1,1'-Biphenyl-2,3,3',4'-tetra-carboxylic acid monohydrate.

In the organic molecule of the title compound, C(16)H(10)O(8)·H(2)O, the dihedral angle between the two benzene rings is 42.30 (11)°. Extensive O-H⋯O hydrogen bonding helps to stabilize the crystal structure.

Related literature

For general background, see: Adadie & Sillion (1991 ▶); Hasegawa et al. (1999 ▶); Hergenrother et al. (2004 ▶); Iataaki & Yoshimoto (1973 ▶); Yang & Su (2005 ▶). For a related structure, see: Holý et al. (2004 ▶).

Experimental

Crystal data

C16H10O8·H2O

M = 348.26

Triclinic,

a = 6.860 (3) Å

b = 11.339 (5) Å

c = 11.562 (4) Å

α = 118.14 (3)°

β = 97.34 (3)°

γ = 94.47 (4)°

V = 776.7 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.13 mm−1

T = 294 (2) K

0.44 × 0.36 × 0.18 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

3389 measured reflections

2889 independent reflections

2074 reflections with I > 2σ(I)

R int = 0.004

3 standard reflections every 250 reflections intensity decay: 1.4%

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.178

S = 0.98

2889 reflections

240 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.31 e Å−3

Data collection: DIFRAC (Gabe et al., 1993 ▶); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808009689/xu2413sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808009689/xu2413Isup2.hkl

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

C16H10O8·H2O1	Z = 2
Mr = 348.26	F000 = 360
Triclinic, P1	Dx = 1.489 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 6.860 (3) Å	Cell parameters from 20 reflections
b = 11.339 (5) Å	θ = 4.5–7.5º
c = 11.562 (4) Å	µ = 0.13 mm−1
α = 118.14 (3)º	T = 294 (2) K
β = 97.34 (3)º	Block, colourless
γ = 94.47 (4)º	0.44 × 0.36 × 0.18 mm
V = 776.7 (5) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.005
Radiation source: fine-focus sealed tube	θmax = 25.5º
Monochromator: graphite	θmin = 2.0º
T = 294(2) K	h = −8→8
ω/2θ scans	k = −5→13
Absorption correction: none	l = −13→12
3389 measured reflections	3 standard reflections
2889 independent reflections	every 250 reflections
2074 reflections with I > 2σ(I)	intensity decay: 1.4%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.178	Calculated w = 1/[σ2(Fo2) + (0.1334P)2] where P = (Fo2 + 2Fc2)/3 ?
S = 0.98	(Δ/σ)max < 0.001
2889 reflections	Δρmax = 0.35 e Å−3
240 parameters	Δρmin = −0.31 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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 > 2σ(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	0.3911 (3)	0.4576 (2)	0.0916 (2)	0.0520 (6)
O2	0.3354 (3)	0.6316 (2)	0.0600 (2)	0.0554 (6)
H2	0.4355	0.6160	0.0268	0.066*
O3	0.0748 (3)	0.25686 (17)	0.03658 (17)	0.0392 (5)
H3	0.1426	0.1961	0.0167	0.047*
O4	0.2316 (3)	0.32664 (18)	0.24633 (18)	0.0397 (5)
O5	−0.5242 (3)	−0.05309 (17)	0.10577 (18)	0.0399 (5)
H5	−0.6058	−0.0072	0.1442	0.048*
O6	−0.2050 (3)	−0.02764 (18)	0.10600 (19)	0.0467 (5)
O7	−0.3954 (3)	−0.00002 (18)	0.37645 (19)	0.0455 (5)
O8	−0.4933 (3)	0.17283 (19)	0.54348 (19)	0.0462 (5)
H8	−0.5046	0.1186	0.5713	0.055*
C1	0.0408 (3)	0.4734 (2)	0.2032 (2)	0.0276 (5)
C2	0.1241 (4)	0.5721 (2)	0.1745 (2)	0.0310 (6)
C3	0.0495 (4)	0.6933 (3)	0.2149 (3)	0.0387 (6)
H3A	0.1048	0.7582	0.1958	0.046*
C4	−0.1069 (5)	0.7174 (3)	0.2834 (3)	0.0481 (7)
H4	−0.1573	0.7983	0.3103	0.058*
C5	−0.1882 (4)	0.6206 (3)	0.3119 (3)	0.0385 (6)
H5A	−0.2929	0.6380	0.3584	0.046*
C6	−0.1176 (4)	0.4980 (2)	0.2728 (2)	0.0288 (5)
C7	−0.2085 (3)	0.3987 (2)	0.3089 (2)	0.0267 (5)
C8	−0.2530 (4)	0.4447 (2)	0.4356 (2)	0.0302 (5)
H8A	−0.2322	0.5371	0.4954	0.036*
C9	−0.3284 (4)	0.3537 (2)	0.4735 (2)	0.0309 (5)
H9	−0.3589	0.3860	0.5583	0.037*
C10	−0.3590 (3)	0.2150 (2)	0.3867 (2)	0.0273 (5)
C11	−0.3206 (3)	0.1679 (2)	0.2579 (2)	0.0269 (5)
C12	−0.2489 (3)	0.2590 (2)	0.2192 (2)	0.0282 (5)
H12	−0.2273	0.2271	0.1324	0.034*
C13	0.2963 (4)	0.5479 (3)	0.1050 (3)	0.0346 (6)
C14	0.1296 (3)	0.3453 (2)	0.1646 (2)	0.0285 (5)
C15	−0.3477 (4)	0.0196 (2)	0.1528 (2)	0.0301 (5)
C16	−0.4193 (4)	0.1204 (2)	0.4366 (2)	0.0308 (5)
O9	0.2047 (4)	0.0732 (2)	0.2263 (2)	0.0527 (6)
H91	0.211 (5)	0.159 (4)	0.235 (3)	0.066 (10)*
H92	0.081 (7)	0.041 (4)	0.191 (4)	0.082 (13)*

	U11	U22	U33	U12	U13	U23
O1	0.0489 (12)	0.0604 (13)	0.0783 (15)	0.0237 (10)	0.0399 (11)	0.0501 (12)
O2	0.0559 (14)	0.0647 (14)	0.0816 (16)	0.0250 (11)	0.0441 (12)	0.0548 (13)
O3	0.0459 (11)	0.0341 (9)	0.0338 (10)	0.0160 (8)	0.0142 (8)	0.0104 (8)
O4	0.0435 (11)	0.0402 (10)	0.0395 (10)	0.0162 (8)	0.0110 (8)	0.0207 (8)
O5	0.0384 (10)	0.0297 (9)	0.0430 (11)	0.0004 (8)	0.0090 (8)	0.0112 (8)
O6	0.0426 (12)	0.0340 (10)	0.0509 (12)	0.0112 (8)	0.0223 (9)	0.0065 (8)
O7	0.0701 (14)	0.0338 (10)	0.0485 (11)	0.0211 (9)	0.0328 (10)	0.0256 (9)
O8	0.0685 (14)	0.0376 (10)	0.0486 (11)	0.0177 (9)	0.0372 (10)	0.0261 (9)
C1	0.0296 (13)	0.0263 (11)	0.0272 (12)	0.0041 (9)	0.0086 (9)	0.0125 (9)
C2	0.0302 (13)	0.0348 (12)	0.0328 (12)	0.0045 (10)	0.0100 (10)	0.0193 (10)
C3	0.0455 (16)	0.0335 (13)	0.0478 (15)	0.0080 (11)	0.0193 (12)	0.0256 (12)
C4	0.062 (2)	0.0344 (14)	0.0627 (19)	0.0210 (13)	0.0308 (15)	0.0287 (13)
C5	0.0379 (15)	0.0367 (13)	0.0493 (16)	0.0143 (11)	0.0251 (12)	0.0224 (12)
C6	0.0315 (13)	0.0271 (11)	0.0284 (12)	0.0047 (9)	0.0107 (9)	0.0128 (10)
C7	0.0234 (12)	0.0275 (11)	0.0312 (12)	0.0067 (9)	0.0112 (9)	0.0139 (10)
C8	0.0339 (13)	0.0236 (11)	0.0298 (12)	0.0048 (10)	0.0131 (10)	0.0085 (9)
C9	0.0326 (13)	0.0321 (12)	0.0277 (12)	0.0053 (10)	0.0128 (10)	0.0125 (10)
C10	0.0256 (12)	0.0292 (12)	0.0320 (12)	0.0072 (9)	0.0116 (9)	0.0168 (10)
C11	0.0227 (12)	0.0262 (11)	0.0311 (12)	0.0047 (9)	0.0087 (9)	0.0124 (10)
C12	0.0298 (12)	0.0285 (11)	0.0280 (12)	0.0048 (9)	0.0111 (9)	0.0138 (10)
C13	0.0336 (14)	0.0382 (13)	0.0383 (14)	0.0040 (11)	0.0118 (10)	0.0226 (11)
C14	0.0265 (12)	0.0301 (12)	0.0299 (12)	0.0039 (9)	0.0127 (9)	0.0137 (10)
C15	0.0325 (13)	0.0268 (11)	0.0306 (12)	0.0040 (10)	0.0112 (10)	0.0126 (10)
C16	0.0334 (14)	0.0318 (12)	0.0316 (12)	0.0077 (10)	0.0109 (10)	0.0174 (10)
O9	0.0371 (13)	0.0471 (12)	0.0768 (16)	0.0105 (10)	0.0122 (11)	0.0315 (11)

O1—C13	1.214 (3)	C4—C5	1.384 (4)
O2—C13	1.307 (3)	C4—H4	0.9300
O2—H2	0.8200	C5—C6	1.393 (4)
O3—C14	1.318 (3)	C5—H5A	0.9300
O3—H3	0.8200	C6—C7	1.494 (3)
O4—C14	1.213 (3)	C7—C8	1.389 (3)
O5—C15	1.302 (3)	C7—C12	1.403 (3)
O5—H5	0.8200	C8—C9	1.388 (3)
O6—C15	1.218 (3)	C8—H8A	0.9300
O7—C16	1.242 (3)	C9—C10	1.390 (3)
O8—C16	1.286 (3)	C9—H9	0.9300
O8—H8	0.8200	C10—C11	1.394 (3)
C1—C6	1.402 (3)	C10—C16	1.493 (3)
C1—C2	1.409 (3)	C11—C12	1.387 (3)
C1—C14	1.509 (3)	C11—C15	1.518 (3)
C2—C3	1.391 (4)	C12—H12	0.9300
C2—C13	1.483 (4)	O9—H91	0.92 (4)
C3—C4	1.383 (4)	O9—H92	0.86 (5)
C3—H3A	0.9300
C13—O2—H2	109.5	C7—C8—H8A	119.8
C14—O3—H3	109.5	C8—C9—C10	121.0 (2)
C15—O5—H5	109.5	C8—C9—H9	119.5
C16—O8—H8	109.5	C10—C9—H9	119.5
C6—C1—C2	119.7 (2)	C9—C10—C11	119.0 (2)
C6—C1—C14	120.6 (2)	C9—C10—C16	119.1 (2)
C2—C1—C14	119.6 (2)	C11—C10—C16	121.8 (2)
C3—C2—C1	120.2 (2)	C12—C11—C10	119.9 (2)
C3—C2—C13	120.2 (2)	C12—C11—C15	115.4 (2)
C1—C2—C13	119.6 (2)	C10—C11—C15	124.7 (2)
C4—C3—C2	120.0 (2)	C11—C12—C7	121.1 (2)
C4—C3—H3A	120.0	C11—C12—H12	119.4
C2—C3—H3A	120.0	C7—C12—H12	119.4
C3—C4—C5	119.7 (2)	O1—C13—O2	123.5 (3)
C3—C4—H4	120.1	O1—C13—C2	122.4 (2)
C5—C4—H4	120.1	O2—C13—C2	114.1 (2)
C4—C5—C6	121.8 (3)	O4—C14—O3	125.3 (2)
C4—C5—H5A	119.1	O4—C14—C1	122.0 (2)
C6—C5—H5A	119.1	O3—C14—C1	112.5 (2)
C5—C6—C1	118.5 (2)	O6—C15—O5	120.3 (2)
C5—C6—C7	119.4 (2)	O6—C15—C11	119.1 (2)
C1—C6—C7	122.1 (2)	O5—C15—C11	120.3 (2)
C8—C7—C12	118.4 (2)	O7—C16—O8	124.1 (2)
C8—C7—C6	119.5 (2)	O7—C16—C10	120.3 (2)
C12—C7—C6	122.1 (2)	O8—C16—C10	115.5 (2)
C9—C8—C7	120.5 (2)	H91—O9—H92	100 (4)
C9—C8—H8A	119.8

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.82	1.87	2.661 (3)	163
O3—H3···O6ii	0.82	1.89	2.640 (3)	152
O5—H5···O9iii	0.82	1.76	2.578 (3)	173
O8—H8···O7iv	0.82	1.84	2.634 (3)	164
O9—H91···O4	0.92 (4)	1.84 (4)	2.761 (3)	178 (3)
O9—H92···O6	0.86 (5)	1.99 (5)	2.853 (3)	178 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.82	1.87	2.661 (3)	163
O3—H3⋯O6ii	0.82	1.89	2.640 (3)	152
O5—H5⋯O9iii	0.82	1.76	2.578 (3)	173
O8—H8⋯O7iv	0.82	1.84	2.634 (3)	164
O9—H91⋯O4	0.92 (4)	1.84 (4)	2.761 (3)	178 (3)
O9—H92⋯O6	0.86 (5)	1.99 (5)	2.853 (3)	178 (4)

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