The title compound, 4a,5,6,8a,9,9a-hexahydro-9a-hydroxy-4,4,7-trimethylnaphtho[2,3-
b]furan-2(4
H)-one, C
15H
20O
3, is a sesquiterpenoid isolated from the marine sponge
Dysidea fragilis. The furodysinin lactone skeleton consists of two six-membered rings, which adopt chair and half-chair conformations, and a furan ring. The molecules are arranged in a helical pattern through O—H
O hydrogen bonds.
Supporting information
CCDC reference: 232178
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.040
- wR factor = 0.104
- Data-to-parameter ratio = 11.0
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT035_ALERT_1_A No _chemical_absolute_configuration info given . ?
Alert level C
ABSTY02_ALERT_1_C An _exptl_absorpt_correction_type has been given without
a literature citation. This should be contained in the
_exptl_absorpt_process_details field.
Absorption correction given as multi-scan
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 28.02
From the CIF: _reflns_number_total 1837
Count of symmetry unique reflns 1878
Completeness (_total/calc) 97.82%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
Crystal data top
C15H20O3 | Dx = 1.235 Mg m−3 |
Mr = 248.31 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 4309 reflections |
a = 7.1736 (7) Å | θ = 2.5–27.7° |
b = 8.7391 (9) Å | µ = 0.09 mm−1 |
c = 21.301 (2) Å | T = 293 K |
V = 1335.4 (2) Å3 | Needle, colourless |
Z = 4 | 0.24 × 0.20 × 0.15 mm |
F(000) = 536 | |
Data collection top
CCD Area Detector diffractometer | 1837 independent reflections |
Radiation source: fine-focus sealed tube | 1705 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
ω scans | θmax = 28.0°, θmin = 1.9° |
Absorption correction: multi-scan | h = −8→9 |
Tmin = 0.980, Tmax = 0.987 | k = −10→11 |
8149 measured reflections | l = −27→28 |
Refinement top
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 1.13 | w = 1/[σ2(Fo2) + (0.058P)2 + 0.1311P] where P = (Fo2 + 2Fc2)/3 |
1837 reflections | (Δ/σ)max < 0.001 |
167 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
Special details top
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 >
σ(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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.4791 (2) | 0.66745 (15) | 0.08407 (6) | 0.0460 (3) | |
O2 | 0.3502 (2) | 0.58560 (19) | −0.00495 (7) | 0.0609 (4) | |
O3 | 0.69330 (18) | 0.84187 (19) | 0.12224 (6) | 0.0494 (4) | |
H3 | 0.7362 | 0.8698 | 0.0884 | 0.074* | |
C1 | 0.3851 (3) | 0.6902 (2) | 0.03000 (9) | 0.0453 (4) | |
C2 | 0.3375 (3) | 0.8525 (2) | 0.02439 (8) | 0.0436 (4) | |
H2 | 0.2720 | 0.8965 | −0.0087 | 0.052* | |
C3 | 0.4028 (2) | 0.9266 (2) | 0.07401 (7) | 0.0361 (4) | |
C4 | 0.3771 (3) | 1.0888 (2) | 0.09503 (8) | 0.0393 (4) | |
C5 | 0.2900 (2) | 1.0833 (2) | 0.16244 (7) | 0.0357 (4) | |
H5 | 0.3029 | 1.1864 | 0.1801 | 0.043* | |
C6 | 0.0830 (3) | 1.0446 (3) | 0.16444 (9) | 0.0474 (5) | |
H6A | 0.0651 | 0.9393 | 0.1513 | 0.057* | |
H6B | 0.0163 | 1.1101 | 0.1353 | 0.057* | |
C7 | 0.0042 (3) | 1.0660 (3) | 0.23023 (10) | 0.0614 (6) | |
H7A | −0.0200 | 1.1739 | 0.2370 | 0.074* | |
H7B | −0.1139 | 1.0124 | 0.2330 | 0.074* | |
C8 | 0.1301 (3) | 1.0093 (2) | 0.28139 (9) | 0.0477 (5) | |
C9 | 0.3038 (3) | 0.9689 (2) | 0.27027 (8) | 0.0431 (4) | |
H9 | 0.3744 | 0.9344 | 0.3040 | 0.052* | |
C10 | 0.3968 (3) | 0.9745 (2) | 0.20673 (7) | 0.0367 (4) | |
H10 | 0.5226 | 1.0159 | 0.2125 | 0.044* | |
C11 | 0.4157 (3) | 0.8116 (2) | 0.18021 (8) | 0.0406 (4) | |
H11A | 0.4914 | 0.7501 | 0.2083 | 0.049* | |
H11B | 0.2934 | 0.7646 | 0.1773 | 0.049* | |
C12 | 0.5046 (3) | 0.8157 (2) | 0.11599 (8) | 0.0374 (4) | |
C13 | 0.0467 (4) | 1.0048 (3) | 0.34651 (10) | 0.0698 (7) | |
H13A | 0.1365 | 0.9643 | 0.3755 | 0.105* | |
H13B | −0.0621 | 0.9409 | 0.3463 | 0.105* | |
H13C | 0.0126 | 1.1065 | 0.3591 | 0.105* | |
C14 | 0.2543 (4) | 1.1749 (3) | 0.04829 (9) | 0.0565 (6) | |
H14A | 0.3174 | 1.1819 | 0.0086 | 0.085* | |
H14B | 0.2297 | 1.2759 | 0.0639 | 0.085* | |
H14C | 0.1388 | 1.1210 | 0.0429 | 0.085* | |
C15 | 0.5670 (3) | 1.1716 (3) | 0.09819 (10) | 0.0526 (5) | |
H15A | 0.6368 | 1.1338 | 0.1334 | 0.079* | |
H15B | 0.5470 | 1.2796 | 0.1029 | 0.079* | |
H15C | 0.6353 | 1.1527 | 0.0602 | 0.079* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0483 (8) | 0.0435 (7) | 0.0461 (7) | 0.0060 (6) | −0.0053 (6) | −0.0060 (6) |
O2 | 0.0618 (10) | 0.0583 (9) | 0.0625 (8) | 0.0016 (8) | −0.0142 (8) | −0.0204 (7) |
O3 | 0.0336 (7) | 0.0677 (9) | 0.0470 (7) | 0.0037 (7) | −0.0056 (6) | −0.0054 (7) |
C1 | 0.0382 (10) | 0.0533 (11) | 0.0444 (9) | −0.0018 (8) | −0.0026 (8) | −0.0080 (8) |
C2 | 0.0421 (10) | 0.0525 (11) | 0.0363 (8) | −0.0010 (9) | −0.0069 (8) | −0.0003 (7) |
C3 | 0.0326 (8) | 0.0445 (9) | 0.0312 (7) | −0.0029 (7) | 0.0008 (6) | 0.0036 (7) |
C4 | 0.0456 (10) | 0.0394 (8) | 0.0329 (7) | −0.0035 (8) | −0.0012 (7) | 0.0049 (7) |
C5 | 0.0377 (9) | 0.0346 (8) | 0.0347 (7) | −0.0004 (7) | −0.0019 (7) | 0.0022 (6) |
C6 | 0.0349 (9) | 0.0574 (11) | 0.0500 (10) | 0.0041 (9) | −0.0043 (8) | 0.0054 (9) |
C7 | 0.0427 (11) | 0.0759 (15) | 0.0656 (13) | 0.0084 (12) | 0.0125 (10) | 0.0047 (12) |
C8 | 0.0563 (12) | 0.0426 (9) | 0.0443 (9) | −0.0056 (9) | 0.0118 (9) | −0.0004 (8) |
C9 | 0.0518 (11) | 0.0446 (9) | 0.0329 (8) | 0.0008 (9) | 0.0010 (8) | 0.0038 (7) |
C10 | 0.0342 (8) | 0.0427 (9) | 0.0332 (7) | −0.0011 (7) | −0.0014 (7) | 0.0019 (7) |
C11 | 0.0433 (10) | 0.0416 (9) | 0.0368 (8) | 0.0061 (8) | −0.0013 (7) | 0.0071 (7) |
C12 | 0.0348 (9) | 0.0406 (9) | 0.0368 (8) | 0.0035 (8) | −0.0026 (7) | −0.0025 (7) |
C13 | 0.0798 (18) | 0.0743 (16) | 0.0553 (12) | −0.0050 (14) | 0.0264 (12) | −0.0023 (11) |
C14 | 0.0772 (15) | 0.0497 (11) | 0.0427 (10) | 0.0100 (11) | −0.0082 (10) | 0.0115 (9) |
C15 | 0.0606 (13) | 0.0508 (11) | 0.0464 (10) | −0.0182 (10) | 0.0085 (9) | 0.0013 (9) |
Geometric parameters (Å, º) top
O1—C1 | 1.349 (2) | C7—H7A | 0.9700 |
O1—C12 | 1.475 (2) | C7—H7B | 0.9700 |
O2—C1 | 1.205 (2) | C8—C9 | 1.316 (3) |
O3—C12 | 1.379 (2) | C8—C13 | 1.511 (3) |
O3—H3 | 0.8200 | C9—C10 | 1.510 (2) |
C1—C2 | 1.463 (3) | C9—H9 | 0.9300 |
C2—C3 | 1.325 (2) | C10—C11 | 1.538 (3) |
C2—H2 | 0.9300 | C10—H10 | 0.9800 |
C3—C4 | 1.498 (3) | C11—C12 | 1.510 (2) |
C3—C12 | 1.508 (2) | C11—H11A | 0.9700 |
C4—C14 | 1.527 (3) | C11—H11B | 0.9700 |
C4—C15 | 1.544 (3) | C13—H13A | 0.9600 |
C4—C5 | 1.566 (2) | C13—H13B | 0.9600 |
C5—C6 | 1.524 (3) | C13—H13C | 0.9600 |
C5—C10 | 1.543 (2) | C14—H14A | 0.9600 |
C5—H5 | 0.9800 | C14—H14B | 0.9600 |
C6—C7 | 1.523 (3) | C14—H14C | 0.9600 |
C6—H6A | 0.9700 | C15—H15A | 0.9600 |
C6—H6B | 0.9700 | C15—H15B | 0.9600 |
C7—C8 | 1.500 (3) | C15—H15C | 0.9600 |
| | | |
C1—O1—C12 | 109.04 (14) | C8—C9—H9 | 117.6 |
C12—O3—H3 | 109.5 | C10—C9—H9 | 117.6 |
O2—C1—O1 | 121.3 (2) | C9—C10—C11 | 109.76 (14) |
O2—C1—C2 | 129.5 (2) | C9—C10—C5 | 110.4 (2) |
O1—C1—C2 | 109.21 (16) | C11—C10—C5 | 112.93 (14) |
C3—C2—C1 | 109.04 (17) | C9—C10—H10 | 107.9 |
C3—C2—H2 | 125.5 | C11—C10—H10 | 107.9 |
C1—C2—H2 | 125.5 | C5—C10—H10 | 107.9 |
C2—C3—C4 | 131.1 (2) | C12—C11—C10 | 110.36 (14) |
C2—C3—C12 | 109.3 (2) | C12—C11—H11A | 109.6 |
C4—C3—C12 | 119.39 (15) | C10—C11—H11A | 109.6 |
C3—C4—C14 | 110.03 (15) | C12—C11—H11B | 109.6 |
C3—C4—C15 | 110.33 (16) | C10—C11—H11B | 109.6 |
C14—C4—C15 | 107.82 (16) | H11A—C11—H11B | 108.1 |
C3—C4—C5 | 107.13 (13) | O3—C12—O1 | 108.2 (2) |
C14—C4—C5 | 112.51 (16) | O3—C12—C11 | 109.4 (1) |
C15—C4—C5 | 109.02 (14) | O1—C12—C11 | 110.13 (15) |
C6—C5—C10 | 109.25 (15) | O3—C12—C3 | 115.2 (2) |
C6—C5—C4 | 114.88 (15) | O1—C12—C3 | 103.36 (13) |
C10—C5—C4 | 112.42 (14) | C11—C12—C3 | 110.37 (14) |
C6—C5—H5 | 106.6 | C8—C13—H13A | 109.5 |
C10—C5—H5 | 106.6 | C8—C13—H13B | 109.5 |
C4—C5—H5 | 106.6 | H13A—C13—H13B | 109.5 |
C5—C6—C7 | 111.12 (17) | C8—C13—H13C | 109.5 |
C5—C6—H6A | 109.4 | H13A—C13—H13C | 109.5 |
C7—C6—H6A | 109.4 | H13B—C13—H13C | 109.5 |
C5—C6—H6B | 109.4 | C4—C14—H14A | 109.5 |
C7—C6—H6B | 109.4 | C4—C14—H14B | 109.5 |
H6A—C6—H6B | 108.0 | H14A—C14—H14B | 109.5 |
C8—C7—C6 | 113.87 (18) | C4—C14—H14C | 109.5 |
C8—C7—H7A | 108.8 | H14A—C14—H14C | 109.5 |
C6—C7—H7A | 108.8 | H14B—C14—H14C | 109.5 |
C8—C7—H7B | 108.8 | C4—C15—H15A | 109.5 |
C6—C7—H7B | 108.8 | C4—C15—H15B | 109.5 |
H7A—C7—H7B | 107.7 | H15A—C15—H15B | 109.5 |
C9—C8—C7 | 121.9 (2) | C4—C15—H15C | 109.5 |
C9—C8—C13 | 122.2 (2) | H15A—C15—H15C | 109.5 |
C7—C8—C13 | 115.9 (2) | H15B—C15—H15C | 109.5 |
C8—C9—C10 | 124.8 (2) | | |
| | | |
C12—O1—C1—O2 | 178.70 (18) | C7—C8—C9—C10 | 0.2 (3) |
C12—O1—C1—C2 | −2.1 (2) | C13—C8—C9—C10 | −178.37 (19) |
O2—C1—C2—C3 | 179.5 (2) | C8—C9—C10—C11 | −105.3 (2) |
O1—C1—C2—C3 | 0.4 (2) | C8—C9—C10—C5 | 19.8 (3) |
C1—C2—C3—C4 | −172.87 (18) | C6—C5—C10—C9 | −49.2 (2) |
C1—C2—C3—C12 | 1.4 (2) | C4—C5—C10—C9 | −177.98 (15) |
C2—C3—C4—C14 | −0.6 (3) | C6—C5—C10—C11 | 74.10 (19) |
C12—C3—C4—C14 | −174.40 (17) | C4—C5—C10—C11 | −54.7 (2) |
C2—C3—C4—C15 | −119.4 (2) | C9—C10—C11—C12 | 178.7 (2) |
C12—C3—C4—C15 | 66.8 (2) | C5—C10—C11—C12 | 55.1 (2) |
C2—C3—C4—C5 | 122.0 (2) | C1—O1—C12—O3 | −119.81 (16) |
C12—C3—C4—C5 | −51.8 (2) | C1—O1—C12—C11 | 120.71 (16) |
C3—C4—C5—C6 | −76.3 (2) | C1—O1—C12—C3 | 2.80 (18) |
C14—C4—C5—C6 | 44.8 (2) | C10—C11—C12—O3 | 75.7 (2) |
C15—C4—C5—C6 | 164.32 (17) | C10—C11—C12—O1 | −165.50 (15) |
C3—C4—C5—C10 | 49.5 (2) | C10—C11—C12—C3 | −52.0 (2) |
C14—C4—C5—C10 | 170.5 (2) | C2—C3—C12—O3 | 115.26 (18) |
C15—C4—C5—C10 | −69.9 (2) | C4—C3—C12—O3 | −69.7 (2) |
C10—C5—C6—C7 | 61.4 (2) | C2—C3—C12—O1 | −2.55 (19) |
C4—C5—C6—C7 | −171.21 (16) | C4—C3—C12—O1 | 172.50 (15) |
C5—C6—C7—C8 | −41.5 (3) | C2—C3—C12—C11 | −120.30 (17) |
C6—C7—C8—C9 | 10.6 (3) | C4—C3—C12—C11 | 54.8 (2) |
C6—C7—C8—C13 | −170.8 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2i | 0.82 | 2.00 | 2.812 (2) | 174 |
Symmetry code: (i) x+1/2, −y+3/2, −z. |