Startseite Crystal structure of (E)-3-(pyren-1-yl)-1-(pyridin-4-yl)prop-2-en-1-one, C24H15NO
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Crystal structure of (E)-3-(pyren-1-yl)-1-(pyridin-4-yl)prop-2-en-1-one, C24H15NO

  • Qiu-Ying Huang , Hong-Ying Wang , Su-Juan Ren und Xiang-Ru Meng EMAIL logo
Veröffentlicht/Copyright: 2. November 2017

Abstract

C24H15NO, monoclinic, P21/n (no. 14), a = 10.3161(3) Å, b = 5.53330(10) Å, c = 29.2019(7) Å, β = 97.341(1)°, V = 1653.24(7) Å3, Z = 4, Rgt(F) = 0.0423, wRref(F2) = 0.1344, T = 294(2) K.

CCDC no.:: 1579090

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 1

Data collection and handling.

Crystal:red block
Size:0.23 × 0.21 × 0.13 mm
Wavelength:Cu Kα radiation (1.54178 Å)
μ:0.64 mm−1
Diffractometer, scan mode:Bruker SMART, φ and ω-scans
2θmax, completeness:68.4°, >99%
N(hkl)measured, N(hkl)unique, Rint:18178, 3026, 0.025
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2697
N(param)refined:235
Programs:Bruker programs [1], SHELX [2]
Table 2

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

AtomxyzUiso*/Ueq
C11.13266(18)0.4802(3)0.69654(5)0.0734(5)
H1A1.18430.61830.70000.088*
C21.05016(17)0.4520(3)0.65563(5)0.0662(4)
H2A1.04710.56920.63270.079*
C30.97281(11)0.2493(2)0.64914(4)0.0432(3)
C40.98248(14)0.0860(3)0.68488(5)0.0595(4)
H4A0.9320−0.05380.68240.071*
C51.06724(16)0.1301(3)0.72436(5)0.0684(4)
H5A1.07190.01660.74800.082*
C60.88559(12)0.1946(2)0.60518(4)0.0469(3)
C70.85779(12)0.3846(2)0.57063(4)0.0488(3)
H7A0.89270.53780.57690.059*
C80.78414(11)0.3453(2)0.53054(4)0.0456(3)
H8A0.74350.19550.52660.055*
C90.76119(11)0.5157(2)0.49218(4)0.0427(3)
C100.84922(12)0.7051(2)0.48882(4)0.0514(3)
H10A0.91880.72460.51210.062*
C110.83639(13)0.8630(2)0.45240(5)0.0554(3)
H11A0.89670.98740.45160.066*
C120.73426(12)0.8399(2)0.41647(4)0.0484(3)
C130.72046(15)0.9974(3)0.37723(5)0.0630(4)
H13A0.78101.12070.37560.076*
C140.62250(16)0.9714(3)0.34280(5)0.0668(4)
H14A0.61671.07620.31770.080*
C150.52691(13)0.7862(3)0.34387(4)0.0570(4)
C160.42289(16)0.7567(4)0.30861(5)0.0712(4)
H16A0.41450.86140.28350.085*
C170.33301(16)0.5749(4)0.31061(5)0.0763(5)
H17A0.26500.55750.28670.092*
C180.34197(14)0.4180(3)0.34758(5)0.0669(4)
H18A0.28010.29630.34830.080*
C190.44338(12)0.4404(3)0.38405(4)0.0516(3)
C200.45603(12)0.2846(3)0.42343(4)0.0550(3)
H20A0.39380.16470.42540.066*
C210.55567(12)0.3066(2)0.45787(4)0.0493(3)
H21A0.56060.20140.48290.059*
C220.65441(10)0.4888(2)0.45682(4)0.0405(3)
C230.64225(11)0.6509(2)0.41870(4)0.0418(3)
C240.53697(11)0.6257(2)0.38224(4)0.0459(3)
N11.14263(13)0.3243(2)0.73074(4)0.0640(3)
O10.84364(12)−0.01056(18)0.59898(4)0.0743(4)

Source of material

1-Pyrenecarboxaldehyde (230 mg, 1.0 mmol) and methanol (30 mL) were placed in a round-bottom flask and stirred at room temperature for 10 min. Then 4-acetylpyridine (145 mg, 1.2 mmol) and NaOH (5 mol/L, 10 mL) were added. The resulting reaction mixture was stirred at room temperature for 30 min. The mixture was extracted with CH2Cl2. The solvent was removed under reduced pressure to give the crude product, which was purified by column chromatography (petroleum ether:ethyl acetate = 1:4) to give the title compound as a red solid (isolated yield 50%). The isolated product was crystallized from CHCl3 to give red single crystals.

Experimental details

All hydrogen H atoms were positioned geometrically and refined using a riding model, with d(C—H) = 0.93 Å and Uiso(H) = 1.2 Ueq(C).

Discussion

Pyrenes are considered to be excellent organic fluorophores and they are applied as environmental probes with distinct morphology and tunable emission in various micro environments due to their polarity dependent vibronic emission, high charge carrier mobility, fluorescence lifetime and chemical stability [3], [4], [5], [6]. Up to now, numerous pyrene derivatives with good fluorescence properties have been reported. For example, (2-pyrene-1-yl-vinyl)pyridine has reversible luminescence and nonlinear optical properties [7], 4-((pyren-1-yl)methyleneamino)-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one exhibits notable aggregation induced emission (AIE) phenomena in both solution and solid state [5]. 1-Methyl benzoate-pyrene displays pure blue monomer photoluminescence and electrogenerated chemiluminescence emissions in non-aqueous media [8]. In order to search for more pyrene-based compounds, in this paper we report a new one.

There is one molecule in the asymmetric unit (cf. the figure). Bond lengths and angles are all in the expected ranges [9]. The non-H atoms of the pyrene ring and pyridine ring are nearly planar, respectively. But the pyrene unit is not coplanar with the pyridine ring (dihedral angle = 12.96(6)°). In addition, there are intermolecular C—H⋯O distances, which may be considered as very weak hydrogen bonds with the bond length of 3.4554(16) Å and bond angle of 145.8° [10]. Molecules are linked leading to one-dimensional chain along the b direction. Two adjacent chains are further connected by another possible C—H⋯O hydrogen bond with the bond length of 3.457(2) Å and a bond angle of 146.0° forming a double chain. The double chains are stacked by van der Waals forces resulting in a three-dimensional supramolecular architecture in the solid state.

Acknowledgement

The authors gratefully acknowledge financial support by Henan Province Science and Technology Project (grant no. 172102210128) and the Foundation of Henan Educational Committee (grant no. 16B150002).

References

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Received: 2017-7-19
Accepted: 2017-10-10
Published Online: 2017-11-2
Published in Print: 2018-1-26

©2018 Huang et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

Artikel in diesem Heft

  1. Cover and Frontmatter
  2. Editorial 2018
  3. Crystal structure of dimethanol-bis{3-(((2-oxidonaphthalen-1-yl)methylene)amino)-2-oxo-2H-chromen-4-olato-κ3O,N:O′}dizinc(II), C42H30Zn2N2O10
  4. Crystal structure of aqua-bis{[2,6-dimethyl-N-(pyridin-2-ylmethylene)aniline-κ2N,N′]}zinc(II) triflate monohydrate [ZnC29H31N4O]CF3SO3⋅H2O
  5. Crystal structure of (E)-1-(4-{[(E)-4-Diethylamino-2-hydroxybenzene methylene]amino}phenyl)ethanone methoxy oxime, C20H27ClN3O3
  6. Crystal structure of (E)-1-(4-(((E)-4-(diethylamino)-2-hydroxybenzylidene)amino)phenyl)ethan-1-one oxime, C19H23N3O2
  7. Crystal structure of poly[(μ2-1,4-bis((2-ethyl-1H-benzo[d]imidazol-1-yl)methyl)benzene-κ2N:N′)-(μ2-4,4′-sulfonyldibenzoato-κ2O:O′)zinc(II)], C40H34N4O6SZn
  8. Crystal structure of catena-poly[diaqua(μ3-pyrazine-2,3-dicarboxylato-κ4O,N:O′:O′′)zinc(II)] 1.25 hydrate, C6H8.5N2O7.25Zn
  9. Crystal structure of fac-(acetylacetonato-κ2O,O′)tricarbonyl(tri-m-tolyl phosphane-κP)rhenium(I), C29H28O5PRe
  10. Crystal structure of bis(μ2-methanolato-κ2O:O)-bis(methanol-κ1O)-bis{3-((4-methoxy-2-oxidobenzylidene)amino)-2-oxo-2H-chromen-4-olato-κ3O,O′,N}dichromium(III), C38H36Cr2N2O14
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  14. Crystal structure of diaqua-bis(N,N-dimethylformamide-κ1O)-bis{3-((5-chloro-2-oxidobenzylidene)amino)-2-oxo-2H-chromen-4-olato-κ4N,O,O′:O′}dinickel(II), C38H34Ni2Cl2N4O12
  15. Crystal structure of tetrakis(methanol-κO)bis{3-((4-methoxy-2-oxidobenzylidene)amino)-2-oxo-2H-chromen-4-olato-κ3O,N,O′}bicobalt(II), C38H38Co2N2O14
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  18. Crystal structure of catena-poly[diaqua-(μ2-5-methylisophthalato-κ2O:O′)(μ2-1,4-bis((1H-1,2,4-triazol-1-yl)methyl)benzene-κ2N:N′)], NiC21H22O6N6
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  52. The crystal structure of (E)-2-((2-(o-tolylcarbamothioyl)hydrazono)methyl)benzoic acid, C16H15N3O2S
  53. Crystal structure of 2-chloro-1,3-di-tert-pentyl-4,4-diphenyl-1,3,2λ3,4-diazaphosphasiletidine, C22H32ClN2PSi
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  58. Crystal structure of 2,6-bis(3-(pyrazin-2-yl)-1H-1,2,4-triazol-5-yl)pyridine – 1-ethyl-3-methyl-1H-imidazol-3-ium bromide (1/1), C23H22N13Br
  59. The crystal structure of (E)-N-benzyl-N′-benzylidene-4-methylbenzenesulfonohydrazide, C21H20N2O2S
  60. Crystal structure of ethyl (E)-5-((2-(3-hydroxybenzoyl)hydrazono)methyl)-3,4-dimethyl-1H-pyrrole-2-carboxylate – water – ethanol (1/1/1), C19H27N3O6
  61. The crystal structure of (E)-4-(3-ethoxy-2-hydroxybenzylideneamino)benzoic acid, C16H15NO4
  62. Crystal structure of (μ2-N,N′-bis((pyridin-4-yl)methyl)ethanediamide-κ2N:N′)-tetrakis(diethylcarbamodithioato-κ2S,S′)dizinc(II), C34H54N8O2S8Zn2
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