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3',6'-Bis(diethyl-amino)-2-phenyl-spiro[isoindoline-1,9'-xanthen]-3-one.

ABSTRACT: The title compound, C(34)H(35)O(2)N(3), was synthesized by the reaction of 2-[3,6-bis-(diethyl-amino)-9H-xanthen-9-yl]benzoyl chloride with aniline. In the mol-ecular structure, the dihedral angles between the isoindoline and xanthene planes and between the isoindoline and benzene planes are 86.9?(3) and 47.0?(2)°, respectively. The mol-ecular packing in the crystal structure is stabilized by weak C-H?O hydrogen bonding.

SUBMITTER: Deng WJ

PROVIDER: S-EPMC2969317 | biostudies-literature | 2009 Jun

REPOSITORIES: biostudies-literature

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3',6'-Bis(diethyl-amino)-2-phenyl-spiro[isoindoline-1,9'-xanthen]-3-one.

Deng Wu-Jian WJ Sun Di D Su Bing-Yuan BY Wang Shu-Ping SP Zheng Hong H

Acta crystallographica. Section E, Structure reports online 20090606 Pt 7

The title compound, C(34)H(35)O(2)N(3), was synthesized by the reaction of 2-[3,6-bis-(diethyl-amino)-9H-xanthen-9-yl]benzoyl chloride with aniline. In the mol-ecular structure, the dihedral angles between the isoindoline and xanthene planes and between the isoindoline and benzene planes are 86.9 (3) and 47.0 (2)°, respectively. The mol-ecular packing in the crystal structure is stabilized by weak C-H⋯O hydrogen bonding. ...[more]

PMID: 21582767

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3',6'-Bis(diethyl-amino)-2-(2-hydroxy-ethyl-amino)spiro-[isoindoline-1,9'-xanthen]-3-one.

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Project description:In the title compound, C(38)H(42)N(4)O(4)·C(2)H(6)O, prepared via a spiro-lactam ring-formation reaction in a rhodamine dye, the xanthene ring system is approximately planar (r.m.s. deviation = 0.0014Å) and subtends dihedral angles of 88.10?(3) and 86.92?(4)° with the spiro-lactam (r.m.s. deviations = 0.0012?Å) and benzene rings, respectively. The crystal structure consists of chains parallel to [-101], formed via O-H?O inter-actions.

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3',6'-Bis(ethyl-amino)-2',7'-dimethyl-2-{[2-[(E)-3,4-methyl-enedioxy-benzyl-idene-amino]eth-yl}spiro-[isoindoline-1,9'-xanthen]-3-one.

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3',6'-Bis(ethyl-amino)-2-[(2-hydroxy-ethyl)-amino]-2',7'-dimethylspiro-[isoindoline-1,9'-xanthen]-3-one.

Project description:In the title compound, C(28)H(32)N(4)O(3), the dihedral angle between the planes of the xanthene ring system and the spiro-lactam ring is 85.99?(3)°. Mol-ecules are linked by inter-molecular O-H?O and N-H?O hydrogen-bonding inter-actions.

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3',6'-Bis(ethyl-amino)-2',7'-dimethyl-2-{2-(E)-[(thio-phen-2-yl)methyl-idene-amino]-eth-yl}spiro-[isoindoline-1,9'-xanthen]-3-one methanol monosolvate.

Project description:The title compound, C(33)H(34)N(4)O(2)S·CH(3)OH, was prepared as a spiro-lactam ring formation of rhodamine 6?G dye for comparison with a ring-opened form. The xanthene and spiro-lactam rings are approximately planar [r.m.s. deviations from planarity = 0.122?(3) and 0.072?(6)?Å, respectively]. The dihedral angles formed by the spiro-lactam and thio-phene rings with the xanthene ring system are 89.7?(6) and 86.5?(2)°, respectively. The crystal structure features N-H?O and C-H?O hydrogen bonds.

| S-EPMC3344655 | biostudies-literature

Crystal structure, Hirshfeld surface analysis and DFT study of 2,2''-({[(1<i>E</i>,1'<i>E</i>)-(diselanedi-yl)bis-(2,1-phenyl-ene)]bis-(methane-ylyl-idene)}bis-(aza-neylyl-idene))bis-[3',6'-bis-(di-ethyl-amino)-4a',9a'-di-hydro-spiro-[isoindoline-1,9'-xanthen]-3-one].

Project description:The title compound, C70H70N8O4Se2, is a spiro bicyclic diselenide, made up of two [SeC6H4CH=N-N(CO)C6H4(C)C6H3NEt2(O)C6H3NEt2] units related by a twofold crystallographic symmetry element bis-ecting the diselenide bond. The compound crystallizes in a non-centrosymmetric polar space group (tetra-gonal, P b2) and the structure was refined as an inversion twin. The two diethyl amine groups and their attached phenyl groups of the xanthene ring are disordered over two orientations, with occupancies of 0.664 (19)/0.336 (19) and 0.665 (11)/0.335 (11), respectively. The dihedral angles between the mean planes of the central isoindoline and the phenyl rings are 26.8 (2) and 2.5 (4)°, respectively. The mean plane of the central xanthene ring forms dihedral angles of 2.0 (5), 8.8 (5), 1.7 (5) and 7.9 (6)° with the peripheral phenyl rings. The isoindoline and xanthene rings subtend a dihedral angle of 89.8 (2)°. The mol-ecular conformation is stabilized by an intra-molecular C-H⋯O hydrogen bond generating an S(6) ring motif. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds together with C-H⋯π (ring) inter-actions, forming a three-dimensional network. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H⋯H (68.1%), C⋯H/H⋯C (21.2%) and O⋯H/H⋯O (8.7%) contacts. The optimized structure calculated using density functional theory (DFT) at the B3LYP/6 - 31 G(d) level is compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was used to determine the energy gap and the mol-ecular electrostatic potential (MEP) of the compound was investigated.

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