Biphenyl-2,4,4′,6-tetra­carb­oxy­lic acid monohydrate

Wang, Y.-N.; Zhao, J.

doi:10.1107/S1600536813019624

organic compounds

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ISSN: 2056-9890

Volume 69| Part 9| September 2013| Page o1373

doi:10.1107/S1600536813019624

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Biphenyl-2,4,4′,6-tetracarboxylic acid monohydrate

Ye-Nan Wang ^a and Jun Zhao ^a ^*

^aCollege of Mechanical and Material Engineering, China Three Gorges University, Yichang 443002' , People's Republic of China
^*Correspondence e-mail: junzhao08@126.com

(Received 11 July 2013; accepted 16 July 2013; online 3 August 2013)

In the title compound, C₁₆H₁₀O₈·H₂O, the dihedral angle between the benzene rings is 71.59 (8)°. The COOH groups make dihedral angles of 10.3 (2), 30.8 (2), 11.3 (2) and 42.3 (2)° with their attached rings. In the crystal, O—H⋯O hydrogen bonds link the components forming a three-dimensional supramolecular network.

Related literature

For general background to the use of aromatic carboxylates as building blocks for the construction of various architectures, see: Yaghi et al. (2003 ); Zhao et al. (2012 ).

Experimental

Crystal data

C₁₆H₁₀O₈·H₂O
M_r = 348.26
Monoclinic, P 2₁ /c
a = 5.638 (4) Å
b = 16.160 (11) Å
c = 16.798 (12) Å
β = 92.524 (12)°
V = 1528.9 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 296 K
0.21 × 0.18 × 0.17 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.974, T_max = 0.979
15936 measured reflections
3516 independent reflections
3070 reflections with I > 2σ(I)
R_int = 0.124

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.152
S = 1.02
3516 reflections
232 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O3ⁱ	0.82	1.87	2.688 (2)	179
O4—H4B⋯O1Wⁱⁱ	0.82	1.91	2.725 (2)	177
O6—H6B⋯O8ⁱⁱⁱ	0.82	1.82	2.636 (2)	178
O7—H7B⋯O1W^iv	0.82	1.87	2.688 (2)	176
O1W—H1WB⋯O1	0.85 (1)	2.09 (1)	2.818 (2)	143 (2)
O1W—H1WA⋯O5^v	0.86 (1)	1.98 (1)	2.787 (2)	157 (2)
Symmetry codes: (i) -x, -y+2, -z; (ii) -x+1, -y+2, -z; (iii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (v) x, y, z+1.

Data collection: SMART (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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813019624/lh5634sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813019624/lh5634Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813019624/lh5634Isup3.cml

checkCIF report

Comment top

Aromatic carboxylates have been proven to be effective building blocks for the design and construction of coordination polymers exhibiting remarkable polymeric structural motifs due to their rich coordination modes (Yaghi et al.,2003; Zhao et al., 2012). Recently, we attempted to synthesize an Sm^III complex with the ligand in hydrothermal synthesis conditions. However the title organic salt was obtained, its structure is reported here.

The molecular structure of the title compound is shown in Fig. 1. The asymmetric unit comprises one bipheny1,2,4,4'6-tetracarboxylic acid and one solvent water molecule. The dihedral angle between the two benzene rings of the bipheny-1,2,4,4'6-tetracarboxylic acid is 71.59 (8)°. This may be the result of intermolecular O—H···O interactions and steric effects. In the crystal, extensive O—H···O hydrogen bonds invoving bipheny-1,2,4,4'6-tetracarboxylic acid molecules and water molecules link the components into a three-dimensional supramolecular network (Fig. 2).

Related literature top

For general background to the use of aromatic carboxylates as building blocks for the construction of various architectures, see: Yaghi et al. (2003); Zhao et al. (2012).

Experimental top

All chemicals were of reagent grade quality obtained from commercial sources and used without further purification. A mixture of bipheny1,2,4,4'6-tetracarboxylic acid (0.0370 g, 0.1 mmol), Sm(NO₃)₃.6H₂O (0.0444 g, 0.1 mmol) and water (12 ml) were placed in a 23 ml Teflon-lined stainless steel reactor and heated at 393 K for 2 days, and then cooled to room temperature at 10 K h^-1 to obtain colorless prism-shaped crystals suitable for X-ray analysis.

Computing details top

Data collection: SMART (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 top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids at the 50% probability level.
	Fig. 2. Part of the crystal structure with hydrogen bonds shown as dashed lines.

Biphenyl-2,4,4',6-tetracarboxylic acid monohydrate top

Crystal data top

C₁₆H₁₀O₈·H₂O	F(000) = 720
M_r = 348.26	D_x = 1.513 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2ybc	Cell parameters from 4298 reflections
a = 5.638 (4) Å	θ = 3.5–27.6°
b = 16.160 (11) Å	µ = 0.13 mm⁻¹
c = 16.798 (12) Å	T = 296 K
β = 92.524 (12)°	Prism, colorless
V = 1528.9 (19) Å³	0.21 × 0.18 × 0.17 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	3516 independent reflections
Radiation source: fine-focus sealed tube	3070 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.124
ϕ and ω scans	θ_max = 27.6°, θ_min = 3.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
T_min = 0.974, T_max = 0.979	k = −20→20
15936 measured reflections	l = −21→21

Refinement top

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.152	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0821P)² + 0.3015P] where P = (F_o² + 2F_c²)/3
3516 reflections	(Δ/σ)_max < 0.001
232 parameters	Δρ_max = 0.30 e Å⁻³
3 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₆H₁₀O₈·H₂O	V = 1528.9 (19) Å³
M_r = 348.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.638 (4) Å	µ = 0.13 mm⁻¹
b = 16.160 (11) Å	T = 296 K
c = 16.798 (12) Å	0.21 × 0.18 × 0.17 mm
β = 92.524 (12)°

Data collection top

Bruker SMART CCD diffractometer	3516 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3070 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.979	R_int = 0.124
15936 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	3 restraints
wR(F²) = 0.152	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.30 e Å⁻³
3516 reflections	Δρ_min = −0.26 e Å⁻³
232 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	−0.0695 (3)	0.89761 (9)	0.06051 (8)	0.0368 (3)
C2	−0.0558 (3)	0.89091 (9)	−0.02802 (8)	0.0319 (3)
C3	0.1413 (3)	0.85407 (10)	−0.06078 (8)	0.0369 (3)
H3A	0.2633	0.8333	−0.0274	0.044*
C4	0.1565 (3)	0.84821 (10)	−0.14271 (8)	0.0368 (3)
H4A	0.2885	0.8236	−0.1641	0.044*
C5	−0.0247 (2)	0.87892 (8)	−0.19285 (7)	0.0298 (3)
C6	−0.2205 (3)	0.91575 (10)	−0.15985 (8)	0.0367 (3)
H6A	−0.3424	0.9365	−0.1932	0.044*
C7	−0.2365 (3)	0.92190 (10)	−0.07773 (8)	0.0366 (3)
H7A	−0.3682	0.9468	−0.0563	0.044*
C8	−0.0256 (2)	0.87106 (8)	−0.28226 (7)	0.0291 (3)
C9	0.1157 (2)	0.92037 (8)	−0.33066 (7)	0.0303 (3)
C10	0.1001 (3)	0.91203 (9)	−0.41364 (8)	0.0336 (3)
H10A	0.2018	0.9420	−0.4448	0.040*
C11	−0.0664 (3)	0.85925 (9)	−0.44958 (7)	0.0336 (3)
C12	−0.2109 (3)	0.81166 (9)	−0.40302 (8)	0.0332 (3)
H12A	−0.3254	0.7773	−0.4270	0.040*
C13	−0.1844 (2)	0.81537 (8)	−0.32018 (7)	0.0305 (3)
C14	0.2767 (2)	0.98523 (9)	−0.29572 (8)	0.0316 (3)
C15	−0.0870 (3)	0.85389 (10)	−0.53843 (8)	0.0375 (3)
C16	−0.3229 (3)	0.75439 (9)	−0.27373 (8)	0.0325 (3)
O1W	0.24574 (18)	0.88370 (7)	0.26856 (6)	0.0378 (3)
H1WB	0.159 (3)	0.8987 (13)	0.2288 (8)	0.057*
O1	0.0881 (3)	0.87787 (9)	0.10711 (6)	0.0544 (4)
O2	−0.2753 (2)	0.92774 (10)	0.08217 (7)	0.0603 (4)
H2A	−0.2625	0.9434	0.1286	0.090*
O3	0.2393 (2)	1.02125 (8)	−0.23453 (6)	0.0467 (3)
O4	0.4623 (2)	1.00041 (8)	−0.33852 (7)	0.0479 (3)
H4B	0.5466	1.0353	−0.3159	0.072*
O5	0.0525 (3)	0.88594 (9)	−0.58157 (6)	0.0556 (4)
O6	−0.2751 (3)	0.81178 (9)	−0.56371 (6)	0.0564 (4)
H6B	−0.2663	0.8019	−0.6114	0.085*
O7	−0.5391 (2)	0.74324 (9)	−0.30234 (8)	0.0545 (4)
H7B	−0.5991	0.7040	−0.2796	0.082*
O8	−0.2375 (2)	0.71750 (8)	−0.21700 (7)	0.0511 (3)
H1WA	0.158 (3)	0.8750 (16)	0.3080 (9)	0.077*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0543 (8)	0.0375 (7)	0.0190 (6)	−0.0055 (6)	0.0060 (5)	−0.0034 (5)
C2	0.0443 (7)	0.0347 (7)	0.0171 (6)	−0.0052 (6)	0.0058 (5)	−0.0024 (5)
C3	0.0435 (7)	0.0483 (8)	0.0189 (6)	0.0039 (6)	0.0000 (5)	−0.0002 (5)
C4	0.0403 (7)	0.0500 (8)	0.0205 (6)	0.0055 (6)	0.0056 (5)	−0.0026 (6)
C5	0.0403 (7)	0.0347 (7)	0.0147 (6)	−0.0033 (5)	0.0041 (5)	−0.0009 (5)
C6	0.0408 (7)	0.0492 (8)	0.0201 (6)	0.0070 (6)	0.0010 (5)	−0.0016 (5)
C7	0.0421 (7)	0.0463 (8)	0.0219 (6)	0.0034 (6)	0.0065 (5)	−0.0053 (5)
C8	0.0387 (6)	0.0347 (7)	0.0142 (5)	0.0040 (5)	0.0038 (5)	−0.0009 (5)
C9	0.0413 (7)	0.0324 (7)	0.0173 (6)	0.0012 (5)	0.0031 (5)	−0.0014 (5)
C10	0.0469 (7)	0.0364 (7)	0.0179 (6)	−0.0033 (6)	0.0069 (5)	−0.0003 (5)
C11	0.0519 (8)	0.0349 (7)	0.0144 (6)	−0.0012 (6)	0.0042 (5)	−0.0004 (5)
C12	0.0479 (7)	0.0346 (7)	0.0173 (6)	−0.0039 (6)	0.0019 (5)	−0.0018 (5)
C13	0.0423 (7)	0.0328 (7)	0.0167 (6)	0.0003 (5)	0.0048 (5)	0.0009 (5)
C14	0.0396 (7)	0.0357 (7)	0.0196 (6)	0.0014 (5)	0.0019 (5)	0.0008 (5)
C15	0.0583 (9)	0.0386 (8)	0.0157 (6)	−0.0041 (6)	0.0040 (5)	−0.0024 (5)
C16	0.0468 (7)	0.0336 (7)	0.0177 (6)	−0.0005 (6)	0.0059 (5)	−0.0008 (5)
O1W	0.0384 (5)	0.0507 (6)	0.0245 (5)	0.0005 (4)	0.0056 (4)	−0.0009 (4)
O1	0.0762 (8)	0.0685 (9)	0.0182 (5)	0.0146 (7)	−0.0019 (5)	−0.0023 (5)
O2	0.0637 (7)	0.0971 (11)	0.0207 (5)	0.0110 (7)	0.0100 (5)	−0.0130 (6)
O3	0.0637 (7)	0.0513 (7)	0.0259 (5)	−0.0128 (5)	0.0106 (5)	−0.0143 (4)
O4	0.0489 (6)	0.0598 (7)	0.0362 (6)	−0.0160 (5)	0.0131 (5)	−0.0146 (5)
O5	0.0808 (9)	0.0689 (8)	0.0179 (5)	−0.0253 (7)	0.0126 (5)	−0.0035 (5)
O6	0.0769 (9)	0.0744 (9)	0.0178 (5)	−0.0256 (7)	0.0019 (5)	−0.0063 (5)
O7	0.0483 (6)	0.0621 (8)	0.0528 (8)	−0.0122 (6)	−0.0002 (5)	0.0241 (6)
O8	0.0701 (8)	0.0563 (7)	0.0265 (5)	−0.0137 (6)	−0.0031 (5)	0.0156 (5)

Geometric parameters (Å, º) top

C1—O1	1.201 (2)	C10—H10A	0.9300
C1—O2	1.324 (2)	C11—C12	1.387 (2)
C1—C2	1.496 (2)	C11—C15	1.494 (2)
C2—C7	1.382 (2)	C12—C13	1.394 (2)
C2—C3	1.395 (2)	C12—H12A	0.9300
C3—C4	1.386 (2)	C13—C16	1.498 (2)
C3—H3A	0.9300	C14—O3	1.2079 (19)
C4—C5	1.387 (2)	C14—O4	1.3181 (19)
C4—H4A	0.9300	C15—O5	1.210 (2)
C5—C6	1.391 (2)	C15—O6	1.314 (2)
C5—C8	1.507 (2)	C16—O8	1.2061 (19)
C6—C7	1.390 (2)	C16—O7	1.303 (2)
C6—H6A	0.9300	O1W—H1WB	0.845 (9)
C7—H7A	0.9300	O1W—H1WA	0.856 (9)
C8—C13	1.403 (2)	O2—H2A	0.8200
C8—C9	1.4099 (19)	O4—H4B	0.8200
C9—C10	1.399 (2)	O6—H6B	0.8200
C9—C14	1.490 (2)	O7—H7B	0.8200
C10—C11	1.387 (2)

O1—C1—O2	123.42 (14)	C11—C10—C9	120.31 (13)
O1—C1—C2	124.02 (15)	C11—C10—H10A	119.8
O2—C1—C2	112.56 (13)	C9—C10—H10A	119.8
C7—C2—C3	119.67 (13)	C12—C11—C10	119.92 (13)
C7—C2—C1	120.35 (13)	C12—C11—C15	120.62 (13)
C3—C2—C1	119.97 (13)	C10—C11—C15	119.46 (13)
C4—C3—C2	120.40 (13)	C11—C12—C13	119.94 (13)
C4—C3—H3A	119.8	C11—C12—H12A	120.0
C2—C3—H3A	119.8	C13—C12—H12A	120.0
C3—C4—C5	120.16 (13)	C12—C13—C8	121.27 (12)
C3—C4—H4A	119.9	C12—C13—C16	117.14 (12)
C5—C4—H4A	119.9	C8—C13—C16	121.51 (12)
C4—C5—C6	119.18 (13)	O3—C14—O4	123.16 (14)
C4—C5—C8	123.02 (12)	O3—C14—C9	123.23 (13)
C6—C5—C8	117.74 (12)	O4—C14—C9	113.60 (12)
C7—C6—C5	120.91 (13)	O5—C15—O6	124.40 (14)
C7—C6—H6A	119.5	O5—C15—C11	123.34 (14)
C5—C6—H6A	119.5	O6—C15—C11	112.26 (13)
C2—C7—C6	119.68 (13)	O8—C16—O7	123.88 (14)
C2—C7—H7A	120.2	O8—C16—C13	122.53 (14)
C6—C7—H7A	120.2	O7—C16—C13	113.54 (12)
C13—C8—C9	117.81 (12)	H1WB—O1W—H1WA	108.9 (14)
C13—C8—C5	118.72 (12)	C1—O2—H2A	109.5
C9—C8—C5	123.37 (12)	C14—O4—H4B	109.5
C10—C9—C8	120.50 (13)	C15—O6—H6B	109.5
C10—C9—C14	118.09 (12)	C16—O7—H7B	109.5
C8—C9—C14	121.35 (12)

O1—C1—C2—C7	−174.12 (16)	C14—C9—C10—C11	−172.69 (13)
O2—C1—C2—C7	5.9 (2)	C9—C10—C11—C12	−2.9 (2)
O1—C1—C2—C3	5.1 (2)	C9—C10—C11—C15	177.47 (13)
O2—C1—C2—C3	−174.80 (15)	C10—C11—C12—C13	−1.6 (2)
C7—C2—C3—C4	−0.2 (2)	C15—C11—C12—C13	177.95 (13)
C1—C2—C3—C4	−179.45 (14)	C11—C12—C13—C8	4.8 (2)
C2—C3—C4—C5	−0.1 (2)	C11—C12—C13—C16	−172.06 (13)
C3—C4—C5—C6	0.2 (2)	C9—C8—C13—C12	−3.2 (2)
C3—C4—C5—C8	−177.01 (14)	C5—C8—C13—C12	173.20 (13)
C4—C5—C6—C7	−0.1 (2)	C9—C8—C13—C16	173.50 (12)
C8—C5—C6—C7	177.24 (13)	C5—C8—C13—C16	−10.09 (19)
C3—C2—C7—C6	0.3 (2)	C10—C9—C14—O3	148.67 (15)
C1—C2—C7—C6	179.54 (14)	C8—C9—C14—O3	−28.5 (2)
C5—C6—C7—C2	−0.1 (2)	C10—C9—C14—O4	−30.44 (18)
C4—C5—C8—C13	107.63 (17)	C8—C9—C14—O4	152.42 (13)
C6—C5—C8—C13	−69.63 (18)	C12—C11—C15—O5	−170.64 (17)
C4—C5—C8—C9	−76.17 (19)	C10—C11—C15—O5	9.0 (2)
C6—C5—C8—C9	106.56 (17)	C12—C11—C15—O6	10.4 (2)
C13—C8—C9—C10	−1.40 (19)	C10—C11—C15—O6	−170.01 (15)
C5—C8—C9—C10	−177.63 (12)	C12—C13—C16—O8	136.42 (16)
C13—C8—C9—C14	175.67 (12)	C8—C13—C16—O8	−40.4 (2)
C5—C8—C9—C14	−0.6 (2)	C12—C13—C16—O7	−41.20 (19)
C8—C9—C10—C11	4.5 (2)	C8—C13—C16—O7	141.96 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3ⁱ	0.82	1.87	2.688 (2)	179
O4—H4B···O1Wⁱⁱ	0.82	1.91	2.725 (2)	177
O6—H6B···O8ⁱⁱⁱ	0.82	1.82	2.636 (2)	178
O7—H7B···O1W^iv	0.82	1.87	2.688 (2)	176
O1W—H1WB···O1	0.85 (1)	2.09 (1)	2.818 (2)	143 (2)
O1W—H1WA···O5^v	0.86 (1)	1.98 (1)	2.787 (2)	157 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3ⁱ	0.82	1.87	2.688 (2)	178.9
O4—H4B···O1Wⁱⁱ	0.82	1.91	2.725 (2)	176.6
O6—H6B···O8ⁱⁱⁱ	0.82	1.82	2.636 (2)	177.9
O7—H7B···O1W^iv	0.82	1.87	2.688 (2)	176.3
O1W—H1WB···O1	0.845 (9)	2.093 (14)	2.818 (2)	143 (2)
O1W—H1WA···O5^v	0.856 (9)	1.981 (12)	2.787 (2)	157 (2)

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

Acknowledgements

The authors are grateful to the Natural Science Foundation of Hubei Province of China (grant No. 2010CDB10707) and the Project of Hubei Provincial Education Office (grant No. Q20101203).

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