5-(Hy-droxy-meth-yl)furan-2-carb-oxy-lic acid.

In the title compound, C(6)H(6)O(4), 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 = 142.11

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.090

S = 1.08

1098 reflections

99 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.21 e Å−3

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.

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

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

Supplementary material file. DOI: 10.1107/S1600536811019489/xu5218Isup3.cml

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

C6H6O4	F(000) = 592
Mr = 142.11	Dx = 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

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

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(Fo2) + (0.0457P)2 + 0.5232P] where P = (Fo2 + 2Fc2)/3
1098 reflections	(Δ/σ)max = 0.001
99 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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

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

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) ; (ii) ; (iii) .