Home Crystal structure of (E)-(3-(furan-2-yl)acryloyl)ferrocene, C17H14FeO2
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Crystal structure of (E)-(3-(furan-2-yl)acryloyl)ferrocene, C17H14FeO2

  • Zhoujing Zhu , Xiaona Xu , Hongjuan Tong ORCID logo and Wenqiang Tang ORCID logo EMAIL logo
Published/Copyright: February 6, 2025
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 240 Issue 2

Abstract

C17H14FeO2, orthorhombic, Pbca (no. 61), a = 9.1480(2) Å, b = 10.2745(2) Å, c = 27.8889(6) Å, V = 2621.31(10) Å3, Z = 8, Rgt(F) = 0.0287, wRref(F2) = 0.0760, T = 170 K.

CCDC no.: 2403107

Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Colourless block
Size: 0.15 × 0.08 × 0.05 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 1.15 mm−1
Diffractometer, scan mode: Bruker D8 Venture, φ and ω scans
θmax, completeness: 26.4°, 100 %
N(hkl)measured, N(hkl)unique, Rint: 28749, 2680, 0.072
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 2,258
N(param)refined: 181
Programs: Bruker, 1 SHELX 2
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

Atom x y z Uiso*/Ueq
Fe1 0.54131 (3) 0.80666 (3) 0.42568 (2) 0.01862 (10)
O1 0.13921 (16) 0.85794 (14) 0.39002 (5) 0.0306 (3)
O2 0.21462 (16) 0.47018 (14) 0.27926 (5) 0.0297 (3)
C1 0.3277 (2) 0.75533 (19) 0.43296 (7) 0.0207 (4)
C2 0.3625 (2) 0.86128 (19) 0.46445 (7) 0.0235 (4)
H2 0.318099 0.944855 0.464322 0.028*
C3 0.4748 (2) 0.8192 (2) 0.49576 (7) 0.0267 (5)
H3 0.519175 0.870057 0.520217 0.032*
C4 0.5101 (2) 0.6880 (2) 0.48438 (7) 0.0263 (4)
H4 0.581160 0.635975 0.500183 0.032*
C5 0.4211 (2) 0.64780 (19) 0.44542 (7) 0.0228 (4)
H5 0.422763 0.564942 0.430315 0.027*
C6 0.2243 (2) 0.76518 (18) 0.39286 (7) 0.0213 (4)
C7 0.2256 (2) 0.66090 (18) 0.35627 (7) 0.0222 (4)
H7 0.288005 0.587705 0.360128 0.027*
C8 0.1393 (2) 0.66970 (19) 0.31786 (7) 0.0247 (4)
H8 0.077599 0.743967 0.316252 0.030*
C9 0.1291 (2) 0.57979 (19) 0.27881 (7) 0.0246 (4)
C10 0.0484 (2) 0.5824 (2) 0.23797 (7) 0.0317 (5)
H10 −0.020255 0.647319 0.229029 0.038*
C11 0.0858 (3) 0.4701 (2) 0.21120 (8) 0.0368 (5)
H11 0.047804 0.445253 0.180862 0.044*
C12 0.1857 (3) 0.4061 (2) 0.23725 (8) 0.0365 (5)
H12 0.230442 0.326642 0.227834 0.044*
C13 0.6032 (2) 0.9644 (2) 0.38569 (7) 0.0287 (5)
H13 0.554798 1.046152 0.384686 0.034*
C14 0.5746 (2) 0.8562 (2) 0.35547 (7) 0.0277 (4)
H14 0.503663 0.852907 0.330614 0.033*
C15 0.6704 (2) 0.7539 (2) 0.36889 (7) 0.0270 (4)
H15 0.674678 0.669918 0.354690 0.032*
C16 0.7584 (2) 0.7991 (2) 0.40716 (7) 0.0271 (4)
H16 0.832471 0.750728 0.423069 0.033*
C17 0.7170 (2) 0.9288 (2) 0.41765 (7) 0.0278 (5)
H17 0.758177 0.982522 0.441859 0.033*

1 Source of materials

The furan-2-carbaldehyde (2.11 g, 22.0 mmol), acetylferrocene (2.28 g, 10.0 mmol) and KOH (0.67 g, 12.0 mmol) were added to the mortar. After stirring well, the reaction mixture was ground for 20 min, until the TLC indicated the reaction was completed, then diluted with water and filtered. The solid was collected and washed with water, and dried overnight under vacuum. The crude product was further purified by flash silica chromatography to afford a single crystal of high quality. For crystal growth, the crude product was dissolved in a minimal amount of hot ethanol and slowly cooled to room temperature.

2 Experimental details

Single-crystal X-ray diffraction data were collected on a Bruker D8 Venture diffractometer at 170 K. 1 The crystal structure was determined by Direct Methods using SHELX-2014 software. 2 Full-matrix least-squares refinement was carried out with all non-hydrogen atoms refined anisotropically. 3 Hydrogen atoms were placed in geometrically idealized positions and refined using a riding model. The calculations were performed within the Olex2 software environment, which provided the crystallographic parameters that verify the high quality of both the data and the structural model. 4

3 Comment

The study of organometallic compounds containing ferrocene derivatives has garnered significant attention due to their unique structural features, electronic properties, and potential applications in materials science, catalysis, and medicinal chemistry. 5 , 6 (E)-(3-(Furan-2-yl)acryloyl) ferrocene represents a hybrid compound combining the redox activity of ferrocene with the conjugated system of a furan-substituted acrylic moiety.

The crystal structure of (E)-(3-(furan-2-yl)acryloyl)ferrocene reveals a distinct molecular architecture in which a 3-(furan-2-yl)acryloyl group replaces a hydrogen atom on one of the cyclopentadienyl rings of the ferrocene unit. Structural analysis shows that the atoms within each cyclopentadienyl ring lie in the same plane, with the two planes forming an interplanar angle of 0.6°, and are bridged by the central iron atom. This geometry is consistent with previously reported structures of ferrocene derivatives, confirming the stability of the ferrocene core and its minimal distortion. 7 , 8 , 9 , 10 , 11 , 12

Additionally, the dihedral angles between the cyclopentadienyl ring and the acryl group (12.7°) and between the acryl group and the furan ring (2.7°) indicate a degree of conjugation between these moieties. The small angles suggest that the conjugation between the acryl and furan groups is pronounced, facilitating electronic delocalization across the substituent and potentially influencing the compound’s electronic properties and reactivity. 13 , 14 , 15

Intermolecular interactions in the crystal structure reveal that the packing is primarily driven by van der Waals forces.

Corresponding author: Wenqiang Tang, Xianyang Key Laboratory of Molecular Imaging and Drug Synthesis, School of Pharmacy, Shaanxi Institute of International Trade & Commerce, Xianyang, Shaanxi, China, E-mail:

Acknowledgments

This work was financially supported by the projects of Natural Science Foundation of Shannxi Province (2024JC–YBMS-733, 2022JM-561), the 2023 research and development project of the Xianyang Science and Technology Bureau (L2023–ZDYF–SF-030), Key Laboratory of Molecular Imaging and Drug Synthesis of Xianyang city (2021QXNL–PT-0008), Doctoral research fund project of Xianyang Vocational and Technical College (2021BK01) and the scientific research fund project of Xianyang Vocational and Technical College (2020KJB02).

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

  3. Research funding: None declared.

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Received: 2024-12-16
Accepted: 2025-01-27
Published Online: 2025-02-06
Published in Print: 2025-04-28

© 2025 the author(s), published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

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https://doi.org/10.1515/ncrs-2024-0476
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of N-(3-bromo-4-fluorophenyl)-N′-hydroxy-4-{[2-(4-methylphenyl)ethyl]amino}-1,2,5-oxadiazole-3-carboximidamide, C18H17BrFN5O2
  4. Synthesis and crystal structure of ethyl (2S,4aS,6aS,6bR,8aR,12aS,12bR,14bR,E)-10-(((3,4-dichlorobenzyl)oxy)imino)-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylate
  5. The crystal structure of pyrazole nitrate
  6. Crystal structure of tetramethyl-bis(μ2-2-(2-hydroxy-3-methoxybenzylidene)-1-(6-(2-(2-hydroxy-3-methoxybenzylidene)hydrazine-1-carbonyl)picolinoyl)hydrazin-1-ido-κ4O,N,O′:O′)ditin(II) ─ ethanol (1/2), C54H62N10O14Sn2
  7. Crystal structure of catena-poly[μ3-iodido-(4-bromopyridine-κ1N)copper(I)], C5H4BrNCuI
  8. The crystal structure of cyclopentadienyl Co–P–C complexes by benzylideneacetone addition, C38H38CoO2P
  9. Synthesis and crystal structure of-(3S,10S,13S,17S)-N-(2-methoxyphenyl)-10,13-dimethyl-17-((R)-1-(phenylamino)ethyl)hexadecahydro-1H-cyclopenta[α]phenanthren-3-amine, C34H48N2O
  10. The crystal structure of (E)-3-((E)-3-(4-ethoxy-3-methoxyphenyl)-1-hydroxyallylidene) chroman-2,4-dione, C21H18O6
  11. The crystal structure of trans–L/D-[bis-(2-methyl-8-hydroxyquinoline-κ2 N,O) bis-(1,3,5-triaza-7-phosphaadamantane-κ2 P)cobalt(III)] tetrafluoroborate
  12. Crystal structure of 9-chloro-2,3,4,4a,5,6-hexahydro-1H-pyrido [1′,2′:1,6]pyrazino[2,3-b]quinoxaline, C14H15ClN4
  13. Crystal structure of 7-(diethylamino)-3-(benzoyl)-2 H -chromen-2-one, C20H19NO3
  14. The crystal structure of 4–bromo-3,5-dinitropyrazole
  15. Crystal structure of 8-hydroxy-3,5,8a-trimethyl-7,8,8a,9-tetrahydronaphtho[2,3-b]furan-4,6-dione, C15H16O4
  16. Crystal structure of 5-hydroxy-3,5,8a-trimethyl-4a,5,6,7,8a,9-hexahydronaphtho[2,3-b]furan-4,8-dione, C15H18O4
  17. Synthesis and crystal structure of-(3S,10S,13S,17S)-N-(2-methoxyphenyl)-10,13-dimethyl-17-((R)-1-(p-tolylamino)ethyl)hexadecahydro-1H-cyclopenta[α]phenanthren-3-amine, C35H50N2O
  18. The crystal structure of catena-poly((μ2-1,3,5-tri(1H- imidazol-1-yl)benzene κ2N:N′)-bis(4-hydroxbenzoato-κ1O)-zinc(II) monohydrate), C29H24N6O7Zn
  19. Crystal structure of 2-(benzo[d]oxazol-2-yl)acetonitrile, C9H6N2O
  20. Crystal structure of 1,3-dihydroxy-6,8-dimethoxy-2-(6-methyltetrahydro-2Hpyran-2-yl)-4a,9a-dihydroanthracene-9,10-dione, C22H22O7
  21. The crystal structure of the double salt potassium 1-methylpiperazine-1,4-di-ium trinitrate, C5H14KN5O9
  22. Crystal structure of 5′-hydroxy-6′-methoxy-1′-methyl-2′,3′,8′,8a′-tetrahydro-1′H-spiro[cyclohexane-1,7′-cyclopenta[ij]isoquinoline]-2,5-dien-4-one, C18H19NO3
  23. The crystal structure of 1,1′-(2,3,5,6-tetramethylpyrazine-1,4-diyl)bis(ethan-1-one), C12H18N2O2
  24. Crystal structure of [μ2-piperazine-1,4-bis(2-hydroxypropanesulfonato-κ2O:O′)] bis(μ2-4,4′-trimethylenedipyridyl-κ2N:N′)disilver(I), C18H24AgN3O4S
  25. Crystal structure of bis ((1-((E)-((4-methoxyphenyl)imino)methyl)naphthalen-2-yl)oxy) copper(II), C36H28CuN2O4
  26. Synthesis and crystal structure of 6,6′-((1E,11E)-5,8-dioxa-2,11-diazadodeca-1,11-diene-1,12-diyl) bis(2,4-di-tert-butylphenol), C36H56N2O4
  27. The crystal structure of barium hexahydroxidoiridate(IV) dihydroxide, Ba2[Ir(OH)6](OH)2
  28. Crystal structure of cinnamoyl ferrocene, C19H16FeO
  29. Crystal structure of (E)-3-(4-butoxyphenyl)acryloylferrocene, C23H24FeO2
  30. Crystal structure of 7-(dimethylamino)-2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-ethyl carboxylate, C15H16F3NO4
  31. The crystal structure of 1-phenylethan-1-aminium 4-hydroxy-3,5-dimethoxybenzoate C17H21NO5
  32. The crystal structure of 1,3,5-trichloro-2-nitrobenzene
  33. The crystal structure of tris(μ2-bromido)-bis(η6-p-cymene)-diosmium(II) tetrafluoroborate, C20H28BBr3F4Os2
  34. Crystal structure of new barium lithium manganese fluorides: Ba14Li1.87Mn14.13F68 with a Jarlite–related structure
  35. Crystal structure of (4-fluorobenzyl)triphenylphosphonium chloride, C25H21ClFP
  36. The crystal structure of calcitriol–chloroform (1/1), C27H44O3⋅CHCl3
  37. The crystal structure of (E)-1-((3)-nitrophenyl)pyren-3-(pyren-1-yl)prop-2-en-1-one, C25H15NO3
  38. Crystal structure of (E)-2-hydroxy-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H16N2O3
  39. Crystal structure of (E)-(3-(thiophen-2-yl)acryloyl)ferrocene, C17H14FeOS
  40. Crystal structure of (E)-(3-(furan-2-yl)acryloyl)ferrocene, C17H14FeO2
  41. Synthesis and crystal structure poly[diaqua(μ3-3-(((7-hydroxy-3-(4-methoxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl) methyl)ammonio)propanoate-κ3 O:O′:O″) sodium(I)] monohydrate, C20H24NNaO12S
  42. Crystal structure of 9-methoxy-4-(2-methoxypyridin-3-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine C19H18N4O2
  43. Synthesis and crystal structure of 4-(difluoromethyl)-1-methyl-N-(pyridin-3-yl)-1H-pyrazole-3-carboxamide hydrate, C11H12F2N4O2
  44. The crystal structure of caesalfurfuric acid B, C22H32O4
  45. The crystal structure of 2-bromo-2-(5-bromo-2-methyl-4-nitro-1H-imidazol-1-yl)-1-phenylethanone, C12H9Br2N3O3
  46. The crystal structure of bis{chlorido-[μ2-(1-oxidopyridin-2-yl)(pyridin-2-yl)amido-κ3 O,N, N′]copper(II)}, C20H16Cl2Cu2N6O2
  47. The crystal structure of 3-amino-2-formyl-1-phenyl-9,10-dihydrophenanthrene-4-carbonitrile, C22H16N2O
  48. The crystal structure of 1,1′-(2,5-dimethylpyrazine-1,4-diyl)bis(ethan-1-one), C10H14N2O2
  49. Crystal structure of 5′-(9-phenyl-9H-carbazol-3-yl)-[2,2′-bithiophene]-5-carbaldehyde, C27H17NOS2
  50. The crystal structure of the double salt dipyridin-1-ium bromide tribromide
  51. Crystal structure of (E)-(3-(3-methylthiophen-2-yl)acryloyl)ferrocene, C18H16FeOS
  52. Crystal structure of (E)-(3-(4-phenoxyphenyl)acryloyl)ferrocene, C25H20FeO2
  53. Crystal structure of (E)-(3-(3,4-dimethylphenyl)acryloyl)ferrocene, C21H20FeO
  54. Crystal structure of [(1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N‴)tetracyanidodiplatinum(II)] dimethyl sulfoxide solvate, C18H36N8O2Pt2S2
  55. Crystal structure of (4-ethoxybenzyl)triphenylphosphonium bromide ethanol solvate, C29H32BrO2P
  56. Crystal structure of (1-naphthalen-1-yl-methyl)triphenylphosphonium chloride ethanol solvate, C31H30ClOP
  57. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)platinum(II) bis[tribromido(dimethyl sulfoxide-κS)platinate(II)], C14H36Br6N4O2Pt3S2
  58. Crystal structure of (2-methylbenzyl)triphenylphosphonium chloride ethanol solvate, C28H30ClOP
  59. Crystal structure of bis(η2, σ1-8-methoxycyclooct-4-enyl)(μ2-1,4,8,11-tetraazacyclotetradecane-κ4 N, N′, N″, N‴)diplatinum(II) dibromide, C28H54Br2N4O2Pt2
  60. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)palladium(II) tetrabromidopalladate(II), C10H24Br4N4Pd2
  61. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)palladium(II) bis[trichlorido(dimethyl sulfoxide-κS)platinate(II)], C14H36Cl6N4O2PdPt2S2
  62. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)palladium(II) tetraiodidopalladate(II), C10H24I4N4Pd2
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