Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807000839/hb2257sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807000839/hb2257Isup2.hkl |
CCDC reference: 638515
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; 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 and PLATON (Spek, 2003).
C20H27NO4 | F(000) = 372 |
Mr = 345.43 | Dx = 1.248 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 11172 reflections |
a = 9.7530 (6) Å | θ = 3.0–27.5° |
b = 9.3216 (8) Å | µ = 0.09 mm−1 |
c = 10.792 (7) Å | T = 173 K |
β = 110.462 (4)° | Block, colourless |
V = 919.2 (6) Å3 | 0.50 × 0.50 × 0.45 mm |
Z = 2 |
Nonius KappaCCD diffractometer | 1472 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.028 |
Graphite monochromator | θmax = 27.5°, θmin = 3.0° |
Detector resolution: 19 vertical, 18 horizontal pixels mm-1 | h = −12→12 |
380 frames via ω–rotation (ΔΩ= 1°) and two times 10 s per frame (four sets at different κ–angles) scans | k = −12→12 |
11172 measured reflections | l = −14→13 |
2232 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.029 | H-atom parameters constrained |
wR(F2) = 0.057 | w = 1/[σ2(Fo2) + (0.0224P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.90 | (Δ/σ)max < 0.001 |
2232 reflections | Δρmax = 0.16 e Å−3 |
232 parameters | Δρmin = −0.12 e Å−3 |
1 restraint | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.038 (2) |
Experimental. IR (KBr pellet), cm-1: 3012 (w), 2979 (m), 2952 (m), 2879 (m), 2837 (m), 1690 (s), 1393 (s), 1362 (s), 1083 (s), [α]D22: +127.5 (c 1/5, CHCl3). NMR (most of the signals are duplicated due to the slow conformational inversion), 1H (400 MHz, CDCl3, room temperature): δ 7.53–7.28 (m, 5H), 6.27 (d, 1H), 5.81 (d, 1H), 4.84 (br s, 2H), 4.18 (dd, 1H), 3.83 (m, 1H), 3.71 (m, 1H), 1.69–1.45 (m, 15H); 13C (100.6 MHz, CDCl3, room temperature): δ 152.0 (d), 139.8 (d), 132.5 (s), 128.7 (d), 128.1 (d), 126.4 (d), 123.4 (d), 94.6 (d), 84.4 (d), 80.1 (d), 76.1 (d), 62.7 (d), 59.1 (d), 28.6 (d), 25.8 (d), 24.3 (d), HRMS calculated for C20H27NO4: [M + H]+ = 346.2018; found 346.2043 [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 | 0.19109 (15) | 0.37201 (15) | −0.05010 (13) | 0.0402 (4) | |
O2 | −0.10422 (13) | 0.38839 (15) | −0.27736 (12) | 0.0338 (3) | |
O3 | 0.17075 (14) | 0.26211 (16) | −0.48039 (14) | 0.0376 (4) | |
O4 | 0.30194 (13) | 0.45437 (14) | −0.36983 (12) | 0.0300 (3) | |
N1 | 0.09469 (15) | 0.39617 (17) | −0.34033 (14) | 0.0276 (4) | |
C1 | 0.2773 (2) | 0.7649 (2) | −0.04852 (18) | 0.0290 (5) | |
C2 | 0.3607 (2) | 0.7913 (2) | −0.1273 (2) | 0.0359 (5) | |
H2 | 0.3949 | 0.7131 | −0.1650 | 0.043* | |
C3 | 0.3945 (2) | 0.9310 (2) | −0.1517 (2) | 0.0421 (6) | |
H3 | 0.4528 | 0.9476 | −0.2047 | 0.051* | |
C4 | 0.3439 (2) | 1.0453 (3) | −0.0994 (2) | 0.0435 (6) | |
H4 | 0.3660 | 1.1407 | −0.1170 | 0.052* | |
C5 | 0.2610 (2) | 1.0203 (2) | −0.0214 (2) | 0.0439 (6) | |
H5 | 0.2259 | 1.0990 | 0.0150 | 0.053* | |
C6 | 0.2284 (2) | 0.8821 (2) | 0.00421 (18) | 0.0358 (5) | |
H6 | 0.1716 | 0.8666 | 0.0588 | 0.043* | |
C7 | 0.2416 (2) | 0.6176 (2) | −0.0206 (2) | 0.0287 (5) | |
C8 | 0.2146 (2) | 0.5703 (2) | 0.0843 (2) | 0.0363 (5) | |
H8 | 0.2131 | 0.6291 | 0.1557 | 0.044* | |
C9 | 0.1868 (2) | 0.4128 (3) | 0.0756 (2) | 0.0423 (6) | |
H9A | 0.2631 | 0.3617 | 0.1475 | 0.051* | |
H9B | 0.0900 | 0.3911 | 0.0816 | 0.051* | |
C10 | 0.2281 (2) | 0.4934 (2) | −0.11403 (18) | 0.0300 (5) | |
H10 | 0.3248 | 0.4761 | −0.1242 | 0.036* | |
C11 | 0.11126 (19) | 0.5180 (2) | −0.25062 (17) | 0.0265 (5) | |
H11 | 0.1358 | 0.6062 | −0.2914 | 0.032* | |
C12 | −0.0442 (2) | 0.5302 (2) | −0.2491 (2) | 0.0320 (5) | |
H12A | −0.0430 | 0.5628 | −0.1614 | 0.038* | |
H12B | −0.1023 | 0.5990 | −0.3171 | 0.038* | |
C13 | −0.0493 (2) | 0.3239 (2) | −0.37114 (19) | 0.0313 (5) | |
C14 | −0.0338 (2) | 0.1652 (2) | −0.3410 (2) | 0.0406 (6) | |
H14A | 0.0327 | 0.1506 | −0.2499 | 0.061* | |
H14B | 0.0059 | 0.1175 | −0.4021 | 0.061* | |
H14C | −0.1299 | 0.1246 | −0.3516 | 0.061* | |
C15 | −0.1492 (2) | 0.3588 (2) | −0.51085 (19) | 0.0402 (6) | |
H15A | −0.2427 | 0.3087 | −0.5298 | 0.060* | |
H15B | −0.1031 | 0.3276 | −0.5737 | 0.060* | |
H15C | −0.1665 | 0.4625 | −0.5193 | 0.060* | |
C16 | 0.1879 (2) | 0.3624 (2) | −0.40352 (18) | 0.0294 (5) | |
C17 | 0.43261 (19) | 0.4217 (2) | −0.40335 (19) | 0.0292 (5) | |
C18 | 0.5320 (2) | 0.5473 (2) | −0.3428 (2) | 0.0376 (5) | |
H18A | 0.4842 | 0.6368 | −0.3829 | 0.056* | |
H18B | 0.6243 | 0.5366 | −0.3590 | 0.056* | |
H18C | 0.5519 | 0.5497 | −0.2473 | 0.056* | |
C19 | 0.3953 (2) | 0.4190 (2) | −0.55272 (18) | 0.0346 (5) | |
H19A | 0.3294 | 0.3385 | −0.5906 | 0.052* | |
H19B | 0.4854 | 0.4077 | −0.5727 | 0.052* | |
H19C | 0.3472 | 0.5091 | −0.5910 | 0.052* | |
C20 | 0.4995 (2) | 0.2824 (2) | −0.3386 (2) | 0.0383 (6) | |
H20A | 0.5142 | 0.2861 | −0.2441 | 0.057* | |
H20B | 0.5939 | 0.2679 | −0.3500 | 0.057* | |
H20C | 0.4338 | 0.2027 | −0.3799 | 0.057* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0570 (9) | 0.0312 (9) | 0.0288 (8) | −0.0044 (7) | 0.0104 (7) | 0.0004 (7) |
O2 | 0.0313 (7) | 0.0401 (9) | 0.0354 (7) | −0.0051 (7) | 0.0184 (6) | −0.0060 (8) |
O3 | 0.0403 (8) | 0.0389 (9) | 0.0377 (8) | −0.0093 (8) | 0.0190 (7) | −0.0152 (8) |
O4 | 0.0252 (7) | 0.0330 (8) | 0.0356 (8) | −0.0048 (6) | 0.0155 (6) | −0.0065 (6) |
N1 | 0.0244 (8) | 0.0310 (10) | 0.0290 (8) | −0.0072 (8) | 0.0114 (7) | −0.0093 (9) |
C1 | 0.0298 (11) | 0.0310 (12) | 0.0228 (11) | −0.0016 (10) | 0.0051 (9) | −0.0029 (10) |
C2 | 0.0355 (12) | 0.0353 (14) | 0.0376 (13) | −0.0027 (10) | 0.0139 (11) | −0.0051 (11) |
C3 | 0.0409 (12) | 0.0464 (17) | 0.0398 (14) | −0.0077 (11) | 0.0150 (11) | 0.0034 (12) |
C4 | 0.0519 (15) | 0.0322 (14) | 0.0376 (13) | −0.0094 (12) | 0.0044 (12) | 0.0004 (11) |
C5 | 0.0551 (15) | 0.0363 (15) | 0.0372 (13) | 0.0053 (12) | 0.0122 (12) | −0.0024 (11) |
C6 | 0.0441 (12) | 0.0332 (14) | 0.0305 (11) | 0.0018 (11) | 0.0137 (9) | −0.0026 (11) |
C7 | 0.0285 (11) | 0.0308 (12) | 0.0255 (11) | −0.0012 (9) | 0.0078 (9) | −0.0027 (10) |
C8 | 0.0411 (12) | 0.0389 (14) | 0.0277 (12) | −0.0048 (10) | 0.0106 (10) | −0.0072 (11) |
C9 | 0.0493 (13) | 0.0463 (15) | 0.0302 (11) | −0.0080 (12) | 0.0124 (10) | 0.0020 (11) |
C10 | 0.0310 (11) | 0.0293 (12) | 0.0287 (11) | 0.0011 (9) | 0.0090 (9) | 0.0003 (10) |
C11 | 0.0273 (10) | 0.0274 (12) | 0.0257 (11) | −0.0010 (9) | 0.0105 (9) | −0.0022 (9) |
C12 | 0.0311 (11) | 0.0344 (14) | 0.0318 (11) | 0.0005 (10) | 0.0126 (9) | −0.0019 (10) |
C13 | 0.0266 (11) | 0.0386 (13) | 0.0307 (12) | −0.0080 (9) | 0.0125 (9) | −0.0063 (10) |
C14 | 0.0395 (13) | 0.0362 (15) | 0.0497 (14) | −0.0097 (10) | 0.0201 (12) | −0.0033 (12) |
C15 | 0.0327 (11) | 0.0523 (16) | 0.0331 (11) | −0.0090 (11) | 0.0084 (9) | −0.0061 (12) |
C16 | 0.0291 (11) | 0.0335 (14) | 0.0258 (11) | −0.0053 (10) | 0.0099 (9) | −0.0005 (11) |
C17 | 0.0249 (10) | 0.0340 (13) | 0.0320 (11) | 0.0016 (9) | 0.0140 (9) | 0.0028 (10) |
C18 | 0.0280 (11) | 0.0390 (14) | 0.0483 (13) | −0.0029 (10) | 0.0164 (10) | 0.0019 (11) |
C19 | 0.0346 (11) | 0.0386 (14) | 0.0349 (12) | 0.0051 (10) | 0.0175 (9) | 0.0051 (11) |
C20 | 0.0351 (12) | 0.0407 (15) | 0.0389 (13) | 0.0068 (11) | 0.0126 (10) | 0.0046 (11) |
O1—C9 | 1.423 (2) | C9—H9B | 0.9900 |
O1—C10 | 1.435 (2) | C10—C11 | 1.533 (3) |
O2—C13 | 1.432 (2) | C10—H10 | 1.0000 |
O2—C12 | 1.435 (2) | C11—C12 | 1.526 (3) |
O3—C16 | 1.222 (2) | C11—H11 | 1.0000 |
O4—C16 | 1.350 (2) | C12—H12A | 0.9900 |
O4—C17 | 1.473 (2) | C12—H12B | 0.9900 |
N1—C16 | 1.350 (2) | C13—C14 | 1.511 (3) |
N1—C11 | 1.464 (2) | C13—C15 | 1.517 (3) |
N1—C13 | 1.487 (2) | C14—H14A | 0.9800 |
C1—C2 | 1.389 (3) | C14—H14B | 0.9800 |
C1—C6 | 1.390 (3) | C14—H14C | 0.9800 |
C1—C7 | 1.474 (3) | C15—H15A | 0.9800 |
C2—C3 | 1.391 (3) | C15—H15B | 0.9800 |
C2—H2 | 0.9500 | C15—H15C | 0.9800 |
C3—C4 | 1.375 (3) | C17—C20 | 1.510 (3) |
C3—H3 | 0.9500 | C17—C18 | 1.515 (3) |
C4—C5 | 1.376 (3) | C17—C19 | 1.524 (3) |
C4—H4 | 0.9500 | C18—H18A | 0.9800 |
C5—C6 | 1.378 (3) | C18—H18B | 0.9800 |
C5—H5 | 0.9500 | C18—H18C | 0.9800 |
C6—H6 | 0.9500 | C19—H19A | 0.9800 |
C7—C8 | 1.324 (3) | C19—H19B | 0.9800 |
C7—C10 | 1.511 (3) | C19—H19C | 0.9800 |
C8—C9 | 1.490 (3) | C20—H20A | 0.9800 |
C8—H8 | 0.9500 | C20—H20B | 0.9800 |
C9—H9A | 0.9900 | C20—H20C | 0.9800 |
C9—O1—C10 | 110.08 (16) | C11—C12—H12A | 110.7 |
C13—O2—C12 | 108.16 (13) | O2—C12—H12B | 110.7 |
C16—O4—C17 | 120.33 (15) | C11—C12—H12B | 110.7 |
C16—N1—C11 | 125.20 (16) | H12A—C12—H12B | 108.8 |
C16—N1—C13 | 122.10 (15) | O2—C13—N1 | 102.07 (14) |
C11—N1—C13 | 112.13 (13) | O2—C13—C14 | 107.05 (16) |
C2—C1—C6 | 118.0 (2) | N1—C13—C14 | 112.32 (16) |
C2—C1—C7 | 121.37 (19) | O2—C13—C15 | 110.07 (16) |
C6—C1—C7 | 120.61 (17) | N1—C13—C15 | 110.72 (15) |
C1—C2—C3 | 120.6 (2) | C14—C13—C15 | 113.88 (18) |
C1—C2—H2 | 119.7 | C13—C14—H14A | 109.5 |
C3—C2—H2 | 119.7 | C13—C14—H14B | 109.5 |
C4—C3—C2 | 120.34 (19) | H14A—C14—H14B | 109.5 |
C4—C3—H3 | 119.8 | C13—C14—H14C | 109.5 |
C2—C3—H3 | 119.8 | H14A—C14—H14C | 109.5 |
C3—C4—C5 | 119.5 (2) | H14B—C14—H14C | 109.5 |
C3—C4—H4 | 120.3 | C13—C15—H15A | 109.5 |
C5—C4—H4 | 120.3 | C13—C15—H15B | 109.5 |
C4—C5—C6 | 120.4 (2) | H15A—C15—H15B | 109.5 |
C4—C5—H5 | 119.8 | C13—C15—H15C | 109.5 |
C6—C5—H5 | 119.8 | H15A—C15—H15C | 109.5 |
C5—C6—C1 | 121.09 (19) | H15B—C15—H15C | 109.5 |
C5—C6—H6 | 119.5 | O3—C16—O4 | 124.96 (16) |
C1—C6—H6 | 119.5 | O3—C16—N1 | 124.37 (17) |
C8—C7—C1 | 128.09 (18) | O4—C16—N1 | 110.67 (17) |
C8—C7—C10 | 108.58 (18) | O4—C17—C20 | 109.58 (15) |
C1—C7—C10 | 123.33 (17) | O4—C17—C18 | 102.26 (15) |
C7—C8—C9 | 111.12 (19) | C20—C17—C18 | 110.93 (16) |
C7—C8—H8 | 124.4 | O4—C17—C19 | 110.87 (14) |
C9—C8—H8 | 124.4 | C20—C17—C19 | 112.31 (17) |
O1—C9—C8 | 104.96 (18) | C18—C17—C19 | 110.44 (16) |
O1—C9—H9A | 110.8 | C17—C18—H18A | 109.5 |
C8—C9—H9A | 110.8 | C17—C18—H18B | 109.5 |
O1—C9—H9B | 110.8 | H18A—C18—H18B | 109.5 |
C8—C9—H9B | 110.8 | C17—C18—H18C | 109.5 |
H9A—C9—H9B | 108.8 | H18A—C18—H18C | 109.5 |
O1—C10—C7 | 105.15 (15) | H18B—C18—H18C | 109.5 |
O1—C10—C11 | 110.67 (15) | C17—C19—H19A | 109.5 |
C7—C10—C11 | 112.94 (16) | C17—C19—H19B | 109.5 |
O1—C10—H10 | 109.3 | H19A—C19—H19B | 109.5 |
C7—C10—H10 | 109.3 | C17—C19—H19C | 109.5 |
C11—C10—H10 | 109.3 | H19A—C19—H19C | 109.5 |
N1—C11—C12 | 100.65 (14) | H19B—C19—H19C | 109.5 |
N1—C11—C10 | 113.15 (16) | C17—C20—H20A | 109.5 |
C12—C11—C10 | 114.06 (15) | C17—C20—H20B | 109.5 |
N1—C11—H11 | 109.5 | H20A—C20—H20B | 109.5 |
C12—C11—H11 | 109.5 | C17—C20—H20C | 109.5 |
C10—C11—H11 | 109.5 | H20A—C20—H20C | 109.5 |
O2—C12—C11 | 105.17 (15) | H20B—C20—H20C | 109.5 |
O2—C12—H12A | 110.7 | ||
C6—C1—C2—C3 | 0.3 (3) | O1—C10—C11—N1 | −60.73 (19) |
C7—C1—C2—C3 | −179.37 (19) | C7—C10—C11—N1 | −178.30 (14) |
C1—C2—C3—C4 | −0.9 (3) | O1—C10—C11—C12 | 53.5 (2) |
C2—C3—C4—C5 | 0.8 (3) | C7—C10—C11—C12 | −64.0 (2) |
C3—C4—C5—C6 | −0.1 (3) | C13—O2—C12—C11 | −36.31 (19) |
C4—C5—C6—C1 | −0.5 (3) | N1—C11—C12—O2 | 26.85 (18) |
C2—C1—C6—C5 | 0.4 (3) | C10—C11—C12—O2 | −94.63 (18) |
C7—C1—C6—C5 | −179.9 (2) | C12—O2—C13—N1 | 28.89 (18) |
C2—C1—C7—C8 | 152.4 (2) | C12—O2—C13—C14 | 147.05 (16) |
C6—C1—C7—C8 | −27.4 (3) | C12—O2—C13—C15 | −88.70 (18) |
C2—C1—C7—C10 | −28.6 (3) | C16—N1—C13—O2 | 177.31 (16) |
C6—C1—C7—C10 | 151.67 (19) | C11—N1—C13—O2 | −10.93 (19) |
C1—C7—C8—C9 | −178.60 (19) | C16—N1—C13—C14 | 63.0 (2) |
C10—C7—C8—C9 | 2.3 (2) | C11—N1—C13—C14 | −125.26 (18) |
C10—O1—C9—C8 | 3.3 (2) | C16—N1—C13—C15 | −65.6 (2) |
C7—C8—C9—O1 | −3.5 (2) | C11—N1—C13—C15 | 106.20 (17) |
C9—O1—C10—C7 | −2.09 (19) | C17—O4—C16—O3 | −12.9 (3) |
C9—O1—C10—C11 | −124.34 (16) | C17—O4—C16—N1 | 166.95 (15) |
C8—C7—C10—O1 | −0.2 (2) | C11—N1—C16—O3 | −178.32 (18) |
C1—C7—C10—O1 | −179.34 (17) | C13—N1—C16—O3 | −7.7 (3) |
C8—C7—C10—C11 | 120.61 (18) | C11—N1—C16—O4 | 1.8 (2) |
C1—C7—C10—C11 | −58.6 (2) | C13—N1—C16—O4 | 172.44 (16) |
C16—N1—C11—C12 | 161.82 (17) | C16—O4—C17—C20 | −59.8 (2) |
C13—N1—C11—C12 | −9.64 (19) | C16—O4—C17—C18 | −177.57 (15) |
C16—N1—C11—C10 | −76.1 (2) | C16—O4—C17—C19 | 64.7 (2) |
C13—N1—C11—C10 | 112.48 (17) |