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The title compound, C13H22O6, packs in the crystal structure utilizing strong O—H...O hydrogen bonds and two weaker C—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806042292/bt2210sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806042292/bt2210Isup2.hkl
Contains datablock I

CCDC reference: 627362

Key indicators

  • Single-crystal X-ray study
  • T = 163 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.043
  • wR factor = 0.103
  • Data-to-parameter ratio = 9.4

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: 0.658 0.994 Tmin(prime) and Tmax expected: 0.922 0.995 RR(prime) = 0.715 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.71
Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.80 mm PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.96 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.63 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7
Alert level G 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 26.38 From the CIF: _reflns_number_total 1701 Count of symmetry unique reflns 1718 Completeness (_total/calc) 99.01% 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 C2 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . R
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT and SADABS (Sheldrick, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

1-D-1,2:5,6-Di-O-isopropylidene-3-O-methyl-chiro- inositol top
Crystal data top
C13H22O6F(000) = 592
Mr = 274.31Dx = 1.282 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5190 reflections
a = 5.6670 (9) Åθ = 2.2–13.3°
b = 9.8516 (16) ŵ = 0.10 mm1
c = 25.447 (4) ÅT = 163 K
V = 1420.7 (4) Å3Needle, colourless
Z = 40.80 × 0.31 × 0.05 mm
Data collection top
Bruker P4 CCD area-detector
diffractometer
1701 independent reflections
Radiation source: fine-focus sealed tube1312 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
Detector resolution: 8.192 pixels mm-1θmax = 26.4°, θmin = 1.6°
φ and ω scansh = 73
Absorption correction: multi-scan
(Blessing, 1995)
k = 1212
Tmin = 0.658, Tmax = 0.994l = 3131
18007 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0673P)2]
where P = (Fo2 + 2Fc2)/3
1701 reflections(Δ/σ)max < 0.001
180 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.24 e Å3
Special details top

Experimental. Crystal decay was monitored by repeating the initial 10 frames at the end of the data collection and analyzing duplicate reflections. The standard 1.0 mm diameter collimator was used.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.6325 (4)0.6862 (2)0.20001 (7)0.0455 (6)
O20.8544 (4)0.85974 (18)0.17091 (7)0.0375 (5)
O31.1899 (3)0.84150 (18)0.07463 (7)0.0293 (5)
O41.0525 (3)0.65201 (19)0.00322 (6)0.0296 (4)
H4O0.924 (5)0.665 (3)0.0144 (11)0.036*
O50.7754 (3)0.42109 (16)0.06337 (7)0.0286 (5)
O60.4813 (3)0.47161 (18)0.12194 (6)0.0329 (5)
C10.7705 (5)0.6306 (3)0.15807 (9)0.0283 (6)
H10.85620.54780.17040.034*
C20.9480 (5)0.7438 (3)0.14432 (9)0.0267 (6)
H21.10590.72070.15940.032*
C30.9738 (5)0.7728 (2)0.08578 (9)0.0235 (6)
H30.83720.82820.07320.028*
C40.9807 (5)0.6361 (2)0.05652 (9)0.0231 (6)
H41.10090.57790.07430.028*
C50.7436 (4)0.5654 (2)0.06161 (9)0.0221 (6)
H50.64240.58940.03080.027*
C60.6086 (5)0.5950 (2)0.11262 (10)0.0238 (6)
H60.49470.67090.10660.029*
C70.7363 (5)0.8113 (3)0.21655 (10)0.0360 (7)
C80.9062 (6)0.7851 (5)0.26123 (11)0.0655 (12)
H8A1.03210.72430.24920.098*
H8B0.82150.74270.29050.098*
H8C0.97510.87120.27290.098*
C90.5427 (7)0.9088 (4)0.23073 (14)0.0645 (11)
H9A0.61070.99820.23800.097*
H9B0.45970.87570.26200.097*
H9C0.43130.91590.20140.097*
C100.5686 (5)0.3663 (3)0.08720 (10)0.0276 (6)
C110.3800 (5)0.3340 (3)0.04687 (11)0.0337 (7)
H11A0.34720.41520.02580.051*
H11B0.23560.30520.06490.051*
H11C0.43530.26090.02380.051*
C120.6437 (6)0.2449 (3)0.11975 (12)0.0431 (8)
H12A0.70010.17260.09640.065*
H12B0.50890.21170.14020.065*
H12C0.77090.27170.14370.065*
C131.1855 (6)0.9836 (3)0.08597 (11)0.0448 (8)
H13A1.05401.02610.06720.067*
H13B1.33431.02500.07470.067*
H13C1.16530.99700.12390.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0562 (14)0.0468 (13)0.0336 (11)0.0225 (12)0.0148 (10)0.0138 (9)
O20.0495 (13)0.0261 (10)0.0368 (10)0.0078 (10)0.0140 (10)0.0117 (8)
O30.0282 (11)0.0196 (9)0.0401 (10)0.0054 (9)0.0042 (9)0.0027 (8)
O40.0293 (11)0.0311 (10)0.0284 (10)0.0042 (9)0.0051 (8)0.0008 (8)
O50.0262 (10)0.0184 (9)0.0413 (10)0.0008 (8)0.0053 (8)0.0050 (8)
O60.0359 (11)0.0243 (10)0.0383 (10)0.0101 (9)0.0109 (9)0.0083 (8)
C10.0363 (16)0.0231 (13)0.0254 (13)0.0016 (13)0.0007 (12)0.0005 (11)
C20.0241 (15)0.0261 (14)0.0299 (13)0.0023 (12)0.0014 (12)0.0044 (11)
C30.0214 (14)0.0206 (13)0.0286 (13)0.0021 (12)0.0017 (11)0.0010 (10)
C40.0212 (14)0.0227 (13)0.0253 (12)0.0006 (12)0.0011 (11)0.0015 (10)
C50.0223 (13)0.0166 (12)0.0275 (12)0.0000 (11)0.0027 (11)0.0027 (10)
C60.0237 (14)0.0162 (12)0.0314 (13)0.0045 (11)0.0015 (11)0.0014 (10)
C70.0367 (17)0.0390 (17)0.0323 (14)0.0131 (15)0.0072 (13)0.0114 (12)
C80.060 (3)0.104 (3)0.0326 (17)0.010 (2)0.0050 (16)0.0175 (19)
C90.069 (3)0.068 (2)0.057 (2)0.008 (2)0.026 (2)0.0138 (18)
C100.0253 (15)0.0239 (14)0.0336 (14)0.0026 (12)0.0047 (12)0.0034 (11)
C110.0311 (16)0.0294 (15)0.0405 (15)0.0054 (14)0.0017 (13)0.0075 (13)
C120.0470 (19)0.0277 (15)0.0545 (18)0.0055 (16)0.0042 (16)0.0064 (13)
C130.062 (2)0.0205 (15)0.0519 (18)0.0109 (16)0.0138 (17)0.0096 (13)
Geometric parameters (Å, º) top
O1—C71.429 (3)C5—H51.0000
O1—C11.432 (3)C6—H61.0000
O2—C71.423 (3)C7—C91.502 (5)
O2—C21.430 (3)C7—C81.512 (4)
O3—C31.428 (3)C8—H8A0.9800
O3—C131.429 (3)C8—H8B0.9800
O4—C41.425 (3)C8—H8C0.9800
O4—H4O0.86 (3)C9—H9A0.9800
O5—C101.426 (3)C9—H9B0.9800
O5—C51.433 (3)C9—H9C0.9800
O6—C61.433 (3)C10—C111.515 (4)
O6—C101.451 (3)C10—C121.516 (4)
C1—C61.517 (3)C11—H11A0.9800
C1—C21.542 (4)C11—H11B0.9800
C1—H11.0000C11—H11C0.9800
C2—C31.524 (3)C12—H12A0.9800
C2—H21.0000C12—H12B0.9800
C3—C41.539 (3)C12—H12C0.9800
C3—H31.0000C13—H13A0.9800
C4—C51.519 (3)C13—H13B0.9800
C4—H41.0000C13—H13C0.9800
C5—C61.535 (4)
C7—O1—C1108.9 (2)O2—C7—O1104.05 (19)
C7—O2—C2107.0 (2)O2—C7—C9109.0 (3)
C3—O3—C13114.1 (2)O1—C7—C9108.7 (3)
C4—O4—H4O105.6 (19)O2—C7—C8111.8 (2)
C10—O5—C5106.60 (19)O1—C7—C8109.7 (3)
C6—O6—C10109.51 (18)C9—C7—C8113.2 (2)
O1—C1—C6109.1 (2)C7—C8—H8A109.5
O1—C1—C2104.40 (19)C7—C8—H8B109.5
C6—C1—C2112.85 (19)H8A—C8—H8B109.5
O1—C1—H1110.1C7—C8—H8C109.5
C6—C1—H1110.1H8A—C8—H8C109.5
C2—C1—H1110.1H8B—C8—H8C109.5
O2—C2—C3110.4 (2)C7—C9—H9A109.5
O2—C2—C1103.21 (19)C7—C9—H9B109.5
C3—C2—C1114.9 (2)H9A—C9—H9B109.5
O2—C2—H2109.4C7—C9—H9C109.5
C3—C2—H2109.4H9A—C9—H9C109.5
C1—C2—H2109.4H9B—C9—H9C109.5
O3—C3—C2111.4 (2)O5—C10—O6105.6 (2)
O3—C3—C4107.26 (19)O5—C10—C11111.8 (2)
C2—C3—C4108.1 (2)O6—C10—C11108.8 (2)
O3—C3—H3110.0O5—C10—C12107.5 (2)
C2—C3—H3110.0O6—C10—C12109.1 (2)
C4—C3—H3110.0C11—C10—C12113.8 (2)
O4—C4—C5112.6 (2)C10—C11—H11A109.5
O4—C4—C3111.83 (19)C10—C11—H11B109.5
C5—C4—C3109.8 (2)H11A—C11—H11B109.5
O4—C4—H4107.5C10—C11—H11C109.5
C5—C4—H4107.5H11A—C11—H11C109.5
C3—C4—H4107.5H11B—C11—H11C109.5
O5—C5—C4110.3 (2)C10—C12—H12A109.5
O5—C5—C6103.00 (19)C10—C12—H12B109.5
C4—C5—C6115.2 (2)H12A—C12—H12B109.5
O5—C5—H5109.4C10—C12—H12C109.5
C4—C5—H5109.4H12A—C12—H12C109.5
C6—C5—H5109.4H12B—C12—H12C109.5
O6—C6—C1112.0 (2)O3—C13—H13A109.5
O6—C6—C5103.28 (19)O3—C13—H13B109.5
C1—C6—C5112.8 (2)H13A—C13—H13B109.5
O6—C6—H6109.5O3—C13—H13C109.5
C1—C6—H6109.5H13A—C13—H13C109.5
C5—C6—H6109.5H13B—C13—H13C109.5
C7—O1—C1—C6129.3 (2)C3—C4—C5—C630.7 (3)
C7—O1—C1—C28.5 (3)C10—O6—C6—C1110.0 (2)
C7—O2—C2—C3153.8 (2)C10—O6—C6—C511.6 (2)
C7—O2—C2—C130.6 (3)O1—C1—C6—O677.1 (3)
O1—C1—C2—O213.3 (3)C2—C1—C6—O6167.4 (2)
C6—C1—C2—O2105.0 (2)O1—C1—C6—C5166.95 (19)
O1—C1—C2—C3133.5 (2)C2—C1—C6—C551.4 (3)
C6—C1—C2—C315.2 (3)O5—C5—C6—O628.4 (2)
C13—O3—C3—C278.8 (3)C4—C5—C6—O6148.5 (2)
C13—O3—C3—C4163.0 (2)O5—C5—C6—C192.7 (2)
O2—C2—C3—O383.8 (3)C4—C5—C6—C127.4 (3)
C1—C2—C3—O3160.0 (2)C2—O2—C7—O136.4 (3)
O2—C2—C3—C4158.5 (2)C2—O2—C7—C9152.2 (2)
C1—C2—C3—C442.4 (3)C2—O2—C7—C881.9 (3)
O3—C3—C4—O447.7 (3)C1—O1—C7—O227.3 (3)
C2—C3—C4—O4168.0 (2)C1—O1—C7—C9143.3 (2)
O3—C3—C4—C5173.41 (18)C1—O1—C7—C892.5 (3)
C2—C3—C4—C566.3 (3)C5—O5—C10—O628.6 (2)
C10—O5—C5—C4158.79 (18)C5—O5—C10—C1189.5 (2)
C10—O5—C5—C635.3 (2)C5—O5—C10—C12145.0 (2)
O4—C4—C5—O588.0 (2)C6—O6—C10—O59.6 (3)
C3—C4—C5—O5146.8 (2)C6—O6—C10—C11110.5 (2)
O4—C4—C5—C6156.0 (2)C6—O6—C10—C12124.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4O···O3i0.87 (3)2.03 (3)2.855 (2)160 (3)
C3—H3···O4i1.02.533.373 (3)141
C6—H6···O3ii1.02.543.530 (3)169
C13—H13C···O20.982.523.112 (4)118
Symmetry codes: (i) x1/2, y+3/2, z; (ii) x1, y, z.
 

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