3-[2-(1,3-Benzothia-zol-2-ylsulfan-yl)eth-yl]-1,3-oxazolidin-2-one.

The title compound, C(12)H(12)N(2)S(2)O(2), consists of a benzothia-zole group and a oxazolidin-1-one linked via a flexible ethane-1,2-diyl spacer. The benzothiazole group and the oxazolidine ring are each almost planar [with maximum deviations of 0.007 (2) and 0.044 (3) Å, respectively] and make a dihedral angle of 9.35 (10)°. In the crystal structure, adjacent mol-ecules were connected through C-H⋯O and C-H⋯N hydrogen bonds, and further extended into a three-dimensional network structure through inter-molecular aromatic π-π stacking inter-actions in which the centroid-centroid distance is 3.590 (1) Å.

Related literature

For background to the applications of 2-oxazolidinones, see: Ippolito et al. (2008 ▶); Mullera et al. (1999 ▶).

Experimental

Crystal data

C12H12N2O2S2

M = 280.36

Triclinic,

a = 6.5804 (4) Å

b = 7.8331 (5) Å

c = 12.5890 (7) Å

α = 99.864 (5)°

β = 97.715 (5)°

γ = 97.011 (5)°

V = 626.49 (7) Å3

Z = 2

Cu Kα radiation

μ = 3.83 mm−1

T = 293 K

0.16 × 0.14 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2005 ▶) T min = 0.572, T max = 1.000

4029 measured reflections

2396 independent reflections

2081 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.111

S = 1.05

2396 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.38 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2005 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2005 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810034264/bv2154sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034264/bv2154Isup2.hkl

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

C12H12N2O2S2	Z = 2
Mr = 280.36	F(000) = 292
Triclinic, P1	Dx = 1.486 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 6.5804 (4) Å	Cell parameters from 2669 reflections
b = 7.8331 (5) Å	θ = 3.6–72.2°
c = 12.5890 (7) Å	µ = 3.83 mm−1
α = 99.864 (5)°	T = 293 K
β = 97.715 (5)°	Rhombus, colourless
γ = 97.011 (5)°	0.16 × 0.14 × 0.10 mm
V = 626.49 (7) Å3

Oxford Diffraction Xcalibur Sapphire3 diffractometer	2396 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2081 reflections with I > 2σ(I)
graphite	Rint = 0.020
Detector resolution: 16.0355 pixels mm-1	θmax = 72.4°, θmin = 3.6°
ω scans	h = −7→5
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2005)	k = −9→8
Tmin = 0.572, Tmax = 1.000	l = −15→15
4029 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.081P)2 + 0.008P] where P = (Fo2 + 2Fc2)/3
2396 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.38 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
S1	0.35142 (6)	0.68528 (6)	0.47728 (3)	0.04252 (17)
S2	−0.03291 (7)	0.79117 (6)	0.57333 (4)	0.04677 (17)
O1	0.2992 (3)	1.2011 (2)	0.90981 (13)	0.0693 (5)
O2	0.6287 (3)	1.1616 (2)	0.95686 (12)	0.0661 (4)
N1	−0.0218 (2)	0.6472 (2)	0.36963 (12)	0.0407 (3)
N2	0.4734 (2)	1.0512 (2)	0.78894 (12)	0.0465 (4)
C1	0.1020 (3)	0.5814 (2)	0.29599 (14)	0.0370 (4)
C2	0.0334 (3)	0.5093 (3)	0.18583 (15)	0.0466 (4)
H2	−0.1048	0.5029	0.1556	0.056*
C3	0.1746 (3)	0.4474 (3)	0.12252 (15)	0.0500 (4)
H3	0.1301	0.3982	0.0492	0.060*
C4	0.3836 (3)	0.4578 (2)	0.16706 (16)	0.0474 (4)
H4	0.4757	0.4152	0.1228	0.057*
C5	0.4548 (3)	0.5301 (2)	0.27549 (15)	0.0424 (4)
H5	0.5937	0.5382	0.3050	0.051*
C6	0.3115 (3)	0.5908 (2)	0.33941 (14)	0.0358 (3)
C7	0.0866 (3)	0.7046 (2)	0.46521 (14)	0.0370 (4)
C8	0.1759 (3)	0.8424 (2)	0.68809 (14)	0.0441 (4)
H8A	0.1174	0.8441	0.7549	0.053*
H8B	0.2621	0.7503	0.6824	0.053*
C9	0.3115 (3)	1.0177 (2)	0.69552 (15)	0.0474 (4)
H9A	0.3729	1.0166	0.6296	0.057*
H9B	0.2267	1.1109	0.7014	0.057*
C10	0.6791 (3)	1.0058 (3)	0.78669 (19)	0.0533 (5)
H10A	0.7520	1.0668	0.7389	0.064*
H10B	0.6755	0.8806	0.7642	0.064*
C11	0.7754 (4)	1.0685 (4)	0.9048 (2)	0.0683 (6)
H11A	0.8023	0.9698	0.9390	0.082*
H11B	0.9054	1.1453	0.9106	0.082*
C12	0.4514 (3)	1.1428 (2)	0.88637 (15)	0.0480 (4)

	U11	U22	U33	U12	U13	U23
S1	0.0296 (2)	0.0517 (3)	0.0405 (3)	0.00659 (18)	−0.00164 (17)	−0.00180 (18)
S2	0.0372 (3)	0.0556 (3)	0.0451 (3)	0.0092 (2)	0.00809 (19)	−0.0001 (2)
O1	0.0739 (11)	0.0767 (11)	0.0617 (9)	0.0256 (9)	0.0276 (8)	0.0019 (8)
O2	0.0723 (10)	0.0682 (10)	0.0476 (8)	0.0023 (8)	−0.0068 (7)	0.0007 (7)
N1	0.0317 (7)	0.0481 (8)	0.0408 (8)	0.0079 (6)	0.0018 (6)	0.0062 (6)
N2	0.0426 (9)	0.0500 (8)	0.0431 (8)	0.0105 (7)	0.0052 (7)	−0.0030 (7)
C1	0.0337 (8)	0.0381 (8)	0.0395 (8)	0.0059 (6)	0.0031 (7)	0.0097 (7)
C2	0.0420 (10)	0.0542 (10)	0.0397 (9)	0.0055 (8)	−0.0022 (7)	0.0063 (8)
C3	0.0567 (11)	0.0524 (10)	0.0382 (9)	0.0068 (9)	0.0046 (8)	0.0043 (8)
C4	0.0509 (11)	0.0448 (9)	0.0485 (10)	0.0101 (8)	0.0163 (8)	0.0055 (8)
C5	0.0355 (9)	0.0411 (9)	0.0497 (10)	0.0065 (7)	0.0073 (7)	0.0055 (7)
C6	0.0325 (8)	0.0348 (7)	0.0380 (8)	0.0026 (6)	0.0021 (6)	0.0055 (6)
C7	0.0304 (8)	0.0379 (8)	0.0412 (9)	0.0049 (6)	0.0027 (7)	0.0055 (7)
C8	0.0489 (10)	0.0438 (9)	0.0393 (9)	0.0074 (8)	0.0074 (8)	0.0061 (7)
C9	0.0554 (11)	0.0409 (9)	0.0434 (9)	0.0079 (8)	0.0032 (8)	0.0044 (7)
C10	0.0478 (11)	0.0488 (10)	0.0680 (13)	0.0128 (8)	0.0168 (10)	0.0146 (9)
C11	0.0440 (12)	0.0807 (16)	0.0786 (16)	0.0031 (11)	−0.0035 (11)	0.0250 (13)
C12	0.0544 (11)	0.0448 (9)	0.0431 (10)	0.0062 (8)	0.0100 (8)	0.0028 (8)

S1—C6	1.7376 (17)	C3—C4	1.401 (3)
S1—C7	1.7564 (17)	C3—H3	0.9300
S2—C7	1.7412 (17)	C4—C5	1.379 (3)
S2—C8	1.8083 (19)	C4—H4	0.9300
O1—C12	1.202 (2)	C5—C6	1.394 (2)
O2—C12	1.343 (2)	C5—H5	0.9300
O2—C11	1.439 (3)	C8—C9	1.525 (3)
N1—C7	1.290 (2)	C8—H8A	0.9700
N1—C1	1.389 (2)	C8—H8B	0.9700
N2—C12	1.346 (2)	C9—H9A	0.9700
N2—C9	1.441 (2)	C9—H9B	0.9700
N2—C10	1.444 (3)	C10—C11	1.509 (3)
C1—C2	1.396 (2)	C10—H10A	0.9700
C1—C6	1.401 (2)	C10—H10B	0.9700
C2—C3	1.382 (3)	C11—H11A	0.9700
C2—H2	0.9300	C11—H11B	0.9700
C6—S1—C7	88.66 (8)	C9—C8—S2	113.55 (13)
C7—S2—C8	103.28 (8)	C9—C8—H8A	108.9
C12—O2—C11	109.30 (16)	S2—C8—H8A	108.9
C7—N1—C1	110.61 (14)	C9—C8—H8B	108.9
C12—N2—C9	122.28 (17)	S2—C8—H8B	108.9
C12—N2—C10	112.88 (17)	H8A—C8—H8B	107.7
C9—N2—C10	124.61 (16)	N2—C9—C8	110.74 (16)
N1—C1—C2	125.28 (16)	N2—C9—H9A	109.5
N1—C1—C6	115.23 (15)	C8—C9—H9A	109.5
C2—C1—C6	119.48 (17)	N2—C9—H9B	109.5
C3—C2—C1	118.82 (18)	C8—C9—H9B	109.5
C3—C2—H2	120.6	H9A—C9—H9B	108.1
C1—C2—H2	120.6	N2—C10—C11	100.92 (18)
C2—C3—C4	121.05 (18)	N2—C10—H10A	111.6
C2—C3—H3	119.5	C11—C10—H10A	111.6
C4—C3—H3	119.5	N2—C10—H10B	111.6
C5—C4—C3	120.99 (18)	C11—C10—H10B	111.6
C5—C4—H4	119.5	H10A—C10—H10B	109.4
C3—C4—H4	119.5	O2—C11—C10	106.53 (17)
C4—C5—C6	117.81 (17)	O2—C11—H11A	110.4
C4—C5—H5	121.1	C10—C11—H11A	110.4
C6—C5—H5	121.1	O2—C11—H11B	110.4
C5—C6—C1	121.83 (16)	C10—C11—H11B	110.4
C5—C6—S1	128.83 (14)	H11A—C11—H11B	108.6
C1—C6—S1	109.34 (13)	O1—C12—O2	123.44 (19)
N1—C7—S2	119.85 (13)	O1—C12—N2	126.8 (2)
N1—C7—S1	116.15 (13)	O2—C12—N2	109.76 (17)
S2—C7—S1	123.99 (10)
C7—N1—C1—C2	179.93 (17)	C8—S2—C7—S1	−1.39 (13)
C7—N1—C1—C6	0.0 (2)	C6—S1—C7—N1	0.16 (14)
N1—C1—C2—C3	−179.38 (17)	C6—S1—C7—S2	179.01 (12)
C6—C1—C2—C3	0.5 (3)	C7—S2—C8—C9	82.41 (15)
C1—C2—C3—C4	−0.6 (3)	C12—N2—C9—C8	−92.9 (2)
C2—C3—C4—C5	0.0 (3)	C10—N2—C9—C8	92.9 (2)
C3—C4—C5—C6	0.7 (3)	S2—C8—C9—N2	179.53 (12)
C4—C5—C6—C1	−0.7 (3)	C12—N2—C10—C11	6.1 (2)
C4—C5—C6—S1	179.22 (14)	C9—N2—C10—C11	−179.26 (19)
N1—C1—C6—C5	−179.97 (15)	C12—O2—C11—C10	7.0 (3)
C2—C1—C6—C5	0.1 (3)	N2—C10—C11—O2	−7.6 (2)
N1—C1—C6—S1	0.08 (19)	C11—O2—C12—O1	176.9 (2)
C2—C1—C6—S1	−179.82 (14)	C11—O2—C12—N2	−3.2 (2)
C7—S1—C6—C5	179.93 (17)	C9—N2—C12—O1	3.0 (3)
C7—S1—C6—C1	−0.13 (13)	C10—N2—C12—O1	177.8 (2)
C1—N1—C7—S2	−179.04 (12)	C9—N2—C12—O2	−176.91 (16)
C1—N1—C7—S1	−0.14 (19)	C10—N2—C12—O2	−2.1 (2)
C8—S2—C7—N1	177.42 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O1i	0.97	2.58	3.466 (3)	152
C3—H3···O1ii	0.93	2.59	3.282 (2)	132
C5—H5···N1i	0.93	2.54	3.445 (2)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯O1i	0.97	2.58	3.466 (3)	152
C3—H3⋯O1ii	0.93	2.59	3.282 (2)	132
C5—H5⋯N1i	0.93	2.54	3.445 (2)	163

Symmetry codes: (i) ; (ii) .