Crystal Structure and Theoretical Study of N,N-di[(5-chloro-2-oxo-2,3-dihydrobenzo[d]oxazole-3-yl)methyl]ethanamine

Abdullah Aydin,Orhan Buyukgungor,Zeynep Soyer,Mehmet Akkurt

doi:10.13189/ujpa.2017.110203

Abdullah Aydin, Orhan Buyukgungor + Show 2 more

Open Access

https://doi.org/10.13189/ujpa.2017.110203

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Abstract

The aim of the present work is to explore crystal and electronic structure of N,N-di[(5-chloro-2-oxo-2,3-dihydrobenzo[d]oxazole-3-yl)methyl]ethanamine. In the title compound, C18H15Cl2N3O4, the two 2, 3-dihydro-1, 3-benzoxazole ring systems are almost planar and make a dihedral angle of 96.12(7) with each other. The ethyl group is disordered over two set of sites with a site-occupancy ratio of 0.766(12):0.234(12). The crystal structure contain intermolecular C—H...O hydrogen bonds which form a zigzag chains along the c-axis, C—H...π interactions and π-π stacking interactions [centroid-centroid distance = 3.5668(19) A].

Highlights

A series N-substituted-5-chloro-2(3H)-benzoxazolone derivatives were synthesized and evaluated by [1] their acetylcholinesterase inhibitory activity. These compounds were synthesized by Mannich reaction of 5-chloro-2(3H)-benzoxazolone with the appropriated amines
The acetylcholinesterase inhibitory activity of the title compounds was determined by colorimetric Ellman\'s method
The crystal structure of the title compound was solved by direct methods and was refined by a full-matrix least-squares method on F2

Summary

Introduction

A series N-substituted-5-chloro-2(3H)-benzoxazolone derivatives were synthesized and evaluated by [1] their acetylcholinesterase inhibitory activity. These compounds were synthesized by Mannich reaction of 5-chloro-2(3H)-benzoxazolone with the appropriated amines. After completion of reaction (by monitoring with TLC), water (10 ml) was added to the reaction mixture and stirred at room temperature for 1 h. The resulting precipitate was filtered and washed with water. After drying the precipitate was by crystallization from ethanol-water (1:1) to yield 5-chloro-2(3H)-benzoxazolone. This compound (2 mmol) was dissolved in methanol (5 ml). The resulting precipitate was filtered and washed with cold methanol. Yield 52%; M.p.: 420 K; MS (ESI) m/z (%): 239 (100), 241 (31), 408 (M+H, 10), 410 (M+H+2, 4), 412 (M+H+4, 1)

Crystal Structure Analysis

Spectral Studies

Description of the Crystal Structure of C18H15Cl2N3O4

Theoretical Study

Conclusions