rac-N,N′-Bis(1-ferrocen­yleth­yl)pyridine-2,6-dicarboxamide

Reddy, P.A.N.; Nasiruzzaman, S.M.; Lee, J.E.; Kim, T.-J.

doi:10.1107/S160053680900422X

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page m264

doi:10.1107/S160053680900422X

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rac-N,N′-Bis(1-ferrocenylethyl)pyridine-2,6-dicarboxamide

Pattubala A. N. Reddy,^a Sk. Md Nasiruzzaman,^a Ji Eun Lee ^b and Tae-Jeong Kim ^a ^*

^aDepartment of Applied Chemistry, College of Engineering, Kyungpook National University, Daegu 702-701, South Korea, and ^bCentral Instrument Facility, Gyeongsang National University, Jinju, South Korea
^*Correspondence e-mail: tjkim@knu.ac.kr

(Received 23 January 2009; accepted 5 February 2009; online 11 February 2009)

The title compound, [Fe₂(C₅H₅)₂(C₂₁H₂₁N₃O₂)], a potential novel N,N′,N′′-tridentate ligand with (non-crystallographic) C₂ axial symmetry, adopts a U-shaped molecular conformation.

Related literature

For the applications of ferrocenes, see: Feng et al. (2008 ). For the use of 1,2-disubstituted planar-chiral ferrocenes in asymmetric catalysis, see: Richards & Locke (1998 ); Kagan & Riant (1997 ). For the use of chiral C2-symmetric bisferrocenylaminophosphine ligands in asymmetric catalysis, see: Cho et al. (1999 ); Song et al. (1999 ). α-Diimine ligands are known to stablize organometallic complexes (van Koten & Vrieze, 1982 ) and have been widely employed in a number of catalytic reactions, see: Fache et al. (2000 ).

Experimental

Crystal data

[Fe₂(C₅H₅)₂(C₂₁H₂₁N₃O₂)]
M_r = 589.29
Monoclinic, P 2₁ /n
a = 13.1787 (8) Å
b = 10.2961 (6) Å
c = 19.8474 (12) Å
β = 103.620 (1)°
V = 2617.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.14 mm⁻¹
T = 298 (2) K
0.41 × 0.19 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Blessing, 1995 ; Sheldrick, 2004 ) T_min = 0.734, T_max = 0.842
14428 measured reflections
5126 independent reflections
3874 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.098
wR(F²) = 0.199
S = 1.20
5126 reflections
343 parameters
H-atom parameters constrained
Δρ_max = 0.75 e Å⁻³
Δρ_min = −0.61 e Å⁻³

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2002 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976 ); software used to prepare material for publication: WinGX Publication routines (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680900422X/tk2359sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680900422X/tk2359Isup2.hkl

checkCIF report

Comment top

Ferrocene derivatives have come a long way as a tool in chemistry, with applications in electrochemistry, materials science, synthesis and catalysis (Feng et al., 2008). The resurgence of interest in 1,2-disubstituted planar-chiral ferrocenes has resulted in numerous interesting compounds which are finding widespread application in asymmetric catalysis (Richards & Locke, 1998; Kagan & Riant, 1997). Our past success in the use of chiral C2-symmetric bisferrocenyl aminophosphine ligands in asymmetric catalysis (Song et al., 1999; Cho et al., 1999) has prompted us to examine related bisferrocenyl analogues, such as the title complex (I), as potential sources of chiral ligand. The α-diimine ligands are now well known to stablize organometallic complexes (van Koten & Vrieze, 1982) and have thus been widely employed in a number of catalytic reactions (Fache et al., 2000). Herein, an example of a completely new class of C2-symmetric bisferrocenyl amides, (I), that was formed via the reaction of 2,6-bis(chlorocarbonyl)pyridine with two equivalents of ferrocenyl ethylamine, is described.

The structure of (I), Fig. 1, shows the conformation of the nearly parallel Cp rings [the dihedral angle between their planes are 2.32 (1) and 1.04 (1)° for Fe1 and Fe2, respectively] is almost eclipsed in one ferrocene unit, whereas staggered by 5(2)° in the other. The two amide groups are nearly coplanar with the pyridine ring. The dihedral angles between the plane of the substituted Cp rings and central pyridyl ring are 86.6 (2) and 42.2 (2)°, respectively.

Related literature top

For the applications of ferrocenes, see: Feng et al. (2008). For the use of 1,2-disubstituted planar-chiral ferrocenes in asymmetric catalysis, see: Richards & Locke (1998); Kagan & Riant (1997). For the use of chiral C2-symmetric bisferrocenylaminophosphine ligands in asymmetric catalysis, see: Cho et al. (1999); Song et al. (1999). α-Diimine ligands are known to stablize organometallic complexes (van Koten & Vrieze, 1982) and have been widely employed in a number of catalytic reactions, see: Fache et al. (2000).

Experimental top

To a mixture of 2,6-bis(chlorocarbonyl)pyridine (244.0 mg, 1.21 mmol) and triethylamine (1.0 ml) in CH₂Cl₂ (10.0 ml) was added a solution of ferrocenyl ethylamine (0.43 g, 2.42 mmol) in CH₂Cl₂ (20.0 ml). The mixture was stirred at room temperature for 8 h after which it was washed with 5% HCl (3 x 20 ml) and 5% NaHCO₃ (4 x 30 ml). The product was separated by extraction with CH₂Cl₂, dried over magnesium sulfate, and the solvent removed. The remaining oily residue was eluted on a silica gel column with a mixture of CH₂Cl₂ and MeOH (95:5). The first orange band was collected, and the solvent evaporated to give an orange solid (750 mg, 65.2% yield). Single crystals were grown by slow diffusion of hexane into a CH₂Cl₂ solution of (I).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: WinGX Publication routines (Farrugia, 1999).

Figures top

Fig. 1. Molecular structure of (I) showing the atom numbering scheme and 30% probability thermal ellipsoids. Hydrogen atoms are omitted for clarity.

rac-N,N'-Bis(1-ferrocenylethyl)pyridine-2,6-dicarboxamide top

Crystal data top

[Fe(C₅H₅)₂(C₂₁H₂₁N₃O₂)]	F(000) = 1224
M_r = 589.29	D_x = 1.495 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4471 reflections
a = 13.1787 (8) Å	θ = 2.2–26.1°
b = 10.2961 (6) Å	µ = 1.14 mm⁻¹
c = 19.8474 (12) Å	T = 298 K
β = 103.620 (1)°	Rectangular, yellow
V = 2617.3 (3) Å³	0.41 × 0.19 × 0.15 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	5126 independent reflections
Radiation source: fine-focus sealed tube	3874 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Blessing, 1995; Sheldrick, 2004)	h = −16→16
T_min = 0.734, T_max = 0.842	k = −12→12
14428 measured reflections	l = −24→17

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)] = 0.098	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.199	H-atom parameters constrained
S = 1.20	w = 1/[σ²(F_o²) + (0.0634P)² + 8.1673P] where P = (F_o² + 2F_c²)/3
5126 reflections	(Δ/σ)_max < 0.001
343 parameters	Δρ_max = 0.75 e Å⁻³
0 restraints	Δρ_min = −0.61 e Å⁻³

Crystal data top

[Fe(C₅H₅)₂(C₂₁H₂₁N₃O₂)]	V = 2617.3 (3) Å³
M_r = 589.29	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.1787 (8) Å	µ = 1.14 mm⁻¹
b = 10.2961 (6) Å	T = 298 K
c = 19.8474 (12) Å	0.41 × 0.19 × 0.15 mm
β = 103.620 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5126 independent reflections
Absorption correction: multi-scan (SADABS; Blessing, 1995; Sheldrick, 2004)	3874 reflections with I > 2σ(I)
T_min = 0.734, T_max = 0.842	R_int = 0.046
14428 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.098	0 restraints
wR(F²) = 0.199	H-atom parameters constrained
S = 1.20	Δρ_max = 0.75 e Å⁻³
5126 reflections	Δρ_min = −0.61 e Å⁻³
343 parameters

Special details top

Experimental. Ratio of minimum to maximum apparent transmission: 0.734422

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Fe1	0.17053 (7)	0.10963 (9)	0.11043 (5)	0.0413 (3)
Fe2	0.53645 (7)	−0.29594 (9)	0.10434 (5)	0.0417 (3)
O1	0.4466 (5)	0.1233 (6)	0.3804 (3)	0.0812 (18)
O2	0.8132 (4)	−0.3087 (6)	0.3000 (3)	0.0715 (16)
N1	0.4599 (4)	0.0710 (6)	0.2728 (3)	0.0547 (16)
H1A	0.4946	0.0250	0.2498	0.066*
N2	0.6319 (4)	−0.0688 (5)	0.3218 (3)	0.0387 (12)
N3	0.7391 (4)	−0.1436 (6)	0.2299 (3)	0.0457 (14)
H3A	0.7067	−0.0710	0.2290	0.055*
C1	0.0384 (6)	0.1732 (8)	0.1360 (4)	0.056 (2)
H1B	0.0060	0.1346	0.1709	0.068*
C2	0.1144 (6)	0.2705 (7)	0.1476 (4)	0.059 (2)
H2B	0.1444	0.3116	0.1924	0.071*
C3	0.1396 (7)	0.3010 (8)	0.0850 (5)	0.071 (2)
H3B	0.1898	0.3667	0.0777	0.085*
C4	0.0788 (8)	0.2198 (10)	0.0346 (4)	0.079 (3)
H4A	0.0799	0.2183	−0.0146	0.095*
C5	0.0169 (6)	0.1404 (9)	0.0659 (4)	0.067 (2)
H5A	−0.0334	0.0752	0.0427	0.081*
C6	0.2467 (6)	−0.0314 (8)	0.0700 (5)	0.068 (2)
H6A	0.2341	−0.0524	0.0205	0.081*
C7	0.1942 (6)	−0.0863 (7)	0.1152 (5)	0.071 (3)
H7A	0.1404	−0.1539	0.1044	0.085*
C8	0.2348 (5)	−0.0303 (6)	0.1797 (4)	0.0555 (19)
H8A	0.2120	−0.0508	0.2220	0.067*
C9	0.3101 (5)	0.0660 (6)	0.1748 (3)	0.0392 (15)
C10	0.3179 (6)	0.0628 (8)	0.1041 (4)	0.060 (2)
H10A	0.3644	0.1158	0.0835	0.072*
C11	0.3724 (5)	0.1462 (7)	0.2333 (4)	0.0527 (18)
H11A	0.3269	0.1681	0.2642	0.063*
C12	0.4101 (7)	0.2730 (8)	0.2075 (5)	0.085 (3)
H12A	0.4491	0.3218	0.2463	0.102*
H12B	0.3510	0.3230	0.1836	0.102*
H12C	0.4539	0.2540	0.1764	0.102*
C13	0.4903 (6)	0.0677 (7)	0.3409 (4)	0.0503 (17)
C14	0.5841 (5)	−0.0196 (6)	0.3682 (3)	0.0412 (15)
C15	0.6128 (6)	−0.0516 (7)	0.4376 (3)	0.0530 (19)
H15A	0.5787	−0.0141	0.4688	0.064*
C16	0.6914 (6)	−0.1384 (8)	0.4601 (4)	0.059 (2)
H16A	0.7109	−0.1616	0.5067	0.071*
C17	0.7422 (6)	−0.1919 (8)	0.4129 (4)	0.058 (2)
H17A	0.7959	−0.2519	0.4267	0.069*
C18	0.7098 (5)	−0.1523 (7)	0.3437 (3)	0.0436 (16)
C19	0.7603 (5)	−0.2092 (8)	0.2893 (4)	0.0521 (18)
C20	0.7665 (5)	−0.1850 (7)	0.1659 (4)	0.0509 (18)
H20A	0.7984	−0.2714	0.1735	0.061*
C21	0.8435 (6)	−0.0937 (9)	0.1456 (5)	0.077 (3)
H21A	0.9051	−0.0880	0.1826	0.092*
H21B	0.8126	−0.0092	0.1365	0.092*
H21C	0.8620	−0.1258	0.1046	0.092*
C22	0.6698 (5)	−0.1939 (7)	0.1077 (3)	0.0482 (16)
C23	0.6523 (6)	−0.2865 (8)	0.0528 (4)	0.061 (2)
H23A	0.6994	−0.3576	0.0476	0.074*
C24	0.5548 (7)	−0.2590 (9)	0.0074 (4)	0.070 (2)
H24A	0.5226	−0.3076	−0.0347	0.083*
C25	0.5118 (6)	−0.1519 (7)	0.0333 (3)	0.058 (2)
H25A	0.4443	−0.1118	0.0124	0.069*
C26	0.5825 (6)	−0.1105 (6)	0.0944 (3)	0.0482 (17)
H26A	0.5719	−0.0371	0.1234	0.058*
C27	0.5281 (6)	−0.4809 (7)	0.1373 (4)	0.063 (2)
H27A	0.5684	−0.5549	0.1266	0.076*
C28	0.5586 (7)	−0.3973 (8)	0.1932 (4)	0.071 (2)
H28A	0.6241	−0.4025	0.2289	0.086*
C29	0.4804 (7)	−0.3058 (8)	0.1908 (4)	0.069 (2)
H29A	0.4817	−0.2353	0.2242	0.082*
C30	0.3991 (6)	−0.3315 (8)	0.1328 (4)	0.063 (2)
H30A	0.3341	−0.2820	0.1182	0.076*
C31	0.4292 (6)	−0.4399 (7)	0.0982 (4)	0.066 (2)
H31A	0.3885	−0.4802	0.0556	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0445 (5)	0.0423 (6)	0.0367 (5)	0.0193 (4)	0.0090 (4)	0.0047 (4)
Fe2	0.0507 (6)	0.0323 (5)	0.0366 (5)	0.0104 (4)	−0.0004 (4)	0.0010 (4)
O1	0.101 (5)	0.083 (4)	0.065 (4)	0.017 (4)	0.031 (3)	−0.022 (3)
O2	0.065 (4)	0.073 (4)	0.074 (4)	0.015 (3)	0.011 (3)	0.018 (3)
N1	0.043 (3)	0.075 (4)	0.044 (3)	0.014 (3)	0.006 (3)	−0.008 (3)
N2	0.036 (3)	0.040 (3)	0.036 (3)	−0.013 (2)	0.000 (2)	−0.003 (2)
N3	0.040 (3)	0.054 (4)	0.038 (3)	0.006 (3)	−0.001 (2)	−0.001 (3)
C1	0.051 (4)	0.064 (5)	0.057 (5)	0.022 (4)	0.017 (4)	−0.014 (4)
C2	0.066 (5)	0.044 (5)	0.062 (5)	0.030 (4)	0.004 (4)	−0.008 (4)
C3	0.077 (6)	0.051 (5)	0.083 (6)	0.038 (4)	0.016 (5)	0.030 (5)
C4	0.096 (7)	0.095 (7)	0.045 (5)	0.060 (6)	0.015 (5)	0.028 (5)
C5	0.050 (5)	0.076 (6)	0.064 (5)	0.033 (4)	−0.010 (4)	−0.020 (4)
C6	0.058 (5)	0.061 (5)	0.077 (6)	0.030 (4)	0.003 (4)	−0.017 (5)
C7	0.056 (5)	0.030 (4)	0.113 (8)	0.005 (3)	−0.005 (5)	−0.005 (4)
C8	0.050 (4)	0.035 (4)	0.073 (5)	0.003 (3)	−0.003 (4)	0.021 (4)
C9	0.033 (3)	0.038 (3)	0.045 (4)	0.012 (3)	0.005 (3)	0.009 (3)
C10	0.041 (4)	0.060 (5)	0.086 (6)	0.024 (4)	0.027 (4)	0.007 (4)
C11	0.041 (4)	0.056 (5)	0.061 (5)	0.008 (3)	0.012 (3)	0.000 (4)
C12	0.069 (6)	0.058 (6)	0.121 (8)	−0.014 (5)	0.006 (5)	−0.006 (5)
C13	0.052 (4)	0.050 (4)	0.047 (4)	−0.017 (3)	0.007 (3)	−0.007 (3)
C14	0.041 (4)	0.047 (4)	0.031 (3)	−0.021 (3)	−0.001 (3)	−0.005 (3)
C15	0.059 (5)	0.066 (5)	0.030 (4)	−0.029 (4)	0.002 (3)	−0.009 (3)
C16	0.061 (5)	0.071 (5)	0.034 (4)	−0.028 (4)	−0.012 (3)	0.013 (4)
C17	0.039 (4)	0.071 (5)	0.053 (4)	−0.019 (4)	−0.008 (3)	0.015 (4)
C18	0.031 (3)	0.057 (4)	0.037 (4)	−0.013 (3)	−0.003 (3)	0.009 (3)
C19	0.031 (4)	0.062 (5)	0.055 (4)	−0.006 (3)	−0.005 (3)	0.010 (4)
C20	0.050 (4)	0.054 (4)	0.050 (4)	0.012 (3)	0.013 (3)	−0.004 (3)
C21	0.057 (5)	0.104 (7)	0.077 (6)	−0.011 (5)	0.030 (4)	−0.015 (5)
C22	0.055 (4)	0.049 (4)	0.045 (4)	−0.001 (3)	0.019 (3)	−0.007 (3)
C23	0.066 (5)	0.069 (5)	0.050 (4)	0.005 (4)	0.016 (4)	−0.014 (4)
C24	0.100 (7)	0.082 (6)	0.026 (4)	−0.003 (5)	0.016 (4)	−0.010 (4)
C25	0.077 (5)	0.058 (5)	0.030 (4)	0.006 (4)	−0.005 (3)	0.021 (3)
C26	0.067 (5)	0.037 (4)	0.041 (4)	0.003 (3)	0.015 (3)	0.006 (3)
C27	0.068 (5)	0.039 (4)	0.074 (5)	0.007 (4)	−0.003 (4)	0.013 (4)
C28	0.077 (6)	0.057 (5)	0.066 (5)	−0.001 (5)	−0.013 (4)	0.034 (4)
C29	0.102 (7)	0.064 (5)	0.045 (4)	−0.022 (5)	0.028 (5)	0.003 (4)
C30	0.060 (5)	0.053 (5)	0.076 (6)	0.004 (4)	0.014 (4)	0.007 (4)
C31	0.059 (5)	0.044 (4)	0.080 (6)	−0.006 (4)	−0.013 (4)	0.005 (4)

Geometric parameters (Å, º) top

Fe1—C1	2.033 (7)	C8—C9	1.422 (9)
Fe1—C2	2.023 (7)	C8—H8A	0.9800
Fe1—C3	2.051 (7)	C9—C10	1.430 (10)
Fe1—C4	2.040 (7)	C9—C11	1.501 (9)
Fe1—C5	2.034 (7)	C10—H10A	0.9800
Fe1—C6	2.035 (7)	C11—C12	1.528 (11)
Fe1—C7	2.040 (7)	C11—H11A	0.9800
Fe1—C8	2.033 (6)	C12—H12A	0.9600
Fe1—C9	2.027 (6)	C12—H12B	0.9600
Fe1—C10	2.033 (7)	C12—H12C	0.9600
Fe2—C28	2.011 (7)	C13—C14	1.521 (10)
Fe2—C25	2.019 (6)	C14—C15	1.378 (9)
Fe2—C29	2.024 (7)	C15—C16	1.362 (11)
Fe2—C27	2.025 (7)	C15—H15A	0.9300
Fe2—C26	2.027 (7)	C16—C17	1.388 (11)
Fe2—C23	2.031 (8)	C16—H16A	0.9300
Fe2—C24	2.031 (7)	C17—C18	1.399 (9)
Fe2—C31	2.031 (8)	C17—H17A	0.9300
Fe2—C22	2.035 (7)	C18—C19	1.513 (10)
Fe2—C30	2.052 (8)	C20—C21	1.507 (10)
O1—C13	1.220 (8)	C20—C22	1.508 (10)
O2—C19	1.230 (8)	C20—H20A	0.9800
N1—C13	1.317 (8)	C21—H21A	0.9600
N1—C11	1.456 (9)	C21—H21B	0.9600
N1—H1A	0.8600	C21—H21C	0.9600
N2—C18	1.332 (8)	C22—C26	1.410 (9)
N2—C14	1.332 (8)	C22—C23	1.425 (9)
N3—C19	1.329 (8)	C23—C24	1.413 (11)
N3—C20	1.463 (8)	C23—H23A	0.9800
N3—H3A	0.8600	C24—C25	1.392 (11)
C1—C5	1.393 (10)	C24—H24A	0.9800
C1—C2	1.397 (11)	C25—C26	1.410 (9)
C1—H1B	0.9800	C25—H25A	0.9800
C2—C3	1.397 (11)	C26—H26A	0.9800
C2—H2B	0.9800	C27—C28	1.387 (11)
C3—C4	1.402 (13)	C27—C31	1.416 (10)
C3—H3B	0.9800	C27—H27A	0.9800
C4—C5	1.400 (12)	C28—C29	1.389 (12)
C4—H4A	0.9800	C28—H28A	0.9800
C5—H5A	0.9800	C29—C30	1.400 (11)
C6—C7	1.377 (12)	C29—H29A	0.9800
C6—C10	1.408 (11)	C30—C31	1.416 (11)
C6—H6A	0.9800	C30—H30A	0.9800
C7—C8	1.391 (11)	C31—H31A	0.9800
C7—H7A	0.9800

C2—Fe1—C9	107.9 (3)	C10—C6—H6A	124.8
C2—Fe1—C1	40.3 (3)	Fe1—C6—H6A	124.8
C9—Fe1—C1	128.2 (3)	C6—C7—C8	106.6 (7)
C2—Fe1—C8	117.6 (3)	C6—C7—Fe1	70.0 (4)
C9—Fe1—C8	41.0 (3)	C8—C7—Fe1	69.8 (4)
C1—Fe1—C8	107.7 (3)	C6—C7—H7A	126.7
C2—Fe1—C10	130.8 (3)	C8—C7—H7A	126.7
C9—Fe1—C10	41.2 (3)	Fe1—C7—H7A	126.7
C1—Fe1—C10	168.0 (3)	C7—C8—C9	110.5 (7)
C8—Fe1—C10	67.8 (3)	C7—C8—Fe1	70.3 (4)
C2—Fe1—C5	67.6 (3)	C9—C8—Fe1	69.3 (4)
C9—Fe1—C5	166.1 (3)	C7—C8—H8A	124.7
C1—Fe1—C5	40.1 (3)	C9—C8—H8A	124.7
C8—Fe1—C5	128.2 (4)	Fe1—C8—H8A	124.7
C10—Fe1—C5	151.4 (3)	C8—C9—C10	105.3 (6)
C2—Fe1—C6	170.1 (4)	C8—C9—C11	126.4 (6)
C9—Fe1—C6	68.4 (3)	C10—C9—C11	128.2 (6)
C1—Fe1—C6	149.2 (4)	C8—C9—Fe1	69.7 (4)
C8—Fe1—C6	66.1 (4)	C10—C9—Fe1	69.6 (4)
C10—Fe1—C6	40.5 (3)	C11—C9—Fe1	128.0 (4)
C5—Fe1—C6	118.2 (3)	C6—C10—C9	107.1 (7)
C2—Fe1—C4	67.0 (3)	C6—C10—Fe1	69.8 (4)
C9—Fe1—C4	151.7 (4)	C9—C10—Fe1	69.2 (4)
C1—Fe1—C4	67.1 (3)	C6—C10—H10A	126.4
C8—Fe1—C4	166.8 (4)	C9—C10—H10A	126.4
C10—Fe1—C4	119.7 (4)	Fe1—C10—H10A	126.4
C5—Fe1—C4	40.2 (4)	N1—C11—C9	110.1 (6)
C6—Fe1—C4	111.6 (4)	N1—C11—C12	110.9 (6)
C2—Fe1—C7	149.0 (4)	C9—C11—C12	111.9 (6)
C9—Fe1—C7	69.2 (3)	N1—C11—H11A	107.9
C1—Fe1—C7	115.9 (4)	C9—C11—H11A	107.9
C8—Fe1—C7	39.9 (3)	C12—C11—H11A	107.9
C10—Fe1—C7	68.3 (3)	C11—C12—H12A	109.5
C5—Fe1—C7	107.5 (3)	C11—C12—H12B	109.5
C6—Fe1—C7	39.5 (3)	H12A—C12—H12B	109.5
C4—Fe1—C7	129.9 (4)	C11—C12—H12C	109.5
C2—Fe1—C3	40.1 (3)	H12A—C12—H12C	109.5
C9—Fe1—C3	117.8 (3)	H12B—C12—H12C	109.5
C1—Fe1—C3	67.7 (3)	O1—C13—N1	124.9 (7)
C8—Fe1—C3	150.9 (4)	O1—C13—C14	121.1 (7)
C10—Fe1—C3	110.5 (4)	N1—C13—C14	114.0 (6)
C5—Fe1—C3	67.9 (4)	N2—C14—C15	122.4 (7)
C6—Fe1—C3	132.6 (4)	N2—C14—C13	117.1 (6)
C4—Fe1—C3	40.1 (4)	C15—C14—C13	120.4 (7)
C7—Fe1—C3	168.8 (4)	C16—C15—C14	119.5 (7)
C28—Fe2—C25	163.7 (4)	C16—C15—H15A	120.2
C28—Fe2—C29	40.3 (3)	C14—C15—H15A	120.2
C25—Fe2—C29	126.7 (4)	C15—C16—C17	119.3 (7)
C28—Fe2—C27	40.2 (3)	C15—C16—H16A	120.3
C25—Fe2—C27	154.7 (3)	C17—C16—H16A	120.3
C29—Fe2—C27	67.7 (4)	C16—C17—C18	117.6 (7)
C28—Fe2—C26	126.1 (3)	C16—C17—H17A	121.2
C25—Fe2—C26	40.8 (3)	C18—C17—H17A	121.2
C29—Fe2—C26	107.9 (3)	N2—C18—C17	122.8 (7)
C27—Fe2—C26	163.2 (3)	N2—C18—C19	116.9 (5)
C28—Fe2—C23	119.7 (4)	C17—C18—C19	120.3 (7)
C25—Fe2—C23	68.2 (3)	O2—C19—N3	124.7 (7)
C29—Fe2—C23	153.8 (3)	O2—C19—C18	121.6 (7)
C27—Fe2—C23	108.2 (3)	N3—C19—C18	113.7 (6)
C26—Fe2—C23	68.2 (3)	N3—C20—C21	111.7 (6)
C28—Fe2—C24	154.6 (4)	N3—C20—C22	110.3 (5)
C25—Fe2—C24	40.2 (3)	C21—C20—C22	109.5 (6)
C29—Fe2—C24	164.0 (4)	N3—C20—H20A	108.4
C27—Fe2—C24	120.7 (4)	C21—C20—H20A	108.4
C26—Fe2—C24	68.1 (3)	C22—C20—H20A	108.4
C23—Fe2—C24	40.7 (3)	C20—C21—H21A	109.5
C28—Fe2—C31	68.3 (3)	C20—C21—H21B	109.5
C25—Fe2—C31	119.9 (3)	H21A—C21—H21B	109.5
C29—Fe2—C31	68.1 (4)	C20—C21—H21C	109.5
C27—Fe2—C31	40.9 (3)	H21A—C21—H21C	109.5
C26—Fe2—C31	154.3 (3)	H21B—C21—H21C	109.5
C23—Fe2—C31	126.8 (3)	C26—C22—C23	106.7 (6)
C24—Fe2—C31	108.4 (4)	C26—C22—C20	127.7 (6)
C28—Fe2—C22	107.1 (3)	C23—C22—C20	125.6 (6)
C25—Fe2—C22	68.8 (3)	C26—C22—Fe2	69.4 (4)
C29—Fe2—C22	118.9 (3)	C23—C22—Fe2	69.3 (4)
C27—Fe2—C22	125.9 (3)	C20—C22—Fe2	128.6 (5)
C26—Fe2—C22	40.6 (3)	C24—C23—C22	108.2 (7)
C23—Fe2—C22	41.0 (3)	C24—C23—Fe2	69.7 (4)
C24—Fe2—C22	68.9 (3)	C22—C23—Fe2	69.7 (4)
C31—Fe2—C22	164.1 (3)	C24—C23—H23A	125.9
C28—Fe2—C30	67.7 (3)	C22—C23—H23A	125.9
C25—Fe2—C30	108.4 (3)	Fe2—C23—H23A	125.9
C29—Fe2—C30	40.2 (3)	C25—C24—C23	108.2 (7)
C27—Fe2—C30	68.0 (3)	C25—C24—Fe2	69.4 (4)
C26—Fe2—C30	119.9 (3)	C23—C24—Fe2	69.6 (4)
C23—Fe2—C30	164.6 (3)	C25—C24—H24A	125.9
C24—Fe2—C30	127.2 (4)	C23—C24—H24A	125.9
C31—Fe2—C30	40.6 (3)	Fe2—C24—H24A	125.9
C22—Fe2—C30	153.4 (3)	C24—C25—C26	108.3 (7)
C13—N1—C11	125.3 (6)	C24—C25—Fe2	70.4 (4)
C13—N1—H1A	117.3	C26—C25—Fe2	69.9 (4)
C11—N1—H1A	117.3	C24—C25—H25A	125.9
C18—N2—C14	118.3 (6)	C26—C25—H25A	125.9
C19—N3—C20	125.4 (6)	Fe2—C25—H25A	125.9
C19—N3—H3A	117.3	C25—C26—C22	108.7 (6)
C20—N3—H3A	117.3	C25—C26—Fe2	69.3 (4)
C5—C1—C2	108.0 (8)	C22—C26—Fe2	70.0 (4)
C5—C1—Fe1	70.0 (4)	C25—C26—H26A	125.6
C2—C1—Fe1	69.5 (4)	C22—C26—H26A	125.6
C5—C1—H1B	126.0	Fe2—C26—H26A	125.6
C2—C1—H1B	126.0	C28—C27—C31	108.0 (7)
Fe1—C1—H1B	126.0	C28—C27—Fe2	69.3 (4)
C1—C2—C3	109.0 (8)	C31—C27—Fe2	69.8 (4)
C1—C2—Fe1	70.2 (4)	C28—C27—H27A	126.0
C3—C2—Fe1	71.0 (4)	C31—C27—H27A	126.0
C1—C2—H2B	125.5	Fe2—C27—H27A	126.0
C3—C2—H2B	125.5	C27—C28—C29	108.7 (7)
Fe1—C2—H2B	125.5	C27—C28—Fe2	70.5 (4)
C2—C3—C4	106.6 (8)	C29—C28—Fe2	70.4 (4)
C2—C3—Fe1	68.9 (4)	C27—C28—H28A	125.7
C4—C3—Fe1	69.5 (5)	C29—C28—H28A	125.7
C2—C3—H3B	126.7	Fe2—C28—H28A	125.7
C4—C3—H3B	126.7	C28—C29—C30	108.6 (8)
Fe1—C3—H3B	126.7	C28—C29—Fe2	69.3 (5)
C5—C4—C3	109.0 (8)	C30—C29—Fe2	71.0 (5)
C5—C4—Fe1	69.7 (4)	C28—C29—H29A	125.7
C3—C4—Fe1	70.4 (4)	C30—C29—H29A	125.7
C5—C4—H4A	125.5	Fe2—C29—H29A	125.7
C3—C4—H4A	125.5	C29—C30—C31	107.5 (7)
Fe1—C4—H4A	125.5	C29—C30—Fe2	68.8 (5)
C1—C5—C4	107.4 (8)	C31—C30—Fe2	68.9 (5)
C1—C5—Fe1	69.9 (4)	C29—C30—H30A	126.2
C4—C5—Fe1	70.1 (5)	C31—C30—H30A	126.2
C1—C5—H5A	126.3	Fe2—C30—H30A	126.2
C4—C5—H5A	126.3	C30—C31—C27	107.2 (7)
Fe1—C5—H5A	126.3	C30—C31—Fe2	70.5 (4)
C7—C6—C10	110.4 (8)	C27—C31—Fe2	69.3 (4)
C7—C6—Fe1	70.5 (5)	C30—C31—H31A	126.4
C10—C6—Fe1	69.7 (4)	C27—C31—H31A	126.4
C7—C6—H6A	124.8	Fe2—C31—H31A	126.4

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)₂(C₂₁H₂₁N₃O₂)]
M_r	589.29
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	13.1787 (8), 10.2961 (6), 19.8474 (12)
β (°)	103.620 (1)
V (Å³)	2617.3 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.14
Crystal size (mm)	0.41 × 0.19 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Blessing, 1995; Sheldrick, 2004)
T_min, T_max	0.734, 0.842
No. of measured, independent and observed [I > 2σ(I)] reflections	14428, 5126, 3874
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.098, 0.199, 1.20
No. of reflections	5126
No. of parameters	343
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.75, −0.61

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976), WinGX Publication routines (Farrugia, 1999).

Acknowledgements

The work was supported by MKE through the Regional Technology Innovation Program (grant No. RTI 04–01–01). We thank Professor Lee Shimsung of Gyeongsang National University for providing instrumental facilities.

References

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