Crystal structure and Hirshfeld surface analysis of (E)- N-(4-propyl-oxybenzyl-idene)benzo[ d]thia-zol-2-amine

Ropak A Sheakh Mohamad; Wali M Hamad; Hashim J Aziz; Necmi Dege

doi:10.1107/S2056989020012128

Crystal structure and Hirshfeld surface analysis of (E)- N-(4-propyl-oxybenzyl-idene)benzo[ d]thia-zol-2-amine

Acta Crystallogr E Crystallogr Commun. 2020 Sep 4;76(Pt 10):1591-1594. doi: 10.1107/S2056989020012128. eCollection 2020 Oct 1.

Authors

Ropak A Sheakh Mohamad¹, Wali M Hamad², Hashim J Aziz³, Necmi Dege⁴

Affiliations

¹ Salahaddin University, College of Science, Department of Chemistry, Erbil, Iraq.
² Koya University, Faculty of Science and Health, Department of Chemistry, Koya, Iraq.
³ Salahaddin University, College of Education, Department of Chemistry, Erbil, Iraq.
⁴ Ondokuz Mayıs University, Faculty of Arts and Sciences, Department of Physics, 55139, Samsun, Turkey.

Abstract

The title compound, C₁₇H₁₆N₂OS, was synthesized by a condensation reaction between 2-amino benzo-thia-zole and 4-N-propoxybenzaldehyde. The benzo[d]thia-zole ring system is nearly planar (r.m.s. deviation 0.0088 Å) and makes a dihedral angle of 3.804 (12)° with the phenyl ring. The configuration about the C=N double bond is E. In the crystal structure, pairs of C-H⋯N hydrogen bonds and C-H⋯π inter-actions link the mol-ecules into inversion dimers with an R ² ₂(16) ring motif. These dimers are additionally linked by weak π-π stacking inter-actions between the phenyl rings, leading to a layered arrangement parallel to (010). Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the packing arrangement are from H⋯H (47.9%) and C⋯H/H⋯C (25.6%) inter-actions.

Keywords: 2-aminobenzothiazole; Hirshfeld surface; Schiff base; crystal structure; heterocyclic compound.

Grants and funding

This work was funded by Ondokuz Mayıs University grant PYO.FEN.1906.19.001.