3-Chloro-4-hydroxy-furan-2(5H)-one.

In the title compound, C(4)H(3)ClO(3), mol-ecules are linked via O-H⋯O hydrogen bonds into an infinite chain with graph-set motif C(6) along the c axis.

Related literature

4-Hydr­oxy-5H-furan-2-one (tetronic acid) forms a subclass of β-hydroxy­butenolides with a generic structure, see: Haynes & Plimmer (1960 ▶). A great number of these compounds and their metabolites are found in many natural products and exhibit a wide array of biological properties, see: Sodeoka et al. (2001 ▶). For related structures, see: Ma et al. (2004 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C4H3ClO3

M = 134.51

Orthorhombic,

a = 12.0437 (6) Å

b = 6.5453 (4) Å

c = 6.3886 (4) Å

V = 503.61 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.65 mm−1

T = 298 K

0.50 × 0.50 × 0.30 mm

Data collection

Oxford Gemini S Ultra diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.736, T max = 0.828

1932 measured reflections

531 independent reflections

500 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.067

S = 1.17

531 reflections

52 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809028724/bx2226sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028724/bx2226Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C4H3ClO3	F(000) = 272
Mr = 134.51	Dx = 1.774 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 1627 reflections
a = 12.0437 (6) Å	θ = 3.1–28.9°
b = 6.5453 (4) Å	µ = 0.65 mm−1
c = 6.3886 (4) Å	T = 298 K
V = 503.61 (5) Å3	Block, yellow
Z = 4	0.50 × 0.50 × 0.30 mm

Oxford Gemini S Ultra diffractometer	531 independent reflections
Radiation source: fine-focus sealed tube	500 reflections with I > 2σ(I)
graphite	Rint = 0.012
Detector resolution: 16.1903 pixels mm-1	θmax = 26.0°, θmin = 3.4°
ω scans	h = −14→14
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −7→8
Tmin = 0.736, Tmax = 0.828	l = −7→7
1932 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.067	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	w = 1/[σ2(Fo2) + (0.0374P)2 + 0.1215P] where P = (Fo2 + 2Fc2)/3
531 reflections	(Δ/σ)max < 0.001
52 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.34253 (4)	0.7500	0.60829 (9)	0.0400 (2)
O1	0.10530 (15)	0.7500	0.8246 (3)	0.0531 (5)
O2	0.24683 (15)	0.7500	0.1417 (2)	0.0409 (4)
O3	0.02339 (12)	0.7500	0.5138 (2)	0.0410 (4)
C1	0.05689 (17)	0.7500	0.2974 (3)	0.0348 (5)
H1A	0.0295	0.8706	0.2259	0.042*	0.50
H1B	0.0295	0.6294	0.2259	0.042*	0.50
C2	0.18096 (17)	0.7500	0.3064 (3)	0.0288 (4)
C3	0.21185 (17)	0.7500	0.5069 (3)	0.0289 (4)
C4	0.11471 (18)	0.7500	0.6361 (3)	0.0335 (5)
H2	0.210 (3)	0.7500	0.037 (5)	0.059 (9)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0274 (3)	0.0523 (4)	0.0403 (3)	0.000	−0.0084 (2)	0.000
O1	0.0421 (9)	0.0940 (14)	0.0231 (8)	0.000	0.0033 (6)	0.000
O2	0.0376 (8)	0.0614 (11)	0.0238 (8)	0.000	0.0062 (7)	0.000
O3	0.0260 (8)	0.0679 (10)	0.0292 (9)	0.000	0.0011 (6)	0.000
C1	0.0308 (10)	0.0487 (12)	0.0249 (11)	0.000	−0.0042 (8)	0.000
C2	0.0284 (10)	0.0337 (10)	0.0241 (10)	0.000	0.0019 (8)	0.000
C3	0.0251 (10)	0.0355 (10)	0.0261 (11)	0.000	−0.0006 (7)	0.000
C4	0.0299 (10)	0.0460 (12)	0.0247 (11)	0.000	0.0006 (8)	0.000

Cl1—C3	1.702 (2)	C1—C2	1.495 (3)
O1—C4	1.210 (3)	C1—H1A	0.9700
O2—C2	1.318 (2)	C1—H1B	0.9700
O2—H2	0.80 (3)	C2—C3	1.334 (3)
O3—C4	1.349 (3)	C3—C4	1.431 (3)
O3—C1	1.440 (3)
C2—O2—H2	109 (2)	O2—C2—C1	124.82 (18)
C4—O3—C1	109.11 (16)	C3—C2—C1	108.38 (17)
O3—C1—C2	104.08 (16)	C2—C3—C4	109.00 (19)
O3—C1—H1A	110.9	C2—C3—Cl1	128.55 (17)
C2—C1—H1A	110.9	C4—C3—Cl1	122.45 (15)
O3—C1—H1B	110.9	O1—C4—O3	120.0 (2)
C2—C1—H1B	110.9	O1—C4—C3	130.6 (2)
H1A—C1—H1B	109.0	O3—C4—C3	109.43 (17)
O2—C2—C3	126.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.80 (3)	1.85 (3)	2.647 (2)	171 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.80 (3)	1.85 (3)	2.647 (2)	171 (3)

Symmetry code: (i) .