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Acta Cryst. (2008). E64, o630    [ doi:10.1107/S1600536807065476 ]

1-Phenyl-3-(pyren-1-yl)prop-2-en-1-one

Y. Wang, Z. Wang, T. Liang, H. Fu and J. Yao

Abstract top

The title compound, C25H16O, was prepared by the condensation reaction of pyrene-1-carbaldehyde and acetophenone in ethanol solution at room temperature. The phenyl ring forms a dihedral angle of 39.10 (11)° with the pyrene ring system. In the crystal structure, adjacent pyrene ring systems are linked by aromatic [pi]-[pi] stacking interactions, with a perpendicular interplanar distance of 3.267 (6) Å and a centroid-centroid offset of 2.946 (7) Å.

Comment top

Chalcone derivatives have always been of interest in the field of inorganic, organic and physical chemists and biology (Strack, 1997) due to their importance in many organic synthetic pathways, biochemical processes and enzymatic mechanisms (Ansari et al., 2005; Pattanaik et al., 2002; Nielsen et al., 2005). In this paper, we report the crystal structure of the title compound, which was obtained by the condensation reaction of pyrene-1-carbaldehyde and acetophenone in ethanol solution at room temperature.

In the title compound, the pyrene ring is substantially planar (maximum displacement 0.011 (4) Å for C12) and forms a dihedral angle of 39.10 (11)° with the phenyl ring. In the crystal packing, adjacent pyrene rings are linked by aromatic π-π stacking interactions, with a centroid-centroid distance of 4.339 (7) Å, a perpendicular interplanar distance of 3.267 (6) Å and a centroid-centroid offset of 2.946 (7) Å.

Related literature top

For related literature, see: Ansari et al. (2005); Nielsen et al. (2005); Pattanaik et al. (2002); Strack (1997).

Experimental top

The title compound was prepared by the condensation reaction of pyrene-1-carbaldehyde (0.05 mol) and acetophenone (0.05 mol) in ethanol (20 ml) at room temperature. Single crystals of the title compound suitable for X-ray measurements were obtained by slow evaporation of an ethanol/acetonitrile solution (1:1 v/v) at room temperature.

Refinement top

All H atoms were fixed geometrically and were treated as riding on the parent C atoms, with C—H distances of 0.93 Å. Uiso(H) = 1.2 Ueq(C). In the absence of significant anomalous scattering effects, Friedel pairs were merged in the final refinement.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: SHELXTL (Sheldrick, 1990).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids and the atom-numbering scheme.
1-Phenyl-3-(pyren-1-yl)prop-2-en-1-one top
Crystal data top
C25H16OF000 = 348
Mr = 332.38Dx = 1.324 Mg m−3
Monoclinic, P21Mo Kα radiation
λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 824 reflections
a = 4.6739 (15) Åθ = 2.6–25.7º
b = 22.535 (7) ŵ = 0.08 mm−1
c = 8.250 (3) ÅT = 294 (2) K
β = 106.45 (2)ºBlock, yellow
V = 833.4 (5) Å30.24 × 0.22 × 0.12 mm
Z = 2
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer		1512 independent reflections
Radiation source: fine-focus sealed tube914 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.038
T = 294(2) Kθmax = 25.0º
φ and ω scansθmin = 2.7º
Absorption correction: multi-scan
(SADABS; Bruker, 2002)		h = −5→5
Tmin = 0.981, Tmax = 0.991k = −26→14
3489 measured reflectionsl = −9→9
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.098  w = 1/[σ2(Fo2) + (0.0466P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
1512 reflectionsΔρmax = 0.11 e Å−3
235 parametersΔρmin = −0.12 e Å−3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
C25H16OV = 833.4 (5) Å3
Mr = 332.38Z = 2
Monoclinic, P21Mo Kα
a = 4.6739 (15) ŵ = 0.08 mm−1
b = 22.535 (7) ÅT = 294 (2) K
c = 8.250 (3) Å0.24 × 0.22 × 0.12 mm
β = 106.45 (2)º
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer		1512 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)		914 reflections with I > 2σ(I)
Tmin = 0.981, Tmax = 0.991Rint = 0.038
3489 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.098Δρmax = 0.11 e Å−3
S = 1.00Δρmin = −0.12 e Å−3
1512 reflectionsAbsolute structure: ?
235 parametersFlack parameter: ?
1 restraintRogers parameter: ?
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O11.0978 (8)0.06540 (14)0.3854 (4)0.0865 (10)
C10.2634 (8)0.31864 (18)0.6348 (5)0.0474 (10)
C20.4014 (8)0.30397 (17)0.5070 (5)0.0456 (10)
C30.5149 (8)0.24553 (17)0.4986 (5)0.0437 (9)
C40.4779 (8)0.20312 (18)0.6221 (5)0.0532 (11)
H40.54700.16460.61910.064*
C50.3463 (9)0.21795 (19)0.7411 (5)0.0558 (11)
H50.32770.18920.81840.067*
C60.2339 (8)0.27586 (18)0.7539 (5)0.0507 (10)
C70.0951 (9)0.2918 (2)0.8760 (6)0.0676 (12)
H70.07540.26370.95470.081*
C8−0.0129 (11)0.3477 (2)0.8831 (6)0.0781 (15)
H8−0.10580.35720.96560.094*
C90.0158 (9)0.3905 (2)0.7673 (6)0.0706 (14)
H9−0.05690.42860.77360.085*
C100.1518 (9)0.37699 (19)0.6421 (5)0.0561 (11)
C110.1810 (9)0.4196 (2)0.5191 (6)0.0657 (13)
H110.10790.45780.52310.079*
C120.3107 (9)0.40594 (19)0.3987 (6)0.0619 (12)
H120.32630.43470.32080.074*
C130.4260 (8)0.34749 (15)0.3881 (5)0.0481 (10)
C140.5642 (9)0.33242 (19)0.2671 (5)0.0555 (11)
H140.58410.36100.18970.067*
C150.6733 (9)0.27656 (17)0.2572 (5)0.0542 (11)
H150.76220.26800.17230.065*
C160.6540 (8)0.23186 (16)0.3724 (5)0.0460 (10)
C170.7838 (9)0.17355 (17)0.3629 (5)0.0527 (10)
H170.78790.14770.45130.063*
C180.8963 (9)0.15305 (17)0.2438 (5)0.0585 (11)
H180.88270.17650.14910.070*
C191.0416 (9)0.09496 (19)0.2545 (6)0.0561 (11)
C201.1212 (8)0.07115 (16)0.1054 (5)0.0486 (9)
C211.3317 (9)0.0265 (2)0.1272 (5)0.0617 (11)
H211.42900.01350.23570.074*
C221.3998 (10)0.00115 (19)−0.0091 (7)0.0751 (14)
H221.5397−0.02930.00760.090*
C231.2618 (11)0.0207 (2)−0.1689 (6)0.0732 (13)
H231.30940.0040−0.26110.088*
C241.0536 (11)0.0648 (2)−0.1928 (5)0.0740 (13)
H240.95810.0777−0.30180.089*
C250.9834 (11)0.09030 (18)−0.0569 (5)0.0632 (13)
H250.84260.1206−0.07470.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.123 (3)0.079 (2)0.0604 (19)0.027 (2)0.0325 (18)0.0182 (18)
C10.035 (2)0.059 (3)0.043 (2)−0.0053 (19)0.0029 (18)−0.007 (2)
C20.038 (2)0.055 (3)0.042 (2)−0.0131 (19)0.0081 (19)−0.0036 (19)
C30.037 (2)0.054 (3)0.037 (2)−0.0056 (19)0.0062 (18)0.0029 (19)
C40.057 (3)0.056 (3)0.048 (2)−0.004 (2)0.017 (2)0.004 (2)
C50.056 (3)0.065 (3)0.047 (3)−0.009 (2)0.015 (2)0.007 (2)
C60.042 (2)0.068 (3)0.041 (2)−0.007 (2)0.0105 (19)−0.003 (2)
C70.056 (3)0.093 (4)0.054 (3)−0.003 (3)0.016 (2)−0.006 (2)
C80.068 (3)0.107 (5)0.064 (3)−0.001 (3)0.026 (3)−0.018 (3)
C90.054 (3)0.085 (4)0.069 (3)0.001 (2)0.011 (3)−0.029 (3)
C100.045 (2)0.065 (3)0.054 (3)−0.005 (2)0.008 (2)−0.016 (2)
C110.056 (3)0.054 (3)0.078 (3)0.004 (2)0.005 (3)−0.002 (2)
C120.060 (3)0.051 (3)0.072 (3)−0.003 (2)0.014 (3)0.008 (2)
C130.041 (2)0.051 (3)0.050 (2)−0.0058 (19)0.009 (2)0.003 (2)
C140.061 (3)0.056 (3)0.051 (3)−0.006 (2)0.019 (2)0.015 (2)
C150.059 (3)0.061 (3)0.045 (2)−0.007 (2)0.018 (2)−0.001 (2)
C160.047 (2)0.047 (3)0.044 (2)−0.009 (2)0.012 (2)0.000 (2)
C170.058 (2)0.055 (3)0.046 (2)−0.004 (2)0.015 (2)−0.001 (2)
C180.077 (3)0.053 (3)0.049 (2)0.004 (2)0.022 (2)0.006 (2)
C190.058 (3)0.056 (3)0.053 (3)0.000 (2)0.013 (2)0.004 (2)
C200.057 (2)0.041 (2)0.050 (2)−0.005 (2)0.0174 (19)−0.0035 (19)
C210.065 (3)0.057 (2)0.058 (3)−0.002 (2)0.009 (2)0.001 (2)
C220.073 (3)0.062 (3)0.091 (4)0.007 (3)0.026 (3)−0.015 (3)
C230.082 (4)0.074 (3)0.070 (3)0.000 (3)0.031 (3)−0.011 (3)
C240.099 (4)0.069 (3)0.054 (3)0.017 (3)0.023 (3)0.001 (2)
C250.086 (3)0.052 (3)0.051 (3)0.017 (2)0.020 (3)0.003 (2)
Geometric parameters (Å, °) top
O1—C191.232 (5)C12—H120.9300
C1—C61.411 (5)C13—C141.377 (5)
C1—C21.422 (4)C14—C151.369 (5)
C1—C101.422 (6)C14—H140.9300
C2—C131.414 (5)C15—C161.405 (5)
C2—C31.429 (5)C15—H150.9300
C3—C161.409 (5)C16—C171.459 (5)
C3—C41.443 (5)C17—C181.322 (5)
C4—C51.340 (5)C17—H170.9300
C4—H40.9300C18—C191.466 (5)
C5—C61.422 (5)C18—H180.9300
C5—H50.9300C19—C201.483 (5)
C6—C71.391 (5)C20—C251.380 (5)
C7—C81.364 (6)C20—C211.382 (5)
C7—H70.9300C21—C221.377 (5)
C8—C91.390 (6)C21—H210.9300
C8—H80.9300C22—C231.366 (6)
C9—C101.392 (5)C22—H220.9300
C9—H90.9300C23—C241.365 (6)
C10—C111.431 (6)C23—H230.9300
C11—C121.338 (6)C24—C251.381 (5)
C11—H110.9300C24—H240.9300
C12—C131.435 (5)C25—H250.9300
C6—C1—C2120.8 (3)C2—C13—C12119.2 (4)
C6—C1—C10119.5 (4)C15—C14—C13121.9 (4)
C2—C1—C10119.7 (4)C15—C14—H14119.0
C13—C2—C1119.7 (3)C13—C14—H14119.0
C13—C2—C3120.1 (3)C14—C15—C16121.5 (4)
C1—C2—C3120.2 (3)C14—C15—H15119.2
C16—C3—C2119.5 (3)C16—C15—H15119.2
C16—C3—C4123.3 (4)C15—C16—C3118.3 (4)
C2—C3—C4117.1 (3)C15—C16—C17120.1 (3)
C5—C4—C3121.6 (4)C3—C16—C17121.5 (3)
C5—C4—H4119.2C18—C17—C16127.9 (4)
C3—C4—H4119.2C18—C17—H17116.1
C4—C5—C6122.6 (4)C16—C17—H17116.1
C4—C5—H5118.7C17—C18—C19122.8 (4)
C6—C5—H5118.7C17—C18—H18118.6
C7—C6—C1119.0 (4)C19—C18—H18118.6
C7—C6—C5123.3 (4)O1—C19—C18121.1 (4)
C1—C6—C5117.7 (3)O1—C19—C20119.3 (4)
C8—C7—C6121.6 (5)C18—C19—C20119.6 (4)
C8—C7—H7119.2C25—C20—C21118.2 (3)
C6—C7—H7119.2C25—C20—C19122.3 (3)
C7—C8—C9120.1 (4)C21—C20—C19119.5 (4)
C7—C8—H8119.9C22—C21—C20121.1 (4)
C9—C8—H8119.9C22—C21—H21119.4
C8—C9—C10120.8 (4)C20—C21—H21119.4
C8—C9—H9119.6C23—C22—C21119.9 (4)
C10—C9—H9119.6C23—C22—H22120.0
C9—C10—C1118.9 (4)C21—C22—H22120.0
C9—C10—C11122.4 (4)C24—C23—C22119.7 (4)
C1—C10—C11118.7 (4)C24—C23—H23120.1
C12—C11—C10121.7 (4)C22—C23—H23120.1
C12—C11—H11119.1C23—C24—C25120.6 (4)
C10—C11—H11119.1C23—C24—H24119.7
C11—C12—C13120.9 (4)C25—C24—H24119.7
C11—C12—H12119.6C20—C25—C24120.3 (4)
C13—C12—H12119.6C20—C25—H25119.8
C14—C13—C2118.6 (4)C24—C25—H25119.8
C14—C13—C12122.1 (4)
C6—C1—C2—C13179.5 (4)C3—C2—C13—C14−0.9 (5)
C10—C1—C2—C13−0.1 (5)C1—C2—C13—C120.0 (5)
C6—C1—C2—C3−0.6 (5)C3—C2—C13—C12−180.0 (3)
C10—C1—C2—C3179.9 (4)C11—C12—C13—C14−179.1 (4)
C13—C2—C3—C160.7 (5)C11—C12—C13—C20.0 (6)
C1—C2—C3—C16−179.3 (3)C2—C13—C14—C151.0 (6)
C13—C2—C3—C4−179.0 (4)C12—C13—C14—C15−179.8 (4)
C1—C2—C3—C41.0 (4)C13—C14—C15—C16−1.1 (6)
C16—C3—C4—C5179.5 (3)C14—C15—C16—C30.8 (6)
C2—C3—C4—C5−0.8 (5)C14—C15—C16—C17−177.4 (4)
C3—C4—C5—C60.2 (6)C2—C3—C16—C15−0.7 (5)
C2—C1—C6—C7−179.4 (3)C4—C3—C16—C15179.0 (3)
C10—C1—C6—C70.1 (5)C2—C3—C16—C17177.5 (3)
C2—C1—C6—C5−0.1 (5)C4—C3—C16—C17−2.8 (6)
C10—C1—C6—C5179.5 (3)C15—C16—C17—C18−8.4 (6)
C4—C5—C6—C7179.6 (4)C3—C16—C17—C18173.5 (4)
C4—C5—C6—C10.3 (6)C16—C17—C18—C19175.2 (4)
C1—C6—C7—C80.0 (6)C17—C18—C19—O1−8.9 (6)
C5—C6—C7—C8−179.3 (4)C17—C18—C19—C20170.8 (4)
C6—C7—C8—C9−0.4 (7)O1—C19—C20—C25157.8 (4)
C7—C8—C9—C100.6 (7)C18—C19—C20—C25−21.9 (6)
C8—C9—C10—C1−0.4 (6)O1—C19—C20—C21−19.5 (6)
C8—C9—C10—C11179.0 (4)C18—C19—C20—C21160.8 (4)
C6—C1—C10—C90.1 (5)C25—C20—C21—C22−0.9 (6)
C2—C1—C10—C9179.6 (3)C19—C20—C21—C22176.5 (4)
C6—C1—C10—C11−179.4 (3)C20—C21—C22—C231.1 (7)
C2—C1—C10—C110.2 (5)C21—C22—C23—C24−0.9 (7)
C9—C10—C11—C12−179.6 (4)C22—C23—C24—C250.7 (7)
C1—C10—C11—C12−0.2 (6)C21—C20—C25—C240.7 (6)
C10—C11—C12—C130.1 (6)C19—C20—C25—C24−176.7 (4)
C1—C2—C13—C14179.1 (3)C23—C24—C25—C20−0.6 (7)
Acknowledgements top

This work was supported by the National Natural Science Foundation of China (Nos. 90301010, 50573084, 90606004),

references
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