Di- n-but-yl[ N'-(3-meth-oxy-2-oxidobenzyl-idene)- N-phenyl-carbamohydrazono-thio-ato]tin(IV): crystal structure, Hirshfeld surface analysis and computational study

Enis Nadia Md Yusof; Huey Chong Kwong; Thiruventhan Karunakaran; Thahira B S A Ravoof; Edward R T Tiekink

doi:10.1107/S2056989021001870

Di- n-but-yl[ N'-(3-meth-oxy-2-oxidobenzyl-idene)- N-phenyl-carbamohydrazono-thio-ato]tin(IV): crystal structure, Hirshfeld surface analysis and computational study

Acta Crystallogr E Crystallogr Commun. 2021 Feb 23;77(Pt 3):286-293. doi: 10.1107/S2056989021001870. eCollection 2021 Mar 1.

Authors

Enis Nadia Md Yusof^{1

2}, Huey Chong Kwong³, Thiruventhan Karunakaran^{4

5}, Thahira B S A Ravoof^{2

6}, Edward R T Tiekink³

Affiliations

¹ Chemistry Section, School of Distance Education, Universiti Sains Malaysia, 11800 USM, Pulau Pinang, Malaysia.
² Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, UPM Serdang 43400, Malaysia.
³ Research Centre for Crystalline Materials, School of Medical and Life Sciences, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia.
⁴ Centre for Drug Research, Universiti Sains Malaysia, 11800 Minden, Pulau Pinang, Malaysia.
⁵ School of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Pulau Pinang, Malaysia.
⁶ 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 diorganotin Schiff base derivative, [Sn(C₄H₉)₂(C₁₅H₁₃N₃O₂S)], features a penta-coordinated tin centre defined by the N,O,S-donor atoms of the di-anionic Schiff base ligand and two methyl-ene-C atoms of the n-butyl substituents. The resultant C₂NOS donor set defines a geometry inter-mediate between trigonal-bipyramidal and square-pyramidal. In the crystal, amine-N-H⋯O(meth-oxy) hydrogen bonding is found in a helical, supra-molecular chain propagating along the b-axis direction. The chains are assembled into a layer parallel to (01) with methyl-ene-C-H⋯π(phen-yl) inter-actions prominent; layers stack without directional inter-actions between them. The analysis of the calculated Hirshfeld surface showed the presence of weak methyl-ene-C-H⋯π(phen-yl) inter-actions and short H⋯H contacts in the inter-layer region. Consistent with the nature of the identified contacts, the stabilization of the crystal is dominated by the dispersion energy term.

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

Grants and funding

This work was funded by Putra Group Initiative grant IPB No. 9581001. Sunway University Sdn Bhd grant GRTIN-IRG-01-2021.