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

Wen-Wen Dong; Dong-Sheng Li; Jun Zhao; Long Tang; Xiang-Yang Hou

doi:10.1107/S1600536808034971

. 2008 Nov 8;64(Pt 12):o2252. doi: 10.1107/S1600536808034971

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

Wen-Wen Dong ^a,^b, Dong-Sheng Li ^a,^b,^*, Jun Zhao ^a,^b, Long Tang ^b, Xiang-Yang Hou ^b

PMCID: PMC2959904 PMID: 21581233

Abstract

In the title compound, C₁₃H₁₄N₂·C₁₄H₁₀O₅, a 1:1 cocrystal of 1,3-di-4-pyridylpropane (bpp) and 4,4′-oxydibenzoic acid (H₂oba), the dihedral angle between the two benzene rings of the flexible H₂oba molecule is 57.07 (1)°; the two pyridine rings of bpp make a dihedral angle of 27.52 (1)°. Strong intermolecular O—H⋯N hydrogen bonds link the molecules into chains, which are then linked into a three-dimensional network through intermolecular C—H⋯O and π–π stacking interactions [centroid–centroid distance = 3.7838 (3) Å].

Related literature

For the use of co-crystallization reactions in developing new methodologies in supramolecular synthesis, see: Desiraju (2003 ▶); Shan et al. (2002 ▶). For hydrogen bonding and π–π stacking in molecular synthesis, see: Shattock et al. (2005 ▶). For a related structure, see: Ma et al. (2006 ▶). An independent determination of this structure is reported in the preceeding paper (Li et al., 2008 ▶).

Experimental

Crystal data

C₁₃H₁₄N₂·C₁₄H₁₀O₅
M _r = 456.48
Triclinic,
a = 6.8927 (12) Å
b = 11.5788 (19) Å
c = 14.974 (3) Å
α = 86.638 (3)°
β = 81.205 (3)°
γ = 73.963 (3)°
V = 1134.9 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 (2) K
0.38 × 0.20 × 0.16 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.966, T _max = 0.985
5767 measured reflections
3965 independent reflections
1530 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.073
wR(F ²) = 0.232
S = 1.01
3965 reflections
309 parameters
H-atom parameters constrained
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; 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: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808034971/fl2224sup1.cif

e-64-o2252-sup1.cif^{(22.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034971/fl2224Isup2.hkl

e-64-o2252-Isup2.hkl^{(194.3KB, 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
O2—H2⋯N2ⁱ	0.82	1.86	2.679 (5)	174
O5—H5⋯N1ⁱⁱ	0.82	1.75	2.566 (5)	175
C4—H4⋯O3ⁱⁱⁱ	0.93	2.55	3.418 (6)	155
C5—H5A⋯O3^iv	0.93	2.48	3.160 (6)	130
C12—H12⋯O4^v	0.93	2.45	3.174 (7)	135

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) .

Acknowledgments

This work was financially supported by the National Natural Science Foundation of China (No. 20773104), the Program for New Century Excellent Talents in Universities (NCET-06–0891), the Key Project of the Chinese Ministry of Education (208143) and the Important Project of Hubei Provincial Education Office (09HB81).

supplementary crystallographic information

Comment

Co-crystallization reactions provide helpful means for probing the importance and balance between different intermolecular interactions, and thus offer practical guidelines for developing new methodologies in supramolecular synthesis (Desiraju,2003; Shan et al., 2002). The role of hydrogen bonding and π–π stacking for these purposes is well established (Shattock et al.,2005). We attempted to synthesize a Cd^II complex with the mixed ligand using hydrothermal synthesis conditions. However, we were not successful and a new co-crystal, (bpp)(H₂oba)(I), was isolated instead and its structure is reported here. A similar structure has been reported (Ma et al., 2006) and an independent determination of the structure of (I) is reported in the preceeding paper (Li et al., 2008).

The asymmetric unit consists of one bpp and one H₂oba as shown in Fig 1. The dihedral angle between the two phenyl rings of the flexible H₂oba molecule is 57.07°, while it is 27.52° for the two phenyl rings of the bpp. The COOH group(O4—C27—O5) is co-planar with the phenyl ring and the other COOH group(O2—C20—O3) is slightly twisted with a the twist angle is 10.507 (8)°. In (I), the protonated carboxylate O2 of the flexible H₂oba molecule forms two kinds of strong intermolecular hydrogen bonds with atoms N1 and N2 of the bpp molecule (Table 1), linking the molecules into one-dimensional chains. C—H···O hydrogen bonds involving the bpp carbon atoms (C4,C5 and C12) and uncoordinated carboxy oxygen atoms (O3 and O4) provide additional attractive forces between adjacent chains. Furthermore, there are π-π aromatic stacking interactions involving bpp ligands of adjacent units [centroid-centroid distance = 3.7838 (3) Å] that taken together with the C-H···O interactions form a three-dimensional supramolecular motif (Fig. 2).

Experimental

All chemicals were of reagent grade quality obtained from commercial sources and used without further purification. H₂oba (0.5 mmol, 0.129 g), Cd(CH₃COO)₂.2H₂O(1.5 mmol, 0.400 g), bpp(0.5 mmol, 0.099 g) and water (15 ml) were placed in a 25 ml Teflon-lined stainless steel reactor and heated at 453 K for five days, and then cooled slowly to 298 K at which time colourless crystals were obtained.The crystal used for data collection was obtained directly from the reaction mixture on cooling without further re-crystallization.