Syntheses and crystal structures of 2-( p -tol-yl)-1 H -perimidine hemihydrate and 1-methyl-2-( p -tol-yl)-1 H -perimidine.

Autor: Kalle P; N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninsky pr. 31, Moscow 119991, Russian Federation., Tatarin SV; N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninsky pr. 31, Moscow 119991, Russian Federation.; Department of Chemistry, Lomonosov Moscow State University, Lenin's Hills, 1-3, Moscow, 119991, Russian Federation., Kiseleva MA; N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninsky pr. 31, Moscow 119991, Russian Federation.; Department of Chemistry, Lomonosov Moscow State University, Lenin's Hills, 1-3, Moscow, 119991, Russian Federation., Zakharov AY; N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninsky pr. 31, Moscow 119991, Russian Federation., Smirnov DE; N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninsky pr. 31, Moscow 119991, Russian Federation.; Department of Chemistry, Lomonosov Moscow State University, Lenin's Hills, 1-3, Moscow, 119991, Russian Federation., Bezzubov SI; N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninsky pr. 31, Moscow 119991, Russian Federation.
Jazyk: angličtina
Zdroj: Acta crystallographica. Section E, Crystallographic communications [Acta Crystallogr E Crystallogr Commun] 2022 Jan 14; Vol. 78 (Pt 2), pp. 169-172. Date of Electronic Publication: 2022 Jan 14 (Print Publication: 2022).
DOI: 10.1107/S2056989022000287
Abstrakt: The title compounds, 2-(4-methylphenyl)-1 H -perimidine hemihydrate ( 1 , C 18 H 14 N 2 ·0.5H 2 O) and 1-methyl-2-(4-methylphenyl)-1 H -perimidine ( 2 , C 19 H 16 N 2 ), were prepared and characterized by 1 H NMR and single-crystal X-ray diffraction. The organic mol-ecule of the hemihydrate lies on a twofold rotation axis while the water mol-ecule lies on the inter-section of three twofold rotation axes (point group symmetry 222). As a consequence, the hydrogen atoms that are part of the N-H group and the water mol-ecule as well as the CH 3 group of the p -tolyl ring are disordered over two positions. In compound 1 , the perimidine and the 2-aryl rings are slightly twisted while its N -methyl-ated derivative 2 has a more distorted conformation because of the steric repulsion between the N -methyl group and the 2-aryl ring. In the crystal structures, mol-ecules of perimidine 2 are held together only by C-H⋯π contacts while the parent perimidine 1 does not exhibit this type of inter-action. Its crystal packing is established by inter-molecular N-H⋯O hydrogen bonds with the solvent water mol-ecules and additionally stabilized by π-π stacking.
(© Kalle et al. 2022.)
Databáze: MEDLINE
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