(4S,5S)-4-Methyl-5-(4-tolyl­thio­carbonyl)­oxazolidin-2-one

The title compound, C₁₂H₁₃NO₃S, is the product of a stereoselective epoxidation reaction, followed by cyclization and hydro­lysis of the resulting epoxide. The heterocyclic ring is slightly twisted. Molecules are linked into a chain through intermolecular N—H...O=C hydrogen-bonding interactions.

Key indicators

• Single-crystal X-ray study
• T = 160 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.027
• wR factor = 0.068
• Data-to-parameter ratio = 10.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



THETM_01  Alert B The value of sine(theta_max)/wavelength is less than 0.575
          Calculated sin(theta_max)/wavelength =    0.5543

Author response: The relatively low \q~max~ value is due to a short crystal-detector distance for this data collection, which was carried out before parameters were optimised for one of the first commercial CCD detector systems. This precise text is given in the Experimental section, which will be published so there is no attempt to hide the minor shortcoming. The data/parameter ratio is still excellent.

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           23.20
         From the CIF: _reflns_number_total               1718
         Count of symmetry unique reflns         1039
         Completeness (_total/calc)            165.35%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured       679
         Fraction of Friedel pairs measured     0.654
         Are heavy atom types Z>Si present          yes
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.


 0 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 0 Alert Level C = Please check

---

Computing details

Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXTL (Sheldrick, 1994); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

(4S,5S)-4-Methyl-5-(4-tolylthiocarbonyl)oxazolidin-2-one

Crystal data

C12H13NO3S	Dx = 1.396 Mg m^−3
Mr = 251.29	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 297 reflections
a = 5.5614 (7) Å	θ = 1.0–23.3°
b = 7.810 (1) Å	µ = 0.27 mm^−1
c = 27.520 (5) Å	T = 160 K
V = 1195.3 (3) Å^3	Block, colourless
Z = 4	0.80 × 0.64 × 0.32 mm
F(000) = 528

Data collection

Siemens SMART 1K CCD diffractometer	1718 independent reflections
Radiation source: sealed tube	1714 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
Detector resolution: 8.192 pixels mm^-1	θmax = 23.2°, θmin = 2.7°
ω rotation with narrow frames scans	h = −6→5
Absorption correction: multi-scan (XPREP in SHELXTL; Sheldrick, 1994)	k = −8→8
Tmin = 0.816, Tmax = 0.891	l = −30→28
4745 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.027	w = 1/[σ^2(Fo^2) + (0.0296P)^2 + 0.3596P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.068	(Δ/σ)max < 0.001
S = 1.11	Δρmax = 0.13 e Å^−3
1718 reflections	Δρmin = −0.16 e Å^−3
160 parameters	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.019 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 669 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.02 (8)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.3723 (3)	0.47104 (18)	0.23386 (5)	0.0327 (4)
C1	0.1963 (4)	0.3595 (2)	0.24743 (7)	0.0275 (5)
N1	0.2229 (3)	0.2127 (2)	0.22354 (6)	0.0303 (4)
H1	0.126 (4)	0.136 (3)	0.2264 (8)	0.036*
C2	0.4005 (4)	0.2215 (2)	0.18450 (7)	0.0288 (4)
H2	0.5139	0.1225	0.1869	0.035*
C3	0.5304 (4)	0.3890 (3)	0.19932 (7)	0.0303 (5)
H3	0.6853	0.3596	0.2158	0.036*
O2	0.0457 (3)	0.40069 (18)	0.27713 (5)	0.0355 (4)
C4	0.5814 (4)	0.5099 (3)	0.15732 (8)	0.0332 (5)
C5	0.2783 (4)	0.2214 (3)	0.13498 (8)	0.0386 (5)
H5A	0.4007	0.2260	0.1094	0.058*
H5B	0.1728	0.3214	0.1323	0.058*
H5C	0.1829	0.1167	0.1313	0.058*
O3	0.7293 (3)	0.4769 (2)	0.12699 (6)	0.0516 (5)
S1	0.39861 (10)	0.69690 (7)	0.158576 (19)	0.03326 (18)
C6	0.4932 (4)	0.8012 (3)	0.10469 (7)	0.0300 (5)
C7	0.7080 (4)	0.8931 (3)	0.10326 (8)	0.0339 (5)
H7	0.8151	0.8905	0.1301	0.041*
C8	0.7637 (4)	0.9882 (3)	0.06227 (7)	0.0332 (5)
H8	0.9099	1.0510	0.0615	0.040*
C9	0.6114 (4)	0.9940 (3)	0.02233 (7)	0.0312 (5)
C10	0.3996 (4)	0.8996 (3)	0.02400 (7)	0.0331 (5)
H10	0.2938	0.9005	−0.0031	0.040*
C11	0.3407 (4)	0.8040 (3)	0.06487 (7)	0.0329 (5)
H11	0.1953	0.7402	0.0655	0.040*
C12	0.6737 (4)	1.1007 (3)	−0.02169 (8)	0.0400 (5)
H12A	0.5457	1.0901	−0.0460	0.060*
H12B	0.8257	1.0604	−0.0356	0.060*
H12C	0.6901	1.2210	−0.0121	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0425 (8)	0.0290 (7)	0.0265 (7)	−0.0063 (7)	0.0041 (7)	−0.0030 (6)
C1	0.0318 (11)	0.0260 (11)	0.0247 (10)	0.0014 (9)	−0.0031 (9)	0.0030 (9)
N1	0.0338 (9)	0.0250 (9)	0.0322 (9)	−0.0038 (9)	0.0036 (8)	−0.0020 (8)
C2	0.0362 (10)	0.0253 (10)	0.0249 (10)	0.0078 (10)	−0.0013 (9)	−0.0005 (8)
C3	0.0272 (11)	0.0356 (11)	0.0282 (11)	0.0023 (9)	0.0010 (8)	0.0022 (9)
O2	0.0423 (9)	0.0326 (8)	0.0317 (8)	0.0072 (7)	0.0097 (7)	0.0034 (6)
C4	0.0317 (11)	0.0317 (11)	0.0363 (11)	0.0013 (10)	0.0034 (11)	0.0017 (10)
C5	0.0517 (14)	0.0327 (11)	0.0314 (11)	0.0062 (11)	−0.0065 (11)	−0.0014 (9)
O3	0.0504 (10)	0.0457 (10)	0.0587 (11)	0.0171 (9)	0.0287 (10)	0.0151 (8)
S1	0.0380 (3)	0.0288 (3)	0.0330 (3)	0.0028 (3)	0.0091 (3)	0.0020 (2)
C6	0.0330 (11)	0.0255 (10)	0.0316 (11)	0.0036 (10)	0.0042 (9)	0.0010 (9)
C7	0.0358 (12)	0.0341 (11)	0.0317 (11)	0.0007 (10)	−0.0025 (9)	0.0025 (10)
C8	0.0313 (11)	0.0352 (11)	0.0331 (11)	−0.0043 (10)	0.0047 (9)	0.0014 (9)
C9	0.0363 (11)	0.0264 (10)	0.0309 (10)	0.0051 (10)	0.0026 (10)	−0.0002 (9)
C10	0.0377 (11)	0.0306 (11)	0.0310 (10)	0.0041 (11)	−0.0047 (10)	−0.0019 (9)
C11	0.0316 (12)	0.0278 (11)	0.0394 (12)	−0.0019 (10)	0.0008 (9)	−0.0048 (10)
C12	0.0487 (14)	0.0373 (12)	0.0342 (11)	0.0005 (11)	0.0012 (10)	0.0058 (10)

Geometric parameters (Å, º)

O1—C1	1.362 (2)	S1—C6	1.772 (2)
O1—C3	1.445 (2)	C6—C7	1.394 (3)
C1—N1	1.330 (3)	C6—C11	1.386 (3)
C1—O2	1.214 (2)	C7—H7	0.950
N1—H1	0.81 (2)	C7—C8	1.386 (3)
N1—C2	1.461 (3)	C8—H8	0.950
C2—H2	1.000	C8—C9	1.388 (3)
C2—C3	1.549 (3)	C9—C10	1.391 (3)
C2—C5	1.523 (3)	C9—C12	1.511 (3)
C3—H3	1.000	C10—H10	0.950
C3—C4	1.519 (3)	C10—C11	1.389 (3)
C4—O3	1.200 (3)	C11—H11	0.950
C4—S1	1.780 (2)	C12—H12A	0.980
C5—H5A	0.980	C12—H12B	0.980
C5—H5B	0.980	C12—H12C	0.980
C5—H5C	0.980
C1—O1—C3	109.51 (15)	H5B—C5—H5C	109.5
O1—C1—N1	109.61 (17)	C4—S1—C6	101.04 (10)
O1—C1—O2	120.73 (17)	S1—C6—C7	120.98 (16)
N1—C1—O2	129.67 (19)	S1—C6—C11	119.14 (16)
C1—N1—H1	120.9 (17)	C7—C6—C11	119.62 (18)
C1—N1—C2	113.50 (17)	C6—C7—H7	120.3
H1—N1—C2	123.8 (17)	C6—C7—C8	119.4 (2)
N1—C2—H2	109.9	H7—C7—C8	120.3
N1—C2—C3	99.26 (15)	C7—C8—H8	119.1
N1—C2—C5	110.89 (18)	C7—C8—C9	121.7 (2)
H2—C2—C3	109.9	H8—C8—C9	119.1
H2—C2—C5	109.9	C8—C9—C10	118.24 (18)
C3—C2—C5	116.37 (17)	C8—C9—C12	120.87 (19)
O1—C3—C2	105.30 (15)	C10—C9—C12	120.9 (2)
O1—C3—H3	109.1	C9—C10—H10	119.6
O1—C3—C4	109.76 (17)	C9—C10—C11	120.76 (19)
C2—C3—H3	109.1	H10—C10—C11	119.6
C2—C3—C4	114.30 (16)	C6—C11—C10	120.27 (19)
H3—C3—C4	109.1	C6—C11—H11	119.9
C3—C4—O3	121.55 (19)	C10—C11—H11	119.9
C3—C4—S1	112.89 (15)	C9—C12—H12A	109.5
O3—C4—S1	125.56 (17)	C9—C12—H12B	109.5
C2—C5—H5A	109.5	C9—C12—H12C	109.5
C2—C5—H5B	109.5	H12A—C12—H12B	109.5
C2—C5—H5C	109.5	H12A—C12—H12C	109.5
H5A—C5—H5B	109.5	H12B—C12—H12C	109.5
H5A—C5—H5C	109.5
C3—O1—C1—N1	−1.7 (2)	C2—C3—C4—S1	108.87 (17)
C3—O1—C1—O2	178.46 (18)	C3—C4—S1—C6	−177.59 (15)
O1—C1—N1—C2	−10.0 (2)	O3—C4—S1—C6	1.7 (2)
O2—C1—N1—C2	169.9 (2)	C4—S1—C6—C7	−78.60 (19)
C1—N1—C2—C3	15.9 (2)	C4—S1—C6—C11	107.20 (18)
C1—N1—C2—C5	−107.0 (2)	S1—C6—C7—C8	−173.07 (17)
C1—O1—C3—C2	11.49 (19)	C11—C6—C7—C8	1.1 (3)
C1—O1—C3—C4	134.98 (17)	C6—C7—C8—C9	−0.3 (3)
N1—C2—C3—O1	−15.57 (18)	C7—C8—C9—C10	−0.7 (3)
N1—C2—C3—C4	−136.11 (17)	C7—C8—C9—C12	179.0 (2)
C5—C2—C3—O1	103.38 (19)	C8—C9—C10—C11	0.9 (3)
C5—C2—C3—C4	−17.2 (2)	C12—C9—C10—C11	−178.9 (2)
O1—C3—C4—O3	171.6 (2)	S1—C6—C11—C10	173.35 (16)
O1—C3—C4—S1	−9.2 (2)	C7—C6—C11—C10	−0.9 (3)
C2—C3—C4—O3	−70.4 (3)	C9—C10—C11—C6	−0.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^i	0.81 (2)	2.07 (2)	2.859 (2)	163 (2)

Symmetry code: (i) −x, y−1/2, −z+1/2.