4,4'-Bipyridine-butane-1,2,3,4-tetra-carboxylic acid (1/1).

The title compound, C(10)H(8)N(2)·C(8)H(10)O(8), is an example of a system with a short O⋯H⋯N hydrogen bond [O⋯N = 2.565 (3) Å]. The crystal structure comprises a 1:1 adduct between 4,4'-bipyridine and butane-1,2,3,4-tetra-carboxylic acid, where both components are centrosymmetric. The component mol-ecules are linked through strong O⋯H⋯N hydrogen bonds, forming chains extending approximately along [11]. The chains are inter-connected by O⋯H⋯O hydrogen bonds and weak stacking inter-actions involving the pyridyl rings of the 4,4'-bipyridine mol-ecules [centroid-centroid distance = 3.73 (2) Å and inter-planar distance = 3.35 (1) Å]. The H atom of the short O⋯H⋯N hydrogen bond is disordered over two positions with site occupancy factors of ca 0.6 and 0.4. One methylene group is disordered over two positions; the site occupancy factors are ca 0.9 and 0.1.

Related literature

For related literature, see: Barnes & Barnes (1996 ▶); Cowan et al. (2003 ▶); Etter et al. (1990 ▶); Majerz et al. (1997 ▶); McKee & Najafpour (2007 ▶); Steiner et al. (2000 ▶, 2001 ▶); Wang & Chen (2005 ▶); Wang & Wei (2006 ▶).

Experimental

Crystal data

C10H8N2·C8H10O8

M = 390.34

Triclinic,

a = 5.642 (4) Å

b = 6.966 (4) Å

c = 11.680 (8) Å

α = 73.55 (5)°

β = 81.34 (5)°

γ = 73.85 (5)°

V = 421.6 (5) Å3

Z = 1

Mo Kα radiation

μ = 0.12 mm−1

T = 100 (2) K

0.40 × 0.18 × 0.04 mm

Data collection

Oxford Diffraction KM-4-CCD diffractometer

Absorption correction: none

3650 measured reflections

1946 independent reflections

1034 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.083

S = 1.01

1946 reflections

135 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011732/tk2261sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011732/tk2261Isup2.hkl

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

C10H8N2·C8H10O8	Z = 1
Mr = 390.34	F000 = 204
Triclinic, P1	Dx = 1.537 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 5.642 (4) Å	Cell parameters from 3002 reflections
b = 6.966 (4) Å	θ = 2–35º
c = 11.680 (8) Å	µ = 0.12 mm−1
α = 73.55 (5)º	T = 100 (2) K
β = 81.34 (5)º	Plate, colourless
γ = 73.85 (5)º	0.40 × 0.18 × 0.04 mm
V = 421.6 (5) Å3

Oxford Diffraction KM-4-CCD diffractometer	1034 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Monochromator: graphite	θmax = 28.4º
T = 100(2) K	θmin = 3.2º
ω scans	h = −7→7
Absorption correction: none	k = −7→9
3650 measured reflections	l = −15→15
1946 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H-atom parameters constrained
wR(F2) = 0.083	w = 1/[σ2(Fo2) + (0.027P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
1946 reflections	Δρmax = 0.30 e Å−3
135 parameters	Δρmin = −0.19 e Å−3
2 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq	Occ. (<1)
O11	0.4836 (2)	0.4390 (2)	0.68732 (11)	0.0338 (4)
H1A	0.6275	0.3764	0.6676	0.051*	0.59 (3)
N1	0.9093 (3)	0.2488 (2)	0.61058 (14)	0.0231 (4)
H1B	0.7625	0.3105	0.6381	0.035*	0.41 (3)
C2	1.0784 (3)	0.1253 (3)	0.68554 (17)	0.0265 (5)
H2	1.0378	0.1051	0.7693	0.032*
C3	1.3105 (3)	0.0261 (3)	0.64525 (16)	0.0272 (5)
H3	1.4260	−0.0608	0.7012	0.033*
C4	1.3754 (3)	0.0531 (3)	0.52342 (16)	0.0208 (4)
C5	1.1967 (3)	0.1826 (3)	0.44570 (16)	0.0232 (5)
H5	1.2318	0.2059	0.3615	0.028*
C6	0.9677 (3)	0.2764 (3)	0.49322 (16)	0.0237 (5)
H6	0.8475	0.3640	0.4398	0.028*
C11	0.1384 (3)	0.4629 (3)	0.97960 (16)	0.0276 (5)
H11	0.2287	0.5506	1.0016	0.033*
C21A	0.1846 (4)	0.4914 (3)	0.84558 (17)	0.0250 (7)	0.940 (6)
H21A	0.1416	0.6412	0.8062	0.030*	0.940 (6)
H21B	0.0719	0.4285	0.8193	0.030*	0.940 (6)
C31	0.4490 (4)	0.3983 (3)	0.80273 (18)	0.0271 (5)
O21	0.6106 (2)	0.29297 (19)	0.87162 (11)	0.0272 (3)
C12	0.2377 (3)	0.2422 (3)	1.05080 (18)	0.0262 (5)
O12	0.1933 (2)	0.1051 (2)	1.00261 (12)	0.0316 (4)
H12	0.2479	−0.0148	1.0450	0.047*
O22	0.3354 (2)	0.1971 (2)	1.14272 (12)	0.0387 (4)
C21B	0.290 (6)	0.552 (3)	0.875 (2)	0.014 (9)*	0.060 (6)
H21C	0.4014	0.6144	0.9028	0.017*	0.060 (6)
H21D	0.1785	0.6655	0.8207	0.017*	0.060 (6)

	U11	U22	U33	U12	U13	U23
O11	0.0236 (8)	0.0379 (10)	0.0249 (9)	0.0087 (7)	0.0034 (6)	−0.0030 (7)
N1	0.0167 (9)	0.0238 (10)	0.0249 (10)	0.0016 (7)	0.0005 (7)	−0.0074 (8)
C2	0.0243 (11)	0.0321 (12)	0.0190 (11)	−0.0009 (10)	0.0012 (9)	−0.0073 (9)
C3	0.0207 (11)	0.0308 (12)	0.0233 (12)	0.0025 (9)	−0.0028 (9)	−0.0042 (10)
C4	0.0178 (10)	0.0214 (11)	0.0220 (11)	−0.0027 (8)	0.0003 (9)	−0.0066 (9)
C5	0.0242 (11)	0.0228 (11)	0.0191 (11)	−0.0023 (9)	0.0016 (9)	−0.0051 (9)
C6	0.0226 (11)	0.0224 (11)	0.0202 (11)	0.0001 (9)	−0.0043 (9)	−0.0006 (9)
C11	0.0227 (11)	0.0240 (12)	0.0251 (11)	0.0066 (9)	0.0032 (9)	−0.0036 (9)
C21A	0.0237 (13)	0.0196 (13)	0.0236 (13)	0.0035 (10)	−0.0008 (10)	−0.0021 (10)
C31	0.0285 (12)	0.0209 (12)	0.0264 (12)	−0.0009 (10)	0.0038 (10)	−0.0056 (10)
O21	0.0232 (7)	0.0243 (8)	0.0267 (8)	0.0026 (6)	−0.0017 (7)	−0.0035 (7)
C12	0.0179 (11)	0.0265 (12)	0.0268 (12)	0.0039 (9)	0.0072 (9)	−0.0088 (10)
O12	0.0290 (8)	0.0227 (8)	0.0353 (9)	0.0008 (7)	−0.0042 (7)	−0.0015 (7)
O22	0.0421 (9)	0.0361 (9)	0.0264 (8)	0.0121 (7)	−0.0098 (7)	−0.0076 (7)

N1—C6	1.332 (2)	C4—C5	1.400 (3)
N1—C2	1.336 (2)	C4—C4i	1.497 (4)
C31—O11	1.293 (3)	C5—C6	1.387 (3)
C31—O21	1.237 (2)	C5—H5	0.95
C12—O12	1.331 (2)	C6—H6	0.95
C12—O22	1.202 (2)	C11—C21A	1.512 (3)
O11—C31	1.293 (2)	C11—C12	1.519 (3)
O11—H1A	0.84	C11—C11ii	1.549 (4)
N1—H1B	0.88	C11—H11	1.00
C2—C3	1.382 (3)	C21A—C31	1.523 (3)
C2—H2	0.95	C21A—H21A	0.99
C3—C4	1.387 (3)	C21A—H21B	0.99
C3—H3	0.95	O12—H12	0.84
C6—N1—C2	118.6 (2)	C4—C5—H5	120.4
C21A—C11—C12	113.4 (2)	N1—C6—C5	122.73 (17)
C21A—C11—C11ii	113.0 (2)	N1—C6—H6	118.6
O21—C31—O11	124.2 (2)	C5—C6—H6	118.6
O22—C12—O12	124.0 (2)	C12—C11—C11ii	109.00 (19)
C31—O11—H1A	109.5	C21A—C11—H11	107.0
C6—N1—H1B	120.7	C12—C11—H11	107.0
C2—N1—H1B	120.7	C11ii—C11—H11	107.0
N1—C2—C3	122.18 (18)	C11—C21A—C31	114.83 (18)
N1—C2—H2	118.9	C11—C21A—H21A	108.6
C3—C2—H2	118.9	C31—C21A—H21A	108.6
C2—C3—C4	120.20 (18)	C11—C21A—H21B	108.6
C2—C3—H3	119.9	C31—C21A—H21B	108.6
C4—C3—H3	119.9	H21A—C21A—H21B	107.5
C3—C4—C5	117.12 (17)	O21—C31—C21A	123.24 (18)
C3—C4—C4i	121.7 (2)	O11—C31—C21A	112.54 (18)
C5—C4—C4i	121.2 (2)	O22—C12—C11	123.9 (2)
C6—C5—C4	119.19 (17)	O12—C12—C11	112.07 (18)
C6—C5—H5	120.4	C12—O12—H12	109.5
C6—N1—C2—C3	0.0 (3)	C11ii—C11—C21A—C31	−173.3 (2)
N1—C2—C3—C4	0.1 (3)	C11—C21A—C31—O21	5.5 (3)
C2—C3—C4—C5	−0.2 (3)	C11—C21A—C31—O11	−175.45 (18)
C2—C3—C4—C4i	−179.6 (2)	C21A—C11—C12—O22	141.0 (2)
C3—C4—C5—C6	0.1 (3)	C11ii—C11—C12—O22	−92.2 (3)
C4i—C4—C5—C6	179.53 (19)	C21A—C11—C12—O12	−42.0 (2)
C2—N1—C6—C5	−0.1 (3)	C11ii—C11—C12—O12	84.8 (2)
C4—C5—C6—N1	0.0 (3)	C5—C4—C4i—C3i	0.6 (4)
C12—C11—C21A—C31	−48.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O11—H1A···N1	0.84	1.73	2.565 (3)	173
N1—H1B···O11	0.88	1.69	2.565 (3)	177
O12—H12···O21iii	0.84	1.91	2.747 (3)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O11—H1A⋯N1	0.84	1.73	2.565 (3)	173
N1—H1B⋯O11	0.88	1.69	2.565 (3)	177
O12—H12⋯O21iii	0.84	1.91	2.747 (3)	175

Symmetry code: (iii) .