Crystal structure of 3a,6,6,9a-tetra-methyl-dodeca-hydro-naphtho-[2,1-b]furan-2-ol.

The title compound (common name: sclaral), C16H28O2, is a sclareolide derivative, which was synthesized from sclareolide itself. In the mol-ecule, the two six-membered rings, A and B, of the labdane skeleton adopt chair conformations and the five-membered O-containing heterocyclic ring C displays an envelope conformation, with the methine C atom of the fused C-C bond as the flap. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds, forming chains propagating along [100].

Related literature

For the chemistry and biological importance of sclareolides and the title compound, see: Dixon et al. (2012 ▸); Michaudel et al. (2015 ▸); Sun et al. (2013 ▸). For previously reported spectroscopic and anal­yt­ical data for the title compound, see: Margaros et al. (2007 ▸). For related structures, see: Martínez-Carrera et al. (1978 ▸); Huang et al. (2008 ▸).

Experimental

Crystal data

C16H28O2

M = 252.38

Orthorhombic,

a = 7.1675 (8) Å

b = 11.2654 (13) Å

c = 18.144 (2) Å

V = 1465.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 296 K

0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▸) T min = 0.984, T max = 0.987

9607 measured reflections

2658 independent reflections

2299 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.127

S = 1.08

2658 reflections

181 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2002 ▸); cell refinement: SAINT (Bruker, 2002 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: SHELXTL (Sheldrick, 2008 ▸) and PLATON (Spek, 2009 ▸); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015016370/su5201sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015016370/su5201Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015016370/su5201Isup3.cdx

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015016370/su5201Isup4.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015016370/su5201fig1.tif

A view of the mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Click here for additional data file.

a . DOI: 10.1107/S2056989015016370/su5201fig2.tif

View along the a axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1), and C-bound H atoms have been omitted for clarity.

CCDC reference: 1421899

Additional supporting information: crystallographic information; 3D view; checkCIF report

C16H28O2	F(000) = 560
Mr = 252.38	Dx = 1.144 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2540 reflections
a = 7.1675 (8) Å	θ = 3.1–21.6°
b = 11.2654 (13) Å	µ = 0.07 mm−1
c = 18.144 (2) Å	T = 296 K
V = 1465.0 (3) Å3	Block, colourless
Z = 4	0.22 × 0.20 × 0.18 mm

Bruker SMART CCD diffractometer	2658 independent reflections
Radiation source: fine-focus sealed tube	2299 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
phi and ω scans	θmax = 25.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −8→8
Tmin = 0.984, Tmax = 0.987	k = −13→13
9607 measured reflections	l = −21→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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0651P)2 + 0.258P] where P = (Fo2 + 2Fc2)/3
2658 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.40 e Å−3
1 restraint	Δρmin = −0.19 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.0482 (3)	0.86847 (19)	0.67801 (12)	0.0348 (5)
C2	0.2058 (3)	0.8474 (2)	0.62309 (12)	0.0392 (5)
C3	0.3421 (3)	0.7594 (2)	0.65591 (13)	0.0469 (6)
H3A	0.4488	0.7504	0.6235	0.056*
H3B	0.2825	0.6826	0.6612	0.056*
C4	0.4067 (3)	0.8050 (2)	0.73202 (13)	0.0443 (5)
H4A	0.4901	0.7471	0.7539	0.053*
H4B	0.4759	0.8783	0.7255	0.053*
C5	0.2429 (3)	0.82737 (18)	0.78462 (12)	0.0342 (5)
C6	0.1029 (3)	0.91962 (17)	0.75332 (11)	0.0339 (5)
C7	0.1778 (4)	1.04780 (19)	0.74731 (14)	0.0515 (6)
H7A	0.1100	1.0896	0.7098	0.077*
H7B	0.3078	1.0459	0.7347	0.077*
H7C	0.1620	1.0875	0.7937	0.077*
C8	−0.0711 (3)	0.9208 (3)	0.80299 (14)	0.0519 (6)
H8A	−0.1541	0.9836	0.7869	0.062*
H8B	−0.1368	0.8460	0.7976	0.062*
C9	−0.0233 (4)	0.9397 (3)	0.88443 (15)	0.0655 (8)
H9A	0.0283	1.0186	0.8910	0.079*
H9B	−0.1363	0.9343	0.9136	0.079*
C10	0.1147 (4)	0.8493 (3)	0.91114 (14)	0.0620 (8)
H10A	0.0560	0.7717	0.9097	0.074*
H10B	0.1444	0.8665	0.9622	0.074*
C11	0.2970 (3)	0.8434 (2)	0.86729 (13)	0.0462 (6)
C12	0.4061 (5)	0.7330 (3)	0.89311 (17)	0.0775 (9)
H12A	0.5323	0.7377	0.8756	0.116*
H12B	0.3480	0.6628	0.8738	0.116*
H12C	0.4059	0.7298	0.9460	0.116*
C13	0.4176 (4)	0.9519 (3)	0.88354 (15)	0.0579 (7)
H13A	0.5198	0.9547	0.8494	0.087*
H13B	0.4652	0.9468	0.9329	0.087*
H13C	0.3438	1.0226	0.8786	0.087*
C14	−0.1012 (4)	0.9213 (2)	0.62815 (14)	0.0520 (6)
H14A	−0.0739	1.0033	0.6157	0.062*
H14B	−0.2240	0.9166	0.6504	0.062*
C15	−0.0850 (3)	0.8402 (2)	0.56099 (14)	0.0495 (6)
H15	−0.112 (4)	0.884 (2)	0.5155 (15)	0.059*
C16	0.3106 (4)	0.9544 (3)	0.59153 (15)	0.0622 (7)
H16A	0.3743	0.9313	0.5472	0.093*
H16B	0.3997	0.9823	0.6270	0.093*
H16C	0.2234	1.0166	0.5805	0.093*
H1	0.007 (3)	0.7879 (18)	0.6884 (10)	0.024 (5)*
H5	0.168 (3)	0.751 (2)	0.7848 (12)	0.040 (6)*
O1	0.1024 (2)	0.79612 (16)	0.56104 (8)	0.0520 (5)
O2	−0.2051 (3)	0.7454 (2)	0.56902 (11)	0.0678 (6)
H1O	−0.242 (4)	0.715 (3)	0.5234 (11)	0.081*

	U11	U22	U33	U12	U13	U23
C1	0.0291 (10)	0.0358 (11)	0.0396 (11)	0.0007 (9)	0.0009 (9)	−0.0037 (9)
C2	0.0342 (10)	0.0491 (12)	0.0342 (11)	−0.0040 (10)	0.0055 (10)	−0.0055 (10)
C3	0.0352 (11)	0.0571 (14)	0.0485 (14)	0.0072 (11)	0.0082 (11)	−0.0129 (11)
C4	0.0313 (10)	0.0529 (13)	0.0485 (14)	0.0097 (10)	0.0001 (10)	−0.0055 (10)
C5	0.0331 (10)	0.0328 (10)	0.0368 (11)	−0.0020 (9)	0.0018 (9)	−0.0018 (9)
C6	0.0270 (9)	0.0355 (10)	0.0393 (11)	0.0012 (9)	0.0011 (9)	−0.0073 (9)
C7	0.0607 (15)	0.0336 (12)	0.0601 (15)	0.0041 (11)	−0.0055 (13)	−0.0088 (11)
C8	0.0304 (11)	0.0749 (16)	0.0503 (14)	0.0045 (11)	0.0059 (11)	−0.0221 (13)
C9	0.0430 (13)	0.104 (2)	0.0498 (15)	−0.0091 (15)	0.0137 (12)	−0.0322 (16)
C10	0.0613 (16)	0.090 (2)	0.0352 (13)	−0.0243 (16)	0.0041 (13)	−0.0063 (13)
C11	0.0474 (13)	0.0528 (13)	0.0385 (12)	−0.0035 (11)	−0.0058 (11)	−0.0025 (10)
C12	0.092 (2)	0.078 (2)	0.0620 (18)	0.0127 (19)	−0.0247 (18)	0.0158 (15)
C13	0.0434 (13)	0.0751 (17)	0.0551 (15)	−0.0065 (13)	−0.0103 (13)	−0.0149 (14)
C14	0.0439 (13)	0.0601 (15)	0.0520 (14)	0.0096 (12)	−0.0092 (12)	−0.0063 (12)
C15	0.0407 (12)	0.0673 (15)	0.0404 (13)	−0.0035 (12)	−0.0050 (11)	−0.0024 (12)
C16	0.0648 (16)	0.0754 (18)	0.0463 (14)	−0.0191 (15)	0.0090 (14)	0.0086 (13)
O1	0.0417 (8)	0.0749 (11)	0.0393 (9)	−0.0020 (9)	0.0020 (8)	−0.0166 (8)
O2	0.0591 (11)	0.0950 (15)	0.0494 (11)	−0.0205 (11)	−0.0057 (10)	−0.0045 (10)

C1—C14	1.523 (3)	C6—C8	1.539 (3)
C1—C2	1.525 (3)	C6—C7	1.544 (3)
C1—C6	1.534 (3)	C8—C9	1.532 (4)
C2—O1	1.466 (3)	C9—C10	1.500 (4)
C2—C3	1.513 (3)	C10—C11	1.531 (3)
C2—C16	1.531 (3)	C11—C13	1.526 (3)
C3—C4	1.544 (3)	C11—C12	1.542 (4)
C4—C5	1.534 (3)	C14—C15	1.527 (3)
C5—C6	1.552 (3)	C15—O2	1.380 (3)
C5—C11	1.560 (3)	C15—O1	1.432 (3)
C14—C1—C2	101.16 (18)	C1—C6—C5	103.87 (16)
C14—C1—C6	124.19 (19)	C8—C6—C5	108.38 (18)
C2—C1—C6	116.81 (16)	C7—C6—C5	115.30 (17)
O1—C2—C3	111.75 (18)	C9—C8—C6	112.63 (18)
O1—C2—C1	100.87 (15)	C10—C9—C8	111.4 (2)
C3—C2—C1	108.84 (18)	C9—C10—C11	115.1 (2)
O1—C2—C16	105.71 (18)	C13—C11—C10	110.4 (2)
C3—C2—C16	110.26 (19)	C13—C11—C12	107.4 (2)
C1—C2—C16	119.00 (19)	C10—C11—C12	108.0 (2)
C2—C3—C4	109.12 (18)	C13—C11—C5	114.8 (2)
C5—C4—C3	112.42 (17)	C10—C11—C5	107.00 (18)
C4—C5—C6	112.15 (17)	C12—C11—C5	109.0 (2)
C4—C5—C11	115.27 (17)	C1—C14—C15	100.75 (19)
C6—C5—C11	115.79 (17)	O2—C15—O1	108.5 (2)
C1—C6—C8	108.51 (17)	O2—C15—C14	109.4 (2)
C1—C6—C7	112.17 (19)	O1—C15—C14	106.16 (19)
C8—C6—C7	108.36 (19)	C15—O1—C2	109.75 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O···O1i	0.93 (2)	1.90 (2)	2.773 (2)	155 (3)

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O2H1OO1i	0.93(2)	1.90(2)	2.773(2)	155(3)

Symmetry code: (i) .