Acridine–benzene-1,3,5-tricarb­oxy­lic acid (3/1)

Hossein Aghabozorg; Saba Goodarzi; Masoud Mirzaei; Behrouz Notash

doi:10.1107/S1600536810050233

. 2010 Dec 15;67(Pt 1):o126. doi: 10.1107/S1600536810050233

Acridine–benzene-1,3,5-tricarboxylic acid (3/1)

Hossein Aghabozorg ^a,^*, Saba Goodarzi ^a, Masoud Mirzaei ^b, Behrouz Notash ^c

PMCID: PMC3050414 PMID: 21522637

Abstract

In the title adduct, 3C₁₃H₉N·C₉H₆O₆ or (acr)₃(btc), associations of one btc and three acr molecules linked by O—H⋯N hydrogen bonds occur. C—H⋯O interactions also occur, resulting in a cyclic hydrogen-bonded synthon R ₂ ¹(6). The acr molecules and the btc molecules also form slipped or offset π–π stacking interactions [centroid–centroid distances of 3.5212 (17) Å for btc rings and 3.703 (2) and 3.731 (2) Å for acr rings]. Together these interactions lead to a three-dimensional network.

Related literature

For background to proton-transfer compounds including acridine, see: Tabatabaee et al. (2009 ▶); Eshtiagh-Hosseini et al. (2010 ▶). For background to co-crystals, see: Dale et al. (2004 ▶).

Experimental

Crystal data

3C₁₃H₉N·C₉H₆O₆
M _r = 747.77
Triclinic,
a = 12.031 (2) Å
b = 13.113 (3) Å
c = 13.220 (3) Å
α = 77.44 (3)°
β = 71.43 (3)°
γ = 72.23 (3)°
V = 1865.9 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.45 × 0.3 × 0.2 mm

Data collection

Stoe IPDS II diffractometer
Absorption correction: numerical (X-RED and X-SHAPE; Stoe & Cie, 2005 ▶) T _min = 0.964, T _max = 0.980
15233 measured reflections
7305 independent reflections
3826 reflections with I > 2σ(I)
R _int = 0.088

Refinement

R[F ² > 2σ(F ²)] = 0.059
wR(F ²) = 0.218
S = 0.95
7305 reflections
526 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; 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 I, global. DOI: 10.1107/S1600536810050233/om2368sup1.cif

e-67-0o126-sup1.cif^{(31.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050233/om2368Isup2.hkl

e-67-0o126-Isup2.hkl^{(357.4KB, 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
O1—H1⋯N1	1.03 (4)	1.62 (4)	2.643 (4)	173 (4)
O3—H3⋯N2	1.08 (6)	1.55 (6)	2.619 (4)	166 (5)
O5—H5⋯N3	1.10 (5)	1.57 (5)	2.659 (4)	171 (6)
C14—H14⋯O6ⁱ	0.93	2.44	3.266 (5)	147
C16—H16⋯O6ⁱ	0.93	2.55	3.355 (5)	145
C18—H18⋯O2ⁱⁱ	0.93	2.54	3.389 (5)	151
C24—H24⋯O5ⁱⁱⁱ	0.93	2.53	3.278 (5)	138
C27—H27⋯O4^iv	0.93	2.59	3.435 (5)	151
C47—H47⋯O3ⁱⁱⁱ	0.93	2.56	3.345 (5)	143

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

Acknowledgments

We are grateful to the Islamic Azad University, North Tehran Branch, for financial support.

supplementary crystallographic information

Comment

Acridine is structurally related to anthracene wherein one of the central CH group is replaced by nitrogen. It is a raw material used for the production of dyes and some valuable drugs. Our research group has recently reported two proton transfer complexes with acridine (Tabatabaee et al., 2009; Eshtiagh-Hosseini et al., 2010). Recently, Dale et al. reported the structure of btc with three pyridines as a cocrystal (Dale et al., 2004). In this article, we report the crystal structure of a new cocrystal system containing acridine and benzenetricarboxylic acid, for the first time.

The title cocrystal structure contains acridine and benzene-1,3,5-tricarboxylic acid in 3:1 molar ratio in the asymmetric unit (Fig. 1). These three bases and one acid formed a cocrystal without any proton transfer. Hence, the acr molecules interact with the carboxylic acid groups of the respective btc molecule through O—H···N and C—H···O hydrogen bonds (Table 1). The latter formed a cyclic hydrogen-bonded synthon R¹₂(6). The acr molecules and also btc molecules form slipped or offset π-π stacking interactions [with centroid···centroid distances of 3.5212 (17) Å for btc rings and 3.703 (2) and 3.731 (2) Å for acr rings]. The dihedral angle of the plane of three carboxylate groups with respect to plane of the central benzene ring in btc are equal to 3.17, 6.46 and 6.52°. Indeed, the crystal structure is stabilized by an extensive series of intermolecular O—H···N and C—H···O hydrogen bonds and π-π stacking interactions, forming a three-dimensional network (Fig. 2).

Experimental

The reaction between a solution of benzenetricarboxylic acid (70 mg, 0.30 mmol) in 5 ml ethanol and acridine (180 mg, 1.0 mmol) in 5 ml ethanol in 1:3 molar ratio at 298 K for 4 hr gave orange block crystals of (acr)₃(btc) after slow evaporation of the solvent at room temperature (m.p. > 260 °C).