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Crystal structure of (4-(4-chlorophenyl)-1H-pyrrole-3-carbonyl)ferrocene, C21H16ClFeNO

  • Xiaohua Li , Xiaolin Dang , Jingyin Yu and Bin Liu ORCID logo EMAIL logo
Published/Copyright: February 27, 2025
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 240 Issue 3

Abstract

C21H16ClFeNO, monoclinic, P21/c (no. 14), a = 14.6936(11) Å, b = 9.3784(6) Å, c = 12.7854(8) Å, β = 105.183(2)°, V = 1700.4(2) Å3, Z = 4, R gt(F) = 0.0584 wR ref(F 2) = 0.1719, T = 170 K.

CCDC no.: 2314040

1 Source of materials

To a solution of 1–ferrocenyl-3-(4-chlorophenyl)-2-propen-1-one (3.50 g, 10 mmol) and tosylmethyl isocyanide (2.15 g, 11 mmol) in N,N-dimethylformamide (25 mL) was added potassium tert-butoxide (2.24 g, 20 mmol). The mixture was stirred at room temperature for 12 h, until the TLC indicated the reaction was completed. The mixture was diluted with brine, and then extracted with ethyl acetate (3 × 30 mL). The organic phase was washed with brine (30 mL), dried with anhydrous sodium sulphate, and then concentrated under pressure. The title compound was separated by silica-gel column chromatography with ethyl acetate-petroleum ether (25 %) gradient solvent system. The target product was obtained as a white solid. Yield: 68.5 %. For crystal growth, the product was dissolved in a minimal amount of hot ethanol and slowly cooled to room temperature (Tables 1 and 2).

Table 1:

Data collection and handling.

Crystal: Red block
Size: 0.11 × 0.09 × 0.05 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 1.05 mm−1
Diffractometer, scan mode: Bruker D8 VENTURE, φ and ω scans
θ max, completeness: 26.6°, 99 %
N(hkl)measured, N(hkl)unique, R int: 12549, 3530, 0.068
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 2,456
N(param)refined: 226
Programs: Bruker, 1 SHELX 2 , 3
Table 2:

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

x y z U iso*/U eq
Fe1 0.12689 (4) 0.40872 (7) 0.37890 (5) 0.0275 (2)
Cl1 0.77898 (10) 0.45575 (17) 0.95474 (11) 0.0551 (4)
O1 0.3348 (2) 0.3562 (4) 0.6660 (2) 0.0292 (7)
N1 0.4420 (2) 0.1944 (4) 0.3871 (3) 0.0288 (9)
H1 0.443510 0.153855 0.325523 0.035*
C1 0.0440 (4) 0.2318 (6) 0.3689 (5) 0.0493 (15)
H1A 0.026590 0.186904 0.427362 0.059*
C2 0.1244 (3) 0.1991 (5) 0.3319 (4) 0.0372 (11)
H2 0.170527 0.128743 0.361498 0.045*
C3 0.1241 (3) 0.2890 (5) 0.2436 (4) 0.0371 (11)
H3 0.169694 0.289950 0.202884 0.045*
C4 0.0438 (4) 0.3776 (6) 0.2263 (4) 0.0480 (15)
H4 0.026161 0.448650 0.171817 0.058*
C5 −0.0059 (3) 0.3429 (7) 0.3036 (5) 0.0555 (17)
H5 −0.062492 0.386282 0.310524 0.067*
C6 0.1058 (3) 0.5863 (5) 0.4622 (4) 0.0297 (10)
H6 0.046317 0.624788 0.463732 0.036*
C7 0.1580 (3) 0.4837 (5) 0.5352 (3) 0.0279 (10)
H7 0.139987 0.441860 0.594392 0.034*
C8 0.2431 (3) 0.4540 (5) 0.5036 (3) 0.0227 (9)
C9 0.2417 (3) 0.5418 (5) 0.4113 (3) 0.0264 (9)
H9 0.289314 0.545450 0.373403 0.032*
C10 0.1577 (3) 0.6215 (5) 0.3865 (4) 0.0324 (11)
H10 0.138905 0.687842 0.328685 0.039*
C11 0.3238 (3) 0.3695 (5) 0.5673 (3) 0.0242 (9)
C12 0.3902 (3) 0.3077 (5) 0.5121 (3) 0.0232 (9)
C13 0.3666 (3) 0.2609 (5) 0.4068 (3) 0.0274 (10)
H13 0.307077 0.273153 0.356037 0.033*
C14 0.5156 (3) 0.2001 (5) 0.4781 (3) 0.0280 (10)
H14 0.576816 0.162377 0.484632 0.034*
C15 0.4868 (3) 0.2692 (5) 0.5584 (3) 0.0231 (9)
C16 0.5523 (3) 0.3104 (5) 0.6626 (3) 0.0224 (9)
C17 0.5507 (3) 0.4485 (5) 0.7038 (3) 0.0262 (9)
H17 0.502167 0.512696 0.669080 0.031*
C18 0.6193 (3) 0.4925 (5) 0.7946 (3) 0.0289 (10)
H18 0.617676 0.586067 0.822470 0.035*
C19 0.6896 (3) 0.3990 (5) 0.8438 (4) 0.0325 (11)
C20 0.6919 (3) 0.2610 (5) 0.8077 (4) 0.0324 (11)
H20 0.740068 0.197122 0.843962 0.039*
C21 0.6222 (3) 0.2166 (5) 0.7170 (4) 0.0300 (10)
H21 0.622439 0.121277 0.691958 0.036*

2 Experimental details

The crystal structure was solved via Direct Methods using the SHELXT program 2 and refined through full-matrix least squares on F 2 using SHELXL. 3 Non-hydrogen atoms were refined anisotropically, while hydrogen atoms were placed in geometrically idealized positions and refined using a riding model.

3 Comment

Ferrocene, known for its robust and well-defined sandwich structure, serves as an ideal scaffold for incorporating diverse functional moieties, 4 The single-crystal structure of (4-(4-chlorophenyl)-1H-pyrrole-3-carbonyl)ferrocene, with the incorporation of a pyrrole-3-carbonyl group, along with a 4-chlorophenyl substituent, introduces additional versatility to the molecule, potentially enhancing its applications in fields. 5 , 6 , 7 , 8 , 9 , 10

In the crystal of the title compound, the iron center of ferrocene is coordinated to two cyclopentadienyl rings, which adopt a parallel alignment, a characteristic feature of the ferrocene structure. 11 , 12 , 13 , 14 The functionalized pyrrole-3-carbonyl group is attached to the ferrocene scaffold through the carbonyl carbon atom (C11), which interacts with the C12 atom and connects the two ring systems. The bond length of C11–C8 is 1.480(6) Å, and the bond length of C11–C12 is 1.465(7) Å. The 4-chlorophenyl group, represented by atoms C16 to C21 in the structure, is positioned at the para position relative to the pyrrole ring, as indicated by the spatial arrangement in the crystal. The chlorine atom (Cl1) is attached to carbon atom C19, and the bond length of Cl1–C19 is 1.745(5) Å.

The dihedral angle between the two cyclopentadienyl rings is measured to be 5.2°, reflecting a nearly parallel alignment, which is in agreement with the structural features observed in other ferrocenyl compounds. 15 , 16 , 17 , 18 Furthermore, the dihedral angle between the chlorophenyl and pyrrole rings is determined to be 42.3°, which is slightly smaller than the 51° angle reported for the analogous compound 4-(2-chlorophenyl)-1H-pyrrol-3-yl (ferrocenyl)methanone. 19

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:

Acknowledgments

This work was financially supported by the projects of Social Development in Shaanxi Province Science and Technology Department (2023–YBSF-036), 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), School-level Scientific and Technological Innovation Team for Design, Synthesis and Structural Modification of Drug Molecules (2024KCTD04).

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Received: 2025-01-19
Accepted: 2025-02-14
Published Online: 2025-02-27
Published in Print: 2025-06-26

© 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-2025-0034
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of 5,5′-bis(2,4,6-trinitrophenyl)-2,2′-bi(1,3,4-oxadiazole), C16H4N10O14
  4. Crystal structure of catena-poly[(μ3-4,4′-oxydibenzoato- κ5 O,O′: O″,O‴:O‴)-bis(2,4,6-tri(3-pyridine)-1,3,5-triazine-κ1 N)cadmium(II)], C50H32CdN12O5
  5. The crystal structure of 1,4-diazepane-1,4-diium potassium trinitrate, C5H14KN5O9
  6. The crystal structure of benzyl 2,2,5,5-tetramethylthiazolidine-4-carboxylate, C15H21NO2S
  7. Crystal structure of 2-hydroxyethyl-triphenylphosphonium tetracyanidoborate, C24H20BN4OP
  8. The crystal structure of 1-methyl-3-(N-methylnitrous amide–N-methylene) imidazolidine-2,4,5-trione
  9. Crystal structure of N-((3-cyano-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(2,2,2-trifluoroacetyl)-1H-pyrazol-5-yl)carbamoyl)-2,6-difluorobenzamide, C20H7Cl2F8N5O3S
  10. Crystal structure of 5-(2,2-difluoropropyl)-5-methylbenzo[4,5]imidazo[2,1-a] isoquinolin-6(5H)-one, C20H18F2N2O
  11. The crystal structure of N′,N″-[1,2-bis(4-chlorophenyl)ethane-1,2-diylidene]bis(furan-2- carbohydrazide), C24H16Cl2N4O4
  12. Crystal structure of [(4-bromobenzyl)triphenylphosphonium] tetrabromoantimony(III), [C25H21BrP]+[SbBr4]−
  13. Crystal structure of [(4-bromobenzyl)triphenylphosphonium] tetrabromidoindium(III), [C25H21BrP]+[InBr4]−
  14. The crystal structure of 4-carboxy-2-oxobutan-1-aminium chloride, C5H10ClNO3
  15. Crystal structure of (4-(4-chlorophenyl)-1H-pyrrole-3-carbonyl)ferrocene, C21H16ClFeNO
  16. The crystal structure of dichlorido(η6-p-cymene)(triphenylarsine)ruthenium(II), C28H29AsCl2Ru
  17. Crystal structure of (Z)-2-hydroxy-N′-(1-(o-tolyl)ethylidene)benzohydrazide, C16H16N2O2
  18. The crystal structure of 10-(1-bromoethyl)-14-(bromomethyl)dibenzo[a, c]acridine, C24H17NBr2
  19. Synthesis and crystal structure of 6-methoxy-7-[(4-methoxyphenyl)methoxy]-2H-1-benzopyran-2-one, C18H16O5
  20. Synthesis and crystal structure of ethyl 4-((4-trifluoromethylbenzyl)amino)benzo, C17H16F3NO2
  21. The crystal structure of (Z)-2-(tert-butyl)-6-(7-(tert-butyl)-5-methylbenzo[d][1,3]oxathiol-2-ylidene)-4-methylcyclohexa-2,4-dien-1-one, C23H28O2S
  22. The crystal structure of (R)-2-aminobutanamide hydrochloride, C4H11ClN2O
  23. Crystal structure of bromido[hydridotris(3-tert-butyl-5-isopropylpyrazolyl)borato-κ3 N,N′,N″]copper(II), C30H52BBrCuN6
  24. Crystal structure of chlorido{hydridotris[3-mesityl-5-methyl-1H-pyrazol-1-yl-κN3]borato}-copper(II) dichloromethane monosolvate
  25. Crystal structure of 4-[3,5-bis(propan-2-yl)-1H-pyrazol-4-yl]pyridine, C14H19N3
  26. Crystal structure of ((4-(4-bromophenyl)-1H-pyrrol-3-yl)methyl)ferrocene, C21H16BrFeNO
  27. Crystal structure of [(4-chlorobenzyl)triphenylphosphonium] dichloridocopper(I), {[C25H21ClP]+[CuCl2]−}n
  28. The crystal structure of {Cu(2,9-diisopropyl-4,7-diphenyl-1,10-phenanthroline)[4,5-bis(diphenylphosphino)-9,9-dimethylxanthene]}+ PF6−·1.5(EtOAC)
  29. Crystal structure of 3,5-bis(t-butyl)-1H-pyrazol-4-amine, C11H21N3
  30. Crystal structure of [(2,4-dichlorobenzyl)triphenylphosphonium] trichloridocopper(II), [C25H20Cl2P]+[CuCl3]−
  31. The crystal structure of dipotassium sulfide, K2S
  32. Crystal structure of (4-(4-methoxyphenyl)-1H-pyrrole-3-carbonyl)ferrocene, C22H19FeNO2
  33. Crystal structure of (E)-6-(4-methylpiperazin-1-yl)-2-(4-(trifluoromethyl)benzylidene)-3, 4-dihydronaphthalen-1(2H)-one, C23H23F3N2O
  34. Crystal structure of (E)-6-morpholino-2-(4-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C22H20F3NO2
  35. Crystal structure of Ce9Ir37Ge25
  36. The crystal structure of ethyl 6-(2-nitrophenyl)imidazo[2,1-b]thiazole-3-carboxylate, C14H11N3O4S
  37. Crystal structure of (4-(4-isopropylphenyl)-1H-pyrrol-3-yl)(ferrocenyl)methanone, C24H23FeNO
  38. Crystal structure of bis(methylammonium) tetrathiotungstate(VI), (CH3NH3)2[WS4]
  39. Crystal structure of 6,11-dihydro-12H-benzo[e]indeno[1,2-b]oxepin-12-one, C17H12O2
  40. Crystal structure of 3-[(4-phenylpiperidin-1-yl)methyl]-5-(thiophen-2-yl)-2,3-dihydro-1,3,4- oxadiazole-2-thione, C18H19N3OS2
  41. Crystal structure of N-isopropyl-1,8-naphthalimide C15H13NO2
  42. TiNiSi-type EuPdBi
  43. Crystal structure of 1-(p-tolylphenyl)-4-(2-thienoyl)-3-methyl-1H-pyrazol-5-ol, C16H14N2O2S
  44. The crystal structure of 3-(3-carboxypropyl)-2-nitro-1H-pyrrole 1-oxide, C7H9N3O5
  45. The crystal structure of tetraaqua-bis(2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetato-k2O:N)-tetrakis(2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetato-k1N)trizinc(II) hexahydrate C36H52N18O32Zn3
  46. The crystal structure of 4-(3-carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 4-hydroxy-3,5-dimethoxybenzoate monohydrate, C25H30FN3O9
  47. Crystal structure of bis(DL-1-carboxy-2-(1H-indol-3-yl)ethan-1-aminium) oxalate — acetic acid (1/2)
  48. Crystal structure of methyl (E)-4-((4-methylphenyl)sulfonamido)but-2-enoate, C12H15NO4S
  49. The crystal structure of actarit, C10H11NO3
  50. The crystal structure of bicyclol, C19H18O9
  51. The crystal structure of topiroxostat, C13H8N6
  52. Crystal structure of 2,2-dichloro-N-methyl-N-(4-p-tolylthiazol-2-yl)acetamide, C13H12Cl2N2OS
  53. Crystal structure of 4-(trifluoromethyl)-7-coumarinyl trifluoromethanesulfonate C11H4F6O5S
  54. Crystal structure of (1,4,7,10,13,16-hexaoxacyclooctadecane-κ6O6)-((Z)-N,N′-bis(2-(dimethylamino)phenyl)carbamimidato-κ1N)potassium(I)
  55. Crystal structure of (Z)-2-(5-((4-(dimethylamino)naphthalen-1-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid, C18H16N2O3S2
  56. Crystal structure of (4-fluorobenzyl)triphenylphosphonium bromide, C25H21BrFP
  57. The crystal structure of dichlorido-[6-(pyridin-2-yl)phenanthridine-κ2N, N′]zinc(II)-chloroform (1/1), C19H13N2ZnCl5
  58. Crystal structure of (E)-(3-(2,4-dichlorophenyl)acryloyl)ferrocene, C19H14Cl2FeO
  59. The crystal structure of (E)-7-chloro-1-cyclopropyl-6-fluoro-3-((2-hydroxybenzylidene)amino)quinolin-4(1H)-one, C19H14ClFN2O2
  60. Crystal structure of 2-bromo-11-(((fluoromethyl)sulfonyl)methyl)-6-methyl-6,11-dihydrodibenzo[c,f][1,2]thiazepine 5,5-dioxide, C16H13BrFNO4S2
  61. Crystal structure of 2-chloro-11-(((fluoromethyl)sulfonyl)methyl)-6-methyl-6,11-dihydrodibenzo[c,f][1,2]thiazepine 5,5-dioxide, C16H13ClFNO4S2
  62. Crystal structure of 5-(2,2-difluoropropyl)-5-methyl-6-oxo-5,6-dihydrobenzo[4,5]imidazo[2,1-a]isoquinoline-3-carbonitrile, C20H15F2N3O
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