A new monoclinic polymorph of N-(3-methylphenyl) ethoxycarbothioamide: Crystal structure and Hirshfeld surface analysis

Mukesh M, and Yeo, Chien Ing * and Tiekink, Edward R. T. * (2017) A new monoclinic polymorph of N-(3-methylphenyl) ethoxycarbothioamide: Crystal structure and Hirshfeld surface analysis. Acta Crystallographica Section E Crystallographic Communications, E73 (12). pp. 1889-1897. ISSN 2056-9890

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Abstract

The title compound, C10H13NOS, is a second monoclinic polymorph (space group P21/c, Z′ = 2) of the previously reported C2/c (Z = 1) polymorph [Tadbuppa & Tiekink (2005). Z. Kristallogr. New Cryst. Struct. 220, 395–396]. Two independent mol­ecules comprise the asymmetric unit of the new polymorph and each of these exists as a thioamide–thione tautomer. In each molecule, the central CNOS chromophore is strictly planar [r.m.s. deviations = 0.0003 and 0.0015 Å] and forms dihedral angles of 6.17 (5) and 20.78 (5)° with the N-bound 3-tolyl rings, thereby representing the major difference between the mol­ecules. The thione-S and thio­amide-N—H atoms are syn in each mol­ecule and this facilitates the formation of an eight-membered thio­amide {...SCNH}2 synthon between them; the dimeric aggregates are consolidated by pairwise 3-tolyl-C—H...S inter­actions. In the extended structure, supra­molecular layers parallel to (102) are formed via a combination of 3-tolyl-C—H...π(3-tol­yl) and weak π–π inter­actions [inter-centroid distance between 3-tolyl rings = 3.8535 (12) Å]. An analysis of the Hirshfeld surfaces calculated for both polymorphs reveals the near equivalence of one of the independent mol­ecules of the P21/c form to that in the C2/c form.

Item Type: Article
Uncontrolled Keywords: crystal structure; carbothioamide; hydrogen bonding; Hirshfeld surface analysis
Subjects: Q Science > QD Chemistry
Divisions: Sunway University > School of Science and Technology > Research Centre for Crystalline Materials
Depositing User: Dr Janaki Sinnasamy
Related URLs:
Date Deposited: 30 Nov 2017 04:21
Last Modified: 22 Apr 2019 06:19
URI: http://eprints.sunway.edu.my/id/eprint/696

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