Biphenyl-3,3',4,4'-tetra-carboxylic acid dihydrate.

The asymmetric unit of the title compound, C(16)H(10)O(8)·2H(2)O, contains one-half of the centrosymmetric organic mol-ecule and one water mol-ecule. The dihedral angles between the carboxyl-ate groups and the adjacent phenyl ring are 71.31 (3) and 16.67 (3)°, while the carboxyl-ate groups are oriented at a dihedral angle of 72.01 (3)°. In the crystal structure, inter-molecular O-H⋯O and bifurcated O-H⋯(O,O) hydrogen bonds link the mol-ecules to form a three-dimensional supra-molecular network.

Related literature

For general background, see: Du et al. (2006 ▶, 2007 ▶); Desiraju (2003 ▶); Yaghi et al. (2003 ▶); Li et al. (2008 ▶). For a related structure, see: Coles et al. (2002 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H10O8·2H2O

M = 366.27

Triclinic,

a = 5.5858 (16) Å

b = 6.6618 (19) Å

c = 11.086 (3) Å

α = 93.126 (5)°

β = 91.404 (4)°

γ = 109.110 (4)°

V = 388.81 (19) Å3

Z = 1

Mo Kα radiation

μ = 0.13 mm−1

T = 296 (2) K

0.28 × 0.24 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.943, T max = 0.973

1992 measured reflections

1362 independent reflections

1222 reflections with I > 2σ(I)

R int = 0.008

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.090

S = 1.08

1362 reflections

120 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.16 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: SHELXTL (Sheldrick, 2008 ▶) and ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808044012/hk2568sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808044012/hk2568Isup2.hkl

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

C16H10O8·2H2O	Z = 1
Mr = 366.27	F(000) = 190
Triclinic, P1	Dx = 1.564 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.5858 (16) Å	Cell parameters from 1245 reflections
b = 6.6618 (19) Å	θ = 3.2–27.8°
c = 11.086 (3) Å	µ = 0.13 mm−1
α = 93.126 (5)°	T = 296 K
β = 91.404 (4)°	Block, colourless
γ = 109.110 (4)°	0.28 × 0.24 × 0.22 mm
V = 388.81 (19) Å3

Bruker SMART CCD area-detector diffractometer	1362 independent reflections
Radiation source: fine-focus sealed tube	1222 reflections with I > 2σ(I)
graphite	Rint = 0.008
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −6→6
Tmin = 0.943, Tmax = 0.973	k = −7→7
1992 measured reflections	l = −9→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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0467P)2 + 0.0831P] where P = (Fo2 + 2Fc2)/3
1362 reflections	(Δ/σ)max < 0.001
120 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.16 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	1.2031 (2)	0.8456 (2)	0.40618 (9)	0.0535 (3)
H1	1.2130	0.8530	0.4803	0.080*
O2	0.7989 (2)	0.6702 (2)	0.43405 (9)	0.0528 (3)
O3	0.8059 (2)	1.09274 (19)	0.35300 (9)	0.0501 (3)
O4	0.5352 (2)	1.08299 (18)	0.20056 (9)	0.0473 (3)
H4	0.4952	1.1658	0.2468	0.071*
O5	0.3760 (2)	0.35552 (17)	0.32212 (8)	0.0433 (3)
H5A	0.2608	0.2949	0.3695	0.065*
H5B	0.4996	0.4558	0.3561	0.065*
C1	0.9670 (3)	0.7526 (2)	0.36863 (12)	0.0355 (3)
C2	0.9236 (2)	0.7450 (2)	0.23342 (11)	0.0327 (3)
C3	1.0093 (3)	0.6076 (2)	0.16299 (12)	0.0352 (3)
H3	1.1062	0.5354	0.1992	0.042*
C4	0.9533 (3)	0.5744 (2)	0.03778 (11)	0.0329 (3)
C5	0.8074 (3)	0.6846 (3)	−0.01240 (12)	0.0426 (4)
H5	0.7650	0.6639	−0.0949	0.051*
C6	0.7238 (3)	0.8241 (3)	0.05735 (12)	0.0423 (4)
H6	0.6272	0.8963	0.0210	0.051*
C7	0.7815 (3)	0.8586 (2)	0.18104 (11)	0.0341 (3)
C8	0.7072 (3)	1.0210 (2)	0.25400 (12)	0.0349 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0436 (6)	0.0853 (9)	0.0246 (5)	0.0135 (6)	−0.0053 (4)	−0.0055 (5)
O2	0.0502 (7)	0.0738 (8)	0.0232 (5)	0.0062 (6)	0.0020 (5)	−0.0023 (5)
O3	0.0567 (7)	0.0651 (7)	0.0316 (6)	0.0290 (6)	−0.0118 (5)	−0.0202 (5)
O4	0.0621 (7)	0.0599 (7)	0.0298 (5)	0.0363 (6)	−0.0068 (5)	−0.0100 (5)
O5	0.0480 (6)	0.0484 (6)	0.0323 (5)	0.0154 (5)	0.0033 (4)	−0.0044 (4)
C1	0.0423 (8)	0.0418 (8)	0.0231 (7)	0.0164 (6)	−0.0016 (6)	−0.0054 (6)
C2	0.0342 (7)	0.0396 (7)	0.0216 (6)	0.0095 (6)	−0.0006 (5)	−0.0030 (5)
C3	0.0408 (8)	0.0430 (8)	0.0240 (7)	0.0175 (6)	−0.0019 (5)	−0.0016 (5)
C4	0.0375 (7)	0.0372 (7)	0.0226 (6)	0.0114 (6)	−0.0003 (5)	−0.0032 (5)
C5	0.0589 (10)	0.0540 (9)	0.0202 (7)	0.0276 (8)	−0.0063 (6)	−0.0065 (6)
C6	0.0559 (9)	0.0521 (9)	0.0265 (7)	0.0297 (8)	−0.0055 (6)	−0.0043 (6)
C7	0.0373 (7)	0.0390 (7)	0.0244 (7)	0.0113 (6)	−0.0004 (5)	−0.0036 (6)
C8	0.0381 (7)	0.0403 (8)	0.0250 (7)	0.0120 (6)	0.0007 (6)	−0.0025 (6)

O1—C1	1.3065 (18)	C2—C7	1.399 (2)
O1—H1	0.8200	C3—C4	1.4047 (19)
O2—C1	1.2031 (18)	C3—H3	0.9300
O3—C8	1.2156 (17)	C4—C5	1.388 (2)
O4—C8	1.3052 (17)	C4—C4i	1.492 (3)
O4—H4	0.8200	C5—C6	1.380 (2)
O5—H5A	0.8500	C5—H5	0.9300
O5—H5B	0.8502	C6—C7	1.3901 (19)
C1—C2	1.5080 (18)	C6—H6	0.9300
C2—C3	1.380 (2)	C7—C8	1.4874 (19)
C1—O1—H1	109.5	C3—C4—C4i	121.05 (15)
C8—O4—H4	109.5	C6—C5—C4	121.45 (13)
H5A—O5—H5B	114.3	C6—C5—H5	119.3
O2—C1—O1	123.81 (12)	C4—C5—H5	119.3
O2—C1—C2	122.09 (13)	C5—C6—C7	121.10 (14)
O1—C1—C2	114.00 (12)	C5—C6—H6	119.5
C3—C2—C7	120.53 (12)	C7—C6—H6	119.5
C3—C2—C1	117.84 (12)	C6—C7—C2	118.11 (13)
C7—C2—C1	121.39 (12)	C6—C7—C8	120.75 (13)
C2—C3—C4	121.34 (13)	C2—C7—C8	121.04 (12)
C2—C3—H3	119.3	O3—C8—O4	123.78 (13)
C4—C3—H3	119.3	O3—C8—C7	122.06 (13)
C5—C4—C3	117.43 (13)	O4—C8—C7	114.11 (11)
C5—C4—C4i	121.52 (14)
O2—C1—C2—C3	−104.45 (17)	C5—C6—C7—C2	−1.1 (2)
O1—C1—C2—C3	72.09 (17)	C5—C6—C7—C8	175.44 (14)
O2—C1—C2—C7	70.0 (2)	C3—C2—C7—C6	1.8 (2)
O1—C1—C2—C7	−113.51 (16)	C1—C2—C7—C6	−172.41 (13)
C7—C2—C3—C4	−1.2 (2)	C3—C2—C7—C8	−174.64 (12)
C1—C2—C3—C4	173.25 (13)	C1—C2—C7—C8	11.1 (2)
C2—C3—C4—C5	−0.3 (2)	C6—C7—C8—O3	−161.23 (14)
C2—C3—C4—C4i	−179.98 (15)	C2—C7—C8—O3	15.2 (2)
C3—C4—C5—C6	1.1 (2)	C6—C7—C8—O4	16.55 (19)
C4i—C4—C5—C6	−179.21 (16)	C2—C7—C8—O4	−167.06 (13)
C4—C5—C6—C7	−0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3ii	0.82	1.88	2.683 (3)	168
O4—H4···O5iii	0.82	1.79	2.599 (3)	169
O5—H5A···O3iv	0.85	2.45	3.129 (3)	137
O5—H5A···O2v	0.85	2.22	2.892 (3)	136
O5—H5B···O2	0.85	1.95	2.801 (3)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3i	0.82	1.88	2.683 (3)	168
O4—H4⋯O5ii	0.82	1.79	2.599 (3)	169
O5—H5A⋯O3iii	0.85	2.45	3.129 (3)	137
O5—H5A⋯O2iv	0.85	2.22	2.892 (3)	136
O5—H5B⋯O2	0.85	1.95	2.801 (3)	175

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