Bi­phenyl-3,3′,5,5′-tetra­carboxyl­ic acid

Coles, S.J.; Holmes, R.; Hursthouse, M.B.; Price, D.J.

doi:10.1107/S1600536802008206

Biphenyl-3,3',5,5'-tetracarboxylic acid

S. J. Coles, R. Holmes, M. B. Hursthouse and D. J. Price

The crystal structure of biphenyl-3,3',5,5'-tetracarboxylic acid, C₁₆H₁₀O₈, forms a supramolecular assembly of three interpenetrating corrugated sheets.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802008206/wn6094sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536802008206/wn6094Isup2.hkl Contains datablock I

CCDC reference: 189376

checkCIF report

Key indicators

Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.005 Å
R factor = 0.067
wR factor = 0.203
Data-to-parameter ratio = 13.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



RINTA_01  Alert C The value of Rint is greater than 0.10
          Rint given   0.122


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

Computing details top

Cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990).

(I) top

Crystal data top

C₁₆H₁₀O₈	F(000) = 680
M_r = 330.24	D_x = 1.643 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.1662 (7) Å	Cell parameters from 19752 reflections
b = 14.3524 (14) Å	θ = 1–27.5°
c = 12.093 (1) Å	µ = 0.14 mm⁻¹
β = 109.590 (4)°	T = 120 K
V = 1335.3 (2) Å³	Block, colourless
Z = 4	0.16 × 0.14 × 0.05 mm

Data collection top

Nonius KappaCCD diffractometer	1309 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.122
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	θ_max = 27.4°, θ_min = 2.7°
T_min = 0.979, T_max = 0.993	h = −10→10
16495 measured reflections	k = −18→18
2965 independent reflections	l = −15→15

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.067	w = 1/[σ²(F_o²) + (0.0991P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.203	(Δ/σ)_max = 0.001
S = 0.98	Δρ_max = 0.38 e Å⁻³
2965 reflections	Δρ_min = −0.29 e Å⁻³
221 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.

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

	x	y	z	U_iso*/U_eq
C1	0.4196 (4)	0.1490 (2)	−0.1141 (3)	0.0247 (8)
H1	0.3206	0.1694	−0.1768	0.03*
C2	0.4148 (4)	0.1477 (2)	−0.0007 (3)	0.0225 (8)
C3	0.5567 (4)	0.1156 (2)	0.0915 (3)	0.0256 (9)
H3	0.5523	0.1137	0.169	0.031*
C4	0.7057 (5)	0.0863 (2)	0.0694 (3)	0.0236 (8)
C5	0.7114 (4)	0.0897 (2)	−0.0435 (3)	0.0247 (8)
H5	0.8142	0.0708	−0.0575	0.03*
C6	0.5689 (4)	0.1206 (2)	−0.1372 (3)	0.0229 (8)
C7	0.2595 (5)	0.1863 (3)	0.0207 (3)	0.0275 (9)
C8	0.8621 (5)	0.0583 (3)	0.1682 (3)	0.0288 (9)
C9	0.5735 (4)	0.1246 (2)	−0.2592 (3)	0.0248 (8)
C10	0.7212 (4)	0.1547 (2)	−0.2815 (3)	0.0249 (8)
H10	0.8221	0.172	−0.2183	0.03*
C11	0.7215 (4)	0.1596 (2)	−0.3965 (3)	0.0236 (8)
C12	0.5777 (4)	0.1337 (2)	−0.4889 (3)	0.0245 (8)
H12	0.5794	0.1366	−0.567	0.029*
C13	0.4296 (4)	0.1033 (2)	−0.4674 (3)	0.0228 (8)
C14	0.4275 (4)	0.0992 (2)	−0.3531 (3)	0.0240 (8)
H14	0.3256	0.079	−0.339	0.029*
C15	0.8779 (5)	0.1969 (2)	−0.4183 (3)	0.0261 (9)
C16	0.2728 (5)	0.0756 (2)	−0.5654 (3)	0.0282 (9)
O1	0.1336 (3)	0.21616 (18)	−0.0592 (2)	0.0359 (7)
O2	0.2709 (3)	0.18813 (19)	0.13099 (19)	0.0347 (7)
H2	0.1804	0.2121	0.137	0.052*
O3	0.8420 (3)	0.05449 (19)	0.2698 (2)	0.0378 (7)
H3A	0.9389	0.0457	0.322	0.057*
O4	1.0026 (3)	0.04366 (18)	0.1520 (2)	0.0363 (7)
O5	1.0046 (3)	0.22595 (19)	−0.3384 (2)	0.0401 (7)
O6	0.8667 (3)	0.19811 (18)	−0.5281 (2)	0.0333 (7)
H6	0.9598	0.2188	−0.5338	0.05*
O7	0.2891 (3)	0.07684 (19)	−0.6680 (2)	0.0368 (7)
H7	0.1918	0.0674	−0.7195	0.055*
O8	0.1352 (3)	0.05385 (18)	−0.5479 (2)	0.0346 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0209 (19)	0.029 (2)	0.0226 (19)	−0.0053 (16)	0.0047 (16)	−0.0010 (15)
C2	0.0242 (19)	0.021 (2)	0.0243 (19)	−0.0028 (15)	0.0103 (17)	−0.0008 (14)
C3	0.031 (2)	0.027 (2)	0.0180 (18)	−0.0071 (16)	0.0065 (17)	−0.0008 (15)
C4	0.029 (2)	0.021 (2)	0.023 (2)	−0.0040 (15)	0.0132 (17)	−0.0025 (14)
C5	0.026 (2)	0.025 (2)	0.0243 (19)	−0.0030 (15)	0.0096 (17)	−0.0025 (15)
C6	0.024 (2)	0.023 (2)	0.0219 (19)	−0.0029 (15)	0.0085 (17)	−0.0023 (14)
C7	0.028 (2)	0.032 (2)	0.023 (2)	−0.0031 (16)	0.0086 (18)	0.0017 (16)
C8	0.034 (2)	0.029 (2)	0.023 (2)	−0.0026 (17)	0.0078 (18)	0.0001 (15)
C9	0.025 (2)	0.025 (2)	0.026 (2)	0.0050 (15)	0.0107 (17)	−0.0002 (15)
C10	0.0238 (19)	0.029 (2)	0.0203 (18)	0.0016 (16)	0.0054 (16)	−0.0027 (15)
C11	0.027 (2)	0.021 (2)	0.0254 (19)	0.0025 (15)	0.0114 (17)	0.0014 (15)
C12	0.030 (2)	0.023 (2)	0.0207 (18)	0.0039 (16)	0.0093 (17)	−0.0014 (14)
C13	0.025 (2)	0.023 (2)	0.0204 (19)	0.0019 (15)	0.0078 (17)	0.0018 (14)
C14	0.023 (2)	0.026 (2)	0.0229 (19)	0.0020 (15)	0.0071 (17)	−0.0014 (15)
C15	0.027 (2)	0.030 (2)	0.022 (2)	0.0008 (16)	0.0090 (18)	−0.0005 (15)
C16	0.032 (2)	0.027 (2)	0.025 (2)	0.0033 (16)	0.0089 (18)	−0.0019 (15)
O1	0.0333 (16)	0.0503 (18)	0.0248 (14)	0.0092 (12)	0.0104 (13)	−0.0018 (12)
O2	0.0315 (16)	0.0534 (19)	0.0238 (14)	0.0038 (12)	0.0154 (12)	0.0022 (12)
O3	0.0302 (16)	0.0588 (19)	0.0209 (14)	−0.0031 (13)	0.0039 (12)	0.0071 (12)
O4	0.0276 (15)	0.0494 (18)	0.0327 (15)	0.0074 (12)	0.0110 (13)	−0.0043 (12)
O5	0.0336 (16)	0.059 (2)	0.0277 (15)	−0.0107 (13)	0.0108 (13)	−0.0002 (13)
O6	0.0305 (15)	0.0457 (18)	0.0286 (15)	−0.0028 (12)	0.0162 (12)	0.0000 (11)
O7	0.0348 (16)	0.0511 (19)	0.0225 (14)	0.0046 (13)	0.0066 (12)	−0.0009 (12)
O8	0.0272 (15)	0.0455 (18)	0.0306 (15)	−0.0019 (12)	0.0091 (13)	0.0014 (12)

Geometric parameters (Å, º) top

C1—C2	1.385 (5)	C10—C11	1.393 (5)
C1—C6	1.400 (5)	C10—H10	0.95
C1—H1	0.95	C11—C12	1.373 (5)
C2—C3	1.390 (4)	C11—C15	1.488 (5)
C2—C7	1.484 (5)	C12—C13	1.390 (5)
C3—C4	1.395 (5)	C12—H12	0.95
C3—H3	0.95	C13—C14	1.389 (5)
C4—C5	1.382 (4)	C13—C16	1.478 (5)
C4—C8	1.483 (5)	C14—H14	0.95
C5—C6	1.397 (4)	C15—O5	1.228 (4)
C5—H5	0.95	C15—O6	1.300 (4)
C6—C9	1.489 (5)	C16—O8	1.251 (4)
C7—O1	1.228 (4)	C16—O7	1.291 (4)
C7—O2	1.305 (4)	O2—H2	0.84
C8—O4	1.245 (4)	O3—H3A	0.84
C8—O3	1.294 (4)	O6—H6	0.84
C9—C10	1.391 (5)	O7—H7	0.84
C9—C14	1.392 (5)

C2—C1—C6	120.6 (3)	C14—C9—C6	120.0 (3)
C2—C1—H1	119.7	C9—C10—C11	120.1 (3)
C6—C1—H1	119.7	C9—C10—H10	119.9
C1—C2—C3	120.4 (3)	C11—C10—H10	119.9
C1—C2—C7	118.5 (3)	C12—C11—C10	120.7 (3)
C3—C2—C7	121.0 (3)	C12—C11—C15	120.3 (3)
C2—C3—C4	119.5 (3)	C10—C11—C15	118.9 (3)
C2—C3—H3	120.3	C11—C12—C13	119.6 (3)
C4—C3—H3	120.3	C11—C12—H12	120.2
C5—C4—C3	120.0 (3)	C13—C12—H12	120.2
C5—C4—C8	120.0 (3)	C14—C13—C12	120.1 (3)
C3—C4—C8	119.9 (3)	C14—C13—C16	119.4 (3)
C4—C5—C6	121.2 (3)	C12—C13—C16	120.6 (3)
C4—C5—H5	119.4	C13—C14—C9	120.6 (3)
C6—C5—H5	119.4	C13—C14—H14	119.7
C5—C6—C1	118.4 (3)	C9—C14—H14	119.7
C5—C6—C9	121.7 (3)	O5—C15—O6	123.4 (3)
C1—C6—C9	119.9 (3)	O5—C15—C11	122.0 (3)
O1—C7—O2	123.4 (3)	O6—C15—C11	114.5 (3)
O1—C7—C2	122.1 (3)	O8—C16—O7	123.6 (3)
O2—C7—C2	114.4 (3)	O8—C16—C13	121.1 (3)
O4—C8—O3	124.0 (3)	O7—C16—C13	115.2 (3)
O4—C8—C4	120.6 (3)	C7—O2—H2	109.5
O3—C8—C4	115.3 (3)	C8—O3—H3A	109.5
C10—C9—C14	118.9 (3)	C15—O6—H6	109.5
C10—C9—C6	121.1 (3)	C16—O7—H7	109.5

C6—C1—C2—C3	−1.8 (5)	C5—C6—C9—C14	140.6 (3)
C6—C1—C2—C7	174.7 (3)	C1—C6—C9—C14	−40.0 (5)
C1—C2—C3—C4	1.2 (5)	C14—C9—C10—C11	0.3 (5)
C7—C2—C3—C4	−175.1 (3)	C6—C9—C10—C11	−178.8 (3)
C2—C3—C4—C5	0.3 (5)	C9—C10—C11—C12	−0.9 (5)
C2—C3—C4—C8	175.7 (3)	C9—C10—C11—C15	176.7 (3)
C3—C4—C5—C6	−1.2 (5)	C10—C11—C12—C13	0.7 (5)
C8—C4—C5—C6	−176.6 (3)	C15—C11—C12—C13	−176.9 (3)
C4—C5—C6—C1	0.6 (5)	C11—C12—C13—C14	0.1 (5)
C4—C5—C6—C9	180.0 (3)	C11—C12—C13—C16	179.7 (3)
C2—C1—C6—C5	0.9 (5)	C12—C13—C14—C9	−0.6 (5)
C2—C1—C6—C9	−178.5 (3)	C16—C13—C14—C9	179.8 (3)
C1—C2—C7—O1	2.6 (5)	C10—C9—C14—C13	0.4 (5)
C3—C2—C7—O1	179.0 (3)	C6—C9—C14—C13	179.6 (3)
C1—C2—C7—O2	−175.6 (3)	C12—C11—C15—O5	175.5 (3)
C3—C2—C7—O2	0.9 (5)	C10—C11—C15—O5	−2.1 (5)
C5—C4—C8—O4	4.8 (5)	C12—C11—C15—O6	−2.9 (5)
C3—C4—C8—O4	−170.6 (3)	C10—C11—C15—O6	179.5 (3)
C5—C4—C8—O3	−177.9 (3)	C14—C13—C16—O8	4.3 (5)
C3—C4—C8—O3	6.6 (5)	C12—C13—C16—O8	−175.3 (3)
C5—C6—C9—C10	−40.2 (5)	C14—C13—C16—O7	−176.5 (3)
C1—C6—C9—C10	139.1 (3)	C12—C13—C16—O7	3.9 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O5ⁱ	0.84	1.80	2.631 (3)	173
O3—H3A···O8ⁱⁱ	0.84	1.84	2.656 (3)	165
O6—H6···O1ⁱⁱⁱ	0.84	1.81	2.637 (3)	168
O7—H7···O4^iv	0.84	1.82	2.650 (3)	170

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

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

Bi­phenyl-3,3',5,5'-tetra­carboxyl­ic acid

Supporting information

Key indicators

checkCIF results

Biphenyl-3,3',5,5'-tetracarboxylic acid