Home Physical Sciences The crystal structure of (Z)-3-((2-(2-(2-aminophenoxy)ethoxy)phenyl)amino)-1-phenylbut-2-en-1-one, C24H24N2O3
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The crystal structure of (Z)-3-((2-(2-(2-aminophenoxy)ethoxy)phenyl)amino)-1-phenylbut-2-en-1-one, C24H24N2O3

  • Weilian Zhang ORCID logo , Zhenyu Zuo EMAIL logo , Chen Yanhui and Liu Bin
Published/Copyright: February 23, 2021
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 236 Issue 3

Abstract

C24H24N2O3, monoclinic, P21/n (no. 14), a = 13.674(3) Å, b = 7.3900(14) Å, c = 20.862(4) Å, β = 106.728(7)°, V = 2018.9(7) Å3, Z = 4, Rgt(F) = 0.0633, wRref(F2) = 0.1804, T = 293 K.

CCDC no.: 2047026

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 block
Size:0.23 × 0.21 × 0.20 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.09 mm−1
Diffractometer, scan mode:Bruker Apex-II, φ and ω
θmax, completeness:25.0°, 99%
N(hkl)measured, N(hkl)unique, Rint:13143, 3530, 0.062
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1844
N(param)refined:264
Programs:Bruker [1], SHELX [2], Olex2 [3]
Table 2:

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

AtomxyzUiso*/Ueq
C10.6986 (2)0.4610 (4)0.33550 (15)0.0508 (8)
C20.7324 (3)0.4662 (4)0.40478 (16)0.0614 (9)
H20.68500.47170.42890.074*
C30.8348 (3)0.4635 (5)0.43842 (17)0.0703 (10)
H30.85580.46850.48490.084*
C40.9066 (3)0.4535 (5)0.40386 (18)0.0737 (10)
H40.97580.45150.42690.088*
C50.8746 (2)0.4462 (5)0.33398 (17)0.0655 (10)
H50.92220.43780.31000.079*
C60.7722 (2)0.4516 (4)0.30107 (15)0.0516 (8)
C70.7976 (2)0.4539 (5)0.19064 (14)0.0549 (8)
H7A0.83900.34510.19670.066*
H7B0.84230.55860.20020.066*
C80.7259 (2)0.4633 (4)0.12108 (14)0.0537 (8)
H8A0.67490.36850.11450.064*
H8B0.69130.57940.11380.064*
C90.7329 (2)0.4139 (4)0.00945 (15)0.0508 (8)
C100.6318 (2)0.4615 (5)−0.01889 (16)0.0598 (9)
H100.59540.51700.00700.072*
C110.5851 (2)0.4265 (5)−0.08572 (17)0.0652 (10)
H110.51710.4585−0.10460.078*
C120.6382 (2)0.3447 (4)−0.12453 (16)0.0632 (9)
H120.60590.3206−0.16940.076*
C130.7390 (2)0.2982 (4)−0.09730 (15)0.0557 (8)
H130.77430.2425−0.12390.067*
C140.7884 (2)0.3334 (4)−0.03082 (15)0.0459 (7)
C150.9706 (2)0.3223 (4)−0.08844 (14)0.0567 (9)
H15A1.03720.3589−0.09010.085*
H15B0.92310.4193−0.10410.085*
H15C0.94910.2180−0.11640.085*
C160.9745 (2)0.2762 (4)−0.01741 (14)0.0445 (7)
C171.0673 (2)0.2308 (4)0.02690 (14)0.0483 (8)
H171.12410.22950.01090.058*
C181.0824 (2)0.1860 (4)0.09499 (15)0.0470 (8)
C191.1877 (2)0.1466 (4)0.14006 (15)0.0465 (8)
C201.2758 (2)0.1954 (4)0.12423 (16)0.0588 (9)
H201.27100.25080.08340.071*
C211.3707 (3)0.1622 (5)0.16862 (18)0.0717 (10)
H211.42940.19600.15770.086*
C221.3785 (3)0.0790 (5)0.22905 (18)0.0719 (10)
H221.44230.05710.25900.086*
C231.2914 (3)0.0287 (4)0.24488 (16)0.0622 (9)
H231.2965−0.02860.28540.075*
C241.1973 (3)0.0624 (4)0.20133 (15)0.0550 (8)
H241.13900.02870.21280.066*
N10.5959 (2)0.4638 (4)0.29936 (14)0.0720 (9)
H1A0.57560.35410.29020.086*
H1B0.56130.51320.32320.086*
N20.89046 (18)0.2845 (3)0.00320 (12)0.0500 (7)
H2A0.90010.25500.04440.060*
O10.73090 (15)0.4513 (3)0.23229 (10)0.0643 (7)
O20.78584 (14)0.4406 (3)0.07565 (9)0.0585 (6)
O31.00963 (16)0.1834 (3)0.12094 (10)0.0664 (7)

Source of material

To the solution of 2,2′-(ethane-1,2-diylbis(oxy))dianiline (0.244 g 1 mmol) in ethanol (20 ml) was added the solution of benzoylacetone 0.162 g (1 mmol) in ethanol (20 ml) dropwisely. The mixture was refluxed for 8 h then cooled and filtered to get a white solid. The solid was washed with ethanol for three times, dried and purified by column chromatography (the developing agent was dichloromethane: Petroleum ether = 1:1) to get (Z)-3-((2-(2-(2-aminophenoxy)ethoxy)phenyl)amino)-1-phenylbut-2-en-1-one (0.194 g, the yield 50%). The single crystal suitable for X-ray diffraction was obtained by recrystallization in diethyl ether.

Experimental details

The data were scaled and corrected for absorption using SADABS-2016/2 (Bruker, APEX–II CCD). The hydrogen atoms were placed at calculated positions and refined as riding atoms with isotropic displacement parameters.

Comment

α,β-Unsaturated ketones [4], [5] are highly appreciated because they have shown promising biological activities such as anti-inflammatory [6], [7], antimicrobial [8], anti-parasitic [9], antibacterial [10], antimalarial [11], antitumor [12], anti-nematodal [13], antioxidant [14] and anti-tubulin [15] activities. The synthesis and activity research of the novel α,β-unsaturated ketones have drawn more and more attentions in recent decades.

This contribution is part of a study on amine-based organic molecules [16]. The title compound (Z)-3-((2-(2-(2-aminophenoxy)ethoxy)phenyl)amino)-1-phenylbut-2-en-1-one was synthesized by condensation reaction using 2,2′-(ethane-1,2-diylbis(oxy))dianiline as the starting material. There is one molecule in the asymmetric unit (see the figure). The angles of O3–C18–C19, C16–N2–C14 and C6–O1–C7 are 117.4(3), 131.5(2) and 119.3(2)° respectively, which are in normal range. Hydrogen bonds were observed as following: N1–H1B⋅⋅⋅O3 hydrogen bond (d(H1B⋅⋅⋅O3) = 2.13 Å, N2–H2A⋅⋅⋅O2 hydrogen bond (d(H2A⋅⋅⋅O2) = 2.31 Å, N2–H2A⋅⋅⋅O3 hydrogen bond (d(H2A⋅⋅⋅O3) = 1.92 Å.

Corresponding author: Zhenyu Zuo, College of Pharmacy, Shaanxi University of Chinese Medicine, Xi’an, Shaanxi, 712046, China; and Shaanxi Key Laboratory of Basic and New Herbal Medicament Research, Xi’an, 712046, China, E-mail:

Funding source: National Key R&D program of China

Award Identifier / Grant number: 2018YFC1706903

Funding source: Key projects of Shaanxi Provincial Education Department

Award Identifier / Grant number: 20JS033

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

  2. Research funding: The research was supported by the National Key R&D program of China (2018YFC1706903), Key projects of Shaanxi Provincial Education Department (20JS033).

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

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Received: 2021-01-14
Accepted: 2021-02-01
Published Online: 2021-02-23
Published in Print: 2021-05-26

© 2021 Weilian Zhang et al., published by De Gruyter, Berlin/Boston

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

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  60. Crystal structure of 1‐tert‐butyl‐3‐(2,6‐diisopropyl‐4‐phenoxyphenyl)‐2-methylisothiourea, C24H34N2OS
  61. Crystal structure of catena-poly[triaqua-(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2N:N′)-(4,4′-(1H-1,2,4-triazole-3,5-diyl)dibenzoato-κ1O)cobalt(II)] — N,N′-dimethylformamide (1/1), C28H34N8O8Co
  62. Crystal structure of tetraaqua-bis(1,4-di(1H-imidazol-1-yl)benzene-κ1N)manganese(II) 2,3-dihydroxyterephthalate, C32H32MnN8O10
https://doi.org/10.1515/ncrs-2021-0022
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of bis(μ2-5-chloro-2-oxido-N-(1-oxidoethylidene)benzohydrazonato-κ5N,O,O′:N′,O′′)hexkis(pyridine-κ1N)trinickel(II) - pyridine (1/1), C63H57Cl2N13Ni3O6
  4. Crystal structure of [(μ2-succinato κ3O,O′:O′′)-bis-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane)]dinickel(II)] diperchlorate, dihydrate C36H82Cl2N8Ni2O15
  5. Crystal structure of catena-poly[aquabis(3-nitrobenzoato-κ2O:O′)-(μ2-pyrazine-N: N′)cadmium(II)], C18H14N4O9Cd
  6. Crystal structure of 4-(2,2-difluoroethyl)-2,4,6-trimethylisoquinoline-1,3(2H,4H)-dione, C14H15F2NO2
  7. The crystal structure of thioxanthen-9-one-10,10-dioxide, C13H8O3S – a second polymorph
  8. Crystal structure of (E)-2-((2-methoxy-3-pyridyl)methylene)-7-fluoro-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2
  9. The crystal structure of diaquahydrogen 2,5-dimethylbenzenesulphonate, C8H14O5S
  10. The crystal structure of N-(4-(cyclohexylimino)pent-2-en-2-yl)cyclohexanamine, C17H30N2
  11. The twinned crystal structure of 1,3-phenylenedimethanaminium dibromide, C8H14Br2N2
  12. Crystal structure of 2,4,7,9-tetranitro-10H-benzofuro[3,2-b]indole – dimethyl sulfoxide (1/1), C16H11N5O10S
  13. Crystal structure of 2,6-bis(2-(pyridin-3-yl)ethyl)pyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-tetraone, C24H18N4O4
  14. The crystal structure of 3,4-dichlorobenzoic acid chloride, C7H3Cl3O
  15. Crystal structure of 1,1′-(1,4-phenylenebis(methylene))bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-k2S:S)zinc(II), C26H18N6ZnS4
  16. Crystal structure of tetrakis(μ-naphthalene-1-carboxylato-κ2O,O′)bis(methanol)copper(II), C46H36Cu2O10
  17. Crystal structure of 9-methyl-3-methylene-1,2,3,9-tetrahydro-4H-carbazol-4-one, C14H13NO
  18. Crystal structure of bis(amino(carbamothioylamino)methaniminium) 3-nitrophthalate monohydrate, C12H19N9O7S2
  19. Crystal structure of 3,3′-(1,2-phenylene-bis(methylene))bis(1-ethyl-1H-imidazol-3-ium) bis(hexafluorophosphate), C18H24F12N4P2
  20. The crystal structure of 5-hydroxy-6,8-dimethoxy-2-methyl-4H-benzo[g]chromen-4-one– rubrofusarin B, C16H14O5
  21. The crystal structure of bis(ethanol-kO)- bis(6-aminopicolinato-k2N,O)manganese(II), C16H22O6N4Mn
  22. The crystal structure of 3,3′-((carbonylbis(azanediyl))bis(ethane-2,1-diyl)) bis(1-methyl-1H-benzo[d]imidazol-3-ium) tetrafluoroborate monohydrate, C21H28N6O3B2F8
  23. Crystal structure of dimethanol-dichlorido-bis( μ2-2-(((1,5-dimethyl-3-oxo-2- phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino)methyl)phenolato- κ4O:O,O′,N)dinickel (II), C20H24ClNiN3O4
  24. The crystal structure of methyl 5-(trifluoromethyl)-1H-pyrrole-2-carboxylate, C7H6F3NO2
  25. Crystal structure of (OC‐6‐13)‐aqua‐tris (3‐bromopyridine‐κ1N)‐bis(trifluoroacetato‐κ1O)cadmium(II) C19H14Br3CdF6N3O5
  26. Crystal structure of methyl (E)-3-(4-(2-ethoxy-2-oxoethoxy)phenyl) acrylate, C14H16O5
  27. Crystal structure of methyl 4-acetoxy-3,5-dimethoxybenzoate, C12H14O6
  28. The crystal structure of 2-(1H-benzimidazol-2-yl)-3-bromo-5-chlorophenol, C13H8BrClN2O
  29. The crystal structure of bis(μ2-5-chloro-N-(2-methyl-1-oxidopropylidene)-2-oxidobenzohydrazonate-κ5N,O,O′:N′,O′′)pentakis(pyridine-κ1N)tricopper(II), C47H45Cl2N9Cu3O6
  30. Synthesis and crystal structure of catena-poly[aqua-bis(nitrato-κ2O:O′)- (μ2-((1 H-imidazol-1-yl)methyl)benzene-κ2 N,N′)-H2O-κ2O]cadmium(II), C14H16N6O7Cd
  31. The crystal structure of pentakis(carbonyl)-{μ-[2,3-bis(sulfanyl)propan-1-olato]}-(triphenylphosphane)diiron (Fe–Fe)C26H21Fe2O6PS2
  32. Crystal structure of ethyl-2-(3-benzoylthioureido)propanoate, C13H16N2O3S
  33. Crystal structure of 2-methoxy-4b,5,14,15-tetrahydro-6H-isoquinolino[2′,1′:1,6] pyrazino[2,3-b]quinoxaline, C19H18N4O
  34. Crystal structure of 2,2′-[ethane-1,2-diylbis(azanylylidenemethylylidene)]bis(6-chlorophenol), C16H14Cl2N2O2
  35. The crystal structure of (Z)-3-((2-(2-(2-aminophenoxy)ethoxy)phenyl)amino)-1-phenylbut-2-en-1-one, C24H24N2O3
  36. The crystal structure of 10-(3,5-di(pyridin-4-yl)phenyl)-10H-phenoxazine dihydrate, C28H23N3O3
  37. Crystal structure of poly[dipoly[aqua-di(µ2-pyrazin-2-olato-κ2N:N′) zinc(II)], C8H8N4O3Zn
  38. Crystal structure of poly[tetra(μ2-cyanido-κ2N:O)-bis(N,N-dimethylformamide-κO)-manganese(II)-platinum(II)], C10H14MnN6O2Pt
  39. The crystal structure of aqua-chlorido-6,6′-((ethane-1,2-diylbis(azaneylylidene))bis(methaneylylidene))bis(2,4-dichlorophenolato-κ4N,N′,O,O′)manganese(III), C16H12Cl5MnN2O3
  40. Crystal structure of [di(µ2-cyanido)-dicyanido-bis(dimethyl sulfoxide-κO)- bis(2,2′-(ethane-1,2-diylbis(azanylylidenemethanylylidene))diphenolato-κ4,N,N′,O,O′)- dimanganese(III)-platinum(II)], C40H40Mn2N8O6PtS2
  41. The crystal structure of (azido)-κ1N-6,6′-((cyclohexane-1,2-diylbis(azanylylidene)) bis(methanylylidene))bis(3-bromophenolato-κ4N,N,O,O)-(methanol)-manganese(III)–methanol(1/1), C22H26Br2MnN5O4
  42. Crystal structure of 7-chloro-N-(4-iodobenzyl)-1,2,3,4-tetrahydroacridin-9-amine, C20H18ClIN2
  43. Crystal structure of catena-poly[(1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N′′′)-bis(μ2-thiocyanato-κ2N:S)-bis(thiocyanato-κS)-nickel(II)palladium(II)], C14H24N8NiPdS4
  44. Crystal structure of 3-chloro-4-(4-ethylpiperazin-1-yl)aniline monohydrate, C12H20ClN3O
  45. Crystal structure of the 2D coordination polymer poly[diaqua-bis(μ2-3- methoxyisonicotinato-κ2N:O)cobalt(II)] — dimethylformamide (1/1), C20H30CoN4O10
  46. Crystal structure of 4-[(5-chloro-2-hydroxybenzylidene)amino]-3-propyl-1H-1,2,4-triazole-5(4H)-thione, C12H13ClN4OS
  47. Crystal structure of N-(5-(2-(benzyl(1-(4-methoxyphenyl)propan-2-yl)amino)-1-hydroxyethyl)-2-(benzyloxy)phenyl)formamide, C33H36N2O4
  48. Crystal structure of 3-(methoxycarbonyl)-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid, C9H12O5
  49. The crystal structure of 1-((dimethylamino)(3-nitrophenyl)methyl)naphthalen-2-ol, C19H18N2O3
  50. Crystal structure of catena-poly[di(μ2-cyanido-κ2C:N)-dicyanido-tetrakis(dimethyl sulfoxide-κO)-manganese(II)-platinum(II)], C12H24MnN4O4PtS4
  51. Crystal structure of 4-amino-N-(2-pyrimidinyl)benzenesulfonamide–1,4-dioxane (1/1), C14H18N4O4S
  52. Crystal structure of bis{1-[(benzotriazol-1-yl)methyl]-1H-1,3-(2-methyl-imidazol)}di-chloridomercury(II), [Hg(C11H11N5)2Cl2], C22H22N10Cl2Hg
  53. Crystal structure of 2, 3-bis((4-methylbenzoyl)oxy) succinic acid–N, N-dimethylformamide (1/1), C23H25NO9
  54. Crystal structure of catena-poly[bis(4-(4-carboxyphenoxy)benzoato-κ1O)-μ2-(1,4-bis(1-imidazolyl)benzene-κ2N:N′)cobalt(II)], C40H28N4O10Co
  55. Crystal structure of 1H-imidazol-3-ium poly[aqua-(μ4-glutarato-κ6O,O′:O′:O′′,O′′′:O′′′)-(nitrato-κ2O,O′)strontium(II)], C8H13N3O8Sr
  56. Crystal structure of (R)-6-(benzo[b]thiophen-5-yl)-2-methyl-2,6-dihydrobenzo [5,6] silino[4,3,2-cd]indole, C23H17NSSi
  57. Crystal structure of catena-poly[bis(μ2-thiocyanato-κ2N:S)-(2-(5-methyl-1H-pyrazol-3-yl)pyridine-κ2N,N′)cadmium(II)]–dioxane (1/1), C15H17CdN5O2S2
  58. Crystal structure of poly[aqua-(μ2-1,4-bis(2′-carboxylatophenoxy)benzene-κ2O:O′)-(μ2-4,4′-bipyridione-κ2N:N′)cadmium(II)] monhydrate, C30H22CdN2O7⋅H2O
  59. Crystal structure of catena-poly[tetraaqua-(μ2-4,4′-bipyridine-k2N:N′)-bis(μ2-4′-methyl-[1,1′-biphenyl]-3,5-dicarboxylato-k4O,O′:O″,O′″)dicadmium(II)] dihydrate, C20H20NO7Cd
  60. Crystal structure of 1‐tert‐butyl‐3‐(2,6‐diisopropyl‐4‐phenoxyphenyl)‐2-methylisothiourea, C24H34N2OS
  61. Crystal structure of catena-poly[triaqua-(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2N:N′)-(4,4′-(1H-1,2,4-triazole-3,5-diyl)dibenzoato-κ1O)cobalt(II)] — N,N′-dimethylformamide (1/1), C28H34N8O8Co
  62. Crystal structure of tetraaqua-bis(1,4-di(1H-imidazol-1-yl)benzene-κ1N)manganese(II) 2,3-dihydroxyterephthalate, C32H32MnN8O10
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