Startseite Crystal structure of 2,3-diphenyl-1-[(dipropylamino)acetyl]-1,3-diazaspiro[4.5]decan-4-one, C28H37N3O2
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Crystal structure of 2,3-diphenyl-1-[(dipropylamino)acetyl]-1,3-diazaspiro[4.5]decan-4-one, C28H37N3O2

  • Rasha M. Hassan , Hazem A. Ghabbour ORCID logo , Mohamed N. Aboul-Enein EMAIL logo , Aida A. El-Azzouny , Ola A. Saleh und Mohamed I. Attia
Veröffentlicht/Copyright: 28. März 2017

Abstract

C28H37N3O2, monoclinic, P21/c (no. 14), a = 11.0454(4) Å, b = 21.9125(8) Å, c = 11.6544(4) Å, β = 111.783(1)°, V = 2619.33(16) Å3, Z = 4, Rgt(F) = 0.0658, wRref(F2) = 0.1940, T = 293(2) K.

CCDC no.:: 1507268

Table 1

Data collection and handling.

Crystal:Colourless block
Size:0.42 × 0.27 × 0.11 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:80.7 cm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
2θmax, completeness:53°, >99%
N(hkl)measured, N(hkl)unique, Rint:38550, 5420, 0.065
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3079
N(param)refined:301
Programs:Bruker programs [1], SHELX [2, 3]

The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 2

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

AtomxyzUiso*/Ueq
O10.48261(18)0.25128(10)1.11038(18)0.0807(7)
O20.2053(2)0.40213(10)0.76116(19)0.0809(7)
N10.55635(19)0.28601(9)0.96390(17)0.0487(5)
N20.39265(19)0.35021(9)0.85567(16)0.0481(5)
N30.2873(2)0.45341(11)0.5799(2)0.0713(7)
C10.5210(2)0.32920(11)0.8608(2)0.0466(6)
H1A0.51160.30750.78440.056*
C20.4692(2)0.28220(12)1.0196(2)0.0536(6)
C30.3515(2)0.32153(11)0.9513(2)0.0486(6)
C40.3271(3)0.36928(13)1.0353(3)0.0674(8)
H4A0.40910.38901.08280.081*
H4B0.26900.40020.98440.081*
C50.2679(4)0.34356(17)1.1240(3)0.0877(10)
H5A0.33080.31711.18350.105*
H5B0.24760.37681.16890.105*
C60.1454(3)0.30788(19)1.0555(4)0.0949(11)
H6A0.11010.29151.11390.114*
H6B0.08050.33470.99910.114*
C70.1750(3)0.25661(16)0.9844(3)0.0809(10)
H7A0.09560.23410.94060.097*
H7B0.23640.22881.04160.097*
C80.2322(3)0.27994(13)0.8920(3)0.0652(7)
H8A0.16550.30240.82730.078*
H8B0.25740.24530.85390.078*
C90.6238(2)0.37832(11)0.8857(2)0.0529(6)
C100.6433(3)0.42103(13)0.9776(3)0.0700(8)
H10A0.59150.42001.02470.084*
C110.7373(4)0.46486(15)1.0009(4)0.0942(11)
H11A0.74920.49331.06330.113*
C120.8135(4)0.4666(2)0.9320(5)0.1121(15)
H12A0.87660.49680.94670.135*
C130.7978(4)0.4238(2)0.8404(5)0.1080(13)
H13A0.85120.42470.79470.130*
C140.7016(3)0.37936(15)0.8171(3)0.0782(9)
H14A0.69000.35050.75530.094*
C150.6764(2)0.25289(11)1.0025(2)0.0518(6)
C160.7058(3)0.21710(14)0.9209(3)0.0783(9)
H16A0.64890.21490.83890.094*
C170.8209(3)0.18395(16)0.9605(4)0.0948(11)
H17A0.84100.15960.90470.114*
C180.9048(3)0.18674(18)1.0805(4)0.0905(11)
H18A0.98180.16431.10700.109*
C190.8748(3)0.2225(2)1.1603(3)0.1077(14)
H19A0.93120.22421.24250.129*
C200.7620(3)0.25640(19)1.1218(3)0.0877(11)
H20A0.74410.28181.17740.105*
C210.3129(3)0.38735(12)0.7644(2)0.0588(7)
C220.3644(3)0.40860(13)0.6659(2)0.0676(8)
H22A0.45120.42520.70750.081*
H22B0.37270.37320.61950.081*
C230.1641(4)0.4297(2)0.4917(3)0.1065(13)
H23A0.16480.38560.49950.128*
H23B0.09380.44510.51450.128*
C240.1358(5)0.4445(3)0.3646(4)0.168(2)
H24A0.21120.43380.34520.202*
H24B0.12490.48840.35540.202*
C250.0205(5)0.4155(3)0.2724(4)0.161(2)
H25A0.01250.42820.19110.241*
H25B−0.05620.42740.28710.241*
H25C0.02990.37190.27890.241*
C260.2777(5)0.51213(17)0.6310(4)0.1036(13)
H26A0.25070.50620.70050.124*
H26B0.21010.53550.56900.124*
C270.4016(7)0.5488(3)0.6737(6)0.180(3)
H27A0.38830.58570.71340.216*
H27B0.46970.52530.73490.216*
C280.4457(9)0.5656(4)0.5737(12)0.283(6)
H28A0.49150.60380.59320.424*
H28B0.37160.56960.49790.424*
H28C0.50280.53450.56470.424*

Source of material

n-Dipropylamine (2.3 g, 0.023 mol) was added to a solution of 1-(chloroacetyl)-2,3-diphenyl-1,3-diazaspiro[4.5]decan-4-one (1.8 g, 0.0047 mol) in toluene (40 mL) and the reaction mixture was heated at 90 °C for 20 h. After cooling to room temperature the solvent was removed under reduced pressure to give a residual oil which was dissolved in dichloromethane (100 mL). The organic phase was washed with water, dried (Na2SO4) and evaporated under vacuum to yield the title compound as a viscous oil. The crude oil was purified by column chromatography using silica gel as a stationary phase and a mixture of petroleum ether (40–60 °C): ethyl acetate (7:3) as a mobile phase to give the title compound as a white solid; m.p. 411–413 K in 65% yield [4]. The title compound was re-crystallized from ethyl acetate to afford colorless single crystals.

Experimental details

Carbon-bound hydrogen atoms were placed in calculated positions and were included in the refinement using the riding model approximation, with Uiso(H) set to 1.2Ueq(C) and 1.5Ueq(Methyl).

Discussion

Epilepsy is a chronic disorder of the brain that affects approximately 50 million people, making it one of the most common neurological diseases worldwide [5]. Many new antiepileptic drugs have been introduced in the market, however the available antiepileptics fail to prevent the seizures in approximately 30% of patients [6]. Moreover, these medications are associated with severe adverse effects such as gingival hyperplasia, megaloblastic anaemia and hepatotoxicity [7, 8] . Therefore, there is a great need for the development of new, more effective and less toxic antiepileptic agents. The title compound displayed 83% protection toward subcutaneous pentylenetetrazole -induced convulsions in mice at dose level 0.035 mmol/kg [3].

In the crystal structure of the title compound, the asymmetric unit contains one independent molecule. Molecules form extended chains along the crystallographic c direction via one non-classical intermolecular hydrogen bond, C1—H1A ⋯O1i, symmetry code: (i) x, − y + 1/2, z-1/2, with a D ⋯A distance of 3.300 Å and a D—H ⋯A angle of 175°.

Acknowledgement

The authors would like to extend their sincere appreciation to the Deanship of Scientific Research at King Saud University for its funding of this research through the Research Group Project No. RGP-196.

References

1 Brucker. APEX2, SAINT and SADABS. Brucker AXS Inc., Madison, Wisconsin, USA, (2009).Suche in Google Scholar

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

3 Sheldrick, G. M.: Crystal structure refinement with SHELXL. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053229614024218Suche in Google Scholar

4 Aboul-Enein, M. N.; El-Azzouny, A. A.; Saleh, O. A.; Amin, K. M.; Maklad, Y. A.; Hassan, R. M.: Synthesis and anticonvulsant activity of aubstituted-1,3-diazaspiro[4.5]decan-4-ones. Arch. Pharm. Chem. Life Sci. 348 (2015) 575–588.10.1002/ardp.201500092Suche in Google Scholar

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7 Lin, Z.; Kadaba, P. K.: Molecular targets for the rational design of antiepileptic drugs and related neuroprotective agents. Med. Res. Rev. 17 (1997) 537–572.10.1002/(SICI)1098-1128(199711)17:6<537::AID-MED3>3.0.CO;2-2Suche in Google Scholar

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Received: 2016-10-5
Accepted: 2017-3-5
Published Online: 2017-3-28
Published in Print: 2017-5-24

©2017 Rasha M. Hassan et al., published by De Gruyter, Berlin/Boston

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

Artikel in diesem Heft

  1. Cover and Frontmatter
  2. Crystal structure of 2,5-diiodo-4-nitro-1H-imidazole hemihydrate, C6H4I4N6O5
  3. Crystal structure of catena-poly[μ2-2,2′-(1,3-phenylene)diacetato-κ4O,O′:O′′,O′′′)-(μ2-1,6-bis(2-methyl-1H-benzo[d]imidazol-1-yl)hexane-κ2N:N′)cadmium(II)], C32H34CdN4O4
  4. Crystal structure of poly[aqua-(2,2′-bipyridine-κN,N′)-(μ4-5,5′-(hexane-1,6-diyl)-bis(oxy)diisophthalato κ8O1,O2:O3,O4:O5,O6:O7,O8)manganese(II)], C21H21MnN2O7
  5. Crystal structure of poly-[(μ2-((1,3-bis(benzimidazol-1-yl)propane-κ2N:N′)(μ2-4-tert-butyl-phthalato-κ2O:O′)cobalt(II)] monohydrate, C29H30CoN4O5
  6. Crystal structure of 2-amino-4-(3,4,5-trimethoxy-phenyl)-5-(oxo-5,6,7,8-tetrahydro-4H-chromene)-3-carbonitrile – ethanol (1/1), C21H26N2O6
  7. Crystal structure of ethyl 1-benzyl-5-phenyl-1H-pyrazole-3-carboxylate, C19H18N2O2
  8. Crystal structure of 2-(1-benzyl-3-phenyl-1H-pyrazol-5-yl)-5-(4-nitrobenzylthio)-1,3,4-oxadiazole, C25H19N5O3S
  9. Structure and photochromism of 1,2-bis[2-methyl-5-(2-chlorophenyl)-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C27H16Cl2F6S2
  10. The crystal structure of the Schiff base (E)-2,6-diisopropyl-N-(pyridin-4-ylmethylene)aniline, C18H22N2
  11. Crystal structure of (E)-2,4-dibromo-6-(((4-methyl-2-nitrophenyl)imino) methyl)phenol, C10H14Br2N2O3
  12. Crystal structure of (bis(2,2′-bipyridine-κ2N,N′))-(3,5-dinitrosalicylato-κ2O,O′)nickel(II), C27H18N6NiO7
  13. Crystal structure of 1-(diethoxy phosphonomethyl) 2-benzoyl-3-chloro-2-cyclohexen-1-ol, C18H24ClO5P
  14. Crystal structure of tetraaqua-bis(1,3-benzimidazol-3-ium-1,3-diacetato-κO)copper(II) hemihydrate, C22H27CuN4O12.50
  15. Crystal structure of 1α,11-dihydroxyeremophil-9-en-8-one, C15H24O3
  16. Crystal structure of 1-ferrocenylsulfonyl-1H-imidazo[4,5-b]pyridine, C16H13FeN3O2S
  17. Crystal structure of bis(μ2-azido-κ2N:N)-dichlorido-bis(μ2-2-(pyridin-2-yl)ethan-1-ol-κ2O,N)dicopper(II), C14H18Cl2Cu2N8O2
  18. Crystal structure of (5,15-cis-bis(2-hydroxy-1-naphthyl)-10-phenyl-20-(4-hydroxyphenyl)-porphyrinato)-(pyridine)-zinc(ii) pyridine solvate, C67H47N7O3Zn
  19. Crystal structure of (μ2-[2,2′-bis(diphenylphosphino)-1,1′-binaphthalene oxide-κ2O,P])-iodido copper(I), C44H32CuIOP2
  20. Crystal structure of 6,8-diphenyl-2-(4-fluorophenyl)-2,3-dihydroquinolin-4(3H)-one, C27H20FNO
  21. Crystal structure of 5,11,17,23-tetra(tert-butyl)-25,26,27,28-tetrahexoxycalix[4]arene, C68H104O4
  22. Crystal structure of N,N′–bis(pyridin-4-ylmethyl)pyrazine-2,3-dicarboxamide dihydrate, C18H20N6O4
  23. Crystal structure of a diaqua-bis(3,5-di(1H-imidazol-1-yl)pyridine-κN)-bis(2-(4-carboxy-phenyl)acetato-κO]manganese(II), C40H36MnN10O10
  24. Crystal structure of 4-(4-hydroxy-3-methoxy-phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid methyl ester, C21H25NO5
  25. Crystal structure of (E)-4,4′-(ethene-1,2-diyl)bis(3-nitrobenzoic acid) 1.5 hydrate, C16H13N2O9.5
  26. Crystal structure of (E)-2-(5-(4-fluorophenyl)-3-(furan-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)-5-((4-fluorophenyl)diazenyl)-4-methylthiazole, C23H17F2N5OS
  27. Crystal structure of the co-crystalline adduct 4-((4,4-dimethyl-2,6-dioxocyclohexylidene)methylamino)-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide - acetic acid (1/1), C21H24N4O4S ⋅ C2H4O2
  28. Synthesis and crystal structure of 2-((5-chlorobenzo[c][1,2,5]thiadiazol-4-yl)amino)-4,5-dihydro-1H-imidazol-3-ium tetraphenylborate, C33H29BClN5S
  29. Crystal structure of (4-chlorophenyl)(3-ferrocenyl-5-(trifluoromethyl)-1H-pyrazol-1-yl)methanone, C21H14ClF3FeN2O
  30. Crystal structure of (S)-benzyl 3-(benzylcarba-moyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate, C25H24N2O3
  31. Crystal structure of 5-acetyl-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one, C15H17FN2O4
  32. Crystal structure of 2-(4-fluorophenyl)-1,3-dimethyl-1H-perimidin-3-ium iodide, C19H16FIN2
  33. Crystal structure of methyl 1H-indole-2-carboxylate, C10H9NO2
  34. Crystal structure of 2,3-diphenyl-1-[(dipropylamino)acetyl]-1,3-diazaspiro[4.5]decan-4-one, C28H37N3O2
  35. Crystal structure of 1-(2H-1,3-benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propan-1-one, C13H12N2O3
  36. Crystal structure of 2,9-dibromo-1,10-phenanthroline, C12H6Br2N2
  37. Crystal structure of 3-(adamantan-1-yl)-4-(4-fluorophenyl)-1H-1,2,4-triazole-5(4H)-thione, C18H20FN3S
  38. Crystal structure of trans-bis((E)-7-oxo-4-(phenyldiazenyl)cyclohepta-1,3,5-trien-1-olato)-κ2O,O′)-bis(pyridine-κN)cobalt(II), C36H28CoN6O4
  39. Crystal structure of 2-(4-methyl-3-phenylthiazol-2(3H)-ylidene)malononitrile, C13H9N3S
  40. Crystal structure of (Z)-3-(adamantan-1-yl)-1-(3-chlorophenyl)-S-benzylisothiourea, C24H27ClN2S
  41. Crystal structure of chlorido{[3-(η5-cyclopenta-dienyl)-2,2,3-trimethyl-1-phenylbutylidene] azanido-κN}[η2(N,O)-N,N-dimethylhydroxylaminato]titanium(IV), C20H27ClN2OTi
  42. Crystal Structure of 1,1′-dimethyl-[4,4′-bipyridine]-1,1′-diium tetrachloridozincate(II), C12H14Cl4N2Zn
  43. Crystal structure of 5-nitro-2-(pyrrolidin-1-yl)benzaldehyde, C11H12N2O3
  44. Crystal structure of 2,3-diphenyl-1-(morpholin-4-ylacetyl)-1,3-diazaspiro[4.5]decan-4-one, C26H31N3O3
  45. Crystal structure of 3,3-dimethyl-3,4-dihydro-1H-benzo[c]chromene-1,6(2H)-dione, C15H14O3
  46. Crystal structure of bis(2-(2-hydroxymethyl)pyridine-κ2N,O)-bis(pivalato-κO)nickel(II), C22H32N2NiO6
  47. Crystal structure of (1,10-phenanthroline-κ2N,N′)-bis(1H-pyrazole-3-carboxylato-κ2N,O)manganese(II) trihydrate, C20H20N6O7Mn
  48. The crystal structure of 3-aminopropan-1-aminium iodide, C3H11N2I
  49. Crystal structure of ethyl 1-(4-chlorophenyl)-5-methyl-1H-1,2,3-triazole-4 carboxylate, C12H12ClN3O2
  50. Crystal structure of 4,4′-((1Z,1′Z)-2,2′-(2,5-diethoxy-1,4-phenylene)bis(ethene-2,1-diyl))dipyridine, C24H24N2O2
  51. Crystal structure of (16S)-12,16-epoxy-11,14-dihydroxy-17(15/16)-abeo-3a,18-cyclo-8,11,13-abietatrien-7-one, C20H24O4
  52. Crystal structure of aquadichlorido(2,4,6-tri-2-pyridyl-1,3,5-triazine-κ3N,N′,N′′)nickel(II) monohydrate, C18H16Cl2N6NiO2
  53. Crystal structure of catena-poly[dichlorido-(μ-ethane-1,2-diyl-bis-(pyridyl-4-carboxylate-κN:N′)mercury(II)], C15H14Cl2HgN2O4
  54. Crystal structure of methyl 2-acetamido-5-chlorbenzoate, C10H10ClNO3
  55. Crystal structure of tetrakis(μ2-3,3-dimethylacrylato-κ2O,O′)-bis(2-aminopyrimidine-κN) dicopper(II), C28H38Cu2N6O8
  56. Crystal structure of 3-amino-8-methoxy-1-phenyl-1H-benzo[f]chromene-2-carbonitrile, C21H16N2O2
  57. Crystal structure of 4-(2-ammonioethyl)morpholin-4-ium dichloride monohydrate, C6H18Cl2N2O2
  58. Crystal structure of 1-(3-((5-bromo-2-hydroxybenzylidene)amino)phenyl)ethanone O-benzyl oxime, C22H19BrN2O2
  59. Crystal structure of 2-(4-(dimethylamino)-2-fluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol monohydrate, C15H20FN7O2
  60. Crystal structure of 4-bromo-2-(1H-pyrazol-3-yl)phenol, C9H7BrN2O
  61. Crystal structure of 1,2,3,4,5-pentamethyl-1,3-cyclopentadiene, C10H16
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