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

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

doi:10.1107/S1600536808025518

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page m1164

doi:10.1107/S1600536808025518

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

Shi-Jia Long,^a Xiao-Lan Liu ^b and Yong-Hong Liu ^b ^*

^aCollege of Life Sciences and Chemistry, Tianshui Normal University, Tianshui 741000, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, People's Republic of China
^*Correspondence e-mail: yhliuyzu@yahoo.com.cn

(Received 29 July 2008; accepted 8 August 2008; online 13 August 2008)

In the title compound, [Fe(C₅H₅)(C₁₅H₁₃O₂)], a conjugated substituent group bridges a five-membered η⁵-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⋯π(Cps) interaction.

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_r = 346.19
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.032
wR(F²) = 0.089
S = 1.02
3787 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the substituted cyclopentadienyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O1	0.93	2.50	2.830 (2)	101
C8—H8⋯O1ⁱ	0.93	2.60	3.345 (2)	137
C9—H9⋯O1ⁱⁱ	0.93	2.54	3.414 (2)	156
C12—H12⋯O1ⁱⁱ	0.93	2.46	3.346 (2)	160
C15—H15⋯O1ⁱⁱ	0.93	2.65	3.441 (2)	143
C19—H19⋯O2ⁱⁱⁱ	0.93	2.59	3.472 (3)	157
C3—H3⋯Cg1ⁱ	0.93	3.24	3.808 (2)	121
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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, 2003 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808025518/pv2096sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808025518/pv2096Isup2.hkl

checkCIF report

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.

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

	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.
	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.
	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.
	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)]	F(000) = 1440
M_r = 346.19	D_x = 1.409 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 6158 reflections
a = 12.3124 (14) Å	θ = 3.0–25.5°
b = 10.2316 (11) Å	µ = 0.93 mm⁻¹
c = 25.914 (3) Å	T = 296 K
V = 3264.5 (6) Å³	Block, red
Z = 8	0.30 × 0.30 × 0.20 mm

Data collection top

Bruker SMART 1000 CCD diffractometer	3787 independent reflections
Radiation source: fine-focus sealed tube	2662 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ϕ and ω scans	θ_max = 27.6°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −14→16
T_min = 0.768, T_max = 0.836	k = −13→13
26999 measured reflections	l = −33→33

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.089	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0396P)² + 0.9963P] where P = (F_o² + 2F_c²)/3
3787 reflections	(Δ/σ)_max = 0.001
209 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

[Fe(C₅H₅)(C₁₅H₁₃O₂)]	V = 3264.5 (6) Å³
M_r = 346.19	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 12.3124 (14) Å	µ = 0.93 mm⁻¹
b = 10.2316 (11) Å	T = 296 K
c = 25.914 (3) Å	0.30 × 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)
T_min = 0.768, T_max = 0.836	R_int = 0.037
26999 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.089	H-atom parameters constrained
S = 1.02	Δρ_max = 0.20 e Å⁻³
3787 reflections	Δρ_min = −0.28 e Å⁻³
209 parameters

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

	x	y	z	U_iso*/U_eq
Fe1	0.47330 (2)	0.24558 (2)	0.447598 (9)	0.03889 (10)
O1	0.17057 (11)	0.14263 (12)	0.41478 (5)	0.0509 (3)
C14	0.14386 (15)	0.45292 (18)	0.30462 (7)	0.0423 (4)
C12	0.22120 (15)	0.35247 (17)	0.38469 (7)	0.0424 (4)
H12	0.2671	0.4235	0.3898	0.051*
C17	0.12977 (17)	0.6313 (2)	0.22287 (7)	0.0502 (5)
C15	0.22061 (16)	0.5508 (2)	0.29796 (7)	0.0502 (5)
H15	0.2777	0.5574	0.3213	0.060*
C13	0.15074 (15)	0.35526 (18)	0.34563 (7)	0.0433 (4)
H13	0.1004	0.2876	0.3444	0.052*
C16	0.21475 (17)	0.6392 (2)	0.25751 (7)	0.0530 (5)
H16	0.2677	0.7033	0.2537	0.064*
C19	0.05897 (17)	0.4478 (2)	0.26898 (8)	0.0552 (5)
H19	0.0062	0.3833	0.2723	0.066*
C11	0.22818 (15)	0.23985 (17)	0.41997 (7)	0.0405 (4)
C18	0.05177 (18)	0.5362 (2)	0.22907 (8)	0.0589 (6)
H18	−0.0062	0.5316	0.2061	0.071*
C7	0.43869 (17)	0.1790 (2)	0.52041 (8)	0.0553 (5)
H7	0.4829	0.1267	0.5409	0.066*
C9	0.36118 (15)	0.35924 (19)	0.48277 (7)	0.0454 (4)
H9	0.3459	0.4455	0.4740	0.055*
C1	0.54687 (18)	0.1382 (2)	0.39076 (8)	0.0580 (5)
H1	0.5308	0.0523	0.3818	0.070*
C6	0.36007 (15)	0.13343 (19)	0.48474 (8)	0.0495 (5)
H6	0.3436	0.0465	0.4778	0.059*
C10	0.31062 (15)	0.24527 (17)	0.46128 (7)	0.0418 (4)
C5	0.49898 (18)	0.2505 (2)	0.36970 (8)	0.0548 (5)
H5	0.4455	0.2521	0.3443	0.066*
C2	0.62385 (17)	0.1786 (2)	0.42794 (8)	0.0600 (6)
H2	0.6674	0.1240	0.4478	0.072*
C3	0.62294 (17)	0.3156 (2)	0.42965 (8)	0.0582 (6)
H3	0.6658	0.3677	0.4509	0.070*
C8	0.43881 (17)	0.3170 (2)	0.51975 (7)	0.0529 (5)
H8	0.4822	0.3709	0.5400	0.064*
C4	0.54580 (18)	0.3608 (2)	0.39360 (8)	0.0569 (5)
H4	0.5288	0.4477	0.3868	0.068*
O2	0.11598 (14)	0.71299 (17)	0.18152 (6)	0.0679 (4)
C20	0.1979 (2)	0.8096 (3)	0.17227 (11)	0.0906 (9)
H20A	0.1996	0.8703	0.2005	0.136*
H20B	0.1818	0.8555	0.1409	0.136*
H20C	0.2674	0.7677	0.1692	0.136*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.03704 (16)	0.03933 (16)	0.04030 (15)	0.00167 (11)	0.00085 (10)	0.00384 (11)
O1	0.0463 (7)	0.0378 (7)	0.0686 (8)	−0.0054 (6)	0.0019 (7)	0.0049 (6)
C14	0.0404 (10)	0.0407 (10)	0.0458 (10)	0.0023 (8)	−0.0012 (8)	−0.0031 (8)
C12	0.0399 (10)	0.0333 (9)	0.0541 (10)	0.0000 (8)	−0.0016 (8)	0.0020 (8)
C17	0.0562 (12)	0.0520 (12)	0.0425 (10)	0.0149 (10)	0.0028 (9)	0.0008 (9)
C15	0.0477 (11)	0.0524 (12)	0.0506 (11)	−0.0053 (10)	−0.0095 (9)	0.0036 (9)
C13	0.0391 (10)	0.0364 (10)	0.0545 (10)	−0.0007 (8)	0.0011 (8)	−0.0001 (8)
C16	0.0561 (13)	0.0490 (12)	0.0541 (11)	−0.0040 (10)	−0.0012 (10)	0.0052 (9)
C19	0.0453 (11)	0.0578 (13)	0.0626 (13)	−0.0075 (10)	−0.0082 (10)	−0.0002 (10)
C11	0.0362 (9)	0.0348 (9)	0.0504 (10)	0.0040 (8)	0.0076 (7)	0.0014 (8)
C18	0.0518 (12)	0.0698 (15)	0.0552 (12)	0.0036 (11)	−0.0159 (10)	0.0025 (11)
C7	0.0519 (12)	0.0666 (14)	0.0475 (11)	0.0084 (11)	0.0023 (10)	0.0179 (10)
C9	0.0462 (10)	0.0434 (10)	0.0466 (10)	0.0056 (9)	0.0033 (9)	−0.0014 (8)
C1	0.0591 (13)	0.0538 (13)	0.0613 (13)	0.0016 (11)	0.0120 (11)	−0.0105 (11)
C6	0.0465 (11)	0.0434 (11)	0.0586 (11)	0.0025 (9)	0.0083 (10)	0.0162 (9)
C10	0.0360 (9)	0.0413 (10)	0.0481 (9)	0.0032 (8)	0.0064 (8)	0.0073 (8)
C5	0.0491 (11)	0.0756 (16)	0.0397 (10)	−0.0032 (11)	0.0015 (8)	0.0007 (10)
C2	0.0431 (12)	0.0792 (17)	0.0578 (12)	0.0134 (11)	0.0053 (10)	0.0048 (12)
C3	0.0454 (12)	0.0774 (16)	0.0516 (12)	−0.0177 (11)	0.0040 (10)	−0.0041 (11)
C8	0.0526 (12)	0.0649 (14)	0.0412 (10)	0.0058 (10)	0.0021 (9)	−0.0020 (10)
C4	0.0665 (14)	0.0525 (13)	0.0518 (11)	−0.0069 (11)	0.0112 (10)	0.0099 (10)
O2	0.0735 (11)	0.0751 (10)	0.0552 (8)	0.0178 (9)	0.0000 (8)	0.0171 (8)
C20	0.0817 (19)	0.103 (2)	0.0877 (18)	0.0128 (17)	0.0247 (16)	0.0454 (17)

Geometric parameters (Å, º) top

Fe1—C9	2.0220 (18)	C11—C10	1.476 (3)
Fe1—C3	2.031 (2)	C18—H18	0.9300
Fe1—C10	2.0341 (18)	C7—C8	1.412 (3)
Fe1—C4	2.036 (2)	C7—C6	1.417 (3)
Fe1—C2	2.041 (2)	C7—H7	0.9300
Fe1—C5	2.044 (2)	C9—C8	1.421 (3)
Fe1—C6	2.0462 (18)	C9—C10	1.434 (3)
Fe1—C1	2.049 (2)	C9—H9	0.9300
Fe1—C7	2.0507 (19)	C1—C5	1.403 (3)
Fe1—C8	2.052 (2)	C1—C2	1.414 (3)
O1—C11	1.229 (2)	C1—H1	0.9300
C14—C15	1.388 (3)	C6—C10	1.432 (2)
C14—C19	1.396 (3)	C6—H6	0.9300
C14—C13	1.461 (2)	C5—C4	1.410 (3)
C12—C13	1.333 (2)	C5—H5	0.9300
C12—C11	1.473 (2)	C2—C3	1.403 (3)
C12—H12	0.9300	C2—H2	0.9300
C17—O2	1.369 (2)	C3—C4	1.410 (3)
C17—C18	1.377 (3)	C3—H3	0.9300
C17—C16	1.381 (3)	C8—H8	0.9300
C15—C16	1.386 (3)	C4—H4	0.9300
C15—H15	0.9300	O2—C20	1.433 (3)
C13—H13	0.9300	C20—H20A	0.9600
C16—H16	0.9300	C20—H20B	0.9600
C19—C18	1.377 (3)	C20—H20C	0.9600
C19—H19	0.9300

C9—Fe1—C3	121.31 (9)	C19—C18—H18	119.8
C9—Fe1—C10	41.42 (7)	C17—C18—H18	119.8
C3—Fe1—C10	159.03 (9)	C8—C7—C6	108.78 (18)
C9—Fe1—C4	106.03 (9)	C8—C7—Fe1	69.92 (11)
C3—Fe1—C4	40.57 (9)	C6—C7—Fe1	69.59 (11)
C10—Fe1—C4	123.54 (8)	C8—C7—H7	125.6
C9—Fe1—C2	157.77 (9)	C6—C7—H7	125.6
C3—Fe1—C2	40.30 (10)	Fe1—C7—H7	126.5
C10—Fe1—C2	159.61 (9)	C8—C9—C10	107.85 (17)
C4—Fe1—C2	67.95 (9)	C8—C9—Fe1	70.72 (11)
C9—Fe1—C5	122.45 (8)	C10—C9—Fe1	69.74 (10)
C3—Fe1—C5	67.96 (9)	C8—C9—H9	126.1
C10—Fe1—C5	108.94 (8)	C10—C9—H9	126.1
C4—Fe1—C5	40.44 (8)	Fe1—C9—H9	125.1
C2—Fe1—C5	67.74 (9)	C5—C1—C2	107.9 (2)
C9—Fe1—C6	69.23 (8)	C5—C1—Fe1	69.76 (12)
C3—Fe1—C6	157.48 (9)	C2—C1—Fe1	69.47 (12)
C10—Fe1—C6	41.08 (7)	C5—C1—H1	126.1
C4—Fe1—C6	161.23 (9)	C2—C1—H1	126.1
C2—Fe1—C6	123.23 (9)	Fe1—C1—H1	126.3
C5—Fe1—C6	125.73 (9)	C7—C6—C10	107.71 (18)
C9—Fe1—C1	159.13 (9)	C7—C6—Fe1	69.93 (11)
C3—Fe1—C1	67.89 (9)	C10—C6—Fe1	69.00 (10)
C10—Fe1—C1	124.04 (8)	C7—C6—H6	126.1
C4—Fe1—C1	67.83 (10)	C10—C6—H6	126.1
C2—Fe1—C1	40.44 (9)	Fe1—C6—H6	126.5
C5—Fe1—C1	40.09 (8)	C6—C10—C9	107.48 (17)
C6—Fe1—C1	109.79 (9)	C6—C10—C11	124.77 (17)
C9—Fe1—C7	68.56 (8)	C9—C10—C11	127.62 (16)
C3—Fe1—C7	121.09 (9)	C6—C10—Fe1	69.91 (10)
C10—Fe1—C7	68.56 (8)	C9—C10—Fe1	68.84 (10)
C4—Fe1—C7	156.32 (9)	C11—C10—Fe1	123.41 (13)
C2—Fe1—C7	107.87 (9)	C1—C5—C4	108.2 (2)
C5—Fe1—C7	161.64 (9)	C1—C5—Fe1	70.15 (12)
C6—Fe1—C7	40.48 (8)	C4—C5—Fe1	69.47 (11)
C1—Fe1—C7	125.11 (9)	C1—C5—H5	125.9
C9—Fe1—C8	40.82 (8)	C4—C5—H5	125.9
C3—Fe1—C8	105.71 (9)	Fe1—C5—H5	126.1
C10—Fe1—C8	68.77 (8)	C3—C2—C1	108.00 (19)
C4—Fe1—C8	120.73 (9)	C3—C2—Fe1	69.48 (12)
C2—Fe1—C8	122.34 (9)	C1—C2—Fe1	70.09 (12)
C5—Fe1—C8	157.40 (9)	C3—C2—H2	126.0
C6—Fe1—C8	68.28 (9)	C1—C2—H2	126.0
C1—Fe1—C8	159.65 (9)	Fe1—C2—H2	126.0
C7—Fe1—C8	40.25 (9)	C2—C3—C4	108.18 (19)
C15—C14—C19	117.06 (18)	C2—C3—Fe1	70.23 (12)
C15—C14—C13	123.00 (17)	C4—C3—Fe1	69.89 (12)
C19—C14—C13	119.92 (18)	C2—C3—H3	125.9
C13—C12—C11	121.71 (17)	C4—C3—H3	125.9
C13—C12—H12	119.1	Fe1—C3—H3	125.5
C11—C12—H12	119.1	C7—C8—C9	108.16 (19)
O2—C17—C18	115.87 (19)	C7—C8—Fe1	69.83 (12)
O2—C17—C16	124.5 (2)	C9—C8—Fe1	68.47 (11)
C18—C17—C16	119.58 (18)	C7—C8—H8	125.9
C16—C15—C14	121.96 (18)	C9—C8—H8	125.9
C16—C15—H15	119.0	Fe1—C8—H8	127.4
C14—C15—H15	119.0	C3—C4—C5	107.7 (2)
C12—C13—C14	127.19 (17)	C3—C4—Fe1	69.53 (11)
C12—C13—H13	116.4	C5—C4—Fe1	70.09 (12)
C14—C13—H13	116.4	C3—C4—H4	126.1
C17—C16—C15	119.55 (19)	C5—C4—H4	126.1
C17—C16—H16	120.2	Fe1—C4—H4	125.8
C15—C16—H16	120.2	C17—O2—C20	117.68 (19)
C18—C19—C14	121.4 (2)	O2—C20—H20A	109.5
C18—C19—H19	119.3	O2—C20—H20B	109.5
C14—C19—H19	119.3	H20A—C20—H20B	109.5
O1—C11—C12	122.11 (17)	O2—C20—H20C	109.5
O1—C11—C10	120.43 (16)	H20A—C20—H20C	109.5
C12—C11—C10	117.43 (16)	H20B—C20—H20C	109.5
C19—C18—C17	120.48 (19)

C19—C14—C15—C16	−0.7 (3)	C8—Fe1—C10—C9	38.10 (11)
C13—C14—C15—C16	177.32 (18)	C9—Fe1—C10—C11	121.93 (19)
C11—C12—C13—C14	−172.39 (17)	C3—Fe1—C10—C11	81.7 (3)
C15—C14—C13—C12	7.6 (3)	C4—Fe1—C10—C11	46.44 (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—C11	3.99 (17)
C18—C17—C16—C15	0.2 (3)	C6—Fe1—C10—C11	−119.1 (2)
C14—C15—C16—C17	0.7 (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—C11	160.03 (17)
C13—C12—C11—O1	0.9 (3)	C2—C1—C5—C4	0.0 (2)
C13—C12—C11—C10	178.68 (17)	Fe1—C1—C5—C4	59.23 (15)
C14—C19—C18—C17	1.0 (3)	C2—C1—C5—Fe1	−59.23 (14)
O2—C17—C18—C19	179.00 (19)	C9—Fe1—C5—C1	−164.59 (12)
C16—C17—C18—C19	−1.1 (3)	C3—Fe1—C5—C1	81.40 (14)
C9—Fe1—C7—C8	−37.40 (12)	C10—Fe1—C5—C1	−120.76 (13)
C3—Fe1—C7—C8	77.12 (15)	C4—Fe1—C5—C1	119.4 (2)
C10—Fe1—C7—C8	−82.06 (13)	C2—Fe1—C5—C1	37.73 (13)
C4—Fe1—C7—C8	43.6 (3)	C6—Fe1—C5—C1	−78.05 (15)
C2—Fe1—C7—C8	119.28 (13)	C7—Fe1—C5—C1	−41.9 (3)
C5—Fe1—C7—C8	−167.7 (2)	C8—Fe1—C5—C1	159.1 (2)
C6—Fe1—C7—C8	−120.12 (17)	C9—Fe1—C5—C4	76.03 (15)
C1—Fe1—C7—C8	160.61 (13)	C3—Fe1—C5—C4	−37.98 (14)
C9—Fe1—C7—C6	82.72 (13)	C10—Fe1—C5—C4	119.86 (13)
C3—Fe1—C7—C6	−162.76 (12)	C2—Fe1—C5—C4	−81.64 (15)
C10—Fe1—C7—C6	38.06 (11)	C6—Fe1—C5—C4	162.57 (12)
C4—Fe1—C7—C6	163.7 (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—C4	39.8 (3)
C1—Fe1—C7—C6	−79.27 (15)	C5—C1—C2—C3	0.1 (2)
C8—Fe1—C7—C6	120.12 (17)	Fe1—C1—C2—C3	−59.36 (14)
C3—Fe1—C9—C8	−77.33 (14)	C5—C1—C2—Fe1	59.41 (15)
C10—Fe1—C9—C8	118.37 (16)	C9—Fe1—C2—C3	−40.4 (3)
C4—Fe1—C9—C8	−118.72 (13)	C10—Fe1—C2—C3	166.3 (2)
C2—Fe1—C9—C8	−48.0 (3)	C4—Fe1—C2—C3	37.87 (12)
C5—Fe1—C9—C8	−159.64 (13)	C5—Fe1—C2—C3	81.70 (13)
C6—Fe1—C9—C8	80.43 (13)	C6—Fe1—C2—C3	−159.21 (12)
C1—Fe1—C9—C8	171.7 (2)	C1—Fe1—C2—C3	119.11 (18)
C7—Fe1—C9—C8	36.90 (13)	C7—Fe1—C2—C3	−117.30 (13)
C3—Fe1—C9—C10	164.30 (11)	C8—Fe1—C2—C3	−75.45 (15)
C4—Fe1—C9—C10	122.91 (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—C10	81.99 (13)	C10—Fe1—C2—C1	47.2 (3)
C6—Fe1—C9—C10	−37.94 (11)	C4—Fe1—C2—C1	−81.24 (15)
C1—Fe1—C9—C10	53.3 (3)	C5—Fe1—C2—C1	−37.41 (13)
C7—Fe1—C9—C10	−81.47 (12)	C6—Fe1—C2—C1	81.68 (15)
C8—Fe1—C9—C10	−118.37 (16)	C7—Fe1—C2—C1	123.59 (14)
C9—Fe1—C1—C5	39.0 (3)	C8—Fe1—C2—C1	165.44 (13)
C3—Fe1—C1—C5	−81.58 (14)	C1—C2—C3—C4	−0.1 (2)
C10—Fe1—C1—C5	78.79 (15)	Fe1—C2—C3—C4	−59.83 (14)
C4—Fe1—C1—C5	−37.62 (13)	C1—C2—C3—Fe1	59.74 (14)
C2—Fe1—C1—C5	−119.17 (19)	C9—Fe1—C3—C2	163.33 (12)
C6—Fe1—C1—C5	122.43 (13)	C10—Fe1—C3—C2	−166.6 (2)
C7—Fe1—C1—C5	165.10 (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—C2	158.2 (2)	C6—Fe1—C3—C2	50.8 (3)
C3—Fe1—C1—C2	37.58 (14)	C1—Fe1—C3—C2	−37.71 (12)
C10—Fe1—C1—C2	−162.04 (13)	C7—Fe1—C3—C2	80.97 (14)
C4—Fe1—C1—C2	81.55 (15)	C8—Fe1—C3—C2	121.84 (13)
C5—Fe1—C1—C2	119.17 (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—C4	118.99 (18)
C8—Fe1—C1—C2	−37.7 (3)	C5—Fe1—C3—C4	37.86 (13)
C8—C7—C6—C10	0.2 (2)	C6—Fe1—C3—C4	169.8 (2)
Fe1—C7—C6—C10	−58.86 (13)	C1—Fe1—C3—C4	81.27 (15)
C8—C7—C6—Fe1	59.10 (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—C7	41.5 (3)	C6—C7—C8—C9	−1.0 (2)
C10—Fe1—C6—C7	−119.15 (17)	Fe1—C7—C8—C9	57.86 (13)
C4—Fe1—C6—C7	−159.5 (2)	C6—C7—C8—Fe1	−58.90 (14)
C2—Fe1—C6—C7	78.32 (15)	C10—C9—C8—C7	1.4 (2)
C5—Fe1—C6—C7	163.36 (13)	Fe1—C9—C8—C7	−58.70 (14)
C1—Fe1—C6—C7	121.33 (13)	C10—C9—C8—Fe1	60.13 (13)
C8—Fe1—C6—C7	−36.99 (12)	C9—Fe1—C8—C7	120.13 (18)
C9—Fe1—C6—C10	38.24 (11)	C3—Fe1—C8—C7	−119.86 (13)
C3—Fe1—C6—C10	160.7 (2)	C10—Fe1—C8—C7	81.49 (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—C7	169.9 (2)
C1—Fe1—C6—C10	−119.52 (12)	C6—Fe1—C8—C7	37.19 (12)
C7—Fe1—C6—C10	119.15 (17)	C1—Fe1—C8—C7	−51.3 (3)
C8—Fe1—C6—C10	82.17 (12)	C3—Fe1—C8—C9	120.01 (13)
C7—C6—C10—C9	0.6 (2)	C10—Fe1—C8—C9	−38.64 (11)
Fe1—C6—C10—C9	−58.79 (13)	C4—Fe1—C8—C9	78.66 (14)
C7—C6—C10—C11	176.81 (17)	C2—Fe1—C8—C9	160.57 (13)
Fe1—C6—C10—C11	117.38 (18)	C5—Fe1—C8—C9	49.8 (3)
C7—C6—C10—Fe1	59.44 (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—C6	59.47 (13)	C7—Fe1—C8—C9	−120.13 (18)
C8—C9—C10—C11	−177.31 (17)	C2—C3—C4—C5	0.1 (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—Fe1	60.04 (14)
O1—C11—C10—C6	24.6 (3)	C1—C5—C4—C3	−0.1 (2)
C12—C11—C10—C6	−153.18 (17)	Fe1—C5—C4—C3	59.60 (14)
O1—C11—C10—C9	−159.99 (18)	C1—C5—C4—Fe1	−59.65 (15)
C12—C11—C10—C9	22.2 (3)	C9—Fe1—C4—C3	119.71 (14)
O1—C11—C10—Fe1	112.17 (18)	C10—Fe1—C4—C3	161.50 (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—C6	165.53 (12)	C1—Fe1—C4—C3	−81.43 (14)
C2—Fe1—C10—C6	46.2 (3)	C7—Fe1—C4—C3	46.7 (3)
C5—Fe1—C10—C6	123.08 (13)	C8—Fe1—C4—C3	77.89 (15)
C1—Fe1—C10—C6	81.19 (14)	C9—Fe1—C4—C5	−121.56 (13)
C7—Fe1—C10—C6	−37.52 (12)	C3—Fe1—C4—C5	118.72 (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—C5	81.10 (14)
C4—Fe1—C10—C9	−75.49 (13)	C6—Fe1—C4—C5	−49.1 (3)
C2—Fe1—C10—C9	165.1 (2)	C1—Fe1—C4—C5	37.30 (13)
C5—Fe1—C10—C9	−117.94 (12)	C7—Fe1—C4—C5	165.4 (2)
C6—Fe1—C10—C9	118.98 (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—C9	81.46 (12)	C16—C17—O2—C20	2.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1	0.93	2.50	2.830 (2)	101
C8—H8···O1ⁱ	0.93	2.60	3.345 (2)	137
C9—H9···O1ⁱⁱ	0.93	2.54	3.414 (2)	156
C12—H12···O1ⁱⁱ	0.93	2.46	3.346 (2)	160
C15—H15···O1ⁱⁱ	0.93	2.65	3.441 (2)	143
C19—H19···O2ⁱⁱⁱ	0.93	2.59	3.472 (3)	157
C3—H3···Cg1ⁱ	0.93	3.24	3.808 (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.

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₁₅H₁₃O₂)]
M_r	346.19
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	12.3124 (14), 10.2316 (11), 25.914 (3)
V (Å³)	3264.5 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.93
Crystal size (mm)	0.30 × 0.30 × 0.20

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.768, 0.836
No. of measured, independent and observed [I > 2σ(I)] reflections	26999, 3787, 2662
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.653

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.089, 1.02
No. of reflections	3787
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.28

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003), 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	2.50	2.830 (2)	101
C8—H8···O1ⁱ	0.93	2.60	3.345 (2)	137
C9—H9···O1ⁱⁱ	0.93	2.54	3.414 (2)	156
C12—H12···O1ⁱⁱ	0.93	2.46	3.346 (2)	160
C15—H15···O1ⁱⁱ	0.93	2.65	3.441 (2)	143
C19—H19···O2ⁱⁱⁱ	0.93	2.59	3.472 (3)	157
C3—H3···Cg1ⁱ	0.93	3.241	3.808 (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

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

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