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Acta Cryst. (2008). E64, m1164    [ doi:10.1107/S1600536808025518 ]

(E)-1-Ferrocenyl-3-(4-methoxyphenyl)prop-2-en-1-one

S.-J. Long, X.-L. Liu and Y.-H. Liu

Abstract top

In the title compound, [Fe(C5H5)(C15H13O2)], a conjugated substituent group bridges a five-membered [eta]5-C5H4 ring and a benzene ring. In the ferrocene unit, the substituted (Cps) and unsubstituted (Cp) cyclopentadienyl rings are eclipsed and almost parallel [Cps-Fe-Cps angle = 176.1 (2)°]. The molecule is linked into an S(5) motif via intramolecular C-H...O hydrogen bonds. The molecules are arranged into a three-dimensional framework by five intermolecular C-H...O hydrogen bonds and one intermolecular C-H...[pi](Cps) interaction.

Comment top

Chalcone and its derivatives, as natural products, have attracted considerable attention for their stronge antibacterial, antifungal, antitumor and anti-inflammatory properties, especially antileishmanial and antimalarial (Zhai et al.,1999; Liu et al., 2001, 2003) over the past years. Some chalcones demonstrated the ability to block voltage-dependent potassium channels (Yarishkin et al., 2008). It was proved that the replacement of the aromatic group by the ferrocenyl moiety in penicillins and cephalosporins improves their antibiotic activity (Edwards et al., 1975). As part of our search for new biologically active compounds (Liu et al.,2008; Shi et al., 2004; Liang et al., 1998), we have synthesized the title compound (I) and describe its structure in this paper.

The molecule of the title compound (I) exists as the most stable configuration of (E)-isomer (Scheme 1, Fig.1) and all carbon atoms (except that of methoxyl group) and O1 are sp2-hybridized and form two large conjugated systems; one is formed by C1 to C5 and the other C6 to C19 including O1, just as its parent compound II (Scheme 2) (Liu et al., 2008). In the molecule there is a C(5) (Bernstein et al., 1995) C–H···O intra-molecular hydrogen-bond which makes the four atoms O1, C11, C12 and C13 be coplanar (plane-1). The Cps (the substituted cyclopentadienyl ring) plane, the plane-1 and plane-2 (the phenyl ring plane) are not coplanar. In the ferrocene moiety, the Cps and the Cp (the unsubstituted cyclopentadienyl ring) planes are almost parallel and the C-atoms of these tings are in an eclipsed conformation. The Fe atom lies in the middle of the two planes of Cp and Cps. The Cgs—Fe—Cg angle is 176.1 (2)°, where Cgs and Cg are the centroids of Cps and Cp rings, respectively.

The molecules are linked into C(5) (Bernstein et al., 1995) chains via C19–H19···O1 inter-molecular hydrogen-bonds, forming zigzag chains (Fig. 2, Table 1) along the b axis. In addition, there are three inter-molecular hydrogen-bonds C9–H9···O1, C12–H12···O1 and C15–H15···O1, thus forming cross edge-fused zigzag C(5), C(4), C(7) chains (Fig. 2) along the b axis. Furthermore, the molecules are linked into C(6) (Bernstein et al., 1995) chains via C8–H8···O1 and C3–H3···π(Cps ring) inter-molecular hydrogen-bonds, along the a axis thus resulting in other zigzag chains (Fig. 3, Table 1). All of the above mentioned inter-molecular hydrogen-bonds link the molecules into a three-dimensional structure of considerable complexity.

Related literature top

For related literature, see: Bernstein et al. (1995); Edwards et al. (1975); Huang et al. (1998); Liang et al. (1998); Liu et al. (2001, 2003, 2008); Shi et al. (2004); Yarishkin et al. (2008); Zhai et al. (1999).

Experimental top

The title compound was synthesized according to the literature procedure (Huang et al. 1998). Crystals of I suitable for X-ray diffraction were obtained by slow evaporation of a solution of the solid in dichloromethane / ether (5:1 v/v) at room temperature over a period of 6 days.

Refinement top

After their location in a difference map, all H atoms were fixed geometrically at ideal positions and allowed to ride on the parent C atoms, with C—H distances of 0.93 – 0.96, and with Uĩso(H) values of 1.2Ueq (C).

Computing details top

Data collection: SMART (Bruker, 2002); 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: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids. The C–H···O intra-molecular hydrogen bond is shown as dashed lines.
[Figure 2] Fig. 2. Unit cell packing of (I) showing the hydrogen bonded chains (dashed lines). For clarity, H atoms not involved in hydrogen bonding have been omitted.
[Figure 3] Fig. 3. Unit cell packing of (I) showing the hydrogen bonded chains via C8–H8···O1 and C3–H3···π(Cps ring) inter-molecular interactions; for clarity, H atoms not involved in hydrogen bonding have been omitted.
[Figure 4] Fig. 4. Schematic representations of the structures of (I) and (II).
(E)-1-Ferrocenyl-3-(4-methoxyphenyl)prop-2-en-1-one top
Crystal data top
[Fe(C5H5)(C15H13O2)]F000 = 1440
Mr = 346.19Dx = 1.409 Mg m−3
Orthorhombic, PbcaMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 6158 reflections
a = 12.3124 (14) Åθ = 3.0–25.5º
b = 10.2316 (11) ŵ = 0.93 mm−1
c = 25.914 (3) ÅT = 296 (2) K
V = 3264.5 (6) Å3Block, red
Z = 80.30 × 0.30 × 0.20 mm
Data collection top
Bruker SMART 1000 CCD
diffractometer		3787 independent reflections
Radiation source: fine-focus sealed tube2662 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.037
T = 296(2) Kθmax = 27.6º
φ and ω scansθmin = 1.6º
Absorption correction: multi-scan
(SADABS; Bruker, 2002)		h = −14→16
Tmin = 0.768, Tmax = 0.836k = −13→13
26999 measured reflectionsl = −33→33
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)] = 0.032H-atom parameters constrained
wR(F2) = 0.089  w = 1/[σ2(Fo2) + (0.0396P)2 + 0.9963P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
3787 reflectionsΔρmax = 0.20 e Å−3
209 parametersΔρmin = −0.28 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Fe(C5H5)(C15H13O2)]V = 3264.5 (6) Å3
Mr = 346.19Z = 8
Orthorhombic, PbcaMo Kα
a = 12.3124 (14) ŵ = 0.93 mm−1
b = 10.2316 (11) ÅT = 296 (2) K
c = 25.914 (3) Å0.30 × 0.30 × 0.20 mm
Data collection top
Bruker SMART 1000 CCD
diffractometer		3787 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)		2662 reflections with I > 2σ(I)
Tmin = 0.768, Tmax = 0.836Rint = 0.037
26999 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.032209 parameters
wR(F2) = 0.089H-atom parameters constrained
S = 1.02Δρmax = 0.20 e Å−3
3787 reflectionsΔρmin = −0.28 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
Fe10.47330 (2)0.24558 (2)0.447598 (9)0.03889 (10)
O10.17057 (11)0.14263 (12)0.41478 (5)0.0509 (3)
C140.14386 (15)0.45292 (18)0.30462 (7)0.0423 (4)
C120.22120 (15)0.35247 (17)0.38469 (7)0.0424 (4)
H120.26710.42350.38980.051*
C170.12977 (17)0.6313 (2)0.22287 (7)0.0502 (5)
C150.22061 (16)0.5508 (2)0.29796 (7)0.0502 (5)
H150.27770.55740.32130.060*
C130.15074 (15)0.35526 (18)0.34563 (7)0.0433 (4)
H130.10040.28760.34440.052*
C160.21475 (17)0.6392 (2)0.25751 (7)0.0530 (5)
H160.26770.70330.25370.064*
C190.05897 (17)0.4478 (2)0.26898 (8)0.0552 (5)
H190.00620.38330.27230.066*
C110.22818 (15)0.23985 (17)0.41997 (7)0.0405 (4)
C180.05177 (18)0.5362 (2)0.22907 (8)0.0589 (6)
H18−0.00620.53160.20610.071*
C70.43869 (17)0.1790 (2)0.52041 (8)0.0553 (5)
H70.48290.12670.54090.066*
C90.36118 (15)0.35924 (19)0.48277 (7)0.0454 (4)
H90.34590.44550.47400.055*
C10.54687 (18)0.1382 (2)0.39076 (8)0.0580 (5)
H10.53080.05230.38180.070*
C60.36007 (15)0.13343 (19)0.48474 (8)0.0495 (5)
H60.34360.04650.47780.059*
C100.31062 (15)0.24527 (17)0.46128 (7)0.0418 (4)
C50.49898 (18)0.2505 (2)0.36970 (8)0.0548 (5)
H50.44550.25210.34430.066*
C20.62385 (17)0.1786 (2)0.42794 (8)0.0600 (6)
H20.66740.12400.44780.072*
C30.62294 (17)0.3156 (2)0.42965 (8)0.0582 (6)
H30.66580.36770.45090.070*
C80.43881 (17)0.3170 (2)0.51975 (7)0.0529 (5)
H80.48220.37090.54000.064*
C40.54580 (18)0.3608 (2)0.39360 (8)0.0569 (5)
H40.52880.44770.38680.068*
O20.11598 (14)0.71299 (17)0.18152 (6)0.0679 (4)
C200.1979 (2)0.8096 (3)0.17227 (11)0.0906 (9)
H20A0.19960.87030.20050.136*
H20B0.18180.85550.14090.136*
H20C0.26740.76770.16920.136*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.03704 (16)0.03933 (16)0.04030 (15)0.00167 (11)0.00085 (10)0.00384 (11)
O10.0463 (7)0.0378 (7)0.0686 (8)−0.0054 (6)0.0019 (7)0.0049 (6)
C140.0404 (10)0.0407 (10)0.0458 (10)0.0023 (8)−0.0012 (8)−0.0031 (8)
C120.0399 (10)0.0333 (9)0.0541 (10)0.0000 (8)−0.0016 (8)0.0020 (8)
C170.0562 (12)0.0520 (12)0.0425 (10)0.0149 (10)0.0028 (9)0.0008 (9)
C150.0477 (11)0.0524 (12)0.0506 (11)−0.0053 (10)−0.0095 (9)0.0036 (9)
C130.0391 (10)0.0364 (10)0.0545 (10)−0.0007 (8)0.0011 (8)−0.0001 (8)
C160.0561 (13)0.0490 (12)0.0541 (11)−0.0040 (10)−0.0012 (10)0.0052 (9)
C190.0453 (11)0.0578 (13)0.0626 (13)−0.0075 (10)−0.0082 (10)−0.0002 (10)
C110.0362 (9)0.0348 (9)0.0504 (10)0.0040 (8)0.0076 (7)0.0014 (8)
C180.0518 (12)0.0698 (15)0.0552 (12)0.0036 (11)−0.0159 (10)0.0025 (11)
C70.0519 (12)0.0666 (14)0.0475 (11)0.0084 (11)0.0023 (10)0.0179 (10)
C90.0462 (10)0.0434 (10)0.0466 (10)0.0056 (9)0.0033 (9)−0.0014 (8)
C10.0591 (13)0.0538 (13)0.0613 (13)0.0016 (11)0.0120 (11)−0.0105 (11)
C60.0465 (11)0.0434 (11)0.0586 (11)0.0025 (9)0.0083 (10)0.0162 (9)
C100.0360 (9)0.0413 (10)0.0481 (9)0.0032 (8)0.0064 (8)0.0073 (8)
C50.0491 (11)0.0756 (16)0.0397 (10)−0.0032 (11)0.0015 (8)0.0007 (10)
C20.0431 (12)0.0792 (17)0.0578 (12)0.0134 (11)0.0053 (10)0.0048 (12)
C30.0454 (12)0.0774 (16)0.0516 (12)−0.0177 (11)0.0040 (10)−0.0041 (11)
C80.0526 (12)0.0649 (14)0.0412 (10)0.0058 (10)0.0021 (9)−0.0020 (10)
C40.0665 (14)0.0525 (13)0.0518 (11)−0.0069 (11)0.0112 (10)0.0099 (10)
O20.0735 (11)0.0751 (10)0.0552 (8)0.0178 (9)0.0000 (8)0.0171 (8)
C200.0817 (19)0.103 (2)0.0877 (18)0.0128 (17)0.0247 (16)0.0454 (17)
Geometric parameters (Å, °) top
Fe1—C92.0220 (18)C11—C101.476 (3)
Fe1—C32.031 (2)C18—H180.9300
Fe1—C102.0341 (18)C7—C81.412 (3)
Fe1—C42.036 (2)C7—C61.417 (3)
Fe1—C22.041 (2)C7—H70.9300
Fe1—C52.044 (2)C9—C81.421 (3)
Fe1—C62.0462 (18)C9—C101.434 (3)
Fe1—C12.049 (2)C9—H90.9300
Fe1—C72.0507 (19)C1—C51.403 (3)
Fe1—C82.052 (2)C1—C21.414 (3)
O1—C111.229 (2)C1—H10.9300
C14—C151.388 (3)C6—C101.432 (2)
C14—C191.396 (3)C6—H60.9300
C14—C131.461 (2)C5—C41.410 (3)
C12—C131.333 (2)C5—H50.9300
C12—C111.473 (2)C2—C31.403 (3)
C12—H120.9300C2—H20.9300
C17—O21.369 (2)C3—C41.410 (3)
C17—C181.377 (3)C3—H30.9300
C17—C161.381 (3)C8—H80.9300
C15—C161.386 (3)C4—H40.9300
C15—H150.9300O2—C201.433 (3)
C13—H130.9300C20—H20A0.9600
C16—H160.9300C20—H20B0.9600
C19—C181.377 (3)C20—H20C0.9600
C19—H190.9300
C9—Fe1—C3121.31 (9)C19—C18—H18119.8
C9—Fe1—C1041.42 (7)C17—C18—H18119.8
C3—Fe1—C10159.03 (9)C8—C7—C6108.78 (18)
C9—Fe1—C4106.03 (9)C8—C7—Fe169.92 (11)
C3—Fe1—C440.57 (9)C6—C7—Fe169.59 (11)
C10—Fe1—C4123.54 (8)C8—C7—H7125.6
C9—Fe1—C2157.77 (9)C6—C7—H7125.6
C3—Fe1—C240.30 (10)Fe1—C7—H7126.5
C10—Fe1—C2159.61 (9)C8—C9—C10107.85 (17)
C4—Fe1—C267.95 (9)C8—C9—Fe170.72 (11)
C9—Fe1—C5122.45 (8)C10—C9—Fe169.74 (10)
C3—Fe1—C567.96 (9)C8—C9—H9126.1
C10—Fe1—C5108.94 (8)C10—C9—H9126.1
C4—Fe1—C540.44 (8)Fe1—C9—H9125.1
C2—Fe1—C567.74 (9)C5—C1—C2107.9 (2)
C9—Fe1—C669.23 (8)C5—C1—Fe169.76 (12)
C3—Fe1—C6157.48 (9)C2—C1—Fe169.47 (12)
C10—Fe1—C641.08 (7)C5—C1—H1126.1
C4—Fe1—C6161.23 (9)C2—C1—H1126.1
C2—Fe1—C6123.23 (9)Fe1—C1—H1126.3
C5—Fe1—C6125.73 (9)C7—C6—C10107.71 (18)
C9—Fe1—C1159.13 (9)C7—C6—Fe169.93 (11)
C3—Fe1—C167.89 (9)C10—C6—Fe169.00 (10)
C10—Fe1—C1124.04 (8)C7—C6—H6126.1
C4—Fe1—C167.83 (10)C10—C6—H6126.1
C2—Fe1—C140.44 (9)Fe1—C6—H6126.5
C5—Fe1—C140.09 (8)C6—C10—C9107.48 (17)
C6—Fe1—C1109.79 (9)C6—C10—C11124.77 (17)
C9—Fe1—C768.56 (8)C9—C10—C11127.62 (16)
C3—Fe1—C7121.09 (9)C6—C10—Fe169.91 (10)
C10—Fe1—C768.56 (8)C9—C10—Fe168.84 (10)
C4—Fe1—C7156.32 (9)C11—C10—Fe1123.41 (13)
C2—Fe1—C7107.87 (9)C1—C5—C4108.2 (2)
C5—Fe1—C7161.64 (9)C1—C5—Fe170.15 (12)
C6—Fe1—C740.48 (8)C4—C5—Fe169.47 (11)
C1—Fe1—C7125.11 (9)C1—C5—H5125.9
C9—Fe1—C840.82 (8)C4—C5—H5125.9
C3—Fe1—C8105.71 (9)Fe1—C5—H5126.1
C10—Fe1—C868.77 (8)C3—C2—C1108.00 (19)
C4—Fe1—C8120.73 (9)C3—C2—Fe169.48 (12)
C2—Fe1—C8122.34 (9)C1—C2—Fe170.09 (12)
C5—Fe1—C8157.40 (9)C3—C2—H2126.0
C6—Fe1—C868.28 (9)C1—C2—H2126.0
C1—Fe1—C8159.65 (9)Fe1—C2—H2126.0
C7—Fe1—C840.25 (9)C2—C3—C4108.18 (19)
C15—C14—C19117.06 (18)C2—C3—Fe170.23 (12)
C15—C14—C13123.00 (17)C4—C3—Fe169.89 (12)
C19—C14—C13119.92 (18)C2—C3—H3125.9
C13—C12—C11121.71 (17)C4—C3—H3125.9
C13—C12—H12119.1Fe1—C3—H3125.5
C11—C12—H12119.1C7—C8—C9108.16 (19)
O2—C17—C18115.87 (19)C7—C8—Fe169.83 (12)
O2—C17—C16124.5 (2)C9—C8—Fe168.47 (11)
C18—C17—C16119.58 (18)C7—C8—H8125.9
C16—C15—C14121.96 (18)C9—C8—H8125.9
C16—C15—H15119.0Fe1—C8—H8127.4
C14—C15—H15119.0C3—C4—C5107.7 (2)
C12—C13—C14127.19 (17)C3—C4—Fe169.53 (11)
C12—C13—H13116.4C5—C4—Fe170.09 (12)
C14—C13—H13116.4C3—C4—H4126.1
C17—C16—C15119.55 (19)C5—C4—H4126.1
C17—C16—H16120.2Fe1—C4—H4125.8
C15—C16—H16120.2C17—O2—C20117.68 (19)
C18—C19—C14121.4 (2)O2—C20—H20A109.5
C18—C19—H19119.3O2—C20—H20B109.5
C14—C19—H19119.3H20A—C20—H20B109.5
O1—C11—C12122.11 (17)O2—C20—H20C109.5
O1—C11—C10120.43 (16)H20A—C20—H20C109.5
C12—C11—C10117.43 (16)H20B—C20—H20C109.5
C19—C18—C17120.48 (19)
C19—C14—C15—C16−0.7 (3)C8—Fe1—C10—C938.10 (11)
C13—C14—C15—C16177.32 (18)C9—Fe1—C10—C11121.93 (19)
C11—C12—C13—C14−172.39 (17)C3—Fe1—C10—C1181.7 (3)
C15—C14—C13—C127.6 (3)C4—Fe1—C10—C1146.44 (18)
C19—C14—C13—C12−174.41 (19)C2—Fe1—C10—C11−72.9 (3)
O2—C17—C16—C15−179.85 (19)C5—Fe1—C10—C113.99 (17)
C18—C17—C16—C150.2 (3)C6—Fe1—C10—C11−119.1 (2)
C14—C15—C16—C170.7 (3)C1—Fe1—C10—C11−37.90 (18)
C15—C14—C19—C18−0.1 (3)C7—Fe1—C10—C11−156.61 (17)
C13—C14—C19—C18−178.24 (19)C8—Fe1—C10—C11160.03 (17)
C13—C12—C11—O10.9 (3)C2—C1—C5—C40.0 (2)
C13—C12—C11—C10178.68 (17)Fe1—C1—C5—C459.23 (15)
C14—C19—C18—C171.0 (3)C2—C1—C5—Fe1−59.23 (14)
O2—C17—C18—C19179.00 (19)C9—Fe1—C5—C1−164.59 (12)
C16—C17—C18—C19−1.1 (3)C3—Fe1—C5—C181.40 (14)
C9—Fe1—C7—C8−37.40 (12)C10—Fe1—C5—C1−120.76 (13)
C3—Fe1—C7—C877.12 (15)C4—Fe1—C5—C1119.4 (2)
C10—Fe1—C7—C8−82.06 (13)C2—Fe1—C5—C137.73 (13)
C4—Fe1—C7—C843.6 (3)C6—Fe1—C5—C1−78.05 (15)
C2—Fe1—C7—C8119.28 (13)C7—Fe1—C5—C1−41.9 (3)
C5—Fe1—C7—C8−167.7 (2)C8—Fe1—C5—C1159.1 (2)
C6—Fe1—C7—C8−120.12 (17)C9—Fe1—C5—C476.03 (15)
C1—Fe1—C7—C8160.61 (13)C3—Fe1—C5—C4−37.98 (14)
C9—Fe1—C7—C682.72 (13)C10—Fe1—C5—C4119.86 (13)
C3—Fe1—C7—C6−162.76 (12)C2—Fe1—C5—C4−81.64 (15)
C10—Fe1—C7—C638.06 (11)C6—Fe1—C5—C4162.57 (12)
C4—Fe1—C7—C6163.7 (2)C1—Fe1—C5—C4−119.4 (2)
C2—Fe1—C7—C6−120.60 (13)C7—Fe1—C5—C4−161.3 (2)
C5—Fe1—C7—C6−47.6 (3)C8—Fe1—C5—C439.8 (3)
C1—Fe1—C7—C6−79.27 (15)C5—C1—C2—C30.1 (2)
C8—Fe1—C7—C6120.12 (17)Fe1—C1—C2—C3−59.36 (14)
C3—Fe1—C9—C8−77.33 (14)C5—C1—C2—Fe159.41 (15)
C10—Fe1—C9—C8118.37 (16)C9—Fe1—C2—C3−40.4 (3)
C4—Fe1—C9—C8−118.72 (13)C10—Fe1—C2—C3166.3 (2)
C2—Fe1—C9—C8−48.0 (3)C4—Fe1—C2—C337.87 (12)
C5—Fe1—C9—C8−159.64 (13)C5—Fe1—C2—C381.70 (13)
C6—Fe1—C9—C880.43 (13)C6—Fe1—C2—C3−159.21 (12)
C1—Fe1—C9—C8171.7 (2)C1—Fe1—C2—C3119.11 (18)
C7—Fe1—C9—C836.90 (13)C7—Fe1—C2—C3−117.30 (13)
C3—Fe1—C9—C10164.30 (11)C8—Fe1—C2—C3−75.45 (15)
C4—Fe1—C9—C10122.91 (12)C9—Fe1—C2—C1−159.5 (2)
C2—Fe1—C9—C10−166.3 (2)C3—Fe1—C2—C1−119.11 (18)
C5—Fe1—C9—C1081.99 (13)C10—Fe1—C2—C147.2 (3)
C6—Fe1—C9—C10−37.94 (11)C4—Fe1—C2—C1−81.24 (15)
C1—Fe1—C9—C1053.3 (3)C5—Fe1—C2—C1−37.41 (13)
C7—Fe1—C9—C10−81.47 (12)C6—Fe1—C2—C181.68 (15)
C8—Fe1—C9—C10−118.37 (16)C7—Fe1—C2—C1123.59 (14)
C9—Fe1—C1—C539.0 (3)C8—Fe1—C2—C1165.44 (13)
C3—Fe1—C1—C5−81.58 (14)C1—C2—C3—C4−0.1 (2)
C10—Fe1—C1—C578.79 (15)Fe1—C2—C3—C4−59.83 (14)
C4—Fe1—C1—C5−37.62 (13)C1—C2—C3—Fe159.74 (14)
C2—Fe1—C1—C5−119.17 (19)C9—Fe1—C3—C2163.33 (12)
C6—Fe1—C1—C5122.43 (13)C10—Fe1—C3—C2−166.6 (2)
C7—Fe1—C1—C5165.10 (13)C4—Fe1—C3—C2−118.99 (18)
C8—Fe1—C1—C5−156.8 (2)C5—Fe1—C3—C2−81.13 (13)
C9—Fe1—C1—C2158.2 (2)C6—Fe1—C3—C250.8 (3)
C3—Fe1—C1—C237.58 (14)C1—Fe1—C3—C2−37.71 (12)
C10—Fe1—C1—C2−162.04 (13)C7—Fe1—C3—C280.97 (14)
C4—Fe1—C1—C281.55 (15)C8—Fe1—C3—C2121.84 (13)
C5—Fe1—C1—C2119.17 (19)C9—Fe1—C3—C4−77.69 (15)
C6—Fe1—C1—C2−118.41 (14)C10—Fe1—C3—C4−47.7 (3)
C7—Fe1—C1—C2−75.73 (16)C2—Fe1—C3—C4118.99 (18)
C8—Fe1—C1—C2−37.7 (3)C5—Fe1—C3—C437.86 (13)
C8—C7—C6—C100.2 (2)C6—Fe1—C3—C4169.8 (2)
Fe1—C7—C6—C10−58.86 (13)C1—Fe1—C3—C481.27 (15)
C8—C7—C6—Fe159.10 (14)C7—Fe1—C3—C4−160.05 (13)
C9—Fe1—C6—C7−80.92 (13)C8—Fe1—C3—C4−119.17 (13)
C3—Fe1—C6—C741.5 (3)C6—C7—C8—C9−1.0 (2)
C10—Fe1—C6—C7−119.15 (17)Fe1—C7—C8—C957.86 (13)
C4—Fe1—C6—C7−159.5 (2)C6—C7—C8—Fe1−58.90 (14)
C2—Fe1—C6—C778.32 (15)C10—C9—C8—C71.4 (2)
C5—Fe1—C6—C7163.36 (13)Fe1—C9—C8—C7−58.70 (14)
C1—Fe1—C6—C7121.33 (13)C10—C9—C8—Fe160.13 (13)
C8—Fe1—C6—C7−36.99 (12)C9—Fe1—C8—C7120.13 (18)
C9—Fe1—C6—C1038.24 (11)C3—Fe1—C8—C7−119.86 (13)
C3—Fe1—C6—C10160.7 (2)C10—Fe1—C8—C781.49 (13)
C4—Fe1—C6—C10−40.3 (3)C4—Fe1—C8—C7−161.21 (13)
C2—Fe1—C6—C10−162.52 (12)C2—Fe1—C8—C7−79.30 (15)
C5—Fe1—C6—C10−77.48 (14)C5—Fe1—C8—C7169.9 (2)
C1—Fe1—C6—C10−119.52 (12)C6—Fe1—C8—C737.19 (12)
C7—Fe1—C6—C10119.15 (17)C1—Fe1—C8—C7−51.3 (3)
C8—Fe1—C6—C1082.17 (12)C3—Fe1—C8—C9120.01 (13)
C7—C6—C10—C90.6 (2)C10—Fe1—C8—C9−38.64 (11)
Fe1—C6—C10—C9−58.79 (13)C4—Fe1—C8—C978.66 (14)
C7—C6—C10—C11176.81 (17)C2—Fe1—C8—C9160.57 (13)
Fe1—C6—C10—C11117.38 (18)C5—Fe1—C8—C949.8 (3)
C7—C6—C10—Fe159.44 (13)C6—Fe1—C8—C9−82.94 (13)
C8—C9—C10—C6−1.3 (2)C1—Fe1—C8—C9−171.5 (2)
Fe1—C9—C10—C659.47 (13)C7—Fe1—C8—C9−120.13 (18)
C8—C9—C10—C11−177.31 (17)C2—C3—C4—C50.1 (2)
Fe1—C9—C10—C11−116.56 (19)Fe1—C3—C4—C5−59.95 (14)
C8—C9—C10—Fe1−60.75 (13)C2—C3—C4—Fe160.04 (14)
O1—C11—C10—C624.6 (3)C1—C5—C4—C3−0.1 (2)
C12—C11—C10—C6−153.18 (17)Fe1—C5—C4—C359.60 (14)
O1—C11—C10—C9−159.99 (18)C1—C5—C4—Fe1−59.65 (15)
C12—C11—C10—C922.2 (3)C9—Fe1—C4—C3119.71 (14)
O1—C11—C10—Fe1112.17 (18)C10—Fe1—C4—C3161.50 (13)
C12—C11—C10—Fe1−65.6 (2)C2—Fe1—C4—C3−37.62 (14)
C9—Fe1—C10—C6−118.98 (16)C5—Fe1—C4—C3−118.72 (19)
C3—Fe1—C10—C6−159.2 (2)C6—Fe1—C4—C3−167.8 (2)
C4—Fe1—C10—C6165.53 (12)C1—Fe1—C4—C3−81.43 (14)
C2—Fe1—C10—C646.2 (3)C7—Fe1—C4—C346.7 (3)
C5—Fe1—C10—C6123.08 (13)C8—Fe1—C4—C377.89 (15)
C1—Fe1—C10—C681.19 (14)C9—Fe1—C4—C5−121.56 (13)
C7—Fe1—C10—C6−37.52 (12)C3—Fe1—C4—C5118.72 (19)
C8—Fe1—C10—C6−80.88 (13)C10—Fe1—C4—C5−79.78 (15)
C3—Fe1—C10—C9−40.3 (3)C2—Fe1—C4—C581.10 (14)
C4—Fe1—C10—C9−75.49 (13)C6—Fe1—C4—C5−49.1 (3)
C2—Fe1—C10—C9165.1 (2)C1—Fe1—C4—C537.30 (13)
C5—Fe1—C10—C9−117.94 (12)C7—Fe1—C4—C5165.4 (2)
C6—Fe1—C10—C9118.98 (16)C8—Fe1—C4—C5−163.38 (13)
C1—Fe1—C10—C9−159.83 (12)C18—C17—O2—C20−177.2 (2)
C7—Fe1—C10—C981.46 (12)C16—C17—O2—C202.9 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C13—H13···O10.932.502.830 (2)101
C8—H8···O1i0.932.603.345 (2)137
C9—H9···O1ii0.932.543.414 (2)156
C12—H12···O1ii0.932.463.346 (2)160
C15—H15···O1ii0.932.653.441 (2)143
C19—H19···O2iii0.932.593.472 (3)157
C3—H3···Cg1i0.933.243.808 (2)121
Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) −x+1/2, y+1/2, z; (iii) −x, y−1/2, −z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C13—H13···O10.932.502.830 (2)101
C8—H8···O1i0.932.603.345 (2)137
C9—H9···O1ii0.932.543.414 (2)156
C12—H12···O1ii0.932.463.346 (2)160
C15—H15···O1ii0.932.653.441 (2)143
C19—H19···O2iii0.932.593.472 (3)157
C3—H3···Cg1i0.933.243.808 (2)121
Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) −x+1/2, y+1/2, z; (iii) −x, y−1/2, −z+1/2.
Acknowledgements top

The authors thank the Natural Science Foundation of Tianshui Normal College (No. TSB0715) and Yangzhou University (No. 2006XJJ03) for financial support of this work.

references
References top

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew Chem. Int. Ed. Engl. 34, 1555–1573.

Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

Edwards, E. I., Epton, R. & Marr, G. (1975). J. Organomet. Chem. 85, C23.

Huang, G.-S., Chen, B.-H., Liu, C.-M., Ma, Y.-X. & Liu, Y.-H. (1998). Transition Met. Chem. 23, 589–592.

Liang, Y.-M., Chen, B.-H., Jin, H.-W., Ma, Y.-X. & Liu, Y.-H. (1998). Synth. React. Inorg. Met. Org. Chem. 28, 803–810.

Liu, Y.-H., Liu, J.-F., Jian, P.-M. & Liu, X.-L. (2008). Acta Cryst. E64, m1001–m1002.

Liu, M., Wilairat, P., Croft, S. L., Tan, A. L. C. & Go, M.-L. (2003). Bioorg. Med. Chem. 11, 2729–2738.

Liu, M., Wilairat, P. & Go, M. L. (2001). J. Med. Chem. 44, 4443–4452.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Shi, Y. C., Yang, H.-M., Song, H.-B. & Liu, Y.-H. (2004). Polyhedron, 23, 1541–1546.

Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.

Yarishkin, O. V., Ryu, H. W., Park, J. Y., Yang, M. S., Hong, S. G. & Park, K. H. (2008). Bioorg. Med. Chem. Lett. 18, 137–140.

Zhai, L., Chen, M., Blom, J., Theander, T. G., Christensen, S. B. & Kharazmi, A. (1999). Antimicrob. Agents Chemother. 43, 793–803.