Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270104012922/ta1451sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270104012922/ta1451Isup2.hkl |
CCDC reference: 213590
General directions have been reported previously (Baker et al., 2000). Dipterocarpus cornutus Dyer (Dipterocarpaceae) flowers were collected at Rimbo Panti, ca 300 m above sea level, 30 km north of Lubuk Sikaping, West Sumatra, Indonesia, in April 2001. The herbarium specimen (DR-150) was identified by Dr Rusjdi Tamin and is deposited at the herbarium of Andalas University. Air-dried flowers (250 g) were steam distilled and the oily distillate was crystallized from ethanol, yielding needles (500 mg) of the eudesmenol (m.p. 421–422 K, not raised on further recrystallization). High-resolution EIMS [M+H]++ found: 222.1985. 12C151H2616O requires m/z 222.1938. IR (max, cm−1, KBr): 3430, 2997, 2930, 2855, 1457, 1377, 1225, 1172, 1143, 1106, 926, 908. 1H NMR (500 MHz, CDC13): δ 0.96 (3H, s, 14-H), 1.05, (1H, m, 1-H), 1.10 (1H, dd, J = 14.9 and 5.5 Hz, 9-H), 1.13 (3H, d, J = 0.8 Hz, 15-H), 1.14 (1H, dd, J = 13.0 and 3.0 Hz, 5-H), 1.31 (1H, m, 3-H), 1.39 (1H, m, 1-H), 1.42 (1H, m, 9-H), 1.55 (2H, m, 2-H), 1.64 (1H, m, 6-H), 1.66 (3H, q, J = 1.1 Hz, 12-H or 13-H), 1.69 (3H, q, J = 1.1 Hz, 12-H or 13-H), 1.80 (1H, dddd, J = 12.5, 3.3, 3.3 and 1.7 Hz, 3-H), 1.89 (1H, dd, J = 14.2 and 14.2 Hz, 8-H), 2.49 (1H, ddddd, J = 14.5, 2.5, 2.5, 2.5 and 2.5 Hz, 8-H), 2.81 (1H, ddd, J = 13.4, 2.2 and 2.2 Hz, 6-H). 13C NMR (125 MHz, CDC13): δ 18.07 (C-14), 20.02 (C-12 or C-13), 20.07 (C-12 or C-13), 20.19 (C-2), 22.04 (C-15), 24.61 (C-6), 25.44 (C-8), 34.81 (C-10), 40.97 (C-1), 43.56 (C-3), 45.23 (C-9), 55.73 (C-5), 72.31 (C-4), 120.96 (C-11), 131.89 (C-7). EIMS: m/z 222, M++ (100%), 205 (16), 204 (81), 190 (15), 189 (100), 162 (10), 161 (55), 149 (20), 148 (20), 147 (19), 137 (23), 136 (11), 135 (56), 134 (25), 133 (35), 123 (28), 122 (35), 121 (45), 119 (19), 109 (35), 108 (19), 107 (37), 105 (38).
H atoms were located from difference Fourier maps, and C-bound H atoms then were placed at idealized positions [C—H = 0.95 Å, and Uiso(H) = 1.25Ueq(C) (CH and CH2) and 1.5Ueq(C,O) (CH3 and OH)] The material was difficult to obtain in a suitably crystalline form and the best available specimen was lost late in the data collection, resulting in 95% completeness after merging equivalents. SADABS (Sheldrick, 1996) was also instrumental (note the unreasonable Tmin and Tmax range) in smoothing irregularities arising from the non-optimal nature of the sample. The subsequent refinement, albeit on weak and limited data, was otherwise smooth and non-idiosyncratic.
Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: Xtal3.5 (Hall et al., 1995); program(s) used to refine structure: CRYLSQ in Xtal3.5; molecular graphics: Xtal3.5; software used to prepare material for publication: BONDLA and CIFIO in Xtal3.5.
C15H26O | Z = 4 |
Mr = 222.37 | F(000) = 496 |
Triclinic, P1 | Dx = 1.138 Mg m−3 |
Hall symbol: -p 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.967 (4) Å | Cell parameters from 1561 reflections |
b = 9.973 (3) Å | θ = 2.4–26.2° |
c = 14.130 (5) Å | µ = 0.07 mm−1 |
α = 96.412 (6)° | T = 150 K |
β = 110.196 (6)° | Bar, colourless |
γ = 95.100 (6)° | 0.22 × 0.1 × 0.08 mm |
V = 1297.6 (8) Å3 |
Bruker SMART CCD diffractometer | 4327 independent reflections |
Radiation source: sealed tube | 2639 reflections with I > 2.00 σ(I) |
Graphite monochromator | Rint = 0.040 |
ω scans | θmax = 25.0°, θmin = 1.6° |
Absorption correction: multi-scan SADABS; Sheldrick, 1996 | h = −11→10 |
Tmin = 0.710, Tmax = 0.97 | k = −11→11 |
9815 measured reflections | l = −16→16 |
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)] = 0.067 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.168 | H-atom parameters not refined |
S = 1.06 | w = 1/(σ2(F) + 0.37F2) |
4327 reflections | (Δ/σ)max = 0.004 |
289 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.49 e Å−3 |
0 constraints |
C15H26O | γ = 95.100 (6)° |
Mr = 222.37 | V = 1297.6 (8) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.967 (4) Å | Mo Kα radiation |
b = 9.973 (3) Å | µ = 0.07 mm−1 |
c = 14.130 (5) Å | T = 150 K |
α = 96.412 (6)° | 0.22 × 0.1 × 0.08 mm |
β = 110.196 (6)° |
Bruker SMART CCD diffractometer | 4327 independent reflections |
Absorption correction: multi-scan SADABS; Sheldrick, 1996 | 2639 reflections with I > 2.00 σ(I) |
Tmin = 0.710, Tmax = 0.97 | Rint = 0.040 |
9815 measured reflections |
R[F2 > 2σ(F2)] = 0.067 | 0 restraints |
wR(F2) = 0.168 | H-atom parameters not refined |
S = 1.06 | Δρmax = 0.41 e Å−3 |
4327 reflections | Δρmin = −0.49 e Å−3 |
289 parameters |
x | y | z | Uiso*/Ueq | ||
C11 | 0.4049 (4) | 0.6188 (4) | 0.6187 (3) | 0.0416 (17) | |
C12 | 0.5610 (4) | 0.6638 (4) | 0.6908 (3) | 0.0407 (16) | |
C13 | 0.5692 (4) | 0.6853 (3) | 0.8003 (3) | 0.0382 (15) | |
C14 | 0.5092 (4) | 0.5596 (3) | 0.8332 (2) | 0.0319 (14) | |
O14 | 0.4971 (3) | 0.6042 (2) | 0.93041 (18) | 0.0404 (11) | |
C15 | 0.3569 (4) | 0.5039 (3) | 0.7553 (2) | 0.0297 (13) | |
C16 | 0.2858 (4) | 0.3769 (3) | 0.7812 (2) | 0.0311 (14) | |
C17 | 0.1271 (4) | 0.3488 (3) | 0.7181 (3) | 0.0352 (15) | |
C18 | 0.1006 (4) | 0.3362 (4) | 0.6056 (3) | 0.0454 (17) | |
C19 | 0.1771 (4) | 0.4584 (4) | 0.5801 (3) | 0.0435 (17) | |
C110 | 0.3396 (4) | 0.4854 (4) | 0.6412 (3) | 0.0336 (14) | |
C111 | 0.0235 (4) | 0.3412 (3) | 0.7576 (3) | 0.0393 (16) | |
C112 | −0.1359 (4) | 0.3223 (5) | 0.6950 (4) | 0.055 (2) | |
C113 | 0.0517 (4) | 0.3511 (4) | 0.8700 (3) | 0.0473 (18) | |
C114 | 0.4088 (4) | 0.3671 (4) | 0.6068 (3) | 0.0432 (17) | |
C115 | 0.6143 (4) | 0.4554 (4) | 0.8536 (3) | 0.0387 (15) | |
C21 | −0.0205 (4) | 0.7232 (4) | 0.7934 (3) | 0.0392 (15) | |
C22 | 0.0177 (4) | 0.7298 (3) | 0.9074 (3) | 0.0363 (15) | |
C23 | 0.1798 (4) | 0.7527 (3) | 0.9623 (3) | 0.0358 (15) | |
C24 | 0.2545 (3) | 0.8802 (3) | 0.9410 (2) | 0.0283 (13) | |
O24 | 0.4074 (2) | 0.8722 (2) | 0.97952 (18) | 0.0357 (10) | |
C25 | 0.2051 (3) | 0.8816 (3) | 0.8259 (2) | 0.0278 (13) | |
C26 | 0.2761 (4) | 1.0070 (3) | 0.7973 (2) | 0.0338 (14) | |
C27 | 0.2522 (4) | 0.9871 (4) | 0.6851 (3) | 0.0390 (16) | |
C28 | 0.0933 (4) | 0.9504 (5) | 0.6203 (3) | 0.0493 (18) | |
C29 | 0.0222 (4) | 0.8310 (4) | 0.6532 (3) | 0.0468 (17) | |
C210 | 0.0403 (3) | 0.8540 (3) | 0.7654 (2) | 0.0319 (14) | |
C211 | 0.3561 (4) | 1.0018 (4) | 0.6477 (3) | 0.0418 (16) | |
C212 | 0.3333 (5) | 0.9782 (5) | 0.5353 (3) | 0.060 (2) | |
C213 | 0.5131 (4) | 1.0440 (4) | 0.7125 (3) | 0.0434 (17) | |
C214 | −0.0447 (4) | 0.9680 (4) | 0.7828 (3) | 0.0413 (16) | |
C215 | 0.2352 (4) | 1.0086 (3) | 1.0026 (3) | 0.0354 (15) | |
H11a | 0.40299 | 0.60489 | 0.55081 | 0.05000* | |
H11b | 0.34809 | 0.68761 | 0.62636 | 0.05000* | |
H12a | 0.59551 | 0.74774 | 0.67523 | 0.04900* | |
H12b | 0.61869 | 0.59695 | 0.68275 | 0.04900* | |
H13a | 0.51441 | 0.75702 | 0.80869 | 0.04400* | |
H13b | 0.66684 | 0.71197 | 0.84339 | 0.04400* | |
H14 | 0.43312 | 0.57191 | 0.95925 | 0.06100* | |
H15 | 0.30502 | 0.57676 | 0.76399 | 0.03700* | |
H16a | 0.29922 | 0.39104 | 0.85170 | 0.03800* | |
H16b | 0.33143 | 0.30076 | 0.76745 | 0.03800* | |
H18a | 0.00025 | 0.32696 | 0.56832 | 0.05700* | |
H18b | 0.13697 | 0.25547 | 0.58560 | 0.05700* | |
H19a | 0.13592 | 0.53734 | 0.59589 | 0.05400* | |
H19b | 0.16208 | 0.44521 | 0.50972 | 0.05400* | |
H112a | −0.15068 | 0.30451 | 0.62403 | 0.08200* | |
H112b | −0.17637 | 0.40311 | 0.70716 | 0.08200* | |
H112c | −0.18543 | 0.24741 | 0.71201 | 0.08200* | |
H113a | −0.00088 | 0.27445 | 0.88194 | 0.07000* | |
H113b | 0.02028 | 0.43214 | 0.89252 | 0.07000* | |
H113c | 0.15298 | 0.35473 | 0.90726 | 0.07000* | |
H114a | 0.36945 | 0.28444 | 0.61996 | 0.06200* | |
H114b | 0.51030 | 0.38259 | 0.64267 | 0.06200* | |
H114c | 0.39012 | 0.36145 | 0.53540 | 0.06200* | |
H115a | 0.57334 | 0.37890 | 0.87367 | 0.05300* | |
H115b | 0.70206 | 0.49505 | 0.90692 | 0.05300* | |
H115c | 0.63340 | 0.42725 | 0.79366 | 0.05300* | |
H21a | −0.12285 | 0.71066 | 0.76093 | 0.04800* | |
H21b | 0.01737 | 0.64906 | 0.76848 | 0.04800* | |
H22a | −0.02106 | 0.64610 | 0.92029 | 0.04400* | |
H22b | −0.02313 | 0.80235 | 0.93172 | 0.04400* | |
H23a | 0.21855 | 0.67581 | 0.94182 | 0.04100* | |
H23b | 0.19909 | 0.76074 | 1.03393 | 0.04100* | |
H24 | 0.41890 | 0.78782 | 0.95580 | 0.03600* | |
H25 | 0.24102 | 0.80377 | 0.80311 | 0.03400* | |
H26a | 0.37710 | 1.02084 | 0.83527 | 0.03900* | |
H26b | 0.23553 | 1.08537 | 0.81389 | 0.03900* | |
H28a | 0.08392 | 0.92672 | 0.55125 | 0.06000* | |
H28b | 0.04517 | 1.02741 | 0.62665 | 0.06000* | |
H29a | 0.06427 | 0.75189 | 0.64078 | 0.06100* | |
H29b | −0.07808 | 0.81586 | 0.61339 | 0.06100* | |
H212a | 0.35763 | 1.06149 | 0.51391 | 0.08800* | |
H212b | 0.23423 | 0.94438 | 0.49624 | 0.08800* | |
H212c | 0.39247 | 0.91352 | 0.52158 | 0.08800* | |
H213a | 0.55699 | 0.96560 | 0.73293 | 0.06400* | |
H213b | 0.52088 | 1.10438 | 0.77213 | 0.06400* | |
H213c | 0.56231 | 1.08954 | 0.67552 | 0.06400* | |
H214a | −0.00733 | 1.04897 | 0.76613 | 0.05900* | |
H214b | −0.03556 | 0.98178 | 0.85258 | 0.05900* | |
H214c | −0.14320 | 0.94299 | 0.74106 | 0.05900* | |
H215a | 0.28302 | 1.08685 | 0.98872 | 0.04800* | |
H215b | 0.27701 | 1.00388 | 1.07408 | 0.04800* | |
H215c | 0.13603 | 1.01647 | 0.98560 | 0.04800* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C11 | 0.037 (2) | 0.052 (2) | 0.037 (2) | 0.0035 (17) | 0.0139 (17) | 0.0123 (17) |
C12 | 0.039 (2) | 0.038 (2) | 0.045 (2) | 0.0029 (16) | 0.0160 (18) | 0.0052 (17) |
C13 | 0.039 (2) | 0.0319 (18) | 0.041 (2) | 0.0002 (15) | 0.0140 (17) | −0.0010 (15) |
C14 | 0.0333 (18) | 0.0281 (17) | 0.0308 (18) | 0.0034 (14) | 0.0088 (15) | −0.0008 (14) |
O14 | 0.0514 (15) | 0.0330 (13) | 0.0345 (13) | −0.0077 (11) | 0.0202 (12) | −0.0086 (10) |
C15 | 0.0335 (18) | 0.0265 (16) | 0.0298 (18) | 0.0091 (14) | 0.0110 (15) | 0.0043 (13) |
C16 | 0.0348 (18) | 0.0330 (18) | 0.0257 (17) | 0.0055 (15) | 0.0105 (14) | 0.0055 (13) |
C17 | 0.0338 (19) | 0.0362 (19) | 0.0320 (19) | −0.0016 (15) | 0.0098 (16) | 0.0030 (15) |
C18 | 0.0266 (18) | 0.067 (3) | 0.035 (2) | −0.0063 (18) | 0.0036 (16) | 0.0102 (18) |
C19 | 0.038 (2) | 0.060 (2) | 0.030 (2) | −0.0008 (18) | 0.0082 (16) | 0.0138 (17) |
C110 | 0.0268 (17) | 0.041 (2) | 0.0299 (18) | 0.0011 (15) | 0.0066 (15) | 0.0080 (15) |
C111 | 0.041 (2) | 0.0321 (19) | 0.043 (2) | 0.0008 (16) | 0.0154 (18) | 0.0033 (16) |
C112 | 0.040 (2) | 0.060 (3) | 0.071 (3) | 0.005 (2) | 0.025 (2) | 0.016 (2) |
C113 | 0.056 (2) | 0.036 (2) | 0.058 (3) | −0.0001 (18) | 0.032 (2) | 0.0037 (18) |
C114 | 0.041 (2) | 0.048 (2) | 0.034 (2) | −0.0057 (17) | 0.0128 (17) | −0.0069 (16) |
C115 | 0.034 (2) | 0.037 (2) | 0.038 (2) | 0.0063 (16) | 0.0058 (16) | −0.0029 (15) |
C21 | 0.0303 (19) | 0.035 (2) | 0.046 (2) | −0.0067 (15) | 0.0115 (17) | −0.0057 (16) |
C22 | 0.036 (2) | 0.0244 (17) | 0.046 (2) | −0.0049 (14) | 0.0153 (17) | −0.0014 (15) |
C23 | 0.038 (2) | 0.0266 (17) | 0.041 (2) | 0.0022 (15) | 0.0123 (16) | 0.0047 (15) |
C24 | 0.0266 (17) | 0.0231 (16) | 0.0321 (18) | 0.0038 (13) | 0.0080 (14) | −0.0008 (13) |
O24 | 0.0309 (13) | 0.0297 (12) | 0.0416 (14) | 0.0063 (10) | 0.0062 (11) | 0.0056 (10) |
C25 | 0.0281 (17) | 0.0234 (16) | 0.0277 (17) | −0.0019 (13) | 0.0088 (14) | −0.0046 (13) |
C26 | 0.0320 (18) | 0.0330 (18) | 0.0291 (18) | −0.0049 (14) | 0.0052 (15) | 0.0014 (14) |
C27 | 0.034 (2) | 0.047 (2) | 0.0298 (19) | −0.0023 (16) | 0.0060 (16) | 0.0035 (16) |
C28 | 0.037 (2) | 0.077 (3) | 0.0255 (19) | −0.004 (2) | 0.0053 (16) | 0.0031 (18) |
C29 | 0.030 (2) | 0.068 (3) | 0.029 (2) | −0.0124 (18) | 0.0035 (16) | −0.0091 (18) |
C210 | 0.0262 (17) | 0.0363 (18) | 0.0268 (17) | −0.0046 (14) | 0.0061 (14) | −0.0042 (14) |
C211 | 0.040 (2) | 0.044 (2) | 0.037 (2) | 0.0010 (17) | 0.0097 (17) | 0.0037 (16) |
C212 | 0.057 (3) | 0.082 (3) | 0.041 (2) | −0.002 (2) | 0.020 (2) | 0.004 (2) |
C213 | 0.038 (2) | 0.044 (2) | 0.046 (2) | 0.0041 (17) | 0.0119 (18) | 0.0096 (17) |
C214 | 0.033 (2) | 0.049 (2) | 0.039 (2) | 0.0034 (17) | 0.0085 (16) | 0.0080 (17) |
C215 | 0.040 (2) | 0.0300 (18) | 0.0312 (18) | 0.0047 (15) | 0.0099 (16) | −0.0050 (14) |
C11—C12 | 1.529 (5) | C21—C22 | 1.514 (5) |
C11—C110 | 1.541 (6) | C21—C210 | 1.539 (5) |
C11—H11a | 0.948 | C21—H21a | 0.953 |
C11—H11b | 0.948 | C21—H21b | 0.946 |
C12—C13 | 1.510 (6) | C22—C23 | 1.514 (5) |
C12—H12a | 0.954 | C22—H22a | 0.951 |
C12—H12b | 0.941 | C22—H22b | 0.949 |
C13—C14 | 1.527 (5) | C23—C24 | 1.528 (5) |
C13—H13a | 0.959 | C23—H23a | 0.949 |
C13—H13b | 0.947 | C23—H23b | 0.955 |
C14—O14 | 1.445 (5) | C24—O24 | 1.444 (4) |
C14—C15 | 1.544 (4) | C24—C25 | 1.530 (5) |
C14—C115 | 1.521 (5) | C24—C215 | 1.531 (5) |
O14—H14 | 0.922 | O24—H24 | 0.902 |
C15—C16 | 1.538 (5) | C25—C26 | 1.543 (5) |
C15—C110 | 1.549 (5) | C25—C210 | 1.550 (4) |
C15—H15 | 0.949 | C25—H25 | 0.953 |
C16—C17 | 1.506 (4) | C26—C27 | 1.506 (5) |
C16—H16a | 0.951 | C26—H26a | 0.952 |
C16—H16b | 0.954 | C26—H26b | 0.954 |
C17—C18 | 1.508 (5) | C27—C28 | 1.517 (5) |
C17—C111 | 1.333 (6) | C27—C211 | 1.320 (6) |
C18—C19 | 1.523 (6) | C28—C29 | 1.528 (6) |
C18—H18a | 0.946 | C28—H28a | 0.947 |
C18—H18b | 0.965 | C28—H28b | 0.953 |
C19—C110 | 1.532 (5) | C29—C210 | 1.521 (5) |
C19—H19a | 0.959 | C29—H29a | 0.953 |
C19—H19b | 0.945 | C29—H29b | 0.951 |
C110—C114 | 1.534 (6) | C210—C214 | 1.525 (5) |
C111—C112 | 1.510 (5) | C211—C212 | 1.512 (6) |
C111—C113 | 1.504 (6) | C211—C213 | 1.507 (5) |
C112—H112a | 0.955 | C212—H212a | 0.954 |
C112—H112b | 0.957 | C212—H212b | 0.957 |
C112—H112c | 0.957 | C212—H212c | 0.959 |
C113—H113a | 0.952 | C213—H213a | 0.955 |
C113—H113b | 0.953 | C213—H213b | 0.955 |
C113—H113c | 0.959 | C213—H213c | 0.954 |
C114—H114a | 0.946 | C214—H214a | 0.947 |
C114—H114b | 0.951 | C214—H214b | 0.951 |
C114—H114c | 0.955 | C214—H214c | 0.947 |
C115—H115a | 0.949 | C215—H215a | 0.953 |
C115—H115b | 0.952 | C215—H215b | 0.959 |
C115—H115c | 0.949 | C215—H215c | 0.946 |
C12—C11—C110 | 112.0 (3) | C22—C21—C210 | 112.3 (3) |
C12—C11—H11a | 108.7 | C22—C21—H21a | 109.1 |
C12—C11—H11b | 109.3 | C22—C21—H21b | 109.5 |
C110—C11—H11a | 108.7 | C210—C21—H21a | 108.2 |
C110—C11—H11b | 108.3 | C210—C21—H21b | 108.3 |
H11a—C11—H11b | 109.9 | H21a—C21—H21b | 109.5 |
C11—C12—C13 | 110.4 (4) | C21—C22—C23 | 110.8 (3) |
C11—C12—H12a | 108.8 | C21—C22—H22a | 108.7 |
C11—C12—H12b | 109.9 | C21—C22—H22b | 109.2 |
C13—C12—H12a | 108.7 | C23—C22—H22a | 109.3 |
C13—C12—H12b | 109.1 | C23—C22—H22b | 109.4 |
H12a—C12—H12b | 109.9 | H22a—C22—H22b | 109.4 |
C12—C13—C14 | 113.9 (3) | C22—C23—C24 | 113.6 (3) |
C12—C13—H13a | 108.5 | C22—C23—H23a | 108.6 |
C12—C13—H13b | 108.8 | C22—C23—H23b | 108.1 |
C14—C13—H13a | 107.7 | C24—C23—H23a | 108.6 |
C14—C13—H13b | 108.9 | C24—C23—H23b | 108.7 |
H13a—C13—H13b | 109.0 | H23a—C23—H23b | 109.1 |
C13—C14—O14 | 106.7 (3) | C23—C24—O24 | 106.9 (3) |
C13—C14—C15 | 109.4 (3) | C23—C24—C25 | 109.9 (2) |
C13—C14—C115 | 111.7 (3) | C23—C24—C215 | 111.0 (3) |
O14—C14—C15 | 108.5 (3) | O24—C24—C25 | 108.7 (3) |
O14—C14—C115 | 105.4 (3) | O24—C24—C215 | 105.4 (2) |
C15—C14—C115 | 114.7 (3) | C25—C24—C215 | 114.6 (3) |
C14—O14—H14 | 130.5 | C24—O24—H24 | 106.9 |
C14—C15—C16 | 113.8 (3) | C24—C25—C26 | 113.4 (2) |
C14—C15—C110 | 116.6 (3) | C24—C25—C210 | 116.8 (3) |
C14—C15—H15 | 101.2 | C24—C25—H25 | 102.2 |
C16—C15—C110 | 111.1 (2) | C26—C25—C210 | 111.4 (3) |
C16—C15—H15 | 107.5 | C26—C25—H25 | 107.4 |
C110—C15—H15 | 105.3 | C210—C25—H25 | 104.3 |
C15—C16—C17 | 110.8 (3) | C25—C26—C27 | 110.9 (3) |
C15—C16—H16a | 109.1 | C25—C26—H26a | 109.4 |
C15—C16—H16b | 108.7 | C25—C26—H26b | 109.0 |
C17—C16—H16a | 109.8 | C27—C26—H26a | 109.0 |
C17—C16—H16b | 109.4 | C27—C26—H26b | 109.5 |
H16a—C16—H16b | 109.1 | H26a—C26—H26b | 109.0 |
C16—C17—C18 | 111.6 (3) | C26—C27—C28 | 111.6 (3) |
C16—C17—C111 | 123.9 (3) | C26—C27—C211 | 124.3 (3) |
C18—C17—C111 | 124.5 (3) | C28—C27—C211 | 124.1 (3) |
C17—C18—C19 | 111.8 (3) | C27—C28—C29 | 112.0 (3) |
C17—C18—H18a | 109.6 | C27—C28—H28a | 108.9 |
C17—C18—H18b | 108.7 | C27—C28—H28b | 108.9 |
C19—C18—H18a | 109.8 | C29—C28—H28a | 109.0 |
C19—C18—H18b | 108.4 | C29—C28—H28b | 108.6 |
H18a—C18—H18b | 108.6 | H28a—C28—H28b | 109.4 |
C18—C19—C110 | 113.4 (3) | C28—C29—C210 | 113.5 (3) |
C18—C19—H19a | 107.9 | C28—C29—H29a | 108.5 |
C18—C19—H19b | 109.5 | C28—C29—H29b | 108.8 |
C110—C19—H19a | 107.8 | C210—C29—H29a | 108.2 |
C110—C19—H19b | 109.0 | C210—C29—H29b | 108.6 |
H19a—C19—H19b | 109.2 | H29a—C29—H29b | 109.2 |
C11—C110—C15 | 108.6 (3) | C21—C210—C25 | 108.2 (3) |
C11—C110—C19 | 109.7 (3) | C21—C210—C29 | 109.5 (3) |
C11—C110—C114 | 108.9 (3) | C21—C210—C214 | 108.8 (3) |
C15—C110—C19 | 106.4 (3) | C25—C210—C29 | 106.1 (3) |
C15—C110—C114 | 115.1 (3) | C25—C210—C214 | 115.6 (2) |
C19—C110—C114 | 108.0 (3) | C29—C210—C214 | 108.6 (3) |
C17—C111—C112 | 124.1 (4) | C27—C211—C212 | 124.6 (3) |
C17—C111—C113 | 123.9 (3) | C27—C211—C213 | 123.8 (3) |
C112—C111—C113 | 112.0 (4) | C212—C211—C213 | 111.6 (4) |
C111—C112—H112a | 110.0 | C211—C212—H212a | 110.3 |
C111—C112—H112b | 110.2 | C211—C212—H212b | 109.9 |
C111—C112—H112c | 110.7 | C211—C212—H212c | 110.7 |
H112a—C112—H112b | 108.4 | H212a—C212—H212b | 108.5 |
H112a—C112—H112c | 108.6 | H212a—C212—H212c | 108.5 |
H112b—C112—H112c | 109.0 | H212b—C212—H212c | 108.9 |
C111—C113—H113a | 109.3 | C211—C213—H213a | 109.7 |
C111—C113—H113b | 109.3 | C211—C213—H213b | 109.5 |
C111—C113—H113c | 110.1 | C211—C213—H213c | 110.6 |
H113a—C113—H113b | 109.0 | H213a—C213—H213b | 108.7 |
H113a—C113—H113c | 110.3 | H213a—C213—H213c | 109.6 |
H113b—C113—H113c | 108.7 | H213b—C213—H213c | 108.9 |
C110—C114—H114a | 109.8 | C210—C214—H214a | 109.1 |
C110—C114—H114b | 109.6 | C210—C214—H214b | 109.1 |
C110—C114—H114c | 109.4 | C210—C214—H214c | 109.2 |
H114a—C114—H114b | 109.7 | H214a—C214—H214b | 109.7 |
H114a—C114—H114c | 109.4 | H214a—C214—H214c | 110.0 |
H114b—C114—H114c | 109.0 | H214b—C214—H214c | 109.6 |
C14—C115—H115a | 109.3 | C24—C215—H215a | 109.7 |
C14—C115—H115b | 109.4 | C24—C215—H215b | 109.6 |
C14—C115—H115c | 109.7 | C24—C215—H215c | 110.3 |
H115a—C115—H115b | 109.4 | H215a—C215—H215b | 108.5 |
H115a—C115—H115c | 109.6 | H215a—C215—H215c | 109.6 |
H115b—C115—H115c | 109.4 | H215b—C215—H215c | 109.1 |
C110—C11—C12—C13 | −59.0 (4) | C210—C21—C22—C23 | −58.8 (4) |
C12—C11—C110—C15 | 54.2 (4) | C22—C21—C210—C25 | 54.4 (4) |
C11—C12—C13—C14 | 57.6 (4) | C21—C22—C23—C24 | 56.5 (4) |
C12—C13—C14—C15 | −51.1 (4) | C22—C23—C24—C25 | −50.2 (4) |
C13—C14—C15—C110 | 48.7 (4) | C23—C24—C25—C210 | 48.7 (4) |
C110—C15—C16—C17 | −59.8 (4) | C210—C25—C26—C27 | −59.3 (4) |
C14—C15—C110—C11 | −50.5 (4) | C24—C25—C210—C21 | −50.7 (4) |
C16—C15—C110—C19 | 58.8 (4) | C26—C25—C210—C29 | 59.2 (4) |
C15—C16—C17—C18 | 55.2 (4) | C25—C26—C27—C28 | 53.6 (4) |
C16—C17—C18—C19 | −52.5 (4) | C26—C27—C28—C29 | −51.2 (4) |
C16—C17—C111—C113 | −3.8 (6) | C26—C27—C211—C213 | −1.8 (6) |
C18—C17—C111—C112 | −1.7 (6) | C28—C27—C211—C212 | −2.7 (7) |
C17—C18—C19—C110 | 55.2 (5) | C27—C28—C29—C210 | 55.0 (5) |
C18—C19—C110—C15 | −56.9 (4) | C28—C29—C210—C25 | −57.3 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O14—H14···O14i | 0.92 | 2.47 | 3.008 (3) | 118 |
O24—H24···O14 | 0.90 | 2.10 | 2.977 (4) | 165 |
Symmetry code: (i) −x+1, −y+1, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C15H26O |
Mr | 222.37 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 150 |
a, b, c (Å) | 9.967 (4), 9.973 (3), 14.130 (5) |
α, β, γ (°) | 96.412 (6), 110.196 (6), 95.100 (6) |
V (Å3) | 1297.6 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.22 × 0.1 × 0.08 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Multi-scan SADABS; Sheldrick, 1996 |
Tmin, Tmax | 0.710, 0.97 |
No. of measured, independent and observed [I > 2.00 σ(I)] reflections | 9815, 4327, 2639 |
Rint | 0.040 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.067, 0.168, 1.06 |
No. of reflections | 4327 |
No. of parameters | 289 |
H-atom treatment | H-atom parameters not refined |
Δρmax, Δρmin (e Å−3) | 0.41, −0.49 |
Computer programs: SMART (Siemens, 1995), SAINT (Siemens, 1995), SAINT, Xtal3.5 (Hall et al., 1995), CRYLSQ in Xtal3.5, BONDLA and CIFIO in Xtal3.5.
In continuation of our studies on the chemical constituents of the flora of Sumatra (Wahyuni et al., 2003) we have investigated the flowers of Dipterocarpus cornutus Dyer (Dipterocarpacaea). This species, known in West Sumatra as kruing, is a resinous tree attaining a height of 20m and its wood is used in joinery. No chemical work has been done previously on this species.
Steam distillation of the flowers yielded a crystalline compound, m.p. 421–422 K, which was devoid of optical rotation. The spectroscopic properties of this racemic compound, which are recorded in the experimental section, suggested that it was eudesm-7(11)-en-4-ol. An enantiomer, (I), of this compound was isolated as an oil from Acritoppus prunifolius (Bohlmann et al., 1982). Although the authors recorded its 1H NMR spectrum, they omitted to record an optical rotation. These authors were apparently unaware that this eudesmenol had previously been synthesized (Chetty et al., 1968) in three steps from β-eudesmol, (II). More recently (Toyota et al., 1999), this laevorotatory compound has been isolated from the liverwort Chiloscyphus polyanthos and its synthesis from (II) was repeated, the absolute stereochemistry being confirmed by X-ray methods on a heavy-atom derivative. However, few spectral data have been recorded.
The dextrorotatory enantiomer, (III), m.p. 349–359 K, of (I) has been isolated from Laggera pterodonta (Zhao et al., 1977). The 1H and 13C NMR spectra recorded for (III) by these workers are similar to those recorded by us, except for one carbon signal.
None of the afore-mentioned authors made reference to the much earlier studies (Motl et al., 1958) on `juniper camphor', m.p. 439.5 K, which was isolated from the juniper oil obtained as a by-product during the fermentation of juniper berries in gin manufacture. On the basis of degradative evidence, these authors proposed structure (I), without specification of stereochemistry, for this compound, which was devoid of optical rotation. Chetty et al. (1968) claimed that the synthetic compound (I) was identical to Sorm's juniper camphor in all respects except optical rotation. The evidence adduced for the structure of the new compound suggests that it is the racemate of (I) and (III). Because of the large difference in melting point between the present compound and juniper camphor, we have confirmed the structural assignment by the determination of the crystal structure.
The results of the single-crystal X-ray study are consistent with the stoichiometry and connectivity proposed, the compound being a racemate, with two similar independent molecules comprising the asymmetric unit of the structure. The chirality of the latter is arbitrarily set, in accordance with that assigned to the earlier determination of the structure of cuauhtemone, (IV) (Ivie et al., 1974; Nakanishi et al., 1974), the conformations of all rings being (quasi-)chair (Fig. 1). In the present structure, the molecules pack with weak hydrogen bonding. The geometric parameters are essentially as expected for the structure of (III).