Literature DB >> 21201612

(E)-1-Ferrocenyl-3-(4-methoxy-phen-yl)-prop-2-en-1-one.

Shi-Jia Long, Xiao-Lan Liu, Yong-Hong Liu.   

Abstract

In the title compound, [Fe(C(5)H(5))(C(15)H(13)O(2))], a conjugated substituent group bridges a five-membered η(5)-C(5)H(4) ring and a benzene ring. In the ferrocene unit, the substituted (Cps) and unsubstituted (Cp) cyclo-penta-dienyl rings are eclipsed and almost parallel [Cps-Fe-Cps angle = 176.1 (2)°]. The mol-ecule is linked into an S(5) motif via intra-molecular C-H⋯O hydrogen bonds. The mol-ecules are arranged into a three-dimensional framework by five inter-molecular C-H⋯O hydrogen bonds and one inter-molecular C-H⋯π(Cps) inter-action.

Entities:  

Year:  2008        PMID： 21201612      PMCID： PMC2960594          DOI： 10.1107/S1600536808025518

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

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

Crystal data

[Fe(C5H5)(C15H13O2)] M = 346.19 Orthorhombic, a = 12.3124 (14) Å b = 10.2316 (11) Å c = 25.914 (3) Å V = 3264.5 (6) Å3 Z = 8 Mo Kα radiation μ = 0.93 mm−1 T = 296 (2) K 0.30 × 0.30 × 0.20 mm

Data collection

Bruker SMART 1000 CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.768, T max = 0.836 26999 measured reflections 3787 independent reflections 2662 reflections with I > 2σ(I) R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.032 wR(F 2) = 0.089 S = 1.02 3787 reflections 209 parameters H-atom parameters constrained Δρmax = 0.20 e Å−3 Δρmin = −0.28 e Å−3 Data collection: SMART (Bruker, 2002 ▶); 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: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808025518/pv2096sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025518/pv2096Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[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
Bruker SMART 1000 CCD diffractometer3787 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 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
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.
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*
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)
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)
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
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the substituted cyclo­penta­dienyl ring.

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) ; (ii) ; (iii) .

  6 in total

1.  Structure-activity relationships of antileishmanial and antimalarial chalcones.

Authors:  Mei Liu; Prapon Wilairat; Simon L Croft; Agnes Lay-Choo Tan; Mei-Lin Go
Journal:  Bioorg Med Chem       Date:  2003-07-03       Impact factor: 3.641

2.  Sulfonate chalcone as new class voltage-dependent K+ channel blocker.

Authors:  Oleg V Yarishkin; Hyung Won Ryu; Jae-Yong Park; Min Suk Yang; Seong-Geun Hong; Ki Hun Park
Journal:  Bioorg Med Chem Lett       Date:  2007-11-04       Impact factor: 2.823

3.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

4.  Antimalarial alkoxylated and hydroxylated chalcones [corrected]: structure-activity relationship analysis.

Authors:  M Liu; P Wilairat; M L Go
Journal:  J Med Chem       Date:  2001-12-06       Impact factor: 7.446

5.  The antileishmanial activity of novel oxygenated chalcones and their mechanism of action.

Authors:  L Zhai; M Chen; J Blom; T G Theander; S B Christensen; A Kharazmi
Journal:  J Antimicrob Chemother       Date:  1999-06       Impact factor: 5.790

6.  (E)-1-Ferrocenyl-3-phenyl-prop-2-en-1-one.

Authors:  Yong-Hong Liu; Jian-Feng Liu; Pan-Ming Jian; Xiao-Lan Liu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-07-05
  6 in total
  1 in total

1.  (2E,6E)-2,6-Bis(ferrocenyl-methyl-idene)cyclo-hexa-none dichloro-methane monosolvate.

Authors:  Shi-Jia Long; Wu Yang; Yong-Hong Liu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-07-14
  1 in total

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