Startseite Crystal structure of 3-(4-methoxyphenyl)-1-(4-methylphenyl)prop-2-en-1-one, C17H16O2
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Crystal structure of 3-(4-methoxyphenyl)-1-(4-methylphenyl)prop-2-en-1-one, C17H16O2

  • Yavuz Köysal EMAIL logo , Hakan Bülbül , Funda Özdemir , İlhan Özer İlhan und Necmi Dege
Veröffentlicht/Copyright: 4. Mai 2017

Abstract

C17H16O2, monoclinic, P21/c (no. 14), a = 11.6963(12) Å, b = 11.1187(8) Å, c = 11.6902(10) Å, β = 115.545(7)°, V = 1371.7(2) Å3, Z = 4, Rgt(F) = 0.0350, wRref(F2) = 0.0865, T = 293 K.

CCDC no.:: 1515321

The asymmetric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Colourless prism
Size:0.36 × 0.27 × 0.12 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.8 cm−1
Diffractometer, scan mode:STOE IPDS 2, ω scans
2θmax, completeness:52°, 98.8%
N(hkl)measured, N(hkl)unique, Rint:7194, 2661, 0.037
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1375
N(param)refined:236
Programs:Stoe programs [1], SHELX [2, 3] , ORTEP [4]
Table 2:

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

AtomxyzUiso*/Ueq
C10.36180(15)0.32004(16)0.61559(16)0.0787(4)
C20.43587(15)0.27272(15)0.73366(16)0.0788(4)
C30.41923(13)0.15512(14)0.75852(14)0.0729(4)
C40.32929(16)0.08557(15)0.66461(16)0.0814(5)
C50.25615(15)0.13408(14)0.54835(16)0.0749(4)
C60.27015(13)0.25269(13)0.52017(13)0.0660(4)
C70.19122(15)0.30866(15)0.39781(15)0.0740(4)
C80.10143(15)0.25798(15)0.29722(15)0.0734(4)
C90.02624(13)0.32677(13)0.18103(13)0.0704(4)
C10−0.05096(13)0.26101(12)0.06163(13)0.0662(4)
C11−0.10413(15)0.32522(16)−0.05156(16)0.0763(4)
C12−0.17460(16)0.26820(16)−0.16466(16)0.0798(5)
C13−0.19631(13)0.14563(15)−0.17099(14)0.0730(4)
C14−0.14285(15)0.08265(16)−0.05865(16)0.0779(4)
C15−0.07184(14)0.13783(13)0.05549(17)0.0746(4)
C16−0.2733(2)0.0836(2)−0.2941(2)0.0986(6)
C170.5723(2)0.1671(2)0.9754(2)0.0991(6)
O10.48553(10)0.09799(10)0.87164(10)0.0952(4)
O20.02810(11)0.43693(9)0.18209(9)0.0926(4)
H10.3737(14)0.4032(15)0.5996(13)0.093(5)*
H20.4969(14)0.3226(13)0.7989(14)0.091(5)*
H40.3196(15)0.0037(15)0.6841(14)0.104(5)*
H50.1935(13)0.0848(12)0.4841(13)0.081(4)*
H70.2070(13)0.3943(13)0.3907(12)0.085(4)*
H80.0821(13)0.1756(14)0.2962(12)0.082(4)*
H11−0.0863(14)0.4102(15)−0.0479(14)0.097(5)*
H12−0.2063(13)0.3136(13)−0.2413(14)0.085(5)*
H14−0.1552(13)−0.0036(14)−0.0611(13)0.092(5)*
H15−0.0377(13)0.0903(13)0.1305(13)0.081(4)*
H17A0.6045(19)0.1107(18)1.048(2)0.143(8)*
H17B0.6404(18)0.2026(17)0.9546(16)0.129(7)*
H17C0.5260(16)0.2375(17)0.9895(14)0.113(6)*
H18A−0.362(2)0.100(2)−0.325(2)0.173(10)*
H18B−0.267(2)−0.001(2)−0.290(2)0.159(9)*
H18C−0.251(2)0.1087(19)−0.361(2)0.159(9)*

Source of material

Equimolar quanities of p-methylacetophenone (0.01 mol) and p-methoxybenzaldehyde (0.01 mol) were dissolved in ethanol (10 mL) under stirring and aq. NaOH (30%) was added dropwise. The reaction mixture was stirred at room temperature for a few hours. The reaction mixture was diluted with water & acidifed with HCl. The separated solid was filtered and recrystallised from ethanol [5].

IR (ATR) cm−1: 2932 (aromatic—CH), 2837 (aliphatic—CH), 1651 (C = O), 1593–1416 (C = C); 1H-NMR (δ): 8.00–6.94 (−CH), 2.41 (−CH3), 3.91 (−OCH3); 13C-NMR (δ): 21.54 (−CH3), 55.51 (−OCH3), 188 (C = O), 163 (HC = CH), 144–120 (aromatic—CH3), 113.81–113.75 (aliphatic—CH). Anal. Calcd. for C17H16O2: C, 80.95; H, 6.34; Found: C, 80.63; H, 6.07.

Experimental details

The structure was solved by direct methods and refined by full-matrix least-square techniques. All the H atoms in the molecular structure were found and located in difference Fourier map and refined freely. H bond lengths vary between 0.952(14) Å and 0.969(15) Å for aromatic rings.

Comment

Chalcones consist of two aromatic rings which are linked by three carbon atoms with a α,β-unsaturated carbonyl system. Chalcones and their derivatives are interesting materials for their biological activities such as anti-viral, anti-malarial, anti-cancer, antioxidant, anti-inflammatory, antifungal, antileishmanial, anti-tubercular, anti-hyperglycemic properties [6], [7], [8], [9], [10], [11]. They are also used in different applications such as agriculture [12], cosmetics and manufacture of pesticides [13].

The title compund, C17H16O2, shows E conformation with respect to the C = C double bond (C7 = C8 = 1.318(2) Å). In the molecular structure, the methoxy substituted phenyl ring and the methyl substituted phenyl ring are inclined by 13.78(6)°. The maximum deviations within the ring systems are 0.0052(2) Å for C4 atom of the C1—C6 ring and 0.0033(2) Å for atom C12 of the C10—C15 ring. The attached methyl group is co-planar with the related aromatic ring system (C10—C15). The methoxy group is slightly twisted with the C4—C3—O1—C17 and C2—C3—O1—C17 torsion angles of −174.97(16)° and 5.0(2)°, respectively. In the molecular structure, the bond lengths and angles are consistent with the related structures [14, 15] . The crystal structure presents at least one very weak intermolecular hydrogen bond, namely C11—H11⋯O2′ (with symmetry code: −x, −y + 1, −z).

Acknowledgement

The related single crystal X-Ray data was collected in Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, by using Stoe IPDS II diffractometer and deposited with the CCDC number of 1515321.

References

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Received: 2016-11-7
Accepted: 2017-4-5
Published Online: 2017-5-4
Published in Print: 2017-7-26

©2017 Yavuz Köysal et al., published by De Gruyter.

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Artikel in diesem Heft

  1. Cover and Frontmatter
  2. Crystal structure of poly[diaqua-(μ2-4,4′-bipyridine-κ2N:N′)manganese(II)] bis(4-chlorobenzenesulfonate) – 4,4′-bipyridine – water (1/1/2) C42H40Cl2MnN6O10S2
  3. The crystal structure of 1,2-bis[2-methyl-5-(3-cyanophenyl)-3-thienyl]-3,3,4,4,5,5-hexafluoro-cyclopent-1-ene, C29H16F6N2S2
  4. Crystal structure of the first characterized polymeric copper and sodium complex diaqua-(tris-acetato-κO,O′)(μ2-acetato-κO′′)dinatrium copper(II) monohydrate, C8H18CuNa2O11
  5. The crystal structure of the Schiff base (E)-2,6-diisopropyl-N-(pyridin-3-yl-methylene)aniline, C18H22N2
  6. Crystal structure of methyl 2,7,7-trimethyl-4-(4-nitrophenyl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylate, C20H22N2O5
  7. Crystal structure of bis(1,3-bis(diphenylphosphino)propane-κ2P,P′)silver(I) trifluorosulfonate–methanol (1:0.5), [Ag(C27H26P2)]SO3CF3⋅0.5CH3OH
  8. Crystal structure of μ-1,4-bis(diphenylphosphine)butane-2,9-dimethyl-1,10-phenanthroline-κ2N:N′-bis(cyano-κC)dicopper(I)]-water, C58H56Cu2N6O2P2
  9. Crystal structure of N2,N6-bis(1-hydrazinyl-2-methyl-1-oxopropan-2-yl) pyridine-2,6-dicarboxamide, C15H23N7O4
  10. Crystal structure of 1,3-dimethyl-2-phenyl-1H-perimidin-3-ium iodide, C19H17IN2
  11. Crystal structure of diaqua-(2,2′-(butane-1,4-diyl)-bis(5-carboxy-1H-imidazole-4-carboxylato)-κ4O,O′,N,N′)cadmium(II) monohydrate, C14H18O11N4Cd
  12. Crystal structure of ethyl (E)-3-(cyclopropylamino)-2-(2,4-dichloro-5-fluorobenzoyl) acrylate, C15H14Cl2FNO3
  13. Crystal structure of bis-(1-(4-chlorophenyl)-3-phenyl-4-thenoyl-1H-pyrazol-5-ol-κ2O,O′)-(N,N-dimethylformamide)zinc(II), C43H31Cl2N5O5S2Zn
  14. Crystal structure of tetrakis(μ3-2-(N-(2-hydroxyethyl)amino)ethoxo)-tetrachloro-tetra-cobalt(II) methanol solvate, C17H44Cl4Co4N4O9
  15. Crystal structure of 3-amino-1-(4-bromophenyl)-9-methoxy-1H-benzo[f]chromene-2-carbonitrile, C21H15BrN2O2
  16. Crystal structure of 2-amino-4-(4-isopropyl-phenyl)-3-cyano-5-oxo-4H,5H-pyrano[3,2-c]chromene, C22H18N2O3
  17. Crystal structure of 3-amino-8-methoxy-1-(4-methoxy phenyl)-1H-benzo[f]chromene-2-carbonitrile, C22H18N2O3
  18. Crystal structure of monoaqua-[6,6′-((1E,1′E)-(1,2-phenylene bis(azanylylidene))bis(methanylylidene))bis(4-bromo-2-nitrophenolato-κ4N,N′,O,O′)]zinc(II), C20H12Br2N4O7Zn
  19. Crystal structure of 11-(4-(dimethylamino)phenyl)-17-hydroxy-13-methyl-17-(prop-1-yn-1-yl)-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one – acetonitril (1/2), C33H41N3O2
  20. Crystal structure of tert-butyl (phenylsulfinyl)carbamate, C11H15NO3S
  21. Crystal structure of catena-poly{diaqua-bis(3-(1H-1,2,4-triazol-1-yl)benzoato-κ2O:N)copper(II)} monohydrate, C18H18CuN6O7
  22. Crystal structure of tetraaqua-bis(3-(4H-1,2,4-triazol-4-yl)benzoato-κN)cobalt(II), C18H20CoN6O8
  23. The crystal structure of 4-bromo-N-cyclopropyl-2,5-difluorobenzenesulfonamide, C9H8BrF2NO2S
  24. Crystal structure of ([3,3′-bipyridine]-6,6′-dicarboxylato-κ2O:O′)-bis(1,2-bis(4-pyridyl)ethane-κ2N:N′)disilver(I) dihydrate, C37H35Ag2N5O6
  25. The crystal structure of (4-(1H-1,2,4-triazol-1-yl)benzoato-κN)-[4-(1H-1,2,4-triazol-1-yl)benzoic acid-κN]silver(I), C18H13AgN6O4
  26. Crystal structure of 3-(4-methoxyphenyl)-1-(4-methylphenyl)prop-2-en-1-one, C17H16O2
  27. Crystal structure of bis(2-((E)-((4-((E)-1-(ethoxyimino)ethyl)phenyl)imino)methyl)-5-methoxyphenolato-κ2O,N)copper(II), C36H38CuN4O6
  28. Crystal structure of poly[1,2-bis(1,2,4-triazol-4-yl)ethane-κ2N:N′]silver(I) bromate monohydrate]silver(I), C6H10AgBrN6O4
  29. The crystal structure of 2,3,5-triphenyl-2,3-dihydro-1H-tetrazol-1-ium 2,3-dioxoindoline-5-sulfonate, C27H19N5O5S
  30. Crystal structure of 3-(2-amino-1,3-selenazol-4-yl)-2H-chromen-2-one – dimethylformamide (1/1), C15H15N3O3Se
  31. Crystal structure of diethyl 3,3′-(diazene-1,2-diyl)(E)-dibenzoate, C18H18N2O4
  32. Crystal structure of cis-bis((1H-benzimidazol-2-yl)methanol-κN,O)-bis(isothiocyanato-κN)nickel(II), C18H16N6NiO2S2
  33. Crystal structure of bis(2-(2′-hydroxy-5′-methoxyphenyl)-1H-benzimidazole)boron – tetrahydrofuran (1/1), C36H37N4O6B
  34. Crystal structure of poly[aqua-bis(nitrato-κ2O,O′)-(μ3-1,3-benzimidazol-3-ium-1,3-diacetato-κ4O,O′:O′′:O′′′)dysprosium(III)], C11H11DyN4O11
  35. Crystal structure of n-butyl-tris(dicyclo-hexylamido)hafnium(IV), C40H75HfN3
  36. Crystal structure of (E)-1-[1-(3-chloro-4-fluoro-phenyl)ethylidene]-2-(2,4-dinitrophenyl)hydrazine, C28H20Cl2F2N8O8
  37. The crystal structure of ethyl 4-((2-hydroxybenzyl)amino)benzoate, a Schiff base, C16H17NO3
  38. Crystal structure of 3-(2-(4-isobutylphenyl)propanoyl)-1-methylimidazolidine-2,4-dione, C17H22N2O3
  39. Crystal structure of poly[(μ3-2-(pyrazin-2-ylthio)acetato-κ3N:O:S)silver(I)], C6H5AgN2O2S
  40. Crystal structure of (E)-1-(3-((E)-((2-hydroxynaphthalen-1-yl)methylene)amino)phenyl)ethanone O-benzyl oxime, C26H22N2O2
  41. Crystal structure of (E)-2,3-dihydroxybenzaldehyde O-(2-((((E)-1-(2,5-dihydroxyphenyl)ethylidene)amino)oxy)ethyl) oxime monohydrate, C17H20N2O7
  42. Crystal structure of 4-(chloromethyl)-3-nitrobenzoic acid, C8H6ClNO4
  43. Crystal stucture of 4-((10H-phenothiazin-10-yl)methyl)-2,6-di-tert-butylphenol, C27H31NOS
  44. The crystal structure of ethyl 1-(4-nitrophenyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate, C13H10F3N3O4
  45. Crystal structure of catena-poly[di-(μ3-oxido-κ3O:O:O)-tetraoxido-(μ2-5′-(pyrazin-2-yl)-1H,2′H-3,3′-bi(1,2,4-triazole)-κ2N:N′)dimolybdenum(VI)], C8H6Mo2N8O6
  46. Crystal structure of (3,6-dioxocyclohexa-1,4-diene-1,4-bis(olato)-κ4O,O′:O′′,O′′′)-bis(tris(2-pyridylmethyl)amine-κ4N,N′,N′′,N′′′))-dizinc(II) bis(hexafluorophosphate(V)), C42H38F12N8O4P2Zn2
  47. Crystal structure of catena-poly[hexakis(μ2-2-acetylphenolato-κ3O:O,O′)trimanganese(II)], C48H42Mn3O12
  48. The crystal structure of 2,2-difluoro-4-(trifluoromethyl)-2,5-dihydro-[1,3,2]dioxaborinino[5,4-c]chromen-3-ium-2-uide, C11H6BF5O3
  49. Crystal structure of methyl (E)-2-(4-(diethylamino)-2-hydroxybenzylidene)hydrazine-1-carboxylate, C13H19N3O3
  50. The crystal structure of tert-butyl 2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylate, C10H15N3O2
  51. Crystal structure of 1,1-bis(η5-adamantylcyclopentadienyl)-3-phenyl-2-trimethylsilyl-2,3-dihydroisotitanazole, C42H55NSiTi
  52. Crystal structure of 2-(4-(2-(4-benzylpiperazin-1-yl)ethyl)benzyl)isoindoline-1,3-dione, C28H29N3O2
  53. Important impurity of Flupirtine – a single crystal study on ethyl (6-amino-5-((ethoxycarbonyl)amino)pyridin-2-yl)(4-fluorobenzyl)carbamate, C18H21FN4O4
  54. Crystal structure of ethyl 3-(4-methoxyphenyl)-1-(2-(4-methoxyphenyl)-2-oxoethyl)-1H-pyrazole-5-carboxylate, C22H22N2O5
  55. Crystal structure of 2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium 5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-olate methanol solvate, C37H35N1O10
  56. The crystal structure of the inner salt of 2-[(aminoiminomethyl)amino]ethylcarbamic acid [systematic name: (2-((diaminomethylene)ammonio)ethyl)carbamate], C4H10N4O2
  57. Crystal structure of (8-hydroxy-5-nitroquinolinium) perchlorate – 8-hydroxy-5-nitroquinoline (1/1), C18H13ClN4O10
  58. The crystal structure of (5-methyl-1,2,4-oxadiazol-3-yl)ferrocene, C13H12FeN2O
  59. Crystal structure of methyl 1-(2-(fluorosulfonyl)ethyl)-2-oxocyclopentanecarboxylate, C9H13FO5S
  60. Crystal structure of the triclinic modification of 1-methyl-4-nitroimidzole, C4H5N3O2
  61. Corrigendum
  62. Crystal structure of 4-bromo-2-(1H-pyrazol-3-yl)phenol, C9H7BrN2O
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