1,4-Diallylquinoxaline-2,3(1H,4H)-dione

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.

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

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S1. Comment

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)°.

S2. Experimental

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

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

Fig. 1. Perspective view of the molecule showing the labelling of the atoms with displacement ellipsoids at the 50% probability level.

(I)

Crystal data

C14H14N2O2	F(000) = 512
Mr = 242.28	Dx = 1.323 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.3000 (5) Å	Cell parameters from 8419 reflections
b = 15.2215 (5) Å	θ = 1–26.3°
c = 9.7195 (5) Å	µ = 0.09 mm^−1
β = 117.883 (2)°	T = 298 K
V = 1216.20 (10) Å^3	Prism, colourless
Z = 4	0.40 × 0.35 × 0.20 mm

Data collection

KappaCCD diffractometer	Rint = 0.040
Radiation source: fine-focus sealed tube	θmax = 26.3°
ϕ scan	h = 0→11
2459 measured reflections	k = 0→18
2352 independent reflections	l = −12→10
1939 reflections with I > 3σ(I)

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: geom, diff
R[F^2 > 2σ(F^2)] = 0.049	H-atom parameters not refined
wR(F^2) = 0.064	Weighting scheme based on measured s.u.'s w = 1/(σ^2(Fo^2) + 0.03Fo^2)
S = 1.17	(Δ/σ)max = 0.022
1939 reflections	Δρmax = 0.17 e Å^−3
163 parameters	Δρmin = −0.14 e Å^−3
Primary atom site location: structure-invariant direct methods

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O14	0.85696 (5)	−0.04852 (2)	0.32547 (5)	0.0824 (2)
O15	1.07376 (5)	0.02847 (2)	0.25103 (5)	0.0850 (2)
N1	0.76808 (4)	0.08507 (2)	0.35808 (4)	0.04602 (19)
N4	0.98845 (4)	0.16385 (2)	0.27648 (4)	0.04288 (18)
C2	0.86428 (6)	0.03162 (3)	0.32342 (6)	0.0529 (2)
C3	0.98396 (5)	0.07448 (3)	0.28060 (5)	0.0524 (2)
C5	0.88959 (4)	0.21695 (3)	0.31653 (4)	0.0359 (2)
C6	0.90080 (5)	0.30850 (3)	0.31747 (5)	0.0438 (2)
C7	0.80387 (5)	0.35919 (3)	0.35761 (5)	0.0497 (2)
C8	0.69490 (5)	0.31999 (3)	0.39716 (6)	0.0514 (2)
C9	0.68261 (5)	0.23001 (3)	0.39763 (5)	0.0459 (2)
C10	0.77982 (4)	0.17733 (3)	0.35785 (5)	0.0372 (2)
C11	0.65263 (6)	0.04392 (3)	0.40239 (6)	0.0624 (3)
C12	0.48081 (6)	0.04530 (3)	0.27624 (7)	0.0668 (3)
C13	0.42997 (6)	0.06273 (4)	0.13123 (7)	0.0715 (3)
C16	1.10207 (5)	0.20509 (3)	0.22986 (5)	0.0543 (3)
C17	1.25717 (5)	0.23463 (4)	0.36380 (6)	0.0620 (3)
C18	1.31233 (6)	0.21249 (3)	0.50775 (6)	0.0621 (3)
H6	0.97694	0.33594	0.29022	0.05937*
H7	0.81264	0.42204	0.35828	0.06433*
H8	0.62649	0.35561	0.42395	0.06700*
H9	0.60694	0.20318	0.42618	0.06244*
H12	0.39397	0.03243	0.30029	0.08121*
H17	1.32656	0.27431	0.34538	0.07745*
H11A	0.66065	0.07496	0.49169	0.07699*
H11B	0.68690	−0.01580	0.43054	0.07699*
H13A	0.30453	0.06287	0.04686	0.08460*
H13B	0.50738	0.08273	0.08585	0.08460*
H16A	1.04617	0.25431	0.16512	0.07106*
H16B	1.12485	0.16255	0.16970	0.07106*
H18A	1.41401	0.23478	0.58701	0.07572*
H18B	1.24931	0.17290	0.53498	0.07572*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O14	0.0844 (3)	0.0340 (2)	0.1007 (3)	0.00440 (17)	0.0398 (2)	−0.00202 (19)
O15	0.0732 (2)	0.0648 (2)	0.0980 (3)	0.02095 (19)	0.0480 (2)	−0.0114 (2)
N1	0.0412 (2)	0.0330 (2)	0.0504 (2)	−0.00009 (15)	0.02017 (18)	0.00457 (17)
N4	0.03480 (19)	0.0449 (2)	0.0391 (2)	0.00347 (15)	0.01812 (16)	−0.00089 (17)
C2	0.0495 (3)	0.0359 (3)	0.0544 (3)	0.0048 (2)	0.0169 (2)	−0.0004 (2)
C3	0.0438 (3)	0.0483 (3)	0.0485 (3)	0.0111 (2)	0.0156 (2)	−0.0053 (2)
C5	0.02982 (19)	0.0360 (2)	0.0321 (2)	0.00357 (17)	0.01241 (17)	0.00178 (18)
C6	0.0378 (2)	0.0385 (2)	0.0428 (2)	−0.00016 (18)	0.0175 (2)	0.00514 (19)
C7	0.0460 (2)	0.0328 (2)	0.0543 (3)	0.00359 (19)	0.0202 (2)	0.0036 (2)
C8	0.0432 (2)	0.0422 (3)	0.0557 (3)	0.0066 (2)	0.0240 (2)	−0.0028 (2)
C9	0.0361 (2)	0.0436 (3)	0.0480 (3)	−0.00037 (19)	0.0225 (2)	0.0006 (2)
C10	0.0329 (2)	0.0313 (2)	0.0357 (2)	0.00095 (16)	0.01253 (18)	0.00276 (18)
C11	0.0643 (3)	0.0409 (3)	0.0661 (3)	−0.0065 (2)	0.0344 (3)	0.0107 (2)
C12	0.0567 (3)	0.0499 (3)	0.0783 (4)	−0.0185 (2)	0.0375 (3)	−0.0059 (3)
C13	0.0572 (3)	0.0640 (4)	0.0724 (4)	−0.0123 (3)	0.0257 (3)	−0.0011 (3)
C16	0.0399 (2)	0.0699 (3)	0.0438 (3)	0.0043 (2)	0.0236 (2)	0.0030 (2)
C17	0.0385 (3)	0.0781 (4)	0.0566 (3)	−0.0035 (2)	0.0233 (2)	0.0047 (3)
C18	0.0496 (3)	0.0644 (3)	0.0526 (3)	−0.0010 (2)	0.0149 (2)	−0.0017 (3)

Geometric parameters (Å, º)

O14—C2	1.2225 (5)	C5—C10	1.3967 (5)
O15—C3	1.2228 (5)	C6—C7	1.3744 (6)
N1—C2	1.3630 (6)	C7—C8	1.3767 (6)
N1—C10	1.4088 (5)	C8—C9	1.3746 (6)
N1—C11	1.4706 (5)	C9—C10	1.3916 (5)
N4—C3	1.3621 (6)	C11—C12	1.4915 (7)
N4—C5	1.4089 (5)	C12—C13	1.2873 (7)
N4—C16	1.4710 (5)	C16—C17	1.4903 (6)
C2—C3	1.5069 (7)	C17—C18	1.2895 (7)
C5—C6	1.3972 (5)
C2—N1—C10	122.30 (4)	N4—C5—C10	119.40 (4)
C2—N1—C11	118.14 (4)	C6—C5—C10	119.41 (4)
C10—N1—C11	119.52 (4)	C5—C6—C7	120.33 (4)
C3—N4—C5	122.14 (4)	C6—C7—C8	120.13 (4)
C3—N4—C16	118.14 (4)	C7—C8—C9	120.41 (4)
C5—N4—C16	119.72 (4)	C8—C9—C10	120.49 (4)
O14—C2—N1	122.93 (5)	N1—C10—C5	119.90 (3)
O14—C2—C3	119.37 (4)	N1—C10—C9	120.87 (4)
N1—C2—C3	117.69 (4)	C5—C10—C9	119.23 (4)
O15—C3—N4	122.10 (5)	N1—C11—C12	113.68 (4)
O15—C3—C2	119.39 (5)	C11—C12—C13	127.34 (5)
N4—C3—C2	118.51 (4)	N4—C16—C17	113.64 (4)
N4—C5—C6	121.18 (4)	C16—C17—C18	126.89 (5)