Synthesis, crystal structure at 219 K and Hirshfeld surface analyses of 1,4,6-tri-methyl-quinoxaline-2,3(1 H,4 H)-dione monohydrate

Ayman Zouitini; Md Serajul Haque Faizi; Younes Ouzidan; Fouad Ouazzani Chahdi; Jérôme Marrot; Damien Prim; Necmi Dege; Ashraf Mashrai

doi:10.1107/S2056989020009573

Synthesis, crystal structure at 219 K and Hirshfeld surface analyses of 1,4,6-tri-methyl-quinoxaline-2,3(1 H,4 H)-dione monohydrate

Acta Crystallogr E Crystallogr Commun. 2020 Jul 17;76(Pt 8):1296-1301. doi: 10.1107/S2056989020009573. eCollection 2020 Aug 1.

Authors

Ayman Zouitini¹, Md Serajul Haque Faizi², Younes Ouzidan³, Fouad Ouazzani Chahdi¹, Jérôme Marrot⁴, Damien Prim⁴, Necmi Dege⁵, Ashraf Mashrai⁶

Affiliations

¹ Laboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, BP 2202, Fez, Morocco.
² Department of Chemistry, Langat Singh College, B.R.A. Bihar University, Muzaffarpur, Bihar-842001, India.
³ Laboratoire de Chimie Physique et Chimie Bio-organique, Faculté des Sciences et Techniques Mohammedia, Université Hassan II, Casablanca, BP 146, 28800, Mohammedia, Morocco.
⁴ Institut Lavoisier de Versailles, UVSQ, CNRS, Université Paris-Saclay, 78035 Versailles, France.
⁵ Department of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, Samsun, 55200, Turkey.
⁶ Department of Pharmacy, University of Science and Technology, Ibb Branch, Ibb, Yemen.

Abstract

The asymmetric unit of the title compound, C₁₁H₁₂N₂O₂·H₂O, contains a mol-ecule of 1,4,6-trimethyl-1,4-di-hydro-quinoxaline-2,3-dione and a solvent water mol-ecule. Four atoms of the benzene ring are disordered over two sets of sites in a 0.706 (7):0.294 (7) ratio while the N-bound methyl groups are rotationally disordered with occupancy ratios of 0.78 (4):0.22 (4) and 0.76 (5):0.24 (5). In the crystal, mol-ecules are linked by O-H⋯O and C-H⋯O hydrogen bonds into layers lying parallel to (10). The Hirshfeld surface analysis indicates that the most important contributions to the packing arrangement are due to H⋯H (51.3%) and O⋯H/H⋯O (28.6%) inter-actions. The mol-ecular structure calculated by density functional theory is compared with the experimentally determined mol-ecular structure, and the HOMO-LUMO energy gap has been calculated.

Keywords: Hirshfeld surface analysis; crystal structure; disorder; hydrogen bonding; quinoxaline-2,3-dione.

Grants and funding

This work was funded by University Grants Commission grant . Université Sidi Mohamed Ben Abdallah, Morocco grant . University of Science and Technology, Ibb Branch, Yemen grant .