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Acta Cryst. (2007). E63, m3079    [ doi:10.1107/S1600536807058503 ]

Bis{[1-(quinolin-2-ylmethylenehydrazono)ethyl]-[eta]5-cyclopentadienyl}iron(II)

J. Zhou, L.-P. Zheng, C.-L. Chen and M.-X. Li

Abstract top

The title complex, [Fe(C17H14N3)2], was prepared by the reaction of 1,1'-diacetylferrocenedihydrazone with 2-quinolinecarboxaldehyde. The title compound adopts a Z configuration, in which the two quinoline groups from the two side chains are perfectly planar and nearly parallel.

Comment top

There is considerable interest in ferrocene-based ligands dueing to their potential application in many and diverse areas of chemistry (Togni & Hayashi, 1995). In addition, ferrocene-containing ligand are versatile ligands which can give rise to different geometries upon coordination to transition metal ions, dependent on the number and distribution of the donor sites and the coordination requirements of the metal (Constable, 1992; Constable, 1994).

The title compound, (I), is an easy-to-prepare ferrocenyl-containing imine-based bis-tridentate system. The average Fe—Cring distance is 2.034 Å, in agreement with the value 2.04 Å of the free ferrocene. The C—C distances (1.4123 Å, average) and C—C—C angles (107.99 °, average) of the ferrocenyl units are all similar to those reported in the literature (Abuhijleh & Woods, 1992; Takusagawa & Koetzle 1979; Allen, & Kennard 1993). The cyclopentadienylrings are perfectly planar and nearly parallel with a dihedral angle of 2.1 ° at Fe1. The two pyridoquinoline groups attached to cyclopentadienyl ring adopt cis configuration corresponding to ferrocenyl. In the two side chains, the bond distances of N2—C10, N3—C11, N4—C23 and N5—C25 are 1.247 (4),1.286 (4), 1.288 (4), and 1.248 (4) Å, respectively. All of the C—N and C—C bond lengths are intermediate between formal single and double bonds. The measured N—N bond distances (N2—N3 = 1.396 (3) Å, N4—N5 = 1.406 (3) Å) are also intermediate between single and double bonds, pointing to extensive electron delocalization over the entire molecular skeleton (Duan et al., 1994; Tian et al., 1996).

Related literature top

For related literature, see: Abuhijleh & Woods (1992); Allen & Kennard (1993); Constable (1992); Duan et al. (1994); Takusagawa & Koetzle (1979); Tian et al. (1996); Togni & Hayashi (1995); Constable (1994).

Experimental top

All reagents were commercially available and of analytical grade. The title compound was synthesized by the reaction of 1,1'-diacetylferrocenedihydrazone (1.2 g, 4 mmol) with 2-quinolinecarboxaldehyde (0.32 g, 8 mmol) in ethanol (15 ml). Five drops of acetic acid were added to the reaction solution as catalyst. After refluxing for 4 h, the solution was allowed to cool to room temperature, a dark-red precipitate was filtered, washed with ethanol, and dried in vacuo (yield 90%).

Refinement top

All H atoms were positioned geometrically and refined as riding with C—H = 0.93 − 0.98Å and with Uiso(H) = 1.2Ueq(C) or1.5Ueq (methyl C).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing atom displacement ellipsoids drawn at the 50% probability level.
Bis{[1-(quinolin-2-ylmethylenehydrazono)ethyl]-η5-cyclopentadienyl}iron(II) top
Crystal data top
[Fe(C17H14N3)2]Z = 4
Mr = 576.47F000 = 1200
Triclinic, P1Dx = 1.369 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 9.5310 (19) ÅCell parameters from 396 reflections
b = 14.174 (3) Åθ = 3.4–27.7º
c = 20.849 (4) ŵ = 0.57 mm−1
α = 86.93 (3)ºT = 293 (2) K
β = 86.54 (3)ºIrregular, red
γ = 84.92 (3)º0.20 × 0.18 × 0.14 mm
V = 2797.1 (10) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		9614 independent reflections
Radiation source: fine-focus sealed tube6494 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.088
T = 293(2) Kθmax = 25.0º
0.3° wide ω scansθmin = 3.4º
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)		h = −11→11
Tmin = 0.894, Tmax = 0.924k = −16→16
12350 measured reflectionsl = −24→24
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.169  w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
9614 reflectionsΔρmax = 1.19 e Å−3
743 parametersΔρmin = −0.44 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Fe(C17H14N3)2]γ = 84.92 (3)º
Mr = 576.47V = 2797.1 (10) Å3
Triclinic, P1Z = 4
a = 9.5310 (19) ÅMo Kα
b = 14.174 (3) ŵ = 0.57 mm−1
c = 20.849 (4) ÅT = 293 (2) K
α = 86.93 (3)º0.20 × 0.18 × 0.14 mm
β = 86.54 (3)º
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		9614 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)		6494 reflections with I > 2σ(I)
Tmin = 0.894, Tmax = 0.924Rint = 0.088
12350 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.057743 parameters
wR(F2) = 0.169H-atom parameters constrained
S = 1.08Δρmax = 1.19 e Å−3
9614 reflectionsΔρmin = −0.44 e Å−3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Fe10.98277 (4)0.30512 (3)0.411550 (18)0.05024 (12)
Fe20.36478 (4)0.60868 (3)0.301205 (17)0.04885 (12)
N11.3011 (3)0.10489 (17)0.74760 (11)0.0582 (7)
N21.0406 (3)0.15162 (18)0.63580 (12)0.0656 (8)
N31.0123 (3)0.2273 (2)0.59149 (12)0.0679 (8)
N41.2728 (3)0.13166 (18)0.47873 (11)0.0615 (7)
N51.3665 (3)0.11010 (19)0.52807 (11)0.0638 (7)
N61.4081 (3)−0.09841 (18)0.62752 (12)0.0650 (7)
N70.9526 (2)0.25644 (15)0.12609 (10)0.0474 (6)
N80.8267 (2)0.44948 (16)0.21873 (10)0.0500 (6)
N90.7077 (2)0.46631 (17)0.25942 (10)0.0509 (6)
N100.4655 (3)0.49048 (18)0.13866 (11)0.0579 (7)
N110.5767 (3)0.47477 (18)0.09280 (11)0.0593 (7)
N120.6870 (3)0.27633 (17)0.00311 (11)0.0560 (7)
C11.3411 (3)0.0433 (2)0.79661 (13)0.0539 (8)
C21.4578 (3)0.0598 (2)0.82998 (16)0.0683 (9)
H2A1.50600.11300.81900.082*
C31.5024 (4)−0.0020 (2)0.87906 (16)0.0734 (10)
H3A1.58180.00970.90020.088*
C41.4327 (4)−0.0808 (2)0.89774 (16)0.0680 (9)
H4A1.4632−0.12090.93180.082*
C51.3194 (3)−0.0991 (2)0.86604 (14)0.0602 (9)
H5A1.2724−0.15260.87810.072*
C61.2716 (3)−0.0378 (2)0.81472 (12)0.0500 (7)
C71.1551 (3)−0.0551 (2)0.77985 (14)0.0618 (9)
H7A1.1051−0.10780.79030.074*
C81.1180 (4)0.0060 (2)0.73119 (14)0.0642 (9)
H8A1.0424−0.00480.70710.077*
C91.1927 (3)0.0866 (2)0.71627 (12)0.0519 (8)
C101.1513 (4)0.1558 (2)0.66412 (13)0.0613 (9)
H10A1.20920.20390.65200.074*
C110.9336 (3)0.2070 (2)0.54707 (14)0.0611 (9)
C120.8850 (5)0.1122 (3)0.54017 (19)0.1035 (14)
H12A0.88580.07750.58100.155*
H12B0.94680.07860.50950.155*
H12C0.79090.11890.52550.155*
C130.8918 (3)0.2837 (2)0.50157 (14)0.0637 (9)
C140.7912 (3)0.2802 (3)0.45176 (16)0.0762 (11)
H14A0.73650.22700.44400.091*
C150.7845 (4)0.3689 (3)0.41886 (18)0.0845 (12)
H15A0.72580.38750.38250.101*
C160.8751 (5)0.4256 (3)0.44423 (18)0.0893 (13)
H16A0.89130.49060.42900.107*
C170.9407 (4)0.3749 (2)0.49468 (15)0.0759 (11)
H17A1.01150.39830.52060.091*
C181.0873 (3)0.1848 (2)0.37868 (14)0.0634 (9)
H18A1.07120.11990.39390.076*
C191.0187 (4)0.2375 (3)0.32838 (15)0.0743 (10)
H19A0.94560.21490.30340.089*
C201.0687 (4)0.3261 (3)0.32020 (15)0.0751 (11)
H20A1.03770.37640.28880.090*
C211.1716 (3)0.3318 (3)0.36578 (14)0.0701 (10)
H21A1.22520.38640.37150.084*
C221.1818 (3)0.2425 (2)0.40305 (13)0.0582 (8)
C231.2747 (3)0.2176 (2)0.45544 (13)0.0584 (9)
C241.3611 (4)0.2902 (3)0.47669 (19)0.0965 (13)
H24A1.42910.26110.50540.145*
H24B1.30130.33790.49850.145*
H24C1.40930.31900.43990.145*
C251.3536 (3)0.0293 (2)0.55350 (15)0.0660 (9)
H25A1.2858−0.00610.53860.079*
C261.4394 (3)−0.0132 (2)0.60572 (14)0.0586 (8)
C271.5442 (3)0.0352 (2)0.62839 (15)0.0664 (9)
H27A1.56200.09510.61110.080*
C281.6206 (4)−0.0069 (2)0.67661 (15)0.0701 (10)
H28A1.69140.02430.69300.084*
C291.5926 (3)−0.0980 (2)0.70168 (14)0.0588 (8)
C301.6675 (4)−0.1473 (3)0.75219 (16)0.0780 (11)
H30A1.7405−0.12010.77010.094*
C311.6310 (4)−0.2351 (3)0.77407 (16)0.0852 (12)
H31A1.6798−0.26700.80720.102*
C321.5241 (4)−0.2772 (3)0.74835 (17)0.0839 (12)
H32A1.5017−0.33690.76420.101*
C331.4513 (4)−0.2325 (2)0.70005 (15)0.0725 (10)
H33A1.3794−0.26160.68280.087*
C341.4846 (3)−0.1417 (2)0.67599 (14)0.0607 (9)
C351.0598 (3)0.2266 (2)0.08375 (12)0.0485 (7)
C361.0570 (4)0.1386 (2)0.05603 (14)0.0635 (9)
H36A0.98330.10110.06750.076*
C371.1609 (4)0.1077 (3)0.01252 (15)0.0782 (11)
H37A1.15870.0491−0.00520.094*
C381.2696 (4)0.1637 (3)−0.00524 (15)0.0792 (11)
H38A1.33920.1428−0.03570.095*
C391.2766 (3)0.2489 (3)0.02104 (14)0.0652 (9)
H39A1.35170.28490.00900.078*
C401.1719 (3)0.2829 (2)0.06606 (12)0.0481 (7)
C411.1721 (3)0.3701 (2)0.09530 (13)0.0526 (8)
H41A1.24650.40790.08620.063*
C421.0645 (3)0.3988 (2)0.13653 (12)0.0465 (7)
H42A1.06310.45680.15540.056*
C430.9545 (3)0.34014 (18)0.15075 (12)0.0415 (7)
C440.8362 (3)0.3689 (2)0.19416 (12)0.0461 (7)
H44A0.76620.32790.20420.055*
C450.6891 (3)0.5537 (2)0.27623 (12)0.0469 (7)
C460.7822 (4)0.6287 (2)0.2558 (2)0.0821 (11)
H46A0.83920.61000.21830.123*
H46B0.84200.63820.28990.123*
H46C0.72590.68660.24580.123*
C470.5704 (3)0.5781 (2)0.32088 (13)0.0532 (8)
C480.4840 (3)0.5132 (2)0.35484 (13)0.0578 (8)
H48A0.49210.44410.35180.069*
C490.3862 (3)0.5676 (3)0.39574 (14)0.0726 (11)
H49A0.31270.54200.42480.087*
C500.4084 (4)0.6631 (3)0.38588 (16)0.0777 (11)
H50A0.35350.71570.40690.093*
C510.5216 (3)0.6717 (2)0.33993 (15)0.0643 (9)
H51A0.56020.73080.32390.077*
C520.2599 (3)0.5326 (2)0.24211 (13)0.0595 (8)
H52A0.27020.46350.23900.071*
C530.1644 (3)0.5841 (3)0.28416 (16)0.0719 (10)
H53A0.09670.55660.31550.086*
C540.1821 (3)0.6806 (3)0.27400 (16)0.0775 (11)
H54A0.12910.73220.29690.093*
C550.2897 (3)0.6912 (2)0.22543 (15)0.0675 (9)
H55A0.32460.75120.20870.081*
C560.3384 (3)0.5991 (2)0.20470 (13)0.0528 (8)
C570.4505 (3)0.5766 (2)0.15611 (12)0.0511 (8)
C580.5361 (4)0.6542 (2)0.13042 (16)0.0751 (10)
H58A0.62800.62790.11580.113*
H58B0.54520.69720.16370.113*
H58C0.49040.68780.09510.113*
C590.5885 (3)0.3914 (2)0.07385 (13)0.0564 (8)
H59A0.52610.34860.09110.068*
C600.6974 (3)0.3601 (2)0.02566 (12)0.0494 (7)
C610.8061 (3)0.4182 (2)0.00656 (14)0.0570 (8)
H61A0.80910.47700.02400.068*
C620.9048 (3)0.3869 (2)−0.03714 (14)0.0610 (9)
H62A0.97820.4240−0.04990.073*
C630.8995 (3)0.2979 (2)−0.06452 (13)0.0538 (8)
C640.9970 (4)0.2602 (3)−0.11112 (15)0.0734 (10)
H64A1.07260.2941−0.12590.088*
C650.9827 (4)0.1745 (3)−0.13520 (16)0.0841 (12)
H65A1.04680.1515−0.16730.101*
C660.8743 (5)0.1214 (3)−0.11252 (18)0.0925 (13)
H66A0.86740.0620−0.12830.111*
C670.7779 (4)0.1554 (2)−0.06750 (16)0.0761 (11)
H67A0.70430.1195−0.05280.091*
C680.7880 (3)0.2446 (2)−0.04266 (13)0.0560 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0442 (2)0.0551 (3)0.0514 (2)−0.00429 (19)−0.00468 (18)−0.00073 (19)
Fe20.0343 (2)0.0612 (3)0.0498 (2)0.00557 (19)0.00104 (17)−0.01042 (18)
N10.0591 (15)0.0533 (15)0.0621 (14)−0.0063 (12)0.0059 (12)−0.0113 (12)
N20.0710 (18)0.0668 (17)0.0564 (14)−0.0017 (14)0.0052 (13)0.0040 (13)
N30.0697 (18)0.0751 (18)0.0568 (14)0.0018 (14)0.0031 (13)−0.0029 (13)
N40.0522 (15)0.0698 (17)0.0588 (14)0.0100 (13)−0.0002 (12)0.0013 (13)
N50.0555 (15)0.0730 (17)0.0602 (15)0.0058 (13)−0.0061 (12)0.0056 (13)
N60.0628 (16)0.0660 (17)0.0638 (15)0.0041 (14)−0.0022 (13)0.0013 (13)
N70.0443 (13)0.0473 (13)0.0500 (12)−0.0024 (11)−0.0002 (10)−0.0006 (10)
N80.0370 (12)0.0559 (15)0.0562 (13)0.0003 (11)0.0024 (10)−0.0063 (11)
N90.0402 (13)0.0571 (15)0.0536 (13)0.0028 (11)0.0027 (10)−0.0042 (11)
N100.0502 (14)0.0643 (16)0.0600 (14)−0.0064 (12)0.0021 (12)−0.0135 (12)
N110.0594 (15)0.0658 (16)0.0529 (13)−0.0039 (13)0.0037 (12)−0.0146 (12)
N120.0545 (15)0.0557 (15)0.0592 (13)−0.0097 (12)0.0007 (12)−0.0127 (11)
C10.0497 (17)0.0547 (17)0.0583 (16)−0.0042 (14)0.0017 (14)−0.0173 (14)
C20.064 (2)0.061 (2)0.083 (2)−0.0146 (16)−0.0005 (17)−0.0128 (17)
C30.065 (2)0.077 (2)0.081 (2)−0.0055 (18)−0.0172 (17)−0.0163 (19)
C40.070 (2)0.064 (2)0.0706 (19)−0.0003 (17)−0.0110 (17)−0.0082 (16)
C50.0587 (19)0.0528 (18)0.0694 (18)−0.0065 (15)0.0015 (16)−0.0091 (15)
C60.0504 (17)0.0489 (17)0.0504 (15)−0.0027 (14)0.0058 (13)−0.0114 (13)
C70.0614 (19)0.063 (2)0.0613 (17)−0.0118 (16)0.0016 (15)−0.0053 (15)
C80.068 (2)0.070 (2)0.0568 (17)−0.0145 (17)−0.0047 (15)−0.0116 (16)
C90.0576 (18)0.0503 (17)0.0473 (15)−0.0055 (15)0.0104 (13)−0.0105 (13)
C100.078 (2)0.0547 (18)0.0500 (16)0.0001 (17)0.0071 (16)−0.0101 (14)
C110.0469 (17)0.076 (2)0.0570 (17)−0.0022 (16)0.0173 (14)−0.0005 (16)
C120.122 (3)0.096 (3)0.100 (3)−0.053 (3)−0.024 (2)0.023 (2)
C130.0545 (18)0.071 (2)0.0607 (17)0.0098 (16)0.0105 (15)−0.0008 (16)
C140.0403 (18)0.108 (3)0.077 (2)0.0015 (18)0.0005 (16)0.007 (2)
C150.058 (2)0.099 (3)0.088 (2)0.031 (2)−0.0005 (18)0.006 (2)
C160.112 (3)0.059 (2)0.093 (3)0.017 (2)−0.006 (2)−0.0040 (19)
C170.103 (3)0.060 (2)0.0641 (19)0.003 (2)−0.0027 (19)−0.0131 (16)
C180.0594 (19)0.072 (2)0.0589 (17)0.0025 (17)−0.0063 (15)−0.0130 (15)
C190.063 (2)0.105 (3)0.0563 (17)0.004 (2)−0.0150 (15)−0.0211 (18)
C200.063 (2)0.108 (3)0.0522 (17)−0.007 (2)−0.0078 (15)0.0181 (18)
C210.0515 (18)0.099 (2)0.0596 (18)−0.0184 (17)−0.0109 (15)0.0233 (17)
C220.0386 (16)0.084 (2)0.0503 (15)−0.0015 (15)0.0055 (13)0.0007 (15)
C230.0408 (16)0.081 (2)0.0504 (16)0.0012 (15)0.0006 (13)0.0071 (15)
C240.081 (2)0.104 (3)0.109 (3)−0.029 (2)−0.040 (2)0.025 (2)
C250.0582 (19)0.073 (2)0.0654 (19)0.0086 (17)−0.0102 (15)−0.0068 (17)
C260.0562 (18)0.0540 (18)0.0632 (18)0.0053 (15)0.0028 (15)−0.0046 (15)
C270.064 (2)0.063 (2)0.0694 (19)0.0049 (17)−0.0006 (16)−0.0008 (16)
C280.065 (2)0.077 (2)0.0679 (19)0.0021 (18)−0.0048 (17)−0.0133 (17)
C290.0535 (18)0.0636 (19)0.0561 (16)0.0133 (15)0.0017 (14)−0.0076 (15)
C300.070 (2)0.096 (3)0.066 (2)0.010 (2)−0.0028 (17)−0.0091 (19)
C310.090 (3)0.097 (3)0.0592 (19)0.026 (2)0.0013 (19)0.0193 (19)
C320.083 (3)0.080 (2)0.080 (2)0.014 (2)0.016 (2)0.015 (2)
C330.070 (2)0.075 (2)0.068 (2)0.0038 (18)0.0034 (17)0.0071 (17)
C340.0533 (18)0.065 (2)0.0597 (17)0.0109 (16)0.0083 (15)−0.0009 (15)
C350.0491 (16)0.0493 (16)0.0465 (14)0.0002 (13)−0.0069 (13)0.0003 (12)
C360.075 (2)0.0506 (18)0.0646 (18)0.0009 (16)−0.0040 (16)−0.0084 (15)
C370.091 (3)0.074 (2)0.069 (2)0.018 (2)−0.0085 (19)−0.0270 (17)
C380.070 (2)0.105 (3)0.0583 (18)0.018 (2)0.0071 (17)−0.0169 (19)
C390.0515 (18)0.090 (2)0.0515 (16)0.0012 (17)0.0084 (14)−0.0039 (16)
C400.0385 (15)0.0585 (17)0.0454 (14)0.0042 (13)−0.0036 (12)0.0035 (13)
C410.0413 (15)0.0593 (18)0.0581 (16)−0.0109 (14)−0.0060 (13)0.0020 (14)
C420.0434 (15)0.0456 (15)0.0508 (14)−0.0010 (13)−0.0073 (12)−0.0047 (12)
C430.0351 (14)0.0432 (15)0.0455 (13)0.0039 (12)−0.0058 (11)−0.0019 (12)
C440.0358 (14)0.0497 (17)0.0524 (15)−0.0026 (13)−0.0024 (12)−0.0011 (13)
C450.0343 (14)0.0605 (18)0.0461 (14)−0.0012 (13)−0.0051 (11)−0.0055 (13)
C460.051 (2)0.066 (2)0.127 (3)−0.0081 (17)0.026 (2)−0.020 (2)
C470.0348 (15)0.074 (2)0.0510 (15)−0.0013 (14)−0.0045 (12)−0.0119 (14)
C480.0435 (16)0.076 (2)0.0508 (15)0.0051 (15)0.0003 (13)0.0015 (15)
C490.0543 (19)0.116 (3)0.0448 (16)0.005 (2)0.0026 (14)−0.0062 (18)
C500.064 (2)0.103 (3)0.0679 (19)0.004 (2)−0.0014 (17)−0.0393 (19)
C510.0436 (17)0.073 (2)0.0782 (19)−0.0010 (16)0.0004 (15)−0.0345 (17)
C520.0408 (16)0.079 (2)0.0602 (17)−0.0095 (15)−0.0073 (14)−0.0104 (16)
C530.0327 (16)0.112 (3)0.0702 (19)0.0010 (18)0.0019 (14)−0.0101 (19)
C540.0469 (18)0.102 (3)0.078 (2)0.0347 (19)−0.0074 (16)−0.011 (2)
C550.062 (2)0.068 (2)0.0683 (19)0.0180 (17)−0.0063 (16)−0.0009 (16)
C560.0454 (16)0.0632 (19)0.0482 (15)0.0069 (14)−0.0067 (13)−0.0007 (14)
C570.0479 (16)0.0605 (19)0.0448 (14)0.0002 (14)−0.0083 (12)−0.0023 (13)
C580.085 (2)0.063 (2)0.073 (2)−0.0018 (19)0.0150 (18)−0.0002 (17)
C590.0501 (17)0.066 (2)0.0554 (16)−0.0117 (15)−0.0018 (14)−0.0098 (15)
C600.0511 (16)0.0502 (17)0.0481 (14)−0.0090 (14)−0.0052 (13)−0.0036 (13)
C610.0616 (19)0.0487 (17)0.0615 (17)−0.0097 (15)−0.0026 (15)−0.0040 (14)
C620.0548 (18)0.0611 (19)0.0662 (18)−0.0108 (15)0.0009 (15)0.0114 (15)
C630.0566 (18)0.0554 (18)0.0473 (15)0.0008 (15)0.0003 (13)0.0035 (13)
C640.067 (2)0.087 (2)0.0606 (18)0.0074 (19)0.0121 (16)0.0067 (18)
C650.094 (3)0.090 (3)0.0621 (19)0.021 (2)0.0111 (19)−0.0158 (19)
C660.117 (3)0.072 (2)0.088 (2)0.012 (2)0.002 (2)−0.032 (2)
C670.086 (3)0.061 (2)0.083 (2)−0.0094 (19)0.007 (2)−0.0239 (18)
C680.0608 (19)0.0553 (18)0.0522 (16)−0.0037 (15)−0.0052 (14)−0.0050 (14)
Geometric parameters (Å, °) top
Fe1—C142.015 (3)C24—H24A0.9600
Fe1—C192.022 (3)C24—H24B0.9600
Fe1—C152.022 (3)C24—H24C0.9600
Fe1—C222.024 (3)C25—C261.472 (4)
Fe1—C182.027 (3)C25—H25A0.9300
Fe1—C132.038 (3)C26—C271.379 (5)
Fe1—C162.041 (4)C27—C281.358 (4)
Fe1—C212.042 (3)C27—H27A0.9300
Fe1—C172.042 (3)C28—C291.408 (5)
Fe1—C202.045 (3)C28—H28A0.9300
Fe2—C482.023 (3)C29—C341.395 (5)
Fe2—C532.027 (3)C29—C301.425 (4)
Fe2—C472.030 (3)C30—C311.368 (5)
Fe2—C542.034 (3)C30—H30A0.9300
Fe2—C512.035 (3)C31—C321.375 (6)
Fe2—C522.040 (3)C31—H31A0.9300
Fe2—C552.041 (3)C32—C331.355 (5)
Fe2—C492.042 (3)C32—H32A0.9300
Fe2—C502.043 (3)C33—C341.412 (5)
Fe2—C562.056 (3)C33—H33A0.9300
N1—C91.307 (4)C35—C361.405 (4)
N1—C11.357 (4)C35—C401.409 (4)
N2—C101.247 (4)C36—C371.361 (4)
N2—N31.396 (3)C36—H36A0.9300
N3—C111.286 (4)C37—C381.381 (5)
N4—C231.288 (4)C37—H37A0.9300
N4—N51.406 (3)C38—C391.361 (5)
N5—C251.248 (4)C38—H38A0.9300
N6—C261.321 (4)C39—C401.399 (4)
N6—C341.368 (4)C39—H39A0.9300
N7—C431.320 (3)C40—C411.408 (4)
N7—C351.363 (3)C41—C421.347 (4)
N8—C441.270 (3)C41—H41A0.9300
N8—N91.386 (3)C42—C431.403 (4)
N9—C451.299 (3)C42—H42A0.9300
N10—C571.286 (4)C43—C441.446 (4)
N10—N111.395 (3)C44—H44A0.9300
N11—C591.260 (4)C45—C471.451 (4)
N12—C601.315 (4)C45—C461.473 (4)
N12—C681.377 (4)C46—H46A0.9600
C1—C21.390 (4)C46—H46B0.9600
C1—C61.401 (4)C46—H46C0.9600
C2—C31.373 (4)C47—C481.422 (4)
C2—H2A0.9300C47—C511.434 (4)
C3—C41.376 (5)C48—C491.427 (4)
C3—H3A0.9300C48—H48A0.9800
C4—C51.350 (4)C49—C501.391 (5)
C4—H4A0.9300C49—H49A0.9800
C5—C61.413 (4)C50—C511.408 (5)
C5—H5A0.9300C50—H50A0.9800
C6—C71.409 (4)C51—H51A0.9800
C7—C81.342 (4)C52—C531.409 (4)
C7—H7A0.9300C52—C561.426 (4)
C8—C91.410 (4)C52—H52A0.9800
C8—H8A0.9300C53—C541.397 (5)
C9—C101.473 (4)C53—H53A0.9800
C10—H10A0.9300C54—C551.409 (5)
C11—C131.449 (4)C54—H54A0.9800
C11—C121.476 (5)C55—C561.427 (4)
C12—H12A0.9600C55—H55A0.9800
C12—H12B0.9600C56—C571.453 (4)
C12—H12C0.9600C57—C581.485 (4)
C13—C171.409 (5)C58—H58A0.9600
C13—C141.461 (5)C58—H58B0.9600
C14—C151.398 (5)C58—H58C0.9600
C14—H14A0.9800C59—C601.457 (4)
C15—C161.376 (6)C59—H59A0.9300
C15—H15A0.9800C60—C611.405 (4)
C16—C171.391 (5)C61—C621.333 (4)
C16—H16A0.9800C61—H61A0.9300
C17—H17A0.9800C62—C631.418 (4)
C18—C221.402 (4)C62—H62A0.9300
C18—C191.413 (4)C63—C641.397 (4)
C18—H18A0.9800C63—C681.398 (4)
C19—C201.381 (5)C64—C651.359 (5)
C19—H19A0.9800C64—H64A0.9300
C20—C211.417 (4)C65—C661.378 (6)
C20—H20A0.9800C65—H65A0.9300
C21—C221.448 (4)C66—C671.350 (5)
C21—H21A0.9800C66—H66A0.9300
C22—C231.456 (4)C67—C681.406 (4)
C23—C241.477 (5)C67—H67A0.9300
C14—Fe1—C19110.07 (16)C20—C21—C22107.4 (3)
C14—Fe1—C1540.52 (14)C20—C21—Fe169.83 (18)
C19—Fe1—C15111.23 (15)C22—C21—Fe168.48 (17)
C14—Fe1—C22140.26 (14)C20—C21—H21A126.3
C19—Fe1—C2268.36 (13)C22—C21—H21A126.3
C15—Fe1—C22179.16 (14)Fe1—C21—H21A126.3
C14—Fe1—C18111.32 (15)C18—C22—C21107.2 (3)
C19—Fe1—C1840.85 (13)C18—C22—C23126.8 (3)
C15—Fe1—C18139.62 (16)C21—C22—C23125.9 (3)
C22—Fe1—C1840.51 (13)C18—C22—Fe169.87 (17)
C14—Fe1—C1342.26 (13)C21—C22—Fe169.79 (17)
C19—Fe1—C13139.51 (15)C23—C22—Fe1126.1 (2)
C15—Fe1—C1368.70 (14)N4—C23—C22115.0 (3)
C22—Fe1—C13112.10 (12)N4—C23—C24126.2 (3)
C18—Fe1—C13111.88 (13)C22—C23—C24118.8 (3)
C14—Fe1—C1668.07 (17)C23—C24—H24A109.5
C19—Fe1—C16138.74 (15)C23—C24—H24B109.5
C15—Fe1—C1639.59 (16)H24A—C24—H24B109.5
C22—Fe1—C16140.28 (16)C23—C24—H24C109.5
C18—Fe1—C16179.21 (16)H24A—C24—H24C109.5
C13—Fe1—C1668.04 (14)H24B—C24—H24C109.5
C14—Fe1—C21176.67 (12)N5—C25—C26123.9 (3)
C19—Fe1—C2167.60 (15)N5—C25—H25A118.1
C15—Fe1—C21137.47 (15)C26—C25—H25A118.1
C22—Fe1—C2141.73 (12)N6—C26—C27124.5 (3)
C18—Fe1—C2168.66 (14)N6—C26—C25115.1 (3)
C13—Fe1—C21141.03 (13)C27—C26—C25120.4 (3)
C16—Fe1—C21111.92 (17)C28—C27—C26118.3 (3)
C14—Fe1—C1768.79 (16)C28—C27—H27A120.8
C19—Fe1—C17178.31 (14)C26—C27—H27A120.8
C15—Fe1—C1767.08 (16)C27—C28—C29119.9 (3)
C22—Fe1—C17113.32 (14)C27—C28—H28A120.1
C18—Fe1—C17140.57 (13)C29—C28—H28A120.1
C13—Fe1—C1740.40 (14)C34—C29—C28118.0 (3)
C16—Fe1—C1739.83 (14)C34—C29—C30118.4 (3)
C21—Fe1—C17113.48 (16)C28—C29—C30123.6 (3)
C14—Fe1—C20136.13 (14)C31—C30—C29119.3 (4)
C19—Fe1—C2039.69 (15)C31—C30—H30A120.3
C15—Fe1—C20110.05 (15)C29—C30—H30A120.3
C22—Fe1—C2069.15 (13)C30—C31—C32121.6 (3)
C18—Fe1—C2068.33 (14)C30—C31—H31A119.2
C13—Fe1—C20178.40 (14)C32—C31—H31A119.2
C16—Fe1—C20111.73 (16)C33—C32—C31120.6 (4)
C21—Fe1—C2040.57 (13)C33—C32—H32A119.7
C17—Fe1—C20140.34 (16)C31—C32—H32A119.7
C48—Fe2—C53119.97 (14)C32—C33—C34119.9 (4)
C48—Fe2—C4741.07 (12)C32—C33—H33A120.0
C53—Fe2—C47157.88 (14)C34—C33—H33A120.0
C48—Fe2—C54155.22 (14)N6—C34—C29121.5 (3)
C53—Fe2—C5440.25 (15)N6—C34—C33118.3 (3)
C47—Fe2—C54161.54 (15)C29—C34—C33120.2 (3)
C48—Fe2—C5169.32 (13)N7—C35—C36119.3 (3)
C53—Fe2—C51157.35 (13)N7—C35—C40121.5 (3)
C47—Fe2—C5141.31 (12)C36—C35—C40119.2 (3)
C54—Fe2—C51123.29 (15)C37—C36—C35120.7 (3)
C48—Fe2—C52106.44 (13)C37—C36—H36A119.7
C53—Fe2—C5240.53 (12)C35—C36—H36A119.7
C47—Fe2—C52123.90 (12)C36—C37—C38119.8 (3)
C54—Fe2—C5268.16 (14)C36—C37—H37A120.1
C51—Fe2—C52161.55 (12)C38—C37—H37A120.1
C48—Fe2—C55162.21 (12)C39—C38—C37121.1 (3)
C53—Fe2—C5568.00 (15)C39—C38—H38A119.4
C47—Fe2—C55126.57 (13)C37—C38—H38A119.4
C54—Fe2—C5540.45 (13)C38—C39—C40120.7 (3)
C51—Fe2—C55109.78 (14)C38—C39—H39A119.7
C52—Fe2—C5568.48 (14)C40—C39—H39A119.7
C48—Fe2—C4941.11 (12)C39—C40—C41123.9 (3)
C53—Fe2—C49104.73 (14)C39—C40—C35118.4 (3)
C47—Fe2—C4968.32 (12)C41—C40—C35117.7 (2)
C54—Fe2—C49119.55 (14)C42—C41—C40119.9 (3)
C51—Fe2—C4967.77 (15)C42—C41—H41A120.1
C52—Fe2—C49121.57 (15)C40—C41—H41A120.1
C55—Fe2—C49156.24 (13)C41—C42—C43119.4 (3)
C48—Fe2—C5068.77 (14)C41—C42—H42A120.3
C53—Fe2—C50120.35 (14)C43—C42—H42A120.3
C47—Fe2—C5068.56 (13)N7—C43—C42122.7 (2)
C54—Fe2—C50106.01 (15)N7—C43—C44116.3 (2)
C51—Fe2—C5040.40 (13)C42—C43—C44121.0 (2)
C52—Fe2—C50156.41 (14)N8—C44—C43120.8 (3)
C55—Fe2—C50122.83 (15)N8—C44—H44A119.6
C49—Fe2—C5039.81 (15)C43—C44—H44A119.6
C48—Fe2—C56124.43 (12)N9—C45—C47117.2 (3)
C53—Fe2—C5668.17 (13)N9—C45—C46125.3 (3)
C47—Fe2—C56110.66 (11)C47—C45—C46117.5 (3)
C54—Fe2—C5668.21 (13)C45—C46—H46A109.5
C51—Fe2—C56125.92 (13)C45—C46—H46B109.5
C52—Fe2—C5640.74 (12)H46A—C46—H46B109.5
C55—Fe2—C5640.76 (12)C45—C46—H46C109.5
C49—Fe2—C56159.55 (14)H46A—C46—H46C109.5
C50—Fe2—C56160.37 (15)H46B—C46—H46C109.5
C9—N1—C1117.8 (3)C48—C47—C51107.8 (3)
C10—N2—N3113.9 (3)C48—C47—C45126.0 (3)
C11—N3—N2113.1 (3)C51—C47—C45126.2 (3)
C23—N4—N5113.1 (3)C48—C47—Fe269.19 (16)
C25—N5—N4111.6 (3)C51—C47—Fe269.52 (17)
C26—N6—C34117.8 (3)C45—C47—Fe2128.01 (19)
C43—N7—C35118.9 (2)C47—C48—C49106.8 (3)
C44—N8—N9113.8 (2)C47—C48—Fe269.74 (16)
C45—N9—N8112.6 (2)C49—C48—Fe270.16 (17)
C57—N10—N11112.6 (2)C47—C48—H48A126.6
C59—N11—N10112.8 (3)C49—C48—H48A126.6
C60—N12—C68117.7 (3)Fe2—C48—H48A126.6
N1—C1—C2119.1 (3)C50—C49—C48109.1 (3)
N1—C1—C6123.0 (3)C50—C49—Fe270.13 (19)
C2—C1—C6117.8 (3)C48—C49—Fe268.73 (16)
C3—C2—C1120.6 (3)C50—C49—H49A125.4
C3—C2—H2A119.7C48—C49—H49A125.4
C1—C2—H2A119.7Fe2—C49—H49A125.4
C2—C3—C4121.7 (3)C49—C50—C51108.6 (3)
C2—C3—H3A119.2C49—C50—Fe270.05 (19)
C4—C3—H3A119.2C51—C50—Fe269.49 (18)
C5—C4—C3119.2 (3)C49—C50—H50A125.7
C5—C4—H4A120.4C51—C50—H50A125.7
C3—C4—H4A120.4Fe2—C50—H50A125.7
C4—C5—C6120.7 (3)C50—C51—C47107.6 (3)
C4—C5—H5A119.7C50—C51—Fe270.11 (19)
C6—C5—H5A119.7C47—C51—Fe269.17 (17)
C1—C6—C7117.6 (3)C50—C51—H51A126.2
C1—C6—C5120.0 (3)C47—C51—H51A126.2
C7—C6—C5122.4 (3)Fe2—C51—H51A126.2
C8—C7—C6118.6 (3)C53—C52—C56107.6 (3)
C8—C7—H7A120.7C53—C52—Fe269.24 (19)
C6—C7—H7A120.7C56—C52—Fe270.21 (17)
C7—C8—C9120.5 (3)C53—C52—H52A126.2
C7—C8—H8A119.8C56—C52—H52A126.2
C9—C8—H8A119.8Fe2—C52—H52A126.2
N1—C9—C8122.6 (3)C54—C53—C52108.9 (3)
N1—C9—C10116.1 (3)C54—C53—Fe270.13 (19)
C8—C9—C10121.3 (3)C52—C53—Fe270.23 (17)
N2—C10—C9121.7 (3)C54—C53—H53A125.6
N2—C10—H10A119.1C52—C53—H53A125.6
C9—C10—H10A119.1Fe2—C53—H53A125.6
N3—C11—C13116.3 (3)C53—C54—C55108.3 (3)
N3—C11—C12124.3 (3)C53—C54—Fe269.62 (18)
C13—C11—C12119.4 (3)C55—C54—Fe270.05 (17)
C11—C12—H12A109.5C53—C54—H54A125.8
C11—C12—H12B109.5C55—C54—H54A125.8
H12A—C12—H12B109.5Fe2—C54—H54A125.8
C11—C12—H12C109.5C54—C55—C56107.9 (3)
H12A—C12—H12C109.5C54—C55—Fe269.50 (18)
H12B—C12—H12C109.5C56—C55—Fe270.16 (16)
C17—C13—C11128.1 (3)C54—C55—H55A126.0
C17—C13—C14106.0 (3)C56—C55—H55A126.0
C11—C13—C14126.0 (3)Fe2—C55—H55A126.0
C17—C13—Fe169.96 (19)C52—C56—C55107.2 (3)
C11—C13—Fe1125.3 (2)C52—C56—C57126.2 (3)
C14—C13—Fe168.01 (17)C55—C56—C57126.6 (3)
C15—C14—C13106.5 (3)C52—C56—Fe269.05 (16)
C15—C14—Fe170.0 (2)C55—C56—Fe269.08 (17)
C13—C14—Fe169.72 (18)C57—C56—Fe2125.5 (2)
C15—C14—H14A126.7N10—C57—C56116.4 (3)
C13—C14—H14A126.7N10—C57—C58125.7 (3)
Fe1—C14—H14A126.7C56—C57—C58117.9 (3)
C16—C15—C14109.8 (3)C57—C58—H58A109.5
C16—C15—Fe170.9 (2)C57—C58—H58B109.5
C14—C15—Fe169.47 (18)H58A—C58—H58B109.5
C16—C15—H15A125.1C57—C58—H58C109.5
C14—C15—H15A125.1H58A—C58—H58C109.5
Fe1—C15—H15A125.1H58B—C58—H58C109.5
C15—C16—C17108.5 (4)N11—C59—C60121.7 (3)
C15—C16—Fe169.5 (2)N11—C59—H59A119.1
C17—C16—Fe170.2 (2)C60—C59—H59A119.1
C15—C16—H16A125.7N12—C60—C61123.9 (3)
C17—C16—H16A125.7N12—C60—C59116.1 (3)
Fe1—C16—H16A125.7C61—C60—C59120.0 (3)
C16—C17—C13109.2 (3)C62—C61—C60118.4 (3)
C16—C17—Fe170.0 (2)C62—C61—H61A120.8
C13—C17—Fe169.64 (18)C60—C61—H61A120.8
C16—C17—H17A125.4C61—C62—C63121.0 (3)
C13—C17—H17A125.4C61—C62—H62A119.5
Fe1—C17—H17A125.4C63—C62—H62A119.5
C22—C18—C19107.7 (3)C64—C63—C68118.3 (3)
C22—C18—Fe169.62 (18)C64—C63—C62124.9 (3)
C19—C18—Fe169.39 (19)C68—C63—C62116.8 (3)
C22—C18—H18A126.2C65—C64—C63120.9 (3)
C19—C18—H18A126.2C65—C64—H64A119.6
Fe1—C18—H18A126.2C63—C64—H64A119.6
C20—C19—C18109.9 (3)C64—C65—C66120.6 (3)
C20—C19—Fe171.0 (2)C64—C65—H65A119.7
C18—C19—Fe169.76 (18)C66—C65—H65A119.7
C20—C19—H19A125.1C67—C66—C65120.3 (4)
C18—C19—H19A125.1C67—C66—H66A119.9
Fe1—C19—H19A125.1C65—C66—H66A119.9
C19—C20—C21107.8 (3)C66—C67—C68120.4 (4)
C19—C20—Fe169.29 (19)C66—C67—H67A119.8
C21—C20—Fe169.60 (17)C68—C67—H67A119.8
C19—C20—H20A126.1N12—C68—C63122.2 (3)
C21—C20—H20A126.1N12—C68—C67118.3 (3)
Fe1—C20—H20A126.1C63—C68—C67119.5 (3)
Acknowledgements top

This work was supported financially by the Natural Science Foundation of Henan Province (No. 0611011900) and the Foundation of the Education Department of Henan Province (No. 2007150012)

references
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