1,1′-Biphenyl-2,3,3′,4′-tetra­carboxylic acid monohydrate

Yan Jiang; Jian Men; Chong-Yi Liu; Yan Zhang; Guo-Wei Gao

doi:10.1107/S1600536808009689

. 2008 Apr 16;64(Pt 5):o846. doi: 10.1107/S1600536808009689

1,1′-Biphenyl-2,3,3′,4′-tetracarboxylic acid monohydrate

Yan Jiang ^a, Jian Men ^a, Chong-Yi Liu ^a, Yan Zhang ^a, Guo-Wei Gao ^a,^*

PMCID: PMC2961247 PMID: 21202334

Abstract

In the organic molecule of the title compound, C₁₆H₁₀O₈·H₂O, 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 _r = 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
Δρ_max = 0.35 e Å⁻³
Δρ_min = −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.

Supplementary Material

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

e-64-0o846-sup1.cif^{(16.5KB, cif)}

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

e-64-0o846-Isup2.hkl^{(141.8KB, hkl)}

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

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⋯O7^iv	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)

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

Acknowledgments

The authors are grateful to the National Undergraduates’ Innovative Experiment Project of China and the Undergraduates’ Innovative Experiment Project of Sichuan University for financial support, and thank Mr Zhi-Hua Mao of Sichuan University for the diffraction data collection.

supplementary crystallographic information

Comment

Aromatic polyimides are well accepted as high-performance polymeric materials because of their excellent thermal and mechanical properties at elevated temperatures (Adadie & Sillion, 1991); 2,3,3',4'-biphenyltetracarboxylic dianhydride is the most important monomer of aromatic polyimides and particularly useful in the preparation of soluble polyimides with high glass transition temperature and high thermoplasticity (Hasegawa et al., 1999; Hergenrother et al., 2004; Yang & Su, 2005). The title compound is a starting reagent for preparing 2,3,3',4'-biphenyltetracarboxylic dianhydride (Iataaki & Yoshimoto, 1973).

The molecular structure of the title compound is shown in Fig. 1. The dihedral angle between the two phenyl rings of 1,1'-biphenyl-2,3,3',4'-tetracarboxylic acid is 42.30 (11)°, which is markedly differ from 88.69° found in the 1,1'-biphenyl-2,2',3,3'-tetracarboxylic acid monohydrate (Holý et al., 2004). This might be a result of intermolecular O—H···O interactions and steric effects of the title compound. The lattice water molecule links with 1,1'-biphenyl-2,3,3',4'-tetracarboxylic acid via O—H···O hydrogen bonding (Table 1). The extensive O—H···O hydrogen bonding between 1,1'-biphenyl-2,3,3',4'-tetracarboxylic acid molecules helps to stabilize the crystal structure.

Experimental

2,3,3',4'-Tetramethyl biphenyltetracarboxylate (20.0 g, 52 mmol), concentrated hydrochloric acid (10 ml) and acetic acid (50 ml) in water (50 ml) were refluxed for 4 h. On concentrating the reaction mixture afforded the crude 1,1'-biphenyl-2,3,3',4'-tetracarboxylic acid. Recrystallization of the crude acid from water gave 1,1'-biphenyl-2,3,3',4'-tetracarboxylic acid (m.p. 468–470 K) (Iataaki & Yoshimoto, 1973). Colorless single crystals suitable for X-ray diffraction were obtained at room temperature by slow evaporation of water over a period of several days.