Naphthalene-1,4,5,8-tetra­carboxylic acid 1,8-anhydride–4,4′-bipyridine (1/1)

Ji-Hua Deng; Meng-Ping Guo; Qiao-Chu Zhang; Lin Yuan; Hui-Rui Guo; Guang-Quan Mei

doi:10.1107/S1600536809044146

. 2009 Oct 31;65(Pt 11):o2912. doi: 10.1107/S1600536809044146

Naphthalene-1,4,5,8-tetracarboxylic acid 1,8-anhydride–4,4′-bipyridine (1/1)

Ji-Hua Deng ^a,^*, Meng-Ping Guo ^b, Qiao-Chu Zhang ^a, Lin Yuan ^a, Hui-Rui Guo ^b, Guang-Quan Mei ^a

PMCID: PMC2970960 PMID: 21578491

Abstract

The title compound, C₁₄H₆O₇·C₁₀H₈N₂, has been hydrothermally synthesized. Structural ananlysis indicates that the crystals are produced by cocrystallization of naphthalene-1,4,5,8-tetracarboxylic acid 1,8-anhydride and 4,4′-bipyridine (bpy) molecules. The crystal packing is stabilized by intermolecular O—H⋯N and C—H⋯O hydrogen bonds and π–π stacking interactions [centroid–centroid distances = 3.5846 (9) Å].

Related literature

For the structures of naphthalene-1,4,5,8-tetracarboxylic acid 1,8-anhydride, its DMSO solvate and several metal complexes, see: Blackburn et al. (1997 ▶); Fitzgerald et al. (1992 ▶); Robl (1987 ▶); Xu et al. (2005a ▶,b ▶.) For hydrogen bonds, see: Desiraju & Steiner (1999 ▶).

Experimental

Crystal data

C₁₄H₆O₇·C₁₀H₈N₂
M _r = 442.37
Triclinic,
a = 9.6193 (8) Å
b = 9.6964 (3) Å
c = 10.192 (1) Å
α = 81.384 (5)°
β = 85.615 (6)°
γ = 83.947 (3)°
V = 932.9 (1) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 173 K
0.28 × 0.24 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T _min = 0.968, T _max = 0.977
6648 measured reflections
3240 independent reflections
2772 reflections with I > 2σ(I)
R _int = 0.017

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.104
S = 1.06
3240 reflections
300 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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/S1600536809044146/im2151sup1.cif

e-65-o2912-sup1.cif^{(19.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044146/im2151Isup2.hkl

e-65-o2912-Isup2.hkl^{(158.9KB, 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	0.84	1.77	2.594 (2)	167
O4—H4A⋯N1ⁱⁱ	0.84	1.74	2.573 (2)	171
C16—H16⋯O1ⁱⁱⁱ	0.95	2.36	3.254 (2)	157
C22—H22⋯O3^iv	0.95	2.57	3.425 (2)	150

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

Acknowledgments

The authors thank the Youth Foundation of Jiangxi Provincial Office of Education (GJJ09605, GJJ09355) and the Natural Science Foundation of Jiangxi Province (2008GZH0063) for financial support.

supplementary crystallographic information

Comment

Several crystal structures of naphthalene-1,4,5,8-tetracarboxylic acid 1,8-anhydride (ntaa) (Xu et al., 2005b), its DMSO solvate (Blackburn et al., 1997) and some metal complexes (Fitzgerald et al., 1992; Robl et al., 1987; Xu et al., 2005a) have been reported in the literature. Herein, we report the synthesis and crystal crystal structure of a new compound of ntaa.

The structure of the title compound, (I), consists of one ntaa molecule and one bpy molecule. The two carboxylate groups of the ntaa are not coplanar with the naphthalene ring. The corresponding dihedral angles O1-C1-C2-C13 and O3-C12-C11-C10 are 50.8 (2)° and 52.7 (2)°, respectively. The two pyridyl rings of the bpy molecule are almost coplanar with a dihedral angle of 3.6 (3)° (Fig. 1).

The molecules are held together by intermolecular hydrogen bonding interactions (Desiraju et al. 1999) and π-π stacking interactions, forming a three-dimensional supramolecular network. Two O–H···N hydrogen bonds with O···O distances of 2.594 (2) and 2.573 (2) Å are formed with the two carboxylic acid OH groups as donors and the N atoms of the two inequivalent bpy molecules as acceptors (Table 1, Fig. 1 and Fig. 2). In addition, π-π stacking interactions between two pyridyl rings (3.346 Å) and two naphthalene rings (3.357 Å), are also observed.

Experimental

A mixture of 0.5 mmol NiCl₂ × 6 H₂O, 0.5 mmol of naphthalene-1,4,5,8-tetracarboxylic acid, 0.5 mmol of 4,4-bipyridine, 1.0 mmol of NaOH and 10 ml distilled water was heated to 383 K for six days in a 20 ml sealed Teflon-lined stainless steel vessel. After the autoclave was cooled to room temperature, block-shaped yellow crystals of (I) were isolated by filtration, washed with water, and dried in air. (yield: 53.2% based on naphthalene-1,4,5,8-tetracarboxylic acid)