4,4'-Bipyridine-trans,trans-hexa-2,4-dienedioic acid (1/1).

The title cocrystal, C(10)H(8)N(2)·C(6)H(6)O(4), crystallizes with half-mol-ecules of 4,4'-bipyridine and trans,trans-hexa-2,4-dienedioic acid in the asymmetric unit, as each is located about a crystallographic inversion center. The bipyridine molecule is planar from symmetry. In the dicarboxylic acid molecule, the O-C-C-C torsion angle is -13.0 (2)°. In the crystal, O-H⋯N and C-H⋯O hydrogen bonds generate a three-dimensional network.

Related literature

For cocrystals of carb­oxy­lic acid and pyridine, see: Bhogala & Nangia (2003 ▶); Hou et al. (2008 ▶); Jiang & Hou (2012 ▶). For background to the applications of cocrystals, see: Bhogala & Nangia (2003 ▶); Gao et al. (2004 ▶); Hori et al. (2009 ▶); Weyna et al. (2009 ▶).

Experimental

Crystal data

C10H8N2·C6H6O4

M = 298.29

Triclinic,

a = 5.8481 (5) Å

b = 7.6348 (6) Å

c = 8.4677 (7) Å

α = 91.837 (5)°

β = 92.584 (5)°

γ = 111.907 (4)°

V = 349.93 (5) Å3

Z = 1

Mo Kα radiation

μ = 0.10 mm−1

T = 173 K

0.40 × 0.26 × 0.24 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.960, T max = 0.976

5973 measured reflections

1517 independent reflections

1336 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.116

S = 1.04

1517 reflections

104 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812012391/sj5219sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012391/sj5219Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812012391/sj5219Isup3.cml

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

C10H8N2·C6H6O4	Z = 1
Mr = 298.29	F(000) = 156
Triclinic, P1	Dx = 1.415 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8481 (5) Å	Cell parameters from 4151 reflections
b = 7.6348 (6) Å	θ = 2.4–28.4°
c = 8.4677 (7) Å	µ = 0.10 mm−1
α = 91.837 (5)°	T = 173 K
β = 92.584 (5)°	Block, colourless
γ = 111.907 (4)°	0.40 × 0.26 × 0.24 mm
V = 349.93 (5) Å3

Bruker APEXII CCD diffractometer	1517 independent reflections
Radiation source: fine-focus sealed tube	1336 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 27.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.960, Tmax = 0.976	k = −9→9
5973 measured reflections	l = −10→10

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0688P)2 + 0.0753P] where P = (Fo2 + 2Fc2)/3
1517 reflections	(Δ/σ)max < 0.001
104 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	0.05949 (18)	1.05053 (14)	0.23387 (13)	0.0414 (3)
H1	0.184 (4)	0.987 (3)	0.271 (3)	0.084 (7)*
O2	0.37461 (17)	1.23144 (14)	0.09959 (12)	0.0394 (3)
C1	0.1653 (2)	1.18769 (18)	0.13952 (14)	0.0285 (3)
C2	−0.0033 (2)	1.28402 (18)	0.09016 (15)	0.0299 (3)
H2	−0.1740	1.2262	0.1077	0.036*
C3	0.0786 (2)	1.44912 (17)	0.02208 (14)	0.0288 (3)
H3	0.2485	1.5031	0.0013	0.035*
N1	0.3031 (2)	0.85144 (15)	0.34658 (13)	0.0331 (3)
C4	0.2266 (3)	0.7745 (2)	0.48325 (17)	0.0374 (3)
H4	0.1161	0.8150	0.5389	0.045*
C5	0.3007 (3)	0.6385 (2)	0.54775 (16)	0.0350 (3)
H5	0.2419	0.5882	0.6458	0.042*
C6	0.4615 (2)	0.57572 (16)	0.46878 (14)	0.0262 (3)
C7	0.5464 (3)	0.6613 (2)	0.32875 (16)	0.0351 (3)
H7	0.6611	0.6270	0.2719	0.042*
C8	0.4627 (3)	0.79683 (19)	0.27252 (16)	0.0362 (3)
H8	0.5224	0.8532	0.1766	0.043*

	U11	U22	U33	U12	U13	U23
O1	0.0346 (5)	0.0401 (6)	0.0593 (7)	0.0222 (4)	0.0127 (5)	0.0259 (5)
O2	0.0314 (5)	0.0469 (6)	0.0488 (6)	0.0229 (4)	0.0109 (4)	0.0174 (5)
C1	0.0283 (6)	0.0293 (6)	0.0319 (6)	0.0148 (5)	0.0032 (5)	0.0056 (5)
C2	0.0260 (6)	0.0327 (7)	0.0355 (6)	0.0156 (5)	0.0037 (5)	0.0077 (5)
C3	0.0270 (6)	0.0324 (6)	0.0316 (6)	0.0156 (5)	0.0042 (5)	0.0067 (5)
N1	0.0322 (6)	0.0287 (6)	0.0407 (6)	0.0141 (5)	−0.0015 (5)	0.0074 (4)
C4	0.0397 (7)	0.0387 (7)	0.0434 (7)	0.0248 (6)	0.0073 (6)	0.0078 (6)
C5	0.0406 (7)	0.0390 (7)	0.0339 (7)	0.0234 (6)	0.0080 (5)	0.0106 (5)
C6	0.0253 (6)	0.0255 (6)	0.0291 (6)	0.0110 (5)	−0.0015 (5)	0.0030 (5)
C7	0.0372 (7)	0.0377 (7)	0.0373 (7)	0.0205 (6)	0.0084 (5)	0.0114 (6)
C8	0.0395 (7)	0.0351 (7)	0.0382 (7)	0.0176 (6)	0.0055 (6)	0.0135 (6)

O1—C1	1.3162 (15)	C4—C5	1.3839 (18)
O1—H1	1.06 (2)	C4—H4	0.9500
O2—C1	1.2096 (16)	C5—C6	1.3907 (17)
C1—C2	1.4873 (16)	C5—H5	0.9500
C2—C3	1.3310 (18)	C6—C7	1.3929 (18)
C2—H2	0.9500	C6—C6ii	1.492 (2)
C3—C3i	1.452 (2)	C7—C8	1.3872 (17)
C3—H3	0.9500	C7—H7	0.9500
N1—C8	1.3286 (17)	C8—H8	0.9500
N1—C4	1.3337 (18)
C1—O1—H1	110.3 (13)	C5—C4—H4	118.5
O2—C1—O1	124.23 (11)	C4—C5—C6	119.86 (12)
O2—C1—C2	124.24 (11)	C4—C5—H5	120.1
O1—C1—C2	111.52 (10)	C6—C5—H5	120.1
C3—C2—C1	121.76 (12)	C5—C6—C7	116.57 (11)
C3—C2—H2	119.1	C5—C6—C6ii	121.53 (14)
C1—C2—H2	119.1	C7—C6—C6ii	121.90 (14)
C2—C3—C3i	123.31 (15)	C8—C7—C6	119.78 (12)
C2—C3—H3	118.3	C8—C7—H7	120.1
C3i—C3—H3	118.3	C6—C7—H7	120.1
C8—N1—C4	117.62 (11)	N1—C8—C7	123.05 (12)
N1—C4—C5	123.05 (12)	N1—C8—H8	118.5
N1—C4—H4	118.5	C7—C8—H8	118.5
O2—C1—C2—C3	−13.0 (2)	C4—C5—C6—C6ii	−177.69 (14)
O1—C1—C2—C3	166.14 (12)	C5—C6—C7—C8	−2.2 (2)
C1—C2—C3—C3i	−177.53 (14)	C6ii—C6—C7—C8	177.72 (14)
C8—N1—C4—C5	−1.8 (2)	C4—N1—C8—C7	1.8 (2)
N1—C4—C5—C6	−0.3 (2)	C6—C7—C8—N1	0.2 (2)
C4—C5—C6—C7	2.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	1.06 (2)	1.58 (2)	2.6148 (14)	164 (2)
C2—H2···O2iii	0.95	2.65	3.5130 (15)	151
C3—H3···O2iv	0.95	2.58	3.4457 (16)	152
C4—H4···O1v	0.95	2.58	3.4848 (17)	160
C8—H8···O2vi	0.95	2.56	3.3555 (17)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	1.06 (2)	1.58 (2)	2.6148 (14)	164 (2)
C2—H2⋯O2i	0.95	2.65	3.5130 (15)	151
C3—H3⋯O2ii	0.95	2.58	3.4457 (16)	152
C4—H4⋯O1iii	0.95	2.58	3.4848 (17)	160
C8—H8⋯O2iv	0.95	2.56	3.3555 (17)	141

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .