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The crystal structure of cyclopentadienyl Co–P–C complexes by benzylideneacetone addition, C38H38CoO2P

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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 240 Issue 2

Abstract

C38H38CoO2P, triclinic, P1̄ (no. 2), a = 10.5200(6) Å, b = 10.5216(6) Å, c = 15.3394(7) Å, α = 102.038(4)°, β = 105.984(4)°, γ = 100.225(5)°, V = 1545.69(15) Å3, Z = 2, R gt (F) = 0.0498, wRref(F2) = 0.1120, T = 173.0(10) K.

CCDC no.: 2351690

The molecular structure is shown in the figure. 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: Brown block
Size: 0.50 × 0.10 × 0.01 mm
Wavelength: Cu Kα radiation (1.54184 Å)
μ: 5.09 mm−1
Diffractometer, scan mode: XtaLAB Synergy, Dualflex, HyPix, ω
θmax, completeness: 76.4°, 98 %
N(hkl)measured, N(hkl)unique, Rint: 14785, 6050, 0.058
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 5,192
N(param)refined: 384
Programs: Bruker, 1 Olex2, 2 SHELX 3 , 4
Table 2:

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

Atom x y z Uiso*/Ueq
C1 0.3228 (3) 0.3829 (3) 0.1533 (2) 0.0261 (6)
C2 0.3105 (3) 0.2672 (3) 0.0840 (2) 0.0249 (6)
C3 0.4302 (3) 0.2847 (3) 0.05475 (19) 0.0248 (6)
C4 0.5151 (3) 0.4171 (3) 0.1067 (2) 0.0275 (6)
C5 0.4493 (3) 0.4761 (3) 0.1673 (2) 0.0261 (6)
C6 0.2248 (3) 0.4113 (3) 0.2052 (2) 0.0378 (7)
H6A 0.1468 0.3358 0.1836 0.057*
H6B 0.1958 0.4895 0.1939 0.057*
H6C 0.2691 0.4266 0.2716 0.057*
C7 0.2055 (3) 0.1357 (3) 0.0594 (2) 0.0274 (6)
H7A 0.2089 0.0737 0.0041 0.033*
H7B 0.1144 0.1501 0.0467 0.033*
C8 0.4482 (3) 0.1921 (3) −0.0269 (2) 0.0348 (7)
H8A 0.5367 0.2249 −0.0315 0.052*
H8B 0.3790 0.1882 −0.0840 0.052*
H8C 0.4407 0.1040 −0.0176 0.052*
C9 0.6466 (3) 0.4807 (3) 0.0955 (2) 0.0370 (8)
H9A 0.6994 0.5517 0.1512 0.055*
H9B 0.6276 0.5168 0.0421 0.055*
H9C 0.6973 0.4146 0.0860 0.055*
C10 0.4949 (4) 0.6148 (3) 0.2329 (2) 0.0393 (8)
H10A 0.4855 0.6108 0.2928 0.059*
H10B 0.4397 0.6699 0.2068 0.059*
H10C 0.5888 0.6526 0.2411 0.059*
C11 0.2421 (3) 0.0798 (3) 0.1455 (2) 0.0253 (6)
H11 0.2242 0.1392 0.1967 0.030*
C12 0.3969 (3) 0.0919 (3) 0.17624 (19) 0.0232 (6)
H12 0.4182 0.0367 0.1249 0.028*
C13 0.4447 (3) 0.0483 (3) 0.2601 (2) 0.0264 (6)
C14 0.5732 (3) −0.0010 (3) 0.2799 (2) 0.0337 (7)
H14A 0.6356 0.0507 0.3408 0.051*
H14B 0.6150 0.0087 0.2326 0.051*
H14C 0.5509 −0.0939 0.2791 0.051*
C15 0.1539 (3) −0.0597 (3) 0.1281 (2) 0.0266 (6)
C16 0.1683 (4) −0.1714 (3) 0.0689 (3) 0.0407 (8)
H16 0.2354 −0.1617 0.0403 0.049*
C17 0.0839 (4) −0.2974 (4) 0.0518 (3) 0.0533 (10)
H17 0.0949 −0.3711 0.0117 0.064*
C18 −0.0158 (4) −0.3147 (3) 0.0934 (3) 0.0461 (9)
H18 −0.0720 −0.3994 0.0819 0.055*
C19 −0.0312 (3) −0.2057 (3) 0.1520 (2) 0.0369 (7)
H19 −0.0986 −0.2161 0.1804 0.044*
C20 0.0531 (3) −0.0794 (3) 0.1696 (2) 0.0298 (6)
H20 0.0417 −0.0064 0.2100 0.036*
C21 0.6995 (3) 0.3412 (3) 0.49884 (19) 0.0245 (6)
C22 0.8219 (3) 0.3955 (3) 0.5729 (2) 0.0307 (7)
H22 0.8850 0.4683 0.5713 0.037*
C23 0.8499 (3) 0.3415 (3) 0.6488 (2) 0.0345 (7)
H23 0.9314 0.3787 0.6984 0.041*
C24 0.7575 (4) 0.2328 (3) 0.6510 (2) 0.0370 (7)
H24 0.7776 0.1954 0.7015 0.044*
C25 0.6358 (4) 0.1793 (3) 0.5789 (2) 0.0395 (8)
H25 0.5731 0.1068 0.5813 0.047*
C26 0.6056 (3) 0.2332 (3) 0.5022 (2) 0.0324 (7)
H26 0.5229 0.1968 0.4535 0.039*
C27 0.7382 (3) 0.5749 (3) 0.4311 (2) 0.0257 (6)
C28 0.7025 (3) 0.6550 (3) 0.5010 (2) 0.0332 (7)
H28 0.6468 0.6152 0.5306 0.040*
C29 0.7495 (4) 0.7931 (3) 0.5262 (3) 0.0422 (8)
H29 0.7254 0.8459 0.5726 0.051*
C30 0.8320 (4) 0.8525 (3) 0.4825 (3) 0.0461 (9)
H30 0.8622 0.9455 0.4989 0.055*
C31 0.8702 (4) 0.7750 (3) 0.4146 (3) 0.0433 (8)
H31 0.9274 0.8159 0.3863 0.052*
C32 0.8233 (3) 0.6361 (3) 0.3882 (2) 0.0328 (7)
H32 0.8487 0.5840 0.3421 0.039*
C33 0.7534 (3) 0.3198 (3) 0.32034 (19) 0.0216 (5)
C34 0.6700 (3) 0.2694 (3) 0.22476 (19) 0.0212 (5)
C35 0.7302 (3) 0.2065 (3) 0.1629 (2) 0.0283 (6)
H35 0.6796 0.1728 0.0993 0.034*
C36 0.8628 (3) 0.1926 (3) 0.1932 (2) 0.0327 (7)
H36 0.8996 0.1513 0.1497 0.039*
C37 0.9414 (3) 0.2405 (3) 0.2885 (2) 0.0342 (7)
H37 1.0298 0.2302 0.3089 0.041*
C38 0.8857 (3) 0.3032 (3) 0.3518 (2) 0.0286 (6)
H38 0.9363 0.3345 0.4156 0.034*
Co1 0.48596 (4) 0.29200 (4) 0.19433 (3) 0.01950 (12)
O1 0.51671 (19) 0.35535 (19) 0.33487 (13) 0.0234 (4)
O2 0.3808 (2) 0.0481 (2) 0.31705 (14) 0.0324 (5)
P1 0.66702 (7) 0.39559 (7) 0.39319 (5) 0.02181 (16)

1 Source of material

The reaction of o-diphenylphosphinylphenyl lithium (2–PPh2C6H4Li) as a ligand precursor was carried out with 0.5 equiv. of the bridging chlorine complex [Cp*Co(μ–Cl)]2 at room temperature for 30 min using THF as a solvent. The phosphine-based aryl complex of cobalt metal, Cp*Co(2–C6H4PPh2), was obtained via a transmetallation reaction. 5 Cp*Co(2–C6H4PPh2) (227 mg, 0.5 mmol) is dissolved in THF (20 mL), Benzylideneacetone (73 mg, 0.5 mmol) is dissolved in THF (10 ml). Benzylideneacetone solution was added to Cp*Co(2–C6H4PPh2) solution slowly. After stirring for 0.5 h at room temperature, the color of the mixture immediately turned from brown to maroon. The solvent was removed under vacuum and the residue was extracted with hexane (3 × 10 mL). After recrystallization from hexane at −30 °C and the was obtained as maroon block crystals.

2 Experimental details

Using Olex2, 1 the structure was solved with the SHELXT 2 structure solution program and refined with the SHELXL 3 , 4 refinement package. o-Diphenylphosphinylphenyl lithium (2-PPh2C6H4Li) and the bridging chlorine complex [Cp*Co(μ-Cl)]2 were prepared according to published methods. 5 And the complex Cp*Co(2–C6H4PPh2) was obtained via a transmetallation reaction of equivalent o-diphenylphosphinylphenyl lithium and [Cp*Co(μ-Cl)]2. To a solution of o-diphenylphosphinophenyl lithium in THF was added a solution of [Cp*Co(μ-Cl)]2 in THF slowly at room temperature and stirred for 0.5 h. The color of the mixture immediately turned from brown to olive. The solvent was removed under vacuum and the residue was extracted with hexane (3 × 10 mL). After recrystallization from hexane at –30 °C the Cp*Co(2-C6H4PPh2) was obtained as olive powder. Yield: 85%.

3 Comment

As a common organic compound, benzylideneacetone is often used in the preparation of organic synthesis intermediates, 6 , 7 , 8 fragrances or aroma enhancers, anti-volatility agents for fragrances, 9 as well as zinc brighteners, 10 pharmaceutical care, 11 and so on. In addition, benzylacetone can be used as an organic ligand to coordinate with metals to obtain organometallic compounds. 12

As displayed in the figure, the crystal structure mentioned in the title is formed by molecules that exhibit characteristic bonds, including Co1–O1, Co1–C12, Co1–C34 and C2–C7, C7–C11, C11–C12. The lengths of these bonds are 2.0273(19) Å, 2.074(3) Å, 1.932(3) Å and 1.513(4) Å, 1.537(4) Å, 1.539(4) Å, respectively. The distance of Cp* plane center to Co1 is 1.704 Å. The angle formed by C34–Co1–O1 is 88.23(10)°; Co1–O1–P1 is 112.87(11)°; C12–Co1–O1 is 96.91(10)°; C12–Co1–C34 is 94.25(11)°; C2–C7–C11 is 106.2(2)°; C7–C11–C12 is 107.6(2)°; C11–C12–Co1 is 105.13(18)°; C11–C12–C13 is 112.7(2)°; C12–C13–O2 is 121.4(3)° and O2–C13–C14 is 117.9(3)°. The bond lengths and angles are in the expected ranges.

Corresponding author: Zhang Shengnan, College of Chemistry and Chemical Engineering, Dezhou University, Dezhou 253023, China, E-mail:

Funding source: Key the Nature Science Foundation of Shandong Province

Award Identifier / Grant number: ZR2023QB190

Funding source: Nature Science Foundation of Shandong Province

Award Identifier / Grant number: ZR2021QB117

Funding source: Doctoral Foundation of Dezhou University

Award Identifier / Grant number: 2022xjrc105

Funding source: Doctoral Foundation of Dezhou University

Award Identifier / Grant number: 2021xjrc202

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

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

  3. Research funding: Key the Nature Science Foundation of Shandong Province (ZR2023QB190), the Nature Science Foundation of Shandong Province (ZR2021QB117), the Doctoral Foundation of Dezhou University (2022xjrc105), the Doctoral Foundation of Dezhou University (2021xjrc202).

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Received: 2024-10-11
Accepted: 2025-01-14
Published Online: 2025-02-06
Published in Print: 2025-04-28

© 2024 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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  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
https://doi.org/10.1515/ncrs-2024-0402
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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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