4,5-Dicarb­oxy­naphthalene-1,8-dicarb­oxy­lic anhydride–1,10-phenanthroline (1/1)

Xiang-Yang Wu; Xiang-Jun Xu; Xiang-Cheng Wang

doi:10.1107/S1600536811002492

. 2011 Jan 22;67(Pt 2):o474. doi: 10.1107/S1600536811002492

4,5-Dicarboxynaphthalene-1,8-dicarboxylic anhydride–1,10-phenanthroline (1/1)

Xiang-Yang Wu ^a,^*, Xiang-Jun Xu ^a, Xiang-Cheng Wang ^b

PMCID: PMC3051702 PMID: 21523132

Abstract

In the crystal structure of the title 1:1 adduct, C₁₂H₈N₂·C₁₄H₆O₇, the carboxyl groups are involved in intermolecular O—H⋯O hydrogen bonds, which link the molecules into centrosymmetric dimers. These dimers are further linked by intermolecular O—H⋯N hydrogen bonds. C—H⋯O interactions also occur between the 1,10-phenanthroline (phen) and 4,5-dicarboxynaphthalene-1,8-dicarboxylic anhydride (H₂NTC) molecules. In addition, the crystal structure exhibits π–π interactions of the phen⋯phen and H₂NTC⋯H₂NTC types with centroid–centroid distances of 3.579 (3) and 3.774 (3) Å, respectively.

Related literature

For background to the importance of 1,4,5,8-naphthalenetetracarboxylic acid and 1,10-phenanthroline, see: Chen et al. (2005 ▶); Che et al. (2006 ▶).

Experimental

Crystal data

C₁₂H₈N₂·C₁₄H₆O₇
M _r = 466.39
Triclinic,
a = 9.0189 (5) Å
b = 10.1588 (7) Å
c = 11.2140 (8) Å
α = 104.267 (6)°
β = 92.278 (5)°
γ = 101.256 (5)°
V = 972.42 (11) Å³
Z = 2
Cu Kα radiation
μ = 0.99 mm⁻¹
T = 293 K
0.35 × 0.25 × 0.2 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T _min = 0.858, T _max = 1.000
6756 measured reflections
3416 independent reflections
2679 reflections with I > 2σ(I)
R _int = 0.061

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.159
S = 0.99
3416 reflections
316 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.41 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: SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811002492/lx2183sup1.cif

e-67-0o474-sup1.cif^{(19.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811002492/lx2183Isup2.hkl

e-67-0o474-Isup2.hkl^{(164.1KB, 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—H2A⋯N1ⁱ	0.82	1.97	2.683 (2)	144
O4—H4⋯O1ⁱⁱ	0.82	1.69	2.4637 (18)	158
C2—H2⋯O5ⁱⁱⁱ	0.93	2.59	3.481 (3)	161
C8—H8⋯O3ⁱⁱ	0.93	2.57	3.312 (3)	137
C10—H10⋯O4^iv	0.93	2.42	3.258 (3)	150

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

Acknowledgments

The authors thank Jiangsu University for supporting this work.

supplementary crystallographic information

Comment

1,4,5,8-Naphthalenetetracarboxylic acid (H₄NTC) is of special interest since its high symmetry and large π-conjugated structure can allow to construct molecular assemblies with novel structure motifs and physical properties (Chen et al., 2005). The 1,10-phenanthroline (phen) has been widely used to build novel supramolecular architectures through aromatic π..π interactions (Che et al., 2006). We report herein on the crystal structure of the title compound (Fig. 1).

In the crystal packing (Fig. 2), the carboxyl groups are involved in intermolecular O–H···O hydrogen bonds, which link the molecules into centrosymmetric dimers. These dimers are further linked by an intermolecular O–H···N hydrogen bond. There are also C–H···O interactions between the phen and H₂NTC (Table 1). In addition, the crystal structure exhibit the π-π interactions between the phen···phen and H₂NTC···H₂NTC, respectively. The π-π interaction distance (Cg1-to-Cg2ⁱ) between the phen···phen is 3.579 (3) Å, and the π-π interaction distance (Cg3-to-Cg4ⁱⁱ) between the H₂NTC···H₂NTC is 3.774 (3) Å (Fig. 3). Cg1, Cg2, Cg3 and Cg4 are centroids of the N2-C2, N1-C7, C18-C20 and C13-C15 ring, respectively.

Experimental

The reagents, purchased from standard commercial sources and without further purification, were 1,4,5,8-naphthalenetetracarboxylic acid and 1,10-phenanthroline. A mixture of H₄NTC (0.0304 g, 0.10 mmol), phen (0.018 g, 0.10 mmol) and water (10 mL) in a 25 mL Teflon-lined stainless steel autoclave was heated for 3 d at 433 K under autogenous pressure and cooled to room temperature. Yellow block crystals were obtained.