Biphenyl-2,2',4,4'-tetra-carb-oxy-lic acid monohydrate.

In the title compound, C(16)H(10)O(8)·H(2)O, the dihedral angle between the two benzene rings is 71.63 (5)°. In the crystal structure, pairs of inversion-related mol-ecules are stacked [mean inter-planar spacing = 3.5195 (18) Å], and O-H⋯O and C-H⋯O hydrogen bonds create a three-dimensional network.

Related literature

For general background to the use of aromatic carboxyl­ates as building blocks for the construction of various architectures, see: Li et al. (2008 ▶); Du et al. (2007 ▶). For previous studies on the synthesis of aromatic carboxyl­ate hydrates, see: Jiang et al. (2008 ▶); Li et al. (2009 ▶).

Experimental

Crystal data

C16H10O8·H2O

M = 348.26

Triclinic,

a = 7.1765 (1) Å

b = 9.4677 (2) Å

c = 11.9301 (2) Å

α = 106.013 (1)°

β = 100.098 (1)°

γ = 96.753 (1)°

V = 755.18 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.13 mm−1

T = 296 K

0.22 × 0.20 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.972, T max = 0.976

13177 measured reflections

2663 independent reflections

2441 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.123

S = 1.03

2663 reflections

236 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.41 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810037438/pk2260sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037438/pk2260Isup2.hkl

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

C16H10O8·H2O	Z = 2
Mr = 348.26	F(000) = 360
Triclinic, P1	Dx = 1.532 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1765 (1) Å	Cell parameters from 9316 reflections
b = 9.4677 (2) Å	θ = 2.8–27.5°
c = 11.9301 (2) Å	µ = 0.13 mm−1
α = 106.013 (1)°	T = 296 K
β = 100.098 (1)°	Block, yellow
γ = 96.753 (1)°	0.22 × 0.20 × 0.19 mm
V = 755.18 (2) Å3

Bruker APEXII CCD area-detector diffractometer	2663 independent reflections
Radiation source: fine-focus sealed tube	2441 reflections with I > 2σ(I)
graphite	Rint = 0.019
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −8→8
Tmin = 0.972, Tmax = 0.976	k = −11→11
13177 measured reflections	l = −14→14

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) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0701P)2 + 0.3599P] where P = (Fo2 + 2Fc2)/3
2663 reflections	(Δ/σ)max < 0.001
236 parameters	Δρmax = 0.22 e Å−3
3 restraints	Δρmin = −0.40 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	0.7651 (3)	1.4462 (2)	0.51405 (19)	0.0815 (6)
H1A	0.8362	1.4851	0.4799	0.122*
O2	1.0447 (2)	1.4309 (2)	0.61981 (17)	0.0734 (5)
O3	0.19262 (18)	1.12724 (18)	0.49778 (13)	0.0522 (4)
H3A	0.0770	1.0941	0.4759	0.078*
O4	0.17196 (18)	0.97698 (17)	0.60878 (13)	0.0518 (4)
O5	0.3535 (2)	1.20930 (14)	0.88045 (14)	0.0531 (4)
O6	0.1817 (2)	1.07466 (14)	0.96298 (13)	0.0448 (3)
H6A	0.1502	1.1551	0.9916	0.067*
O7	0.4508 (2)	0.46084 (14)	0.83504 (15)	0.0531 (4)
H7A	0.4132	0.3873	0.8539	0.080*
O8	0.2313 (2)	0.55361 (14)	0.92899 (13)	0.0474 (4)
O9	0.1086 (2)	1.34013 (16)	1.05603 (16)	0.0556 (4)
C1	0.7674 (2)	1.1428 (2)	0.77090 (16)	0.0376 (4)
H1	0.8355	1.1113	0.8306	0.045*
C2	0.8611 (3)	1.2492 (2)	0.73154 (17)	0.0398 (4)
H2	0.9908	1.2877	0.7640	0.048*
C3	0.7614 (2)	1.29848 (19)	0.64325 (15)	0.0341 (4)
C4	0.5674 (2)	1.24238 (18)	0.59864 (14)	0.0308 (4)
H4	0.4990	1.2783	0.5419	0.037*
C5	0.4723 (2)	1.13359 (17)	0.63672 (13)	0.0273 (3)
C6	0.5744 (2)	1.08125 (17)	0.72423 (14)	0.0283 (4)
C7	0.4997 (2)	0.95149 (17)	0.76245 (14)	0.0278 (3)
C8	0.3751 (2)	0.95295 (17)	0.84121 (14)	0.0275 (3)
C9	0.3250 (2)	0.82523 (17)	0.87296 (14)	0.0288 (4)
H9	0.2409	0.8259	0.9241	0.035*
C10	0.3984 (2)	0.69691 (17)	0.82967 (14)	0.0298 (4)
C11	0.5231 (3)	0.69593 (18)	0.75326 (15)	0.0346 (4)
H11	0.5729	0.6103	0.7236	0.041*
C12	0.5734 (2)	0.82211 (19)	0.72119 (15)	0.0337 (4)
H12	0.6588	0.8206	0.6707	0.040*
C13	0.8643 (3)	1.4007 (2)	0.59059 (18)	0.0441 (5)
C14	0.2659 (2)	1.07440 (18)	0.57925 (14)	0.0289 (4)
C15	0.3025 (2)	1.09080 (18)	0.89507 (15)	0.0305 (4)
C16	0.3493 (2)	0.56452 (18)	0.86928 (15)	0.0326 (4)
H9B	0.0046 (19)	1.370 (2)	1.0685 (19)	0.049*
H9A	0.177 (2)	1.4042 (19)	1.037 (2)	0.049*

	U11	U22	U33	U12	U13	U23
O1	0.0562 (10)	0.1074 (15)	0.0975 (14)	−0.0142 (10)	0.0034 (9)	0.0776 (12)
O2	0.0451 (9)	0.0946 (13)	0.0903 (13)	−0.0128 (8)	0.0080 (8)	0.0581 (11)
O3	0.0305 (7)	0.0725 (10)	0.0609 (9)	−0.0063 (6)	−0.0048 (6)	0.0472 (8)
O4	0.0309 (7)	0.0645 (9)	0.0665 (9)	−0.0116 (6)	−0.0020 (6)	0.0463 (8)
O5	0.0791 (10)	0.0269 (7)	0.0717 (10)	0.0150 (6)	0.0410 (8)	0.0268 (6)
O6	0.0483 (8)	0.0325 (7)	0.0667 (9)	0.0130 (6)	0.0330 (7)	0.0210 (6)
O7	0.0648 (9)	0.0334 (7)	0.0836 (10)	0.0199 (7)	0.0408 (8)	0.0341 (7)
O8	0.0514 (8)	0.0381 (7)	0.0709 (9)	0.0136 (6)	0.0310 (7)	0.0326 (7)
O9	0.0501 (9)	0.0410 (8)	0.0905 (11)	0.0181 (6)	0.0342 (8)	0.0280 (8)
C1	0.0303 (9)	0.0426 (10)	0.0421 (9)	−0.0012 (7)	0.0001 (7)	0.0243 (8)
C2	0.0291 (9)	0.0432 (10)	0.0462 (10)	−0.0070 (7)	0.0026 (7)	0.0210 (8)
C3	0.0327 (9)	0.0336 (9)	0.0372 (9)	−0.0034 (7)	0.0087 (7)	0.0158 (7)
C4	0.0323 (9)	0.0319 (8)	0.0319 (8)	0.0013 (7)	0.0071 (7)	0.0172 (7)
C5	0.0268 (8)	0.0283 (8)	0.0293 (8)	0.0022 (6)	0.0083 (6)	0.0125 (6)
C6	0.0290 (8)	0.0278 (8)	0.0306 (8)	0.0020 (6)	0.0081 (6)	0.0130 (6)
C7	0.0270 (8)	0.0286 (8)	0.0292 (8)	0.0011 (6)	0.0027 (6)	0.0147 (6)
C8	0.0264 (8)	0.0256 (8)	0.0328 (8)	0.0024 (6)	0.0051 (6)	0.0144 (6)
C9	0.0288 (8)	0.0274 (8)	0.0350 (8)	0.0029 (6)	0.0103 (6)	0.0156 (6)
C10	0.0315 (8)	0.0252 (8)	0.0349 (8)	0.0028 (6)	0.0063 (7)	0.0142 (6)
C11	0.0409 (9)	0.0277 (8)	0.0401 (9)	0.0095 (7)	0.0136 (7)	0.0138 (7)
C12	0.0378 (9)	0.0340 (9)	0.0356 (9)	0.0068 (7)	0.0148 (7)	0.0164 (7)
C13	0.0344 (10)	0.0508 (11)	0.0503 (11)	−0.0077 (8)	0.0054 (8)	0.0289 (9)
C14	0.0274 (8)	0.0321 (8)	0.0310 (8)	0.0028 (6)	0.0075 (6)	0.0159 (6)
C15	0.0309 (8)	0.0277 (8)	0.0371 (8)	0.0049 (6)	0.0078 (7)	0.0165 (7)
C16	0.0337 (9)	0.0264 (8)	0.0422 (9)	0.0048 (6)	0.0097 (7)	0.0170 (7)

O1—C13	1.260 (2)	C3—C4	1.384 (2)
O1—H1A	0.8200	C3—C13	1.486 (2)
O2—C13	1.256 (2)	C4—C5	1.391 (2)
O3—C14	1.274 (2)	C4—H4	0.9300
O3—H3A	0.8200	C5—C6	1.405 (2)
O4—C14	1.243 (2)	C5—C14	1.489 (2)
O5—C15	1.207 (2)	C6—C7	1.498 (2)
O6—C15	1.309 (2)	C7—C12	1.391 (2)
O6—H6A	0.8200	C7—C8	1.405 (2)
O7—C16	1.309 (2)	C8—C9	1.390 (2)
O7—H7A	0.8200	C8—C15	1.484 (2)
O8—C16	1.211 (2)	C9—C10	1.385 (2)
O9—H9B	0.852 (9)	C9—H9	0.9300
O9—H9A	0.843 (9)	C10—C11	1.384 (2)
C1—C2	1.378 (2)	C10—C16	1.483 (2)
C1—C6	1.389 (2)	C11—C12	1.380 (2)
C1—H1	0.9300	C11—H11	0.9300
C2—C3	1.387 (3)	C12—H12	0.9300
C2—H2	0.9300
C13—O1—H1A	109.5	C9—C8—C15	119.43 (14)
C14—O3—H3A	109.5	C7—C8—C15	120.93 (14)
C15—O6—H6A	109.5	C10—C9—C8	121.11 (15)
C16—O7—H7A	109.5	C10—C9—H9	119.4
H9B—O9—H9A	109.6 (14)	C8—C9—H9	119.4
C2—C1—C6	122.08 (16)	C11—C10—C9	119.36 (14)
C2—C1—H1	119.0	C11—C10—C16	120.69 (15)
C6—C1—H1	119.0	C9—C10—C16	119.91 (15)
C1—C2—C3	119.76 (16)	C12—C11—C10	119.95 (15)
C1—C2—H2	120.1	C12—C11—H11	120.0
C3—C2—H2	120.1	C10—C11—H11	120.0
C4—C3—C2	119.01 (15)	C11—C12—C7	121.64 (15)
C4—C3—C13	120.32 (16)	C11—C12—H12	119.2
C2—C3—C13	120.49 (16)	C7—C12—H12	119.2
C3—C4—C5	121.54 (15)	O2—C13—O1	123.66 (18)
C3—C4—H4	119.2	O2—C13—C3	118.64 (17)
C5—C4—H4	119.2	O1—C13—C3	117.59 (16)
C4—C5—C6	119.40 (14)	O4—C14—O3	122.26 (15)
C4—C5—C14	117.74 (14)	O4—C14—C5	121.23 (14)
C6—C5—C14	122.84 (14)	O3—C14—C5	116.51 (14)
C1—C6—C5	118.14 (14)	O5—C15—O6	122.33 (16)
C1—C6—C7	115.96 (14)	O5—C15—C8	123.22 (15)
C5—C6—C7	125.51 (14)	O6—C15—C8	114.42 (14)
C12—C7—C8	118.34 (14)	O8—C16—O7	123.12 (15)
C12—C7—C6	115.43 (14)	O8—C16—C10	124.19 (15)
C8—C7—C6	126.07 (14)	O7—C16—C10	112.68 (14)
C9—C8—C7	119.59 (15)
C6—C1—C2—C3	0.5 (3)	C8—C9—C10—C11	−0.2 (2)
C1—C2—C3—C4	1.7 (3)	C8—C9—C10—C16	177.30 (15)
C1—C2—C3—C13	−173.46 (18)	C9—C10—C11—C12	0.2 (3)
C2—C3—C4—C5	−2.7 (3)	C16—C10—C11—C12	−177.33 (16)
C13—C3—C4—C5	172.56 (16)	C10—C11—C12—C7	−0.9 (3)
C3—C4—C5—C6	1.3 (2)	C8—C7—C12—C11	1.7 (2)
C3—C4—C5—C14	−176.96 (15)	C6—C7—C12—C11	177.43 (15)
C2—C1—C6—C5	−1.9 (3)	C4—C3—C13—O2	−168.9 (2)
C2—C1—C6—C7	171.29 (17)	C2—C3—C13—O2	6.2 (3)
C4—C5—C6—C1	1.0 (2)	C4—C3—C13—O1	7.5 (3)
C14—C5—C6—C1	179.14 (15)	C2—C3—C13—O1	−177.4 (2)
C4—C5—C6—C7	−171.49 (15)	C4—C5—C14—O4	179.96 (16)
C14—C5—C6—C7	6.6 (2)	C6—C5—C14—O4	1.8 (3)
C1—C6—C7—C12	−67.3 (2)	C4—C5—C14—O3	0.9 (2)
C5—C6—C7—C12	105.40 (19)	C6—C5—C14—O3	−177.24 (16)
C1—C6—C7—C8	108.06 (19)	C9—C8—C15—O5	173.05 (17)
C5—C6—C7—C8	−79.3 (2)	C7—C8—C15—O5	−4.3 (3)
C12—C7—C8—C9	−1.7 (2)	C9—C8—C15—O6	−5.2 (2)
C6—C7—C8—C9	−176.93 (15)	C7—C8—C15—O6	177.43 (15)
C12—C7—C8—C15	175.65 (15)	C11—C10—C16—O8	−174.54 (17)
C6—C7—C8—C15	0.5 (2)	C9—C10—C16—O8	8.0 (3)
C7—C8—C9—C10	1.0 (2)	C11—C10—C16—O7	6.9 (2)
C15—C8—C9—C10	−176.42 (14)	C9—C10—C16—O7	−170.53 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O9	0.82	1.79	2.6076 (18)	174
C4—H4···O3	0.93	2.37	2.706 (2)	101
C9—H9···O6	0.93	2.38	2.711 (2)	101
O1—H1A···O2i	0.82	1.87	2.680 (2)	169
O3—H3A···O4ii	0.82	1.84	2.6400 (17)	166
O7—H7A···O5iii	0.82	1.82	2.6280 (17)	171
O9—H9B···O8iv	0.85 (1)	1.92 (1)	2.7616 (19)	170 (2)
O9—H9A···O8v	0.84 (1)	2.20 (1)	2.983 (2)	154 (2)
C12—H12···O3vi	0.93	2.57	3.451 (2)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6A⋯O9	0.82	1.79	2.6076 (18)	174
O1—H1A⋯O2i	0.82	1.87	2.680 (2)	169
O3—H3A⋯O4ii	0.82	1.84	2.6400 (17)	166
O7—H7A⋯O5iii	0.82	1.82	2.6280 (17)	171
O9—H9B⋯O8iv	0.85 (1)	1.92 (1)	2.7616 (19)	170 (2)
O9—H9A⋯O8v	0.84 (1)	2.20 (1)	2.983 (2)	154 (2)
C12—H12⋯O3vi	0.93	2.57	3.451 (2)	159

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