Biphenyl-2,2′,4,4′-tetra­carb­oxy­lic acid monohydrate

In the title compound, C₁₆H₁₀O₈·H₂O, the dihedral angle between the two benzene rings is 71.63 (5)°. In the crystal structure, pairs of inversion-related mol­ecules are stacked [mean inter­planar spacing = 3.5195 (18) Å], and O—H...O and C—H...O hydrogen bonds create a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.123
• Data-to-parameter ratio = 11.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O1     --  C13     ..       6.50 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O2     --  C13     ..       6.51 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.34
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              H2 O

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          3
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal  (x 10000)        100 Deg.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Aromatic carboxylates have been proven to be effective building blocks in constructing various architectures (Li et al., 2008; Du et al., 2007). Many crystal structures of aromatic carboxylic hydrates have been reported (Jiang et al., 2008; Li et al., 2009). In this paper, we report the synthesis and structure of a new aromatic carboxylic hydrate, biphenyl-2, 2', 4, 4' -tetracarboxylic acid monohydrate, (Fig. 1).

The dihedral angle between the two benzene rings of biphenyl-2, 2', 4, 4' -tetracarboxylic acid monohydrate is 71.63 (5)°, which is markedly different from 42.30 (11)° found in the biphenyl-2, 3, 3', 4'-tetracarboxylic acid monohydrate (Jiang et al., 2008). This might be a result of the hydrogen bonding ineractions of the title compound. The lattice water molecule links with biphenyl-2, 2', 4, 4'-tetracarboxylic acid via O—H···O hydrogen bonding. The extensive O—H···O hydrogen bonding and a weak intermolecular C—H···O hydrogen bond helps to stabilize the crystal structure (Fig. 2 and Table 1). In addition, pairs of inversion related molecules are stacked with mean interplanar spacing = 3.5195 (18)Å)

Related literature

For general background to the use of aromatic carboxylates as building blocks, 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).

S2. Experimental

A mixture of C₁₆H₁₀O₈ (0.3360 g), BaCl₂ (0.3451 g) and water (12 ml) was stirred at room temperature for 6 h. The solution was filtered and the filtrate was left to stand undisturbed. Upon slow evaporation at room temperature, a colorless crystalline solid appeared about a month later. The resulting colorless blocks were filtered off washed with water and dried at ambient temperature.

S3. Refinement

The H atoms of water molecules were located in difference Fourier maps and refined. All other hydrogen atoms were included in calculated positions and refined using a riding model with isotropic thermal parameters derived from the parent atoms (C—H = 0.93Å, O—H = 0.82 Å, U_iso (H) = 1.2Ueq (C) or 1.5Ueq (O)).

Computing details

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures

	Fig. 1. The structure of the title compound showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level
	Fig. 2. The O···H—O and C—H···O hydrogen bonds of biphenyl-2, 2', 4, 4' -tetracarboxylic acid monhydrate.

Biphenyl-2,2',4,4'-tetracarboxylic acid monohydrate

Crystal data

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) Å^3

Data collection

Bruker APEXII CCD area-detector diffractometer	2663 independent reflections
Radiation source: fine-focus sealed tube	2441 reflections with I > 2σ(I)
Graphite monochromator	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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0701P)^2 + 0.3599P] where P = (Fo^2 + 2Fc^2)/3
2663 reflections	(Δ/σ)max < 0.001
236 parameters	Δρmax = 0.22 e Å^−3
3 restraints	Δρmin = −0.41 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

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···O2^i	0.82	1.87	2.680 (2)	169
O3—H3A···O4^ii	0.82	1.84	2.6400 (17)	166
O7—H7A···O5^iii	0.82	1.82	2.6280 (17)	171
O9—H9B···O8^iv	0.85 (1)	1.92 (1)	2.7616 (19)	170 (2)
O9—H9A···O8^v	0.84 (1)	2.20 (1)	2.983 (2)	154 (2)
C12—H12···O3^vi	0.93	2.57	3.451 (2)	159

Symmetry codes: (i) −x+2, −y+3, −z+1; (ii) −x, −y+2, −z+1; (iii) x, y−1, z; (iv) −x, −y+2, −z+2; (v) x, y+1, z; (vi) −x+1, −y+2, −z+1.