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The title compound, C6H12O4, exists in a chair form, with three of the four OH groups equatorially disposed. All four hydr­oxy groups participate in extensive inter­molecular O—H...O hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805006653/ob6485sup1.cif
Contains datablocks global, 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805006653/ob64851sup2.hkl
Contains datablock 1

CCDC reference: 270498

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.029
  • wR factor = 0.081
  • Data-to-parameter ratio = 8.6

checkCIF/PLATON results

No syntax errors found



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 26.35 From the CIF: _reflns_number_total 814 Count of symmetry unique reflns 817 Completeness (_total/calc) 99.63% 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
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2003).

(1R*,2S*,4S*,5S*)-Cyclohexane-1,2,4,5-tetraol top
Crystal data top
C6H12O4F(000) = 320
Mr = 148.16Dx = 1.471 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 700 reflections
a = 6.756 (2) Åθ = 2.9–27.0°
b = 8.783 (3) ŵ = 0.12 mm1
c = 11.271 (4) ÅT = 296 K
V = 668.8 (4) Å3Block, colorless
Z = 40.40 × 0.35 × 0.30 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
814 independent reflections
Radiation source: fine focus sealed tube800 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
φ and ω scansθmax = 26.4°, θmin = 2.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 88
Tmin = 0.922, Tmax = 0.964k = 1010
5158 measured reflectionsl = 1413
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029H-atom parameters constrained
wR(F2) = 0.081 w = 1/[σ2(Fo2) + (0.0517P)2 + 0.064P]
where P = (Fo2 + 2Fc2)/3
S = 1.18(Δ/σ)max = 0.002
814 reflectionsΔρmax = 0.23 e Å3
95 parametersΔρmin = 0.16 e Å3
0 restraintsAbsolute structure: see text
Primary atom site location: structure-invariant direct methods
Special details top

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
C10.5986 (2)1.03548 (18)0.39802 (15)0.0264 (4)
C20.6345 (2)0.9495 (2)0.28261 (14)0.0267 (3)
C30.7890 (2)0.82414 (19)0.29957 (15)0.0277 (4)
C40.9837 (2)0.88982 (18)0.34483 (14)0.0243 (3)
C50.9491 (2)0.97142 (19)0.46199 (14)0.0252 (3)
C60.7938 (2)1.09584 (18)0.44614 (15)0.0280 (4)
O10.50885 (16)0.93627 (14)0.48315 (11)0.0323 (3)
O20.45593 (16)0.89111 (15)0.23335 (11)0.0350 (3)
O31.13323 (17)0.77544 (13)0.35428 (11)0.0297 (3)
O41.13133 (16)1.03623 (15)0.50163 (11)0.0333 (3)
H10.50961.12130.38260.032*
H20.68891.02240.22550.032*
H3A0.73970.74970.35580.033*
H3B0.81150.77280.22460.033*
H41.02910.96550.28710.029*
H50.90220.89790.52110.030*
H6A0.77011.14460.52210.034*
H6B0.84471.17240.39220.034*
H1O0.39170.95870.49080.048*
H2O0.38970.85150.28590.053*
H3O1.10080.71290.40470.044*
H4O1.11891.06590.57020.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0196 (7)0.0287 (7)0.0308 (8)0.0041 (6)0.0001 (6)0.0068 (6)
C20.0203 (7)0.0340 (7)0.0258 (7)0.0028 (7)0.0020 (6)0.0054 (6)
C30.0246 (8)0.0309 (8)0.0277 (8)0.0003 (7)0.0001 (7)0.0035 (7)
C40.0204 (7)0.0268 (7)0.0258 (7)0.0014 (6)0.0028 (6)0.0013 (6)
C50.0176 (6)0.0315 (7)0.0265 (7)0.0022 (7)0.0009 (6)0.0009 (6)
C60.0240 (7)0.0275 (7)0.0326 (8)0.0007 (7)0.0009 (7)0.0023 (7)
O10.0190 (5)0.0444 (7)0.0335 (6)0.0030 (5)0.0050 (5)0.0115 (5)
O20.0235 (6)0.0536 (8)0.0280 (6)0.0076 (6)0.0040 (5)0.0060 (5)
O30.0225 (5)0.0305 (5)0.0360 (6)0.0056 (5)0.0063 (5)0.0026 (5)
O40.0185 (5)0.0481 (7)0.0333 (6)0.0037 (5)0.0002 (5)0.0114 (6)
Geometric parameters (Å, º) top
C1—H10.9800C6—C51.526 (2)
C2—C11.524 (2)C6—H6A0.9700
C2—H20.9800C6—H6B0.9700
C3—C21.529 (2)O1—C11.431 (2)
C3—C41.524 (2)O1—H1O0.8200
C3—H3A0.9700O2—C21.4237 (19)
C3—H3B0.9700O2—H2O0.8200
C4—C51.521 (2)O3—C41.4289 (18)
C4—H40.9800O3—H3O0.8200
C5—H50.9800O4—C51.4279 (18)
C6—C11.521 (2)O4—H4O0.8200
C1—C2—C3111.04 (13)C5—C6—H6A109.0
C1—C6—C5112.86 (13)C5—C6—H6B109.0
C1—C2—H2107.3C5—O4—H4O109.5
C1—C6—H6A109.0C6—C1—C2109.83 (12)
C1—C6—H6B109.0C6—C1—H1109.1
C1—O1—H1O109.5C6—C5—H5109.2
C2—C1—H1109.1O1—C1—C2109.75 (13)
C2—C3—H3A109.4O1—C1—C6109.91 (13)
C2—C3—H3B109.4O1—C1—H1109.1
C2—O2—H2O109.5O2—C2—C1112.11 (12)
C3—C2—H2107.3O2—C2—C3111.61 (14)
C3—C4—H4107.8O2—C2—H2107.3
C4—C3—C2111.01 (13)O3—C4—C3111.66 (12)
C4—C5—C6109.96 (13)O3—C4—C5112.03 (12)
C4—C3—H3A109.4O3—C4—H4107.8
C4—C3—H3B109.4O4—C5—C4109.11 (12)
C4—C5—H5109.2O4—C5—C6110.14 (13)
C4—O3—H3O109.5O4—C5—H5109.2
C5—C4—C3109.68 (12)H3A—C3—H3B108.0
C5—C4—H4107.8H6A—C6—H6B107.8
C1—C6—C5—C456.85 (17)C4—C3—C2—C157.77 (17)
C1—C6—C5—O4177.12 (12)C4—C3—C2—O2176.35 (12)
C2—C3—C4—C558.74 (17)C5—C6—C1—C255.06 (18)
C2—C3—C4—O3176.46 (12)C5—C6—C1—O165.79 (16)
C3—C2—C1—C654.71 (17)O2—C2—C1—C6179.68 (13)
C3—C4—C5—C657.40 (17)O2—C2—C1—O159.38 (17)
C3—C2—C1—O166.22 (16)O3—C4—C5—C6178.01 (12)
C3—C4—C5—O4178.30 (13)O3—C4—C5—O457.11 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···O4i0.821.892.705 (2)172
O2—H2O···O3i0.822.012.765 (2)153
O3—H3O···O1ii0.821.922.742 (2)176
O4—H4O···O2iii0.821.942.752 (2)169
Symmetry codes: (i) x1, y, z; (ii) x+1/2, y+3/2, z+1; (iii) x+3/2, y+2, z+1/2.
 

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