Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100012099/qa0365sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100012099/qa0365Isup2.hkl |
CCDC reference: 152677
Crystals of 1,2,7,8-tetra-O-acetylaustraline were obtained as a minor component following acetylation and chromatographic fractionation of the mother liquor remaining after crystallizing castanospermine from extracts of Castanospermine australe seeds.
All H atoms were constrained to an isotropic displacement parameter 1.2 times that of the Ueq value of their parent atom. No Friedel pairs were collected. The absolute configuration cannot be determined from this experiment and was assumed from the synthesis.
Data collection: R3m Software (Siemens, 1983); cell refinement: R3m Software; data reduction: R3m Software; program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.
C16H23NO8 | F(000) = 380 |
Mr = 357.35 | Dx = 1.367 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71069 Å |
a = 9.586 (3) Å | Cell parameters from 25 reflections |
b = 8.279 (2) Å | θ = 4.9–14.2° |
c = 11.096 (5) Å | µ = 0.11 mm−1 |
β = 99.74 (2)° | T = 173 K |
V = 867.9 (5) Å3 | Translucent, colourless |
Z = 2 | 0.44 × 0.26 × 0.16 mm |
Siemens R3m/scintillation counter diffractometer | Rint = 0.026 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.2° |
Graphite monochromator | h = 0→11 |
ω scans | k = 0→9 |
1794 measured reflections | l = −13→13 |
1648 independent reflections | 3 standard reflections every 97 reflections |
1190 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0442P)2] where P = (Fo2 + 2Fc2)/3 |
1648 reflections | (Δ/σ)max < 0.001 |
228 parameters | Δρmax = 0.22 e Å−3 |
1 restraint | Δρmin = −0.27 e Å−3 |
C16H23NO8 | V = 867.9 (5) Å3 |
Mr = 357.35 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 9.586 (3) Å | µ = 0.11 mm−1 |
b = 8.279 (2) Å | T = 173 K |
c = 11.096 (5) Å | 0.44 × 0.26 × 0.16 mm |
β = 99.74 (2)° |
Siemens R3m/scintillation counter diffractometer | Rint = 0.026 |
1794 measured reflections | 3 standard reflections every 97 reflections |
1648 independent reflections | intensity decay: none |
1190 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.053 | 1 restraint |
wR(F2) = 0.108 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.22 e Å−3 |
1648 reflections | Δρmin = −0.27 e Å−3 |
228 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 for observed reflections. Methyl H atoms on C13 and c17 were refined in two orientation sets. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.4488 (3) | 0.1870 (5) | 0.1999 (3) | 0.0230 (8) | |
O2 | 0.4176 (4) | −0.0022 (5) | 0.3389 (3) | 0.0275 (9) | |
O3 | 0.6802 (3) | 0.1739 (5) | 0.0381 (3) | 0.0236 (8) | |
O4 | 0.5324 (5) | 0.3446 (6) | −0.0757 (4) | 0.0499 (12) | |
O5 | 0.8429 (4) | 0.5629 (4) | 0.1582 (4) | 0.0287 (10) | |
O6 | 1.0267 (4) | 0.6673 (5) | 0.0856 (4) | 0.0381 (10) | |
O7 | 0.7386 (4) | −0.0139 (4) | 0.4296 (3) | 0.0228 (9) | |
O8 | 0.6866 (4) | −0.1321 (5) | 0.6003 (4) | 0.0414 (11) | |
N4 | 0.7935 (4) | 0.3287 (5) | 0.3422 (4) | 0.0214 (10) | |
C1 | 0.5988 (4) | 0.1725 (7) | 0.2361 (4) | 0.0203 (11) | |
H1 | 0.6269 | 0.0561 | 0.2370 | 0.024* | |
C2 | 0.6736 (5) | 0.2652 (6) | 0.1480 (5) | 0.0208 (12) | |
H2 | 0.6269 | 0.3721 | 0.1275 | 0.025* | |
C3 | 0.8223 (5) | 0.2882 (6) | 0.2208 (5) | 0.0217 (12) | |
H3 | 0.8715 | 0.1813 | 0.2262 | 0.026* | |
C5 | 0.9026 (5) | 0.2856 (7) | 0.4457 (5) | 0.0283 (13) | |
H5A | 0.9625 | 0.3804 | 0.4734 | 0.034* | |
H5B | 0.9638 | 0.1984 | 0.4227 | 0.034* | |
C6 | 0.8233 (5) | 0.2283 (7) | 0.5468 (5) | 0.0272 (13) | |
H6A | 0.8815 | 0.1534 | 0.6040 | 0.033* | |
H6B | 0.7931 | 0.3203 | 0.5932 | 0.033* | |
C7 | 0.6966 (5) | 0.1422 (6) | 0.4719 (5) | 0.0221 (13) | |
H7 | 0.6165 | 0.1317 | 0.5185 | 0.026* | |
C7A | 0.6579 (5) | 0.2507 (6) | 0.3602 (5) | 0.0219 (12) | |
H7A | 0.5907 | 0.3361 | 0.3786 | 0.026* | |
C8 | 0.9140 (5) | 0.4091 (6) | 0.1690 (5) | 0.0266 (13) | |
H8A | 1.0067 | 0.4189 | 0.2236 | 0.032* | |
H8B | 0.9309 | 0.3727 | 0.0877 | 0.032* | |
C10 | 0.3695 (5) | 0.0857 (7) | 0.2568 (5) | 0.0259 (13) | |
C11 | 0.2161 (5) | 0.0968 (8) | 0.1977 (5) | 0.0368 (16) | |
H11A | 0.1597 | 0.0226 | 0.2387 | 0.055* | |
H11B | 0.2066 | 0.0675 | 0.1111 | 0.055* | |
H11C | 0.1823 | 0.2075 | 0.2047 | 0.055* | |
C12 | 0.6052 (5) | 0.2281 (7) | −0.0677 (5) | 0.0264 (13) | |
C13 | 0.6243 (6) | 0.1182 (8) | −0.1718 (5) | 0.0347 (16) | |
H13A | 0.6899 | 0.0309 | −0.1411 | 0.052* | 0.17 (6) |
H13B | 0.6628 | 0.1800 | −0.2339 | 0.052* | 0.17 (6) |
H13C | 0.5326 | 0.0720 | −0.2080 | 0.052* | 0.17 (6) |
H13D | 0.5670 | 0.1577 | −0.2476 | 0.052* | 0.83 (6) |
H13E | 0.5941 | 0.0086 | −0.1548 | 0.052* | 0.83 (6) |
H13F | 0.7243 | 0.1166 | −0.1807 | 0.052* | 0.83 (6) |
C14 | 0.9127 (5) | 0.6843 (7) | 0.1142 (5) | 0.0259 (12) | |
C15 | 0.8318 (7) | 0.8384 (8) | 0.1081 (6) | 0.0403 (16) | |
H15A | 0.8824 | 0.9220 | 0.0702 | 0.060* | |
H15B | 0.8221 | 0.8721 | 0.1910 | 0.060* | |
H15C | 0.7377 | 0.8224 | 0.0592 | 0.060* | |
C16 | 0.7157 (5) | −0.1426 (7) | 0.4995 (5) | 0.0279 (13) | |
C17 | 0.7289 (6) | −0.2969 (7) | 0.4312 (5) | 0.0300 (14) | |
H17A | 0.7535 | −0.2719 | 0.3510 | 0.045* | 0.25 (5) |
H17B | 0.6387 | −0.3552 | 0.4202 | 0.045* | 0.25 (5) |
H17C | 0.8033 | −0.3641 | 0.4778 | 0.045* | 0.25 (5) |
H17D | 0.7102 | −0.3889 | 0.4816 | 0.045* | 0.75 (5) |
H17E | 0.8250 | −0.3057 | 0.4125 | 0.045* | 0.75 (5) |
H17F | 0.6604 | −0.2967 | 0.3549 | 0.045* | 0.75 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0232 (17) | 0.020 (2) | 0.026 (2) | 0.0025 (17) | 0.0026 (14) | 0.0010 (18) |
O2 | 0.035 (2) | 0.025 (2) | 0.023 (2) | −0.0033 (18) | 0.0054 (16) | 0.0083 (19) |
O3 | 0.0339 (19) | 0.021 (2) | 0.0155 (19) | 0.0048 (18) | 0.0039 (14) | 0.0012 (18) |
O4 | 0.063 (3) | 0.051 (3) | 0.033 (2) | 0.032 (3) | 0.000 (2) | 0.007 (2) |
O5 | 0.040 (2) | 0.014 (2) | 0.036 (3) | 0.0053 (17) | 0.0189 (19) | 0.0076 (18) |
O6 | 0.033 (2) | 0.024 (2) | 0.061 (3) | 0.004 (2) | 0.0204 (19) | 0.015 (2) |
O7 | 0.031 (2) | 0.017 (2) | 0.021 (2) | 0.0035 (16) | 0.0045 (16) | 0.0035 (17) |
O8 | 0.070 (3) | 0.027 (3) | 0.032 (3) | 0.002 (2) | 0.022 (2) | 0.002 (2) |
N4 | 0.022 (2) | 0.018 (3) | 0.023 (3) | −0.0002 (19) | 0.0017 (18) | 0.001 (2) |
C1 | 0.015 (2) | 0.021 (3) | 0.025 (3) | 0.003 (2) | 0.0019 (19) | 0.006 (3) |
C2 | 0.026 (3) | 0.012 (3) | 0.024 (3) | 0.005 (2) | 0.005 (2) | 0.000 (2) |
C3 | 0.027 (3) | 0.014 (3) | 0.025 (3) | −0.001 (2) | 0.007 (2) | −0.001 (2) |
C5 | 0.027 (3) | 0.030 (3) | 0.029 (3) | −0.005 (3) | 0.007 (2) | 0.002 (3) |
C6 | 0.032 (3) | 0.029 (4) | 0.020 (3) | 0.000 (2) | 0.003 (2) | −0.002 (3) |
C7 | 0.029 (3) | 0.020 (3) | 0.017 (3) | 0.003 (2) | 0.004 (2) | −0.003 (2) |
C7A | 0.026 (3) | 0.017 (3) | 0.023 (3) | 0.004 (2) | 0.004 (2) | 0.002 (2) |
C8 | 0.032 (3) | 0.017 (3) | 0.033 (4) | 0.004 (3) | 0.013 (2) | 0.002 (3) |
C10 | 0.026 (3) | 0.023 (3) | 0.031 (3) | −0.005 (3) | 0.012 (2) | −0.011 (3) |
C11 | 0.021 (3) | 0.045 (4) | 0.044 (4) | 0.002 (3) | 0.008 (2) | 0.005 (3) |
C12 | 0.031 (3) | 0.025 (3) | 0.023 (3) | −0.003 (3) | 0.006 (2) | 0.007 (3) |
C13 | 0.037 (3) | 0.046 (4) | 0.020 (3) | −0.009 (3) | 0.002 (2) | −0.005 (3) |
C14 | 0.030 (3) | 0.021 (3) | 0.027 (3) | −0.001 (3) | 0.007 (2) | 0.002 (3) |
C15 | 0.052 (4) | 0.024 (4) | 0.051 (4) | 0.000 (3) | 0.026 (3) | 0.007 (3) |
C16 | 0.035 (3) | 0.021 (3) | 0.028 (3) | 0.003 (3) | 0.006 (3) | 0.004 (3) |
C17 | 0.037 (3) | 0.019 (3) | 0.035 (4) | −0.004 (3) | 0.010 (3) | 0.000 (3) |
O1—C10 | 1.357 (7) | C7—C7A | 1.525 (7) |
O1—C1 | 1.431 (5) | C7—H7 | 1.0000 |
O2—C10 | 1.196 (7) | C7A—H7A | 1.0000 |
O3—C12 | 1.345 (6) | C8—H8A | 0.9900 |
O3—C2 | 1.446 (6) | C8—H8B | 0.9900 |
O4—C12 | 1.185 (7) | C10—C11 | 1.508 (7) |
O5—C14 | 1.344 (6) | C11—H11A | 0.9800 |
O5—C8 | 1.440 (6) | C11—H11B | 0.9800 |
O6—C14 | 1.196 (5) | C11—H11C | 0.9800 |
O7—C16 | 1.358 (6) | C12—C13 | 1.506 (8) |
O7—C7 | 1.455 (6) | C13—H13A | 0.9800 |
O8—C16 | 1.200 (6) | C13—H13B | 0.9800 |
N4—C3 | 1.458 (6) | C13—H13C | 0.9800 |
N4—C5 | 1.461 (6) | C13—H13D | 0.9800 |
N4—C7A | 1.494 (6) | C13—H13E | 0.9800 |
C1—C2 | 1.515 (7) | C13—H13F | 0.9800 |
C1—C7A | 1.541 (7) | C14—C15 | 1.488 (8) |
C1—H1 | 1.0000 | C15—H15A | 0.9800 |
C2—C3 | 1.527 (7) | C15—H15B | 0.9800 |
C2—H2 | 1.0000 | C15—H15C | 0.9800 |
C3—C8 | 1.509 (7) | C16—C17 | 1.502 (8) |
C3—H3 | 1.0000 | C17—H17A | 0.9800 |
C5—C6 | 1.533 (7) | C17—H17B | 0.9800 |
C5—H5A | 0.9900 | C17—H17C | 0.9800 |
C5—H5B | 0.9900 | C17—H17D | 0.9800 |
C6—C7 | 1.527 (7) | C17—H17E | 0.9800 |
C6—H6A | 0.9900 | C17—H17F | 0.9800 |
C6—H6B | 0.9900 | ||
C10—O1—C1 | 115.7 (4) | C10—C11—H11C | 109.5 |
C12—O3—C2 | 117.9 (4) | H11A—C11—H11C | 109.5 |
C14—O5—C8 | 115.7 (4) | H11B—C11—H11C | 109.5 |
C16—O7—C7 | 115.6 (4) | O4—C12—O3 | 123.9 (5) |
C3—N4—C5 | 116.6 (4) | O4—C12—C13 | 125.5 (5) |
C3—N4—C7A | 109.2 (4) | O3—C12—C13 | 110.5 (5) |
C5—N4—C7A | 108.2 (4) | C12—C13—H13A | 109.5 |
O1—C1—C2 | 109.8 (4) | C12—C13—H13B | 109.5 |
O1—C1—C7A | 114.6 (4) | H13A—C13—H13B | 109.5 |
C2—C1—C7A | 102.8 (4) | C12—C13—H13C | 109.5 |
O1—C1—H1 | 109.8 | H13A—C13—H13C | 109.5 |
C2—C1—H1 | 109.8 | H13B—C13—H13C | 109.5 |
C7A—C1—H1 | 109.8 | C12—C13—H13D | 109.5 |
O3—C2—C1 | 111.8 (4) | H13A—C13—H13D | 141.1 |
O3—C2—C3 | 110.0 (4) | H13B—C13—H13D | 56.3 |
C1—C2—C3 | 102.9 (4) | H13C—C13—H13D | 56.3 |
O3—C2—H2 | 110.6 | C12—C13—H13E | 109.5 |
C1—C2—H2 | 110.6 | H13A—C13—H13E | 56.3 |
C3—C2—H2 | 110.6 | H13B—C13—H13E | 141.1 |
N4—C3—C8 | 114.4 (4) | H13C—C13—H13E | 56.3 |
N4—C3—C2 | 102.2 (4) | H13D—C13—H13E | 109.5 |
C8—C3—C2 | 115.6 (4) | C12—C13—H13F | 109.5 |
N4—C3—H3 | 108.1 | H13A—C13—H13F | 56.3 |
C8—C3—H3 | 108.1 | H13B—C13—H13F | 56.3 |
C2—C3—H3 | 108.1 | H13C—C13—H13F | 141.1 |
N4—C5—C6 | 105.8 (4) | H13D—C13—H13F | 109.5 |
N4—C5—H5A | 110.6 | H13E—C13—H13F | 109.5 |
C6—C5—H5A | 110.6 | O6—C14—O5 | 122.7 (5) |
N4—C5—H5B | 110.6 | O6—C14—C15 | 125.5 (5) |
C6—C5—H5B | 110.6 | O5—C14—C15 | 111.7 (4) |
H5A—C5—H5B | 108.7 | C14—C15—H15A | 109.5 |
C7—C6—C5 | 101.2 (4) | C14—C15—H15B | 109.5 |
C7—C6—H6A | 111.5 | H15A—C15—H15B | 109.5 |
C5—C6—H6A | 111.5 | C14—C15—H15C | 109.5 |
C7—C6—H6B | 111.5 | H15A—C15—H15C | 109.5 |
C5—C6—H6B | 111.5 | H15B—C15—H15C | 109.5 |
H6A—C6—H6B | 109.4 | O8—C16—O7 | 124.1 (6) |
O7—C7—C7A | 107.7 (4) | O8—C16—C17 | 125.8 (6) |
O7—C7—C6 | 110.7 (4) | O7—C16—C17 | 110.1 (4) |
C7A—C7—C6 | 103.2 (4) | C16—C17—H17A | 109.5 |
O7—C7—H7 | 111.6 | C16—C17—H17B | 109.5 |
C7A—C7—H7 | 111.6 | H17A—C17—H17B | 109.5 |
C6—C7—H7 | 111.6 | C16—C17—H17C | 109.5 |
N4—C7A—C7 | 105.4 (4) | H17A—C17—H17C | 109.5 |
N4—C7A—C1 | 105.0 (4) | H17B—C17—H17C | 109.5 |
C7—C7A—C1 | 118.7 (5) | C16—C17—H17D | 109.5 |
N4—C7A—H7A | 109.1 | H17A—C17—H17D | 141.1 |
C7—C7A—H7A | 109.1 | H17B—C17—H17D | 56.3 |
C1—C7A—H7A | 109.1 | H17C—C17—H17D | 56.3 |
O5—C8—C3 | 108.7 (4) | C16—C17—H17E | 109.5 |
O5—C8—H8A | 110.0 | H17A—C17—H17E | 56.3 |
C3—C8—H8A | 110.0 | H17B—C17—H17E | 141.1 |
O5—C8—H8B | 110.0 | H17C—C17—H17E | 56.3 |
C3—C8—H8B | 110.0 | H17D—C17—H17E | 109.5 |
H8A—C8—H8B | 108.3 | C16—C17—H17F | 109.5 |
O2—C10—O1 | 123.8 (5) | H17A—C17—H17F | 56.3 |
O2—C10—C11 | 126.2 (5) | H17B—C17—H17F | 56.3 |
O1—C10—C11 | 110.0 (5) | H17C—C17—H17F | 141.1 |
C10—C11—H11A | 109.5 | H17D—C17—H17F | 109.5 |
C10—C11—H11B | 109.5 | H17E—C17—H17F | 109.5 |
H11A—C11—H11B | 109.5 | ||
C10—O1—C1—C2 | 168.1 (4) | C3—N4—C7A—C7 | 121.0 (4) |
C10—O1—C1—C7A | −76.9 (6) | C5—N4—C7A—C7 | −6.8 (5) |
C12—O3—C2—C1 | 112.7 (5) | C3—N4—C7A—C1 | −5.1 (5) |
C12—O3—C2—C3 | −133.7 (4) | C5—N4—C7A—C1 | −133.0 (4) |
O1—C1—C2—O3 | −81.2 (5) | O7—C7—C7A—N4 | −87.8 (5) |
C7A—C1—C2—O3 | 156.5 (4) | C6—C7—C7A—N4 | 29.2 (5) |
O1—C1—C2—C3 | 160.8 (4) | O7—C7—C7A—C1 | 29.3 (6) |
C7A—C1—C2—C3 | 38.5 (5) | C6—C7—C7A—C1 | 146.4 (4) |
C5—N4—C3—C8 | −82.3 (6) | O1—C1—C7A—N4 | −140.1 (4) |
C7A—N4—C3—C8 | 154.7 (4) | C2—C1—C7A—N4 | −21.0 (5) |
C5—N4—C3—C2 | 151.9 (4) | O1—C1—C7A—C7 | 102.5 (5) |
C7A—N4—C3—C2 | 29.0 (5) | C2—C1—C7A—C7 | −138.4 (4) |
O3—C2—C3—N4 | −161.1 (4) | C14—O5—C8—C3 | 179.3 (4) |
C1—C2—C3—N4 | −41.8 (5) | N4—C3—C8—O5 | −60.9 (6) |
O3—C2—C3—C8 | 74.0 (6) | C2—C3—C8—O5 | 57.5 (6) |
C1—C2—C3—C8 | −166.7 (5) | C1—O1—C10—O2 | 5.8 (8) |
C3—N4—C5—C6 | −141.9 (4) | C1—O1—C10—C11 | −171.9 (4) |
C7A—N4—C5—C6 | −18.4 (6) | C2—O3—C12—O4 | −1.3 (7) |
N4—C5—C6—C7 | 35.9 (5) | C2—O3—C12—C13 | −179.8 (4) |
C16—O7—C7—C7A | −151.5 (4) | C8—O5—C14—O6 | 0.0 (8) |
C16—O7—C7—C6 | 96.4 (5) | C8—O5—C14—C15 | −179.2 (5) |
C5—C6—C7—O7 | 75.6 (5) | C7—O7—C16—O8 | −12.8 (7) |
C5—C6—C7—C7A | −39.3 (5) | C7—O7—C16—C17 | 166.0 (4) |
Experimental details
Crystal data | |
Chemical formula | C16H23NO8 |
Mr | 357.35 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 173 |
a, b, c (Å) | 9.586 (3), 8.279 (2), 11.096 (5) |
β (°) | 99.74 (2) |
V (Å3) | 867.9 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.44 × 0.26 × 0.16 |
Data collection | |
Diffractometer | Siemens R3m/scintillation counter diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1794, 1648, 1190 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.108, 1.01 |
No. of reflections | 1648 |
No. of parameters | 228 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.22, −0.27 |
Computer programs: R3m Software (Siemens, 1983), R3m Software, SHELXS86 (Sheldrick, 1985), SHELXL97 (Sheldrick, 1997), SHELXL97.
O1—C10 | 1.357 (7) | C1—C7A | 1.541 (7) |
O1—C1 | 1.431 (5) | C2—C3 | 1.527 (7) |
N4—C3 | 1.458 (6) | C3—C8 | 1.509 (7) |
N4—C5 | 1.461 (6) | C5—C6 | 1.533 (7) |
N4—C7A | 1.494 (6) | C6—C7 | 1.527 (7) |
C1—C2 | 1.515 (7) | C7—C7A | 1.525 (7) |
C10—O1—C1 | 115.7 (4) | N4—C3—C2 | 102.2 (4) |
C3—N4—C5 | 116.6 (4) | C8—C3—C2 | 115.6 (4) |
C3—N4—C7A | 109.2 (4) | N4—C5—C6 | 105.8 (4) |
C5—N4—C7A | 108.2 (4) | C7—C6—C5 | 101.2 (4) |
O1—C1—C2 | 109.8 (4) | N4—C7A—C7 | 105.4 (4) |
O1—C1—C7A | 114.6 (4) | C7—C7A—C1 | 118.7 (5) |
C2—C1—C7A | 102.8 (4) | O2—C10—O1 | 123.8 (5) |
C1—C2—C3 | 102.9 (4) | O2—C10—C11 | 126.2 (5) |
N4—C3—C8 | 114.4 (4) | O1—C10—C11 | 110.0 (5) |
C10—O1—C1—C2 | 168.1 (4) | C7A—N4—C5—C6 | −18.4 (6) |
C12—O3—C2—C1 | 112.7 (5) | N4—C5—C6—C7 | 35.9 (5) |
C7A—C1—C2—C3 | 38.5 (5) | C5—C6—C7—C7A | −39.3 (5) |
C5—N4—C3—C2 | 151.9 (4) | C3—N4—C7A—C7 | 121.0 (4) |
C7A—N4—C3—C2 | 29.0 (5) | C5—N4—C7A—C7 | −6.8 (5) |
C1—C2—C3—N4 | −41.8 (5) | C2—C1—C7A—N4 | −21.0 (5) |
C3—N4—C5—C6 | −141.9 (4) | C2—C1—C7A—C7 | −138.4 (4) |
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The title compound, (I), was studied to confirm the stereochemistry as there was some ambiguity between the observed and published NMR spectra. It was isolated as an acylated precursor in the preparation of substituted australine derivatives (Furneaux et al., 1994). The structure consists of independent molecules with normal bond lengths and angles (Allen et al., 1992). There are no close intermolecular contacts and the methyl H atoms on C13 and C17 are disordered over two orientations.
The fused ring C1/C2/C3/N4/C7a is in an envelope conformation with flap atom C2 0.623 (8) Å from the C1/C7a/N4/C3 plane, and with Q(2) = 0.409 (5) Å and ϕ = 247 (1)° (Cremer & Pople, 1975). This conformation has been found in all previously determined australine structures (Furneaux et al., 1994; Denmark & Herbet, 1998; Nash et al., 1994) except one, namely 1,2,7-tri-O-acetyl-8-deoxy-8-fluoro-australine (Furneaux et al., 1994; hereafter WEJVOW), where the twist ring description based on C1—C2 applies [Q(2) = 0.453 Å and ϕ = 239°]. The fused ring N4/C5/C6/C7/C7a adopts the twist-ring conformation based on C5—C6, with Q(2) = 0.394 (6) Å and ϕ = 82.1 (8)°, very similar to that found in WEJVOW [Q(2) = 0.414 Å and ϕ = 83°]. We note the close stereochemical similarity with the published structures which indicates that for australine derivatives the molecular geometry is not perturbed by intermolecular hydrogen-bonding crystal-packing forces; for example, in casaurine (Nash et al., 1994), all five hydroxyl protons are involved in O—H···O hydrogen bonds.