Issue 7, 2007
From the journal:

CrystEngComm

Principles of crystal packing in O-isopropyl-N-aryl-thiocarbamides: iPrOC([double bond, length as m-dash]S)N(H)C6H4-4-Y: Y = H, Cl, and Me

Fong Sheen Kuan,a   Fabian Mohr,b   Primjira P. Tadbuppaa  and  Edward R. T. Tiekink*c  

* Corresponding authors

a Department of Chemistry, National University of Singapore, Singapore

b Fachbereich C - Anorganische Chemie, Bergische Universität Wuppertal, 42119 Wuppertal, Germany

c Department of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA
E-mail: Edward.Tiekink@utsa.edu
Fax: 1 210 458 7428
Tel: 1 210 458 5774

Abstract

Crystallographic analysis shows no significant influence is exerted by the nature of Y upon the molecular parameters of the central O–C([double bond, length as m-dash]S)–N(H) chromophore in the structures of iPrOC([double bond, length as m-dash]S)N(H)C6H4-4-Y, for Y = H (1), Cl (2), and Me (3); this is verified by a theoretical study. The crystal structures each feature dimeric aggregates as a result of the uniform formation of the {⋯H–N–C[double bond, length as m-dash]S}2, thioamide, synthon. An analysis of the crystal structures shows that the substitution of the chloride atom in (2) by a methyl group, leading to (3), has a profound influence on the crystal packing owing to the participation of the chloride atom in structure directing C–H⋯Cl interactions that link the dimeric aggregates into a double layer structure. In the structures of (1) and (3), C–H⋯S interactions serve to connect molecules into columnar and layer structures, respectively, with weak C–H⋯O (and π⋯π interactions in (3)) further reinforcing the crystal packing.

Graphical abstract: Principles of crystal packing in O-isopropyl-N-aryl-thiocarbamides: iPrOC( [[double bond, length as m-dash]] S)N(H)C6H4-4-Y: Y = H, Cl, and Me

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/B701489A
Article type
Paper
Submitted
31 Jan 2007
Accepted
20 Mar 2007
First published
30 Mar 2007

CrystEngComm, 2007,9, 574-581

Permissions

Request permissions

Principles of crystal packing in O-isopropyl-N-aryl-thiocarbamides: iPrOC([double bond, length as m-dash]S)N(H)C6H4-4-Y: Y = H, Cl, and Me

F. S. Kuan, F. Mohr, P. P. Tadbuppa and E. R. T. Tiekink, CrystEngComm, 2007, 9, 574 DOI: 10.1039/B701489A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements