Abstract
C11H16N2O, orthorhombic, Pbca (no. 61), a = 10.7388(6) Å, b = 9.8449(5) Å, c = 21.1259(14) Å, V = 2233.5(2) Å3, Z = 8, Rgt(F) = 0.0582, wRref(F2) = 0.1795, T = 293 K.
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Zeitschrift für Kristallographie - New Crystal Structures
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Crystal structure of 1,1-dimethyl-3-(2-phenylethyl)urea, C11H16N2O
Gamal A. El-Hiti / Keith Smith / Mohammed B. Alshammari / Mohammad Hayal Alotaibi / Benson M. Kariuki
Published Online: 2016-05-21 | DOI: https://doi.org/10.1515/ncrs-2016-0052
Open Access
This article offers supplementary material which is provided at the end of the article.
CCDC no.:: 1478571
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
1,1-Dimethyl-3-(2-phenylethyl)urea was synthesized from reaction of (2-phenylethyl)amine with dimethylcarbamoyl chloride (1.1 mole equivalents) in the presence of triethylamine (1.4 mole equivalents) in dichloromethane under reflux for 1 h. Recrystallization using a mixture of ethyl acetate and diethyl ether (1:3 by volume) gave the title compound (~99%) as colourless crystals, mp 89–90 °C (lit. 88–90 °C [1]; 81–82 °C [2]).
Experimental details
All H atoms were placed in calculated positions and refined using a riding model. For the methyl groups, C—H bonds were fixed at 0.96 Å and Uiso(H) set to 1.5 Ueq(C) with free rotation around the C—C bond (HFIX 137 in SHELX [13]). For the rest of the hydrogens, Uiso(H) was set to 1.2 Ueq(C) with aromatic C—H and N—H distances of 0.93 and 0.86 Å, respectively.
Discussion
The synthesis of substituted ureas is of great interest for both academia and industry since ureas represent various biologically active compounds [2], [3], [4]. Urea derivatives can be synthesized using various efficient procedures [5], [6], [7]. Regioselective lithiation of aromatic ureas with lithium reagents followed by reaction with electrophiles at low temperatures is considered to be one of the most clean, efficient and convenient processes for the production of a large number of substituted derivatives in high yields [8], [9], [10], [11].
The asymetric unit (Figure) of the crystal structure consists of a molecule of C11H16N2O. In the crystal, the amide group is involved in N—H⋯O hydrogen bonding (N⋯O distance = 2.850(2) Å, N—H⋯O angle = 152.4°) leading to the formation of C(4) chains [12] along the [010] direction.
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.
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About the article
Received: 2016-03-14
Accepted: 2016-05-08
Published Online: 2016-05-21
Published in Print: 2016-12-01
Citation Information: Zeitschrift für Kristallographie - New Crystal Structures, Volume 231, Issue 4, Pages 1065–1066, ISSN (Online) 2197-4578, ISSN (Print) 1433-7266, DOI: https://doi.org/10.1515/ncrs-2016-0052.
©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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