


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808026330/lh2673sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536808026330/lh2673Isup2.hkl |
CCDC reference: 702415
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.004 Å
- R factor = 0.029
- wR factor = 0.078
- Data-to-parameter ratio = 15.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C5 -- C10 .. 5.91 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C17 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Fe1
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Ferrocenecarbaldehyde (1.2 g, 2.79 mmol) was dissolved in 30 ml benzene at room temperature, after the material had dissolved completely, 0.8 g naphthylamine (5.58 mmol) was added to the solution. The mixture was refluxed with a Dean-Stark apparatus to remove the water produced during the reaction. After 5 h, the solvents were removed on a rotary evaporator and the residue was recrystallized in ether to give orange crystals 1.55 g. Yield 82%.
H atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.98 Å and with Uiso(H) = 1.2 times Ueq(C).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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).
![]() | Fig. 1. Molecular structure of title compound. Displacement ellipsoids are drawn at the 30% probability for non-H atoms. |
[Fe(C5H5)(C16H12N)] | F(000) = 1408 |
Mr = 339.21 | Dx = 1.396 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 8631 reflections |
a = 19.5283 (4) Å | θ = 2.2–26.9° |
b = 7.3578 (2) Å | µ = 0.93 mm−1 |
c = 23.7390 (5) Å | T = 293 K |
β = 108.826 (1)° | Block, orange |
V = 3228.47 (13) Å3 | 0.24 × 0.20 × 0.15 mm |
Z = 8 |
Bruker SMART 1000 CCD diffractometer | 3164 independent reflections |
Radiation source: fine-focus sealed tube | 2740 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
ϕ and ω scans | θmax = 26.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −24→24 |
Tmin = 0.807, Tmax = 0.873 | k = −9→8 |
18034 measured reflections | l = −29→29 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.028 | H-atom parameters constrained |
wR(F2) = 0.078 | w = 1/[σ2(Fo2) + (0.0401P)2 + 1.5179P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
3164 reflections | Δρmax = 0.19 e Å−3 |
209 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00052 (11) |
[Fe(C5H5)(C16H12N)] | V = 3228.47 (13) Å3 |
Mr = 339.21 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 19.5283 (4) Å | µ = 0.93 mm−1 |
b = 7.3578 (2) Å | T = 293 K |
c = 23.7390 (5) Å | 0.24 × 0.20 × 0.15 mm |
β = 108.826 (1)° |
Bruker SMART 1000 CCD diffractometer | 3164 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2740 reflections with I > 2σ(I) |
Tmin = 0.807, Tmax = 0.873 | Rint = 0.022 |
18034 measured reflections |
R[F2 > 2σ(F2)] = 0.028 | 0 restraints |
wR(F2) = 0.078 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.19 e Å−3 |
3164 reflections | Δρmin = −0.19 e Å−3 |
209 parameters |
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 | 0.244742 (12) | 0.85825 (3) | 0.123387 (10) | 0.04360 (11) | |
N1 | 0.38867 (8) | 0.9603 (2) | 0.28006 (7) | 0.0572 (4) | |
C1 | 0.48453 (10) | 0.8798 (3) | 0.39478 (9) | 0.0601 (5) | |
H1 | 0.4528 | 0.7910 | 0.3734 | 0.072* | |
C2 | 0.53061 (11) | 0.8400 (4) | 0.45027 (10) | 0.0738 (6) | |
H2 | 0.5295 | 0.7251 | 0.4663 | 0.089* | |
C3 | 0.57918 (12) | 0.9697 (5) | 0.48302 (11) | 0.0864 (8) | |
H3 | 0.6108 | 0.9408 | 0.5206 | 0.104* | |
C4 | 0.58042 (11) | 1.1370 (4) | 0.46033 (12) | 0.0839 (8) | |
H4 | 0.6129 | 1.2226 | 0.4828 | 0.101* | |
C5 | 0.53241 (16) | 1.3586 (4) | 0.37809 (14) | 0.0928 (9) | |
H5 | 0.5645 | 1.4463 | 0.3997 | 0.111* | |
C6 | 0.48643 (18) | 1.4021 (4) | 0.32367 (15) | 0.0979 (9) | |
H6 | 0.4867 | 1.5187 | 0.3086 | 0.118* | |
C7 | 0.43728 (14) | 1.2685 (3) | 0.28922 (11) | 0.0792 (6) | |
H7 | 0.4055 | 1.2983 | 0.2518 | 0.095* | |
C8 | 0.43708 (10) | 1.0975 (3) | 0.31132 (9) | 0.0592 (5) | |
C9 | 0.48424 (9) | 1.0520 (3) | 0.36948 (9) | 0.0566 (5) | |
C10 | 0.53325 (11) | 1.1864 (3) | 0.40271 (11) | 0.0706 (6) | |
C11 | 0.38579 (9) | 0.9244 (3) | 0.22709 (8) | 0.0521 (4) | |
H11 | 0.4169 | 0.9852 | 0.2110 | 0.063* | |
C12 | 0.33590 (9) | 0.7921 (3) | 0.19079 (7) | 0.0478 (4) | |
C13 | 0.33816 (9) | 0.7214 (3) | 0.13539 (8) | 0.0522 (4) | |
H13 | 0.3747 | 0.7495 | 0.1165 | 0.063* | |
C14 | 0.27871 (11) | 0.6024 (3) | 0.11281 (9) | 0.0582 (5) | |
H14 | 0.2666 | 0.5353 | 0.0752 | 0.070* | |
C15 | 0.23897 (11) | 0.5992 (2) | 0.15338 (9) | 0.0559 (5) | |
H15 | 0.1945 | 0.5302 | 0.1485 | 0.067* | |
C16 | 0.27343 (9) | 0.7156 (3) | 0.20106 (8) | 0.0527 (4) | |
H16 | 0.2573 | 0.7409 | 0.2353 | 0.063* | |
C17 | 0.23857 (15) | 1.1334 (3) | 0.11874 (14) | 0.0953 (10) | |
H17 | 0.2738 | 1.2181 | 0.1443 | 0.114* | |
C18 | 0.24075 (12) | 1.0616 (3) | 0.06452 (12) | 0.0833 (7) | |
H18 | 0.2775 | 1.0878 | 0.0456 | 0.100* | |
C19 | 0.18066 (11) | 0.9451 (3) | 0.04201 (9) | 0.0702 (6) | |
H19 | 0.1680 | 0.8761 | 0.0047 | 0.084* | |
C20 | 0.14173 (10) | 0.9477 (3) | 0.08299 (10) | 0.0702 (6) | |
H20 | 0.0976 | 0.8786 | 0.0792 | 0.084* | |
C21 | 0.17731 (13) | 1.0623 (3) | 0.13038 (12) | 0.0843 (7) | |
H21 | 0.1623 | 1.0891 | 0.1651 | 0.101* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.04306 (15) | 0.03924 (16) | 0.04794 (16) | 0.00129 (10) | 0.01389 (11) | 0.00106 (10) |
N1 | 0.0501 (8) | 0.0651 (11) | 0.0572 (9) | −0.0100 (7) | 0.0186 (7) | −0.0072 (8) |
C1 | 0.0467 (9) | 0.0704 (14) | 0.0648 (12) | −0.0069 (9) | 0.0201 (9) | −0.0205 (10) |
C2 | 0.0598 (12) | 0.0917 (18) | 0.0681 (13) | 0.0069 (11) | 0.0181 (11) | −0.0153 (12) |
C3 | 0.0578 (12) | 0.120 (2) | 0.0766 (15) | 0.0029 (14) | 0.0148 (11) | −0.0353 (16) |
C4 | 0.0484 (11) | 0.117 (2) | 0.0868 (17) | −0.0228 (13) | 0.0227 (11) | −0.0562 (16) |
C5 | 0.0972 (19) | 0.090 (2) | 0.109 (2) | −0.0442 (15) | 0.0583 (18) | −0.0454 (17) |
C6 | 0.135 (3) | 0.0633 (16) | 0.125 (2) | −0.0290 (16) | 0.082 (2) | −0.0183 (16) |
C7 | 0.0958 (17) | 0.0693 (16) | 0.0859 (16) | −0.0127 (13) | 0.0480 (14) | −0.0083 (13) |
C8 | 0.0545 (10) | 0.0604 (13) | 0.0720 (12) | −0.0114 (9) | 0.0333 (10) | −0.0141 (10) |
C9 | 0.0427 (9) | 0.0695 (13) | 0.0647 (11) | −0.0123 (9) | 0.0271 (8) | −0.0253 (10) |
C10 | 0.0572 (11) | 0.0777 (16) | 0.0901 (16) | −0.0231 (11) | 0.0421 (12) | −0.0372 (13) |
C11 | 0.0422 (8) | 0.0560 (11) | 0.0589 (10) | 0.0003 (8) | 0.0174 (8) | 0.0008 (9) |
C12 | 0.0443 (8) | 0.0480 (10) | 0.0505 (9) | 0.0060 (8) | 0.0144 (7) | 0.0054 (8) |
C13 | 0.0516 (9) | 0.0475 (11) | 0.0619 (11) | 0.0077 (8) | 0.0247 (8) | −0.0005 (9) |
C14 | 0.0682 (12) | 0.0426 (10) | 0.0664 (12) | 0.0032 (9) | 0.0253 (10) | −0.0086 (9) |
C15 | 0.0606 (10) | 0.0410 (10) | 0.0665 (12) | −0.0043 (8) | 0.0211 (9) | 0.0063 (9) |
C16 | 0.0544 (10) | 0.0558 (11) | 0.0497 (9) | −0.0005 (9) | 0.0190 (8) | 0.0075 (8) |
C17 | 0.0882 (19) | 0.0363 (13) | 0.131 (3) | 0.0101 (11) | −0.0070 (18) | 0.0084 (13) |
C18 | 0.0686 (13) | 0.0715 (16) | 0.1028 (19) | 0.0034 (12) | 0.0181 (13) | 0.0452 (15) |
C19 | 0.0632 (12) | 0.0800 (16) | 0.0589 (12) | 0.0044 (11) | 0.0078 (9) | 0.0219 (11) |
C20 | 0.0472 (10) | 0.0786 (16) | 0.0771 (14) | 0.0138 (10) | 0.0092 (10) | 0.0123 (12) |
C21 | 0.0770 (15) | 0.0724 (16) | 0.0928 (17) | 0.0347 (13) | 0.0126 (13) | −0.0089 (14) |
Fe1—C13 | 2.0219 (17) | C7—C8 | 1.364 (3) |
Fe1—C17 | 2.029 (2) | C7—H7 | 0.9300 |
Fe1—C18 | 2.031 (2) | C8—C9 | 1.430 (3) |
Fe1—C12 | 2.0317 (16) | C9—C10 | 1.424 (3) |
Fe1—C19 | 2.0362 (19) | C11—C12 | 1.448 (3) |
Fe1—C16 | 2.0366 (17) | C11—H11 | 0.9300 |
Fe1—C14 | 2.0379 (18) | C12—C13 | 1.428 (2) |
Fe1—C20 | 2.0383 (19) | C12—C16 | 1.434 (2) |
Fe1—C21 | 2.039 (2) | C13—C14 | 1.414 (3) |
Fe1—C15 | 2.0506 (18) | C13—H13 | 0.9800 |
N1—C11 | 1.269 (2) | C14—C15 | 1.419 (3) |
N1—C8 | 1.418 (2) | C14—H14 | 0.9800 |
C1—C2 | 1.366 (3) | C15—C16 | 1.406 (3) |
C1—C9 | 1.402 (3) | C15—H15 | 0.9800 |
C1—H1 | 0.9300 | C16—H16 | 0.9800 |
C2—C3 | 1.393 (3) | C17—C18 | 1.405 (4) |
C2—H2 | 0.9300 | C17—C21 | 1.412 (4) |
C3—C4 | 1.347 (4) | C17—H17 | 0.9800 |
C3—H3 | 0.9300 | C18—C19 | 1.412 (3) |
C4—C10 | 1.428 (4) | C18—H18 | 0.9800 |
C4—H4 | 0.9300 | C19—C20 | 1.415 (3) |
C5—C6 | 1.352 (4) | C19—H19 | 0.9800 |
C5—C10 | 1.393 (4) | C20—C21 | 1.398 (3) |
C5—H5 | 0.9300 | C20—H20 | 0.9800 |
C6—C7 | 1.432 (4) | C21—H21 | 0.9800 |
C6—H6 | 0.9300 | ||
C13—Fe1—C17 | 122.66 (10) | C1—C9—C10 | 118.8 (2) |
C13—Fe1—C18 | 107.24 (9) | C1—C9—C8 | 122.50 (18) |
C17—Fe1—C18 | 40.48 (10) | C10—C9—C8 | 118.7 (2) |
C13—Fe1—C12 | 41.27 (7) | C5—C10—C9 | 119.0 (2) |
C17—Fe1—C12 | 107.65 (9) | C5—C10—C4 | 123.4 (2) |
C18—Fe1—C12 | 123.20 (8) | C9—C10—C4 | 117.7 (2) |
C13—Fe1—C19 | 122.71 (8) | N1—C11—C12 | 122.42 (17) |
C17—Fe1—C19 | 68.15 (11) | N1—C11—H11 | 118.8 |
C18—Fe1—C19 | 40.61 (9) | C12—C11—H11 | 118.8 |
C12—Fe1—C19 | 159.46 (8) | C13—C12—C16 | 107.11 (16) |
C13—Fe1—C16 | 69.13 (7) | C13—C12—C11 | 125.31 (16) |
C17—Fe1—C16 | 123.88 (11) | C16—C12—C11 | 127.49 (16) |
C18—Fe1—C16 | 160.13 (10) | C13—C12—Fe1 | 69.00 (10) |
C12—Fe1—C16 | 41.27 (7) | C16—C12—Fe1 | 69.55 (10) |
C19—Fe1—C16 | 157.80 (8) | C11—C12—Fe1 | 123.92 (13) |
C13—Fe1—C14 | 40.77 (8) | C14—C13—C12 | 107.99 (16) |
C17—Fe1—C14 | 158.57 (11) | C14—C13—Fe1 | 70.23 (10) |
C18—Fe1—C14 | 122.49 (11) | C12—C13—Fe1 | 69.73 (9) |
C12—Fe1—C14 | 68.81 (8) | C14—C13—H13 | 126.0 |
C19—Fe1—C14 | 107.33 (10) | C12—C13—H13 | 126.0 |
C16—Fe1—C14 | 68.30 (8) | Fe1—C13—H13 | 126.0 |
C13—Fe1—C20 | 159.35 (9) | C13—C14—C15 | 108.38 (17) |
C17—Fe1—C20 | 67.66 (10) | C13—C14—Fe1 | 69.01 (10) |
C18—Fe1—C20 | 68.01 (9) | C15—C14—Fe1 | 70.18 (10) |
C12—Fe1—C20 | 158.25 (8) | C13—C14—H14 | 125.8 |
C19—Fe1—C20 | 40.63 (8) | C15—C14—H14 | 125.8 |
C16—Fe1—C20 | 122.26 (8) | Fe1—C14—H14 | 125.8 |
C14—Fe1—C20 | 123.46 (9) | C16—C15—C14 | 108.16 (16) |
C13—Fe1—C21 | 158.81 (9) | C16—C15—Fe1 | 69.35 (10) |
C17—Fe1—C21 | 40.62 (11) | C14—C15—Fe1 | 69.22 (10) |
C18—Fe1—C21 | 68.36 (11) | C16—C15—H15 | 125.9 |
C12—Fe1—C21 | 122.47 (9) | C14—C15—H15 | 125.9 |
C19—Fe1—C21 | 68.33 (10) | Fe1—C15—H15 | 125.9 |
C16—Fe1—C21 | 107.57 (10) | C15—C16—C12 | 108.36 (16) |
C14—Fe1—C21 | 159.17 (10) | C15—C16—Fe1 | 70.42 (10) |
C20—Fe1—C21 | 40.11 (9) | C12—C16—Fe1 | 69.18 (9) |
C13—Fe1—C15 | 68.67 (8) | C15—C16—H16 | 125.8 |
C17—Fe1—C15 | 159.62 (11) | C12—C16—H16 | 125.8 |
C18—Fe1—C15 | 158.31 (11) | Fe1—C16—H16 | 125.8 |
C12—Fe1—C15 | 68.67 (8) | C18—C17—C21 | 108.5 (2) |
C19—Fe1—C15 | 122.37 (9) | C18—C17—Fe1 | 69.86 (13) |
C16—Fe1—C15 | 40.24 (8) | C21—C17—Fe1 | 70.08 (13) |
C14—Fe1—C15 | 40.60 (8) | C18—C17—H17 | 125.7 |
C20—Fe1—C15 | 107.88 (9) | C21—C17—H17 | 125.7 |
C21—Fe1—C15 | 123.16 (10) | Fe1—C17—H17 | 125.7 |
C11—N1—C8 | 118.44 (16) | C17—C18—C19 | 107.9 (2) |
C2—C1—C9 | 121.2 (2) | C17—C18—Fe1 | 69.66 (13) |
C2—C1—H1 | 119.4 | C19—C18—Fe1 | 69.88 (12) |
C9—C1—H1 | 119.4 | C17—C18—H18 | 126.0 |
C1—C2—C3 | 120.6 (3) | C19—C18—H18 | 126.0 |
C1—C2—H2 | 119.7 | Fe1—C18—H18 | 126.0 |
C3—C2—H2 | 119.7 | C18—C19—C20 | 107.3 (2) |
C4—C3—C2 | 120.0 (2) | C18—C19—Fe1 | 69.51 (12) |
C4—C3—H3 | 120.0 | C20—C19—Fe1 | 69.76 (11) |
C2—C3—H3 | 120.0 | C18—C19—H19 | 126.4 |
C3—C4—C10 | 121.8 (2) | C20—C19—H19 | 126.4 |
C3—C4—H4 | 119.1 | Fe1—C19—H19 | 126.4 |
C10—C4—H4 | 119.1 | C21—C20—C19 | 108.9 (2) |
C6—C5—C10 | 122.0 (2) | C21—C20—Fe1 | 69.98 (12) |
C6—C5—H5 | 119.0 | C19—C20—Fe1 | 69.60 (11) |
C10—C5—H5 | 119.0 | C21—C20—H20 | 125.5 |
C5—C6—C7 | 120.0 (3) | C19—C20—H20 | 125.5 |
C5—C6—H6 | 120.0 | Fe1—C20—H20 | 125.5 |
C7—C6—H6 | 120.0 | C20—C21—C17 | 107.3 (2) |
C8—C7—C6 | 119.9 (3) | C20—C21—Fe1 | 69.91 (12) |
C8—C7—H7 | 120.1 | C17—C21—Fe1 | 69.30 (13) |
C6—C7—H7 | 120.1 | C20—C21—H21 | 126.3 |
C7—C8—N1 | 122.6 (2) | C17—C21—H21 | 126.3 |
C7—C8—C9 | 120.4 (2) | Fe1—C21—H21 | 126.3 |
N1—C8—C9 | 116.87 (18) |
Experimental details
Crystal data | |
Chemical formula | [Fe(C5H5)(C16H12N)] |
Mr | 339.21 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 293 |
a, b, c (Å) | 19.5283 (4), 7.3578 (2), 23.7390 (5) |
β (°) | 108.826 (1) |
V (Å3) | 3228.47 (13) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.93 |
Crystal size (mm) | 0.24 × 0.20 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART 1000 CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.807, 0.873 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18034, 3164, 2740 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.028, 0.078, 1.05 |
No. of reflections | 3164 |
No. of parameters | 209 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.19 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Transition metal complexes derived from ferrocene have attracted great intrest due to their applications as precursors for the synthesis of organic as well as organometallic compounds (Johnson & Sames, 2000), in homogeneous catalysis (Baar et al., 2000), or even in biological chemistry (Staveren & Metzler-Nolte, 2004). In this paper we reported the synthesis and crystal structure of the title compound (1). The molecular structure of (I) [Fig. 1] consists of a naphthyliminomethyl moiety and a ferrocene unit. In the ferrocene unit, the unsubstituted cyclopentadienyl ring and the substituted cyclopentadienyl ring are approximately eclipsed, and the interplannar angle is 0.8 (7)°. The Fe atom is slightly closer to the substituted cyclopentadienyl ring with a Fe···ring centroid distance of 1.639 (2) vs. 1.645 (2) for the other ring. The C=N double bond is almost parallel to the substituted cyclopentadienyl ring with the deviation 10.3 (1)°. The angle formed by the C=N double bond and the naphthyl ring is 47.1 (1) °. The torsion angle C-N=C-C is 177.32 (5)°.