Ethyl 1-acetyl-1H-indole-3-carboxylate

Abstract

The title compound, C13H13NO3, was synthesized by acetyl­ation of ethyl 1H-indole-3-carboxyl­ate. The aromatic ring system of the mol­ecule is essentially planar, but the saturated ethyl group is also located within this plane and the overall r.m.s. deviation from planarity is only 0.034 Å. Pairs of C—H⋯O inter­actions connect mol­ecules into chains along the diagonal of the unit cell. Mol­ecules also form weakly connected dimers via π⋯π stacking inter­actions of the indole rings with centroid–centroid separations of 3.571 (1) Å. C—H⋯π inter­actions between methyl­ene and methyl groups and the indole and benzene ring complete the directional inter­molecular inter­actions found in the crystal structure.

Methyl 3-[(1-butyl-1H-indol-3-yl)carbonylamino]propionate

“…In (I) ( Fig.1), all bond lengths and angles are unexceptional and correspond to those observed in the related compounds (Zeng et al, 2005;Siddiquee et al, 2009). In the crystal structure, adjacent molecules are linked through N2-H2A•••O1 hydrogen bonds, forming chains extending along the c axis.…”

“…For the bioactivity of indole derivatives, see: Fabio et al (2007); Sharma et al (2004). For related structures, see: Zeng et al (2005); Siddiquee et al (2009). Table 1 Hydrogen-bond geometry (Å , ).…”

Methyl 3-(1H-indole-3-carboxamido)propionate hemihydrate

“…Also the five and six-membered rings of the indole systems are inclined at 1.67 (8) ° and 1.50 (8) ° in A and B respectively. Bond lengths in both molecules are unexceptional (Allen et al, 1987) and are comparable to those found in similar structures (Huang et al, 2009;Siddiquee et al, 2009).…”