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

Shaaban K Mohamed; Joel T Mague; Mehmet Akkurt; Abdallah M Alfayomy; Sahar M Abou Seri; Shaban A A Abdel-Raheem; Mokhtar A Abd Ul-Malik

doi:10.1107/S205698902200603X

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

Acta Crystallogr E Crystallogr Commun. 2022 Jul 26;78(Pt 8):846-850. doi: 10.1107/S205698902200603X. eCollection 2022 Aug 1.

Authors

Shaaban K Mohamed^{1

2}, Joel T Mague³, Mehmet Akkurt⁴, Abdallah M Alfayomy⁵, Sahar M Abou Seri⁶, Shaban A A Abdel-Raheem⁷, Mokhtar A Abd Ul-Malik⁸

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 Soil, Water, and Environment Research Institute, Agricultural Research Center, Giza, Egypt.
⁸ Chemistry Department, Faculty of Applied Science, Taiz University, Taiz, Yemen.

Abstract

In the title mol-ecule, C₂₃H₂₀Cl₂N₄O₃S, the thia-zole ring is planar while the pyrimidine unit fused to it adopts a screw-boat conformation. In the crystal, thick sheets parallel to the bc plane are formed by N-H⋯N, C-H⋯N and C-H⋯O hydrogen bonds together with π-π inter-actions between the formamido carbonyl groups and the thia-zole rings. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (30.9%), Cl⋯H/H⋯Cl (20.7%), C⋯H/H⋯C (16.8%) and O⋯H/H⋯O (11.4%) inter-actions.

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.