Directionality and site selectivity of N⋯Cl halogen bonding in two azaaromatic chloride crystals

Zhu, Yi; Miao, Ti Fang; Yang, Yang Yi; Zhuang, Dong Yue; Zheng, Kang; Wong, Wing Tak

doi:10.1016/j.molstruc.2010.04.035

Cited by 5 publications

(2 citation statements)

References 46 publications

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“…In the 13 Compound 1a was crystallized in the monoclinic system with space group P2 1 /n. In the molecule of 1a (as shown in Figure 4), the bond lengths and angles were very similar to those of methyl p-hydroxybenzoate derivatives [29,30] the benzene ring carbons of compounds 2b and 2c are basically consistent with the ab situation.…”

Section: Nmr Spectral Characterizationsupporting

confidence: 56%

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Synthesis, Crystal Structure, Spectral Characterization and Antifungal Activity of Novel Phenolic Acid Triazole Derivatives

Xiao,

Song,

Xiong

et al. 2023

Molecules

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At present, phenolic acid derivatives and triazole derivatives have a good antifungal effect, which has attracted widespread attention. A series of novel phenolic acid triazole derivatives were synthesized, and their structures were characterized by IR, MS, NMR, and X-ray crystal diffraction. Compound methyl 4-(2-bromoethoxy)benzoate, methyl 4-(2-(1H-1,2,4-triazol-1-yl) ethoxy)benzoate, 4-(2-(1H-1,2,4-triazol-1-yl)ethoxy)benzoic acid and 4-(2-(1H-1,2,4-triazol-1-yl) ethoxy)-3-methoxybenzoic acid crystallize in the monoclinic system with space group P21/n, the monoclinic system with space group P21, the monoclinic system with space group P21 and the orthorhombic system with space group Pca21, respectively. At a concentration of 100 μg/mL and 200 μg/mL, the antifungal activity against seven plant pathogen fungi was determined. Compound methyl 4-(2-bromoethoxy)benzoate has the best inhibitory effect on Rhizoctonia solani AG1, and the inhibitory rate reached 88.6% at 200 μg/mL. The inhibitory rates of compound methyl 4-(2-(1H-1,2,4-triazol-1-yl) ethoxy)benzoate against Fusarium moniliforme and Sphaeropsis sapinea at a concentration of 200 μg/mL were 76.1% and 75.4%, respectively, which were better than that of carbendazim.

show abstract

Section: Nmr Spectral Characterizationsupporting

confidence: 56%

“…Compound 1a was crystallized in the monoclinic system with space group P21/n the molecule of 1a (as shown in Figure 4), the bond lengths and angles were very sim to those of methyl p-hydroxybenzoate derivatives [29,30]…”

Section: Crystal Structure Of Compound 1amentioning

confidence: 99%

Synthesis, Crystal Structure, Spectral Characterization and Antifungal Activity of Novel Phenolic Acid Triazole Derivatives

Xiao,

Song,

Xiong

et al. 2023

Molecules

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Triazines, Tetrazines, and Fused Ring Polyaza Systems

Prokhorov

Kozhevnikov

2011

Progress in Heterocyclic Chemistry

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Evidence of Weak Halogen Bonding: New Insights on Itraconazole and its Succinic Acid Cocrystal

Nonappa

Lahtinen

Kolehmainen

et al. 2012

Crystal Growth & Design

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Exact knowledge of the crystal structure of drugs and lead compounds plays a significant role in the fields of crystal engineering, docking, computational modeling (drug−receptor interactions), and rational design of potent drugs in pharmaceutical chemistry. The succinic acid cocrystal of the systemic antifungal drug, itraconazole, reported by Remenar et al. (J. Am. Chem. Soc. 2003, 125, 8456−8457) (CSD: IKEQEU), represents one of the classical examples displaying a molecular fitting mechanism in the solid state. In this work, we disclose the X-ray single-crystal structure of the cis-itraconazole−succinic acid (2:1) cocrystal and found that it differs slightly from the previously reported structure by the location of the elements (C, H, and N) in the 1,2,4-triazol-5-one ring. By making use of the new solid-state structure, we have also applied an enhanced disorder model, which, in turn, uncovered the intriguing halogen bond (XB) interactions (0.86 × van der Waals distance of C−Cl•••N), which were previously unnoticed. Furthermore, the crystal structure of cis-itraconazole reported by Peeters et al. (Acta Crystallogr. 1996, C52, 2225−2229 (CSD: TEHZIP) is also revisited. For the structure of neat cis-itraconazole, new low-temperature as well as a revised ambient temperature (0 °C) X-ray single crystal structures with new disorder models are described. More importantly, a weak halogen bonding interaction (0.9 × van der Waals distance of C− Cl•••O) has now been perceived in this structure. The XB contacts remained without consideration in the original report primarily due to the lack of its recognition, at that time. In addition to these new findings, solid-state NMR and the thermoanalytical properties were examined by thermogravimetric analysis and differential scanning calorimetry.

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Directionality and site selectivity of N⋯Cl halogen bonding in two azaaromatic chloride crystals

Cited by 5 publications

References 46 publications

Synthesis, Crystal Structure, Spectral Characterization and Antifungal Activity of Novel Phenolic Acid Triazole Derivatives

Synthesis, Crystal Structure, Spectral Characterization and Antifungal Activity of Novel Phenolic Acid Triazole Derivatives

Triazines, Tetrazines, and Fused Ring Polyaza Systems

Evidence of Weak Halogen Bonding: New Insights on Itraconazole and its Succinic Acid Cocrystal

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