5-(Hy­droxy­meth­yl)furan-2-carb­oxy­lic acid

Liu, J.-L.; Xu, Q.-Y.

doi:10.1107/S1600536811019489

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1548

doi:10.1107/S1600536811019489

Open

access

5-(Hydroxymethyl)furan-2-carboxylic acid

Jun-Liang Liu ^a and Qing-Yan Xu ^a ^*

^aLaboratory of Microbial Pharmaceutical Engineering, Xiamen University, Xiamen 361005, People's Republic of China
^*Correspondence e-mail: xuqingyan@xmu.edu.cn

(Received 21 May 2011; accepted 23 May 2011; online 28 May 2011)

In the title compound, C₆H₆O₄, the furan ring is nearly coplanar with the carboxyl group, the maximum atomic deviation being 0.0248 (9) Å. The crystal packing is stabilized by classical O—H⋯O and weak C—H⋯O hydrogen bonding.

Related literature

For the biochemical significance of the title compound, see: Mrochek & Rainey (1972 ).

Experimental

Crystal data

C₆H₆O₄
M_r = 142.11
Orthorhombic, P b c a
a = 10.838 (3) Å
b = 7.2601 (17) Å
c = 15.526 (4) Å
V = 1221.7 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 294 K
0.32 × 0.22 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
5637 measured reflections
1098 independent reflections
1033 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.090
S = 1.08
1098 reflections
99 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O3ⁱ	0.87 (2)	1.83 (2)	2.6951 (16)	169.2 (19)
O4—H4A⋯O1ⁱⁱ	0.96 (2)	1.61 (2)	2.5643 (17)	171 (2)
C7—H7A⋯O4ⁱⁱⁱ	0.97	2.45	3.265 (2)	142
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x+2, -y, -z+1.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811019489/xu5218sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811019489/xu5218Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811019489/xu5218Isup3.cml

checkCIF report

Comment top

In the molecular structure of the compound, all the carbon atoms locate in the same plane. The crystal packing is stabilized by O—H···O and weak C—H···O hydrogen bonding (Table 1).

Related literature top

For the biochemical significance of the title compound, see: Mrochek & Rainey (1972).

Experimental top

The title compound was obtained from the fermentation of Aspergillus sp. by column chromatography. The strain was isolated from a soil sample collected from Jinjiang salt-field, Fujian, China. The strain was cultured using half sea-water Potato Dextrose Agar medium at 28 degrees celsius for 14 days. The fermentation (40 liters) was extracted with ethyl acetate (EtOAc). The EtOAc extract (18.0 g) eluted with methanol-water (30%, 50%, 70%, 100%; V/V) to yield 12 fractions by column chromatography RP-18. Fraction 1 was further puried by Sephadex LH-20 (140 g) chromatography with methanol. Then 1–4 eluted with acetone by Sephadex LH-20 (80 g) chromatography, then the main components further puried by silica-gel column chromatography to afford the title compound (8.0 mg).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with 50% probability ellipsoids.

5-(Hydroxymethyl)furan-2-carboxylic acid top

Crystal data top

C₆H₆O₄	F(000) = 592
M_r = 142.11	D_x = 1.545 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 10988 reflections
a = 10.838 (3) Å	θ = 2.6–25.2°
b = 7.2601 (17) Å	µ = 0.13 mm⁻¹
c = 15.526 (4) Å	T = 294 K
V = 1221.7 (5) Å³	Block, colourless
Z = 8	0.32 × 0.22 × 0.12 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1033 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.025
Graphite monochromator	θ_max = 25.2°, θ_min = 2.6°
ϕ and ω scans	h = −12→12
5637 measured reflections	k = −8→8
1098 independent reflections	l = −18→13

Refinement top

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0457P)² + 0.5232P] where P = (F_o² + 2F_c²)/3
1098 reflections	(Δ/σ)_max = 0.001
99 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₆H₆O₄	V = 1221.7 (5) Å³
M_r = 142.11	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 10.838 (3) Å	µ = 0.13 mm⁻¹
b = 7.2601 (17) Å	T = 294 K
c = 15.526 (4) Å	0.32 × 0.22 × 0.12 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1033 reflections with I > 2σ(I)
5637 measured reflections	R_int = 0.025
1098 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.19 e Å⁻³
1098 reflections	Δρ_min = −0.21 e Å⁻³
99 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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

	x	y	z	U_iso*/U_eq
O1	0.93802 (10)	0.18266 (16)	0.31353 (7)	0.0276 (3)
O2	0.84194 (9)	0.14583 (14)	0.49749 (6)	0.0216 (3)
O3	0.68657 (9)	0.30625 (16)	0.68473 (7)	0.0300 (3)
O4	0.88618 (9)	0.26469 (16)	0.65427 (7)	0.0282 (3)
C5	0.74292 (13)	0.19201 (19)	0.54835 (9)	0.0204 (3)
C6	0.79370 (13)	0.08250 (18)	0.42169 (8)	0.0208 (3)
C7	0.88366 (14)	0.0247 (2)	0.35516 (9)	0.0262 (4)
H7A	0.9481	−0.0487	0.3817	0.031*
H7B	0.8424	−0.0510	0.3125	0.031*
C8	0.76830 (13)	0.2598 (2)	0.63503 (9)	0.0219 (3)
C9	0.66913 (13)	0.0865 (2)	0.42436 (9)	0.0243 (4)
H9A	0.6155	0.0498	0.3809	0.029*
C10	0.63590 (14)	0.1574 (2)	0.50616 (9)	0.0242 (3)
H10A	0.5564	0.1765	0.5268	0.029*
H4A	0.898 (2)	0.290 (3)	0.7143 (16)	0.060 (6)*
H1A	1.018 (2)	0.179 (3)	0.3204 (13)	0.051 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0203 (6)	0.0392 (7)	0.0235 (6)	−0.0018 (5)	0.0007 (4)	0.0040 (5)
O2	0.0178 (5)	0.0265 (6)	0.0205 (5)	0.0012 (4)	0.0005 (4)	−0.0004 (4)
O3	0.0213 (5)	0.0445 (7)	0.0242 (6)	0.0059 (5)	0.0039 (4)	−0.0031 (5)
O4	0.0188 (5)	0.0425 (7)	0.0231 (6)	0.0034 (5)	−0.0003 (4)	−0.0070 (5)
C5	0.0189 (7)	0.0215 (7)	0.0209 (7)	0.0024 (5)	0.0044 (6)	0.0035 (5)
C6	0.0257 (8)	0.0178 (7)	0.0188 (7)	−0.0001 (6)	−0.0015 (6)	0.0010 (5)
C7	0.0273 (8)	0.0281 (8)	0.0232 (8)	0.0002 (6)	0.0018 (6)	−0.0014 (6)
C8	0.0188 (7)	0.0223 (7)	0.0246 (7)	0.0016 (6)	0.0018 (6)	0.0030 (6)
C9	0.0237 (8)	0.0251 (8)	0.0242 (8)	−0.0019 (6)	−0.0038 (6)	−0.0003 (6)
C10	0.0179 (7)	0.0282 (8)	0.0265 (8)	0.0002 (6)	0.0021 (6)	0.0022 (6)

Geometric parameters (Å, º) top

O1—C7	1.4421 (19)	C5—C8	1.459 (2)
O1—H1A	0.88 (2)	C6—C9	1.351 (2)
O2—C6	1.3675 (17)	C6—C7	1.481 (2)
O2—C5	1.3739 (16)	C7—H7A	0.9700
O3—C8	1.2224 (18)	C7—H7B	0.9700
O4—C8	1.3124 (18)	C9—C10	1.417 (2)
O4—H4A	0.96 (2)	C9—H9A	0.9300
C5—C10	1.355 (2)	C10—H10A	0.9300

C7—O1—H1A	109.0 (13)	O1—C7—H7B	109.5
C6—O2—C5	106.15 (11)	C6—C7—H7B	109.5
C8—O4—H4A	111.1 (13)	H7A—C7—H7B	108.1
C10—C5—O2	110.21 (12)	O3—C8—O4	123.66 (14)
C10—C5—C8	132.03 (13)	O3—C8—C5	122.60 (13)
O2—C5—C8	117.72 (12)	O4—C8—C5	113.74 (12)
C9—C6—O2	110.38 (12)	C6—C9—C10	106.82 (13)
C9—C6—C7	133.27 (13)	C6—C9—H9A	126.6
O2—C6—C7	116.35 (12)	C10—C9—H9A	126.6
O1—C7—C6	110.88 (12)	C5—C10—C9	106.44 (13)
O1—C7—H7A	109.5	C5—C10—H10A	126.8
C6—C7—H7A	109.5	C9—C10—H10A	126.8

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O3ⁱ	0.87 (2)	1.83 (2)	2.6951 (16)	169.2 (19)
O4—H4A···O1ⁱⁱ	0.96 (2)	1.61 (2)	2.5643 (17)	171 (2)
C7—H7A···O4ⁱⁱⁱ	0.97	2.45	3.265 (2)	142

Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) x, −y+1/2, z+1/2; (iii) −x+2, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₆H₆O₄
M_r	142.11
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	294
a, b, c (Å)	10.838 (3), 7.2601 (17), 15.526 (4)
V (Å³)	1221.7 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.32 × 0.22 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5637, 1098, 1033
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.090, 1.08
No. of reflections	1098
No. of parameters	99
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.21

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O3ⁱ	0.87 (2)	1.83 (2)	2.6951 (16)	169.2 (19)
O4—H4A···O1ⁱⁱ	0.96 (2)	1.61 (2)	2.5643 (17)	171 (2)
C7—H7A···O4ⁱⁱⁱ	0.97	2.45	3.265 (2)	142

Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) x, −y+1/2, z+1/2; (iii) −x+2, −y, −z+1.

Acknowledgements

The authors acknowledge financial support by the Fundamental Research Funds for the Central Universities, China (2010121092).

References

Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Mrochek, J. & Rainey, W. (1972). Clin. Chem. 18, 821-828. CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar