Crystal structure of 2-benzyl-amino-4-(4-bromo-phen-yl)-6,7-di-hydro-5H-cyclo-penta-[b]pyridine-3-carbo-nitrile.

R A Nagalakshmi,S Maharani,J Suresh,P L Nilantha Lakshman,R Ranjith Kumar

doi:10.1107/s2056989015002820

R A Nagalakshmi, S Maharani + Show 3 more

Open Access

https://doi.org/10.1107/s2056989015002820

Copy DOI

Abstract

In the title compound C22H18BrN3, the cyclo-pentane ring adopts an envelope conformation with the central methyl-ene C atom as the flap. The dihedral angles between the central pyridine ring and the pendant benzyl and and bromo-benzene rings are 82.65 (1) and 47.23 (1)°, respectively. In the crystal, inversion dimers linked by pairs of N-H⋯Nn (n = nitrile) hydrogen bonds generate R 2 (2)(12) loops. These dimers are linked by weak π-π inter-actions [centroid-centroid distance = 3.7713 (14) Å] into a layered structure.

Highlights

Cyanopyridine derivatives exhibit useful anticancer and antiviral activities (Cocco et al, 2005; El-Hawash & Abdel Wahab, 2006). 3-Cyanopyridine derivatives have been reported for their wide range of applications such as in their antimicrobial, analgesic, anti-hyperglycemic, antiproliferative and antitumor activities (Brandt et al, 2010; El-Sayed et al, 2011; Ji et al, 2007)
As part of our ongoing work in this area, we synthesized the title compound, which contains a pyridine 3-carbonitrile group, and we report on its crystal structure
The cyclopentane ring fused with the pyridine ring adopts an envelope conformation with atom

Summary

Chemical context

Cyanopyridine derivatives exhibit useful anticancer and antiviral activities (Cocco et al, 2005; El-Hawash & Abdel Wahab, 2006). 3-Cyanopyridine derivatives have been reported for their wide range of applications such as in their antimicrobial, analgesic, anti-hyperglycemic, antiproliferative and antitumor activities (Brandt et al, 2010; El-Sayed et al, 2011; Ji et al., 2007). Cyanopyridine derivatives exhibit useful anticancer and antiviral activities (Cocco et al, 2005; El-Hawash & Abdel Wahab, 2006). 3-Cyanopyridine derivatives have been reported for their wide range of applications such as in their antimicrobial, analgesic, anti-hyperglycemic, antiproliferative and antitumor activities (Brandt et al, 2010; El-Sayed et al, 2011; Ji et al., 2007). As part of our ongoing work in this area, we synthesized the title compound, which contains a pyridine 3-carbonitrile group, and we report on its crystal structure

Structural commentary

Database survey

Supramolecular features

Refinement