(E)-1-Ferrocenyl-3-(2-fur­yl)prop-2-en-1-one

Liu, Y.-H.; Guo, R.

doi:10.1107/S1600536810011001

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page m479

doi:10.1107/S1600536810011001

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(E)-1-Ferrocenyl-3-(2-furyl)prop-2-en-1-one

Yong-Hong Liu ^a and Rong Guo ^a ^*

^aCollege of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, People's Republic of China
^*Correspondence e-mail: guorong@yzu.edu.cn

(Received 11 March 2010; accepted 24 March 2010; online 31 March 2010)

The title compound, [Fe(C₅H₅)(C₁₂H₉O₂)], exhibits an E configuration. In the ferrocene unit, the two cyclopentadienyl rings are almost parallel [dihedral angle = 0.76 (12)°] and the C atoms are in an eclipsed conformation. An intramolecular C—H⋯O hydrogen bond generates an S(5) ring. In the crystal, the molecules are linking into zigzag chains via two C—H⋯O hydrogen-bonding interactions along the c axis and neighbouring chains are stabilized by electrostatic interaction forces.

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_r = 306.13
Orthorhombic, P c a 2₁
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[F² > 2σ(F²)] = 0.023
wR(F²) = 0.058
S = 1.00
3012 reflections
182 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.19 e Å⁻³
Absolute structure: Flack (1983 ), 1340 Friedel pairs
Flack parameter: 0.012 (14)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O1	0.93	2.45	2.797 (3)	102
C6—H6⋯O1ⁱ	0.93	2.56	3.473 (3)	166
C12—H12⋯O1ⁱ	0.93	2.71	3.576 (4)	155
Symmetry code: (i) $[-x+{\script{1\over 2}}, y, z-{\script{1\over 2}}]$ .

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).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810011001/pv2265sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810011001/pv2265Isup2.hkl

checkCIF report

Comment top

Chalcone and its derivatives, as a natural produce, have shown strong antibacterial, antifungal, antitumor and anti-inflammatory properties (Liu et al., 2003). Some chalcones demonstrated the ability to block voltage-dependent potassium channels (Yarishkin et al., 2008). It has been demonstrated that the replacement of the aromatic group by the ferrocenyl moiety in penicillins and cephalosporins could improve their antibiotic activity (Edwards et al., 1975). As on going research (Liu & Liu et al., 2008; Shi et al., 2004), we report herein the structure of the title compound.

The molecule of the title compound exists in the most stable configuration of (E)-isomer (Fig. 1). All of the C and O atoms are sp²-hybrid resulting in two large conjugated systems: one is formed by C1-C5 atoms and the other by the rest of the atoms. There is an intra-molecular hydrogen-bond C13–H13···O1 resulting in a five membered ring, S(5) in graph set notation (Bernstein et al., 1995). The atoms O1/C11/C12/C13 are essentially planar and their mean-plane lies at 3.10 (14) and 16.35 (13) °, respectively, with the mean-planes of the furyl ring and the substituted cyclopentadienyl ring. In the ferrocene moiety, the Cps plane and Cp (the unsubstituted cyclopentadienyl ring) plane are almost parallel and the C atoms of Cp and Cps are in the eclipsed conformation. The Fe atom is slightly near the Cps palne as the distances Fe–Cgs and Fe–Cg are 1.6464 (9) and 1.6574 (10) Å, respectively, where Cgs and Cg are the centroids of Cps and Cp, respectively. The Cgs—Fe—Cg angle is 179.02 (5)°. The molecular dimensions agree very well with the corresponding dimensions reparted for the crystal structure of a similar compound (Liu & Ye et al., 2008).

In the crystal structure, inter-molecular hydrogen-bonds of the type C—H···O, along the c axis, generate a R₂¹(7) motif (Bernstein et al., 1995), linking the adjacent molecules into a zig-zag chain (Fig. 2, Tab. 1). Further more, the chain and its neighboring inverse parallel chains are stablilized by electrostatic interaction forces.

Related literature top

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 [on what subject?], see: Zhai et al. (1999).

Experimental top

The title compound was synthesized according to the literature procedure (Huang et al., 1998). An aqueous solution of potassium hydroxide (5%, 5 ml) was added slowly with stirring to a mixture of 2-furanylaldehyde (4.0 g, 0.043 mol) and acetoylferrocene (0.98 g, 0.043 mol) in ethanol (20 ml) in ice bath. The resulting mixture was stirred at room temperature for 4 h. The dark-red precipitated solid was filtered off, washed with water, dried and recrystallized from 95% ethanol (yield, 83%; M.P. 429.5-430.8 K. Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of a solution of the solid in dichloromethane/ ether (4:1 v/v) at room temperature over a period of 6 d.

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, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability ellipsoids. The C–H···O intra-molecular hydrogen bond is shown as dashed lines.
	Fig. 2. Unit cell packing of the title compound, showing the inter-molecular hydrogen bonds C–H···O as dashed lines. For the sake of clarity, H atoms not involved in hydrogen bonding have been omitted.

(E)-1-Ferrocenyl-3-(2-furyl)prop-2-en-1-one top

Crystal data top

[Fe(C₅H₅)(C₁₂H₉O₂)]	D_x = 1.504 Mg m⁻³
M_r = 306.13	Melting point: 429.5 K
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 6056 reflections
a = 9.0677 (13) Å	θ = 2.7–27.4°
b = 14.222 (2) Å	µ = 1.11 mm⁻¹
c = 10.4846 (15) Å	T = 296 K
V = 1352.1 (3) Å³	Prism, orange
Z = 4	0.28 × 0.25 × 0.22 mm
F(000) = 632

Data collection top

Bruker SMART 1000 CCD diffractometer	3012 independent reflections
Radiation source: fine-focus sealed tube	2772 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ϕ and ω scans	θ_max = 27.7°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −11→11
T_min = 0.746, T_max = 0.792	k = −18→16
11058 measured reflections	l = −13→13

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.023	w = 1/[σ²(F_o²) + (0.0253P)² + 0.1177P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.058	(Δ/σ)_max = 0.001
S = 1.00	Δρ_max = 0.20 e Å⁻³
3012 reflections	Δρ_min = −0.19 e Å⁻³
182 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0184 (11)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1340 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.012 (14)

Crystal data top

[Fe(C₅H₅)(C₁₂H₉O₂)]	V = 1352.1 (3) Å³
M_r = 306.13	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 9.0677 (13) Å	µ = 1.11 mm⁻¹
b = 14.222 (2) Å	T = 296 K
c = 10.4846 (15) Å	0.28 × 0.25 × 0.22 mm

Data collection top

Bruker SMART 1000 CCD diffractometer	3012 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	2772 reflections with I > 2σ(I)
T_min = 0.746, T_max = 0.792	R_int = 0.035
11058 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	H-atom parameters constrained
wR(F²) = 0.058	Δρ_max = 0.20 e Å⁻³
S = 1.00	Δρ_min = −0.19 e Å⁻³
3012 reflections	Absolute structure: Flack (1983), 1340 Friedel pairs
182 parameters	Absolute structure parameter: 0.012 (14)
1 restraint

Special details top

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.

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

	x	y	z	U_iso*/U_eq
Fe1	−0.04553 (2)	0.652980 (14)	0.19388 (4)	0.03343 (8)
O1	0.35975 (15)	0.71855 (11)	0.24502 (15)	0.0524 (4)
O2	0.28635 (15)	0.93776 (10)	−0.13390 (15)	0.0525 (3)
C1	−0.1739 (2)	0.76594 (14)	0.1431 (2)	0.0523 (5)
H1	−0.1789	0.7934	0.0627	0.063*
C2	−0.26341 (18)	0.69146 (14)	0.1893 (3)	0.0522 (4)
H2	−0.3381	0.6615	0.1440	0.063*
C3	−0.2206 (2)	0.67061 (16)	0.3142 (2)	0.0550 (6)
H3	−0.2613	0.6243	0.3661	0.066*
C4	−0.1041 (2)	0.73260 (17)	0.3481 (2)	0.0582 (6)
H4	−0.0554	0.7344	0.4261	0.070*
C5	−0.0756 (2)	0.79058 (15)	0.2428 (3)	0.0555 (6)
H5	−0.0042	0.8374	0.2390	0.067*
C6	0.0731 (2)	0.61272 (14)	0.03780 (19)	0.0430 (4)
H6	0.0722	0.6417	−0.0417	0.052*
C7	−0.0200 (2)	0.53753 (14)	0.0779 (2)	0.0484 (5)
H7	−0.0924	0.5087	0.0287	0.058*
C8	0.0167 (2)	0.51418 (13)	0.2055 (3)	0.0493 (5)
H8	−0.0278	0.4675	0.2543	0.059*
C9	0.13284 (19)	0.57416 (13)	0.2463 (2)	0.0455 (4)
H9	0.1776	0.5736	0.3261	0.055*
C10	0.16853 (19)	0.63550 (13)	0.14257 (19)	0.0385 (4)
C11	0.27507 (18)	0.71373 (13)	0.15362 (18)	0.0386 (4)
C12	0.2747 (2)	0.78616 (13)	0.05229 (18)	0.0398 (4)
H12	0.2132	0.7793	−0.0181	0.048*
C13	0.3620 (2)	0.86111 (13)	0.06132 (19)	0.0418 (4)
H13	0.4231	0.8638	0.1325	0.050*
C14	0.3723 (2)	0.93831 (14)	−0.02664 (19)	0.0436 (4)
C15	0.4527 (2)	1.01887 (16)	−0.0245 (2)	0.0568 (6)
H15	0.5206	1.0363	0.0376	0.068*
C17	0.3148 (3)	1.02013 (17)	−0.1960 (3)	0.0614 (6)
H16	0.2704	1.0383	−0.2720	0.074*
C16	0.4146 (3)	1.07107 (16)	−0.1333 (3)	0.0630 (6)
H17	0.4516	1.1295	−0.1569	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.03501 (11)	0.03456 (13)	0.03073 (12)	−0.00320 (8)	0.00069 (13)	−0.00016 (13)
O1	0.0483 (7)	0.0608 (9)	0.0481 (8)	−0.0051 (6)	−0.0080 (6)	0.0125 (7)
O2	0.0544 (8)	0.0487 (8)	0.0545 (9)	−0.0015 (6)	−0.0052 (7)	0.0061 (7)
C1	0.0495 (11)	0.0416 (11)	0.0659 (14)	0.0076 (8)	−0.0004 (9)	0.0000 (9)
C2	0.0351 (7)	0.0549 (10)	0.0666 (13)	−0.0006 (7)	−0.0031 (11)	−0.0056 (15)
C3	0.0449 (10)	0.0650 (14)	0.0551 (14)	−0.0073 (9)	0.0148 (9)	−0.0063 (11)
C4	0.0514 (11)	0.0724 (15)	0.0507 (13)	−0.0033 (10)	0.0060 (9)	−0.0240 (12)
C5	0.0476 (10)	0.0414 (11)	0.0775 (17)	−0.0027 (8)	0.0095 (10)	−0.0170 (10)
C6	0.0554 (10)	0.0400 (10)	0.0336 (10)	0.0012 (8)	0.0074 (8)	−0.0022 (8)
C7	0.0596 (11)	0.0368 (10)	0.0487 (12)	−0.0034 (9)	0.0028 (9)	−0.0078 (9)
C8	0.0535 (9)	0.0335 (8)	0.0611 (14)	−0.0005 (7)	0.0061 (12)	0.0097 (12)
C9	0.0433 (9)	0.0439 (11)	0.0493 (11)	0.0046 (8)	0.0006 (8)	0.0142 (8)
C10	0.0380 (8)	0.0394 (9)	0.0380 (9)	0.0069 (7)	0.0059 (7)	0.0036 (7)
C11	0.0328 (8)	0.0436 (10)	0.0394 (10)	0.0044 (7)	0.0058 (7)	0.0046 (7)
C12	0.0391 (9)	0.0454 (10)	0.0348 (10)	−0.0003 (8)	0.0023 (7)	0.0036 (8)
C13	0.0436 (9)	0.0451 (10)	0.0365 (10)	−0.0010 (8)	0.0045 (7)	0.0005 (8)
C14	0.0460 (10)	0.0441 (11)	0.0408 (10)	−0.0008 (8)	0.0072 (8)	−0.0030 (8)
C15	0.0697 (14)	0.0522 (13)	0.0486 (13)	−0.0186 (10)	0.0019 (9)	−0.0009 (10)
C17	0.0744 (14)	0.0521 (13)	0.0578 (15)	0.0124 (11)	0.0043 (12)	0.0136 (10)
C16	0.0848 (16)	0.0428 (12)	0.0614 (15)	−0.0070 (12)	0.0217 (13)	0.0049 (11)

Geometric parameters (Å, º) top

Fe1—C10	2.0295 (18)	C5—H5	0.9300
Fe1—C6	2.0404 (19)	C6—C7	1.426 (3)
Fe1—C5	2.041 (2)	C6—C10	1.435 (3)
Fe1—C9	2.0431 (18)	C6—H6	0.9300
Fe1—C3	2.044 (2)	C7—C8	1.418 (4)
Fe1—C4	2.044 (2)	C7—H7	0.9300
Fe1—C2	2.0506 (17)	C8—C9	1.421 (3)
Fe1—C1	2.054 (2)	C8—H8	0.9300
Fe1—C7	2.056 (2)	C9—C10	1.431 (3)
Fe1—C8	2.0566 (18)	C9—H9	0.9300
O1—C11	1.230 (2)	C10—C11	1.478 (3)
O2—C17	1.365 (3)	C11—C12	1.480 (3)
O2—C14	1.369 (2)	C12—C13	1.331 (3)
C1—C5	1.418 (3)	C12—H12	0.9300
C1—C2	1.419 (3)	C13—C14	1.437 (3)
C1—H1	0.9300	C13—H13	0.9300
C2—C3	1.398 (4)	C14—C15	1.358 (3)
C2—H2	0.9300	C15—C16	1.404 (4)
C3—C4	1.421 (3)	C15—H15	0.9300
C3—H3	0.9300	C17—C16	1.332 (4)
C4—C5	1.402 (4)	C17—H16	0.9300
C4—H4	0.9300	C16—H17	0.9300

C10—Fe1—C6	41.30 (8)	C5—C4—C3	107.8 (2)
C10—Fe1—C5	108.18 (8)	C5—C4—Fe1	69.82 (13)
C6—Fe1—C5	122.75 (9)	C3—C4—Fe1	69.63 (12)
C10—Fe1—C9	41.14 (7)	C5—C4—H4	126.1
C6—Fe1—C9	69.16 (9)	C3—C4—H4	126.1
C5—Fe1—C9	124.36 (9)	Fe1—C4—H4	126.0
C10—Fe1—C3	157.20 (9)	C4—C5—C1	108.63 (19)
C6—Fe1—C3	159.93 (9)	C4—C5—Fe1	70.04 (12)
C5—Fe1—C3	67.88 (9)	C1—C5—Fe1	70.24 (12)
C9—Fe1—C3	121.09 (9)	C4—C5—H5	125.7
C10—Fe1—C4	121.74 (9)	C1—C5—H5	125.7
C6—Fe1—C4	157.94 (9)	Fe1—C5—H5	125.6
C5—Fe1—C4	40.14 (11)	C7—C6—C10	107.50 (18)
C9—Fe1—C4	107.27 (10)	C7—C6—Fe1	70.23 (11)
C3—Fe1—C4	40.70 (9)	C10—C6—Fe1	68.95 (11)
C10—Fe1—C2	161.43 (10)	C7—C6—H6	126.3
C6—Fe1—C2	124.34 (11)	C10—C6—H6	126.3
C5—Fe1—C2	67.74 (8)	Fe1—C6—H6	126.1
C9—Fe1—C2	156.26 (9)	C8—C7—C6	108.35 (18)
C3—Fe1—C2	39.92 (11)	C8—C7—Fe1	69.85 (12)
C4—Fe1—C2	67.69 (10)	C6—C7—Fe1	69.03 (11)
C10—Fe1—C1	124.69 (8)	C8—C7—H7	125.8
C6—Fe1—C1	108.09 (9)	C6—C7—H7	125.8
C5—Fe1—C1	40.50 (9)	Fe1—C7—H7	126.9
C9—Fe1—C1	161.34 (8)	C7—C8—C9	108.49 (18)
C3—Fe1—C1	67.89 (10)	C7—C8—Fe1	69.82 (11)
C4—Fe1—C1	67.95 (10)	C9—C8—Fe1	69.21 (10)
C2—Fe1—C1	40.46 (8)	C7—C8—H8	125.8
C10—Fe1—C7	68.76 (8)	C9—C8—H8	125.8
C6—Fe1—C7	40.74 (8)	Fe1—C8—H8	126.8
C5—Fe1—C7	158.29 (10)	C8—C9—C10	107.7 (2)
C9—Fe1—C7	68.39 (9)	C8—C9—Fe1	70.23 (10)
C3—Fe1—C7	123.40 (9)	C10—C9—Fe1	68.92 (10)
C4—Fe1—C7	159.94 (10)	C8—C9—H9	126.1
C2—Fe1—C7	107.92 (9)	C10—C9—H9	126.1
C1—Fe1—C7	122.34 (9)	Fe1—C9—H9	126.3
C10—Fe1—C8	68.64 (8)	C9—C10—C6	107.91 (16)
C6—Fe1—C8	68.50 (10)	C9—C10—C11	123.17 (18)
C5—Fe1—C8	160.39 (11)	C6—C10—C11	128.60 (17)
C9—Fe1—C8	40.57 (8)	C9—C10—Fe1	69.94 (10)
C3—Fe1—C8	107.12 (10)	C6—C10—Fe1	69.76 (10)
C4—Fe1—C8	123.79 (12)	C11—C10—Fe1	120.80 (13)
C2—Fe1—C8	121.45 (8)	O1—C11—C10	120.74 (17)
C1—Fe1—C8	157.13 (10)	O1—C11—C12	121.46 (17)
C7—Fe1—C8	40.33 (11)	C10—C11—C12	117.79 (16)
C17—O2—C14	106.22 (17)	C13—C12—C11	120.34 (18)
C5—C1—C2	107.0 (2)	C13—C12—H12	119.8
C5—C1—Fe1	69.26 (12)	C11—C12—H12	119.8
C2—C1—Fe1	69.63 (11)	C12—C13—C14	127.24 (19)
C5—C1—H1	126.5	C12—C13—H13	116.4
C2—C1—H1	126.5	C14—C13—H13	116.4
Fe1—C1—H1	126.2	C15—C14—O2	108.90 (19)
C3—C2—C1	108.6 (2)	C15—C14—C13	132.0 (2)
C3—C2—Fe1	69.77 (11)	O2—C14—C13	119.06 (17)
C1—C2—Fe1	69.91 (10)	C14—C15—C16	107.5 (2)
C3—C2—H2	125.7	C14—C15—H15	126.3
C1—C2—H2	125.7	C16—C15—H15	126.3
Fe1—C2—H2	126.2	C16—C17—O2	111.1 (2)
C2—C3—C4	108.0 (2)	C16—C17—H16	124.4
C2—C3—Fe1	70.31 (12)	O2—C17—H16	124.4
C4—C3—Fe1	69.67 (12)	C17—C16—C15	106.3 (2)
C2—C3—H3	126.0	C17—C16—H17	126.9
C4—C3—H3	126.0	C15—C16—H17	126.9
Fe1—C3—H3	125.6

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1	0.93	2.45	2.797 (3)	102
C6—H6···O1ⁱ	0.93	2.56	3.473 (3)	166
C12—H12···O1ⁱ	0.93	2.71	3.576 (4)	155

Symmetry code: (i) −x+1/2, y, z−1/2.

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₁₂H₉O₂)]
M_r	306.13
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	296
a, b, c (Å)	9.0677 (13), 14.222 (2), 10.4846 (15)
V (Å³)	1352.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.11
Crystal size (mm)	0.28 × 0.25 × 0.22

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.746, 0.792
No. of measured, independent and observed [I > 2σ(I)] reflections	11058, 3012, 2772
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.654

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.058, 1.00
No. of reflections	3012
No. of parameters	182
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.19
Absolute structure	Flack (1983), 1340 Friedel pairs
Absolute structure parameter	0.012 (14)

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1	0.93	2.45	2.797 (3)	102
C6—H6···O1ⁱ	0.93	2.56	3.473 (3)	166
C12—H12···O1ⁱ	0.93	2.71	3.576 (4)	155

Symmetry code: (i) −x+1/2, y, z−1/2.

Acknowledgements

The authors thank the National Nautral Science Foundation of China (No. 20773106) and the Natural Science Foundation of Yangzhou University (No. 2006XJJ03) for financial support of this work.

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