(E)-N²-{4-[(E)-2-(4-Chlorobenzoyl)ethenyl]-3-methyl-1-phenyl-1H-pyrazol-5-yl}-N¹,N¹-dimethylformamidine: polarized molecules within sheets of π-stacked hydrogen-bonded chains

Abstract

The molecules of the title compound, C(22)H(21)ClN(4)O, are conformationally chiral, and in the space group P2(1)2(1)2(1) each crystal contains only one conformational enantiomer. The intramolecular dimensions provide evidence for polarization of the electronic structure. Molecules are linked by a single C-H...pi(arene) hydrogen bond into chains, which are themselves weakly linked into sheets by an aromatic pi-pi stacking interaction.

N3-[(E)-Morpholin-4-ylmethylidene]-1-phenyl-1H-1,2,4-triazole-3,5-diamine monohydrate

“…Although the formally single bond N6-C1 (1.337 (2) Å) is longer than the double bond N3-C1 (1.297 (2) Å), it is sufficiently shorter than the purely single Nsp2-Csp2 bond (1.43-1.45 Å) (Burke-Laing & Laing,1976;Allen et al, 1987). Apparently, that is caused by conjugation of the N6 atom lone pair with the N3-C1 double bond, analogously to the other hetaryl substituted formamidines (Ryng & Glowiak, 1998;Kurbatov et al, 2006;Xie et al, 2007;Lyakhov et al, 2008;Quiroga et al, 2010). Atom N6 of morpholine cycle has a slightly pyramidalized trigonal configuration (sum of valence angles is supporting information sup-2 Acta Cryst.…”

“…For crystal structures of substituted 3,5diamino-1,2,4-triazoles, see: Ried et al (1983); Dunstan et al (1998); Chernyshev et al (2006Chernyshev et al ( , 2007Chernyshev et al ( , 2009. For crystal structures of hetaryl substituted amidines, see: Ryng & Glowiak (1998); Kurbatov et al (2006); Xie et al (2007); Lyakhov et al (2008); Quiroga et al (2010). The synthesis of mesoionic [1,2,4]triazolo [4,3-a]pyrimidines from N-(5-amino-1-R-1,2,4-triazol-3-yl)-substituted enaminoesters was described by Chernyshev et al (2010).…”