3-[2-(3-Methyl-2-oxo-1,2-dihydro-quinoxalin-1-yl)eth-yl]oxazolidin-2-one.

The title heterocyclic compound, C(14)H(15)N(3)O(3), is a new synthetic mol-ecule 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 C(2) 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 mol-ecules and by weak π-π stacking between symmetry-related mol-ecules, with an inter-planar distance of 3.579 Å and a centroid-centroid distance of 3.800 (1) Å. Inter-molecular 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 = 273.29

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.157

S = 1.04

4108 reflections

204 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.24 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: 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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H15N3O3	F(000) = 1152
Mr = 273.29	Dx = 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

Bruker X8 APEXII CCD area-detector diffractometer	Rint = 0.033
graphite	θmax = 30.9°, θmin = 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 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(Fo2) + (0.081P)2 + 0.6684P] where P = (Fo2 + 2Fc2)/3
4108 reflections	(Δ/σ)max = 0.001
204 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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

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

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) .