(3S,3aS,6R,6aR)-2-Oxohexa-hydro-furo[3,2-b]furan-3,6-diyl dibenzoate.

The title compound, C20H16O7, contains a cis-fused γ-lactone tetra-hydro-furan ring system functionalized with two benzo-yloxy groups. Both rings adopt an envelope conformation. The mol-ecule assumes an elongated shape and exibits non-crystallographic C 2 symmetry. The benzo-yloxy groups are almost planar [maximum deviations of 0.0491 (15) and 0.0336 (17) Å for the O atoms] and their mean planes are inclined to one another by 16.51 (4)°. The crystal packing features weak C-H⋯O inter-actions. The aryl groups of adjacent mol-ecules are parallel shifted with face-to-face contacts and a shortest inter-molecular C⋯C distance of 3.482 (4) Å.

Related literature

For the use of carbohydrate in the synthesis of complex natural chiral substances, see: Hanessian (1993 ▶). For mannitol as chiral reagent and as a precursor of biologically active derivatives, see: Masaki et al. (1999 ▶); Lohray et al. (1999 ▶). For oxidative processes mediated by transition metal oxo-species, see: De Champdorè et al.. (1998 ▶); Piccialli (2007 ▶); Piccialli, Oliviero et al. (2013 ▶); Piccialli, Tuzi et al. (2013 ▶). For the catalytic use of chloro­chromato­periodate, see: Piccialli, D’Errico et al. (2013 ▶); Piccialli et al. (2012 ▶). For the synthesis of the precursor, see: Hockett et al. (1946 ▶).

Experimental

Crystal data

C20H16O7

M = 368.33

Orthorhombic,

a = 7.4870 (7) Å

b = 10.2050 (14) Å

c = 22.232 (2) Å

V = 1698.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 173 K

0.50 × 0.40 × 0.08 mm

Data collection

Bruker–Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.947, T max = 0.991

8078 measured reflections

2108 independent reflections

1797 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.078

S = 1.07

2108 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.19 e Å−3

Data collection: COLLECT (Nonius, 1999 ▶); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000 ▶); data reduction: EVALCCD (Duisenberg et al., 2003 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681302391X/zp2007sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681302391X/zp2007Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681302391X/zp2007Isup3.cml

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

C20H16O7	F(000) = 768
Mr = 368.33	Dx = 1.440 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 119 reflections
a = 7.4870 (7) Å	θ = 3.8–22.3°
b = 10.2050 (14) Å	µ = 0.11 mm−1
c = 22.232 (2) Å	T = 173 K
V = 1698.6 (3) Å3	Block, white
Z = 4	0.50 × 0.40 × 0.08 mm

Bruker–Nonius KappaCCD diffractometer	2108 independent reflections
Radiation source: normal-focus sealed tube	1797 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 9 pixels mm-1	θmax = 27.5°, θmin = 3.3°
CCD rotation images, thick slices scans	h = −9→5
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −12→13
Tmin = 0.947, Tmax = 0.991	l = −28→28
8078 measured reflections

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0383P)2 + 0.2376P] where P = (Fo2 + 2Fc2)/3
2108 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.16 e Å−3
0 restraints	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	0.7473 (3)	0.5893 (2)	0.57766 (9)	0.0274 (5)
C2	0.7006 (3)	0.45523 (19)	0.55289 (9)	0.0256 (5)
H2	0.7605	0.4416	0.5132	0.031*
C3	0.5016 (3)	0.46156 (19)	0.54459 (9)	0.0248 (5)
H3	0.4587	0.4085	0.5096	0.030*
C4	0.4649 (3)	0.60851 (19)	0.53746 (9)	0.0260 (5)
H4	0.4546	0.6345	0.4942	0.031*
C5	0.2879 (3)	0.6297 (2)	0.57190 (9)	0.0276 (5)
H5	0.1904	0.6574	0.5439	0.033*
C6	0.2490 (3)	0.4957 (2)	0.59859 (11)	0.0324 (5)
H6A	0.2004	0.5045	0.6398	0.039*
H6B	0.1612	0.4480	0.5735	0.039*
C7	0.7436 (3)	0.2341 (2)	0.57841 (9)	0.0277 (5)
C8	0.8031 (3)	0.1437 (2)	0.62616 (9)	0.0267 (5)
C9	0.7809 (3)	0.0097 (2)	0.61663 (11)	0.0350 (6)
H9	0.7348	−0.0215	0.5795	0.042*
C10	0.8264 (4)	−0.0772 (2)	0.66150 (12)	0.0425 (7)
H10	0.8131	−0.1687	0.6551	0.051*
C11	0.8912 (4)	−0.0320 (2)	0.71559 (12)	0.0425 (6)
H11	0.9204	−0.0925	0.7465	0.051*
C12	0.9142 (4)	0.1007 (2)	0.72531 (11)	0.0369 (6)
H12	0.9591	0.1314	0.7627	0.044*
C13	0.8714 (3)	0.1880 (2)	0.68034 (10)	0.0320 (5)
H13	0.8889	0.2793	0.6865	0.038*
C14	0.3130 (3)	0.8490 (2)	0.60421 (9)	0.0271 (5)
C15	0.3326 (3)	0.9379 (2)	0.65625 (9)	0.0256 (5)
C16	0.3399 (3)	1.0720 (2)	0.64556 (10)	0.0330 (5)
H16	0.3290	1.1049	0.6058	0.040*
C17	0.3629 (4)	1.1568 (2)	0.69311 (11)	0.0381 (6)
H17	0.3679	1.2485	0.6860	0.046*
C18	0.3788 (4)	1.1098 (2)	0.75109 (10)	0.0382 (6)
H18	0.3943	1.1689	0.7837	0.046*
C19	0.3722 (4)	0.9768 (2)	0.76157 (10)	0.0349 (6)
H19	0.3843	0.9443	0.8014	0.042*
C20	0.3479 (3)	0.8907 (2)	0.71458 (9)	0.0282 (5)
H20	0.3418	0.7992	0.7221	0.034*
O1	0.6118 (2)	0.67337 (13)	0.56690 (6)	0.0276 (4)
O2	0.4158 (2)	0.42772 (14)	0.59961 (6)	0.0294 (4)
O3	0.7629 (2)	0.36076 (13)	0.59524 (6)	0.0272 (4)
O4	0.6838 (3)	0.20348 (14)	0.53016 (7)	0.0386 (4)
O5	0.3071 (2)	0.72131 (13)	0.62053 (6)	0.0268 (4)
O6	0.3053 (3)	0.88274 (15)	0.55255 (6)	0.0438 (5)
O7	0.8798 (2)	0.62237 (15)	0.60320 (8)	0.0403 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0279 (12)	0.0252 (11)	0.0292 (11)	−0.0009 (10)	0.0049 (10)	−0.0007 (8)
C2	0.0339 (14)	0.0222 (10)	0.0206 (9)	0.0002 (10)	0.0014 (9)	−0.0017 (8)
C3	0.0318 (13)	0.0251 (11)	0.0177 (9)	−0.0011 (10)	−0.0012 (9)	−0.0012 (8)
C4	0.0293 (13)	0.0264 (11)	0.0221 (10)	−0.0009 (10)	−0.0022 (9)	−0.0007 (8)
C5	0.0300 (13)	0.0289 (11)	0.0239 (10)	0.0003 (10)	−0.0025 (10)	−0.0022 (9)
C6	0.0274 (13)	0.0300 (12)	0.0397 (12)	−0.0024 (10)	0.0035 (11)	−0.0020 (9)
C7	0.0276 (12)	0.0250 (11)	0.0304 (11)	0.0039 (10)	0.0073 (10)	−0.0055 (8)
C8	0.0243 (12)	0.0254 (11)	0.0304 (10)	0.0043 (9)	0.0051 (10)	−0.0006 (9)
C9	0.0356 (15)	0.0260 (12)	0.0434 (13)	0.0029 (11)	0.0049 (12)	−0.0042 (9)
C10	0.0460 (17)	0.0242 (12)	0.0572 (16)	0.0052 (12)	0.0121 (14)	0.0036 (11)
C11	0.0402 (15)	0.0370 (13)	0.0504 (14)	0.0098 (12)	0.0072 (14)	0.0157 (12)
C12	0.0339 (15)	0.0401 (13)	0.0368 (12)	0.0060 (12)	−0.0029 (11)	0.0037 (10)
C13	0.0300 (13)	0.0286 (12)	0.0373 (12)	0.0045 (10)	−0.0009 (11)	0.0006 (9)
C14	0.0267 (13)	0.0269 (11)	0.0278 (10)	0.0039 (10)	−0.0028 (10)	0.0047 (9)
C15	0.0216 (12)	0.0292 (11)	0.0260 (10)	0.0011 (9)	0.0022 (9)	0.0012 (8)
C16	0.0365 (15)	0.0301 (11)	0.0323 (11)	−0.0007 (11)	0.0047 (10)	0.0066 (9)
C17	0.0419 (16)	0.0269 (11)	0.0455 (13)	−0.0077 (11)	0.0102 (12)	−0.0020 (10)
C18	0.0389 (15)	0.0370 (13)	0.0388 (12)	−0.0091 (12)	0.0047 (12)	−0.0110 (10)
C19	0.0364 (15)	0.0432 (13)	0.0252 (10)	−0.0033 (12)	0.0007 (10)	−0.0004 (10)
C20	0.0284 (13)	0.0292 (11)	0.0270 (10)	−0.0002 (10)	0.0008 (9)	0.0040 (9)
O1	0.0274 (9)	0.0222 (7)	0.0332 (8)	−0.0002 (7)	0.0008 (7)	−0.0023 (6)
O2	0.0310 (9)	0.0285 (7)	0.0289 (7)	−0.0023 (7)	0.0029 (7)	0.0048 (6)
O3	0.0341 (9)	0.0211 (7)	0.0263 (7)	0.0024 (6)	−0.0015 (7)	−0.0005 (6)
O4	0.0540 (12)	0.0322 (8)	0.0297 (8)	0.0067 (8)	−0.0043 (8)	−0.0092 (6)
O5	0.0332 (9)	0.0238 (7)	0.0233 (7)	0.0034 (7)	−0.0001 (7)	−0.0001 (6)
O6	0.0734 (14)	0.0335 (8)	0.0245 (7)	0.0041 (9)	−0.0101 (9)	0.0054 (6)
O7	0.0302 (10)	0.0341 (9)	0.0568 (10)	−0.0025 (8)	−0.0076 (9)	−0.0079 (8)

C1—O7	1.191 (3)	C9—C10	1.377 (3)
C1—O1	1.350 (3)	C9—H9	0.9500
C1—C2	1.516 (3)	C10—C11	1.376 (4)
C2—O3	1.426 (2)	C10—H10	0.9500
C2—C3	1.502 (3)	C11—C12	1.381 (4)
C2—H2	1.0000	C11—H11	0.9500
C3—O2	1.424 (2)	C12—C13	1.377 (3)
C3—C4	1.533 (3)	C12—H12	0.9500
C3—H3	1.0000	C13—H13	0.9500
C4—O1	1.441 (3)	C14—O6	1.200 (2)
C4—C5	1.545 (3)	C14—O5	1.353 (2)
C4—H4	1.0000	C14—C15	1.477 (3)
C5—O5	1.436 (2)	C15—C20	1.388 (3)
C5—C6	1.519 (3)	C15—C16	1.390 (3)
C5—H5	1.0000	C16—C17	1.377 (3)
C6—O2	1.428 (3)	C16—H16	0.9500
C6—H6A	0.9900	C17—C18	1.381 (3)
C6—H6B	0.9900	C17—H17	0.9500
C7—O4	1.204 (3)	C18—C19	1.378 (3)
C7—O3	1.354 (2)	C18—H18	0.9500
C7—C8	1.475 (3)	C19—C20	1.377 (3)
C8—C13	1.385 (3)	C19—H19	0.9500
C8—C9	1.394 (3)	C20—H20	0.9500
O7—C1—O1	121.98 (19)	C10—C9—H9	120.3
O7—C1—C2	128.4 (2)	C8—C9—H9	120.3
O1—C1—C2	109.61 (19)	C11—C10—C9	120.3 (2)
O3—C2—C3	115.75 (18)	C11—C10—H10	119.9
O3—C2—C1	107.13 (16)	C9—C10—H10	119.9
C3—C2—C1	103.58 (18)	C10—C11—C12	120.6 (2)
O3—C2—H2	110.0	C10—C11—H11	119.7
C3—C2—H2	110.0	C12—C11—H11	119.7
C1—C2—H2	110.0	C13—C12—C11	119.5 (2)
O2—C3—C2	109.37 (17)	C13—C12—H12	120.3
O2—C3—C4	104.18 (16)	C11—C12—H12	120.3
C2—C3—C4	103.46 (18)	C12—C13—C8	120.4 (2)
O2—C3—H3	113.0	C12—C13—H13	119.8
C2—C3—H3	113.0	C8—C13—H13	119.8
C4—C3—H3	113.0	O6—C14—O5	122.07 (19)
O1—C4—C3	105.38 (17)	O6—C14—C15	125.32 (19)
O1—C4—C5	111.41 (15)	O5—C14—C15	112.60 (16)
C3—C4—C5	103.87 (17)	C20—C15—C16	119.9 (2)
O1—C4—H4	111.9	C20—C15—C14	121.81 (18)
C3—C4—H4	111.9	C16—C15—C14	118.32 (19)
C5—C4—H4	111.9	C17—C16—C15	119.5 (2)
O5—C5—C6	108.12 (16)	C17—C16—H16	120.2
O5—C5—C4	112.23 (18)	C15—C16—H16	120.2
C6—C5—C4	103.39 (18)	C16—C17—C18	120.6 (2)
O5—C5—H5	110.9	C16—C17—H17	119.7
C6—C5—H5	110.9	C18—C17—H17	119.7
C4—C5—H5	110.9	C19—C18—C17	119.8 (2)
O2—C6—C5	106.02 (19)	C19—C18—H18	120.1
O2—C6—H6A	110.5	C17—C18—H18	120.1
C5—C6—H6A	110.5	C20—C19—C18	120.3 (2)
O2—C6—H6B	110.5	C20—C19—H19	119.8
C5—C6—H6B	110.5	C18—C19—H19	119.8
H6A—C6—H6B	108.7	C19—C20—C15	119.9 (2)
O4—C7—O3	122.27 (19)	C19—C20—H20	120.0
O4—C7—C8	126.27 (19)	C15—C20—H20	120.0
O3—C7—C8	111.46 (17)	C1—O1—C4	111.24 (15)
C13—C8—C9	119.8 (2)	C3—O2—C6	105.25 (16)
C13—C8—C7	122.24 (19)	C7—O3—C2	115.35 (16)
C9—C8—C7	117.9 (2)	C14—O5—C5	115.34 (15)
C10—C9—C8	119.5 (2)
O7—C1—C2—O3	39.4 (3)	C7—C8—C13—C12	175.6 (2)
O1—C1—C2—O3	−140.40 (18)	O6—C14—C15—C20	−177.3 (3)
O7—C1—C2—C3	162.3 (2)	O5—C14—C15—C20	1.7 (3)
O1—C1—C2—C3	−17.6 (2)	O6—C14—C15—C16	1.2 (4)
O3—C2—C3—O2	31.1 (2)	O5—C14—C15—C16	−179.9 (2)
C1—C2—C3—O2	−85.81 (19)	C20—C15—C16—C17	0.2 (4)
O3—C2—C3—C4	141.68 (16)	C14—C15—C16—C17	−178.3 (2)
C1—C2—C3—C4	24.7 (2)	C15—C16—C17—C18	0.0 (4)
O2—C3—C4—O1	90.05 (19)	C16—C17—C18—C19	0.2 (4)
C2—C3—C4—O1	−24.3 (2)	C17—C18—C19—C20	−0.6 (4)
O2—C3—C4—C5	−27.2 (2)	C18—C19—C20—C15	0.9 (4)
C2—C3—C4—C5	−141.55 (16)	C16—C15—C20—C19	−0.6 (4)
O1—C4—C5—O5	7.1 (2)	C14—C15—C20—C19	177.8 (2)
C3—C4—C5—O5	120.05 (18)	O7—C1—O1—C4	−177.88 (19)
O1—C4—C5—C6	−109.20 (19)	C2—C1—O1—C4	2.0 (2)
C3—C4—C5—C6	3.8 (2)	C3—C4—O1—C1	14.2 (2)
O5—C5—C6—O2	−98.2 (2)	C5—C4—O1—C1	126.26 (18)
C4—C5—C6—O2	20.9 (2)	C2—C3—O2—C6	151.80 (17)
O4—C7—C8—C13	179.6 (3)	C4—C3—O2—C6	41.7 (2)
O3—C7—C8—C13	−0.8 (3)	C5—C6—O2—C3	−39.8 (2)
O4—C7—C8—C9	−3.5 (4)	O4—C7—O3—C2	2.5 (3)
O3—C7—C8—C9	176.2 (2)	C8—C7—O3—C2	−177.11 (18)
C13—C8—C9—C10	0.4 (4)	C3—C2—O3—C7	69.5 (2)
C7—C8—C9—C10	−176.7 (2)	C1—C2—O3—C7	−175.54 (18)
C8—C9—C10—C11	0.8 (4)	O6—C14—O5—C5	−1.1 (3)
C9—C10—C11—C12	−1.1 (4)	C15—C14—O5—C5	179.92 (18)
C10—C11—C12—C13	0.1 (4)	C6—C5—O5—C14	−169.6 (2)
C11—C12—C13—C8	1.1 (4)	C4—C5—O5—C14	77.1 (2)
C9—C8—C13—C12	−1.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O6i	1.00	2.34	2.974 (2)	121
C3—H3···O4ii	1.00	2.51	3.356 (3)	142
C10—H10···O7iii	0.95	2.48	3.353 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O6i	1.00	2.34	2.974 (2)	121
C3—H3⋯O4ii	1.00	2.51	3.356 (3)	142
C10—H10⋯O7iii	0.95	2.48	3.353 (3)	154

Symmetry codes: (i) ; (ii) ; (iii) .