2-Amino­terephthalic acid–4,4′-bipyridine (1/1)

Wenzhi Xiao; Ruiting Xue; Yansheng Yin

doi:10.1107/S1600536811016448

. 2011 May 7;67(Pt 6):o1333. doi: 10.1107/S1600536811016448

2-Aminoterephthalic acid–4,4′-bipyridine (1/1)

Wenzhi Xiao ^a, Ruiting Xue ^b, Yansheng Yin ^b,^*

PMCID: PMC3120464 PMID: 21754729

Abstract

The asymmetric unit of the title compound, C₁₀H₈N₂·C₈H₇NO₄, contains two half-molecules, which constitute a 1:1 co-crystal. The 2-aminoterephthalic acid molecule is situated on an inversion center being disordered between two orientations in a 1:1 ratio. In the 4,4′-bipyridine molecule, which is situated on a twofold rotational axis, the two pyridine rings form a dihedral angle of 37.5 (1)°. In the crystal, molecules are held together via intermolecular N—H⋯O and O—H⋯N hydrogen bonds. The crystal packing exhibits π–π interactions between the aromatic rings with a centroid–centroid distance of 3.722 (3) Å.

Related literature

For the crystal structures of polymeric coordination polymers with 2-aminoterephthalic acid linkers, see: Ma et al. (2005) ▶; Bauer et al. (2008 ▶).

Experimental

Crystal data

C₁₀H₈N₂·C₈H₇NO₄
M _r = 337.33
Monoclinic,
a = 16.9501 (18) Å
b = 11.1959 (13) Å
c = 9.251 (1) Å
β = 116.986 (2)°
V = 1564.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.33 × 0.19 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.967, T _max = 0.989
3865 measured reflections
1370 independent reflections
894 reflections with I > 2σ(I)
R _int = 0.075

Refinement

R[F ² > 2σ(F ²)] = 0.067
wR(F ²) = 0.199
S = 1.00
1370 reflections
118 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 global, I. DOI: 10.1107/S1600536811016448/cv5085sup1.cif

e-67-o1333-sup1.cif^{(13.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016448/cv5085Isup2.hkl

e-67-o1333-Isup2.hkl^{(67.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811016448/cv5085Isup3.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
N1—H1A⋯O2ⁱ	0.86	2.08	2.931 (5)	172
N1—H1B⋯O2ⁱⁱ	0.86	1.95	2.619 (5)	133
O1—H1⋯N2ⁱⁱⁱ	0.82	1.82	2.635 (3)	170

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

Acknowledgments

The authors acknowledge the Scientific Research Fund of Hunan Provincial Education Department (grant No. 10 C0559) and the National Science Foundation of China (grant No. 50672090).

supplementary crystallographic information

Comment

Bipyridine is a well known molecule often used as a linker in polymeric coordination compounds. 2-Aminoterephthalic acid is also sometimes used as a linker in polymeric compounds (Ma et al., 2005; Bauer et al., 2008). The title compound (I) is a 1:1 cocrystal of the aforementioned linkers. Herewith we present its crystal structure.

In (I) (Fig. 1), the 2-aminoterephthalic acid molecule is situated on an inversion center, therefore, it is disordered (namely, the amino group is disordered between two positions). The carboxyl groups are twisted from the benzene ring plane at 11.4 (1)°. The 4,4'-bipyridine molecule is situated on a twofold rotational axis, and two pyridine rings form a dihedral angle of 37.5 (1)°.

In the crystal structure, the molecules are held together via intermolecular N—H···O and O—H···N hydrogen bonds. The crystal packing exhibits π—π interactions between the aromatic rings with the centroid-to-centroid distance of 3.722 (3) Å.

Experimental

2-Diaminoterephthalic acid(10 mmol) and 4,4'-bipyridine(10 mmol) were dissolved to methanol (10 ml) and then hydrochloric acid(5 ml) was added. A few minutes later, an methanol solution (10 ml) of tin tetrachloride (5 mmol) was added with stirring. The reaction mixture was stirred for 4 h. The solution was held at room temperature for about two weeks, whereupon yellow crystals of the title compound, which were beyond expectations, were obtained.