Butane-1,2,3,4-tetra-carboxylic acid dihydrate.

The asymmetric unit of the title compound, C(8)H(10)O(8)·2H(2)O, contains one half-mol-ecule of butane-1,2,3,4-tetra-carboxylic acid and a water mol-ecule, with the complete tetra-acid generated by crystallographic inversion symmetry. Inter-molecular O-H⋯O hydrogen bonds form an extensive three-dimensional network, which consolidates the crystal packing.

Related literature

For applications of butane-1,2,3,4-tetra­carboxylic acid in metal -organic coordination polymers, see: Delgado et al. (2007 ▶); Liu et al. (2008 ▶). For related crystal structures, see: McKee et al. (2007 ▶); Najafpour et al. (2008 ▶).

Experimental

Crystal data

C8H10O8·2H2O

M = 270.19

Monoclinic,

a = 7.4668 (15) Å

b = 9.3385 (19) Å

c = 8.8406 (18) Å

β = 109.60 (3)°

V = 580.7 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.15 mm−1

T = 293 K

0.55 × 0.46 × 0.26 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.921, T max = 0.965

5478 measured reflections

1327 independent reflections

960 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.116

S = 1.17

1327 reflections

82 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.23 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809009970/cv2528sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009970/cv2528Isup2.hkl

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

C8H10O8·2H2O	F(000) = 284
Mr = 270.19	Dx = 1.545 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5478 reflections
a = 7.4668 (15) Å	θ = 3.3–27.4°
b = 9.3385 (19) Å	µ = 0.15 mm−1
c = 8.8406 (18) Å	T = 293 K
β = 109.60 (3)°	Platelet, colorless
V = 580.7 (2) Å3	0.55 × 0.46 × 0.26 mm
Z = 2

Rigaku R-AXIS RAPID diffractometer	1327 independent reflections
Radiation source: fine-focus sealed tube	960 reflections with I > 2σ(I)
graphite	Rint = 0.027
Detector resolution: 0 pixels mm-1	θmax = 27.4°, θmin = 3.3°
ω scans	h = −9→9
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −12→12
Tmin = 0.921, Tmax = 0.965	l = −11→11
5478 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 1.17	w = 1/[σ2(Fo2) + (0.0345P)2 + 0.3695P] where P = (Fo2 + 2Fc2)/3
1327 reflections	(Δ/σ)max < 0.001
82 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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	0.1296 (3)	0.38628 (19)	0.1509 (2)	0.0561 (5)
O2	0.0636 (2)	0.20225 (18)	−0.0167 (2)	0.0494 (5)
H2C	−0.0132	0.1808	0.0327	0.074*
C1	0.1546 (3)	0.3207 (2)	0.0422 (2)	0.0319 (5)
C2	0.2916 (3)	0.3636 (2)	−0.0416 (2)	0.0371 (5)
H2A	0.2201	0.3991	−0.1479	0.044*
H2B	0.3613	0.2795	−0.0547	0.044*
C3	0.4336 (3)	0.4784 (2)	0.0479 (2)	0.0294 (4)
H3A	0.3640	0.5630	0.0633	0.035*
C4	0.5554 (3)	0.4210 (2)	0.2107 (2)	0.0299 (4)
O3	0.6322 (3)	0.30568 (17)	0.23027 (19)	0.0510 (5)
O4	0.5724 (2)	0.50976 (17)	0.33017 (16)	0.0454 (4)
H4A	0.6470	0.4737	0.4186	0.068*
O5	0.8064 (2)	0.09678 (15)	0.10900 (16)	0.0369 (4)
H5A	0.7639	0.1616	0.1518	0.055*
H5B	0.8321	0.0309	0.1725	0.055*

	U11	U22	U33	U12	U13	U23
O1	0.0693 (12)	0.0600 (11)	0.0536 (10)	−0.0267 (9)	0.0398 (9)	−0.0219 (8)
O2	0.0483 (9)	0.0517 (10)	0.0578 (10)	−0.0243 (8)	0.0303 (8)	−0.0182 (8)
C1	0.0289 (10)	0.0377 (11)	0.0272 (9)	−0.0048 (8)	0.0069 (8)	0.0003 (8)
C2	0.0337 (10)	0.0477 (13)	0.0309 (10)	−0.0117 (9)	0.0124 (8)	−0.0073 (9)
C3	0.0267 (9)	0.0347 (11)	0.0286 (9)	−0.0025 (8)	0.0116 (8)	−0.0012 (8)
C4	0.0275 (9)	0.0348 (11)	0.0294 (9)	−0.0040 (8)	0.0122 (8)	−0.0023 (8)
O3	0.0669 (11)	0.0366 (9)	0.0451 (9)	0.0151 (8)	0.0126 (8)	−0.0019 (7)
O4	0.0549 (10)	0.0470 (9)	0.0278 (7)	0.0170 (7)	0.0054 (7)	−0.0057 (6)
O5	0.0434 (8)	0.0352 (8)	0.0358 (7)	−0.0005 (6)	0.0182 (6)	0.0018 (6)

O1—C1	1.206 (2)	C3—C3i	1.559 (3)
O2—C1	1.311 (2)	C3—H3A	0.9800
O2—H2C	0.8523	C4—O3	1.205 (2)
C1—C2	1.505 (3)	C4—O4	1.315 (2)
C2—C3	1.528 (3)	O4—H4A	0.8618
C2—H2A	0.9700	O5—H5A	0.8314
C2—H2B	0.9700	O5—H5B	0.8111
C3—C4	1.518 (3)
C1—O2—H2C	110.1	C4—C3—C3i	108.55 (18)
O1—C1—O2	123.13 (18)	C2—C3—C3i	110.94 (19)
O1—C1—C2	124.71 (18)	C4—C3—H3A	109.3
O2—C1—C2	112.15 (17)	C2—C3—H3A	109.3
C1—C2—C3	113.57 (16)	C3i—C3—H3A	109.3
C1—C2—H2A	108.9	O3—C4—O4	122.30 (18)
C3—C2—H2A	108.9	O3—C4—C3	123.80 (18)
C1—C2—H2B	108.9	O4—C4—C3	113.89 (17)
C3—C2—H2B	108.9	C4—O4—H4A	110.0
H2A—C2—H2B	107.7	H5A—O5—H5B	105.9
C4—C3—C2	109.54 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2C···O5ii	0.85	1.87	2.707 (2)	167
O4—H4A···O5iii	0.86	1.83	2.689 (2)	178
O5—H5A···O3	0.83	1.93	2.754 (2)	172
O5—H5B···O1iv	0.81	2.01	2.814 (2)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2C⋯O5i	0.85	1.87	2.707 (2)	167
O4—H4A⋯O5ii	0.86	1.83	2.689 (2)	178
O5—H5A⋯O3	0.83	1.93	2.754 (2)	172
O5—H5B⋯O1iii	0.81	2.01	2.814 (2)	170

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