Crystal structure of 2-(2-bromophenyl)-4-(1H-indol-3-yl)-6-(thiophen-2-yl)pyridine-3-carbonitrile

Abstract

In the title compound, C24H14BrN3S, the dihedral angles between the planes of the pyridine ring and the pendant thio­phene ring, the indole ring system (r.m.s. deviation = 0.022 Å) and the bromo­benzene ring are 9.37 (17), 21.90 (12) and 69.01 (15)°, respectively. The approximate coplanarity of the central ring and the indole ring system is supported by two intra­molecular C—H⋯N inter­actions. In the crystal, inversion dimers linked by pairs of N—H⋯N hydrogen bonds generate R 2 2(16) loops and the dimers are linked by C—H⋯π and aromatic π–π stacking [shortest centroid–centroid separation = 3.729 (3) Å] into a three-dimensional network.

5-(2-Hydroxybenzoyl)-2-(1H-indol-3-yl)pyridine-3-carbonitrile

“…1. The C-N distances range from 1.345 (2) to 1.370 (2) Å , and are in good agreement with the related reported values (Vishnupriya et al, 2014). The C14-O1 and C21-N3 bond lengths are 1.2347 (14) Å and 1.1413 (16) Å , respectively, in agreement with values reported by Vimala et al (2015), confirming the presence of double and triple bonds.…”

Crystal structure and Hirshfeld surface analysis of 2-amino-6-[(1-phenylethyl)amino]-4-(thiophen-2-yl)pyridine-3,5-dicarbonitrile

“…The four related compounds found as a result of the search for '2,6-diamino-4-(thiophen-2-yl)pyridine-3,5-dicarbonitrile' in the Cambridge Structure Database (CSD, Version 5.42, update of September 2021; Groom et al, 2016) are MUCLAA (Vu Quoc et al, 2019), WOJCIJ (Vishnupriya et al, 2014a), WOPLAQ (Vishnupriya et al, 2014b) and DOPWOW (Vishnupriya et al, 2014c).…”

Crystal structure of 2-(4-chlorophenyl)-4-(1H-indol-3-yl)-6-phenylpyridine-3-carbonitrile

“…For the biological activity of substituted pyridine derivatives, see: Yao et al (1994). For a related structure, see: Vishnupriya et al (2014 Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.…”

“…Thienopyridines have been used as antithrombotic agents (Yao et al, 1994) against platelet aggregation. As part of our ongoing studies in this area (Vishnupriya et al, 2014) the title compound was investigated.…”