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9-(5-Bromo-1H-indol-3-yl)-1,2,3,4,5,6,7,8,9,10-deca-hydro-acridine-1,8-dione dimethyl sulfoxide monosolvate.

ABSTRACT: In the title compound, C21H19BrN2O2·C2H6OS, the indole ring system is essentially planar, with a maximum deviation of 0.050 (3) Å for the non-bridgehead C atom adjacent to the N atom. The two cyclo-hex-2-enone rings adopt half-chair conformations. An intra-molecular C-H⋯O hydrogen bond occurs. The solvent mol-ecule exhibits minor disorder of the S atom [site occupancies = 0.8153 (16) and 0.1847 (18)]. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, forming layers parallel to the bc plane.

SUBMITTER: El-Khouly A

PROVIDER: S-EPMC3588939 | biostudies-literature | 2012 Dec

REPOSITORIES: biostudies-literature

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9-(5-Bromo-1H-indol-3-yl)-1,2,3,4,5,6,7,8,9,10-deca-hydro-acridine-1,8-dione dimethyl sulfoxide monosolvate.

El-Khouly Ahmed A Oztürk Yildirim Sema S Butcher Ray J RJ Simsek Rahime R Safak Cihat C

Acta crystallographica. Section E, Structure reports online 20121110 Pt 12

In the title compound, C21H19BrN2O2·C2H6OS, the indole ring system is essentially planar, with a maximum deviation of 0.050 (3) Å for the non-bridgehead C atom adjacent to the N atom. The two cyclo-hex-2-enone rings adopt half-chair conformations. An intra-molecular C-H⋯O hydrogen bond occurs. The solvent mol-ecule exhibits minor disorder of the S atom [site occupancies = 0.8153 (16) and 0.1847 (18)]. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, forming layers parallel to the b ...[more]

PMID: 23476175

Similar Datasets

3,3,6,6-Tetra-methyl-9-(1-methyl-1H-indol-2-yl)-1,2,3,4,5,6,7,8,9,10-deca-hydro-acridine-1,8-dione.

Project description:In the acridine system of the title mol-ecule, C26H30N2O2, both cyclo-hex-2-enone rings adopt sofa conformations. The indole ring system is essentially planar, with a maximum deviation of 0.017 (2) Å for a bridgehead C atom. An intra-molecular C-H⋯O hydrogen bond occurs. The mol-ecules assemble into C(6) chains in the crystal by way of N-H⋯O hydrogen bonds.

| S-EPMC3588962 | biostudies-literature

9-(3-Fluoro-phen-yl)-3,3,6,6-tetra-methyl-1,2,3,4,5,6,7,8,9,10-deca-hydro-acridine-1,8-dione.

Project description:In the title mol-ecule, C23H26FNO2, the central ring of the acridinedione system adopts a slight boat conformation and the four essentially planar atoms of this ring [maximum deviation = 0.019 (1) Å] form a dihedral angle of 89.98 (6)° with the benzene ring. The two outer rings of the acridinedione system adopt sofa conformations. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules, forming chains along [001].

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9-(3,4-Dimeth-oxy-phen-yl)-3,3,6,6-tetra-methyl-1,2,3,4,5,6,7,8,9,10-deca-hydro-acridine-1,8-dione.

Project description:The asymmetric unit of the title compound, C(25)H(31)NO(4), contains two independent mol-ecules. In one mol-ecule, the benzene ring and an attached meth-oxy group were refined as disordered over two sets of sites in a 0.65 (4): 0.35 (4) ratio. In both mol-ecules, the central ring of the acridinedione system adopts a flattened boat conformation. The four essentially planar atoms of this ring [maximum deviations = 0.006 (5) Å in both mol-ecules] forms dihedral angles of 86.8 (2) and 87.6 (2)°, respectively, with the major and minor components in the disordered benzene ring and 87.3 (2)° with the benzene ring in the fully ordered mol-ecule. The two outer rings of the acridinedione system adopt sofa conformations in both mol-ecules. In the crystal, N-H⋯O hydrogen bonds form two independent chains along [100]. C-H⋯O hydrogen bonds link the chains, forming a three-dimensional network.

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9-(3-Bromo-5-chloro-2-hy-droxy-phen-yl)-10-(2-hy-droxy-eth-yl)-1,2,3,4,5,6,7,8,9,10-deca-hydro-acridine-1,8-dione.

Project description:In the title compound, C21H21BrClNO4, the dihydro-pyridine ring adopts a flattened boat conformation. The 3-bromo-5-chloro-2-hy-droxy-phenyl ring forms a dihedral angles of 84.44 (7)° with the dihydro-pyridine mean plane. The mol-ecular conformation is stabilized by an intra-molecular O-H⋯O hydrogen bond, with an S(8) ring motif. In the crystal, O-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules, forming a three-dimensional network.

| S-EPMC3588342 | biostudies-literature

9-(5-Bromo-2-hy-droxy-phen-yl)-10-(2-hy-droxy-prop-yl)-3,3,6,6-tetra-methyl-1,2,3,4,5,6,7,8,9,10-deca-hydro-acridine-1,8-dione.

Project description:The dihydro-pyridine ring in the title compound, C(26)H(32)BrNO(4), adopts an envelope conformation with the methine C atom representing the flap. The cyclo-hexenone rings also adopt envelope conformations. The phenolic hy-droxy group forms an intra-molecular hydrogen bond to one of the two keto O atoms. Inter-molecular weak C-H⋯O hydrogen bonding is present in the crystal structure. The hy-droxy-propyl group is disordered over two sets of sites with an occupancy ratio of 0.636 (6):0.364 (6).

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3,3-Dimethyl-10-(4-methoxy-phen-yl)-9-(4-nitro-phen-yl)-1,2,3,4,5,6,7,8,9,10-deca-hydro-acridine-1,8-dione.

Project description:The title compound, C(28)H(28)N(2)O(5), consists of a partially hydrogenated acridine ring system with two substituted phenyl substituents on the dihydro-pyridine ring which are both nearly perpendicular to the mean plane of the acridine unit [dihedral angles of 81.3 (1) and 89.6 (1)° between the central ring of acridine and the methoxyphenyl and nitrophenyl rings, respectively]. The dihydro-pyridine ring is almost planar, whereas both the outer unsymmetrical six-membered rings adopt half-chair conformations.

| S-EPMC2961676 | biostudies-literature

9-(4-Hy-droxy-3-meth-oxy-phen-yl)-3,3,6,6-tetra-methyl-1,2,3,4,5,6,7,8,9,10-deca-hydro-acridine-1,8-dione.

Project description:In the title mol-ecule, C24H29NO4, the central ring of the acridinedione system adopts a flat boat conformation and the four essentially planar atoms of this ring [maximum deviation = 0.001 (2) Å] form a dihedral angle of 85.99 (12)° with the benzene ring. The two outer rings of the acridinedione system adopt sofa conformations. In the crystal, O-H⋯O and N-H⋯O hydrogen bonds link the mol-ecules, forming a two-dimensional network parallel to (100).

| S-EPMC3588262 | biostudies-literature

10-(2-Hy-droxy-eth-yl)-9-(2-hy-droxy-phen-yl)-3,3,6,6-tetra-methyl-1,2,3,4,5,6,7,8,9,10-deca-hydro-acridine-1,8-dione.

Project description:The dihydro-pyridine ring in the title compound, C(25)H(31)NO(4), adopts an envelope conformation with the methine C atom representing the flap. The cyclo-hexenone rings also adopt envelope conformations with the C atoms bearing the methyl C atoms representing the flaps. The phenolic hy-droxy group forms an intra-molecular hydrogen bond to one of the two keto O atoms. The hy-droxy group of the N-bonded alkyl chain forms an inter-molecular hydrogen bond to the other keto O atom of an adjacent mol-ecule. The latter hydrogen bond leads to the formation of a helical chain running along the b axis.

| S-EPMC3051986 | biostudies-literature

2,2,7,7-Tetra-methyl-1,2,3,4,5,6,7,8-octa-hydro-acridine-1,8-dione.

Project description:The whole molecule of the title compound, C17H21NO2, is generated by twofold rotational symmetry. The N atom and the C and H atoms in position 4 of the pyridine ring lie on the twofold axis. The cyclohexene ring has a sofa conformation with the CH2 C atom adjacent to the dimethyl-substituted C atom displaced by 0.5949 (16) Å from the mean plane of the other five C atoms. In the crystal, weak C-H⋯O inter-actions link the mol-ecules into chains parallel to the a axis. In addition, π-π stacking inter-actions [centroid-centroid distance = 3.8444 (7) Å] contribute to the stabilization of the crystal structure.

| S-EPMC3588388 | biostudies-literature

Crystal structure of ethyl 2-[9-(5-bromo-2-hy-droxy-phen-yl)-1,8-dioxo-1,2,3,4,5,6,7,8,9,10-deca-hydro-acridin-10-yl]acetate.

Project description:In the title compound, C23H24BrNO5, the central 1,4-di-hydro-pyridine ring of the 1,2,3,4,5,6,7,8,9,10-deca-hydro-acridine ring system adopts a half-chair conformation. The two cyclo-hexene rings fused to the central ring both have a twisted-boat conformation. The mean planes of the bromo-hydroxy-phenyl ring and the major and minor components of the disordered ethyl amino-acetate moiety make dihedral angles of 78.99 (12), 85.9 (2) and 88.3 (9)°, respectively, with the 1,4-di-hydro-pyridine ring. The terminal ethyl group of the ethyl amino-acetate moiety is disordered over two sets of sites with refined occupancies of 0.768 (17) and 0.232 (17). The mol-ecular conformation is stabilized by an intra-molecular O-H⋯O hydrogen bond, forming an S(8) ring motif. In the crystal, C-H⋯O hydrogen bonds connect the mol-ecules into layers parallel to (001), enclosing R 1 (2)(7) ring motifs.

| S-EPMC4719938 | biostudies-literature

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