4,4′-(Propane-1,3-di­yl)dibenzoic acid

Jia Hua; Lu Gao

doi:10.1107/S1600536809033005

. 2009 Aug 26;65(Pt 9):o2233. doi: 10.1107/S1600536809033005

4,4′-(Propane-1,3-diyl)dibenzoic acid

Jia Hua ^a,^*, Lu Gao ^a

PMCID: PMC2969863 PMID: 21577632

Abstract

The complete molecule of the title compound, C₁₇H₁₆O₄, is generated by crystallographic twofold symmetry, with the central C atom lying on the rotation axis and a dihedral angle between the benzene rings of 81.9 (2)°. In the crystal, molecules are linked by O—H⋯O hydrogen bonding between carboxyl groups, forming one-dimensional supramolecular chains.

Related literature

For general background, see: Bradshaw et al. (2005 ▶); Eddaoudi et al. (2001 ▶); Heo et al. (2007 ▶); Kesanli & Lin (2003 ▶). For related structures, see: Dai et al. (2005 ▶); Li et al. (2007 ▶); Ma et al. (2006 ▶). For the synthesis, see: Cram & Steinberg (1951 ▶).

Experimental

Crystal data

C₁₇H₁₆O₄
M _r = 284.30
Monoclinic,
a = 14.569 (3) Å
b = 4.7337 (6) Å
c = 21.463 (3) Å
β = 102.722 (10)°
V = 1443.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.48 × 0.20 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.947, T _max = 0.989
3830 measured reflections
1276 independent reflections
688 reflections with I > 2σ(I)
R _int = 0.059

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.115
S = 0.94
1276 reflections
96 parameters
H-atom parameters constrained
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809033005/xu2559sup1.cif

e-65-o2233-sup1.cif^{(13.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033005/xu2559Isup2.hkl

e-65-o2233-Isup2.hkl^{(63.1KB, 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⋯O1ⁱ	0.82	1.84	2.642 (2)	168

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the National Natural Science Foundation of China.

supplementary crystallographic information

Comment

In the past decades the design and synthesis of metal-organic frameworks have received extensive attention in the field of supra-molecular chemistry and crystal engineering (Bradshaw et al., 2005; Eddaoudi et al., 2001; Heo et al., 2007; Kesanli et al., 2003). As part of our investigation on the metal-organic frameworks (Dai et al., 2005; Li et al., 2007; Ma et al., 2006), we report here the crystal structure of the title compound.

In the crystal structure, the title molecule has site symmetry 2, the C1 atom is located on a twofold rotation axis. The two symmetry-related benzene rings are twisted with respect to each other with a dihedral angle of 81.9 (2)° (Fig. 1). The carboxylic acid groups of neighboring molecules form strong intermolecular O—H···O hydrogen bonds (Table 1), linking the molecules into the one-dimensional supra-molecular chains (Fig. 2).

Experimental

4,4'-(Propane-1,3-diyl)dibenzoic acid was synthesized according to literature methods (Cram & Steinberg, 1951), and other reagents were commercially obtained without further purification. In a typical synthesis procedure for the title compound, the reactants Zn(NO₃)₂.6H₂O (0.149 g, 0.5 mmol), 4,4'-(propane-1,3-diyl)dibenzoic acid (0.142 g, 0.5 mmol), HCl (38%, 0.30 ml) and triethylamine (0.35 ml) were mixed in water (5 ml). The mixture was placed in a 15 ml Teflon-lined stainless steel autoclave with a filling capacity of 37.7% and heated under autogenous pressure for 5 d at 453 K. After slow cooling to room temperature, the block-shaped colourless crystals suitable for X-ray diffraction were obtained.