Back to Search Start Over

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

Authors :
Huiqi Qu
Ruixin Chen
Yiru Ma
Na Li
Mingjuan Zhang
Yueqin Yu
Zhiguo Lv
Kang Liu
Source :
Crystals, Vol 13, Iss 3, p 402 (2023)
Publication Year :
2023
Publisher :
MDPI AG, 2023.

Abstract

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.

Details

Language :
English
ISSN :
20734352
Volume :
13
Issue :
3
Database :
Directory of Open Access Journals
Journal :
Crystals
Publication Type :
Academic Journal
Accession number :
edsdoj.b61cf79f3e09446a94ed89bd25d84abc
Document Type :
article
Full Text :
https://doi.org/10.3390/cryst13030402