organic compounds
1,1′-Biphenyl-2,3,3′,4′-tetracarboxylic acid monohydrate
aCollege of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China
*Correspondence e-mail: gaosunday@yahoo.com.cn
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
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Data collection
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Refinement
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Data collection: DIFRAC (Gabe et al., 1993); cell 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.
Supporting information
10.1107/S1600536808009689/xu2413sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808009689/xu2413Isup2.hkl
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.
H atoms of the water molecule were located in a difference Fourier map and refined isotropically. Other H atoms were positioned geometrically with C—H = 0.93 Å and O—H = 0.82 Å, and refined using a riding model with Uiso(H) = 1.2Ueq(C,O).
Data collection: DIFRAC (Gabe et al., 1993); cell
DIFRAC (Gabe et al., 1993); 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 (Sheldrick, 2008).Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level. |
C16H10O8·H2O | Z = 2 |
Mr = 348.26 | F(000) = 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 = 4.5–7.5° |
c = 11.562 (4) Å | µ = 0.13 mm−1 |
α = 118.14 (3)° | T = 294 K |
β = 97.34 (3)° | Block, colourless |
γ = 94.47 (4)° | 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 = 25.5°, θmin = 2.0° |
Graphite monochromator | h = −8→8 |
ω/2θ scans | k = −5→13 |
3389 measured reflections | l = −13→12 |
2889 independent reflections | 3 standard reflections every 250 reflections |
2074 reflections with I > 2σ(I) | intensity decay: 1.4% |
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)] = 0.056 | Hydrogen site location: mixed |
wR(F2) = 0.178 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.98 | Calculated w = 1/[σ2(Fo2) + (0.1334P)2] where P = (Fo2 + 2Fc2)/3 |
2889 reflections | (Δ/σ)max < 0.001 |
240 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
C16H10O8·H2O | γ = 94.47 (4)° |
Mr = 348.26 | V = 776.7 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.860 (3) Å | Mo Kα radiation |
b = 11.339 (5) Å | µ = 0.13 mm−1 |
c = 11.562 (4) Å | T = 294 K |
α = 118.14 (3)° | 0.44 × 0.36 × 0.18 mm |
β = 97.34 (3)° |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.005 |
3389 measured reflections | 3 standard reflections every 250 reflections |
2889 independent reflections | intensity decay: 1.4% |
2074 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.178 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.98 | Δρmax = 0.35 e Å−3 |
2889 reflections | Δρmin = −0.31 e Å−3 |
240 parameters |
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) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y, −z; (iii) x−1, y, z; (iv) −x−1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C16H10O8·H2O |
Mr | 348.26 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 294 |
a, b, c (Å) | 6.860 (3), 11.339 (5), 11.562 (4) |
α, β, γ (°) | 118.14 (3), 97.34 (3), 94.47 (4) |
V (Å3) | 776.7 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.13 |
Crystal size (mm) | 0.44 × 0.36 × 0.18 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3389, 2889, 2074 |
Rint | 0.005 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.178, 0.98 |
No. of reflections | 2889 |
No. of parameters | 240 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.35, −0.31 |
Computer programs: DIFRAC (Gabe et al., 1993), NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 0.82 | 1.87 | 2.661 (3) | 163.2 |
O3—H3···O6ii | 0.82 | 1.89 | 2.640 (3) | 151.6 |
O5—H5···O9iii | 0.82 | 1.76 | 2.578 (3) | 172.9 |
O8—H8···O7iv | 0.82 | 1.84 | 2.634 (3) | 163.8 |
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) −x+1, −y+1, −z; (ii) −x, −y, −z; (iii) x−1, y, z; (iv) −x−1, −y, −z+1. |
Acknowledgements
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.
References
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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.