Acta Cryst. (2007). E63, o3941 [ doi:10.1107/S1600536807038731 ]
The title compound, C24H26N2O7, is an intermediate in the resolution of a tertiary alcohol using a chiral isocyanate reagent. On the basis of the unchanging S configuration of the chiral C atom introduced by the isocyanate reagent, the chiral centre on the tricyclo ring system is shown to adopt an S configuration. In the crystal structure, N-H
O hydrogen bonds link the molecules into chains.
The (S)-isocyanate 2 (2.0 mmol) was added to a mixture of alcohol 1 (1.0 mmol) and reagent grade CuCl (0.2 mmol) in dry CH2Cl2 (12 ml) at room temperature (Scheme 2; Duggan & Imagire, 1989). After stirring for 12 h, the reaction mixture was filtered and the filtrate was diluted with CH2Cl2 (20 ml), washed with H2O (20 ml) and brine (20 ml), dried over MgSO4 and concentrated. The crude product (0.43 g, 94%) was recrystallized from 2-propanol (31 ml) to yield a white powder (m.p. 485 K). Crystals suitable for X-ray analysis were obtained from ethyl acetate.
All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.98 Å and N—H = 0.88 Å, and with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for other H atoms. The methyl groups were allowed to rotate about their local threefold axes. In the absence of significant anomalous scattering effects, Friedel pairs have been merged as equivalent data. The absolute structure was assigned on the basis of the unchanging chiral centre C17, originating from the isocyanate reactant.
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
![[Figure 1]](./bi2220fig1thm.gif)
| Fig. 1. The molecular structure of the title compound showing displacement ellipsoids at 30% probability for non-H atoms. |
![[Figure 2]](./bi2220fig2thm.gif)
| Fig. 2. Unit-cell contents viewed along the b axis. |
![[Figure 3]](./bi2220fig3thm.gif)
| Fig. 3. The formation of the title compound. |
| C24H26N2O7 | F000 = 480 |
| Mr = 454.47 | Dx = 1.352 Mg m−3 |
| Monoclinic, P21 | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: P 2yb | Cell parameters from 2722 reflections |
| a = 7.3998 (10) Å | θ = 2.2–25.4º |
| b = 16.383 (2) Å | µ = 0.10 mm−1 |
| c = 9.2162 (13) Å | T = 296 (2) K |
| β = 92.322 (2)º | Prism, colourless |
| V = 1116.4 (3) Å3 | 0.30 × 0.25 × 0.20 mm |
| Z = 2 |
| Bruker SMART APEX II CCD diffractometer | 2612 independent reflections |
| Radiation source: fine-focus sealed tube | 2352 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.023 |
| T = 296(2) K | θmax = 27.5º |
| φ and ω scans | θmin = 2.2º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→9 |
| Tmin = 0.971, Tmax = 0.980 | k = −18→21 |
| 7148 measured reflections | l = −9→11 |
| Refinement on F2 | H-atom parameters constrained |
| Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0485P)2 + 0.0587P] where P = (Fo2 + 2Fc2)/3 |
| R[F2 > 2σ(F2)] = 0.034 | (Δ/σ)max < 0.001 |
| wR(F2) = 0.087 | Δρmax = 0.21 e Å−3 |
| S = 1.06 | Δρmin = −0.13 e Å−3 |
| 2612 reflections | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| 302 parameters | Extinction coefficient: 0.015 (3) |
| 1 restraint | Absolute structure: Friedel pairs merged as equivalent data |
| Primary atom site location: structure-invariant direct methods | Flack parameter: ? |
| Secondary atom site location: difference Fourier map | Rogers parameter: ? |
| Hydrogen site location: inferred from neighbouring sites |
| C24H26N2O7 | V = 1116.4 (3) Å3 |
| Mr = 454.47 | Z = 2 |
| Monoclinic, P21 | Mo Kα |
| a = 7.3998 (10) Å | µ = 0.10 mm−1 |
| b = 16.383 (2) Å | T = 296 (2) K |
| c = 9.2162 (13) Å | 0.30 × 0.25 × 0.20 mm |
| β = 92.322 (2)º |
| Bruker SMART APEX II CCD diffractometer | 2612 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2352 reflections with I > 2σ(I) |
| Tmin = 0.971, Tmax = 0.980 | Rint = 0.023 |
| 7148 measured reflections |
| R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
| wR(F2) = 0.087 | Δρmax = 0.21 e Å−3 |
| S = 1.06 | Δρmin = −0.13 e Å−3 |
| 2612 reflections | Absolute structure: Friedel pairs merged as equivalent data |
| 302 parameters | Flack parameter: ? |
| 1 restraint | Rogers parameter: ? |
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 > 2sigma(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 | 0.9756 (3) | 0.86809 (10) | 0.37052 (17) | 0.0497 (4) | |
| O2 | 1.0016 (3) | 0.90832 (11) | 0.14679 (19) | 0.0571 (5) | |
| O3 | 0.8961 (2) | 0.75590 (10) | 0.03780 (15) | 0.0361 (3) | |
| O4 | 0.6197 (2) | 0.46524 (11) | 0.2027 (2) | 0.0518 (4) | |
| O5 | 0.8933 (2) | 0.44686 (10) | 0.31575 (17) | 0.0438 (4) | |
| O6 | 0.8228 (2) | 0.68765 (11) | 0.66980 (16) | 0.0445 (4) | |
| O7 | 1.1799 (2) | 0.74245 (12) | 0.13801 (17) | 0.0483 (4) | |
| N1 | 0.7652 (2) | 0.59843 (11) | 0.48365 (19) | 0.0342 (4) | |
| N2 | 1.1043 (3) | 0.69448 (13) | −0.0887 (2) | 0.0429 (5) | |
| H2 | 1.0138 | 0.6919 | −0.1538 | 0.043 (7)* | |
| C1 | 0.9037 (3) | 0.81619 (15) | 0.4800 (2) | 0.0415 (5) | |
| H1A | 0.8013 | 0.8434 | 0.5212 | 0.050* | |
| H1B | 0.9953 | 0.8090 | 0.5573 | 0.050* | |
| C2 | 0.9466 (3) | 0.85775 (14) | 0.2281 (2) | 0.0395 (5) | |
| C3 | 0.8317 (3) | 0.78525 (13) | 0.1735 (2) | 0.0337 (4) | |
| C4 | 0.8214 (3) | 0.71695 (12) | 0.2830 (2) | 0.0314 (4) | |
| C5 | 0.7784 (3) | 0.63660 (14) | 0.2365 (2) | 0.0343 (4) | |
| H5 | 0.7661 | 0.6238 | 0.1383 | 0.041* | |
| C6 | 0.7561 (3) | 0.57932 (13) | 0.3391 (2) | 0.0331 (4) | |
| C7 | 0.7254 (3) | 0.48743 (13) | 0.3259 (3) | 0.0382 (5) | |
| C8 | 0.6437 (3) | 0.46579 (16) | 0.4706 (3) | 0.0479 (6) | |
| H8A | 0.5127 | 0.4682 | 0.4625 | 0.057* | |
| H8B | 0.6798 | 0.4113 | 0.5012 | 0.057* | |
| C9 | 0.7175 (3) | 0.52940 (15) | 0.5779 (3) | 0.0442 (6) | |
| H9A | 0.6265 | 0.5453 | 0.6454 | 0.053* | |
| H9B | 0.8230 | 0.5090 | 0.6323 | 0.053* | |
| C10 | 0.8130 (3) | 0.67425 (14) | 0.5379 (2) | 0.0342 (4) | |
| C11 | 0.8446 (3) | 0.73440 (13) | 0.4266 (2) | 0.0326 (4) | |
| C12 | 0.9214 (4) | 0.43939 (19) | 0.1647 (3) | 0.0581 (7) | |
| H12A | 0.9934 | 0.3915 | 0.1447 | 0.070* | |
| H12B | 0.9815 | 0.4873 | 0.1281 | 0.070* | |
| C13 | 0.7343 (5) | 0.4315 (2) | 0.0987 (3) | 0.0685 (9) | |
| H13A | 0.7230 | 0.4613 | 0.0078 | 0.082* | |
| H13B | 0.7046 | 0.3746 | 0.0804 | 0.082* | |
| C14 | 0.6397 (3) | 0.81741 (16) | 0.1294 (2) | 0.0432 (5) | |
| H14A | 0.6488 | 0.8518 | 0.0444 | 0.052* | |
| H14B | 0.5640 | 0.7712 | 0.1018 | 0.052* | |
| C15 | 0.5467 (3) | 0.86541 (17) | 0.2454 (3) | 0.0510 (6) | |
| H15A | 0.6108 | 0.9155 | 0.2638 | 0.076* | |
| H15B | 0.5456 | 0.8338 | 0.3330 | 0.076* | |
| H15C | 0.4247 | 0.8773 | 0.2127 | 0.076* | |
| C16 | 1.0725 (3) | 0.73094 (14) | 0.0376 (2) | 0.0357 (5) | |
| C17 | 1.2862 (3) | 0.66796 (18) | −0.1258 (3) | 0.0493 (6) | |
| H17 | 1.3694 | 0.7138 | −0.1083 | 0.059* | |
| C18 | 1.3521 (6) | 0.5967 (3) | −0.0323 (3) | 0.0880 (13) | |
| H18A | 1.2645 | 0.5535 | −0.0383 | 0.132* | |
| H18B | 1.3680 | 0.6143 | 0.0668 | 0.132* | |
| H18C | 1.4653 | 0.5774 | −0.0662 | 0.132* | |
| C19 | 1.2817 (3) | 0.64878 (15) | −0.2861 (2) | 0.0378 (5) | |
| C20 | 1.2066 (3) | 0.57611 (15) | −0.3382 (2) | 0.0424 (5) | |
| H20 | 1.1624 | 0.5383 | −0.2732 | 0.051* | |
| C21 | 1.1968 (4) | 0.55937 (18) | −0.4847 (3) | 0.0517 (7) | |
| H21 | 1.1485 | 0.5100 | −0.5175 | 0.062* | |
| C22 | 1.2572 (4) | 0.6144 (2) | −0.5813 (3) | 0.0611 (8) | |
| H22 | 1.2488 | 0.6030 | −0.6803 | 0.073* | |
| C23 | 1.3300 (4) | 0.6861 (2) | −0.5336 (3) | 0.0696 (9) | |
| H23 | 1.3713 | 0.7237 | −0.6003 | 0.084* | |
| C24 | 1.3436 (4) | 0.70394 (18) | −0.3862 (3) | 0.0558 (7) | |
| H24 | 1.3945 | 0.7531 | −0.3547 | 0.067* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0722 (12) | 0.0424 (9) | 0.0346 (8) | −0.0192 (9) | 0.0029 (8) | −0.0057 (7) |
| O2 | 0.0855 (14) | 0.0408 (9) | 0.0462 (10) | −0.0161 (10) | 0.0177 (9) | −0.0003 (8) |
| O3 | 0.0421 (8) | 0.0407 (8) | 0.0254 (7) | 0.0030 (7) | 0.0020 (6) | −0.0044 (6) |
| O4 | 0.0513 (9) | 0.0465 (10) | 0.0567 (11) | −0.0033 (8) | −0.0082 (8) | −0.0087 (8) |
| O5 | 0.0487 (9) | 0.0429 (9) | 0.0396 (8) | 0.0118 (7) | 0.0007 (7) | −0.0048 (7) |
| O6 | 0.0530 (9) | 0.0532 (10) | 0.0274 (8) | 0.0067 (8) | −0.0001 (7) | −0.0026 (7) |
| O7 | 0.0462 (9) | 0.0642 (12) | 0.0339 (8) | 0.0019 (8) | −0.0043 (7) | −0.0097 (8) |
| N1 | 0.0365 (9) | 0.0356 (10) | 0.0306 (9) | 0.0042 (8) | 0.0044 (7) | 0.0025 (7) |
| N2 | 0.0400 (10) | 0.0571 (13) | 0.0313 (9) | 0.0084 (9) | −0.0022 (8) | −0.0104 (9) |
| C1 | 0.0527 (13) | 0.0394 (12) | 0.0324 (11) | −0.0061 (11) | 0.0010 (10) | −0.0039 (10) |
| C2 | 0.0478 (12) | 0.0348 (12) | 0.0363 (12) | −0.0035 (10) | 0.0083 (10) | −0.0043 (10) |
| C3 | 0.0405 (11) | 0.0331 (10) | 0.0274 (10) | 0.0012 (9) | 0.0020 (8) | −0.0041 (8) |
| C4 | 0.0326 (10) | 0.0323 (10) | 0.0295 (10) | 0.0019 (8) | 0.0021 (8) | −0.0033 (8) |
| C5 | 0.0413 (11) | 0.0341 (11) | 0.0274 (10) | −0.0003 (9) | −0.0010 (8) | −0.0046 (8) |
| C6 | 0.0326 (10) | 0.0322 (11) | 0.0344 (11) | 0.0026 (8) | 0.0008 (8) | −0.0044 (9) |
| C7 | 0.0394 (11) | 0.0310 (11) | 0.0441 (13) | 0.0014 (9) | 0.0010 (9) | 0.0002 (9) |
| C8 | 0.0508 (13) | 0.0394 (13) | 0.0545 (15) | 0.0010 (11) | 0.0133 (11) | 0.0048 (11) |
| C9 | 0.0528 (14) | 0.0399 (12) | 0.0408 (13) | 0.0058 (11) | 0.0130 (10) | 0.0095 (10) |
| C10 | 0.0339 (10) | 0.0393 (11) | 0.0295 (10) | 0.0065 (9) | 0.0019 (8) | −0.0020 (9) |
| C11 | 0.0343 (10) | 0.0357 (11) | 0.0278 (10) | 0.0018 (9) | 0.0016 (8) | −0.0045 (8) |
| C12 | 0.0686 (18) | 0.0605 (17) | 0.0456 (14) | 0.0120 (14) | 0.0076 (13) | −0.0118 (13) |
| C13 | 0.087 (2) | 0.0624 (19) | 0.0550 (16) | 0.0104 (16) | −0.0080 (15) | −0.0230 (15) |
| C14 | 0.0458 (12) | 0.0446 (13) | 0.0390 (12) | 0.0085 (10) | 0.0000 (10) | −0.0004 (10) |
| C15 | 0.0477 (13) | 0.0490 (14) | 0.0567 (15) | 0.0068 (12) | 0.0083 (11) | −0.0009 (12) |
| C16 | 0.0439 (11) | 0.0357 (11) | 0.0276 (10) | 0.0011 (9) | 0.0021 (9) | −0.0009 (9) |
| C17 | 0.0441 (13) | 0.0624 (17) | 0.0411 (13) | 0.0119 (11) | −0.0027 (10) | −0.0115 (12) |
| C18 | 0.110 (3) | 0.115 (3) | 0.0382 (15) | 0.065 (3) | −0.0092 (16) | −0.0031 (17) |
| C19 | 0.0324 (10) | 0.0446 (13) | 0.0365 (12) | 0.0058 (9) | 0.0046 (8) | −0.0024 (10) |
| C20 | 0.0445 (12) | 0.0438 (13) | 0.0390 (12) | 0.0037 (10) | 0.0025 (10) | 0.0011 (10) |
| C21 | 0.0482 (14) | 0.0552 (15) | 0.0512 (15) | 0.0099 (12) | −0.0054 (11) | −0.0172 (12) |
| C22 | 0.0525 (15) | 0.092 (2) | 0.0383 (14) | 0.0138 (15) | 0.0034 (12) | −0.0036 (14) |
| C23 | 0.0656 (18) | 0.093 (3) | 0.0515 (17) | −0.0036 (18) | 0.0146 (14) | 0.0258 (17) |
| C24 | 0.0545 (15) | 0.0497 (15) | 0.0633 (18) | −0.0088 (12) | 0.0033 (13) | 0.0010 (13) |
| O1—C2 | 1.333 (3) | C9—H9A | 0.970 |
| O1—C1 | 1.438 (3) | C9—H9B | 0.970 |
| O2—C2 | 1.199 (3) | C10—C11 | 1.448 (3) |
| O3—C16 | 1.369 (3) | C12—C13 | 1.495 (5) |
| O3—C3 | 1.439 (2) | C12—H12A | 0.970 |
| O4—C7 | 1.400 (3) | C12—H12B | 0.970 |
| O4—C13 | 1.419 (4) | C13—H13A | 0.970 |
| O5—C7 | 1.416 (3) | C13—H13B | 0.970 |
| O5—C12 | 1.421 (3) | C14—C15 | 1.515 (3) |
| O6—C10 | 1.235 (3) | C14—H14A | 0.970 |
| O7—C16 | 1.210 (3) | C14—H14B | 0.970 |
| N1—C6 | 1.368 (3) | C15—H15A | 0.960 |
| N1—C10 | 1.380 (3) | C15—H15B | 0.960 |
| N1—C9 | 1.478 (3) | C15—H15C | 0.960 |
| N2—C16 | 1.337 (3) | C17—C19 | 1.510 (3) |
| N2—C17 | 1.468 (3) | C17—C18 | 1.519 (4) |
| N2—H2 | 0.88 | C17—H17 | 0.980 |
| C1—C11 | 1.487 (3) | C18—H18A | 0.960 |
| C1—H1A | 0.970 | C18—H18B | 0.960 |
| C1—H1B | 0.970 | C18—H18C | 0.960 |
| C2—C3 | 1.534 (3) | C19—C24 | 1.382 (4) |
| C3—C4 | 1.511 (3) | C19—C20 | 1.391 (3) |
| C3—C14 | 1.553 (3) | C20—C21 | 1.377 (3) |
| C4—C11 | 1.358 (3) | C20—H20 | 0.930 |
| C4—C5 | 1.417 (3) | C21—C22 | 1.356 (4) |
| C5—C6 | 1.347 (3) | C21—H21 | 0.930 |
| C5—H5 | 0.930 | C22—C23 | 1.359 (5) |
| C6—C7 | 1.527 (3) | C22—H22 | 0.930 |
| C7—C8 | 1.528 (3) | C23—C24 | 1.390 (4) |
| C8—C9 | 1.523 (4) | C23—H23 | 0.930 |
| C8—H8A | 0.970 | C24—H24 | 0.930 |
| C8—H8B | 0.970 | ||
| C2—O1—C1 | 124.53 (18) | O5—C12—C13 | 103.7 (2) |
| C16—O3—C3 | 116.79 (16) | O5—C12—H12A | 111.0 |
| C7—O4—C13 | 108.6 (2) | C13—C12—H12A | 111.0 |
| C7—O5—C12 | 105.57 (19) | O5—C12—H12B | 111.0 |
| C6—N1—C10 | 124.12 (18) | C13—C12—H12B | 111.0 |
| C6—N1—C9 | 113.22 (18) | H12A—C12—H12B | 109.0 |
| C10—N1—C9 | 122.67 (18) | O4—C13—C12 | 105.1 (2) |
| C16—N2—C17 | 122.03 (19) | O4—C13—H13A | 110.7 |
| C16—N2—H2 | 117.3 | C12—C13—H13A | 110.7 |
| C17—N2—H2 | 120.3 | O4—C13—H13B | 110.7 |
| O1—C1—C11 | 114.38 (17) | C12—C13—H13B | 110.7 |
| O1—C1—H1A | 108.7 | H13A—C13—H13B | 108.8 |
| C11—C1—H1A | 108.7 | C15—C14—C3 | 115.36 (19) |
| O1—C1—H1B | 108.7 | C15—C14—H14A | 108.4 |
| C11—C1—H1B | 108.7 | C3—C14—H14A | 108.4 |
| H1A—C1—H1B | 107.6 | C15—C14—H14B | 108.4 |
| O2—C2—O1 | 118.8 (2) | C3—C14—H14B | 108.4 |
| O2—C2—C3 | 121.9 (2) | H14A—C14—H14B | 107.5 |
| O1—C2—C3 | 119.10 (18) | C14—C15—H15A | 109.5 |
| O3—C3—C4 | 111.14 (17) | C14—C15—H15B | 109.5 |
| O3—C3—C2 | 110.17 (16) | H15A—C15—H15B | 109.5 |
| C4—C3—C2 | 113.39 (17) | C14—C15—H15C | 109.5 |
| O3—C3—C14 | 102.54 (16) | H15A—C15—H15C | 109.5 |
| C4—C3—C14 | 110.84 (18) | H15B—C15—H15C | 109.5 |
| C2—C3—C14 | 108.18 (18) | O7—C16—N2 | 127.0 (2) |
| C11—C4—C5 | 120.59 (19) | O7—C16—O3 | 123.32 (19) |
| C11—C4—C3 | 119.16 (18) | N2—C16—O3 | 109.65 (18) |
| C5—C4—C3 | 120.17 (18) | N2—C17—C19 | 107.78 (18) |
| C6—C5—C4 | 117.85 (19) | N2—C17—C18 | 111.8 (3) |
| C6—C5—H5 | 121.1 | C19—C17—C18 | 112.9 (2) |
| C4—C5—H5 | 121.1 | N2—C17—H17 | 108.1 |
| C5—C6—N1 | 121.5 (2) | C19—C17—H17 | 108.1 |
| C5—C6—C7 | 130.8 (2) | C18—C17—H17 | 108.1 |
| N1—C6—C7 | 107.74 (18) | C17—C18—H18A | 109.5 |
| O4—C7—O5 | 106.74 (19) | C17—C18—H18B | 109.5 |
| O4—C7—C6 | 113.41 (19) | H18A—C18—H18B | 109.5 |
| O5—C7—C6 | 109.87 (18) | C17—C18—H18C | 109.5 |
| O4—C7—C8 | 114.8 (2) | H18A—C18—H18C | 109.5 |
| O5—C7—C8 | 109.14 (19) | H18B—C18—H18C | 109.5 |
| C6—C7—C8 | 102.82 (19) | C24—C19—C20 | 117.9 (2) |
| C9—C8—C7 | 105.3 (2) | C24—C19—C17 | 121.5 (2) |
| C9—C8—H8A | 110.7 | C20—C19—C17 | 120.6 (2) |
| C7—C8—H8A | 110.7 | C21—C20—C19 | 120.9 (2) |
| C9—C8—H8B | 110.7 | C21—C20—H20 | 119.6 |
| C7—C8—H8B | 110.7 | C19—C20—H20 | 119.6 |
| H8A—C8—H8B | 108.8 | C22—C21—C20 | 120.4 (3) |
| N1—C9—C8 | 103.28 (19) | C22—C21—H21 | 119.8 |
| N1—C9—H9A | 111.1 | C20—C21—H21 | 119.8 |
| C8—C9—H9A | 111.1 | C21—C22—C23 | 119.9 (3) |
| N1—C9—H9B | 111.1 | C21—C22—H22 | 120.0 |
| C8—C9—H9B | 111.1 | C23—C22—H22 | 120.0 |
| H9A—C9—H9B | 109.1 | C22—C23—C24 | 120.7 (3) |
| O6—C10—N1 | 121.4 (2) | C22—C23—H23 | 119.6 |
| O6—C10—C11 | 124.9 (2) | C24—C23—H23 | 119.6 |
| N1—C10—C11 | 113.73 (18) | C19—C24—C23 | 120.1 (3) |
| C4—C11—C10 | 121.9 (2) | C19—C24—H24 | 119.9 |
| C4—C11—C1 | 122.42 (19) | C23—C24—H24 | 119.9 |
| C10—C11—C1 | 115.64 (17) | ||
| C2—O1—C1—C11 | 19.3 (3) | C6—N1—C9—C8 | −9.5 (2) |
| C1—O1—C2—O2 | 174.3 (2) | C10—N1—C9—C8 | 170.22 (18) |
| C1—O1—C2—C3 | −1.0 (3) | C7—C8—C9—N1 | 23.0 (2) |
| C16—O3—C3—C4 | −68.2 (2) | C6—N1—C10—O6 | −178.39 (19) |
| C16—O3—C3—C2 | 58.3 (2) | C9—N1—C10—O6 | 1.9 (3) |
| C16—O3—C3—C14 | 173.30 (18) | C6—N1—C10—C11 | 3.0 (3) |
| O2—C2—C3—O3 | 38.1 (3) | C9—N1—C10—C11 | −176.68 (18) |
| O1—C2—C3—O3 | −146.7 (2) | C5—C4—C11—C10 | −5.0 (3) |
| O2—C2—C3—C4 | 163.4 (2) | C3—C4—C11—C10 | 171.69 (18) |
| O1—C2—C3—C4 | −21.4 (3) | C5—C4—C11—C1 | 175.1 (2) |
| O2—C2—C3—C14 | −73.2 (3) | C3—C4—C11—C1 | −8.2 (3) |
| O1—C2—C3—C14 | 102.0 (2) | O6—C10—C11—C4 | −176.1 (2) |
| O3—C3—C4—C11 | 150.41 (18) | N1—C10—C11—C4 | 2.5 (3) |
| C2—C3—C4—C11 | 25.7 (3) | O6—C10—C11—C1 | 3.8 (3) |
| C14—C3—C4—C11 | −96.2 (2) | N1—C10—C11—C1 | −177.63 (18) |
| O3—C3—C4—C5 | −32.9 (3) | O1—C1—C11—C4 | −14.4 (3) |
| C2—C3—C4—C5 | −157.67 (18) | O1—C1—C11—C10 | 165.72 (18) |
| C14—C3—C4—C5 | 80.4 (2) | C7—O5—C12—C13 | −31.7 (3) |
| C11—C4—C5—C6 | 2.0 (3) | C7—O4—C13—C12 | −3.3 (3) |
| C3—C4—C5—C6 | −174.58 (19) | O5—C12—C13—O4 | 21.5 (3) |
| C4—C5—C6—N1 | 3.3 (3) | O3—C3—C14—C15 | −170.4 (2) |
| C4—C5—C6—C7 | −174.3 (2) | C4—C3—C14—C15 | 70.9 (3) |
| C10—N1—C6—C5 | −6.0 (3) | C2—C3—C14—C15 | −54.0 (3) |
| C9—N1—C6—C5 | 173.7 (2) | C17—N2—C16—O7 | −4.6 (4) |
| C10—N1—C6—C7 | 172.05 (18) | C17—N2—C16—O3 | 174.3 (2) |
| C9—N1—C6—C7 | −8.3 (2) | C3—O3—C16—O7 | −10.1 (3) |
| C13—O4—C7—O5 | −16.4 (3) | C3—O3—C16—N2 | 170.89 (18) |
| C13—O4—C7—C6 | 104.7 (2) | C16—N2—C17—C19 | −166.5 (2) |
| C13—O4—C7—C8 | −137.5 (2) | C16—N2—C17—C18 | 68.9 (3) |
| C12—O5—C7—O4 | 30.5 (3) | N2—C17—C19—C24 | 99.6 (3) |
| C12—O5—C7—C6 | −92.8 (2) | C18—C17—C19—C24 | −136.5 (3) |
| C12—O5—C7—C8 | 155.1 (2) | N2—C17—C19—C20 | −77.4 (3) |
| C5—C6—C7—O4 | −35.3 (3) | C18—C17—C19—C20 | 46.5 (3) |
| N1—C6—C7—O4 | 146.85 (19) | C24—C19—C20—C21 | 0.9 (4) |
| C5—C6—C7—O5 | 84.0 (3) | C17—C19—C20—C21 | 177.9 (2) |
| N1—C6—C7—O5 | −93.8 (2) | C19—C20—C21—C22 | −1.3 (4) |
| C5—C6—C7—C8 | −159.9 (2) | C20—C21—C22—C23 | 0.8 (4) |
| N1—C6—C7—C8 | 22.3 (2) | C21—C22—C23—C24 | 0.0 (5) |
| O4—C7—C8—C9 | −151.2 (2) | C20—C19—C24—C23 | 0.0 (4) |
| O5—C7—C8—C9 | 89.0 (2) | C17—C19—C24—C23 | −177.1 (3) |
| C6—C7—C8—C9 | −27.6 (2) | C22—C23—C24—C19 | −0.4 (5) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H2···O6i | 0.88 | 2.11 | 2.988 (2) | 173 |
| Symmetry codes: (i) x, y, z−1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H2···O6i | 0.88 | 2.11 | 2.988 (2) | 173 |
| Symmetry codes: (i) x, y, z−1. |
Bruker (1997). SMART (Version 5.611), SAINT (Version 6.0) and SHELXTL (Version 5.10). Bruker AXS Inc., Madison, Wisconsin, USA.
Duggan, M. E. & Imagire, J. S. (1989). Synthesis, 2, 131–132.
Gibbs, R. A., Bartels, K., Lee, R. W. K. & Okamura, W. H. (1989). J. Am. Chem. Soc. 111, 3717–3725.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany.
The method for resolution of a tertiary alcohol using a chiral isocyanate reagent has been widely applied (Gibbs et al., 1989). The title compound is a key intermediate in the resolution process of alcohol 1 using the (S)-isocyanate 2 (Scheme 2).
On the basis of the unchanging S configuration of C17, the molecular structure (Figure 1) indicates that the chiral C atom C3 adopts an S configuration. The six-membered lactone ring is twisted with an O1/C2/C3/C4 torsion angle of −21.4 (3) °. The pyrrole ring is also twisted, with a N1/C6/C7/C8 torsion angle of 22.3 (2) °. N—H···O hydrogen bonds exist between molecules, linking them into chains along the c axis.