A monoclinic form of dendocarbin A: a borderline case of one-dimensional isostructural polymorphism

The title compound, dendocarbin A [systematic name: (1R,5aS,9aS,9bR)-1-hy­droxy-6,6,9a-tri­methyl­dodeca­hydro­naphtho­[1,2-c]furan-3-one], C₁₅H₂₂O₃, is a sesquiterpene lactone isolated from Drimys winteri var chilensis. The monoclinic phase described herein displays an identical mol­ecular structure to the ortho­rhom­bic phase that we reported previously [Paz Robles et al. (2014). Acta Cryst. C70, 1007-1010], while varying significantly in chain pitch, and can thus be considered as a borderline case of one-dimensional isostructural polymorphism.

Computing details

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2008) and PLATON (Spek, 2009).

(1R,5aS,9aS,9bR)-1-Hydroxy-6,6,9a-trimethyldodecahydronaphtho[1,2-c]furan-3-one

Crystal data

C15H22O3	F(000) = 272
Mr = 250.32	Dx = 1.152 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 8.2892 (10) Å	Cell parameters from 3400 reflections
b = 8.3401 (7) Å	θ = 3.9–25.4°
c = 11.0225 (13) Å	µ = 0.08 mm^−1
β = 108.750 (13)°	T = 295 K
V = 721.58 (15) Å^3	Block, colourless
Z = 2	0.24 × 0.18 × 0.12 mm

Data collection

Oxford Diffraction Gemini CCD S Ultra diffractometer	2519 reflections with I > 2σ(I)
ω scans, thick slices	Rint = 0.032
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	θmax = 28.8°, θmin = 3.9°
Tmin = 0.967, Tmax = 0.988	h = −11→11
11012 measured reflections	k = −11→11
3411 independent reflections	l = −14→14

Refinement

Refinement on F^2	1 restraint
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2) + (0.0402P)^2 + 0.0646P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
3411 reflections	Δρmax = 0.15 e Å^−3
170 parameters	Δρmin = −0.16 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.3432 (2)	0.3387 (3)	0.3519 (2)	0.0627 (5)
H1O	0.308 (4)	0.309 (4)	0.409 (3)	0.073 (10)*
O2	0.7646 (2)	0.6896 (2)	0.46443 (18)	0.0591 (5)
O3	0.5689 (2)	0.5045 (2)	0.45756 (17)	0.0553 (5)
C1	0.5275 (4)	0.0419 (3)	0.2243 (3)	0.0612 (7)
H1A	0.4799	0.0129	0.2909	0.073*
H1B	0.4386	0.0943	0.1562	0.073*
C2	0.5820 (5)	−0.1096 (4)	0.1718 (3)	0.0824 (10)
H2A	0.6639	−0.1675	0.2408	0.099*
H2B	0.4838	−0.1783	0.1357	0.099*
C3	0.6610 (5)	−0.0691 (4)	0.0695 (3)	0.0839 (10)
H3A	0.5760	−0.0165	−0.0010	0.101*
H3B	0.6932	−0.1679	0.0371	0.101*
C4	0.8176 (4)	0.0393 (3)	0.1162 (3)	0.0650 (8)
C5	0.7668 (3)	0.1913 (3)	0.1786 (2)	0.0468 (6)
H5	0.6822	0.2465	0.1078	0.056*
C6	0.9134 (3)	0.3110 (3)	0.2271 (3)	0.0609 (7)
H6A	1.0134	0.2543	0.2801	0.073*
H6B	0.9401	0.3543	0.1541	0.073*
C7	0.8772 (3)	0.4465 (3)	0.3024 (2)	0.0514 (6)
H7	0.9555	0.5297	0.3282	0.062*
C8	0.7363 (3)	0.4511 (3)	0.3333 (2)	0.0423 (5)
C9	0.6015 (3)	0.3248 (3)	0.2981 (2)	0.0397 (5)
H9	0.5178	0.3558	0.2162	0.048*
C10	0.6744 (3)	0.1602 (3)	0.2793 (2)	0.0425 (5)
C11	0.5168 (3)	0.3423 (3)	0.4014 (2)	0.0457 (6)
H11	0.5577	0.2592	0.4670	0.055*
C12	0.6971 (3)	0.5629 (3)	0.4220 (2)	0.0467 (6)
C13	0.9684 (5)	−0.0556 (4)	0.2049 (3)	0.0888 (11)
H13A	0.9368	−0.1005	0.2743	0.133*
H13B	1.0641	0.0148	0.2386	0.133*
H13C	0.9986	−0.1403	0.1573	0.133*
C14	0.8664 (5)	0.0924 (5)	−0.0011 (3)	0.0933 (11)
H14A	0.8705	0.0004	−0.0524	0.140*
H14B	0.9762	0.1431	0.0270	0.140*
H14C	0.7830	0.1667	−0.0512	0.140*
C15	0.7933 (3)	0.0989 (3)	0.4082 (2)	0.0506 (6)
H15A	0.7319	0.0925	0.4685	0.076*
H15B	0.8876	0.1713	0.4399	0.076*
H15C	0.8350	−0.0055	0.3968	0.076*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0392 (10)	0.0867 (14)	0.0655 (12)	−0.0038 (9)	0.0214 (9)	0.0109 (11)
O2	0.0632 (12)	0.0465 (10)	0.0743 (12)	−0.0044 (9)	0.0315 (10)	−0.0102 (10)
O3	0.0548 (10)	0.0582 (10)	0.0636 (11)	−0.0037 (8)	0.0337 (9)	−0.0075 (9)
C1	0.0668 (17)	0.0648 (18)	0.0476 (13)	−0.0229 (14)	0.0124 (12)	−0.0067 (13)
C2	0.109 (3)	0.0650 (19)	0.0684 (19)	−0.0350 (18)	0.0211 (19)	−0.0268 (16)
C3	0.116 (3)	0.073 (2)	0.0601 (18)	−0.011 (2)	0.0242 (19)	−0.0281 (16)
C4	0.082 (2)	0.0631 (18)	0.0529 (15)	0.0051 (15)	0.0252 (15)	−0.0128 (14)
C5	0.0521 (14)	0.0506 (14)	0.0389 (12)	−0.0007 (12)	0.0166 (10)	−0.0026 (11)
C6	0.0585 (16)	0.0675 (17)	0.0694 (17)	−0.0092 (14)	0.0384 (14)	−0.0122 (15)
C7	0.0540 (15)	0.0499 (14)	0.0571 (14)	−0.0124 (12)	0.0274 (12)	−0.0041 (12)
C8	0.0460 (13)	0.0422 (12)	0.0418 (12)	−0.0017 (11)	0.0187 (10)	0.0038 (10)
C9	0.0371 (11)	0.0480 (13)	0.0329 (11)	−0.0022 (10)	0.0099 (9)	0.0051 (10)
C10	0.0450 (13)	0.0446 (13)	0.0350 (11)	−0.0066 (10)	0.0088 (10)	−0.0011 (10)
C11	0.0397 (13)	0.0534 (15)	0.0457 (12)	−0.0018 (11)	0.0160 (10)	0.0056 (12)
C12	0.0469 (14)	0.0450 (14)	0.0515 (13)	0.0041 (11)	0.0203 (11)	0.0042 (12)
C13	0.107 (3)	0.075 (2)	0.087 (2)	0.027 (2)	0.035 (2)	−0.0165 (19)
C14	0.123 (3)	0.104 (3)	0.070 (2)	0.012 (2)	0.055 (2)	−0.016 (2)
C15	0.0584 (15)	0.0479 (14)	0.0418 (13)	0.0033 (11)	0.0108 (11)	0.0013 (11)

Geometric parameters (Å, º)

O1—C11	1.365 (3)	C6—C7	1.489 (3)
O1—H1O	0.81 (3)	C6—H6A	0.9700
O2—C12	1.217 (3)	C6—H6B	0.9700
O3—C12	1.337 (3)	C7—C8	1.318 (3)
O3—C11	1.493 (3)	C7—H7	0.9300
C1—C2	1.518 (4)	C8—C12	1.461 (3)
C1—C10	1.533 (3)	C8—C9	1.493 (3)
C1—H1A	0.9700	C9—C11	1.525 (3)
C1—H1B	0.9700	C9—C10	1.540 (3)
C2—C3	1.512 (5)	C9—H9	0.9800
C2—H2A	0.9700	C10—C15	1.533 (3)
C2—H2B	0.9700	C11—H11	0.9800
C3—C4	1.529 (4)	C13—H13A	0.9600
C3—H3A	0.9700	C13—H13B	0.9600
C3—H3B	0.9700	C13—H13C	0.9600
C4—C13	1.536 (5)	C14—H14A	0.9600
C4—C14	1.539 (4)	C14—H14B	0.9600
C4—C5	1.563 (4)	C14—H14C	0.9600
C5—C6	1.531 (3)	C15—H15A	0.9600
C5—C10	1.560 (3)	C15—H15B	0.9600
C5—H5	0.9800	C15—H15C	0.9600
C11—O1—H1O	107 (2)	C7—C8—C9	124.3 (2)
C12—O3—C11	111.10 (18)	C12—C8—C9	108.38 (19)
C2—C1—C10	113.0 (2)	C8—C9—C11	102.97 (18)
C2—C1—H1A	109.0	C8—C9—C10	111.75 (17)
C10—C1—H1A	109.0	C11—C9—C10	118.68 (18)
C2—C1—H1B	109.0	C8—C9—H9	107.6
C10—C1—H1B	109.0	C11—C9—H9	107.6
H1A—C1—H1B	107.8	C10—C9—H9	107.6
C3—C2—C1	110.6 (3)	C1—C10—C15	110.2 (2)
C3—C2—H2A	109.5	C1—C10—C9	109.34 (19)
C1—C2—H2A	109.5	C15—C10—C9	109.63 (18)
C3—C2—H2B	109.5	C1—C10—C5	109.53 (19)
C1—C2—H2B	109.5	C15—C10—C5	113.5 (2)
H2A—C2—H2B	108.1	C9—C10—C5	104.54 (17)
C2—C3—C4	113.9 (2)	O1—C11—O3	108.23 (19)
C2—C3—H3A	108.8	O1—C11—C9	112.26 (19)
C4—C3—H3A	108.8	O3—C11—C9	104.75 (18)
C2—C3—H3B	108.8	O1—C11—H11	110.5
C4—C3—H3B	108.8	O3—C11—H11	110.5
H3A—C3—H3B	107.7	C9—C11—H11	110.5
C3—C4—C13	109.8 (3)	O2—C12—O3	121.0 (2)
C3—C4—C14	108.1 (3)	O2—C12—C8	129.6 (2)
C13—C4—C14	107.6 (3)	O3—C12—C8	109.4 (2)
C3—C4—C5	107.9 (2)	C4—C13—H13A	109.5
C13—C4—C5	114.7 (2)	C4—C13—H13B	109.5
C14—C4—C5	108.5 (3)	H13A—C13—H13B	109.5
C6—C5—C10	112.09 (18)	C4—C13—H13C	109.5
C6—C5—C4	112.8 (2)	H13A—C13—H13C	109.5
C10—C5—C4	116.2 (2)	H13B—C13—H13C	109.5
C6—C5—H5	104.8	C4—C14—H14A	109.5
C10—C5—H5	104.8	C4—C14—H14B	109.5
C4—C5—H5	104.8	H14A—C14—H14B	109.5
C7—C6—C5	114.2 (2)	C4—C14—H14C	109.5
C7—C6—H6A	108.7	H14A—C14—H14C	109.5
C5—C6—H6A	108.7	H14B—C14—H14C	109.5
C7—C6—H6B	108.7	C10—C15—H15A	109.5
C5—C6—H6B	108.7	C10—C15—H15B	109.5
H6A—C6—H6B	107.6	H15A—C15—H15B	109.5
C8—C7—C6	121.4 (2)	C10—C15—H15C	109.5
C8—C7—H7	119.3	H15A—C15—H15C	109.5
C6—C7—H7	119.3	H15B—C15—H15C	109.5
C7—C8—C12	126.7 (2)