A furodysinin lactone derivative from the marine sponge Dysidea fragilis

The title compound, 4a,5,6,8a,9,9a-hexahydro-9a-hydroxy-4,4,7-trimethylnaphtho[2,3-b]furan-2(4H)-one, C₁₅H₂₀O₃, 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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](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

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Computing details

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).

Furodysinin lactone

Crystal data

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) Å^3	Needle, colourless
Z = 4	0.24 × 0.20 × 0.15 mm
F(000) = 536

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.104	H-atom parameters constrained
S = 1.13	w = 1/[σ^2(Fo^2) + (0.058P)^2 + 0.1311P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2^i	0.82	2.00	2.812 (2)	174

Symmetry code: (i) x+1/2, −y+3/2, −z.