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ISSN: 2056-9890

3-Chloro-4-hy­droxy­furan-2(5H)-one

aDepartment of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, People's Republic of China, and bState Key Laboratory for Physical Chemistry of Solid Surfaces, Xiamen University, Xiamen 361005, People's Republic of China
*Correspondence e-mail: zywu@xmu.edu.cn

(Received 12 July 2009; accepted 20 July 2009; online 25 July 2009)

In the title compound, C4H3ClO3, mol­ecules 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[Haynes, L. J. & Plimmer, J. R. (1960). Q. Rev. Chem. Soc. 14, 292-315.]). 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[Sodeoka, M., Sampe, R., Kojima, S., Baba, Y., Usui, T., Ueda, K. & Osada, H. (2001). J. Med. Chem. 44, 3216-3222.]). For related structures, see: Ma et al. (2004[Ma, S. M., Wu, B. & Shi, Z. J. (2004). J. Org. Chem. 69, 1429-1431.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C4H3ClO3

  • Mr = 134.51

  • Orthorhombic, P n m a

  • 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[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.736, Tmax = 0.828

  • 1932 measured reflections

  • 531 independent reflections

  • 500 reflections with I > 2σ(I)

  • Rint = 0.012

Refinement
  • R[F2 > 2σ(F2)] = 0.026

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2⋯O1i 0.80 (3) 1.85 (3) 2.647 (2) 171 (3)
Symmetry code: (i) x, y, z-1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2009[Westrip, S. (2009). publCIF. In preparation.]).

Supporting information


Comment top

4-hydroxy-5H-furan-2-one (Tetronic acid) form a subclass of β-hydroxybutenolides with the generic structure (Haynes & Plimmer, 1960). The best known members of this family are vitamin C (ascorbic acid) and pennicillic acid. A great number of these compounds and their metabolites are found in many natural products, which exhibit a wide array of biological properties (Sodeoka et al., 2001). In the present study, the title comound (I) has been determined as product of double-molecular ring closure of monochloroacetic acid which is halo-substituted tetronic acid.

The molecular structure is depicted in Fig. 1. Bond lengths and angles are in good agreement with previous reported for similar compounds (Ma et al., 2004). The crystal structure is stabilized by O—H···O hydrogen bonding and the molecules are linked in an infinite chain along the c axis, with graph-set motifs C(6) through O— H··· O hydrogen bonds (Bernstein et al., 1995) (Fig. 2, Table 1).

Related literature top

4-Hydroxy-5H-furan-2-one (Tetronic acid) forms a subclass of β-hydroxybutenolides with the generic structure, see: Haynes & Plimmer (1960). A great number of these compounds and their metabolites, which are found in many natural products, 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 top

All reagents and solvents were used as obtained commercially without further purification. To a stirred solution of monochloroacetic acid(2 mmol, 137µL) in 5 mL dry THF is added sodium(1 mmol, 23 mg) under N2. After the solution has been stirred at room temperature for 24 h, the resulting pale yellow solution was kept in darkness for four days, yellow well formed block-shaped crystals were obtained.

Refinement top

The aromatic H atoms were generated geometrically (C—H 0.93 Å) and were allowed to ride on their parent atoms in the riding model approximations, with their temperature factors set to 1.2 times those of the parent atoms. The position and Ueq of the hydroxyl H atom were refined with O—H distance restrained to 0.85 Å.

Computing details top

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

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability label and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. Partial packing view showing the O—H···O interactions (dashed lines) and the formation of a chain parallel to the c axis.
3-Chloro-4-hydroxyfuran-2(5H)-one top
Crystal data top
C4H3ClO3F(000) = 272
Mr = 134.51Dx = 1.774 Mg m3
Orthorhombic, PnmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 1627 reflections
a = 12.0437 (6) Åθ = 3.1–28.9°
b = 6.5453 (4) ŵ = 0.65 mm1
c = 6.3886 (4) ÅT = 298 K
V = 503.61 (5) Å3Block, yellow
Z = 40.50 × 0.50 × 0.30 mm
Data collection top
Oxford Gemini S Ultra
diffractometer
531 independent reflections
Radiation source: fine-focus sealed tube500 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.012
Detector resolution: 16.1903 pixels mm-1θmax = 26.0°, θmin = 3.4°
ω scansh = 1414
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2008)
k = 78
Tmin = 0.736, Tmax = 0.828l = 77
1932 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)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.067H 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 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.20 e Å3
Crystal data top
C4H3ClO3V = 503.61 (5) Å3
Mr = 134.51Z = 4
Orthorhombic, PnmaMo Kα radiation
a = 12.0437 (6) ŵ = 0.65 mm1
b = 6.5453 (4) ÅT = 298 K
c = 6.3886 (4) Å0.50 × 0.50 × 0.30 mm
Data collection top
Oxford Gemini S Ultra
diffractometer
531 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2008)
500 reflections with I > 2σ(I)
Tmin = 0.736, Tmax = 0.828Rint = 0.012
1932 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0260 restraints
wR(F2) = 0.067H atoms treated by a mixture of independent and constrained refinement
S = 1.17Δρmax = 0.25 e Å3
531 reflectionsΔρmin = 0.20 e Å3
52 parameters
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*/UeqOcc. (<1)
Cl10.34253 (4)0.75000.60829 (9)0.0400 (2)
O10.10530 (15)0.75000.8246 (3)0.0531 (5)
O20.24683 (15)0.75000.1417 (2)0.0409 (4)
O30.02339 (12)0.75000.5138 (2)0.0410 (4)
C10.05689 (17)0.75000.2974 (3)0.0348 (5)
H1A0.02950.87060.22590.042*0.50
H1B0.02950.62940.22590.042*0.50
C20.18096 (17)0.75000.3064 (3)0.0288 (4)
C30.21185 (17)0.75000.5069 (3)0.0289 (4)
C40.11471 (18)0.75000.6361 (3)0.0335 (5)
H20.210 (3)0.75000.037 (5)0.059 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0274 (3)0.0523 (4)0.0403 (3)0.0000.0084 (2)0.000
O10.0421 (9)0.0940 (14)0.0231 (8)0.0000.0033 (6)0.000
O20.0376 (8)0.0614 (11)0.0238 (8)0.0000.0062 (7)0.000
O30.0260 (8)0.0679 (10)0.0292 (9)0.0000.0011 (6)0.000
C10.0308 (10)0.0487 (12)0.0249 (11)0.0000.0042 (8)0.000
C20.0284 (10)0.0337 (10)0.0241 (10)0.0000.0019 (8)0.000
C30.0251 (10)0.0355 (10)0.0261 (11)0.0000.0006 (7)0.000
C40.0299 (10)0.0460 (12)0.0247 (11)0.0000.0006 (8)0.000
Geometric parameters (Å, º) top
Cl1—C31.702 (2)C1—C21.495 (3)
O1—C41.210 (3)C1—H1A0.9700
O2—C21.318 (2)C1—H1B0.9700
O2—H20.80 (3)C2—C31.334 (3)
O3—C41.349 (3)C3—C41.431 (3)
O3—C11.440 (3)
C2—O2—H2109 (2)O2—C2—C1124.82 (18)
C4—O3—C1109.11 (16)C3—C2—C1108.38 (17)
O3—C1—C2104.08 (16)C2—C3—C4109.00 (19)
O3—C1—H1A110.9C2—C3—Cl1128.55 (17)
C2—C1—H1A110.9C4—C3—Cl1122.45 (15)
O3—C1—H1B110.9O1—C4—O3120.0 (2)
C2—C1—H1B110.9O1—C4—C3130.6 (2)
H1A—C1—H1B109.0O3—C4—C3109.43 (17)
O2—C2—C3126.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.80 (3)1.85 (3)2.647 (2)171 (3)
Symmetry code: (i) x, y, z1.

Experimental details

Crystal data
Chemical formulaC4H3ClO3
Mr134.51
Crystal system, space groupOrthorhombic, Pnma
Temperature (K)298
a, b, c (Å)12.0437 (6), 6.5453 (4), 6.3886 (4)
V3)503.61 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.65
Crystal size (mm)0.50 × 0.50 × 0.30
Data collection
DiffractometerOxford Gemini S Ultra
diffractometer
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2008)
Tmin, Tmax0.736, 0.828
No. of measured, independent and
observed [I > 2σ(I)] reflections
1932, 531, 500
Rint0.012
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.026, 0.067, 1.17
No. of reflections531
No. of parameters52
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.25, 0.20

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.80 (3)1.85 (3)2.647 (2)171 (3)
Symmetry code: (i) x, y, z1.
 

References

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
First citationHaynes, L. J. & Plimmer, J. R. (1960). Q. Rev. Chem. Soc. 14, 292–315.  CrossRef CAS Web of Science Google Scholar
First citationMa, S. M., Wu, B. & Shi, Z. J. (2004). J. Org. Chem. 69, 1429–1431.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationOxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSodeoka, M., Sampe, R., Kojima, S., Baba, Y., Usui, T., Ueda, K. & Osada, H. (2001). J. Med. Chem. 44, 3216–3222.  Web of Science CrossRef PubMed CAS Google Scholar
First citationWestrip, S. (2009). publCIF. In preparation.  Google Scholar

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ISSN: 2056-9890
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