3-Methyl-1-(prop-2-en-1-yl)quinoxalin-2(1H)-one

Ramli, Y.; Slimani, R.; Zouihri, H.; Lazar, S.; Essassi, E.M.

doi:10.1107/S1600536810023640

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1767

doi:10.1107/S1600536810023640

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3-Methyl-1-(prop-2-en-1-yl)quinoxalin-2(1H)-one

Youssef Ramli,^a Rachid Slimani,^b Hafid Zouihri,^c Saïd Lazar ^b ^* and E. M. Essassi ^d

^aLaboratoire Nationale de Contrôle des Médicaments, Direction du Médicament et de la Pharmacie, BP 6206, 10000 Rabat, Morocco, ^bLaboratoire de Biochimie, Environnement et Agroalimentaire (URAC 36), Faculté des Sciences et Techniques Mohammedia, Université Hassan II Mohammedia-Casablana, BP 146, 20800 Mohammedia, Morocco, ^cLaboratoires de Diffraction des Rayons X, Division UATRS, Centre National pour la Recherche Scientifique et Technique, Rabat, Morocco, and ^dLaboratoire de Chimie Organique Hétérocyclique, Université Mohammed, V-Agdal, BP 1014, Rabat, Morocco
^*Correspondence e-mail: lazar_said@yahoo.fr

(Received 11 June 2010; accepted 18 June 2010; online 23 June 2010)

In the molecule of the title compound, C₁₂H₁₂N₂O, the quinoxaline ring is planar with an r.m.s. deviation of 0.007 (15) Å. The dihedral angle between the quinoxaline and propenyl planes is 82.1 (2)°. The crystal packing is stabilized by offset π–π stacking between the quinoxaline rings [centroid–centroid distance = 3.8832 (9) Å].

Related literature

For biological activity of quinoxaline derivatives, see: Kleim et al. (1995 ). For their antitumor, and antituberculous properties, see: Abasolo et al. (1987 ); Rodrigo et al. (2002 ). For the antifungal, herbicidal, antidyslipidemic and anti-oxidative activities of quinoxaline derivatives, see: Jampilek et al. (2005 ); Sashidhara et al. (2009 ); Watkins et al. (2009 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₂H₁₂N₂O
M_r = 200.24
Monoclinic, P 2₁ /c
a = 5.0722 (5) Å
b = 13.4707 (13) Å
c = 15.0507 (13) Å
β = 95.082 (5)°
V = 1024.31 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.32 × 0.31 × 0.13 mm

Data collection

Bruker X8 APEXII CCD area-detector diffractometer
11850 measured reflections
2546 independent reflections
1726 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.151
S = 1.08
2546 reflections
137 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ), ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536810023640/dn2579sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810023640/dn2579Isup2.hkl

checkCIF report

Comment top

Quinoxaline derivatives are a very important class of nitrogen-containing compounds and have been widely used in dyes, pharmaceuticals and electrical/photochemical materials. Quinoxaline ring moiety constitute part of the chemical structures of various antibiotics such as Echinomycin, Levomycin and Actinoleutin that are known to inhibit growth of gram positive bacteria and are active against various transplantable tumors.

Quinoxaline derivatives were found to exhibit antimicrobial [Kleim et al. 1995], antitumor [Abasolo et al. 1987], and antituberculous activity [Rodrigo et al.2002]. They, also, exhibit interesting antifungal, herbicidal, Antidyslipidemic and antioxidative activities of quinoxaline derivatives, see: (Jampilek et al. 2005, Sashidhara et al. 2009, Watkins et al. 2009).

The dihedral angle between the quinoxaline and propenyl planes is 82.1 (2) (Fig. 1). Bond lengths and angles in title molecule are normal (Allen et al., 1987). The crystal packing is stabilized by offset π-π stacking between the quinoxalin rings.

Related literature top

For biological activity of quinoxaline derivatives, see: Kleim et al. (1995). For their antitumor, and antituberculous properties, see: Abasolo et al. (1987); Rodrigo et al. (2002). For the antifungal, herbicidal, antidyslipidemic and anti-oxidative activities of quinoxaline derivatives, see: Jampilek et al. (2005); Sashidhara et al. (2009); Watkins et al. (2009). For bond-length data, see: Allen et al. (1987).

Experimental top

To a solution of 3-methylquinoxali-2(1H)-one (1 g) in 20 ml of dimethylformamide was added allylchloride (0.85 ml),K2CO3 (0.95 g) and catalytic amont of tetrabutylammonium bromide.The mixture was stirred at room temperature for 24 h.Then the solvent was remdove under reduce pressure,the residue was cristallized in ethanol to afford the product.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. : Molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. : Packing view of the crystal structure of the title compound.

3-Methyl-1-(prop-2-en-1-yl)quinoxalin-2(1H)-one top

Crystal data top

C₁₂H₁₂N₂O	F(000) = 424
M_r = 200.24	D_x = 1.298 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 1486 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.0722 (5) Å	Cell parameters from 2764 reflections
b = 13.4707 (13) Å	θ = 2.4–27.4°
c = 15.0507 (13) Å	µ = 0.09 mm⁻¹
β = 95.082 (5)°	T = 296 K
V = 1024.31 (17) Å³	Block, colourless
Z = 4	0.32 × 0.31 × 0.13 mm

Data collection top

Bruker X8 APEXII CCD area-detector diffractometer	1726 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.049
Graphite monochromator	θ_max = 28.3°, θ_min = 2.7°
ϕ and ω scans	h = −6→6
11850 measured reflections	k = 0→17
2546 independent reflections	l = 0→20

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0723P)² + 0.0888P] where P = (F_o² + 2F_c²)/3
2546 reflections	(Δ/σ)_max = 0.001
137 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₂H₁₂N₂O	V = 1024.31 (17) Å³
M_r = 200.24	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.0722 (5) Å	µ = 0.09 mm⁻¹
b = 13.4707 (13) Å	T = 296 K
c = 15.0507 (13) Å	0.32 × 0.31 × 0.13 mm
β = 95.082 (5)°

Data collection top

Bruker X8 APEXII CCD area-detector diffractometer	1726 reflections with I > 2σ(I)
11850 measured reflections	R_int = 0.049
2546 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.151	H-atom parameters constrained
S = 1.08	Δρ_max = 0.23 e Å⁻³
2546 reflections	Δρ_min = −0.17 e Å⁻³
137 parameters

Special details top

Experimental. The data collection nominally covered a sphere of reciprocal space, by a combination of seven sets of exposures; each set had a different ϕ angle for the crystal and each exposure covered 0.5° in ω and 30 s in time. The crystal-to-detector distance was 37.5 mm.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimatedusing the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL datawill be even larger.

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

	x	y	z	U_iso*/U_eq
O1	−0.3390 (2)	0.34712 (9)	0.06022 (9)	0.0657 (4)
N1	−0.0193 (2)	0.29591 (9)	0.16502 (8)	0.0408 (3)
N2	0.1311 (2)	0.49458 (9)	0.18738 (8)	0.0445 (3)
C1	0.2649 (3)	0.41959 (11)	0.23590 (9)	0.0408 (3)
C2	0.4769 (3)	0.44552 (13)	0.29645 (10)	0.0514 (4)
H2	0.5253	0.5119	0.3030	0.062*
C3	0.6150 (3)	0.37488 (15)	0.34638 (11)	0.0589 (5)
H3	0.7560	0.3931	0.3868	0.071*
C4	0.5434 (3)	0.27599 (15)	0.33625 (11)	0.0579 (5)
H4	0.6364	0.2278	0.3704	0.069*
C5	0.3375 (3)	0.24845 (13)	0.27651 (11)	0.0503 (4)
H5	0.2932	0.1817	0.2698	0.060*
C6	0.1937 (3)	0.31975 (11)	0.22568 (9)	0.0395 (3)
C7	−0.1541 (3)	0.36731 (11)	0.11482 (10)	0.0441 (4)
C8	−0.0643 (3)	0.47053 (11)	0.13088 (9)	0.0424 (4)
C9	−0.2158 (3)	0.54800 (12)	0.07845 (11)	0.0543 (4)
H9A	−0.3878	0.5548	0.0997	0.081*
H9B	−0.2343	0.5293	0.0167	0.081*
H9C	−0.1233	0.6101	0.0850	0.081*
C10	−0.1160 (3)	0.19385 (11)	0.15522 (11)	0.0483 (4)
H10A	−0.3032	0.1956	0.1355	0.058*
H10B	−0.0975	0.1621	0.2133	0.058*
C11	0.0207 (3)	0.13211 (13)	0.09201 (12)	0.0578 (5)
H11	−0.0243	0.0652	0.0896	0.069*
C12	0.1942 (4)	0.16040 (15)	0.04015 (13)	0.0669 (5)
H12A	0.2467	0.2265	0.0398	0.080*
H12B	0.2672	0.1147	0.0030	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0682 (8)	0.0524 (8)	0.0700 (8)	−0.0060 (6)	−0.0296 (7)	0.0027 (6)
N1	0.0443 (6)	0.0358 (7)	0.0413 (6)	−0.0016 (5)	−0.0024 (5)	0.0006 (5)
N2	0.0518 (7)	0.0402 (7)	0.0407 (6)	−0.0005 (5)	−0.0013 (5)	−0.0018 (5)
C1	0.0435 (7)	0.0433 (9)	0.0353 (7)	0.0004 (6)	0.0020 (6)	−0.0008 (6)
C2	0.0527 (9)	0.0550 (10)	0.0452 (8)	−0.0061 (7)	−0.0038 (7)	−0.0033 (7)
C3	0.0527 (9)	0.0755 (13)	0.0458 (9)	−0.0016 (8)	−0.0107 (7)	−0.0006 (8)
C4	0.0592 (10)	0.0648 (12)	0.0474 (9)	0.0098 (8)	−0.0080 (7)	0.0103 (8)
C5	0.0568 (9)	0.0471 (9)	0.0460 (8)	0.0046 (7)	−0.0014 (7)	0.0053 (7)
C6	0.0416 (7)	0.0415 (9)	0.0352 (7)	0.0006 (6)	0.0026 (6)	−0.0005 (6)
C7	0.0464 (8)	0.0423 (9)	0.0420 (8)	0.0003 (6)	−0.0045 (6)	−0.0002 (6)
C8	0.0487 (8)	0.0398 (8)	0.0380 (7)	0.0027 (6)	0.0003 (6)	−0.0005 (6)
C9	0.0653 (10)	0.0439 (9)	0.0518 (9)	0.0069 (7)	−0.0059 (8)	0.0015 (7)
C10	0.0488 (8)	0.0387 (9)	0.0560 (9)	−0.0052 (6)	−0.0032 (7)	0.0022 (7)
C11	0.0625 (10)	0.0455 (10)	0.0633 (10)	−0.0042 (8)	−0.0060 (9)	−0.0077 (8)
C12	0.0696 (11)	0.0701 (13)	0.0602 (11)	−0.0030 (9)	0.0008 (9)	−0.0162 (9)

Geometric parameters (Å, º) top

O1—C7	1.2215 (18)	C5—C6	1.393 (2)
N1—C7	1.3683 (19)	C5—H5	0.9300
N1—C6	1.3889 (18)	C7—C8	1.476 (2)
N1—C10	1.4629 (19)	C8—C9	1.482 (2)
N2—C8	1.2887 (18)	C9—H9A	0.9600
N2—C1	1.3881 (19)	C9—H9B	0.9600
C1—C2	1.391 (2)	C9—H9C	0.9600
C1—C6	1.397 (2)	C10—C11	1.481 (2)
C2—C3	1.367 (2)	C10—H10A	0.9700
C2—H2	0.9300	C10—H10B	0.9700
C3—C4	1.386 (3)	C11—C12	1.285 (3)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.368 (2)	C12—H12A	0.9300
C4—H4	0.9300	C12—H12B	0.9300

C7—N1—C6	121.48 (13)	O1—C7—C8	121.81 (14)
C7—N1—C10	117.26 (12)	N1—C7—C8	116.08 (13)
C6—N1—C10	121.20 (12)	N2—C8—C7	123.57 (13)
C8—N2—C1	118.41 (13)	N2—C8—C9	120.44 (14)
N2—C1—C2	118.39 (14)	C7—C8—C9	115.99 (13)
N2—C1—C6	122.20 (13)	C8—C9—H9A	109.5
C2—C1—C6	119.41 (14)	C8—C9—H9B	109.5
C3—C2—C1	120.95 (16)	H9A—C9—H9B	109.5
C3—C2—H2	119.5	C8—C9—H9C	109.5
C1—C2—H2	119.5	H9A—C9—H9C	109.5
C2—C3—C4	119.49 (15)	H9B—C9—H9C	109.5
C2—C3—H3	120.3	N1—C10—C11	114.87 (13)
C4—C3—H3	120.3	N1—C10—H10A	108.6
C5—C4—C3	120.70 (16)	C11—C10—H10A	108.6
C5—C4—H4	119.7	N1—C10—H10B	108.6
C3—C4—H4	119.7	C11—C10—H10B	108.6
C4—C5—C6	120.41 (16)	H10A—C10—H10B	107.5
C4—C5—H5	119.8	C12—C11—C10	127.48 (17)
C6—C5—H5	119.8	C12—C11—H11	116.3
N1—C6—C5	122.71 (14)	C10—C11—H11	116.3
N1—C6—C1	118.25 (13)	C11—C12—H12A	120.0
C5—C6—C1	119.04 (14)	C11—C12—H12B	120.0
O1—C7—N1	122.11 (14)	H12A—C12—H12B	120.0

C12—C11—C10—N1	−6.7 (3)

Experimental details

Crystal data
Chemical formula	C₁₂H₁₂N₂O
M_r	200.24
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	5.0722 (5), 13.4707 (13), 15.0507 (13)
β (°)	95.082 (5)
V (Å³)	1024.31 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.32 × 0.31 × 0.13

Data collection
Diffractometer	Bruker X8 APEXII CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11850, 2546, 1726
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.151, 1.08
No. of reflections	2546
No. of parameters	137
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.17

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and publCIF (Westrip, 2010).

Offset π–π stacking between the quinoxaline rings. top

Cg1 is the centroid of ring N1,C6,C1,N2,C8,C7 and Cg2 the centroid of ring C1–C6.

	Centroid-to-centroid(Å)	plane-to-plane(Å)	offset(°)
Cg1–Cg2ⁱ	3.8832 (9)	3.509	25.4

Symmetry code: (i) -1+x, y, z.

Acknowledgements

The authors thank the CNRST of Morocco for making this work possible.

References

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