Levulinic Acid.

THE TITLE COMPOUND (SYSTEMATIC NAME: 4-oxo-penta-noic acid), C5H8O3, is close to planar (r.m.s. deviation = 0.0762 Å). In the crystal, the mol-ecules inter-act via O-H⋯O hydrogen bonds in which the hy-droxy O atoms act as donors and the ketone O atoms in adjacent mol-ecules as acceptors, forming C(7) chains along [20-1].

Related literature

For uses of levulinic acid, see: Timokhin et al. (1999 ▶). For density functional and Møller–Plesset perturbation theory calculations for levulinic acid, see: Reichert et al. (2010 ▶); Kim et al. (2011 ▶). For typical bond lengths and angles, see: Allen et al. (1987 ▶); Borthwick (1980 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶); Etter et al. (1990 ▶). For background to the study, see: Flakus & Hachuła (2008 ▶); Flakus & Stachowska (2006 ▶).

Experimental

Crystal data

C5H8O3

M = 116.11

Monoclinic,

a = 4.8761 (2) Å

b = 12.1025 (4) Å

c = 9.8220 (3) Å

β = 99.112 (3)°

V = 572.31 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.44 × 0.21 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire3 detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.585, T max = 1.000

7178 measured reflections

1013 independent reflections

902 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.114

S = 1.06

1013 reflections

77 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813021090/ff2114sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813021090/ff2114Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813021090/ff2114Isup3.cml

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

C5H8O3	F(000) = 248
Mr = 116.11	Dx = 1.348 Mg m−3
Monoclinic, P21/c	Melting point = 303–306 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 4.8761 (2) Å	Cell parameters from 6623 reflections
b = 12.1025 (4) Å	θ = 3.4–34.5°
c = 9.8220 (3) Å	µ = 0.11 mm−1
β = 99.112 (3)°	T = 100 K
V = 572.31 (3) Å3	Polyhedron, colourless
Z = 4	0.44 × 0.21 × 0.16 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire3 detector	1013 independent reflections
Radiation source: fine-focus sealed tube	902 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 16.0328 pixels mm-1	θmax = 25.1°, θmin = 3.4°
ω scan	h = −5→4
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −14→14
Tmin = 0.585, Tmax = 1.000	l = −11→11
7178 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0797P)2 + 0.128P] where P = (Fo2 + 2Fc2)/3
1013 reflections	(Δ/σ)max < 0.001
77 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Experimental. CrysAlis RED (Oxford Diffraction, 2006). Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
O1	0.4194 (2)	0.16988 (8)	1.05179 (10)	0.0186 (3)
O2	0.3930 (2)	0.35384 (9)	1.06449 (12)	0.0286 (4)
O3	1.0589 (2)	0.31839 (8)	0.73324 (10)	0.0197 (3)
C1	0.4836 (3)	0.27238 (11)	1.01688 (14)	0.0159 (4)
C2	0.6782 (3)	0.27359 (12)	0.91177 (14)	0.0164 (4)
H2A	0.5932	0.2323	0.8288	0.020*
H2B	0.8537	0.2361	0.9505	0.020*
C3	0.7411 (3)	0.39098 (12)	0.87113 (14)	0.0170 (4)
H3A	0.5641	0.4276	0.8328	0.020*
H3B	0.8221	0.4319	0.9552	0.020*
C4	0.9364 (3)	0.39950 (11)	0.76733 (13)	0.0163 (4)
C5	0.9722 (3)	0.51213 (13)	0.70857 (16)	0.0242 (4)
H5A	1.1394	0.5130	0.6648	0.036*
H5B	0.9909	0.5671	0.7827	0.036*
H5C	0.8097	0.5299	0.6398	0.036*
H1	0.311 (4)	0.1766 (16)	1.108 (2)	0.036*

	U11	U22	U33	U12	U13	U23
O1	0.0253 (6)	0.0186 (6)	0.0137 (5)	−0.0011 (4)	0.0093 (4)	0.0006 (4)
O2	0.0435 (7)	0.0204 (6)	0.0275 (7)	0.0010 (5)	0.0231 (5)	−0.0016 (5)
O3	0.0240 (6)	0.0218 (6)	0.0148 (5)	0.0025 (4)	0.0072 (4)	0.0001 (4)
C1	0.0200 (7)	0.0187 (7)	0.0088 (7)	−0.0002 (6)	0.0020 (5)	0.0003 (5)
C2	0.0202 (7)	0.0187 (8)	0.0112 (7)	0.0017 (5)	0.0050 (5)	−0.0009 (5)
C3	0.0218 (7)	0.0183 (8)	0.0118 (7)	−0.0002 (5)	0.0060 (6)	−0.0015 (5)
C4	0.0183 (7)	0.0207 (8)	0.0092 (7)	0.0000 (5)	0.0001 (5)	−0.0016 (6)
C5	0.0334 (8)	0.0224 (8)	0.0195 (8)	0.0008 (6)	0.0125 (6)	0.0036 (6)

O1—C1	1.3373 (17)	C3—C4	1.5050 (19)
O1—H1	0.83 (2)	C3—H3A	0.9900
O2—C1	1.2044 (17)	C3—H3B	0.9900
O3—C4	1.2231 (17)	C4—C5	1.501 (2)
C1—C2	1.5092 (19)	C5—H5A	0.9800
C2—C3	1.520 (2)	C5—H5B	0.9800
C2—H2A	0.9900	C5—H5C	0.9800
C2—H2B	0.9900
C1—O1—H1	106.3 (14)	C4—C3—H3B	108.6
O2—C1—O1	123.01 (13)	C2—C3—H3B	108.6
O2—C1—C2	124.51 (13)	H3A—C3—H3B	107.6
O1—C1—C2	112.48 (12)	O3—C4—C5	122.14 (13)
C1—C2—C3	111.32 (12)	O3—C4—C3	121.30 (12)
C1—C2—H2A	109.4	C5—C4—C3	116.57 (12)
C3—C2—H2A	109.4	C4—C5—H5A	109.5
C1—C2—H2B	109.4	C4—C5—H5B	109.5
C3—C2—H2B	109.4	H5A—C5—H5B	109.5
H2A—C2—H2B	108.0	C4—C5—H5C	109.5
C4—C3—C2	114.68 (12)	H5A—C5—H5C	109.5
C4—C3—H3A	108.6	H5B—C5—H5C	109.5
C2—C3—H3A	108.6
O2—C1—C2—C3	−1.2 (2)	C2—C3—C4—O3	−8.66 (18)
O1—C1—C2—C3	178.42 (10)	C2—C3—C4—C5	171.36 (11)
C1—C2—C3—C4	179.46 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3i	0.83 (2)	1.87 (2)	2.6977 (13)	176 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3i	0.83 (2)	1.87 (2)	2.6977 (13)	176 (2)

Symmetry code: (i) .