Benzene-1,3-dicarb­oxy­lic acid–1,2-bis­(4-pyrid­yl)ethene (1/1)

Dong Liu; Ni-Ya Li

doi:10.1107/S1600536811043418

. 2011 Oct 29;67(Pt 11):o3039. doi: 10.1107/S1600536811043418

Benzene-1,3-dicarboxylic acid–1,2-bis(4-pyridyl)ethene (1/1)

Dong Liu ^a,^*, Ni-Ya Li ^a

PMCID: PMC3247433 PMID: 22220051

Abstract

In the title compound, C₁₂H₁₀N₂·C₈H₆O₄, the asymmetric unit contains two halves of 1,2-bis(4-pyridyl)ethene (bpe) molecules and one benzene-1,3-dicarboxylic acid (1,3-H₂BDC) molecule. These bpe and 1,3-H₂BDC molecules are linked by classical O—H⋯N hydrogen bonds, forming an extended one-dimensional zigzag chain. Each chain is further linked with neighboring ones by π–π interactions between the pyridine and aromatic rings [centroid–centroid distances = 3.9306 (15) Å] and the pyridine rings of pairs of symmetry-related molecules [centroid–centroid distances = 3.5751 (15), 3.7350 (15) and 3.6882 (15) Å], with the formation of a three-dimensional supramolecular framework.

Related literature

For structures and properties of self-assembled supramolecular compounds, see: Lehn (1990 ▶). For hydrogen-bonding interactions and π–π interactions in supramolecular compounds, see: Biradha (2003 ▶); Shan & Jones (2003 ▶); Weyna et al. (2009 ▶).

Experimental

Crystal data

C₁₂H₁₀N₂·C₈H₆O₄
M _r = 348.35
Triclinic,
a = 6.8331 (14) Å
b = 6.8804 (14) Å
c = 18.618 (4) Å
α = 99.47 (3)°
β = 93.87 (3)°
γ = 102.69 (3)°
V = 837.4 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 223 K
0.40 × 0.40 × 0.35 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T _min = 0.962, T _max = 0.967
8280 measured reflections
3054 independent reflections
2153 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.137
S = 1.06
3054 reflections
238 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: CrystalClear (Rigaku, 2001 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811043418/rk2306sup1.cif

e-67-o3039-sup1.cif^{(17.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043418/rk2306Isup2.hkl

e-67-o3039-Isup2.hkl^{(149.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811043418/rk2306Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1ⁱ	0.83	1.77	2.597 (2)	176
O3—H3⋯N2	0.83	1.79	2.618 (2)	176

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the Research Start-Up Fund for New Staff of Huaibei Normal University (grant No. 600581).

supplementary crystallographic information

Comment

In the past decades, the supramolecular synthesis of multicomponent organic materials has attracted considerable attention due to their functional properties (Lehn, 1990). The facile way of synthesizing these co-crystals is to employ the components containing complementary functional groups such as pyridine and carboxylic acid. Owing to the hydrogen-bonds and π–π stacking between these types of groups, several multicomponent cocrystals containing various network geometries were prepared using these two functional groups (Biradha, 2003; Shan & Jones, 2003; Weyna et al., 2009).

The hydrothermal reaction of 1,2-bis(4-pyridyl)ethene (bpe) with benzene-1,3-dicarboxylic acid (1,3-H₂BDC) resulted in the cocrystals of C₁₂H₁₀N₂.C₈H₆O₄, I. In I, the asymmetric unit is formed by two halves of bpe molecules and one 1,3-H₂BDC molecule (Fig. 1). These molecular units are linked by classical O–H···N hydrogen-bonds (O1–H1···N1ⁱⁱⁱ, O1···N1ⁱⁱⁱ = 2.597 (2)Å; O3–H3···N2, O3···N2 = 2.618 (2)Å) forming an extended one-dimensional zigzag chain (Table 1, Fig. 2). Furthermore, the adjacent one-dimensional chains are interconnected each other through π–π interactions between pairs of molecules [Cg1···Cg1^iv = 3.5751 (15)Å; Cg1···Cg3 = 3.9306 (15)Å; Cg2···Cg2^v = 3.7350 (15)Å; Cg2···Cg2^vi = 3.7350 (15)Å form a three-dimensional framework (Fig. 3). The Cg1, Cg2 and Cg3, are the centroids of the rings N1/C9-C13, N2/C15-C19 and C1-C6. Symmetry codes: (iii) -x+1, y, z; (iv) -x+1, -y+1, -z+2; (v) -x+1, -y+1, -z+1; (vi) -x+2, -y+1, -z+1 .

Experimental

To a 10 mL Pyrex glass tube was loaded 1,2-bis(4-pyridyl)ethene (18 mg, 0.1 mmol), benzene-1,3-dicarboxylic acid (17 mg, 0.1 mmol) and 3 ml of H₂O. The tube was sealed and heated in an oven to 423 K for three days, and then cooled to ambient temperature at the rate of 5 K h^-1 to form yellow crystals.