1,3-Di-4-pyridylpropane–4,4′-oxy­dibenzoic acid (1/1)

Guangzhe Li; Chris Salim; Hirofumi Hinode

doi:10.1107/S160053680803331X

. 2008 Nov 8;64(Pt 12):o2251. doi: 10.1107/S160053680803331X

1,3-Di-4-pyridylpropane–4,4′-oxydibenzoic acid (1/1)

Guangzhe Li ^a, Chris Salim ^a, Hirofumi Hinode ^a,^*

PMCID: PMC2960149 PMID: 21581232

Abstract

The hydrothermal reaction of Cd(NO₃)₂·4H₂O, 1,3-di-4-pyridylpropane (BPP) and 4,4′-oxydibenzoic acid (OBA) led to the formation of the title compound, C₁₃H₁₄N₂·C₁₄H₁₀O₅. The asymmetric unit consists of one molecule of OBA and one of BPP. In the OBA molecule, one COOH group is nearly planar with its attached benzene ring [dihedral angle = 0.9 (1)°], while the other COOH group is slightly twisted with a dihedral angle of 10.8 (3)°. The carboxyl groups form strong intermolecular O—H⋯N hydrogen bonds with N atoms of the pyridine rings in BPP, linking the molecules into zigzag chains.

Related literature

For general background see: Belcher et al. (2002 ▶); Hagrman et al. (1999 ▶); Han et al. (2007 ▶); Luan et al. (2005 ▶); Nguyen et al. (2006 ▶); Wang et al. (2005 ▶); Yaghi et al. (1998 ▶). For related structures, see: Dai et al. (2005 ▶); Ma et al. (2006 ▶); Hou et al. (2008 ▶); Lee et al. (2003 ▶); Wang et al. (2008 ▶); Najafpour et al. (2008 ▶). For an idependent determination of this structure, see: Dong et al. (2008 ▶).

Experimental

Crystal data

C₁₃H₁₄N₂·C₁₄H₁₀O₅
M _r = 456.48
Triclinic,
a = 6.8938 (3) Å
b = 11.5869 (6) Å
c = 14.9570 (9) Å
α = 86.493 (4)°
β = 81.157 (4)°
γ = 74.016 (3)°
V = 1134.67 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 (2) K
0.47 × 0.45 × 0.45 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T _min = 0.957, T _max = 0.962
8404 measured reflections
5645 independent reflections
2932 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.147
S = 1.01
5645 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXS97; software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680803331X/fl2221sup1.cif

e-64-o2251-sup1.cif^{(20.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803331X/fl2221Isup2.hkl

e-64-o2251-Isup2.hkl^{(276.3KB, hkl)}

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
O3—H3⋯N1ⁱ	0.82	1.78	2.598 (2)	174
O5—H5⋯N2ⁱⁱ	0.82	1.87	2.685 (2)	177

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors thank Tokyo Institute of Technology and MEXT for the financial support of this work.

supplementary crystallographic information

Comment

Over the past decades, the rational design and synthesis of metal-organic frameworks have received extensive attention in the fields of supramolecular chemistry and crystal engineering (Hagrman et al., 1999; Yaghi et al., 1998). These materials exhibit interesting functions such as catalysis, biology, electrical conductivity, magnetism and photochemistry. In the past five years, there has been a growing interest in metal-organic frameworks based on 1,3-di-4-pyridylpropane and 4,4'-oxydibenzoic acid ligands (Wang et al., 2005; Luan et al., 2005; Belcher et al., 2002; Han et al., 2007; Nguyen et al., 2006). Recently, we have focused on preparing metal-organic frameworks containing such organic ligands and metal ions. During the process, a new cocrystal of 1,3-di-4-pyridylpropane and 4,4'-oxydibenzoic acid was obtained which assembled by H-bondin and we report its synthesis and crystal structure here. The structures of some similar molecular materials have been reported (Dai et al., 2005; Lee et al., 2003; Ma et al., 2006; Wang et al., 2008; Hou et al., 2008; Najafpour et al., 2008). An independent study of (I) has also been published (Dong et al., 2008).

As shown in Fig. 1, the asymmetric unit contains one 1,3-di-4-pyridylpropane molecule and one 4,4'-oxydibenzoic acid molecule. The bond lengths and angles are within normal ranges. In 4,4'-oxydibenzoic acid molecule, one COOH group (C7/O2/O3) is nearly planar with one benzene ring (C1/C2/C3/C4/C5/C6, dihedral angle of 0.9 °), while another COOH group (C14/O4/O5) has a dihedral angle of 10.8 ° with another benzene ring (C8/C9/C10/C11/C12/C13). The dihedral angle between two benzene ring of a 4,4'-oxydibenzoic acid molecule is 57.0 °. In 1,3-di-4-pyridylpropane molecule, the dihedral angle between two pyridyl rings is 26.9 °. The carboxylic acid groups form strong intermolecular O—H···N hydrogen bonds (Table 1) with N atoms of the pyriding rings, linking the molecules into one-dimensional zigzag chains (Fig.2). Intermolecular C—H···O hydrogen bonds may be effective in the stabilization of the crystal structure.

Experimental

In a typical synthesis for the title compound, a mixture of Cd(NO₃)₂.4H₂O 120 mg, 4,4'-oxydibenzoic acid 52 mg, 1,3-bis(4-pyridyl)propane 20 mg, HCl (38%) 0.1 ml, NH₃.H₂O 0.08 ml, N,N-dimethylformamide (DMF) 3.0 ml and H₂O 6.0 ml were sealed in a 15 ml Teflon-lined stainless steel autoclave and heated under autogenous pressure for five days at 393 K. After slow cooling to room temperature, the block-shaped colourless crystalline product was filtered, washed with distilled water, and dried at ambient temperature. The crystal used for data collection was obtained directly from the sample that was washed and dried without further re-crystallization.