Crystal structure and theoretical study of N, N-bis-[(5-chloro-2-oxo-2,3-di-hydro-benzo[ d]oxazol-3-yl)meth-yl]-2-phenyl-ethanamine

Abdullah Aydın; Zeynep Soyer; Mehmet Akkurt; Orhan Büyükgüngör

doi:10.1107/S2056989018005984

Crystal structure and theoretical study of N, N-bis-[(5-chloro-2-oxo-2,3-di-hydro-benzo[ d]oxazol-3-yl)meth-yl]-2-phenyl-ethanamine

Acta Crystallogr E Crystallogr Commun. 2018 Apr 27;74(Pt 5):757-760. doi: 10.1107/S2056989018005984. eCollection 2018 May 1.

Authors

Abdullah Aydın¹, Zeynep Soyer², Mehmet Akkurt³, Orhan Büyükgüngör⁴

Affiliations

¹ Department of Mathematics and Science Education, Faculty of Education, Kastamonu University, 37200 Kastamonu, Turkey.
² Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ege University, 35100 Izmir, Turkey.
³ Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey.
⁴ Department of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey.

Abstract

In the mol-ecular structure of the title compound, C₂₄H₁₉Cl₂N₃O₄, the three C atoms of the central N,N-di-methyl-methanamine 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 methyl-benzene group. One of the nine-membered 2,3-di-hydro-1,3-benzoxazole rings and the phenyl ring are almost parallel to each other, making a dihedral angle of 5.30 (18)°, but they are almost normal to the mean plane of the other nine-membered 2,3-di-hydro-1,3-benzoxazole ring, subtending dihedral angles of 89.29 (16) and 85.41 (18)°, respectively. The crystal structure features C-H⋯O hydrogen bonds and π-π stacking inter-actions [centroid-to-centroid distances = 3.5788 (19) Å, slippage = 0.438 and 3.7773 (16) Å, and slippage = 0.716 Å].

Keywords: 2,3-dihydro-1,3-benzoxazole ring; HOMO; LUMO; crystal structure; semi-empirical CNDO/2 method.