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Syntheses, crystal structures and Hirshfeld surface analyses of N-aryl-sulfonyl derivatives of cytisine.

ABSTRACT: By aryl-sulfonyl-ation of cytisine in the presence of tri-ethyl-amine, three new compounds have been obtained in good yields: (7R,9R)-N-[(4-ethyl-phen-yl)sulfon-yl]cytisine, C₁₉H₂₂N₂O₃S (I) {systematic name: (1R,5R)-3-[(4-ethyl-phen-yl)sulfon-yl]-1,2,3,4,5,6-hexa-hydro-8H-1,5-methano-pyrido[1,2-a][1,5]diazo-cin-8-one}, (7R,9R)-N-[(4-chloro-phen-yl)sulfon-yl]cytisine, C₁₇H₁₇ClN₂O₃S (II) {systematic name: (1R,5R)-3-[(4-chloro-phen-yl)sulfon-yl]-1,2,3,4,5,6-hexa-hydro-8H-1,5-methano-pyrido[1,2-a][1,5]diazo-cin-8-one} and (7R,9R)-N-[(3-nitro-phen-yl)sulfon-yl]cytisine, C₁₇H₁₇N₃O₅S (III) {systematic name: (1R,5R)-3-[(3-nitro-phen-yl)sulfon-yl]-1,2,3,4,5,6-hexa-hydro-8H-1,5-methano-pyrido[1,2-a][1,5]diazo-cin-8-one}. The crystal structures of the compounds were determined on the basis of single-crystal X-ray diffraction data. The crystal structures of (I)-(III) are distinguished by the arrangement of two fragments of the mol-ecule around the sulfonyl site. For all structures, weak C-H⋯O hydrogen bonds are developed. Hirshfeld surface analysis shows that H⋯H (for I and II) and H⋯O/O⋯H (for III) inter-actions make the most important contribution to the crystal packing.

SUBMITTER: Okmanov RY

PROVIDER: S-EPMC10088325 | biostudies-literature | 2023 Mar

REPOSITORIES: biostudies-literature

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Syntheses, crystal structures and Hirshfeld surface analyses of N-aryl-sulfonyl derivatives of cytisine.

Okmanov Rasul Ya RY Olimova Manzura I MI Karabaeva Surayyo B SB Sapaev Frunza A FA Abdireymov Kudaybergen B KB

Acta crystallographica. Section E, Crystallographic communications 20230310 Pt 4

By aryl-sulfonyl-ation of cytisine in the presence of tri-ethyl-amine, three new compounds have been obtained in good yields: (7R,9R)-N-[(4-ethyl-phen-yl)sulfon-yl]cytisine, C19H22N2O3S (I) {systematic name: (1R,5R)-3-[(4-ethyl-phen-yl)sulfon-yl]-1,2,3,4,5,6-hexa-hydro-8H-1,5-methano-pyrido[1,2-a][1,5]diazo-cin-8-one}, (7R,9R)-N-[(4-chloro-phen-yl)sulfon-yl]cytisine, C17< ...[more]

PMID: 37057015

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Project description:The structures and Hirshfeld surface analysis of three salts of 1-(4-nitro-phenyl)-piperazine are discussed. In 4-(4-nitro-phen-yl)piperazin-1-ium salicylate (C10H14N3O2 +·C7H5O3 -), there are strong hydrogen bonds between cation and anion and the 4-nitro-phenyl substituent occupies an equatorial position in the piperazinium ring. The cation and anion are linked together by supra-molecular inter-actions [graph-set notation of hydrogen bonding (6) propagating in the a-axis direction]. Additionally, there is π-π stacking involving the salicylate anion and the piperazinium cation in adjacent asymmetric units as well as a C-H⋯π inter-action between a hydrogen atom on the piperazine ring and the phenyl ring within the salicyclate anion. In bis-[4-(4-nitro-phen-yl)piperazin-1-ium] bis-(4-fluoro-benzoate) trihydrate (2C10H14N3O2 +·2C7H4FO2 -·3H2O), there are two cations, two anions, and three water mol-ecules of solvation in the asymmetric unit, all linked by hydrogen bonds [graph-set notation of hydrogen bonding R 2 2(20) between adjacent cations and R 3 3(9) between a cation and its adjacent anion]. In the anion, the 4-nitro-phenyl ring occupies an axial substitution position in the piperazinium ring, which is relatively rare. Within the asymmetric unit, the phenyl groups in the cations show an offset π-π inter-action. Additionally, there is a C-H⋯π inter-action between a hydrogen atom on the phenyl ring within a cation and the phenyl ring within an anion. In 4-(4-nitro-phen-yl)piperazin-1-ium 3,5-di-nitro-benzoate (C10H14N3O2 +·C7H4N2O6 -), there is a strong N-H⋯O hydrogen bond linking the cation and anion and the 4-nitro-phenyl ring occupies an axial substitution position in the piperazinium ring, as seen in the previous structure. In the crystal, the cation and the anion form a complex three-dimensional hydrogen-bonded array involving R 2 2(8), R 4 4(12) and R 4 4(20) rings propogating in the a-axis direction. The nitro-phenyl group is disordered with occupancies of 0.806 (10) and 0.194 (10).

Dataset Information

Syntheses, crystal structures and Hirshfeld surface analyses of N-aryl-sulfonyl derivatives of cytisine.

Publications

Syntheses, crystal structures and Hirshfeld surface analyses of <i>N</i>-aryl-sulfonyl derivatives of cytisine.

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