Home Synthesis and crystal structure of (E)-1-benzyl-3-(4-methoxystyryl)quinoxalin-2(1H)-one, C24H20N2O2
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Synthesis and crystal structure of (E)-1-benzyl-3-(4-methoxystyryl)quinoxalin-2(1H)-one, C24H20N2O2

  • Mohcine Missioui , El Mokhtar Essassi , Joel T. Mague and Youssef Ramli ORCID logo EMAIL logo
Published/Copyright: July 15, 2020

Abstract

C24H20N2O2, monoclinic, P21/c (no. 14), a = 11.1713(3) Å, b = 17.7718(5) Å, c = 10.9852(3) Å, β = 118.990(1)°, V = 1907.67(9) Å3, Z = 4, Rgt(F) = 0.0538, wRref(F2) = 0.1582, T = 296(2) K.

CCDC no.: 2006147

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:Yellow block
Size:0.37 × 0.36 × 0.28 mm
Wavelength:Cu Kα radiation (1.54178 Å)
μ:0.66 mm−1
Diffractometer, scan mode:Bruker D8 VENTURE PHOTON 100 CMOS, ω
θmax, completeness:72.5°, 99%
N(hkl)measured, N(hkl)unique, Rint:14266, 3708, 0.032
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3032
N(param)refined:255
Programs:Bruker [1], [2], SHELX [3], [4], Diamond [5]
Table 2:

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

AtomxyzUiso*/Ueq
O10.42090(14)0.30337(7)0.50175(14)0.0800(4)
O20.11095(17)0.34160(10)−0.38584(15)0.0973(5)
N10.42507(12)0.39399(7)0.64889(13)0.0583(3)
N20.31361(13)0.49376(7)0.42404(13)0.0612(3)
C10.34999(14)0.51788(9)0.55669(16)0.0574(4)
C20.32838(18)0.59338(10)0.57641(19)0.0692(4)
H20.2901020.6257480.5003940.083*
C30.3627(2)0.62020(11)0.7056(2)0.0802(5)
H30.3462270.6702410.7174640.096*
C40.4219(3)0.57247(12)0.8182(2)0.0878(6)
H40.4468930.5910290.9065160.105*
C50.4448(2)0.49811(11)0.80297(19)0.0776(5)
H50.4855060.4669160.8805590.093*
C60.40724(14)0.46935(9)0.67173(16)0.0575(4)
C70.39769(15)0.36851(9)0.52022(17)0.0603(4)
C80.33550(15)0.42407(9)0.40464(16)0.0584(4)
C90.46967(16)0.33806(9)0.76112(17)0.0644(4)
H9A0.4352640.2891230.7198400.077*
H9B0.4283600.3504050.8185300.077*
C100.62167(15)0.33245(8)0.85298(16)0.0559(4)
C110.67210(19)0.29902(9)0.98287(17)0.0675(4)
H110.6118750.2826581.0131570.081*
C120.8114(2)0.28995(11)1.0673(2)0.0831(6)
H120.8445620.2681321.1547430.100*
C130.9013(2)0.31302(12)1.0228(2)0.0866(6)
H130.9949630.3066241.0796770.104*
C140.85219(19)0.34547(12)0.8941(2)0.0808(5)
H140.9127000.3607490.8634010.097*
C150.71331(17)0.35553(10)0.80997(18)0.0676(4)
H150.6809930.3781080.7232920.081*
C160.29872(16)0.39615(10)0.26666(17)0.0648(4)
H160.3221490.3468680.2587840.078*
C170.23374(17)0.43660(10)0.15108(18)0.0670(4)
H170.2084700.4851620.1607320.080*
C180.19795(16)0.41265(10)0.01056(17)0.0656(4)
C190.21993(19)0.33988(11)−0.02119(19)0.0744(5)
H190.2580750.3045930.0501110.089*
C200.1878(2)0.31831(12)−0.15244(19)0.0786(5)
H200.2030890.268950−0.1695080.094*
C210.13372(18)0.36854(12)−0.25801(19)0.0750(5)
C220.1077(2)0.44130(13)−0.2344(2)0.0891(6)
H220.0688150.475568−0.3073830.107*
C230.1407(2)0.46317(12)−0.0987(2)0.0847(5)
H230.1238310.512328−0.0821500.102*
C240.0463(2)0.38768(18)−0.5028(2)0.1077(8)
H24A0.1027230.430717−0.4914220.162*
H24B−0.0402880.404026−0.5137630.162*
H24C0.0318880.360020−0.5839030.162*

Source of material

To a solution of 3-methylquinoxalin-2(1H)-one (3.59 mmol) in N,N-dimethylformamide (20 mL) was added potassium carbonate (5.38 mmol) and the mixture was stirred at 80 °C for 1 h. After cooling benzylchloride (5.38 mmol) and a catalytic amount of tetrabutylammonium bromide was added and stirring was continued at room temperature for 24 h. After completion of the reaction (monitored by TLC), the solution was concentrated and the residue was purified by column chromatography on silica gel using a hexane/ethyl acetate mixture (7/3, v/v) as eluent. A portion of the product was dissolved in hot ethanol, the solution was filtered and the filtrate was left undisturbed for 10 days to form clear, colorless block crystals.

Experimental details

Hydrogen atoms attached to carbon were placed in calculated positions (C—H = 0.95 − 0.99 Å) and included as riding contributions with isotropic displacement parameters 1.2 − 1.5 times those of the attached atoms. A Hirshfeld Test Diff for C21—C22 indicated 7.5 s.u. This may be the result of some minor disorder at this point but it was not enough to model effectively.

Comment

Quinoxaline and its derivatives have received considerable attention due to their biological and industrial properties [6], [7]. These molecules exhibit a wide range of pharmacological applications and are potentially useful in medicinal chemistry research and have therapeutic applications because of their anticancer [8], antimicrobial [9], [10], [11], anti-inflammatory [12], antihistaminic [13] and antidiabetic activities [14]. As a continuation of our research on the synthesis of quinoxaline derivatives [15], [16], [17], [18], [19], [20], [21] we report the molecular and crystal structures of the title compound. For directly related structures, see: [22], [23].

The asymmetric unit consists of one molecule of (E)-1-benzyl-3-(4-methoxystyryl)quinoxalin-2(1H)-one. The quinoxaline moiety is not exactly planar as indicated by the dihedral angle of 1.64(5)° between its constituent planes. The C10⋯C15 and C18⋯C23 benzene rings are inclined to the mean plane of the heterocyclic ring by 82.78(6) and 2.00(6)°, respectively. The latter indicates that the styryl moiety is nearly coplanar with the quinoxaline unit while the C6—N1—C9—C10 torsion angle of −85.40(17)° indicates the benzyl substituent to be oriented well out of the above plane (see the Figure). All bond distances and interbond angles appear as expected for the given formulation. In the crystal, chains of molecules extending along the c-axis direction are formed by C11—H11⋯O1 and C20—H20⋯O1 hydrogen bonds reinforced by C24—H24A⋯Cg1 interactions. The chains are linked along the a-axis direction by C14—H14⋯Cg4 interactions to form layers parallel to the ac plane. The layers pack with inversion-related C1⋯C6 rings appearing to ovelap but the centroid⋯centroid distance of 3.8871(10) Å and the slippage of 1.734 Å suggest that this is more to minimize void space rather than any significant π-stacking interaction.

References

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Received: 2020-06-18
Accepted: 2020-07-08
Published Online: 2020-07-15
Published in Print: 2020-10-27

©2020 Mohcine Missioui 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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  52. Crystal structure of (μ2-1,1′-bis(diphenylphosphino)butane-κ2P,P′)-bis[(Z)-N-(3-fluorophenyl)-O-methylthiocarbamato-κS]-di-gold(I), C44H42Au2F2N2O2P2S2
  53. Crystal structure of (μ2-1,1′-bis(diphenylphosphino)hexane-κ2P,P′)-bis[(Z)-N-(3-fluorophenyl)-O-methylthiocarbamato-κS]digold(I), C46H46Au2F2N2O2P2S2
  54. Crystal structure of tetrakis (N-(2-hydroxyethyl)-N-isopropylcarbamodithioato-κS,S′)-(μ2(2-(pyridin-4-yl)vinyl)pyridine-κN,N′)dicadmium(II), C36H58Cd2N6O4S8
  55. Crystal structure of 4-(2-(benzo[b]thiophen-2-yl)-3,3,4,4,5,5-hexafluorocyclopent-1-en-1-yl)-1,5-dimethyl-1H-pyrrole-2-carbonitrile, C20H12F6N2S
  56. Crystal structure of bis(octahydrocyclopenta[c]pyrrolium)pentachlorobismuthate(III), (C7NH14)2BiCl5
  57. The crystal structure of diaqua-tris(nitrato-κ2O,O′)-bis(4,4,5,5-tetramethyl-2-(p-pyridyl)imidazoline-1-oxyl 3-oxide-κN)samarium(III), C24H36N9O15Sm
  58. Synthesis and crystal structure of methyl 2-(2-((tert-butoxycarbonyl)amino)phenyl)-2-(4-oxo-4H-chromen-3-yl)acetate, C23H23NO6
  59. Crystal structure of O-hexyl benzoylcarbamothioate, C14H19NO2S
  60. Crystal structure of chlorido-(O-methyl phenylcarbamothioamide-κS)-bis(triphenylphosphane-κP)silver(I), C44H39AgClNOP2S
  61. Crystal structure of chlorido-(O-ethyl phenylcarbamothioamide-κS)-bis(triphenylphosphane-κP)-silver(I), C45H41AgClNOP2S
  62. Crystal structure of 4-[(2-methoxyphenyl)carbamoyl]butanoic acid, C12H15NO4
  63. Crystal structure of ethyl 4-methyl-2-oxo-5-phenyl-1,3,4-oxadiazinane-3-carboxylate, C13H16N2O4
  64. Crystal structure of catena-poly[diaqua(μ2-2-(hydroxymethyl)-1H-imidazole-4,5-dicarboxylato)cadmium(II)], C6H8CdN2O7
  65. Crystal structure of (1S)-N-(chloromethyl)-1-((4S,6aR,8aS, 8bR,9aR)-4-methoxy-6a,8a-dimethyl-1,3,4, 5,6,6a,6b,7,8,8a,9a,10,10a,10b-tetradecahydro-8bH-naphtho[2′,1′:4,5] indeno[1,2-b]oxiren-8b-yl)-N-methylethan-1-amine, C24H46ClNO5
  66. Crystal structure of 4-[(3,5-dichlorophenyl)carbamoyl]butanoic acid, C11H11Cl2NO3
  67. Crystal structure of (2Z)-2-amino-3-[(E)-[(2,4-dihydroxyphenyl)methylidene]-amino]but-2-enedinitrile, C11H8N4O2
  68. Crystal structure of 3-methyl-1-[(E)-(4-phenylbutan-2-ylidene)amino]thiourea, C12H17N3S
  69. Crystal structure of carbonyl{hydridotris[3-phenyl-5-methylpyrazol-1-yl]borato-κ3N,N′N′′}copper(I), C31H28BCuN6O
  70. Crystal structure of ethane-1,2-diylbis(diphenylphosphine oxide) – dihydrogenperoxide (1/2), C26H28O6P2
  71. Crystal structure of 2-(pyridin-2-ylamino)pyridinium chloride dibenzyldichlorostannane, [C10H10N3]Cl, C14H14Cl2Sn
  72. Crystal structure of 4-[(3-methoxyphenyl)carbamoyl]butanoic acid, C12H15NO4
  73. Crystal structure of dichlorido-bis(tri-4-tolylphosphane oxide-κO)-di(4-chlorophenyl-κC)tin(IV), C54H50Cl4O2P2Sn
  74. Crystal structure of dichloridodimethylbis(tri-4-tolylphosphane oxide-κO)-tin(IV), C44H48Cl2O2P2Sn
  75. Crystal structure of chlorido(2-methylquinolin-8-olato-κ2N,O)-bis(4-tolyl-κC)tin(IV), C24H22ClNOSn
  76. Crystal structure of (E)-dichloro(1-chloro-3-methoxyprop-1-en-2-yl)(4-methoxyphenyl)-λ4-tellane, C11H13Cl3O2Te
  77. Crystal structure of bis{N-methyl-N′-[3-(4-methoxyphenyl)-1-methylpropane-1-ylidene]carbamohydrazonothioato}zinc(II), C26H36N6O2S2Zn
  78. Crystal structure of (2-carboxy-4-(3-carboxy-5-carboxylatophenoxy)benzoato-κ2O,O′)bis(1,10-phenantroline-κ2N,N′)cobalt(II), C40H24N4O9Co
  79. The crystal structure of (3S,8R,10R,14R)-17-((2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyltetrahydrofuran-2-yl)-4,4,8,10,14-pentamethyl-12-oxohexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate, C32H52O5
  80. Crystal structure of (μ2-1,1′-bis(diphenylphosphino)ferrocene-κ2P,P′)-bis[(Z)N-(3-fluorophenyl)-O-methylthiocarbamato-S]digold(I) chloroform solvate, C50H42Au2F2FeN2O2P2S2, CHCl3
  81. Crystal structure of poly[bis(μ2-1,4-di(1H-imidazol-1-yl)benzene-κ2N:N′)-(μ2-tetraoxidomolybdato(VI)-κ2O:O′)cobalt(II)], C24H20N8O4MoCo
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