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The structure of the title compound, C14H14N2O2, has been established. The plane formed by the atoms of the quinoxaline is almost perpendicular to the two allyl groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801001076/cf6031sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801001076/cf6031Isup2.hkl
Contains datablock I

CCDC reference: 159759

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.001 Å
  • R factor = 0.049
  • wR factor = 0.064
  • Data-to-parameter ratio = 11.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry




Comment top

La chimie des quinoxalines a connu une attention particulière ces dernières décennies, inhérente à la mize en évidence des différentes applications, de plusieurs dérivés quinoxaliniques dans divers domaines. En effet, ils sont utilisés comme colorants pour la détection des métaux, stabilisateurs d'huile (Campaigne & Mclaughlin, 1983), et ils sont commercialisés comme antibiotiques (Ungermach, 1996), antiparasitaires (Ikeda et al., 1992; Romer et al., 1995; Sutherland et al., 1996) et anticonvulsiants (Loscher et al., 1999). Il nous a paru intéressant de poursuivre nos recherches dans ce domaine, en examinant la synthèse de nouveaux dérivés de la quinoxaline susceptibles de présenter des propriétés biologiques et pharmacologiques intéressantes. La méthode de synthèse que nous avons adoptée met en jeu l'action du chlorure d'allyle en excès sur la quinoxaline-2,3-dione dans le diméthyl formamide, en présence de deux équivalents de carbonate de potassium et de bromure de tétra n-butylammonium comme catalyseur. L'identification de (I) a été réalisée sur la base des données spectrales RMN 1H, 13C, masse et par diffraction X. Les douze atomes du groupement quinoxaline-2,3-dione forment un plan (d.c.m.: 0.0186 Å) et les deux bras allyliques, situés de part et d'autre de ce plan, sont presque perpendiculaires au plan quinoxaline: N1/C11/C12/C13 (d.c.m.: 0.0455 Å) est à 83.4 (4)° et N4/C16/C17/C18 (d.c.m.: 0.0498 Å) à 92.6 (4)°.

Experimental top

A 0,06 mole de la quinoxaline-2,3-dione dans 30 ml de diméthyl formamide, on ajoute 0,012 mole du bromure d'allyle, 0,012 mole de K2CO3 et 0,001 mole de bromure de tétra n-butylammonium. Le mélange est laissé sous agitation énergique pendant 24 h. Après filtration de la solution, le solvant est évaporé sous pression réduite, le résidu obtenu est chromatographié sur colonne de silice (éluant: hexane/acétate diéthyle: 95/5). Rendement: 70%; Point de fusion: 438–440 K.

Computing details top

Data collection: KappaCCD Reference Manual (Nonius, 1998); data reduction: DENZO and SCALEPAK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: maXus (Mackay et al., 1999); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: maXus.

Figures top
[Figure 1] Fig. 1. Perspective view of the molecule showing the labelling of the atoms with displacement ellipsoids at the 50% probability level.
(I) top
Crystal data top
C14H14N2O2F(000) = 512
Mr = 242.28Dx = 1.323 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.3000 (5) ÅCell parameters from 8419 reflections
b = 15.2215 (5) Åθ = 1–26.3°
c = 9.7195 (5) ŵ = 0.09 mm1
β = 117.883 (2)°T = 298 K
V = 1216.20 (10) Å3Prism, colourless
Z = 40.40 × 0.35 × 0.20 mm
Data collection top
KappaCCD
diffractometer
Rint = 0.040
Radiation source: fine-focus sealed tubeθmax = 26.3°
ϕ scanh = 011
2459 measured reflectionsk = 018
2352 independent reflectionsl = 1210
1939 reflections with I > 3σ(I)
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: geom, diff
R[F2 > 2σ(F2)] = 0.049H-atom parameters not refined
wR(F2) = 0.064Weighting scheme based on measured s.u.'s w = 1/(σ2(Fo2) + 0.03Fo2)
S = 1.17(Δ/σ)max = 0.022
1939 reflectionsΔρmax = 0.17 e Å3
163 parametersΔρmin = 0.14 e Å3
Primary atom site location: structure-invariant direct methods
Crystal data top
C14H14N2O2V = 1216.20 (10) Å3
Mr = 242.28Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.3000 (5) ŵ = 0.09 mm1
b = 15.2215 (5) ÅT = 298 K
c = 9.7195 (5) Å0.40 × 0.35 × 0.20 mm
β = 117.883 (2)°
Data collection top
KappaCCD
diffractometer
1939 reflections with I > 3σ(I)
2459 measured reflectionsRint = 0.040
2352 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.049163 parameters
wR(F2) = 0.064H-atom parameters not refined
S = 1.17Δρmax = 0.17 e Å3
1939 reflectionsΔρmin = 0.14 e Å3
Special details top

Geometry. All standard uncertainties (except dihedral angles between l.s. planes) are estimated using the full covariance matrix. The standard uncertainties in cell dimensions are are used in calculating the standard uncertainties of bond distances, angles and torsion angles. Angles between l.s. planes have standard uncertainties calculated from atomic positional standard uncertainties; the errors in cell dimensions are not used in this case.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O140.85696 (5)0.04852 (2)0.32547 (5)0.0824 (2)
O151.07376 (5)0.02847 (2)0.25103 (5)0.0850 (2)
N10.76808 (4)0.08507 (2)0.35808 (4)0.04602 (19)
N40.98845 (4)0.16385 (2)0.27648 (4)0.04288 (18)
C20.86428 (6)0.03162 (3)0.32342 (6)0.0529 (2)
C30.98396 (5)0.07448 (3)0.28060 (5)0.0524 (2)
C50.88959 (4)0.21695 (3)0.31653 (4)0.0359 (2)
C60.90080 (5)0.30850 (3)0.31747 (5)0.0438 (2)
C70.80387 (5)0.35919 (3)0.35761 (5)0.0497 (2)
C80.69490 (5)0.31999 (3)0.39716 (6)0.0514 (2)
C90.68261 (5)0.23001 (3)0.39763 (5)0.0459 (2)
C100.77982 (4)0.17733 (3)0.35785 (5)0.0372 (2)
C110.65263 (6)0.04392 (3)0.40239 (6)0.0624 (3)
C120.48081 (6)0.04530 (3)0.27624 (7)0.0668 (3)
C130.42997 (6)0.06273 (4)0.13123 (7)0.0715 (3)
C161.10207 (5)0.20509 (3)0.22986 (5)0.0543 (3)
C171.25717 (5)0.23463 (4)0.36380 (6)0.0620 (3)
C181.31233 (6)0.21249 (3)0.50775 (6)0.0621 (3)
H60.976940.335940.290220.05937*
H70.812640.422040.358280.06433*
H80.626490.355610.423950.06700*
H90.606940.203180.426180.06244*
H120.393970.032430.300290.08121*
H171.326560.274310.345380.07745*
H11A0.660650.074960.491690.07699*
H11B0.686900.015800.430540.07699*
H13A0.304530.062870.046860.08460*
H13B0.507380.082730.085850.08460*
H16A1.046170.254310.165120.07106*
H16B1.124850.162550.169700.07106*
H18A1.414010.234780.587010.07572*
H18B1.249310.172900.534980.07572*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O140.0844 (3)0.0340 (2)0.1007 (3)0.00440 (17)0.0398 (2)0.00202 (19)
O150.0732 (2)0.0648 (2)0.0980 (3)0.02095 (19)0.0480 (2)0.0114 (2)
N10.0412 (2)0.0330 (2)0.0504 (2)0.00009 (15)0.02017 (18)0.00457 (17)
N40.03480 (19)0.0449 (2)0.0391 (2)0.00347 (15)0.01812 (16)0.00089 (17)
C20.0495 (3)0.0359 (3)0.0544 (3)0.0048 (2)0.0169 (2)0.0004 (2)
C30.0438 (3)0.0483 (3)0.0485 (3)0.0111 (2)0.0156 (2)0.0053 (2)
C50.02982 (19)0.0360 (2)0.0321 (2)0.00357 (17)0.01241 (17)0.00178 (18)
C60.0378 (2)0.0385 (2)0.0428 (2)0.00016 (18)0.0175 (2)0.00514 (19)
C70.0460 (2)0.0328 (2)0.0543 (3)0.00359 (19)0.0202 (2)0.0036 (2)
C80.0432 (2)0.0422 (3)0.0557 (3)0.0066 (2)0.0240 (2)0.0028 (2)
C90.0361 (2)0.0436 (3)0.0480 (3)0.00037 (19)0.0225 (2)0.0006 (2)
C100.0329 (2)0.0313 (2)0.0357 (2)0.00095 (16)0.01253 (18)0.00276 (18)
C110.0643 (3)0.0409 (3)0.0661 (3)0.0065 (2)0.0344 (3)0.0107 (2)
C120.0567 (3)0.0499 (3)0.0783 (4)0.0185 (2)0.0375 (3)0.0059 (3)
C130.0572 (3)0.0640 (4)0.0724 (4)0.0123 (3)0.0257 (3)0.0011 (3)
C160.0399 (2)0.0699 (3)0.0438 (3)0.0043 (2)0.0236 (2)0.0030 (2)
C170.0385 (3)0.0781 (4)0.0566 (3)0.0035 (2)0.0233 (2)0.0047 (3)
C180.0496 (3)0.0644 (3)0.0526 (3)0.0010 (2)0.0149 (2)0.0017 (3)
Geometric parameters (Å, º) top
O14—C21.2225 (5)C5—C101.3967 (5)
O15—C31.2228 (5)C6—C71.3744 (6)
N1—C21.3630 (6)C7—C81.3767 (6)
N1—C101.4088 (5)C8—C91.3746 (6)
N1—C111.4706 (5)C9—C101.3916 (5)
N4—C31.3621 (6)C11—C121.4915 (7)
N4—C51.4089 (5)C12—C131.2873 (7)
N4—C161.4710 (5)C16—C171.4903 (6)
C2—C31.5069 (7)C17—C181.2895 (7)
C5—C61.3972 (5)
C2—N1—C10122.30 (4)N4—C5—C10119.40 (4)
C2—N1—C11118.14 (4)C6—C5—C10119.41 (4)
C10—N1—C11119.52 (4)C5—C6—C7120.33 (4)
C3—N4—C5122.14 (4)C6—C7—C8120.13 (4)
C3—N4—C16118.14 (4)C7—C8—C9120.41 (4)
C5—N4—C16119.72 (4)C8—C9—C10120.49 (4)
O14—C2—N1122.93 (5)N1—C10—C5119.90 (3)
O14—C2—C3119.37 (4)N1—C10—C9120.87 (4)
N1—C2—C3117.69 (4)C5—C10—C9119.23 (4)
O15—C3—N4122.10 (5)N1—C11—C12113.68 (4)
O15—C3—C2119.39 (5)C11—C12—C13127.34 (5)
N4—C3—C2118.51 (4)N4—C16—C17113.64 (4)
N4—C5—C6121.18 (4)C16—C17—C18126.89 (5)

Experimental details

Crystal data
Chemical formulaC14H14N2O2
Mr242.28
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)9.3000 (5), 15.2215 (5), 9.7195 (5)
β (°) 117.883 (2)
V3)1216.20 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.40 × 0.35 × 0.20
Data collection
DiffractometerKappaCCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 3σ(I)] reflections
2459, 2352, 1939
Rint0.040
(sin θ/λ)max1)0.623
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.064, 1.17
No. of reflections1939
No. of parameters163
No. of restraints?
H-atom treatmentH-atom parameters not refined
Δρmax, Δρmin (e Å3)0.17, 0.14

Computer programs: KappaCCD Reference Manual (Nonius, 1998), DENZO and SCALEPAK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), maXus (Mackay et al., 1999), ORTEPII (Johnson, 1976), maXus.

 

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