Crystal structure, DFT calculations and Hirshfeld surface analysis of 3-(4-methyl-phen-yl)-6-nitro-1 H-indazole

Ali Ben-Yahia; Youness El Bakri; Chin-Hung Lai; El Mokhtar Essassi; Joel T Mague

doi:10.1107/S205698901801647X

Crystal structure, DFT calculations and Hirshfeld surface analysis of 3-(4-methyl-phen-yl)-6-nitro-1 H-indazole

Acta Crystallogr E Crystallogr Commun. 2018 Nov 22;74(Pt 12):1857-1861. doi: 10.1107/S205698901801647X. eCollection 2018 Dec 1.

Authors

Ali Ben-Yahia¹, Youness El Bakri^{1

2}, Chin-Hung Lai³, El Mokhtar Essassi¹, Joel T Mague⁴

Affiliations

¹ Laboratoire de Chimie Organique Hétérocyclique, Centre de Recherche des Sciences des Médicaments, URAC 21, Pôle de Compétence Pharmacochimie, Av Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco.
² Department of Chemistry, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St, Moscow 117198, Russian Federation.
³ Department of Medical Applied Chemistry, Chung Shan Medical University, Taichung 40241, Taiwan.
⁴ Department of Chemistry, Tulane University, New Orleans, LA 70118, USA.

Abstract

The asymmetric unit of the title compound, C₁₄H₁₁N₃O₃, consists of two independent mol-ecules having very similar conformations in which the indazole moieties are planar. The independent mol-ecules are distinguished by small differences in the rotational orientations of the nitro groups. In the crystal, N-H⋯O and C-H⋯O hydrogen bonds form zigzag chains along the b-axis direction. Additional C-H⋯O hydrogen bonds link the chains into layers parallel to (10). These are connected by slipped π-stacking and C-H⋯π(ring) inter-actions.

Keywords: crystal structure; hydrogen bonds; indazole; π-stacking.

Grants and funding

This work was funded by Tulane University grant . RUDN University Program 5–100 grant .