(E)-3-Dimethylamino-2-(1H-indol-3-ylcarbonyl)acrylonitrile: a chain of edge-fused rings built from a three-centre N—H...(N,O) hydrogen bond

Abstract

In the title compound, C(14)H(13)N(3)O, the intramolecular distances provide evidence for polarization of the molecular-electronic structure. A single three-centre N-H...(N,O) hydrogen bond links the molecules into chains of edge-fused R(2)(2)(16) and R(2)(4)(12) rings. Comparison with a number of related structures identifies factors of significance controlling the pattern of supramolecular aggregation.

Crystal structure of 2-benzoylamino-N′-(4-hydroxybenzylidene)-3-(thiophen-2-yl)prop-2-enohydrazide

“…water (4/3) (Glidewell et al, 2002) there are six different threecentre hydrogen bonds, two of which, both of O-HÁ Á Á(N,O) type, show asymmetries comparable with that found here in (I); markedly asymmetric N-HÁ Á Á(N,O) systems occur in the structures of 2-amino-4,6-bis(benzyloxy)-5-nitrosopyrimidine (Quesada et al, 2002), and in (E)-3-dimethylamino-2-(1Hindol-3-ylcarbonyl)acrylonitrile, where the two acceptors form parts of different molecules (Galvez et al, 2008); and a very asymmetric N-HÁ Á Á(O) 2 hydrogen bond having the two acceptors in different molecules occurs in the structure of 3,3difluoro-5-nitro-1H-indol-2(3H)-one (Glidewell et al, 2005).…”

Synthesis of New (E)-2-(1H-Indole-3-ylcarbonyl)-3-heteroaryl-acrylonitriles via Microwave-Assisted Knoevenagel Condensation

“…In our work, the product obtained was assigned as isomer, assuming it as the thermodynamically more stable isomer. As previously reported with products of similar structural characteristics which also showed preference for the isomer [8,10,53,71,72].…”

2-Cyano-N-(2,6-dimethoxypyrimidin-4-yl)-3-[4-(dimethylamino)phenyl]acrylamide and dimethylammonium 6-cyano-1,3-dimethyl-2,4,5-trioxo-1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidin-8-ide: a π-stacked dimer and a hydrogen-bonded ribbon containing three types of ring

“…The formation of the salt (II) in the reaction of dimethylformamide dimethylacetal with a cyanoacetylpyrimidine derivative may be contrasted with the reaction (Galvez et al, 2008) of the same acetal with a cyanoacetylindole derivative to form the neutral compound, (III) (see scheme 3). Here, the intramolecular distances indicate that both of the polarized forms, (IIIa) and (IIIb), are significant contributors to the overall electronic structure.…”