Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807050295/hb2580sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807050295/hb2580Isup2.hkl |
CCDC reference: 669140
To a solution of (S)-4-isopropyl-5,5-diphenyl-3-propionyloxazolidin-2-one (1.6 g, 4.8 mmol, 1.0 eq) in 20 ml dry THF was added dropwise via syringe a freshly prepared solution of lithium diisoproylamide (6.2 mmol, 1.3 eq) in 12 ml dry THF at 195 K. The solution was stirred at 195 K for 30 min and then a solution of 1.4 g (6.2 mmol dry ZnBr2 in 12 ml dry THF was added via syringe at 195 K. After stirring for 30 min at 195 K 5.1 ml (50 mmol, 10 eq) 3-bromo-2-methylprop-1-ene were added in one portion via syringe. The mixture was allowed to warm to 258 K and stirred at 258 K for 20 h, treated with 20 ml saturated aqueous NH4Cl solution and diluted with 50 ml Et2O. The organic layer was separated and washed with 5% aqueous HCl solution (2 × 20 ml), 5% aqueous NaOH solution (2 × 20 ml) and brine (1 × 15 ml). The solution was dried with MgSO4, filtered and concentrated to give 1.9 g of a light yellow solid. Recrystallization with Et2O/pentane afforded 1.4 g (75%) of (I) as colourless blocks.
[α]273D -190.5 (c 1.0, CHCl3); mp 392.5–393.0 K; Rf = 0.43 (cyclohexane/ethyl acetate 19:1); 1H NMR (500.1 MHz, CDCl3) δ = 7.46 (d, J = 8.2 Hz, 2H), 7.40 (d, J = 7.7 Hz, 2H), 7.34 (dd, J = 16.4, 8.1 Hz, 4H), 7.30–7.25 (m, 2H, p-phenyl), 5.38 (d, J = 3.0 Hz, 1H, NCH) 4.77 (s, 1H, =CHH), 4.74 (s, 1H, =CHH), 3.96–3.87 (m, 1H, O=C—CH), 2.57 (dd, J = 14.0, 7.2 Hz, 1H, CHH), 2.02 (dd, J = 14.0, 7.5 Hz, 1H, CHH), 1.99–1.92 (m, 1H, CH3—CH-CH3), 1.76 (s, 3H, =C—CH3), 0.86 (d, J = 7.0 Hz, 3H, O=C—C—CH3), 0.80 (d, J = 6.8 Hz, 3H, CH3-CH—CH3), 0.76 (d, J = 6.7 Hz, 3H, CH3—CH—CH3); 13C NMR (125.8 MHz, CDCl3) δ = 176.6 (C=O), 152.9 (C=O), 143.0 (quart. arom. C), 142.4 (quart. arom. C), 138.2 (C=CH2), 128.8 (2x, arom. CH), 128.5 (arom. CH), 128.4 (2x, arom. CH), 127.9 (arom. CH), 125.9 (2x, arom. CH), 125.6 (2x, arom. CH), 112.2 (C=CH2), 64.5 (CH), 41.7 (CH2), 35.4 (CH), 29.8 (CH), 22.2 (CH3), 21.7 (CH3), 16.3 (CH3), 16.3(CH3); HRMS (FAB): m/z calculated for C25H30NO3; [M+H]+: 392.2220; found: 392.2244.
Anomalous dispersion was negligible and Friedel pairs were merged before refinement.
The H atoms were placed in calculated positions, with C—H = 0.93–0.98 Å and were refined as riding, with Uiso(H)= 1.5Ueq(C) for methyl and 1.2Ueq(C) for all other H atoms; the methyl groups were allowed to rotate but not to tip to best fit the electron density.
The title compound, (I), was synthesized in the course of the generation of depsipeptide libraries resembling the Jasplakinolide family of natural products (Hu et al., 2007). The relative configuration of (I) is in accordance with the model for diastereoselective alkylation of acylated chiral oxazolidinones derived from amino acids (Evans & Takacs, 1980) and their modified diphenyl analogs (Hintermann & Seebach, 1998). The stereogenic centres were assigned based on the known chirality of the starting material (C3 S and C7 R).
For related literature, see: Evans & Takacs (1980); Hintermann & Seebach (1998); Hu et al. (2007).
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003).
Fig. 1. : The molecular structure of (I). Displacement ellipsoids for the non-hydrogen atoms are shown at the 20% probability level. |
C25H29NO3 | F(000) = 840 |
Mr = 391.49 | Dx = 1.186 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 15624 reflections |
a = 8.7567 (11) Å | θ = 3.1–25.0° |
b = 10.0467 (17) Å | µ = 0.08 mm−1 |
c = 24.921 (5) Å | T = 291 K |
V = 2192.4 (6) Å3 | Block, colourless |
Z = 4 | 0.25 × 0.25 × 0.23 mm |
Nonius KappaCCD area-detector diffractometer | 628 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.064 |
Graphite monochromator | θmax = 25.0°, θmin = 3.1° |
Detector resolution: 19 vertical, 18 horizontal pixels mm-1 | h = −10→10 |
338 frames via ω–rotation (Δω = 1%) and two times 20 s per frame (three sets at different κ–angles) scans | k = −11→11 |
15624 measured reflections | l = −29→29 |
2223 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.086 | H-atom parameters constrained |
S = 1.01 | [1.0 exp(7.90(sinθ/λ)2)]/[σ2(Fo2)] |
2223 reflections | (Δ/σ)max < 0.001 |
262 parameters | Δρmax = 0.10 e Å−3 |
0 restraints | Δρmin = −0.13 e Å−3 |
C25H29NO3 | V = 2192.4 (6) Å3 |
Mr = 391.49 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 8.7567 (11) Å | µ = 0.08 mm−1 |
b = 10.0467 (17) Å | T = 291 K |
c = 24.921 (5) Å | 0.25 × 0.25 × 0.23 mm |
Nonius KappaCCD area-detector diffractometer | 628 reflections with I > 2σ(I) |
15624 measured reflections | Rint = 0.064 |
2223 independent reflections |
R[F2 > 2σ(F2)] = 0.032 | 0 restraints |
wR(F2) = 0.086 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.10 e Å−3 |
2223 reflections | Δρmin = −0.13 e Å−3 |
262 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.2130 (4) | 0.6030 (4) | 0.84026 (17) | 0.0393 (11) | |
O2 | 0.3031 (5) | 0.4620 (4) | 0.77804 (16) | 0.0449 (12) | |
O3 | 0.6121 (5) | 0.3935 (4) | 0.90646 (18) | 0.0455 (13) | |
N | 0.4382 (5) | 0.5084 (5) | 0.85736 (18) | 0.0387 (14) | |
C1 | 0.6965 (6) | 0.7027 (6) | 0.8894 (2) | 0.055 (2) | |
H1A | 0.7582 | 0.7774 | 0.8790 | 0.083* | |
H1B | 0.7215 | 0.6274 | 0.8674 | 0.083* | |
H1C | 0.7155 | 0.6816 | 0.9263 | 0.083* | |
C2 | 0.5262 (7) | 0.7379 (6) | 0.8820 (2) | 0.0410 (17) | |
H2A | 0.5021 | 0.8103 | 0.9069 | 0.049* | |
C3 | 0.4273 (6) | 0.6170 (6) | 0.8977 (2) | 0.0384 (17) | |
H3A | 0.4581 | 0.5839 | 0.9330 | 0.046* | |
C4 | 0.2510 (6) | 0.6376 (6) | 0.8961 (3) | 0.0402 (18) | |
C5 | 0.3168 (8) | 0.5165 (6) | 0.8208 (3) | 0.0427 (18) | |
C6 | 0.5360 (8) | 0.3987 (7) | 0.8662 (3) | 0.0458 (19) | |
C7 | 0.5342 (7) | 0.2882 (6) | 0.8239 (2) | 0.0381 (17) | |
H7A | 0.5001 | 0.3252 | 0.7896 | 0.046* | |
C8 | 0.6941 (7) | 0.2323 (6) | 0.8174 (2) | 0.0461 (19) | |
H8A | 0.6878 | 0.1522 | 0.7957 | 0.055* | |
H8B | 0.7316 | 0.2065 | 0.8525 | 0.055* | |
C9 | 0.8104 (8) | 0.3254 (7) | 0.7918 (3) | 0.049 (2) | |
C10 | 0.7793 (8) | 0.4454 (7) | 0.7734 (2) | 0.054 (2) | |
H10A | 0.6803 | 0.4785 | 0.7756 | 0.065* | |
H10B | 0.8563 | 0.4969 | 0.7583 | 0.065* | |
C11 | 0.4984 (7) | 0.7896 (6) | 0.8246 (2) | 0.052 (2) | |
H11A | 0.5617 | 0.8660 | 0.8182 | 0.078* | |
H11B | 0.3930 | 0.8142 | 0.8207 | 0.078* | |
H11C | 0.5230 | 0.7211 | 0.7992 | 0.078* | |
C12 | 0.4201 (6) | 0.1795 (6) | 0.8422 (2) | 0.057 (2) | |
H12A | 0.4171 | 0.1096 | 0.8160 | 0.086* | |
H12B | 0.3203 | 0.2178 | 0.8459 | 0.086* | |
H12C | 0.4524 | 0.1437 | 0.8761 | 0.086* | |
C13 | 0.9699 (7) | 0.2650 (6) | 0.7874 (2) | 0.062 (2) | |
H13A | 1.0378 | 0.3283 | 0.7711 | 0.093* | |
H13B | 0.9657 | 0.1862 | 0.7657 | 0.093* | |
H13C | 1.0067 | 0.2426 | 0.8225 | 0.093* | |
C21 | 0.1919 (7) | 0.7761 (7) | 0.9059 (3) | 0.0411 (17) | |
C22 | 0.2239 (7) | 0.8402 (7) | 0.9540 (3) | 0.048 (2) | |
H22A | 0.2860 | 0.7991 | 0.9794 | 0.057* | |
C23 | 0.1631 (7) | 0.9663 (7) | 0.9646 (3) | 0.055 (2) | |
H23A | 0.1856 | 1.0092 | 0.9967 | 0.066* | |
C24 | 0.0692 (8) | 1.0271 (7) | 0.9271 (3) | 0.058 (2) | |
H24A | 0.0279 | 1.1106 | 0.9340 | 0.070* | |
C25 | 0.0375 (8) | 0.9627 (7) | 0.8796 (3) | 0.059 (2) | |
H25A | −0.0237 | 1.0041 | 0.8540 | 0.071* | |
C26 | 0.0958 (7) | 0.8368 (7) | 0.8694 (3) | 0.049 (2) | |
H26A | 0.0701 | 0.7930 | 0.8378 | 0.059* | |
C27 | 0.1700 (7) | 0.5358 (6) | 0.9326 (3) | 0.0373 (17) | |
C28 | 0.0354 (7) | 0.4759 (6) | 0.9156 (2) | 0.0416 (17) | |
H28A | −0.0045 | 0.4956 | 0.8819 | 0.050* | |
C29 | −0.0390 (7) | 0.3871 (7) | 0.9487 (3) | 0.0485 (19) | |
H29A | −0.1289 | 0.3475 | 0.9369 | 0.058* | |
C30 | 0.0162 (7) | 0.3552 (6) | 0.9990 (3) | 0.052 (2) | |
H30A | −0.0341 | 0.2942 | 1.0208 | 0.062* | |
C31 | 0.1508 (8) | 0.4179 (7) | 1.0162 (3) | 0.056 (2) | |
H31A | 0.1902 | 0.3990 | 1.0500 | 0.067* | |
C32 | 0.2255 (7) | 0.5080 (7) | 0.9831 (3) | 0.049 (2) | |
H32A | 0.3137 | 0.5499 | 0.9952 | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.039 (3) | 0.041 (3) | 0.038 (3) | 0.006 (3) | 0.001 (2) | −0.005 (2) |
O2 | 0.048 (3) | 0.056 (3) | 0.031 (3) | 0.004 (3) | 0.000 (3) | −0.005 (3) |
O3 | 0.054 (3) | 0.039 (3) | 0.043 (3) | 0.005 (3) | −0.010 (3) | −0.005 (3) |
N | 0.038 (3) | 0.039 (4) | 0.039 (4) | 0.010 (3) | −0.005 (3) | −0.004 (3) |
C1 | 0.050 (4) | 0.056 (5) | 0.059 (5) | −0.011 (4) | 0.003 (4) | −0.006 (4) |
C2 | 0.047 (4) | 0.036 (4) | 0.040 (5) | 0.004 (4) | 0.004 (4) | −0.002 (4) |
C3 | 0.042 (4) | 0.041 (4) | 0.032 (4) | −0.004 (4) | −0.004 (3) | −0.009 (4) |
C4 | 0.039 (4) | 0.042 (5) | 0.040 (5) | 0.001 (4) | −0.007 (4) | −0.002 (4) |
C5 | 0.050 (5) | 0.035 (5) | 0.043 (5) | −0.008 (4) | −0.006 (5) | 0.010 (4) |
C6 | 0.043 (5) | 0.047 (5) | 0.047 (5) | −0.012 (5) | 0.018 (4) | −0.007 (5) |
C7 | 0.040 (4) | 0.039 (4) | 0.036 (5) | 0.011 (4) | 0.001 (4) | 0.001 (4) |
C8 | 0.059 (5) | 0.041 (4) | 0.038 (4) | 0.002 (4) | −0.007 (4) | −0.007 (4) |
C9 | 0.051 (5) | 0.050 (5) | 0.045 (5) | −0.005 (5) | 0.000 (4) | −0.011 (4) |
C10 | 0.065 (5) | 0.051 (5) | 0.047 (5) | 0.001 (4) | 0.010 (4) | −0.002 (4) |
C11 | 0.058 (5) | 0.042 (5) | 0.057 (5) | −0.001 (4) | 0.005 (4) | 0.003 (4) |
C12 | 0.056 (5) | 0.052 (5) | 0.063 (5) | −0.014 (4) | −0.007 (4) | −0.007 (4) |
C13 | 0.046 (5) | 0.075 (6) | 0.066 (6) | 0.002 (5) | −0.004 (4) | 0.005 (5) |
C21 | 0.041 (4) | 0.046 (5) | 0.037 (5) | 0.001 (4) | 0.015 (4) | 0.006 (4) |
C22 | 0.054 (5) | 0.047 (5) | 0.042 (5) | 0.004 (4) | 0.002 (4) | −0.002 (4) |
C23 | 0.061 (6) | 0.046 (5) | 0.058 (5) | −0.006 (5) | 0.015 (4) | −0.011 (5) |
C24 | 0.064 (5) | 0.043 (5) | 0.067 (6) | 0.010 (5) | 0.024 (5) | −0.005 (5) |
C25 | 0.066 (5) | 0.045 (5) | 0.067 (6) | 0.007 (5) | 0.008 (5) | 0.013 (5) |
C26 | 0.056 (5) | 0.041 (5) | 0.051 (5) | 0.011 (4) | 0.006 (4) | −0.012 (4) |
C27 | 0.039 (4) | 0.033 (4) | 0.039 (5) | 0.011 (4) | 0.005 (4) | 0.001 (4) |
C28 | 0.044 (4) | 0.037 (4) | 0.043 (4) | 0.010 (4) | −0.006 (4) | 0.001 (4) |
C29 | 0.047 (4) | 0.042 (5) | 0.056 (5) | −0.005 (4) | −0.011 (4) | −0.008 (4) |
C30 | 0.048 (5) | 0.047 (5) | 0.061 (6) | 0.005 (4) | 0.010 (4) | 0.005 (4) |
C31 | 0.062 (6) | 0.063 (6) | 0.041 (5) | −0.010 (5) | −0.011 (4) | 0.008 (4) |
C32 | 0.049 (5) | 0.055 (5) | 0.044 (5) | −0.014 (4) | 0.001 (4) | −0.003 (4) |
O1—C5 | 1.348 (7) | C11—H11B | 0.9600 |
O1—C4 | 1.471 (7) | C11—H11C | 0.9600 |
O2—C5 | 1.203 (7) | C12—H12A | 0.9600 |
O3—C6 | 1.205 (7) | C12—H12B | 0.9600 |
N—C5 | 1.404 (7) | C12—H12C | 0.9600 |
N—C6 | 1.413 (7) | C13—H13A | 0.9600 |
N—C3 | 1.486 (6) | C13—H13B | 0.9600 |
C1—C2 | 1.543 (7) | C13—H13C | 0.9600 |
C1—H1A | 0.9600 | C21—C26 | 1.382 (8) |
C1—H1B | 0.9600 | C21—C22 | 1.390 (8) |
C1—H1C | 0.9600 | C22—C23 | 1.399 (8) |
C2—C11 | 1.541 (7) | C22—H22A | 0.9300 |
C2—C3 | 1.542 (7) | C23—C24 | 1.387 (8) |
C2—H2A | 0.9800 | C23—H23A | 0.9300 |
C3—C4 | 1.558 (7) | C24—C25 | 1.377 (7) |
C3—H3A | 0.9800 | C24—H24A | 0.9300 |
C4—C21 | 1.505 (8) | C25—C26 | 1.388 (7) |
C4—C27 | 1.541 (8) | C25—H25A | 0.9300 |
C6—C7 | 1.531 (8) | C26—H26A | 0.9300 |
C7—C8 | 1.517 (7) | C27—C32 | 1.379 (7) |
C7—C12 | 1.549 (7) | C27—C28 | 1.390 (7) |
C7—H7A | 0.9800 | C28—C29 | 1.380 (7) |
C8—C9 | 1.523 (8) | C28—H28A | 0.9300 |
C8—H8A | 0.9700 | C29—C30 | 1.381 (8) |
C8—H8B | 0.9700 | C29—H29A | 0.9300 |
C9—C10 | 1.318 (7) | C30—C31 | 1.403 (7) |
C9—C13 | 1.527 (7) | C30—H30A | 0.9300 |
C10—H10A | 0.9300 | C31—C32 | 1.387 (8) |
C10—H10B | 0.9300 | C31—H31A | 0.9300 |
C11—H11A | 0.9600 | C32—H32A | 0.9300 |
C5—O1—C4 | 109.9 (5) | C2—C11—H11B | 109.5 |
C5—N—C6 | 127.3 (6) | H11A—C11—H11B | 109.5 |
C5—N—C3 | 110.4 (5) | C2—C11—H11C | 109.5 |
C6—N—C3 | 120.4 (5) | H11A—C11—H11C | 109.5 |
C2—C1—H1A | 109.5 | H11B—C11—H11C | 109.5 |
C2—C1—H1B | 109.5 | C7—C12—H12A | 109.5 |
H1A—C1—H1B | 109.5 | C7—C12—H12B | 109.5 |
C2—C1—H1C | 109.5 | H12A—C12—H12B | 109.5 |
H1A—C1—H1C | 109.5 | C7—C12—H12C | 109.5 |
H1B—C1—H1C | 109.5 | H12A—C12—H12C | 109.5 |
C11—C2—C1 | 110.0 (5) | H12B—C12—H12C | 109.5 |
C11—C2—C3 | 114.3 (5) | C9—C13—H13A | 109.5 |
C1—C2—C3 | 109.4 (5) | C9—C13—H13B | 109.5 |
C11—C2—H2A | 107.6 | H13A—C13—H13B | 109.5 |
C1—C2—H2A | 107.6 | C9—C13—H13C | 109.5 |
C3—C2—H2A | 107.6 | H13A—C13—H13C | 109.5 |
N—C3—C2 | 111.7 (5) | H13B—C13—H13C | 109.5 |
N—C3—C4 | 98.3 (5) | C26—C21—C22 | 119.1 (6) |
C2—C3—C4 | 116.5 (5) | C26—C21—C4 | 120.7 (6) |
N—C3—H3A | 109.9 | C22—C21—C4 | 120.0 (7) |
C2—C3—H3A | 109.9 | C21—C22—C23 | 120.4 (7) |
C4—C3—H3A | 109.9 | C21—C22—H22A | 119.8 |
O1—C4—C21 | 107.2 (5) | C23—C22—H22A | 119.8 |
O1—C4—C27 | 107.3 (5) | C24—C23—C22 | 119.8 (7) |
C21—C4—C27 | 111.0 (5) | C24—C23—H23A | 120.1 |
O1—C4—C3 | 102.5 (5) | C22—C23—H23A | 120.1 |
C21—C4—C3 | 117.3 (5) | C25—C24—C23 | 119.5 (7) |
C27—C4—C3 | 110.6 (5) | C25—C24—H24A | 120.3 |
O2—C5—O1 | 123.1 (7) | C23—C24—H24A | 120.3 |
O2—C5—N | 128.6 (7) | C24—C25—C26 | 120.7 (7) |
O1—C5—N | 108.3 (6) | C24—C25—H25A | 119.6 |
O3—C6—N | 119.9 (6) | C26—C25—H25A | 119.6 |
O3—C6—C7 | 123.2 (7) | C21—C26—C25 | 120.4 (7) |
N—C6—C7 | 116.9 (6) | C21—C26—H26A | 119.8 |
C8—C7—C6 | 109.5 (5) | C25—C26—H26A | 119.8 |
C8—C7—C12 | 111.4 (5) | C32—C27—C28 | 119.3 (6) |
C6—C7—C12 | 108.4 (5) | C32—C27—C4 | 120.8 (6) |
C8—C7—H7A | 109.2 | C28—C27—C4 | 119.8 (6) |
C6—C7—H7A | 109.2 | C29—C28—C27 | 119.9 (6) |
C12—C7—H7A | 109.2 | C29—C28—H28A | 120.1 |
C7—C8—C9 | 115.8 (5) | C27—C28—H28A | 120.1 |
C7—C8—H8A | 108.3 | C28—C29—C30 | 121.9 (6) |
C9—C8—H8A | 108.3 | C28—C29—H29A | 119.0 |
C7—C8—H8B | 108.3 | C30—C29—H29A | 119.0 |
C9—C8—H8B | 108.3 | C29—C30—C31 | 117.8 (7) |
H8A—C8—H8B | 107.4 | C29—C30—H30A | 121.1 |
C10—C9—C8 | 124.7 (7) | C31—C30—H30A | 121.1 |
C10—C9—C13 | 121.8 (7) | C32—C31—C30 | 120.5 (6) |
C8—C9—C13 | 113.5 (6) | C32—C31—H31A | 119.7 |
C9—C10—H10A | 120.0 | C30—C31—H31A | 119.7 |
C9—C10—H10B | 120.0 | C27—C32—C31 | 120.6 (6) |
H10A—C10—H10B | 120.0 | C27—C32—H32A | 119.7 |
C2—C11—H11A | 109.5 | C31—C32—H32A | 119.7 |
C5—N—C3—C2 | −95.7 (5) | C12—C7—C8—C9 | 171.5 (5) |
C6—N—C3—C2 | 99.1 (6) | C7—C8—C9—C10 | −3.3 (9) |
C5—N—C3—C4 | 27.2 (6) | C7—C8—C9—C13 | 178.8 (5) |
C6—N—C3—C4 | −138.1 (5) | O1—C4—C21—C26 | 11.1 (7) |
C11—C2—C3—N | 51.9 (7) | C27—C4—C21—C26 | −105.8 (7) |
C1—C2—C3—N | −71.9 (6) | C3—C4—C21—C26 | 125.6 (6) |
C11—C2—C3—C4 | −59.9 (7) | O1—C4—C21—C22 | −174.0 (5) |
C1—C2—C3—C4 | 176.3 (5) | C27—C4—C21—C22 | 69.1 (7) |
C5—O1—C4—C21 | 151.1 (5) | C3—C4—C21—C22 | −59.5 (8) |
C5—O1—C4—C27 | −89.6 (5) | C26—C21—C22—C23 | −1.9 (9) |
C5—O1—C4—C3 | 27.0 (6) | C4—C21—C22—C23 | −176.8 (6) |
N—C3—C4—O1 | −30.9 (6) | C21—C22—C23—C24 | 0.6 (9) |
C2—C3—C4—O1 | 88.4 (6) | C22—C23—C24—C25 | −0.4 (10) |
N—C3—C4—C21 | −148.0 (6) | C23—C24—C25—C26 | 1.4 (10) |
C2—C3—C4—C21 | −28.6 (8) | C22—C21—C26—C25 | 2.8 (9) |
N—C3—C4—C27 | 83.2 (6) | C4—C21—C26—C25 | 177.8 (6) |
C2—C3—C4—C27 | −157.4 (5) | C24—C25—C26—C21 | −2.6 (10) |
C4—O1—C5—O2 | 172.0 (6) | O1—C4—C27—C32 | 154.9 (5) |
C4—O1—C5—N | −10.2 (6) | C21—C4—C27—C32 | −88.3 (7) |
C6—N—C5—O2 | −30.7 (10) | C3—C4—C27—C32 | 43.8 (8) |
C3—N—C5—O2 | 165.3 (6) | O1—C4—C27—C28 | −28.2 (7) |
C6—N—C5—O1 | 151.7 (5) | C21—C4—C27—C28 | 88.6 (7) |
C3—N—C5—O1 | −12.3 (6) | C3—C4—C27—C28 | −139.3 (5) |
C5—N—C6—O3 | −163.2 (6) | C32—C27—C28—C29 | −1.6 (9) |
C3—N—C6—O3 | −0.6 (9) | C4—C27—C28—C29 | −178.5 (6) |
C5—N—C6—C7 | 14.5 (9) | C27—C28—C29—C30 | 0.1 (10) |
C3—N—C6—C7 | 177.1 (5) | C28—C29—C30—C31 | 1.0 (10) |
O3—C6—C7—C8 | −38.4 (9) | C29—C30—C31—C32 | −0.5 (10) |
N—C6—C7—C8 | 144.0 (5) | C28—C27—C32—C31 | 2.0 (9) |
O3—C6—C7—C12 | 83.4 (7) | C4—C27—C32—C31 | 178.9 (6) |
N—C6—C7—C12 | −94.3 (6) | C30—C31—C32—C27 | −1.0 (10) |
C6—C7—C8—C9 | −68.6 (7) |
Experimental details
Crystal data | |
Chemical formula | C25H29NO3 |
Mr | 391.49 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 291 |
a, b, c (Å) | 8.7567 (11), 10.0467 (17), 24.921 (5) |
V (Å3) | 2192.4 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.25 × 0.25 × 0.23 |
Data collection | |
Diffractometer | Nonius KappaCCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15624, 2223, 628 |
Rint | 0.064 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.086, 1.01 |
No. of reflections | 2223 |
No. of parameters | 262 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.10, −0.13 |
Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1991), SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003).
The title compound, (I), was synthesized in the course of the generation of depsipeptide libraries resembling the Jasplakinolide family of natural products (Hu et al., 2007). The relative configuration of (I) is in accordance with the model for diastereoselective alkylation of acylated chiral oxazolidinones derived from amino acids (Evans & Takacs, 1980) and their modified diphenyl analogs (Hintermann & Seebach, 1998). The stereogenic centres were assigned based on the known chirality of the starting material (C3 S and C7 R).