3-(1-{[1-(4-Bromophenyl)-1H-1,2,3-triazol-4-yl]methyl}piperidin-4-yl)-6-fluoro-1,2-benzoxazole hemihydrate

N Ashwini,S Naveen,N K Lokanath,K S Rangappa,K S Rakesh

doi:10.1107/s241431461502458x

Abstract

The title compound, C21H19BrFN5O·0.5H2O, crystallizes as a hemihydrate with the water molecule located on a twofold rotation axis. The piperidine ring has a chair conformation, whereas the triazole and the benzisoxazole rings are planar (r.m.s. deviations = 0.006 and 0.009 Å, respectively). The N—C and C—C bonds connecting the triazole and benzisoxazole rings, respectively, to the piperidine ring lie in equatorial positions. In the crystal, molecules related by a twofold rotation axis are linkedviaO—H...N hydrogen bonds involving the water molecule and a pair of C—H...N hydrogen bonds forming dimers. The dimers are linkedviaa pair of C—H...F hydrogen bonds leading to the formation of chains propagating along [101].

Highlights

The title compound, C21H19BrFN5OÁ0.5H2O, crystallizes as a hemihydrate with the water molecule located on a twofold rotation axis
Molecules related by a twofold rotation axis are linked via O—HÁ Á ÁN hydrogen bonds involving the water molecule and a pair of C—HÁ Á ÁN hydrogen bonds forming dimers
The dimers are linked via a pair of C—HÁ Á ÁF hydrogen bonds leading to the formation of chains propagating along [101]

Summary

Structure description

Benzisoxazoles display a wide spectrum of biological activities namely antipsychotic, antitumor (Jain & Kwon, 2003), anticonvulsant, antimicrobial (Priya et al, 2005), antithrombotic and cholinesterase inhibiting (Alzheimer’s disease) properties (Rangappa & Basappa, 2005). The piperidine ring has a chair conformation whereas the triazole and the benzisoxazole rings are planar (r.m.s. deviations are 0.006 and 0.009 A , respectively). The bonds N4—C17 and C11—C9 connecting the triazole and the benzisoxazole rings, respectively, lie in equatorial positions on the piperidine ring. Molecules related by a twofold rotation axis are linked via O—HÁ Á ÁN hydrogen bonds, involving the water molecule, and a pair of C—HÁ Á ÁN hydrogen bonds forming dimers. The combined organic layer was washed with water (10 ml), followed by brine (10 ml) and Figure 2 A view in projection along the b axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines (see Table 1), and H atoms not involved in hydrogen bonding have been omitted for clarity

DÁ Á ÁA

Data collection Diffractometer Absorption correction

Data collection

Special details