(1R,2S,4S,4aS,8S,8aS)-4-Hy-droxy-8,8a-dimethyl-10-oxo-2,3,4,7,8,8a-hexa-hydro-1H-4a,1-(ep-oxy-methano)-naphthalen-2-yl acetate.

The title compound, C15H20O5, presents a bis-norsesquiterpene skeleton, with a trans-deca-line backbone constrained by the lactone bridge. The α-hy-droxy substituent and the methyl group belonging to the two deca-line rings are in axial positions, whereas the other methyl group and the acyl group occupy the sterically preferred equatorial positions. The mol-ecular structure is stabilized by an intra-molecular C-H⋯O hydrogen bond. In the crystal, mol-ecules are linked into chains along [010] by O-H⋯O hydrogen bonds.

Related literature

For the synthesis, see: Selaimia-Ferdjani et al. (2013 ▶). For the biological activity of the natural lactone Paralemnolide A analogue of the title compound, see: Wang et al. (2012 ▶) and of related nardosinane sesquiterpene derivatives, see: Bishara et al. (2008 ▶); Huang et al. (2011 ▶); Petit et al. (2004 ▶); Lu et al. (2011 ▶). For related nardosinane sesquiterpenes whose biological activity has not been investigated, see: El-Gamal et al. (2005 ▶); Huang et al. (2006 ▶); Wang & Duh (2007 ▶); Wang et al. (2010 ▶).

Experimental

Crystal data

C15H20O5

M = 280.3

Monoclinic,

a = 10.3312 (10) Å

b = 7.1692 (8) Å

c = 10.8502 (6) Å

β = 115.958 (5)°

V = 722.56 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.48 × 0.42 × 0.30 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: gaussian (JANA2006; Petříček et al., 2006) ▶ T min = 0.967, T max = 0.972

12282 measured reflections

3328 independent reflections

2774 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.138

S = 1.84

3328 reflections

185 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.12 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: EVALCCD (Duisenberg et al., 2003 ▶); data reduction: COLLECT (Nonius, 1998 ▶); program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: JANA2006 (Petříček et al., 2006) ▶; molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: JANA2006 ▶.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813013524/bt6907sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813013524/bt6907Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H20O5	Z = 2
Mr = 280.3	F(000) = 300
Monoclinic, P21	Dx = 1.288 Mg m−3
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71069 Å
a = 10.3312 (10) Å	µ = 0.10 mm−1
b = 7.1692 (8) Å	T = 293 K
c = 10.8502 (6) Å	Block, colourless
β = 115.958 (5)°	0.48 × 0.42 × 0.30 mm
V = 722.56 (12) Å3

Nonius KappaCCD diffractometer	3328 independent reflections
Radiation source: X-ray tube	2774 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
CCD, φ and ω frames scans	θmax = 28.1°, θmin = 6.5°
Absorption correction: gaussian (JANA2006; Petříček et al., 2006)	h = −13→13
Tmin = 0.967, Tmax = 0.972	k = −9→9
12282 measured reflections	l = −14→14

Refinement on F2	77 constraints
R[F2 > 2σ(F2)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.138	Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0025000002I2)
S = 1.84	(Δ/σ)max = 0.013
3328 reflections	Δρmax = 0.15 e Å−3
185 parameters	Δρmin = −0.12 e Å−3
0 restraints

	x	y	z	Uiso*/Ueq
O4a	−0.24245 (17)	−0.3248 (2)	−0.96277 (13)	0.0469 (6)
O2	0.13229 (15)	−0.5347 (2)	−0.74186 (16)	0.0540 (6)
O9	−0.1870 (2)	−0.6248 (2)	−0.95660 (17)	0.0580 (7)
O4	−0.0236 (2)	0.0757 (2)	−0.7741 (2)	0.0747 (9)
O12	0.3391 (2)	−0.4418 (4)	−0.5763 (2)	0.0969 (10)
C1	−0.0910 (2)	−0.4390 (3)	−0.74640 (18)	0.0373 (6)
C2	0.0592 (2)	−0.3717 (3)	−0.7223 (2)	0.0452 (8)
C3	0.0495 (3)	−0.2237 (3)	−0.8268 (3)	0.0614 (11)
C4	−0.0719 (3)	−0.0820 (3)	−0.8628 (3)	0.0554 (10)
C5	−0.3316 (3)	−0.0382 (3)	−0.9057 (3)	0.0649 (10)
C6	−0.4264 (3)	−0.0442 (5)	−0.8551 (3)	0.0789 (12)
C7	−0.4257 (3)	−0.1856 (5)	−0.7544 (3)	0.0787 (13)
C8	−0.3245 (2)	−0.3495 (4)	−0.7387 (2)	0.0565 (9)
C9	−0.1760 (2)	−0.4802 (3)	−0.8969 (2)	0.0409 (7)
C10	−0.0991 (3)	−0.1656 (4)	−0.5957 (2)	0.0558 (9)
C11	−0.3100 (3)	−0.4779 (6)	−0.6212 (3)	0.0855 (15)
C12	0.2732 (2)	−0.5534 (3)	−0.6613 (2)	0.0504 (8)
C13	0.3297 (3)	−0.7288 (4)	−0.6924 (3)	0.0661 (11)
C8a	−0.1778 (2)	−0.2776 (3)	−0.72788 (18)	0.0400 (7)
C4a	−0.2064 (2)	−0.1689 (3)	−0.8603 (2)	0.0446 (7)
H1c5	−0.343345	0.053419	−0.97428	0.0778*
H1c6	−0.500769	0.048719	−0.885126	0.0947*
H1c7	−0.521658	−0.231528	−0.781906	0.0945*
H2c7	−0.398331	−0.127184	−0.666953	0.0945*
H1c8	−0.365931	−0.42545	−0.819637	0.0678*
H1c11	−0.262203	−0.590901	−0.625442	0.1026*
H2c11	−0.254686	−0.416546	−0.535349	0.1026*
H3c11	−0.403884	−0.507108	−0.628833	0.1026*
H1c10	−0.162091	−0.070956	−0.590084	0.0669*
H2c10	−0.070651	−0.247485	−0.518177	0.0669*
H3c10	−0.015259	−0.108038	−0.595774	0.0669*
H1c1	−0.078238	−0.541924	−0.68555	0.0448*
H1c2	0.108852	−0.317946	−0.632628	0.0543*
H1c13	0.266544	−0.830237	−0.698342	0.0793*
H2c13	0.335007	−0.715916	−0.778133	0.0793*
H3c13	0.42399	−0.753581	−0.620827	0.0793*
H1c3	0.041767	−0.283227	−0.908981	0.0736*
H2c3	0.139807	−0.159392	−0.795406	0.0736*
H1c4	−0.099131	−0.040857	−0.955087	0.0665*
H1	−0.056 (5)	0.173 (7)	−0.818 (4)	0.107 (13)*

	U11	U22	U33	U12	U13	U23
O4a	0.0587 (9)	0.0363 (7)	0.0343 (7)	−0.0011 (7)	0.0100 (6)	−0.0009 (5)
O2	0.0389 (8)	0.0493 (8)	0.0649 (9)	0.0047 (7)	0.0145 (7)	−0.0114 (8)
O9	0.0699 (11)	0.0392 (7)	0.0577 (9)	−0.0061 (8)	0.0212 (8)	−0.0126 (7)
O4	0.0777 (13)	0.0319 (8)	0.0961 (15)	−0.0112 (8)	0.0212 (11)	−0.0057 (9)
O12	0.0516 (11)	0.1034 (17)	0.1043 (16)	0.0019 (11)	0.0053 (10)	−0.0446 (15)
C1	0.0363 (9)	0.0341 (8)	0.0368 (9)	−0.0012 (8)	0.0116 (7)	0.0027 (8)
C2	0.0379 (10)	0.0385 (9)	0.0574 (12)	−0.0036 (8)	0.0191 (9)	−0.0110 (9)
C3	0.0679 (15)	0.0409 (10)	0.0914 (18)	−0.0106 (11)	0.0498 (14)	−0.0025 (12)
C4	0.0704 (16)	0.0313 (10)	0.0618 (14)	−0.0047 (10)	0.0264 (12)	0.0031 (9)
C5	0.0615 (15)	0.0462 (11)	0.0603 (14)	0.0115 (12)	0.0022 (12)	0.0025 (11)
C6	0.0530 (15)	0.0752 (17)	0.0814 (18)	0.0256 (15)	0.0043 (13)	−0.0116 (16)
C7	0.0430 (13)	0.105 (2)	0.0816 (18)	0.0144 (15)	0.0214 (12)	−0.0156 (17)
C8	0.0391 (11)	0.0744 (15)	0.0528 (12)	−0.0025 (11)	0.0171 (9)	−0.0064 (12)
C9	0.0448 (10)	0.0342 (9)	0.0414 (9)	−0.0066 (8)	0.0168 (8)	−0.0016 (8)
C10	0.0477 (12)	0.0648 (14)	0.0440 (11)	0.0048 (11)	0.0100 (9)	−0.0161 (11)
C11	0.0634 (18)	0.123 (3)	0.0822 (18)	−0.0143 (19)	0.0428 (15)	0.011 (2)
C12	0.0388 (10)	0.0562 (12)	0.0541 (12)	0.0009 (10)	0.0183 (9)	0.0023 (11)
C13	0.0491 (13)	0.0702 (15)	0.0796 (16)	0.0127 (12)	0.0289 (12)	0.0025 (14)
C8a	0.0353 (9)	0.0430 (9)	0.0351 (9)	0.0008 (8)	0.0091 (7)	−0.0031 (8)
C4a	0.0498 (11)	0.0325 (8)	0.0406 (10)	0.0004 (8)	0.0097 (8)	−0.0019 (8)

O4a—C9	1.340 (2)	C5—H1c5	0.96
O4a—C4a	1.504 (2)	C6—C7	1.488 (5)
O2—C2	1.456 (3)	C6—H1c6	0.96
O2—C12	1.337 (2)	C7—C8	1.532 (4)
O9—C9	1.201 (3)	C7—H1c7	0.96
O4—C4	1.426 (3)	C7—H2c7	0.96
O4—H1	0.83 (5)	C8—C11	1.526 (5)
O12—C12	1.185 (3)	C8—C8a	1.556 (3)
C1—C2	1.535 (3)	C8—H1c8	0.96
C1—C9	1.507 (3)	C10—C8a	1.531 (3)
C1—C8a	1.530 (3)	C10—H1c10	0.96
C1—H1c1	0.96	C10—H2c10	0.96
C2—C3	1.524 (4)	C10—H3c10	0.96
C2—H1c2	0.96	C11—H1c11	0.96
C3—C4	1.526 (4)	C11—H2c11	0.96
C3—H1c3	0.96	C11—H3c11	0.96
C3—H2c3	0.96	C12—C13	1.486 (4)
C4—C4a	1.534 (4)	C13—H1c13	0.96
C4—H1c4	0.96	C13—H2c13	0.96
C5—C6	1.316 (5)	C13—H3c13	0.96
C5—C4a	1.495 (3)	C8a—C4a	1.545 (3)
C9—O4a—C4a	108.72 (13)	C7—C8—H1c8	108.87
C2—O2—C12	118.11 (17)	C11—C8—C8a	113.63 (18)
C4—O4—H1	111 (3)	C11—C8—H1c8	105.3
C2—C1—C9	108.2 (2)	C8a—C8—H1c8	106.65
C2—C1—C8a	110.30 (16)	O4a—C9—O9	121.67 (17)
C2—C1—H1c1	107.44	O4a—C9—C1	109.53 (16)
C9—C1—C8a	101.19 (14)	O9—C9—C1	128.80 (17)
C9—C1—H1c1	115.73	C8a—C10—H1c10	109.47
C8a—C1—H1c1	113.8	C8a—C10—H2c10	109.47
O2—C2—C1	105.87 (16)	C8a—C10—H3c10	109.47
O2—C2—C3	108.7 (2)	H1c10—C10—H2c10	109.47
O2—C2—H1c2	112.88	H1c10—C10—H3c10	109.47
C1—C2—C3	111.08 (17)	H2c10—C10—H3c10	109.47
C1—C2—H1c2	110.54	C8—C11—H1c11	109.47
C3—C2—H1c2	107.84	C8—C11—H2c11	109.47
C2—C3—C4	115.7 (3)	C8—C11—H3c11	109.47
C2—C3—H1c3	109.47	H1c11—C11—H2c11	109.47
C2—C3—H2c3	109.47	H1c11—C11—H3c11	109.47
C4—C3—H1c3	109.47	H2c11—C11—H3c11	109.47
C4—C3—H2c3	109.47	O2—C12—O12	122.1 (2)
H1c3—C3—H2c3	102.43	O2—C12—C13	111.11 (19)
O4—C4—C3	110.43 (19)	O12—C12—C13	126.8 (2)
O4—C4—C4a	111.3 (3)	C12—C13—H1c13	109.47
O4—C4—H1c4	108.45	C12—C13—H2c13	109.47
C3—C4—C4a	111.97 (19)	C12—C13—H3c13	109.47
C3—C4—H1c4	107.71	H1c13—C13—H2c13	109.47
C4a—C4—H1c4	106.8	H1c13—C13—H3c13	109.47
C6—C5—C4a	122.5 (3)	H2c13—C13—H3c13	109.47
C6—C5—H1c5	118.76	C1—C8a—C8	110.28 (18)
C4a—C5—H1c5	118.76	C1—C8a—C10	114.76 (15)
C5—C6—C7	124.3 (3)	C1—C8a—C4a	98.29 (18)
C5—C6—H1c6	117.87	C8—C8a—C10	110.2 (2)
C7—C6—H1c6	117.87	C8—C8a—C4a	108.26 (15)
C6—C7—C8	112.8 (3)	C10—C8a—C4a	114.46 (17)
C6—C7—H1c7	109.47	O4a—C4a—C4	102.8 (2)
C6—C7—H2c7	109.47	O4a—C4a—C5	108.89 (15)
C8—C7—H1c7	109.47	O4a—C4a—C8a	101.37 (14)
C8—C7—H2c7	109.47	C4—C4a—C5	113.57 (19)
H1c7—C7—H2c7	105.88	C4—C4a—C8a	114.52 (16)
C7—C8—C11	111.6 (3)	C5—C4a—C8a	114.1 (2)
C7—C8—C8a	110.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H1c8···C9	0.96	2.48	2.913 (4)	107.28
C10—H3c10···O4	0.96	2.31	2.946 (4)	122.91
C2—H1c2···O12	0.96	2.36	2.668 (3)	98.20
O4—H1···O9i	0.83 (5)	2.10 (4)	2.907 (2)	165 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H3c10⋯O4	0.96	2.31	2.946 (4)	122.91
O4—H1⋯O9i	0.83 (5)	2.10 (4)	2.907 (2)	165 (4)

Symmetry code: (i) .