3-Hydr-oxy-3-(methoxy-carbon-yl)penta-nedioic acid.

In the title compound, C(7)H(10)O(7), the aliphatic chain is approximately planar [maximum deviation = 0.013 (1) Å] and makes a dihedral angle of 78.75 (7)° with the methoxy-carbonyl group. In the crystal, mol-ecules are linked via inter-molecular O-H⋯O and C-H⋯O hydrogen bonds into sheets parallel to (100). In the sheet, O-H⋯O hydrogen bonds generate R(2) (2)(9) and R(2) (2)(8) ring motifs.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C7H10O7

M = 206.15

Orthorhombic,

a = 12.7110 (4) Å

b = 5.8323 (2) Å

c = 23.8844 (7) Å

V = 1770.65 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.14 mm−1

T = 100 K

0.54 × 0.18 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.927, T max = 0.985

54585 measured reflections

4404 independent reflections

4059 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.107

S = 1.12

4404 reflections

167 parameters

All H-atom parameters refined

Δρmax = 0.56 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809025598/ci2844sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025598/ci2844Isup2.hkl

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

C7H10O7	F(000) = 864
Mr = 206.15	Dx = 1.547 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9850 reflections
a = 12.7110 (4) Å	θ = 3.2–36.7°
b = 5.8323 (2) Å	µ = 0.14 mm−1
c = 23.8844 (7) Å	T = 100 K
V = 1770.65 (10) Å3	Plate, colourless
Z = 8	0.54 × 0.18 × 0.11 mm

Bruker SMART APEXII CCD area-detector diffractometer	4404 independent reflections
Radiation source: fine-focus sealed tube	4059 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 36.7°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −21→21
Tmin = 0.927, Tmax = 0.985	k = −8→9
54585 measured reflections	l = −39→39

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	All H-atom parameters refined
S = 1.12	w = 1/[σ2(Fo2) + (0.0517P)2 + 0.4849P] where P = (Fo2 + 2Fc2)/3
4404 reflections	(Δ/σ)max = 0.001
167 parameters	Δρmax = 0.56 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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 > 2sigma(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	0.02576 (5)	0.61486 (11)	0.25826 (2)	0.01728 (11)
O2	0.17885 (5)	0.80419 (12)	0.24936 (3)	0.01938 (12)
O3	0.08405 (4)	0.23143 (9)	0.34206 (2)	0.01268 (10)
O4	0.12975 (5)	0.07178 (11)	0.47512 (3)	0.01837 (12)
O5	−0.02721 (4)	0.24507 (10)	0.46792 (2)	0.01487 (11)
O6	−0.11179 (4)	0.42068 (10)	0.35333 (2)	0.01375 (10)
O7	−0.04401 (4)	0.74583 (10)	0.38809 (3)	0.01586 (11)
C1	0.10969 (5)	0.67852 (13)	0.27732 (3)	0.01260 (11)
C2	0.14594 (5)	0.62879 (13)	0.33592 (3)	0.01235 (11)
C3	0.07801 (5)	0.45077 (12)	0.36661 (3)	0.01026 (11)
C4	0.12280 (5)	0.42501 (12)	0.42612 (3)	0.01211 (11)
C5	0.06767 (5)	0.23834 (12)	0.45814 (3)	0.01218 (11)
C6	−0.03676 (5)	0.53355 (12)	0.36864 (3)	0.01112 (11)
C7	−0.14757 (6)	0.85003 (15)	0.38333 (4)	0.02113 (15)
H2A	0.1457 (11)	0.771 (2)	0.3557 (6)	0.020 (3)*
H2B	0.2200 (10)	0.580 (2)	0.3349 (6)	0.021 (3)*
H4A	0.1116 (10)	0.567 (2)	0.4477 (6)	0.016 (3)*
H4B	0.1959 (10)	0.390 (2)	0.4241 (5)	0.015 (3)*
H7A	−0.1957 (12)	0.773 (3)	0.4079 (7)	0.033 (4)*
H7B	−0.1406 (11)	1.010 (3)	0.3934 (6)	0.023 (3)*
H7C	−0.1741 (14)	0.827 (3)	0.3455 (7)	0.039 (4)*
H1O2	0.1539 (13)	0.834 (3)	0.2177 (7)	0.038 (4)*
H1O3	0.0466 (12)	0.225 (3)	0.3117 (7)	0.032 (4)*
H1O4	0.0934 (14)	−0.032 (4)	0.4959 (8)	0.046 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0175 (2)	0.0178 (3)	0.0166 (2)	−0.00488 (19)	−0.00472 (18)	0.00421 (19)
O2	0.0153 (2)	0.0256 (3)	0.0172 (3)	−0.0040 (2)	−0.00089 (18)	0.0107 (2)
O3	0.0149 (2)	0.0102 (2)	0.0130 (2)	0.00161 (16)	−0.00136 (16)	−0.00159 (16)
O4	0.0142 (2)	0.0180 (3)	0.0229 (3)	0.00341 (19)	0.00330 (19)	0.0089 (2)
O5	0.0123 (2)	0.0159 (2)	0.0164 (2)	0.00103 (17)	0.00198 (16)	0.00301 (18)
O6	0.0111 (2)	0.0156 (2)	0.0145 (2)	−0.00290 (17)	−0.00018 (16)	−0.00210 (17)
O7	0.0116 (2)	0.0115 (2)	0.0245 (3)	0.00166 (17)	−0.00251 (18)	−0.00385 (19)
C1	0.0128 (2)	0.0115 (3)	0.0135 (3)	0.0001 (2)	0.00038 (19)	0.0027 (2)
C2	0.0111 (2)	0.0132 (3)	0.0128 (3)	−0.0015 (2)	−0.00051 (19)	0.0029 (2)
C3	0.0101 (2)	0.0097 (2)	0.0110 (2)	−0.00015 (19)	−0.00016 (18)	0.00032 (19)
C4	0.0120 (2)	0.0133 (3)	0.0110 (3)	−0.0015 (2)	−0.00097 (19)	0.0013 (2)
C5	0.0129 (2)	0.0136 (3)	0.0100 (2)	0.0004 (2)	0.00019 (18)	0.0006 (2)
C6	0.0110 (2)	0.0106 (3)	0.0118 (3)	−0.00047 (19)	−0.00006 (18)	0.0002 (2)
C7	0.0146 (3)	0.0169 (3)	0.0319 (4)	0.0051 (3)	−0.0034 (3)	−0.0041 (3)

O1—C1	1.2179 (9)	C2—C3	1.5365 (9)
O2—C1	1.3251 (9)	C2—H2A	0.956 (14)
O2—H1O2	0.838 (17)	C2—H2B	0.984 (13)
O3—C3	1.4094 (9)	C3—C6	1.5373 (9)
O3—H1O3	0.869 (16)	C3—C4	1.5386 (9)
O4—C5	1.3156 (9)	C4—C5	1.5037 (10)
O4—H1O4	0.91 (2)	C4—H4A	0.984 (13)
O5—C5	1.2290 (9)	C4—H4B	0.953 (13)
O6—C6	1.2152 (8)	C7—H7A	0.960 (16)
O7—C6	1.3256 (9)	C7—H7B	0.966 (15)
O7—C7	1.4543 (10)	C7—H7C	0.973 (17)
C1—C2	1.5020 (10)
C1—O2—H1O2	108.5 (12)	C5—C4—C3	111.60 (6)
C3—O3—H1O3	111.0 (11)	C5—C4—H4A	106.0 (8)
C5—O4—H1O4	110.8 (12)	C3—C4—H4A	110.4 (8)
C6—O7—C7	115.21 (6)	C5—C4—H4B	108.9 (8)
O1—C1—O2	124.15 (7)	C3—C4—H4B	109.6 (8)
O1—C1—C2	123.93 (6)	H4A—C4—H4B	110.4 (11)
O2—C1—C2	111.90 (6)	O5—C5—O4	123.61 (7)
C1—C2—C3	113.75 (6)	O5—C5—C4	122.06 (6)
C1—C2—H2A	107.0 (8)	O4—C5—C4	114.32 (6)
C3—C2—H2A	110.5 (8)	O6—C6—O7	123.84 (6)
C1—C2—H2B	109.1 (8)	O6—C6—C3	124.41 (6)
C3—C2—H2B	110.7 (8)	O7—C6—C3	111.74 (6)
H2A—C2—H2B	105.5 (12)	O7—C7—H7A	109.5 (10)
O3—C3—C2	112.60 (5)	O7—C7—H7B	107.5 (8)
O3—C3—C6	110.48 (5)	H7A—C7—H7B	111.0 (13)
C2—C3—C6	109.64 (5)	O7—C7—H7C	109.2 (10)
O3—C3—C4	106.00 (5)	H7A—C7—H7C	106.4 (14)
C2—C3—C4	107.38 (5)	H7B—C7—H7C	113.3 (13)
C6—C3—C4	110.65 (5)
O1—C1—C2—C3	11.29 (11)	C3—C4—C5—O4	120.28 (7)
O2—C1—C2—C3	−170.15 (6)	C7—O7—C6—O6	−7.76 (11)
C1—C2—C3—O3	65.49 (8)	C7—O7—C6—C3	170.92 (7)
C1—C2—C3—C6	−57.93 (8)	O3—C3—C6—O6	2.90 (9)
C1—C2—C3—C4	−178.20 (6)	C2—C3—C6—O6	127.56 (7)
O3—C3—C4—C5	−54.29 (7)	C4—C3—C6—O6	−114.18 (8)
C2—C3—C4—C5	−174.86 (6)	O3—C3—C6—O7	−175.77 (6)
C6—C3—C4—C5	65.51 (7)	C2—C3—C6—O7	−51.11 (8)
C3—C4—C5—O5	−60.67 (9)	C4—C3—C6—O7	67.15 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O6i	0.84 (2)	1.85 (2)	2.6838 (8)	173 (2)
O3—H1O3···O1ii	0.87 (2)	2.01 (2)	2.8549 (8)	163 (2)
O4—H1O4···O5iii	0.91 (2)	1.73 (2)	2.6391 (9)	176 (2)
C4—H4A···O5iv	0.99 (1)	2.53 (1)	3.4035 (9)	147 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯O6i	0.84 (2)	1.85 (2)	2.6838 (8)	173 (2)
O3—H1O3⋯O1ii	0.87 (2)	2.01 (2)	2.8549 (8)	163 (2)
O4—H1O4⋯O5iii	0.91 (2)	1.73 (2)	2.6391 (9)	176 (2)
C4—H4A⋯O5iv	0.99 (1)	2.53 (1)	3.4035 (9)	147 (1)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .