Biphenyl-3,3'-dicarb-oxy-lic acid.

The asymmetric unit of the title compound, C(14)H(10)O(4), contains one half mol-ecule, the complete mol-ecule being generated by a twofold axis. The two benzene rings form a dihedral angle of 43.11 (5)°. Inter-molecular O-H⋯O hydrogen bonds link the mol-ecules into one-dimensional zigzag chains. These chains are further connected into two-dimensional supra-molecular layers by weak π-π stacking inter-actions between neighbouring benzene rings, with centroid-centroid distances of 3.7648 (8) Å.

Related literature

For general background non-covalent intermolecular interactions, see: Etter et al. (1990 ▶); Desiraju (2003 ▶); Yaghi et al. (2003 ▶); Li et al. (2010 ▶). For the structures of related complexes, see: Wang et al. (2005 ▶); Zhu (2010 ▶).

Experimental

Crystal data

C14H10O4

M = 242.22

Monoclinic,

a = 6.6123 (9) Å

b = 3.7648 (8) Å

c = 22.554 (3) Å

β = 93.14 (2)°

V = 560.61 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.21 × 0.18 × 0.13 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.978, T max = 0.986

5212 measured reflections

1286 independent reflections

1006 reflections with I > 2σ(I)

R int = 0.107

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.155

S = 1.04

1286 reflections

83 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811014334/zq2097sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014334/zq2097Isup2.hkl

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

C14H10O4	F(000) = 252
Mr = 242.22	Dx = 1.435 Mg m−3
Monoclinic, P2/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yac	Cell parameters from 1286 reflections
a = 6.6123 (9) Å	θ = 3.2–27.6°
b = 3.7648 (8) Å	µ = 0.11 mm−1
c = 22.554 (3) Å	T = 296 K
β = 93.14 (2)°	Prism, colourless
V = 560.61 (15) Å3	0.21 × 0.18 × 0.13 mm
Z = 2

Bruker SMART CCD diffractometer	1286 independent reflections
Radiation source: fine-focus sealed tube	1006 reflections with I > 2σ(I)
graphite	Rint = 0.107
φ and ω scans	θmax = 27.6°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.978, Tmax = 0.986	k = −4→4
5212 measured reflections	l = −29→28

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) = 0.155	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0843P)2] where P = (Fo2 + 2Fc2)/3
1286 reflections	(Δ/σ)max < 0.001
83 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.73331 (19)	0.2984 (4)	0.48869 (5)	0.0617 (5)
H1	0.6601	0.3923	0.5124	0.093*
C2	0.7741 (2)	0.2032 (4)	0.38631 (6)	0.0340 (4)
O2	0.48155 (17)	0.4652 (4)	0.42503 (5)	0.0527 (4)
C3	0.6866 (2)	0.2063 (4)	0.32849 (6)	0.0323 (4)
H3	0.5542	0.2860	0.3216	0.039*
C4	0.79643 (19)	0.0906 (4)	0.28086 (6)	0.0321 (4)
C1	0.6531 (2)	0.3318 (4)	0.43585 (6)	0.0373 (4)
C5	0.9952 (2)	−0.0282 (4)	0.29269 (7)	0.0384 (4)
H5	1.0701	−0.1063	0.2615	0.046*
C7	0.9722 (2)	0.0838 (4)	0.39736 (7)	0.0402 (4)
H7	1.0301	0.0811	0.4359	0.048*
C6	1.0825 (2)	−0.0316 (4)	0.35005 (8)	0.0421 (4)
H6	1.2149	−0.1110	0.3570	0.050*

	U11	U22	U33	U12	U13	U23
O1	0.0573 (8)	0.1005 (11)	0.0274 (6)	0.0284 (7)	0.0010 (5)	−0.0027 (6)
C2	0.0336 (7)	0.0401 (7)	0.0285 (7)	0.0010 (6)	0.0038 (5)	0.0021 (6)
O2	0.0415 (7)	0.0832 (9)	0.0336 (6)	0.0178 (6)	0.0024 (5)	−0.0019 (5)
C3	0.0270 (7)	0.0397 (7)	0.0305 (7)	0.0014 (5)	0.0030 (5)	0.0024 (5)
C4	0.0297 (7)	0.0374 (7)	0.0295 (8)	−0.0018 (5)	0.0033 (5)	0.0013 (5)
C1	0.0352 (8)	0.0475 (8)	0.0291 (7)	0.0020 (6)	0.0012 (5)	0.0009 (6)
C5	0.0294 (7)	0.0501 (9)	0.0363 (8)	0.0027 (6)	0.0071 (6)	−0.0010 (6)
C7	0.0350 (8)	0.0520 (9)	0.0332 (8)	0.0019 (6)	−0.0028 (5)	0.0037 (6)
C6	0.0272 (7)	0.0571 (9)	0.0418 (9)	0.0075 (6)	0.0014 (6)	0.0046 (7)

O1—C1	1.2837 (17)	C4—C5	1.400 (2)
O1—H1	0.8200	C4—C4i	1.490 (3)
C2—C7	1.394 (2)	C5—C6	1.388 (2)
C2—C3	1.3975 (19)	C5—H5	0.9300
C2—C1	1.490 (2)	C7—C6	1.394 (2)
O2—C1	1.2520 (18)	C7—H7	0.9300
C3—C4	1.399 (2)	C6—H6	0.9300
C3—H3	0.9300
C1—O1—H1	109.5	O2—C1—C2	120.13 (13)
C7—C2—C3	120.43 (13)	O1—C1—C2	116.90 (12)
C7—C2—C1	120.56 (13)	C6—C5—C4	121.26 (13)
C3—C2—C1	119.01 (12)	C6—C5—H5	119.4
C2—C3—C4	120.53 (12)	C4—C5—H5	119.4
C2—C3—H3	119.7	C2—C7—C6	119.28 (14)
C4—C3—H3	119.7	C2—C7—H7	120.4
C3—C4—C5	118.33 (13)	C6—C7—H7	120.4
C3—C4—C4i	120.83 (14)	C5—C6—C7	120.16 (13)
C5—C4—C4i	120.83 (14)	C5—C6—H6	119.9
O2—C1—O1	122.97 (13)	C7—C6—H6	119.9
C7—C2—C3—C4	−0.1 (2)	C3—C2—C1—O1	174.69 (14)
C1—C2—C3—C4	179.39 (13)	C3—C4—C5—C6	−0.1 (2)
C2—C3—C4—C5	0.1 (2)	C4i—C4—C5—C6	−179.54 (11)
C2—C3—C4—C4i	179.53 (10)	C3—C2—C7—C6	0.2 (2)
C7—C2—C1—O2	174.22 (14)	C1—C2—C7—C6	−179.33 (14)
C3—C2—C1—O2	−5.3 (2)	C4—C5—C6—C7	0.2 (2)
C7—C2—C1—O1	−5.8 (2)	C2—C7—C6—C5	−0.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ii	0.82	1.82	2.6268 (17)	169.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82	1.82	2.6268 (17)	169

Symmetry code: (i) .