Startseite Crystal structure of 1,2,3-trimethyl-2,3-dihydro-1H-perimidine, C14H16N2
Artikel Open Access

Crystal structure of 1,2,3-trimethyl-2,3-dihydro-1H-perimidine, C14H16N2

  • Zhong-Yan Li , Xian-You Yuan , Lin Yuan EMAIL logo und Min Zhang EMAIL logo
Veröffentlicht/Copyright: 24. Oktober 2016

Abstract

C14H16N2, monoclinic, C2/c (no. 15), a = 32.300(3) Å, b = 7.2653(6) Å, c = 10.4316(10) Å, β = 102.133(5)°, V =2393.3(4) Å3, Z = 8, Rgt(F) = 0.0464, wRref(F2) = 0.1411, T = 296(2) K.

CCDC no.:: 1471471

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 blocks
Size:0.41 × 0.38 × 0.29 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.7 cm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
2θmax, completeness:50°, >99%
N(hkl)measured, N(hkl)unique, Rint:7687, 2111, 0.015
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1593
N(param)refined:148
Programs:SHELX [10, 11], Bruker programs [12]
Table 2:

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

AtomxyzUiso*/Ueq
N10.09162(4)0.09647(16)0.68751(12)0.0530(4)
N20.16555(4)0.10822(17)0.70616(12)0.0566(4)
C10.12033(4)0.28185(17)0.53648(12)0.0431(4)
C50.07324(6)0.4657(2)0.37256(16)0.0701(5)
H50.06890.54750.30240.084*
C60.11503(5)0.40982(19)0.43173(14)0.0547(4)
C20.08428(4)0.21484(18)0.58082(13)0.0458(4)
C130.12998(5)−0.0142(2)0.70547(15)0.0557(4)
H130.1341−0.07100.79250.067*
C140.12678(6)−0.1691(2)0.60560(18)0.0780(6)
H14A0.1523−0.24090.62400.117*
H14B0.1230−0.11780.51910.117*
H14C0.1030−0.24620.61070.117*
C100.16197(4)0.22733(18)0.60095(14)0.0486(4)
C110.20685(6)0.0385(3)0.7683(2)0.0974(7)
H11A0.22530.13970.79990.146*
H11B0.2184−0.03090.70580.146*
H11C0.2042−0.03950.84050.146*
C120.05608(6)0.0140(3)0.73012(19)0.0796(6)
H12A0.0402−0.06000.66060.119*
H12B0.03820.10910.75250.119*
H12C0.0662−0.06190.80550.119*
C30.04454(5)0.2754(2)0.52104(16)0.0614(4)
H30.02090.23280.54970.074*
C40.03967(6)0.4008(2)0.41734(17)0.0721(5)
H40.01260.44080.37810.086*
C90.19636(5)0.3015(2)0.55970(18)0.0673(5)
H90.22360.26700.60090.081*
C80.19039(7)0.4281(3)0.4563(2)0.0787(6)
H80.21390.47730.43030.094*
C70.15122(7)0.4804(2)0.39331(18)0.0720(5)
H70.14810.56350.32410.086*

Source of material

Iodomethane (3.02 g, 0.021 mol) was added in one portion to a solution of 1,2-dimethyl-1H-perimidine (1.96 g, 0.01 mol) in dimethylformamide (15 mL) at 373 K. The mixture was heated for 6 h, giving a yellow precipitate. After cooling, the yellow solid was filtered and dried under vacuum to give 1,2,3-trimethyl-1H-perimidin-3-ium iodide (2.37 g, 70%), which was used in the next reaction without purification. Sodium borohydride (0.57 g, 0.015 mol) was added batch-wise to a solution of 1,2,3-trimethyl-1H-perimidin-3-ium iodide (3.38 g, 0.01 mol) in methanol (25 mL) under nitrogen atmosphere. The mixture was stirred at room temperature for 30 min, giving a white precipitate. After the completion of the reaction, the white solid was filtered, washed with water and dried under vacuum to yield the desired product (1.38 g, 65%). Colorless prisms of the product were obtained upon recrystallization from anhydrous ethanol.

Experimental details

All hydrogen atoms were identified in difference Fourier synthesis. The methyl groups were idealized and refined using rigid groups allowed to rotate about the N—C bond and C—C bond (AFIX 137 option of the SHELXL program [11]). The Uiso values of the hydrogen atoms of methyl groups were set to 1.5Ueq(C) and the Uiso values of all other hydrogen atons were set to 1.2Ueq(C).

Discussion

Multi-nuclear N-heterocyclic compounds like perimidines have drawn extensive examinations of many researchers for a long time, because they exhibit a diverse range of biological activities [1; 2; 3]. Perimidines also can be used as dyes and have a wide application in industrial field, and the famous product was reported as solvent black 3 [4]. There are several preparative methods for the synthesis of perimidine derivatives [5; 6; 7; 8; 9]. A new 1,2-dimethyl-1H-perimidine was synthesized and characterized by single-crystal X-ray diffraction.

All bond lengths and angles are in the expected ranges. The whole molecule shows almost mirror symmetry.

Award Identifier / Grant number: 2016

Funding statement: This work was financially supported by the Science and Technology Planning Project of Hunan Province (2015GK3037), the Scientific Research Fund of Hunan Provincial Education Department (14A058), the Construct Program of the Key Discipline in Hunan Province (2016).

Acknowledgements

This work was financially supported by the Science and Technology Planning Project of Hunan Province (2015GK3037), the Scientific Research Fund of Hunan Provincial Education Department (14A058), the Construct Program of the Key Discipline in Hunan Province (2016).

References

1 Bu, X.; Deady, L. W.; Finlay, G. J.; Baguley, B. C.; Denny, W. A.: Synthesis and cytotoxic activity of 7-Oxo-7H-dibenz[f,ij]isoquinoline and 7-oxo-7H-benzo[e]perimidine derivatives. J. Med. Chem. 44 (2001) 2004–2014.10.1021/jm010041lSuche in Google Scholar

2 Ye, J.; Sun, X. X.; Qiu, S. Y.; Hu, A. X.: Synthesis, crystal structure and fungicidal activity of N-(4-tert-buty)-5-(1,2,4-triazol-1-yl)thiazol-2-yl) propionamide. Chin. J. Struct. Chem. 3 (2014) 429–433.Suche in Google Scholar

3 Fu, C. R.; Pei, J.; Ning, Y.; Liu, M.; Shan, P. C.; Liu, J.; Li, Y. Q.; Hu, F. Z.; Zhu, Y. Q.; Yang, H. Z.; Zou, X. M.: Synthesis and insecticidal activities of novel pyrazole oxime ether derivatives with different substituted pyridyl rings. Pest Manag. Sci. 70 (2013) 1207–1214.10.1002/ps.3672Suche in Google Scholar

4 Hashim, J. A.; Kezhal, M. S.: Synthesis, characterization and biological activity of 2-Aryl-2,3-dihydro-1H-perimidine. Res. Pharm. Biotech. 5 (2014) 1–6.Suche in Google Scholar

5 Vanden, E. J. J.; Delfosse, F.; Mayence, A.; Haverbeke, Y. V.: Old reagents, new results-aromatization of Hantzsch 1,4-dihydropyridines with manganese-dioxide and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. Tetrahedron 51 (1995) 5813–5818.10.1016/0040-4020(95)00318-3Suche in Google Scholar

6 Hendrickson, J. B.; Hussoin, M. S.: Seeking the ideal dehydrating reagent. J. Org. Chem. 52 (1987) 4137–4139.10.1021/jo00227a041Suche in Google Scholar

7 Deady, L. W.; Rodemann, T. J.: Synthesis of perimidine and fused perimidine derivatives from reaction of 1,8-naphthalenediamine with an iminoisocoumarin. Heterocycl. Chem. 35 (1998) 1417–1419.10.1002/jhet.5570350633Suche in Google Scholar

8 Mueller-Westerhoff, U. T.; Vance, B.; Dong. I. Y.: The synthesis of dithiolene dyes with strong near-IR absorption. Tetrahedron 47 (1991) 909–932.10.1016/S0040-4020(01)80932-7Suche in Google Scholar

9 Starshikov, M.; Pozharskii, F. T.: Synthesis of 2-(5-halogeno-2-furyl)-2,3-dihydroperimidines. Chem. Heterocycl. Compd. 9 (1973) 922–924.10.1007/BF00471584Suche in Google Scholar

10 Sheldrick, G. M.: SHELXS-97: Program for the Solution of Crystal Structures. University of Göttingen, Germany, 1997.Suche in Google Scholar

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

12 Bruker. APEX2, SAINT and SADABS. Brucker AXS Inc., Madison, WI, USA, 2013.Suche in Google Scholar

Received: 2016-4-24
Accepted: 2016-10-7
Published Online: 2016-10-24
Published in Print: 2017-1-1

©2016 Zhong-Yan Li 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
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  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
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  45. Crystal structure of (E)-2-({4-hydroxy-5-methoxy-3-[(4-methyl-1-piperazinyl)methyl]phenyl} methylidene)-1-indanone, C23H26N2O3
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  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
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  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
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