Acta Cryst. (2011). E67, m1113 [ doi:10.1107/S1600536811026341 ]
In the title compound, [Fe(C5H5)(C15H11N2O)], the cyclopentadienyl rings are essentially eclipsed, and the dihedral angle between the cyclopentadienyl ring planes is 0.632 (10)°. The Fe atom is slightly closer to the substituted cyclopentadienyl ring, with an Fe-centroid distance of 1.6374 (3) Å [1.6494 (3) Å for the unsubstituted ring]. The amide group is essentially coplanar with the substituted cyclopentadienyl ring, with an N-C(O)-C-C torsion angle of 2.3 (3)°.
A solution of Chlorocarbonyl ferrocene (0.248 g, 1 mmol) in CH2Cl2 (20 ml) was added dropwise to a vigorously stirred solution of the 8-Aminoquinoline (0.144 g, 1 mmol) in CH2Cl2 (20 ml) containing pyridine (0.5 ml). The stirred reaction mixture was maintained at room temperature for 4 h. Removal of the solvent afforded the crude amide and the residue was recrystallized in dichloromethane/ether to give orange crystals 0.325 g. Yield 91.3%.
H atom bonded to N atom was located from difference Fourier maps and refined with a DFIX restraint of 0.86 (2) Å. Aromatic H atoms were positioned geometrically with C—H = 0.95 Å and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C).
Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear (Rigaku, 2000); data reduction: CrystalClear (Rigaku, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL97 (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./fj2441fig1thm.gif)
| Fig. 1. The molecular structure of the title compound, showing the atomic numbering and 30% probability displacement ellipsoids. |
| [Fe(C5H5)(C15H11N2O)] | F(000) = 1472 |
| Mr = 356.20 | Dx = 1.471 Mg m−3 |
| Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ac 2ab | θ = 1.6–28.3° |
| a = 10.1680 (17) Å | µ = 0.95 mm−1 |
| b = 12.133 (2) Å | T = 296 K |
| c = 26.079 (4) Å | Block, orange |
| V = 3217.4 (10) Å3 | 0.46 × 0.37 × 0.25 mm |
| Z = 8 |
| Rigaku Mercury CCD diffractometer | 3940 independent reflections |
| Radiation source: fine-focus sealed tube | 2996 reflections with I > 2σ(I) |
| graphite | Rint = 0.031 |
| ω scan | θmax = 28.3°, θmin = 1.6° |
| Absorption correction: multi-scan (CrystalClear; Rigaku, 2000) | h = −13→13 |
| Tmin = 0.668, Tmax = 0.795 | k = −12→15 |
| 18658 measured reflections | l = −34→29 |
| 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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.097 | H-atom parameters constrained |
| S = 1.01 | w = 1/[σ2(Fo2) + (0.P)2 + 1.0596P] where P = (Fo2 + 2Fc2)/3 |
| 3940 reflections | (Δ/σ)max = 0.001 |
| 222 parameters | Δρmax = 0.26 e Å−3 |
| 0 restraints | Δρmin = −0.37 e Å−3 |
| [Fe(C5H5)(C15H11N2O)] | V = 3217.4 (10) Å3 |
| Mr = 356.20 | Z = 8 |
| Orthorhombic, Pbca | Mo Kα radiation |
| a = 10.1680 (17) Å | µ = 0.95 mm−1 |
| b = 12.133 (2) Å | T = 296 K |
| c = 26.079 (4) Å | 0.46 × 0.37 × 0.25 mm |
| Rigaku Mercury CCD diffractometer | 3940 independent reflections |
| Absorption correction: multi-scan (CrystalClear; Rigaku, 2000) | 2996 reflections with I > 2σ(I) |
| Tmin = 0.668, Tmax = 0.795 | Rint = 0.031 |
| 18658 measured reflections | θmax = 28.3° |
| R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
| wR(F2) = 0.097 | Δρmax = 0.26 e Å−3 |
| S = 1.01 | Δρmin = −0.37 e Å−3 |
| 3940 reflections | Absolute structure: ? |
| 222 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 | ||
| Fe1 | 0.08194 (2) | 0.61371 (2) | 0.324077 (9) | 0.03985 (12) | |
| O1 | −0.14938 (18) | 0.85691 (16) | 0.34733 (7) | 0.0757 (5) | |
| N1 | 0.02468 (18) | 0.87266 (15) | 0.40153 (7) | 0.0471 (4) | |
| N2 | 0.19232 (16) | 0.94139 (13) | 0.47326 (6) | 0.0433 (4) | |
| C1 | −0.04130 (18) | 0.69359 (18) | 0.37255 (7) | 0.0432 (4) | |
| C2 | −0.1135 (2) | 0.6191 (2) | 0.34083 (8) | 0.0509 (5) | |
| H2 | −0.1811 | 0.6384 | 0.3186 | 0.061* | |
| C3 | −0.0656 (2) | 0.5119 (2) | 0.34881 (8) | 0.0580 (6) | |
| H3 | −0.0959 | 0.4483 | 0.3328 | 0.070* | |
| C4 | 0.0368 (2) | 0.5175 (2) | 0.38554 (8) | 0.0585 (6) | |
| H4 | 0.0856 | 0.4581 | 0.3977 | 0.070* | |
| C5 | 0.0521 (2) | 0.62850 (18) | 0.40057 (7) | 0.0484 (5) | |
| H5 | 0.1122 | 0.6549 | 0.4245 | 0.058* | |
| C6 | 0.1656 (3) | 0.7278 (2) | 0.27759 (10) | 0.0756 (8) | |
| H6 | 0.1460 | 0.8027 | 0.2772 | 0.091* | |
| C7 | 0.1037 (2) | 0.6449 (3) | 0.24815 (9) | 0.0741 (8) | |
| H7 | 0.0355 | 0.6550 | 0.2249 | 0.089* | |
| C8 | 0.1644 (3) | 0.5444 (3) | 0.26050 (10) | 0.0736 (8) | |
| H8 | 0.1437 | 0.4758 | 0.2468 | 0.088* | |
| C9 | 0.2604 (3) | 0.5657 (3) | 0.29680 (10) | 0.0767 (8) | |
| H9 | 0.3153 | 0.5133 | 0.3117 | 0.092* | |
| C10 | 0.2614 (2) | 0.6765 (3) | 0.30727 (11) | 0.0775 (8) | |
| H10 | 0.3171 | 0.7115 | 0.3304 | 0.093* | |
| C11 | −0.06124 (18) | 0.81347 (19) | 0.37209 (7) | 0.0475 (5) | |
| C12 | 0.02430 (18) | 0.98542 (16) | 0.41223 (7) | 0.0419 (4) | |
| C13 | −0.0553 (2) | 1.0624 (2) | 0.38937 (8) | 0.0525 (5) | |
| H13 | −0.1144 | 1.0406 | 0.3641 | 0.063* | |
| C14 | −0.0483 (2) | 1.1737 (2) | 0.40382 (9) | 0.0602 (6) | |
| H14 | −0.1021 | 1.2247 | 0.3875 | 0.072* | |
| C15 | 0.0351 (2) | 1.20882 (19) | 0.44113 (9) | 0.0583 (5) | |
| H15 | 0.0374 | 1.2829 | 0.4503 | 0.070* | |
| C16 | 0.1185 (2) | 1.13215 (16) | 0.46605 (7) | 0.0437 (4) | |
| C17 | 0.11420 (17) | 1.02001 (15) | 0.45129 (6) | 0.0381 (4) | |
| C18 | 0.2047 (2) | 1.16091 (17) | 0.50584 (8) | 0.0506 (5) | |
| H18 | 0.2107 | 1.2338 | 0.5166 | 0.061* | |
| C19 | 0.2793 (2) | 1.08233 (18) | 0.52850 (8) | 0.0512 (5) | |
| H19 | 0.3351 | 1.1000 | 0.5555 | 0.061* | |
| C20 | 0.2707 (2) | 0.97401 (17) | 0.51045 (7) | 0.0489 (5) | |
| H20 | 0.3241 | 0.9213 | 0.5258 | 0.059* | |
| H1 | 0.078 (2) | 0.8400 (19) | 0.4191 (8) | 0.046 (6)* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Fe1 | 0.03308 (17) | 0.0496 (2) | 0.03683 (16) | −0.00552 (11) | 0.00144 (10) | −0.00378 (11) |
| O1 | 0.0693 (11) | 0.0826 (12) | 0.0752 (11) | 0.0229 (10) | −0.0350 (9) | −0.0182 (9) |
| N1 | 0.0441 (9) | 0.0508 (10) | 0.0464 (9) | 0.0082 (8) | −0.0110 (7) | −0.0072 (7) |
| N2 | 0.0460 (9) | 0.0388 (9) | 0.0451 (8) | 0.0007 (7) | −0.0054 (7) | −0.0007 (7) |
| C1 | 0.0344 (9) | 0.0619 (13) | 0.0334 (8) | −0.0037 (9) | 0.0001 (7) | −0.0077 (8) |
| C2 | 0.0341 (10) | 0.0756 (16) | 0.0431 (10) | −0.0137 (10) | 0.0019 (8) | −0.0091 (10) |
| C3 | 0.0572 (13) | 0.0613 (15) | 0.0554 (12) | −0.0254 (11) | 0.0076 (10) | −0.0071 (11) |
| C4 | 0.0674 (14) | 0.0551 (13) | 0.0530 (12) | −0.0080 (11) | 0.0008 (10) | 0.0106 (10) |
| C5 | 0.0501 (11) | 0.0597 (13) | 0.0356 (9) | −0.0065 (10) | −0.0038 (8) | 0.0002 (9) |
| C6 | 0.0774 (18) | 0.0681 (17) | 0.0813 (17) | −0.0078 (14) | 0.0356 (15) | 0.0080 (14) |
| C7 | 0.0482 (13) | 0.133 (3) | 0.0411 (11) | −0.0043 (15) | 0.0088 (9) | 0.0110 (14) |
| C8 | 0.0768 (18) | 0.0833 (19) | 0.0608 (14) | −0.0106 (15) | 0.0243 (13) | −0.0214 (13) |
| C9 | 0.0494 (14) | 0.106 (2) | 0.0749 (16) | 0.0155 (15) | 0.0118 (12) | −0.0030 (16) |
| C10 | 0.0445 (13) | 0.113 (3) | 0.0748 (16) | −0.0260 (15) | 0.0118 (12) | −0.0170 (16) |
| C11 | 0.0408 (10) | 0.0643 (14) | 0.0374 (9) | 0.0060 (9) | −0.0037 (8) | −0.0098 (9) |
| C12 | 0.0406 (10) | 0.0467 (11) | 0.0385 (9) | 0.0054 (8) | 0.0056 (7) | −0.0018 (8) |
| C13 | 0.0492 (12) | 0.0625 (14) | 0.0457 (10) | 0.0110 (10) | −0.0004 (9) | 0.0057 (10) |
| C14 | 0.0623 (14) | 0.0544 (14) | 0.0640 (13) | 0.0192 (11) | 0.0068 (11) | 0.0163 (11) |
| C15 | 0.0645 (14) | 0.0443 (12) | 0.0660 (13) | 0.0077 (11) | 0.0078 (11) | 0.0087 (10) |
| C16 | 0.0476 (10) | 0.0360 (10) | 0.0475 (10) | 0.0009 (8) | 0.0121 (8) | 0.0050 (8) |
| C17 | 0.0390 (9) | 0.0388 (10) | 0.0366 (8) | 0.0017 (8) | 0.0064 (7) | 0.0027 (7) |
| C18 | 0.0603 (13) | 0.0368 (10) | 0.0548 (11) | −0.0077 (9) | 0.0087 (10) | −0.0059 (9) |
| C19 | 0.0599 (13) | 0.0455 (11) | 0.0483 (10) | −0.0104 (10) | −0.0063 (9) | −0.0018 (9) |
| C20 | 0.0562 (12) | 0.0390 (10) | 0.0515 (10) | −0.0009 (9) | −0.0102 (9) | 0.0011 (8) |
| Fe1—C10 | 2.026 (2) | C6—C10 | 1.391 (4) |
| Fe1—C5 | 2.0258 (19) | C6—C7 | 1.413 (4) |
| Fe1—C1 | 2.0268 (19) | C6—H6 | 0.9300 |
| Fe1—C6 | 2.028 (2) | C7—C8 | 1.404 (4) |
| Fe1—C7 | 2.028 (2) | C7—H7 | 0.9300 |
| Fe1—C9 | 2.034 (2) | C8—C9 | 1.384 (4) |
| Fe1—C4 | 2.036 (2) | C8—H8 | 0.9300 |
| Fe1—C2 | 2.036 (2) | C9—C10 | 1.372 (4) |
| Fe1—C8 | 2.039 (2) | C9—H9 | 0.9300 |
| Fe1—C3 | 2.048 (2) | C10—H10 | 0.9300 |
| O1—C11 | 1.224 (2) | C12—C13 | 1.372 (3) |
| N1—C11 | 1.367 (3) | C12—C17 | 1.432 (3) |
| N1—C12 | 1.396 (3) | C13—C14 | 1.405 (4) |
| N1—H1 | 0.81 (2) | C13—H13 | 0.9300 |
| N2—C20 | 1.316 (2) | C14—C15 | 1.359 (3) |
| N2—C17 | 1.367 (2) | C14—H14 | 0.9300 |
| C1—C2 | 1.429 (3) | C15—C16 | 1.417 (3) |
| C1—C5 | 1.435 (3) | C15—H15 | 0.9300 |
| C1—C11 | 1.469 (3) | C16—C18 | 1.402 (3) |
| C2—C3 | 1.404 (3) | C16—C17 | 1.415 (3) |
| C2—H2 | 0.9300 | C18—C19 | 1.354 (3) |
| C3—C4 | 1.417 (3) | C18—H18 | 0.9300 |
| C3—H3 | 0.9300 | C19—C20 | 1.399 (3) |
| C4—C5 | 1.412 (3) | C19—H19 | 0.9300 |
| C4—H4 | 0.9300 | C20—H20 | 0.9300 |
| C5—H5 | 0.9300 | ||
| C10—Fe1—C5 | 108.35 (10) | C5—C4—H4 | 125.8 |
| C10—Fe1—C1 | 120.82 (10) | C3—C4—H4 | 125.8 |
| C5—Fe1—C1 | 41.47 (8) | Fe1—C4—H4 | 126.3 |
| C10—Fe1—C6 | 40.16 (12) | C4—C5—C1 | 108.12 (18) |
| C5—Fe1—C6 | 126.24 (11) | C4—C5—Fe1 | 70.04 (12) |
| C1—Fe1—C6 | 107.81 (10) | C1—C5—Fe1 | 69.30 (10) |
| C10—Fe1—C7 | 67.67 (11) | C4—C5—H5 | 125.9 |
| C5—Fe1—C7 | 164.01 (13) | C1—C5—H5 | 125.9 |
| C1—Fe1—C7 | 125.97 (11) | Fe1—C5—H5 | 126.3 |
| C6—Fe1—C7 | 40.79 (11) | C10—C6—C7 | 107.2 (3) |
| C10—Fe1—C9 | 39.50 (13) | C10—C6—Fe1 | 69.85 (15) |
| C5—Fe1—C9 | 120.23 (10) | C7—C6—Fe1 | 69.62 (15) |
| C1—Fe1—C9 | 155.04 (10) | C10—C6—H6 | 126.4 |
| C6—Fe1—C9 | 67.18 (12) | C7—C6—H6 | 126.4 |
| C7—Fe1—C9 | 67.32 (11) | Fe1—C6—H6 | 125.7 |
| C10—Fe1—C4 | 126.11 (12) | C8—C7—C6 | 107.4 (2) |
| C5—Fe1—C4 | 40.68 (9) | C8—C7—Fe1 | 70.25 (14) |
| C1—Fe1—C4 | 69.13 (10) | C6—C7—Fe1 | 69.59 (14) |
| C6—Fe1—C4 | 163.18 (11) | C8—C7—H7 | 126.3 |
| C7—Fe1—C4 | 154.22 (12) | C6—C7—H7 | 126.3 |
| C9—Fe1—C4 | 108.19 (11) | Fe1—C7—H7 | 125.4 |
| C10—Fe1—C2 | 156.06 (12) | C9—C8—C7 | 107.7 (3) |
| C5—Fe1—C2 | 68.87 (8) | C9—C8—Fe1 | 69.94 (14) |
| C1—Fe1—C2 | 41.18 (8) | C7—C8—Fe1 | 69.38 (14) |
| C6—Fe1—C2 | 121.07 (11) | C9—C8—H8 | 126.1 |
| C7—Fe1—C2 | 108.08 (10) | C7—C8—H8 | 126.1 |
| C9—Fe1—C2 | 162.73 (11) | Fe1—C8—H8 | 126.1 |
| C4—Fe1—C2 | 68.23 (10) | C10—C9—C8 | 108.9 (3) |
| C10—Fe1—C8 | 66.96 (11) | C10—C9—Fe1 | 69.91 (14) |
| C5—Fe1—C8 | 153.99 (11) | C8—C9—Fe1 | 70.33 (14) |
| C1—Fe1—C8 | 163.43 (10) | C10—C9—H9 | 125.5 |
| C6—Fe1—C8 | 67.85 (12) | C8—C9—H9 | 125.5 |
| C7—Fe1—C8 | 40.38 (12) | Fe1—C9—H9 | 125.8 |
| C9—Fe1—C8 | 39.72 (11) | C9—C10—C6 | 108.8 (2) |
| C4—Fe1—C8 | 119.76 (12) | C9—C10—Fe1 | 70.60 (15) |
| C2—Fe1—C8 | 126.08 (10) | C6—C10—Fe1 | 70.00 (14) |
| C10—Fe1—C3 | 162.78 (13) | C9—C10—H10 | 125.6 |
| C5—Fe1—C3 | 68.49 (9) | C6—C10—H10 | 125.6 |
| C1—Fe1—C3 | 68.83 (9) | Fe1—C10—H10 | 125.4 |
| C6—Fe1—C3 | 155.20 (12) | O1—C11—N1 | 122.5 (2) |
| C7—Fe1—C3 | 120.02 (11) | O1—C11—C1 | 122.14 (19) |
| C9—Fe1—C3 | 126.23 (12) | N1—C11—C1 | 115.31 (17) |
| C4—Fe1—C3 | 40.59 (9) | C13—C12—N1 | 125.55 (19) |
| C2—Fe1—C3 | 40.22 (9) | C13—C12—C17 | 119.11 (19) |
| C8—Fe1—C3 | 107.98 (10) | N1—C12—C17 | 115.32 (16) |
| C11—N1—C12 | 128.71 (18) | C12—C13—C14 | 120.5 (2) |
| C11—N1—H1 | 119.1 (16) | C12—C13—H13 | 119.7 |
| C12—N1—H1 | 111.5 (16) | C14—C13—H13 | 119.7 |
| C20—N2—C17 | 116.78 (17) | C15—C14—C13 | 121.7 (2) |
| C2—C1—C5 | 106.7 (2) | C15—C14—H14 | 119.2 |
| C2—C1—C11 | 123.43 (18) | C13—C14—H14 | 119.2 |
| C5—C1—C11 | 129.84 (17) | C14—C15—C16 | 119.8 (2) |
| C2—C1—Fe1 | 69.76 (11) | C14—C15—H15 | 120.1 |
| C5—C1—Fe1 | 69.23 (11) | C16—C15—H15 | 120.1 |
| C11—C1—Fe1 | 123.63 (14) | C18—C16—C17 | 117.39 (18) |
| C3—C2—C1 | 108.78 (19) | C18—C16—C15 | 123.4 (2) |
| C3—C2—Fe1 | 70.34 (12) | C17—C16—C15 | 119.2 (2) |
| C1—C2—Fe1 | 69.06 (11) | N2—C17—C16 | 122.62 (17) |
| C3—C2—H2 | 125.6 | N2—C17—C12 | 117.68 (17) |
| C1—C2—H2 | 125.6 | C16—C17—C12 | 119.70 (17) |
| Fe1—C2—H2 | 126.6 | C19—C18—C16 | 119.8 (2) |
| C2—C3—C4 | 108.1 (2) | C19—C18—H18 | 120.1 |
| C2—C3—Fe1 | 69.44 (12) | C16—C18—H18 | 120.1 |
| C4—C3—Fe1 | 69.24 (12) | C18—C19—C20 | 118.7 (2) |
| C2—C3—H3 | 125.9 | C18—C19—H19 | 120.7 |
| C4—C3—H3 | 125.9 | C20—C19—H19 | 120.7 |
| Fe1—C3—H3 | 127.0 | N2—C20—C19 | 124.65 (19) |
| C5—C4—C3 | 108.3 (2) | N2—C20—H20 | 117.7 |
| C5—C4—Fe1 | 69.29 (12) | C19—C20—H20 | 117.7 |
| C3—C4—Fe1 | 70.16 (12) | ||
| C10—Fe1—C1—C2 | 159.14 (15) | C5—Fe1—C6—C7 | −167.14 (16) |
| C5—Fe1—C1—C2 | −117.82 (19) | C1—Fe1—C6—C7 | −124.89 (16) |
| C6—Fe1—C1—C2 | 117.14 (16) | C9—Fe1—C6—C7 | 81.22 (18) |
| C7—Fe1—C1—C2 | 75.68 (18) | C4—Fe1—C6—C7 | 158.4 (3) |
| C9—Fe1—C1—C2 | −168.8 (2) | C2—Fe1—C6—C7 | −81.73 (18) |
| C4—Fe1—C1—C2 | −80.40 (15) | C8—Fe1—C6—C7 | 38.08 (16) |
| C8—Fe1—C1—C2 | 45.1 (4) | C3—Fe1—C6—C7 | −47.0 (3) |
| C3—Fe1—C1—C2 | −36.77 (13) | C10—C6—C7—C8 | −0.3 (3) |
| C10—Fe1—C1—C5 | −83.03 (17) | Fe1—C6—C7—C8 | −60.39 (16) |
| C6—Fe1—C1—C5 | −125.04 (14) | C10—C6—C7—Fe1 | 60.05 (17) |
| C7—Fe1—C1—C5 | −166.50 (15) | C10—Fe1—C7—C8 | 80.21 (18) |
| C9—Fe1—C1—C5 | −51.0 (3) | C5—Fe1—C7—C8 | 158.8 (3) |
| C4—Fe1—C1—C5 | 37.42 (12) | C1—Fe1—C7—C8 | −167.07 (14) |
| C2—Fe1—C1—C5 | 117.82 (19) | C6—Fe1—C7—C8 | 118.2 (2) |
| C8—Fe1—C1—C5 | 163.0 (3) | C9—Fe1—C7—C8 | 37.31 (16) |
| C3—Fe1—C1—C5 | 81.05 (14) | C4—Fe1—C7—C8 | −47.7 (3) |
| C10—Fe1—C1—C11 | 41.8 (2) | C2—Fe1—C7—C8 | −124.92 (16) |
| C5—Fe1—C1—C11 | 124.8 (2) | C3—Fe1—C7—C8 | −82.58 (17) |
| C6—Fe1—C1—C11 | −0.25 (19) | C10—Fe1—C7—C6 | −37.94 (17) |
| C7—Fe1—C1—C11 | −41.7 (2) | C5—Fe1—C7—C6 | 40.7 (4) |
| C9—Fe1—C1—C11 | 73.8 (3) | C1—Fe1—C7—C6 | 74.78 (18) |
| C4—Fe1—C1—C11 | 162.22 (18) | C9—Fe1—C7—C6 | −80.84 (18) |
| C2—Fe1—C1—C11 | −117.4 (2) | C4—Fe1—C7—C6 | −165.9 (2) |
| C8—Fe1—C1—C11 | −72.3 (4) | C2—Fe1—C7—C6 | 116.93 (17) |
| C3—Fe1—C1—C11 | −154.15 (18) | C8—Fe1—C7—C6 | −118.2 (2) |
| C5—C1—C2—C3 | −0.4 (2) | C3—Fe1—C7—C6 | 159.27 (16) |
| C11—C1—C2—C3 | 176.95 (18) | C6—C7—C8—C9 | 0.3 (3) |
| Fe1—C1—C2—C3 | 59.31 (14) | Fe1—C7—C8—C9 | −59.66 (17) |
| C5—C1—C2—Fe1 | −59.67 (13) | C6—C7—C8—Fe1 | 59.97 (16) |
| C11—C1—C2—Fe1 | 117.64 (18) | C10—Fe1—C8—C9 | 36.84 (19) |
| C10—Fe1—C2—C3 | −169.1 (2) | C5—Fe1—C8—C9 | −47.9 (3) |
| C5—Fe1—C2—C3 | −81.27 (14) | C1—Fe1—C8—C9 | 158.4 (3) |
| C1—Fe1—C2—C3 | −120.17 (18) | C6—Fe1—C8—C9 | 80.49 (19) |
| C6—Fe1—C2—C3 | 158.25 (14) | C7—Fe1—C8—C9 | 118.9 (2) |
| C7—Fe1—C2—C3 | 115.40 (16) | C4—Fe1—C8—C9 | −82.8 (2) |
| C9—Fe1—C2—C3 | 43.8 (4) | C2—Fe1—C8—C9 | −166.38 (17) |
| C4—Fe1—C2—C3 | −37.43 (13) | C3—Fe1—C8—C9 | −125.57 (18) |
| C8—Fe1—C2—C3 | 74.31 (18) | C10—Fe1—C8—C7 | −82.11 (19) |
| C10—Fe1—C2—C1 | −48.9 (3) | C5—Fe1—C8—C7 | −166.9 (2) |
| C5—Fe1—C2—C1 | 38.90 (13) | C1—Fe1—C8—C7 | 39.4 (4) |
| C6—Fe1—C2—C1 | −81.57 (16) | C6—Fe1—C8—C7 | −38.46 (16) |
| C7—Fe1—C2—C1 | −124.43 (16) | C9—Fe1—C8—C7 | −118.9 (2) |
| C9—Fe1—C2—C1 | 164.0 (3) | C4—Fe1—C8—C7 | 158.25 (16) |
| C4—Fe1—C2—C1 | 82.75 (14) | C2—Fe1—C8—C7 | 74.68 (19) |
| C8—Fe1—C2—C1 | −165.52 (15) | C3—Fe1—C8—C7 | 115.49 (17) |
| C3—Fe1—C2—C1 | 120.17 (18) | C7—C8—C9—C10 | −0.2 (3) |
| C1—C2—C3—C4 | 0.1 (2) | Fe1—C8—C9—C10 | −59.46 (18) |
| Fe1—C2—C3—C4 | 58.59 (15) | C7—C8—C9—Fe1 | 59.30 (16) |
| C1—C2—C3—Fe1 | −58.52 (14) | C5—Fe1—C9—C10 | −82.30 (19) |
| C10—Fe1—C3—C2 | 164.9 (3) | C1—Fe1—C9—C10 | −45.7 (3) |
| C5—Fe1—C3—C2 | 82.30 (13) | C6—Fe1—C9—C10 | 37.51 (17) |
| C1—Fe1—C3—C2 | 37.62 (12) | C7—Fe1—C9—C10 | 81.92 (19) |
| C6—Fe1—C3—C2 | −49.2 (3) | C4—Fe1—C9—C10 | −125.21 (17) |
| C7—Fe1—C3—C2 | −82.63 (16) | C2—Fe1—C9—C10 | 159.7 (3) |
| C9—Fe1—C3—C2 | −165.24 (14) | C8—Fe1—C9—C10 | 119.8 (3) |
| C4—Fe1—C3—C2 | 119.84 (19) | C3—Fe1—C9—C10 | −166.61 (16) |
| C8—Fe1—C3—C2 | −125.11 (15) | C10—Fe1—C9—C8 | −119.8 (3) |
| C10—Fe1—C3—C4 | 45.1 (4) | C5—Fe1—C9—C8 | 157.87 (17) |
| C5—Fe1—C3—C4 | −37.54 (14) | C1—Fe1—C9—C8 | −165.6 (2) |
| C1—Fe1—C3—C4 | −82.22 (15) | C6—Fe1—C9—C8 | −82.32 (19) |
| C6—Fe1—C3—C4 | −169.0 (2) | C7—Fe1—C9—C8 | −37.91 (18) |
| C7—Fe1—C3—C4 | 157.53 (16) | C4—Fe1—C9—C8 | 114.96 (18) |
| C9—Fe1—C3—C4 | 74.93 (18) | C2—Fe1—C9—C8 | 39.9 (4) |
| C2—Fe1—C3—C4 | −119.84 (19) | C3—Fe1—C9—C8 | 73.6 (2) |
| C8—Fe1—C3—C4 | 115.05 (16) | C8—C9—C10—C6 | −0.1 (3) |
| C2—C3—C4—C5 | 0.3 (2) | Fe1—C9—C10—C6 | −59.78 (17) |
| Fe1—C3—C4—C5 | 58.97 (15) | C8—C9—C10—Fe1 | 59.72 (18) |
| C2—C3—C4—Fe1 | −58.72 (15) | C7—C6—C10—C9 | 0.3 (3) |
| C10—Fe1—C4—C5 | 75.47 (18) | Fe1—C6—C10—C9 | 60.15 (18) |
| C1—Fe1—C4—C5 | −38.14 (12) | C7—C6—C10—Fe1 | −59.90 (16) |
| C6—Fe1—C4—C5 | 44.4 (4) | C5—Fe1—C10—C9 | 115.56 (16) |
| C7—Fe1—C4—C5 | −169.1 (2) | C1—Fe1—C10—C9 | 159.40 (15) |
| C9—Fe1—C4—C5 | 115.51 (15) | C6—Fe1—C10—C9 | −119.5 (2) |
| C2—Fe1—C4—C5 | −82.48 (14) | C7—Fe1—C10—C9 | −80.97 (18) |
| C8—Fe1—C4—C5 | 157.37 (14) | C4—Fe1—C10—C9 | 73.90 (19) |
| C3—Fe1—C4—C5 | −119.6 (2) | C2—Fe1—C10—C9 | −165.3 (2) |
| C10—Fe1—C4—C3 | −164.95 (16) | C8—Fe1—C10—C9 | −37.05 (16) |
| C5—Fe1—C4—C3 | 119.6 (2) | C3—Fe1—C10—C9 | 39.1 (4) |
| C1—Fe1—C4—C3 | 81.44 (15) | C5—Fe1—C10—C6 | −124.94 (17) |
| C6—Fe1—C4—C3 | 164.0 (3) | C1—Fe1—C10—C6 | −81.10 (18) |
| C7—Fe1—C4—C3 | −49.6 (3) | C7—Fe1—C10—C6 | 38.53 (17) |
| C9—Fe1—C4—C3 | −124.92 (16) | C9—Fe1—C10—C6 | 119.5 (2) |
| C2—Fe1—C4—C3 | 37.09 (13) | C4—Fe1—C10—C6 | −166.60 (16) |
| C8—Fe1—C4—C3 | −83.05 (17) | C2—Fe1—C10—C6 | −45.8 (3) |
| C3—C4—C5—C1 | −0.5 (2) | C8—Fe1—C10—C6 | 82.45 (19) |
| Fe1—C4—C5—C1 | 59.03 (14) | C3—Fe1—C10—C6 | 158.6 (3) |
| C3—C4—C5—Fe1 | −59.52 (15) | C12—N1—C11—O1 | 5.3 (3) |
| C2—C1—C5—C4 | 0.5 (2) | C12—N1—C11—C1 | −174.16 (18) |
| C11—C1—C5—C4 | −176.56 (19) | C2—C1—C11—O1 | 6.2 (3) |
| Fe1—C1—C5—C4 | −59.49 (15) | C5—C1—C11—O1 | −177.1 (2) |
| C2—C1—C5—Fe1 | 60.01 (13) | Fe1—C1—C11—O1 | 92.8 (2) |
| C11—C1—C5—Fe1 | −117.1 (2) | C2—C1—C11—N1 | −174.32 (18) |
| C10—Fe1—C5—C4 | −124.51 (17) | C5—C1—C11—N1 | 2.3 (3) |
| C1—Fe1—C5—C4 | 119.40 (18) | Fe1—C1—C11—N1 | −87.69 (19) |
| C6—Fe1—C5—C4 | −165.47 (16) | C11—N1—C12—C13 | −8.9 (3) |
| C7—Fe1—C5—C4 | 162.7 (3) | C11—N1—C12—C17 | 169.84 (19) |
| C9—Fe1—C5—C4 | −82.90 (17) | N1—C12—C13—C14 | 179.05 (19) |
| C2—Fe1—C5—C4 | 80.77 (15) | C17—C12—C13—C14 | 0.4 (3) |
| C8—Fe1—C5—C4 | −49.6 (3) | C12—C13—C14—C15 | −1.0 (3) |
| C3—Fe1—C5—C4 | 37.46 (14) | C13—C14—C15—C16 | 0.6 (3) |
| C10—Fe1—C5—C1 | 116.08 (15) | C14—C15—C16—C18 | −178.2 (2) |
| C6—Fe1—C5—C1 | 75.13 (16) | C14—C15—C16—C17 | 0.5 (3) |
| C7—Fe1—C5—C1 | 43.3 (4) | C20—N2—C17—C16 | 1.9 (3) |
| C9—Fe1—C5—C1 | 157.69 (15) | C20—N2—C17—C12 | −177.45 (17) |
| C4—Fe1—C5—C1 | −119.40 (18) | C18—C16—C17—N2 | −1.8 (3) |
| C2—Fe1—C5—C1 | −38.63 (13) | C15—C16—C17—N2 | 179.49 (18) |
| C8—Fe1—C5—C1 | −169.0 (2) | C18—C16—C17—C12 | 177.61 (17) |
| C3—Fe1—C5—C1 | −81.94 (14) | C15—C16—C17—C12 | −1.1 (3) |
| C5—Fe1—C6—C10 | 74.7 (2) | C13—C12—C17—N2 | −179.88 (17) |
| C1—Fe1—C6—C10 | 116.98 (17) | N1—C12—C17—N2 | 1.3 (2) |
| C7—Fe1—C6—C10 | −118.1 (2) | C13—C12—C17—C16 | 0.7 (3) |
| C9—Fe1—C6—C10 | −36.91 (16) | N1—C12—C17—C16 | −178.11 (16) |
| C4—Fe1—C6—C10 | 40.3 (4) | C17—C16—C18—C19 | −0.1 (3) |
| C2—Fe1—C6—C10 | 160.14 (15) | C15—C16—C18—C19 | 178.6 (2) |
| C8—Fe1—C6—C10 | −80.05 (18) | C16—C18—C19—C20 | 1.7 (3) |
| C3—Fe1—C6—C10 | −165.1 (2) | C17—N2—C20—C19 | −0.2 (3) |
| C10—Fe1—C6—C7 | 118.1 (2) | C18—C19—C20—N2 | −1.6 (3) |
We gratefully acknowledge financial support from the Foundation of Henan Educational Committee (2011B150001) and the Foundation of Henan University of Urban Construction (2010JYB007).
Abd-El-Aziz, A. S. & Manners, I. (2007). In Frontiers in Transition Metal-Containing Polymers. Hoboken, NJ: Wiley.
Fang, C. J., Duan, C. Y., Guo, D., He, C., Meng, Q. J., Wang, Z. M. & Yan, C. H. (2001). Chem. Commun. pp. 2540–2541.
Li, X., Liu, W., Zhang, H. Y. & Wu, B. L. (2008). J. Organomet. Chem. 693, 3295–3302.
Li, X., Wu, B. L., Liu, W., Niu, C. Y., Niu, Y. Y. & Zhang, H. Y. (2009). J. Coord. Chem. 62, 3142–3156.
Mata, J. A., Peris, E., Asselberghs, I., Van Boxel, R. & Persoons, A. (2001). New J. Chem. 25, 1043–1046.
Rigaku (2000). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Togni, A. & Hayashi, T. (1995). In Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science. New York: VCH Publishers.
Due to its special chemical, stereochemical and electrochemical properties (Togni et al., 1995), ferrocene has been extensively incorporated into larger compounds in order to take advantage of these properties (Mata et al., 2001; Abd-El-Aziz et al., 2007; Fang et al., 2001). As a continuation of our research related to ferrocenyl derivatives and their metal complexes (Li et al., 2008; Li et al., 2009), herein we report the crystal structure of 8-(Ferrocenoylamino)quinoline.
The molecular structure of the title compound is composed of a ferrocenyl group and a quinolyl group joined by an organic amide spacer. The Fe—C bond distances within the ferrocene group are in the range of 2.0259 (19)–2.048 (2) Å for the substituted cyclopentadienyl (Cp) ring [C1—C5] and 2.026 (2)–2.039 (2) Å for the unsubstituted Cp ring [C6—C10]. The planar cyclopentadienyl rings of the ferrocenyl unit are nearly parallel to each other [the interplanar angle is 0.632 (10) °]. The Cp rings are essentially eclipsed and the Fe-centroid distances are 1.6374 (3) Å (Cg1) and 1.6494 (3) Å (Cg2) with Cg1 and Cg2 are the centroids of the [C1—C5] and [C6—C10] rings. The [Cg1—Fe1—Cg2] angle is 179.324 (17) °. The carbamoyl group is essentially coplanar with the substituted cyclopentadienyl ring with a deviation of 4.9 (2) °. The angle formed by the carbamoyl group and the quinolyl group system is 9.4 (3) °.