metal-organic compounds
The molecular structure of the title compound, [Fe2(C5H5)2(C12H10N2)], is centrosymmetric, with bond parameters similar to its analogue [4](1)(1,4-dimethyl-2,3-diazabuta-1,3-diene)ferrocenophane. The cyclopentadienyl rings of the ferrocene moieties are eclipsed and their average dihedral angle with the Schiff base C=N-N=C fragment is 8.5 (4)°.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803002691/ob6213sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803002691/ob6213Isup2.hkl |
CCDC reference: 206758
Computing details top
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
[4](1)(2,3-diazabuta-1,3-dien)ferrocenophane top
Crystal data top
[Fe2(C5H5)2(C12H10N2)] | F(000) = 436 |
Mr = 424.10 | Dx = 1.573 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.5844 (11) Å | Cell parameters from 812 reflections |
b = 10.0804 (14) Å | θ = 2.7–27.5° |
c = 12.1698 (16) Å | µ = 1.63 mm−1 |
β = 105.726 (3)° | T = 293 K |
V = 895.6 (2) Å3 | Slab, dark orange |
Z = 2 | 0.24 × 0.16 × 0.02 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 2066 independent reflections |
Radiation source: fine-focus sealed tube | 1439 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.051 |
Detector resolution: 83.66 pixels mm-1 | θmax = 27.5°, θmin = 2.7° |
ω scans | h = −9→9 |
Absorption correction: empirical (SADABS; Sheldrick, 1996) | k = −13→12 |
Tmin = 0.696, Tmax = 0.968 | l = −15→8 |
5939 measured reflections |
Refinement top
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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.136 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0611P)2] where P = (Fo2 + 2Fc2)/3 |
2066 reflections | (Δ/σ)max < 0.001 |
119 parameters | Δρmax = 0.64 e Å−3 |
0 restraints | Δρmin = −0.42 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Fe1 | 0.21391 (8) | 0.17990 (6) | 0.66550 (5) | 0.0382 (2) | |
N1 | 0.5127 (5) | 0.0291 (4) | 0.9489 (3) | 0.0515 (10) | |
C1 | 0.3819 (6) | 0.0329 (4) | 0.7474 (4) | 0.0413 (10) | |
C2 | 0.4848 (6) | 0.1360 (5) | 0.7116 (4) | 0.0481 (12) | |
H2 | 0.5824 | 0.1893 | 0.7614 | 0.058* | |
C3 | 0.4218 (7) | 0.1455 (5) | 0.5915 (4) | 0.0513 (12) | |
H3 | 0.4665 | 0.2079 | 0.5435 | 0.062* | |
C4 | 0.2792 (7) | 0.0515 (5) | 0.5526 (4) | 0.0531 (12) | |
H4 | 0.2086 | 0.0384 | 0.4730 | 0.064* | |
C5 | 0.2544 (6) | −0.0188 (4) | 0.6473 (4) | 0.0463 (11) | |
H5 | 0.1648 | −0.0895 | 0.6453 | 0.056* | |
C6 | 0.0924 (7) | 0.2555 (5) | 0.7805 (4) | 0.0588 (14) | |
H6 | 0.1121 | 0.2259 | 0.8596 | 0.071* | |
C7 | 0.1899 (7) | 0.3549 (5) | 0.7429 (5) | 0.0596 (14) | |
H7 | 0.2913 | 0.4062 | 0.7912 | 0.072* | |
C8 | 0.1201 (7) | 0.3685 (5) | 0.6254 (5) | 0.0598 (14) | |
H8 | 0.1639 | 0.4308 | 0.5768 | 0.072* | |
C9 | −0.0228 (7) | 0.2761 (6) | 0.5883 (5) | 0.0637 (15) | |
H9 | −0.0973 | 0.2631 | 0.5096 | 0.076* | |
C10 | −0.0407 (7) | 0.2067 (5) | 0.6852 (5) | 0.0588 (14) | |
H10 | −0.1301 | 0.1367 | 0.6860 | 0.071* | |
C11 | 0.3885 (7) | −0.0100 (4) | 0.8623 (4) | 0.0493 (11) | |
H11 | 0.2990 | −0.0680 | 0.8728 | 0.059* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0403 (4) | 0.0338 (3) | 0.0438 (4) | 0.0017 (3) | 0.0170 (3) | −0.0024 (3) |
N1 | 0.051 (2) | 0.051 (2) | 0.052 (3) | 0.0000 (19) | 0.013 (2) | 0.008 (2) |
C1 | 0.047 (3) | 0.037 (2) | 0.041 (3) | 0.005 (2) | 0.012 (2) | 0.004 (2) |
C2 | 0.036 (2) | 0.046 (3) | 0.065 (4) | 0.002 (2) | 0.019 (2) | −0.001 (2) |
C3 | 0.059 (3) | 0.045 (3) | 0.061 (3) | 0.009 (2) | 0.035 (3) | 0.003 (2) |
C4 | 0.070 (3) | 0.044 (3) | 0.048 (3) | 0.011 (2) | 0.020 (2) | −0.003 (2) |
C5 | 0.061 (3) | 0.034 (2) | 0.048 (3) | 0.004 (2) | 0.022 (2) | −0.007 (2) |
C6 | 0.069 (4) | 0.062 (3) | 0.057 (3) | 0.012 (3) | 0.037 (3) | −0.003 (3) |
C7 | 0.062 (3) | 0.044 (3) | 0.079 (4) | 0.002 (2) | 0.028 (3) | −0.023 (3) |
C8 | 0.067 (4) | 0.043 (3) | 0.079 (4) | 0.018 (3) | 0.036 (3) | 0.012 (3) |
C9 | 0.056 (3) | 0.071 (4) | 0.059 (3) | 0.026 (3) | 0.006 (3) | −0.008 (3) |
C10 | 0.048 (3) | 0.045 (3) | 0.093 (4) | −0.002 (2) | 0.036 (3) | −0.012 (3) |
C11 | 0.053 (3) | 0.042 (3) | 0.053 (3) | 0.003 (2) | 0.015 (2) | 0.007 (2) |
Geometric parameters (Å, º) top
Fe1—C6 | 2.022 (4) | C1—C5 | 1.432 (6) |
Fe1—C2 | 2.027 (4) | C1—C2 | 1.436 (6) |
Fe1—C10 | 2.027 (4) | C1—C11 | 1.451 (6) |
Fe1—C7 | 2.031 (5) | C2—C3 | 1.412 (7) |
Fe1—C1 | 2.031 (4) | C3—C4 | 1.419 (6) |
Fe1—C9 | 2.033 (5) | C4—C5 | 1.409 (6) |
Fe1—C8 | 2.042 (5) | C6—C7 | 1.394 (7) |
Fe1—C4 | 2.044 (4) | C6—C10 | 1.404 (7) |
Fe1—C3 | 2.047 (4) | C7—C8 | 1.390 (8) |
Fe1—C5 | 2.048 (4) | C8—C9 | 1.408 (7) |
N1—C11 | 1.271 (6) | C9—C10 | 1.409 (7) |
N1—N1i | 1.436 (7) | ||
C6—Fe1—C2 | 120.6 (2) | C1—Fe1—C5 | 41.11 (17) |
C6—Fe1—C10 | 40.6 (2) | C9—Fe1—C5 | 123.8 (2) |
C2—Fe1—C10 | 157.4 (2) | C8—Fe1—C5 | 159.7 (2) |
C6—Fe1—C7 | 40.2 (2) | C4—Fe1—C5 | 40.27 (17) |
C2—Fe1—C7 | 105.9 (2) | C3—Fe1—C5 | 68.31 (18) |
C10—Fe1—C7 | 67.8 (2) | C11—N1—N1i | 110.4 (5) |
C6—Fe1—C1 | 106.18 (19) | C5—C1—C2 | 107.6 (4) |
C2—Fe1—C1 | 41.46 (17) | C5—C1—C11 | 123.3 (4) |
C10—Fe1—C1 | 122.0 (2) | C2—C1—C11 | 128.9 (4) |
C7—Fe1—C1 | 122.0 (2) | C5—C1—Fe1 | 70.1 (2) |
C6—Fe1—C9 | 68.2 (2) | C2—C1—Fe1 | 69.1 (2) |
C2—Fe1—C9 | 159.1 (2) | C11—C1—Fe1 | 122.9 (3) |
C10—Fe1—C9 | 40.6 (2) | C3—C2—C1 | 107.7 (4) |
C7—Fe1—C9 | 67.7 (2) | C3—C2—Fe1 | 70.5 (3) |
C1—Fe1—C9 | 158.9 (2) | C1—C2—Fe1 | 69.4 (2) |
C6—Fe1—C8 | 67.6 (2) | C2—C3—C4 | 108.3 (4) |
C2—Fe1—C8 | 122.1 (2) | C2—C3—Fe1 | 69.0 (2) |
C10—Fe1—C8 | 67.9 (2) | C4—C3—Fe1 | 69.6 (2) |
C7—Fe1—C8 | 39.9 (2) | C5—C4—C3 | 108.7 (4) |
C1—Fe1—C8 | 158.1 (2) | C5—C4—Fe1 | 70.0 (2) |
C9—Fe1—C8 | 40.4 (2) | C3—C4—Fe1 | 69.8 (3) |
C6—Fe1—C4 | 160.6 (2) | C4—C5—C1 | 107.7 (4) |
C2—Fe1—C4 | 68.6 (2) | C4—C5—Fe1 | 69.7 (3) |
C10—Fe1—C4 | 125.2 (2) | C1—C5—Fe1 | 68.8 (2) |
C7—Fe1—C4 | 158.5 (2) | C7—C6—C10 | 107.9 (5) |
C1—Fe1—C4 | 68.51 (18) | C7—C6—Fe1 | 70.2 (3) |
C9—Fe1—C4 | 109.6 (2) | C10—C6—Fe1 | 69.9 (3) |
C8—Fe1—C4 | 124.1 (2) | C8—C7—C6 | 108.7 (5) |
C6—Fe1—C3 | 156.7 (2) | C8—C7—Fe1 | 70.5 (3) |
C2—Fe1—C3 | 40.57 (19) | C6—C7—Fe1 | 69.6 (3) |
C10—Fe1—C3 | 161.2 (2) | C7—C8—C9 | 108.1 (5) |
C7—Fe1—C3 | 121.9 (2) | C7—C8—Fe1 | 69.6 (3) |
C1—Fe1—C3 | 68.67 (18) | C9—C8—Fe1 | 69.4 (3) |
C9—Fe1—C3 | 124.5 (2) | C8—C9—C10 | 107.5 (5) |
C8—Fe1—C3 | 108.2 (2) | C8—C9—Fe1 | 70.1 (3) |
C4—Fe1—C3 | 40.61 (18) | C10—C9—Fe1 | 69.5 (3) |
C6—Fe1—C5 | 123.6 (2) | C6—C10—C9 | 107.9 (5) |
C2—Fe1—C5 | 69.24 (19) | C6—C10—Fe1 | 69.5 (3) |
C10—Fe1—C5 | 108.58 (19) | C9—C10—Fe1 | 69.9 (3) |
C7—Fe1—C5 | 159.2 (2) | N1—C11—C1 | 122.0 (4) |
Symmetry code: (i) −x+1, −y, −z+2. |