Complex interplay of hydrogen bonding, halogen bonding and π-interactions in methyl 2-(7-chloro-1H-pyrazolo[3,4-b]quinolin-1-yl)acetate: Synthesis, X-ray crystallography, energetic features and anti-urease efficacy

Abstract

The present study investigates the influence of noncovalent interactions in the design and structural control of crystal packing of pyrazoloquinoline derivative. Compound 3 was prepared in a two-step process in excellent yield. The reaction of 2,7-dichloroquinoline-3-carbaldehyde (1) and hydrazine monohydrate gave access to intermediate 2 which was alkylated regioselectively at the N1 pyrazole nitrogen. The synergistic effects of noncovalent interactions such as H-bonding (C-H…O, C-H…N), halogen bonding (Cl…O) and π-contacts (π…π, Cl…π and CH…π) remained crucial in leading the structural topology of pyrazoloquinoline skeleton. The types of noncovalent interactions was energetically evaluated..