ABSTRACT
The title compound, C30H34N2O9 (4), is a product of the Michael reaction of aza-crown ether with dimethyl acetyl-enedi-carboxyl-ate modified by an addition of NH3 (aq.) at 298â K. The aza-14-crown-4-ether ring adopts a bowl conformation. The dihedral angle between the planes of the benzene rings fused to the aza-14-crown-4-ether moiety is 8.65â (5)°. The tetra-hydro-pyridine ring has a boat conformation. The mol-ecular conformation is supported by one N-Hâ¯O and two C-Hâ¯O intra-molecular hydrogen bonds. Both heterocyclic and amino N atoms have essentially planar configurations (sums of the bond angles are 359.35 and 358.00°). Compound 4 crystallizes as a racemate consisting of enanti-omeric pairs of the 1R,21S diastereomer. In the crystal, mol-ecules of 4 are connected by N-Hâ¯O hydrogen bonds, forming chains along [100]. According to the PASS program (computer prediction of biological activities), compound 4 may exhibit anti-allergic (72% probability) and anti-asthmatic (67%) activity, as well as be a membrane permeability inhibitor (65%).
ABSTRACT
The title compound, C24H29NO4, is the product of a Petrenko-Kritchenko condensation of 1,5-bis-(2-formyl-phen-oxy)-3-oxa-pentane, pentan-3-one and methyl-ammonium acetate in ethanol. The mol-ecule has mirror symmetry. The aza-14-crown-3 ether ring adopts a bowl conformation stabilized by a weak intra-molecular C-Hâ¯O hydrogen bond. The conformation of the C-O-C-C-O-C-C-O-C polyether chain is t-g+-t-t-g--t (t = trans, 180°; g = gauche, ±60°). The dihedral angle between the benzene rings fused to the aza-14-crown-4-ether moiety is 72.68â (4)°. The piperidinone ring adopts a chair conformation. The nitro-gen atom has a trigonal-pyramidal geometry, the sum of the bond angles being 335.9°. In the crystal, the mol-ecules are linked by weak C-Hâ¯O inter-actions, forming zigzag chains propagating along the [100] direction.
ABSTRACT
The title compound, C30H29NO4, is a tetra-cyclic system containing a 4-aryl-pyridine fragment, two benzene rings and an aza-17-crown-5 ether moiety, in a bowl-like arrangement. The pyridine ring is inclined to the 4-methyl-phenyl ring by 26.64â (6)°, and by 57.43â (6) and 56.81â (6)° to the benzene rings. The benzene rings are inclined to one another by 88.32â (6)°. In the crystal, mol-ecules are linked by pairs of C-Hâ¯N hydrogen bonds, forming inversion dimers with an R 2 (2)(14) ring motif. The dimers are linked via a number of C-Hâ¯π inter-actions, forming a three-dimensional architecture.
ABSTRACT
The title compound, C26H32N2O4(M)·C2H4O2, (I), is the product of the Petrenko-Kritchenko condensation of N-propyl-piperidinone with 1,5-bis-(2-formyl-phen-oxy)-3-oxa-pentane and ammonium acetate. In M, the aza-14-crown-3-ether ring adopts a bowl conformation, with the configuration of the C-O-C-C -O-C-C-O-C polyether chain being t-g ((-))-t-t-g ((+))-t (t = trans, 180°; g = gauche, ±60°). The dihedral angle between the planes of the benzene rings fused to the aza-14-crown-4-ether moiety is 62.75â (5)°. The central piperidinone ring has a boat conformation, whereas the terminal piperidinone ring adopts a chair conformation. The boat conformation of the central piperidinone ring is supported by the bifurcated intra-molecular N-Hâ¯O hydrogen bond. In the crystal, each solvent mol-ecule is linked to mol-ecule M via strong O-Hâ¯N hydrogen bonding, forming hydrogen-bonded pairs of mol-ecules, which further inter-act through weak C-Hâ¯O hydrogen bonds, forming layers parallel to the ac plane.
ABSTRACT
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 aza-crown macrocycle exhibits a bowl conformation with a dihedral angle of 70.82â (5)° between the benzene rings fused to it. The piperidine ring adopts a chair conformation and the methyl ethyl ethyl-enedi-carboxyl-ate fragment has a cis conformation, with a dihedral angle of 66.51â (7)° between the two carboxyl-ate groups. The ethyl group is disordered over two sites with occupancies of 0.70â (1):0.30â (1). In the crystal, mol-ecules form inversion dimers, via pairs of O-Hâ¯O hydrogen bonds, that stack along the a axis.
ABSTRACT
In the title compound, C15H25NO2, all three six-membered rings adopt chair conformations. The cyclo-hexane and piperidine rings within the perhydro-isoquinoline are trans-trans fused. The N atom has a trigonal-pyramidal geometry (the sum of the bond angles is 328.0°). The methyl substituent occupies the sterically preferrable equatorial position. In the crystal, mol-ecules form infinite [100] chains via O-Hâ¯N hydrogen bonds.
ABSTRACT
The title compound, C33H35N3O5, is the product of the multicomponent condensation of 1-benzyl-4-eth-oxy-carbonyl-piperidin-3-one with 1,5-bis-(2-formyl-phen-oxy)-3-oxapentane and ammonium acetate. The mol-ecule comprises a penta-cyclic system containing the aza-14-crown-4-ether macrocycle, tetra-hydro-pyrimidine, tetra-hydro-pyridine and two benzene rings. The aza-14-crown-4-ether ring adopts a bowl conformation with a dihedral angle of 62.37â (5)° between the benzene rings. The tetra-hydro-pyrimidine ring has an envelope conformation with the chiral C atom as the flap, whereas the tetra-hydro-pyridine ring adopts a distorted chair conformation. Two amino groups are involved in intra-molecular N-Hâ¯O hydrogen bonds. In the crystal, weak C-Hâ¯O hydrogen bonds link the mol-ecules into layers parallel to the ab plane.
ABSTRACT
The title compound crystallizes as a chloro-form solvate, C(20)H(23)N(3)O(3)S·CHCl(3), with two crystallographically independent units. The independent units have distinctly different inter-action patterns between the aza-crown macrocycle and the chloro-form solvent mol-ecule. In one of them, the chloro-form mol-ecule forms C-Hâ¯N and Clâ¯H-C hydrogen bonds with the aza-crown macrocycle (as a proton donor and an acceptor, respectively), whereas in the other, one of the chloro-form mol-ecules is bound to the aza-crown macrocycle by an attractive Clâ¯O [3.080â (3)â Å] inter-action. The aza-crown 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 60.7â (1) and 68.0â (1)°. The triazinane-thione ring in both cases has a sofa conformation. The crystal packing is characterized by N-Hâ¯S, N-Hâ¯O, C-Hâ¯Cl and C-Hâ¯S hydrogen bonds.
ABSTRACT
The title compound, C(31)H(34)N(2)O(9), is a product of the Michael addition of the cyclic secondary amine subunit of the (bis-pidino)aza-14-crown-4 ether to dimethyl acetyl-ene-dicarboxyl-ate. The mol-ecule 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 51.14â (5)°. The central piperidone ring has a boat conformation, whereas the terminal piperidone ring adopts a chair conformation. The dimethyl ethyl-enedicarboxyl-ate fragment has a cis configuration with a dihedral angle of 56.56â (7)° between the two carboxyl-ate groups. The crystal packing is stabilized by weak C-Hâ¯O hydrogen bonds.
ABSTRACT
The title compound, C(25)H(28)N(2)O(5), is a product of the Petrenko-Kritchenko condensation of N-acetyl-piperidone with 1,5-bis-(2-formyl-phen-oxy)-3-oxapentane and ammonium acetate. The mol-ecule comprises a fused penta-cyclic 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 70.18â (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 intra-molecular N-Hâ¯O hydrogen bonds. In the crystal, mol-ecules are linked by weak C-Hâ¯O inter-actions into chains along [010].
ABSTRACT
The title compound, C(29)H(33)NO(8), is a product of the Michael addition of the cyclic secondary amine subunit of the aza-14-crown-4 ether to dimethyl acetyl-enedicarboxyl-ate. The piperidinone ring exhibits a distorted chair conformation, and the dimethyl ethylenedicarboxylate fragment has a cis configuration with a dihedral angle of 78.96â (5)° between the two carboxyl-ate groups. The crystal packing is stabilized by weak C-Hâ¯O hydrogen bonds.
ABSTRACT
The title compound, C(39)H(37)NO(8), is a product of the Michael addition of the cyclic secondary amine subunit of aza-14-crown-4 ether to dimethyl acetyl-enedicarboxyl-ate. The piperidinone ring exhibits a distorted chair conformation and the dimethyl acetyl-enedicarboxyl-ate fragment has a cis configuration with a dihedral angle of 56.61â (5)° between the two carboxyl-ate groups. The crystal packing is stabilized by the weak C-Hâ¯O hydrogen bonds.
ABSTRACT
The title compound, C(23)H(23)NO, is the product of a tandem transformation of the double Mannich base bis-(1-oxo-1,2,3,4-tertrahydro-2-naphtho-ylmeth-yl)amine hydro-chloride in HBr solution upon heating. The tetra-hydro-pyridine ring has a non-symmetrical half-chair conformation, whereas the cyclo-hexa-diene and cyclo-hexene rings adopt non-symmetrical half-boat conformations. The dihedral angle between the planes of the terminal benzene rings is 62.85â (6)°. The N atom has a trigonal-pyramidal geometry [sum of the bond angles = 332.4â (3)°]. In the crystal, mol-ecules form [001] chains via weak non-classical C-Hâ¯N hydrogen bonds. The chains are stacked along the b axis.
ABSTRACT
The title compound, C(40)H(40)O(9), is a product of the double crotonic condensation of bis-(2-acetyl-phen-oxy)-3-oxapentane with bis-(2-formyl-phen-oxy)-3,6-dioxaoctane. The title macromolecule includes the 31-crown-7-ether skeletal unit and adopts a saddle-like conformation. The two ethyl-ene fragments have E configurations. The volume of the inter-nal cavity of the macrocycle is approximately 125â Å(3). In the crystal, the mol-ecules are arranged at van der Waals distances.
ABSTRACT
The title compound, C(36)H(31)N(2)O(3) (+),C(2)H(3)O(2) (-)·2C(2)H(5)OH, the product of a domino condensation of dibenzyl ketone with salicylic aldehyde and ammonium acetate, crystallized as the ethanol disolvate. The cation of the salt comprises a fused tricyclic system containing three six-membered rings (piperidine, dihydro-2H-pyran and benzene). The piperidine ring has the usual chair conformation, while the dihydro-pyran ring adopts a slightly distorted sofa conformation. In the crystal, there are six (one intra- and five inter-molecular) independent hydrogen-bonding inter-actions: the inter-molecular hydrogen bonds link the cations and anions and ethanol solvent mol-ecules into ribbons along [001]. The ribbons are stacked along the a axis.
