organic compounds
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—HO=C hydrogen-bonding interactions.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802010711/bt6151sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802010711/bt6151Isup2.hkl |
CCDC reference: 189902
Key indicators
- Single-crystal X-ray study
- T = 160 K
- Mean (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 top
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 top
Crystal data top
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) Å3 | Block, colourless |
Z = 4 | 0.80 × 0.64 × 0.32 mm |
F(000) = 528 |
Data collection top
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 top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.027 | w = 1/[σ2(Fo2) + (0.0296P)2 + 0.3596P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 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+0.001xFc2λ3/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 (Å2) top
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 (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.81 (2) | 2.07 (2) | 2.859 (2) | 163 (2) |
Symmetry code: (i) −x, y−1/2, −z+1/2. |