Crystal structure and Hirshfeld surface analysis of ethyl (3 E)-5-(4-fluoro-phen-yl)3-{[(4-meth-oxy-phen-yl)formamido]-imino}-7-methyl-2 H,3 H,5 H-[1,3]thia-zolo[3,2- a]pyrimidine-6-carboxyl-ate 0.25-hydrate

Shaaban K Mohamed; Joel T Mague; Mehmet Akkurt; Abdallah M Alfayomy; Fatma A F Ragab; Mokhtar A Abd Ul-Malik

doi:10.1107/S2056989022006041

Crystal structure and Hirshfeld surface analysis of ethyl (3 E)-5-(4-fluoro-phen-yl)3-{[(4-meth-oxy-phen-yl)formamido]-imino}-7-methyl-2 H,3 H,5 H-[1,3]thia-zolo[3,2- a]pyrimidine-6-carboxyl-ate 0.25-hydrate

Acta Crystallogr E Crystallogr Commun. 2022 Aug 9;78(Pt 9):880-884. doi: 10.1107/S2056989022006041. eCollection 2022 Sep 1.

Authors

Shaaban K Mohamed^{1

2}, Joel T Mague³, Mehmet Akkurt⁴, Abdallah M Alfayomy⁵, Fatma A F Ragab⁶, Mokhtar A Abd Ul-Malik⁷

Affiliations

¹ Chemistry and Environmental Division, Manchester Metropolitan University, Manchester, M1 5GD, England.
² Chemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt.
³ Department of Chemistry, Tulane University, New Orleans, LA 70118, USA.
⁴ Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey.
⁵ Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Al-Azhar University, Assiut, 71524, Egypt.
⁶ Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Cairo University, Kasr El-Aini Street, Cairo, PO Box, 11562, Egypt.
⁷ Chemistry Department, Faculty of Applied Science, Taiz University, Taiz, Yemen.

Abstract

In the title compound, C₂₄H₂₃FN₄O₄S·0.25H₂O, the di-hydro-pyrimidine ring is distinctly non-planar, with the flap C atom deviating by 0.297 (2) Å from the least-squares plane. In the crystal, zigzag chains are formed by N-H⋯N hydrogen bonds parallel to [010] and are connected into layers parallel to (100) by O-H⋯O, O-H⋯F, C-H⋯O, C-H⋯F and C-H⋯N hydrogen bonds. Additional C-H⋯O hydrogen bonds connect the layers into a three-dimensional network. A Hirshfeld surface analysis indicates that the most significant contributions to the crystal packing are from H⋯H (42.6%), O⋯H/H⋯O (16.8%) and C⋯H/H⋯C (15.5%) contacts.

Keywords: Hirshfeld surface analysis; crystal structure; hydrogen bond; pyrimidine; thiazole.

Grants and funding

The support of NSF-MRI grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.