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In the title compound, C6H10O4, the mol­ecule sits on a twofold axis such that there is one half-mol­ecule in the asymmetric unit. In the crystal structure, there are one intra- and one intermolecular O—H...O hydrogen bonds, resulting in an infinite zigzag chain.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805005556/fl6147sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805005556/fl6147Isup2.hkl
Contains datablock I

CCDC reference: 269559

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.048
  • wR factor = 0.128
  • Data-to-parameter ratio = 13.6

checkCIF/PLATON results

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Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Bruker, 2002); software used to prepare material for publication: SHELXL97.

threo-3,4-dihydroxyhexane-2,5-dione top
Crystal data top
C6H10O4F(000) = 312
Mr = 146.14Dx = 1.329 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C2ycCell parameters from 791 reflections
a = 17.041 (4) Åθ = 3.2–24.5°
b = 4.8657 (10) ŵ = 0.11 mm1
c = 11.656 (3) ÅT = 298 K
β = 130.910 (3)°Block, colorless
V = 730.4 (3) Å30.26 × 0.25 × 0.22 mm
Z = 4
Data collection top
Bruker APEX area-detector
diffractometer
652 independent reflections
Radiation source: fine-focus sealed tube580 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
φ and ω scansθmax = 25.2°, θmin = 3.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 1920
Tmin = 0.964, Tmax = 0.976k = 55
1780 measured reflectionsl = 1310
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0655P)2 + 0.5476P]
where P = (Fo2 + 2Fc2)/3
652 reflections(Δ/σ)max < 0.001
48 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.16 e Å3
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
O10.58833 (12)0.7146 (3)0.12074 (18)0.0608 (5)
O20.41927 (12)0.6742 (4)0.08467 (17)0.0634 (6)
H20.43440.60650.03690.095*
C10.66922 (17)1.0785 (5)0.2980 (3)0.0592 (6)
H1A0.71401.00630.39940.089*
H1B0.64011.24970.29550.089*
H1C0.70851.10790.26670.089*
C20.58435 (15)0.8800 (4)0.1937 (2)0.0419 (5)
C30.48714 (13)0.8920 (4)0.17381 (19)0.0406 (5)
H30.45101.06410.12160.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0674 (10)0.0696 (11)0.0621 (9)0.0024 (8)0.0497 (9)0.0123 (8)
O20.0591 (9)0.0843 (12)0.0575 (9)0.0256 (8)0.0429 (8)0.0319 (8)
C10.0537 (12)0.0634 (14)0.0654 (14)0.0088 (10)0.0412 (11)0.0057 (11)
C20.0473 (10)0.0471 (11)0.0356 (9)0.0030 (8)0.0290 (8)0.0068 (8)
C30.0420 (10)0.0459 (11)0.0332 (9)0.0003 (8)0.0244 (8)0.0001 (7)
Geometric parameters (Å, º) top
O1—C21.205 (2)C1—H1B0.9600
O2—C31.402 (2)C1—H1C0.9600
O2—H20.8200C2—C31.516 (3)
C1—C21.483 (3)C3—C3i1.526 (3)
C1—H1A0.9600C3—H30.9800
C3—O2—H2109.5O1—C2—C3118.61 (17)
C2—C1—H1A109.5C1—C2—C3118.78 (17)
C2—C1—H1B109.5O2—C3—C2111.88 (16)
H1A—C1—H1B109.5O2—C3—C3i109.36 (13)
C2—C1—H1C109.5C2—C3—C3i111.71 (17)
H1A—C1—H1C109.5O2—C3—H3107.9
H1B—C1—H1C109.5C2—C3—H3107.9
O1—C2—C1122.58 (18)C3i—C3—H3107.9
Symmetry code: (i) x+1, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O10.822.182.632 (2)115
O2—H2···O1ii0.822.242.987 (2)151
Symmetry code: (ii) x+1, y+1, z.
 

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