metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 11| November 2014| Pages m369-m370

Crystal structure of 4-methyl-2-oxo-2H-chromen-7-yl ferrocene­carboxyl­ate

aSchool of Pharmacy, Anhui University of Chinese Medicine, Hefei 230038, People's Republic of China
*Correspondence e-mail: great7701@126.com, wdl8105@126.com

Edited by M. Weil, Vienna University of Technology, Austria (Received 24 September 2014; accepted 7 October 2014; online 15 October 2014)

The title mol­ecule, [Fe(C5H5)(C16H11O4)], consists of a ferrocenyl moiety and a 4-methyl­coumarin group linked through an ester unit to one of the cyclo­penta­dienyl (Cp) rings. The two Cp rings are virually parallel, with an angle between the two least-squares planes of 0.74 (16)°. The distances between the FeII atom and the centroids of the two Cp rings are 1.639 (2) and 1.652 (2) Å. The conformation of the ferrocenyl moiety is slightly away from eclipsed. The dihedral angle between the coumarin ring system and the ferrocenyl ester moiety is 69.17 (19)°. ππ stacking inter­actions involving the benzene rings of neighbouring coumarin moieties, with centroid–centroid distances of 3.739 (2) Å, consolidate the crystal packing.

1. Related literature

For background to ferrocene and its derivatives, see: Štěpnička (2002[Štěpnička, P. (2002). New J. Chem. 26, 567-575.]). For coumarin and its pharmacological activities, see: Peng et al. (2013[Peng, X. M. L. V., Damu, G. & Zhou, H. (2013). Curr. Pharm. Des. 19, 3884-3930.]). For the crystal structures of related ferrocenyl derivatives, see: Chen & Lu (2004[Chen, W. Y. & Lu, J. (2004). Chin. Chem. Lett. 15, 1146-1148.]); Imrie et al. (2002[Imrie, C., Elago, E. R. T., McCleland, C. W. & Williams, N. (2002). Green Chem. 4, 159-160.], 2005[Imrie, C., Elago, E. R. T., Williams, N., McCleland, C. W. & Engelbrecht, P. (2005). J. Organomet. Chem. 690, 4959-4966.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • [Fe(C5H5)(C16H11O4)]

  • Mr = 388.19

  • Monoclinic, P 21 /c

  • a = 7.8678 (11) Å

  • b = 20.294 (4) Å

  • c = 11.1455 (18) Å

  • β = 108.243 (14)°

  • V = 1690.1 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.92 mm−1

  • T = 293 K

  • 0.20 × 0.10 × 0.10 mm

2.2. Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.838, Tmax = 0.914

  • 11857 measured reflections

  • 2979 independent reflections

  • 2398 reflections with I > 2σ(I)

  • Rint = 0.031

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.031

  • wR(F2) = 0.087

  • S = 1.16

  • 2979 reflections

  • 236 parameters

  • H-atom parameters constrained

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Related literature top

For background to ferrocene and its derivatives, see: Štěpnička (2002). For coumarin and its pharmacological activities, see: Peng et al. (2013). For the crystal structures of related ferrocenyl derivatives, see: Chen & Lu (2004); Imrie et al. (2002, 2005).

Experimental top

To a CH2Cl2 solution (30 ml) of ferrocenylcarboxylic acid (1.0 g, 4.3 mmol), 7-hydroxy-4-methylcoumarin (0.76 g, 4.3 mmol), 1-ethyl-3-(dimethylaminopropyl)carbodimide hydrochloride (EDCI) (0.89 g, 4.5 mmol) and N,N-dimethylaminopyridine (DMAP) (0.26 g, 2.2 mmol) were added into a 50 ml round bottom flask. Then the reaction mixture was stirred at room temperature. The reaction process was monitored by thin layer chromatography (TLC). After completion of the reaction, the product was extracted with ethyl acetate. The extracts were combined, washed with water and dried over anhydrous Na2SO4. After removing ethyl acetate under reduced pressure, the crude product was purified by column chromatography using petroleum ether/EtOAc (8:1) as eluent. Yellow crystals were obtained by slow evaporation of an ether/EtOAc (8:1) solution to give 1.03 g (62% yield) of the title compound, 1H-NMR (CDCl3, δ p.p.m.), 2.48 (s, 2H, CH3), 4.34 (s, 5H, C5H5), 4.57 (s, 2H, C5H2), 5.00 (s, 2H, C5H2), 7.18–7.22 (m, 2H, ArH), 7.68 (d, 1H, ArH).

Refinement top

All hydrogen atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.93 Å and Uiso(H) = 1.2 Ueq.

Computing details top

Data collection: APEX2 (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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
The molecular structure of the title compound showing atoms as ellipsoids at the 30% probability level.
4-Methyl-2-oxo-2H-chromen-7-yl ferrocenecarboxylate top
Crystal data top
[Fe(C5H5)(C16H11O4)]F(000) = 800
Mr = 388.19Dx = 1.526 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3613 reflections
a = 7.8678 (11) Åθ = 2.7–23.4°
b = 20.294 (4) ŵ = 0.92 mm1
c = 11.1455 (18) ÅT = 293 K
β = 108.243 (14)°Block, yellow
V = 1690.1 (5) Å30.20 × 0.10 × 0.10 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer
2979 independent reflections
Radiation source: fine-focus sealed tube2398 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ϕ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
h = 99
Tmin = 0.838, Tmax = 0.914k = 2424
11857 measured reflectionsl = 1312
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H-atom parameters constrained
S = 1.16 w = 1/[σ2(Fo2) + (0.0432P)2]
where P = (Fo2 + 2Fc2)/3
2979 reflections(Δ/σ)max = 0.001
236 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
[Fe(C5H5)(C16H11O4)]V = 1690.1 (5) Å3
Mr = 388.19Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.8678 (11) ŵ = 0.92 mm1
b = 20.294 (4) ÅT = 293 K
c = 11.1455 (18) Å0.20 × 0.10 × 0.10 mm
β = 108.243 (14)°
Data collection top
Bruker APEXII CCD
diffractometer
2979 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
2398 reflections with I > 2σ(I)
Tmin = 0.838, Tmax = 0.914Rint = 0.031
11857 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0310 restraints
wR(F2) = 0.087H-atom parameters constrained
S = 1.16Δρmax = 0.23 e Å3
2979 reflectionsΔρmin = 0.18 e Å3
236 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
xyzUiso*/Ueq
Fe10.74731 (4)0.157566 (14)0.42513 (3)0.04477 (13)
O10.4801 (2)0.07407 (8)0.61150 (16)0.0717 (5)
O20.7574 (2)0.09846 (8)0.74074 (15)0.0695 (5)
O30.7829 (2)0.13167 (8)0.81894 (15)0.0654 (5)
O40.7893 (3)0.23952 (9)0.8434 (2)0.0910 (6)
C10.7620 (3)0.25205 (11)0.4903 (2)0.0620 (7)
H10.84640.28570.48110.074*
C20.5913 (3)0.24019 (11)0.4035 (2)0.0616 (6)
H20.53720.26400.32420.074*
C30.5129 (3)0.18719 (11)0.4494 (2)0.0549 (6)
H30.39430.16830.40830.066*
C40.6368 (3)0.16608 (10)0.5653 (2)0.0490 (5)
C50.7925 (3)0.20659 (10)0.5906 (2)0.0560 (6)
H50.90010.20370.66440.067*
C60.9160 (4)0.15047 (13)0.3194 (3)0.0734 (8)
H60.98040.18690.29550.088*
C70.7462 (4)0.12856 (15)0.2511 (2)0.0771 (8)
H70.66980.14640.17070.093*
C80.7034 (4)0.07557 (13)0.3160 (3)0.0764 (8)
H80.59280.04970.28970.092*
C90.8462 (4)0.06495 (12)0.4251 (3)0.0758 (9)
H90.85440.03100.48920.091*
C100.9783 (4)0.11104 (14)0.4274 (3)0.0737 (8)
H101.09460.11550.49290.088*
C110.6091 (3)0.10858 (11)0.6366 (2)0.0533 (6)
C120.7538 (3)0.04467 (11)0.8189 (2)0.0573 (6)
C130.7677 (3)0.01842 (12)0.7792 (2)0.0586 (6)
H130.77360.02680.69860.070*
C140.7727 (3)0.06931 (11)0.8629 (2)0.0497 (5)
C150.7663 (3)0.05849 (10)0.9842 (2)0.0478 (5)
C160.7540 (3)0.00656 (11)1.0201 (2)0.0609 (6)
H160.75090.01551.10120.073*
C170.7463 (3)0.05785 (12)0.9382 (2)0.0633 (7)
H170.73610.10100.96310.076*
C180.7724 (3)0.11504 (12)1.0658 (2)0.0528 (6)
C190.7797 (3)0.17514 (12)1.0191 (3)0.0624 (7)
H190.78260.21131.07090.075*
C200.7833 (3)0.18689 (13)0.8926 (3)0.0674 (7)
C210.7700 (4)0.10441 (13)1.1988 (2)0.0731 (8)
H21A0.77150.14631.23920.110*
H21B0.66360.08081.19720.110*
H21C0.87330.07941.24490.110*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0529 (2)0.03700 (19)0.0492 (2)0.00541 (13)0.02285 (16)0.00617 (13)
O10.0629 (11)0.0796 (12)0.0749 (12)0.0128 (10)0.0250 (10)0.0156 (10)
O20.0814 (12)0.0671 (11)0.0539 (10)0.0207 (9)0.0125 (9)0.0164 (8)
O30.0824 (13)0.0564 (10)0.0612 (10)0.0045 (9)0.0279 (9)0.0112 (8)
O40.1009 (15)0.0562 (11)0.1085 (16)0.0149 (10)0.0219 (13)0.0211 (11)
C10.0792 (19)0.0351 (11)0.0761 (18)0.0034 (11)0.0306 (16)0.0030 (12)
C20.0711 (17)0.0467 (13)0.0711 (17)0.0193 (12)0.0282 (14)0.0145 (12)
C30.0530 (14)0.0545 (13)0.0617 (15)0.0134 (11)0.0244 (12)0.0002 (12)
C40.0602 (15)0.0440 (12)0.0487 (13)0.0060 (10)0.0253 (12)0.0004 (10)
C50.0695 (16)0.0426 (12)0.0558 (14)0.0003 (11)0.0196 (12)0.0036 (11)
C60.089 (2)0.0639 (16)0.090 (2)0.0025 (15)0.0609 (19)0.0054 (15)
C70.100 (2)0.0832 (19)0.0534 (16)0.0245 (17)0.0307 (16)0.0026 (15)
C80.082 (2)0.0568 (16)0.106 (2)0.0087 (14)0.052 (2)0.0307 (16)
C90.106 (2)0.0499 (14)0.096 (2)0.0350 (16)0.067 (2)0.0242 (14)
C100.0569 (16)0.089 (2)0.0793 (19)0.0225 (15)0.0268 (15)0.0039 (16)
C110.0627 (16)0.0550 (14)0.0498 (14)0.0015 (12)0.0285 (13)0.0003 (11)
C120.0632 (16)0.0573 (14)0.0481 (14)0.0121 (11)0.0128 (12)0.0100 (11)
C130.0683 (16)0.0676 (16)0.0429 (13)0.0056 (13)0.0218 (12)0.0003 (12)
C140.0499 (13)0.0500 (12)0.0511 (14)0.0007 (10)0.0187 (11)0.0044 (11)
C150.0503 (13)0.0486 (12)0.0468 (13)0.0011 (10)0.0184 (11)0.0001 (10)
C160.0886 (18)0.0535 (14)0.0466 (14)0.0041 (13)0.0298 (13)0.0036 (11)
C170.092 (2)0.0468 (13)0.0555 (16)0.0043 (12)0.0292 (14)0.0028 (11)
C180.0517 (14)0.0540 (14)0.0550 (14)0.0031 (10)0.0199 (12)0.0082 (11)
C190.0591 (16)0.0518 (14)0.0778 (18)0.0053 (12)0.0234 (14)0.0106 (13)
C200.0589 (16)0.0546 (15)0.085 (2)0.0083 (12)0.0177 (14)0.0042 (15)
C210.092 (2)0.0718 (17)0.0631 (17)0.0049 (15)0.0353 (15)0.0209 (13)
Geometric parameters (Å, º) top
Fe1—C42.019 (2)C6—C101.400 (4)
Fe1—C72.024 (2)C6—H60.9793
Fe1—C82.026 (2)C7—C81.395 (4)
Fe1—C52.027 (2)C7—H70.9791
Fe1—C92.034 (2)C8—C91.390 (4)
Fe1—C62.037 (3)C8—H80.9793
Fe1—C32.037 (2)C9—C101.393 (4)
Fe1—C12.041 (2)C9—H90.9794
Fe1—C102.042 (2)C10—H100.9796
Fe1—C22.047 (2)C12—C131.370 (3)
O1—C111.192 (3)C12—C171.376 (3)
O2—C111.379 (3)C13—C141.384 (3)
O2—C121.402 (3)C13—H130.9300
O3—C141.368 (3)C14—C151.387 (3)
O3—C201.388 (3)C15—C161.391 (3)
O4—C201.208 (3)C15—C181.456 (3)
C1—C21.408 (3)C16—C171.373 (3)
C1—C51.411 (3)C16—H160.9300
C1—H10.9799C17—H170.9300
C2—C31.413 (3)C18—C191.335 (3)
C2—H20.9799C18—C211.503 (3)
C3—C41.419 (3)C19—C201.439 (4)
C3—H30.9800C19—H190.9300
C4—C51.428 (3)C21—H21A0.9600
C4—C111.466 (3)C21—H21B0.9600
C5—H50.9800C21—H21C0.9600
C6—C71.387 (4)
C4—Fe1—C7153.19 (12)C1—C5—Fe170.25 (13)
C4—Fe1—C8120.07 (10)C4—C5—Fe169.05 (13)
C7—Fe1—C840.29 (11)C1—C5—H5126.3
C4—Fe1—C541.35 (9)C4—C5—H5126.4
C7—Fe1—C5164.06 (12)Fe1—C5—H5126.4
C8—Fe1—C5153.89 (12)C7—C6—C10107.9 (3)
C4—Fe1—C9109.67 (9)C7—C6—Fe169.54 (16)
C7—Fe1—C967.55 (11)C10—C6—Fe170.10 (15)
C8—Fe1—C940.03 (12)C7—C6—H6125.7
C5—Fe1—C9119.71 (11)C10—C6—H6126.4
C4—Fe1—C6165.92 (12)Fe1—C6—H6126.2
C7—Fe1—C639.94 (11)C6—C7—C8108.1 (3)
C8—Fe1—C667.30 (11)C6—C7—Fe170.52 (15)
C5—Fe1—C6126.92 (12)C8—C7—Fe169.91 (15)
C9—Fe1—C667.43 (10)C6—C7—H7126.4
C4—Fe1—C340.94 (9)C8—C7—H7125.5
C7—Fe1—C3118.74 (12)Fe1—C7—H7125.9
C8—Fe1—C3109.32 (11)C9—C8—C7108.2 (3)
C5—Fe1—C369.04 (10)C9—C8—Fe170.30 (15)
C9—Fe1—C3129.41 (11)C7—C8—Fe169.80 (15)
C6—Fe1—C3151.50 (12)C9—C8—H8125.3
C4—Fe1—C168.54 (9)C7—C8—H8126.5
C7—Fe1—C1126.66 (11)Fe1—C8—H8126.0
C8—Fe1—C1164.88 (13)C8—C9—C10107.8 (2)
C5—Fe1—C140.59 (9)C8—C9—Fe169.67 (14)
C9—Fe1—C1152.77 (13)C10—C9—Fe170.30 (14)
C6—Fe1—C1107.33 (10)C8—C9—H9126.7
C3—Fe1—C168.16 (10)C10—C9—H9125.5
C4—Fe1—C10128.88 (11)Fe1—C9—H9126.0
C7—Fe1—C1067.28 (12)C9—C10—C6108.0 (3)
C8—Fe1—C1067.12 (12)C9—C10—Fe169.73 (14)
C5—Fe1—C10108.31 (11)C6—C10—Fe169.76 (15)
C9—Fe1—C1039.97 (11)C9—C10—H10126.3
C6—Fe1—C1040.14 (11)C6—C10—H10125.6
C3—Fe1—C10167.07 (11)Fe1—C10—H10125.9
C1—Fe1—C10118.65 (11)O1—C11—O2122.9 (2)
C4—Fe1—C268.50 (9)O1—C11—C4126.9 (2)
C7—Fe1—C2107.62 (11)O2—C11—C4110.1 (2)
C8—Fe1—C2128.22 (13)C13—C12—C17121.7 (2)
C5—Fe1—C268.47 (10)C13—C12—O2120.5 (2)
C9—Fe1—C2166.40 (13)C17—C12—O2117.7 (2)
C6—Fe1—C2117.71 (10)C12—C13—C14117.9 (2)
C3—Fe1—C240.49 (9)C12—C13—H13121.0
C1—Fe1—C240.30 (9)C14—C13—H13121.0
C10—Fe1—C2151.52 (11)O3—C14—C13116.2 (2)
C11—O2—C12117.52 (18)O3—C14—C15121.31 (19)
C14—O3—C20121.64 (19)C13—C14—C15122.5 (2)
C2—C1—C5108.8 (2)C14—C15—C16117.2 (2)
C2—C1—Fe170.10 (13)C14—C15—C18118.70 (19)
C5—C1—Fe169.16 (13)C16—C15—C18124.1 (2)
C2—C1—H1125.3C17—C16—C15121.4 (2)
C5—C1—H1125.9C17—C16—H16119.3
Fe1—C1—H1125.6C15—C16—H16119.3
C1—C2—C3108.1 (2)C16—C17—C12119.2 (2)
C1—C2—Fe169.60 (13)C16—C17—H17120.4
C3—C2—Fe169.36 (12)C12—C17—H17120.4
C1—C2—H2125.9C19—C18—C15118.3 (2)
C3—C2—H2125.9C19—C18—C21122.1 (2)
Fe1—C2—H2125.8C15—C18—C21119.6 (2)
C2—C3—C4107.8 (2)C18—C19—C20123.4 (2)
C2—C3—Fe170.14 (13)C18—C19—H19118.3
C4—C3—Fe168.86 (13)C20—C19—H19118.3
C2—C3—H3126.0O4—C20—O3116.0 (3)
C4—C3—H3126.1O4—C20—C19127.3 (3)
Fe1—C3—H3126.3O3—C20—C19116.6 (2)
C3—C4—C5108.0 (2)C18—C21—H21A109.5
C3—C4—C11123.9 (2)C18—C21—H21B109.5
C5—C4—C11127.9 (2)H21A—C21—H21B109.5
C3—C4—Fe170.20 (12)C18—C21—H21C109.5
C5—C4—Fe169.60 (13)H21A—C21—H21C109.5
C11—C4—Fe1121.63 (15)H21B—C21—H21C109.5
C1—C5—C4107.3 (2)
C4—Fe1—C1—C281.64 (15)C5—Fe1—C6—C1073.7 (2)
C7—Fe1—C1—C272.90 (19)C9—Fe1—C6—C1037.39 (17)
C8—Fe1—C1—C245.9 (5)C3—Fe1—C6—C10169.9 (2)
C5—Fe1—C1—C2120.3 (2)C1—Fe1—C6—C10114.14 (18)
C9—Fe1—C1—C2173.15 (19)C2—Fe1—C6—C10156.54 (17)
C6—Fe1—C1—C2112.64 (16)C10—C6—C7—C80.2 (3)
C3—Fe1—C1—C237.43 (14)Fe1—C6—C7—C860.10 (18)
C10—Fe1—C1—C2154.74 (15)C10—C6—C7—Fe159.88 (19)
C4—Fe1—C1—C538.64 (14)C4—Fe1—C7—C6170.58 (19)
C7—Fe1—C1—C5166.82 (16)C8—Fe1—C7—C6118.6 (2)
C8—Fe1—C1—C5166.2 (4)C5—Fe1—C7—C639.2 (5)
C9—Fe1—C1—C552.9 (3)C9—Fe1—C7—C681.18 (18)
C6—Fe1—C1—C5127.08 (17)C3—Fe1—C7—C6154.99 (15)
C3—Fe1—C1—C582.85 (16)C1—Fe1—C7—C671.9 (2)
C10—Fe1—C1—C584.98 (17)C10—Fe1—C7—C637.73 (16)
C2—Fe1—C1—C5120.3 (2)C2—Fe1—C7—C6112.36 (17)
C5—C1—C2—C30.3 (3)C4—Fe1—C7—C851.9 (3)
Fe1—C1—C2—C358.83 (16)C5—Fe1—C7—C8157.9 (3)
C5—C1—C2—Fe158.48 (16)C9—Fe1—C7—C837.47 (18)
C4—Fe1—C2—C181.76 (15)C6—Fe1—C7—C8118.6 (2)
C7—Fe1—C2—C1126.44 (17)C3—Fe1—C7—C886.37 (19)
C8—Fe1—C2—C1166.21 (15)C1—Fe1—C7—C8169.44 (17)
C5—Fe1—C2—C137.16 (14)C10—Fe1—C7—C880.91 (19)
C9—Fe1—C2—C1166.6 (4)C2—Fe1—C7—C8128.99 (18)
C6—Fe1—C2—C184.32 (18)C6—C7—C8—C90.4 (3)
C3—Fe1—C2—C1119.7 (2)Fe1—C7—C8—C960.04 (18)
C10—Fe1—C2—C151.8 (3)C6—C7—C8—Fe160.48 (18)
C4—Fe1—C2—C337.91 (14)C4—Fe1—C8—C985.15 (18)
C7—Fe1—C2—C3113.89 (17)C7—Fe1—C8—C9119.1 (2)
C8—Fe1—C2—C374.12 (19)C5—Fe1—C8—C947.3 (3)
C5—Fe1—C2—C382.52 (15)C6—Fe1—C8—C981.44 (18)
C9—Fe1—C2—C346.9 (5)C3—Fe1—C8—C9128.94 (16)
C6—Fe1—C2—C3156.00 (16)C1—Fe1—C8—C9153.4 (4)
C1—Fe1—C2—C3119.7 (2)C10—Fe1—C8—C937.73 (16)
C10—Fe1—C2—C3171.4 (2)C2—Fe1—C8—C9170.38 (15)
C1—C2—C3—C40.2 (3)C4—Fe1—C8—C7155.77 (17)
Fe1—C2—C3—C458.74 (15)C5—Fe1—C8—C7166.4 (2)
C1—C2—C3—Fe158.98 (16)C9—Fe1—C8—C7119.1 (2)
C4—Fe1—C3—C2119.3 (2)C6—Fe1—C8—C737.64 (17)
C7—Fe1—C3—C283.65 (19)C3—Fe1—C8—C7111.99 (18)
C8—Fe1—C3—C2126.80 (18)C1—Fe1—C8—C734.3 (5)
C5—Fe1—C3—C281.00 (16)C10—Fe1—C8—C781.35 (18)
C9—Fe1—C3—C2167.16 (17)C2—Fe1—C8—C770.5 (2)
C6—Fe1—C3—C249.0 (3)C7—C8—C9—C100.5 (3)
C1—Fe1—C3—C237.26 (14)Fe1—C8—C9—C1060.22 (18)
C10—Fe1—C3—C2161.5 (4)C7—C8—C9—Fe159.72 (18)
C7—Fe1—C3—C4157.10 (15)C4—Fe1—C9—C8113.68 (17)
C8—Fe1—C3—C4113.95 (16)C7—Fe1—C9—C837.70 (17)
C5—Fe1—C3—C438.26 (13)C5—Fe1—C9—C8158.13 (16)
C9—Fe1—C3—C473.59 (19)C6—Fe1—C9—C881.09 (19)
C6—Fe1—C3—C4168.2 (2)C3—Fe1—C9—C871.81 (19)
C1—Fe1—C3—C481.99 (15)C1—Fe1—C9—C8165.2 (2)
C10—Fe1—C3—C442.2 (5)C10—Fe1—C9—C8118.6 (2)
C2—Fe1—C3—C4119.3 (2)C2—Fe1—C9—C833.9 (5)
C2—C3—C4—C50.1 (3)C4—Fe1—C9—C10127.68 (17)
Fe1—C3—C4—C559.59 (15)C7—Fe1—C9—C1080.94 (18)
C2—C3—C4—C11175.0 (2)C8—Fe1—C9—C10118.6 (2)
Fe1—C3—C4—C11115.4 (2)C5—Fe1—C9—C1083.24 (18)
C2—C3—C4—Fe159.54 (15)C6—Fe1—C9—C1037.54 (17)
C7—Fe1—C4—C349.2 (3)C3—Fe1—C9—C10169.56 (16)
C8—Fe1—C4—C385.19 (17)C1—Fe1—C9—C1046.6 (3)
C5—Fe1—C4—C3118.92 (19)C2—Fe1—C9—C10152.6 (4)
C9—Fe1—C4—C3128.09 (16)C8—C9—C10—C60.4 (3)
C6—Fe1—C4—C3156.4 (4)Fe1—C9—C10—C659.46 (18)
C1—Fe1—C4—C380.97 (15)C8—C9—C10—Fe159.82 (17)
C10—Fe1—C4—C3168.86 (15)C7—C6—C10—C90.1 (3)
C2—Fe1—C4—C337.51 (14)Fe1—C6—C10—C959.44 (17)
C7—Fe1—C4—C5168.1 (2)C7—C6—C10—Fe159.53 (19)
C8—Fe1—C4—C5155.88 (16)C4—Fe1—C10—C973.2 (2)
C9—Fe1—C4—C5112.99 (16)C7—Fe1—C10—C981.66 (19)
C6—Fe1—C4—C537.5 (4)C8—Fe1—C10—C937.79 (17)
C3—Fe1—C4—C5118.92 (19)C5—Fe1—C10—C9114.70 (18)
C1—Fe1—C4—C537.95 (14)C6—Fe1—C10—C9119.2 (2)
C10—Fe1—C4—C572.22 (18)C3—Fe1—C10—C938.7 (5)
C2—Fe1—C4—C581.41 (15)C1—Fe1—C10—C9157.75 (17)
C7—Fe1—C4—C1169.1 (3)C2—Fe1—C10—C9166.9 (2)
C8—Fe1—C4—C1133.1 (3)C4—Fe1—C10—C6167.59 (16)
C5—Fe1—C4—C11122.8 (3)C7—Fe1—C10—C637.55 (17)
C9—Fe1—C4—C119.8 (2)C8—Fe1—C10—C681.42 (19)
C6—Fe1—C4—C1185.3 (4)C5—Fe1—C10—C6126.09 (18)
C3—Fe1—C4—C11118.3 (3)C9—Fe1—C10—C6119.2 (2)
C1—Fe1—C4—C11160.7 (2)C3—Fe1—C10—C6158.0 (4)
C10—Fe1—C4—C1150.6 (3)C1—Fe1—C10—C683.04 (19)
C2—Fe1—C4—C11155.8 (2)C2—Fe1—C10—C647.7 (3)
C2—C1—C5—C40.3 (3)C12—O2—C11—O10.4 (3)
Fe1—C1—C5—C459.37 (15)C12—O2—C11—C4179.32 (19)
C2—C1—C5—Fe159.06 (16)C3—C4—C11—O13.3 (4)
C3—C4—C5—C10.2 (3)C5—C4—C11—O1177.3 (2)
C11—C4—C5—C1174.9 (2)Fe1—C4—C11—O189.5 (3)
Fe1—C4—C5—C160.13 (16)C3—C4—C11—O2176.36 (19)
C3—C4—C5—Fe159.97 (15)C5—C4—C11—O22.4 (3)
C11—C4—C5—Fe1114.8 (2)Fe1—C4—C11—O290.1 (2)
C4—Fe1—C5—C1118.4 (2)C11—O2—C12—C1372.1 (3)
C7—Fe1—C5—C141.8 (4)C11—O2—C12—C17111.6 (3)
C8—Fe1—C5—C1171.8 (2)C17—C12—C13—C140.5 (4)
C9—Fe1—C5—C1155.16 (16)O2—C12—C13—C14176.7 (2)
C6—Fe1—C5—C172.29 (19)C20—O3—C14—C13178.0 (2)
C3—Fe1—C5—C180.49 (15)C20—O3—C14—C151.4 (3)
C10—Fe1—C5—C1112.95 (17)C12—C13—C14—O3178.7 (2)
C2—Fe1—C5—C136.90 (14)C12—C13—C14—C150.8 (4)
C7—Fe1—C5—C4160.2 (4)O3—C14—C15—C16179.2 (2)
C8—Fe1—C5—C453.5 (3)C13—C14—C15—C160.2 (4)
C9—Fe1—C5—C486.45 (17)O3—C14—C15—C180.6 (3)
C6—Fe1—C5—C4169.33 (14)C13—C14—C15—C18180.0 (2)
C3—Fe1—C5—C437.89 (13)C14—C15—C16—C170.8 (4)
C1—Fe1—C5—C4118.4 (2)C18—C15—C16—C17179.1 (2)
C10—Fe1—C5—C4128.67 (15)C15—C16—C17—C121.1 (4)
C2—Fe1—C5—C481.48 (15)C13—C12—C17—C160.4 (4)
C4—Fe1—C6—C7162.3 (3)O2—C12—C17—C16175.9 (2)
C8—Fe1—C6—C737.96 (18)C14—C15—C18—C191.5 (3)
C5—Fe1—C6—C7167.46 (16)C16—C15—C18—C19178.3 (2)
C9—Fe1—C6—C781.50 (19)C14—C15—C18—C21178.6 (2)
C3—Fe1—C6—C751.0 (3)C16—C15—C18—C211.6 (4)
C1—Fe1—C6—C7126.98 (17)C15—C18—C19—C200.5 (4)
C10—Fe1—C6—C7118.9 (2)C21—C18—C19—C20179.6 (2)
C2—Fe1—C6—C784.58 (19)C14—O3—C20—O4178.6 (2)
C4—Fe1—C6—C1043.5 (5)C14—O3—C20—C192.4 (3)
C7—Fe1—C6—C10118.9 (2)C18—C19—C20—O4179.7 (3)
C8—Fe1—C6—C1080.92 (19)C18—C19—C20—O31.4 (4)

Experimental details

Crystal data
Chemical formula[Fe(C5H5)(C16H11O4)]
Mr388.19
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)7.8678 (11), 20.294 (4), 11.1455 (18)
β (°) 108.243 (14)
V3)1690.1 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.92
Crystal size (mm)0.20 × 0.10 × 0.10
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2007)
Tmin, Tmax0.838, 0.914
No. of measured, independent and
observed [I > 2σ(I)] reflections
11857, 2979, 2398
Rint0.031
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.087, 1.16
No. of reflections2979
No. of parameters236
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.18

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

This work was supported by a grant from the National Natural Science Foundation of China (No. 81403318) and the Natural Science Foundation of Education Committee of Anhui Province (No. KJ2014A134).

References

First citationBruker (2007). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationChen, W. Y. & Lu, J. (2004). Chin. Chem. Lett. 15, 1146–1148.  CAS Google Scholar
First citationImrie, C., Elago, E. R. T., McCleland, C. W. & Williams, N. (2002). Green Chem. 4, 159–160.  Web of Science CrossRef CAS Google Scholar
First citationImrie, C., Elago, E. R. T., Williams, N., McCleland, C. W. & Engelbrecht, P. (2005). J. Organomet. Chem. 690, 4959–4966.  Web of Science CrossRef CAS Google Scholar
First citationPeng, X. M. L. V., Damu, G. & Zhou, H. (2013). Curr. Pharm. Des. 19, 3884–3930.  CrossRef CAS PubMed Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationŠtěpnička, P. (2002). New J. Chem. 26, 567–575.  Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 11| November 2014| Pages m369-m370
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds