Le Tuan Anh

Dimethyl 2-[23-oxo-22,24-diphenyl-8,11,14-trioxa-25-aza­tetra­cyclo­[19.3.1.02,7.015,20]penta­cosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate

The title compound, C39H37NO8, is a product of the Michael addition of the cyclic secondary amine subunit of aza-14-crown-4 ether to dimethyl acetylenedicarboxylate. The piperidinone ring exhibits a distorted chair conformation and the dimethyl acetylenedicarboxylate fragment has a cis configuration with a dihedral angle of 56.61 (5)° between the two carboxylate groups. The crystal packing is stabilized by the weak C—H⋯O hydrogen bonds.

Dimethyl 2-[22,24-dimethyl-23-oxo-8,11,14-trioxa-25-aza­tetra­cyclo­[19.3.1.02,7.015,20]penta­cosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate

The title compound, C29H33NO8, is a product of the Michael addition of the cyclic secondary amine subunit of the aza-14-crown-4 ether to dimethyl acetylenedicarboxylate. The piperidinone ring exhibits a distorted chair conformation, and the dimethyl ethylenedicarboxylate fragment has a cis configuration with a dihedral angle of 78.96 (5)° between the two carboxylate groups. The crystal packing is stabilized by weak C—H⋯O hydrogen bonds.

Dimethyl 2-[24-acetyl-28-oxo-8,11,14-trioxa-24,27-diaza­penta­cyclo­[19.5.1.122,26.02,7.015,20]octa­cosa-2,4,6,15(20),16,18-hexaen-27-yl]but-2-enedioate

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.

24-Acetyl-8,11,14-trioxa-24,27-diaza­penta­cyclo­[19.5.1.122,26.02,7.015,20]octa­cosa-2,4,6,15(20),16,18-hexaen-28-one

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].

meso-(1S*,21R*)-25-Methyl-8,11,14-trioxa-22,24,25-triaza­tetra­cyclo­[19.3.1.02,7.015,20]penta­cosa-2,4,6,15(20),16,18-hexa­ene-23-thione chloro­form monosolvate

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.

Crystal structure of 26-(4-methyl­phen­yl)-8,11,14,17-tetra­oxa-28-aza­tetra­cyclo[22.3.1.02,7.018,23]hexa­cosa-2,4,6,18(23),19,21,24(1),25,27-nona­ene

The title compound is the product of the Chichibabin domino reaction of 1,8-bis(2-acetylphenoxy)-3,6-dioxaoctane with 4-methylbenzaldehyde and ammonium acetate in acetic acid. It is of interest with respect to its potential anticancer activity. The compound has a bowl-like conformation comprising a fused tetracyclic system containing a 4-arylpyridine fragment, two benzene rings and an aza-17-crown-5 ether moiety.

1-Methyl-3-(2-oxo-2H-chromen-3-yl)-1H-imidazol-3-ium picrate

The title salt, C13H11N2O2 +·C6H2N3O7 −, is the unexpected product of a domino reaction of 3-cyanomethyl-1-methylimidazolium chloride with salicylic aldehyde in the presence of picric acid. In the cation, the 1H-imidazole ring is twisted by 63.2 (1)° from the 2H-chromen plane. In the crystal, cations and anions are alternately stacked along the a axis through π–π stacking interactions between the almost parallel aromatic rings [centroid–centroid distances = 3.458 (2) and 3.678 (2) Å]. The stacks are further linked by C—H⋯O hydrogen bonds into a two-tier layer parallel to (001).

Ethyl 23-benzyl-8,11,14-trioxa-23,28,29-triaza­penta­cyclo­[19.7.1.02,7.015,20.022,27]nona­cosa-2,4,6,15(20),16,18,21,26-octa­ene-26-carboxyl­ate

The title compound, C33H35N3O5, is the product of the multicomponent condensation of 1-benzyl-4-ethoxycarbonylpiperidin-3-one with 1,5-bis(2-formylphenoxy)-3-oxapentane and ammonium acetate. The molecule comprises a pentacyclic system containing the aza-14-crown-4-ether macrocycle, tetrahydropyrimidine, tetrahydropyridine and two benzene rings. The aza-14-crown-4-ether ring adopts a bowl conformation with a dihedral angle of 62.37 (5)° between the benzene rings. The tetrahydropyrimidine ring has an envelope conformation with the chiral C atom as the flap, whereas the tetrahydropyridine ring adopts a distorted chair conformation. Two amino groups are involved in intramolecular N—H⋯O hydrogen bonds. In the crystal, weak C—H⋯O hydrogen bonds link the molecules into layers parallel to the ab plane.

Crystal structure of (1RS,21SR,22RS,24SR)-28-oxo-24-propyl-8,11,14-trioxa-24,27-di­aza­penta­cyclo[19.5.1.122,26.02,7.015,20]octa­cosa-2,4,6,15(20),16,18-hexa­ene acetic acid monosolvate

The crystal structure of a product of the Petrenko–Kritchenko condensation of N-propylpiperidone with 1,5-bis(2-formylphenoxy)-3-oxapentane and ammonium acetate was studied by X-ray diffraction

(1R*,21S*,22R*,24S*)-Methyl ethyl 2-[23-hy­droxy-22,24-diphenyl-8,11,14-trioxa-25-aza­tetra­cyclo­[19.3.1.02,7.015,20]penta­cosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate

The title compound, C40H41NO8, is a product of the reduction of the cyclic carbonyl group of the γ-piperidone subunit of the aza-14-crown-4 ether with subsequent re-esterification of its dimethyl butenoate substituent into a monoethyl monomethyl group. The azacrown macrocycle exhibits a bowl conformation with a dihedral angle of 70.82 (5)° between the benzene rings fused to it. The piperidine ring adopts a chair conformation and the methyl ethyl ethylenedicarboxylate fragment has a cis conformation, with a dihedral angle of 66.51 (7)° between the two carboxylate groups. The ethyl group is disordered over two sites with occupancies of 0.70 (1):0.30 (1). In the crystal, molecules form inversion dimers, via pairs of O—H⋯O hydrogen bonds, that stack along the a axis.