Crystal structure of 2-{[5-amino-1-(phenylsulfonyl)-1H-pyrazol-3-yl]oxy}-1-(4-methylphenyl)ethan-1-one

Abstract

In the title compound, C18H17N3O4S, the pyrazole ring is planar, with the sulfur atom lying 0.558 (1) Å out of the ring plane. The NH2 group is involved in an intramolecular hydrogen bond to a sulfonyl oxygen atom; its other hydrogen atom forms an asymmetric three-centre hydrogen bond to the two oxygen atoms of the —O—CH2—C=O— grouping, via the 21 screw axis, forming a ribbon structure parallel to the b axis. Translationally adjacent, coplanar ribbons form a layer parallel to (10\overline{4}).

Crystal structure of 2-[(5-amino-1-tosyl-1H-pyrazol-3-yl)oxy]-1-(4-methoxyphenyl)ethan-1-one 1,4-dioxane monosolvate

“…Dioxanes 1 are omitted. In our previous structure (5; Metwally et al, 2021b), the molecules also associate via hydrogen bonds N-H� � �O carbonyl , to form a broad ribbon structure.…”

“…We have previously prepared both N-alkylated (Metwally et al, 2021a) and O-alkylated (Metwally et al, 2021b) derivatives of N-tosylpyrazole 1. In order to determine which factors lead to the formation of N-alkylated or O-alkylated products of Ntosylpyrazole, a reaction (Fig.…”

“…The structure of 4 0 should be compared with the closely related 2-[(5-amino-1-(phenylsulfonyl)-1H-pyrazol-3-yl)oxy]-1-(p-tolyl)ethan-1-one 5 (Metwally et al, 2021b), which has a tosylsulfonyl rather than a phenylsulfonyl group, and a 4methyl rather than a 4-methoxy substituent at the other phenyl ring; this compound, however, crystallized solvent-free, so that the two structures cannot be isotypic. It forms an analogous intramolecular hydrogen bond to that of 4 0 .…”

“…Figure 3A least-squares fit of 4 and the structure of the closely related (but solvent-free) 2-[(5-amino-1-(phenylsulfonyl)-1H-pyrazol-3-yl)oxy]-1-(ptolyl)ethan-1-one 5(Metwally et al, 2021b); the latter is shown with dashed bonds.…”