Crystal structure and Hirshfeld surface analysis of 3-(4-meth-oxy-phen-yl)-1-methyl-4-phenyl-1 H-pyrazolo-[3,4- d]pyrimidine

Mohamed El Hafi; Sevgi Kansiz; Sanae Lahmidi; Mohammed Boulhaoua; Youssef Ramli; Necmi Dege; El Mokhtar Essassi; Joel T Mague

doi:10.1107/S2056989019004894

Crystal structure and Hirshfeld surface analysis of 3-(4-meth-oxy-phen-yl)-1-methyl-4-phenyl-1 H-pyrazolo-[3,4- d]pyrimidine

Acta Crystallogr E Crystallogr Commun. 2019 Apr 16;75(Pt 5):638-641. doi: 10.1107/S2056989019004894. eCollection 2019 May 1.

Authors

Mohamed El Hafi¹, Sevgi Kansiz², Sanae Lahmidi¹, Mohammed Boulhaoua¹, Youssef Ramli³, Necmi Dege², El Mokhtar Essassi¹, Joel T Mague⁴

Affiliations

¹ Laboratoire de Chimie Organique Hétérocyclique, Centre de Recherche Des Sciences des Médicaments, Pôle de Compétence Pharmacochimie, Av Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco.
² Ondokuz Mayıs University, Faculty of Arts and Sciences, Department of Physics, 55139, Kurupelit, Samsun, Turkey.
³ Laboratory of Medicinal Chemistry, Faculty of Medicine and Pharmacy, Mohammed V, University Rabat, Morocco.
⁴ Department of Chemistry, Tulane University, New Orleans, LA 70118, USA.

Abstract

In the title mol-ecule, C₁₉H₁₆N₄O, the planar pyrazolo-pyrimidine moiety is inclined to the attached phenyl rings by 35.42 (4) and 54.51 (6)°. In the crystal, adjacent mol-ecules are linked into chains parallel to [110] and [10] by C-H⋯O and C-H⋯N hydrogen bonds. Additional C-H⋯π(ring) inter-actions lead to the formation of the final three-dimensional network structure. The Hirshfeld surface analysis of the title compound suggests that the most significant contributions to the crystal packing are from H⋯H (48.2%), C⋯H/H⋯C (23.9%) and N⋯H/H⋯N (17.4%) contacts.

Keywords: C—H⋯π(ring) interactions; Hirshfeld surface analysis; crystal structure; hydrogen bond; pyrazolopyrimidine.

Grants and funding

This work was funded by National Science Foundation grant 1228232. Tulane University grant .