3,5-Di-O-benzoyl-1,2-O-isopropyl-idene-α-d-ribo-hexos-3-ulo-1,4:3,6-difuran-ose.

The title compound, C(23)H(22)O(8), is a binary benzoyl ester whose nucleus consists of a fused system made up of a methyl-enedi-oxy ring and two tetra-hydro-furan rings. One of the benzoyl ester groups is attached at the junction of the two tetra-hydro-furan rings. The other is attached to the outer tetra-furan ring. Both the benzoyl ester groups are in an axial conformation with respect to the outer tetrhydro-furan ring. In the crystal, mol-ecules are linked by two weak C-H⋯O hydrogen bonds, forming a chain running parallel to the a axis.

Related literature

For details of the synthesis and absolute configuration of the nucleus, see: Tronchet & Bourgeois (1971 ▶). For applications of the nucleus, see: Xavier et al. (2009 ▶); Rajwanshi et al. (1999 ▶). For structure of a bicyclo-glycosyl compound, see: Zhang et al. (2011 ▶).

Experimental

Crystal data

C23H22O8

M = 426.41

Orthorhombic,

a = 6.05837 (10) Å

b = 8.33827 (14) Å

c = 40.9992 (7) Å

V = 2071.13 (6) Å3

Z = 4

Cu Kα radiation

μ = 0.87 mm−1

T = 291 K

0.30 × 0.30 × 0.25 mm

Data collection

Agilent Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.780, T max = 0.812

10556 measured reflections

2421 independent reflections

2335 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.094

S = 1.06

2421 reflections

282 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811024317/lw2067sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024317/lw2067Isup2.hkl

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

C23H22O8	Dx = 1.367 Mg m−3
Mr = 426.41	Melting point = 459–460 K
Orthorhombic, P212121	Cu Kα radiation, λ = 1.5418 Å
a = 6.05837 (10) Å	Cell parameters from 5890 reflections
b = 8.33827 (14) Å	θ = 3.2–72.3°
c = 40.9992 (7) Å	µ = 0.87 mm−1
V = 2071.13 (6) Å3	T = 291 K
Z = 4	Prism, colourless
F(000) = 896	0.30 × 0.30 × 0.25 mm

Agilent Xcalibur Eos Gemini diffractometer	2421 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2335 reflections with I > 2σ(I)
graphite	Rint = 0.026
Detector resolution: 16.2312 pixels mm-1	θmax = 72.3°, θmin = 4.3°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −9→10
Tmin = 0.780, Tmax = 0.812	l = −21→50
10556 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0643P)2 + 0.1182P] where P = (Fo2 + 2Fc2)/3
2421 reflections	(Δ/σ)max = 0.001
282 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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.

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
O1	0.7379 (3)	1.23548 (17)	0.88731 (3)	0.0556 (4)
O2	0.8454 (3)	1.07286 (15)	0.84526 (3)	0.0553 (4)
O3	0.7285 (2)	0.70109 (16)	0.88507 (3)	0.0458 (3)
O4	0.4603 (2)	1.04625 (17)	0.88971 (3)	0.0460 (3)
O5	0.4346 (2)	0.82295 (17)	0.93608 (3)	0.0462 (3)
O6	0.1023 (3)	0.9393 (3)	0.94092 (4)	0.0694 (5)
O7	0.6458 (2)	0.78758 (16)	0.83253 (3)	0.0396 (3)
O8	1.0139 (2)	0.75343 (19)	0.82694 (3)	0.0477 (3)
C1	0.6881 (4)	1.0796 (2)	0.89615 (4)	0.0436 (4)
H1	0.7261	1.0586	0.9190	0.052*
C2	0.8210 (3)	0.9737 (2)	0.87294 (4)	0.0388 (3)
H2	0.9629	0.9401	0.8822	0.047*
C3	0.6676 (3)	0.8329 (2)	0.86608 (4)	0.0359 (3)
C4	0.4365 (3)	0.8886 (2)	0.87778 (4)	0.0395 (4)
H4	0.3302	0.8855	0.8598	0.047*
C5	0.3748 (4)	0.7633 (2)	0.90435 (4)	0.0469 (4)
H5	0.2192	0.7316	0.9032	0.056*
C6	0.5277 (4)	0.6267 (2)	0.89661 (5)	0.0576 (6)
H6B	0.5562	0.5628	0.9159	0.069*
H6A	0.4647	0.5581	0.8799	0.069*
C7	0.8226 (4)	1.2368 (2)	0.85457 (4)	0.0457 (4)
C8	0.6599 (5)	1.3136 (4)	0.83165 (6)	0.0666 (6)
H8C	0.6363	1.4231	0.8380	0.100*
H8B	0.5225	1.2564	0.8325	0.100*
H8A	0.7170	1.3102	0.8098	0.100*
C9	1.0429 (4)	1.3199 (3)	0.85511 (7)	0.0701 (6)
H9B	1.1420	1.2623	0.8691	0.105*
H9C	1.0248	1.4273	0.8631	0.105*
H9A	1.1025	1.3232	0.8334	0.105*
C10	0.8314 (3)	0.7426 (2)	0.81616 (4)	0.0361 (3)
C11	0.7740 (3)	0.6775 (2)	0.78333 (4)	0.0369 (3)
C12	0.9415 (4)	0.6641 (3)	0.76038 (4)	0.0491 (4)
H12	1.0828	0.7009	0.7652	0.059*
C13	0.8968 (4)	0.5954 (3)	0.73032 (5)	0.0582 (5)
H13	1.0080	0.5875	0.7148	0.070*
C14	0.6894 (5)	0.5390 (3)	0.72342 (5)	0.0623 (6)
H14	0.6609	0.4922	0.7033	0.075*
C15	0.5228 (4)	0.5511 (3)	0.74619 (6)	0.0621 (6)
H15	0.3831	0.5112	0.7415	0.075*
C16	0.5637 (3)	0.6229 (3)	0.77623 (5)	0.0479 (4)
H16	0.4507	0.6341	0.7914	0.057*
C17	0.2826 (3)	0.9126 (3)	0.95157 (4)	0.0477 (4)
C18	0.3653 (4)	0.9719 (2)	0.98356 (4)	0.0475 (4)
C19	0.5728 (5)	0.9336 (3)	0.99530 (5)	0.0605 (5)
H19	0.6685	0.8707	0.9830	0.073*
C20	0.6362 (6)	0.9909 (4)	1.02587 (6)	0.0791 (8)
H20	0.7746	0.9653	1.0342	0.095*
C21	0.4942 (7)	1.0852 (4)	1.04379 (6)	0.0831 (9)
H21	0.5379	1.1235	1.0641	0.100*
C22	0.2893 (6)	1.1233 (4)	1.03201 (6)	0.0788 (8)
H22	0.1942	1.1865	1.0443	0.095*
C23	0.2242 (5)	1.0674 (3)	1.00179 (5)	0.0606 (6)
H23	0.0856	1.0939	0.9936	0.073*

	U11	U22	U33	U12	U13	U23
O1	0.0844 (11)	0.0392 (6)	0.0433 (7)	−0.0017 (7)	0.0146 (7)	−0.0098 (5)
O2	0.0874 (11)	0.0392 (6)	0.0392 (6)	−0.0010 (7)	0.0204 (7)	−0.0044 (5)
O3	0.0562 (8)	0.0416 (6)	0.0396 (6)	0.0110 (6)	0.0062 (6)	0.0031 (5)
O4	0.0521 (7)	0.0434 (6)	0.0424 (6)	0.0123 (6)	0.0078 (6)	−0.0030 (5)
O5	0.0523 (7)	0.0552 (7)	0.0311 (5)	0.0076 (6)	0.0072 (5)	−0.0005 (5)
O6	0.0528 (8)	0.1047 (14)	0.0508 (8)	0.0200 (10)	−0.0035 (7)	−0.0178 (9)
O7	0.0390 (6)	0.0500 (6)	0.0298 (5)	0.0027 (5)	0.0007 (4)	−0.0102 (5)
O8	0.0401 (6)	0.0607 (8)	0.0424 (6)	0.0043 (6)	−0.0024 (5)	−0.0143 (6)
C1	0.0598 (10)	0.0410 (8)	0.0299 (7)	0.0052 (8)	0.0020 (8)	−0.0058 (7)
C2	0.0439 (8)	0.0417 (8)	0.0307 (7)	0.0037 (7)	0.0010 (7)	−0.0056 (6)
C3	0.0413 (8)	0.0388 (8)	0.0275 (7)	0.0060 (7)	−0.0009 (6)	−0.0032 (6)
C4	0.0408 (8)	0.0491 (9)	0.0286 (7)	0.0049 (8)	0.0027 (6)	−0.0056 (7)
C5	0.0541 (10)	0.0506 (9)	0.0360 (8)	−0.0012 (9)	0.0097 (7)	−0.0050 (7)
C6	0.0780 (15)	0.0425 (9)	0.0523 (10)	0.0011 (10)	0.0217 (11)	−0.0001 (8)
C7	0.0545 (10)	0.0393 (8)	0.0435 (9)	0.0008 (9)	0.0076 (8)	−0.0036 (7)
C8	0.0701 (15)	0.0739 (14)	0.0559 (12)	0.0172 (13)	−0.0006 (12)	−0.0003 (11)
C9	0.0634 (14)	0.0671 (14)	0.0800 (15)	−0.0100 (13)	0.0069 (12)	−0.0134 (13)
C10	0.0408 (8)	0.0361 (7)	0.0315 (7)	0.0021 (7)	0.0025 (7)	−0.0039 (6)
C11	0.0454 (9)	0.0364 (7)	0.0290 (6)	0.0051 (7)	0.0004 (6)	−0.0020 (6)
C12	0.0515 (10)	0.0567 (10)	0.0391 (8)	0.0000 (9)	0.0066 (8)	−0.0065 (8)
C13	0.0734 (14)	0.0667 (12)	0.0346 (8)	0.0088 (12)	0.0122 (9)	−0.0097 (9)
C14	0.0805 (15)	0.0693 (13)	0.0370 (8)	0.0155 (13)	−0.0122 (10)	−0.0208 (9)
C15	0.0572 (12)	0.0734 (14)	0.0558 (11)	0.0064 (12)	−0.0127 (10)	−0.0247 (11)
C16	0.0473 (10)	0.0549 (10)	0.0414 (8)	0.0027 (9)	−0.0010 (8)	−0.0117 (8)
C17	0.0512 (11)	0.0564 (10)	0.0355 (8)	0.0069 (9)	0.0068 (8)	0.0003 (8)
C18	0.0607 (11)	0.0502 (9)	0.0315 (7)	0.0008 (9)	0.0058 (8)	0.0047 (7)
C19	0.0694 (13)	0.0703 (13)	0.0420 (9)	0.0067 (13)	−0.0031 (10)	0.0033 (9)
C20	0.091 (2)	0.0973 (19)	0.0493 (11)	−0.0043 (17)	−0.0210 (13)	0.0079 (13)
C21	0.123 (3)	0.0871 (18)	0.0391 (10)	−0.017 (2)	−0.0067 (14)	−0.0085 (12)
C22	0.114 (2)	0.0735 (15)	0.0488 (11)	−0.0001 (17)	0.0131 (15)	−0.0166 (12)
C23	0.0725 (14)	0.0620 (12)	0.0473 (10)	0.0087 (12)	0.0082 (10)	−0.0061 (9)

O1—C1	1.382 (2)	C8—H8A	0.9600
O1—C7	1.437 (2)	C9—H9B	0.9600
O2—C2	1.412 (2)	C9—H9C	0.9600
O2—C7	1.426 (2)	C9—H9A	0.9600
O3—C3	1.397 (2)	C10—C11	1.492 (2)
O3—C6	1.445 (3)	C11—C16	1.384 (3)
O4—C4	1.410 (2)	C11—C12	1.389 (3)
O4—C1	1.432 (3)	C12—C13	1.386 (3)
O5—C17	1.346 (2)	C12—H12	0.9300
O5—C5	1.439 (2)	C13—C14	1.371 (4)
O6—C17	1.197 (3)	C13—H13	0.9300
O7—C10	1.362 (2)	C14—C15	1.378 (4)
O7—C3	1.4328 (17)	C14—H14	0.9300
O8—C10	1.194 (2)	C15—C16	1.392 (3)
C1—C2	1.528 (2)	C15—H15	0.9300
C1—H1	0.9800	C16—H16	0.9300
C2—C3	1.523 (3)	C17—C18	1.489 (3)
C2—H2	0.9800	C18—C19	1.383 (3)
C3—C4	1.551 (2)	C18—C23	1.387 (3)
C4—C5	1.555 (3)	C19—C20	1.395 (3)
C4—H4	0.9800	C19—H19	0.9300
C5—C6	1.502 (3)	C20—C21	1.378 (5)
C5—H5	0.9800	C20—H20	0.9300
C6—H6B	0.9700	C21—C22	1.369 (5)
C6—H6A	0.9700	C21—H21	0.9300
C7—C9	1.503 (3)	C22—C23	1.381 (3)
C7—C8	1.505 (3)	C22—H22	0.9300
C8—H8C	0.9600	C23—H23	0.9300
C8—H8B	0.9600
C1—O1—C7	109.27 (13)	C7—C8—H8A	109.5
C2—O2—C7	109.65 (13)	H8C—C8—H8A	109.5
C3—O3—C6	107.35 (16)	H8B—C8—H8A	109.5
C4—O4—C1	110.09 (14)	C7—C9—H9B	109.5
C17—O5—C5	116.50 (16)	C7—C9—H9C	109.5
C10—O7—C3	118.02 (13)	H9B—C9—H9C	109.5
O1—C1—O4	110.15 (17)	C7—C9—H9A	109.5
O1—C1—C2	105.39 (15)	H9B—C9—H9A	109.5
O4—C1—C2	106.30 (14)	H9C—C9—H9A	109.5
O1—C1—H1	111.6	O8—C10—O7	124.12 (14)
O4—C1—H1	111.6	O8—C10—C11	125.24 (15)
C2—C1—H1	111.6	O7—C10—C11	110.64 (14)
O2—C2—C3	111.52 (14)	C16—C11—C12	120.26 (16)
O2—C2—C1	102.53 (14)	C16—C11—C10	121.59 (15)
C3—C2—C1	103.82 (16)	C12—C11—C10	118.05 (17)
O2—C2—H2	112.7	C13—C12—C11	119.6 (2)
C3—C2—H2	112.7	C13—C12—H12	120.2
C1—C2—H2	112.7	C11—C12—H12	120.2
O3—C3—O7	110.60 (13)	C14—C13—C12	120.3 (2)
O3—C3—C2	110.03 (14)	C14—C13—H13	119.9
O7—C3—C2	115.89 (13)	C12—C13—H13	119.9
O3—C3—C4	107.55 (14)	C13—C14—C15	120.39 (18)
O7—C3—C4	107.02 (13)	C13—C14—H14	119.8
C2—C3—C4	105.26 (13)	C15—C14—H14	119.8
O4—C4—C3	107.09 (15)	C14—C15—C16	120.0 (2)
O4—C4—C5	114.09 (13)	C14—C15—H15	120.0
C3—C4—C5	103.45 (14)	C16—C15—H15	120.0
O4—C4—H4	110.6	C11—C16—C15	119.44 (19)
C3—C4—H4	110.6	C11—C16—H16	120.3
C5—C4—H4	110.6	C15—C16—H16	120.3
O5—C5—C6	107.33 (18)	O6—C17—O5	123.76 (18)
O5—C5—C4	109.90 (15)	O6—C17—C18	124.54 (19)
C6—C5—C4	102.30 (15)	O5—C17—C18	111.69 (17)
O5—C5—H5	112.3	C19—C18—C23	120.3 (2)
C6—C5—H5	112.3	C19—C18—C17	122.40 (19)
C4—C5—H5	112.3	C23—C18—C17	117.3 (2)
O3—C6—C5	105.23 (16)	C18—C19—C20	118.9 (3)
O3—C6—H6B	110.7	C18—C19—H19	120.5
C5—C6—H6B	110.7	C20—C19—H19	120.5
O3—C6—H6A	110.7	C21—C20—C19	120.2 (3)
C5—C6—H6A	110.7	C21—C20—H20	119.9
H6B—C6—H6A	108.8	C19—C20—H20	119.9
O2—C7—O1	106.09 (14)	C22—C21—C20	120.7 (2)
O2—C7—C9	111.09 (19)	C22—C21—H21	119.7
O1—C7—C9	107.87 (18)	C20—C21—H21	119.7
O2—C7—C8	107.70 (18)	C21—C22—C23	119.8 (3)
O1—C7—C8	110.62 (18)	C21—C22—H22	120.1
C9—C7—C8	113.3 (2)	C23—C22—H22	120.1
C7—C8—H8C	109.5	C22—C23—C18	120.1 (3)
C7—C8—H8B	109.5	C22—C23—H23	120.0
H8C—C8—H8B	109.5	C18—C23—H23	120.0
C7—O1—C1—O4	−93.88 (18)	O5—C5—C6—O3	−81.08 (19)
C7—O1—C1—C2	20.4 (2)	C4—C5—C6—O3	34.6 (2)
C4—O4—C1—O1	141.46 (13)	C2—O2—C7—O1	−11.8 (2)
C4—O4—C1—C2	27.76 (18)	C2—O2—C7—C9	105.2 (2)
C7—O2—C2—C3	133.74 (17)	C2—O2—C7—C8	−130.29 (19)
C7—O2—C2—C1	23.2 (2)	C1—O1—C7—O2	−6.4 (2)
O1—C1—C2—O2	−26.6 (2)	C1—O1—C7—C9	−125.5 (2)
O4—C1—C2—O2	90.33 (18)	C1—O1—C7—C8	110.2 (2)
O1—C1—C2—C3	−142.79 (15)	C3—O7—C10—O8	−7.7 (3)
O4—C1—C2—C3	−25.87 (18)	C3—O7—C10—C11	171.87 (13)
C6—O3—C3—O7	−91.18 (17)	O8—C10—C11—C16	159.8 (2)
C6—O3—C3—C2	139.50 (15)	O7—C10—C11—C16	−19.8 (2)
C6—O3—C3—C4	25.35 (17)	O8—C10—C11—C12	−16.5 (3)
C10—O7—C3—O3	−66.81 (19)	O7—C10—C11—C12	163.94 (17)
C10—O7—C3—C2	59.3 (2)	C16—C11—C12—C13	−0.1 (3)
C10—O7—C3—C4	176.32 (14)	C10—C11—C12—C13	176.24 (18)
O2—C2—C3—O3	149.85 (14)	C11—C12—C13—C14	−0.9 (3)
C1—C2—C3—O3	−100.44 (16)	C12—C13—C14—C15	0.5 (4)
O2—C2—C3—O7	23.5 (2)	C13—C14—C15—C16	0.9 (4)
C1—C2—C3—O7	133.17 (15)	C12—C11—C16—C15	1.5 (3)
O2—C2—C3—C4	−94.54 (16)	C10—C11—C16—C15	−174.7 (2)
C1—C2—C3—C4	15.16 (17)	C14—C15—C16—C11	−1.9 (4)
C1—O4—C4—C3	−17.61 (17)	C5—O5—C17—O6	2.7 (3)
C1—O4—C4—C5	96.22 (18)	C5—O5—C17—C18	−178.13 (16)
O3—C3—C4—O4	117.80 (14)	O6—C17—C18—C19	177.9 (2)
O7—C3—C4—O4	−123.34 (14)	O5—C17—C18—C19	−1.3 (3)
C2—C3—C4—O4	0.50 (16)	O6—C17—C18—C23	−1.5 (3)
O3—C3—C4—C5	−3.04 (17)	O5—C17—C18—C23	179.36 (19)
O7—C3—C4—C5	115.82 (15)	C23—C18—C19—C20	0.8 (4)
C2—C3—C4—C5	−120.34 (15)	C17—C18—C19—C20	−178.5 (2)
C17—O5—C5—C6	−161.55 (18)	C18—C19—C20—C21	−0.6 (4)
C17—O5—C5—C4	87.9 (2)	C19—C20—C21—C22	0.4 (5)
O4—C4—C5—O5	−21.2 (2)	C20—C21—C22—C23	−0.4 (5)
C3—C4—C5—O5	94.79 (16)	C21—C22—C23—C18	0.6 (4)
O4—C4—C5—C6	−134.95 (18)	C19—C18—C23—C22	−0.8 (4)
C3—C4—C5—C6	−18.98 (19)	C17—C18—C23—C22	178.6 (2)
C3—O3—C6—C5	−38.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O6i	0.98	2.55	3.2793 (17)	131
C4—H4···O8ii	0.98	2.59	3.4882 (16)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O6i	0.98	2.55	3.2793 (17)	131
C4—H4⋯O8ii	0.98	2.59	3.4882 (16)	153

Symmetry codes: (i) ; (ii) .