Home The crystal structure of 1-(3-oxo-1-phenyl-3-(p-tolyl) propylidene)-1,3-dihydro-2H-inden-2-one, C25H20O2
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The crystal structure of 1-(3-oxo-1-phenyl-3-(p-tolyl) propylidene)-1,3-dihydro-2H-inden-2-one, C25H20O2

  • Mengdan Wang ORCID logo EMAIL logo , Weiwei Lu , Junling Wang ORCID logo , Mengyang Li , Yuanyuan Feng and Jun-Ying Ma
Published/Copyright: November 8, 2023
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 239 Issue 1

Abstract

C25H20O2, triclininc, P 1 ‾ (no. 2), a = 9.821(2) Å, b = 10.141(2) Å, c = 10.679(2) Å, α = 61.688(4)°, β = 86.002(4)°, γ = 84.220(4)°, V = 931.3(3) Å3, Z = 2, R gt (F) = 0.0522, wR ref (F2) = 0.1437, T = 293 K.

CCDC no.: 2295930

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: Colourless prismatic
Size: 0.20 × 0.16 × 0.13 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.08 mm−1
Diffractometer, scan mode: φ and ω
θmax, completeness: 25.0°, 94 %
N(hkl)measured, N(hkl)unique, Rint: 4808, 3160, 0.032
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 2395
N(param)refined: 245
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
O1 1.16664 (16) 0.4745 (2) 0.16075 (18) 0.0716 (5)
O2 1.09645 (17) 0.13049 (17) 0.37400 (15) 0.0644 (5)
C1 0.9374 (2) 0.6383 (2) 0.3278 (2) 0.0505 (5)
C2 0.8906 (3) 0.7222 (2) 0.3955 (3) 0.0652 (7)
H2 0.9443 0.7926 0.3956 0.078*
C3 0.7640 (3) 0.7006 (3) 0.4624 (3) 0.0696 (7)
H3 0.7316 0.7568 0.5077 0.083*
C4 0.6852 (3) 0.5963 (3) 0.4626 (2) 0.0656 (7)
H4 0.5998 0.5824 0.5085 0.079*
C5 0.7306 (2) 0.5116 (2) 0.3959 (2) 0.0533 (6)
H5 0.6764 0.4405 0.3979 0.064*
C6 0.8572 (2) 0.5328 (2) 0.3257 (2) 0.0436 (5)
C7 0.93268 (19) 0.4553 (2) 0.25143 (19) 0.0427 (5)
C8 1.0715 (2) 0.5146 (2) 0.2154 (2) 0.0520 (6)
C9 1.0723 (2) 0.6375 (2) 0.2562 (2) 0.0616 (6)
H9A 1.1462 0.6168 0.3203 0.074*
H9B 1.0833 0.7336 0.1726 0.074*
C10 0.89310 (19) 0.3540 (2) 0.21590 (19) 0.0415 (5)
C11 0.9896 (2) 0.2779 (2) 0.1501 (2) 0.0479 (5)
H11A 1.0419 0.3535 0.0741 0.057*
H11B 0.9360 0.2349 0.1076 0.057*
C12 1.0890 (2) 0.1548 (2) 0.2521 (2) 0.0446 (5)
C13 1.17693 (19) 0.0649 (2) 0.19648 (19) 0.0418 (5)
C14 1.1787 (2) 0.0933 (3) 0.0564 (2) 0.0610 (6)
H14 1.1235 0.1736 −0.0084 0.073*
C15 1.2603 (3) 0.0055 (3) 0.0109 (3) 0.0690 (7)
H15 1.2584 0.0264 −0.0837 0.083*
C16 1.3451 (2) −0.1134 (2) 0.1033 (3) 0.0579 (6)
C17 1.3437 (2) −0.1408 (2) 0.2425 (3) 0.0581 (6)
H17 1.4001 −0.2201 0.3069 0.070*
C18 1.2617 (2) −0.0547 (2) 0.2888 (2) 0.0516 (5)
H18 1.2628 −0.0769 0.3838 0.062*
C19 1.4312 (3) −0.2121 (3) 0.0548 (3) 0.0881 (9)
H19A 1.3746 −0.2793 0.0466 0.132*
H19B 1.5009 −0.2692 0.1228 0.132*
H19C 1.4733 −0.1510 −0.0360 0.132*
C20 0.75196 (19) 0.3076 (2) 0.23806 (18) 0.0390 (5)
C21 0.6419 (2) 0.4113 (2) 0.1751 (2) 0.0459 (5)
H21 0.6573 0.5120 0.1181 0.055*
C22 0.5110 (2) 0.3679 (2) 0.1955 (2) 0.0532 (6)
H22 0.4384 0.4392 0.1534 0.064*
C23 0.4868 (2) 0.2191 (3) 0.2783 (2) 0.0602 (6)
H23 0.3979 0.1895 0.2937 0.072*
C24 0.5950 (3) 0.1146 (3) 0.3378 (3) 0.0632 (6)
H24 0.5792 0.0136 0.3922 0.076*
C25 0.7258 (2) 0.1575 (2) 0.3180 (2) 0.0523 (5)
H25 0.7980 0.0853 0.3587 0.063*

1 Source of material

In a Schlenk tube 3-phenyl-1-(p-tolyl)prop-2-yn-1-one (66.1 mg, 0.30 mmol), 1,3-dihydro-2H-inden-2-one (79.3 mg, 0.60 mmol), Cs2CO3 (195.5 mg, 0.60 mmol) and toluene (3.0 mL) were stirred at 100 °C under N2 for 3 h. The reaction mixture was then quenched by water, and the water layers were extracted with ethyl acetate (10 mL × 3). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. Purification by chromatography on silica gel (petroleum ether/ethyl acetate = 5:1) afforded desired compound (yellow solid, 91.8 mg, 87 %). Single crystals were obtained by crystallization of the title compound from a mixture of dichloromethane (10 mL) and petroleum ether (2 mL). Melting point: 177–178 °C. 1H NMR (400 MHz, CDCl3) δ 2.39 (s, 3H), 3.52 (s, 2H), 4.80 (s, 2H), 6.38–6.35 (m, 1H), 6.92–6.87 (m, 1H), 7.46–7.13 (m, 9H), 7.91–7.88 (m, 2H); 13C NMR (100 MHz, CDCl3) δ 206.0, 196.3, 145.3, 144.0, 142.5, 139.5, 137.7, 135.0, 133.7, 129.5, 129.4, 128.5, 128.5, 128.4, 127.1, 126.9, 125.1, 124.4, 46.0, 42.3, 21.3.

2 Experimental details

Using Olex2 [2], the structure was solved with the SHELXT [3] structure solution program and refined with the SHELXL [4] refinement package.

3 Comment

α,β-Unsaturated carbonyls that contain an electron-deficient carbon–carbon double bond are not only versatile synthetic intermediates but also a structural motif in biologically active molecules [5], [6], [7], [8]. In this paper we report the synthesis and crystal structure of a novel α,β-unsaturated carbonyl compound. In the crystal structure, there are two carbonyl groups and a carbon–carbon double bond. The two carbonyl groups are linked by carbon–carbon double bond. The carbon–carbon double bond length of C(7)–C(10) is 1.350(3) Å and this is typical for carbon–carbon double bond [9]. The bond lengths of the two carbonyl groups are almost the same (1.205 Å and 1.211 Å), which is similar to that reported [10].

The complete set of X-ray diffraction data for the title compound was deposited to the Cambridge Crystallographic Data Centre (CCDC entry no. 2295930).

Corresponding authors: Mengdan Wang, School of Chemistry and Chemical Engineering, Henan University of Science and Technology, Luoyang, Henan 471003, P.R. China, E-mail: ; and Jun-Ying Ma, School of Chemistry and Chemical Engineering, Henan University of Science and Technology, Provincial and Ministerial Co-construction of Collaborative Innovation Center for Non-ferrous Metal New Materials and Advanced Processing Technology, Luoyang, Henan 471003, P.R. China, E-mail:

Funding source: The Doctor Start-Up Funds of Henan University of Science and Technology.

  1. Research funding: This work was supported by the Doctor Start-up Funds of Henan University of Science and Technology (no. 13480078).

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

References

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Received: 2023-09-21
Accepted: 2023-10-20
Published Online: 2023-11-08
Published in Print: 2024-02-26

© 2023 the author(s), published by De Gruyter, Berlin/Boston

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

Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of poly[diaqua-(μ4-3,3′-di(1H-1,2,4-triazol-1-yl)-[1,1′-biphenyl]-4,4′-dicarboxylate-N:N′:O:O′)cadmium(II)], C18H14N6O6Cd
  4. Crystal structure of (8R,8′S,13S,13′R)-8,8′-bis(hydroxymethyl)-9,9′,10,10′-tetramethoxy-5,5′,6,6′,8,8′,13,13′-octahydro-[13,13′-bi[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline]-7,7′-diium chloride-methanol (1/2), C46H58N2O14Cl2
  5. The crystal structure of 8-methoxy-2,2-diphenyl-tosyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ig]quinoline, C29H25BN2O3S
  6. Crystal structure of aqua-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)copper(II) 5-carboxyisophthalate tetrahydrate, C25H50N4CuO11
  7. The crystal structure of 1-(naphthalen-2-ylsulfonyl)-2,2-diphenyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ij]quinoline, C31H23BN2O2S
  8. Crystal structure of iodido-(η6-benzene) (1-(pyridin-2-yl)-N-(p-fluoro-methanamine)-κ2N,Nʹ)ruthenium(II) hexaflourophosphate, (C18H15F7IN2RuP)
  9. The crystal structure of 1-(3-oxo-1-phenyl-3-(p-tolyl) propylidene)-1,3-dihydro-2H-inden-2-one, C25H20O2
  10. Crystal structure of tricyclohexyl[4-(4H-1,2,4-triazol-4-yl)-benzoato-κO]tin(IV), C27H39N3O2Sn
  11. Crystal structure of [triaqua-(8-carboxymethoxy-quinoline-2-carboxylate-κ4N,O,O,O)cadmium(II)]monohydrate, C12H15NO9Cd
  12. Crystal structure of ethyl 2-((4-(3,5-dimethylisoxazol-4-yl)-2,6-difluorophenyl)amino)benzoate, C20H18F2N2O3
  13. The crystal structure of 2-(hydroxymethyl)-2-(4H-1,2,4-triazol-4-yl)propane-1,3-diol, C6H11N3O3
  14. The crystal structure of 1,2-bis(2,4-dinitrophenyl) hydrazine, C12H8N6O8
  15. Crystal structure of 1-(2,6-dichloro-4-(3,5-dimethylisoxazol-4-yl)phenyl)-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-one, C19H14Cl2N2O3
  16. The crystal structure of 5-amino-5-oxo-4-(1-oxo-4-(2-oxopyrrolidin-1-yl)isoindolin-2-yl)pentanoic acid, C17H19N3O5
  17. Crystal structure of N2,N6-bis(2-(((Z)-5-bromo-2-hydroxybenzylidene)amino) phenyl)pyridine-2,6-dicarboxamide, C33H23Br2N5O4
  18. The crystal structure of (E)-2-methoxy-6-(((5-methyl-1,3,4-thiadiazol-2-yl)imino)methyl)phenol, C11H11N3O2S
  19. The crystal structure of 3-((tert-butyldiphenylsilyl)methyl)-5,5-diphenyl-6-(p-tolyl) tetrahydro-2H-pyran-2-one, C41H42O2Si
  20. Crystal structure of 9-fluoro-4-(6-methoxypyridin-3-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine, C18H15FN4O
  21. The crystal structure of 2-bromo-5-(4-cyanophenoxy)benzyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate, C21H19BrN2O3
  22. Crystal structure of 3,3′-(1,4-phenylenebis(methylene))bis(1-isopropyl-1H-imidazol-3-ium) bis(hexafluorophosphate(V)), C10H14F6N2P
  23. The crystal structure of 2,2-di(thiophen-3-yl)-1-tosyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ig]quinoline, C24H19BN2O2S3
  24. Crystal structure of 5-bromo-1-(2-iodobenzoyl)-1H-indole-3-carbaldehyde, C16H9BrINO2
  25. The crystal structure of monocarbonyl-2-carboxypyridinato-κ2N,O-triphenylphosphine-rhodium(I) acetonitrile solvate, C26H20.50N1.50O3PRh
  26. Crystal structure of dichlorido-tetrakis(1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol-κ1N)manganese(II), C60H68O4N12Cl10Mn
  27. Crystal structure of 3-(tert-butyldiphenylsilyl)-1-(2,6-dichlorophenyl)-2,2-diphenylpropan-1-ol, C37H36Cl2OSi
  28. Crystal structure of langite from Mine du Pradet (France)
  29. The crystal structure of 5′-(furan-2-yl)-3′-((4-methylphenyl)sulfonamido)-3′,4′,5′,6′-tetrahydro-[1,1′:3′,1″-terphenyl]-4′-carboxylic acid, C30H27NO5S
  30. Synthesis and crystal structure of bis{2-(((4-acetophenone)imino)methyl)-4-fluorophenolato-κ2N,O}zinc(II), C30H22F2N2O4Zn
  31. The crystal structure of poly[(tripyridine-κ3N,N′,N″) μ3-(pyridine-3,4-dicarboxylate-κ3N:O:O′) manganese(II)], C22H22N4O8Mn
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https://doi.org/10.1515/ncrs-2023-0418
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of poly[diaqua-(μ4-3,3′-di(1H-1,2,4-triazol-1-yl)-[1,1′-biphenyl]-4,4′-dicarboxylate-N:N′:O:O′)cadmium(II)], C18H14N6O6Cd
  4. Crystal structure of (8R,8′S,13S,13′R)-8,8′-bis(hydroxymethyl)-9,9′,10,10′-tetramethoxy-5,5′,6,6′,8,8′,13,13′-octahydro-[13,13′-bi[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline]-7,7′-diium chloride-methanol (1/2), C46H58N2O14Cl2
  5. The crystal structure of 8-methoxy-2,2-diphenyl-tosyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ig]quinoline, C29H25BN2O3S
  6. Crystal structure of aqua-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)copper(II) 5-carboxyisophthalate tetrahydrate, C25H50N4CuO11
  7. The crystal structure of 1-(naphthalen-2-ylsulfonyl)-2,2-diphenyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ij]quinoline, C31H23BN2O2S
  8. Crystal structure of iodido-(η6-benzene) (1-(pyridin-2-yl)-N-(p-fluoro-methanamine)-κ2N,Nʹ)ruthenium(II) hexaflourophosphate, (C18H15F7IN2RuP)
  9. The crystal structure of 1-(3-oxo-1-phenyl-3-(p-tolyl) propylidene)-1,3-dihydro-2H-inden-2-one, C25H20O2
  10. Crystal structure of tricyclohexyl[4-(4H-1,2,4-triazol-4-yl)-benzoato-κO]tin(IV), C27H39N3O2Sn
  11. Crystal structure of [triaqua-(8-carboxymethoxy-quinoline-2-carboxylate-κ4N,O,O,O)cadmium(II)]monohydrate, C12H15NO9Cd
  12. Crystal structure of ethyl 2-((4-(3,5-dimethylisoxazol-4-yl)-2,6-difluorophenyl)amino)benzoate, C20H18F2N2O3
  13. The crystal structure of 2-(hydroxymethyl)-2-(4H-1,2,4-triazol-4-yl)propane-1,3-diol, C6H11N3O3
  14. The crystal structure of 1,2-bis(2,4-dinitrophenyl) hydrazine, C12H8N6O8
  15. Crystal structure of 1-(2,6-dichloro-4-(3,5-dimethylisoxazol-4-yl)phenyl)-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-one, C19H14Cl2N2O3
  16. The crystal structure of 5-amino-5-oxo-4-(1-oxo-4-(2-oxopyrrolidin-1-yl)isoindolin-2-yl)pentanoic acid, C17H19N3O5
  17. Crystal structure of N2,N6-bis(2-(((Z)-5-bromo-2-hydroxybenzylidene)amino) phenyl)pyridine-2,6-dicarboxamide, C33H23Br2N5O4
  18. The crystal structure of (E)-2-methoxy-6-(((5-methyl-1,3,4-thiadiazol-2-yl)imino)methyl)phenol, C11H11N3O2S
  19. The crystal structure of 3-((tert-butyldiphenylsilyl)methyl)-5,5-diphenyl-6-(p-tolyl) tetrahydro-2H-pyran-2-one, C41H42O2Si
  20. Crystal structure of 9-fluoro-4-(6-methoxypyridin-3-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine, C18H15FN4O
  21. The crystal structure of 2-bromo-5-(4-cyanophenoxy)benzyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate, C21H19BrN2O3
  22. Crystal structure of 3,3′-(1,4-phenylenebis(methylene))bis(1-isopropyl-1H-imidazol-3-ium) bis(hexafluorophosphate(V)), C10H14F6N2P
  23. The crystal structure of 2,2-di(thiophen-3-yl)-1-tosyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ig]quinoline, C24H19BN2O2S3
  24. Crystal structure of 5-bromo-1-(2-iodobenzoyl)-1H-indole-3-carbaldehyde, C16H9BrINO2
  25. The crystal structure of monocarbonyl-2-carboxypyridinato-κ2N,O-triphenylphosphine-rhodium(I) acetonitrile solvate, C26H20.50N1.50O3PRh
  26. Crystal structure of dichlorido-tetrakis(1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol-κ1N)manganese(II), C60H68O4N12Cl10Mn
  27. Crystal structure of 3-(tert-butyldiphenylsilyl)-1-(2,6-dichlorophenyl)-2,2-diphenylpropan-1-ol, C37H36Cl2OSi
  28. Crystal structure of langite from Mine du Pradet (France)
  29. The crystal structure of 5′-(furan-2-yl)-3′-((4-methylphenyl)sulfonamido)-3′,4′,5′,6′-tetrahydro-[1,1′:3′,1″-terphenyl]-4′-carboxylic acid, C30H27NO5S
  30. Synthesis and crystal structure of bis{2-(((4-acetophenone)imino)methyl)-4-fluorophenolato-κ2N,O}zinc(II), C30H22F2N2O4Zn
  31. The crystal structure of poly[(tripyridine-κ3N,N′,N″) μ3-(pyridine-3,4-dicarboxylate-κ3N:O:O′) manganese(II)], C22H22N4O8Mn
  32. The crystal structure of (E)-4-chloro-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H15ClN2O2
  33. Synthesis and crystal structure of bis{2-(tert-butyl)-6-((E)-((4-((E)-1-(methoxyimino) ethyl)phenyl)imino)methyl)phenolato-κ2N,O}cobalt(II), C40H46CoN4O4
  34. Crystal structure of tetraaqua-[(1-(carboxymethyl)-1H-pyrazole-3-carboxylato-κ2N,O)cobalt(II)], C6H12CoN2O8
  35. (6R,7S)-2,3,13-trimethoxy-6,7-dimethyl-5,6,7,8-tetrahydrobenzo[3′,4′]cycloocta [1′,2′:4,5]benzo[1,2-d][1,3]dioxol-1-ol, C22H26O6
  36. Crystal structure of 2-((2,6-dichloro-4-(3,5-dimethylisoxazol-4-yl)phenyl)amino)benzoic acid, C18H14Cl2N2O3
  37. Crystal structure of (5aS,6aS,8aR,9R,11aS, 11bS,13R,13aS)-1,1,8a,11a-tetramethyl-9-((S)-1-((S)-5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl)-3-oxo-1,7,8,8a,9,10,11,11a,11b,12,13,13a-dodecahydro-3H,6H-cyclopenta[5,6]cyclopropa[1,8a]naphtho[2,1-c]oxepin-13-yl acetate, C32H44O6
  38. Crystal structure of catena-poly[triaqua-(μ2-1-(4-carboxylatophenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylato-O,O′:O″)cobalt(II)], C12H12N2O8Co
  39. Crystal structure of 3-[(furan-2-ylmethyl)-amino]-2-(2,3,4,5-tetrafluoro-benzoyl)-acrylic acid ethyl ester, C17H13F4NO4
  40. Crystal structure of methyl 4-(2-ethoxy-2-oxoethoxy)-3-methoxybenzoate, C13H16O6
  41. Crystal structure of 4-bromo-2-(4-chlorophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile, C13H7BrClF3N2
  42. The crystal structure of triaqua-(8-carboxymethoxy-quinoline-2-carboxylate-κ3N,O,O)nickel(II) monohydrate, C12H15NO9Ni
  43. Crystal structure of dihydroxy(2,4,6-triisopro-pylphenyl)telluronium trifluoromethanesulfonate, C16H25F3O5STe
  44. The crystal structure of 1-(carboxymethyl)-1H-imidazole 3-oxide
  45. The crystal structure of 1,3,5-tris(dibromomethyl)benzene, C9H6Br6
  46. Crystal structure of (Z)-3-(4-methoxyphenyl)-4-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-N-phenylthiazol-2(3H)-imine, C25H21N5OS
  47. Crystal structure of (Z)-3-(3-(4-hydroxyphenyl)-2-(phenylimino)-2,3-dihydrothiazol-4-yl)-2H-chromen-2-one, C24H16N2O3S
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