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

Two isomers were isolated during the reaction between 3-methyl-quinoxalin-2-one and bis-(2-chloro-ethyl)amine hydro-chloride. The crystal structure of one isomer has already been reported [Caleb, Bouhfid, Essassi & El Ammari (2009). Acta Cryst. E65, o2024-o2025], while that of the second isomer is the subject of this work. The title compound, C(14)H(15)N(3)O(3), has a new structure containing oxazolidine and quinoxaline rings linked by an eth-oxy group. The main difference between the two isomers is the position of the oxazolidine group with respect to the quinoxaline system. The dihedral angle between the fused planar rings and the oxazolidin-2-one ring is 41.63 (8)° in the title mol-ecule.

Related literature

For the biological activity of 3-[2-(3-methyl-1,2-dihydro­quin­oxalin-2-yl­oxy)eth­yl]oxazolidin-2-one, see: Madhusudhan et al. (2004 ▶); Soad et al. (2006 ▶); Sriharsha & Shashikanth (2006 ▶); Menoret et al. (2009 ▶); Wilhelmsson et al. (2008 ▶). For the structure of the isomer of the title compound, see: Caleb et al. (2009 ▶). For related structures, see: Doubia et al. (2007 ▶); Mamedov et al. (2007 ▶); Aschwanden et al.(1976 ▶)

Experimental

Crystal data

C14H15N3O3

M = 273.29

Triclinic,

a = 6.9936 (3) Å

b = 7.6916 (3) Å

c = 13.3709 (6) Å

α = 86.649 (2)°

β = 77.044 (2)°

γ = 71.141 (2)°

V = 663.23 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.41 × 0.33 × 0.20 mm

Data collection

Bruker X8 APEXII CCD area-detector diffractometer

15358 measured reflections

3030 independent reflections

2358 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.121

S = 1.06

3030 reflections

198 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (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/S1600536810012687/dn2552sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012687/dn2552Isup2.hkl

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

C14H15N3O3	Z = 2
Mr = 273.29	F(000) = 288
Triclinic, P1	Dx = 1.368 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9936 (3) Å	Cell parameters from 15358 reflections
b = 7.6916 (3) Å	θ = 2.8–27.5°
c = 13.3709 (6) Å	µ = 0.10 mm−1
α = 86.649 (2)°	T = 296 K
β = 77.044 (2)°	Prism, colourless
γ = 71.141 (2)°	0.41 × 0.33 × 0.20 mm
V = 663.23 (5) Å3

Bruker X8 APEXII CCD area-detector diffractometer	2358 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
graphite	θmax = 27.5°, θmin = 2.8°
φ and ω scans	h = −9→9
15358 measured reflections	k = −9→9
3030 independent reflections	l = −17→17

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0643P)2 + 0.0716P] where P = (Fo2 + 2Fc2)/3
3030 reflections	(Δ/σ)max < 0.001
198 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using 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 data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.31122 (17)	0.72867 (15)	0.95763 (8)	0.0378 (3)
C2	0.08813 (17)	0.80823 (15)	1.11146 (8)	0.0382 (3)
C3	−0.11007 (19)	0.83829 (18)	1.17492 (10)	0.0470 (3)
C4	−0.1442 (2)	0.8837 (2)	1.27638 (10)	0.0531 (3)
C5	0.0143 (2)	0.90272 (19)	1.31801 (10)	0.0540 (3)
C6	0.2068 (2)	0.87655 (18)	1.25750 (10)	0.0503 (3)
C7	0.24799 (18)	0.82807 (16)	1.15335 (9)	0.0403 (3)
C8	0.47691 (17)	0.75240 (16)	0.99773 (9)	0.0412 (3)
C9	0.68526 (19)	0.7217 (2)	0.92895 (11)	0.0546 (3)
H9A	0.7371	0.5987	0.9015	0.082*
H9B	0.7784	0.7393	0.9674	0.082*
H9C	0.6743	0.8075	0.8737	0.082*
C10	0.21267 (19)	0.63937 (19)	0.81444 (9)	0.0465 (3)
H10A	0.1105	0.7551	0.8041	0.056*
H10B	0.1429	0.5643	0.8593	0.056*
C11	0.3226 (2)	0.54186 (19)	0.71328 (10)	0.0523 (3)
H11A	0.4218	0.4258	0.7258	0.063*
H11B	0.2221	0.5146	0.6826	0.063*
C12	0.3726 (3)	0.7066 (2)	0.55269 (11)	0.0625 (4)
C13	0.6852 (3)	0.7454 (3)	0.54185 (14)	0.0820 (5)
H13A	0.6957	0.8634	0.5570	0.098*
H13B	0.8151	0.6739	0.4986	0.098*
C14	0.6363 (3)	0.6450 (3)	0.63974 (11)	0.0682 (4)
H14A	0.7319	0.5209	0.6375	0.082*
H14B	0.6394	0.7098	0.6991	0.082*
N1	0.12438 (14)	0.75658 (13)	1.01023 (7)	0.0406 (2)
N2	0.44386 (15)	0.80020 (15)	1.09343 (8)	0.0462 (3)
N3	0.43028 (18)	0.64507 (16)	0.64066 (8)	0.0534 (3)
O1	0.36793 (12)	0.67107 (12)	0.85906 (6)	0.0460 (2)
O2	0.2172 (2)	0.70974 (18)	0.52691 (9)	0.0879 (4)
O3	0.5186 (2)	0.76983 (16)	0.49204 (8)	0.0829 (4)
H3	−0.220 (2)	0.8300 (19)	1.1449 (11)	0.052 (4)*
H4	−0.280 (2)	0.908 (2)	1.3175 (13)	0.068 (4)*
H5	−0.009 (2)	0.934 (2)	1.3883 (14)	0.064 (4)*
H6	0.322 (3)	0.889 (2)	1.2864 (13)	0.071 (4)*

	U11	U22	U33	U12	U13	U23
C1	0.0389 (6)	0.0433 (6)	0.0313 (6)	−0.0140 (5)	−0.0066 (4)	0.0011 (4)
C2	0.0413 (6)	0.0410 (6)	0.0317 (6)	−0.0135 (5)	−0.0066 (4)	0.0011 (4)
C3	0.0439 (7)	0.0559 (7)	0.0406 (7)	−0.0189 (6)	−0.0031 (5)	−0.0016 (5)
C4	0.0526 (7)	0.0592 (8)	0.0396 (7)	−0.0161 (6)	0.0039 (6)	−0.0019 (6)
C5	0.0656 (8)	0.0568 (8)	0.0317 (7)	−0.0106 (6)	−0.0064 (6)	−0.0048 (5)
C6	0.0545 (8)	0.0564 (8)	0.0388 (7)	−0.0113 (6)	−0.0162 (6)	−0.0043 (5)
C7	0.0415 (6)	0.0427 (6)	0.0354 (6)	−0.0106 (5)	−0.0097 (5)	−0.0003 (5)
C8	0.0366 (6)	0.0476 (6)	0.0391 (6)	−0.0127 (5)	−0.0083 (5)	−0.0005 (5)
C9	0.0394 (6)	0.0745 (9)	0.0505 (8)	−0.0210 (6)	−0.0050 (5)	−0.0066 (6)
C10	0.0446 (6)	0.0629 (8)	0.0351 (6)	−0.0211 (6)	−0.0079 (5)	−0.0038 (5)
C11	0.0608 (8)	0.0600 (8)	0.0381 (7)	−0.0217 (6)	−0.0093 (6)	−0.0066 (5)
C12	0.0842 (11)	0.0549 (8)	0.0358 (7)	−0.0028 (8)	−0.0139 (7)	−0.0097 (6)
C13	0.0972 (13)	0.0874 (12)	0.0545 (10)	−0.0363 (10)	0.0076 (9)	0.0021 (8)
C14	0.0723 (10)	0.0929 (11)	0.0440 (8)	−0.0373 (9)	−0.0061 (7)	0.0036 (7)
N1	0.0385 (5)	0.0515 (6)	0.0331 (5)	−0.0169 (4)	−0.0062 (4)	−0.0017 (4)
N2	0.0400 (5)	0.0571 (6)	0.0425 (6)	−0.0140 (5)	−0.0120 (4)	−0.0036 (5)
N3	0.0602 (7)	0.0644 (7)	0.0316 (5)	−0.0157 (5)	−0.0071 (5)	−0.0024 (5)
O1	0.0409 (4)	0.0667 (6)	0.0316 (4)	−0.0203 (4)	−0.0035 (3)	−0.0063 (4)
O2	0.1019 (9)	0.0914 (9)	0.0633 (8)	−0.0034 (7)	−0.0421 (7)	−0.0077 (6)
O3	0.1211 (10)	0.0797 (8)	0.0399 (6)	−0.0288 (7)	−0.0081 (6)	0.0096 (5)

C1—N1	1.2932 (14)	C9—H9C	0.9600
C1—O1	1.3457 (13)	C10—O1	1.4398 (13)
C1—C8	1.4458 (15)	C10—C11	1.5041 (18)
C2—N1	1.3777 (14)	C10—H10A	0.9700
C2—C3	1.4083 (16)	C10—H10B	0.9700
C2—C7	1.4099 (15)	C11—N3	1.4523 (17)
C3—C4	1.3695 (18)	C11—H11A	0.9700
C3—H3	0.966 (14)	C11—H11B	0.9700
C4—C5	1.397 (2)	C12—O2	1.2046 (19)
C4—H4	0.949 (16)	C12—N3	1.3394 (19)
C5—C6	1.3646 (19)	C12—O3	1.357 (2)
C5—H5	0.948 (17)	C13—O3	1.424 (2)
C6—C7	1.4045 (17)	C13—C14	1.510 (2)
C6—H6	0.999 (17)	C13—H13A	0.9700
C7—N2	1.3793 (15)	C13—H13B	0.9700
C8—N2	1.3013 (15)	C14—N3	1.4379 (19)
C8—C9	1.4923 (16)	C14—H14A	0.9700
C9—H9A	0.9600	C14—H14B	0.9700
C9—H9B	0.9600
N1—C1—O1	121.60 (10)	C11—C10—H10A	110.3
N1—C1—C8	124.34 (10)	O1—C10—H10B	110.3
O1—C1—C8	114.06 (9)	C11—C10—H10B	110.3
N1—C2—C3	119.79 (10)	H10A—C10—H10B	108.6
N1—C2—C7	120.95 (10)	N3—C11—C10	114.20 (11)
C3—C2—C7	119.25 (11)	N3—C11—H11A	108.7
C4—C3—C2	119.75 (12)	C10—C11—H11A	108.7
C4—C3—H3	121.5 (9)	N3—C11—H11B	108.7
C2—C3—H3	118.7 (8)	C10—C11—H11B	108.7
C3—C4—C5	121.01 (12)	H11A—C11—H11B	107.6
C3—C4—H4	118.6 (10)	O2—C12—N3	127.96 (16)
C5—C4—H4	120.3 (10)	O2—C12—O3	122.31 (14)
C6—C5—C4	120.14 (12)	N3—C12—O3	109.73 (14)
C6—C5—H5	118.9 (9)	O3—C13—C14	106.05 (14)
C4—C5—H5	120.9 (9)	O3—C13—H13A	110.5
C5—C6—C7	120.42 (12)	C14—C13—H13A	110.5
C5—C6—H6	120.9 (10)	O3—C13—H13B	110.5
C7—C6—H6	118.6 (10)	C14—C13—H13B	110.5
N2—C7—C6	119.74 (10)	H13A—C13—H13B	108.7
N2—C7—C2	120.85 (10)	N3—C14—C13	101.80 (14)
C6—C7—C2	119.41 (11)	N3—C14—H14A	111.4
N2—C8—C1	119.95 (10)	C13—C14—H14A	111.4
N2—C8—C9	120.35 (10)	N3—C14—H14B	111.4
C1—C8—C9	119.70 (11)	C13—C14—H14B	111.4
C8—C9—H9A	109.5	H14A—C14—H14B	109.3
C8—C9—H9B	109.5	C1—N1—C2	115.96 (9)
H9A—C9—H9B	109.5	C8—N2—C7	117.92 (10)
C8—C9—H9C	109.5	C12—N3—C14	112.13 (13)
H9A—C9—H9C	109.5	C12—N3—C11	122.09 (13)
H9B—C9—H9C	109.5	C14—N3—C11	123.42 (12)
O1—C10—C11	106.91 (10)	C1—O1—C10	117.34 (9)
O1—C10—H10A	110.3	C12—O3—C13	109.59 (12)