4,4′-Bipyridine–trans,trans-hexa-2,4-dienedioic acid (1/1)

Moon, S.-H.; Park, K.-M.

doi:10.1107/S1600536812012391

organic compounds

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Volume 68| Part 4| April 2012| Page o1201

doi:10.1107/S1600536812012391

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4,4′-Bipyridine–trans,trans-hexa-2,4-dienedioic acid (1/1)

Suk-Hee Moon ^a and Ki-Min Park ^b ^*

^aDepartment of Food and Nutrition, Kyungnam College of Information and Technology, Busan 617-701, Republic of Korea, and ^bDepartment of Chemistry and Research Institute of Natural Sciences, Gyeongsang, National University, Jinju 660-701, Republic of Korea
^*Correspondence e-mail: kmpark@gnu.ac.kr

(Received 20 March 2012; accepted 22 March 2012; online 28 March 2012)

The title cocrystal, C₁₀H₈N₂·C₆H₆O₄, crystallizes with half-molecules 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_r = 298.29
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.040
wR(F²) = 0.116
S = 1.04
1517 reflections
104 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.25 e Å⁻³

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⋯O2^iv	0.95	2.56	3.3555 (17)	141
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+3, -z; (iii) -x, -y+2, -z+1; (iv) -x+1, -y+2, -z.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812012391/sj5219sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812012391/sj5219Isup3.cml

checkCIF report

Comment top

Considerable effort has been devoted to form co-crystals made up of two or more components because of their potential applications in pharmaceutical chemisty (Weyna et al., 2009), supramolecular chemistry (Bhogala & Nangia, 2003; Gao et al., 2004) and materials chemistry (Hori et al., 2009). In particular, numerous studies have focused on hydrogen bonding between carboxylic acid and pyridine molecules (Bhogala & Nangia, 2003; Hou et al., 2008; Jiang & Hou, 2012). We report here the structure of a co-crystal of trans, trans-hexa-2,4-dienedioic acid with 4,4'-bipyridine in the solid state.

The title compound is shown in Fig. 1. The asymmetric unit contains half-molecules of 4,4'-bipyridine and trans,trans-1,3 -butadiene-1,4-dicarboxylic acid each located on crystallographic inversion centers. Both components are planar by symmetry and tilted by 32.02 (7)° with respect to each other.

In the crystal, the dicarboxylic acid molecules are arranged side by side by intermolecular C—H···O hydrogen bonds between the dicarboxylic acid molecules, leading to the formation of a one dimensional chain. Moreover, intermolecular O—H···N and C—H···O hydrogen bonds between dicarboxylic acid and 4,4'-bipyridine molecules generate a three-dimensional network (Fig. 2, Table 1).

Related literature top

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

Experimental top

A mixture of stoichiometric amounts of trans, trans-hexa-2,4-dienedioic acid and 4,4'-bipyridine in DMF (in a 1:1 volume ratio) was heated until the two components dissolved and was then kept at room temperature. Upon slow evaporation of the solvent, X–ray quality single crystals were obtained.

Structure description top

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines. (Symmetry codes: i) -x + 1, -y + 1, -z + 1; ii) -x, -y + 3, -z.)
	Fig. 2. Crystal packing of the title compound with intermolecular O—H···N and C—H···O hydrogen bonds shown as dashed lines. (Symmetry codes: i) -x + 1, -y + 1, -z + 1; ii) -x, -y + 2, -z + 1; iii) x, y - 1, z + 1; iv) -x + 1, -y + 2, -z + 1; v) x + 1, y + 1, z + 1; vi) -x + 1, -y + 2, -z.)

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

Crystal data top

C₁₀H₈N₂·C₆H₆O₄	Z = 1
M_r = 298.29	F(000) = 156
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0688P)² + 0.0753P] where P = (F_o² + 2F_c²)/3
1517 reflections	(Δ/σ)_max < 0.001
104 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₀H₈N₂·C₆H₆O₄	γ = 111.907 (4)°
M_r = 298.29	V = 349.93 (5) Å³
Triclinic, P1	Z = 1
a = 5.8481 (5) Å	Mo Kα radiation
b = 7.6348 (6) Å	µ = 0.10 mm⁻¹
c = 8.4677 (7) Å	T = 173 K
α = 91.837 (5)°	0.40 × 0.26 × 0.24 mm
β = 92.584 (5)°

Data collection top

Bruker APEXII CCD diffractometer	1517 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1336 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.976	R_int = 0.031
5973 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.24 e Å⁻³
1517 reflections	Δρ_min = −0.25 e Å⁻³
104 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.

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry codes: (i) −x, −y+3, −z; (ii) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

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···O2^iv	0.95	2.58	3.4457 (16)	152
C4—H4···O1^v	0.95	2.58	3.4848 (17)	160
C8—H8···O2^vi	0.95	2.56	3.3555 (17)	141

Symmetry codes: (iii) x−1, y, z; (iv) −x+1, −y+3, −z; (v) −x, −y+2, −z+1; (vi) −x+1, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₁₀H₈N₂·C₆H₆O₄
M_r	298.29
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	5.8481 (5), 7.6348 (6), 8.4677 (7)
α, β, γ (°)	91.837 (5), 92.584 (5), 111.907 (4)
V (Å³)	349.93 (5)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.40 × 0.26 × 0.24

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.960, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	5973, 1517, 1336
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.116, 1.04
No. of reflections	1517
No. of parameters	104
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.25

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXTL (Sheldrick, 2008), SHELXTL and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top

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)	150.9
C3—H3···O2ⁱⁱ	0.95	2.58	3.4457 (16)	152.1
C4—H4···O1ⁱⁱⁱ	0.95	2.58	3.4848 (17)	159.7
C8—H8···O2^iv	0.95	2.56	3.3555 (17)	141.0

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+3, −z; (iii) −x, −y+2, −z+1; (iv) −x+1, −y+2, −z.

Acknowledgements

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (grant No. 2011-0026744).

References

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