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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807014584/lh2351sup1.cif
Contains datablocks 3, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807014584/lh23513sup2.hkl
Contains datablock 3

CCDC reference: 647277

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.038
  • wR factor = 0.106
  • Data-to-parameter ratio = 11.5

checkCIF/PLATON results

No syntax errors found



Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.500 1.000 Tmin(prime) and Tmax expected: 0.950 0.996 RR(prime) = 0.524 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.52
Alert level C PLAT602_ALERT_4_C VERY LARGE Solvent Accessible VOID(S) in Structure !
Alert level G REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values From the CIF: _diffrn_reflns_theta_max 27.47 From the CIF: _reflns_number_total 2078 From the CIF: _diffrn_reflns_limit_ max hkl 0. 20. 16. From the CIF: _diffrn_reflns_limit_ min hkl -17. 0. 0. TEST1: Expected hkl limits for theta max Calculated maximum hkl 20. 20. 16. Calculated minimum hkl -20. -20. -16. REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.47 From the CIF: _reflns_number_total 2078 Count of symmetry unique reflns 2092 Completeness (_total/calc) 99.33% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . R
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 6 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

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
C14H22O6Dx = 1.087 Mg m3
Mr = 286.33Mo Kα radiation, λ = 0.71073 Å
Hexagonal, P65Cell parameters from 2079 reflections
Hall symbol: P 65θ = 5–27°
a = 15.6104 (3) ŵ = 0.09 mm1
c = 12.4340 (3) ÅT = 150 K
V = 2624.03 (10) Å3Plate, colourless
Z = 60.60 × 0.10 × 0.05 mm
F(000) = 924
Data collection top
Bruker–Nonius KappaCCD
diffractometer
1777 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
ω scansθmax = 27.5°, θmin = 5.2°
Absorption correction: multi-scan
(DENZO/SCALEPACK; Otwinowski & Minor, 1997)
h = 170
Tmin = 0.50, Tmax = 1.00k = 020
18890 measured reflectionsl = 016
2078 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-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 reflectionsΔρmax = 0.26 e Å3
181 parametersΔρmin = 0.21 e Å3
1 restraint
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.52862 (15)0.70492 (15)0.6157 (2)0.0258
C20.45506 (15)0.59201 (15)0.6198 (2)0.0264
C30.49461 (16)0.52260 (16)0.5919 (2)0.0281
O40.41240 (11)0.42364 (11)0.60692 (15)0.0308
C50.40360 (16)0.36401 (16)0.5145 (2)0.0305
O60.49116 (11)0.42071 (11)0.45314 (15)0.0311
C70.52147 (17)0.52263 (16)0.4731 (2)0.0297
C80.4022 (2)0.27094 (18)0.5503 (2)0.0390
C90.31198 (17)0.34378 (18)0.4518 (2)0.0376
C100.57739 (19)0.53762 (19)0.6674 (2)0.0362
O110.37730 (11)0.57465 (10)0.54273 (15)0.0287
C120.38233 (15)0.66020 (16)0.5118 (2)0.0294
C130.46748 (15)0.74744 (15)0.5694 (2)0.0270
O140.53119 (11)0.82388 (11)0.49895 (15)0.0308
C150.60291 (15)0.79997 (16)0.4590 (2)0.0315
O160.60032 (11)0.72638 (11)0.53116 (15)0.0289
C170.70331 (19)0.89353 (19)0.4634 (3)0.0479
C180.57661 (19)0.7564 (2)0.3467 (2)0.0383
O190.32558 (13)0.66156 (13)0.4474 (2)0.0405
C200.57951 (19)0.75069 (18)0.7212 (2)0.0360
H210.42590.57600.69390.0313*
H710.59200.56320.46190.0370*
H720.48450.54500.42580.0372*
H810.39370.23050.48680.0582*
H820.46470.28970.58760.0579*
H830.34560.23250.59760.0581*
H910.30360.30180.38950.0586*
H920.31810.40530.42750.0592*
H930.25470.30900.49890.0591*
H1010.59250.48460.65360.0582*
H1020.63700.60220.65590.0583*
H1030.55320.53190.74120.0581*
H1310.44190.77400.62710.0327*
H1710.75180.87780.43620.0657*
H1720.71540.91190.53950.0662*
H1730.70460.94660.42030.0662*
H1810.62520.73840.32440.0679*
H1820.57780.80580.29940.0685*
H1830.51050.69770.34940.0679*
H2010.62030.82300.71200.0562*
H2020.53200.73480.77730.0563*
H2030.62440.72560.73820.0564*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0290 (9)0.0258 (9)0.0250 (10)0.0154 (8)0.0032 (9)0.0025 (9)
C20.0292 (10)0.0279 (9)0.0250 (11)0.0165 (8)0.0012 (9)0.0029 (9)
C30.0301 (10)0.0290 (10)0.0279 (12)0.0168 (9)0.0028 (9)0.0041 (9)
O40.0363 (8)0.0275 (7)0.0284 (9)0.0159 (6)0.0089 (7)0.0038 (7)
C50.0359 (11)0.0313 (10)0.0283 (12)0.0199 (9)0.0039 (10)0.0006 (10)
O60.0363 (8)0.0295 (7)0.0335 (9)0.0209 (6)0.0062 (7)0.0000 (7)
C70.0358 (11)0.0302 (11)0.0290 (12)0.0208 (9)0.0065 (10)0.0020 (9)
C80.0512 (14)0.0312 (11)0.0397 (15)0.0245 (11)0.0032 (12)0.0016 (11)
C90.0361 (12)0.0433 (12)0.0355 (13)0.0216 (10)0.0003 (11)0.0051 (12)
C100.0417 (12)0.0423 (12)0.0335 (13)0.0276 (11)0.0017 (11)0.0025 (11)
O110.0290 (7)0.0281 (7)0.0323 (9)0.0168 (6)0.0003 (7)0.0008 (7)
C120.0309 (10)0.0295 (10)0.0323 (12)0.0185 (9)0.0033 (10)0.0045 (9)
C130.0299 (10)0.0278 (10)0.0260 (11)0.0164 (8)0.0035 (9)0.0031 (9)
O140.0344 (8)0.0279 (7)0.0333 (9)0.0180 (7)0.0062 (7)0.0066 (7)
C150.0325 (11)0.0316 (11)0.0339 (13)0.0187 (9)0.0061 (10)0.0067 (10)
O160.0296 (7)0.0322 (7)0.0285 (8)0.0183 (6)0.0047 (7)0.0048 (7)
C170.0387 (12)0.0375 (12)0.064 (2)0.0163 (11)0.0079 (14)0.0108 (14)
C180.0489 (14)0.0491 (14)0.0291 (13)0.0336 (12)0.0063 (11)0.0037 (11)
O190.0361 (8)0.0395 (9)0.0485 (10)0.0208 (8)0.0109 (8)0.0012 (9)
C200.0409 (12)0.0371 (12)0.0305 (12)0.0199 (10)0.0044 (11)0.0024 (10)
Geometric parameters (Å, º) top
C1—C21.550 (3)C9—H930.975
C1—C131.522 (3)C10—H1010.983
C1—O161.447 (3)C10—H1020.982
C1—C201.515 (3)C10—H1030.979
C2—C31.531 (3)O11—C121.354 (2)
C2—O111.462 (3)C12—C131.524 (3)
C2—H211.002C12—O191.202 (3)
C3—O41.444 (2)C13—O141.412 (3)
C3—C71.535 (3)C13—H1311.005
C3—C101.518 (3)O14—C151.434 (3)
O4—C51.441 (3)C15—O161.442 (3)
C5—O61.423 (3)C15—C171.518 (3)
C5—C81.509 (3)C15—C181.516 (4)
C5—C91.517 (3)C17—H1710.965
O6—C71.437 (3)C17—H1720.979
C7—H710.967C17—H1730.979
C7—H721.002C18—H1810.971
C8—H810.977C18—H1820.963
C8—H820.984C18—H1830.980
C8—H830.979C20—H2010.987
C9—H910.981C20—H2020.957
C9—H920.964C20—H2030.981
C2—C1—C13103.82 (16)H92—C9—H93110.5
C2—C1—O16109.57 (17)C3—C10—H101107.9
C13—C1—O16101.88 (17)C3—C10—H102111.4
C2—C1—C20115.01 (19)H101—C10—H102109.7
C13—C1—C20114.64 (19)C3—C10—H103107.8
O16—C1—C20110.93 (17)H101—C10—H103109.2
C1—C2—C3117.73 (17)H102—C10—H103110.8
C1—C2—O11105.26 (16)C2—O11—C12111.71 (16)
C3—C2—O11108.14 (18)O11—C12—C13110.04 (18)
C1—C2—H21107.5O11—C12—O19121.8 (2)
C3—C2—H21109.0C13—C12—O19128.18 (19)
O11—C2—H21109.0C12—C13—C1104.16 (17)
C2—C3—O4105.70 (16)C12—C13—O14113.2 (2)
C2—C3—C7115.12 (19)C1—C13—O14105.82 (16)
O4—C3—C7102.78 (18)C12—C13—H131110.8
C2—C3—C10111.34 (19)C1—C13—H131112.0
O4—C3—C10108.54 (18)O14—C13—H131110.5
C7—C3—C10112.56 (19)C13—O14—C15107.86 (15)
C3—O4—C5109.54 (17)O14—C15—O16106.08 (17)
O4—C5—O6105.91 (17)O14—C15—C17107.56 (18)
O4—C5—C8109.7 (2)O16—C15—C17110.4 (2)
O6—C5—C8107.68 (18)O14—C15—C18111.34 (18)
O4—C5—C9108.64 (17)O16—C15—C18108.79 (18)
O6—C5—C9111.5 (2)C17—C15—C18112.5 (2)
C8—C5—C9113.1 (2)C1—O16—C15110.27 (15)
C5—O6—C7106.15 (16)C15—C17—H171107.8
C3—C7—O6103.15 (18)C15—C17—H172105.8
C3—C7—H71111.1H171—C17—H172110.6
O6—C7—H71109.7C15—C17—H173111.7
C3—C7—H72111.2H171—C17—H173109.6
O6—C7—H72110.8H172—C17—H173111.2
H71—C7—H72110.6C15—C18—H181108.5
C5—C8—H81108.4C15—C18—H182108.1
C5—C8—H82108.6H181—C18—H182110.6
H81—C8—H82111.6C15—C18—H183108.1
C5—C8—H83109.9H181—C18—H183110.5
H81—C8—H83107.5H182—C18—H183111.0
H82—C8—H83110.9C1—C20—H201109.0
C5—C9—H91110.0C1—C20—H202110.7
C5—C9—H92109.9H201—C20—H202110.8
H91—C9—H92109.4C1—C20—H203108.0
C5—C9—H93108.3H201—C20—H203107.5
H91—C9—H93108.9H202—C20—H203110.8
 

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