Literature DB >> 21580559

(E)-1-Ferrocenyl-3-(2-fur-yl)prop-2-en-1-one.

Yong-Hong Liu1, Rong Guo.   

Abstract

The title compound, [Fe(C(5)H(5))(C(12)H(9)O(2))], exhibits an E configuration. In the ferrocene unit, the two cyclo-penta-dienyl rings are almost parallel [dihedral angle = 0.76 (12)°] and the C atoms are in an eclipsed conformation. An intra-molecular C-H⋯O hydrogen bond generates an S(5) ring. In the crystal, the mol-ecules are linking into zigzag chains via two C-H⋯O hydrogen-bonding inter-actions along the c axis and neighbouring chains are stabilized by electrostatic inter-action forces.

Entities:  

Year:  2010        PMID： 21580559      PMCID： PMC2983834          DOI： 10.1107/S1600536810011001

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


Related literature

For the biological activity of chalcones and chalcone derivatives, see: Liu et al. (2003 ▶). For the ability of some chalcones to block voltage-dependent potassium channels, see: Yarishkin et al. (2008 ▶). Replacement of the aromatic group of penicillins and cephalosporins by a ferrocenyl group could improve their anti­biotic activity, see: Edwards et al. (1975 ▶). For our ongoing research in this area, see: Shi et al. (2004 ▶); Liu, Liu et al. (2008 ▶). For the synthesis, see: Huang et al. (1998 ▶). For a related structure, see: Liu, Ye et al. (2008 ▶) For graph-set notations of ring systems, see: Bernstein et al. (1995 ▶). For related literature, see: Zhai et al. (1999 ▶).

Experimental

Crystal data

[Fe(C5H5)(C12H9O2)] M = 306.13 Orthorhombic, a = 9.0677 (13) Å b = 14.222 (2) Å c = 10.4846 (15) Å V = 1352.1 (3) Å3 Z = 4 Mo Kα radiation μ = 1.11 mm−1 T = 296 K 0.28 × 0.25 × 0.22 mm

Data collection

Bruker SMART 1000 CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.746, T max = 0.792 11058 measured reflections 3012 independent reflections 2772 reflections with I > 2σ(I) R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.023 wR(F 2) = 0.058 S = 1.00 3012 reflections 182 parameters 1 restraint H-atom parameters constrained Δρmax = 0.20 e Å−3 Δρmin = −0.19 e Å−3 Absolute structure: Flack (1983 ▶), 1340 Friedel pairs Flack parameter: 0.012 (14) 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, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810011001/pv2265sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011001/pv2265Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Fe(C5H5)(C12H9O2)]Dx = 1.504 Mg m−3
Mr = 306.13Melting point: 429.5 K
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 6056 reflections
a = 9.0677 (13) Åθ = 2.7–27.4°
b = 14.222 (2) ŵ = 1.11 mm−1
c = 10.4846 (15) ÅT = 296 K
V = 1352.1 (3) Å3Prism, orange
Z = 40.28 × 0.25 × 0.22 mm
F(000) = 632
Bruker SMART 1000 CCD diffractometer3012 independent reflections
Radiation source: fine-focus sealed tube2772 reflections with I > 2σ(I)
graphiteRint = 0.035
φ and ω scansθmax = 27.7°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2002)h = −11→11
Tmin = 0.746, Tmax = 0.792k = −18→16
11058 measured reflectionsl = −13→13
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.023w = 1/[σ2(Fo2) + (0.0253P)2 + 0.1177P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.058(Δ/σ)max = 0.001
S = 1.00Δρmax = 0.20 e Å−3
3012 reflectionsΔρmin = −0.18 e Å−3
182 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.0184 (11)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 1340 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: 0.012 (14)
Experimental. Analysis found (calculated) for C17H14FeO2 (%): C 66.61 (66.70), H 4.56 (4.61).
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Fe1−0.04553 (2)0.652980 (14)0.19388 (4)0.03343 (8)
O10.35975 (15)0.71855 (11)0.24502 (15)0.0524 (4)
O20.28635 (15)0.93776 (10)−0.13390 (15)0.0525 (3)
C1−0.1739 (2)0.76594 (14)0.1431 (2)0.0523 (5)
H1−0.17890.79340.06270.063*
C2−0.26341 (18)0.69146 (14)0.1893 (3)0.0522 (4)
H2−0.33810.66150.14400.063*
C3−0.2206 (2)0.67061 (16)0.3142 (2)0.0550 (6)
H3−0.26130.62430.36610.066*
C4−0.1041 (2)0.73260 (17)0.3481 (2)0.0582 (6)
H4−0.05540.73440.42610.070*
C5−0.0756 (2)0.79058 (15)0.2428 (3)0.0555 (6)
H5−0.00420.83740.23900.067*
C60.0731 (2)0.61272 (14)0.03780 (19)0.0430 (4)
H60.07220.6417−0.04170.052*
C7−0.0200 (2)0.53753 (14)0.0779 (2)0.0484 (5)
H7−0.09240.50870.02870.058*
C80.0167 (2)0.51418 (13)0.2055 (3)0.0493 (5)
H8−0.02780.46750.25430.059*
C90.13284 (19)0.57416 (13)0.2463 (2)0.0455 (4)
H90.17760.57360.32610.055*
C100.16853 (19)0.63550 (13)0.14257 (19)0.0385 (4)
C110.27507 (18)0.71373 (13)0.15362 (18)0.0386 (4)
C120.2747 (2)0.78616 (13)0.05229 (18)0.0398 (4)
H120.21320.7793−0.01810.048*
C130.3620 (2)0.86111 (13)0.06132 (19)0.0418 (4)
H130.42310.86380.13250.050*
C140.3723 (2)0.93831 (14)−0.02664 (19)0.0436 (4)
C150.4527 (2)1.01887 (16)−0.0245 (2)0.0568 (6)
H150.52061.03630.03760.068*
C170.3148 (3)1.02013 (17)−0.1960 (3)0.0614 (6)
H160.27041.0383−0.27200.074*
C160.4146 (3)1.07107 (16)−0.1333 (3)0.0630 (6)
H170.45161.1295−0.15690.076*
U11U22U33U12U13U23
Fe10.03501 (11)0.03456 (13)0.03073 (12)−0.00320 (8)0.00069 (13)−0.00016 (13)
O10.0483 (7)0.0608 (9)0.0481 (8)−0.0051 (6)−0.0080 (6)0.0125 (7)
O20.0544 (8)0.0487 (8)0.0545 (9)−0.0015 (6)−0.0052 (7)0.0061 (7)
C10.0495 (11)0.0416 (11)0.0659 (14)0.0076 (8)−0.0004 (9)0.0000 (9)
C20.0351 (7)0.0549 (10)0.0666 (13)−0.0006 (7)−0.0031 (11)−0.0056 (15)
C30.0449 (10)0.0650 (14)0.0551 (14)−0.0073 (9)0.0148 (9)−0.0063 (11)
C40.0514 (11)0.0724 (15)0.0507 (13)−0.0033 (10)0.0060 (9)−0.0240 (12)
C50.0476 (10)0.0414 (11)0.0775 (17)−0.0027 (8)0.0095 (10)−0.0170 (10)
C60.0554 (10)0.0400 (10)0.0336 (10)0.0012 (8)0.0074 (8)−0.0022 (8)
C70.0596 (11)0.0368 (10)0.0487 (12)−0.0034 (9)0.0028 (9)−0.0078 (9)
C80.0535 (9)0.0335 (8)0.0611 (14)−0.0005 (7)0.0061 (12)0.0097 (12)
C90.0433 (9)0.0439 (11)0.0493 (11)0.0046 (8)0.0006 (8)0.0142 (8)
C100.0380 (8)0.0394 (9)0.0380 (9)0.0069 (7)0.0059 (7)0.0036 (7)
C110.0328 (8)0.0436 (10)0.0394 (10)0.0044 (7)0.0058 (7)0.0046 (7)
C120.0391 (9)0.0454 (10)0.0348 (10)−0.0003 (8)0.0023 (7)0.0036 (8)
C130.0436 (9)0.0451 (10)0.0365 (10)−0.0010 (8)0.0045 (7)0.0005 (8)
C140.0460 (10)0.0441 (11)0.0408 (10)−0.0008 (8)0.0072 (8)−0.0030 (8)
C150.0697 (14)0.0522 (13)0.0486 (13)−0.0186 (10)0.0019 (9)−0.0009 (10)
C170.0744 (14)0.0521 (13)0.0578 (15)0.0124 (11)0.0043 (12)0.0136 (10)
C160.0848 (16)0.0428 (12)0.0614 (15)−0.0070 (12)0.0217 (13)0.0049 (11)
Fe1—C102.0295 (18)C5—H50.9300
Fe1—C62.0404 (19)C6—C71.426 (3)
Fe1—C52.041 (2)C6—C101.435 (3)
Fe1—C92.0431 (18)C6—H60.9300
Fe1—C32.044 (2)C7—C81.418 (4)
Fe1—C42.044 (2)C7—H70.9300
Fe1—C22.0506 (17)C8—C91.421 (3)
Fe1—C12.054 (2)C8—H80.9300
Fe1—C72.056 (2)C9—C101.431 (3)
Fe1—C82.0566 (18)C9—H90.9300
O1—C111.230 (2)C10—C111.478 (3)
O2—C171.365 (3)C11—C121.480 (3)
O2—C141.369 (2)C12—C131.331 (3)
C1—C51.418 (3)C12—H120.9300
C1—C21.419 (3)C13—C141.437 (3)
C1—H10.9300C13—H130.9300
C2—C31.398 (4)C14—C151.358 (3)
C2—H20.9300C15—C161.404 (4)
C3—C41.421 (3)C15—H150.9300
C3—H30.9300C17—C161.332 (4)
C4—C51.402 (4)C17—H160.9300
C4—H40.9300C16—H170.9300
C10—Fe1—C641.30 (8)C5—C4—C3107.8 (2)
C10—Fe1—C5108.18 (8)C5—C4—Fe169.82 (13)
C6—Fe1—C5122.75 (9)C3—C4—Fe169.63 (12)
C10—Fe1—C941.14 (7)C5—C4—H4126.1
C6—Fe1—C969.16 (9)C3—C4—H4126.1
C5—Fe1—C9124.36 (9)Fe1—C4—H4126.0
C10—Fe1—C3157.20 (9)C4—C5—C1108.63 (19)
C6—Fe1—C3159.93 (9)C4—C5—Fe170.04 (12)
C5—Fe1—C367.88 (9)C1—C5—Fe170.24 (12)
C9—Fe1—C3121.09 (9)C4—C5—H5125.7
C10—Fe1—C4121.74 (9)C1—C5—H5125.7
C6—Fe1—C4157.94 (9)Fe1—C5—H5125.6
C5—Fe1—C440.14 (11)C7—C6—C10107.50 (18)
C9—Fe1—C4107.27 (10)C7—C6—Fe170.23 (11)
C3—Fe1—C440.70 (9)C10—C6—Fe168.95 (11)
C10—Fe1—C2161.43 (10)C7—C6—H6126.3
C6—Fe1—C2124.34 (11)C10—C6—H6126.3
C5—Fe1—C267.74 (8)Fe1—C6—H6126.1
C9—Fe1—C2156.26 (9)C8—C7—C6108.35 (18)
C3—Fe1—C239.92 (11)C8—C7—Fe169.85 (12)
C4—Fe1—C267.69 (10)C6—C7—Fe169.03 (11)
C10—Fe1—C1124.69 (8)C8—C7—H7125.8
C6—Fe1—C1108.09 (9)C6—C7—H7125.8
C5—Fe1—C140.50 (9)Fe1—C7—H7126.9
C9—Fe1—C1161.34 (8)C7—C8—C9108.49 (18)
C3—Fe1—C167.89 (10)C7—C8—Fe169.82 (11)
C4—Fe1—C167.95 (10)C9—C8—Fe169.21 (10)
C2—Fe1—C140.46 (8)C7—C8—H8125.8
C10—Fe1—C768.76 (8)C9—C8—H8125.8
C6—Fe1—C740.74 (8)Fe1—C8—H8126.8
C5—Fe1—C7158.29 (10)C8—C9—C10107.7 (2)
C9—Fe1—C768.39 (9)C8—C9—Fe170.23 (10)
C3—Fe1—C7123.40 (9)C10—C9—Fe168.92 (10)
C4—Fe1—C7159.94 (10)C8—C9—H9126.1
C2—Fe1—C7107.92 (9)C10—C9—H9126.1
C1—Fe1—C7122.34 (9)Fe1—C9—H9126.3
C10—Fe1—C868.64 (8)C9—C10—C6107.91 (16)
C6—Fe1—C868.50 (10)C9—C10—C11123.17 (18)
C5—Fe1—C8160.39 (11)C6—C10—C11128.60 (17)
C9—Fe1—C840.57 (8)C9—C10—Fe169.94 (10)
C3—Fe1—C8107.12 (10)C6—C10—Fe169.76 (10)
C4—Fe1—C8123.79 (12)C11—C10—Fe1120.80 (13)
C2—Fe1—C8121.45 (8)O1—C11—C10120.74 (17)
C1—Fe1—C8157.13 (10)O1—C11—C12121.46 (17)
C7—Fe1—C840.33 (11)C10—C11—C12117.79 (16)
C17—O2—C14106.22 (17)C13—C12—C11120.34 (18)
C5—C1—C2107.0 (2)C13—C12—H12119.8
C5—C1—Fe169.26 (12)C11—C12—H12119.8
C2—C1—Fe169.63 (11)C12—C13—C14127.24 (19)
C5—C1—H1126.5C12—C13—H13116.4
C2—C1—H1126.5C14—C13—H13116.4
Fe1—C1—H1126.2C15—C14—O2108.90 (19)
C3—C2—C1108.6 (2)C15—C14—C13132.0 (2)
C3—C2—Fe169.77 (11)O2—C14—C13119.06 (17)
C1—C2—Fe169.91 (10)C14—C15—C16107.5 (2)
C3—C2—H2125.7C14—C15—H15126.3
C1—C2—H2125.7C16—C15—H15126.3
Fe1—C2—H2126.2C16—C17—O2111.1 (2)
C2—C3—C4108.0 (2)C16—C17—H16124.4
C2—C3—Fe170.31 (12)O2—C17—H16124.4
C4—C3—Fe169.67 (12)C17—C16—C15106.3 (2)
C2—C3—H3126.0C17—C16—H17126.9
C4—C3—H3126.0C15—C16—H17126.9
Fe1—C3—H3125.6
D—H···AD—HH···AD···AD—H···A
C13—H13···O10.932.452.797 (3)102
C6—H6···O1i0.932.563.473 (3)166
C12—H12···O1i0.932.713.576 (4)155
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C13—H13⋯O10.932.452.797 (3)102
C6—H6⋯O1i0.932.563.473 (3)166
C12—H12⋯O1i0.932.713.576 (4)155

Symmetry code: (i) .

  7 in total

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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
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3.  A short history of SHELX.

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4.  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

5.  (E)-1-Ferrocenyl-3-(3-nitro-phen-yl)prop-2-en-1-one.

Authors:  Yong-Hong Liu; Jun Ye; Xiao-Lan Liu; Wen-Long Liu; Yao-Cheng Shi
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-09-06

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

7.  Structure validation in chemical crystallography.

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

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  1 in total

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