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, R
 gt
 (F) = 0.0582, wR
 ref
 (F
 2) = 0.1795, T = 293 K.</jats:p

Alotaibi, Mohammad Hayal

Alshammari, Mohammed B.

El-Hiti, Gamal A.

Kariuki, Benson M.

Smith, Keith

Gamal A. El-Hiti

Keith Smith

Mohammed B. Alshammari

Mohammad Hayal Alotaibi

Benson M. Kariuki

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Zeitschrift für Kristallographie - New Crystal Structures

Crystal structure of 1,1-dimethyl-3-(2-phenylethyl)urea, C11H16N2O

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Z. Kristallogr. NCS 2016; 231(4): 1065–1066Open AccessGamal A. El-Hiti*, Keith Smith, Mohammed B. Alshammari, Mohammad Hayal Alotaibi andBenson M. KariukiCrystal structure of 1,1-dimethyl-3-(2-phenylethyl)urea, C11H16N2ODOI 10.1515/ncrs-2016-0052Received March 14, 2016; accepted May 8, 2016; availableonline May 21, 2016AbstractC11H16N2O, 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.CCDC no.: 1478571Tables 1 and 2 contain details of the measurement methodand a list of the atoms including atomic coordinates anddisplacement parameters.Source of material1,1-Dimethyl-3-(2-phenylethyl)urea was synthesized fromreaction of (2-phenylethyl)amine with dimethylcarbamoylchloride (1.1 mole equivalents) in the presence of triethy-lamine (1.4 mole equivalents) in dichloromethane underreux for 1 h. Recrystallizationusing amixture of ethyl acetate*Corresponding author: Gamal A. El-Hiti, Cornea Research Chair,Department of Optometry, College of Applied Medical Sciences,King Saud University, P.O. Box 10219, Riyadh 11433, Saudi Arabia,e-mail: gelhiti@ksu.edu.saKeith Smith and Benson M. Kariuki: School of Chemistry, CardiUniversity, Main Building, Park Place, Cardi CF10 3AT, UKMohammed B. Alshammari: Chemistry Department, College ofSciences and Humanities, Prince Sattam bin Abdulaziz University,P.O. Box 83, Al-Kharij 11942, Saudi ArabiaMohammad Hayal Alotaibi: National Center for PetrochemicalsTechnology, King Abdulaziz City for Science and Technology, P.O.Box 6086, Riyadh 11442, Saudi ArabiaTable 1: Data collection and handling.Crystal: Colourless, blockSize 0.370.170.10 mmWavelength: Mo Kα radiation (0.71073 Å)µ: 0.8 cm 1Diractometer, scan mode: SuperNova, ω2θmax, completeness: 59.4°, >99%N(hkl)measured, N(hkl)unique, Rint: 7627, 2680, 0.025Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 1669N(param)rened: 129Programs: SHELX [13], CrysAlisPRO [14],WinGX [15]Table 2: Fractional atomic coordinates and isotropic or equivalentisotropic displacement parameters (Å2).Atom x y z Uiso*/UeqC1 0.48541(18) 0.06211(19) 0.35228(8) 0.0580(5)C2 0.5322(2) 0.1652(2) 0.31509(11) 0.0743(6)H2 0.6015 0.2135 0.3288 0.089*C3 0.4777(3) 0.1979(3) 0.25766(12) 0.0921(8)H3 0.5107 0.2678 0.2333 0.111*C4 0.3765(3) 0.1288(3) 0.23680(13) 0.0993(8)H4 0.3409 0.1505 0.1980 0.119*C5 0.3273(2) 0.0284(3) 0.27259(13) 0.0975(8)H5 0.2573  0.0183 0.2586 0.117*C6 0.3810(2)  0.0053(2) 0.33001(11) 0.0784(6)H6 0.3463  0.0746 0.3542 0.094*C7 0.54501(19) 0.0256(2) 0.41422(9) 0.0687(6)H7A 0.4881  0.0306 0.4384 0.082*H7B 0.5599 0.1080 0.4382 0.082*C8 0.66752(18)  0.04998(19) 0.40590(9) 0.0618(5)H8A 0.6514  0.1347 0.3839 0.074*H8B 0.7222 0.0041 0.3794 0.074*C9 0.79739(16) 0.01667(16) 0.49494(10) 0.0565(5)C10 0.8638(2)  0.1564(2) 0.57266(11) 0.0833(7)H10A 0.7839  0.1822 0.5891 0.125*H10B 0.9248  0.1612 0.6058 0.125*H10C 0.8868  0.2170 0.5390 0.125*C11 0.9276(2) 0.0821(2) 0.58375(12) 0.0848(7)H11A 0.9358 0.1629 0.5587 0.127*H11B 1.0088 0.0470 0.5934 0.127*H11C 0.8846 0.1031 0.6224 0.127*N1 0.73091(15)  0.07966(14) 0.46471(7) 0.0604(4)H1 0.7261  0.1599 0.4806 0.072*N2 0.85761(15)  0.01881(16) 0.54863(8) 0.0675(5)O1 0.80282(14) 0.13384(12) 0.47359(8) 0.0751(5)© 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.Brought to you by | Cardiff UniversityAuthenticatedDownload Date | 11/29/16 3:49 PM1066 | El-Hiti et al.: C11H16N2Oand 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 detailsAll H atoms were placed in calculated positions and renedusing a riding model. For the methyl groups, C—H bondswere xed at 0.96 Å and U iso(H) set to 1.5 Ueq(C) with freerotation around the C—C bond (HFIX 137 in SHELX [13]).For the rest of the hydrogens, U iso(H) was set to 1.2 Ueq(C)with aromatic C—H and N—H distances of 0.93 and 0.86 Å,respectively.DiscussionThe synthesis of substituted ureas is of great interest for bothacademia and industry since ureas represent various biologi-cally active compounds [2–4]. Urea derivatives can be synthe-sized using various ecient procedures [5–7]. Regioselectivelithiation of aromatic ureas with lithium reagents followed byreaction with electrophiles at low temperatures is consideredto be one of themost clean, ecient and convenient processesfor the production of a large number of substituted derivativesin high yields [8–11].The asymetric unit (Figure) of the crystal structureconsists of a molecule of C11H16N2O. In the crystal, the amidegroup is involved in N—H· · ·O hydrogen bonding (N· · ·Odistance= 2.850(2) Å, N—H· · ·O angle= 152.4°) leading tothe formation of C(4) chains [12] along the [010] direction.Acknowledgements: The authors extend their appreciationto the College of Applied Medical Sciences Research Cen-tre and the Deanship of Scientic Research at King SaudUniversity for their funding of this research.References1. Smith, K.; El-Hiti, G. A.; Alshammari, M. B.: Lithiation andsubstitution of N′-(ω-phenylalkyl)-N,N-dimethylureas.Synthesis 44 (2012) 20139–2022.2. Wilson, A. A.; Garcia, A.; Houle, S.; Sadovski, O.; Vasdev, N.:Synthesis and application of isocyanates radiolabeled withcarbon-11. Chem. Eur. J. 17 (2011) 259–264.3. Gennäs, G. B.; Mologni, L.; Ahmed, S.; Rajaratnam, M.;Marin, O.; Lindholm, N.; Viltadi, M.; Gambacorti-Passerini, C.;Scapozza, L.; Yli-Kauhaluoma, J.: Design, synthesis,and biological activity of urea derivatives as anaplasticlymphoma kinase inhibitors. Chem. Med. Chem. 6 (2011)1680–1692.4. Kocyigit-Kaymakcioglu, B.; Celen, A. O.; Tabanca, N.;Ali, A.; Khan, S. I.; Khan, I. A.; Wedge, D. E.: Synthesis andbiological activity of substituted urea and thiourea derivativescontaining 1,2,4-triazole moieties. Molecules 18 (2013)3562–3576.5. Artuso, E.; Degani, I.; Fochi, R.; Magistris, C.: Preparationof mono-, di-,and trisubstituted ureas by carbonylation ofaliphatic amines with S,S-dimethyl dithiocarbonate. Synthesis22 (2007) 3497–3506.6. Mizuno, T.; Nakai, T.; Mihara, M.: Synthesis of unsymmetricalureas by sulfur-assisted carbonylation with carbon monoxideand oxidation with molecular oxygen under mild conditions.Synthesis 15 (2009) 2492–2496.7. Thalluri, K.; Manne, S. R.; Dev, D.; Mandal, B.: Ethyl 2-cyano-2-(4-nitrophenylsulfonyloxyimino)acetate-mediated Lossenrearrangement: single-pot racemization-free synthesis ofhydroxamic acids and ureas from carboxylic acids. J. Org.Chem. 79 (2014) 3765–3775.8. Smith, K.; El-Hiti, G. A.; Alshammari, M. B.: Directed lithiationof N′-(2-(4-methoxyphenyl)ethyl)-N,N-dimethylurea and tert-butyl (2-(4-methoxyphenyl)ethyl)carbamate. Synthesis 46(2014) 394–402.9. Smith, K.; El-Hiti, G. A.; Alshammari, M. B.: Control of site oflithiation of 3-(aminomethyl)pyridine derivatives. Synthesis 45(2013) 3426–3434.10. Smith, K.; El-Hiti, G. A.; Alshammari, M. B.: Variation in the siteof lithiation of 2-(2-methylphenyl)ethanamine derivatives. J.Org. Chem. 77 (2012) 11210–11215.11. Smith, K.; El-Hiti, G. A.; Hegazy, A. S.: Lateral lithiationof N′-(2-methylbenzyl)-N,N-dimethylurea and N-(2-methylbenzyl)pivalamide: synthesis of tetrahydroisoquino-lines. Synthesis 8 (2010) 1371–1380.12. Grell, J.; Bernstein, J.; Tinhofer, G.: Investigation of hydrogenbond patterns: a review of mathematical tools for the graph setapproach. Crystallogr. Rev. 8 (2002) 1–56.13. Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr.A64 (2008) 112–122.14. Agilent. CrysAlisPRO. Agilent Technologies, Yarnton, England,2014.15. Farrugia, L. J.: WinGX and ORTEP for Windows: an update. J.Appl. Crystallogr. 45 (2012) 849–854.Brought to you by | Cardiff UniversityAuthenticatedDownload Date | 11/29/16 3:49 PM

Crystal structure of 1,1-dimethyl-3-(2-phenylethyl)urea, C11H16N2O

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Crystal structure of 1,1-dimethyl-3-(2-phenylethyl)urea, C11H16N2O

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