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Crystal structure and DFT study of (E)-N-[2-(1H-indol-3-yl)eth-yl]-1-(anthracen-9-yl)methanimine.


ABSTRACT: The title compound, C25H20N2, (I), was synthesized from the condensation reaction of anthracene-9-carbaldehyde and tryptamine in dry ethanol. The indole ring system (r.m.s. deviation = 0.016?Å) makes a dihedral angle of 63.56?(8)° with the anthracene ring (r.m.s. deviation = 0.023?Å). There is a short intra-molecular C-H?N inter-action present, and a C-H?? inter-action involving the two ring systems. In the crystal, the indole H atom forms an inter-molecular N-H?? inter-action, linking mol-ecules to form chains along the b-axis direction. There are also C-H?? inter-actions present, involving the central and terminal rings of the anthracene unit, linking the chains to form an overall two-dimensional layered structure, with the layers parallel to the bc plane. The density functional theory (DFT) optimized structure, at the B3LYP/6-311?G(d,p) level, is compared with the experimentally determined mol-ecular structure in the solid state.

SUBMITTER: Faizi MSH 

PROVIDER: S-EPMC5588573 | biostudies-literature | 2017 Sep

REPOSITORIES: biostudies-literature

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Crystal structure and DFT study of (<i>E</i>)-<i>N</i>-[2-(1<i>H</i>-indol-3-yl)eth-yl]-1-(anthracen-9-yl)methanimine.

Faizi Md Serajul Haque MSH   Dege Necmi N   Malinkin Sergey S   Sliva Tetyana Yu TY  

Acta crystallographica. Section E, Crystallographic communications 20170811 Pt 9


The title compound, C<sub>25</sub>H<sub>20</sub>N<sub>2</sub>, (<b>I</b>), was synthesized from the condensation reaction of anthracene-9-carbaldehyde and tryptamine in dry ethanol. The indole ring system (r.m.s. deviation = 0.016 Å) makes a dihedral angle of 63.56 (8)° with the anthracene ring (r.m.s. deviation = 0.023 Å). There is a short intra-molecular C-H⋯N inter-action present, and a C-H⋯π inter-action involving the two ring systems. In the crystal, the indole H atom forms an inter-molecul  ...[more]

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