Home Crystal structure of bis(acridin-10-ium) 2,5-dihydroxyterephthalate — 2,5-dihydroxyterephthalic acid (1/1), C21H15NO6
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Crystal structure of bis(acridin-10-ium) 2,5-dihydroxyterephthalate — 2,5-dihydroxyterephthalic acid (1/1), C21H15NO6

  • Xin-Hong Chang ORCID logo EMAIL logo
Published/Copyright: September 17, 2019

Abstract

C21H15NO6, triclinic, P1̄ (no. 2), a = 9.3591(4) Å, b = 9.4371(5) Å, c = 10.1106(5) Å, α = 102.581(4)°, β = 92.929(4)°, γ = 102.573(4)°, V = 846.09(7) Å3, Z = 2, Rgt(F) = 0.0452, wRref(F2) = 0.1135, T = 288.7(3) K.

CCDC no.: 1947088

The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Brown block
Size:0.26 × 0.23 × 0.16 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.11 mm−1
Diffractometer, scan mode:SuperNova, ω
θmax, completeness:25.5°, 98%
N(hkl)measured, N(hkl)unique, Rint:10752, 3060, 0.026
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2499
N(param)refined:256
Programs:CrysAlisPRO [1], SHELX [2], [3]
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

AtomxyzUiso*/Ueq
N10.41853(16)0.38719(18)0.79478(15)0.0292(4)
H10.49150.39390.74630.035*
C10.4759(2)0.6554(2)0.8570(2)0.0345(5)
H1A0.55370.66090.80320.041*
C20.4447(2)0.7815(2)0.9303(2)0.0420(5)
H20.50220.87390.92620.050*
C30.3272(3)0.7760(2)1.0126(2)0.0433(6)
H30.30920.86431.06270.052*
C40.2404(2)0.6430(2)1.0191(2)0.0385(5)
H40.16280.64081.07310.046*
C50.2671(2)0.5063(2)0.94356(18)0.0296(4)
C60.1825(2)0.3661(2)0.94405(19)0.0326(5)
H60.10100.35890.99330.039*
C70.2163(2)0.2362(2)0.87274(19)0.0309(5)
C80.1334(2)0.0897(2)0.8707(2)0.0430(5)
H80.05040.07800.91770.052*
C90.1739(3)−0.0322(3)0.8013(2)0.0479(6)
H90.1182−0.12700.80020.057*
C100.3009(3)−0.0164(2)0.7303(2)0.0451(6)
H100.3284−0.10150.68460.054*
C110.3831(2)0.1201(2)0.7276(2)0.0371(5)
H110.46620.12870.68040.045*
C120.3410(2)0.2495(2)0.79748(18)0.0287(4)
C130.3882(2)0.5152(2)0.86381(18)0.0277(4)
O10.60291(14)0.34549(17)0.44697(14)0.0433(4)
O20.66247(14)0.43920(16)0.67028(14)0.0384(4)
O30.92840(15)0.57414(19)0.76347(13)0.0462(4)
H3A0.84000.54320.76660.069*
C140.89348(19)0.4251(2)0.39358(18)0.0268(4)
H140.82180.37490.32170.032*
C150.85271(19)0.45881(19)0.52453(17)0.0236(4)
C160.6944(2)0.4114(2)0.54846(19)0.0282(4)
C170.9612(2)0.5355(2)0.63228(17)0.0264(4)
O4−0.13293(16)0.18322(16)0.67900(16)0.0454(4)
H4A−0.21040.13510.69720.068*
O50.33512(14)0.26655(15)0.47314(15)0.0378(4)
H50.42300.28640.46280.057*
O60.33634(17)0.05419(18)0.32518(18)0.0578(5)
C180.13156(19)0.0637(2)0.45407(18)0.0267(4)
C190.0605(2)0.1523(2)0.54319(19)0.0284(4)
H190.10090.25450.57170.034*
C20−0.0696(2)0.0910(2)0.59015(19)0.0290(4)
C210.2764(2)0.1284(2)0.4111(2)0.0320(5)

Source of material

In a typical experiment, 2,5-dihydroxyterephthalic acid (0.02 g, 0.1 mmol) is dissolved in 5 mL of absolute ethanol, acridine (0.02 g, 0.1 mmol) is dissolved in another 5 mL of absolute ethanol. The two solutions are mixed. The mixture was left at room temperature for 10 minutes to get red block crystals of the title compound.

Experimental details

The hydrogen atoms were placed at calculated positions with the SHELX program (AFIX options: 43 and 147).

Comment

Over the past few decades, the design and assembly of organic cocrystals molecular materials has gained considerable interest [4], [5], [6] due to their potential applications such as luminescence and polarized emission [7], [8], luminescent sensors [9], [10] and tunable mechanical properties [11]. Synthesis methods of organic cocrystals mainly include solution processes [12], [13], vacuum sublimation [14] and external stimuli [15]. The most frequently used method for preparing cocrystals is a solution process and single crystals are grown by slow evaporation of the solvents. But it is still difficult to predict the generation of a new cocrystal. In order to further study the formation conditions of cocrystals, in this article, we use 2,5-dihydroxyterephthalic acid (H2diph) and acridine (AD) to synthesize a cocrystal.

The asymmetric unit of the cocrystal contains one acridinium cation, one half of a 2,5-dihydroxyterephthalic acid molecule and one half 2,5-dihydroxyterephthalate dianion. In the cocrystal, π-π intermolecular interactions between benzene rings of AD molecules and pyridine rings of AD molecules (3.722 Å), benzene rings of H2diph molecules and benzene rings of AD molecules (3.593 Å), and hydrogen bonding from O(5)—H(5)⋯O(1)a (distance: 2.49 Å, angle: 174°), C(6)—H(6)⋯O(3) (distance: 3.16 Å, angle: 133°), and N(1)—H(1)⋯O(2)b (distance: 2.67 Å, angle: 169°) form a three-dimensional structure. The cocrystal structure is similar to the structures of cocrystals reported by Christian Wolf’s group [16]. They reported a series of cocrystals by acridine and dicarboxylic acids. All these cocrystal molecules are stabilized by π-stacking and hydrogen bonding.

Acknowledgements

This work was supported by key scientific research projects of higher education of Henan Province (16 A150016) and Henan Province Natural Science Foundation (182300410166).

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Received: 2019-05-28
Accepted: 2019-08-14
Published Online: 2019-09-17
Published in Print: 2019-11-26

©2019 Xin-Hong Chang, published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 Public License.

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