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The crystal structure of the title compound, C12H21NO4, has been determined. The conformation in the solid state is compared to the transition state in nucleophilic addition reactions predicted by the Felkin-Anh model.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802002477/cv6085sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802002477/cv6085Isup2.hkl
Contains datablock I

CCDC reference: 183776

Key indicators

  • Single-crystal X-ray study
  • T = 123 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.038
  • wR factor = 0.104
  • Data-to-parameter ratio = 21.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: COLLECT (Nonius, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97.

tert-Butyl 4-acetyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate top
Crystal data top
C12H21NO4F(000) = 528
Mr = 243.30Dx = 1.174 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 18700 reflections
a = 13.6452 (5) Åθ = 1–28.3°
b = 10.1594 (5) ŵ = 0.09 mm1
c = 10.0848 (4) ÅT = 123 K
β = 100.163 (2)°Prisms, colourless
V = 1376.09 (10) Å30.45 × 0.30 × 0.15 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
2879 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
Graphite monochromatorθmax = 28.3°, θmin = 3.0°
rotation in φ and ω (2°) scansh = 1818
18786 measured reflectionsk = 1313
3392 independent reflectionsl = 1313
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0517P)2 + 0.2788P]
where P = (Fo2 + 2Fc2)/3
3392 reflections(Δ/σ)max < 0.001
155 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.26 e Å3
Special details top

Experimental. dx = 40 mm, 120 sec./°, 2 °., 5 sets, 274 frames, mos.= 0.661 (2) °.

TLC: 10:1 cyclohexane-ethyl acetate, Rf: 0.15; 1H-NMR (400 MHz, CDCl3, mixture of rotamers): δ 1.34 - 1.61 (m, 15H; CH3), 2.10 (m, 3H; COCH3), 3.85 (dd, J = 3.0 Hz, J = 9.4 Hz, 1H; H-5a), 4.07 (dd, J = 7.6 Hz, J = 9.4 Hz, 1H; H-5b), 4.23 (dd, J = 3.0 Hz, J = 7.6 Hz, 1H; H-4); 13C-NMR (100 MHz, CDCl3, mixture of rotamers): δ 23.46 (COCH3), 25.77, 26.11, 26.20, 28.09 and 28.10 (CH3), 64.91 (C-4), 65.41 (C-5), 80.60 (C(CH3)3), 94.81 (C-2), 151.13 (NCO), 206.11 (COCH3); elemental analyses (%): C12H21NO4 (243.28): calc.: C 59.24, H 8.70, N 5.76; found: C 59.11, H 8.76, N 5.90; FAB-MS (3-Nitrobenzoic acid): 244.1 (M+H)+.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.59623 (6)0.72722 (9)0.66002 (8)0.0376 (2)
O20.87852 (5)0.58418 (7)0.71822 (8)0.03025 (19)
O30.81878 (5)0.76638 (7)0.59736 (7)0.02400 (17)
O40.61279 (5)0.42996 (7)0.50018 (8)0.02846 (18)
C10.65940 (7)0.64629 (10)0.46822 (10)0.0215 (2)
H10.68970.70000.40280.026*
C110.59243 (7)0.73206 (10)0.53929 (10)0.0245 (2)
C120.52408 (9)0.82412 (11)0.45065 (12)0.0330 (3)
H12A0.46570.84270.49190.050*
H12B0.50260.78340.36220.050*
H12C0.55920.90650.43990.050*
N20.73619 (6)0.57901 (8)0.56148 (8)0.02250 (19)
C210.81696 (7)0.63927 (10)0.63436 (10)0.0223 (2)
C220.89930 (7)0.85519 (10)0.66076 (10)0.0238 (2)
C231.00106 (8)0.80249 (12)0.64504 (13)0.0347 (3)
H23A1.00330.79070.54920.052*
H23B1.01270.71770.69150.052*
H23C1.05270.86520.68430.052*
C240.87587 (9)0.98012 (11)0.58031 (12)0.0366 (3)
H24A0.88170.96390.48620.055*
H24B0.92281.04920.61770.055*
H24C0.80781.00830.58480.055*
C250.89144 (10)0.87565 (13)0.80714 (11)0.0380 (3)
H25A0.90680.79300.85660.057*
H25B0.82360.90340.81350.057*
H25C0.93880.94370.84610.057*
C30.71045 (7)0.43952 (10)0.58056 (11)0.0259 (2)
C310.69978 (9)0.40783 (12)0.72429 (12)0.0346 (3)
H31A0.76510.41350.78290.052*
H31B0.67320.31850.72820.052*
H31C0.65410.47090.75470.052*
C320.78226 (9)0.34808 (11)0.52649 (13)0.0364 (3)
H32A0.84850.35580.58220.055*
H32B0.78570.37240.43340.055*
H32C0.75880.25710.52900.055*
C50.60364 (7)0.52779 (10)0.39727 (10)0.0254 (2)
H5A0.53290.54950.36370.031*
H5B0.63460.49800.32080.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0370 (4)0.0510 (5)0.0254 (4)0.0041 (4)0.0070 (3)0.0054 (4)
O20.0261 (4)0.0262 (4)0.0344 (4)0.0026 (3)0.0059 (3)0.0069 (3)
O30.0227 (3)0.0203 (3)0.0271 (4)0.0042 (3)0.0011 (3)0.0033 (3)
O40.0247 (4)0.0249 (4)0.0326 (4)0.0055 (3)0.0038 (3)0.0031 (3)
C10.0203 (4)0.0226 (5)0.0207 (4)0.0003 (3)0.0014 (4)0.0011 (4)
C110.0233 (5)0.0236 (5)0.0266 (5)0.0034 (4)0.0043 (4)0.0029 (4)
C120.0342 (6)0.0254 (5)0.0407 (6)0.0064 (4)0.0099 (5)0.0018 (5)
N20.0207 (4)0.0194 (4)0.0256 (4)0.0014 (3)0.0008 (3)0.0028 (3)
C210.0213 (4)0.0213 (5)0.0240 (5)0.0017 (4)0.0033 (4)0.0016 (4)
C220.0251 (5)0.0223 (5)0.0234 (5)0.0069 (4)0.0024 (4)0.0001 (4)
C230.0256 (5)0.0347 (6)0.0438 (7)0.0078 (4)0.0063 (5)0.0046 (5)
C240.0429 (6)0.0240 (5)0.0400 (6)0.0079 (5)0.0003 (5)0.0056 (5)
C250.0490 (7)0.0393 (7)0.0271 (5)0.0123 (5)0.0106 (5)0.0047 (5)
C30.0234 (5)0.0205 (5)0.0312 (5)0.0041 (4)0.0025 (4)0.0020 (4)
C310.0340 (6)0.0331 (6)0.0343 (6)0.0093 (5)0.0008 (5)0.0099 (5)
C320.0349 (6)0.0250 (5)0.0462 (7)0.0041 (4)0.0018 (5)0.0029 (5)
C50.0250 (5)0.0247 (5)0.0250 (5)0.0004 (4)0.0003 (4)0.0015 (4)
Geometric parameters (Å, º) top
O1—C111.2104 (13)C23—H23A0.9800
O2—C211.2179 (12)C23—H23B0.9800
O3—C211.3456 (12)C23—H23C0.9800
O3—C221.4773 (11)C24—H24A0.9800
O4—C51.4264 (13)C24—H24B0.9800
O4—C31.4357 (12)C24—H24C0.9800
C1—N21.4498 (12)C25—H25A0.9800
C1—C111.5295 (14)C25—H25B0.9800
C1—C51.5323 (13)C25—H25C0.9800
C1—H11.0000C3—C311.5167 (16)
C11—C121.4999 (15)C3—C321.5196 (16)
C12—H12A0.9800C31—H31A0.9800
C12—H12B0.9800C31—H31B0.9800
C12—H12C0.9800C31—H31C0.9800
N2—C211.3578 (12)C32—H32A0.9800
N2—C31.4807 (13)C32—H32B0.9800
C22—C241.5099 (15)C32—H32C0.9800
C22—C251.5132 (15)C5—H5A0.9900
C22—C231.5223 (15)C5—H5B0.9900
C21—O3—C22120.99 (7)C22—C24—H24B109.5
C5—O4—C3108.48 (7)H24A—C24—H24B109.5
N2—C1—C11112.81 (8)C22—C24—H24C109.5
N2—C1—C5100.08 (8)H24A—C24—H24C109.5
C11—C1—C5112.20 (8)H24B—C24—H24C109.5
N2—C1—H1110.5C22—C25—H25A109.5
C11—C1—H1110.5C22—C25—H25B109.5
C5—C1—H1110.5H25A—C25—H25B109.5
O1—C11—C12122.46 (10)C22—C25—H25C109.5
O1—C11—C1121.68 (9)H25A—C25—H25C109.5
C12—C11—C1115.85 (9)H25B—C25—H25C109.5
C11—C12—H12A109.5O4—C3—N2102.08 (7)
C11—C12—H12B109.5O4—C3—C31106.81 (8)
H12A—C12—H12B109.5N2—C3—C31113.10 (9)
C11—C12—H12C109.5O4—C3—C32110.43 (9)
H12A—C12—H12C109.5N2—C3—C32110.83 (9)
H12B—C12—H12C109.5C31—C3—C32112.95 (9)
C21—N2—C1124.28 (8)C3—C31—H31A109.5
C21—N2—C3123.35 (8)C3—C31—H31B109.5
C1—N2—C3112.00 (7)H31A—C31—H31B109.5
O2—C21—O3126.11 (9)C3—C31—H31C109.5
O2—C21—N2124.27 (9)H31A—C31—H31C109.5
O3—C21—N2109.60 (8)H31B—C31—H31C109.5
O3—C22—C24102.12 (8)C3—C32—H32A109.5
O3—C22—C25109.31 (8)C3—C32—H32B109.5
C24—C22—C25111.35 (10)H32A—C32—H32B109.5
O3—C22—C23111.25 (8)C3—C32—H32C109.5
C24—C22—C23110.50 (9)H32A—C32—H32C109.5
C25—C22—C23111.90 (9)H32B—C32—H32C109.5
C22—C23—H23A109.5O4—C5—C1103.61 (8)
C22—C23—H23B109.5O4—C5—H5A111.0
H23A—C23—H23B109.5C1—C5—H5A111.0
C22—C23—H23C109.5O4—C5—H5B111.0
H23A—C23—H23C109.5C1—C5—H5B111.0
H23B—C23—H23C109.5H5A—C5—H5B109.0
C22—C24—H24A109.5
N2—C1—C11—O19.76 (14)C21—O3—C22—C2566.93 (12)
C5—C1—C11—O1102.38 (11)C21—O3—C22—C2357.14 (12)
N2—C1—C11—C12168.83 (9)C5—O4—C3—N225.74 (10)
C5—C1—C11—C1279.04 (11)C5—O4—C3—C31144.67 (9)
C11—C1—N2—C2172.11 (12)C5—O4—C3—C3292.16 (10)
C5—C1—N2—C21168.47 (9)C21—N2—C3—O4170.20 (9)
C11—C1—N2—C3101.07 (10)C1—N2—C3—O43.05 (11)
C5—C1—N2—C318.35 (10)C21—N2—C3—C3155.82 (13)
C22—O3—C21—O21.14 (15)C1—N2—C3—C31117.43 (9)
C22—O3—C21—N2179.84 (8)C21—N2—C3—C3272.19 (12)
C1—N2—C21—O2175.70 (10)C1—N2—C3—C32114.56 (9)
C3—N2—C21—O23.27 (16)C3—O4—C5—C138.01 (10)
C1—N2—C21—O35.57 (13)N2—C1—C5—O433.05 (9)
C3—N2—C21—O3177.99 (9)C11—C1—C5—O486.81 (9)
C21—O3—C22—C24175.04 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C23—H23C···O2i0.982.543.4630 (14)156
C24—H24A···O2ii0.982.743.7160 (15)175
C1—H1···O1ii1.002.663.3330 (12)125
C12—H12B···O1ii0.982.593.2939 (15)129
Symmetry codes: (i) x+2, y+1/2, z+3/2; (ii) x, y+3/2, z1/2.
 

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