threo-3,4-Di­hydroxy­hexane-2,5-dione

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.

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

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

Crystal data

C6H10O4	F(000) = 312
Mr = 146.14	Dx = 1.329 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C2yc	Cell parameters from 791 reflections
a = 17.041 (4) Å	θ = 3.2–24.5°
b = 4.8657 (10) Å	µ = 0.11 mm^−1
c = 11.656 (3) Å	T = 298 K
β = 130.910 (3)°	Block, colorless
V = 730.4 (3) Å^3	0.26 × 0.25 × 0.22 mm
Z = 4

Data collection

Bruker APEX area-detector diffractometer	652 independent reflections
Radiation source: fine-focus sealed tube	580 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 25.2°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −19→20
Tmin = 0.964, Tmax = 0.976	k = −5→5
1780 measured reflections	l = −13→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.128	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0655P)^2 + 0.5476P] where P = (Fo^2 + 2Fc^2)/3
652 reflections	(Δ/σ)max < 0.001
48 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.58833 (12)	0.7146 (3)	0.12074 (18)	0.0608 (5)
O2	0.41927 (12)	0.6742 (4)	0.08467 (17)	0.0634 (6)
H2	0.4344	0.6065	0.0369	0.095*
C1	0.66922 (17)	1.0785 (5)	0.2980 (3)	0.0592 (6)
H1A	0.7140	1.0063	0.3994	0.089*
H1B	0.6401	1.2497	0.2955	0.089*
H1C	0.7085	1.1079	0.2667	0.089*
C2	0.58435 (15)	0.8800 (4)	0.1937 (2)	0.0419 (5)
C3	0.48714 (13)	0.8920 (4)	0.17381 (19)	0.0406 (5)
H3	0.4510	1.0641	0.1216	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0674 (10)	0.0696 (11)	0.0621 (9)	−0.0024 (8)	0.0497 (9)	−0.0123 (8)
O2	0.0591 (9)	0.0843 (12)	0.0575 (9)	−0.0256 (8)	0.0429 (8)	−0.0319 (8)
C1	0.0537 (12)	0.0634 (14)	0.0654 (14)	−0.0088 (10)	0.0412 (11)	−0.0057 (11)
C2	0.0473 (10)	0.0471 (11)	0.0356 (9)	0.0030 (8)	0.0290 (8)	0.0068 (8)
C3	0.0420 (10)	0.0459 (11)	0.0332 (9)	−0.0003 (8)	0.0244 (8)	−0.0001 (7)

Geometric parameters (Å, º)

O1—C2	1.205 (2)	C1—H1B	0.9600
O2—C3	1.402 (2)	C1—H1C	0.9600
O2—H2	0.8200	C2—C3	1.516 (3)
C1—C2	1.483 (3)	C3—C3^i	1.526 (3)
C1—H1A	0.9600	C3—H3	0.9800
C3—O2—H2	109.5	O1—C2—C3	118.61 (17)
C2—C1—H1A	109.5	C1—C2—C3	118.78 (17)
C2—C1—H1B	109.5	O2—C3—C2	111.88 (16)
H1A—C1—H1B	109.5	O2—C3—C3^i	109.36 (13)
C2—C1—H1C	109.5	C2—C3—C3^i	111.71 (17)
H1A—C1—H1C	109.5	O2—C3—H3	107.9
H1B—C1—H1C	109.5	C2—C3—H3	107.9
O1—C2—C1	122.58 (18)	C3^i—C3—H3	107.9

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.82	2.18	2.632 (2)	115
O2—H2···O1^ii	0.82	2.24	2.987 (2)	151

Symmetry code: (ii) −x+1, −y+1, −z.