Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802002477/cv6085sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802002477/cv6085Isup2.hkl |
CCDC reference: 183776
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.
C12H21NO4 | F(000) = 528 |
Mr = 243.30 | Dx = 1.174 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 18700 reflections |
a = 13.6452 (5) Å | θ = 1–28.3° |
b = 10.1594 (5) Å | µ = 0.09 mm−1 |
c = 10.0848 (4) Å | T = 123 K |
β = 100.163 (2)° | Prisms, colourless |
V = 1376.09 (10) Å3 | 0.45 × 0.30 × 0.15 mm |
Z = 4 |
Nonius KappaCCD diffractometer | 2879 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.032 |
Graphite monochromator | θmax = 28.3°, θmin = 3.0° |
rotation in φ and ω (2°) scans | h = −18→18 |
18786 measured reflections | k = −13→13 |
3392 independent reflections | l = −13→13 |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.104 | H-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 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.59623 (6) | 0.72722 (9) | 0.66002 (8) | 0.0376 (2) | |
O2 | 0.87852 (5) | 0.58418 (7) | 0.71822 (8) | 0.03025 (19) | |
O3 | 0.81878 (5) | 0.76638 (7) | 0.59736 (7) | 0.02400 (17) | |
O4 | 0.61279 (5) | 0.42996 (7) | 0.50018 (8) | 0.02846 (18) | |
C1 | 0.65940 (7) | 0.64629 (10) | 0.46822 (10) | 0.0215 (2) | |
H1 | 0.6897 | 0.7000 | 0.4028 | 0.026* | |
C11 | 0.59243 (7) | 0.73206 (10) | 0.53929 (10) | 0.0245 (2) | |
C12 | 0.52408 (9) | 0.82412 (11) | 0.45065 (12) | 0.0330 (3) | |
H12A | 0.4657 | 0.8427 | 0.4919 | 0.050* | |
H12B | 0.5026 | 0.7834 | 0.3622 | 0.050* | |
H12C | 0.5592 | 0.9065 | 0.4399 | 0.050* | |
N2 | 0.73619 (6) | 0.57901 (8) | 0.56148 (8) | 0.02250 (19) | |
C21 | 0.81696 (7) | 0.63927 (10) | 0.63436 (10) | 0.0223 (2) | |
C22 | 0.89930 (7) | 0.85519 (10) | 0.66076 (10) | 0.0238 (2) | |
C23 | 1.00106 (8) | 0.80249 (12) | 0.64504 (13) | 0.0347 (3) | |
H23A | 1.0033 | 0.7907 | 0.5492 | 0.052* | |
H23B | 1.0127 | 0.7177 | 0.6915 | 0.052* | |
H23C | 1.0527 | 0.8652 | 0.6843 | 0.052* | |
C24 | 0.87587 (9) | 0.98012 (11) | 0.58031 (12) | 0.0366 (3) | |
H24A | 0.8817 | 0.9639 | 0.4862 | 0.055* | |
H24B | 0.9228 | 1.0492 | 0.6177 | 0.055* | |
H24C | 0.8078 | 1.0083 | 0.5848 | 0.055* | |
C25 | 0.89144 (10) | 0.87565 (13) | 0.80714 (11) | 0.0380 (3) | |
H25A | 0.9068 | 0.7930 | 0.8566 | 0.057* | |
H25B | 0.8236 | 0.9034 | 0.8135 | 0.057* | |
H25C | 0.9388 | 0.9437 | 0.8461 | 0.057* | |
C3 | 0.71045 (7) | 0.43952 (10) | 0.58056 (11) | 0.0259 (2) | |
C31 | 0.69978 (9) | 0.40783 (12) | 0.72429 (12) | 0.0346 (3) | |
H31A | 0.7651 | 0.4135 | 0.7829 | 0.052* | |
H31B | 0.6732 | 0.3185 | 0.7282 | 0.052* | |
H31C | 0.6541 | 0.4709 | 0.7547 | 0.052* | |
C32 | 0.78226 (9) | 0.34808 (11) | 0.52649 (13) | 0.0364 (3) | |
H32A | 0.8485 | 0.3558 | 0.5822 | 0.055* | |
H32B | 0.7857 | 0.3724 | 0.4334 | 0.055* | |
H32C | 0.7588 | 0.2571 | 0.5290 | 0.055* | |
C5 | 0.60364 (7) | 0.52779 (10) | 0.39727 (10) | 0.0254 (2) | |
H5A | 0.5329 | 0.5495 | 0.3637 | 0.031* | |
H5B | 0.6346 | 0.4980 | 0.3208 | 0.031* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0370 (4) | 0.0510 (5) | 0.0254 (4) | 0.0041 (4) | 0.0070 (3) | −0.0054 (4) |
O2 | 0.0261 (4) | 0.0262 (4) | 0.0344 (4) | −0.0026 (3) | −0.0059 (3) | 0.0069 (3) |
O3 | 0.0227 (3) | 0.0203 (3) | 0.0271 (4) | −0.0042 (3) | −0.0011 (3) | 0.0033 (3) |
O4 | 0.0247 (4) | 0.0249 (4) | 0.0326 (4) | −0.0055 (3) | −0.0038 (3) | 0.0031 (3) |
C1 | 0.0203 (4) | 0.0226 (5) | 0.0207 (4) | 0.0003 (3) | 0.0014 (4) | 0.0011 (4) |
C11 | 0.0233 (5) | 0.0236 (5) | 0.0266 (5) | −0.0034 (4) | 0.0043 (4) | −0.0029 (4) |
C12 | 0.0342 (6) | 0.0254 (5) | 0.0407 (6) | 0.0064 (4) | 0.0099 (5) | 0.0018 (5) |
N2 | 0.0207 (4) | 0.0194 (4) | 0.0256 (4) | −0.0014 (3) | −0.0008 (3) | 0.0028 (3) |
C21 | 0.0213 (4) | 0.0213 (5) | 0.0240 (5) | −0.0017 (4) | 0.0033 (4) | 0.0016 (4) |
C22 | 0.0251 (5) | 0.0223 (5) | 0.0234 (5) | −0.0069 (4) | 0.0024 (4) | 0.0001 (4) |
C23 | 0.0256 (5) | 0.0347 (6) | 0.0438 (7) | −0.0078 (4) | 0.0063 (5) | −0.0046 (5) |
C24 | 0.0429 (6) | 0.0240 (5) | 0.0400 (6) | −0.0079 (5) | −0.0003 (5) | 0.0056 (5) |
C25 | 0.0490 (7) | 0.0393 (7) | 0.0271 (5) | −0.0123 (5) | 0.0106 (5) | −0.0047 (5) |
C3 | 0.0234 (5) | 0.0205 (5) | 0.0312 (5) | −0.0041 (4) | −0.0025 (4) | 0.0020 (4) |
C31 | 0.0340 (6) | 0.0331 (6) | 0.0343 (6) | −0.0093 (5) | −0.0008 (5) | 0.0099 (5) |
C32 | 0.0349 (6) | 0.0250 (5) | 0.0462 (7) | 0.0041 (4) | −0.0018 (5) | −0.0029 (5) |
C5 | 0.0250 (5) | 0.0247 (5) | 0.0250 (5) | −0.0004 (4) | −0.0003 (4) | −0.0015 (4) |
O1—C11 | 1.2104 (13) | C23—H23A | 0.9800 |
O2—C21 | 1.2179 (12) | C23—H23B | 0.9800 |
O3—C21 | 1.3456 (12) | C23—H23C | 0.9800 |
O3—C22 | 1.4773 (11) | C24—H24A | 0.9800 |
O4—C5 | 1.4264 (13) | C24—H24B | 0.9800 |
O4—C3 | 1.4357 (12) | C24—H24C | 0.9800 |
C1—N2 | 1.4498 (12) | C25—H25A | 0.9800 |
C1—C11 | 1.5295 (14) | C25—H25B | 0.9800 |
C1—C5 | 1.5323 (13) | C25—H25C | 0.9800 |
C1—H1 | 1.0000 | C3—C31 | 1.5167 (16) |
C11—C12 | 1.4999 (15) | C3—C32 | 1.5196 (16) |
C12—H12A | 0.9800 | C31—H31A | 0.9800 |
C12—H12B | 0.9800 | C31—H31B | 0.9800 |
C12—H12C | 0.9800 | C31—H31C | 0.9800 |
N2—C21 | 1.3578 (12) | C32—H32A | 0.9800 |
N2—C3 | 1.4807 (13) | C32—H32B | 0.9800 |
C22—C24 | 1.5099 (15) | C32—H32C | 0.9800 |
C22—C25 | 1.5132 (15) | C5—H5A | 0.9900 |
C22—C23 | 1.5223 (15) | C5—H5B | 0.9900 |
C21—O3—C22 | 120.99 (7) | C22—C24—H24B | 109.5 |
C5—O4—C3 | 108.48 (7) | H24A—C24—H24B | 109.5 |
N2—C1—C11 | 112.81 (8) | C22—C24—H24C | 109.5 |
N2—C1—C5 | 100.08 (8) | H24A—C24—H24C | 109.5 |
C11—C1—C5 | 112.20 (8) | H24B—C24—H24C | 109.5 |
N2—C1—H1 | 110.5 | C22—C25—H25A | 109.5 |
C11—C1—H1 | 110.5 | C22—C25—H25B | 109.5 |
C5—C1—H1 | 110.5 | H25A—C25—H25B | 109.5 |
O1—C11—C12 | 122.46 (10) | C22—C25—H25C | 109.5 |
O1—C11—C1 | 121.68 (9) | H25A—C25—H25C | 109.5 |
C12—C11—C1 | 115.85 (9) | H25B—C25—H25C | 109.5 |
C11—C12—H12A | 109.5 | O4—C3—N2 | 102.08 (7) |
C11—C12—H12B | 109.5 | O4—C3—C31 | 106.81 (8) |
H12A—C12—H12B | 109.5 | N2—C3—C31 | 113.10 (9) |
C11—C12—H12C | 109.5 | O4—C3—C32 | 110.43 (9) |
H12A—C12—H12C | 109.5 | N2—C3—C32 | 110.83 (9) |
H12B—C12—H12C | 109.5 | C31—C3—C32 | 112.95 (9) |
C21—N2—C1 | 124.28 (8) | C3—C31—H31A | 109.5 |
C21—N2—C3 | 123.35 (8) | C3—C31—H31B | 109.5 |
C1—N2—C3 | 112.00 (7) | H31A—C31—H31B | 109.5 |
O2—C21—O3 | 126.11 (9) | C3—C31—H31C | 109.5 |
O2—C21—N2 | 124.27 (9) | H31A—C31—H31C | 109.5 |
O3—C21—N2 | 109.60 (8) | H31B—C31—H31C | 109.5 |
O3—C22—C24 | 102.12 (8) | C3—C32—H32A | 109.5 |
O3—C22—C25 | 109.31 (8) | C3—C32—H32B | 109.5 |
C24—C22—C25 | 111.35 (10) | H32A—C32—H32B | 109.5 |
O3—C22—C23 | 111.25 (8) | C3—C32—H32C | 109.5 |
C24—C22—C23 | 110.50 (9) | H32A—C32—H32C | 109.5 |
C25—C22—C23 | 111.90 (9) | H32B—C32—H32C | 109.5 |
C22—C23—H23A | 109.5 | O4—C5—C1 | 103.61 (8) |
C22—C23—H23B | 109.5 | O4—C5—H5A | 111.0 |
H23A—C23—H23B | 109.5 | C1—C5—H5A | 111.0 |
C22—C23—H23C | 109.5 | O4—C5—H5B | 111.0 |
H23A—C23—H23C | 109.5 | C1—C5—H5B | 111.0 |
H23B—C23—H23C | 109.5 | H5A—C5—H5B | 109.0 |
C22—C24—H24A | 109.5 | ||
N2—C1—C11—O1 | −9.76 (14) | C21—O3—C22—C25 | −66.93 (12) |
C5—C1—C11—O1 | 102.38 (11) | C21—O3—C22—C23 | 57.14 (12) |
N2—C1—C11—C12 | 168.83 (9) | C5—O4—C3—N2 | 25.74 (10) |
C5—C1—C11—C12 | −79.04 (11) | C5—O4—C3—C31 | 144.67 (9) |
C11—C1—N2—C21 | −72.11 (12) | C5—O4—C3—C32 | −92.16 (10) |
C5—C1—N2—C21 | 168.47 (9) | C21—N2—C3—O4 | 170.20 (9) |
C11—C1—N2—C3 | 101.07 (10) | C1—N2—C3—O4 | −3.05 (11) |
C5—C1—N2—C3 | −18.35 (10) | C21—N2—C3—C31 | 55.82 (13) |
C22—O3—C21—O2 | −1.14 (15) | C1—N2—C3—C31 | −117.43 (9) |
C22—O3—C21—N2 | −179.84 (8) | C21—N2—C3—C32 | −72.19 (12) |
C1—N2—C21—O2 | 175.70 (10) | C1—N2—C3—C32 | 114.56 (9) |
C3—N2—C21—O2 | 3.27 (16) | C3—O4—C5—C1 | −38.01 (10) |
C1—N2—C21—O3 | −5.57 (13) | N2—C1—C5—O4 | 33.05 (9) |
C3—N2—C21—O3 | −177.99 (9) | C11—C1—C5—O4 | −86.81 (9) |
C21—O3—C22—C24 | 175.04 (9) |
D—H···A | D—H | H···A | D···A | D—H···A |
C23—H23C···O2i | 0.98 | 2.54 | 3.4630 (14) | 156 |
C24—H24A···O2ii | 0.98 | 2.74 | 3.7160 (15) | 175 |
C1—H1···O1ii | 1.00 | 2.66 | 3.3330 (12) | 125 |
C12—H12B···O1ii | 0.98 | 2.59 | 3.2939 (15) | 129 |
Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) x, −y+3/2, z−1/2. |