Dimethyl 2-[22,24-dimethyl-23-oxo-8,11,14-trioxa-25-azatetracyclo[19.3.1.0<sup>2,7</sup>.0<sup>15,20</sup>]pentacosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate

et al. 2012

Self Cite

The title compound, C31H34N2O9, is a product of the Michael addition of the cyclic secondary amine subunit of the (bispidino)aza-14-crown-4 ether to dimethyl acetylenedicarboxylate. The molecule comprises a tricyclic system containing the aza-14-crown-3 ether macrocycle and two six-membered piperidinone rings. The aza-14-crown-3-ether ring adopts a bowl conformation with a dihedral angle between the planes of the fused benzene rings of 51.14 (5)°. The central piperidone ring has a boat conformation, whereas the terminal piperidone ring adopts a chair conformation. The dimethyl ethylenedicarboxylate fragment has a cis configuration with a dihedral angle of 56.56 (7)° between the two carboxylate groups. The crystal packing is stabilized by weak C—H⋯O hydrogen bonds.

Section: S1 Commentmentioning

confidence: 99%

Dimethyl 2-[24-acetyl-28-oxo-8,11,14-trioxa-24,27-diazapentacyclo[19.5.1.1^22,26.0^2,7.0^15,20]octacosa-2,4,6,15(20),16,18-hexaen-27-yl]but-2-enedioate

Hieu¹,

Anh²,

et al. 2012

Self Cite

“…Design, synthesis and applications of macrocyclic ligands for coordination and supramolecular chemistry draw very great attention of investigators during the last several decades (Hiraoka, 1978;Pedersen, 1988;Gokel & Murillo, 1996;Bradshaw & Izatt, 1997). Recently we have developed the effective methods of synthesis of azacrown ethers containing piperidine (Levov et al, 2006(Levov et al, , 2008Anh et al, 2008Anh et al, , 2012aAnh et al, , 2012b, perhydropyrimidine (Hieu et al, 2011), perhydrotriazine (Khieu et al, 2011) and bispidine (Komarova et al, 2008;Sokol et al, 2011) subunits.…”

Section: S1 Commentmentioning

confidence: 99%

24-Acetyl-8,11,14-trioxa-24,27-diazapentacyclo[19.5.1.1^22,26.0^2,7.0^15,20]octacosa-2,4,6,15(20),16,18-hexaen-28-one

Anh¹,

Hieu²,

et al. 2012

Self Cite

The title compound, C25H28N2O5, is a product of the Petrenko–Kritchenko condensation of N-acetylpiperidone with 1,5-bis(2-formylphenoxy)-3-oxapentane and ammonium acetate. The molecule comprises a fused pentacyclic system containing an aza-14-crown-3-ether macrocycle, two piperidone and two benzene rings. The aza-14-crown-3-ether ring adopts a bowl conformation. The dihedral angle between the benzene rings fused to the aza-14-crown-4-ether unit is 70.18 (4)°. The central piperidone ring has a boat conformation, whereas the terminal piperidone ring adopts a chair conformation. The conformation of the central piperidone ring is determined by two intramolecular N—H⋯O hydrogen bonds. In the crystal, molecules are linked by weak C—H⋯O interactions into chains along [010].

“…Supramolecular chemistry of azacrown ethers draws a great attention of researchers during the last decades (Hiraoka, 1982;Pedersen, 1988;Gokel & Murillo, 1996;Bradshaw & Izatt, 1997). Recently, we have developed effective methods of synthesis of azacrown ethers containing piperidine (Levov et al, 2006(Levov et al, , 2008Anh et al, 2008Anh et al, , 2012aAnh et al, , 2012b, perhydropyrimidine (Hieu et al, 2011) and perhydrotriazine (Hieu et al, 2009;Khieu et al, 2011) subunits.…”

Section: S1 Commentmentioning

confidence: 99%

meso-(1S,21R)-25-Methyl-8,11,14-trioxa-22,24,25-triazatetracyclo[19.3.1.0^2,7.0^15,20]pentacosa-2,4,6,15(20),16,18-hexaene-23-thione chloroform monosolvate

Hieu¹,

Anh²,

et al. 2012

Self Cite

The title compound crystallizes as a chloroform solvate, C20H23N3O3S·CHCl3, with two crystallographically independent units. The independent units have distinctly different interaction patterns between the azacrown macrocycle and the chloroform solvent molecule. In one of them, the chloroform molecule forms C—H⋯N and Cl⋯H—C hydrogen bonds with the azacrown macrocycle (as a proton donor and an acceptor, respectively), whereas in the other, one of the chloroform molecules is bound to the azacrown macrocycle by an attractive Cl⋯O [3.080 (3) Å] interaction. The azacrown macrocycles of different units are structurally similar; the aza-14-crown-3-ether ring adopts a bowl conformation with dihedral angles between the planes of the fused benzene rings of 60.7 (1) and 68.0 (1)°. The triazinanethione ring in both cases has a sofa conformation. The crystal packing is characterized by N—H⋯S, N—H⋯O, C—H⋯Cl and C—H⋯S hydrogen bonds.