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

Jiang, Y.; Men, J.; Liu, C.-Y.; Zhang, Y.; Gao, G.-W.

doi:10.1107/S1600536808009689

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o846

doi:10.1107/S1600536808009689

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

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

^aCollege of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China
^*Correspondence e-mail: gaosunday@yahoo.com.cn

(Received 29 March 2008; accepted 8 April 2008; online 16 April 2008)

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, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.056
wR(F²) = 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

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)
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x, -y, -z; (iii) x-1, y, z; (iv) -x-1, -y, -z+1.

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.

Supporting information

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

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

checkCIF report

Comment top

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.

Related literature top

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 top

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.

Computing details top

Data collection: DIFRAC (Gabe et al., 1993); cell refinement: 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).

Figures top

Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level.

1,1'-Biphenyl-2,3,3',4'-tetracarboxylic acid monohydrate top

Crystal data top

C₁₆H₁₀O₈·H₂O	Z = 2
M_r = 348.26	F(000) = 360
Triclinic, P1	D_x = 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

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.005
Radiation source: fine-focus sealed tube	θ_max = 25.5°, θ_min = 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 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)] = 0.056	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(F_o²) + (0.1334P)²] where P = (F_o² + 2F_c²)/3
2889 reflections	(Δ/σ)_max < 0.001
240 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₆H₁₀O₈·H₂O	γ = 94.47 (4)°
M_r = 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)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.005
3389 measured reflections	3 standard reflections every 250 reflections
2889 independent reflections	intensity decay: 1.4%
2074 reflections with I > 2σ(I)

Refinement top

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	Δρ_max = 0.35 e Å⁻³
2889 reflections	Δρ_min = −0.31 e Å⁻³
240 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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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)

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
M_r	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
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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···O7^iv	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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