Crystal structure and DFT study of 2-(pyren-1-yl)-1 H-benzimidazole

Md Serajul Haque Faizi; Necmi Dege; S Malinkin

doi:10.1107/S2056989017010271

Crystal structure and DFT study of 2-(pyren-1-yl)-1 H-benzimidazole

Acta Crystallogr E Crystallogr Commun. 2017 Jul 17;73(Pt 8):1180-1183. doi: 10.1107/S2056989017010271. eCollection 2017 Jul 1.

Authors

Md Serajul Haque Faizi¹, Necmi Dege², S Malinkin³

Affiliations

¹ Department of Chemistry, College of Science, Sultan Qaboos University, PO Box 36 Al-Khod 123, Muscat, Sultanate of Oman.
² Ondokuz Mayıs University, Arts and Sciences Faculty, Department of Physics, 55139 Atakum-Samsun, Turkey.
³ Department of Chemistry, National Taras Shevchenko University of Kiev, 64/13, Volodymyrska Street, City of Kyiv 01601, Ukraine.

Abstract

In the title compound, C₂₃H₁₄N₂, (I), the dihedral angle between the mean planes of the pyrene and benzimidazole ring systems is 42.08 (5)°, with a bridging C-C bond length of 1.463 (3) Å. In the crystal, mol-ecules are linked by N-H⋯N hydrogen bonds, forming columns propagating along the b-axis direction. The columns are linked via C-H⋯π inter-actions, forming slabs parallel to the ab plane. There are no significant π-π inter-actions present in the crystal structure. The density functional theory (DFT) optimized structure, at the B3LYP/ 6-311G(d,p) level, is compared with the experimentally determined solid-state structure of the title compound.

Keywords: C—H⋯π interactions; DFT; N—H⋯N hydrogen bonding; benzimidazole; crystal structure; o-phenylenediamine; pyrene-1-carbaldehyde.