The Role of Weak C–H···X (X = O, π) Interactions in Three 1-Hydroxy-2-naphthoic Acid Cocrystals with N-Containing Heteroaromatics: Structural Characterization and Synthon Cooperation
Huiqi Qu,
Ruixin Chen,
Yiru Ma,
Na Li,
Mingjuan Zhang,
Yueqin Yu,
Zhiguo Lv,
Kang Liu
Affiliations
Huiqi Qu
College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, China
Ruixin Chen
Department of Mathematics, College of Mathematics and Physics, Qingdao University of Science and Technology, Qingdao 266061, China
Yiru Ma
Key Laboratory of Eco-Chemical Engineering, International Science and Technology Cooperation Base of Eco-Chemical Engineering and Green Manufacturing, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, China
Na Li
Key Laboratory of Eco-Chemical Engineering, International Science and Technology Cooperation Base of Eco-Chemical Engineering and Green Manufacturing, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, China
Mingjuan Zhang
Key Laboratory of Eco-Chemical Engineering, International Science and Technology Cooperation Base of Eco-Chemical Engineering and Green Manufacturing, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, China
Yueqin Yu
Key Laboratory of Eco-Chemical Engineering, International Science and Technology Cooperation Base of Eco-Chemical Engineering and Green Manufacturing, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, China
Zhiguo Lv
College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, China
Kang Liu
Key Laboratory of Eco-Chemical Engineering, International Science and Technology Cooperation Base of Eco-Chemical Engineering and Green Manufacturing, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, China
Herein, three novel cocrystals of 1-hydroxy-2-naphthoic acid: tetramethylpyrazine, 1-hydroxy-2-naphthoic acid:1,10-phenanthroline, and 1-hydroxy-2-naphthoic acid:1,4-bis(imidazol-1-ylmethyl)benzene (L2) were obtained by crystallization in methanol–water mixed solvent via a slow evaporation method. The cocrystalline products 1−3 were carried out by a range of techniques, including single-crystal X-ray diffraction, Fourier transform–infrared spectroscopy, elemental analysis, and thermogravimetric testing. We analyzed the crystal structures of the cocrystals 1−3 and found that weak interactions C–H···X (X = O or π) were of great importance in the process of self-assembly as well as strong and conventional hydrogen bonds (N–H···O, O–H···N, O–H···O), leading to a stable and diverse multidimensional supramolecular architecture. It is worth noting that a series of ring motifs with different sizes were explored in the crystal structures of the above complexes, such as R22(5), R22(7), R22(8), R23(13), R24(16), R44(16), R44(22), and so on. The classical and robust supramolecular synthon intermolecular bond between acid and pyridine (acid···pyridine) heterosynthon R22(7), commonly found in organic solids containing carboxylic acids with other N-containing heteroaromatics, was further demonstrated to be involved in the construction of the hydrogen-bond networks of cocrystal 1. The thermogravimetric technique used in this study proved that the mass losses of these three cocrystals were closely related to the strength of the hydrogen bonds in the package fraction.
