Dataset Information

Syntheses and crystal structures of a nitro-anthracene-isoxazole and its oxidation product.

ABSTRACT: The syntheses and structures of an unexpected by-product from an iodination reaction, namely, ethyl 5-methyl-3-(10-nitro-anthracen-9-yl)isoxazole-4-carb-oxy-l-ate, C₂₁H₁₆N₂O₅, (I), and its oxidation product, ethyl 3-(9-hy-droxy-10-oxo-9,10-di-hydro-anthracen-9-yl)-5-methyl-isoxazole-4-carboxyl-ate, C₂₁H₁₇NO₅ (V) are described. Compound (I) crystallizes with two mol-ecules in the asymmetric unit in which the dihedral angles between the anthracene fused-ring systems and isoxazole ring mean planes are 88.67 (16) and 85.64 (16)°; both mol-ecules feature a disordered nitro group. In (V), which crystallizes with one mol-ecule in the asymmetric unit, the equivalent dihedral angle between the almost planar anthrone ring system (r.m.s. deviation = 0.029 Å) and the pendant isoxazole ring is 89.65 (5)°. In the crystal of (I), the mol-ecules are linked by weak C-H⋯O inter-actions into a three-dimensional network and in the extended structure of (V), inversion dimers linked by pairwise O-H⋯O hydrogen bonds generate R ₂ ²(14) loops.

SUBMITTER: Li C

PROVIDER: S-EPMC9260358 | biostudies-literature | 2022 Jul

REPOSITORIES: biostudies-literature

ACCESS DATA

Publications

Syntheses and crystal structures of a nitro-anthracene-isoxazole and its oxidation product.

Li Chun C Weaver Matthew J MJ Campbell Michael J MJ Natale Nicholas R NR

Acta crystallographica. Section E, Crystallographic communications 20220610 Pt 7

The syntheses and structures of an unexpected by-product from an iodination reaction, namely, ethyl 5-methyl-3-(10-nitro-anthracen-9-yl)isoxazole-4-carb-oxy-l-ate, C21H16N2O5, (I), and its oxidation product, ethyl 3-(9-hy-droxy-10-oxo-9,10-di-hydro-anthracen-9-yl)-5-methyl-isoxazole-4-carboxyl-ate, C21H17NO5 (V) are described. Compound (I) crystallizes with two mol-ecules in the asymmetric unit in which the dihedral ang ...[more]

PMID: 35855371

Similar Datasets

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 and crystal structures of a nitro-anthracene-isoxazole and its oxidation product.

Publications

Syntheses and crystal structures of a nitro-anthracene-isoxazole and its oxidation product.

Similar Datasets

OmicsDI is part of the ELIXIR infrastructure

Tweets