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

ABSTRACT: In the title compound, C33H27BrClNO4, the di-hydro-pyridine ring adopts a flattened boat conformation. 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, C-H?O and C-H?Cl hydrogen bonds, and C-H?? inter-actions link the mol-ecules, forming a three-dimensional network. In the acridinedione ring system, the two ring C atoms at the 2- and 3-positions, and the C atom at the 6-position and the atoms of the phenyl ring attached to the C atom at the 6-position are disordered over two sets of sites with occupancy ratios of 0.783?(5):0.217?(5) and 0.526?(18):0.474?(18), respectively.

SUBMITTER: Akkurt M

PROVIDER: S-EPMC4051074 | biostudies-literature | 2014 Jun

REPOSITORIES: biostudies-literature

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

Akkurt Mehmet M Mohamed Shaaban K SK Abdelhamid Antar A AA Gaber Abdel-Aal M AA Albayati Mustafa R MR

Acta crystallographica. Section E, Structure reports online 20140517 Pt 6

In the title compound, C33H27BrClNO4, the di-hydro-pyridine ring adopts a flattened boat conformation. 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, C-H⋯O and C-H⋯Cl hydrogen bonds, and C-H⋯π inter-actions link the mol-ecules, forming a three-dimensional network. In the acridinedione ring system, the two ring C atoms at the 2- and 3-positions, and the C atom at the 6-position and the atoms of the phenyl ring a ...[more]

PMID: 24940246

Similar Datasets

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

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

Crystal structure of 9-(3-bromo-5-chloro-2-hydroxy-phen-yl)-10-(2-hy-droxy-eth-yl)-3,3,6,6-tetra-methyl-3,4,6,7,9,10-hexa-hydro-acridine-1,8(2H,5H)-dione.

Project description:The title compound C25H29BrClNO4, comprises a 3,3,6,6-tetra-methyl-tetra-hydro-acridine-1,8-dione ring system that carries a hy-droxy-ethyl substituent on the acridine N atom and a 3-bromo-5-chloro-2-hy-droxy-phenyl ring on the central methine C atom of the di-hydro-pyridine ring. The benzene ring is inclined to the acridine ring system at an angle of 89.84?(6)° and this conformation is stabilized by an intra-molecular O-H?O hydrogen bond between the hy-droxy substituent on the benzene ring and one of the carbonyl groups of the acridinedione unit. In the crystal, O-H?O, C-H?O and C-H?Br hydrogen bonds combine to stack mol-ecules in inter-connected columns propagating along the a-axis direction.

| S-EPMC4158539 | biostudies-literature

The structure of 9-(3-bromo-6-chloro-2-hy-droxy-phen-yl)-10-(2-hy-droxy-ethyl)-3,6-diphenyl-3,4,5,6,7,9-hexa-hydro-2<i>H</i>-acridine-1,8-dione.

Project description:In the structure of the title compound C33H29BrClNO4, (I), the hexa-hydro-2H-acridine ring system has a hy-droxy-ethyl substituent on the N atom and a 3-bromo-6-chloro-2-hy-droxy-phenyl substituent on the central C atom at the 9-position. An unusual feature of the mol-ecule is that the substituents at the 3- and 5-positions of the outer cyclo-hexenone rings are phenyl rings rather than the more common dimethyl substituents. C atoms on both of the cyclo-hexenone rings are disordered over two sites. In the crystal structure, O-H⋯O, C-H⋯O and C-H⋯π(ring) hydrogen bonds combine with an Br-O and unusual C-Br⋯π(ring) halogen bonds to generate a three dimensional network with mol-ecules stacked along the a-axis direction.

| S-EPMC6127693 | biostudies-literature

10-Benzyl-9-(4-eth-oxy-phen-yl)-3,3,6,6-tetra-methyl-3,4,6,7,9,10-hexa-hydro-acridine-1,8(2H,5H)-dione.

Project description:In the title compound, C(32)H(37)NO(3), the central dihydro-pyridine ring adopts a nearly planar flattened-boat conformation, whereas both cyclo-hexenone rings adopt half-chair conformations. The mean and maximum deviations from the mean plane of the dihydro-pyridine ring are 0.1252 (9) and 0.188 (1) Å, respectively. The 4-eth-oxy-phenyl and phenyl rings form dihedral angles of 75.20 (4) and 82.14 (5)° with the dihydro-pyridine mean plane, respectively.

| S-EPMC3435766 | biostudies-literature

10-[2-(Dimethyl-amino)eth-yl]-9-(4-methoxy-phen-yl)-3,3,6,6-tetra-methyl-3,4,6,7,9,10-hexa-hydro-acridine-1,8(2H,5H)-dione.

Project description:In the title compound, C(28)H(38)N(2)O(3), the central ring of the acridinedione system adopts a boat conformation, while one of the outer rings adopts a half-chair conformation and the conformation of the other outer ring is between a sofa and a half-chair. The acridinedione system is buckled, with an angle of 22.01?(3)°. The crystal packing comprises layers of mol-ecules laid parallel to the ac plane, being reinforced by an intermolecular C-H?O interaction.

| S-EPMC2968240 | 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

Crystal structure, Hirshfeld surface and frontier mol-ecular orbital analysis of 10-benzyl-9-(3-eth-oxy-4-hy-droxy-phen-yl)-3,3,6,6-tetra-methyl-3,4,6,7,9,10-hexa-hydro-acridine-1,8(2H,5H)-dione.

Project description:In the fused ring system of the title compound, C32H37NO4, the central di-hydro-pyridine ring adopts a flattened boat conformation, the mean and maximum deviations of the di-hydro-pyridine ring being 0.1429?(2) and 0.2621?(2)?Å, respectively. The two cyclo-hexenone rings adopt envelope conformations with the tetra-substituted C atoms as flap atoms. The benzene and phenyl rings form dihedral angles of 85.81?(2) and 88.90?(2)°, respectively, with the mean plane of the di-hydro-pyridine ring. In the crystal, mol-ecules are linked via an O-H?O hydrogen bond, forming a helical chain along the b-axis direction. A Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H?H (65.2%), O?H/H?O (18.8%) and C?H/H?C (13.9%) contacts. Quantum chemical calculations for the frontier mol-ecular orbitals were undertake to determine the chemical reactivity of the title compound.

| S-EPMC7133029 | biostudies-literature

1-(2-Hy-droxy-eth-yl)pyrrole-2,5-dione.

Project description:The asymmetric unit of the title compound, C(6)H(7)NO(3), contains two mol-ecules (A and B) related by a non-crystallographic twofold pseudo-axis. The mol-ecules are joined in the (AABB)(n) manner by O-H⋯O hydrogen bonds between their hy-droxy groups, thus forming C(2) chains along the a-axis direction. Neighboring mol-ecules of the same kind (A and A, or B and B) are related by inversion centers, so that all hy-droxy H atoms are disordered other two sets of sites with half occupancies (superimposed O-H⋯O and O⋯H-O fragments). The mol-ecules are further linked by C-H⋯O inter-actions, which can be considered to be weak hydrogen bonds.

| S-EPMC3343945 | 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).

| S-EPMC3089333 | biostudies-other

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