Startseite Crystal structure of cinnamoyl ferrocene, C19H16FeO
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Crystal structure of cinnamoyl ferrocene, C19H16FeO

  • Qiaru Wang , Xiaona Xu , Mo Du , Wenqiang Tang ORCID logo und Bin Liu ORCID logo EMAIL logo
Veröffentlicht/Copyright: 27. Januar 2025
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Zeitschrift für Kristallographie - New Crystal Structures
Aus der Zeitschrift Zeitschrift für Kristallographie - New Crystal Structures Band 240 Heft 2

Abstract

C19H16FeO, orthorhombic, Pna21 (no. 33), a = 40.8379(12) Å, b = 5.7993(2) Å, c = 11.9680(3) Å, V = 2834.40(15) Å3, Z = 8, R gt (F) = 0.0397, wR ref (F2) = 0.0834, T = 170 K. CCDC no.: 2403075.

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: Red block
Size: 0.16 × 0.09 × 0.06 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 1.06 mm−1
Diffractometer, scan mode: Bruker D8 Venture, φ and ω
θmax, completeness: 26.4°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 11333, 5319, 0.055
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 4,750
N(param)refined: 379
Programs: Bruker, 1 SHELX, 2 , 3 Olex2 4
Table 2:

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

Atom x y z Uiso*/Ueq
C1 0.75412 (11) 0.5718 (9) 0.3786 (4) 0.0202 (10)
H1 0.758252 0.728838 0.396199 0.024*
C2 0.72970 (11) 0.4271 (9) 0.4298 (3) 0.0182 (10)
C3 0.73207 (11) 0.2053 (9) 0.3782 (4) 0.0205 (11)
H3 0.718952 0.074764 0.395343 0.025*
C4 0.75710 (12) 0.2133 (10) 0.2978 (4) 0.0238 (12)
H4 0.763772 0.089140 0.251334 0.029*
C5 0.77083 (12) 0.4397 (10) 0.2979 (4) 0.0249 (12)
H5 0.788191 0.492144 0.251591 0.030*
C6 0.70830 (11) 0.5026 (9) 0.5221 (4) 0.0194 (11)
C7 0.68749 (11) 0.3241 (9) 0.5754 (4) 0.0196 (10)
H7 0.688197 0.170945 0.547336 0.024*
C8 0.66794 (11) 0.3708 (9) 0.6609 (4) 0.0210 (11)
H8 0.669080 0.522516 0.690584 0.025*
C9 0.64468 (11) 0.2121 (9) 0.7147 (4) 0.0178 (10)
C10 0.63736 (11) −0.0032 (9) 0.6697 (4) 0.0218 (11)
H10 0.648267 −0.053411 0.603940 0.026*
C11 0.61430 (12) −0.1452 (10) 0.7198 (4) 0.0250 (12)
H11 0.609136 −0.290026 0.687131 0.030*
C12 0.59880 (12) −0.0771 (10) 0.8171 (4) 0.0248 (12)
H12 0.583315 −0.175896 0.852054 0.030*
C13 0.60595 (11) 0.1354 (10) 0.8632 (4) 0.0231 (11)
H13 0.595430 0.182708 0.930210 0.028*
C14 0.62852 (12) 0.2802 (9) 0.8119 (4) 0.0220 (11)
H14 0.632980 0.427264 0.843320 0.026*
C15 0.80951 (13) 0.3988 (10) 0.5658 (4) 0.0334 (14)
H15 0.814905 0.554445 0.582380 0.040*
C16 0.82412 (12) 0.2601 (9) 0.4820 (4) 0.0267 (12)
H16 0.841042 0.305785 0.432246 0.032*
C17 0.80880 (12) 0.0397 (9) 0.4861 (4) 0.0251 (12)
H17 0.813878 −0.088109 0.439604 0.030*
C18 0.78482 (12) 0.0432 (9) 0.5708 (4) 0.0247 (12)
H18 0.770776 −0.080722 0.590678 0.030*
C19 0.78538 (14) 0.2635 (10) 0.6206 (4) 0.0309 (14)
H19 0.771892 0.313054 0.680685 0.037*
C20 0.57331 (12) 0.7782 (10) 0.2231 (4) 0.0260 (12)
H20 0.567545 0.905090 0.269266 0.031*
C21 0.59872 (13) 0.7751 (9) 0.1423 (4) 0.0250 (11)
H21 0.612914 0.899925 0.125072 0.030*
C22 0.59935 (13) 0.5549 (10) 0.0917 (4) 0.0274 (12)
H22 0.613979 0.505456 0.034845 0.033*
C23 0.57390 (12) 0.4195 (10) 0.1419 (4) 0.0251 (11)
H23 0.568651 0.264274 0.124013 0.030*
C24 0.55798 (12) 0.5578 (10) 0.2227 (4) 0.0247 (12)
H24 0.540188 0.511627 0.268728 0.030*
C25 0.62487 (11) 0.6042 (9) 0.4144 (4) 0.0215 (11)
H25 0.617927 0.728200 0.460518 0.026*
C26 0.61125 (11) 0.3762 (9) 0.4130 (4) 0.0206 (10)
C27 0.62910 (12) 0.2469 (9) 0.3312 (4) 0.0210 (11)
H27 0.625442 0.089987 0.312067 0.025*
C28 0.65300 (12) 0.3923 (10) 0.2842 (4) 0.0272 (12)
H28 0.668267 0.350177 0.227891 0.033*
C29 0.65042 (12) 0.6117 (10) 0.3349 (4) 0.0245 (11)
H29 0.663641 0.742081 0.318390 0.029*
C30 0.58321 (11) 0.2872 (9) 0.4777 (3) 0.0210 (11)
C31 0.56507 (11) 0.4578 (9) 0.5461 (4) 0.0213 (11)
H31 0.563466 0.613159 0.521549 0.026*
C32 0.55088 (11) 0.3939 (9) 0.6425 (4) 0.0211 (11)
H32 0.552110 0.235540 0.662402 0.025*
C33 0.53352 (12) 0.5498 (9) 0.7200 (4) 0.0210 (11)
C34 0.53011 (12) 0.4819 (10) 0.8314 (4) 0.0259 (12)
H34 0.538322 0.336613 0.855028 0.031*
C35 0.51464 (13) 0.6274 (11) 0.9081 (5) 0.0347 (14)
H35 0.512945 0.582800 0.984223 0.042*
C36 0.50189 (13) 0.8346 (11) 0.8737 (5) 0.0363 (14)
H36 0.491123 0.932209 0.925743 0.044*
C37 0.50476 (12) 0.9011 (10) 0.7628 (6) 0.0359 (13)
H37 0.495857 1.044137 0.738876 0.043*
C38 0.52060 (12) 0.7590 (9) 0.6869 (4) 0.0274 (12)
H38 0.522595 0.806126 0.611150 0.033*
Fe1 0.77508 (2) 0.28965 (11) 0.45323 (5) 0.01647 (16)
Fe2 0.60687 (2) 0.52737 (11) 0.26023 (6) 0.01738 (16)
O1 0.70740 (8) 0.7045 (6) 0.5524 (3) 0.0255 (8)
O2 0.57629 (8) 0.0826 (6) 0.4784 (3) 0.0264 (8)

1 Source of materials

The benzaldehyde (2.33 g, 22.0 mmol), acetyl ferrocene (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 grind 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

X-ray diffraction data were collected on a Bruker D8 Venture diffractometer with Mo Kα radiation. 1 The structure was solved using Direct Methods and refined with SHELX-2014. 2 , 3 , 4 Non-hydrogen atoms were refined anisotropically, while hydrogen atoms were placed in calculated positions and refined using a riding model.

3 Comment

Ferrocene-based compounds have garnered significant attention in various research fields due to their unique structural and electronic properties. The ferrocene unit is highly versatile and has been extensively utilized in ligand design, materials science, pharmaceuticals, and analytical chemistry. 5 Among these, cinnamoyl ferrocene, as a derivative incorporating both ferrocene and cinnamoyl groups, represents an interesting target for investigation.

Cinnamoyl ferrocene crystallizes in the orthorhombic crystal system with the space group Pna21. The asymmetric unit contains eight cinnamoyl ferrocene molecules, with the ferrocene unit adopting a nearly eclipsed conformation. The ferrocene unit remains intact, with an average Fe–C bond length of approximately 2.05 Å, consistent with previously reported ferrocene derivatives. 6 , 7 , 8 , 9 , 10 , 11 The molecular packing in the crystal is stabilized by a combination of π–π stacking and weak C–H⋯π interactions. These interactions, along with van der Waals forces, contribute to the overall crystal stability. Additionally, the ferrocene units are arranged in a manner that minimizes steric hindrance while preserving structural integrity. 12 , 13 , 14 The crystal structure of cinnamoyl ferrocene highlights the interplay of intramolecular conjugation and intermolecular forces, providing a foundation for further exploration of its physicochemical properties and potential applications.

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

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

  2. Research funding: Natural Science Foundation of Shannxi Province (2024JC-YBMS-733), 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).

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

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Received: 2024-11-30
Accepted: 2025-01-14
Published Online: 2025-01-27
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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  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
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  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
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  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
https://doi.org/10.1515/ncrs-2024-0457
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Artikel in diesem Heft

  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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Heruntergeladen am 4.10.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2024-0457/html
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