Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803004288/om6134sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803004288/om6134IIsup2.hkl |
CCDC reference: 209914
Compound (II) was prepared by the procedure described for (I) (Xie et al., 2003), except that the brown pasty solid obtained after the addition of 3 N HCl was left untouched for several days before being treated with p-TsOH·H2O. The resulting solid product was purified by recrystallization (ethyl acetate-hexane; m.p. 410.6–411.4 K) and shown to be (II). GC–MS: M+ 302, W·W. calculated: 302; NMR (CDCl3), 1H (300 MHz): δ 0.73 (t, J = 7.5 Hz, 3H), 1.02 (d, J = 6.9 Hz, 3H), 1.12 (s, 3H),1.18 (s, 3H), 1.53 (m, J = 7.2 Hz, 2H), 1.66 (d, J = 10.5 Hz, 1H), 1.67 (d, J = 7.5 Hz, 1H), 2.06 (s, 1H), 2.44 (q, J = 6.9 Hz, 1H), 2.92 (dd, J = 7.8 Hz, 10.5 Hz, 1H), 3.79 (s, 3H), 6.83 (d, J = 9.0 Hz, 2H), 7.24 (d, J = 9.0 Hz, 2H); 13C (75 MHz): δ 6.72, 14.30, 23.68, 25.99, 28.30, 31.80, 39.49, 44.49, 44.95, 55.16, 59.84, 91.52, 113.69, 129.66, 133.67 (2 C), 158.33 (2 C), 177.72.
The rotational orientations of the methyl H atoms were refined by the circular Fourier method available in SHELXL97 (Sheldrick, 1997). All H atoms were refined as riding, with C—H distances ranging from 0.93 to 0.98 Å.
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1996); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: PROCESS in TEXSAN (Molecular Structure Corporation, 1997); program(s) used to solve structure: SIR92 (Burla et al., 1989); program(s) used to refine structure: LS in TEXSAN and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN, SHELXL97 and PLATON (Spek, 2000).
Fig. 1. The molecular structure and atom-numbering scheme for (II), with displacement ellipsoids at the 30% probability level. |
C19H26O3 | F(000) = 656 |
Mr = 302.40 | Dx = 1.194 Mg m−3 |
Monoclinic, P21/c | Melting point = 410.6–411.4 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71069 Å |
a = 18.318 (2) Å | Cell parameters from 25 reflections |
b = 7.597 (3) Å | θ = 19.6–21.3° |
c = 12.0935 (13) Å | µ = 0.08 mm−1 |
β = 91.86 (1)° | T = 296 K |
V = 1682.2 (7) Å3 | Prism, colorless |
Z = 4 | 0.48 × 0.46 × 0.27 mm |
Rigaku AFC-5S diffractometer | Rint = 0.008 |
Radiation source: fine-focus sealed tube | θmax = 25.1°, θmin = 2.2° |
Graphite monochromator | h = 0→21 |
ω scans | k = 0→9 |
3069 measured reflections | l = −14→14 |
2971 independent reflections | 3 standard reflections every 100 reflections |
2145 reflections with I > 2σ(I) | intensity decay: 1.6% |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0574P)2 + 0.3918P] where P = (Fo2 + 2Fc2)/3 |
2971 reflections | (Δ/σ)max < 0.001 |
204 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C19H26O3 | V = 1682.2 (7) Å3 |
Mr = 302.40 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 18.318 (2) Å | µ = 0.08 mm−1 |
b = 7.597 (3) Å | T = 296 K |
c = 12.0935 (13) Å | 0.48 × 0.46 × 0.27 mm |
β = 91.86 (1)° |
Rigaku AFC-5S diffractometer | Rint = 0.008 |
3069 measured reflections | 3 standard reflections every 100 reflections |
2971 independent reflections | intensity decay: 1.6% |
2145 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.14 e Å−3 |
2971 reflections | Δρmin = −0.19 e Å−3 |
204 parameters |
x | y | z | Uiso*/Ueq | ||
O1 | 0.93628 (7) | 0.3563 (2) | 0.63097 (11) | 0.0632 (4) | |
O2 | 0.53075 (6) | 0.60610 (17) | 0.89125 (10) | 0.0534 (3) | |
O6 | 0.81709 (6) | 0.38375 (14) | 0.59134 (9) | 0.0392 (3) | |
C1 | 0.89193 (9) | 0.5729 (2) | 0.49339 (13) | 0.0396 (4) | |
C2 | 0.88546 (9) | 0.7544 (2) | 0.55194 (14) | 0.0442 (4) | |
C3 | 0.81738 (9) | 0.7504 (2) | 0.62315 (14) | 0.0429 (4) | |
C4 | 0.74931 (8) | 0.6614 (2) | 0.56946 (13) | 0.0367 (4) | |
C5 | 0.77099 (8) | 0.4869 (2) | 0.51302 (12) | 0.0360 (4) | |
C7 | 0.88847 (9) | 0.4283 (2) | 0.57833 (14) | 0.0420 (4) | |
C8 | 0.82449 (9) | 0.5286 (2) | 0.42097 (13) | 0.0385 (4) | |
C9 | 0.95324 (10) | 0.7874 (3) | 0.62595 (18) | 0.0647 (6) | |
C10 | 0.87955 (12) | 0.9020 (2) | 0.46579 (18) | 0.0618 (5) | |
C11 | 0.70693 (9) | 0.3694 (2) | 0.48118 (15) | 0.0457 (4) | |
C12 | 0.65405 (11) | 0.4516 (3) | 0.39665 (17) | 0.0639 (6) | |
C13 | 0.83925 (11) | 0.3767 (2) | 0.34180 (15) | 0.0531 (5) | |
C14 | 0.68951 (8) | 0.6455 (2) | 0.65255 (13) | 0.0371 (4) | |
C15 | 0.69860 (9) | 0.5449 (2) | 0.74874 (14) | 0.0438 (4) | |
C16 | 0.64470 (9) | 0.5352 (2) | 0.82512 (14) | 0.0441 (4) | |
C17 | 0.57972 (9) | 0.6252 (2) | 0.80858 (13) | 0.0395 (4) | |
C18 | 0.56888 (9) | 0.7245 (2) | 0.71410 (14) | 0.0444 (4) | |
C19 | 0.62381 (9) | 0.7334 (2) | 0.63789 (14) | 0.0432 (4) | |
C20 | 0.46665 (11) | 0.7094 (3) | 0.88672 (19) | 0.0685 (6) | |
H1 | 0.9367 | 0.5653 | 0.4514 | 0.048* | |
H3a | 0.8048 | 0.8705 | 0.6419 | 0.051* | |
H3b | 0.8298 | 0.6896 | 0.6917 | 0.051* | |
H4 | 0.7310 | 0.7402 | 0.5108 | 0.044* | |
H8 | 0.8081 | 0.6327 | 0.3793 | 0.046* | |
H9a | 0.9957 | 0.7904 | 0.5815 | 0.097* | |
H9b | 0.9583 | 0.6946 | 0.6795 | 0.097* | |
H9c | 0.9483 | 0.8981 | 0.6633 | 0.097* | |
H10a | 0.8331 | 0.8948 | 0.4269 | 0.093* | |
H10b | 0.9180 | 0.8897 | 0.4142 | 0.093* | |
H10c | 0.8838 | 1.0139 | 0.5022 | 0.093* | |
H11a | 0.6807 | 0.3409 | 0.5472 | 0.055* | |
H11b | 0.7254 | 0.2602 | 0.4513 | 0.055* | |
H12a | 0.6319 | 0.5537 | 0.4282 | 0.096* | |
H12b | 0.6169 | 0.3677 | 0.3760 | 0.096* | |
H12c | 0.6800 | 0.4855 | 0.3323 | 0.096* | |
H13a | 0.8790 | 0.4075 | 0.2956 | 0.080* | |
H13b | 0.7963 | 0.3543 | 0.2964 | 0.080* | |
H13c | 0.8518 | 0.2730 | 0.3836 | 0.080* | |
H15 | 0.7419 | 0.4833 | 0.7614 | 0.053* | |
H16 | 0.6521 | 0.4674 | 0.8885 | 0.053* | |
H18 | 0.5252 | 0.7849 | 0.7015 | 0.053* | |
H19 | 0.6161 | 0.8012 | 0.5745 | 0.052* | |
H20a | 0.4796 | 0.8316 | 0.8830 | 0.103* | |
H20b | 0.4393 | 0.6887 | 0.9518 | 0.103* | |
H20c | 0.4375 | 0.6780 | 0.8223 | 0.103* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0442 (7) | 0.0797 (10) | 0.0655 (8) | 0.0093 (7) | −0.0023 (6) | 0.0243 (8) |
O2 | 0.0429 (7) | 0.0645 (8) | 0.0537 (7) | 0.0063 (6) | 0.0142 (6) | 0.0048 (6) |
O6 | 0.0373 (6) | 0.0401 (6) | 0.0403 (6) | 0.0004 (5) | 0.0023 (5) | 0.0101 (5) |
C1 | 0.0382 (9) | 0.0418 (9) | 0.0393 (8) | −0.0025 (7) | 0.0085 (7) | 0.0018 (7) |
C2 | 0.0416 (9) | 0.0449 (10) | 0.0464 (9) | −0.0106 (7) | 0.0052 (7) | −0.0039 (8) |
C3 | 0.0425 (9) | 0.0420 (9) | 0.0443 (9) | −0.0051 (7) | 0.0036 (7) | −0.0075 (7) |
C4 | 0.0374 (8) | 0.0356 (9) | 0.0371 (8) | −0.0002 (7) | 0.0010 (7) | 0.0025 (7) |
C5 | 0.0387 (8) | 0.0333 (8) | 0.0359 (8) | −0.0022 (7) | −0.0022 (7) | 0.0047 (7) |
C7 | 0.0389 (9) | 0.0467 (10) | 0.0407 (9) | 0.0004 (8) | 0.0034 (7) | 0.0030 (8) |
C8 | 0.0479 (9) | 0.0329 (8) | 0.0349 (8) | −0.0002 (7) | 0.0026 (7) | 0.0025 (7) |
C9 | 0.0440 (11) | 0.0780 (14) | 0.0720 (13) | −0.0166 (10) | 0.0013 (9) | −0.0165 (11) |
C10 | 0.0754 (14) | 0.0426 (11) | 0.0683 (13) | −0.0161 (10) | 0.0129 (11) | 0.0041 (9) |
C11 | 0.0458 (10) | 0.0404 (9) | 0.0507 (10) | −0.0084 (8) | −0.0043 (8) | −0.0009 (8) |
C12 | 0.0617 (12) | 0.0611 (13) | 0.0675 (13) | −0.0088 (10) | −0.0210 (10) | −0.0027 (10) |
C13 | 0.0697 (13) | 0.0463 (10) | 0.0438 (10) | 0.0014 (9) | 0.0074 (9) | −0.0042 (8) |
C14 | 0.0360 (8) | 0.0380 (9) | 0.0372 (8) | 0.0005 (7) | −0.0006 (7) | 0.0007 (7) |
C15 | 0.0375 (9) | 0.0481 (10) | 0.0459 (9) | 0.0100 (7) | 0.0011 (7) | 0.0062 (8) |
C16 | 0.0459 (10) | 0.0439 (10) | 0.0426 (9) | 0.0066 (8) | 0.0035 (8) | 0.0092 (8) |
C17 | 0.0358 (9) | 0.0406 (9) | 0.0423 (9) | −0.0008 (7) | 0.0049 (7) | −0.0017 (7) |
C18 | 0.0348 (9) | 0.0493 (10) | 0.0491 (9) | 0.0078 (7) | −0.0014 (7) | 0.0013 (8) |
C19 | 0.0415 (9) | 0.0459 (10) | 0.0420 (9) | 0.0045 (8) | −0.0025 (7) | 0.0069 (8) |
C20 | 0.0459 (11) | 0.0875 (16) | 0.0731 (13) | 0.0171 (11) | 0.0182 (10) | 0.0035 (12) |
C1—C7 | 1.507 (2) | C3—H3a | 0.9700 |
O6—C7 | 1.3646 (19) | C3—H3b | 0.9700 |
O6—C5 | 1.4741 (18) | C4—H4 | 0.9800 |
O1—C7 | 1.198 (2) | C8—H8 | 0.9800 |
O2—C17 | 1.3724 (19) | C9—H9a | 0.9600 |
O2—C20 | 1.412 (2) | C9—H9b | 0.9600 |
C1—C8 | 1.529 (2) | C9—H9c | 0.9600 |
C1—C2 | 1.556 (2) | C10—H10a | 0.9600 |
C2—C9 | 1.528 (2) | C10—H10b | 0.9600 |
C2—C10 | 1.532 (3) | C10—H10c | 0.9600 |
C2—C3 | 1.539 (2) | C11—H11a | 0.9700 |
C3—C4 | 1.543 (2) | C11—H11b | 0.9700 |
C4—C14 | 1.515 (2) | C12—H12a | 0.9600 |
C4—C5 | 1.549 (2) | C12—H12b | 0.9600 |
C5—C11 | 1.514 (2) | C12—H12c | 0.9600 |
C5—C8 | 1.540 (2) | C13—H13a | 0.9600 |
C8—C13 | 1.529 (2) | C13—H13b | 0.9600 |
C11—C12 | 1.520 (3) | C13—H13c | 0.9600 |
C14—C19 | 1.383 (2) | C15—H15 | 0.9300 |
C14—C15 | 1.397 (2) | C16—H16 | 0.9300 |
C15—C16 | 1.376 (2) | C18—H18 | 0.9300 |
C16—C17 | 1.382 (2) | C19—H19 | 0.9300 |
C17—C18 | 1.378 (2) | C20—H20a | 0.9600 |
C18—C19 | 1.388 (2) | C20—H20b | 0.9600 |
C1—H1 | 0.9800 | C20—H20c | 0.9600 |
O1—C7—C1 | 130.46 (16) | C5—C4—H4 | 106.9 |
C1—C7—O6 | 108.74 (14) | C13—C8—H8 | 110.2 |
C5—O6—C7 | 108.97 (11) | C1—C8—H8 | 110.2 |
C17—O2—C20 | 118.39 (14) | C5—C8—H8 | 110.2 |
C7—C1—C8 | 100.30 (13) | C2—C9—H9a | 109.5 |
C7—C1—C2 | 109.29 (13) | C2—C9—H9b | 109.5 |
C8—C1—C2 | 112.57 (14) | H9a—C9—H9b | 109.5 |
C9—C2—C10 | 108.45 (16) | C2—C9—H9c | 109.5 |
C9—C2—C3 | 109.48 (14) | H9a—C9—H9c | 109.5 |
C10—C2—C3 | 110.76 (15) | H9b—C9—H9c | 109.5 |
C9—C2—C1 | 109.85 (15) | C2—C10—H10a | 109.5 |
C10—C2—C1 | 110.11 (14) | C2—C10—H10b | 109.5 |
C3—C2—C1 | 108.19 (13) | H10a—C10—H10b | 109.5 |
C2—C3—C4 | 115.57 (13) | C2—C10—H10c | 109.5 |
C14—C4—C3 | 110.34 (13) | H10a—C10—H10c | 109.5 |
C14—C4—C5 | 115.17 (13) | H10b—C10—H10c | 109.5 |
C3—C4—C5 | 110.21 (13) | H11a—C11—H11b | 107.7 |
O6—C5—C11 | 105.83 (12) | C5—C11—H11a | 108.8 |
O6—C5—C8 | 102.06 (11) | C12—C11—H11a | 108.8 |
C11—C5—C8 | 116.32 (13) | C5—C11—H11b | 108.8 |
O6—C5—C4 | 108.76 (12) | C12—C11—H11b | 108.8 |
C11—C5—C4 | 114.16 (14) | C11—C12—H12a | 109.5 |
C8—C5—C4 | 108.73 (12) | C11—C12—H12b | 109.5 |
O1—C7—O6 | 120.80 (15) | H12a—C12—H12b | 109.5 |
C13—C8—C1 | 111.65 (14) | C11—C12—H12c | 109.5 |
C13—C8—C5 | 115.31 (14) | H12a—C12—H12c | 109.5 |
C1—C8—C5 | 98.78 (12) | H12b—C12—H12c | 109.5 |
C5—C11—C12 | 113.60 (15) | C8—C13—H13a | 109.5 |
C19—C14—C15 | 116.79 (15) | C8—C13—H13b | 109.5 |
C19—C14—C4 | 121.43 (14) | H13a—C13—H13b | 109.5 |
C15—C14—C4 | 121.77 (14) | C8—C13—H13c | 109.5 |
C16—C15—C14 | 121.30 (15) | H13a—C13—H13c | 109.5 |
C15—C16—C17 | 120.66 (15) | H13b—C13—H13c | 109.5 |
O2—C17—C18 | 125.58 (15) | C14—C19—H19 | 118.7 |
O2—C17—C16 | 115.00 (14) | C18—C19—H19 | 118.7 |
C18—C17—C16 | 119.42 (15) | O2—C20—H20a | 109.5 |
C17—C18—C19 | 119.29 (15) | O2—C20—H20b | 109.5 |
C14—C19—C18 | 122.54 (15) | H20a—C20—H20b | 109.5 |
C7—C1—H1 | 111.4 | O2—C20—H20c | 109.5 |
C8—C1—H1 | 111.4 | H20a—C20—H20c | 109.5 |
C2—C1—H1 | 111.4 | H20b—C20—H20c | 109.5 |
C2—C3—H3a | 108.4 | C16—C15—H15 | 119.3 |
C4—C3—H3a | 108.4 | C14—C15—H15 | 119.3 |
C2—C3—H3b | 108.4 | C15—C16—H16 | 119.7 |
C4—C3—H3b | 108.4 | C17—C16—H16 | 119.7 |
H3a—C3—H3b | 107.4 | C17—C18—H18 | 120.4 |
C14—C4—H4 | 106.9 | C19—C18—H18 | 120.4 |
C3—C4—H4 | 106.9 | ||
C1—C7—O6—C5 | 3.11 (17) | C7—C1—C8—C13 | −78.85 (16) |
C3—C4—C14—C19 | 115.85 (17) | C2—C1—C8—C13 | 165.11 (13) |
C3—C4—C14—C15 | −62.6 (2) | C7—C1—C8—C5 | 42.94 (14) |
C7—C1—C2—C9 | 67.45 (18) | C2—C1—C8—C5 | −73.10 (15) |
C8—C1—C2—C9 | 177.97 (14) | O6—C5—C8—C13 | 77.10 (16) |
C7—C1—C2—C10 | −173.18 (15) | C11—C5—C8—C13 | −37.5 (2) |
C8—C1—C2—C10 | −62.66 (18) | C4—C5—C8—C13 | −168.08 (14) |
C7—C1—C2—C3 | −52.01 (17) | O6—C5—C8—C1 | −41.99 (14) |
C8—C1—C2—C3 | 58.51 (17) | C11—C5—C8—C1 | −156.63 (14) |
C9—C2—C3—C4 | −161.17 (16) | C4—C5—C8—C1 | 72.83 (14) |
C10—C2—C3—C4 | 79.29 (18) | O6—C5—C11—C12 | −177.93 (15) |
C1—C2—C3—C4 | −41.48 (19) | C8—C5—C11—C12 | −65.4 (2) |
C2—C3—C4—C14 | 172.88 (14) | C4—C5—C11—C12 | 62.49 (19) |
C2—C3—C4—C5 | 44.59 (19) | C5—C4—C14—C19 | −118.61 (17) |
C7—O6—C5—C11 | 147.30 (13) | C5—C4—C14—C15 | 62.9 (2) |
C7—O6—C5—C8 | 25.17 (15) | C19—C14—C15—C16 | −0.3 (2) |
C7—O6—C5—C4 | −89.63 (15) | C4—C14—C15—C16 | 178.20 (15) |
C14—C4—C5—O6 | −76.93 (15) | C14—C15—C16—C17 | 0.0 (3) |
C3—C4—C5—O6 | 48.68 (16) | C20—O2—C17—C18 | −6.9 (3) |
C14—C4—C5—C11 | 40.99 (18) | C20—O2—C17—C16 | 172.94 (17) |
C3—C4—C5—C11 | 166.60 (13) | C15—C16—C17—O2 | −179.41 (15) |
C14—C4—C5—C8 | 172.69 (12) | C15—C16—C17—C18 | 0.5 (3) |
C3—C4—C5—C8 | −61.70 (16) | O2—C17—C18—C19 | 179.23 (16) |
C5—O6—C7—O1 | −177.40 (16) | C16—C17—C18—C19 | −0.6 (3) |
C8—C1—C7—O1 | 150.4 (2) | C15—C14—C19—C18 | 0.2 (2) |
C2—C1—C7—O1 | −91.1 (2) | C4—C14—C19—C18 | −178.38 (15) |
C8—C1—C7—O6 | −30.16 (16) | C17—C18—C19—C14 | 0.3 (3) |
C2—C1—C7—O6 | 88.32 (16) |
Experimental details
Crystal data | |
Chemical formula | C19H26O3 |
Mr | 302.40 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 18.318 (2), 7.597 (3), 12.0935 (13) |
β (°) | 91.86 (1) |
V (Å3) | 1682.2 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.48 × 0.46 × 0.27 |
Data collection | |
Diffractometer | Rigaku AFC-5S diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3069, 2971, 2145 |
Rint | 0.008 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.113, 1.01 |
No. of reflections | 2971 |
No. of parameters | 204 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.14, −0.19 |
Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1996), MSC/AFC Diffractometer Control Software, PROCESS in TEXSAN (Molecular Structure Corporation, 1997), SIR92 (Burla et al., 1989), LS in TEXSAN and SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), TEXSAN, SHELXL97 and PLATON (Spek, 2000).
O1—C7—C1 | 130.46 (16) | C5—O6—C7 | 108.97 (11) |
C1—C7—O6 | 108.74 (14) | ||
C1—C7—O6—C5 | 3.11 (17) | C3—C4—C14—C15 | −62.6 (2) |
C3—C4—C14—C19 | 115.85 (17) |
We recently described the preparation, isolation and X-ray analysis of bicyclic δ-lactone (I) (Xie et al., 2003), which is the kinetically favored lactone formed in the reaction of (±)-cis-2,6,6-trimethyl-trans-3-ethyl-4-oxocyclohexanecarboxylic acid with p-methoxyphenylmagnesium bromide, followed by acidification with excess 3 N HCl, and the mixture worked up within an hour. When the acidified mixture was worked up after several days, the thermodynamically favored isomeric bicyclic γ-lactone, namely (±)-5-ethyl-endo-4-(4-methoxyphenyl)-2,2,anti-8-trimethyl-6- oxabicyclo[3.2.1]octan-7-one, (II), was obtained as the major product. This reaction is described in detail in the preceding paper (Xie et al., 2003).
The structure and atom numbering of (II) are shown in Fig. 1. Lactone (II) is basically composed of an aromatic ring appended to a [3.2.1] bicyclic system. The O—C(O)—C group is asymmetric, its O—C═O angle being 120.80 (15)° and its O═C—C angle being 130.46 (16)°. The four atoms comprising the lactone moiety, C1/C7/O6/C5, are essentially coplanar, as evidenced by the torsion angle, and the least-squares plane of this moiety is nearly perpendicular to the cyclohexane ring, the angle being 89.75 (8)°. Geometric values of interest are given in Table 1.