Crystal structure of (4R,5S)-4-methyl-3-methyl-sulfinyl-5-phenyl-1,3-oxazolidin-2-one.

The absolute structure of the chiral asymmetric indole precursor title compound, C11H13NO3S, was confirmed by refinement of the Flack and Hooft parameters and is that expected based on the starting materials for the synthesis. The phenyl group subtends a dihedral angle of 56.40 (5)° with the mean plane of the oxazolidinone ring, which adopts an envelope conformation, with the C atom bearing the methyl group as the flap. In the crystal, no significant directional inter-actions beyond van der Waals contacts are observed.

Related literature

For general background to the preparation of naturally occurring alkaloids, see: Marino et al. (1992 ▶). For further synthetic details, see: Silveira & Marino, 2013 ▶. For related structures, see: Evans et al. (1992 ▶); Silveira et al. (2013 ▶); Silveira et al. (2012 ▶); Clara-Sosa et al. (2004 ▶); Romanenko et al. (2003 ▶). A statistical analysis (Hooft et al., 2008 ▶) was used to corroborate that the correct enanti­omorph of the space group and hence handedness of the mol­ecule had been determined.

Experimental

Crystal data

C11H13NO3S

M = 239.28

Orthorhombic,

a = 6.1605 (4) Å

b = 11.8490 (8) Å

c = 15.3861 (11) Å

V = 1123.12 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 100 K

0.22 × 0.09 × 0.06 mm

Data collection

Bruker X8 APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.707, T max = 0.746

30938 measured reflections

3761 independent reflections

3507 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.070

S = 1.03

3761 reflections

147 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack x determined using 1431 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▶)

Absolute structure parameter: −0.012 (16)

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: XCIF (Sheldrick, 2008 ▶), enCIFer (Allen et al., 2004 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814024702/hb7309sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814024702/hb7309Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814024702/hb7309Isup3.cml

Click here for additional data file.

R S . DOI: 10.1107/S1600536814024702/hb7309fig1.tif

Labelling scheme for (4R,5S)-4-methyl-3-methylsulfinyl-5-phenyl-1,3-oxazolidin-2-one. Thermal displacement ellipsoids are depicted at the 50% probability level.

CCDC reference: 1033536

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

C11H13NO3S	Dx = 1.415 Mg m−3
Mr = 239.28	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 9865 reflections
a = 6.1605 (4) Å	θ = 3.2–31.4°
b = 11.8490 (8) Å	µ = 0.28 mm−1
c = 15.3861 (11) Å	T = 100 K
V = 1123.12 (13) Å3	Rod, colorless
Z = 4	0.22 × 0.09 × 0.06 mm
F(000) = 504

Bruker X8 APEXII CCD diffractometer	3761 independent reflections
Radiation source: fine-focus sealed tube	3507 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 8.33 pixels mm-1	θmax = 31.6°, θmin = 2.2°
φ and ω scans	h = −8→9
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −17→17
Tmin = 0.707, Tmax = 0.746	l = −21→22
30938 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.027	w = 1/[σ2(Fo2) + (0.0431P)2 + 0.127P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.070	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.31 e Å−3
3761 reflections	Δρmin = −0.18 e Å−3
147 parameters	Absolute structure: Flack x determined using 1431 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: −0.012 (16)

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.

	x	y	z	Uiso*/Ueq
S1	0.97856 (6)	0.27012 (3)	0.33636 (2)	0.01721 (9)
N1	0.8121 (2)	0.16070 (11)	0.31202 (8)	0.0153 (2)
O1	0.74140 (17)	0.00157 (9)	0.24121 (6)	0.0175 (2)
O2	1.04668 (18)	0.09415 (9)	0.20595 (7)	0.0194 (2)
O3	1.13406 (18)	0.23613 (11)	0.40470 (7)	0.0241 (2)
C1	0.5547 (2)	0.02282 (12)	0.29661 (9)	0.0156 (3)
H1	0.4376	0.0589	0.2612	0.019*
C2	0.6387 (2)	0.10893 (12)	0.36433 (9)	0.0152 (3)
H2	0.5236	0.1659	0.3775	0.018*
C3	0.8831 (2)	0.08716 (12)	0.24861 (9)	0.0154 (3)
C4	0.4715 (2)	−0.08568 (12)	0.33334 (9)	0.0155 (2)
C5	0.5964 (2)	−0.18255 (12)	0.33741 (10)	0.0169 (2)
H5	0.7380	−0.1831	0.3130	0.020*
C6	0.5153 (3)	−0.27897 (12)	0.37712 (9)	0.0190 (3)
H6	0.6021	−0.3451	0.3803	0.023*
C7	0.3081 (3)	−0.27882 (14)	0.41209 (9)	0.0208 (3)
H7	0.2528	−0.3447	0.4394	0.025*
C8	0.1815 (3)	−0.18222 (14)	0.40706 (10)	0.0221 (3)
H8	0.0387	−0.1823	0.4304	0.026*
C9	0.2623 (2)	−0.08596 (14)	0.36827 (10)	0.0204 (3)
H9	0.1755	−0.0198	0.3653	0.025*
C10	0.7241 (3)	0.05758 (13)	0.44793 (10)	0.0189 (3)
H10A	0.8343	0.0006	0.4342	0.028*
H10B	0.6043	0.0221	0.4796	0.028*
H10C	0.7889	0.1169	0.4840	0.028*
C11	0.7753 (3)	0.35377 (13)	0.38865 (10)	0.0211 (3)
H11A	0.7344	0.3184	0.4439	0.032*
H11B	0.6474	0.3592	0.3510	0.032*
H11C	0.8327	0.4295	0.3997	0.032*

	U11	U22	U33	U12	U13	U23
S1	0.01616 (15)	0.01850 (15)	0.01696 (15)	−0.00282 (12)	−0.00025 (12)	0.00138 (12)
N1	0.0135 (5)	0.0171 (5)	0.0154 (5)	−0.0015 (4)	0.0024 (4)	0.0005 (4)
O1	0.0169 (5)	0.0178 (5)	0.0179 (5)	−0.0019 (4)	0.0058 (4)	−0.0002 (4)
O2	0.0158 (5)	0.0222 (5)	0.0202 (5)	0.0013 (4)	0.0045 (4)	0.0026 (4)
O3	0.0191 (5)	0.0288 (6)	0.0245 (5)	0.0005 (5)	−0.0068 (4)	−0.0011 (5)
C1	0.0114 (6)	0.0180 (6)	0.0174 (6)	0.0006 (5)	0.0021 (5)	0.0025 (5)
C2	0.0136 (6)	0.0147 (6)	0.0172 (6)	0.0011 (5)	0.0045 (5)	0.0010 (5)
C3	0.0147 (6)	0.0162 (6)	0.0152 (6)	0.0017 (5)	−0.0004 (5)	0.0027 (5)
C4	0.0133 (5)	0.0183 (6)	0.0149 (5)	−0.0014 (5)	−0.0004 (5)	0.0014 (5)
C5	0.0160 (6)	0.0185 (6)	0.0160 (6)	−0.0004 (5)	0.0011 (5)	−0.0016 (5)
C6	0.0243 (7)	0.0161 (6)	0.0166 (6)	−0.0003 (6)	−0.0016 (5)	−0.0021 (5)
C7	0.0245 (7)	0.0225 (7)	0.0155 (6)	−0.0078 (6)	−0.0025 (5)	0.0029 (6)
C8	0.0148 (6)	0.0311 (8)	0.0203 (7)	−0.0040 (6)	0.0007 (5)	0.0065 (6)
C9	0.0140 (6)	0.0252 (7)	0.0221 (7)	0.0015 (6)	−0.0004 (5)	0.0060 (6)
C10	0.0229 (7)	0.0185 (7)	0.0153 (6)	−0.0003 (6)	0.0031 (6)	0.0003 (5)
C11	0.0240 (7)	0.0173 (6)	0.0220 (7)	0.0020 (6)	0.0001 (6)	0.0004 (6)

S1—O3	1.4783 (12)	C5—C6	1.389 (2)
S1—N1	1.6948 (13)	C5—H5	0.9500
S1—C11	1.7882 (16)	C6—C7	1.385 (2)
N1—C3	1.3791 (18)	C6—H6	0.9500
N1—C2	1.4716 (18)	C7—C8	1.387 (2)
O1—C3	1.3428 (17)	C7—H7	0.9500
O1—C1	1.4534 (16)	C8—C9	1.380 (2)
O2—C3	1.2056 (17)	C8—H8	0.9500
C1—C4	1.4952 (19)	C9—H9	0.9500
C1—C2	1.547 (2)	C10—H10A	0.9800
C1—H1	1.0000	C10—H10B	0.9800
C2—C10	1.517 (2)	C10—H10C	0.9800
C2—H2	1.0000	C11—H11A	0.9800
C4—C5	1.3832 (19)	C11—H11B	0.9800
C4—C9	1.396 (2)	C11—H11C	0.9800
O3—S1—N1	109.93 (7)	C4—C5—H5	119.9
O3—S1—C11	106.55 (7)	C6—C5—H5	119.9
N1—S1—C11	95.73 (7)	C7—C6—C5	120.08 (14)
C3—N1—C2	110.71 (12)	C7—C6—H6	120.0
C3—N1—S1	116.62 (10)	C5—C6—H6	120.0
C2—N1—S1	129.58 (10)	C6—C7—C8	119.83 (14)
C3—O1—C1	109.49 (11)	C6—C7—H7	120.1
O1—C1—C4	110.13 (11)	C8—C7—H7	120.1
O1—C1—C2	104.16 (11)	C9—C8—C7	120.21 (14)
C4—C1—C2	115.28 (11)	C9—C8—H8	119.9
O1—C1—H1	109.0	C7—C8—H8	119.9
C4—C1—H1	109.0	C8—C9—C4	120.09 (14)
C2—C1—H1	109.0	C8—C9—H9	120.0
N1—C2—C10	112.29 (12)	C4—C9—H9	120.0
N1—C2—C1	98.58 (11)	C2—C10—H10A	109.5
C10—C2—C1	114.99 (12)	C2—C10—H10B	109.5
N1—C2—H2	110.2	H10A—C10—H10B	109.5
C10—C2—H2	110.2	C2—C10—H10C	109.5
C1—C2—H2	110.2	H10A—C10—H10C	109.5
O2—C3—O1	123.30 (13)	H10B—C10—H10C	109.5
O2—C3—N1	127.34 (14)	S1—C11—H11A	109.5
O1—C3—N1	109.34 (11)	S1—C11—H11B	109.5
C5—C4—C9	119.60 (13)	H11A—C11—H11B	109.5
C5—C4—C1	122.67 (12)	S1—C11—H11C	109.5
C9—C4—C1	117.65 (13)	H11A—C11—H11C	109.5
C4—C5—C6	120.18 (13)	H11B—C11—H11C	109.5
O3—S1—N1—C3	−88.16 (11)	C2—N1—C3—O2	−165.15 (14)
C11—S1—N1—C3	161.92 (11)	S1—N1—C3—O2	−3.1 (2)
O3—S1—N1—C2	69.87 (14)	C2—N1—C3—O1	13.73 (15)
C11—S1—N1—C2	−40.05 (14)	S1—N1—C3—O1	175.77 (9)
C3—O1—C1—C4	−145.05 (12)	O1—C1—C4—C5	19.91 (18)
C3—O1—C1—C2	−20.89 (14)	C2—C1—C4—C5	−97.55 (16)
C3—N1—C2—C10	96.80 (14)	O1—C1—C4—C9	−163.13 (12)
S1—N1—C2—C10	−62.25 (16)	C2—C1—C4—C9	79.41 (16)
C3—N1—C2—C1	−24.78 (14)	C9—C4—C5—C6	−0.9 (2)
S1—N1—C2—C1	176.17 (11)	C1—C4—C5—C6	175.97 (13)
O1—C1—C2—N1	26.31 (13)	C4—C5—C6—C7	0.6 (2)
C4—C1—C2—N1	147.08 (12)	C5—C6—C7—C8	0.2 (2)
O1—C1—C2—C10	−93.27 (14)	C6—C7—C8—C9	−0.8 (2)
C4—C1—C2—C10	27.50 (17)	C7—C8—C9—C4	0.5 (2)
C1—O1—C3—O2	−175.68 (13)	C5—C4—C9—C8	0.4 (2)
C1—O1—C3—N1	5.38 (15)	C1—C4—C9—C8	−176.66 (14)