Startseite Crystal structure of 3-(2-(4-chlorophenyl)-3-hydroxy-3,3-diphenylpropyl)-1,1-dimethylurea, C24H25ClN2O2
Artikel Open Access

Crystal structure of 3-(2-(4-chlorophenyl)-3-hydroxy-3,3-diphenylpropyl)-1,1-dimethylurea, C24H25ClN2O2

  • Mohammed B. Alshammari , Keith Smith , Amany S. Hegazy , Benson M. Kariuki und Gamal A. El-Hiti EMAIL logo
Veröffentlicht/Copyright: 15. Oktober 2016

Abstract

C24H25ClN2O2, orthorhombic, P212121 (no. 19), a = 5.9066(2) Å, b = 15.7928(3) Å, c = 21.7829(6) Å, V = 2031.95(10) Å3, Z = 4, Rgt(F) = 0.0319, wRref(F2) = 0.0838, T = 150(2) K.

CCDC no.:: 1506294

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.

Crystal:Colourless plate Size 0.21 × 0.10 × 0.03 mm
Wavelength:Cu Kα radiation (1.54184 Å)
μ:18.4 cm−1
Diffractometer, scan mode:SuperNova, ω-scans
2θmax, completeness:147.6°, >98%
N(hkl)measured, N(hkl)unique, Rint:7255, 3968, 0.020
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3613
N(param)refined:265
Programs:CrysAlisPRO [13], SHELX [14], WinGX [15], CHEMDRAW [16]
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

AtomxyzUiso*/Ueq
C10.5633(4)0.96117(14)1.08808(11)0.0266(5)
H10.72360.98091.09180.032*
C20.5183(5)0.89733(14)1.14050(11)0.0329(5)
H2A0.36100.87651.13630.039*
H2B0.62000.84821.13450.039*
C30.3692(5)0.95721(16)1.23638(12)0.0334(6)
C40.6414(6)0.9787(2)1.32070(13)0.0448(7)
H4A0.71010.92421.31010.067*
H4B0.63200.98401.36550.067*
H4C0.73451.02471.30420.067*
C50.2545(6)1.0375(2)1.32561(14)0.0477(7)
H5A0.31531.09511.32820.072*
H5B0.22711.01571.36710.072*
H5C0.11191.03821.30260.072*
C60.5425(4)0.91177(14)1.02844(11)0.0262(5)
C70.7246(4)0.90766(15)0.98796(12)0.0296(5)
H70.85800.93900.99680.035*
C80.7159(4)0.85859(15)0.93468(12)0.0307(5)
H80.84170.85630.90760.037*
C90.5217(5)0.81369(14)0.92218(10)0.0276(5)
C100.3370(4)0.81533(15)0.96129(11)0.0274(5)
H100.20490.78330.95230.033*
C110.3487(4)0.86494(15)1.01423(11)0.0275(5)
H110.22230.86691.04120.033*
C120.4074(4)1.04095(14)1.08983(11)0.0259(5)
C130.4692(4)1.10383(13)1.14145(11)0.0261(5)
C140.3042(4)1.16086(15)1.16002(12)0.0302(5)
H140.15841.15861.14170.036*
C150.3481(5)1.22138(16)1.20493(12)0.0350(6)
H150.23321.26011.21690.042*
C160.5594(5)1.22496(16)1.23214(12)0.0352(6)
H160.58941.26541.26340.042*
C170.7270(5)1.16927(16)1.21362(12)0.0343(6)
H170.87261.17171.23200.041*
C180.6824(4)1.10974(15)1.16810(12)0.0314(5)
H180.79951.07261.15500.038*
C190.4242(4)1.08905(14)1.02868(11)0.0262(5)
C200.6204(5)1.13290(17)1.01401(12)0.0337(5)
H200.74481.13221.04170.040*
C220.6375(5)1.17801(18)0.95920(14)0.0385(6)
H220.77291.20770.94970.046*
C230.4576(5)1.17962(16)0.91871(12)0.0373(6)
H230.46961.20970.88110.045*
C240.2603(5)1.13720(17)0.93318(13)0.0370(6)
H240.13531.13890.90570.044*
C250.2438(4)1.09192(16)0.98791(12)0.0324(5)
H250.10771.06270.99740.039*
N10.5478(4)0.92760(13)1.20296(10)0.0337(5)
H1A0.68360.92681.21960.040*
N20.4156(4)0.98348(15)1.29458(11)0.0380(5)
O10.1736(3)0.95873(12)1.21521(8)0.0381(4)
O20.1771(3)1.01443(10)1.09648(8)0.0274(4)
H20.16220.98781.12960.041*
Cl10.51034(11)0.75092(4)0.85623(2)0.03654(15)

Source of material

3-(2-(4-Chlorophenyl)-3-hydroxy-3,3-diphenylpropyl)-1,1-dime thylurea was synthesized via double lithiation of 3-(2-(4-chlorophenyl)ethyl)-1,1-dimethylurea with excess tert-butyllithium (3.3 mole equivalents) at −60 °C in anhydrous tetrahydrofuran (THF) under an inert atmosphere. The dilithium reagent produced in-situ was allowed to react with a solution of benzophenone (2.2 mole equivalents) in THF, added via a syringe. The reaction mixture was stirred and allowed to warm up to room temperature over 2 h. Following work-up, the crude product was purified by column chromatography (silica gel) using a mixture of diethyl ether and hexane (1:3 by volume) to give the title compound (87%). Crystallization from a mixture of diethyl ether and ethyl acetate (4:1 by volume) gave colorless crystals, Mp 164–165 °C.

Experimental details

All hydrogen atoms were placed in calculated positions and refined using a riding model. Methyl C—H bonds were fixed at 0.98 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 0.95 Å and N—H set to 0.88 Å with Uiso set to 1.2 times the Ueq for the atoms to which they are bonded.

Discussion

Urea derivatives show various biological activities [1], [2], [3], [4]. They can be synthesized efficiently in high yields using simple procedures [4], [5], [6], [7]. Aromatic substituted ureas can be further easily substituted via lithiation followed by reactions with electrophiles [8], [9], [10], [11], [12].

In the crystal structure, the asymmetric unit comprises one molecule of C24H25ClN2O2. An intramolecular O—H⋯O hydrogen bond is observed in the molecule with an O2⋯O1 distance of 2.732(3) Å and O2—H2⋯O1 angle of 161.7°. Two weak intermolecular C—H⋯Cl interactions occur in the crystal structure (with geometry: C2⋯Cl1 = 3.806(3) Å, C2—H2a⋯Cl1 = 153.9° and C2⋯Cl1 = 3.733(3) Å, C2—H2b⋯Cl1 = 158.4°) leading to the formation of molecular chains along [100]. The structure is racemically twinned.

Award Identifier / Grant number: 2015/01/5162

Funding statement: This project was supported by the Deanship of Scientific Research at Prince Sattam bin Abdulaziz University under the research project 2015/01/5162 and thanks are also due to Cardiff University for continued support.

Acknowledgements

This project was supported by the Deanship of Scientific Research at Prince Sattam bin Abdulaziz University under the research project 2015/01/5162 and thanks are also due to Cardiff University for continued support.

References

1. Kocyigit-Kaymakcioglu, B.; Celen, A. O.; Tabanca, N.; Ali, A.; Khan, S. I.; Khan, I. A.; Wedge, D. E.: Synthesis and biological activity of substituted urea and thiourea derivatives containing 1,2,4-triazole moieties. Molecules 18 (2013) 3562–3576.10.3390/molecules18033562Suche in Google Scholar PubMed PubMed Central

2. Wilson, A. A.; Garcia, A.; Houle, S.; Sadovski, O.; Vasdev, N.: Synthesis and application of isocyanates radiolabeled with carbon-11. Chem. Eur. J. 17 (2011) 259–264.10.1002/chem.201002345Suche in Google Scholar PubMed

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 anaplastic lymphoma kinase inhibitors. Chem. Med. Chem. 6 (2011) 1680–1692.10.1002/cmdc.201100168Suche in Google Scholar PubMed

4. Chen, J.-N.; Wang, X.-F.; Li, T.; Wu, D.-W.; Fu, X.-B.; Zhang, G.-J.; Shen, X.-C.; Wang, H.-S. Design, synthesis, and biological evaluation of novel quinazolinyl-diaryl urea derivatives as potential anticancer agents. Eur. J. Med. Chem. 107 (2016) 12–25.10.1016/j.ejmech.2015.10.045Suche in Google Scholar PubMed

5. Carnaroglio, D.; Martina, K.; Palmisano, G.; Penoni, A.; Domini, C.; Cravotto, G. One-pot sequential synthesis of isocyanates and urea derivatives via a microwave-assisted Staudinger-aza-Wittig reaction. Beilstein J. Org. Chem. 9 (2013) 2378–2386.10.3762/bjoc.9.274Suche in Google Scholar PubMed PubMed Central

6. Vinogradova, E. V.; Fors, B. P.; Buchwald, S. L. Palladium-catalyzed cross-coupling of aryl chlorides and triflates with sodium cyanate: a practical synthesis of unsymmetrical ureas. J. Am. Chem. Soc. 134 (2012) 11132–11135.10.1021/ja305212vSuche in Google Scholar PubMed PubMed Central

7. Wu, C.; Cheng, H.; Liu, R.; Wang, Q.; Hao, Y.; Yu, Y.; Zhao, F. Synthesis of urea derivatives from amines and CO2 in the absence of catalyst and. Solvent. Green Chem. 12 (2010) 1811–1816.10.1039/c0gc00059kSuche in Google Scholar

8. Smith, K.; El-Hiti, G. A.; Alshammari, M. B.: Directed lithiation of N’-(2-(4-methoxyphenyl)ethyl)-N,N-dimethylurea and tert-butyl (2-(4-methoxyphenyl)ethyl)carbamate. Synthesis 46 (2014) 394–402.10.1055/s-0033-1338570Suche in Google Scholar

9. Smith, K.; El-Hiti, G. A.; Alshammari, M. B.: Control of site of lithiation of 3-(aminomethyl)pyridine derivatives. Synthesis 45 (2013) 3426–3434.10.1055/s-0033-1338547Suche in Google Scholar

10. Smith, K.; El-Hiti, G. A.; Alshammari, M. B.: Lithiation and substitution of N′-(ω-phenylalkyl)-N,N-dimethylureas. Synthesis 44 (2012) 20139–2022.10.1055/s-0031-1291008Suche in Google Scholar

11. Smith, K.; El-Hiti, G. A.; Alshammari, M. B.: Variation in the site of lithiation of 2-(2-methylphenyl)ethanamine derivatives. J. Org. Chem. 77 (2012) 11210–11215.10.1021/jo3023445Suche in Google Scholar PubMed

12. Smith, K.; El-Hiti, G. A.; Hegazy, A. S.: Lateral lithiation of N′-(2-methylbenzyl)-N,N-dimethylurea and N-(2-methylbenzyl)pivalamide: Synthesis of tetrahydroisoquinolines. Synthesis 42 (2010) 1371–1380.10.1055/s-0029-1219277Suche in Google Scholar

13. Agilent. CrysAlisPRO. Agilent Technologies, Yarnton, England, (2014).Suche in Google Scholar

14. Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Suche in Google Scholar PubMed

15. Farrugia, L. J.: WinGX and ORTEP for Windows: an update. J. Appl. Crystallogr. 45 (2012) 849–854.10.1107/S0021889812029111Suche in Google Scholar

16. Cambridge Soft. CHEMDRAW Ultra. Cambridge Soft Corporation, Cambridge, Massachusetts, USA, (2001).Suche in Google Scholar

Received: 2016-5-26
Accepted: 2016-9-26
Published Online: 2016-10-15
Published in Print: 2017-1-1

©2016 Mohammed B. Alshammari et al., published by De Gruyter.

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Artikel in diesem Heft

  1. Cover and Frontmatter
  2. Editorial
  3. Twenty years of crystal structure publication and the road ahead
  4. Crystal Structures
  5. Crystal structure of poly-[triaqua-(μ4-5′-carboxy-[1,1′-biphenyl]-2,3,3′-tricarboxylate-κ6O1,O2:O3,O4:O5:O6)praseodymium(III), C16H13O11Pr
  6. Crystal structure of (R)-1-(2,3-dihydro-1H-pyrrolizin-5-yl)-2,3-dihydroxypropan-1-one, C10H13NO3
  7. Crystal structure of (E)-4-nitro-2-((2-phenoxyphenylimino)methyl)phenol, C19H14N2O4
  8. Crystal structure of 3,3′-di(furan-2-yl)-5,5′-bi-1,2,4-triazine
  9. Crystal structure of 11-(p-coumaroyloxy)-tremetone, C22H20O5
  10. The crystal structure of 1,3-bis(2,6-diiso-propylphenyl)imidazol-2-ylidene)-dibromido-(1-methyl-1H-imidazole-κ1N)palladium(II) – ethyl acetate – water (1/1/1), C31H42Br2N4Pd
  11. Crystal structure of 2-((3-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)methylene)-1H-indene-1,3(2H)-dione, C28H19N5O2
  12. Crystal structure of 2-(5-(4-fluorophenyl)-3-p-tolyl-4,5-dihydro-1H-pyrazol-1-yl)-4-(5-methyl-1-p-tolyl-1H-1,2,3-triazol-4-yl)thiazole, C29H25FN6S
  13. Crystal structure of poly-[aqua-(μ7-benzene-1,3,5-tricarboxylato)-(μ3-1,2,4-triazol-1-ido)dicobalt(II)], C11H7Co2N3O7
  14. Crystal constructure of 16(S)-methyl-6α-carboxy-1, 15-dioxo-6, 7-seco-ent-kaur-2-en-7, 20-olide, C20H24O6
  15. Crystal structure of 1-(benzo[d]thiazol-2-yl)-3-phenylthiourea, C14H11N3S2
  16. Crystal structure of 3-(2-bromophenyl)-1,1-dimethylthiourea, C9H11BrN2S
  17. Crystal structure of 1-(adamantan-1-yl)-3-(3-chlorophenyl)thiourea, C17H21ClN2S
  18. Crystal structure of 3-(adamantan-1-yl)-1-(4-bromophenyl)urea, C17H21BrN2O
  19. Crystal structure of (Z)-Ethyl 2-cyano-2-(3-phenylthiazolidin-2-ylidene) acetate, C14H14N2O2S
  20. Crystal structure of methyl 2b-ethyl-1a,2a,2b,2b1,3,5,10,11-octahydro-1H-oxireno[2′,3′:6,7]indolizino[8,1-cd]carbazole-4-carboxylate, C21H24N2O3
  21. Crystal structure of 2-amino-5-oxo-4-(3,4,5-trimethoxy-phenyl)-4,5,6,7-tetrahydro-cyclopenta[b]pyran-3-carbonitrile, C18H18N2O5
  22. Crystal structure of 1,2,3-trimethyl-2,3-dihydro-1H-perimidine, C14H16N2
  23. Crystal structure of bis(2,6-dihydroxymethyl)pyridine-κ3N,O,O′)-bis(μ2-6-chloropyridin-2-olato-κ3N,O:O)-bis(6-chloropyridin-2-olato-κO)-bis(nitrato-κ2O,O′)digadolinium(III), C34H30Cl4Gd2N8O14
  24. Crystal structure of 8-isopropyl-8-aza-bicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate, C19H27NO3
  25. Crystal structure of 1-methyl-3-[((naphthalen-2-ylsulfonyl)oxy)imino]indolin-2-one, C19H14N2O4S
  26. Crystal structure (7,8-bis(diisopropylphosphino)-7,8-dicarba-nido-undecaborane-κ2P,P′)-(benzoato-κ2O,O′)nickel(II), C21H42B9NiO2P2
  27. Crystal structure of methyl-2-methyl-4-(2-oxo-2-phenylethyl)-5-phenyl-1H-pyrrole-3-carboxylate, C21H19NO3
  28. Crystal structure of 2-[(2-oxo-thiazolidine-3-carbonyl)sulfamoyl]-methy-benzoic acid methyl ester, C13H14N2O6S2
  29. Crystal structure of N′-(2-phenylacetyl)thiophene-2-carbohydrazide monohydrate, C13H14N2O3S
  30. Crystal structure of 1,1′-(hexane-1,6-diyl)bis(3-methyl-1H-imidazol-3-ium) bis(hexafluoro phosphate), C14H24F12N4P2
  31. Crystal structure of di-μ-chlorido-bis[1,2-bis(dicyclohexylphosphino)-1,2-dicarba-closo-dodecaborane-κ2P,P′]zinc(II), C52H108B20Cl2P4Zn2
  32. Crystal structure of dibromido-bis[μ-1-[(2-methyl-1H-benzoimidazol-1-yl)methyl]-1H-benzotriazole-κN]mercury(II), C30H26Br2HgN10
  33. Crystal structure of bis(μ-nitrato-κ2O:O)-bis[1,2-bis(diphenylphosphino)-1,2-dicarba-closo-dodecaborane-κ2P,P′]disilver(I) dicloromethane monosolvate, C54H64B20Cl4O6P4Ag2
  34. Crystal structure of dinuclear dichloridobis(dimethylformamide-kO)bis[μ2-3-(2-oxyphenyl)-5-(pyrazin-2-yl)-1,2,4-triazol-1ido-κ4-O,N:N′,N′′(2)]diiron(III) dimethylformamide (1/1), C36H42Cl2Fe2N14O6
  35. Crystal structure of diaqua-dinitrato-κO-bis(4-(1H-pyrazol-3-yl)pyridine-κN)manganese(II), C16H18MnN8O8
  36. Crystal structure of (Z)-6-methoxy-2-(2,2,2-trifluoro-1-hydroxyethylidene)-2,3-dihydro-1H-inden-1-one, C12H6F6O3
  37. Crystal Structure of 4-(2-chloroacetamido)pyridinium chloride monohydrate, C7H10Cl2N2O2
  38. Crystal structure of 2-amino-4-(4-chloro-phenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, C16H13ClN2O2
  39. Crystal structure of (E)-1-(2-(thiophen-2-ylmethylene)hydrazinyl)phthalazine hydrochloride–ethanol (1/1), C15H17ClN4OS
  40. Crystal structure of N,N-diethyl-5-bromo-3,4-dihydro-2,4-dioxopyrimidine-1(2H)-carboxamide, C9H12BrN3O3
  41. Crystal structure of 3-(2-(4-chlorophenyl)-3-hydroxy-3,3-diphenylpropyl)-1,1-dimethylurea, C24H25ClN2O2
  42. Crystal structure of 3-(4-chlorophenyl)-1,1-dimethylthiourea, C9H11ClN2S
  43. Crystal structure of 2-amino-4-(4-bromo-phenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carbonitrile, C16H11BrN2O3
  44. Crystal structure of 4-(3,4-dimethyl-phenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester, C21H25NO3
  45. Crystal structure of (E)-2-({4-hydroxy-5-methoxy-3-[(4-methyl-1-piperazinyl)methyl]phenyl} methylidene)-1-indanone, C23H26N2O3
  46. Crystal structure of tripropylammonium 2′-carboxy-[1,1′-biphenyl]-2-carboxylate – [1,1′-biphenyl]-2,2′-dicarboxylic acid (2/1), C60H72N2O12
  47. Crystal structure of catena-poly-{aqua-[μ2-1,2-bis((1H-imidazol-1-yl)methyl)benzene-κ2N:N′]-[μ2-4,4′-(dimethylsilanediyl)dibenzato-κ3O,O′:O′]nickel(II)}, C30H30N4NiO5Si
  48. The crystal structure of 1-(4-bromophenyl)-2-(4-(4-fluorophenyl)piperazin-1-yl)ethanol, C18H20BrFN2O1
  49. Crystal structure of trimethylammonium 4-((4-carboxyphenyl)sulfonyl)benzoate, C17H19NO6S
  50. Crystal structure of syn-2,4-di-o-tolylpentane-2,4-diol, C19H24O2
  51. Crystal structure of 2-[3,5-bis(trifluoromethyl)benzylsulfanyl]-5-(5-bromothiophen-2-yl)-1,3,4-oxadiazole, C15H7BrF6N2OS2
  52. Crystal structure of (E)-3-((naphthalen-1-ylimino)methyl)-4-nitrophenol, C17H12N2O3
  53. Crystal structure of 2-dichloromethyl-2-p-nitrophenyl-1,3-dioxolane, C10H9Cl2NO4
  54. Crystal structure of (1,4,8,11-tetraazacyclotetradecane)palladium(II) tetracyanopalladate(II), C14H24N8Pd2
  55. Crystal structure of 2-(4-oxo-2-thioxothiazolidin-3-yl)acetic acid monohydrate, C5H7NO4S2
  56. Crystal structure of a P4-bridged (η5-pentamethyl-cyclopentadienyl)(η5-adamantylcyclopentadienyl) titanium(III)complex, C50H66P4Ti2
  57. Crystal structure of cis-bis(2,2′-bipyrimidine-κ2N,N′)bis(thiocyanato-κN)nickel(II), C18H12N10NiS2
  58. Crystal structure of cis-bis(2,2′-bipyridine-κ2N,N′)dibromidomanganese(II), C20H16Br2MnN4
  59. Crystal structure of cis-bis(2,2′-bipyridine-κ2N,N′)bis(thiocyanato-κN)nickel(II), C22H16N6NiS2
  60. Crystal structure of trans-dibromido(1,4,8,11-tetraazacyclotetradecane)nickel(II), C10H24Br2N4Ni
  61. Crystal structure of cis-tetrabromidobis(pyridine-κN)platinum(IV), C10H10Br4N2Pt
  62. Crystal structure of (E)-5-((4-chlorophenyl)diazenyl)-2-(5-(4-fluorophenyl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)-4-methylthiazole, C23H17ClFN5S2
  63. The crystal structure of 3-((1R,2S)-1-methylpyrrolidin-1-ium-2-yl)pyridin-1-ium tetrachloridocobaltate(II) monohydrate, C10H18Cl4CoN2O
Heruntergeladen am 19.11.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2016-0170/html
Button zum nach oben scrollen