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

ABSTRACT: In the title mol-ecule, C(30)H(36)N(4)O(3), the dihedral angle between the planes of the xanthene and spiro-lactam rings systems is 88.69?(4)°. Both C atoms of one of the ethyl groups are disordered over two sites with occupancies 0.72?(2)/0.28?(2). The conformation of the mol-ecule may be influenced by two intra-molecular hydrogen bonds.

SUBMITTER: Tian MZ

PROVIDER: S-EPMC2961713 | biostudies-literature | 2008 Jun

REPOSITORIES: biostudies-literature

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

Tian Mao-Zhong MZ Peng Xiao-Jun XJ

Acta crystallographica. Section E, Structure reports online 20080613 Pt 7

In the title mol-ecule, C(30)H(36)N(4)O(3), the dihedral angle between the planes of the xanthene and spiro-lactam rings systems is 88.69 (4)°. Both C atoms of one of the ethyl groups are disordered over two sites with occupancies 0.72 (2)/0.28 (2). The conformation of the mol-ecule may be influenced by two intra-molecular hydrogen bonds. ...[more]

PMID: 21202886

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3',6'-Bis(diethyl-amino)-2-phenyl-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)-[(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.

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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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