Crystal structure and theoretical study of N,N-bis[(5-chloro-2-oxo-2,3-dihydrobenzo[d]-oxazol-3-yl)methyl]-2-phenylethanamine

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AYDIN A., SOYER Z., AKKURT M., Buyukgungor O.

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, vol.74, pp.757-766, 2018 (ESCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 74
  • Publication Date: 2018
  • Doi Number: 10.1107/s2056989018005984
  • Journal Indexes: Emerging Sources Citation Index (ESCI), Scopus
  • Page Numbers: pp.757-766
  • Keywords: crystal structure, 2,3-dihydro-1,3-benzoxazole ring, semi-empirical CNDO/2 method, HOMO, LUMO, DERIVATIVES, 2(3H)-BENZOXAZOLONE, BENZOXAZOLONE
  • Ondokuz Mayıs University Affiliated: Yes


In the molecular structure of the title compound, C24H19Cl2N3O4, the three C atoms of the central N, N-dimethylmethanamine moiety are bonded to the N atoms of the two 5-chloro-1,3-benzoxazol-2(3H)-one groups and to the methyl C atom of the methylbenzene group. One of the nine-membered 2,3-dihydro-1,3-benzoxazole rings and the phenyl ring are almost parallel to each other, making a dihedral angle of 5.30 (18)degrees, but they are almost normal to the mean plane of the other nine-membered 2,3-dihydro-1,3-benzoxazole ring, subtending dihedral angles of 89.29 (16) and 85.41 (18)degrees, respectively. The crystal structure features C-H center dot center dot center dot O hydrogen bonds and pi-pi stacking interactions [centroid-to-centroid distances = 3.5788 (19) angstrom, slippage = 0.438 and 3.7773 (16) angstrom, and slippage = 0.716 angstrom].