3-[2-(3-Methyl-2-oxo-1,2-dihydro­quinoxalin-1-yl)eth­yl]oxazolidin-2-one

Caleb, A.A.; Bouhfid, R.; Essassi, E.M.; El Ammari, L.

doi:10.1107/S1600536809028736

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 8| August 2009| Pages o2024-o2025

doi:10.1107/S1600536809028736

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3-[2-(3-Methyl-2-oxo-1,2-dihydroquinoxalin-1-yl)ethyl]oxazolidin-2-one

Ahoya Anothane Caleb,^a Rachid Bouhfid,^a El Mokhtar Essassi ^a and Lahcen El Ammari ^b ^*

^aLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences, Pharmacochimie, Av Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V-Agdal, Rabat, Morocco, and ^bLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
^*Correspondence e-mail: l_elammari@fsr.ac.ma

(Received 29 June 2009; accepted 20 July 2009; online 29 July 2009)

The title heterocyclic compound, C₁₄H₁₅N₃O₃, is a new synthetic molecule containing oxazolidine and quinoxaline rings. It is built up from two fused six-membered rings linked to a five-membered oxazolidin-2-one ring by a C₂ chain. Both ring systems are essentially planar [maximum deviation = 0.894 (3) Å, r.m.s. deviation = 0.0043 Å]. The structure is held together by van der Waals forces [electrostatic interactions between dipoles, O⋯C = 3.002 (2) Å] between molecules and by weak π–π stacking between symmetry-related molecules, with an interplanar distance of 3.579 Å and a centroid–centroid distance of 3.800 (1) Å. Intermolecular C—H⋯O hydrogen bonds are also observed in the crystal structure.

Related literature

For the biological activity of 3–2(-(3-methyl-2-oxoquinoxalin-1(2H)-yl) ethyl)oxazolidin-2-one, see: Ferfra (2001 ); Habib & El-hawash (1997 ); Romer et al. (1995 ). For pharmaceutical agrochemicals, see: Badran et al. (2003 ); Madhusudhan et al. (2004 ); Soad et al. (2006 ); Sriharsha & Shashikanth (2006 ); Sarro et al. (2002 ). For a related structure, see: Doubia et al. (2007 ).

Experimental

Crystal data

C₁₄H₁₅N₃O₃
M_r = 273.29
Monoclinic, C 2/c
a = 12.280 (3) Å
b = 10.736 (3) Å
c = 20.406 (4) Å
β = 102.32 (1)°
V = 2628.3 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.28 × 0.17 × 0.12 mm

Data collection

Bruker X8 APEXII CCD area-detector diffractometer
Absorption correction: none
21237 measured reflections
4108 independent reflections
2727 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.157
S = 1.04
4108 reflections
204 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H5⋯O3ⁱ	0.98 (2)	2.54 (2)	3.462 (2)	157 (2)
C10—H10A⋯O3ⁱ	0.97	2.43	3.348 (2)	157
Symmetry code: (i) $[-x, y, -z+{\script{1\over 2}}]$ .

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: SHELXS97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809028736/fj2233sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809028736/fj2233Isup2.hkl

checkCIF report

Comment top

The heterocyclic compounds to 5 or 6 Chains occupying a capital in fields as varied,quinoxalines pharmacy (Madhusudhan et al. 2004 and Sarro et al.2002) in agrochemicals (Romer et al. 1995, Habib et al. 1997) biology (Ferfra 2001)etc. The quinoxalines and the oxazolidines are subjets of numerous articles in describing the synthesis of new derivatives presentery antibacterial properties (Badran et al. 2003, Sriharsha et al. 2006) and anti tumor (Soad et al. 2006). We describe here the synthesis of compound 3 to side of the compound 2 per share on the dichlorodiéthylmine quinoxaline-2-one fusion as show in the chemical structural diagram (Fig.1).

The 3–2(-(3-methyl-2-oxoquinoxalin-1(2H)-yl)ethyl)oxazolidin-2-one (I) molecule structure is built up from two fused six-membered rings linked to a five-membered ring (oxazolidin-2-one) by an ethylic groupe. The both rings are essentially planar and forms a dihedral angle of 20.46 (6)° with the oxazolidin-2-one ring. The molecular structure of (I) is shown in Fig.2. The geometric parameters (bond lenghths and angles) are very similar to those observed in previously reported structures (Doubia et al. 2007).

An intermolecular C—H···O hydrogen bond is observed in the cristal structure as shown in the partial plot of the structure (Fig.3). Furthermore, the structure is stabilized by Van der Waals forces and together by weak slipped π-π stzcking between symmetry related molecules (C to C ring) with interplanar distance of 3.579 Å and centroid to centroid vector of 3.800 (1) Å.

Related literature top

For the biological activity of 3–2(-(3-methyl-2-oxoquinoxalin-1(2H)-yl) ethyl)oxazolidin-2-one, see: Ferfra (2001); Habib & El-hawash (1997); Romer et al. (1995). For pharmacy agrochemicals, see: Badran et al. (2003); Madhusudhan et al. (2004); Soad et al. (2006); Sriharsha & Shashikanth (2006); Sarro et al. (2002). For a related structure, see: Doubia et al. (2007).

Experimental top

It reacted 0.0125 moles of quinoxaline-2-one with 2.66 moles of dichlorodiéthylamine in 40 ml dimethyl formamide in the presence of 2.87 moles of K₂CO₃ and a few milligrams of BTBA. The mixture was brought to reflux in a bath of sand magnetic stirring for 6 h. After vacuum concentration, the separation of compounds was done by column chromatography eluant 4 / 6(hexane - ethyl acetate). Recrystallization occurred in the same eluent. This compound was obtained in 60% and his melting point is 175°C.

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: SHELXS97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. : Schematic of the chemical reaction leading to the title compound.
	Fig. 2. : 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 small circles.
	Fig. 3. : Partial packing view showing the C—H···O interactions (dashed lines).

3-[2-(3-Methyl-2-oxo-1,2-dihydroquinoxalin-1-yl)ethyl]oxazolidin-2-one top

Crystal data top

C₁₄H₁₅N₃O₃	F(000) = 1152
M_r = 273.29	D_x = 1.381 Mg m⁻³
Monoclinic, C2/c	Melting point: 448 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 12.280 (3) Å	Cell parameters from 21279 reflections
b = 10.736 (3) Å	θ = 2.6–30.9°
c = 20.406 (4) Å	µ = 0.10 mm⁻¹
β = 102.32 (1)°	T = 298 K
V = 2628.3 (11) Å³	Prism, colourless
Z = 8	0.28 × 0.17 × 0.12 mm

Data collection top

Bruker X8 APEXII CCD area-detector diffractometer	R_int = 0.033
Graphite monochromator	θ_max = 30.9°, θ_min = 2.6°
ϕ and ω scans	h = −17→17
21237 measured reflections	k = −15→15
4108 independent reflections	l = −26→29
2727 reflections with I > 2σ(I)

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.157	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.081P)² + 0.6684P] where P = (F_o² + 2F_c²)/3
4108 reflections	(Δ/σ)_max = 0.001
204 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₄H₁₅N₃O₃	V = 2628.3 (11) Å³
M_r = 273.29	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 12.280 (3) Å	µ = 0.10 mm⁻¹
b = 10.736 (3) Å	T = 298 K
c = 20.406 (4) Å	0.28 × 0.17 × 0.12 mm
β = 102.32 (1)°

Data collection top

Bruker X8 APEXII CCD area-detector diffractometer	2727 reflections with I > 2σ(I)
21237 measured reflections	R_int = 0.033
4108 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.157	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.29 e Å⁻³
4108 reflections	Δρ_min = −0.24 e Å⁻³
204 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 data will be even larger.

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

	x	y	z	U_iso*/U_eq
O1	0.11176 (11)	0.25753 (10)	0.54216 (6)	0.0630 (3)
O2	−0.13309 (10)	0.52714 (11)	0.26113 (5)	0.0598 (3)
O3	−0.13793 (10)	0.32026 (12)	0.24503 (6)	0.0662 (4)
N1	0.11384 (8)	0.15986 (10)	0.44405 (5)	0.0353 (2)
N2	0.16192 (10)	−0.06171 (10)	0.51654 (5)	0.0422 (3)
N3	−0.06491 (10)	0.40729 (10)	0.34753 (5)	0.0411 (3)
C1	0.12314 (11)	0.16145 (12)	0.51219 (6)	0.0387 (3)
C2	0.14895 (11)	0.04062 (12)	0.54680 (6)	0.0385 (3)
C3	0.15128 (10)	−0.05948 (12)	0.44748 (6)	0.0375 (3)
C4	0.16612 (13)	−0.17122 (14)	0.41519 (8)	0.0499 (4)
H4	0.1830 (15)	−0.2426 (16)	0.4433 (9)	0.064 (5)*
C5	0.15685 (13)	−0.17446 (16)	0.34713 (8)	0.0550 (4)
H5	0.0990 (14)	0.1222 (17)	0.3136 (8)	0.061 (5)*
C6	0.13209 (13)	−0.06520 (17)	0.31028 (8)	0.0524 (4)
H6	0.1300 (16)	−0.0693 (17)	0.2637 (11)	0.070 (6)*
C7	0.11673 (12)	0.04585 (15)	0.34045 (7)	0.0452 (3)
H7	0.1688 (16)	−0.2533 (17)	0.3259 (9)	0.064 (5)*
C8	0.12719 (10)	0.05051 (11)	0.40996 (6)	0.0341 (3)
C9	0.15977 (14)	0.04223 (15)	0.62100 (7)	0.0522 (4)
H9A	0.1775	−0.0400	0.6386	0.090*
H9B	0.0907	0.0690	0.6313	0.080*
H9C	0.2181	0.0987	0.6409	0.071 (6)*
C10	0.08780 (11)	0.27856 (12)	0.40844 (7)	0.0414 (3)
H10A	0.1230	0.2811	0.3702	0.053 (4)*
H10B	0.1171	0.3469	0.4381	0.047 (4)*
C11	−0.03761 (11)	0.29325 (13)	0.38470 (7)	0.0457 (3)
H11A	−0.0670	0.2231	0.3565	0.062 (5)*
H11B	−0.0723	0.2934	0.4232	0.069 (5)*
C12	−0.0550 (2)	0.52845 (15)	0.37655 (9)	0.0767 (6)
H12A	0.0221	0.5485	0.3962	0.090*
H12B	−0.0990	0.5361	0.4106	0.088*
C13	−0.10029 (16)	0.61022 (15)	0.31685 (9)	0.0625 (5)
H13A	−0.1637	0.6578	0.3242	0.081 (6)*
H13B	−0.0435	0.6676	0.3088	0.089 (7)*
C14	−0.11293 (11)	0.40817 (14)	0.28215 (7)	0.0429 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0931 (9)	0.0442 (6)	0.0505 (6)	0.0055 (6)	0.0130 (6)	−0.0100 (5)
O2	0.0708 (8)	0.0578 (7)	0.0454 (6)	0.0030 (5)	0.0000 (5)	0.0146 (5)
O3	0.0708 (8)	0.0718 (8)	0.0502 (6)	0.0112 (6)	0.0005 (5)	−0.0246 (6)
N1	0.0362 (5)	0.0336 (5)	0.0352 (5)	0.0005 (4)	0.0053 (4)	0.0056 (4)
N2	0.0472 (6)	0.0398 (6)	0.0353 (6)	−0.0030 (5)	−0.0010 (4)	0.0057 (4)
N3	0.0502 (7)	0.0332 (5)	0.0361 (6)	0.0048 (4)	0.0009 (5)	0.0017 (4)
C1	0.0397 (6)	0.0385 (6)	0.0363 (6)	−0.0027 (5)	0.0048 (5)	−0.0001 (5)
C2	0.0369 (6)	0.0425 (7)	0.0329 (6)	−0.0078 (5)	0.0005 (5)	0.0033 (5)
C3	0.0360 (6)	0.0370 (6)	0.0368 (6)	0.0008 (5)	0.0016 (5)	0.0028 (5)
C4	0.0525 (8)	0.0400 (7)	0.0528 (8)	0.0061 (6)	0.0013 (6)	−0.0023 (6)
C5	0.0513 (9)	0.0561 (9)	0.0557 (9)	0.0062 (7)	0.0075 (7)	−0.0160 (7)
C6	0.0475 (8)	0.0734 (11)	0.0373 (7)	0.0010 (7)	0.0110 (6)	−0.0072 (7)
C7	0.0434 (7)	0.0566 (8)	0.0360 (7)	0.0010 (6)	0.0091 (5)	0.0063 (6)
C8	0.0289 (6)	0.0381 (6)	0.0345 (6)	0.0004 (4)	0.0050 (4)	0.0036 (5)
C9	0.0595 (9)	0.0622 (9)	0.0319 (6)	−0.0168 (7)	0.0030 (6)	0.0035 (6)
C10	0.0425 (7)	0.0341 (6)	0.0463 (7)	−0.0008 (5)	0.0066 (5)	0.0103 (5)
C11	0.0426 (7)	0.0387 (7)	0.0533 (8)	0.0001 (5)	0.0044 (6)	0.0121 (6)
C12	0.1231 (18)	0.0380 (8)	0.0533 (10)	0.0076 (9)	−0.0162 (10)	−0.0075 (7)
C13	0.0684 (11)	0.0380 (8)	0.0734 (11)	0.0008 (7)	−0.0019 (8)	0.0086 (7)
C14	0.0399 (7)	0.0513 (8)	0.0368 (6)	0.0074 (6)	0.0067 (5)	−0.0016 (6)

Geometric parameters (Å, º) top

O1—C1	1.2223 (17)	C5—H7	0.976 (19)
O2—C14	1.3532 (18)	C6—C7	1.373 (2)
O2—C13	1.434 (2)	C6—H6	0.95 (2)
O3—C14	1.2080 (18)	C7—C8	1.3975 (18)
N1—C1	1.3708 (16)	C7—H5	0.984 (18)
N1—C8	1.3921 (16)	C9—H9A	0.9600
N1—C10	1.4680 (16)	C9—H9B	0.9600
N2—C2	1.2868 (18)	C9—H9C	0.9600
N2—C3	1.3874 (17)	C10—C11	1.5208 (19)
N3—C14	1.3387 (17)	C10—H10A	0.9700
N3—C12	1.4237 (19)	C10—H10B	0.9700
N3—C11	1.4415 (16)	C11—H11A	0.9700
C1—C2	1.4787 (18)	C11—H11B	0.9700
C2—C9	1.4915 (19)	C12—C13	1.508 (2)
C3—C4	1.3991 (19)	C12—H12A	0.9700
C3—C8	1.4041 (17)	C12—H12B	0.9700
C4—C5	1.369 (2)	C13—H13A	0.9700
C4—H4	0.953 (17)	C13—H13B	0.9700
C5—C6	1.392 (2)

C14—O2—C13	109.55 (11)	C2—C9—H9B	109.5
C1—N1—C8	121.61 (10)	H9A—C9—H9B	109.5
C1—N1—C10	116.97 (11)	C2—C9—H9C	109.5
C8—N1—C10	121.42 (10)	H9A—C9—H9C	109.5
C2—N2—C3	118.58 (11)	H9B—C9—H9C	109.5
C14—N3—C12	112.86 (11)	N1—C10—C11	110.28 (10)
C14—N3—C11	122.27 (11)	N1—C10—H10A	109.6
C12—N3—C11	124.57 (12)	C11—C10—H10A	109.6
O1—C1—N1	121.63 (12)	N1—C10—H10B	109.6
O1—C1—C2	122.48 (12)	C11—C10—H10B	109.6
N1—C1—C2	115.89 (11)	H10A—C10—H10B	108.1
N2—C2—C1	123.75 (11)	N3—C11—C10	111.20 (11)
N2—C2—C9	120.25 (12)	N3—C11—H11A	109.4
C1—C2—C9	116.00 (12)	C10—C11—H11A	109.4
N2—C3—C4	118.03 (12)	N3—C11—H11B	109.4
N2—C3—C8	122.11 (12)	C10—C11—H11B	109.4
C4—C3—C8	119.85 (12)	H11A—C11—H11B	108.0
C5—C4—C3	120.55 (14)	N3—C12—C13	102.23 (13)
C5—C4—H4	123.4 (11)	N3—C12—H12A	111.3
C3—C4—H4	116.1 (11)	C13—C12—H12A	111.3
C4—C5—C6	119.21 (14)	N3—C12—H12B	111.3
C4—C5—H7	119.0 (11)	C13—C12—H12B	111.3
C6—C5—H7	121.8 (11)	H12A—C12—H12B	109.2
C7—C6—C5	121.64 (14)	O2—C13—C12	105.73 (13)
C7—C6—H6	120.9 (11)	O2—C13—H13A	110.6
C5—C6—H6	117.4 (11)	C12—C13—H13A	110.6
C6—C7—C8	119.63 (14)	O2—C13—H13B	110.6
C6—C7—H5	120.6 (10)	C12—C13—H13B	110.6
C8—C7—H5	119.8 (10)	H13A—C13—H13B	108.7
N1—C8—C7	122.83 (12)	O3—C14—N3	128.19 (14)
N1—C8—C3	118.06 (11)	O3—C14—O2	122.27 (13)
C7—C8—C3	119.10 (12)	N3—C14—O2	109.53 (12)
C2—C9—H9A	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H5···O3ⁱ	0.98 (2)	2.54 (2)	3.462 (2)	157 (2)
C10—H10A···O3ⁱ	0.97	2.43	3.348 (2)	157

Symmetry code: (i) −x, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₅N₃O₃
M_r	273.29
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	12.280 (3), 10.736 (3), 20.406 (4)
β (°)	102.32 (1)
V (Å³)	2628.3 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.28 × 0.17 × 0.12

Data collection
Diffractometer	Bruker X8 APEXII CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	21237, 4108, 2727
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.723

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.157, 1.04
No. of reflections	4108
No. of parameters	204
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.24

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H5···O3ⁱ	0.98 (2)	2.54 (2)	3.462 (2)	157 (2)
C10—H10A···O3ⁱ	0.97	2.43	3.348 (2)	157

Symmetry code: (i) −x, y, −z+1/2.

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for making possible the present work. They also thank Professors B. Jaber and M. Benaissa for useful discussions and H. Zouihri for his technical assistance during the X-ray measurements.

References

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