Abstract
C9H11ClN2S, monoclinic, Pc (no. 7), a = 14.8440(4) Å, b = 7.2002(2) Å, c = 10.0920(2) Å, β = 99.733(2)°, V = 1063.10(5) Å3, Z = 4, Rgt(F) = 0.0399, wRref(F2) = 0.1099, T = 296(2) K.
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Zeitschrift für Kristallographie - New Crystal Structures
Editor-in-Chief: Huppertz, Hubert
Ed. by Reiß, Guido
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Crystal structure of 3-(4-chlorophenyl)-1,1-dimethylthiourea, C9H11ClN2S
Published Online: 2016-10-29 | DOI: https://doi.org/10.1515/ncrs-2016-0171
Open Access
This article offers supplementary material which is provided at the end of the article.
CCDC no.:: 1508746
The asymmetric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters.
Table 1
Data collection and handling.
Table 2
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).
Source of material
3-(4-Chlorophenyl)-1,1-dimethylthiourea was synthesized from reaction of 4-chlorophenyl isothiocyanate and dimethylamine (1.1 equivalents) in anhydrous dioxane at low temperature for 1 h. After work-up, the crude product obtained was purified by crystallization from hexane to give the title compound (95%) as colourless crystals, Mp 151–152 °C (lit. 149–151 °C [1], 151 °C [2], 150–151.5 °C [3], 152 °C [4]).
Experimental details
All hydrogen atoms were placed in calculated positions and refined using a riding model. Methyl C—H bonds were fixed at 0.96 Å and the groups were allowed to spin about the C—C bond with displacement parameters 1.5 times Ueq(C). Aromatic C—H distances were set to 0.93 Å and N—H set to 0.86 Å with Uiso set to 1.2 times the Ueq for the parent atoms. The absolute structure was established by a refinement of the Flack parameter (0.09(2)) using 423 quotients [(I+) − (I−)]/[(I+) + (I−)].
Discussion
Thioureas can be synthesized using various procedures and have been used as intermediates in organic syntheses [5; 6; 7; 8; 9; 10; 11]. Some derivatives show interesting applications as biologically active compounds [12; 13; 14; 15; 16; 17].
In the crystal structure of the title compound, the asymmetric unit comprises two crystallographically independent molecules of C9H11ClN2S. In the two molecules, the dimethylthiourea groups are planar (apart from the methyl H atoms). A twist between the chlorophenyl and dimethylthiourea groups is observed in the molecules, in a manner similar to 3-(4-chlorophenyl)-1,1-dimethylurea [18] and 1,1-dimethyl-3-phenylthiourea [19]. The angles between the least-squares planes through the chlorophenyl and dimethylthiourea groups are 55.89(15) and 58.01(12)°, respectively. N—H⋯S interactions occur, forming chains along [001] with geometry: N1⋯S1 = 3.549(4) Å, N1—H1⋯S1 = 128.3° and N3⋯S2 = 3.530(4) Å, N3—H3a⋯S2 = 127.1°
Acknowledgements
The authors extend their appreciation to the College of Applied Medical Sciences Research Centre and the Deanship of Scientific Research at King Saud University for their funding of this research and to Cardiff University for continued support.
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About the article
Received: 2016-05-26
Accepted: 2016-10-08
Published Online: 2016-10-29
Published in Print: 2017-01-01
Citation Information: Zeitschrift für Kristallographie - New Crystal Structures, Volume 232, Issue 1, Pages 105–107, ISSN (Online) 2197-4578, ISSN (Print) 1433-7266, DOI: https://doi.org/10.1515/ncrs-2016-0171.
©2016 Gamal A. El-Hiti et al., published by De Gruyter.. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License. BY-NC-ND 3.0
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