organic compounds
The relative configuration at C-2 of the title lactone, C14H22O6, which exists in the five-membered ring form, was unequivocally established by X-ray crystallographic analysis. The absolute configuration was determined by the use of 2,4-di-C-methyl-L-arabinose as the starting material.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807014584/lh2351sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807014584/lh23513sup2.hkl |
CCDC reference: 647277
Computing details top
Data collection: COLLECT (Nonius, 2001); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS.
2,3:5,6-Di-O-isopropylidene-3,5-di-C-methyl-L-mannono-1,4-
lactone top
Crystal data top
C14H22O6 | Dx = 1.087 Mg m−3 |
Mr = 286.33 | Mo Kα radiation, λ = 0.71073 Å |
Hexagonal, P65 | Cell parameters from 2079 reflections |
Hall symbol: P 65 | θ = 5–27° |
a = 15.6104 (3) Å | µ = 0.09 mm−1 |
c = 12.4340 (3) Å | T = 150 K |
V = 2624.03 (10) Å3 | Plate, colourless |
Z = 6 | 0.60 × 0.10 × 0.05 mm |
F(000) = 924 |
Data collection top
Bruker–Nonius KappaCCD diffractometer | 1777 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.054 |
ω scans | θmax = 27.5°, θmin = 5.2° |
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997) | h = −17→0 |
Tmin = 0.50, Tmax = 1.00 | k = 0→20 |
18890 measured reflections | l = 0→16 |
2078 independent reflections |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.106 | w = 1/[σ2(F2) + (0.08P)2 + 0.05P], where P = [max(Fo2,0) + 2Fc2]/3 |
S = 0.97 | (Δ/σ)max = 0.019 |
2078 reflections | Δρmax = 0.26 e Å−3 |
181 parameters | Δρmin = −0.21 e Å−3 |
1 restraint |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
C1 | 0.52862 (15) | 0.70492 (15) | 0.6157 (2) | 0.0258 | |
C2 | 0.45506 (15) | 0.59201 (15) | 0.6198 (2) | 0.0264 | |
C3 | 0.49461 (16) | 0.52260 (16) | 0.5919 (2) | 0.0281 | |
O4 | 0.41240 (11) | 0.42364 (11) | 0.60692 (15) | 0.0308 | |
C5 | 0.40360 (16) | 0.36401 (16) | 0.5145 (2) | 0.0305 | |
O6 | 0.49116 (11) | 0.42071 (11) | 0.45314 (15) | 0.0311 | |
C7 | 0.52147 (17) | 0.52263 (16) | 0.4731 (2) | 0.0297 | |
C8 | 0.4022 (2) | 0.27094 (18) | 0.5503 (2) | 0.0390 | |
C9 | 0.31198 (17) | 0.34378 (18) | 0.4518 (2) | 0.0376 | |
C10 | 0.57739 (19) | 0.53762 (19) | 0.6674 (2) | 0.0362 | |
O11 | 0.37730 (11) | 0.57465 (10) | 0.54273 (15) | 0.0287 | |
C12 | 0.38233 (15) | 0.66020 (16) | 0.5118 (2) | 0.0294 | |
C13 | 0.46748 (15) | 0.74744 (15) | 0.5694 (2) | 0.0270 | |
O14 | 0.53119 (11) | 0.82388 (11) | 0.49895 (15) | 0.0308 | |
C15 | 0.60291 (15) | 0.79997 (16) | 0.4590 (2) | 0.0315 | |
O16 | 0.60032 (11) | 0.72638 (11) | 0.53116 (15) | 0.0289 | |
C17 | 0.70331 (19) | 0.89353 (19) | 0.4634 (3) | 0.0479 | |
C18 | 0.57661 (19) | 0.7564 (2) | 0.3467 (2) | 0.0383 | |
O19 | 0.32558 (13) | 0.66156 (13) | 0.4474 (2) | 0.0405 | |
C20 | 0.57951 (19) | 0.75069 (18) | 0.7212 (2) | 0.0360 | |
H21 | 0.4259 | 0.5760 | 0.6939 | 0.0313* | |
H71 | 0.5920 | 0.5632 | 0.4619 | 0.0370* | |
H72 | 0.4845 | 0.5450 | 0.4258 | 0.0372* | |
H81 | 0.3937 | 0.2305 | 0.4868 | 0.0582* | |
H82 | 0.4647 | 0.2897 | 0.5876 | 0.0579* | |
H83 | 0.3456 | 0.2325 | 0.5976 | 0.0581* | |
H91 | 0.3036 | 0.3018 | 0.3895 | 0.0586* | |
H92 | 0.3181 | 0.4053 | 0.4275 | 0.0592* | |
H93 | 0.2547 | 0.3090 | 0.4989 | 0.0591* | |
H101 | 0.5925 | 0.4846 | 0.6536 | 0.0582* | |
H102 | 0.6370 | 0.6022 | 0.6559 | 0.0583* | |
H103 | 0.5532 | 0.5319 | 0.7412 | 0.0581* | |
H131 | 0.4419 | 0.7740 | 0.6271 | 0.0327* | |
H171 | 0.7518 | 0.8778 | 0.4362 | 0.0657* | |
H172 | 0.7154 | 0.9119 | 0.5395 | 0.0662* | |
H173 | 0.7046 | 0.9466 | 0.4203 | 0.0662* | |
H181 | 0.6252 | 0.7384 | 0.3244 | 0.0679* | |
H182 | 0.5778 | 0.8058 | 0.2994 | 0.0685* | |
H183 | 0.5105 | 0.6977 | 0.3494 | 0.0679* | |
H201 | 0.6203 | 0.8230 | 0.7120 | 0.0562* | |
H202 | 0.5320 | 0.7348 | 0.7773 | 0.0563* | |
H203 | 0.6244 | 0.7256 | 0.7382 | 0.0564* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0290 (9) | 0.0258 (9) | 0.0250 (10) | 0.0154 (8) | 0.0032 (9) | 0.0025 (9) |
C2 | 0.0292 (10) | 0.0279 (9) | 0.0250 (11) | 0.0165 (8) | 0.0012 (9) | 0.0029 (9) |
C3 | 0.0301 (10) | 0.0290 (10) | 0.0279 (12) | 0.0168 (9) | 0.0028 (9) | 0.0041 (9) |
O4 | 0.0363 (8) | 0.0275 (7) | 0.0284 (9) | 0.0159 (6) | 0.0089 (7) | 0.0038 (7) |
C5 | 0.0359 (11) | 0.0313 (10) | 0.0283 (12) | 0.0199 (9) | 0.0039 (10) | 0.0006 (10) |
O6 | 0.0363 (8) | 0.0295 (7) | 0.0335 (9) | 0.0209 (6) | 0.0062 (7) | 0.0000 (7) |
C7 | 0.0358 (11) | 0.0302 (11) | 0.0290 (12) | 0.0208 (9) | 0.0065 (10) | 0.0020 (9) |
C8 | 0.0512 (14) | 0.0312 (11) | 0.0397 (15) | 0.0245 (11) | 0.0032 (12) | 0.0016 (11) |
C9 | 0.0361 (12) | 0.0433 (12) | 0.0355 (13) | 0.0216 (10) | −0.0003 (11) | −0.0051 (12) |
C10 | 0.0417 (12) | 0.0423 (12) | 0.0335 (13) | 0.0276 (11) | −0.0017 (11) | 0.0025 (11) |
O11 | 0.0290 (7) | 0.0281 (7) | 0.0323 (9) | 0.0168 (6) | −0.0003 (7) | 0.0008 (7) |
C12 | 0.0309 (10) | 0.0295 (10) | 0.0323 (12) | 0.0185 (9) | 0.0033 (10) | 0.0045 (9) |
C13 | 0.0299 (10) | 0.0278 (10) | 0.0260 (11) | 0.0164 (8) | 0.0035 (9) | 0.0031 (9) |
O14 | 0.0344 (8) | 0.0279 (7) | 0.0333 (9) | 0.0180 (7) | 0.0062 (7) | 0.0066 (7) |
C15 | 0.0325 (11) | 0.0316 (11) | 0.0339 (13) | 0.0187 (9) | 0.0061 (10) | 0.0067 (10) |
O16 | 0.0296 (7) | 0.0322 (7) | 0.0285 (8) | 0.0183 (6) | 0.0047 (7) | 0.0048 (7) |
C17 | 0.0387 (12) | 0.0375 (12) | 0.064 (2) | 0.0163 (11) | 0.0079 (14) | 0.0108 (14) |
C18 | 0.0489 (14) | 0.0491 (14) | 0.0291 (13) | 0.0336 (12) | 0.0063 (11) | 0.0037 (11) |
O19 | 0.0361 (8) | 0.0395 (9) | 0.0485 (10) | 0.0208 (8) | −0.0109 (8) | 0.0012 (9) |
C20 | 0.0409 (12) | 0.0371 (12) | 0.0305 (12) | 0.0199 (10) | −0.0044 (11) | −0.0024 (10) |
Geometric parameters (Å, º) top
C1—C2 | 1.550 (3) | C9—H93 | 0.975 |
C1—C13 | 1.522 (3) | C10—H101 | 0.983 |
C1—O16 | 1.447 (3) | C10—H102 | 0.982 |
C1—C20 | 1.515 (3) | C10—H103 | 0.979 |
C2—C3 | 1.531 (3) | O11—C12 | 1.354 (2) |
C2—O11 | 1.462 (3) | C12—C13 | 1.524 (3) |
C2—H21 | 1.002 | C12—O19 | 1.202 (3) |
C3—O4 | 1.444 (2) | C13—O14 | 1.412 (3) |
C3—C7 | 1.535 (3) | C13—H131 | 1.005 |
C3—C10 | 1.518 (3) | O14—C15 | 1.434 (3) |
O4—C5 | 1.441 (3) | C15—O16 | 1.442 (3) |
C5—O6 | 1.423 (3) | C15—C17 | 1.518 (3) |
C5—C8 | 1.509 (3) | C15—C18 | 1.516 (4) |
C5—C9 | 1.517 (3) | C17—H171 | 0.965 |
O6—C7 | 1.437 (3) | C17—H172 | 0.979 |
C7—H71 | 0.967 | C17—H173 | 0.979 |
C7—H72 | 1.002 | C18—H181 | 0.971 |
C8—H81 | 0.977 | C18—H182 | 0.963 |
C8—H82 | 0.984 | C18—H183 | 0.980 |
C8—H83 | 0.979 | C20—H201 | 0.987 |
C9—H91 | 0.981 | C20—H202 | 0.957 |
C9—H92 | 0.964 | C20—H203 | 0.981 |
C2—C1—C13 | 103.82 (16) | H92—C9—H93 | 110.5 |
C2—C1—O16 | 109.57 (17) | C3—C10—H101 | 107.9 |
C13—C1—O16 | 101.88 (17) | C3—C10—H102 | 111.4 |
C2—C1—C20 | 115.01 (19) | H101—C10—H102 | 109.7 |
C13—C1—C20 | 114.64 (19) | C3—C10—H103 | 107.8 |
O16—C1—C20 | 110.93 (17) | H101—C10—H103 | 109.2 |
C1—C2—C3 | 117.73 (17) | H102—C10—H103 | 110.8 |
C1—C2—O11 | 105.26 (16) | C2—O11—C12 | 111.71 (16) |
C3—C2—O11 | 108.14 (18) | O11—C12—C13 | 110.04 (18) |
C1—C2—H21 | 107.5 | O11—C12—O19 | 121.8 (2) |
C3—C2—H21 | 109.0 | C13—C12—O19 | 128.18 (19) |
O11—C2—H21 | 109.0 | C12—C13—C1 | 104.16 (17) |
C2—C3—O4 | 105.70 (16) | C12—C13—O14 | 113.2 (2) |
C2—C3—C7 | 115.12 (19) | C1—C13—O14 | 105.82 (16) |
O4—C3—C7 | 102.78 (18) | C12—C13—H131 | 110.8 |
C2—C3—C10 | 111.34 (19) | C1—C13—H131 | 112.0 |
O4—C3—C10 | 108.54 (18) | O14—C13—H131 | 110.5 |
C7—C3—C10 | 112.56 (19) | C13—O14—C15 | 107.86 (15) |
C3—O4—C5 | 109.54 (17) | O14—C15—O16 | 106.08 (17) |
O4—C5—O6 | 105.91 (17) | O14—C15—C17 | 107.56 (18) |
O4—C5—C8 | 109.7 (2) | O16—C15—C17 | 110.4 (2) |
O6—C5—C8 | 107.68 (18) | O14—C15—C18 | 111.34 (18) |
O4—C5—C9 | 108.64 (17) | O16—C15—C18 | 108.79 (18) |
O6—C5—C9 | 111.5 (2) | C17—C15—C18 | 112.5 (2) |
C8—C5—C9 | 113.1 (2) | C1—O16—C15 | 110.27 (15) |
C5—O6—C7 | 106.15 (16) | C15—C17—H171 | 107.8 |
C3—C7—O6 | 103.15 (18) | C15—C17—H172 | 105.8 |
C3—C7—H71 | 111.1 | H171—C17—H172 | 110.6 |
O6—C7—H71 | 109.7 | C15—C17—H173 | 111.7 |
C3—C7—H72 | 111.2 | H171—C17—H173 | 109.6 |
O6—C7—H72 | 110.8 | H172—C17—H173 | 111.2 |
H71—C7—H72 | 110.6 | C15—C18—H181 | 108.5 |
C5—C8—H81 | 108.4 | C15—C18—H182 | 108.1 |
C5—C8—H82 | 108.6 | H181—C18—H182 | 110.6 |
H81—C8—H82 | 111.6 | C15—C18—H183 | 108.1 |
C5—C8—H83 | 109.9 | H181—C18—H183 | 110.5 |
H81—C8—H83 | 107.5 | H182—C18—H183 | 111.0 |
H82—C8—H83 | 110.9 | C1—C20—H201 | 109.0 |
C5—C9—H91 | 110.0 | C1—C20—H202 | 110.7 |
C5—C9—H92 | 109.9 | H201—C20—H202 | 110.8 |
H91—C9—H92 | 109.4 | C1—C20—H203 | 108.0 |
C5—C9—H93 | 108.3 | H201—C20—H203 | 107.5 |
H91—C9—H93 | 108.9 | H202—C20—H203 | 110.8 |