Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100014797/qa0410sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100014797/qa0410Isup2.hkl |
CCDC reference: 156204
The EtOH extract of Myoporum bontioides was chromatographed on a silica-gel column using stepwise solvent gradient method (EtOH/petroleum ether). The title compound was obtained from the 12% EtOH/petroleum ether fraction (0.02% dry wt) and crystallized from EtOH yielding colourless crystals (m.p. 474–475 K). Its molecular formula was determined as C22H30O5 from the mass spectrum and elemental analysis. The experimental sample was recrystallized from ethyl alchol/acetone.
The data set is complete to about θ = 27°, but beyond that some data are missing due to locally imposed instrumental conditions. The data set contained no Friedel pairs; anomalous dispersion effects are negigible.
Data collection: CAD-4 Users Manual (Enraf-Nonius, 1985); cell refinement: CAD-4 Users Manual; data reduction: Xtal3.4 ADDREF SORTRF (Hall et al., 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: Xtal3.4 CRYLSQ; molecular graphics: Xtal3.4; software used to prepare material for publication: Xtal3.4 BONDLA CIFIO.
C22H30O5 | Dx = 1.309 Mg m−3 |
Mr = 374.46 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 20 reflections |
a = 8.854 (1) Å | θ = 8.0–15.5° |
b = 12.122 (1) Å | µ = 0.09 mm−1 |
c = 17.708 (2) Å | T = 293 K |
V = 1900.6 (3) Å3 | Block, colourless |
Z = 4 | 0.4 × 0.3 × 0.2 mm |
F(000) = 808 |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.048 |
Radiation source: fine-focus sealed tube | θmax = 28.7° |
Graphite monochromator | h = −10→10 |
ω–2θ scans | k = 0→14 |
4692 measured reflections | l = 0→23 |
2348 independent reflections | 3 standard reflections every 60 min |
2348 reflections with F2 > 0 | intensity decay: 0.1% |
Refinement on F2 | 2 restraints |
Least-squares matrix: full | 0 constraints |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters not refined |
wR(F2) = 0.039 | Calculateda w = 1/[σ2(Fo2) + (0.1253P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.42 | (Δ/σ)max = 0.011 |
2347 reflections | Δρmax = 0.34 e Å−3 |
244 parameters | Δρmin = −0.23 e Å−3 |
C22H30O5 | V = 1900.6 (3) Å3 |
Mr = 374.46 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 8.854 (1) Å | µ = 0.09 mm−1 |
b = 12.122 (1) Å | T = 293 K |
c = 17.708 (2) Å | 0.4 × 0.3 × 0.2 mm |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.048 |
4692 measured reflections | 3 standard reflections every 60 min |
2348 independent reflections | intensity decay: 0.1% |
2348 reflections with F2 > 0 |
R[F2 > 2σ(F2)] = 0.040 | 2 restraints |
wR(F2) = 0.039 | H-atom parameters not refined |
S = 1.42 | Δρmax = 0.34 e Å−3 |
2347 reflections | Δρmin = −0.23 e Å−3 |
244 parameters |
Experimental. The data set is not complete beyond approx. theta = 27 degrees due to instrumental restrictions |
x | y | z | Uiso*/Ueq | ||
O1 | 0.8868 (2) | −0.33387 (13) | 1.13666 (9) | 0.0627 (10) | |
O2 | 0.7934 (2) | 0.08168 (12) | 0.94647 (8) | 0.0542 (9) | |
O3 | 0.8237 (2) | −0.05402 (15) | 0.87217 (9) | 0.0808 (13) | |
O4 | 1.0715 (2) | 0.17485 (13) | 0.90985 (8) | 0.0625 (10) | |
O5 | 1.1944 (3) | 0.1088 (2) | 0.82234 (11) | 0.1156 (18) | |
C1 | 1.2085 (3) | −0.0684 (2) | 1.01138 (13) | 0.0658 (16) | |
H1A | 1.29940 | −0.07730 | 1.03680 | 0.08000* | |
H1B | 1.19020 | −0.12720 | 0.97540 | 0.08000* | |
C2 | 1.2133 (3) | 0.0483 (2) | 0.98130 (13) | 0.0662 (16) | |
H2A | 1.22960 | 0.10770 | 1.01990 | 0.08000* | |
H2B | 1.29550 | 0.05410 | 0.96060 | 0.08000* | |
C3 | 1.0728 (3) | 0.06705 (18) | 0.94176 (11) | 0.0552 (13) | |
H3 | 1.05840 | 0.02080 | 0.90440 | 0.08000* | |
C4 | 0.9330 (3) | 0.06386 (17) | 0.98797 (10) | 0.0497 (12) | |
C5 | 0.9232 (3) | −0.05092 (17) | 1.02170 (11) | 0.0459 (11) | |
H5 | 0.91000 | −0.10010 | 0.97770 | 0.08000* | |
C6 | 0.7839 (3) | −0.06505 (18) | 1.06645 (12) | 0.0546 (13) | |
H6A | 0.77790 | −0.00250 | 1.10050 | 0.08000* | |
H6B | 0.69110 | −0.05390 | 1.04330 | 0.08000* | |
C7 | 0.7883 (3) | −0.17564 (18) | 1.10221 (11) | 0.0527 (12) | |
C8 | 0.9100 (3) | −0.23626 (18) | 1.10075 (12) | 0.0525 (13) | |
C9 | 1.0591 (3) | −0.2146 (2) | 1.06945 (12) | 0.0583 (14) | |
H9A | 1.13390 | −0.23160 | 1.08940 | 0.08000* | |
H9B | 1.06630 | −0.24970 | 1.02950 | 0.08000* | |
C10 | 1.0720 (3) | −0.08926 (17) | 1.05685 (11) | 0.0504 (12) | |
C11 | 0.6762 (3) | −0.23234 (19) | 1.13978 (14) | 0.0585 (14) | |
C12 | 0.7415 (3) | −0.3262 (2) | 1.15965 (13) | 0.0684 (17) | |
H12 | 0.70720 | −0.39950 | 1.18540 | 0.08000* | |
C13 | 0.5154 (3) | −0.1954 (2) | 1.15280 (15) | 0.084 (2) | |
H13A | 0.50210 | −0.12250 | 1.13330 | 0.12500* | |
H13B | 0.49590 | −0.19370 | 1.20710 | 0.12500* | |
H13C | 0.44720 | −0.24530 | 1.12970 | 0.12500* | |
C14 | 0.9241 (3) | 0.16239 (18) | 1.03529 (13) | 0.0669 (15) | |
H14A | 0.83220 | 0.15890 | 1.06530 | 0.10300* | |
H14B | 0.92220 | 0.22680 | 1.00490 | 0.10300* | |
H14C | 1.00890 | 0.16440 | 1.06910 | 0.10300* | |
C15 | 0.7592 (3) | 0.02475 (19) | 0.89090 (13) | 0.0601 (15) | |
C16 | 0.6200 (3) | 0.0705 (2) | 0.85794 (17) | 0.085 (2) | |
H16A | 0.59260 | 0.13700 | 0.88470 | 0.12400* | |
H16B | 0.54170 | 0.01780 | 0.86150 | 0.12400* | |
H16C | 0.63910 | 0.08890 | 0.80590 | 0.12400* | |
C17 | 1.1330 (3) | 0.1847 (2) | 0.84955 (13) | 0.0719 (18) | |
C18 | 1.1106 (4) | 0.3026 (3) | 0.82369 (14) | 0.095 (2) | |
C19 | 1.2114 (5) | 0.3447 (3) | 0.78680 (15) | 0.099 (2) | |
H19 | 1.17730 | 0.43070 | 0.76930 | 0.08000* | |
C20 | 0.9568 (4) | 0.3584 (2) | 0.84507 (18) | 0.098 (2) | |
H20A | 0.89630 | 0.30910 | 0.87330 | 0.14700* | |
H20B | 0.90370 | 0.37970 | 0.79920 | 0.14700* | |
H20C | 0.97580 | 0.42470 | 0.87390 | 0.14700* | |
C21 | 1.3502 (4) | 0.2963 (3) | 0.76509 (16) | 0.089 (2) | |
H21A | 1.40890 | 0.34900 | 0.73690 | 0.12900* | |
H21B | 1.33290 | 0.23220 | 0.73540 | 0.12900* | |
H21C | 1.40650 | 0.27610 | 0.81010 | 0.12900* | |
C22 | 1.0972 (3) | −0.0324 (2) | 1.12993 (11) | 0.0675 (15) | |
H22A | 1.01040 | −0.04490 | 1.16010 | 0.09500* | |
H22B | 1.11030 | 0.04370 | 1.11940 | 0.09500* | |
H22C | 1.18480 | −0.06350 | 1.15200 | 0.09500* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0742 (13) | 0.0503 (9) | 0.0636 (9) | −0.0061 (9) | −0.0125 (9) | 0.0204 (8) |
O2 | 0.0694 (11) | 0.0432 (7) | 0.0501 (8) | 0.0102 (8) | −0.0033 (9) | −0.0003 (7) |
O3 | 0.1002 (15) | 0.0737 (12) | 0.0685 (11) | 0.0227 (11) | −0.0245 (10) | −0.0230 (9) |
O4 | 0.0942 (13) | 0.0486 (9) | 0.0448 (7) | −0.0111 (10) | −0.0053 (9) | 0.0085 (7) |
O5 | 0.187 (3) | 0.0850 (15) | 0.0751 (13) | 0.0063 (18) | 0.0457 (16) | 0.0322 (11) |
C1 | 0.0546 (16) | 0.0823 (18) | 0.0606 (13) | 0.0050 (15) | 0.0057 (12) | 0.0274 (13) |
C2 | 0.0521 (16) | 0.086 (2) | 0.0601 (13) | −0.0063 (15) | 0.0048 (13) | 0.0098 (14) |
C3 | 0.0752 (17) | 0.0423 (12) | 0.0481 (11) | −0.0103 (12) | 0.0015 (13) | 0.0016 (10) |
C4 | 0.0693 (16) | 0.0401 (12) | 0.0398 (9) | −0.0006 (12) | −0.0039 (11) | 0.0030 (9) |
C5 | 0.0541 (14) | 0.0383 (10) | 0.0454 (10) | −0.0006 (11) | 0.0013 (11) | 0.0007 (8) |
C6 | 0.0610 (16) | 0.0428 (12) | 0.0602 (12) | 0.0011 (11) | 0.0045 (12) | 0.0071 (10) |
C7 | 0.0549 (14) | 0.0586 (13) | 0.0444 (10) | −0.0055 (14) | −0.0007 (12) | 0.0065 (11) |
C8 | 0.0595 (14) | 0.0515 (14) | 0.0465 (11) | −0.0080 (12) | −0.0081 (12) | 0.0096 (10) |
C9 | 0.0613 (17) | 0.0551 (13) | 0.0586 (12) | 0.0105 (12) | −0.0078 (12) | 0.0095 (11) |
C10 | 0.0549 (15) | 0.0466 (12) | 0.0498 (10) | −0.0015 (12) | −0.0034 (12) | 0.0091 (10) |
C11 | 0.0672 (16) | 0.0561 (14) | 0.0522 (12) | −0.0072 (13) | 0.0004 (12) | 0.0064 (11) |
C12 | 0.078 (2) | 0.0638 (15) | 0.0635 (14) | −0.0179 (16) | −0.0090 (14) | 0.0156 (13) |
C13 | 0.078 (2) | 0.092 (2) | 0.0818 (19) | −0.0131 (18) | 0.0103 (16) | 0.0078 (16) |
C14 | 0.109 (2) | 0.0380 (10) | 0.0534 (12) | −0.0093 (15) | −0.0009 (15) | −0.0025 (10) |
C15 | 0.0723 (18) | 0.0510 (14) | 0.0570 (13) | 0.0069 (14) | 0.0022 (13) | −0.0043 (12) |
C16 | 0.087 (2) | 0.0786 (19) | 0.0893 (19) | 0.0092 (17) | −0.0247 (17) | 0.0031 (17) |
C17 | 0.100 (2) | 0.0655 (18) | 0.0501 (15) | −0.0093 (15) | 0.0075 (15) | 0.0151 (13) |
C18 | 0.143 (3) | 0.097 (2) | 0.0454 (14) | −0.048 (2) | −0.0150 (18) | 0.0133 (15) |
C19 | 0.150 (4) | 0.095 (2) | 0.0527 (16) | −0.009 (3) | −0.009 (2) | 0.0051 (15) |
C20 | 0.110 (3) | 0.076 (2) | 0.106 (2) | 0.0336 (18) | −0.002 (2) | 0.0267 (16) |
C21 | 0.100 (2) | 0.105 (2) | 0.0621 (16) | 0.004 (2) | 0.0281 (16) | 0.0054 (16) |
C22 | 0.0793 (19) | 0.0721 (15) | 0.0511 (12) | −0.0177 (15) | −0.0095 (13) | 0.0038 (12) |
O1—C8 | 1.359 (3) | C9—C10 | 1.539 (3) |
O1—C12 | 1.352 (3) | C10—C22 | 1.483 (3) |
O2—C4 | 1.454 (3) | C11—C12 | 1.325 (3) |
O2—C15 | 1.240 (3) | C11—C13 | 1.510 (4) |
O3—C15 | 1.161 (3) | C12—H12 | 1.043 (3) |
O4—C3 | 1.424 (3) | C13—H13A | 0.956 (3) |
O4—C17 | 1.205 (3) | C13—H13B | 0.977 (3) |
O5—C17 | 1.172 (4) | C13—H13C | 0.948 (3) |
C1—H1A | 0.929 (3) | C14—H14A | 0.973 (3) |
C1—H1B | 0.970 (3) | C14—H14B | 0.948 (2) |
C1—C2 | 1.512 (4) | C14—H14C | 0.960 (3) |
C1—C10 | 1.474 (3) | C15—C16 | 1.472 (4) |
C2—H2A | 1.003 (3) | C16—H16A | 0.966 (3) |
C2—H2B | 0.818 (2) | C16—H16B | 0.945 (3) |
C2—C3 | 1.445 (3) | C16—H16C | 0.963 (3) |
C3—H3 | 0.876 (2) | C17—C18 | 1.514 (4) |
C3—C4 | 1.484 (3) | C18—C19 | 1.218 (5) |
C4—C5 | 1.517 (3) | C18—C20 | 1.567 (5) |
C4—C14 | 1.461 (3) | C19—H19 | 1.129 (3) |
C5—H5 | 0.988 (2) | C19—C21 | 1.415 (5) |
C5—C6 | 1.476 (3) | C20—H20A | 0.946 (3) |
C5—C10 | 1.529 (3) | C20—H20B | 0.973 (3) |
C6—H6A | 0.970 (2) | C20—H20C | 0.966 (3) |
C6—H6B | 0.928 (2) | C21—H21A | 0.963 (3) |
C6—C7 | 1.483 (3) | C21—H21B | 0.950 (3) |
C7—C8 | 1.305 (3) | C21—H21C | 0.972 (3) |
C7—C11 | 1.379 (3) | C22—H22A | 0.948 (2) |
C8—C9 | 1.456 (4) | C22—H22B | 0.949 (3) |
C9—H9A | 0.779 (2) | C22—H22C | 0.946 (3) |
C9—H9B | 0.828 (2) | ||
C8—O1—C12 | 103.03 (18) | C9—C10—C22 | 110.05 (17) |
C4—O2—C15 | 121.78 (18) | C7—C11—C12 | 104.0 (2) |
C3—O4—C17 | 116.0 (2) | C7—C11—C13 | 127.2 (2) |
H1A—C1—H1B | 112.2 (3) | C12—C11—C13 | 128.8 (2) |
H1A—C1—C2 | 104.8 (2) | O1—C12—C11 | 113.2 (2) |
H1A—C1—C10 | 115.2 (2) | O1—C12—H12 | 110.5 (2) |
H1B—C1—C2 | 117.5 (2) | C11—C12—H12 | 136.1 (3) |
H1B—C1—C10 | 95.5 (2) | C11—C13—H13A | 109.6 (3) |
C2—C1—C10 | 112.1 (2) | C11—C13—H13B | 108.8 (3) |
C1—C2—H2A | 115.8 (2) | C11—C13—H13C | 110.2 (3) |
C1—C2—H2B | 105.3 (3) | H13A—C13—H13B | 108.4 (3) |
C1—C2—C3 | 107.1 (2) | H13A—C13—H13C | 110.9 (3) |
H2A—C2—H2B | 96.6 (3) | H13B—C13—H13C | 109.0 (3) |
H2A—C2—C3 | 109.9 (2) | C4—C14—H14A | 108.8 (2) |
H2B—C2—C3 | 122.4 (2) | C4—C14—H14B | 110.4 (2) |
O4—C3—C2 | 110.1 (2) | C4—C14—H14C | 109.6 (2) |
O4—C3—H3 | 106.64 (18) | H14A—C14—H14B | 109.3 (3) |
O4—C3—C4 | 103.64 (18) | H14A—C14—H14C | 108.3 (2) |
C2—C3—H3 | 113.0 (2) | H14B—C14—H14C | 110.3 (3) |
C2—C3—C4 | 116.51 (18) | O2—C15—O3 | 124.3 (2) |
H3—C3—C4 | 106.2 (2) | O2—C15—C16 | 108.0 (2) |
O2—C4—C3 | 115.23 (16) | O3—C15—C16 | 127.5 (2) |
O2—C4—C5 | 106.67 (18) | C15—C16—H16A | 109.3 (3) |
O2—C4—C14 | 97.05 (19) | C15—C16—H16B | 109.4 (3) |
C3—C4—C5 | 106.78 (18) | C15—C16—H16C | 108.7 (3) |
C3—C4—C14 | 109.9 (2) | H16A—C16—H16B | 110.3 (3) |
C5—C4—C14 | 121.40 (17) | H16A—C16—H16C | 108.7 (3) |
C4—C5—H5 | 104.46 (16) | H16B—C16—H16C | 110.4 (3) |
C4—C5—C6 | 111.44 (19) | O4—C17—O5 | 119.7 (3) |
C4—C5—C10 | 112.95 (19) | O4—C17—C18 | 107.6 (2) |
H5—C5—C6 | 104.7 (2) | O5—C17—C18 | 132.7 (2) |
H5—C5—C10 | 103.88 (19) | C17—C18—C19 | 117.5 (3) |
C6—C5—C10 | 117.78 (17) | C17—C18—C20 | 116.6 (3) |
C5—C6—H6A | 106.8 (2) | C19—C18—C20 | 125.9 (3) |
C5—C6—H6B | 119.1 (2) | C18—C19—H19 | 109.7 (3) |
C5—C6—C7 | 108.18 (19) | C18—C19—C21 | 127.5 (3) |
H6A—C6—H6B | 96.4 (2) | H19—C19—C21 | 122.7 (3) |
H6A—C6—C7 | 116.3 (2) | C18—C20—H20A | 110.3 (3) |
H6B—C6—C7 | 110.1 (2) | C18—C20—H20B | 109.4 (3) |
C6—C7—C8 | 121.5 (2) | C18—C20—H20C | 109.6 (3) |
C6—C7—C11 | 129.6 (2) | H20A—C20—H20B | 109.5 (4) |
C8—C7—C11 | 108.9 (2) | H20A—C20—H20C | 110.2 (3) |
O1—C8—C7 | 110.9 (2) | H20B—C20—H20C | 107.7 (3) |
O1—C8—C9 | 118.2 (2) | C19—C21—H21A | 109.5 (3) |
C7—C8—C9 | 130.9 (2) | C19—C21—H21B | 110.5 (3) |
C8—C9—H9A | 123.4 (2) | C19—C21—H21C | 109.1 (3) |
C8—C9—H9B | 107.6 (2) | H21A—C21—H21B | 110.0 (3) |
C8—C9—C10 | 107.5 (2) | H21A—C21—H21C | 108.4 (3) |
H9A—C9—H9B | 100.7 (3) | H21B—C21—H21C | 109.3 (3) |
H9A—C9—C10 | 105.3 (2) | C10—C22—H22A | 107.2 (2) |
H9B—C9—C10 | 112.2 (2) | C10—C22—H22B | 107.4 (2) |
C1—C10—C5 | 115.57 (18) | C10—C22—H22C | 107.4 (2) |
C1—C10—C9 | 108.0 (2) | H22A—C22—H22B | 111.4 (3) |
C1—C10—C22 | 105.9 (2) | H22A—C22—H22C | 111.6 (2) |
C5—C10—C9 | 107.15 (19) | H22B—C22—H22C | 111.6 (3) |
C5—C10—C22 | 110.11 (19) |
Experimental details
Crystal data | |
Chemical formula | C22H30O5 |
Mr | 374.46 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 293 |
a, b, c (Å) | 8.854 (1), 12.122 (1), 17.708 (2) |
V (Å3) | 1900.6 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.4 × 0.3 × 0.2 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed (F2 > 0) reflections | 4692, 2348, 2348 |
Rint | 0.048 |
(sin θ/λ)max (Å−1) | 0.676 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.039, 1.42 |
No. of reflections | 2347 |
No. of parameters | 244 |
No. of restraints | 2 |
H-atom treatment | H-atom parameters not refined |
Δρmax, Δρmin (e Å−3) | 0.34, −0.23 |
Computer programs: CAD-4 Users Manual (Enraf-Nonius, 1985), CAD-4 Users Manual, Xtal3.4 ADDREF SORTRF (Hall et al., 1995), SHELXS97 (Sheldrick, 1997), Xtal3.4 CRYLSQ, Xtal3.4 BONDLA CIFIO.
In the course of a search for bioactive drugs, Myoporum bontioides, which is widespread in the northwest of China, was selected as it has efficiency as an antipyretic and detoxicate, and is used for relieving uneasiness and fever in folk medicine. A study with somewhat larger amounts of the plant material and careful chromatography have allowed the isolation of 3β-angloyloxy-4αacetoxy-5αH-furanoeudesmane, named Furanoeudesmane-B. The title compound, (I), was a new eudesmane sesquiterpenoid. Several similar eudesmane derivatives (Bohlmann & Zdero, 1977) and quite a few eremophilane sesquiterpenoids (Bohlmann et al., 1978, 1979), which have the same elemental composition as the title compound, have been reported previously. \scheme
The skeleton of Furanoeudesmane consists of two six-membered rings and a furan ring connected together (labelled A–C left-to-right in the Scheme). Ring A (C1–C5 and C10) takes a chair conformation, with C4 0.653 (3) Å above and C1 0.609 (4) Å below the plane; ring B (C5–C10) takes a half-chair conformation as a result of the neighbouring furan ring, with C10 0.662 (3) Å above. Furan ring C (C7, C8, C11, C12 and O1) is essentially planar, including the C13 methyl group. The dihedral angle between the planar parts of rings A and B is 32.4 (2)°, and 34.0 (2)° between the planar segment of A and C; the planar segments of B and C are almost coplanar, the dihedral angle being only 4.6 (2)°.