Crystal structure of (E)-(3-(4-fluorophenyl)acryloyl)ferrocene, C19H15FFeO
-
Bin Liu
,
Xiaona Xu
Abstract
C19H15FFeO, orthorhombic, P212121 (no. 19), a = 5.9299(10) Å, b = 11.0947(16) Å, c = 22.793(4) Å, V = 1499.5(4) Å3, Z = 4, R gt(F) = 0.0337 wR ref (F 2) = 0.0822, T = 260 K.
The molecular structure is shown in the figure. Table 1 contains the crystallographic data and the list of the atoms including atomic coordinates and displacement parameters can be found in the cif-file attached to this article.
Data collection and handling.
| Crystal: | Darkred block |
| Size: | 0.16 × 0.15 × 0.13 mm |
| Wavelength: | Mo Kα radiation (0.71073 Å) |
| μ: | 1.01 mm−1 |
| Diffractometer, scan mode: | Bruker APEX2, φ and ω scans |
| θ max, completeness: | 28.4°, 100 % |
| N(hkl)measured , N(hkl)unique, R int: | 44139, 3741, 0.127 |
| Criterion for I obs, N(hkl)gt: | I obs > 2 σ(I obs), 3048 |
| N(param)refined: | 200 |
| Programs: | Bruker, 1 SHELX, 2 , 3 Olex2 4 |
1 Source of materials
Single crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of a solution of (E)-(3-(4-fluorophenyl)acryloyl)ferrocene, which was purchased from Aladdin, in a mixture of dichloromethane and n-hexane (approximately 1:2 v/v) at room temperature over a period of one week. Over a period of some days, well-formed, dark red, block crystals suitable for single-crystal X-ray diffraction analysis had deposited at the interface of the two solvents.
2 Experimental details
The single-crystal X-ray diffraction experiment was conducted at room temperature using a Bruker D8 Venture diffractometer with MoKα radiation. 1 The structure was solved with ShelXT 2 and refined in ShelXL, 3 both implemented within the Olex2 interface. 4 Hydrogen atoms were placed in idealized positions and refined using a riding model with isotropic displacement parameters.
3 Comment
Ferrocene-based compounds have attracted sustained research interest due to their unique electrochemical properties, structural versatility, and widespread applications in catalysis, materials science, and medicinal chemistry. 5 , 6 The introduction of a conjugated enone bridge functionalized with an electron-withdrawing group, such as a 4-fluorophenyl moiety, is known to enhance molecular polarization and offers potential for non-linear optical behavior. Determining the precise molecular and supramolecular structure through single-crystal X-ray diffraction is crucial for understanding the relationship between the structure and physicochemical properties.
The molecular structure of (E)-(3-(4-fluorophenyl)acryloyl)ferrocene reveals a nearly planar conformation of the enone bridge [O=C–C=C], which adopts a typical trans (E) configuration. The dihedral angle of O1–C9–C8–C7 is only 4.5°. The ferrocene unit exhibits slightly tilted cyclopentadienyl (Cp) rings, with the substituted Cp ring rotated to maximize conjugation with the acryloyl chain. 7 , 8 , 9 , 10 The dihedral angle between this Cp ring and the fluorophenyl ring is minimal, indicating effective electronic communication across the entire π-system, a feature critical for its electronic and redox properties. 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18
In the crystal lattice, molecules are primarily connected through weak intermolecular vdW interactions. These supramolecular features, combined with the inherent dipole moment from the polarized C=O bond and electron-withdrawing fluorine atom, facilitate a well-organized and stable crystal packing.
Funding source: Natural Science Foundation of Shaanxi Province
Award Identifier / Grant number: 2025JC–YBMS-888
Award Identifier / Grant number: 2025JC–YBMS-1084
Funding source: Shaanxi Provincial Department of Education
Award Identifier / Grant number: 24JS004
Funding source: Key Laboratory of Molecular Imaging and Drug Synthesis of Xianyang city
Award Identifier / Grant number: 2021QXNL–PT-0008
Funding source: School-level Scientific and Technological Innovation Team for Design, Synthesis and Structural Modification of Drug Molecules
Award Identifier / Grant number: 2024KCTD04
Acknowledgments
This work was financially supported by the projects of Natural Science Foundation of Shaanxi Province (2025JC–YBMS-888, 2025JC–YBMS-1084); The 2024 Key Scientific Research Program Projects of the Shaanxi Provincial Department of Education (Key Laboratory Projects, 24JS004); Key Laboratory of Molecular Imaging and Drug Synthesis of Xianyang city (2021QXNL–PT-0008), School-level Scientific and Technological Innovation Team for Design, Synthesis and Structural Modification of Drug Molecules (2024KCTD04).
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