Bis{ N'-[3-(4-nitro-phen-yl)-1-phenyl-prop-2-en-1-yl-idene]- N-phenyl-carbamimido-thio-ato}zinc(II): crystal structure, Hirshfeld surface analysis and computational study

Ming Yueh Tan; Huey Chong Kwong; Karen A Crouse; Thahira B S A Ravoof; Edward R T Tiekink

doi:10.1107/S2056989021007398

Bis{ N'-[3-(4-nitro-phen-yl)-1-phenyl-prop-2-en-1-yl-idene]- N-phenyl-carbamimido-thio-ato}zinc(II): crystal structure, Hirshfeld surface analysis and computational study

Acta Crystallogr E Crystallogr Commun. 2021 Jul 27;77(Pt 8):839-846. doi: 10.1107/S2056989021007398. eCollection 2021 Aug 1.

Authors

Ming Yueh Tan¹, Huey Chong Kwong², Karen A Crouse^{3

4}, Thahira B S A Ravoof^{3

5}, Edward R T Tiekink²

Affiliations

¹ Department of Physical Science, Faculty of Applied Sciences, Tunku Abdul Rahman University College, 50932 Setapak, Kuala Lumpur, Malaysia.
² Research Centre for Crystalline Materials, School of Medical and Life Sciences, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia.
³ Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, UPM, Serdang 43400, Malaysia.
⁴ Department of Chemistry, St. Francis Xavier University, PO Box 5000, Antigonish, NS B2G 2W5, Canada.
⁵ Foundry of Reticular Materials for Sustainability (FORMS), Materials Synthesis and Characterization Laboratory, Institute of Advanced Technology, Universiti Putra Malaysia, 43400 Serdang, Selangor Darul, Ehsan, Malaysia.

Abstract

The title zinc bis-(thio-semicarbazone) complex, [Zn(C₂₂H₁₇N₄O₂S)₂], comprises two N,S-donor anions, leading to a distorted tetra-hedral N₂S₂ donor set. The resultant five-membered chelate rings are nearly planar and form a dihedral angle of 73.28 (3)°. The configurations about the endocyclic- and exocyclic-imine bonds are Z and E, respectively, and that about the ethyl-ene bond is E. The major differences in the conformations of the ligands are seen in the dihedral angles between the chelate ring and nitro-benzene rings [40.48 (6) cf. 13.18 (4)°] and the N-bound phenyl and nitro-benzene ring [43.23 (8) and 22.64 (4)°]. In the crystal, a linear supra-molecular chain along the b-axis direction features amine-N-H⋯O(nitro) hydrogen bonding. The chains assemble along the 2₁-screw axis through a combination of phenyl-C-H⋯O(nitro) and π(chelate ring)-π(phen-yl) contacts. The double chains are linked into a three-dimensional architecture through phenyl-C-H⋯O(nitro) and nitro-O⋯π(phen-yl) inter-actions.

Keywords: Hirshfeld surface analysis; Schiff base; crystal structure; hydrogen bonding; thiosemicarbazone; zinc.

Grants and funding

This work was funded by Research University Grant Scheme grants 9199834 and 9174000; Malaysian Ministry of Science, Technology and Innovatio grant 09-02-04-0752-EA001; Sunway University Sdn Bhd grant GRTIN-IRG-01-2021.