A triclinic polymorph of miconazole

Hanna Kaspiaruk; Lilianna Chęcińska

doi:10.1107/S2056989024000276

A triclinic polymorph of miconazole

Acta Crystallogr E Crystallogr Commun. 2024 Jan 26;80(Pt 2):196-200. doi: 10.1107/S2056989024000276. eCollection 2024 Feb 1.

Authors

Hanna Kaspiaruk^{1

2}, Lilianna Chęcińska²

Affiliations

¹ University of Lodz Doctoral School of Exact and Natural Sciences, Narutowicza 68, 90-136 Łódź, Poland.
² University of Lodz, Faculty of Chemistry, Pomorska 163/165, 90-236 Łódź, Poland.

Abstract

The crystal structure of the new triclinic polymorph of miconazole {MIC; C₁₈H₁₄Cl₄N₂O; systematic name: (RS)-1-[2-(2,4-di-chloro-benz-yloxy)-2-(2,4-di-chloro-phen-yl)eth-yl]-1H-imidazole} is reported and compared with the monoclinic form of solvent-free miconazole previously reported [Kaspiaruk & Chęcińska (2022 ▸). Acta Cryst. C78, 343-350]. A comparison shows a different orientation of imidazole and one di-chloro-phenyl ring between polymorphic mol-ecules. In the crystal structure of the title compound, only weak halogen bonds and C-H⋯π(arene) inter-actions are found. Hirshfeld surface analysis and energy framework calculations complement the comparison of the two polymorphic forms of the miconazole drug.

Keywords: Hirshfeld surface; crystal structure; energy frameworks; miconazole.