organic compounds
2,3-O-Isopropylidene-3-C-phenylerythrofuranose
aDiscipline of Chemistry, University of Adelaide, 5005 South Australia, Australia, bDiscipline of Wine and Horticulture, University of Adelaide, Waite Campus, Glen, Osmond 5064, South Australia, Australia, and cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: edward.tiekink@gmail.com
The title compound, C13H16O, comprises two fused five-membered rings. Each ring has an with the ether O atom in the furanose ring, and the CMe2 atom in the acetonide ring as the flap atoms. In the crystal, centrosymmetrically related molecules associate via hydroxy–ether O—H⋯O hydrogen bonds and the resulting dimers are linked into a supramolecular chain with a flattened topology via C—H⋯Ohydroxy contacts, and aligned in the a-axis direction.
Related literature
For the relevance and chemistry of systems related to the title compound, see: Pedersen et al. (2009); Robinson et al. (2006, 2009); Valente et al. (2009). For the reactions of Co(II) complexes with endoperoxides, see: Boyd et al. (1980); Sutbeyaz et al. (1988); Greatrex et al. (2003); Greatrex & Taylor (2005).
Experimental
Crystal data
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Refinement
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Data collection: CrystalClear (Rigaku/MSC, 2005); cell CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2009).
Supporting information
10.1107/S160053680904848X/sj2687sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053680904848X/sj2687Isup2.hkl
For full synthetic procedures and characterization data see Pedersen et al. (2009) and Robinson et al. (2009). To a stirred solution of Co(salen)2 (17 mg, 0.05 mmol) in THF (5 ml) at ambient temperature was added (3aR,7aS)-3a-phenyl-tetrahydro-2,2-dimethyl-[1,3]dioxolo[4,5-d][1,2]dioxine (501 mg, 2.12 mmol), and the reaction left to stir until complete by TLC (~16 h). All volatiles were removed in vacuo giving a crude mixture of regioisomers in a 40:60 ratio. The isomers were fully separated by flash
giving a combined total yield of 496 mg (99%). Compound (I) was isolated as a colourless solid (198 mg), and the pure material was recrystallized from a slowly evaporating 1:1 mixture of dichloromethane/heptane to give colourless prisms, m. pt. 424–425 K. The compound was found to exist solely in its cyclic hemi-acetal form(s) both as a solid indicated by IR (absence of carbonyl signal), and in CDCl3 solution which revealed a 90:10 ratio of anomers.Carbon-bound H-atoms were placed in calculated positions (C–H 0.95–1.00 Å) and were included in the
in the riding model approximation with Uiso(H) set to 1.2–1.5Ueq(C). The O–bound H-atom was located in a difference Fourier map and was refined with an O–H restraint of 0.840±0.001 Å, and with Uiso(H) = 1.5Ueq(O).Data collection: CrystalClear (Rigaku/MSC, 2005); cell
CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2009).C13H16O4 | Z = 2 |
Mr = 236.26 | F(000) = 252 |
Triclinic, P1 | Dx = 1.337 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71070 Å |
a = 5.716 (2) Å | Cell parameters from 2428 reflections |
b = 9.201 (4) Å | θ = 3.5–27.5° |
c = 11.871 (6) Å | µ = 0.10 mm−1 |
α = 89.76 (3)° | T = 173 K |
β = 78.72 (2)° | Prism, pale-yellow |
γ = 73.70 (2)° | 0.35 × 0.35 × 0.10 mm |
V = 586.9 (4) Å3 |
Rigaku AFC12κ/SATURN724 diffractometer | 2408 independent reflections |
Radiation source: fine-focus sealed tube | 2361 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ω scans | θmax = 26.5°, θmin = 1.8° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −7→7 |
Tmin = 0.773, Tmax = 1.000 | k = −10→11 |
14572 measured reflections | l = −14→14 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.157 | H-atom parameters constrained |
S = 1.16 | w = 1/[σ2(Fo2) + (0.0929P)2 + 0.1356P] where P = (Fo2 + 2Fc2)/3 |
2408 reflections | (Δ/σ)max < 0.001 |
157 parameters | Δρmax = 0.27 e Å−3 |
1 restraint | Δρmin = −0.25 e Å−3 |
C13H16O4 | γ = 73.70 (2)° |
Mr = 236.26 | V = 586.9 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.716 (2) Å | Mo Kα radiation |
b = 9.201 (4) Å | µ = 0.10 mm−1 |
c = 11.871 (6) Å | T = 173 K |
α = 89.76 (3)° | 0.35 × 0.35 × 0.10 mm |
β = 78.72 (2)° |
Rigaku AFC12κ/SATURN724 diffractometer | 2408 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 2361 reflections with I > 2σ(I) |
Tmin = 0.773, Tmax = 1.000 | Rint = 0.030 |
14572 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 1 restraint |
wR(F2) = 0.157 | H-atom parameters constrained |
S = 1.16 | Δρmax = 0.27 e Å−3 |
2408 reflections | Δρmin = −0.25 e Å−3 |
157 parameters |
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 | ||
O1 | −0.11375 (18) | 0.89747 (11) | 0.40885 (9) | 0.0294 (3) | |
O2 | 0.29860 (19) | 0.86868 (13) | 0.42473 (9) | 0.0335 (3) | |
H2O | 0.2683 | 0.9394 | 0.4747 | 0.050* | |
O3 | 0.1029 (2) | 0.87393 (12) | 0.15795 (9) | 0.0321 (3) | |
O4 | −0.09610 (17) | 0.69527 (11) | 0.20274 (8) | 0.0270 (3) | |
C2 | 0.1242 (3) | 0.91139 (17) | 0.35425 (12) | 0.0281 (3) | |
H2 | 0.1102 | 1.0170 | 0.3296 | 0.034* | |
C3 | 0.2058 (3) | 0.79968 (16) | 0.25019 (12) | 0.0264 (3) | |
H3 | 0.3905 | 0.7548 | 0.2291 | 0.032* | |
C4 | 0.0642 (2) | 0.67820 (16) | 0.28391 (11) | 0.0248 (3) | |
C5 | −0.0944 (3) | 0.73843 (16) | 0.40319 (12) | 0.0273 (3) | |
H5A | −0.2612 | 0.7226 | 0.4120 | 0.033* | |
H5B | −0.0130 | 0.6864 | 0.4645 | 0.033* | |
C6 | −0.0013 (3) | 0.77251 (17) | 0.10732 (12) | 0.0300 (4) | |
C41 | 0.2235 (2) | 0.51612 (16) | 0.28472 (12) | 0.0263 (3) | |
C42 | 0.4230 (3) | 0.48304 (18) | 0.34152 (13) | 0.0322 (4) | |
H42 | 0.4620 | 0.5630 | 0.3772 | 0.039* | |
C43 | 0.5645 (3) | 0.33463 (19) | 0.34623 (15) | 0.0380 (4) | |
H43 | 0.7000 | 0.3135 | 0.3849 | 0.046* | |
C44 | 0.5092 (3) | 0.21693 (18) | 0.29478 (14) | 0.0378 (4) | |
H44 | 0.6059 | 0.1151 | 0.2982 | 0.045* | |
C45 | 0.3115 (3) | 0.24891 (18) | 0.23827 (13) | 0.0362 (4) | |
H45 | 0.2735 | 0.1686 | 0.2025 | 0.043* | |
C46 | 0.1683 (3) | 0.39770 (17) | 0.23361 (12) | 0.0307 (4) | |
H46 | 0.0323 | 0.4184 | 0.1953 | 0.037* | |
C61 | 0.1984 (3) | 0.6632 (2) | 0.02004 (14) | 0.0398 (4) | |
H61A | 0.1252 | 0.5942 | −0.0141 | 0.060* | |
H61B | 0.3294 | 0.6045 | 0.0582 | 0.060* | |
H61C | 0.2701 | 0.7202 | −0.0405 | 0.060* | |
C62 | −0.2175 (3) | 0.8637 (2) | 0.05769 (14) | 0.0397 (4) | |
H62A | −0.2898 | 0.7948 | 0.0229 | 0.060* | |
H62B | −0.1591 | 0.9276 | −0.0011 | 0.060* | |
H62C | −0.3439 | 0.9279 | 0.1191 | 0.060* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0253 (5) | 0.0272 (6) | 0.0334 (6) | −0.0055 (4) | −0.0032 (4) | −0.0028 (4) |
O2 | 0.0280 (6) | 0.0361 (6) | 0.0352 (6) | −0.0045 (4) | −0.0103 (4) | −0.0069 (4) |
O3 | 0.0409 (6) | 0.0306 (6) | 0.0301 (6) | −0.0151 (5) | −0.0124 (4) | 0.0082 (4) |
O4 | 0.0261 (5) | 0.0309 (6) | 0.0258 (5) | −0.0093 (4) | −0.0082 (4) | 0.0054 (4) |
C2 | 0.0248 (7) | 0.0279 (7) | 0.0316 (7) | −0.0071 (5) | −0.0062 (5) | 0.0009 (6) |
C3 | 0.0258 (7) | 0.0266 (7) | 0.0272 (7) | −0.0083 (5) | −0.0051 (5) | 0.0028 (5) |
C4 | 0.0236 (7) | 0.0282 (8) | 0.0237 (7) | −0.0080 (5) | −0.0066 (5) | 0.0025 (5) |
C5 | 0.0258 (7) | 0.0279 (8) | 0.0274 (7) | −0.0071 (5) | −0.0042 (5) | 0.0014 (5) |
C6 | 0.0343 (8) | 0.0326 (8) | 0.0258 (7) | −0.0128 (6) | −0.0079 (6) | 0.0056 (6) |
C41 | 0.0265 (7) | 0.0271 (8) | 0.0243 (6) | −0.0075 (6) | −0.0030 (5) | 0.0025 (5) |
C42 | 0.0308 (8) | 0.0308 (8) | 0.0358 (8) | −0.0077 (6) | −0.0105 (6) | 0.0022 (6) |
C43 | 0.0332 (8) | 0.0367 (9) | 0.0420 (9) | −0.0038 (6) | −0.0114 (7) | 0.0070 (7) |
C44 | 0.0419 (9) | 0.0275 (8) | 0.0365 (8) | −0.0006 (6) | −0.0037 (7) | 0.0053 (6) |
C45 | 0.0479 (9) | 0.0276 (8) | 0.0325 (8) | −0.0108 (7) | −0.0065 (7) | 0.0011 (6) |
C46 | 0.0347 (8) | 0.0304 (8) | 0.0283 (7) | −0.0102 (6) | −0.0080 (6) | 0.0031 (6) |
C61 | 0.0430 (9) | 0.0468 (10) | 0.0281 (8) | −0.0141 (7) | −0.0015 (6) | −0.0018 (7) |
C62 | 0.0437 (9) | 0.0442 (10) | 0.0355 (8) | −0.0130 (7) | −0.0176 (7) | 0.0125 (7) |
O1—C2 | 1.4278 (18) | C41—C46 | 1.388 (2) |
O1—C5 | 1.4370 (19) | C41—C42 | 1.397 (2) |
O2—C2 | 1.3972 (17) | C42—C43 | 1.385 (2) |
O2—H2O | 0.8400 | C42—H42 | 0.9500 |
O3—C6 | 1.4295 (18) | C43—C44 | 1.385 (3) |
O3—C3 | 1.4254 (17) | C43—H43 | 0.9500 |
O4—C6 | 1.4323 (18) | C44—C45 | 1.386 (2) |
O4—C4 | 1.4339 (16) | C44—H44 | 0.9500 |
C2—C3 | 1.522 (2) | C45—C46 | 1.391 (2) |
C2—H2 | 1.0000 | C45—H45 | 0.9500 |
C3—C4 | 1.563 (2) | C46—H46 | 0.9500 |
C3—H3 | 1.0000 | C61—H61A | 0.9800 |
C4—C41 | 1.515 (2) | C61—H61B | 0.9800 |
C4—C5 | 1.535 (2) | C61—H61C | 0.9800 |
C5—H5A | 0.9900 | C62—H62A | 0.9800 |
C5—H5B | 0.9900 | C62—H62B | 0.9800 |
C6—C62 | 1.509 (2) | C62—H62C | 0.9800 |
C6—C61 | 1.513 (2) | ||
C2—O1—C5 | 106.30 (11) | O4—C6—C61 | 111.43 (13) |
C2—O2—H2O | 107.7 | C62—C6—C61 | 113.45 (14) |
C6—O3—C3 | 107.42 (11) | C46—C41—C42 | 118.91 (14) |
C6—O4—C4 | 108.29 (10) | C46—C41—C4 | 120.93 (13) |
O2—C2—O1 | 111.99 (12) | C42—C41—C4 | 120.10 (13) |
O2—C2—C3 | 108.35 (12) | C43—C42—C41 | 120.58 (15) |
O1—C2—C3 | 104.47 (11) | C43—C42—H42 | 119.7 |
O2—C2—H2 | 110.6 | C41—C42—H42 | 119.7 |
O1—C2—H2 | 110.6 | C44—C43—C42 | 120.26 (15) |
C3—C2—H2 | 110.6 | C44—C43—H43 | 119.9 |
O3—C3—C2 | 108.22 (12) | C42—C43—H43 | 119.9 |
O3—C3—C4 | 104.64 (11) | C43—C44—C45 | 119.46 (15) |
C2—C3—C4 | 104.60 (11) | C43—C44—H44 | 120.3 |
O3—C3—H3 | 112.9 | C45—C44—H44 | 120.3 |
C2—C3—H3 | 112.9 | C46—C45—C44 | 120.51 (15) |
C4—C3—H3 | 112.9 | C46—C45—H45 | 119.7 |
O4—C4—C41 | 112.22 (11) | C44—C45—H45 | 119.7 |
O4—C4—C5 | 108.90 (11) | C45—C46—C41 | 120.27 (14) |
C41—C4—C5 | 112.12 (12) | C45—C46—H46 | 119.9 |
O4—C4—C3 | 103.36 (10) | C41—C46—H46 | 119.9 |
C41—C4—C3 | 116.44 (11) | C6—C61—H61A | 109.5 |
C5—C4—C3 | 102.99 (11) | C6—C61—H61B | 109.5 |
O1—C5—C4 | 105.33 (11) | H61A—C61—H61B | 109.5 |
O1—C5—H5A | 110.7 | C6—C61—H61C | 109.5 |
C4—C5—H5A | 110.7 | H61A—C61—H61C | 109.5 |
O1—C5—H5B | 110.7 | H61B—C61—H61C | 109.5 |
C4—C5—H5B | 110.7 | C6—C62—H62A | 109.5 |
H5A—C5—H5B | 108.8 | C6—C62—H62B | 109.5 |
O3—C6—O4 | 104.00 (11) | H62A—C62—H62B | 109.5 |
O3—C6—C62 | 109.07 (13) | C6—C62—H62C | 109.5 |
O4—C6—C62 | 108.34 (12) | H62A—C62—H62C | 109.5 |
O3—C6—C61 | 110.10 (13) | H62B—C62—H62C | 109.5 |
C5—O1—C2—O2 | −76.45 (14) | C3—O3—C6—O4 | 34.96 (14) |
C5—O1—C2—C3 | 40.60 (13) | C3—O3—C6—C62 | 150.39 (12) |
C6—O3—C3—C2 | −133.84 (12) | C3—O3—C6—C61 | −84.52 (14) |
C6—O3—C3—C4 | −22.73 (13) | C4—O4—C6—O3 | −33.70 (14) |
O2—C2—C3—O3 | −154.79 (11) | C4—O4—C6—C62 | −149.65 (13) |
O1—C2—C3—O3 | 85.67 (13) | C4—O4—C6—C61 | 84.87 (14) |
O2—C2—C3—C4 | 94.07 (13) | O4—C4—C41—C46 | −14.92 (18) |
O1—C2—C3—C4 | −25.47 (13) | C5—C4—C41—C46 | 108.02 (15) |
C6—O4—C4—C41 | −107.03 (13) | C3—C4—C41—C46 | −133.74 (14) |
C6—O4—C4—C5 | 128.23 (12) | O4—C4—C41—C42 | 167.76 (12) |
C6—O4—C4—C3 | 19.23 (13) | C5—C4—C41—C42 | −69.29 (16) |
O3—C3—C4—O4 | 2.14 (13) | C3—C4—C41—C42 | 48.95 (18) |
C2—C3—C4—O4 | 115.84 (12) | C46—C41—C42—C43 | 0.4 (2) |
O3—C3—C4—C41 | 125.66 (12) | C4—C41—C42—C43 | 177.73 (13) |
C2—C3—C4—C41 | −120.64 (13) | C41—C42—C43—C44 | −0.2 (2) |
O3—C3—C4—C5 | −111.22 (12) | C42—C43—C44—C45 | 0.2 (2) |
C2—C3—C4—C5 | 2.48 (13) | C43—C44—C45—C46 | −0.4 (2) |
C2—O1—C5—C4 | −39.18 (13) | C44—C45—C46—C41 | 0.6 (2) |
O4—C4—C5—O1 | −88.03 (13) | C42—C41—C46—C45 | −0.6 (2) |
C41—C4—C5—O1 | 147.17 (11) | C4—C41—C46—C45 | −177.92 (13) |
C3—C4—C5—O1 | 21.22 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2o···O1i | 0.84 | 1.93 | 2.755 (2) | 166 |
C5—H5a···O2ii | 0.99 | 2.47 | 3.296 (3) | 140 |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C13H16O4 |
Mr | 236.26 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 173 |
a, b, c (Å) | 5.716 (2), 9.201 (4), 11.871 (6) |
α, β, γ (°) | 89.76 (3), 78.72 (2), 73.70 (2) |
V (Å3) | 586.9 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.35 × 0.35 × 0.10 |
Data collection | |
Diffractometer | Rigaku AFC12κ/SATURN724 diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.773, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14572, 2408, 2361 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.157, 1.16 |
No. of reflections | 2408 |
No. of parameters | 157 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.27, −0.25 |
Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2o···O1i | 0.84 | 1.93 | 2.755 (2) | 166 |
C5—H5a···O2ii | 0.99 | 2.47 | 3.296 (3) | 140 |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) x−1, y, z. |
Footnotes
‡Additional correspondence author, e-mail: dennis.taylor@adelaide.edu.au.
Acknowledgements
We are grateful to the Australian Research Council for financial support. TVR thanks the Commonwealth Government of Australia for a postgraduate scholarship.
References
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The dihydroxyation of monocyclic and bicyclic 1,2-dioxines has provided a new route for the stereoselective synthesis of a diverse range of carbohydrates and related compounds (Pedersen et al., 2009; Robinson et al., 2006; Robinson et al., 2009; Valente et al., 2009). During the course of these studies, the title compound, (I), was obtained by the Co(II)-mediated ring-opening of the precursor 1,2-dioxane, post dihydroxyation. The reactions of Co(II) complexes with endoperoxides have been well documented (Boyd et al., 1980; Sutbeyaz et al., 1988; Greatrex et al., 2003; Greatrex & Taylor, 2005).
The molecular structure of (I), Fig. 1, comprises two fused five-membered rings linked at the C3—C4 bond. Each of the five-membered rings adopts an envelope conformation, on atom O1 for the furanose (O1, C2—C5) ring, and on atom C6 for the acetonide (O3, O4, C3, C4, C6) ring. When viewed down the C3—C4 axis, the O1 atom lies above the plane through the four remaining atoms, away from the phenyl substituent and the C6 atom lies below the plane, being orientated in the same direction as the phenyl ring. In the crystal structure centrosymmetrically related pairs of molecules associate via O—H···O hydrogen bonds to form an eight-membered {···OCOH}2 synthon, Table 1 and Fig. 2. The dimers are linked into a supramolecular chain via C—H···O contacts and ten-membered {···OH···OCH}2 synthons, Table 1. The resulting chain comprising alternating eight- and ten-membered synthons has a flattened topology, Fig. 2, and is aligned along the a axis.