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

Valdebenito, C.; Garland, M.T.; Fuentealba, M.; Escobar, C.A.

doi:10.1107/S1600536810023378

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page m838

doi:10.1107/S1600536810023378

Open

access

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

C. Valdebenito,^a M. T. Garland,^b M. Fuentealba ^a ^* and C. A. Escobar ^a

^aUniversidad Andres Bello, Departamento de Ciencias Químicas, Santiago, Chile, and ^bLaboratorio de Cristalografía, Departamento de Física, Facultad de Ciencias Físicas y Matemáticas, Universidad de Chile, Santiago, Chile
^*Correspondence e-mail: mfuentealba@unab.cl

(Received 19 May 2010; accepted 16 June 2010; online 23 June 2010)

The molecular structure of the title compound, [Fe(C₅H₅)(C₁₄H₁₁O₂)] consists of a ferrocenyl and 2-hydroxyphenyl group linked through the prop-2-en-1-one spacer and is stabilized by an intramolecular O—H⋯O hydrogen bond between the hydroxyl and the carbonyl groups.

Related literature

For biological activity of chalcones, see: Liu et al. (2001 ); Rao et al. (2004 ); Wu et al. (2002 , 2006 ); Xiang et al. (2006 ); Zsoldos-Mady et al. (2006 ). For their non-linear optical properties, see: Shettigar et al. (2006 ). For electro-active fluorescent materials, see: Belavaux-Nicot et al. (2005 ). For related structures, see: Escobar et al. (2008 ). For metallocene derivatives, see: Kudar et al. (2005 ).

Experimental

Crystal data

[Fe(C₅H₅)(C₁₄H₁₁O₂)]
M_r = 332.17
Monoclinic, P 2₁ /c
a = 10.8264 (12) Å
b = 12.0358 (13) Å
c = 11.8150 (13) Å
β = 103.839 (2)°
V = 1494.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.01 mm⁻¹
T = 298 K
0.25 × 0.19 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SABABS; Bruker, 2000 ) T_min = 0.741, T_max = 0.859
11654 measured reflections
3319 independent reflections
2734 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.120
S = 1.02
3319 reflections
199 parameters
16 restraints
H-atom parameters constrained
Δρ_max = 0.69 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1	0.82	1.79	2.523 (3)	148

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536810023378/rk2207sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810023378/rk2207Isup2.hkl

checkCIF report

Comment top

Chalcones are a family of aromatic ketones bearing two aromatic groups bridged together trough a central prop-2-en-1-one core. They have a wide range of applications covering from materials with various biological activities (Xiang et al., 2006; Wu et al., 2002, 2006; Liu et al., 2001; Zsoldos-Mady et al., 2006) to non-linear optics (Shettigar et al., 2006), including also electroactive fluorescent materials (Belavaux-Nicot et al., (2005). Ferrocene containing chalcones are also useful precursors for the synthesis of more complex heterocyclic metallocene derivatives (Kudar et al., (2005). Typically this kind of precursors are prepared trough a Claisen Shmidt condensation, reacting a ketone or an aldehyde with the appropriated ferrocene substituted aldehyde or ketone depending on the position were the ferrocenyl substituent is required.

For the case of 1-(2'-hydroxyphenyl)-substituted prop-2-en-1-ones (as the title compound) the presence of an intense H-bonding has been previously described (Escobar et al., 2008) this structural characteristic has been recognized to play a key role in its biological activity (Rao et al., (2004).

The molecular structure of the title compound is composed by the ferrocenyl moiety and the 2'-hydroxyphenyl group joined by the organic prop-2-en-1-one spacer.

The dihedral angle between the two aromatic rings joined by the conjugated organic spacer is 12.01 (9)°. The distances between the C₅H₅- and C₅H₄-ring centroids to the iron atom are 1.653 (1)Å and 1.648 (1)Å, respectively. Both cyclopentadienyl rings of the ferrocenyl group are coplanar with a dihedral angle 1.6 (1)°. These metrical parameters are typical of the η⁵···Fe···η⁵ coordination of the ferrocenyl moiety.

The main feature of the structure is an intramolecular hydrogen bond O—H···O between the hydroxyl and the carbonyl group forming a six-membered ring helping the molecular stabilization, this characteristic has been previously observed in other 2'-hydroxy chalcones (Escobar et al., 2008). This intramolecular bond leads the carbonyl group to display an S-cis-configuration in relation to the double bond. The double bond distance C═C is 1.325 (3)Å and exhibits a cis-conformation.

Finally, no intermolecular hydrogen bonds are observed in the crystalline packing of title compound.

Related literature top

For biological activity of chalcones, see: Liu et al. (2001); Rao et al. (2004); Wu et al. (2002, 2006); Xiang et al. (2006); Zsoldos-Mady et al. (2006). For their non-linear optical properties, see: Shettigar et al. (2006). For electro-active fluorescent materials, see: Belavaux-Nicot et al. (2005). For related structures, see: Escobar et al. (2008). For metallocene derivatives, see: Kudar et al. (2005).

Experimental top

The title compound was prepared as follows: a solution of potassium hydroxide (2 g in 30 ml methanol) was added to a mixture of ferrocenecarboxaldehyde (0.6 g 4.4 mmol) and 2-hydroxyacetophenone (0.94 g 4.4 mmol). The mixture was allowed to react for three days under continuous stirring. Then, methanol was evaporated in a rotatory evaporator and the crude reaction mixture was submitted to column chromatography (silica gel 60, Ethyl acetate: Hexane = 1: 20 v/v). The combined fractions containing the title compound were evaporated in vacuo, redissolved in methanol, and allowed to crystallize, to give violet crystals (65%), mp. 405.3–406.6 °C. IR (KBr) cm^-1: 3456 (OH), 3105 (C—H), 3086 (C—H), 1630 (C═O). ¹H NMR (CDCl₃, 400 MHz): δ 4.22 (5H, s, C₅H₅), 4.56 (2H, s, –C₅H₄), 4.65 (2H, s, –C₅H₄), 6.95 (1H, t, J = 7.2 Hz, H_arom), 7.26 (1H, d, J = 15 Hz, ═CH), 7.45 (1H, t, J = 7.2 Hz, H_arom), 7.88 (1H, d, J = 9.1 Hz, H_arom), 7.92 (1H, d, J = 15 Hz, ═CH), 13.08 (1H, s, OH). ¹³C NMR (CDCl₃, 400 MHz): δ: 31.34, 69.51, 69.71, 70.36, 72.27, 117.15, 119.00, 119.10, 129.79, 136.30, 148.36, 164.03, 193.17.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

Fig. 1. The molecular structure of title compound with the atom numbering scheme. Displacement ellipsoids are presented at 30% probability level. H atoms are shown as a small spheres of arbitrary radius.

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

Crystal data top

[Fe(C₅H₅)(C₁₄H₁₁O₂)]	F(000) = 688
M_r = 332.17	D_x = 1.476 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4215 reflections
a = 10.8264 (12) Å	θ = 2.5–25.7°
b = 12.0358 (13) Å	µ = 1.01 mm⁻¹
c = 11.8150 (13) Å	T = 298 K
β = 103.839 (2)°	Prism, violet
V = 1494.9 (3) Å³	0.25 × 0.19 × 0.15 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3319 independent reflections
Radiation source: fine-focus sealed tube	2734 reflections with I > 2σ(I)
Parallel, graphite monochromator	R_int = 0.016
ϕ– and ω–scans	θ_max = 27.8°, θ_min = 1.9°
Absorption correction: multi-scan (SABABS; Bruker, 2000)	h = −14→13
T_min = 0.741, T_max = 0.859	k = −15→15
11654 measured reflections	l = −15→15

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0672P)² + 0.5241P] where P = (F_o² + 2F_c²)/3
3319 reflections	(Δ/σ)_max = 0.001
199 parameters	Δρ_max = 0.69 e Å⁻³
16 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

[Fe(C₅H₅)(C₁₄H₁₁O₂)]	V = 1494.9 (3) Å³
M_r = 332.17	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.8264 (12) Å	µ = 1.01 mm⁻¹
b = 12.0358 (13) Å	T = 298 K
c = 11.8150 (13) Å	0.25 × 0.19 × 0.15 mm
β = 103.839 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3319 independent reflections
Absorption correction: multi-scan (SABABS; Bruker, 2000)	2734 reflections with I > 2σ(I)
T_min = 0.741, T_max = 0.859	R_int = 0.016
11654 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	16 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 1.02	Δρ_max = 0.69 e Å⁻³
3319 reflections	Δρ_min = −0.21 e Å⁻³
199 parameters

Special details top

Experimental. The data collection nominally covered a full sphere of reciprocal space by a combination of 5 sets of ω-scans each set at different ϕ- and/or 2θ-angles and each scan (10.00 s exposure) covering -0.300° in ω. The crystal to detector distance was 6.275 cm.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.61269 (3)	0.33755 (3)	0.17323 (3)	0.05064 (15)
C1	0.5167 (5)	0.2765 (4)	0.2865 (3)	0.1144 (12)
H1	0.5238	0.2999	0.3673	0.137*
C2	0.5826 (4)	0.1914 (3)	0.2476 (4)	0.1009 (10)
H2	0.6489	0.1457	0.2973	0.121*
C3	0.5421 (3)	0.1817 (3)	0.1306 (3)	0.0842 (8)
H3	0.5750	0.1285	0.0823	0.101*
C4	0.4497 (3)	0.2579 (3)	0.0903 (3)	0.0835 (8)
H4	0.4060	0.2682	0.0082	0.100*
C5	0.4286 (4)	0.3200 (3)	0.1808 (5)	0.1027 (10)
H5	0.3656	0.3793	0.1767	0.123*
C6	0.7415 (2)	0.44963 (19)	0.2599 (2)	0.0506 (5)
C7	0.8045 (2)	0.3637 (2)	0.2124 (2)	0.0532 (5)
H7	0.8698	0.3134	0.2565	0.064*
C8	0.7558 (2)	0.3642 (2)	0.0898 (2)	0.0584 (6)
H8	0.7808	0.3132	0.0345	0.070*
C9	0.6634 (2)	0.4489 (2)	0.0607 (2)	0.0596 (6)
H9	0.6137	0.4670	−0.0179	0.072*
C10	0.6540 (2)	0.5021 (2)	0.1649 (2)	0.0556 (6)
H10	0.5972	0.5640	0.1711	0.067*
C11	0.7555 (2)	0.4760 (2)	0.3823 (2)	0.0545 (6)
H11	0.6998	0.5281	0.4005	0.065*
C12	0.8411 (2)	0.4321 (2)	0.4701 (2)	0.0554 (6)
H12	0.8994	0.3811	0.4543	0.066*
C13	0.8463 (2)	0.4620 (2)	0.5922 (2)	0.0562 (6)
C14	0.9390 (2)	0.40822 (19)	0.6881 (2)	0.0531 (5)
C15	0.9355 (3)	0.4298 (2)	0.8046 (2)	0.0617 (6)
C16	1.0187 (3)	0.3761 (3)	0.8961 (2)	0.0715 (8)
H16	1.0132	0.3887	0.9724	0.086*
C17	1.1078 (3)	0.3054 (3)	0.8743 (3)	0.0740 (8)
H17	1.1643	0.2709	0.9361	0.089*
C18	1.1157 (3)	0.2841 (3)	0.7616 (3)	0.0693 (7)
H18	1.1776	0.2358	0.7479	0.083*
C19	1.0325 (2)	0.3339 (2)	0.6694 (2)	0.0567 (6)
H19	1.0380	0.3184	0.5937	0.068*
O1	0.7687 (2)	0.52989 (18)	0.61393 (17)	0.0793 (6)
O2	0.8498 (3)	0.5003 (2)	0.83039 (17)	0.0900 (7)
H2A	0.8062	0.5269	0.7700	0.135*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0501 (2)	0.0550 (2)	0.0459 (2)	−0.00450 (14)	0.00977 (15)	0.00348 (13)
C1	0.141 (3)	0.145 (3)	0.0747 (14)	−0.082 (2)	0.0616 (16)	−0.0231 (17)
C2	0.099 (2)	0.099 (2)	0.0958 (17)	−0.0357 (15)	0.0057 (16)	0.0430 (17)
C3	0.081 (2)	0.0678 (17)	0.1030 (17)	−0.0195 (12)	0.0212 (16)	−0.0147 (15)
C4	0.0549 (15)	0.109 (2)	0.0805 (15)	−0.0214 (12)	0.0050 (12)	0.0021 (14)
C5	0.074 (2)	0.097 (2)	0.159 (3)	−0.0151 (14)	0.071 (2)	−0.0085 (19)
C6	0.0511 (12)	0.0509 (12)	0.0483 (12)	−0.0034 (10)	0.0088 (10)	0.0028 (10)
C7	0.0466 (12)	0.0587 (13)	0.0531 (13)	0.0017 (10)	0.0098 (10)	0.0019 (10)
C8	0.0563 (14)	0.0698 (15)	0.0527 (13)	0.0011 (12)	0.0202 (11)	−0.0004 (12)
C9	0.0608 (14)	0.0674 (16)	0.0486 (13)	−0.0015 (12)	0.0093 (11)	0.0130 (11)
C10	0.0566 (13)	0.0506 (13)	0.0579 (14)	0.0029 (11)	0.0102 (11)	0.0079 (10)
C11	0.0583 (14)	0.0496 (12)	0.0553 (13)	−0.0034 (11)	0.0131 (11)	−0.0032 (10)
C12	0.0608 (14)	0.0560 (13)	0.0484 (13)	−0.0028 (11)	0.0110 (11)	−0.0026 (10)
C13	0.0636 (15)	0.0491 (12)	0.0536 (13)	−0.0032 (11)	0.0094 (11)	−0.0047 (10)
C14	0.0602 (14)	0.0474 (12)	0.0492 (12)	−0.0122 (10)	0.0082 (10)	−0.0038 (10)
C15	0.0763 (17)	0.0538 (14)	0.0520 (13)	−0.0079 (13)	0.0096 (12)	−0.0074 (11)
C16	0.087 (2)	0.0692 (17)	0.0514 (15)	−0.0145 (16)	0.0036 (14)	−0.0036 (13)
C17	0.0640 (17)	0.0815 (19)	0.0657 (17)	−0.0105 (15)	−0.0056 (14)	0.0130 (15)
C18	0.0521 (14)	0.0751 (18)	0.0782 (19)	−0.0040 (13)	0.0104 (13)	0.0095 (15)
C19	0.0525 (14)	0.0614 (15)	0.0557 (14)	−0.0074 (11)	0.0121 (11)	0.0005 (11)
O1	0.1007 (15)	0.0734 (13)	0.0587 (11)	0.0266 (12)	0.0092 (11)	−0.0091 (10)
O2	0.1251 (19)	0.0873 (15)	0.0560 (11)	0.0263 (14)	0.0186 (12)	−0.0127 (10)

Geometric parameters (Å, º) top

Fe1—C1	2.020 (3)	C7—H7	0.9800
Fe1—C5	2.027 (3)	C8—C9	1.412 (4)
Fe1—C2	2.027 (3)	C8—H8	0.9800
Fe1—C6	2.032 (2)	C9—C10	1.413 (4)
Fe1—C10	2.038 (2)	C9—H9	0.9800
Fe1—C4	2.041 (3)	C10—H10	0.9800
Fe1—C7	2.041 (2)	C11—C12	1.325 (3)
Fe1—C3	2.042 (3)	C11—H11	0.9300
Fe1—C8	2.051 (2)	C12—C13	1.476 (3)
Fe1—C9	2.053 (2)	C12—H12	0.9300
C1—C2	1.388 (6)	C13—O1	1.242 (3)
C1—C5	1.474 (6)	C13—C14	1.471 (3)
C1—H1	0.9800	C14—C19	1.407 (4)
C2—C3	1.352 (5)	C14—C15	1.411 (3)
C2—H2	0.9800	C15—O2	1.346 (4)
C3—C4	1.357 (5)	C15—C16	1.389 (4)
C3—H3	0.9800	C16—C17	1.357 (5)
C4—C5	1.369 (5)	C16—H16	0.9300
C4—H4	0.9800	C17—C18	1.379 (4)
C5—H5	0.9800	C17—H17	0.9300
C6—C7	1.426 (3)	C18—C19	1.374 (4)
C6—C10	1.431 (3)	C18—H18	0.9300
C6—C11	1.453 (3)	C19—H19	0.9300
C7—C8	1.419 (4)	O2—H2A	0.8200

C1—Fe1—C5	42.73 (19)	C5—C4—H4	125.0
C1—Fe1—C2	40.12 (18)	Fe1—C4—H4	125.0
C5—Fe1—C2	68.23 (17)	C4—C5—C1	105.9 (4)
C1—Fe1—C6	107.93 (13)	C4—C5—Fe1	70.88 (18)
C5—Fe1—C6	127.61 (14)	C1—C5—Fe1	68.4 (2)
C2—Fe1—C6	121.30 (13)	C4—C5—H5	127.1
C1—Fe1—C10	122.65 (16)	C1—C5—H5	127.1
C5—Fe1—C10	109.42 (13)	Fe1—C5—H5	127.1
C2—Fe1—C10	157.53 (15)	C7—C6—C10	107.5 (2)
C6—Fe1—C10	41.17 (9)	C7—C6—C11	127.2 (2)
C1—Fe1—C4	67.95 (15)	C10—C6—C11	125.2 (2)
C5—Fe1—C4	39.32 (15)	C7—C6—Fe1	69.85 (13)
C2—Fe1—C4	65.85 (15)	C10—C6—Fe1	69.62 (13)
C6—Fe1—C4	164.59 (13)	C11—C6—Fe1	122.83 (16)
C10—Fe1—C4	127.41 (13)	C8—C7—C6	107.6 (2)
C1—Fe1—C7	124.25 (16)	C8—C7—Fe1	70.09 (14)
C5—Fe1—C7	164.50 (16)	C6—C7—Fe1	69.18 (13)
C2—Fe1—C7	107.18 (14)	C8—C7—H7	126.2
C6—Fe1—C7	40.97 (9)	C6—C7—H7	126.2
C10—Fe1—C7	68.79 (10)	Fe1—C7—H7	126.2
C4—Fe1—C7	153.78 (13)	C9—C8—C7	108.7 (2)
C1—Fe1—C3	66.89 (16)	C9—C8—Fe1	69.97 (14)
C5—Fe1—C3	66.53 (15)	C7—C8—Fe1	69.34 (14)
C2—Fe1—C3	38.79 (16)	C9—C8—H8	125.6
C6—Fe1—C3	154.81 (13)	C7—C8—H8	125.6
C10—Fe1—C3	162.56 (13)	Fe1—C8—H8	125.6
C4—Fe1—C3	38.82 (14)	C8—C9—C10	108.0 (2)
C7—Fe1—C3	119.85 (13)	C8—C9—Fe1	69.78 (14)
C1—Fe1—C8	160.64 (19)	C10—C9—Fe1	69.20 (14)
C5—Fe1—C8	154.32 (17)	C8—C9—H9	126.0
C2—Fe1—C8	124.21 (17)	C10—C9—H9	126.0
C6—Fe1—C8	68.40 (10)	Fe1—C9—H9	126.0
C10—Fe1—C8	67.98 (11)	C9—C10—C6	108.1 (2)
C4—Fe1—C8	120.54 (13)	C9—C10—Fe1	70.40 (15)
C7—Fe1—C8	40.57 (10)	C6—C10—Fe1	69.21 (13)
C3—Fe1—C8	107.83 (13)	C9—C10—H10	125.9
C1—Fe1—C9	157.92 (19)	C6—C10—H10	125.9
C5—Fe1—C9	120.96 (16)	Fe1—C10—H10	125.9
C2—Fe1—C9	160.54 (17)	C12—C11—C6	125.4 (2)
C6—Fe1—C9	68.60 (10)	C12—C11—H11	117.3
C10—Fe1—C9	40.39 (10)	C6—C11—H11	117.3
C4—Fe1—C9	109.26 (12)	C11—C12—C13	121.6 (2)
C7—Fe1—C9	68.36 (10)	C11—C12—H12	119.2
C3—Fe1—C9	125.61 (14)	C13—C12—H12	119.2
C8—Fe1—C9	40.25 (10)	O1—C13—C14	120.1 (2)
C2—C1—C5	105.2 (3)	O1—C13—C12	119.6 (2)
C2—C1—Fe1	70.23 (19)	C14—C13—C12	120.3 (2)
C5—C1—Fe1	68.89 (18)	C19—C14—C15	117.3 (2)
C2—C1—H1	127.4	C19—C14—C13	122.9 (2)
C5—C1—H1	127.4	C15—C14—C13	119.8 (2)
Fe1—C1—H1	127.4	O2—C15—C16	118.1 (3)
C3—C2—C1	109.6 (4)	O2—C15—C14	121.2 (2)
C3—C2—Fe1	71.20 (19)	C16—C15—C14	120.6 (3)
C1—C2—Fe1	69.6 (2)	C17—C16—C15	120.2 (3)
C3—C2—H2	125.2	C17—C16—H16	119.9
C1—C2—H2	125.2	C15—C16—H16	119.9
Fe1—C2—H2	125.2	C16—C17—C18	120.7 (3)
C2—C3—C4	109.4 (4)	C16—C17—H17	119.6
C2—C3—Fe1	70.0 (2)	C18—C17—H17	119.6
C4—C3—Fe1	70.52 (19)	C19—C18—C17	120.3 (3)
C2—C3—H3	125.3	C19—C18—H18	119.9
C4—C3—H3	125.3	C17—C18—H18	119.9
Fe1—C3—H3	125.3	C18—C19—C14	120.9 (3)
C3—C4—C5	110.0 (4)	C18—C19—H19	119.6
C3—C4—Fe1	70.66 (18)	C14—C19—H19	119.6
C5—C4—Fe1	69.8 (2)	C15—O2—H2A	109.5
C3—C4—H4	125.0

C5—Fe1—C1—C2	115.9 (3)	C5—Fe1—C6—C11	43.5 (3)
C6—Fe1—C1—C2	−117.6 (2)	C2—Fe1—C6—C11	−41.9 (3)
C10—Fe1—C1—C2	−160.5 (2)	C10—Fe1—C6—C11	119.4 (3)
C4—Fe1—C1—C2	78.2 (2)	C4—Fe1—C6—C11	71.9 (5)
C7—Fe1—C1—C2	−75.3 (3)	C7—Fe1—C6—C11	−122.0 (3)
C3—Fe1—C1—C2	36.0 (2)	C3—Fe1—C6—C11	−73.7 (4)
C8—Fe1—C1—C2	−41.8 (5)	C8—Fe1—C6—C11	−159.8 (2)
C9—Fe1—C1—C2	165.2 (3)	C9—Fe1—C6—C11	156.8 (2)
C2—Fe1—C1—C5	−115.9 (3)	C10—C6—C7—C8	0.1 (3)
C6—Fe1—C1—C5	126.5 (2)	C11—C6—C7—C8	176.3 (2)
C10—Fe1—C1—C5	83.6 (2)	Fe1—C6—C7—C8	59.81 (17)
C4—Fe1—C1—C5	−37.7 (2)	C10—C6—C7—Fe1	−59.67 (16)
C7—Fe1—C1—C5	168.8 (2)	C11—C6—C7—Fe1	116.5 (2)
C3—Fe1—C1—C5	−79.8 (2)	C1—Fe1—C7—C8	163.7 (2)
C8—Fe1—C1—C5	−157.7 (3)	C5—Fe1—C7—C8	−166.8 (5)
C9—Fe1—C1—C5	49.4 (4)	C2—Fe1—C7—C8	122.9 (2)
C5—C1—C2—C3	0.2 (4)	C6—Fe1—C7—C8	−118.8 (2)
Fe1—C1—C2—C3	−60.2 (2)	C10—Fe1—C7—C8	−80.49 (16)
C5—C1—C2—Fe1	60.4 (2)	C4—Fe1—C7—C8	52.9 (3)
C1—Fe1—C2—C3	120.3 (4)	C3—Fe1—C7—C8	82.7 (2)
C5—Fe1—C2—C3	79.2 (3)	C9—Fe1—C7—C8	−36.95 (16)
C6—Fe1—C2—C3	−159.1 (2)	C1—Fe1—C7—C6	−77.5 (2)
C10—Fe1—C2—C3	167.5 (3)	C5—Fe1—C7—C6	−48.0 (5)
C4—Fe1—C2—C3	36.4 (2)	C2—Fe1—C7—C6	−118.3 (2)
C7—Fe1—C2—C3	−116.5 (2)	C10—Fe1—C7—C6	38.31 (14)
C8—Fe1—C2—C3	−75.2 (3)	C4—Fe1—C7—C6	171.7 (3)
C9—Fe1—C2—C3	−43.0 (5)	C3—Fe1—C7—C6	−158.51 (17)
C5—Fe1—C2—C1	−41.1 (3)	C8—Fe1—C7—C6	118.8 (2)
C6—Fe1—C2—C1	80.7 (3)	C9—Fe1—C7—C6	81.85 (15)
C10—Fe1—C2—C1	47.3 (5)	C6—C7—C8—C9	−0.2 (3)
C4—Fe1—C2—C1	−83.9 (3)	Fe1—C7—C8—C9	59.06 (18)
C7—Fe1—C2—C1	123.2 (2)	C6—C7—C8—Fe1	−59.24 (17)
C3—Fe1—C2—C1	−120.3 (4)	C1—Fe1—C8—C9	−164.6 (4)
C8—Fe1—C2—C1	164.5 (2)	C5—Fe1—C8—C9	51.8 (4)
C9—Fe1—C2—C1	−163.3 (3)	C2—Fe1—C8—C9	164.04 (19)
C1—C2—C3—C4	−0.4 (4)	C6—Fe1—C8—C9	−81.97 (16)
Fe1—C2—C3—C4	−59.7 (2)	C10—Fe1—C8—C9	−37.47 (15)
C1—C2—C3—Fe1	59.3 (2)	C4—Fe1—C8—C9	84.0 (2)
C1—Fe1—C3—C2	−37.2 (3)	C7—Fe1—C8—C9	−120.1 (2)
C5—Fe1—C3—C2	−84.0 (3)	C3—Fe1—C8—C9	124.51 (19)
C6—Fe1—C3—C2	45.8 (4)	C1—Fe1—C8—C7	−44.5 (5)
C10—Fe1—C3—C2	−164.0 (4)	C5—Fe1—C8—C7	171.9 (3)
C4—Fe1—C3—C2	−120.3 (3)	C2—Fe1—C8—C7	−75.8 (2)
C7—Fe1—C3—C2	80.2 (3)	C6—Fe1—C8—C7	38.16 (14)
C8—Fe1—C3—C2	122.9 (3)	C10—Fe1—C8—C7	82.67 (16)
C9—Fe1—C3—C2	163.8 (2)	C4—Fe1—C8—C7	−155.85 (18)
C1—Fe1—C3—C4	83.1 (3)	C3—Fe1—C8—C7	−115.35 (18)
C5—Fe1—C3—C4	36.3 (2)	C9—Fe1—C8—C7	120.1 (2)
C2—Fe1—C3—C4	120.3 (3)	C7—C8—C9—C10	0.1 (3)
C6—Fe1—C3—C4	166.1 (2)	Fe1—C8—C9—C10	58.82 (18)
C10—Fe1—C3—C4	−43.7 (5)	C7—C8—C9—Fe1	−58.68 (18)
C7—Fe1—C3—C4	−159.51 (19)	C1—Fe1—C9—C8	166.5 (3)
C8—Fe1—C3—C4	−116.9 (2)	C5—Fe1—C9—C8	−156.6 (2)
C9—Fe1—C3—C4	−75.9 (2)	C2—Fe1—C9—C8	−43.0 (4)
C2—C3—C4—C5	0.5 (4)	C6—Fe1—C9—C8	81.43 (16)
Fe1—C3—C4—C5	−58.9 (2)	C10—Fe1—C9—C8	119.5 (2)
C2—C3—C4—Fe1	59.4 (2)	C4—Fe1—C9—C8	−114.86 (18)
C1—Fe1—C4—C3	−80.1 (3)	C7—Fe1—C9—C8	37.23 (15)
C5—Fe1—C4—C3	−121.0 (3)	C3—Fe1—C9—C8	−74.8 (2)
C2—Fe1—C4—C3	−36.4 (2)	C1—Fe1—C9—C10	47.0 (4)
C6—Fe1—C4—C3	−157.4 (4)	C5—Fe1—C9—C10	83.9 (2)
C10—Fe1—C4—C3	164.9 (2)	C2—Fe1—C9—C10	−162.6 (4)
C7—Fe1—C4—C3	43.4 (4)	C6—Fe1—C9—C10	−38.09 (15)
C8—Fe1—C4—C3	80.4 (2)	C4—Fe1—C9—C10	125.63 (18)
C9—Fe1—C4—C3	123.3 (2)	C7—Fe1—C9—C10	−82.28 (16)
C1—Fe1—C4—C5	40.9 (3)	C3—Fe1—C9—C10	165.73 (17)
C2—Fe1—C4—C5	84.6 (3)	C8—Fe1—C9—C10	−119.5 (2)
C6—Fe1—C4—C5	−36.5 (6)	C8—C9—C10—C6	0.0 (3)
C10—Fe1—C4—C5	−74.1 (3)	Fe1—C9—C10—C6	59.13 (17)
C7—Fe1—C4—C5	164.4 (3)	C8—C9—C10—Fe1	−59.18 (18)
C3—Fe1—C4—C5	121.0 (3)	C7—C6—C10—C9	−0.1 (3)
C8—Fe1—C4—C5	−158.6 (2)	C11—C6—C10—C9	−176.3 (2)
C9—Fe1—C4—C5	−115.7 (3)	Fe1—C6—C10—C9	−59.87 (18)
C3—C4—C5—C1	−0.3 (4)	C7—C6—C10—Fe1	59.81 (16)
Fe1—C4—C5—C1	−59.7 (2)	C11—C6—C10—Fe1	−116.5 (2)
C3—C4—C5—Fe1	59.4 (2)	C1—Fe1—C10—C9	−160.9 (2)
C2—C1—C5—C4	0.1 (4)	C5—Fe1—C10—C9	−115.3 (2)
Fe1—C1—C5—C4	61.4 (2)	C2—Fe1—C10—C9	164.8 (4)
C2—C1—C5—Fe1	−61.3 (2)	C6—Fe1—C10—C9	119.3 (2)
C1—Fe1—C5—C4	−116.6 (3)	C4—Fe1—C10—C9	−75.0 (2)
C2—Fe1—C5—C4	−78.0 (3)	C7—Fe1—C10—C9	81.12 (16)
C6—Fe1—C5—C4	168.50 (19)	C3—Fe1—C10—C9	−42.0 (5)
C10—Fe1—C5—C4	125.9 (2)	C8—Fe1—C10—C9	37.34 (15)
C7—Fe1—C5—C4	−153.6 (4)	C1—Fe1—C10—C6	79.8 (2)
C3—Fe1—C5—C4	−35.9 (2)	C5—Fe1—C10—C6	125.4 (2)
C8—Fe1—C5—C4	46.5 (4)	C2—Fe1—C10—C6	45.6 (4)
C9—Fe1—C5—C4	82.8 (3)	C4—Fe1—C10—C6	165.71 (16)
C2—Fe1—C5—C1	38.6 (2)	C7—Fe1—C10—C6	−38.13 (14)
C6—Fe1—C5—C1	−74.9 (3)	C3—Fe1—C10—C6	−161.2 (4)
C10—Fe1—C5—C1	−117.5 (2)	C8—Fe1—C10—C6	−81.91 (16)
C4—Fe1—C5—C1	116.6 (3)	C9—Fe1—C10—C6	−119.3 (2)
C7—Fe1—C5—C1	−36.9 (6)	C7—C6—C11—C12	8.4 (4)
C3—Fe1—C5—C1	80.8 (3)	C10—C6—C11—C12	−176.1 (2)
C8—Fe1—C5—C1	163.1 (3)	Fe1—C6—C11—C12	96.9 (3)
C9—Fe1—C5—C1	−160.6 (2)	C6—C11—C12—C13	−178.5 (2)
C1—Fe1—C6—C7	122.0 (2)	C11—C12—C13—O1	0.1 (4)
C5—Fe1—C6—C7	165.5 (2)	C11—C12—C13—C14	177.5 (2)
C2—Fe1—C6—C7	80.0 (2)	O1—C13—C14—C19	−177.5 (2)
C10—Fe1—C6—C7	−118.6 (2)	C12—C13—C14—C19	5.2 (4)
C4—Fe1—C6—C7	−166.1 (4)	O1—C13—C14—C15	3.2 (4)
C3—Fe1—C6—C7	48.3 (3)	C12—C13—C14—C15	−174.2 (2)
C8—Fe1—C6—C7	−37.80 (15)	C19—C14—C15—O2	179.5 (2)
C9—Fe1—C6—C7	−81.21 (15)	C13—C14—C15—O2	−1.1 (4)
C1—Fe1—C6—C10	−119.4 (2)	C19—C14—C15—C16	−2.2 (4)
C5—Fe1—C6—C10	−75.9 (2)	C13—C14—C15—C16	177.2 (2)
C2—Fe1—C6—C10	−161.4 (2)	O2—C15—C16—C17	−179.1 (3)
C4—Fe1—C6—C10	−47.5 (5)	C14—C15—C16—C17	2.6 (4)
C7—Fe1—C6—C10	118.6 (2)	C15—C16—C17—C18	−1.3 (5)
C3—Fe1—C6—C10	166.9 (3)	C16—C17—C18—C19	−0.4 (5)
C8—Fe1—C6—C10	80.80 (16)	C17—C18—C19—C14	0.7 (4)
C9—Fe1—C6—C10	37.39 (15)	C15—C14—C19—C18	0.6 (4)
C1—Fe1—C6—C11	0.0 (3)	C13—C14—C19—C18	−178.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1	0.82	1.79	2.523 (3)	148

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₁₄H₁₁O₂)]
M_r	332.17
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.8264 (12), 12.0358 (13), 11.8150 (13)
β (°)	103.839 (2)
V (Å³)	1494.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.01
Crystal size (mm)	0.25 × 0.19 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SABABS; Bruker, 2000)
T_min, T_max	0.741, 0.859
No. of measured, independent and observed [I > 2σ(I)] reflections	11654, 3319, 2734
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.657

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.120, 1.02
No. of reflections	3319
No. of parameters	199
No. of restraints	16
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.69, −0.21

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1	0.82	1.79	2.523 (3)	147.7

Acknowledgements

The authors gratefully acknowledge generous financial support from FONDECYT (1080147 and 11080044).

References

Belavaux-Nicot, B., Maynadie, J., Lavabre, D., Lepetit, C. & Donnadieu, B. (2005). Eur. J. Inorg. Chem. pp. 2493–2505. Google Scholar
Bruker (2000). SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2001). SMART. Bruker AXS Inc., Madison, Wisconsin, USA Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Escobar, C. A., Vega, A., Sicker, D. & Ibañez, A. (2008). Acta Cryst. E64, o1834. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kudar, V., Zsoldos-Mady, V., Simon, K., Csampai, A. & Sohar, P. (2005). J. Organomet. Chem. 690, 4018–4026. Web of Science CSD CrossRef CAS Google Scholar
Liu, M., Wilairat, P. & Go, M. L. (2001). J. Med. Chem. 44, 4443–4452. Web of Science CrossRef PubMed CAS Google Scholar
Rao, Y. K., Fang, S.-H. & Tzeng, Y.-M. (2004). Bioorg. Med. Chem. 12, 2679–2686. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shettigar, S., Chandrasekharan, K., Umesh, G., Sarojini, B. K. & Narayana, B. (2006). Polymer, 47, 3565–3567. Web of Science CrossRef CAS Google Scholar
Wu, X., Tiekink, E. R. T., Kostetski, I., Kocherginsky, N., Tan, A. L. C., Khoo, S. B., Wilairat, P. & Go, M. L. (2006). Eur. J. Pharm. Sci. 27, 175–187. Web of Science CSD CrossRef PubMed CAS Google Scholar
Wu, X., Wilairat, P. & Go, M. L. (2002). Bioorg. Med. Chem. Lett. 12, 2299–2302. Web of Science CrossRef PubMed CAS Google Scholar
Xiang, W., Tiekinke, R. T., Kostetski, I., Kocherginsky, N., Tan, A. L. C., Soo, B. K., Wilairat, P. & Go, M. L. (2006). Eur. J. Pharm. Sci. 27,175–187. Web of Science PubMed Google Scholar
Zsoldos-Mady, V., Csampai, A., Szabo, R., Meszaros-Alapi, E., Pasztor, J., Hudecz, F. & Sohar, P. (2006). Chem. Med. Chem. 1, 1119–1125. Web of Science PubMed CAS Google Scholar