(E)-1-Ferrocenyl-3-phenyl­prop-2-en-1-one

Liu, Y.-H.; Liu, J.-F.; Jian, P.-M.; Liu, X.-L.

doi:10.1107/S1600536808020059

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Pages m1001-m1002

doi:10.1107/S1600536808020059

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(E)-1-Ferrocenyl-3-phenylprop-2-en-1-one

Yong-Hong Liu,^a ^* Jian-Feng Liu,^b Pan-Ming Jian ^a and Xiao-Lan Liu ^a

^aCollege of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, People's Republic of China, and ^bTechnology Center, Jiuquan Iron and Steel (Group) Co. Ltd, Jiayuguan 735100, People's Republic of China
^*Correspondence e-mail: xiaolanliu998@yahoo.com.cn

(Received 19 June 2008; accepted 1 July 2008; online 5 July 2008)

The title compound, [Fe(C₅H₅)(C₁₄H₁₁O)], exists as the E isomer, and the substituent is fully conjugated with the attached five-membered ring. In the ferrocene unit, the substituted cyclopentadienyl ring (Cps) plane and unsubstituted cyclopentadienyl ring (Cp) plane are almost parallel, and the C atoms in Cp and Cps are in an eclipsed conformation. In the crystal structure, molecules are linked into C(5) chains via intermolecular C—H⋯O hydrogen bonds, and neighbouring chains are assembled into sheets by intermolecular C—H⋯π(arene) hydrogen bonds along the c axis.

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)(C₁₄H₁₁O)]
M_r = 316.17
Orthorhombic, P n a 2₁
a = 22.717 (3) Å
b = 5.8173 (9) Å
c = 11.1789 (17) Å
V = 1477.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.02 mm⁻¹
T = 296 (2) K
0.32 × 0.28 × 0.27 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.272, T_max = 0.318 (expected range = 0.650–0.760)
9864 measured reflections
2547 independent reflections
2409 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.055
S = 1.00
2547 reflections
190 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.31 e Å⁻³
Absolute structure: Flack (1983 ), 1181 Friedel pairs
Flack parameter: 0.013 (16)

Table 1
Dihedral angles (°) for selected planes

	Atoms defining plane	1-Plane	2-Plane	Cp plane
1-Plane	C11–C13/O1	–	–	–
2-Plane	C14–C19	33.0 (1)	–	–
Cp plane	C1–C5	17.9 (2)	50.6 (4)	–
Cps plane	C6–C10	17.0 (1)	49.9 (1)	1.8 (1)

Table 2
Hydrogen-bond geometry (Å, °)

δ is the angle that the C1/H1 group makes with the normal to the Cp plane, and Cg3 is the centroid of the Cp ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O1ⁱ	0.98	2.67	3.538 (3)	148
C1—H1⋯Cg3ⁱⁱ	0.98	2.75	3.596 (2)	145 (δ = 64)
Symmetry codes: (i) x, y+1, z; (ii) $[-x+1, -y, z+{1\over2}]$ .

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808020059/om2243sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808020059/om2243Isup2.hkl

checkCIF report

Comment top

Chalcone and its derivatives, as a natural products, have shown stronge antibacterial, antifungal, antitumor and anti-inflammatory properties, especially antileishmanial, and antimalarial (Zhai et al., 1999; Liu et al., 2001, 2003). 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 could improve their antibiotic activity (Edwards et al., 1975). As ongoing research (Liu et al., 2008; Shi et al., 2004; Liang et al., 1998), we report herein the structure of the title compound.

The molecule of the title compound exists as the most stable configuration of (E)-isomer (Fig.1), and all carbon atoms are sp²-hybridized. Although the carbon atoms and a oxygen atom form a large conjugated system, the Cps (the substituted cyclopentadienyl ring) plane and 1-plane (defined by the atoms of C11, C12, O1 and C13) and 2-plane (the phenyl ring plane) are not coplanar (Table 1). In the ferrocene moiety, the Cps plane and Cp (the unsubstituted cyclopentadienyl ring) plane are almost parallel, and the carbon atoms of Cp and Cps are in the eclipsed conformation. The Fe atom is slightly nearer to the Cps plane because the Fe–Cgs and Fe–Cg distances are 1.651 (1) and 1.658 (1) Å, respectively, where Cgs and Cg are the centroids of Cps and Cp, respectively. The Cgs-Fe-Cg angle is 178.0 (2)°.

In its packing structure, the molecules are linked into C(5) (Bernstein et al., 1995) chains via C–H···O inter-molecular hydrogen-bonds. Further more the chains and their neighboring inverse parallel chains are made up into sheets by C–H···π (arene) inter-molecular hydrogen-bonds along the c axis (Fig. 2, Table 2).

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 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 4 d.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability ellipsoids.
	Fig. 2. Part of the crystal structure of the title compound, showing the inter-molecular hydrogen bonds of C–H···O and C–H···π as dashed lines. For the sake of clarity, H atoms not involved in hydrogen bonding have been omitted.

(E)-1-Ferrocenyl-3-phenylprop-2-en-1-one top

Crystal data top

[Fe(C₅H₅)(C₁₄H₁₁O)]	D_x = 1.422 Mg m⁻³
M_r = 316.17	Melting point: 416 K
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P2c-2n	Cell parameters from 5183 reflections
a = 22.717 (3) Å	θ = 2.5–27.5°
b = 5.8173 (9) Å	µ = 1.02 mm⁻¹
c = 11.1789 (17) Å	T = 296 K
V = 1477.3 (4) Å³	Block, dark-red
Z = 4	0.32 × 0.28 × 0.27 mm
F(000) = 656.0

Data collection top

Bruker SMART 1000 CCD diffractometer	2547 independent reflections
Radiation source: fine-focus sealed tube	2409 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −27→27
T_min = 0.272, T_max = 0.318	k = −6→6
9864 measured reflections	l = −13→13

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.022	H-atom parameters constrained
wR(F²) = 0.055	w = 1/[σ²(F_o²) + (0.0324P)² + 0.1121P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
2547 reflections	Δρ_max = 0.11 e Å⁻³
190 parameters	Δρ_min = −0.31 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1181 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.013 (16)

Crystal data top

[Fe(C₅H₅)(C₁₄H₁₁O)]	V = 1477.3 (4) Å³
M_r = 316.17	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 22.717 (3) Å	µ = 1.02 mm⁻¹
b = 5.8173 (9) Å	T = 296 K
c = 11.1789 (17) Å	0.32 × 0.28 × 0.27 mm

Data collection top

Bruker SMART 1000 CCD diffractometer	2547 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2409 reflections with I > 2σ(I)
T_min = 0.272, T_max = 0.318	R_int = 0.024
9864 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	H-atom parameters constrained
wR(F²) = 0.055	Δρ_max = 0.11 e Å⁻³
S = 1.00	Δρ_min = −0.31 e Å⁻³
2547 reflections	Absolute structure: Flack (1983), 1181 Friedel pairs
190 parameters	Absolute structure parameter: 0.013 (16)
1 restraint

Special details top

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	0.306705 (9)	0.01465 (4)	0.47590 (5)	0.03375 (9)
C1	0.39580 (9)	0.0389 (4)	0.4986 (2)	0.0520 (7)
H1	0.4258	−0.0099	0.4410	0.062*
C2	0.36997 (8)	0.2578 (4)	0.50508 (19)	0.0486 (5)
H2	0.3789	0.3888	0.4530	0.058*
C3	0.32944 (10)	0.2565 (4)	0.6003 (2)	0.0511 (5)
H3	0.3050	0.3865	0.6257	0.061*
C4	0.32990 (12)	0.0378 (5)	0.6524 (2)	0.0578 (7)
H4	0.3059	−0.0117	0.7205	0.069*
C5	0.37087 (11)	−0.0994 (4)	0.5899 (2)	0.0563 (6)
H5	0.3806	−0.2602	0.6070	0.068*
C6	0.26327 (8)	−0.2636 (4)	0.40577 (18)	0.0403 (4)
H6	0.2711	−0.4253	0.4243	0.048*
C7	0.22257 (8)	−0.1193 (4)	0.4653 (2)	0.0474 (5)
H7	0.1978	−0.1633	0.5333	0.057*
C8	0.22496 (9)	0.1022 (4)	0.4118 (2)	0.0464 (5)
H8	0.2019	0.2363	0.4366	0.056*
C9	0.26678 (8)	0.0985 (4)	0.31925 (18)	0.0396 (4)
H9	0.2772	0.2278	0.2672	0.047*
C10	0.29116 (8)	−0.1304 (3)	0.31345 (17)	0.0355 (4)
C11	0.33810 (8)	−0.2129 (3)	0.23428 (18)	0.0379 (4)
C12	0.37129 (9)	−0.0364 (3)	0.16579 (18)	0.0374 (4)
H12	0.3723	0.1141	0.1938	0.045*
C13	0.39948 (8)	−0.0888 (4)	0.06591 (18)	0.0381 (4)
H13	0.3976	−0.2411	0.0409	0.046*
C14	0.43347 (7)	0.0699 (4)	−0.0094 (2)	0.0390 (4)
C15	0.45591 (9)	0.2760 (4)	0.0339 (2)	0.0527 (6)
H15	0.4490	0.3180	0.1129	0.063*
C16	0.48835 (10)	0.4192 (4)	−0.0396 (3)	0.0685 (8)
H16	0.5037	0.5557	−0.0096	0.082*
C17	0.49790 (11)	0.3598 (6)	−0.1577 (3)	0.0731 (9)
H17	0.5196	0.4565	−0.2071	0.088*
C18	0.47553 (11)	0.1595 (6)	−0.2020 (2)	0.0706 (8)
H18	0.4815	0.1212	−0.2819	0.085*
C19	0.44402 (11)	0.0134 (4)	−0.1287 (2)	0.0551 (7)
H19	0.4297	−0.1243	−0.1592	0.066*
O1	0.34891 (7)	−0.4180 (3)	0.22424 (15)	0.0537 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.03735 (13)	0.03089 (14)	0.03302 (14)	−0.00503 (9)	0.00318 (15)	−0.00068 (16)
C1	0.0383 (9)	0.0610 (14)	0.0566 (19)	0.0006 (9)	−0.0049 (10)	−0.0147 (12)
C2	0.0470 (10)	0.0456 (12)	0.0533 (14)	−0.0170 (9)	−0.0010 (10)	−0.0027 (10)
C3	0.0575 (13)	0.0428 (13)	0.0530 (13)	−0.0073 (10)	0.0028 (11)	−0.0170 (11)
C4	0.0663 (15)	0.0747 (19)	0.0325 (12)	−0.0195 (13)	−0.0021 (11)	−0.0014 (12)
C5	0.0718 (14)	0.0403 (12)	0.0567 (15)	0.0009 (11)	−0.0294 (13)	−0.0010 (11)
C6	0.0472 (11)	0.0342 (11)	0.0394 (11)	−0.0132 (9)	−0.0020 (9)	0.0020 (9)
C7	0.0396 (9)	0.0548 (12)	0.0476 (12)	−0.0150 (8)	0.0054 (11)	0.0046 (14)
C8	0.0378 (11)	0.0476 (13)	0.0539 (12)	0.0006 (9)	0.0044 (9)	0.0009 (11)
C9	0.0393 (10)	0.0385 (11)	0.0408 (11)	0.0010 (9)	−0.0019 (8)	0.0050 (10)
C10	0.0413 (10)	0.0305 (10)	0.0346 (10)	−0.0065 (8)	−0.0032 (8)	0.0007 (8)
C11	0.0441 (10)	0.0383 (12)	0.0314 (10)	−0.0018 (8)	−0.0038 (8)	−0.0008 (9)
C12	0.0432 (10)	0.0308 (11)	0.0381 (12)	−0.0012 (8)	−0.0005 (8)	−0.0009 (8)
C13	0.0378 (9)	0.0379 (11)	0.0387 (11)	−0.0001 (9)	−0.0023 (8)	−0.0024 (9)
C14	0.0351 (8)	0.0464 (10)	0.0357 (12)	0.0030 (7)	0.0003 (9)	0.0035 (11)
C15	0.0501 (12)	0.0518 (14)	0.0563 (13)	−0.0021 (10)	0.0126 (10)	−0.0032 (11)
C16	0.0554 (12)	0.0530 (13)	0.097 (2)	−0.0041 (10)	0.0196 (16)	0.0093 (19)
C17	0.0561 (14)	0.087 (2)	0.076 (2)	0.0034 (15)	0.0202 (14)	0.0359 (17)
C18	0.0613 (14)	0.110 (2)	0.0409 (13)	0.0016 (16)	0.0054 (11)	0.0166 (15)
C19	0.0490 (13)	0.0759 (19)	0.0402 (14)	0.0005 (11)	−0.0025 (11)	−0.0008 (11)
O1	0.0756 (10)	0.0308 (8)	0.0548 (10)	0.0035 (7)	0.0113 (8)	−0.0010 (8)

Geometric parameters (Å, º) top

Fe1—C9	2.032 (2)	C7—H7	0.9800
Fe1—C10	2.033 (2)	C8—C9	1.405 (3)
Fe1—C2	2.0427 (19)	C8—H8	0.9800
Fe1—C3	2.044 (2)	C9—C10	1.443 (3)
Fe1—C1	2.045 (2)	C9—H9	0.9800
Fe1—C4	2.047 (2)	C10—C11	1.467 (3)
Fe1—C5	2.047 (2)	C11—O1	1.223 (2)
Fe1—C6	2.0513 (19)	C11—C12	1.486 (3)
Fe1—C8	2.055 (2)	C12—C13	1.323 (3)
Fe1—C7	2.0673 (17)	C12—H12	0.9300
C1—C2	1.404 (3)	C13—C14	1.469 (3)
C1—C5	1.417 (4)	C13—H13	0.9300
C1—H1	0.9800	C14—C15	1.390 (3)
C2—C3	1.407 (3)	C14—C19	1.393 (3)
C2—H2	0.9800	C15—C16	1.383 (4)
C3—C4	1.399 (3)	C15—H15	0.9300
C3—H3	0.9800	C16—C17	1.382 (4)
C4—C5	1.411 (4)	C16—H16	0.9300
C4—H4	0.9800	C17—C18	1.364 (4)
C5—H5	0.9800	C17—H17	0.9300
C6—C7	1.415 (3)	C18—C19	1.381 (4)
C6—C10	1.438 (3)	C18—H18	0.9300
C6—H6	0.9800	C19—H19	0.9300
C7—C8	1.421 (3)

C9—Fe1—C10	41.60 (8)	C3—C4—H4	125.9
C9—Fe1—C2	106.59 (9)	C5—C4—H4	125.9
C10—Fe1—C2	123.51 (8)	Fe1—C4—H4	125.9
C9—Fe1—C3	122.27 (9)	C4—C5—C1	107.4 (2)
C10—Fe1—C3	159.53 (9)	C4—C5—Fe1	69.84 (14)
C2—Fe1—C3	40.28 (9)	C1—C5—Fe1	69.67 (12)
C9—Fe1—C1	122.18 (10)	C4—C5—H5	126.3
C10—Fe1—C1	108.15 (9)	C1—C5—H5	126.3
C2—Fe1—C1	40.18 (8)	Fe1—C5—H5	126.3
C3—Fe1—C1	67.54 (9)	C7—C6—C10	107.81 (18)
C9—Fe1—C4	158.46 (10)	C7—C6—Fe1	70.51 (11)
C10—Fe1—C4	158.91 (9)	C10—C6—Fe1	68.72 (10)
C2—Fe1—C4	67.63 (9)	C7—C6—H6	126.1
C3—Fe1—C4	40.01 (9)	C10—C6—H6	126.1
C1—Fe1—C4	67.71 (11)	Fe1—C6—H6	126.1
C9—Fe1—C5	158.82 (10)	C6—C7—C8	108.35 (19)
C10—Fe1—C5	123.03 (9)	C6—C7—Fe1	69.30 (10)
C2—Fe1—C5	67.91 (9)	C8—C7—Fe1	69.34 (10)
C3—Fe1—C5	67.65 (10)	C6—C7—H7	125.8
C1—Fe1—C5	40.52 (10)	C8—C7—H7	125.8
C4—Fe1—C5	40.34 (10)	Fe1—C7—H7	125.8
C9—Fe1—C6	69.22 (8)	C9—C8—C7	108.77 (19)
C10—Fe1—C6	41.22 (8)	C9—C8—Fe1	69.01 (11)
C2—Fe1—C6	161.06 (8)	C7—C8—Fe1	70.31 (11)
C3—Fe1—C6	157.58 (9)	C9—C8—H8	125.6
C1—Fe1—C6	125.31 (8)	C7—C8—H8	125.6
C4—Fe1—C6	122.96 (9)	Fe1—C8—H8	125.6
C5—Fe1—C6	108.95 (9)	C8—C9—C10	107.86 (18)
C9—Fe1—C8	40.22 (8)	C8—C9—Fe1	70.77 (12)
C10—Fe1—C8	68.56 (8)	C10—C9—Fe1	69.27 (11)
C2—Fe1—C8	121.33 (9)	C8—C9—H9	126.1
C3—Fe1—C8	107.15 (10)	C10—C9—H9	126.1
C1—Fe1—C8	157.07 (10)	Fe1—C9—H9	126.1
C4—Fe1—C8	123.54 (10)	C6—C10—C9	107.21 (17)
C5—Fe1—C8	160.26 (10)	C6—C10—C11	125.25 (18)
C6—Fe1—C8	68.13 (9)	C9—C10—C11	127.45 (18)
C9—Fe1—C7	68.19 (9)	C6—C10—Fe1	70.06 (11)
C10—Fe1—C7	68.41 (9)	C9—C10—Fe1	69.13 (11)
C2—Fe1—C7	157.00 (9)	C11—C10—Fe1	123.27 (13)
C3—Fe1—C7	122.13 (10)	O1—C11—C10	121.38 (18)
C1—Fe1—C7	161.47 (9)	O1—C11—C12	121.64 (18)
C4—Fe1—C7	108.53 (11)	C10—C11—C12	116.97 (17)
C5—Fe1—C7	124.88 (11)	C13—C12—C11	121.42 (19)
C6—Fe1—C7	40.19 (8)	C13—C12—H12	119.3
C8—Fe1—C7	40.35 (9)	C11—C12—H12	119.3
C2—C1—C5	108.1 (2)	C12—C13—C14	126.4 (2)
C2—C1—Fe1	69.83 (11)	C12—C13—H13	116.8
C5—C1—Fe1	69.81 (12)	C14—C13—H13	116.8
C2—C1—H1	125.9	C15—C14—C19	118.3 (2)
C5—C1—H1	125.9	C15—C14—C13	122.3 (2)
Fe1—C1—H1	125.9	C19—C14—C13	119.4 (2)
C1—C2—C3	107.9 (2)	C16—C15—C14	120.5 (3)
C1—C2—Fe1	69.98 (11)	C16—C15—H15	119.7
C3—C2—Fe1	69.92 (11)	C14—C15—H15	119.7
C1—C2—H2	126.1	C17—C16—C15	120.0 (3)
C3—C2—H2	126.1	C17—C16—H16	120.0
Fe1—C2—H2	126.1	C15—C16—H16	120.0
C4—C3—C2	108.4 (2)	C18—C17—C16	120.2 (2)
C4—C3—Fe1	70.09 (12)	C18—C17—H17	119.9
C2—C3—Fe1	69.80 (12)	C16—C17—H17	119.9
C4—C3—H3	125.8	C17—C18—C19	120.2 (2)
C2—C3—H3	125.8	C17—C18—H18	119.9
Fe1—C3—H3	125.8	C19—C18—H18	119.9
C3—C4—C5	108.2 (2)	C18—C19—C14	120.8 (2)
C3—C4—Fe1	69.90 (13)	C18—C19—H19	119.6
C5—C4—Fe1	69.82 (13)	C14—C19—H19	119.6

C9—Fe1—C1—C2	77.16 (16)	C10—C6—C7—C8	−0.3 (2)
C10—Fe1—C1—C2	120.82 (14)	Fe1—C6—C7—C8	58.49 (14)
C3—Fe1—C1—C2	−37.83 (14)	C10—C6—C7—Fe1	−58.80 (13)
C4—Fe1—C1—C2	−81.25 (15)	C9—Fe1—C7—C6	83.20 (13)
C5—Fe1—C1—C2	−119.2 (2)	C10—Fe1—C7—C6	38.26 (12)
C6—Fe1—C1—C2	163.27 (13)	C2—Fe1—C7—C6	164.2 (2)
C8—Fe1—C1—C2	43.1 (3)	C3—Fe1—C7—C6	−161.47 (13)
C7—Fe1—C1—C2	−163.1 (3)	C1—Fe1—C7—C6	−44.5 (4)
C9—Fe1—C1—C5	−163.61 (13)	C4—Fe1—C7—C6	−119.50 (15)
C10—Fe1—C1—C5	−119.96 (14)	C5—Fe1—C7—C6	−77.76 (17)
C2—Fe1—C1—C5	119.2 (2)	C8—Fe1—C7—C6	120.1 (2)
C3—Fe1—C1—C5	81.40 (15)	C9—Fe1—C7—C8	−36.94 (14)
C4—Fe1—C1—C5	37.98 (14)	C10—Fe1—C7—C8	−81.88 (15)
C6—Fe1—C1—C5	−77.51 (16)	C2—Fe1—C7—C8	44.1 (3)
C8—Fe1—C1—C5	162.3 (2)	C3—Fe1—C7—C8	78.39 (17)
C7—Fe1—C1—C5	−43.9 (4)	C1—Fe1—C7—C8	−164.6 (3)
C5—C1—C2—C3	0.4 (2)	C4—Fe1—C7—C8	120.36 (15)
Fe1—C1—C2—C3	59.90 (14)	C5—Fe1—C7—C8	162.10 (14)
C5—C1—C2—Fe1	−59.53 (14)	C6—Fe1—C7—C8	−120.1 (2)
C9—Fe1—C2—C1	−120.56 (15)	C6—C7—C8—C9	0.0 (2)
C10—Fe1—C2—C1	−78.18 (17)	Fe1—C7—C8—C9	58.43 (15)
C3—Fe1—C2—C1	118.8 (2)	C6—C7—C8—Fe1	−58.46 (14)
C4—Fe1—C2—C1	81.47 (16)	C10—Fe1—C8—C9	−38.75 (13)
C5—Fe1—C2—C1	37.73 (15)	C2—Fe1—C8—C9	78.34 (15)
C6—Fe1—C2—C1	−46.4 (3)	C3—Fe1—C8—C9	120.02 (14)
C8—Fe1—C2—C1	−161.85 (14)	C1—Fe1—C8—C9	47.3 (3)
C7—Fe1—C2—C1	166.3 (3)	C4—Fe1—C8—C9	160.81 (13)
C9—Fe1—C2—C3	120.67 (14)	C5—Fe1—C8—C9	−168.5 (2)
C10—Fe1—C2—C3	163.06 (13)	C6—Fe1—C8—C9	−83.26 (13)
C1—Fe1—C2—C3	−118.8 (2)	C7—Fe1—C8—C9	−120.2 (2)
C4—Fe1—C2—C3	−37.29 (14)	C9—Fe1—C8—C7	120.2 (2)
C5—Fe1—C2—C3	−81.03 (16)	C10—Fe1—C8—C7	81.47 (15)
C6—Fe1—C2—C3	−165.1 (3)	C2—Fe1—C8—C7	−161.44 (14)
C8—Fe1—C2—C3	79.38 (16)	C3—Fe1—C8—C7	−119.75 (15)
C7—Fe1—C2—C3	47.6 (3)	C1—Fe1—C8—C7	167.5 (2)
C1—C2—C3—C4	−0.2 (2)	C4—Fe1—C8—C7	−78.97 (17)
Fe1—C2—C3—C4	59.71 (15)	C5—Fe1—C8—C7	−48.3 (3)
C1—C2—C3—Fe1	−59.94 (14)	C6—Fe1—C8—C7	36.97 (14)
C9—Fe1—C3—C4	163.52 (14)	C7—C8—C9—C10	0.4 (2)
C10—Fe1—C3—C4	−163.4 (2)	Fe1—C8—C9—C10	59.58 (13)
C2—Fe1—C3—C4	−119.4 (2)	C7—C8—C9—Fe1	−59.23 (15)
C1—Fe1—C3—C4	−81.62 (17)	C10—Fe1—C9—C8	118.64 (17)
C5—Fe1—C3—C4	−37.62 (16)	C2—Fe1—C9—C8	−119.21 (13)
C6—Fe1—C3—C4	48.0 (3)	C3—Fe1—C9—C8	−78.08 (16)
C8—Fe1—C3—C4	122.12 (16)	C1—Fe1—C9—C8	−160.23 (13)
C7—Fe1—C3—C4	80.54 (17)	C4—Fe1—C9—C8	−48.3 (3)
C9—Fe1—C3—C2	−77.13 (15)	C5—Fe1—C9—C8	169.3 (2)
C10—Fe1—C3—C2	−44.0 (3)	C6—Fe1—C9—C8	80.31 (13)
C1—Fe1—C3—C2	37.74 (14)	C7—Fe1—C9—C8	37.05 (13)
C4—Fe1—C3—C2	119.4 (2)	C2—Fe1—C9—C10	122.15 (12)
C5—Fe1—C3—C2	81.74 (15)	C3—Fe1—C9—C10	163.28 (12)
C6—Fe1—C3—C2	167.4 (2)	C1—Fe1—C9—C10	81.12 (13)
C8—Fe1—C3—C2	−118.52 (14)	C4—Fe1—C9—C10	−166.9 (2)
C7—Fe1—C3—C2	−160.10 (14)	C5—Fe1—C9—C10	50.6 (3)
C2—C3—C4—C5	0.0 (3)	C6—Fe1—C9—C10	−38.33 (11)
Fe1—C3—C4—C5	59.53 (16)	C8—Fe1—C9—C10	−118.64 (17)
C2—C3—C4—Fe1	−59.53 (15)	C7—Fe1—C9—C10	−81.59 (12)
C9—Fe1—C4—C3	−40.8 (3)	C7—C6—C10—C9	0.5 (2)
C10—Fe1—C4—C3	163.9 (2)	Fe1—C6—C10—C9	−59.41 (13)
C2—Fe1—C4—C3	37.54 (14)	C7—C6—C10—C11	177.20 (18)
C1—Fe1—C4—C3	81.14 (15)	Fe1—C6—C10—C11	117.27 (19)
C5—Fe1—C4—C3	119.3 (2)	C7—C6—C10—Fe1	59.92 (14)
C6—Fe1—C4—C3	−160.25 (13)	C8—C9—C10—C6	−0.5 (2)
C8—Fe1—C4—C3	−76.15 (17)	Fe1—C9—C10—C6	60.00 (13)
C7—Fe1—C4—C3	−118.23 (15)	C8—C9—C10—C11	−177.12 (18)
C9—Fe1—C4—C5	−160.1 (2)	Fe1—C9—C10—C11	−116.59 (19)
C10—Fe1—C4—C5	44.6 (3)	C8—C9—C10—Fe1	−60.53 (14)
C2—Fe1—C4—C5	−81.75 (16)	C9—Fe1—C10—C6	−118.36 (16)
C3—Fe1—C4—C5	−119.3 (2)	C2—Fe1—C10—C6	164.95 (12)
C1—Fe1—C4—C5	−38.15 (14)	C3—Fe1—C10—C6	−162.5 (2)
C6—Fe1—C4—C5	80.46 (17)	C1—Fe1—C10—C6	123.29 (13)
C8—Fe1—C4—C5	164.56 (14)	C4—Fe1—C10—C6	48.3 (3)
C7—Fe1—C4—C5	122.48 (15)	C5—Fe1—C10—C6	81.11 (15)
C3—C4—C5—C1	0.2 (3)	C8—Fe1—C10—C6	−80.85 (12)
Fe1—C4—C5—C1	59.80 (15)	C7—Fe1—C10—C6	−37.34 (12)
C3—C4—C5—Fe1	−59.57 (16)	C2—Fe1—C10—C9	−76.69 (14)
C2—C1—C5—C4	−0.4 (2)	C3—Fe1—C10—C9	−44.1 (3)
Fe1—C1—C5—C4	−59.91 (16)	C1—Fe1—C10—C9	−118.35 (12)
C2—C1—C5—Fe1	59.54 (15)	C4—Fe1—C10—C9	166.7 (2)
C9—Fe1—C5—C4	159.8 (2)	C5—Fe1—C10—C9	−160.53 (13)
C10—Fe1—C5—C4	−162.47 (14)	C6—Fe1—C10—C9	118.36 (16)
C2—Fe1—C5—C4	80.99 (15)	C8—Fe1—C10—C9	37.51 (12)
C3—Fe1—C5—C4	37.32 (14)	C7—Fe1—C10—C9	81.02 (12)
C1—Fe1—C5—C4	118.4 (2)	C9—Fe1—C10—C11	121.9 (2)
C6—Fe1—C5—C4	−118.98 (15)	C2—Fe1—C10—C11	45.2 (2)
C8—Fe1—C5—C4	−41.1 (3)	C3—Fe1—C10—C11	77.8 (3)
C7—Fe1—C5—C4	−77.16 (18)	C1—Fe1—C10—C11	3.54 (19)
C9—Fe1—C5—C1	41.4 (3)	C4—Fe1—C10—C11	−71.5 (3)
C10—Fe1—C5—C1	79.12 (14)	C5—Fe1—C10—C11	−38.6 (2)
C2—Fe1—C5—C1	−37.42 (12)	C6—Fe1—C10—C11	−119.8 (2)
C3—Fe1—C5—C1	−81.09 (14)	C8—Fe1—C10—C11	159.39 (19)
C4—Fe1—C5—C1	−118.4 (2)	C7—Fe1—C10—C11	−157.09 (19)
C6—Fe1—C5—C1	122.61 (13)	C6—C10—C11—O1	15.5 (3)
C8—Fe1—C5—C1	−159.5 (3)	C9—C10—C11—O1	−168.5 (2)
C7—Fe1—C5—C1	164.43 (13)	Fe1—C10—C11—O1	103.5 (2)
C9—Fe1—C6—C7	−80.41 (14)	C6—C10—C11—C12	−165.28 (18)
C10—Fe1—C6—C7	−119.08 (18)	C9—C10—C11—C12	10.7 (3)
C2—Fe1—C6—C7	−160.9 (3)	Fe1—C10—C11—C12	−77.3 (2)
C3—Fe1—C6—C7	44.9 (3)	O1—C11—C12—C13	22.2 (3)
C1—Fe1—C6—C7	164.17 (16)	C10—C11—C12—C13	−157.06 (18)
C4—Fe1—C6—C7	79.60 (17)	C11—C12—C13—C14	179.80 (18)
C5—Fe1—C6—C7	122.05 (15)	C12—C13—C14—C15	21.4 (3)
C8—Fe1—C6—C7	−37.10 (14)	C12—C13—C14—C19	−158.8 (2)
C9—Fe1—C6—C10	38.67 (11)	C19—C14—C15—C16	−0.7 (3)
C2—Fe1—C6—C10	−41.8 (3)	C13—C14—C15—C16	179.1 (2)
C3—Fe1—C6—C10	164.0 (2)	C14—C15—C16—C17	1.0 (4)
C1—Fe1—C6—C10	−76.75 (15)	C15—C16—C17—C18	−0.2 (4)
C4—Fe1—C6—C10	−161.32 (13)	C16—C17—C18—C19	−1.0 (4)
C5—Fe1—C6—C10	−118.87 (13)	C17—C18—C19—C14	1.4 (4)
C8—Fe1—C6—C10	81.98 (12)	C15—C14—C19—C18	−0.5 (3)
C7—Fe1—C6—C10	119.08 (18)	C13—C14—C19—C18	179.6 (2)

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₁₄H₁₁O)]
M_r	316.17
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	296
a, b, c (Å)	22.717 (3), 5.8173 (9), 11.1789 (17)
V (Å³)	1477.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.02
Crystal size (mm)	0.32 × 0.28 × 0.27

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.272, 0.318
No. of measured, independent and observed [I > 2σ(I)] reflections	9864, 2547, 2409
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.055, 1.00
No. of reflections	2547
No. of parameters	190
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.11, −0.31
Absolute structure	Flack (1983), 1181 Friedel pairs
Absolute structure parameter	0.013 (16)

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Dihedral angles (°) for selected planes top

	Atoms defining plane	1-Plane	2-Plane	Cp plane
1-Plane	C11–C13/O1
2-Plane	C14–C19	33.0 (1)
Cp plane	C1–C5	17.9 (2)	50.6 (4)
Cps plane	C6–C10	17.0 (1)	49.9 (1)	1.8 (1)

Hydrogen-bond geometry (Å, °) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1ⁱ	0.98	2.67	3.538 (3)	148
C1—H1···Cg3ⁱⁱ	0.98	2.75	3.596 (2)	145 (δ = 64)

δ is the angle the C1/H1 group makes with the normal to the Cp plane, and Cg3 is the centroid of the Cp ring. Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y, z+1/2.

Acknowledgements

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

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