O-Ethyl S-{(S)-1-oxo-1-[(R)-2-oxo-4-phenyl-oxazolidin-3-yl]propan-2-yl} carbonodi-thio-ate.

In the title compound, C15H17NO4S2, synthesized by addition of O-ethylxanthic acid potassium salt to a diastereomeric mixture of (4R)-3-(2-chloro-propano-yl)-4-phenyl-oxazolidin-2-one, the oxazolidinone ring has a twist conformation on the C-C bond. The phenyl ring is inclined to the mean plane of the oxazolidinone ring by 76.4 (3)°. In the chain the methine H atom is involved in a C-H⋯S and a C-H⋯O intra-molecular inter-action. In the crystal, mol-ecules are linked by C-H⋯π inter-actions, forming chains along [001]. The S configuration at the C atom to which the xanthate group is attached was determined by comparison to the known R configuration of the C atom to which the phenyl group is attached.

Related literature

For the use of chiral oxazolidinones auxiliaries in asymmetric synthesis, see: Evans (1982 ▶); Ager et al. (1997 ▶). For the oral activity of oxazolidinonas against multidrug-resistant Gram-positive bacteria, see: Müller & Schimz (1999 ▶). For our work on the synthesis of novel heterocyclic compounds, see for example: López-Ruiz et al. (2011 ▶). For the crystal structures of similar compounds, see: Bartczak et al. (2001 ▶); Kruszynski et al. (2001 ▶); Wouters et al. (1997 ▶). For the crystal structures of 3,4-disubstituted oxazolidinone derivatives, see: Marsh et al. (1992 ▶); Evain et al. (2002 ▶); Hwang et al. (2006 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For ring puckering analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C15H17NO4S2

M = 339.42

Monoclinic,

a = 10.8558 (15) Å

b = 6.1867 (9) Å

c = 12.3057 (17) Å

β = 94.911 (4)°

V = 823.4 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.34 mm−1

T = 293 K

0.2 × 0.17 × 0.16 mm

Data collection

Bruker SMART CCD diffractometer

10191 measured reflections

3223 independent reflections

1681 reflections with I > 2σ(I)

R int = 0.152

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.191

S = 0.87

3223 reflections

201 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.35 e Å−3

Absolute structure: Flack (1983 ▶), 6968 Friedel pairs

Absolute structure parameter: 0.08 (18)

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814007636/su2715sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814007636/su2715Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814007636/su2715Isup3.cml

CCDC reference: 995594

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H17NO4S2	F(000) = 356
Mr = 339.42	Dx = 1.369 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1321 reflections
a = 10.8558 (15) Å	θ = 1.7–26.0°
b = 6.1867 (9) Å	µ = 0.34 mm−1
c = 12.3057 (17) Å	T = 293 K
β = 94.911 (4)°	Block, colourless
V = 823.4 (2) Å3	0.2 × 0.17 × 0.16 mm
Z = 2

Bruker SMART CCD diffractometer	1681 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.152
Graphite monochromator	θmax = 26.0°, θmin = 1.7°
φ and ω scans	h = −13→13
10191 measured reflections	k = −7→7
3223 independent reflections	l = −15→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.067	H-atom parameters constrained
wR(F2) = 0.191	w = 1/[σ2(Fo2) + (0.0945P)2] where P = (Fo2 + 2Fc2)/3
S = 0.87	(Δ/σ)max < 0.001
3223 reflections	Δρmax = 0.38 e Å−3
201 parameters	Δρmin = −0.35 e Å−3
1 restraint	Absolute structure: Flack (1983), 6968 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.08 (18)

Experimental. Spectroscopic data for the title compound: 1H NMR (400 MHz, CDCl3)δ: 7.2 (m, 5H, CH, arom), 5.6 (q, 1H, CH (H-4), J= 7.3 Hz), 5.4 (dd, CH (H-9), J1= 3.2 Hz, J2=8.6 Hz), 4.7 (t, 1H (H-8a), CH2, J= 8.8 Hz), 4.6 (m, 2H, CH2(H-2)), 4.3 (dd, 1H (H-8 b), J1= 3.2 Hz, J2= 8.6 Hz), 1.4 (d,3H,CH3 (H-5), J= 7.3 Hz), 1.4 (t, 3H,CH3 (H-1), J= 7.3 Hz); 13C NMR (100 MHz, CDCl3) δ: 213 (CS), 171.05 (CO), 153.53 (CO), 138.74 (C), 129.33 (CH), 128.93 (2CH), 125.90 (CH), 70.35 (2CH2), 58.03 (CH), 57.94 (CH), 47.20 (CH), 15.80 (CH3), 13.60 (CH3).

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.8431 (7)	0.9153 (19)	1.0271 (7)	0.101 (3)
H1A	0.8415	0.9226	0.9491	0.151*
H1B	0.9209	0.9693	1.0591	0.151*
H1C	0.7772	1.0015	1.0513	0.151*
C2	0.8275 (6)	0.6889 (16)	1.0609 (6)	0.082 (2)
H2A	0.8932	0.6011	1.0354	0.098*
H2B	0.8328	0.6804	1.1399	0.098*
C3	0.6967 (6)	0.5034 (10)	0.9216 (5)	0.0560 (17)
C4	0.5331 (5)	0.2814 (10)	0.7734 (5)	0.0479 (15)
H4	0.6011	0.3210	0.7298	0.057*
C5	0.5440 (7)	0.0432 (10)	0.8030 (6)	0.069 (2)
H5A	0.4763	0.0023	0.8439	0.103*
H5B	0.6206	0.0185	0.8462	0.103*
H5C	0.5421	−0.0415	0.7375	0.103*
C6	0.4117 (6)	0.3295 (9)	0.7086 (5)	0.0459 (14)
C7	0.4827 (6)	0.1846 (9)	0.5343 (5)	0.0481 (15)
C8	0.2958 (6)	0.1740 (13)	0.4298 (5)	0.0613 (17)
H8A	0.2566	0.0348	0.4153	0.074*
H8B	0.2653	0.2748	0.3734	0.074*
C9	0.2687 (5)	0.2584 (10)	0.5439 (4)	0.0458 (14)
H9	0.2434	0.4104	0.5388	0.055*
C10	0.1727 (5)	0.1287 (9)	0.5970 (4)	0.0420 (14)
C11	0.0555 (5)	0.2134 (10)	0.6019 (5)	0.0516 (16)
H11	0.0357	0.3479	0.5715	0.062*
C12	−0.0328 (6)	0.0959 (11)	0.6529 (6)	0.0632 (19)
H12	−0.1116	0.1528	0.6567	0.076*
C13	−0.0047 (6)	−0.1024 (13)	0.6975 (5)	0.066 (2)
H13	−0.0641	−0.1776	0.7324	0.080*
C14	0.1105 (7)	−0.1919 (11)	0.6912 (6)	0.0673 (19)
H14	0.1292	−0.3279	0.7204	0.081*
C15	0.1990 (5)	−0.0740 (13)	0.6399 (5)	0.0583 (15)
H15	0.2770	−0.1332	0.6346	0.070*
N1	0.3934 (4)	0.2412 (7)	0.6027 (4)	0.0423 (11)
O1	0.7069 (4)	0.6056 (9)	1.0155 (4)	0.0770 (15)
O2	0.3286 (4)	0.4268 (9)	0.7448 (3)	0.0631 (11)
O3	0.5918 (4)	0.1651 (7)	0.5559 (4)	0.0566 (12)
O4	0.4291 (4)	0.1544 (7)	0.4330 (3)	0.0551 (11)
S1	0.80766 (14)	0.4339 (4)	0.84599 (14)	0.0760 (6)
S2	0.53803 (14)	0.4534 (3)	0.89279 (13)	0.0631 (5)

	U11	U22	U33	U12	U13	U23
C1	0.068 (5)	0.143 (8)	0.091 (6)	−0.024 (6)	−0.002 (4)	0.019 (7)
C2	0.054 (4)	0.126 (8)	0.063 (4)	0.001 (4)	−0.010 (4)	−0.019 (5)
C3	0.049 (3)	0.072 (5)	0.046 (4)	0.001 (3)	0.002 (3)	0.003 (3)
C4	0.040 (3)	0.054 (4)	0.051 (3)	0.004 (3)	0.011 (3)	−0.003 (3)
C5	0.081 (5)	0.067 (5)	0.057 (4)	0.006 (4)	0.000 (4)	0.006 (3)
C6	0.048 (3)	0.043 (3)	0.048 (4)	−0.006 (3)	0.011 (3)	−0.002 (3)
C7	0.057 (4)	0.038 (3)	0.051 (4)	−0.003 (3)	0.016 (3)	0.002 (3)
C8	0.053 (4)	0.083 (5)	0.048 (4)	−0.002 (3)	0.005 (3)	−0.002 (4)
C9	0.041 (3)	0.050 (3)	0.046 (3)	−0.002 (3)	0.005 (3)	0.002 (3)
C10	0.045 (3)	0.039 (3)	0.042 (3)	−0.004 (3)	0.003 (3)	−0.003 (3)
C11	0.049 (4)	0.056 (4)	0.049 (4)	0.007 (3)	0.003 (3)	−0.002 (3)
C12	0.040 (3)	0.076 (5)	0.075 (5)	−0.007 (4)	0.010 (3)	−0.013 (4)
C13	0.056 (4)	0.085 (6)	0.060 (4)	−0.034 (4)	0.016 (3)	−0.003 (4)
C14	0.060 (4)	0.070 (5)	0.071 (4)	−0.009 (4)	0.000 (4)	0.007 (4)
C15	0.042 (3)	0.060 (4)	0.073 (4)	−0.001 (4)	0.010 (3)	−0.003 (4)
N1	0.034 (2)	0.050 (3)	0.044 (3)	0.000 (2)	0.009 (2)	0.000 (2)
O1	0.049 (3)	0.116 (4)	0.065 (3)	−0.009 (3)	0.003 (2)	−0.028 (3)
O2	0.047 (2)	0.088 (3)	0.055 (2)	0.014 (3)	0.0065 (19)	−0.019 (3)
O3	0.044 (3)	0.065 (3)	0.063 (3)	0.006 (2)	0.015 (2)	−0.006 (2)
O4	0.059 (3)	0.061 (3)	0.047 (3)	−0.001 (2)	0.017 (2)	−0.004 (2)
S1	0.0462 (9)	0.1207 (15)	0.0621 (10)	−0.0011 (13)	0.0095 (7)	−0.0115 (13)
S2	0.0438 (8)	0.0872 (12)	0.0585 (9)	−0.0036 (10)	0.0067 (7)	−0.0216 (10)

C1—C2	1.475 (13)	C7—O4	1.344 (7)
C1—H1A	0.9600	C7—N1	1.382 (7)
C1—H1B	0.9600	C8—O4	1.449 (8)
C1—H1C	0.9600	C8—C9	1.550 (8)
C2—O1	1.472 (8)	C8—H8A	0.9700
C2—H2A	0.9700	C8—H8B	0.9700
C2—H2B	0.9700	C9—N1	1.483 (7)
C3—O1	1.313 (7)	C9—C10	1.507 (8)
C3—S1	1.642 (6)	C9—H9	0.9800
C3—S2	1.756 (6)	C10—C15	1.381 (9)
C4—C6	1.511 (8)	C10—C11	1.383 (8)
C4—C5	1.520 (8)	C11—C12	1.395 (9)
C4—S2	1.811 (6)	C11—H11	0.9300
C4—H4	0.9800	C12—C13	1.367 (10)
C5—H5A	0.9600	C12—H12	0.9300
C5—H5B	0.9600	C13—C14	1.376 (10)
C5—H5C	0.9600	C13—H13	0.9300
C6—O2	1.201 (7)	C14—C15	1.399 (9)
C6—N1	1.411 (7)	C14—H14	0.9300
C7—O3	1.198 (8)	C15—H15	0.9300
C2—C1—H1A	109.5	C9—C8—H8A	110.6
C2—C1—H1B	109.5	O4—C8—H8B	110.6
H1A—C1—H1B	109.5	C9—C8—H8B	110.6
C2—C1—H1C	109.5	H8A—C8—H8B	108.7
H1A—C1—H1C	109.5	N1—C9—C10	112.7 (5)
H1B—C1—H1C	109.5	N1—C9—C8	100.5 (4)
O1—C2—C1	110.2 (6)	C10—C9—C8	113.9 (5)
O1—C2—H2A	109.6	N1—C9—H9	109.8
C1—C2—H2A	109.6	C10—C9—H9	109.8
O1—C2—H2B	109.6	C8—C9—H9	109.8
C1—C2—H2B	109.6	C15—C10—C11	119.2 (5)
H2A—C2—H2B	108.1	C15—C10—C9	121.4 (5)
O1—C3—S1	127.9 (5)	C11—C10—C9	119.3 (5)
O1—C3—S2	105.7 (4)	C10—C11—C12	119.5 (6)
S1—C3—S2	126.4 (4)	C10—C11—H11	120.2
C6—C4—C5	111.4 (5)	C12—C11—H11	120.2
C6—C4—S2	106.1 (4)	C13—C12—C11	120.6 (6)
C5—C4—S2	112.3 (5)	C13—C12—H12	119.7
C6—C4—H4	109.0	C11—C12—H12	119.7
C5—C4—H4	109.0	C12—C13—C14	120.8 (6)
S2—C4—H4	109.0	C12—C13—H13	119.6
C4—C5—H5A	109.5	C14—C13—H13	119.6
C4—C5—H5B	109.5	C13—C14—C15	118.5 (7)
H5A—C5—H5B	109.5	C13—C14—H14	120.7
C4—C5—H5C	109.5	C15—C14—H14	120.7
H5A—C5—H5C	109.5	C10—C15—C14	121.3 (6)
H5B—C5—H5C	109.5	C10—C15—H15	119.4
O2—C6—N1	119.1 (5)	C14—C15—H15	119.4
O2—C6—C4	123.5 (5)	C7—N1—C6	127.6 (5)
N1—C6—C4	117.3 (5)	C7—N1—C9	112.3 (5)
O3—C7—O4	122.3 (5)	C6—N1—C9	118.2 (4)
O3—C7—N1	128.5 (6)	C3—O1—C2	120.5 (5)
O4—C7—N1	109.3 (5)	C7—O4—C8	111.5 (5)
O4—C8—C9	105.7 (5)	C3—S2—C4	103.2 (3)
O4—C8—H8A	110.6
C5—C4—C6—O2	108.2 (7)	O3—C7—N1—C9	177.2 (6)
S2—C4—C6—O2	−14.3 (7)	O4—C7—N1—C9	−1.9 (6)
C5—C4—C6—N1	−67.3 (7)	O2—C6—N1—C7	158.5 (6)
S2—C4—C6—N1	170.3 (4)	C4—C6—N1—C7	−25.8 (8)
O4—C8—C9—N1	−8.7 (6)	O2—C6—N1—C9	−4.6 (8)
O4—C8—C9—C10	−129.5 (5)	C4—C6—N1—C9	171.1 (5)
N1—C9—C10—C15	−40.0 (8)	C10—C9—N1—C7	128.3 (5)
C8—C9—C10—C15	73.6 (7)	C8—C9—N1—C7	6.7 (6)
N1—C9—C10—C11	140.7 (5)	C10—C9—N1—C6	−66.1 (6)
C8—C9—C10—C11	−105.7 (6)	C8—C9—N1—C6	172.3 (5)
C15—C10—C11—C12	1.9 (9)	S1—C3—O1—C2	5.3 (10)
C9—C10—C11—C12	−178.7 (5)	S2—C3—O1—C2	−175.1 (6)
C10—C11—C12—C13	−0.3 (10)	C1—C2—O1—C3	92.6 (8)
C11—C12—C13—C14	−1.2 (10)	O3—C7—O4—C8	176.3 (6)
C12—C13—C14—C15	1.1 (10)	N1—C7—O4—C8	−4.5 (6)
C11—C10—C15—C14	−2.0 (9)	C9—C8—O4—C7	8.6 (7)
C9—C10—C15—C14	178.6 (6)	O1—C3—S2—C4	−172.4 (5)
C13—C14—C15—C10	0.5 (10)	S1—C3—S2—C4	7.2 (5)
O3—C7—N1—C6	13.3 (10)	C6—C4—S2—C3	−149.4 (4)
O4—C7—N1—C6	−165.8 (5)	C5—C4—S2—C3	88.8 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···S1	0.98	2.65	3.180 (9)	114
C4—H4···O3	0.98	2.34	2.895 (10)	115
C2—H2B···Cgi	0.97	2.90	3.807 (8)	156

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C10–C15 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯S1	0.98	2.65	3.180 (9)	114
C4—H4⋯O3	0.98	2.34	2.895 (10)	115
C2—H2B⋯Cg i	0.97	2.90	3.807 (8)	156

Symmetry code: (i) .