81.71 (19) | C14—Fe1—C15—C16 | −118.7 (2) |
| C16—Fe1—C9—C13 | −49.5 (3) | C17—Fe1—C15—C16 | −37.88 (17) |
| C14—Fe1—C9—C13 | −124.09 (17) | C11—Fe1—C15—C16 | 45.3 (4) |
| C17—Fe1—C9—C13 | 165.6 (3) | C12—Fe1—C15—C16 | 76.3 (2) |
| C11—Fe1—C9—C13 | 81.00 (18) | C18—Fe1—C15—C16 | −81.18 (18) |
| C12—Fe1—C9—C13 | 37.23 (17) | C9—Fe1—C15—C14 | −81.2 (2) |
| C18—Fe1—C9—C13 | −164.85 (17) | C10—Fe1—C15—C14 | −47.6 (3) |
| C10—Fe1—C9—C1 | −123.3 (3) | C13—Fe1—C15—C14 | −124.39 (18) |
| C13—Fe1—C9—C1 | 118.2 (3) | C16—Fe1—C15—C14 | 118.7 (2) |
| C15—Fe1—C9—C1 | 36.5 (3) | C17—Fe1—C15—C14 | 80.83 (19) |
| C16—Fe1—C9—C1 | 68.8 (3) | C11—Fe1—C15—C14 | 164.0 (3) |
| C14—Fe1—C9—C1 | −5.9 (2) | C12—Fe1—C15—C14 | −164.95 (18) |
| C17—Fe1—C9—C1 | −76.1 (4) | C18—Fe1—C15—C14 | 37.54 (18) |
| C11—Fe1—C9—C1 | −160.8 (2) | C14—C15—C16—C17 | 0.0 (3) |
| C12—Fe1—C9—C1 | 155.5 (2) | Fe1—C15—C16—C17 | 59.63 (19) |
| C18—Fe1—C9—C1 | −46.6 (3) | C14—C15—C16—Fe1 | −59.7 (2) |
| C13—C9—C10—C11 | −0.1 (3) | C9—Fe1—C16—C15 | −45.2 (3) |
| C1—C9—C10—C11 | 174.8 (3) | C10—Fe1—C16—C15 | 161.5 (3) |
| Fe1—C9—C10—C11 | 59.68 (19) | C13—Fe1—C16—C15 | −80.76 (19) |
| C13—C9—C10—Fe1 | −59.74 (18) | C14—Fe1—C16—C15 | 38.04 (17) |
| C1—C9—C10—Fe1 | 115.1 (3) | C17—Fe1—C16—C15 | 118.9 (2) |
| C9—Fe1—C10—C11 | −119.1 (2) | C11—Fe1—C16—C15 | −164.53 (16) |
| C13—Fe1—C10—C11 | −80.61 (18) | C12—Fe1—C16—C15 | −123.09 (17) |
| C15—Fe1—C10—C11 | −165.7 (2) | C18—Fe1—C16—C15 | 81.77 (18) |
| C16—Fe1—C10—C11 | 44.4 (4) | C9—Fe1—C16—C17 | −164.1 (2) |
| C14—Fe1—C10—C11 | 160.21 (17) | C10—Fe1—C16—C17 | 42.6 (4) |
| C17—Fe1—C10—C11 | 77.1 (2) | C13—Fe1—C16—C17 | 160.32 (16) |
| C12—Fe1—C10—C11 | −37.27 (17) | C15—Fe1—C16—C17 | −118.9 (2) |
| C18—Fe1—C10—C11 | 117.87 (18) | C14—Fe1—C16—C17 | −80.88 (19) |
| C13—Fe1—C10—C9 | 38.50 (16) | C11—Fe1—C16—C17 | 76.6 (2) |
| C15—Fe1—C10—C9 | −46.6 (3) | C12—Fe1—C16—C17 | 118.00 (18) |
| C16—Fe1—C10—C9 | 163.6 (3) | C18—Fe1—C16—C17 | −37.15 (18) |
| C14—Fe1—C10—C9 | −80.67 (19) | C15—C16—C17—C18 | 0.3 (3) |
| C17—Fe1—C10—C9 | −163.83 (16) | Fe1—C16—C17—C18 | 59.8 (2) |
| C11—Fe1—C10—C9 | 119.1 (2) | C15—C16—C17—Fe1 | −59.5 (2) |
| C12—Fe1—C10—C9 | 81.85 (17) | C9—Fe1—C17—C18 | 38.9 (4) |
| C18—Fe1—C10—C9 | −123.01 (17) | C10—Fe1—C17—C18 | 75.2 (2) |
| C9—C10—C11—C12 | 0.0 (3) | C13—Fe1—C17—C18 | −164.7 (2) |
| Fe1—C10—C11—C12 | 58.9 (2) | C15—Fe1—C17—C18 | −81.65 (18) |
| C9—C10—C11—Fe1 | −58.87 (18) | C16—Fe1—C17—C18 | −119.5 (2) |
| C9—Fe1—C11—C10 | 38.25 (16) | C14—Fe1—C17—C18 | −37.57 (17) |
| C13—Fe1—C11—C10 | 82.96 (18) | C11—Fe1—C17—C18 | 116.99 (18) |
| C15—Fe1—C11—C10 | 160.6 (3) | C12—Fe1—C17—C18 | 159.84 (17) |
| C16—Fe1—C11—C10 | −164.66 (16) | C9—Fe1—C17—C16 | 158.5 (3) |
| C14—Fe1—C11—C10 | −45.5 (4) | C10—Fe1—C17—C16 | −165.28 (16) |
| C17—Fe1—C11—C10 | −122.69 (17) | C13—Fe1—C17—C16 | −45.1 (3) |
| C12—Fe1—C11—C10 | 120.1 (2) | C15—Fe1—C17—C16 | 37.89 (17) |
| C18—Fe1—C11—C10 | −80.5 (2) | C14—Fe1—C17—C16 | 81.96 (18) |
| C9—Fe1—C11—C12 | −81.84 (18) | C11—Fe1—C17—C16 | −123.48 (18) |
| C10—Fe1—C11—C12 | −120.1 (2) | C12—Fe1—C17—C16 | −80.6 (2) |
| C13—Fe1—C11—C12 | −37.14 (17) | C18—Fe1—C17—C16 | 119.5 (3) |
| C15—Fe1—C11—C12 | 40.5 (4) | C16—C17—C18—C14 | −0.4 (3) |
| C16—Fe1—C11—C12 | 75.2 (2) | Fe1—C17—C18—C14 | 58.8 (2) |
| C14—Fe1—C11—C12 | −165.6 (3) | C16—C17—C18—Fe1 | −59.2 (2) |
| C17—Fe1—C11—C12 | 117.21 (18) | C15—C14—C18—C17 | 0.4 (3) |
| C18—Fe1—C11—C12 | 159.45 (17) | Fe1—C14—C18—C17 | −59.0 (2) |
| C10—C11—C12—C13 | 0.1 (3) | C15—C14—C18—Fe1 | 59.4 (2) |
| Fe1—C11—C12—C13 | 58.7 (2) | C9—Fe1—C18—C17 | −166.23 (16) |
| C10—C11—C12—Fe1 | −58.7 (2) | C10—Fe1—C18—C17 | −123.81 (17) |
| C9—Fe1—C12—C13 | −38.26 (17) | C13—Fe1—C18—C17 | 159.1 (3) |
| C10—Fe1—C12—C13 | −82.77 (18) | C15—Fe1—C18—C17 | 81.67 (18) |
| C15—Fe1—C12—C13 | 74.1 (2) | C16—Fe1—C18—C17 | 37.69 (17) |
| C16—Fe1—C12—C13 | 115.86 (18) | C14—Fe1—C18—C17 | 119.5 (2) |
| C14—Fe1—C12—C13 | 41.2 (4) | C11—Fe1—C18—C17 | −81.6 (2) |
| C17—Fe1—C12—C13 | 158.37 (17) | C12—Fe1—C18—C17 | −46.9 (3) |
| C11—Fe1—C12—C13 | −119.8 (3) | C9—Fe1—C18—C14 | 74.3 (2) |
| C18—Fe1—C12—C13 | −168.1 (2) | C10—Fe1—C18—C14 | 116.72 (18) |
| C9—Fe1—C12—C11 | 81.58 (18) | C13—Fe1—C18—C14 | 39.6 (4) |
| C10—Fe1—C12—C11 | 37.07 (17) | C15—Fe1—C18—C14 | −37.81 (17) |
| C13—Fe1—C12—C11 | 119.8 (3) | C16—Fe1—C18—C14 | −81.79 (18) |
| C15—Fe1—C12—C11 | −166.04 (16) | C17—Fe1—C18—C14 | −119.5 (2) |
| C16—Fe1—C12—C11 | −124.31 (18) | C11—Fe1—C18—C14 | 158.89 (17) |
| C14—Fe1—C12—C11 | 161.0 (3) | C12—Fe1—C18—C14 | −166.4 (2) |
| C17—Fe1—C12—C11 | −81.8 (2) |
The author thanks the Deutsche Forschungsgemeinschaft (SFB 436) for financial support.
Imhof, W. (1997). J. Organomet. Chem. 541, 109–116.
Imhof, W. (1998). Inorg. Chim. Acta, 282, 111–118.
Imhof, W. (2004). Acta Cryst. E60, m1234–m1236.
Imhof, W. (2005). Z. Anorg. Allg. Chem. 631, 174–177.
Nonius (1998). COLLECT, Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.
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Siemens (1990). XP. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
In the course of a study on imines derived from aldehydes and amines exhibiting ferrocenyl substituents we recognized that ferrocenyl-prop-2-enal as well as some of the corresponding imines crystallize in non-centrosymmetric space groups (Imhof, 1997, 1998, 2004, 2005). The title compound crystallizes in the centrosymmetric space group P1. All bond lengths and bond angles are of expected values. The Cp rings are coplanar (dihedral angle 1.4 (3)°) and the imine function is situated in the same plane. The aromatic substituent is bent out of the plane of the Cp the imine moiety is attached to by 44.5 (4)°. The shortest intermolecular distances are observed between fluorine atoms and hydrogen atoms of a Cp ring. Nevertheless, since the CF3 substituent is highly disordered these contacts should not be discussed as C–H···F hydrogen bonds.