[4](1)(2,3-Di­aza­buta-1,3-diene)­ferrocenophane

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)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.059
• wR factor = 0.136
• Data-to-parameter ratio = 17.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

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

Crystal data

[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) Å^3	Slab, dark orange
Z = 2	0.24 × 0.16 × 0.02 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.136	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0611P)^2] where P = (Fo^2 + 2Fc^2)/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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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—N1^i	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—N1^i	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.