1,1′-Biphenyl-2,2′,5,5′-tetra­carb­oxy­lic acid

In the title compound, C₁₆H₁₀O₈ or H₄bptc, the dihedral angle between the planes of the phenyl rings is 51.90 (4)°. The asymmetric unit contains one half-mol­ecule; complete mol­ecules are generated by a twofold rotation axis. In the crystal, O—H...O and C—H...O hydrogen-bonding generate a two-dimensional supra­molecular network. In addition, weak π–π inter­actions are also observed.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.035
• wR factor = 0.099
• Data-to-parameter ratio = 10.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.4 Note

Alert level G
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still          68 %
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           4 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

1,1'-Biphenyl-2,2',5,5'-tetracarboxylic acid

Crystal data

C16H10O8	F(000) = 680
Mr = 330.24	Dx = 1.595 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.5105 (15) Å	Cell parameters from 4946 reflections
b = 7.7068 (7) Å	θ = 2.0–28.7°
c = 10.6885 (13) Å	µ = 0.13 mm^−1
β = 107.553 (1)°	T = 298 K
V = 1375.3 (2) Å^3	Block, colorless
Z = 4	0.22 × 0.19 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer	979 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
φ and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −20→20
Tmin = 0.679, Tmax = 0.746	k = −9→6
3734 measured reflections	l = −12→12
1227 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.035	w = 1/[σ^2(Fo^2) + (0.0493P)^2 + 0.7133P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.099	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.18 e Å^−3
1227 reflections	Δρmin = −0.18 e Å^−3
113 parameters

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.00860 (9)	0.2360 (2)	0.18570 (15)	0.0226 (4)
C2	−0.04525 (9)	0.2980 (2)	0.06844 (15)	0.0246 (4)
C3	−0.02754 (9)	0.2807 (2)	−0.04963 (16)	0.0291 (4)
H3	−0.0642	0.3189	−0.1271	0.035*
C4	0.04383 (10)	0.2077 (2)	−0.05290 (16)	0.0289 (4)
H4	0.0553	0.1973	−0.1320	0.035*
C5	0.09824 (9)	0.1500 (2)	0.06265 (16)	0.0264 (4)
C6	0.07976 (9)	0.1613 (2)	0.17983 (16)	0.0255 (4)
H6	0.1158	0.1180	0.2562	0.031*
C7	−0.12042 (9)	0.3912 (2)	0.06627 (16)	0.0279 (4)
C8	0.17699 (10)	0.0806 (2)	0.06039 (16)	0.0300 (4)
O1	−0.12872 (7)	0.46968 (17)	0.16061 (12)	0.0367 (4)
O2	−0.17566 (7)	0.3840 (2)	−0.04713 (12)	0.0498 (4)
H2	−0.2235 (13)	0.448 (3)	−0.0423 (7)	0.075*
O3	0.19187 (7)	0.04896 (19)	−0.04157 (12)	0.0443 (4)
O4	0.22832 (7)	0.0609 (2)	0.17623 (12)	0.0534 (5)
H4A	0.2783 (14)	0.021 (3)	0.1674 (3)	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0187 (8)	0.0260 (8)	0.0230 (8)	−0.0030 (6)	0.0059 (6)	−0.0011 (6)
C2	0.0186 (8)	0.0289 (9)	0.0258 (8)	−0.0002 (7)	0.0058 (7)	−0.0010 (7)
C3	0.0226 (8)	0.0394 (10)	0.0236 (9)	0.0040 (7)	0.0043 (7)	0.0007 (7)
C4	0.0285 (8)	0.0373 (10)	0.0231 (8)	0.0018 (8)	0.0109 (7)	−0.0014 (7)
C5	0.0207 (8)	0.0316 (10)	0.0270 (9)	0.0005 (7)	0.0075 (7)	−0.0028 (7)
C6	0.0194 (8)	0.0304 (9)	0.0251 (9)	0.0021 (7)	0.0044 (6)	0.0017 (7)
C7	0.0212 (8)	0.0362 (10)	0.0254 (9)	0.0027 (7)	0.0057 (7)	0.0024 (7)
C8	0.0238 (9)	0.0386 (10)	0.0280 (9)	0.0041 (7)	0.0084 (8)	−0.0030 (8)
O1	0.0270 (6)	0.0499 (8)	0.0329 (7)	0.0103 (6)	0.0085 (6)	−0.0054 (6)
O2	0.0270 (7)	0.0843 (11)	0.0315 (8)	0.0225 (7)	−0.0014 (6)	−0.0091 (7)
O3	0.0282 (7)	0.0753 (10)	0.0306 (7)	0.0160 (7)	0.0106 (6)	−0.0064 (7)
O4	0.0265 (7)	0.1027 (13)	0.0284 (7)	0.0241 (7)	0.0044 (6)	−0.0048 (7)

Geometric parameters (Å, º)

C1—C6	1.391 (2)	C5—C6	1.388 (2)
C1—C2	1.405 (2)	C5—C8	1.486 (2)
C1—C1^i	1.493 (3)	C6—H6	0.9300
C2—C3	1.394 (2)	C7—O1	1.221 (2)
C2—C7	1.494 (2)	C7—O2	1.3040 (19)
C3—C4	1.381 (2)	C8—O3	1.219 (2)
C3—H3	0.9300	C8—O4	1.301 (2)
C4—C5	1.386 (2)	O2—H2	0.99 (3)
C4—H4	0.9300	O4—H4A	0.96 (3)
C6—C1—C2	118.01 (14)	C4—C5—C8	119.52 (15)
C6—C1—C1^i	118.27 (16)	C6—C5—C8	120.50 (15)
C2—C1—C1^i	123.60 (15)	C5—C6—C1	121.52 (15)
C3—C2—C1	120.16 (14)	C5—C6—H6	119.2
C3—C2—C7	117.87 (14)	C1—C6—H6	119.2
C1—C2—C7	121.91 (14)	O1—C7—O2	123.28 (15)
C4—C3—C2	120.80 (15)	O1—C7—C2	123.30 (15)
C4—C3—H3	119.6	O2—C7—C2	113.40 (14)
C2—C3—H3	119.6	O3—C8—O4	123.70 (15)
C3—C4—C5	119.49 (15)	O3—C8—C5	122.41 (16)
C3—C4—H4	120.3	O4—C8—C5	113.87 (14)
C5—C4—H4	120.3	C7—O2—H2	109.5
C4—C5—C6	119.96 (14)	C8—O4—H4A	109.5
C6—C1—C2—C3	1.3 (2)	C2—C1—C6—C5	0.9 (2)
C1^i—C1—C2—C3	−174.80 (12)	C1^i—C1—C6—C5	177.23 (13)
C6—C1—C2—C7	−175.63 (15)	C3—C2—C7—O1	−151.99 (17)
C1^i—C1—C2—C7	8.3 (2)	C1—C2—C7—O1	25.0 (3)
C1—C2—C3—C4	−1.9 (3)	C3—C2—C7—O2	26.5 (2)
C7—C2—C3—C4	175.08 (16)	C1—C2—C7—O2	−156.53 (16)
C2—C3—C4—C5	0.4 (3)	C4—C5—C8—O3	−10.7 (3)
C3—C4—C5—C6	1.8 (3)	C6—C5—C8—O3	170.92 (17)
C3—C4—C5—C8	−176.53 (16)	C4—C5—C8—O4	167.89 (16)
C4—C5—C6—C1	−2.5 (2)	C6—C5—C8—O4	−10.5 (2)
C8—C5—C6—C1	175.82 (15)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O3^ii	0.93	2.52	3.438 (2)	168
O2—H2···O3^iii	0.99	1.67	2.6615 (17)	176
O4—H4A···O1^iv	0.96	1.70	2.6535 (16)	174

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