[(2S,3aR,6aR)-5-Oxohexa-hydro-furo[3,2-b]furan-2-yl]methyl acetate.

The title compound, C9H12O5, is a bicyclic lactone, presenting a 2,6-dioxabi-cyclo-[3.3.0]octan-3-one skeleton, which was obtained through an intra-molecular lactonization. The bicyclic lactone presents a cis ring-junction and a 1,5-trans-substituted tetra-hydro-furan. Both five-membered rings are in twisted envelope conformations with one of the fused C atoms as the flap. The dihedral angle between the mean planes of the bicyclic lactone residue, defined by the di-hydro-furan-2(3H)-one and the tetra-hydro-furan rings, is 69.5 (2)°. The atoms of the ester chain are coplanar [maximum deviation = 0.013 (2) Å]. The absolute structure was not determined.

Related literature

For the stereoselective synthesis, applications and structures of related 2,6-dioxabi­cyclo­[3.3.0]octan-3-ones, see: Agrawal et al. (2006 ▶); Banda & Chakravarthy (2006 ▶); Paddon-Jones et al. (2001 ▶). For the biological activity of target compounds, see: Hayes et al. (2003 ▶). For the synthesis of chiral tetra­hydro­furans using l-malic acid, see: Álvarez et al. (2010 ▶). For pseudorotation parameters, see: Rao et al. (1981 ▶).

Experimental

Crystal data

C9H12O5

M = 200.19

Monoclinic,

a = 10.015 (5) Å

b = 4.647 (3) Å

c = 10.904 (5) Å

β = 109.755 (7)°

V = 477.6 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 293 K

0.49 × 0.11 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T min = 0.602, T max = 0.745

2551 measured reflections

1530 independent reflections

1313 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.097

S = 1.07

1530 reflections

128 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813010313/go2086sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813010313/go2086Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813010313/go2086Isup3.cml

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

C9H12O5	Dx = 1.392 Mg m−3
Mr = 200.19	Melting point: 360.15(4) K
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 10.015 (5) Å	Cell parameters from 1040 reflections
b = 4.647 (3) Å	θ = 2.4–24.1°
c = 10.904 (5) Å	µ = 0.12 mm−1
β = 109.755 (7)°	T = 293 K
V = 477.6 (4) Å3	Needle, colourless
Z = 2	0.49 × 0.11 × 0.10 mm
F(000) = 212

Bruker APEXII CCD diffractometer	1530 independent reflections
Radiation source: fine-focus sealed tube	1313 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 25.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −11→11
Tmin = 0.602, Tmax = 0.745	k = −5→5
2551 measured reflections	l = −13→12

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0377P)2 + 0.1292P] where P = (Fo2 + 2Fc2)/3
1530 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.14 e Å−3
1 restraint	Δρmin = −0.16 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	0.3092 (3)	0.6053 (7)	0.9619 (3)	0.0455 (7)
H1	0.3648	0.4273	0.9825	0.055*
O2	0.38327 (19)	0.8441 (5)	1.04241 (19)	0.0546 (6)
C3	0.3280 (3)	0.9021 (7)	1.1363 (3)	0.0518 (8)
O3	0.3786 (3)	1.0867 (6)	1.2155 (2)	0.0788 (7)
C4	0.2033 (3)	0.7134 (8)	1.1221 (2)	0.0522 (8)
H4A	0.1233	0.8252	1.1265	0.063*
H4B	0.2263	0.5674	1.1896	0.063*
O6	0.07106 (19)	0.7479 (6)	0.89421 (18)	0.0656 (7)
C5	0.1713 (3)	0.5796 (7)	0.9901 (3)	0.0459 (7)
H5	0.1407	0.3790	0.9887	0.055*
C7	0.1203 (3)	0.8206 (7)	0.7894 (3)	0.0452 (7)
H7	0.1309	1.0299	0.7865	0.054*
C8	0.2656 (3)	0.6782 (8)	0.8200 (3)	0.0530 (8)
H8A	0.2589	0.5060	0.7679	0.064*
H8B	0.3329	0.8095	0.8034	0.064*
C1'	0.0167 (3)	0.7196 (8)	0.6629 (3)	0.0487 (7)
H1A	0.0550	0.7489	0.5932	0.058*
H1B	−0.0025	0.5161	0.6677	0.058*
O2'	−0.1124 (2)	0.8846 (5)	0.63829 (18)	0.0533 (5)
C3'	−0.2165 (3)	0.8315 (7)	0.5261 (3)	0.0504 (7)
O3'	−0.2036 (3)	0.6670 (6)	0.4477 (2)	0.0807 (8)
C4'	−0.3452 (3)	1.0036 (8)	0.5127 (3)	0.0659 (10)
H4E	−0.3893	0.9331	0.5725	0.099*
H4D	−0.4104	0.9876	0.4252	0.099*
H4C	−0.3192	1.2017	0.5318	0.099*

	U11	U22	U33	U12	U13	U23
C1	0.0348 (13)	0.0492 (18)	0.0516 (16)	0.0035 (14)	0.0136 (12)	0.0035 (14)
O2	0.0410 (10)	0.0622 (14)	0.0599 (12)	−0.0120 (11)	0.0162 (9)	−0.0041 (11)
C3	0.0467 (17)	0.057 (2)	0.0405 (16)	0.0046 (16)	0.0004 (13)	0.0065 (15)
O3	0.0824 (16)	0.0760 (18)	0.0616 (14)	−0.0014 (15)	0.0029 (12)	−0.0152 (14)
C4	0.0471 (16)	0.067 (2)	0.0430 (15)	0.0067 (15)	0.0164 (12)	0.0106 (14)
O6	0.0410 (11)	0.116 (2)	0.0426 (11)	0.0232 (12)	0.0172 (9)	0.0155 (12)
C5	0.0432 (15)	0.0489 (17)	0.0472 (15)	−0.0005 (14)	0.0173 (12)	0.0039 (14)
C7	0.0463 (15)	0.0496 (19)	0.0414 (14)	−0.0019 (14)	0.0173 (12)	−0.0020 (14)
C8	0.0455 (16)	0.067 (2)	0.0514 (17)	0.0022 (15)	0.0227 (13)	−0.0015 (15)
C1'	0.0545 (17)	0.0462 (16)	0.0460 (15)	0.0030 (15)	0.0179 (13)	−0.0009 (14)
O2'	0.0481 (11)	0.0631 (14)	0.0418 (11)	0.0103 (11)	0.0062 (9)	−0.0075 (10)
C3'	0.0558 (17)	0.0529 (19)	0.0402 (16)	−0.0051 (15)	0.0131 (14)	0.0017 (15)
O3'	0.0845 (17)	0.088 (2)	0.0559 (13)	0.0072 (14)	0.0055 (12)	−0.0251 (15)
C4'	0.0491 (18)	0.084 (3)	0.054 (2)	0.0063 (16)	0.0039 (15)	0.0061 (17)

C1—O2	1.453 (3)	C7—C8	1.530 (4)
C1—C8	1.498 (4)	C7—H7	0.9800
C1—C5	1.518 (4)	C8—H8A	0.9700
C1—H1	0.9800	C8—H8B	0.9700
O2—C3	1.345 (4)	C1'—O2'	1.448 (3)
C3—O3	1.201 (4)	C1'—H1A	0.9700
C3—C4	1.490 (4)	C1'—H1B	0.9700
C4—C5	1.500 (4)	O2'—C3'	1.335 (3)
C4—H4A	0.9700	C3'—O3'	1.186 (4)
C4—H4B	0.9700	C3'—C4'	1.481 (4)
O6—C5	1.415 (3)	C4'—H4E	0.9600
O6—C7	1.430 (3)	C4'—H4D	0.9600
C5—H5	0.9800	C4'—H4C	0.9600
C7—C1'	1.494 (4)
O2—C1—C8	111.3 (2)	O6—C7—H7	109.3
O2—C1—C5	104.6 (2)	C1'—C7—H7	109.3
C8—C1—C5	105.0 (2)	C8—C7—H7	109.3
O2—C1—H1	111.8	C1—C8—C7	104.3 (2)
C8—C1—H1	111.8	C1—C8—H8A	110.9
C5—C1—H1	111.8	C7—C8—H8A	110.9
C3—O2—C1	110.8 (2)	C1—C8—H8B	110.9
O3—C3—O2	120.5 (3)	C7—C8—H8B	110.9
O3—C3—C4	129.1 (3)	H8A—C8—H8B	108.9
O2—C3—C4	110.4 (3)	O2'—C1'—C7	107.6 (2)
C3—C4—C5	104.1 (2)	O2'—C1'—H1A	110.2
C3—C4—H4A	110.9	C7—C1'—H1A	110.2
C5—C4—H4A	110.9	O2'—C1'—H1B	110.2
C3—C4—H4B	110.9	C7—C1'—H1B	110.2
C5—C4—H4B	110.9	H1A—C1'—H1B	108.5
H4A—C4—H4B	109.0	C3'—O2'—C1'	116.4 (2)
C5—O6—C7	111.7 (2)	O3'—C3'—O2'	122.5 (3)
O6—C5—C4	110.4 (3)	O3'—C3'—C4'	125.4 (3)
O6—C5—C1	105.9 (2)	O2'—C3'—C4'	112.0 (3)
C4—C5—C1	104.3 (2)	C3'—C4'—H4E	109.5
O6—C5—H5	111.9	C3'—C4'—H4D	109.5
C4—C5—H5	111.9	H4E—C4'—H4D	109.5
C1—C5—H5	111.9	C3'—C4'—H4C	109.5
O6—C7—C1'	110.1 (2)	H4E—C4'—H4C	109.5
O6—C7—C8	106.5 (2)	H4D—C4'—H4C	109.5
C1'—C7—C8	112.2 (2)
C8—C1—O2—C3	130.1 (2)	C8—C1—C5—C4	−141.0 (3)
C5—C1—O2—C3	17.2 (3)	C5—O6—C7—C1'	123.3 (3)
C1—O2—C3—O3	177.4 (3)	C5—O6—C7—C8	1.4 (4)
C1—O2—C3—C4	−3.3 (3)	O2—C1—C8—C7	−87.8 (3)
O3—C3—C4—C5	167.1 (3)	C5—C1—C8—C7	24.8 (3)
O2—C3—C4—C5	−12.1 (3)	O6—C7—C8—C1	−16.7 (3)
C7—O6—C5—C4	126.7 (3)	C1'—C7—C8—C1	−137.3 (3)
C7—O6—C5—C1	14.4 (3)	O6—C7—C1'—O2'	66.4 (3)
C3—C4—C5—O6	−91.7 (3)	C8—C7—C1'—O2'	−175.2 (2)
C3—C4—C5—C1	21.6 (3)	C7—C1'—O2'—C3'	177.6 (2)
O2—C1—C5—O6	92.8 (3)	C1'—O2'—C3'—O3'	−2.9 (4)
C8—C1—C5—O6	−24.5 (3)	C1'—O2'—C3'—C4'	178.0 (3)
O2—C1—C5—C4	−23.7 (3)